14 comments/  38562 views/  27 favorites

Caught For the Last Time Ch. 01

By: TGJamie



I should have known something was up. When I arrived home, I was greeted with a big hug and a long, passionate kiss as I walked in the door. This was not quite the usual greeting, but it was a nice change. 

Then she slowly slid her hand down the back of my pants, pushed me back and yelled..."What are you wearing??"

That day, like many others, I had slipped on a pair of panties before I left the house for work, and while I should have known better, I did not change back into my guy briefs before I got home. 

I keep a small stash of panties hidden in my closet and I guess I had gotten a bit careless, but you do that when you think you are going undetected.

The truth is, I've been underdressing in lingerie for years, and while I would go through the purchase and purge routine every so many months, no matter what I tried, the desire to wear women's lingerie was always there.

It was hard not to confess. There I was, wearing a cute pair of Body by Victoria panties. Not much room for good excuses. I tried to calmly explain that certain days I just feel like wearing a pair of panties and this was one of those days. And this wasn't the first time she found them either. Sometimes it was panties, sometimes a bra, camisoles, and even nighties. 

At least my story agreed with what she was seeing. She had found out where I was hiding my panties. And to be honest, I was running out of good hiding places. 

She must go on treasure hunts looking for them because the panties were neatly folded and tucked in an inside pocket of a winter jacket I hardly ever wear. She must have found them and then noticed that one day, one pair was missing and then they were returned the following day. Several days later, another pair was missing for a day, etc. She had to have been checking every day. Today she knew a pair was missing and that's why decided to check me. It was like a sting operation.

Despite our multiple discussions in the past over her finding lingerie in the most unusual places, it never seemed to change anything. The discovery was always so upsetting to her that we never really talked about it beyond in that moment. There would be a flare up, I'd feel guilty, she would toss the items she found, and that would be the end of it. 

So here we are again, having another heated discussion that probably won't go anywhere. This one ended with the silent treatment, with her shaking her head in disappointment and her walking away. We went on with our lives.

But then something different happened a few days later. During dinner we got into a serious discussion about my wearing women's lingerie. She explain passionately that her world has being turned upside down by all this and that she was always wondering about what else I was doing besides just wearing lingerie. She was genuinely concerned. I told her I could see that and that I understood. 

I then tried to explain my side of it, sharing with her for the umpteenth time that I've had this desire ever since I was teenager and that I really just enjoy wearing them. That's all I ever wanted to do. I'm not gay and I don't want to be with anyone else. And my desire to wear women's underwear was probably never going to go away.

I think she acknowledged my side as well, although she did not necessarily understand or agree with it. 

She must have been thinking about this for the past few days because she offered a thought. 

"Rather than me always waiting and wondering if you are underdressed as you call it, couldn't you just establish some sort of a plan or timetable that on some certain day of the week you were going to wear panties? Basically, just let me know so I could at least be prepared." 

I was stunned. I was not expecting this at all. Needless to say, I readily agreed to think about it and give her a proposal. 

For the next day or two I spent time thinking about some solid, responsible options and weighing them against some unbelievable fantasies. It wasn't easy. I didn't want to go too responsible and have her say, is that it? Nor did I want to go over the top and have her think even worse of me. And trying to find the right time to sit down with your wife to talk about wearing women's panties is not quite in any marriage handbook. 

So Thursday night while we were sitting at the sofa watching TV, a Victoria Secret's commercial came on promoting one of their big upcoming infomercials. I got a little embarrassed and was about to quickly switch channels, when she interrupted and commented..."Oh look, aren't those the same cute Victoria Secret's panties you were wearing?"

Gulp. "Probably not", I murmured. "They only have a few styles that really fit me well. And I only buy them if they are on sale. They are very expensive otherwise." 

"Well, at least I know you are budget conscious. I suppose that is a plus. And while we are on the topic, did you give any thought to my request of coming up with a plan?" 

I told her I had some ideas but had not quite thought out everything. 

"Well, let's hear what you have." 

I then offered, "Maybe something like this would work? During the week, say on every Monday and Friday, I would wear a pair of panties under my work clothes, and then I could wash them on the weekend with my normal wash." 

Slowly she responded, "Alright. That sounds acceptable. What about the weekends?" 

"That's what I was having problems with. I really would like to be able to wear a pair while at home every so often, but I know that might be upsetting to you. When I wear them it's actually like a calming influence on me, kind of like I'm relaxed or feeling normal. I know that sounds weird, but for me having to wait until after the weekend to wear them on Monday may be more of a distraction to me over the weekend."

She thought for a moment and replied. "You are right. That does sound weird. But you make a good point and I can see you have weighed this in your mind a lot. Here's a thought, as long as you do not flaunt it on the weekend, maybe one day on the weekend would be OK as well. We could at least try it. At this stage I am willing to try anything. I am really at my wits end."

Wow, this was a huge concession. I was secretly hoping for this but really did not see this one coming. I was getting what I really wanted and could eliminate the sneaking around. This could give both of us this peace of mind.

But, she said, "I am adding a few conditions. First, you never ever wear my stuff. You will have your own things. And rather than hiding them, I want you to keep them in your dresser drawer so I can see what you are wearing and when. Also, you never wear them to bed." 

I could easily agree to those terms. It sounded like a great plan. No more sneaking around. I readily agreed.

With that she reached beside her and pulled out the three pair of Victoria Secret panties she had taken a few days earlier. With very little emotion, she placed them on the sofa beside me and went back to her reading. 

Rather than me sitting there looking at them neatly folded on the sofa, I took them upstairs and placed them in my dresser drawer with my other underwear and came back down for the evening. I tried not to look too excited when I came down the stairs but I was thrilled. I could not help but think, only 10 more hours to wait to wear them! Tomorrow was Friday!

The next morning, I awoke at the normal time, showered and selected the pink pair of Victoria Secret's panties. For some reason, I felt so relaxed and comfortable sliding them on. They felt nice and sexy on, and my heart wasn't racing like other days thinking that I might get caught. 

I could actually enjoy this. I put on my slacks and got fully dressed, grabbed a coffee and some fresh fruit with my wife, gave her a nice kiss and headed out.

When I came home, she had already arrived home so I know that if she had not checked my drawer right after I left for work, she certainly checked my drawer before I came home. I was waiting for the full body scan at the door, but there was none. Just a nice hello, a quick kiss and a pleasant "What would you like for dinner?"

I went upstairs and changed, but kept the panties on with a pair of comfortable shorts and a polo shirt. We talked about the day's activities, had dinner and settled in for some TV. There was not a single mention of the panties. It was like it never happened. I changed out of the panties before we went to bed and all was calm for day one. 

The weekend was equally uneventful. On Saturday I got up, showered and put on a different pair, this time a powder blue with lace. I love this Body by Victoria line. They really fit the best. 

I had a chance to do my laundry including the pink pair I wore yesterday and carefully put them away in my drawer beside my black pair that I was planning to wear on Monday.

I kept waiting for either some sweet comment or a massive blow-up over the weekend, but it didn't happen. The days turned into weeks, it was almost as if nothing had changed. There were times I wanted to shout out...I'm wearing panties! But heck, she didn't when she wore her panties so why should I.

In the weeks that passed, there were no conversations about the lingerie at all. It was decidedly quiet on that front...almost spooky.

My routine stayed very simple and very subtle just as she asked. Twice a week I would get dressed in the morning for work and put on a pair of my panties. To be honest, those work days were exciting for me. There was always something special about the days I would wear them. 

Was I more diligent at work? Did I sit up straighter? Was my attitude better? I think that was a yes on all counts. Heck, even people at work noticed I seemed a bit happier. 

And at night, before going to bed, I would always change out of them. No more sneaking into or out of the house. I am sure she was still counting and keeping track of what I was wearing and when, so I definitely wanted to keep wearing them on just a periodic basis.

I just kept waiting for something to happen...and then it did. But it was not what I expected...

Caught For the Last Time Ch. 02



During the week, one of my wife's Soma lingerie catalogs arrived in the mail. I tried not to look at her looking at it while on the sofa, but she knew better. She looked over at me and asked..."Have you ever been to Soma?" 

I replied "Yes, but they are a bit pricey." 

"Well, Soma has these wonderful panties on sale right now. You been wearing those three pair of Victoria Secret so many times, I am afraid that you are going to wear them out and then start looking for other pairs on your own. Would any of these be of interest you?"

With that she showed me the pictures in the catalog and I have to admit the models would make any panties look great. It's hard to tell from a picture but at 5 pair of panties for $35 it sounded like a good deal and just her offer alone was worth me saying I was interested. It was weird. We were both looking at a lingerie catalog for ourselves.

As she turned the pages with me, there were bras, gorgeous nightgowns and long summery dresses. "Have you ever had your own bra?" 

My answer was "Yes, but they were pretty ill-fitting ones over the years, but never like these. In fact, I think you found one or two of them tossed them." 

"Oh yeah" she said..."bad question. Oh look, these camisole bras are quite nice." I was shocked, but thrilled that there was some communication after weeks of absolutely nothing.

At that time, her cell phone rang, she closed the catalog and the conversation ended. I felt a bit awkward the rest of the night, not wanting to bring it back up but knowing we left the conversation hanging.

For the next two days I had trouble concentrating at work because I was not sure where this new discussion was heading. When I arrived at home on Thursday I was about to change when she did the same move of kissing me and reaching into my pants, only to find my boring guy underpants. "So you've been good I see?" 

"Yes, I'm trying to keep Monday and Friday as the days I wear them to work. I told you the desire is not all the time, but it's definitely still there a lot." That at least gave me a little credibility.

I finished changing and while we were having dinner she said she had been thinking more about our brief discussion the other night and she had actually headed over to the Soma store at lunch. 

She said, "I got to talking to one of the sales associates and found that it seems that a lot a men purchase Soma lingerie for themselves...more than I ever realized." 

She went on to say, "I tried to research it online, but you never can trust what you read on the internet that's why I went in person. She told me many of the men are professionals like yourself, and they are regular customers. In fact the sales associate seemed to brush it off as a relatively routine event when I asked her more about it." 

She then continued, "So, I got to thinking. You have done exactly what you said you were going to do as it comes to wearing the panties, and I really appreciate it. I was afraid that you were going to be prancing around the house in them and I could use that as a reason to ask you to stop. That did not happen. I'm beginning to feel I can actually trust you even though it's been only a month." 

"Here's what I propose. I would like to offer you the option to buy some lingerie at Soma, but I want to know what it is you are buying. No sneaking around anymore. Here is a $100 Soma Gift card. Consider it an early birthday present. When you go there, I want you to ask for Carol. She is the person I spoke to and she will make the visit comfortable for you. She was very helpful in talking to me about your cross dressing."

"But", I replied, "the panties we saw in the catalog sale were 5 pair for $35. What about the other $65?" 

"Use your discretion. When I consider all the items of yours I have tossed over the years, I am certain you can find something appropriate at Soma. I want to see how you use your judgment. You do not need to spend it all, but you can. Carol works tomorrow and the sale ends of Sunday, so I would head over there tomorrow."

That really lifted my spirits. On Friday morning I happily put one of my three rotating pair of panties and headed off to work. When work ended I headed straight over to the mall where Soma was located. I was both nervous and excited, and walked by the store entrance about 5 times before I actually entered.

There were two sales associates on and only one other customer in store. I started browsing the items and was greeted by one of the ladies. She was slightly older than myself, but very nice. She asked if there was anything special I was looking for. 

Even though she introduced herself, I could also see from her badge that she was Carol. I did not want to blurt out why I was here right away so I said, "I saw the Sale sign and wanted to look around."

Carol said, "Feel free to ask me any questions at all", and headed back to straightening the racks.

Soma is like a large boutique store. Imagine setting up and having your very own lingerie room at home...that's Soma. 

After looking at nearly everything in the store, Carol came back over and asked again if I needed any help. Now that I felt more comfortable and oriented in the store, I mentioned that my wife was in yesterday and suggested I come by and see you. Carol said, "Oh yes, say no more." 

She immediately put me at ease by sharing some fun stories of other men who come in. "There are some regulars who show up for all the big sales and I know them by their first names, and then there are others who come in and say they are buying for their wives or girlfriends who just happen to be the "exact" same size as them. We really believe those stories! But, we respect their privacy and they are good customers too."

"Now as I recall, we have $100 to spend, correct?" 

"Good memory. Well, I have a $100 gift card but don't have to spend it all." 

She countered with..."Now what fun would that be if we didn't? Your wife and I went through the entire store and she first looked at the panties. So let's start there. My guess is you are a size 7 and these are the ones on sale over here. Let me show you a few things. Many Soma panties have a band of elastic around the inside on the legs so they don't ride up and don't show a line. I love them. Why don't you look through these for a bit and find some you like."

Soma does make good quality. Within 15 minutes I had been through the entire display and found 5 pair that I liked. Carol returned, approved 4 of them and suggested one other pair for me. "That will be your five for now. Those are all wonderful. Now, let's find a bra for you."

"A bra, really? I was thinking that might be a little much for my first purchase." 

"Hmmm." She replied, "Based upon what your wife said to me, I think she was expecting you to buy one. We just need to find the right one that fits you perfectly."

I was shocked. "Carol, are you sure?" 

"Yes, and we have a great sale on these camisole bras. They have lace in the front and do a nice job of covering up any little chest hair. While you were over at the panties, I looked for what I think your size is. What do you think of these?" 

Carol had already picked 5 different styles. "Let's try each of these one and let me see each one when you are ready. I want to make sure the fit is right." 

I was escorted to one of the last fitting rooms, removed just my polo shirt and tried on the first one. Carol asked to see each one so she could observe the fit. Some were tight on the straps, some seemed to cut a bit under the arms, and one style seemed just about right. 

"Good, let me get a few variations of this style for as well as a few different colors. I'll be right back she said." 

Of all the ones she picked I liked the black camisole bra the best but she said it was still just a little bit tight around the back strap.

"Here's what I want you to do. Give me the black bra and I'm going to get a bra extender. Now, slip these black panties on...they are one of the five you are buying and I will be right back." When she returned she handed me the bra over the door and I slid it on. 

It now fit perfectly with the extender...who knew. I was now wearing a bra that was actually fit to me! 

For the first time ever I was now seeing myself in a matching bra and panties...and from Soma. It nearly took my breath away. She asked me through the door..."Is it a good fit? Do you like it?" 

"Oh yes. They are perfect."

"Great!" She replied, "Now get dressed and we have one more thing to look at." 

This all takes more time than I ever imagined. I have now been in Soma for an hour and all I have to show for it is one bra and 5 pair of panties. I'm not complaining, I'm just saying. And I loved the attention.

Carol walked me over to the nightgowns and loungewear, sorted through the racks, held up a gorgeous long black gown against herself and asked "How do you feel about something like this?" 

It was beautiful. The fabric was so soft and it hung graciously on the hanger. I told her, "I have only had inexpensive nightgowns from places like Kmart, never anything like this. But my concern was not over the idea, but over how my wife would take this." 

Carol confided in me that there were 3 categories my wife looked at with her while at the store...panties, bras, and loungewear. And like yourself, it was this area she felt uncertain as to how you would feel. I felt like Carol was now more of a friend than just some nameless sales associate. 

As we looked through the items, they were simply too pricey for my $100 gift card so even though I loved them, they would not fit it in my budget. Then Carol brought me to the back of the store where the markdowns were. 

We went to the large and XL part of the rack and there were probably about 10 different items that were there. This was now more difficult because of my budget and their limited availability. From the rack we were able to select 4 possible items. 2 babydoll style nighties, one chemise and one longer outfit with pants.

Back to the dressing room. The first baby doll nightie was simply too tight around the chest and was a no go. The second baby doll was very flexible on top and was a definite possibility. The chemise was cut so well and hung perfectly, and the loungewear outfit with pants was simply elegant. And, any one of the three would keep me under the total budget of $100. 

"Carol??? I need your help." She was standing relatively close and came right over. Now other than helping me with the bra fitting, Carol had not seen me with anything on so this was strange. When I called her I was wearing the loungewear with pants.

She said, "Let me see what the fit looks like." I opened the door and she looked at me head to toe...nodded and said she loved it. She said the fit was perfect, and she liked how the flow of the long top and pants worked well with my shape. She adjusted the shoulders a bit and checked it out one more time and said...that will work perfectly. 

"Now let's see the chemise."

I quickly changed to the chemise in its rich blue colors, and she loved that one too. The chemise not only hung well but had a nice flare at the hips. She said, "The flare makes it look more feminine on you even though you have no hips. See how it gives you balance and shape? Watch for that if you ever buy one in the future as well. Now, let's see that baby doll."

I carefully removed the chemise and slid the babydoll nightie on. 

"Wow" she said, "the baby doll does fit extremely well and you look sexy in it. But, it may be a bit too much, or better yet...too little, for right now. Sexy may not be the look you are looking for today." 

She had a good point. I was getting excited just trying it on!

I tried on each item one more time for myself, looking in the mirror from all different directions, wanting to buy them all, but finally deciding on the loungewear top with pants. 

Reluctantly, I got dressed and when we settled up it all came to $96. 

Carol said, "I really hope that you can come in again...we always have sales...and I know your wife will be pleased with your purchases. And if I am not in, just tell any other sales associate that I helped you and they will all be just as nice." I kept the receipt and walked out with my Soma bag in hand.

As I was getting close to the house, I started getting all nervous again, but a different type of nervousness. This was nervousness as to uncertainty. She had given me the card to spend and I was nervous that she might not approve of what I bought. 

As I walked up to the door, I got even more nervous. Would she want me to hide them away and never see them herself? Would she want me to just show them to her? Or would I have to model them? I had no idea. 

"Where have you been for so long? I cannot believe you spent more than two hours at Soma!" I stood there shocked and in disbelief. 

Then she laughed and said..."I'm just kidding. Shopping is quite an experience. Now you know what I go through all the time. I'm starved, let's a have a quick bite to eat and you can tell me all about it." She was more upbeat that I expected, so that was real good. 

I put the bag down and we had a nice salad and some wine. I gave her a complete description from me arriving at Soma and being totally nervous through my finally checking out, and now feeling a bit nervous all over again. Then she said..."Don't be nervous...let's see them." 

I reached for the bag and started to take then out she said, "Oh no. These are now yours and if you are going to wear them, I want to see them on you at least once so I know what they look like on you. I only caught a glance of you that time I caught you in those little Victoria Secret panties. I need to know what these look like." 

"Are you sure? It would be faster to just show you them here." 

"Nope, go put them on. And let's see the panties first."

I brought the bag into the bathroom, stripped down and put on the panties. I decided to start with the most conservative pair. I selected the simple white pair first which had a cute lace pattern along the waist band. 

It's funny, except for the black pair I had never actually tried any of these other ones on at Soma. They looked as good as I hoped they would. I slowly opened the door and asked..."Ready?"

She said yes but I was not sure if I was. 

"Come on, let's see." 

As I stepped out I could see her struggling to offer a comment. She was now seeing what she must have been visualizing for years. I was not quite the model in the catalog, and to be honest, I was not feeling as comfortable as I thought I would...I was standing here modeling just a pair of panties. I may have even been a little red faced. 

All she could muster up was, "They are a good fit and they were pretty." It was like hearing you had a nice personality.

The peach colored ones were next and they also had a little more lace and were fairly conservative as well. I think by the second pair the initial shock for both of us was over. She said, "The peach color looks good on you. That was at least an improvement.

I then modeled for her the pink ones with the lace panels on the side and a cute bow. She actually perked up and said, "I love the bow on the front. It's cute."

"I like it as well", I replied.

They were then followed by the red pair. These were relatively simple but the fabric was much softer and the legs had a lot of lace on them. 

She actually asked me to come closer so she could examine the lace and the fit. These got the best response. "You look really good in those." 

I saved the black pair for last. When I asked. "Do you want to see these with the bra as well?" she said "Of course."

This was the big build up. I made it through showing her the pink and red panties so this should be easy. But this was the first time she would see me standing there in a bra and panties. Waiting until now to put the bra on was a good idea. I had built up at least some courage. A model I am not. 

When I walked out, she actually complimented me on the combination. She said, "Having the bra and panties on together make you look better...kind of completing the look. You seem more balanced. I actually really like that look on you." 

She asked me to come over so she could see closer. I had to turn around for her slowly and she commented that the fit of the bra fit was very good as well. 

The last item was the loungewear. It was also black with a little gold trim. I decided to keep the bra and panties on to keep any excitement down, and then slid on the long pants on and then the top. I checked myself out in the mirror and straightened out the top like Carol did. 

Before heading out I tried to stand up straight and keep my shoulders back. Strangely, the outfit I felt most uncomfortable with buying was now going to be the easiest to show her. I now felt like a girl!

As I walked out with my hands lightly clasped in front of me and my shoulders back, there was no response from her. 

She had me turn around and finally asked, "Does all this really make you that happy?"

That was a real downer. As happy as I thought I would be, I was not feeling that way at all after she asked me that. 

I responded as nicely as I could, "Yes it does and I thought I did a good job of shopping and buying nice things." 

I was now so glad I did not buy the baby doll nightie. That could have been a nightmare. I returned to the bathroom and changed back. 

When I put everything away in the bag and came out she said, "OK, here are the rules. You may keep them in your dresser, but all in one lower drawer. You now have a lot of things. You may wear the panties any time you want except to bed. You now have plenty to go around."

"As to the bra, please wear it only when you are at home and please wear it under some shirt or sweater. Try to be subtle. And when I am out of the house, you may wear the loungewear. You don't see me prancing around the house in my lingerie so I don't expect you too either. Are we clear on this?"

I tried to smile, but I still felt like I was someone who had been caught all over again. I told her that I totally understood. 

I was now getting the freedom I was hoping for and now had to work on being about as normal as I could. This was not going to be easy but it's a challenge I was looking forward to. I went upstairs and moved a few things around in my dresser and folded up everything neatly in the bottom drawer.

I was so happy that at least tomorrow was Saturday. This was going to be the first time I could wear a bra at home. 

On Saturday I got up at my normal time, showered and wore my black bra and panties under one of my looser dark shirts and pants. Heck, I couldn't tell I even had it on as I checked myself out in the mirror. 

I went downstairs, made coffee and waited for the wife. After a bit, she made her way downstairs and I could tell she was taking glances at me from different angles...is he or isn't he wearing the bra? But she would not say a thing.

Seriously, after about an hour of starting laundry, cleaning up some bills and putting things away, I forgot I had a bra on and I think she did too. I wore it through until dinner on Saturday night and decided that 8 hours in a bra was more than enough for the first day. 

And when I changed and looked in the mirror, I actually loved the telltale signs of the bra straps on my shoulders and back...that was so cool. 

And again, like before, not a word from her.

Anticipation for the new week was now growing. I now had 8 pair panties to choose from and my own bra and loungewear. Each day I got up and selected an appropriate colored pair of panties, got dressed, had a light breakfast, said goodbye and headed off to work. But I did not underdress every day, but I did many for many of them.




Caught For the Last Time Ch. 02



In my mind I could see her running upstairs each day to see what I had selected for the day, but that was not my worry anymore. It was now so peaceful. The days went fine, in fact maybe a felt a bit more productive because of my overall attitude.

On the weekdays when I decided to wear a bra at home, I always made sure I had a shirt or sweater on that would mask the bra a bit. I usually, but not always, got home first. So changing and deciding what to wear with the bra was easy. I could try different combinations. 

With whatever I chose, I always enjoyed checking myself out in front the mirror with the bra on first...love that bra...and then to see how the shirt would look with it. Trying to be discreet was always the challenge. 

And she would always tell me when she was going out shopping and for about how long. I suppose that was my cue that I could safely wear the loungewear. It seemed to be working fine. No fireworks, no anything for that matter. This routine was working fine for over a month. Maybe she thought if she ignored it I would get over this dressing thing. 

And it didn't affect our sex life. That was always robust, and she liked me being her man. I think that's why she insisted that I didn't wear any lingerie to bed. I could tell she was trying to balance this all out in her head as well.

But it was still hard to figure her out. While I was really enjoying the freedom I was having, I just wish I knew what she was thinking. And then came the break I was looking for...



Caught For the Last Time Ch. 03



So one evening while watching TV, she was sitting there sifting through catalogs and mailers. As she tossed another one on the floor she asked "Have you noticed how many sales there are on lingerie at the different stores right now?"

Trying to be oblivious, I said "Not really, they always seem to have sales." But I said to myself, heck, I've noticed all my life!

She just smiled and said, "I suppose you're right. I've been doing a lot of thinking these past couple of weeks, but not a lot of talking. I know that must be frustrating for you. I just wanted to let you know how responsible you have been from my standpoint."

"I'm not worried about you like before. You've been doing your laundry, and keeping things in your drawers like I asked. I even have trouble telling which days you are wearing things under your clothes or not. Like, do you even have a bra on now?

"No, not tonight. But hearing you say that makes me feel a lot better. You have been pretty quiet since the day I did my shopping at Soma. I am never sure that I am supposed to bring things up with you or not." 

"You're right, it's still awkward for me, but I'm dealing it with."

Then she asked, "Have you ever heard of Tshirt bras?" 

"Is that a bra made out of Tshirt material?" 

"No silly. They're bras made for you to wear under Tshirts. The reason I ask is that I am getting a little concerned that you are going to stretch out that nice bra you bought at Soma's, and I know how much you like it. That's kind of why I asked it you were wearing it tonight."

"A couple of days ago when you were working on paying the household bills, I saw you reach under your shirt and adjust one of the bra straps a bit and then go right back to doing what you were doing. That actually looked cute. Until then I really had no idea you were wearing a bra. I appreciate that." 

That was like the first positive comment about dressing I actually had heard. She went on to say...

"So, I was over at Kohl's today and they were having this sale on Tshirt bras. I was not positive about your size because different brands fit differently, but I took a chance that this size 38B might fit you." 

With that, she reached over and pulled out a small bag from Kohl's from beside the sofa. "Here take a look at these."

Inside the bag was a white bra and with matching panties. The cup and straps were much different than the Soma bra. They were soft and smooth, and more flexible. I really liked the feel of it.

I said, "They look very nice. May I try them on?" 

She smiled and said, "Of course silly." 

Her demeanor was much nicer tonight. It was almost as if she was trying to please me for a change. "And when you come out, put on just a Tshirt so I can see how it looks. After all it is a Tshirt bra!"

I went upstairs and first put on the new white panties. They were your basic simple modal fabric panties and they fit just fine. 

When I slid the bra on it was a perfect fit as well. I really liked it because it seemed to hug me around my chest a little nicer. Having a soft smooth B cup really makes a difference. And because it was a bit more flexible, I did not need a bra extender.

I then spent a few minutes going through my Tshirt drawer and found one that I liked that was rather soft and comfy, and hung just below my butt. 

When I looked in the mirror, I could actually see the Tshirt cling a bit to my new shape. It was amazing. Unlike wearing the heavier shirts and sweaters, this was much more revealing and flattering! 

As I headed downstairs, I did not remember whether she had said, put on a Tshirt or put on just a Tshirt. I was hoping the latter and carried my jeans down just in case. I did not want to ruin this moment.

When I walked into the room, my wife said..."Wow. I did not expect that much of a difference. That actually looks cute on you. Now, turn and let me see you from the side...and now the back. Very nice."

"Come over here for a minute." I walked over to her and sat on the couch. I pulled my legs up under me and turned to her. It felt a little awkward sitting there in just a Tshirt, bra and panties...just a little too exposed. 

"So tell me. What do you think of the fit?" she asked. 

I told her, "It could not fit any better, and I especially liked the feel of the fabric and cup. The bra seemed to embrace me more and feels so comfortable." 

"And now for the look. Go over and stand in front of the mirror for me." 

I got up, walked over to the mirror and she asked, "Can you see how the white color of the bra against your flesh makes the bra actually visible under the Tshirt?"

I looked in a couple of directions and sure enough, I could see the white against my skin and through my Tshirt.

"That's why they also make bras in the nude or neutral color so they will disappear against your flesh. Sometimes you want a bra to show, and sometimes you don't." 

She then asked, "Can you tell which color bra I am wearing tonight?"

"Sure, it's black. I can see it through the lace in your blouse." 

"Good, that's because I wanted you to see it.", she said coyly.

After we chit chatted about the finer points of bras for a bit she said, "Here's what I want you to do tomorrow after work."

"Head over to Kohl's and buy yourself a few sets of bras and panties. You now know that this style of Maidenform bra fits you perfectly and I know they have other colors. Find some colors you like and buy the matching panties. Think of it as another reward for being so responsible." 

I was really beginning to like this responsible thing! 

I gave her a kiss and she lightly rubbed her hand on my back where the strap was and said, "I'm glad you like it too." 

I then stood up and slid my jeans on over the panties. 

As I was about to sit down she said..."One more request. Before you sit down, please take your Tshirt off and let me see the bra with the just jeans." 

I reached down and pulled my Tshirt over my head in one movement. "OK, now turn around for me." She just smiled and said..."Perfect...I really like the look and fit."

I scooted over to the mirror to check it out as well. It was cool. This was another nice reason to be fit.

I put the Tshirt back on and continued to wear the new bra for the rest of the evening. At night before bed I was careful to remove it and the panties and tuck them away in my drawer.

The next night I went to Kohls right after work. It took a few minutes to locate the Maidenform area because there were way too many bras at Kohl's. But what was important was that I now know which ones fit me. I located the right size and now began putting together some sets. 

First off was the neutral color. That was easy. She had commented on that color so it seemed only appropriate to buy that one. Now for the other colors. 

I had a black bra so let's try pink...OK, there's the pink 38B and here are matching panties. Great, now, let's get one more set. 

I was looking at the both red and the deep blue bras, and was really torn between the two colors. Then a cute sales associate came up behind me and said..."Hi, I'm Erin. That's quite a collection you have...someone is going to be very happy." 

I replied, "That's for sure". 

I then asked for her advice. "Which color do you suggest? I already have a white one and am getting these two." (I tried to be kind of vague on who it was for). 

"That's a tough call. Both are bold and both are great colors. Go with the blue. That's my favorite. Save the red for a holiday like Valentines or Christmas." 

I thanked her and she replied with, "Hope she, or whoever, enjoys them!"

Within 15 minutes off arriving at Kohl's I was ready to checkout...much quicker than at Soma.

Since it was such a quick trip, I even got into the house before my wife got home did so I thought I would surprise her a bit with the new purchases. 

I changed into my jeans and put on the nude color bra and panties with a nice classy white Tshirt from a trip we recently made. 

I was amazed that you really could not see the bra through the Tshirt because of the nude color. The bra actually disappears. And the Tshirt was loose enough and did not cling. 

I spent about an hour cleaning up the place a bit, putting dishes away, folding some laundry, and she finally arrived. She had been grocery shopping and I helped her take in the bags and put away the groceries. As I bent over to pick up the last of the bags to be put away, she rubbed my back. 

Teasingly she said, "Is that a bra strap I feel?" 

"Yes it is...and a new one as well." 

"Let me guess, it's the neutral color because I could not even tell you had one on until you bent over." 

"You are good."

As we put away the rest of the groceries, she commented on how nice everything looked in the house and what a big help I had been these past few weeks. It was nice to get a compliment.

"OK," she said, "Now show me what you bought." 

This time I opened the bag and laid out the other two bras and matching panties on the table by color. She approved and was pleased with the colors and the fact I only bought three sets.

"Same rules," she said. "You may wear these bras at home. And feel free to wear them under Tshirts or polos, rather than the loose shirts and sweaters. These Tshirt bras are much less obvious than the fancy Soma bra."

"And to be honest, I was getting tired of seeing you in some of those oversized shirts you picked. And I know you were doing it for me because I asked. You were being sweet."

I now had 12 pair of panties and 5 bras, and loungewear. They took up almost my entire bottom drawer. 

And it was so nice now to have choices. Slowly, I started wearing panties and bras just a little more often. Weekends at home were now falling into a comfortable routine. After showering in the morning I would throw on a pair of cutoff shorts, maybe the pink bra and matching panties and a Tshirt, and I was good for the day as long as we were around the house. Even wearing the white set was fun. 

And weekdays, I now had plenty of options. I could wear the panties all day at work, come home and toss on a bra and then change at night before bed. I still was careful to not wear panties every day to work or bras all the time. She still liked me being a guy.

Keeping a simple routine and not going overboard still seemed to be important to her so I tried to be aware of her concerns as well. Nothing was ever worn to bed and our sex life could not have been better. 

What was not to like.

++++++++++++++++++++++++++++

All went well for months until her sister got sick and needed someone to watch the kids for a few days while she had some minor surgery. My wife volunteered to cover the time for her out of state and needed to be away for four days. 

"No problem. Go", I said. "I can take care of myself, and since they are weekdays, I'll be at work anyway." 

So after a day of scrambling and doing errands so she could leave, we had a sit down discussion about my dressing while she was away. She started off by saying...

"I'm not worried about you during the day. I know you are responsible, but I am a bit worried at night. 

I assume you would want to dress a lot more while I am away so let me ask you, what would like wear when you come home from work if you could wear anything at all? I'd rather ask you now and not worry about you than keep second guessing while I am away." 

I did not see this one coming. I thought for a moment and answered,

"Well, since in these warmer months when I do decide to dress, I usually put on shorts with a bra and nice Tshirt, maybe a simple skirt and a nice pretty top would work?" 

"OK, that makes sense. Better get two tops though. It's getting warm out and it's nice to have a fresh change ready." 

I almost fell over. That was way too easy. I then made another suggestion and held my breath.

"And at night, I would really like a nightgown to wear to bed." 

I kind of stumbled that one out a bit. I had never asked before, but this seemed like a perfect time. The bedroom was still a taboo but she was going to be away. 

"Hmmm. If I say yes, I don't expect any funny business."

"Haven't I been good with the loungewear?"

"You have, I know that. It's just that nightwear is different wearing a bra. OK, here's what I'm comfortable with. Carol over at Soma told me how cute you looked in the baby doll nightie and chemise. Maybe they have similar ones still on sale. They have quality items that are not that erotic. I can't stand those stupid nighties with cut-outs and fur around them and split crotches."

"Yeah, I'd look awesome in one of those." I added. We both kind of laughed at that. 

I never knew if she and Carol had ever talked after I made the purchase made months ago but it sure seems they did.

Within a few minutes she grabbed a cab to the airport and like that, I was home alone for a few days. 

It was too late to go out shopping so I made my way upstairs and put on my Soma loungewear. I made myself a little snack and sat down on the sofa to watch a little television. 

This was kind of fun, but lonely at the same time. I watched a few shows and decided to call it a night because I had a busy week coming up. I went upstairs and for the first time slept in my Soma nightgown.

When Monday morning came, waking up in a nightie was surreal. I went downstairs in my nightie, made my coffee in my nightie, and had breakfast in my nightie. I really loved the morning. 

After showering I put on my deep blue panties and carried my matching Tshirt bra out to the car for later on. Work really dragged today but finally it was time to head out. I was wearing a dark shirt today, so I took a chance and changed into the bra at work in the restroom before leaving. 

I had never done that before but I was one of the last to leave so I felt safe. There was something special about walking to the car wearing both my bra and panties.

I had been thinking of where to go shopping and realized that maybe Kohl's would be the easiest to buy something relatively inexpensive. My first stop was the separates area. I could not believe how many tops and skirts there were. I literally was in no rush at all and spent a real long time looking. I finally ended up with a kicky little black flared skirt and several nice tops. 

Not exactly knowing my size in clothes I was thinking that I would have to buy them and return them if they didn't fit. But as I was walking around the store there was the men's fitting room, completely unattended. I scooted in, tried everything on...loved the skirt and decided on the deep purple jersey top and the ivory lace top. I put the other items back and checked out. These came to a whopping total of $33. I love Kohls!

My next stop was to Soma. As luck would have it, Carol was working and she recognized me immediately even though it had been months. It was like old times. There was no more nervousness. 

We spent some time just chit chatting about how things went from my perspective and I told her I was looking for a couple of nighties. We knew exactly where to look. Sadly, the ones I saw before were gone but she suggested some other ones. And as she opened the fitting room door for me she whispered to me, "And my, my, you're wearing a bra tonight. Aren't you the brave soul?" 

"You can tell? Really?"

"It's my job." She replied with a smile.

Markdown racks are amazing. I found a perfect baby doll for $23 and cute chemise for $20. I tried them on and they both fit perfectly. I showed Carol each one of them and she whole hearted approved. 

She even said, "I even like these on me more than the ones several months ago...and definitely come back again! It was wonderful seeing you again!"

I really enjoyed shopping and I really enjoyed getting home and changing. I could now say that dressing at home was much more relaxing than I ever thought. Each day this week I would come home and change immediately. The freedom of wearing a skirt with a pretty top, and feeling the soft breeze of the air blow by as I worked around the house was a sensation that I loved.

I found myself walking all over the house just to enjoy the feel. Upstairs and down, into the basement to do laundry, and cooking at the stove. I could not get enough. 

And the Tshirt bras on under the tops really completed the picture. It was more fun doing tasks around the house and I made sure the place was spotless when she came home. I could feel myself becoming more of the girl at home doing chores rather than just pretending in my mind. It was awesome.

Wearing the nighties was the real challenge. As an evening grew on, I found myself wanting to change a bit earlier than ever before. They were so comfortable and really looked so good that I could not understand why women would not wear them more often. 

I also found myself touching myself more. While watching TV I found that a light movement of the nightie would cause my nipples to get hard. I really enjoyed that feeling...a lot. And when they got hard, so did another part of me. Learning to control my feelings was going to be a challenge. Nights were long and there was no rush to the finish line if you know what I mean. I think I masturbated every night even though I promised myself I would not. I swear I could hear my mom in the back of my head telling me I was going to go blind.

Work dragged and nights flew. It was finally Friday night and she was coming home. I was actually looking forward to it. The problem was I had changed in just this week alone while she had been away. Could I hold it all together and not be so girlie she would erupt. 

So when the cab pulled up, I walked out to the driveway to greet her and pick up her bags.I was wearing a nice pair of slacks, a dark crew neck shirt and my pink bra and panties. She always thought they were cute, so I wore them for her even though she could not actually see them. 

She gave me a real big hug and rubbed my back, acknowledging the bra. That got a grin from her and a little shake of the head. It was so nice not hiding and there were no eruptions. I carried her bags in for her and then she gave me a big kiss inside.

I let her tell me about all the fun with the kids and how well her sister was now doing, and then she shifted the story to me. 

"Tell me about your days." 

I started by first telling her "It was fun shopping and dressing up at first, but it got lonely after a while by myself. But changing into the skirt and blouse after work, that was way cool. I never knew how great a skirt could feel!" 

"And it was fun sleeping in the new nighties but once you were asleep, well, you were asleep. Having someone to share the fun of shopping with is much more fun than simple shopping by yourself and not sharing." She said she totally understood and gave me a hug.

I had prepared a nice meal for her and we had a little wine with it.

It was a long day for her so she asked, "Could we call it an early night? 

I carried her bags upstairs, and as she was unpacking upstairs she said, "While I was away I really missed being with you. My sister's husband could not have been less attentive to the kids and me. I had to do everything around the house. And the place was in complete disarray."

"The big lunk just comes home from work, opens a can of beer and plunks himself in front of the TV or his computer. Seeing that first hand makes me really appreciate you, even with all your little quirks."

As I started changing for bed she had a request..."Would you show me the new nightie you bought?" 

"Sure, no problem."

As I reach down to the bottom drawer to get it, she said, "And I would really to see it on you." 

I was a bit surprised because I really thought she did not want me to wear nightwear in the bed room. 

"Which one? I bought a chemise and a baby doll, or both?" 




Caught For the Last Time Ch. 03



"Let's start with the baby doll."

I went into the bathroom, changed into my black panties and slid the nightie on. The baby doll was classic Soma, nice quality, not a see through, and hung perfectly. It was not one of those cheap flimsy see through ones. 

Like the loungewear earlier, it was black with nice lace around the bodice and gold edging. The lights in the bedroom were low and when I walked in she smiled and said..."That is so you."

As I walked over to her slowly, I felt like she was checking me out with her darting eyes. She reached out and took both of my hands and gave me a long kiss. She was still dressed from her trip and there I was in a nightie. This was a totally different experience. 

I've tried not to get aroused in front of her while dressed in the past, but this was a challenge. I could feel myself getting excited. 

While standing there, her hand moved to on top of my breast and I could feel my nipples getting hard. She then placed her other hand on my other breast and began lightly stroking each one. She then kissed me deeply again and kept this up for what seem like forever but it was only a few minutes. My knees became weak. Then she gently slid the strap off my shoulder and took my nipple in her mouth. 

Slowly she used her tongue on my nipple and my pleasure increased. This was beyond anything I imagined. I could feel that she was beginning to use her teeth and it actually felt wonderful. Her other hand continually squeezed my breast and she played with that nipple as well. 

Just as she was slipping her hand down the back of my panties she suddenly backed off and asked me to change. She wasn't angry. She just said she was sorry for what just happened. 

Maybe it was the wine, or the fatigue of travel. Regardless of what it was, it happened and I thought it was wonderful. She had her doubts and that was OK. 

After changing out of the nightie and putting on my regular old briefs we did celebrate in the traditional way. But the experience, while it lasted, was wonderful.

++++++++++++++++++++++++

The next day was Saturday and was a bit awkward at first because of the bedroom encounter. I decided to be safe and dress in my regular guy clothes. We had fun sharing more details of our little adventures throughout the morning. 

AS we started cleaning up the breakfast dishes she put her arms around me and said, "I'd like to see what you bought. Would you give me a little fashion show?" 

I eagerly agreed and headed upstairs and carried the items down to the downstairs bath. I made a quick change and started with the new chemise. She said, "That is really nice. You look so good in it. Carol did a nice job of helping in the selection and fitting process. Plus, I love the way you are standing with your shoulders back and your back arched just a bit."

"Come over here. Are your nipples hard again?" She could see my nipples were rock hard under the soft fabric. 

She gently caressed my breasts and whispered, "And I thought I was the only one in the family whose nipples got hard. Now let's see the rest before we go too far."

When it came to the skirts and tops, this was a little different feel. I love the outfits not only for their look but also for how they make me act. It was one thing wearing a bra and panties under my shirt and pants, but it was another thing wearing them under a skirt and blouse. 

As she sat and waited, I went to the other room and put on the deep blue bra and panties with the new purple jersey top and the black skirt. This felt so cute while she was away...how was this going to play out in real life. 

As I rounded the doorway she said..."That is sooo adorable! Did you pick that yourself?" 

That was a huge relief. I loved the outfit myself, but now I was totally out there. As I stood there with my legs together I gave a little shrug of a shoulder and said "Yes, all by myself." I felt a whole lot better. 

"You know", she said, "You need a simple pair of slides to go with that outfit...something to give you just a little lift. Turn around...that is so cute. Let me see" 

I then scooted over to her and let her feel the skirt's fabric and she playfully peeked at my underwear. "You are such a girl."

I then went to try on the ivory lace top. I changed into my nude bra and put the top on. This was a more elegant look, but still very simple. When I walked out with confidence she said..."That is so nice. It is a good fit, and with that bra it is real feminine. Plus it's a wonderful color on you."

She asked me to sit down and as I did, I sat with my knees together. 

"Looks like you've been practicing a bit too. I'm impressed. I've been doing a lot of thinking on the trip. It's been a challenge for me thinking about this whole thing but it's been about six months now and I am actually getting to like this side of you. I still really struggling with the sex part though so bear with me. I'm trying, I really am."

"I had all these terrible visions of what it would be like and they just never materialized. You certainly seem happier than ever before, even when you are not dressed. And from what I've also noticed, you are naturally adapting to it as well. You can be a girl, and a guy. I'm slowly beginning to understand."

"Do me a favor. Put the purple top back on and wear it with the skirt for a while today. It's going to be a lazy day around here today and I want to get used to you in it before I decide how we should proceed. Would you be OK with that?"

I thought about it for about one second and said "Absolutely"

Saturdays were usually running errands, picking up the place, laundry, relaxing, and catching a movie. Occasionally it was getting together with friends, but not this weekend. I started with some online bill paying and spent some time straighten up the files. There was really not that much to do because I had been home all week alone in the house and been keeping up with things. 

My wife was busy doing her laundry and putting some items away from her trip, so we were really on two different paths for the better part of the morning. But every so often when I would walk by to get something, she would turn, look at me in the skirt and top, take a little breath and say..."still not quite used to this. But I'm getting there."

For lunch that day we decided on a light sandwich. I told her I had noticed at how little I had been eating these past few months, mostly because I was concerned with how I looked in clothes...a little vain perhaps but I wanted to look good. 

Lunch was another good time to talk. She said, "It is easier seeing you dressed like this for a continued time period rather than just every so often. I just need to get to the place where I don't keep saying to myself, "Oh yes, he's dressed." I hope you understand." 

And the more we chatted about it the more she was comfortable sharing her feelings. She had always been concerned that there was someone else...and now that she has learned more about me, she learned that the someone else was actually me. I tried to explain that it was just another part of me that has always been here and now you get to see what I have been always feeling. That part was still difficult to comprehend.

She then said, "Hey, let's do something special for dinner. I'll run out this afternoon and get some cheese and some wine that I heard about, and we will have like a French theme evening. We can have candles and maybe you could wear the new ivory lace top for dinner. Does that sound like fun?"

How much more fun than dressing all the day and then at night get? She headed out to go shopping and I, well, stayed at home dressed. Her going out was no longer a code word to change as I already was dressed. But it was a time to start putting together some fun things for this evening. 

I went upstairs and tried on a couple of different bras with the lace top to see what the look would be like. I had worn the nude bra with it because it did not show, but wearing the white one that actually did show through actually made the top look a bit sexier, so I decided to wear white later on tonight. 

When she came back from shopping I was still dressed in the purple top and skirt. She had several different bags with her. While I did not go out to the car to get them, I did stand at the door and help bring them in. It was such fun standing at the door in a skirt! 

"And no peeking yet" as she clutched two of the bags close to her.

The rest of the afternoon was spent together and I tried my best to walk with just a bit of a girlish swish as well. It was hard not to when in a skirt. I just didn't want to be grinding all over the house like a hooker. 

As we got close to dinner time she said, "I have two things for you for tonight. First, a pair of slides with a slight heel. They're from Payless and with these you don't have to fuss with ankle straps and they are feminine enough to go with your top. They are called slides because there so easy to just slide them on."

"The other surprise is a new skirt. This one is just below your knee and I think goes better with that ivory lace top you bought." I tried it on immediately and it fit perfectly. It was a very light fabric, solid color, and almost see through. It flared a bit and hung so perfectly. I loved it.

"The wine is almost chilled so let's change and meet downstairs in 15 minutes or so."

We went into different rooms to change. I didn't have that much to change so I took my time and changed my bra and panties to the white ones, and then put on the new skirt and ivory top. I was looking at it from all different angles in the bathroom door mirror, and thought they looked perfect together, especially with the new delicate slides. The lift really helped make the look. I made it downstairs first. 

My wife then made her entrance in a new dress. It was made out of the lightest chiffon, in a multi-color print and the top was virtually see through. And in classic French style, she was wearing the sheerest of bras...also new.

"Wow, you look amazing", I said. 

"Hey, you can't have all the fun", she said sweetly.

We sipped wine in candle light and pretended to share stories from our day in France. After a candlelight dinner we watched a French movie with subtitles. The movie had some amazing hot love scenes in it and this got a bit uncomfortable as I was dressed. At one point she whispered..."Come here." 

As I moved over, she slowly removed my top, and began caressing my nipples through the bra. She then had me stand up as she slid off my skirt and I stood there in my bra, panties and heels. My hands reached down and felt her breasts which were already hard. 

She then reached behind me and removed by bra and dropped it to the floor, and then slowly slid my panties down to my ankles as she dropped to her knees and started giving me a blow job. 

She then reached behind and had me slip out of my one of shoes, and by then I figured out that she wanted me, but as a guy. I kicked of the other shoe and she drew me back onto the couch on top of her. 

I never found out how the movie ended. She woke me up in the morning with a sensuous kiss. I looked around and all of our clothes had been picked up and put in the laundry.

She can buy new clothes any time she wants!

Maybe we had turned a corner.



Caught For the Last Time Ch. 04



So here we are in the early fall. Another three months have passed and all I can say is what a summer. My dressing at home had calmed down a bit and was now pretty normal. I could actually get dressed and not get a raging hard on every time. I actually liked that.

We modified some of the dressing at home rules to make both our lives easier. 

If during the week I arrived home from work earlier than she did, and I wanted to put on a skirt and top, I could. Knowing that my car was in the driveway was at least a heads up to her that I may be dressed. Not that I was, but I may be.

Weekends at home were still about the same with one added plus. On Saturdays or Sundays I was usually dressed while we worked around the house and every so often I could change into the loungewear or chemise at night to relax if we were staying in. 

It was fun and sometimes playful, but never more than that. A squeeze, a hug, a touch, a tease. 

I did not dress every day and that was OK with me, and apparently with her was well. Our sex was good sex. We were active and she was playful. She was amazing in bed, or in the living room, or the kitchen, wherever. 

But I was still yet to have sex with her while dressed. 

Strangely, that was no longer a burning desire of mine because I could wear almost whatever I liked whenever I liked. And I never wanted dressing to interfere with our sex life, and I could see how it could if I pushed it.

I think she knew that it frustrated me. I had pretty much resigned myself to taking matters into my own hands. I was still masturbating a couple of times a week while dressed so that at least satisfied those yearnings. 

On the positive front, I was also able to purchase several more items over the summer through mutual consent, mostly because I think she was tired of seeing me in the same clothes when I did dress. I purchased a nice denim skirt with a bit of a stretch to it, and went back to Kohl's to purchase some camisoles tops. 

I think I had gotten a bit too cavalier in my shopping because when I was at Kohl's buying the camisoles the same cute sales associate Erin came over to me and asked, "Back again?

"You remember?"

"Sure. I especially remember all my guy customers. We get a lot. As I remember you were buying some bras and panties last time. What do you need now?"

I tried to roll right along with the conversation and said, "Erin, I'm looking for some camisoles. Do you have any suggestions?"

She said, "Personally, I like these. They're cute, have a nice band of lace on the bottom so they are fun to wear out over your jeans. And they have adjustable straps so they should fit you no problem. I'm guessing you're a large, maybe an extra large because of the length."

She started looking for some different ones and helped me find a few.

"Oh, and Maidenform has some too, didn't you buy a pink Maidenform bra? I love pink camisoles."

"How do you remember all this?" 

She just smiled and whispered, "Everyone buys a pink bra."

We walked over and got one and she said it will match perfectly. I had never even through the matching aspect.

"What are these?"

"Oh, those are rompers. They are like camis, but longer with legs. They are so cute. I've got a couple of those as well and love them. Do you want to try it on to see if they will fit? They're kind of tricky to size"

This was amazing as she grabbed three different ones. All I could say was, "Thanks, that's a good idea." She pointed out a neutral changing room to me that I didn't even know existed and tried the rompers on as well as the camis.

I loved the rompers. I decided on getting one of those and 2 camisoles, the pink one and a black one. 

When I came out I thanked her for the suggestions and she said, "Anytime. Seriously, I have a lot of male customers and fitting is always a challenge. I'm glad to help you anytime." 

The entire purchase cost $35. I found that I even could wear the camis even without a bra if I wanted. They were cute and easy to pop on and off. And my wife approved as well. 

When my wife saw the romper she said, "A romper, what a great idea! Did you get me one? I love these". I wish I had known.

Some of the more fun memories of the summer would be her coming home a little later than me at night when I was preparing the dinner. I might have on the black skirt and just a camisole top. She would walk over and from behind me, squeeze my butt...or slide her hands around the front and cup both of my breasts. 

It would hardly ever go much further than that, but it was always a thrill to have it done. And yes, the nipples would get hard and she would always tease me about that...like..."You are such a girl."

+++++++++++++++++++++

And perhaps one of the scariest days of the summer for me came one early evening while sitting at the kitchen table. I was wearing a pair of my shorts and Tshirt over my bra and panties. My wife was outside in the garden while I was going through the mail. It was a beautiful early night and one of her friends stopped by as she was driving by the house. 

I never heard the car door close and it was not until the kitchen door opened and they both walked in that I heard..."Honey. Guess who stopped by? My good friend Sally."

Crap. The good news was that I was not in a skirt. But, the Tshirt was a bit tight and girlish so I tried to sit to minimize the exposure as I sat there in kind of a bit of a defensive position. They chatted about how nice the yard looked and my wife commented on how helpful I had been on keeping it up in the hot summer months. 

My wife then tried to move their conversation into another room but Sally asked me how work was? It was kind of hard not to answer her direct questions. I tried to make the answers short and sweet, but the more I did that, the more she asked. 

I could not help but notice that her eyes kept glancing down towards my Tshirt every so often. It was more of a quisical look than a stare. Part of me wanted to crawl under the table and the other part of me wanted to ask where she buys her lingerie. She always dressed so well. 

Regardless, the conversation finally ended and they headed into another room. I basically did as well and headed the basement. While my wife and I chuckled over it at dinner, I was still very nervous about anyone else finding out.

++++++++++++++++++++++++++++++

And there was one night when I was sitting there in one my softer Tshirts, bra and panties over my jeans and she said, let's go out to the movies. It was one of those lazy Saturday nights, at the end of the summer, and the nights were just beginning to turn cool. 

I had kind of settled in but I said, "Sure, let me change and we can go."

She then tossed me my light nylon windbreaker and said, "Not tonight. We're going to see a chick flick and what better way than wearing your bra and panties. It'll be fun. Besides, no one will know but us." 

I was a bit hesitant about this but was thrilled she suggested it. She then said, "Look, you wear panties to work on some days, don't you? How much harder will this be?" 

It's true, and I had no problem with that. So off we went.

She drove and on the drive over she kept teasing me about being outside in my bra. I actually kind of liked being teased and loved how the car's shoulder seat belt split my breasts and gave me a little more cleavage. I sat there feeling a little prouder as we drove through town. 

When we arrived at the theater I tossed my jacket on but left it unzipped. It covered me just fine but there was the fun of being a little exposed. There were 2 movies playing at our theater and she wanted to see the chick flick.

And what a surprise, the chick flick was attended by a lot of chicks, and not just young ones. I must have been one of the only 10 guys there. 

As we waiting in line for tickets, I was real apprehensive. But as I looked around I could tell that no one was really looking at me or my chest, so I felt more comfortable. 

While we waited in the lobby, my wife kept asking me things like..."Do you like her skirt?... Her top is adorable don't you think?... Look at that camisole, that is so cute. It's like yours. ...And that dress...she is about your size...let me go ask where she bought it." 

It became like a mini fashion show. We were having so much fun it was almost a shame we had to go into a theater. Once inside I found the confidence to remove my jacket as we were sitting down in the slightly darkened theater. 

This felt good until people starting coming into our aisle and I had to keep standing up to let them by. I am not sure anyone noticed I was wearing a bra when I stood up but it was fun. 

The movie was a lot more enjoyable than I thought it was going to be and it did have some racy moments in it including a time when the husband surprised his wife by wearing her panties to bed and had real passionate sex. Awkward, but it got a good chuckle out of both of us. 

In one of the more intimate romantic scenes, my wife actually reached over and slid her hand under my shirt and inside my bra and whispered, "That's how a girl likes to be touched". It was no surprise that my nipples were hard at that point. I'm so glad that scene lasted for several minutes. She kept softly caressing my breasts and lightly squeezing my nipples through the whole scene. 

It was probably the one time I wish I was wearing a skirt in public as well! But what happens at the dark theater stays in the dark theater. And other than the suggestion we do this again sometime, there was no reruns of the bra scene when we got home. There was still that line that apparently only she could cross but not me. 

++++++++++++++++

It was now late-September, and it was getting darker and cooler earlier at night. The summer clothes no longer seemed as appropriate as before. I did not want to bring up the clothing issue, but I was afraid I was going to have to. She was always the one who initiated the conversation on new clothes.

While watching the news on TV, one of the reporters had this real cute fall outfit on and my wife commented how nice she looked. This was my opening. 

"Honey, I hate to bring this up, but on certain days, especially in the evening, I feel a bit chilled at home wearing the short skirt along with the short sleeved top. Do you think I could get perhaps a longer skirt and a longer pretty top??" I held my breath.

She said, "I've noticed that you do look a little out of season. I think you're right. Maybe you should have a few items for the cooler weather."

"I'm not sure I could find you that same outfit the cute little size 5 weather girl has on, but give me a few days to think about." We laughed together which was good.

Plus, I said it nicely and the response was relatively positive. At least she had been thinking about it as well. I always liked her plans so who was I to argue.

On that Friday night, I came home and changed into my dark blue bra and panties, and wore a lighter colored jersey top and a pair of skinny jeans. It was probably my best girl look in guy clothes I had. In the mirror I could clearly not only see the dark bra color through the shirt, but it also had this clingy feel that I loved. I was really enjoying this freedom. 

And then the phone rang. My wife said she would be home in about 30 minutes and was stopping by with a friend. But she went on to say, "Being a Friday night I can already guess what you are wearing. Why don't you just keep the bra and panties on, but just put on one of your more discreet shirts you used to wear."

I was so glad for the heads up. I quickly changed my shirt right away, checked myself out and relaxed with a book, all the while wondering who was coming over.

So there I was sitting in the living room, casually reading when my wife walked in...with Sally. 

Crap, here I am with Sally, the gal with once saw me in the bra and Tshirt at the kitchen table. I'm still wearing a bra and panties but at least this time I was sitting in the love seat and looked fairly guy normal. 

"Honey, I caught up with Sally earlier this evening and asked her to come over." 

I went to stand up to say hello, but she said, "Oh please don't get up." 

Thank goodness because I know she'd be checking me out. She'd probably give me a hug and rub my back as well.

There was some idle talk and then my wife said, "Sally's been a good friend for the last five or six years and we have had lots of girl talk times over the years. One thing she shared with me several years ago was that her younger brother was a crossdresser." 

All of the sudden the room got very warm and my face got flushed. I was trapped and I did not feel at all comfortable with where this conversation may be headed. 

She then added, "I would like Sally to tell you a little more about him and her experiences." 

I felt even more trapped but I trusted my wife and stayed.

Then Sally spoke. And this was a more serious Sally, not the fun loving one I had seen in the past. 

"When I was in high school, I was loving life. Being the oldest of two children in the house, and being the only girl had its privileges. My mom and I would go shopping all the time. Between dance and cheerleading, I had a full life and quite a collection of wonderful clothes. I had my own room with a huge walk in closet, a wonderful chest of drawers, and other great girly things in my room."

"I never really thought much about that until one day after I came home from my dance class and showered, I noticed that when I went to my underwear drawer, something seemed a little out of place. Not a lot, but just a little. I shook it off as maybe my mom was looking for something and then I forgot about it. No big deal."

"That was until a few days later after cheerleading practice, the same thing occurred. I again thought it was my mom, but she had been out for the entire day. I was puzzled. I then thought about Tommy, my younger brother, but dismissed this as, no not my brother."

"This routine continued for a few more weeks and the more I looked, the more I found things slightly out of place. A dress hanging in the closet with the hanger facing in the wrong direction. A blouse from my hamper turned inside out. A nightie from my drawer improperly folded. I was now becoming more of a detective every time I entered my room." 

"I tried to stay calm and think through how I was going to confront him if it even was Tommy, and what I would say to him. I had read some articles about boys wearing articles of female clothing, but the stories always were the perverted type. I did not want this story to end that way nor did I want to think anything bad of Tommy."

"So I crafted a plan to see if I could catch him in the act. On the kitchen wall we had the family calendar and I had on it a dance class that was really not happening that Tuesday. It had been cancelled." 

"I told Tommy that Tuesday morning that I would see him at night and headed out to school that day as normal. After school, I hung around with friends for a while and planned to hit the house after he arrived home from school but before the time my mom would arrive home from work."

"I quietly entered the house and went upstairs. I peeked in my room and as expected, there he was. He was standing in front of my full length mirror in one of my tops and skirts. He was pretending to me, talking to the mirror, swaying left and right, checking himself out from all the angles. It was actually kind of cute."

"He then did a full twirl and spotted me at the door." 

"Sally! What are you doing home so early?"

"I sternly replied...never mind that, what are you doing in my clothes?" 

"Tommy was so embarrassed and stammered out some lame excuse that wasn't even a sentence. I walked over, sat in my chair, folded my arms and told him to take off my blouse of right away. He said he would and started walking into my closet to do it. 

"No. Take it off right here and now, or I will tell mom and dad." Pouting a bit, he undid the blouse and handed it to me. 

When he did, he was now standing there in my black bra with a black skirt. This made him even more embarrassed if that was even possible. But between you and me, he looked kind of cute!"

"Now the skirt I said. Reluctantly he unzipped the skirt and as it fell to the floor, I was at least glad to see he was wearing matching panties...but I didn't let him know that either."

"I then had a sisterly talk with him as he stood there in my bra and panties. I told him I did not like him violating my space and if he ever did it again, he would wish he hadn't. He apologized a dozen times, and after probably the longest 10 minutes of his life, I told him to remove the bra."

"This was the part that amazed me the most. He reached his hands behind his back, undid the strap with amazing ease and handed me the bra. He did that better than most girls...this was not his first time he had removed a bra. Or even worse...my bra! Now, go into your room and change and then put the panties into the hamper in here."

By now, I was fascinated by Sally's story. I now had a totally different perspective on her. I then asked her..."Did he ever go into your room again?"

"Not for a few weeks. And even at that it was very periodic so I let it slide. I really loved this kid and I needed to really think through what my next steps would be. I could see that he was now being extra nice to me all the time, even complimenting me at times on how nice I looked...seriously, a brother complimenting his older sister. It was a good feeling."

"Then one weekend my parents were going away and I was to watch over Tommy. I had done it before so it was not an issue. But I wanted to use this time to have some more meaningful discussions with him. I knew he was still getting into my clothes. I think he was trying on a few outfits from my closet and probably some under things from the hamper, but he was being very discreet."

"So on the Friday night that my parents were leaving, we all had dinner together and we gave them hugs goodbye. Tommy and I finished up the dishes and decided to watch a movie at home. It was a funny one and one of his favorites. It left him in a good mood." 

"When it was over I asked him if he would help me move something up in my room. He agreed and when we walked in the room, I am sure that he could not help but notice what I had laid out on the bed as we moved a small piece of furniture." 

"In a nice orderly pattern, I had placed five pair of my panties and two of my bras on my bed. I saw him glance over at them more than once and then I made a simple statement like... 

"I've been getting the feeling that you have been trying real hard not to wear any of my clothes these past two months. But you have been, shall we say, struggling a bit." 

Sheepishly he agreed. "The feeling is there he said...a lot. Try as I might, I am still attracted by them." 

Then being nice, and not accusatory, I told him "I think I am beginning to understand. The fact that you are wearing my clothing when I am not here still bothers me so I have come up with this plan. Do you see those bras and panties on the bed?"

"Yes" he replied.

"From now on they are yours."

His eyes lit up and his embarrassment was replaced with surprise..."Really?" 

"Yes. What I am going to do is put them in the third drawer in this other small dresser we just moved. You can keep them in here when you are not wearing them. That way mom will not find them stashed away in your room and go crazy on you." 

"And in my closet, I put together two of my skirts that I do not wear all that much, several tops and two simple sundresses. I am putting them together on the right side of the closet. Feel free to wear them as often as you like and then neatly hang them up again. And just this side of the closet...got it?"




Caught For the Last Time Ch. 04



He nodded as he stood there in disbelief.

"If you are good with these and don't touch anything else, we can keep this as our secret. But, if I ever find anything else missing or moved, you will regret it. Are we clear?"

Again, he nodded in agreement.

"Now before we leave my room, do you have any questions?"

He thought for a minute and asked..."Can I have a nightie as well?" 

"Seriously, a nightie?" He barely got red and said "Yes. I would really like to wear one at night." 

I took a deep breath and went to my nightie drawer and laid out every one of them all on the bed. I had no idea I had so many of them. From baby dolls to full length...quite a collection if you ask me.

Tommy eyed them all over and said "These two fit the best." 

He used the past tense which means he probably had tried all of them on. I rolled my eyes. 

One was a baby doll and one was a chemise, both very soft. The good news was that I hardly ever wore either of them so I "reluctantly" agreed to part with them. 

And what was fun for Tommy is that the baby doll had matching panties he was not aware of. I added them to his little collection. We moved them to that special drawer as well.

Then I said, "Look, mom and dad are away. Let's do this. Bring the bras, panties, nighties...everything into your room for the weekend and we can move it back Sunday afternoon." 

"What was not to like with this arrangement and we carried everything over to his room."

"I excused myself to go downstairs to watch some TV and he asked if he minded if he stayed in his room. That made complete sense to me and we said goodnight."

"That first night went fine. I asked him in the morning if he slept in the nightie and in which one. He was still a bit nervous talking to me about it but was pretty open and said the baby doll. After a few chores he retreated to his room and I did not see that much of him the rest of the day. When Sunday afternoon came, everything went back into my room as planned."

"For weeks, this arrangement worked very well. In fact, I was so pleased he was staying out of my stuff that one day while shopping with mom I specifically bought two extra pair of panties that I earmarked in my mind for Tommy and placed them in his drawer. He was so surprised."

Sally continued..."As the months rolled into years, he would sometimes beg me to let him wear certain dresses, which was a hoot. He especially loved all the new ones I bought and I would let him slip one on just to get it out of his system. He was like a sister!"

"To this day, he keeps a separate area in his apartment for just his female clothes and other than a few friends, no one knows. If anyone asks, he just says they belong to his sister who visits him on occasion."

Then my wife cut in and added, "I hope you can now understand why I asked Sally over. She had shared with me her stories years before I fully knew about you and I always kept them private. Even though I knew about your crossdressing before I met Sally, her sharing this with me allowed me to process my feelings." 

"It wasn't until earlier this year when I found the panties, again, that I needed to confide in her. I did not know where else to turn. She has been a big help to me and I'm so glad she has been there for me." 

Sally continued, "And when I was over in the late summer and saw you in the bra at the kitchen table, it got me thinking about Tommy, a lot." 

"I had been going through my fall collection and had a number of long skirts that were no longer fitting my fancy, as well as some tops, light sweaters, and other items and thought that maybe you would be interested in at least taking a look them." 

My head was still spinning from all this, but as reality took over I muttered a "Yes, and that sounds like a wonderful offer. I'm not sure what to say." While Sally was not exactly my size, she was a relatively tall woman and wore great clothes.

With that, Sally stepped outside to her car and brought in three large bags of clothing. She placed them on the living room floor and said, "You don't have to go through them now, but please, take your time and keep what you like." Sally turned, gave a big hug to my wife and left.

I was still in shock and was running all kinds of scenarios in my mind. I was happy and embarrassed all at the same time. My wife then apologized to me repeatedly for not saying anything earlier, but felt that this was the best way. 

She moved the bags into the other room, walked over and gave me a big hug, and said..."Let's do this in the morning...it'll be Saturday and we have the whole weekend ahead of us. I think we will be in a better state of mind in the morning. I'm curious to what she had brought you as well."

All night long I mulled this in my head until I finally dozed off.



Caught For the Last Time Ch. 05



In the morning I woke up in a much better state of mind. Less confusion and perhaps a better outlook on what had happened the prior night with Sally. 

Still, I was not all that comfortable with someone else knowing about my crossdressing, but at the same time, having someone for my wife to talk to was better than the way it was before, way better.

We had a real quick breakfast and my wife said, "Let's see what she brought. I truly have no idea."

We opened up all three bags in the living room. There were skirts, blouses, tops, dresses, sweaters, slips, nightgowns, jewelry...and wigs. Sally did have amazing taste in clothes and my wife was looking at the labels she said, "These must have cost her literally hundreds of dollars." 

I was like a kid at Christmas looking at everything and holding them up. 

My wife said, "Why don't you go upstairs and change into your bra and panties? Looks like we're going to be here for a while."

By now I was a seasoned pro in terms of what to wear. I tossed on the neutral colored bra and panties. No need to have pink ruin the look of anything I was going to be trying on. When I got downstairs she already had an ivory top in her hands.

"Let's start with this cute top while you try on the skirts." She then handed me one skirt at a time to first see if they fit, and then determine if I wanted to keep them. 

Skirts are always fun to try on and easy fit. I even had brought down my slides on for a little extra lift and loved how the long skirts just flowed. There were 5 skirts in total ranging from floor length to a mini...they all fit perfectly. And, we both loved them all. They were all were keepers. 

My wife helped match up three tunic tops with two different skirts and was able to mix and match to come up with several different outfits. They looked great on. Unfortunately not all the tops she gave me fit because of the shoulders. I just needed a little more stretch in them up top. But still there were six other tops, ranging from a pretty stretch lace to button up ¾ length sleeve blouses that worked. 

While I was doing all this changing my wife was brushing out the two wigs. One was a short bob with auburn highlights and the other one was shoulder length and had a dirty blonde look to it. I had never had a wig on before.

When I was standing there in one of the outfits my wife said..."Hold still. Let me brush this out on you and see what we have." When she was done all she could say was, "Oh my." 

"Stay right there one more minute and don't look." She quickly got some of her lipstick and said she needed to add a little just to give my face some balance. It was probably one of the few times in my life when I was glad I was relatively fair skinned and not a lot of facial hair.

When she finally let me look at myself in the full length mirror, I had the first glimpse at what I had been imagining all my life. I actually looked like a female, not a guy wearing women's clothes. I loved it!

We kept going through piles of clothing. The dresses were really nice. The dress lines Sally like were long. No horizontal patterns, no silly abstracts, just class. One did not fit as it was too tight in the bodice, but next three fit perfectly. I especially liked the one with the stretch lace bodice and empire waist. Five dresses were ideal.

We switched off the wigs on each outfit and my wife said how nice different jewelry would look on each one...sometimes holding up a long necklace and sometime a short one.

The slips were fine and the sweaters were great as well.

Last up were the nightgowns. The nightgowns were long and sexy in the purest sense of the word. One of them had a gown with a robe that flowed to the ground. I loved how it looked as I walked across the room...almost in slow motion!

"Hmmm." She said.

"You like it?"

"Yes and no," as she walked around me, fixed the robe a bit and slid her hands across my back and down my sides.

"Yes?" I asked.

"Yes, because it really, really looks nice on you, especially with the wig."

"And no?" 

"No, because it really, really looks nice on you, especially with the wig."

We both laughed. She walked behind me, placed her head against me and quietly gave me a real long squeeze. She just stood there for a moment holding me.

For the first time this morning, my excitement from wearing these clothes showed. I tried to hide it a bit and she said softly, "We'll have time for that later on. We have a few more nighties to try on."

The other 3 nighties were gorgeous and fit as well. 

I changed back into one of the more casual dresses and kept checking myself out in the mirror. I then turned and said, 

"I never expected all this and I'm so glad you suggested waiting until morning. I really love these clothes and this look."

"Nor did I. When Sally told me she had some things, I was thinking a few like, 3. You have an entire fall wardrobe."

Then I asked, "Given the circumstances, would it be possible for me to stay dressed for the whole weekend?"

As she had been watching me in the mirror playing with my hair and looking at myself from all directions, she said, "I think that would be a good idea...for both of us. I need to get more used to this full look as well."

It was difficult to figure out what to do the rest of the day. My brain was truly scattered. 

One thing for sure was that I had to figure out where to keep all this. This was not the same as buying 3 bras at Kohls. For now, the least I could do was bring it upstairs to the bedroom and go from there. 

My wife called Sally later that day and thanked her for both us. I heard her describe in detail the process of what fit and what didn't. It was almost like hearing a Tommy story all over again. Over and over again she explained how happy I was. 

My wife seemed comfortable speaking to her about me the whole time and even the responses to Sally's questions, were upbeat, some laughing, some serious like..."Absolutely", "That would be fun", "Definitely could see that", "He sure did", "We can only wait and see", "Adorable", and "Perhaps." 

After she hung up, she came over and gave me a big hug and said "Sally is real happy for you and is glad so many items fit you, and that you like them."

"I had misjudged Sally," I replied, "You've got a good friend." 

Around 3PM, as I was standing in front of the mirror, again, my wife said, "I'm going out to do a little shopping. I'll just leave you two alone."

We both chuckled at that one and off she went.

While she was out I tried on a few more combinations and settled into a nice skirt and longer top for the evening. I found some jewelry that worked and literally was floating around the house looking for things to do and catch myself in mirrors. 

I set up the table for a nice meal and really enjoyed the full experience of being dressed. I really felt like the woman of the house and just loved the idea of being fully dressed.

My wife arrived back home in one of those secretive...you have to wait and see...moods. I always loved those. 

All throughout the dinner that I had prepared, she kept looking at me. I knew something was different. Maybe it was the way I was acting...trying to be as feminine as possible or maybe it was just seeing me in a wig and make-up that made a difference to her. Whatever it was I was liking it. 

We sat and chatted, mostly about clothes and how much fun they were. And then she suggested we call it an early night. That was generally her code word for let's have sex, but tonight I hated the idea of getting changed back to the other me. 

We both headed upstairs and as I started to remove the wig in the bathroom she asked, "Aren't you wearing the wig with one of the new nightgowns to bed?" 

"I really wasn't sure how you would feel about it."

"Well, when you asked me if you could stay dressed for the whole weekend I really thought you meant the whole weekend."

"Sorry, I just wasn't sure."

"Seriously, it's OK with me if you wear them. I've been kind of getting ready for this during the day and figure there's no better time than tonight."

As I headed over to where I had placed the nightgowns she said, "I'll be right back."

I was now looking at the four nightgowns in a whole different light. I tried to pick one that was sexy but also a bit conservative. The good news was that these from Sally were all a bit conservative. The one I finally selected was ivory and had a soft lace bodice with long slit up the front and matching panties. 

When she came up to the bedroom she was carrying a chilled bottle of white wine and two glasses. "I think we could each use this after these last 24 hours. Maybe I should have brought up 2 bottles?" she joked.

She looked over at the bed where I had laid out my selection and she said, "I had hoped you were wearing that one...I love it!"

She then popped the cork and poured out the two glasses. She then walked over, gave me a kiss and handed me the glass of wine and said, "Here's to a new beginning." 

We each had a sip and she whispered, "Let me go change as well." 

I got changed with renewed excitement. Wearing the gown with the wig and make-up made such a difference. I stood there sipping the wine and looking at myself in the mirror. What I saw was what I was hoping for. I could feel my nipples getting hard and I let myself enjoy the feeling as I waited. 

In about five minutes she returned wearing just a new black robe with just matching black string bikini panties with cute side ties. Her robe was open and her breasts were just asking to be kissed. She was gorgeous. 

"Let me refresh your glass first," she said. Mine was barely down a notch but hers was empty already. 

She gave me a deep kiss, caressed my nipples, thought for a moment and said, "I'll be right back."

In another five minutes she returned in another new outfit. She was in all black. She was now in loungewear with these sexy long leggings that flared at the bottom. Her matching top clung against her body. Every curve showed and she knew it.

She was wearing black heels and had her hair tied back in a ponytail. She looked so freaking hot. She reminded me of Courtney Cox in a Charlie's Angels fight scene.

She reached over and poured herself some more wine and asked if I wanted any more. 

She took me by my hand and we both sat on the bed facing each other. She began to caress my arms and my thighs gently with her hand. There was a soft kiss on my shoulders and then on my back as she crawled around behind me like a cat.

"When I saw you in the wig today, it got me so excited." She continued to kiss and caress me.

She reached around in front of me and caressed my breasts as she kissed my shoulders and back. 

"You looked so radiant and excited as you tried on each outfit. I could tell, just from your face."

More kisses, more circling around me.

"It was like the wig transformed you, not just in your eyes, but mine as well." She kissed my shoulders and then crawled around in front of me.

"I may have been mistaken, but never once, until you put on the nightgown did you even get aroused. Maybe you did but I didn't notice. You seemed so natural."

I closed my eyes and started drifting away as she played with my nipples.

"But for that entire time, as you were trying on outfit after outfit, you and I were both seeing a different side of you. A side, like you had told me so many times, that has always been there. Perhaps a side that does not need to be there all the time, but one that wants to come out fully on occasion...like tonight"

She then took my hands and looked me straight in the eyes.

"And seeing you like that brought up feelings and memories that I had not had in almost ten years. And they were good memories, not bad." She continued, 

"I've never shared this with you, but when I was in college I played volleyball." She kissed me deeply and I replied, 

"Yes, I knew that. And you were awesome."

"And I had some great teammates and they were all awesome and very fit."

"Yes, I've seen the pictures, and you looked hot, especially in those tight volleyball pants," I replied.

"I know, and so did my teammates. In fact, we all kind of thought we were all hot." 

"And to me, I thought Stef was the hottest. She was a sophomore and cute as could be. I was a junior and was all about my fitness, my core, my crunches."

"Stef had long, dark curly hair, was one of our diggers, and she had a great pair of breasts. I liked mine and all, but hers were just so damn perfect." 

She began sighing deeply and fondling her own breasts, and then reached over to mine again. I could sense the wine kicking in.

"We trained together, traveled together, celebrated our wins together, and cried over our defeats together. She was my roommate on the road and at times we actually had to share the same double or queen bed on the road."

"It started innocently after a tough defeat when we were both crying and we hugged each other, and then the passions rose. It was that night that we became more that just teammates. For that season and for most of the rest of the year, we were intimate with each other. Not all the time, but on occasion. It was almost always when we traveled as a team, and then some other times on campus." 

"Stef enjoyed being the passive one and I loved the active role. And with those breasts, who could blame me?" She kissed me again and began stroking my hair and face.

"Stef and her magnificent breasts transferred to another school the following year and I became interested in boys again, and then I met you. Stef was just a brief moment in my life, but an important one as I look back. I realized that I was not always the person I thought I was."

"Over the years that we have been married, I realized that I have been acting like a prude when it comes to you wanting to wear lingerie every so often. I had been hiding my past and afraid of letting you live something that I kind of did. It was my own defense mechanism I guess." 

"I had not felt this way until I saw you in the wig. I saw how genuinely excited you were about being someone different." 

"I don't ever want you to stop being my guy husband, I love him, but if being this other you every so often will work for both of us, let's do it. I can handle it."

"So tonight," reaching over and taking another long sip of wine, "is your night." 

She crawled on top of me and began to kiss me from my neck down. I felt like I was wisked away to another planet. My back arched up to have my nipples thrust in her mouth. She was massaging my other breast with her hand through the nightie.

As she kissed me, she spread my legs apart with hers. I knew she was strong but never imagined her getting between me would feel so good. I now understood why she changed her outfit, she wanted to be the dominant one tonight.

She was grinding her body all over mine. She kept driving her pelvis into mine and I thought I was going to explode. 

With my legs spread open, the nightgown had now fallen open to either side of me. Choosing the nightgown one with the slit front was now a wonderful idea. As I reached down to put my hands under my hips, I loved the soft feel of the nightie around me.

It was wonderful being underneath her. I could just enjoy every minute as she stayed on top of me. She kept kissing, sucking and biting on my nipples while all the time sliding her body up and down on me. I had all I could do from exploding all over her. 

She sensed it and slowed down the pace and began a long slow thrusting motion, almost like I was getting laid. I did my best to wrap my legs around her as she continued faster and harder. At times I thought I was going to split apart. I couldn't hold it and I knew she could feel the heat pulsing through her clothes as I became to cum.

She never stopped and she began to moan deeper and deeper. Then with one long passionate moan she collapsed in my arms and her body became so relaxed. I just held onto her and lightly caressed her back. 

She rolled over on her back and said, "That was so freaking amazing! You are definitely keeping that nightie."

I'm not sure how long we just lied there, but we were not in any rush to move. Finally, she rolled over and whispered "I'm taking a quick shower and will be right back."

Seeing her walking away in her black lounge pants and tight top just reinforced what had just happened. I was really hoping that this was not the last time.

I used her shower time to make a quick assessment of myself. My panties were still on but drenched. I tried not to move too much but I knew my cock was deep purple from holding on so long. My nipples were beet red and wonderfully sore. My hips almost felt out of place. This was awesome!! 

She returned wearing the first robe and panties she had on tonight, gave me a cute kiss and I headed in to the shower next. I could barely stand. The hot shower felt so good. 

As I was toweling off I noticed there was one of Sally's nighties and panties hanging on the back of the bathroom door. Since they weren't there when I started, I assumed it was her way of saying, please wear this one to bed.

When I got into bed, there wasn't a word as she cuddled up to me and fell asleep.

+++++++++++++++++++++++++++++++

Needless to say, we got a real late start on Sunday. I still awoke before she did and took a long shower. Waking up beside my wife while wearing a nightie was wonderful...so much more fun that by myself when she was away. But my breasts were real tender.

I still wanted to stay dressed today and get used to a few of the new outfits. I decided to go casual at first and put on a skirt with one of the buttoned blouses and the other wig. I loved that look as well. 

I went to the kitchen and started preparing a real nice breakfast, practically a brunch by now. It must have been the smell that woke her up.

"Isn't this nice?", she said as she almost stumbled into the kitchen in her robe. I got a big kiss followed by a long hug. 

She continued, "I could get used to mornings like this. Did you enjoy last night?"

"It was better than I ever expected. You were amazing. I loved your new outfit too, both of them. That was a nice touch."

"I just had to get them. I thought the look would be appropriate for the night. And how are those nipples, girl?"

"Does it hurt you this much the day after?" I asked.

"Maybe not as much as it does you this morning, but you'll get used to it."

As the day went on, I kept wandering around the house looking for things to do. I know I was going to drive my wife crazy if all I did was look at myself in the mirror so I said,

"Can we just get out of here for a while? I'm not sure I can take this for a whole day. Let me just clean up a bit, toss on one of my softer bras, a shirt and pants and just head out. I can always dress later on tonight."

She laughed and said, "That sounds like a plan." She then came up behind me and playfully squeezed my breasts again as I winced in pain. She whispered, "Oh yeah, we had a good night..."



Caught For the Last Time Ch. 06



That afternoon we drove for about a half an hour over to the small mountain range and took a walk on one of the trails. As we walked, we talked about last night. The talk was a lot less awkward than I thought it was going to be.

"The sex was good last night, real good," she said as she was holding my arm.

"It really was," I replied. "I never knew I could get that excited in certain parts of my body, like my nipples. I've always loved your teasing, but this went well beyond that." 

I continued, "And not being inside you actually made it so much easier for me to hang on longer, a lot longer. I was not expecting that at all. That was real nice."

And she replied, "Hey, it was nice for me as well. I don't remember ever having that many orgasms in a row. My head is still spinning."

"That almost sounds bad." I replied.

"Not at all. When you're in me, my orgasms are like explosions....really big explosions. But when I was on top of you, I could control myself a little more and for a lot longer....they were more like waves that kept rolling over me...one after another, after another, after another. It was wonderful getting into that groove." 

She gave me a big squeeze of my arm as she finished the sentence.

"So, given this mutual positive experience, we can leave the door open to doing this again...sometime?" I held my breath as I waiting for her answer.

"Absolutely. Last night was definitely an unusual night. But even discounting the new clothes, the wig, the wine, it was still great. I just think that if it becomes too often or too planned, it might not be a great idea."

"I was thinking the same thing. Plus, my nipples definitely need a major recovery period." 

We laughed and she said, "Welcome to my world." 

On our walk, she also said, "And dinner with you last night was so nice as well. Let's not forget about that. You looked so nice all dressed up. Those outfits are just so classic and fit you so well. Plus I got to dress up as well. I like to dress up at home too, you know." 

She then said, "Too bad Sally couldn't see you dressed like that." 

That caused me to pause but I quickly discounted any thought of having anyone see me dressed but my wife.

She went on, "You know, she really supports you. She has lived through this with her brother and she may be a good person to stay in touch with."

"What do you say if we invite her over next weekend for dinner? You could wear one of the outfits she gave you and we could do the whole thing, complete with the wig and make-up."

My reaction was still no, but the more we walked and discussed it, the more intriguing it became. Sally did have a lot of good stories about her brother and might be able to shed more insight. By the end of the walk, I agreed and we decided to ask her.

We grabbed a quick bite to eat on the way home at one of our favorite places and held hands we walked back to the car. It was such a nice, relaxing afternoon.

When we were just a few minutes from home she started stretching out a bit in the car and ran her hands down her body to her thighs.

"Are you still frisky?" she asked.

"Why? What did you have in mind?"

She said, "I loved what we did last night but I think I could use a real good pounding right about now and I know just the person I want to give it to me."

Toying with me she was now focusing her attention just on her pelvis and lifting her hips up to her hands. She kept it up and reached over with her left hand and began slightly caressing me through my pants. This was a playful side of her I had not seen in a while.

We barely got into the house and never made it upstairs. We stripped the clothes off each other and she drew me down on top of her on the living room rug. 

I could tell from her panties that she was already wet before we even started. Lying on her back, she wrapped her legs around me as I penetrated her. I went right in. 

While on her back, she kept banging the floor with her arms as she was driving her body up into mine. 

She was so ready. I could tell by her deep moaning and quivering that she was having a huge orgasm. This afternoon was all about her and I kept at it, holding my breath at times just so I wouldn't go off first. 

Then, she collapsed right back down on her back. I was finishing right at the same time and she exclaimed....."I needed that so freaking bad!"

++++++++++++++++++++++++++++++++++

I never changed back into any of Sally's clothes that night. Somehow it did not seem that important. We both slept commando that night and the last thing I remembered was that she softly kissed my nipples good night.

Monday morning came way too soon, but I happily changed into a pair of panties before I headed off to work. With all new my clothes, I was sad it was all I could wear. When I returned home from work, my wife greeted me with a big kiss and said, 

"Sally is free on Saturday night. Let's plan a delightful dinner for her."

The rest of the week we discussed the menu, what to wear, topics of conversation, how to sit, everything. The closer Saturday came the more excited we got.

On Friday night we did a dry run of exactly what I was going to wear. I must have tried on every outfit I had! After mixing and matching outfits, we decided on the ¾ length skirt, the ivory tunic top, a long necklace, some bangly bracelets and the slingback heels. 

I missed having the make-up on but we still had fun pretending. As I had the wig on and turned around and modeled the final selection, my wife kept looking at me and said you need something else. 

"Here's what you should do tomorrow. Run over to Kohl's and get a 38C bra. I know the B's are great for around here, but with that tunic top, your "girls" could use a bit more perkiness."

"And while you are there, Maidenform has some body shapers that will help pull you in around the middle and pop you out a bit on top. Look for one of those as well. They are really tight to get on but can work wonders."

On Saturday I was all nerves, not because of Kohl's but because Sally was coming over. Dressing at home was easy, but being in front of Sally, or anyone, this was a whole new level. 

I hit Kohl's first thing and you know who was there. Erin. 

I walked up to her and asked, "Do you ever leave?"

"It's retail, what can I say? What brings you in so early this morning?"

"Do you have a minute? It's a long story."

"Look around, there is no one here. I'm all ears."

I explained what I needed and why, and Erin said, "Wow, that is amazing. I think I know just the thing." 

She walked over to the Maidenform bras, picked out a neutral colored 38C and handed it to me like we had been doing this all our lives. 

"Let's see, body shapers, body shapers....here, let's try these two." 

"Oh, and one more thing, come here for a second." From behind the counter she pulled out two silicon breast inserts.

"I sell a lot of these, especially to the guys. They will make you look and feel natural, they are much better than socks. And once you wear them once, you will never not wear them.....trust me...I know first hand."

I did my best not to look down at her but I just had. "Yup," she said, "I'm just a little girl underneath....could you tell?"

I was deep red by then and just kind of murmured "I had no idea."

"Come. Let's try these on." We walked over to the ladies fitting area and she said, "No one is in yet so let's get a larger room. You're going to need help with these. Just keep your voice down in case someone comes in. We don't need to worry the female customers."

She told me to remove my shirt and turn around. Very professionally, Erin reached around me and slid the bra over my arms and attached the strap.

"Wow, you really are a perfect 38C in this brand. And I love those panties you're wearing. I can see them peeking over the top of your jeans...Soma?"

Not wanting to speak I nodded. "Class, real class", she said.

"OK, open the silicon box for me." As I turned to get it off the bench, she quietly slid her top off and I almost said something when I turned around and saw her in just her bra. 

"Shhhh" she said.

"Now, do what I do." She literally removed her insert and said, "Place the concave side of it against yourself like this, and make sure the angle follows the flow of your body."

I could not believe she was showing me how to do it. 

"The wrong way would look like this....the right way like this. Make sense?" 

She was making me laugh with her faces as she showed me each way which kept the discussion fun and not sexually arousing.

Once in place she reached over and gave each one of mine a little push. "They feel good," she said. 

She also did the same with hers and said, "See, these girls are not going anywhere.....look." She bounced up and down a few times and wiggled side to side.

I whispered, "They look so real."

"They do and you really forget they are even on after about 10 seconds. And now the body shaper. This is not as easy. Please put your hands up and let's pull this down over your head."

This was tough. She worked the back of it while I pulled the front down. There was actually not much of a front because the design of it was to push you in on the sides and move your breasts up and out.

Erin helped move everything around until she finally said, "Damn girl, you look great!"

My little C's looked fantastic. I actually had cleavage. Erin put her top back on and I struggled out of the body shaper with her help and finished getting dressed. 

She opened the door, looked around and said, "Let's go, the coast in clear."

On the way to the checkout she said "And I want to see pictures." 

"Really?" I asked.

"Yes really. I think you are going to look spectacular from both what you have told me and what I see here," she said with a wink.

"You should see the different shapes of men that come in for bra fittings or to try things on. They think that a guy the size of a middle linebacker can look like a size 5 Victoria Secret model. Realistically, that is not happening. But, in their mind they do and that is the most important for all my customers, male or female. I love my job and my customers."

"But you are different. You are a delight to talk with and to fit. I love your attitude. Trust me, I don't do this little show or tell this too many customers, but I wanted to show you that everything isn't always the way it appears."

She looked down at her slightly enhanced breasts and pouted a bit while she said, "Sometimes even a flat chested little girl like me can look and feel like a model too." 

She then stopped, smiled and said, "Your wife is so lucky to have you. Oh, and if she ever comes in with you, I am discreet over what I say so I will follow your lead. "

"Erin, I'm at a loss for words. You are amazing and I will definitely get you some pictures."

"You do that and when you come back next time, I've got some great ideas for some other outfits for you!"

++++++++++++++++++++++++++

Around 5:00 I started getting dressed for a 7:00 dinner...good grief this takes a long time to get dressed. I started with my new bra, inserts and shaper. My wife looked at me and could only say, "Oh my."

I also gave her an abridged Erin story.

She spent a lot of time on my make-up and said that with the dirty blonde wig, the smokey eyes would be a good look for me tonight. Wow! She was right. I finished getting dressed and I seemed to be fussing with my hair every two minutes. 

My wife kept saying "Leave it alone....you look fine. Now hold still so I can get some pictures of you so you can show your little Kohl's associate." I think she took 20 pictures from all kinds of angles. 

Then the doorbell rang and my nerves kicked in all over again. My wife answered the door and I stayed back in the living room, waiting nervously. Sally walked in dressed in a smartly styled long skirt and a beautiful silk blouse. 

I had never seen her dressed up before and with her hair slightly wavy, make-up and heels, she was quite attractive. I had forgotten how I looked because I was too busy looking at her.

She came over to me, took both of my hands and said, "You look amazing in those clothes. Someone has real good taste! And your make-up is just perfect. Truthfully, if I did not know any better, I would not know it was you. Turn around dear and let me see you from all sides."

I was so glad we moved up from a B cup to a C cup. With the wig and more padding here and pulling in there, it was really the look that was missing. 

We had some wine before the meal and stood around talking about clothes and shopping and it was such fun. Our dining room looked wonderful with candles, nice china, and pink place settings. It was elegant. 

We dined over salad, some light vegetables and wonderfully tender veal. For dessert it was a very light soufflé and with coffee it was perfect.

After dinner we retired to the living room. After a while our conversation drifted over to Tommy. Sally shared that perhaps one of the more interesting times she vividly recalled was about a month after she and Tommy had their little encounter and she gave him her clothes.

"My mom and dad took off for another weekend. Now up until that time, Tommy had been amazingly good to me and by all accounts, stayed out of my clothes. His special drawer had grown by a little as I added a new bra and even a few more panties to it. He had been real nice to me so to be honest, buying him a $5 pair of panties was a nice trade off. I know my mom never expected anything as she never hinted even a word to me."

"The only concern I ever had was that Tommy would now spend a lot more time in his room. And except for that one day, I had never seen him dressed again. And I know he was dressing behind his closed bedroom doors." 

"So maybe this weekend would be different." She continued...

On Friday night after my parents left I said, "I've got a surprise for you!" His eyes lit up like before and I asked him to come up to the room.

I went to my closet and pulled out one of my favorite dresses of the past. I know it was one that he liked. Between you and me, I did not wear it anymore but I knew it would fit him. "Here, I want you to have this dress as well. But let's see if it fits first." 

He looked a little embarrassed but I encouraged him by saying, "Go put on your favorite bra and panties, get dressed and let's see what it looks like." I think by calling them his bra and his panties I sounded more accepting and I wanted to show my willingness to make this as normal as possible. 

He took the items into my closet, which is huge, and he changed. When he stepped out of the closet into the room and I gasped. He looked amazing. The dress fit beautifully and he was standing tall and proud. He immediately went to the full length mirror and kept admiring himself. I asked, "Do you like it?" 

"I love it!" he said.

"Come over here and sit down." He slowly walked over and slid his hands behind the dress, straightening it before he sat down....he was good...even crossing his ankles as he sat up straight and tall.

"Tommy, you look great and you look so natural. Here is what I would like to do this weekend. I want to pretend that you are my younger sister Tammi. And we are going to have sister fun, starting with you changing into one of your skirts and blouses and meeting me downstairs. Does that sound like a plan?" 

Of course he loved it. This was now going to be like a little game of pretend so now dressing in front of me was more fun than embarrassing. 

He was changed and downstairs in a flash. We cleaned up the kitchen from our dinner meal....watched some TV....some silly girl shows and he sat on the sofa with his legs tucked up himself and loved it. A little later that evening I gave him another surprise....a new nightie. 

It was a cute pink baby doll with matching panties, not too revealing but cute. What he did not know is I bought myself one as well. I asked him to go into his room, put his clothes away and meet me in my room in his new nightie. 

I changed as well and got ready for the next part of the night. When he walked in wearing the nightie, I just said" Hi" like it was no big deal and asked, "Let me see your toes. Oh my, they need a new coat of polish." 

Of course, they were not polished at all so he kind of laughed. He first objected and then agreed when I promised him that the nail polish would come off. 

"Do you think this pink nail polish will match your new nightie? Or maybe this color?" When he finally decided which color, I shaped this nails and gave him a mani and pedi. He just stared at this hands and feet for the longest time. Plus the smell of nail polish was wonderful to him. 

We chit chatted for a while, watched TV together on the couch and then we said good night. "I will see you in the morning and I want you to come to breakfast in your nightie...you can't do that while mom and dad are home." 

In the morning he came down as requested and he was so giddy. I had made a little breakfast and we sat down to discuss the day. I didn't mention it but I noticed he was wearing a different pair of panties than the matching set he was wearing at night. I had a real strong feeling he really enjoyed wearing the new nightie to bed. 

After breakfast I told him to shower, put on a skirt and blouse as we had some morning chores to do. It was so much fun. Once the chores were finished I told him he had the afternoon to do anything he wanted but at 5:00 I had another surprise for him. 

One thing he opted for in the afternoon was to get his homework out of the way and that involved a lot of reading. So there he was, sitting downstairs, curled up on the couch in his skirt and blouse doing his homework...he was so adorable.

At 5:00 he sort of hinted it was time and we headed upstairs. I asked him to take off just the skirt and blouse, put on one of my robes, and sit at my dressing table. I looked him straight in the eye and said..."You need a little make-up to freshen up your face. Hold still while I put a little on." He never even objected in the least.

A little make-up took me 30 minutes as I explained everything I was doing. He did tell me that other than some lipstick, he had never used any make-up so this was finally a real first. Finally!

When I was comfortable with the look I reached over and pulled a shoulder length wig from a bag. This was total surprise to him as well. After brushing it out I slowly placed it on his head, adjusted it and brushed it until it was perfect. 

I sat back, admired my own work and he was no longer Tommy. Then I added some clip-on earrings. He wanted to see himself sooo bad. "No peeking yet," I said.

"Now, put on the new dress I gave you yesterday. And no peeking! And toss on my slides in closet....you need a little lift and they should fit you."

I then took him by the hand....."Keep your eyes close until I tell you." I walked him to in front of the full length mirror, stepped away and said, "Alright, you may now open your eyes." 

He never moved once he saw himself. He just stood there and stared, and admired, and turned his head left and right. It was like an awakening.

"Tammi, you look beautiful." He twirled, spun around and looked at himself from every direction. He loved it and I did too.

After about 10 minutes of Tammi enjoying her new look, I said,

"I told mom I was going to make my closet a priority this weekend and was going to go through everything in it. What I did not tell her is that we were going to do it together. Would you like to help?"

That evening we both tried on every single dress, skirt, and blouse in my closet. We were primping with each other, mixing and matching outfits, and having such girl fun. 

There was even one time early on that I said...."It looks like Tommy really likes that dress"....emphasizing the name Tommy as he was getting a tad too excited in one of my slinky dresses. 




Caught For the Last Time Ch. 06



Tommy excused himself for a few minutes and came back as a much more relaxed Tammi. A blushing Tammi said...."Sorry." 

I told her no worries and shared that I feel the same way some times but it just does not show like yours. And then I whispered to him like in girl talk, "And, you can always tell when a boy really likes you too!" 

A good number of the outfits either didn't fit Tammi or the color wasn't the best. But when we were done after three hours, the mystique of my closet was over. I had identified a total of 7 dresses I no longer wanted and would fit Tammi. Four of them were casual dresses that looked good on her, two were nice dresses she could even wear out, and one formal gown was gorgeous. 

We clustered these all together in the closet and they became the ones she could use at any time. All the other ones that did not fit either me or Tammi were going to be donated. And my closet looked great!

When the Tammi story ended, Sally turned to me and asked, "Oh, I never asked. What name would you like to be called? Somehow calling you James does not seem right anymore."

Ah, the moment of truth...."I was thinking about Jamie. It's always been James or Jim all my life, but never Jamie. I have always liked that name on girls I have met."

My wife nodded in agreement and said, "That does fit you. I like it too. We'll be Kelsey and Jamie, and no one will ever know what gender we are." We all laughed a bit.

We continued talking and I did not want this evening to end. Not only listening to the stories but being able to watch Sally all night was awesome. Watching her arm and hand movements, how she sat and her mannerisms made me more aware of all the fun things I could work on. 

But as the evening wore down, it got to the time to say good night. Sally gave me a real long hug, and it was genuine. 

She said to both of us, "And I want to see more of Jamie. I love what I have seen so far...especially in those killer clothes!" We all laughed.

After Sally left, my wife turned to me and asked, "Well?" 

"This was a great idea. Thank you for insisting we do this."

As we were then putting away the food she asked, "Are you up for a "Jamie night", Jamie? Wouldn't want all this fine make-up to go to waste."

"Only if you pick what you want me to wear to bed," I replied.

With that she went into the other room, brought out a nicely wrapped present and handed it to me.

"I love seeing how happy you are. And I love seeing you balancing our relationship. I know I have not been too involved in your clothes purchasing, but wanted to let you know I'm supportive."

I opened the box and removed a beautiful ivory lace babydoll nightie. It was pure class and I knew it was expensive. She whispered, "Give me fifteen minutes and I'll be right up."

I went upstairs, removed my clothes and my new undergarments. I was so glad I had bought them, they really made such a difference. Even just standing in the bra and panties with the inserts with the wig and make-up made me excited.

I quickly freshened up and put on the new nightie and matching panties. They were soft and elegant. I really felt like I didn't deserve anything this nice. I could feel myself being transformed. 

Just putting on the nightie and the panties made my nipples hard and I actually could not wait for them to be played with.

In the bedroom I softened the lights until Kelsey arrived in her new dark purple camisole, matching palazzo styled pants, heels and hair tied back in a ponytail. She looked ready for business.

"Honey, you look amazing in that outfit," I whispered as she came over and planted a huge kiss on me.

"And Jamie, you look so sexy in that babydoll, " she said as she walked around me and lightly ran her hands all over my body.

She then toyed with my nipples and asked, "Have they recovered?" I closed my eyes and nodded a yes as she began slowly caressing them and then squeezing them gently. "Jamie seems to like this," she said.

She then lowered me to the bed and mounted me, spreading my legs open with hers as she knelt over me. I reached up and grabbed her breasts which were now inches from my face. 

Slowly she began grinding her pelvis into my outstretched legs. I swear I was going to break but it felt so good.

I don't know how long we spent in pure grabbing, grinding and kissing each other, but she was on fire. She rolled over to her back and with her hands led me to straddle her cowgirl style, a position she had done with me many times. 

She reached up and grabbed my breasts and squeezed my nipples as she slowly began lifting her pelvis into mine.

By now my nipples were already sore but I loved the feeling of her squeezing them and then letting them recover. 

The more she drove her pelvis and thighs into me, the more I could tell from her breathing and moans that she was enjoying a series of orgasms.

She whispered, "Stay with me Jamie" as she continued to lift me with each lunge. Each thrust was longer and faster, and she moaned deeper with each one.

There was no way I wanted this to stop. Now that I knew what she liked, I enjoyed this all the more. 

As she slowed the pace down and she had this real satisfied look on her face. She slid me up further on her reached up under the babydoll and slid it up so she could put my breasts in her mouth. 

She toyed with my nipples with her tongue and then began to nibble at them, almost giggling as she was having fun now. Her nibbles turned into bites as I drove my small breasts deeper against her mouth.

Her hands were now around my backside and she was so close to penetrating me with her fingers, but did not. It was such a tease. 

While still on her back she lifted her top and I began rubbing my body against her breasts as I moved up further on her. I could feel myself so close to going off but just wanted to keep this going....but it was impossible. 

I unleashed this massive load on her and she held me tight until my body quivered for the last time knowing that it was my time.

She rolled me over onto my back, removed her drenched top and cleaned me up as we laid there exhausted. 

The last thing I remembered before I drifted off to sleep was her lightly kissing my tender red nipples through the soft babydoll.



Caught For the Last Time Ch. 07



We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top.

"That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head.

Then there was her obligatory nipple touching. "Wow, you barely even flinched. I told you you'd get used to it."

"I'm actually beginning to like it," I replied.

"I was hoping you would. Well, Jamie, what would you like to do today? You've got the whole day ahead of you."

There was a light rain falling outside and it really felt like one of those lazy days.

"After listening to Sally last night and then our amazing time together, I'd like to be Jamie for the day and stay around here. I'm just in that kind of a mood."

"I think that would be perfect and fitting after yesterday and last night," she replied.

I looked around, tried to take an inventory of myself and said, "My face has got to be a wreck so let me do this. I'm going to shower and clean up a bit. Then I would like to make you a really nice breakfast. You relax here in bed and I'll see you downstairs in an hour."

She made one of her infamous, long cat stretches and said, "That would work real nice. Knock yourself out babe."

The shower felt extra nice today and I decided that one of the short chemises with a long robe would be best. I finished a light make-up application on myself downstairs and started making breakfast.

When Kelsey came down she had on a pair of jeans and a nice Tshirt top with no bra. She came up from behind and gave me a real nice squeeze and said, "I'm really liking these mornings...how's my girl doing?"

"I just love it when you do that," I replied.

After a nice breakfast, I cleaned up the dishes, headed upstairs and changed into a skirt and top that would be casual enough for household chores. 

The rest of the day I spent cleaning up from the other night with Sally, doing laundry, and trying to arrange all my female clothes into some semblance of order. 

By now, my closet at home was beginning to look way too jammed. It was like having storage for two different people. Kelsey actually suggested that we begin keeping Jamie's dresses, skirts and blouses in the spare room closet. I had to agree. 

Getting dressed to work each day and grabbing my guy dress shirt from beside my Jamie blouse was a temptation that I did not need to have. I was struggling on how to keep the two worlds separate, and this was a good idea. 

After I had moved all the clothing over I was surprised on how much I had gathered in such a short period. As a nice touch, my wife helped and let me use a few of her hangers for some of the more delicate dresses.

Strangely, there was no strong desire for sex that day. There was a lot of hugging, cuddling and small talk. It was fun, and even just sitting around at night in my Soma loungewear outfit from what now seemed so long ago with her while watching Netflix was fun. It was actually nice that sex did not always have to be a part of the crossdressing experience.

The next day we were off to visit some relatives and when I got up I put all my Jamie clothes away and in the hamper, and actually wore a pair of guy underwear and a nice pair of slacks and shirt. 

As I was getting dressed, she hugged me and said, "I love Jamie, but I love my guy even more." She put on a cute dress which is rare for a weekend and I had to compliment her on how wonderful she looked. She was beautiful.

We actually had a great time together visiting and had amazing sex that night. It was nice being able to balance the two worlds.

++++++++++++++++++++++++++++++++++++

From that day on, things at home stabilized. Oh, I still underdressed for work. And there were days when I would be just a regular guy and not even hint at wanting to get dressed. 

I limited the full make-up thing to weekends. Realistically, it was a time commitment. But it was easy for me to balance a couple of nights a week being partially dressed with light make-up at home with being fully dressed with lots of make-up. In my mind, at least, I was fully dressed all the time.

With so many clothes from Sally, I didn't need to purchase that many things but I did purchase some cute, stretch jersey tops with little Erin's help at Kohls. They were perfect for at home on top of a pair of jeans with a Tshirt bra and I could also wear them out without a bra. Having some dual purpose tops was a thrill. 

My wife even met Erin on that trip and showed her the pictures of me dressed from the night Sally came over. Kelsey really liked Erin and Erin complimented me on being such a perfect gentleman and how lucky Kelsey was to have me as a husband. That was a nice touch.

Erin loved the pictures so much she to keep one picture to show other people she works with. And we departed with her saying, "Please, both of you come back again. The spring clothes will be coming soon and I have some great ideas for you!" 

I think I also became a bit obsessed with my weight and my build. I was now seeing myself dressed in a mirror, a lot. It really made a difference. And now I had pictures as well...good ones and some bad ones. I really needed to work on my posture and my smile. 

And Sally. Her coming over was becoming a routine. My nervousness was totally gone with her and I actually enjoyed her company. Sometimes she dropped by on a weeknight when I was just in my guy clothes just to chitchat with my wife. I would be around, but not really part of the conversation. 

Other times it was a Saturday afternoon when we were all casual and I could be in a bra that was somewhat noticeable. It never seemed to matter to her or me anymore. I would get a hug and she would always playfully rub my bra strap.

And whenever she came over announced, I always put on a wig and at least some light make-up, but unless it was a fancy evening, it was never a lot of make-up. She would inevitably bring me something she was no longer fond or something she thought I would enjoy. She knew my tastes all too well.

In fact, she had "donated" so many items to me that the extra closet now had about 8 skirts, 6 dresses, a dozen tops, 5 pairs of shoes, and 4 wigs. Plus I moved a small dresser into that room that had two drawers full of different types of nighties.

The other factor that changed was wearing things to bed. My wife seemed to enjoy what she called "Jamie Nights". They tended to be weekend nights, especially Friday after a long week work week.

And the Jamie Nights were not always nights, nor were they always predictable either. I remember one Saturday morning when she headed out for some shopping and I stayed at home doing some work around the house. I was wearing a wig, pair of cut-off jeans over my pink panties and a cute top and matching bra. Nothing outrageous, just cute.

She came back around noon with some groceries and a bag from Nordstrom's. "What did you get?" I asked.

"Nordstrom Rack was having a big sale so I thought I would stop by and look while I was out. I looked at a lot of items and realized there was nothing I really needed...until I went to the nightgown area. Look what I found!"

From the bag she pulled out a beautiful white night gown, with a robe and matching white lace panties. The gown had a long split up the side and was so amazingly soft.

I told her "That is so beautiful and I can't wait to see it on you!!" 

"No silly, it's not for me, it's for you! Now go upstairs, try it on and let's have some Jamie time."

"Now?"

She just smiled and nodded, "Do you mind a little Afternoon Delight?"

I did not need much more encouragement and headed up to change. I chose long dark wig and upgraded my make-up. The gown was gorgeous. I stripped down and slid the panties on first. Besides being lace, they had bow ties on the side. I loved that look. The gown fit perfect and the side slit made the cut look sexy as well. 

When I gave her the "all ready" call, she walked in wearing new clingy, deep purple loungewear. Apparently she found something for herself as well. The pants fit her hips perfectly and the top was comprised of a camisole like t-shirt and a long flowing top that opened in the front. In her hands she had two long stem glasses and a bottle of chilled wine. 

She laid the items on the dressing table where I was sitting and gave me a long deep kiss. Slowly she began caressing my breasts. She really did not need to because my nipples were already hard and pressing though the nightie. 

"I can see you like the nightie," she whispered. 

With her auburn hair was pulled back in a ponytail, she looked so hot in her outfit. This was her signature look and got me horny every time I saw her like that. 

After a few minutes she opened the bottle of wine and poured us each a glass. It was wonderful and we sat on the bench and lightly caressed each other until we had finished two glasses of wine. 

She then asked me to put on a little fashion show. With the wig, make-up and white nightgown, I felt like a new bride. I walked, twirled, posed, and played coyly with her in my new gown. The afternoon wine had really loosened us both up.

I then slinked backed over to the bench where she was sitting, hiked the gown up just a bit, and straddled her as she had done with me so many times. Her hands could not have been any more active. Gently, she slid the robe off my shoulders and it softly fell to the floor. 

The feeling was amazing...her legs, now between mine were slowly lifting me up and I began grinding downwards towards hers in a rhythmic motion. 

After a few minutes, she whispered that we should move over to the bed. She removed her robe and laid on her back wearing just her camisole top and long pants. I slowly mounted her again and as I had a chance to ride her cowgirl style, she began to slowly lift her hips and legs towards mine. I loved the feeling of being spread legged over her. 

As we rolled over in the bed, I moved my back up against the headboard and with my legs spread, held her with her back against me. I now had the chance to caress her breasts with my hands and finger tips. 

I slowly moved my hands down her stomach to her pelvis and began massaging her just like she does to herself when she stretches. She loved this and began arching her back and slowly grinding her hips upwards. 

The feel of my legs spread apart coupled with her pressing against me with hers as she was arching back was so erotic. 

I never penetrated her with my fingers but kept rubbing that spot that she was directing my fingers to. I could tell she was having these long deep orgasms and anytime I tried to move my hands, she repositioned them to exactly the right spot.

This continued for the longest time until she almost collapsed with the deepest of sighs. I was still hard and horny and she knew it. After a few minutes, she rolled over and with my legs still apart, slid down and whispered, "It's Jamie's time now."

I laid there in the white gown and was so glad there was a long split up the front. She slid the panties over to the side and took my cock in her mouth. I so wanted to hold on as long as I could.

"Does Jamie like me playing with her?" she asked, and then went right back to kissing and sucking my cock.

"I do, it feels so wonderful," I quietly replied. I began squeezing my own nipples and lifting my hips. 

"Is Jamie going to have an orgasm?"

"I am but I want to wait, but can't. You feel so good," I replied.

"Then let it go Jamie..." 

And with that I started driving my hips upwards like she had done for me so many times to me. She was holding me so tight around my butt and staying with me, drinking ever drop. I could not ever recall ever going that long.

The next thing I remember was waking up around 6:00 when she crept back into the bed, all washed and showered and asked if I wanted pizza for dinner. 

I looked at her in that awakened stupor and she said, "Yes, my little angel, you've been sleeping for 4 hours."

+++++++++++++++++++++++++++++++++++++++++++++++++++++++

I could almost end the story of Jamie here. And while there were so many more positives to write about, so many fun things we did, there were still things we both knew we needed to explore, but it had to be at the right time. I think the next big step came when Sally dropped by...

It was a late Saturday afternoon when my wife called saying that Sally was coming over. It was a casual day and I was wearing one of her skirts, a cute top, and my short wig with light make-up. I got a big hug when she arrived.

Sally remarked that Tammi had an outfit similar to that one and it reminded her of another story. We all sat at the kitchen table and had some coffee as she began explaining what happened as she was getting ready to leave for college years ago.

"My senior year of high school was full of so much excitement. I never wanted it to end but I was so excited about going to college. Tommy liked the idea as well because it seemed that every time a new school event came up, mom would take me shopping for a new outfit. He could hardly ever wait to see what I had bought"

"We had rules, and he was now really good at keeping them. Unless I gave him express permission, he was not to wear my new clothes. But then again, I gave him permission a lot once the event was over. And frequently I would actually help him dress up or do his make-up so I knew what he was wearing."

"But the reality of it all was...I was heading out to college and it was coming too fast. With spring came summer and soon I was beginning the process of packing up for college."

"My mom was taking it hard as her little girl was leaving. We had been doing so many things together that I was truly going to miss her as well. My dad had become a bit more distance as his work kept him traveling a lot, sometimes at a week on end, and my mom was struggling to do all the chores around the house that he could not get to while he was away."

"One reality that hit me was how Tommy was going to handle keeping his secret while I was away. In my room he had a complete collection of clothes and two full drawers of bras, panties and nighties that he wore on a routine basis."

"We talked at length about possible solutions, and while they would work for a while, he was bound to get caught by mom. We had to somehow get her into the mix."

"Then it was the day for me to officially leave for college. I knew Tommy was going to have a tough time adjusting from having full reign of my clothes to sneaking around again."

"For a while we chatted by phone every day, and then every couple of days. He was doing OK, but his dressing time and washing clothes, etc., was always fraught with a little fear."

"By the time Halloween came near, Tommy and I crafted a plan where he was going to tell mom that he was going to a Halloween party and wanted to go dressed as a girl." 

"Tommy would ask mom if she would call me at school and ask if it would be OK for him to use some of my older clothes that I no longer wore." 

"It seemed like a good plan, but my mom thought that I would never agree to it. But, at least agreed to call me and ask." 

"She did call, and after a phone call or two, Mom and I agreed on a couple of different outfits and I gave mom some hints. I tried to be genuinely surprised, but generally supportive of this idea, explaining that I knew of guys that did that for Halloween."

"Several days prior to the party, mom laid out all the items I suggested on my bed. Dresses, skirts, blouses, bras and panties, even shoes and a wig. She was truly nervous about this whole idea." 

"Tommy's role was to fake his understanding of girl's clothes and to act embarrassed but excited all at the same time. He did not disappoint." 

"Mom first had Tommy go into my closet and try an outfit on to make sure it fit before she attempted any make-up. Tommy had already worn everything he was trying on so that was a really no brainer." 

"Mom then told him to come out in the outfit and he did, but he was shy. She then did his make-up using the colors I suggested." 

"Once she brushed out the wig and put it on, mom nearly cried. She told him how much he looked like me. It was not quite the reaction he was expecting."

"Mom made a few adjustments and he tried on the other outfits I had suggested. He could not decide which one he like more and neither could mom. Tommy then tried on everything again, loving every moment of it."

"She then said, "Tommy, any of those three will work. Why don't you just clean up, change and come down when you're ready. I have a few more things to do downstairs for dinner.""

Tommy spent a little more time in my room and had a chance to try on a few other things he had missed wearing since I was away. He did go downstairs but mom did not talk too much about it.

Just prior to Halloween, mom and I talked again and I kept asking her how he looked. She kept saying how nice he looked and I kept prodding her to let Tommy know as well. He needs your reassurance.

When Halloween arrived, she helped get him all dressed and dropped him off at the party. As it turned out, Tommy never went into the party but walked around trick or treating instead. That was the plan anyway.

That night when he came back in Mom told him again how good he looked dressed up as me. And how no one even knew it was him. 

He then sheepishly confided in her that he actually enjoyed it more than he thought. And, that girls were so lucky to have such nice clothes all the time. He did not rush to change out of the clothes that night as he told mom all about the party (that really did not happen).

With dad away a lot, mom and Tommy got a lot closer. They didn't talk much about Halloween and dressing up, but they did get closer.

Thanksgiving break was just around the corner and I could not wait to get home from college. On the Friday after Thanksgiving, dad flew out on another trip and the three of us we were chatting in the afternoon. Mom brought up Halloween and said how wonderful Tommy looked all dressed up. I then had an idea. 

Since I never had a chance to see Tommy made up for Halloween, I said, "Let's do it tonight! And then we can have dinner together. It's just the three of us. And it will be a dress-up night for all of us!"

Tommy thought it was a "dumb idea" but "reluctantly" agreed. I offered to do his make-up.

At dinner the three of us were wearing real pretty dresses. I asked. "Mom, give him some advice like you used to tell me." 

She smiled and said, "Please sit taller, keep your legs together, take smaller bites." 

It was fake basic training all over again. Mom was really getting into it. 

After dinner we chatted some more, watched TV and just before retiring for bed I ran upstairs and got one of the nighties that was earmarked in Tommy's drawer and brought it down.

"If you're going to wear a pretty dress you might as well sleep in a pretty nightie as well."

Both mom and Tommy looked shocked at my offer. Mom then broke the silence and said..."Why not Tommy? Do it for your sister." 

Before I headed back to school I told mom and Tommy, together, that I would see them at Christmas break, and that Tommy had permission to wear anything he wants at any time...and maybe we can do it again when I came back at break.

That really opened up the door for Tommy. He used that opening to bring in one bra, a pair of panties and a nightie into his room and kept them in his top drawer. Mom never said anything but I'm sure she saw them.

But then, it wasn't but a week later that there was a small freak snow storm in December that cancelled school, so Tommy was going to stay home alone. Mom said she had to go to work but maybe they would close early. 




Caught For the Last Time Ch. 07



Within an hour of mom leaving for work, Tommy had changed into a simple skirt and blouse, along with bra and panties, he applied some light make-up and with the wig on headed down stairs. 

He started in the kitchen by doing the dishes and had just started the laundry when mom walked in and said, 

"Good news! They sent us all home." 

When she saw Tommy all dressed she was a bit surprised but not upset. Tommy was feeling real comfortable, but tried to act a bit embarrassed and said "Sally said I could wear some of her clothes. I just felt like wearing them today while I did some chores. I hope this is OK with you mom?"

"OK? I think it's wonderful. I was afraid that you were embarrassed the other night when Sally was home and we spent the night together. I have been fretting about it ever since." She gave him a big hug.

That began a long and different relationship between my mom and Tommy. In the two weeks building up to Christmas break, he dressed a couple of more times at home, usually on weekends with mom's help. He really spent a lot of time with her and their relationship got better.

When the Christmas break came and I hauled all my clothes back from college. I went through them and told my mom that Tommy could have some that I know longer needed at college. 

As a special treat at Christmas, she and I actually bought him two sets of bras that fit him and matching panties to put under the tree so that they could really be his. I think he liked that a lot.

Tommy started dressing a tad more unisex after that so as the winter became the spring, he was comfortable being at home with mom is whatever clothes he had on. 

My dad became more and more distance in our lives and by the summer, mom said that they decided to separate for a while until he figured some things out. She took it pretty hard.

Then Sally, wanting to end on a high note, said, "So, one of the other reasons I wanted to come over was that I got a call from Tommy just this week. He has a business trip coming up very soon to this area. I'd like him to meet you."

+++++++++++++++++++++++++++++++++++

It wasn't but two weeks later that Kelsey got a call from Sally letting us know that Tommy would be flying in the following Sunday and was wondering if it would fit our calendar. We had talked about it and decided this would be a good step for me. I realistically had no one to talk to besides Kelsey and Sally.

We decided to meet a restaurant for dinner on the Sunday night he arrived. It would be just the four of us at dinner and to clarify, we were all dressed in our respective male and female attire. I have to say we all looked good that night.

We had a great time getting to know each other. Tommy was everything Sally described. He shared that he has a successful career in the aerospace industry and loves his work environment. 

Several of his coworkers knew of his crossdressing but he never dressed openly at work. He said he had no compulsion to do so as he enjoys being a guy. He just likes going out and presenting as a female sometimes.

Going out dressed was something really foreign and scary to me so I asked him, "May I ask where do you go and how often?"

He said "When I first moved to Chicago it was big and unknown to me. But I had a good job and it was a good career move."

"I checked the internet and found a lot of different transgender or crossdressing groups so I began researching which ones were active and where the members hung out. I actually went to a few of the locations in stealth male mode on nights when the groups were meeting just to get the feel of the group."

"For example, one group met in the corner of a small bar and were dressed in clubbing type clothes. Another group met at a nice local restaurant and were dressed nicely and conducted themselves as ladies, barely giving rise to any patrons."

"It took a couple of months of checking things out before I ventured out anywhere. I also shopped at all of the Dress Barns, Lane Bryant, specialty shops, etc., bought a few things here or there and asked the sales staff. They had so many male clients that they were always helpful in giving me thoughts on where to go out."

"I remember my first outing was in the suburbs in the restaurant setting. I had contacted the group and asked if I could attend. They were so happy I did and eagerly invited me."

"They told me all the little things like it was a family restaurant, dress appropriately, etc., but I already knew that. It was one of the places I stopped at early and had checked them out. But I let them fully explain it. And it was a weeknight so my first dining out experience in Chicago would be easy."

"That night I wore a very conservative button up the front blouse, no cleavage, a skirt just below my knees, low heels, and really worked on my make-up to give me that every day look."

"After dressing for years and with the help of Sally, I was really good with my make-up and my outfits were really nice. My poise and confidence levels were also high so I had no problem arriving at the restaurant, talking to the hostess and walking through the restaurant to the table." 

"I introduced myself and met some really nice people that evening. The conversation that evening was all about me, the "new girl", so I told them about my wonderful sister and some of the fun things we did growing up. I did not disclose too much about my everyday job but it was nice to hear that I was in the company of a doctor, attorney, architect and another engineer."

"As we talked, they asked if I had been anywhere else in Chicago and I said no, mostly staying in, but I asked if they had any recommendations?" 

"They started listing the places they went to. Sometimes they would go as a group of 4-5 and other times just a couple of them. Two of them were headed out on that Friday night to a club downtown that had alternative lifestyle night and thought I might like that. I got their email addresses and said I would think about it."

"The idea of trying a new place was intriguing and hanging with new friends would be good as well. I'm not into solo action in a new city. I checked out the club's website and got some ideas as to what I would wear and decided to have a go of it. But I was still unsure."

"Checking out a website versus reality leaves a lot to be desired. So I drove by the place one night and realized that if it looked as bad in the inside as the outside, I was not going in. I contacted one of my new friends who told me the inside was amazing and I should definitely dress for a club scene." 

"I went into my closet and start putting together an outfit. Actually two outfits that night. One to drive in and another to wear at club. My driving outfit had to be easy to remove...a front buttoned blouse, a ¾ length skirt and some flats."

"Since I had to walk out of my condo association I wanted to draw as little attention to myself as possible." 

"For at the club I had the shortest black flounce skirt, a gold sparkly cowl neck draped top and spiked heels. Just a little different." 

"Before I left my condo, I went heavy on the make-up and walked cautiously out of my condo in my conservative clothes. No one even looked twice."

"When I arrived at the club I parked in the adjacent garage and quickly slid my club clothes on. I can do that in a heartbeat, and as a hint...always leave the heels for last." 

"I left the parking garage and headed across the street. As I walked into the club, the place was hopping and real classy! There was every lifestyle imaginable. Lots of Goth, dykes, lesbians, crossdressers, gay...and straight as well."

"I fully expected all the attention to be on me but it was just the opposite. Every little group seemed more interested in their own little group. It was an interesting dynamic." 

"When I saw my little group of two I recognized them right away but they did not recognize me. I was wearing a blonde wig tonight with heavy make-up rather than the brown wig and light make-up I wore at the restaurant."

"I decided to have some fun and stand near them but not acknowledge them for a while. With my heels I was standing at six feet tall, legs up to my whatever, and looking like Taylor Swift. Not the demure Tammi they met the other night."

"With the music so loud, when I did say hi, they still didn't recognize me as I was shouting out my name. They were all surprised when they realized it was me and got a laugh."

"I met about other 10 other people that night. We had a great time dancing, drinking and chatting. After the evening I headed back to my car and changed back into a more conservative me."

"I always, to this day, get a little nervous about too many people knowing about me, including my neighbors at the condo association. But if they know, they know. I try to low key the outside dressing but am comfortable dressing at home on weekends, getting out with friends and a couple of nights a week if I have time."

With that Tommy asked me "Have you ever been out?"

"Gosh, other than underdressing at the movies that one time and putting on some outfits at various shops, the answer has to be no."

Tommy then said, "Sally told me you look fantastic when you are all made up. How about we all go out to a place far away from here where no one will know you for a dinner one evening?"

"We can all wear wigs, even the ladies, just in case you know someone there. It would be a lot of fun."

Strangely, it sounded interesting and my wife agreed as well. 

Tommy continued, "Since I am only here this week, let's go this Tuesday night. I have no meetings that night. I had looked up a few places already and checked with some friends who have frequented your fine city and they recommended these." 

The good news is that I had never heard of these restaurants and did not know of anyone living in the nearby towns so I felt a bit more comfortable with the idea. 

On Monday night my wife and I spent over an hour deciding what to wear and decided on a Sally outfit...slightly longer skirt, tunic top, lots of drapey jewelry and low heels. My wife decided on similar attire. 

We left our house on Tuesday in the cloak of darkness. It was the first time I had been outside dressed. 

When we arrived at Sally's to pick them up I was so shocked to see what a transformation Tommy had made into Tammi. If I had not met him before I would not have recognized him. 

Sally immediately stepped in and said, "Tammi, I'd like you to meet Jamie." We gave each other a girl hug and air kiss, and complimented each other on our outfits. 

We stood around primping a bit while we enjoyed a glass of white wine, took a lot of pictures and then headed out.

Going out with a group of four is so much fun. With Sally and my wife wearing high heels, and Tammi and I wearing lower heels, it helped take the pressure off of us towering over them. Plus having Sally and Kelsey in wigs changed their looks entirely.

At the restaurant my nerves kicked in again. I kept telling myself I looked good, no one knows me and I can do this. I tried to follow Tammi's lead walking in and became like her shadow. 

Tammi walked right up to the hostess and gave her our names. With a wonderful smile, she welcomed us and complimented us on how well we all looked this evening. Wow, one hurdle out of the way.

We had our own special table near the windows, which meant we had to walk through the entire restaurant. The restaurant had about 25 tables so it was not huge, but there were enough other diners in there. 

Tammi loved every minute of the walk and I was dying a thousand deaths with every step. She glided through the restaurant and the only heads that turned were a few guys who were checking Tammi out. I did not feel like I was gliding but at least I did not trip. 

But, we made it to the table. The waitress could not have been nicer and addressed us as ladies all evening. 

Throughout the meal, Tammi and Sally shared story after story, including times he visited her at college, to dating some of her guy friends and to the struggles he still has with relationships. 

The stories were griping and gave me lots to think about in terms of my own feelings.

We had a wonderful dinner and as we looked around, I think we were the last to leave, so we gave them a nice tip. The hostess came over to us several times during the evening to make sure we were having a wonderful time, and as we left, asked us to please come back again. I assured her we would.

That was the last we would see Tammi or Tommy on his trip, but we agreed that maybe we could take a trip up to Chicago and visit him some long weekend.

Our trip home after dropping Tammi and Sally off was quiet.

"Are you OK babe?" she asked after several minutes of silence.

"I am, and I'm so glad we went out, and I really hope we can do it again. It was more fun than I ever expected and I love being Jamie with you."

That got a nice little squeeze from her.

"But talking to Tommy as Tammi for the whole evening, and not really seeing him inside there, but her was hard for me to process. He was Tammi, not some guy dressed up as Tammi. Does that make sense?"

Quietly she said, "Yes, it does."

"I guess for the first time in a long time, I felt more like a guy in a dress rather than the girl I feel like at home when I'm dressed and with you. I just need time to process this." 

"I think we both do," she replied. "And even though it's Tuesday, I think that cute ivory babydoll would be perfect for tonight, don't you?" 

"Yes, perfect."



Caught For the Last Time Ch. 08



In the week that followed Tommy's leaving, I kind of felt that a void was created. Seeing him and speaking with him as both Tommy and Tammi, rather than just hearing stories of him, had a profound impact on me. It made me a little jealous and a little sad.

I was basically dwelling on the question of, now what? I can dress at home whenever I want, have an overly supportive wife, our sex is good, no, it is great, I can shop almost at will and I've been out dressed and survived.

Kelsey was sensing this in me as I did not dress as much during the week. I was also a bit distant in my thoughts, so she asked me one night,

"What's up. I've been seeing a little less of Jamie. I don't mind that, but that little bounce in your step is not there."

I shared with her my thoughts and she said,

"Maybe we need to do something different."

"How so?"

"When we went out with Tammi and Sally to the restaurant, you first felt nervous, then excited and then comfortable."

"Yes. It ended up being a lot easier than I thought."

"Why was that do you suppose?"

"Well, going to a place where no one knew us was a plus, and Tammi gave me encouragement. You know, if she could do it, I could do it." 

"Anything else?"

"I got to stay be Jamie from when we left the house that night, then to Sally's and then the restaurant and home. It was probably 5 hours being Jamie in front of other people while being out. That made a difference."

"It was a big step and you did well."

Kelsey then added, "What if we took a trip somewhere where you could be Jamie for a long period of time again, maybe several days in a row?" 

I thought for a minute and replied, "That might be fun. You know, going to work all day, and coming home and changing for a few hours is great and all. But being able to be dressed and being Jamie for an extended period of time might be a good solution to the funk I am in right now."

Kelsey then added, "Truthfully, I don't have any real desire to go to Chicago where Tommy lives, but maybe we could get a nice package deal for some place fun like Las Vegas for a few days. We both have enough vacation time accumulated."

We talked through the idea a while and then Kelsey, the consummate planner began looking at dates and found that we could get good airfare to Vegas just over a month from now. Anything closer was way too expensive plus too difficult to get off from work. 

While she was looking at that, I sent an email to Tommy, asking if he had any ideas. Tommy replied with an essay of ideas. He had been to Vegas a number of times. 

He said in one part, "The biggest challenge in Vegas is deciding where to stay. Staying at the Bellagio is awesome, but changing in your room, taking an elevator with other people to the lobby, walking a mile through the casino dressed, returning to the hotel, walking another mile, showing your room key to hotel security and knowing you are on a ton of casino cameras is a big step. I personally love it now but it was a challenge for me at first. Make that your second trip "

That paragraph resonated with me. Realistically, I had trouble walking 100 feet through a restaurant hiding behind him. Walking through a casino with all those beautiful people could be a challenge I wasn't ready for. 

So we began looking at other casinos to stay at. In Vegas, it probably didn't matter which one we stayed in for location purposes because we were renting a car to get around. Las Vegas was just so big. 

While Kelsey worked on the travel arrangements, I started to "train." I now had a goal. 

It was like the Rocky training scenes as I began thinking through every day and night, figuring out what to wear, pretending that I was ...no, not pretending, but being Jamie each day and night.

First up, I realized that I needed to get out more as Jamie. As excited as I was about taking a trip, I had only been out of the house once. 

I shared this thought with Kelsey and said, "We're going out this Tuesday night again to that same restaurant, but I'm taking the role of Tammi."

"I like that," she replied. "Plus you know the hostess and they were all friendly. Good idea."

Since we now knew the style of clothes they wore in that restaurant, I took my outfit down a notch to a nice casual dress. That would blend in better with the patrons. We were a bit overdressed the first time.

The same hostess greeted us, took my hand, complimented me and the Kelsey on our outfits and sat us at a nice table. "I am so glad you came back. I hope you two become regulars."

The restaurant was much easier to walk through this time and I loved it this time.

I tried to never once think of myself as anyone but Jamie and that made me feel that much more comfortable being there. In fact, at one time my wife leaned in and asked, "Are you flirting with our waiter?"

"I didn't think I was," I replied, "I'm really sorry if it seemed that way."

"No, it was actually cute. You seem so at ease to night. I love seeing that."

After a wonderful night at the restaurant, Kelsey suggested we take a walk through a nice area of the downtown area. I was nervous but agreed. 

The shops had just closed up and there was very little foot traffic. We did some window shopping, stopping and looking along the way. It was such a nice night to be out.

That little walk was more important than I though. I could now see a reflection of all of me in the large store windows as we walked and stopped at different windows.

I was shocked to see how much I looked like guy standing there in my reflection as compared with my wife. Depression immediately set in.

"What am I doing wrong?" I asked.

Realistically, I knew I was never going to look like Kelsey, but I could definitely do better than this. 

"Hun, try keeping your shoulders back further for starters." That little adjustment made a big difference.

I did that for a couple of minutes, then quickly forgot and slipped out of that posture back to my comfortable guy stance. 

My reflection got worse again. Why didn't my reflection look like I felt? This was not easy.

We made other adjustments as well, like learning how to hold my shoulder purse strap with my right hand in order to keep my guy elbows closer to my body. "Closer, no, even closer, that's better," she would say.

The large windows caused me to continually check and re-check my posture and poise. It must have been annoying for my wife. 

But as we continued the walk, the "me" in the windows slowly looked at least a little better.

"Looking good girl," my wife said as I kept trying to work on my posture. She was so encouraging. There were signs of progress.

At home that night, I was more upbeat having been out and having added walking to my experience. But I really wanted to keep the Jamie theme going. I quietly slipped into one of my prettier nightgowns and waited in bed for Kelsey. 

I took a real passive role that night and as Kelsey ravished every inch of me, I made sure than I was expressing myself vocally to her. "I love it when you play with my nipples." 

"So my girl likes this. I love hearing that," she said as she lightly kissed and bit my nipples through the nightie.

"You always feel so good when you're on me," I whispered as she stayed on top of me, grinding her pelvis into me. 

I knew there was a passionate Jamie deeper inside me and I wanted so bad for her to come out. I just needed to take more positive steps on my own and give her voice.

++++++++++++++++++++

Getting out to restaurants then became a weekly thing. Mid-weeks were an easy night because of smaller crowds, and we got a list from Tammi of places her friends recommended. They were perfect choices. 

We always added in a stroll somewhere, either at the beginning or end of the night, just to work on my poise. This was an ongoing process, even at home. I watched women walk when we were out as well as on TV. There were so many different styles and I needed to find mine. 

I vividly remember one night when we were out walking that Kelsey secretly videotaped me for about 10 seconds and then showed me. I looked awful.

I then said, "I want a do over." Even with me focusing on my walking, I still need improvement after she shot another sequence. This was not easy. 

"Let's do it again," I said. We critiqued each walk. I swear I walked down that same block ten times before I began to feel even comfortable with what it looked like. 

Truthfully, I really felt that I was already exaggerating my movements, but it wasn't until I saw the final video that I realized I needed to go that bold to look right. Feeling like a girl and looking like one when walking are two different things. Maybe Vegas was a bad idea.

On another night, we hit a younger place that Tommy suggested. We made that a real casual jeans night as this place had booths and great music. For some shape, I had put on the hip pads and the body shaper which really helped me in the middle and push out my boobs. 

I loved this casual look and so did a few of the female wait staff who commented with phrases like, "I hate you girl. You've got better curves that me."

That evening was a quick meal so we ventured into our first store together after dinner. 

It was one of those exterior mall complexes, so walking about was so easy, like window shopping. We selected two shops to visit. Lane Bryant and Chicos. I had been to both in guy mode before but never dressed. 

Lane Bryant was easy, and realistically, not the place I needed to shop, but could. "Shoulders back hun," Kelsey whispered as we were about to enter the store. This girl stuff was not easy.

As soon as we entered we were greeted with, "Good evening ladies!" 

Wow, that was so nice. 

"Is there something special we can help you with?" they both asked almost together.

"We're going to Vegas in two weeks and Jamie needs a dress that will just pop! Any suggestions?"

The younger sales associated thought for a bit and pulled out 3 different dresses and a couple of tops as well.

"Let me set up a room for you!"

This was freaking awesome. 

After each outfit, the associate made me come out and show her. She either made a size change or came back with yet another dress.

While the Lane Bryant dresses did not really do anything for me, I loved one of the tops. It was sparkly, fit my shoulders well and went well with my skinny jeans. We actually took a few pictures of me in it. We did buy it, plus it was on sale. 

And the sales associate said, "Please come back any time. You two were a delight!" 

Chico's was no different. They have weird sizing and the associate explained I was probably a 3. I was thrilled until I realized they start at zero and go up to a 3. The 3 was my size. 

The more I looked and tried a few things on, the more I realized this is probably where Sally shopped. Too many outfits looked like ones I already had so we didn't buy anything there. I guess I was already a Chico's girl. But it was a fun experience none the less. 

After our little shopping excursion, my wife suggested that I stop by Kohl's and check with Erin. With Kelsey having met Erin, and vice versus, I think I earned an element of trust. 

After work I stopped in at Kohls, and there she was. "Yes, you're back!" she said.

I then said to Erin, "We are heading to Las Vegas where it will be hot and I'm looking for a couple of evening outfits as well as a few day ones. Any ideas?"

Erin located about 4 tops that I liked and a several skirts that worked well with them. One of the tops reminded me of the gold top Tammi told us of in her story, so I had to get that one as well. I tried them on with my bra and panties I was wearing and Erin gave her approval.

"You and your wife are my favorite customers now. You seem to have so much fun together. And now Vegas. Promise me..."

"Pictures...yes, I will bring you lots of them."

Before I left, Erin stopped me and said, "Wait, I have an idea, my friend Joy works at a boutique about 5 miles from here. It's got real nice designer stuff and sometimes amazing sales. She works Thursday through Saturday. I'll send her a text tonight if that's OK with you. And bring pictures, and maybe even your wig and shoes to try things on." 

I told Kelsey but she couldn't join me and said, "Go, but don't break the bank."

On Thursday night after work, I slipped on a bra under my work shirt and headed north. The boutique was so small I actually drove by it once by mistake. 

When I arrived, there were no customers in the store, just the sales associate...and the store was small, real small. As I wandered in I got a very friendly "Hello, my name is Joy, thank you for stopping by. Is there anything I can help you with?" 

Joy reminded me so much of Erin. I liked that a lot.

I introduced myself and told her about my Vegas trip. She said, "Oh good, it's you. Joy texted me the other night. I am so glad you came, she even gave me your size."

I showed her some of my pictures on my phone and she loved them. 

"That's wonderful. This is a perfect time to be in. We have some great sales going on. Let me show you around and then you can browse for a while."

"Let's start with the dresses. The size you are looking for are right in this area."

"Over here we have our skirts in all lengths and colors. And over here we have the blouses and tops. They are always popular because you can mix and match and have so much fun."

"On this side of the store we have our special occasion or what I like to call party dresses...we have a big sale on these right now because we are well past the holiday season. And over on these racks are the long, more formal dresses. Some of my favorite designer dresses are in this area."

"I will give you some time to browse first, but feel free to ask me any questions."

Off she went and off I went. For 30 minutes I meticulously went through every dress, skirt and blouse in my size, as well as looking a size up and down because different manufacturers run differently in sizes. 

While I was shopping only one person came in and she stayed for all but 10 minutes. In a small store like this, you get to see and hear every conversation. 

After a while Joy stopped over and said, "I hope you do not mind but I was trying to imagine which outfits would look the best on you once I saw you and your pictures, and these came to mind."

She then asked, "Is it OK to start with these for a fitting of sorts and we can go from there?"

Did I mind? This was like a dream come true.

"Joy, before we start, I brought a wig and shoes with me, should I get those?"

"Absolutely, that will definitely help with the fit. And that was good thinking on your part to wear your bra tonight."

And I thought the bra could not be seen...oh well.

What's so different about the boutique is that they had this great little area to try things on. Once you changed into the outfit, you were able to step out of your changing room into a common area with lots and lots of mirrors. It was wonderful. 

Joy kept my enthusiasm level high even when the dress did not look good on me or did not fit. What was nice is that Joy always made it the dress's fault if it did not look good on me. She was good. 

We tried different colors and different lengths and styles. After trying on a half dozen dresses she said "It seems that the A line dresses fit you best, with a bit of an empire style to it."

After over an hour, we decided on one dress and kept another one aside as a back-up. I was very pleased and could have easily selected five dresses, but I only needed one. 

I can best describe my selection as a little black cocktail dress. It had cute straps, cut a little shorter than I expected would look good on me...especially with the heels, and had some subtle glitter on it. 

"But before you go", Joy asked, "I have a favor ask. Would you try on several of these longer formal outfits? Some of these just came in and I have yet to see them on anyone. I think someone with your height would look great in them."

Let's see I thought. You are asking me if I wouldn't mind trying on ultra-expensive designer dresses? I smiled and said, "I would be delighted to do it." 

For nearly an hour I tried on 8 different gowns. From full frontal coverage to spaghetti straps, they were absolutely gorgeous. And with each one, Joy spent time critiquing each dress for me. What she liked about each one and what she did not like. 

And she also helped with my poise. Try and move your shoulders back a bit more. If you can, squeeze your elbows in closer to your body. Stand sideways and turn your head this way. Try walking by placing one foot directly in front of the other and that will make your hips swing a bit more. All things I thought I was already doing. Oh well. This was going to be a long process.

She then told me I had a real knack at being a model and she would love to have me in more often to try on her new arrivals as well as some of her own designs. I did not know if she was serious or not, but I did not care...I loved the attention.

When I arrived home, Kelsey was as excited to hear about my story as well as see the new dress. I quickly tossed it on with my wig and heels, and she said it was elegant and the fit was perfect. Then she said coyly, "Let's try it tomorrow night at home with some real nice make-up. I think we could each use a Jamie night."

Tomorrow could not come soon enough. Shortly after I got home from work and had a bite to eat, I changed into my black bra and panties. Kelsey worked on my make-up. She was really going for the sultry evening look. Even standing there with just my wig, make-up, with the black bra with my silicon inserts and panties, I was excited.

Kelsey stood up beside me and began caressing my body just as I would hers. "I love you even in just these." 

She then helped me slide on the hip pads and body shaper, and then the dress. This looked better than I ever imagined. Kelsey took dozens pictures, including some of my holding a glass of wine in different settings. We took simple pictures and sexy ones. It was so much fun. But we also deleted dozens and took more until I felt that I had each pose down. It's tough looking into a camera and smiling. 

"Let's go for a drive," she said.

"But it's early."

"All the better."

As we started out, Kelsey drove and simply said, walking around Vegas in that outfit will turn heads. Let's get used to it a little bit." I was a bit panicked.

As we drove, we talked more about Vegas. I then realized she was heading in the direction of the boutique shop. 

"Are we going back to the boutique?"

"Yes we are."

Kelsey purposely parked across the street and we had to walk about a block to get to the store.

"Look at the babe in the windows," she exclaimed.

I could not believe it but I was actually pulling it off. It almost looked like two girls walking down the street. The heels, the dress, and the excitement of being out was now all coming together.

When we walked in I was surprised to see both Joy and Erin from Kohl's there. "We wanted to surprise you, and see you all dressed. Let's see!"

I modeled the outfit for them and they took a bunch of pictures.

Joy then said, "Erin and I talked on last night and wanted your wife to see you in some of the gowns you tried on. Hope you don't mind. You looked so good in them." 

"I've selected these four outfits for you to try on first. The first is a bridesmaid dress. Given your color scheme I have tried a deep purple and the fabric is a soft, free flowing jersey. There is some ruching at the bodice and I think the lines will work well with you.

I felt like I was on Say Yes to the Dress. My wife and Erin were sitting outside in the viewing area and Joy was working with me getting everything perfect. It is so nice when someone knows your size and what style works best on you. I have seen brides and bridesmaids walk out in ridiculous gowns on those shows because that style did not fit their body. Joy knew what would work.




Caught For the Last Time Ch. 08



Joy took me by the hands and asked, "Are you ready?" 

She adjusted my hair one more time and looked me over top to bottom. "You are beautiful", she whispered.

When I walked out, my wife gasped. She took around 10 different shots from different angles.

At this point a customer walked into the boutique. Because it is such a small place she wandered right by where we were. 

Joy immediately went over and greeted her. I heard the customer say to Joy, "She looks beautiful in that gown."

"Yes she does...it's for a wedding in two months."

"Tell her to buy it!"

The next two were great as well and my last one was one of those short dresses that really flared out at the hips...almost doll like. I was a bit hesitant thinking it might not be age appropriate, but Joy said..."just think of this as you are a cougar and you will be just fine."

It was a tough sell in my mind but I gave myself a bit of an internal pep talk, looked at myself in the mirror one more time and headed out with my hands on my hips.

My wife was already on her feet waiting with the camera and the comments I got from both Erin and my wife were like..."You go girl!" After the obligatory photo shots, it was time for a change.

Erin switched places with Joy as another customer came in, and she reached over and handed me a different wig and said, "I would like to see you in a short auburn wig for these next dresses." 

It was the long black empire gown with rhinestone around the straps I loved earlier from yesterday. It was a beautiful gown. Erin pushed a little of my hair in front of my eyes and that gave me that sultry look! I had never tried that with a wig before!

"I need you to sell this dress. Tilt your head downwards a little...try giving that seductive look...and look them right in the eye. Your arm carriage is perfect, but let's get those shoulders back a wee bit more... take smaller steps when you walk out...and cross one foot in front of the other as you walk. Can you remember all that?"

In all, I tried on eight dresses, all with different looks. All the while different customers came in, even couples and Joy always engaged them in conversation as they browsed and looked at me trying them on. The comments were always like, "She looks wonderful...I wish I had her figure...what's the event, she looks great" 

After the last dress, it was time to change. I had been in the shop for nearly two hours and loved every minute of it. 

As I changed back into the little black dress, I asked Kelsey, "I do not want to waste this make-up. What should we do now?"

"Joy, Erin, do you have any suggestions?" 

"We close up in 10 minutes, do you want to go a bar we go to? I know the people there and I know you'd feel comfortable."

"Only if we can buy the first round."

We browsed a little until they closed, and at closing time we drove about 2 miles to this really loud but friendly bar. There were lots of people there in all kinds of outfits. In fact, there were so many people that we were practically invisible.

Erin and Joy introduced us around, and everyone was so nice. We actually stayed for a couple of rounds and then headed home.

"You ready for Vegas babe?" Kelsey asked. 

"I am. Thank you so much for pulling this together."

At home Kelsey seductively disrobed me in the bedroom down to my bra and panties. "This outfit will be great for Vega," she said as sat in front of me and slipped the bra strap off my shoulder. As she began playing with my nipple with her tongue and then teeth she said seductively,

"And I'm going to be Jamie's lover for four days as well."

She dropped her hands down to my penis and said, "You can be as active or passive as you want, but I will be there for you each day and night...and what happens in Vegas may or may not stay in Vegas."

Kelsey knelt down and gently took my cock into her mouth. Slowly, as I stood there watching her and me in the mirror, I played with my nipples and quietly exploded into her mouth. She stayed with me until I was done.



Caught For the Last Time Ch. 09



End of Series Notes

While not the last chapter in this couple's life, it is the last chapter in this series. Finding the right theme to end a series with is not easy, but it was through the wonderful emails I received from so many, that is was easy for me to keep Jamie and Kelsey in love with each other, and only each other until the end.

There were many real moments in this final chapter for me and many "I wish they were real and still hope they will be real" ones as well. I hope you enjoy.

++++++++++++++++++++++++++

Several nights before we were to leave, we invited Sally to come out to dinner with us. She was so impressed with my overall poise since our first dining experience. 

"I need to let Tammi know how much you've changed. You have to put Chicago on your tour next year and I'll come too. We will have so much fun."

By the time our Vegas trip had rolled around I had gone out six times, mostly nights but we even did a day trip and took a little walk. It was scary at first, but the practice of walking in open spaces was good. I even got a pair of flats, two pair of low heels and a pair of sandals to make the walk more comfortable. There was a lot to planning this trip.

Packing was the most difficult part. We literally laid out clothes for each day and night, undergarments, shoes, and nighties. Plus, we were hoping to buy a few things out there. Kelsey even bought me a beautiful black baby doll nightie as a special gift for all the hard work I had put in.

We had decided on a four night package at the Palace Station and kept the itinerary simple. Our first night would be an easy night. Get dress, drive around the strip a bit and wander into a couple of the casinos. 

Second night we would catch a show, Divas Las Vegas and maybe head over the Bellagio and watch the fountains. 

Third night would be dining out and then an evening at the Stratosphere lounge and maybe Fremont Street.

And our final night would be early dining at the Wynn Resort, then catch the show LaReve. 

Daytime would include some mandatory shopping, some touring and going to the pool. My only concession on dressing was that I was not going to wear a girl's bathing suit and wig to the pool. 

But as we got closer, I did buy two inexpensive two piece bathing suits just in case I got the courage. Maybe, I would wear the bottoms, but I could not see me in the top at a pool. 

Kelsey said, "You know, you could walk to the pool in a feminine top and shorts as a cover up and flip flops. Let's not say no quite yet."

As I modeled the bathing suits in a wig for her, she smiled a bit and said, "But, if you're going to wear that, you will need to do a little shaving girl. Even I have to." 

"I'm game," I replied.

++++++++++++++++++++++++

As we headed to the airport, I tried to go as girlie as I could with a nice camisole and panties underneath a pair of skinny jeans and a nice unisex top. Even my shoes were a bit girlish, but not outlandish. All my guy clothes were staying home.

"You're Jamie all this weekend," she reminded me as we stood in line for TSA.

We touched down in Vegas, grabbed the rental car and headed right to the hotel. The Palace Station was nice, easy to maneuver in and had a good set up for what we wanted. Our room had a great view of the strip, but the hotel was not on the strip. At least we were facing it.

Vegas looked so different by day, it was almost disappointing. So hot and dry. Well, it is in a desert.

Once in, we unpacked and set up a Jamie side of the closet and dresser and a Kelsey side. That alone was so much fun.

It was still afternoon so we took a drive over to a nail salon Tommy had recommended. The Asian girls there could not have been nicer. I showed them some pictures and they loved my Jamie look. 

We got the full mani-pedi, foot massage, etc. I went with a subtle OPI Bubble Bath color which was a light pink and Kelsey went with a dark red. I was so glad Kelsey made me pack sandals for afterwards...nails need to try.

So while waiting for the nails to dry we read all the brochures and magazines on Vegas and began refining the trip. This was so cool. We were really in Vegas!

With the strip still quiet, we did a drive up it and got a good lay of the land. These casinos were huge! Tommy was right. Walking in Vegas in heels would not be a good idea. Cars or taxis were the way to go. 

Before returning to the Palace Station we stopped in a cute restaurant and grabbed a quick salad. I felt special being in the restaurant with nail polish but no one seemed to even notice. Welcome to Las Vegas.

We decided that we would change and head out around 8:00 as the lights were coming up. I was still a bit nervous about being out and about in the casinos, so we decided to start right here at the Palace Station. 

I probably wore my most conservative outfit, a black skirt that fell just above my knee, heels and a silver and purple sequin top. 

It was fun zig zagging through all the machines and tables, and watching people gamble away their money. As I walked, I kept thinking of all the things I had practiced with regards to walking and just wanted to blend in.

After a little tour, we settled into some dollar slots and ordered a drink from a hostess. She made it a point of complimenting me on my outfit. My first Vegas compliment!

As we first wandered around the casino a little more, it was like watching magic. But then, after about an hour it was, "OK, let's go somewhere else." We have actually seen all of this casino, twice.

As we got to the car in the amazing dry heat and headed out, we drove by this really cool looking adult shop called the Lion's Den. Kelsey said, "I remember seeing an ad for this in the magazine...let's go in."

The Lion's Den was really nice and clean, and it was actually fun to just browse the adult toys. They were expensive but very nice.

Kelsey was looking at the Venus butterfly and said, "I've heard of these but never actually seen one." Then teasingly she said, "Can I get one to try?"

I kind of rolled my eyes.

She then walked over to the strap-ons, picked one off the wall, came up behind me with it, poked me in the butt with it and playfully asked, "Would this interest you?"

Even under the make-up I was getting red. After looking at a few of them, a cute, normal looking sales associate came over and asked if she could answer any questions.

"Uhhh, this would be our first time buying or uhhh, even trying one of these. Any recommendations?" Kelsey asked. We both looked so embarrassed.

"Sure, I'd be glad to help. First, you both look fantastic. Is this your first trip to Vegas?"

"Yes, and our first day here as well."

"Well my name is Maddie and Welcome to Las Vegas."

"There are several things to look for on your first purchase of a strap-on. First, I think a smooth surface is the most important...like this one. The ribbed ones are OK, but not right now."

"Then sizing. If it's your first, trust me there's no rush to buy a large one. You are buying this for your pleasure right now. And third, the strap to hold it on. That is really so important.

Maddie then showed Kelsey, "See this part here? You want that to sit right here on you so you can enjoy it as much as she does. This isn't pleasure just for her but you as well." 

I really liked her referring to me as a "she" and "her".

"Personally," reaching up and bringing another one down, "this is my favorite brand to wear. It fits me the best and my partners enjoy it as well. Seems pretty universal. But definitely go with the smaller size right now. Too many people buy the larger size and never actually get it inside which is the whole point."

Maddie then asked my wife, "Do you have any butterflies of your own? I saw you looking at them."

Kelsey was a bit more embarrassed this time and said, "No, but do you have some suggestions?

Maddie walked over and said, "I have these three. This is my favorite one most of the time, especially if I am alone. It works for me in minutes and then for a long time thereafter. It has nice control settings. May I ask, are you super responsive?"

Wow, this was an interesting exchange.

"'I'd say not super but I am stimulated fairly easily there when we're together."

"Well, this is my second favorite. I can wear this discretely even during the day and it works its magic even if I'm just sitting at a desk or waiting here for a customer. Some nights are really slow." she said with a smile. "You might like this one because it also has very nice controls and is quiet."

"And this other one has a few little extra pieces built in, and might be good for a later purchase." 

Kelsey and I spent about another 30 minutes browsing the store, and ended up purchasing a strap-on, a butterfly, three scented lotions and a porn video featuring crossdressers just for fun.

"If you get a chance, please come back and let me know how things went, that is if you feel comfortable enough sharing. Maybe you will see a few more things you like. We truly have one of the nicest collections on the strip."

We then decided to try another casino and drove over to the Rio. The magazine at the nail salon said they had a free evening show in the air celebrating Rio and thought it would be something fun to see. 

It wasn't bad but really was not all that exciting. We browsed the shops on the upper and lower levels, and Kelsey and I even tried on some slinky dresses. It was all fun and we could tease each other with the erotic clothes.

After our stroll, we decided to head back to the Palace Station. Now returning to our home base was easy. We played a few more slots, watched some hookers strut the floor and hang out near the elevators, and just enjoyed the awesome dresses some of the ladies were wearing before heading up to our room.

It was great getting the heels off, and everything else for that matter.

"Anything special you want me to wear for our first night?" I asked.

"Absolutely. That new black babydoll has first night written all over it."

Kelsey said, "I'm showering first," and jumped in the shower to freshen up. She came out with just a robe on, flowing openly as she walked by, her breasts bouncing and said "I'll change out here, your turn."

The shower felt so good. I was careful as not to wet my natural hair or make-up. As I was drying off I noticed that Kelsey left one container of lotion for me on the counter. Interesting, she didn't say anything.

After a quick shower, I brushed out my wig, re-applied my lipstick and slid on the new black panties. I loved getting new clothes and wearing them for the first time, and even as tired as I was, I got excited.

My nipples were rock hard with even just the panties on. I just stood there looking at myself in the floor to ceiling mirrors as I was caressing my breasts and squeezing my nipples.

"I still need a few minutes," I heard Kelsey say and I replied back, "Me too, no rush."

As I slid the new black babydoll on I realized I could go even heavier on my make-up so I spent a few minutes on that. I then picked up the lotion and opened it. I loved the strawberry scent.

It was still quiet from the other room so I slid my black panties down and applied some lotion on my middle finger. As I lifted my leg on the small stool in the bathroom, I slid my finger inside my butt hole. 

Was tonight going to be the night? This felt so comfortable. I closed my eyes as I continued to massage myself. This was feeling so good. I was not going to masturbate, but it felt so good to stroke my cock while slowly penetrating myself as well.

After a few minutes, I probed a little more but the angle wasn't the best. But still, it felt so nice.

Finally I heard, "Any time, hun." That was my call and I lightly washed up, tried to cool down with a cool face cloth and headed into the room.

The lights were low and Kelsey was standing at the window with her back to me wearing a new black, skin tight body suit. This was really tight, almost like spanx material

"Come, join me over here," she asked.

I slinked over beside her and cuddled up to her. Now, the bright lights from the strip could be seen from the other side of the highway from where we were. 

"I love it here," she said. "I didn't think I would, but it is so different than anything thing at home."

I just stood there and felt her hands moving under the front of the babydoll and then onto my breasts.

"Tonight, you are all mine," she whispered. She moved behind me and as I continued looking out the window, she caressed my body from my shoulders down to my legs. 

It felt so good that I was reaching up and squeezing my own nipples. This was so erotic. 

The huge lighted signs from the strip kept changing, displaying who was performing now and who was coming soon. It was like a bright, colored silent movie. I was hoping no one could see us standing in the window and at the same time was hoping every one could.

I could feel myself getting more excited and took Kelsey's hand and led her over to the bed. Laying on my back I spread my legs open and invited her on top of me. As she stood over me in her all black outfit, I just had these visions of her taking me tonight.

She reached down and pressed her hands against my breasts, and then stomach and then my pelvis. My cock had already sprung out of the panties but she didn't seem interested in it.

As she climbed on top of me, we kissed, lightly at first and then deeper as the time slipped away. I could feel her slowly beginning to grind her pelvis and thighs against mine. I loved her slow rhythm.

When I reached up for her breasts, the tightness and firmness of her outfit made any semblance of a woman on her disappear. I knew she was excited, but her nipples were not poking through the material. I reached my arms around her and wrapped my legs around hers, drawing her body in closer to mine.

After a long while, Kelsey literally slid down me and began teasing my cock with her fingers as she slid the black panties with the little black bow ties off me. I so wanted her to take me in her mouth. I had not been this excited before without cumming...but she did not.

She was going for a long wonderful night. As the reflections of the Vegas lights danced on our wall, she kept lightly caressing my cock, then playing with just my balls with her fingers. 

Several times she brought me to a climax with her fingers alone, but then skillfully backed away. And then she began rubbing underneath me as she knelt over me. 

As I kept my legs spread open, I could smell a sweet vanilla fragrance and felt a little pressure around my hole. I bent my knees up a bit more and could sense one of her fingers beginning to probe me. She went around and around, and then slid her finger in a little more. "Oh, that feels so good," I sighed.

After a while, I caught another scent of the vanilla as she added some more lotion to her fingers and began putting two fingers in me. "Tell me if this hurts babe. I just want to please you tonight," she whispered.

With the added lotion and her slow prodding, I could finally feel my muscles relaxing and was opening up more and more. "Oh, this is wonderful...don't stop" I soft replied.

With each few minutes, she went deeper and deeper, and I could feel myself opening up wider and wider as she added a third finger. I could feel her spreading her fingers inside me, at times causing a little pain and then pleasure again. I'm not sure I could take much more but I wanted her in me.

"Ohhh," I cried as she pushed her fingers in even deeper. I was breathing so deeply now that all I could think of was her being in me. I grabbed my knees and pulled myself up as far as I could and she slid in even deeper than before.

"Stay with me babe. You're a big girl. You can do this."

Kelsey rested for a while with her fingers in me. I then felt myself relaxing even more as she had to have had all four fingers inside me. I just could not tell anymore.

"That's my girl. You feel so warm inside. I love how you feel inside."

She stayed right there longer and longer, and it felt so good. Lightly her fingers were moving inside me, creating pleasure and pain with every push.

"Roll over hun," she whispered to me.

As I rolled over, she ever so slowly removed her fingers and got up. In the silhouette of the window I could see her putting on the strap-on. Her black outfit and ponytail, with the strap-on against the Vegas lights was an image that will always stay with me.

"Kneel on the bed right over here," she whispered as she walked back over. I could tell she was putting lubricant on the strap on cock and slowly began working it against me.

"Jamie, I have wanted to do you for so long." Kelsey began pressing the strap on against me and slowly I was able to accept it. 

I could immediately tell this was not her finger. I felt this amazing pressure building inside me, and then the cock slid into me a little more.

"Ohhhh, Kelsey, I can't...no...please stay right there... Ohhh, please, come in me just a little more."

I had this series of emotions running from stop to don't stop.

"I love my Jamie," she whispered. "Your ass feels so good around my cock."

The deeper she went, the more we were both enjoying it. I pushed back on her to allow her even deeper. 

"Oh fuck, this is sooo good," she said out loud as she began slowly rocking against me, driving her hips into me. I could tell she was having one of her long slow orgasms.

The more vocal she got, the harder I pushed back. She was holding onto my hips so tight that I thought she was going to give me bruises. Her body was quivering and finally she started slowing down.

By now my head was spinning. This felt so freaking good. Carefully and slowly, she withdrew strap-on from me and gave me this huge hug from the back and just held on to me.

I literally couldn't move. This had not only taken my breath away but also wiped me out emotionally as well. 

Kelsey was sweet enough to bring me in a warm cloth from the bathroom and help clean me up while I was still lying on the bed in a fetal position.

"If I had one, you're having one too," she whispered. 

She rolled me over onto my back and finally started sucking my cock. I was rock hard but could barely respond. I just laid there with my legs spread wide open as she kissed and sucked my cock from all sides and caressed my balls with her hands. She then closed my legs.

Her body suit had a slight slit in the crotch and as she slowly spread that covering apart she straddled me cowgirl style, and just ground the living crap out of me. She was rising and falling on me as she drove her fingers into her own pelvis. As she began having even another orgasm, I exploded in her.

I don't remember falling asleep that night but the hot desert sun came streaming in our window all too early in the morning from the open drapes of last night.

I staggered up and closed the drapes, and then headed into the bathroom. My make-up was a wreck and my body was even worse, but I was real satisfied. I cleaned up as well as I could and climbed back into bed. Kelsey, still in her black cat suit, never stirred.

It wasn't until about 8AM Vegas time that we woke up. She crawled on top me and said, "I love you." I loved hearing those words.

We both needed long showers and we really took our time getting ready.

"It's going to be a full Jamie day, remember," she said quietly.

"I know, and I can't wait."

Kelsey helped me with some daytime make-up and we prepared for our first Vegas buffet. I actually felt quite good about going down dressed, especially after last night. Kelsey was really treating me like Jamie and I was enjoying it.

I went with a jeans skirt that buttoned down the front, an ivory lacy top and my flats. Real simple and it fit in perfectly with the crowd here. My butt was a bit tender but I wore it like a badge of honor.




Caught For the Last Time Ch. 09



Even at 10AM, there aren't too many people up and awake in the morning in Vegas. Just some conference folk, a few adventuresome couples and families with kids. Too be honest, only a few people gave me a second look as we walked to the buffet. A couple of conference guys shook their heads and muttered something like faggot under their breath, but I was expecting a lot worse.

If I had done one thing right before coming to Vegas, it was practicing getting out. All my practicing walking and shopping outside really paid off. I felt real comfortable moving about.

Once at the buffet, sure, I got a few stares at the stations, but so did other people. I was at least wearing nicer clothes than them and was in much better shape.

One tall, moderately attractive woman actually came up to me while I was waiting at the omelet station and said, "You look wonderful."

"Thank you so much. That means a lot to me," I replied.

"When I saw you, I told my husband he should try this while we're here. He likes to wear my clothes at home but never dares to go out like you. Good for you girl." 

"Well I'm Jamie and my wife Kelsey is right over there."

"And I'm Casey and my husband Rick is over there at the carving station." 

As we waited, it turned out they Casey and Rick lived just two states away from us, and in Vegas that made them like neighbors.

As Kelsey and I were finishing up our relaxing buffet, they stopped by before they left.

"How long are you staying here?" she asked.

"We have three more nights," I replied. 

"I know we just met, but my husband and I were just talking. If your schedule allows it, could we join you one evening? I can't believe I am asking this, but Rick would really like to go out after seeing you...you are so comfortable walking around the buffet...and well, now he's kicking himself for not doing it."

Rick jumped in, "Seriously, Jamie, you look great. I toyed with the idea before coming here but decided against it. That was a huge mistake now that I'm here."

I kept trying to visualize him dressed and if I looked closely, I could see him all made up.

I looked at Kelsey who nodded and responded, "Let's see if something would work tomorrow night. We were going to have dinner that night and then go to the jazz lounge up on top of the Stratosphere. Maybe that could work." We exchanged room numbers and were all genuinely excited.

After they left, Kelsey turned to me and said, "Aren't you the brave little girl? I'm impressed."

"I hope it's OK, I'm enjoying this full-time Jamie stuff."

"I'm good if you're good. Just no messing around...you're all mine." 

We headed back to our room, freshened up a bit and we stayed with our game plan. We jumped in car and drove over to the Fashion Show Mall to do some shopping. It was huge and all underground. 

We visited a Soma at Carol's advice and met a sales associate, Amanda, who Carol referred us to. It was like old home week. 

I told Amanda, "My Soma bra was my first one and it is still one of my favorites." I told her about some of my Soma outfits and while there I tried on a few outfits as well, but nothing really fit my fancy for Vegas.

As we were telling Amanda about our Vegas plans she said, "One of the places you have to go to is the Glamour Boutique over on Sahara. I think it's called "Just You" now, but we still call it the Glamour Boutique. They do makeovers and have a wonderful collection of clothes to rent for the night."

"A lot of my male customers come here for their bras, panties and nighties when they arrive here on business, and then go see Amy at the Glamour Boutique for a makeover and a nighttime excursions to the casinos. She has a huge following."

We thanked her so much and continued our shopping. We casually shopped at about 10 different shops, including Chico's and even had little dessert and coffee at one of the tables set out in the mall. 

Kelsey said to me as we were sitting there, "You are so comfortable here, aren't you."

"Except for the giggles from a few young girls, which I'm beginning to actually enjoy, yes."

After heading back to the car, we checked the map and found we were only a mile from the Glamour Boutique and decided to head over. We easily found the place and it was much bigger than I ever imagined.

Amy greeted us and complimented me on my look. "Not too many of my girls go out during the day, we tend to be creatures of the night. You look wonderful."

She gave us a tour of her boutique and I was in love with all the photos of makeovers she had on the wall.

"Where are you going tonight?" she asked. 

"We're seeing Divas Las Vegas."

"That's my favorite show. I've seen it many times and the cast are such great people. Do you have time for a makeover before the show? I'd love to do yours, and your wife's as well. We have a couples' special."

The more I looked at the photos the more I liked the idea.

"Seriously," she added, "if you're going to have a makeover, this is the show you want it for."

"I'm going to be busy tonight but I can do you at 7:00." 

"Perfect"

It was still only 3:00 in the afternoon and it really seemed like another day already. We drove back to the hotel which was all of 10 minutes away and decided to just relax in the room before we were to head out for the night.

I went into the bathroom to freshen up and Kelsey shouted out, "I don't want to scare you but I'm going to lay on the bed naked and try out this butterfly thing for a bit."

I had forgotten all about it. If she was going to lie about naked, I was at least going to put on a comfortable nightie. When I came out she was lying spread eagle on the bed with that little gel device strapped to her with the control unit in her hand. 

She quietly said, "This is real relaxing. Come lay down beside me." She had the radio on softly and was listening to a classical station. It was real soothing. 

"You look pretty in that nightie babe," she whispered and then closed her eyes. After about ten minutes she whispered, "Turn around." 

It took me a second to figure out her request and then I got it. 

I moved so I was still on my back lying beside her but with my feet near her head and hers near mine.

She now easily reached over and lightly held my cock through the panties. 

I could hear a slight hum of the butterfly and noticed her breathing slowly getting deeper. "This is so relaxing, and stimulating," she sighed.

Lying on the bed was relaxing for me as well and I could play with my nipples as she fondled my cock. As time passed, I almost nodded off. Then I heard to hum change a bit and she took a deeper breath and squeezed my cock all at the same time.

"Can I do anything?" I quietly asked.

"Just stay here beside me babe. I want you here." 

She then removed her hand from my cock for a minute and I smelled the vanilla scent from the other night. When she reached over the next time and slid her hand inside my panties, I could feel that her hand was warm and moist with the lotion. It easily slid up and down in a slow motion on my cock that mimicked her breathing.

After another 10 minutes there was another change in sound, I felt her legs quiver and she said, "Oh fuck!" 

She was now stroking my cock harder. As she recovered, her breathing settled back in down and she lightly fondled my balls as I was now lying there with my legs open.

A little later, another change in speed and she began driving her pelvis up off the bed and grabbed her own nipples with her free hand. "Oh...oh, shit!"

Her excitement got me excited and I began playing with my nipples more as she was now nearly ripping my cock off in her hand. I was doing all I could not to ruin her moment and did all I could not to cum.

She has had orgasms before but never like this. Finally, she shut the butterfly off and her legs dropped down on the bed. I was still hard as a rock and she loosened her grip on me, almost collapsing.

"Thank you..." She said quietly.

"But I didn't do anything."

"Yes you did. By being there beside me, I was with you the whole time."

She then rolled over, reached over and started caressing my cock again. "Now it's my girl's time."

Kelsey slowly and methodically touched me in all the right places. As I got harder and bigger she said, "Cum for me Jamie. I want to watch you have one too."

With each stroke, my cock got hotter and harder. She kept going at this real slow and sensual pace. 

"I love getting you this excited." She whispered. 

"Come on Jamie, let's see you cum for me." I finally I erupted all over her hands and my nightie. With both hands she kept stroking me until I totally stopped.

"Girl, you're a mess. I didn't realize you were such a squirter." She laid back down on her back and relaxed.

Fortunately she had set the alarm for 5:30 PM because it woke us both up. We were dazed. After a quick shower a well needed shower, we went out with minimal make-up on and with our change of clothes for tonight in a little travel bag.

Just before 7:00 we arrived at the Glamour Boutique and Amy introduced us to three of her clients who were in for their makeovers a bit earlier. All three were at conferences and did not know each other until tonight. Two of them had never been out dressed before and the other had been to Vegas several times. 

They were all different sizes but were all so excited about being dressed. "Where are you going tonight?" I asked.

"First up to Pete's for a drink or two, have a little bit to eat, and then out to a casino." 

"Sounds like such fun."

"And you?"

"After our makeover we are going to see Diva Las Vegas up at the LINQ. It'll be our first Vegas show."

Amy brought us into the make-up room and explained everything she was doing as she applied my make-up first. She was so good and matched the style with my black flounce skirt and silver glitter top.

"And Kelsey, what look are you going for tonight?"

"Do you have some suggestions?"

Looking at her from a couple of different angles she said, "I love your features. I'm seeing a little UmaThurman Pulp Fiction look here. Would you like to try that?"

"I'd love it. Let's do it," Kelsey replied.

As Amy applied the make-up, I was not quite seeing the look, but without a doubt Amy did. Amy then walked into the other room and brought back in that classic black wig, brushed it out and adjusted it to Kelsey's head.

"Well?" she asked as she turned the chair to the mirror.

There was Uma. It was perfect and Kelsey loved it. When she got up she even did that little eye dance thing from the movie.

We settled up and even bought the black wig and some of Amy's make-up products, especially the foundation.

We then asked if Amy would have time tomorrow for a couple we met today, Rick and Casey. We told her a little about them and she said, "Absolutely. And let me recommend that you eat at the Artisan. It's a great restaurant that you will love, and will be a great place for her on her first trip. 

We called Rick and Casey and left them a message on their room voicemail.

Amy then said, "Your show is at 9:30 and its right down the street, maybe 10 minutes. Take this note and give it to the hostess at the show when you check in and she will take you backstage to meet some of the cast."

"Eddie Edwards is a good friend of mine and he's the one that does Barbra Streisand. You can get photos together and meet the other "gals" behind the magic." 

"And if you want a quick bite to eat, stop at Firefly's. It's on the way. They have amazing tapas and my girls love going there!"

Firefly's had only a 10 minute wait and we were seated in no time. Sangria and tapas. It was perfect and we could now add another experience to our Vegas trip. 

And Divas Las Vegas was amazing. Frank Marino was the perfect MC and the different acts were so well done. It was the fastest 75 minutes of my life as it went from song to song with Frank adding his comedy and gorgeous fashion changes between acts. This show never stops.

At the end we were ushered backstage and felt like celebrities as the rest of the audience departed. The cast really loved Kelsey's Uma look and jokingly asked if she wanted to appear tomorrow night with them.

Backstage Eddie really did not look like Barbra up close, but he was spot on up on the stage. He told me, "Jamie, it's all about the illusion. Remember, act like a girl and not a guy in a dress pretending to be a girl. Be Jamie."

We got pictures with Tina Turner, Diana Ross and Barbra. It was so special.

It was still early in the night as far as Vegas goes and right up the street was the Bellagio, so we left the car and took a cab over. Wow, what a difference in clientele. 

The beautiful people were just coming out of the Bellagio and the outfits the girls had on were beyond amazing. Their heels could not have been higher, nor could their dresses. They all looked great under the casino lights. 

We walked through the lobby and saw the famous glass balloons in the ceiling and heard the pianist play the closing song from Ocean's Eleven as we had a drink at the lounge area. We wandered through the shops and tried on some shoes at this killer shoe place. We are definitely staying here next time. 

We caught the last show of The Fountains at Bellagio. Magnificent doesn't do it justice. We strolled the strip and walked back to the LINQ, picked up the car and called it a night. I was dragging.

It was now well past midnight but it felt like 3AM. Getting the make-up off was a chore but even after 6 hours it looked fresh. Amy did amazing work.

When I finally changed into the pink nightie, Kelsey was sitting on the bed with another bottle of lotion by her side and the video in the player. "We have to watch this."

The plot line was about a guy needing a job and decides to dress up as a girl to get one as a secretary. It went downhill from there. But it was interesting watching how hung some of these actors were and just how much cock some of these "girls" could take both orally and anally. 

Kelsey turned to me joking, I think, and said "My little girl will be able to do that someday."

The more we watched, the bad acting stopped bothering us and the sex part both with and without the toys actually got pretty good. 

"I think we need another trip to the Lion's Den," she said coyly.

As the action got more heated, she placed some lotion on her fingers and slid my panties down. I raised my knees up and she slid her middle finger into me. At first I winced from the other night, and then it felt better. Slowly she kept massaging me and I could feel my muscles relax.

We must have stayed watching the video for nearly a half hour and by then I was ready for almost anything. I was hard and she was teasing me and biting my nipples.

This time, Kelsey put the strap-on around her naked body. I could see her positioning the base in different places until it would press on her in just the right place. "Found it," she said with a smile and a deep breath.

I laid on my back in the bed and wanted her in me missionary style. I knew this was going to be different and it hurt a little more she went deeper into me earlier.

"Let me know how deep I can go babe," she whispered.

I had no idea how much of the cock was in me but I wanted more. I knew she was struggling to stay on top of me without going in me too deep. Slowly she dropped her hips into me and she went deeper and deeper, and then stopped.

I could barely breathe but I knew I could take this. "Are you good babe?" she asked quietly.

All I could give was a quick nod. My breathing steadied and I could feel her pressure in me deep.

Kelsey sensed I was relaxing more and began shifting her weight forward and back, just a little. I could sense every movement and at times it hurt, but felt so good.

I knew from her breathing that she was beginning those early signs of an orgasm. I pulled my knees back even more and that allowed a little more space inside me as she began a slow rhythmic motion. 

"Don't stop," I whispered as she continued her pace. I found the place where I could enjoy her the most and stayed right there. "Nice and slow," I whispered this time.

I could feel her pace beginning to pick up and her breathing getting deeper. "I want to so bad," I murmured. Her pace was now even faster.

"Oh...oh crap...this is so good," she yelled. Within minutes I could feel her leg and stomach muscles quiver and then she collapsed on me.

"You OK babe?" she whispered. 

I could only nod again. Slowly she removed the strap on from me and began caressing my cock as I laid on my back.

"Is my girl ready for a double today?" she asked quietly. I nodded again.

Kelsey took my hand as I mounted her cowgirl style. I was exhausted but she began rubbing my cock all over and between her breasts. 

She grabbed some more lotion and spread it over her breast and nipples and kept rubbing me against her. "Cum for me Jamie," she whispered. "Cum all over me."

It didn't take long until I unleashed all over her breasts. I was almost too tired to do anything but lie on the bed. I never woke up until morning.

+++++++++++++++++++++

That second morning we slept in later and I was tender. No, I actually hurt in places, but it was OK. 

Slowly the haze of last night cleared, and I shower and slowly got dressed. I was now looking forward to going to the breakfast buffet. I put on a cute flowered skirt with sandals and a pullover top. This was now so easy. 

The service staff greeted us with a friendly, "Good to see you two again. Love your skirt." There was a lot of interaction with other guests who recognized me from yesterday. This was too much fun. 

"Looks like my girl has found some friends." I kept thinking to myself, they only know me as Jamie. How cool is this?

We wanted to get an early jump on the pool today so after breakfast we made a quick change, a clean-up of the light make-up and headed down. I wore a pair of neutral shorts and a cute baby tee and sandals. This was as compromised as I was going to go without my wig. 

At the pool there was more flesh than I had seen in a long time. And that was not on the beautiful people. They don't stay at this casino. Some people at this casino should not wear string bikinis, but they did anyway.

Looking around, wearing my female purple bathing suit bottoms was no big deal. Some guys were wearing thong type bathing suits and they really should not have been. Now I wish I had string ties on mine.

Because of the hot sun we barely stayed two hours at the pool, but the pool felt real soothing on my butt. We had a few drinks as well and then headed back to the room. 

For fun I put the bathing suit top on while I did my make-up. It really fit well and Kelsey teased me about it and said I should really think about wearing it and the wig tomorrow, but there was just no way.

When we got back to the room there was a message from Rick and Casey saying they booked a makeover at the Glamour Boutique and maybe we could meet them there tonight at 7:30. They were so excited.

Today we had decided to go to the Wax Museum and then shop the Canal Shoppes at the Venetian. We dressed up a little more since we would be with the beautiful people. I wore a flowing skirt with low heels and a Sally top. I even perched my sunglasses on top of my hair as we entered the casino to walk to the Canal Shoppes. I felt so cosmopolitan! 

We took pictures at lots of locations and asked other travelers to take pictures of us. We loved the time out. 

I must have tried on 5 or 6 different dresses at the various Canal Shoppes. They were way out of our price range but so much fun to try styles you only see in catalogs. I was never once denied access to the changing rooms. 

After we had seen enough, it was time to return to the hotel and rest up for tonight. On the way back to the hotel Kelsey suggested we stop at the Lion's Den again. Maddie was working and immediately recognized us.




Caught For the Last Time Ch. 09



"Well?"

"We loved them. Do you have any more suggestions?"

"A couple," she smiled.

"Sometimes when I'm alone but want a little companionship at home, I use this."

She picked up what looked like a cock on a stand. "All you do is place it on the surface that's a good height for you and, well, sit on it."

Looking at me she said, "I like this because you can use it at your own pace and even use it before you get to active. It's pretty simple."

"And how was the sizing on the strap on?"

I replied, "Since it's all new, it seemed a little tight at first, but I worked up to it slowly."

"She sure did," replied Kelsey with a smile.

"That's so good to hear. Then this would be a good size as a starter for you."

And turning to Kelsey, she walked over to another area and picked up something that looked like an L shaped dildo. Maddie said, "This dildo is not quite a strap on but it goes inside of you right here. It takes some time to get used to, but you can both enjoy it."

Kelsey picked it up, looked at it a few different ways and said, "Oh I get it." She picked up a few and said, "I think this one would be good for me."

"And did you watch the video?"

"Parts of it. What great suspense and drama!" I said.

Maddie looked up and I laughed. "It was pretty bad, but some parts were OK."

"That's about the best you'll get I'm afraid."

We purchased the two items, thanked her and pretty much said our goodbyes. She was awesome and we gave her a $20 tip for being so nice.

We headed back to the hotel to rest up before dinner.

I was still a bit tender from last night but was really interested in trying the new cock out.

"Slow down Jamie, there's no rush. You don't need to do this now."

"I know, but we've got a couple of hours and I just wanted to see."

"You can see at home, let's just cuddle for a while. Seriously, we don't even have this much sex at home. And we got a long night ahead of us."

She then sat up on the bed with her back against the headboard and I placed my head in her lap as I had done with her so many times before. It was peaceful and we just rested for the next hour or so. It was good just to relax. I swear I nodded off for a while.

At 6:00 we started getting ready and I dressed up in the gold draped top and black skirt. I loved this outfit! Kelsey went real heavy on my make-up knowing that Amy was going to do a great job on Rick.

Before heading over to meet them at the Glamour Boutique we drove over to the Artisan just to scope it out. It was much classier than I expected with an inside water fountain and wonder décor. It was definitely an alternative lifestyle crowd. This would be perfect for Rick and Casey. We confirmed our 8:00 reservations.

Pulling into the Glamour Boutique for the third time in two days was like old home week.

"We're here to meet up with Rick and Casey." I said as we walked in. 

"There's no Rick here," Amy said, "but I found a Rachel".

There she was...a little nervous, but beautiful. "Wow, Rachel, you look beautiful! And Casey, you look great as a redhead!"

Rachel did present real well, almost too good as far as I was concerned. She was a dirty blonde, with hair just falling over her eyes. "Amy you're brilliant. Awesome job."

"Now, everyone, let's get a group photo or two," she said. 

After accolades all around we headed out to dinner in our rental car. Four hot ladies going out to dinner in Vegas. This was going to be fun.

I took the lead at the Artisan as if I owned the place and Rachel did real well. She so reminded of me of my first time out with Tammi. That now seemed so long ago. 

We had so much fun waiting for the table at the bar, taking pictures, and meeting other people. Everyone had a kind word. It was awesome.

The Artisan is a real restaurant in a small hotel, and the food and service was perfect. Rachel and I shared stories of crossdressing in our moms', sisters' and aunts' clothing. We had so much in common, and so did Kelsey and Casey living with us. 

They even shared a few intimate tales, but kept it very clean. They were good friends right away.

"Is anyone up for the Stratosphere?" We were just blocks away and decided to grab drinks in the lounge high above the strip. There was a jazz band playing and we took turns buying rounds of drinks.

In a surprise move, two older gentlemen came over asked our wives' permission if they could dance with us. Kelsey and Casey granted them permission but said we had to behave. 

It was a thrill and the gents knew it. It is a tad awkward dancing backwards, but fun. How many people have danced in the Stratosphere lounge while dressed?

We could only sit there and admire the sights from the Stratosphere for so long before we decided to head down to Fremont Street, the old Vegas. We were definitely overdressed and knew that we were being captured on cell phone videos and would probably be on YouTube within the hour, but who cared.

I worked my best sexy walk and even posed for a few pictures with Rachel for some tourists. 

By midnight, we ended up at the Golden Nugget for a quick bite and a drink. Our feet had had it and we all decided to call it a night. They were leaving in the morning so we exchanged email addresses and promised to stay in touch. Rachel had the time of her life.

When we arrived back at the Palace Station, it took everything I had to look spry as we walked in. We headed up to the room, watched cable for a bit and literally feel asleep in our clothes. We both needed it.

When the sun woke us up the next morning, we laughed at getting so old we fell asleep in Vegas, but we were beat. Waking up fresh though was good for our last full day.

We decided to try breakfast at another casino and drove up to the Paris Casino. I loved the theme of this place and wanted to check out the shops. 

The buffet was great but the clientele was a little snobby. Seriously, get a grip people. I did get a few more stares but at this point, I did not care. The wait staff was great and the food wonderful.

Afterwards we shopped all the shops along the LeBoulevard. It was such fun. Kelsey bought herself a cute French bra and panties set for a mere $100. They were classic. I loved the shops and as far as I was concerned, we could come back here anytime.

After the leaving Paris, we drove around a bit more and by 1:00 we were back at the Palace Station. It was pool time. I think I stayed in the pool two hours. We ordered drinks in there as well and just enjoyed our time. 

++++++++++++++++++++++++++++

Our last night in Las Vegas was amazing. I wore the black cocktail dress with matching black bra and panties. Kelsey wore her new French bra and panties set over a wonderful black top and long flowing pants and heels. We looked great together.

We had an early dinner at the Wynn and were treated with the utmost respect. I loved the attention I was receiving. At the Wynn they took pictures of us at our dining table and then again in our seats at LaReve. What a spellbinding performance!

After the show we wandered the shops and casino. What another wonderful place to stay. We were already planning our next trip.

Our last night together in Vegas was our best. She was my consummate lover and I only remember waking in the morning. Our time together in bed was a wonderful blur. 

The next day as we cleared security and waited for the plane, there was a sadness of sorts. Four days as Jamie was coming to an end. 

We got to relax in the plane on the way back, and we both nodded off at times.

In the weeks and months that followed we had lots of great talks. More open than ever before. 

We agreed on a number of things. I could be Jamie as much as I wanted at home, and she could enjoy being my lover, but we just won't overdo it. She didn't want to lose her man and I had no problem with that at all.

We were going to make going out together a more regular part of our life and make an effort find other people, like ourselves that we could enjoy their company, like Sally and Tommy, and Rick and Casey. Life was simply too short. 

And most of all, we agreed that we loved each other deeply and we were only going to be with just each other.