3 comments/ 31675 views/ 32 favorites Boyshorts in the Dressing Room By: mikee_43 I woke up this morning horny. Probably most guys do that, so I am not necessarily any different than any other guy in that area. I decided to put on a pair of my black lacy boyshorts because when I am horny, they take me to the next level. I love how they feel on my cock. I think it is the fact that they are so lightweight, they fit fairly loose, and the lacy part rubs my cock. Anyway, I had them on this particular morning, but ran out of time to play. I had to run into town to pick up a few things. I never wear the boyshorts under my clothes because (this may sound goofy) I don't want to be in a car wreck and have them on at a hospital. (goes back to Mom saying to always wear clean underwear in case you are in a car wreck - laughing at the thought) Anyway, I decided I was going to play when I got back home from my errands around town, and since I was still horny I took a chance and left them on under my jeans. I finished getting ready and headed into town. I stopped by the hardware store to pick up a few things I needed for a project I was going to do. Then I got in the mood to run by a department store to look at jeans, and just see how busy the women's section of the store was in case I might want another pair of boyshorts. I did not want to shop for boyshorts with a bunch of women in that section. I was hoping there would be no one there except for a cashier. I got into the store, and the women's section is right next to the men's area. So, as I went towards the men's department I looked over at the women's area and saw there was no one in that area, just like I was hoping. So, I redirected my steps and headed into the women's area. I found the boyshorts right away. I picked out a pair of royal blue lacy ones in an 1 x size, which I knew would fit me fine. I am average size, (5'10, 187) but have learned that I need a 1 x in women's boyshorts to fit me. Then, I headed to the counter where a woman in her later 50's or early 60's, was working. She said "Hi, is this all you need?" I said "Yep, that is all for today?" "Buying some cute boyshorts for the girlfriend or wife?" She asked. I could have easily said "Yep", but I decided to just see what this woman might say if I responded different. So, I said "Well, this may sound weird to you, but they are actually for me." She was startled a bit with my answer, and said "Oh really?" I said "Yes. I am not gay, or a cross dresser, or weird, so don't get me wrong. I just think it is a bummer that women get to wear all the silky, sexy underwear that feel good against their skin, and guys don't. I have one pair of these in lacy black and I love how they feel on me." I figured I sent her over the edge with that one, but, I just wanted to see how she would respond. It was kind of fun to test the waters, so to speak, with a woman her age. (Not that I am a lot younger than her. I am 43) Her response surprised me. I really figured she would have the typical, tactful cashier response, something like "Well, cool", and then drop the subject. Instead, she said "Now that is an image that sounds interesting. I haven't seen a guy in a pair of those before. I have to admit it might be kind of sexy." "Well, I don't wear them to be sexy, I just love how they feel on me," I said. "Besides, I would be worried the average woman would think I was weird if they knew I wore them. I would never tell the average woman because of that." "Can I ask you what you mean with 'you love how they feel on you?' " She said this more quietly, even though no one else was in that department at the time. "You want me to be blunt?" I said with a smile. "Hmmm. Sure" she answered back. I was hesitant, and still testing the waters, so I said "Uh, well, they feel good on my, uh, you know." "Oh really? And, that is why you like to wear them?" she asked. "Yep. They hold things kind of like a hand would", then I laughed. "Interesting. I can get a visual on that too" she said. I smiled, not knowing what to say. She was not the kind of woman that would strike me as adventurous in the sex department, so to speak. Maybe I thought that solely based on her age. She was dressed nicely, looked to be at least within 15 lbs of in shape. She was dressed up, like a professional woman would look. She didn't look like a prude, so don't get me wrong. And, she didn't look like someone that might call security on me. I felt I could easily say a few things to her about the boyshorts and get away with it, or I would not have dared saying anything at all. She finally broke the ice, and said "So you wear them under your jeans?" I said "Actually I don't. It is one of those things like Mothers always say 'Wear clean underwear in case you are ever in an accident and have to go to the hospital'. Well, for me I guess I don't want to be caught at the hospital wearing boyshorts. So, I just wear them around the house." "Hmmmm, this is interesting to me" she said. I had already paid for everything by now, and the boyshorts were in the bag with the receipt. We were just standing there talking. I could tell she wanted to continue the conversation, but it was also awkward, too. Then, I guess she just took a chance and suddenly said "Well, if you ever want to model them for someone, let me know. I would love to see you in them." I was stunned. Then, I said "I would be happy to model them for you anytime you want. I have never let a woman see me in them, so it might be kind of fun." She was getting gutsier and gutsier, and she said "Well, you could show them to me now." I thought for a second, and then said "Sure, like in the dressing room?" She said "Yes. No one is in here, so you can go in and try them on. Then, I will come by and you can open the door and show me." I was getting very intrigued with this older woman. I guess I didn't expect the conversation to go like it did. I figured I would make a couple of teasing comments just to see her response, then I would leave. I was actually getting very turned on by her comments. Plus, I am the kind of guy that loves to be asked to do something sexual for someone. So, this whole thing was definitely turning me on. "Okay, I might actually enjoy doing that for you," as I smiled back at her. We headed toward the dressing room so she could unlock one of the rooms. As she was doing so, she turned to me and boldly said "Wear them with nothing else on. No shirt, nothing but the boyshorts." My cock jumped inside my jeans. This was my kind of woman - ornery, adventurous, and telling me what to do. My mind started racing to wondering what she would be like in everyday life. Would she be like this in a relationship? I dated a girl my age a long time ago that was always coming up with new sexy things to do. So, I found myself wondering if this older woman was like that, too. I said "I love your comments. You are fun. Whatever you want, I will do for you." I told her that in case other things entered her mind. This way she had the freedom to just say them, knowing she was safe with our little game. I closed the door and stripped completely, then put on the royal blue, lacy boyshorts. I never told her that I had black boyshorts on when I came to the store. Anyway, the royal blue ones fit me perfectly. My cock was 3/4 hard, and I was already leaking precum. I knew that my hard cock was going to be very evident through the lace, but I thought that she might actually like that. So, I wasn't worried at all. I then opened the door slightly in case anyone else was around and said "You ready?" She was just outside the dressing room and came in immediately. She said "It's still safe. No one is here right now," as she slowly pushed open the door the rest of the way. Her expression on her face was priceless. She paused and then said "Oh my gosh, you are hot. I love those on you. You have a great looking body. Mmmm. If you were at my house I would tell you to wear nothing but those for me all day long." My cock was growing even harder from the attention. I then said "Well, you give me the address and I might just do that for you in exchange for a great lunch." "How about tomorrow? I am off all day," she said. I was thinking "Gosh I love this woman. I love the way she thinks." I said "You got it. Write your address down and I will be there." She said "Wear them under your jeans." Then she paused and said "I will reward you." Gosh what a little tease she was. She then said "One more thing. Hang on." Then she quickly looked around the corner to see if the place was still empty. After doing so, she said "I think you like being asked to do stuff. Slide the boyshorts down to your thighs. I want to see it all." I did not even hesitate. I slid my thumbs under both sides, and slowly pushed them past my cock, then down to my thighs. I haven't said it yet, but another thing I love along with being told what to do, is the feeling of being exposed for someone. She wanted my boyshorts down to my thighs. To me, this is being exposed to her. In my mind it is sexier to be partially undressed at someone's request, than it is to be totally naked. So my cock was fully hard from me standing there exposed to her like this. She looked back around the corner again, then quickly came back. She walked inside the dressing room with me, closed the door, locked it, dropped to her knees and started sucking me off. Her mouth felt hot and wonderful. She massaged my balls with her one hand, while using the other hand to stroke my cock in the area that was not in her mouth. She did this for about 30 seconds, then looked up at me and said "My guess is you will not last long. I think you have enjoyed our little teasing game. You can cum in my mouth whenver you are ready, so we do not have a mess, okay?" I said "This is wonderful. I love how your mouth feels on me, and yes, that sounds great." She sucked me so sensually that it was like my cock was a treasure to her, and she wanted me to enjoy every second of what she was doing to me. And, she was right, I did not last long until I exploded in her mouth. I probably made it about 3 minutes. The pleasure was unbelievable. Even though the blow job was short, all the tease beforehand is why I could never last. I had no idea that a few comments to a cashier could turn into something like this. She then got up, wiped her mouth, and said "You will have to understand why I have to leave quickly. I don't want to get caught. Stop by the counter on your way out and I will give you my address. Be there around 10am in the morning?" I said "You bet I will." She said "Make sure you are wearing the royal blue boyshorts under your jeans. And, bring any other pairs that you have. I will make tomorrow worth your while. I am fun, a bit of a tease, a great cook, and love to reward guys who do things for me. Who knows what all I might come up with. See you then, okay?" We exchanged phone numbers, just in case some unexpected thing came up. I then headed home, thinking about the sexy talk we had and all that happened, and wondering what tomorrow might be like. To be continued... Boyshorts in the Dressing Room Ch. 02 I could not wait for this day to arrive. My little adventure with the older woman at the Department store was hot, to say the least. The day I met her, she invited me to her house the next day, and gave me her address. We planned it for 10 am and exchanged phone numbers. She instructed me to wear my newly purchased royal blue lace boyshorts under my jeans, and to bring other sexy undies. Sounds like she wanted "a show," so to speak. So, this morning when I woke up, I was definitely looking forward to this day. I needed to leave around 9:30 am, or so, to get there by 10 am by my calculations. Around 9 am my phone rang. It was her. I immediately thought to myself "Oh, no. I hope she is not going to cancel." I answered the phone and she said "Hi, this is Claire from the Department store." "Hi, how are you?" I answered, waiting to hear what she might say. Then she surprised me with "I learned yesterday that you seem like you enjoy being told what to do. Was I right?" I said "Yea, I do enjoy that, as long as it is not mean, or degrading." "I thought so" was her reply. Then she continued with "Here is what I want you to do. I figure it is, what, about a 20 minute drive for you to get here?" "Yes, 20-25 is my guess," I said. "Okay. I live in a neighborhood, but I am somewhat secluded, too. I do not have neighbors, except for down the street from me. So, you are going to strip down for me to wearing nothing but your royal blue lacy boyshorts. You will drive from your house to my house like that. You can bring your regular clothes with you in the car, but you are to wear nothing but the boyshorts in the car. When you pull up to my house, just leave your clothes in the car, and come up to the house in just the boyshorts. This is how you will be dressed today. Oh, and don't forget to bring all of your feminine sexy undies with you. And, uh, one more thing. I hope a cop doesn't stop you on the way." Then she laughed. I was getting tingles in my groin area as she told me all of this. Not sure if everyone gets those or not, but I do when I am starting to get turned on. What she just said to me was a huge turn on to me. I said "Okay, if that will turn you on, consider it done. By the way, I love how you think. See you in about 25 minutes." Unlike Claire, I do have neighbors where I live, so I waited until I got in the car to strip down. I got an almost instant hard on as I stripped down in the car. I looked down and could easily see my hard cock inside the lace. I have to admit, it was rather sexy looking, at least in my opinion. I brought with me 3 other pair of lacy boyshorts – one red, one black, and one white. Plus, I had 3 pairs of silky thong undies – one red pair, one royal blue, and one black. Once I was stripped down to the boyshorts and nothing else, I pulled out of the driveway to head toward her house. It was a little weird trying to drive barefooted. I hadn't done that before, but all in all, I got used to it, and did alright. I stayed hard most of the way to Claire's house. In fact, I was even leaking precum. I kept hoping that Claire would come up with more sexy things for me to do, because I love all she had thought of , so far. The trip seemed to go by quickly because of the excitement I had about this whole ordeal. And, luckily I never got pulled over by a cop. I pulled into her driveway, left everything in the car including my car keys (there was no place to put them), and walked up to the door. I was still about halfway hard when I knocked on her door. She answered fairly quick. She opened the door up, and just stood there looking at me like she was totally enjoying the view. She was smiling. Then she finally said "Well, looks like someone, and their big little friend, enjoyed the trip. Hope it wasn't too HARD on you." Then she laughed. "Come on in. I don't want the other neighbor women down the street to see the little prize I have today." Once inside, she closed the door, stepped close to me and gave me the most sensual kiss I think I have ever had. She had her arms around me and both her hands were planted firmly on my ass as she pulled me towards her. The kiss must have lasted a full minute. By the end of it, I was as hard as a rock. She reached down, and pulled down my boyshorts just enough to release my cock,. Then she grabbed a hold of it, and pulled me towards the bedroom as she said "I will give you a tour of the house real quick." So, she guided me around, room by room, by pulling my cock. My cock was throbbing. "Gosh, I love this woman," is what I was thinking. After the tour, she said to me "I want to be in control today, okay? Don't get me wrong, I am not a controlling person, but it turns me on a lot to control sex with someone who will let me. To be honest I have wanted to do this all my life, I just couldn't find a guy that I thought would let me until I met you yesterday. I love taking the lead sexually, as much as I think you like to be led. So, let me do it, okay?" At least she was kind about it. That is important to me. My answer was "Whatever you want, hun. You are in control of the sex." She said "Good." Then she got on her knees and sucked my cock for a good 3-4 minutes. Then she suddenly stopped, and stood back up. "That is enough for now. Remember what I told you yesterday?" "Which part?" I asked. "The part about I reward my guys," she said. "Yes, I do remember that." "Well, you did what I told you to do on the way here, so I guided you around the house with your hard cock, and now I sucked you for several minutes. So, as much as you love to be told things sexually, the bonus will be there will always be an additional reward for you," she said with a big smile. My heart was pounding in my chest. Again, my thoughts were "Gosh I love this woman." She put my cock back inside the boyshorts, and we walked toward the bedroom. Once inside she unbuttoned her top. She had no bra on. I was shocked that a woman her age (which I did not know what her age was yet) had that nice of tits. They were gorgeous. They sagged some, probably were 38 C or D, not sure. All I know is I loved seeing them. But, I am one of those guys that kind of likes tits that sag some. Her other clothes that she was wearing was a skirt, stockings, and high heels. She looked at me and said "You like my tits?" I felt like a little boy when I stumbled with my words and answered "Gosh yes, Claire. Your tits are gorgeous. They are a huge turn on for me." "Good boy. So, now I will let you see them all day long. What I have on will be my outfit for the first part of the day. Later on , I will take off the skirt," she said. "Sounds good to me. Can't wait to see what is under the skirt." I said. We then headed toward the kitchen, and as usual, she guided me by reaching down into my boyshorts, pulling out my cock, and holding onto it as she guided me. Once we reached the kitchen, she tucked my cock back inside my boyshorts, and then we sat down at the kitchen table to start talking. I was glad we did this because I was too turned on and could have cum in less than 5 minutes. This gave me the chance to calm down some. Sex to me is a mind thing, in a lot of ways. What I mean is, each of us have things that turn us on. A person doesn't even have to touch us yet, and they can still have us ready for sex. I have met so many people who do not understand that. I have met many women who do not understand that. In fact, I would be willing to say most women I have met, and maybe even most guys, do not have a clue that sex is a mind thing first. Claire was doing all the right things that was playing into my mind, and turning me on. It was all the things that make me unique in what I enjoy sexually. She figured me out fairly quick, and was using what turns me on. I was so turned on that I was almost shaking. And I know I was dripping precum everywhere. So, when we sat down in the kitchen to talk, I was very glad. I needed to calm down. Claire was a joy to talk to. We sat and talked about life, and what we enjoyed, hobbies, and everything except sex. This conversation continued for a long time, maybe 1 ½ hrs? She would get up to make coffee, and we kept talking as she made it, and as she poured it, and as we continued to sit together. I found out all kinds of things about her that helped me to know her better. I am big on relationships. I am probably unusual compared to most guys, in that I do not just want sex. If I am going to have sex, I want a great relationship with it. So, I was totally enjoying getting to know her. I finally found out her age, which was older than I thought. She was 62. She said she had never smoked, and said that is one of the main reasons why she looked much younger than she was. I also found out she had a boyfriend, who was around 65, and owned a business. She said their relationship was just a fun relationship that involved some sex. They mainly saw each other on weekends, and talked, maybe, 3 times a week. She reiterated that it was friendship, with benefits, and nothing more. Then she finally took our talk back towards sex. She told me that she always wanted a hot relationship where she could do all kinds of sexual things with a guy, but figured she would never find it. She even admitted that she occasionally fantasized about dating a younger guy in his 20's or so, because she thought maybe a young guy would be open to trying different things. She then said "I am going to go for broke here, and admit to you that I even bought a cam for my computer and have stripped online with some younger guys while I told them what to do for me. As they obeyed what I asked, I stripped more and more for them." Then she admitted "Gosh, every time I have done it, I came incredibly hard after we were done." I kept thinking to myself "This is my perfect woman if she was about 20 years younger." I did tell her at that point that I totally loved how her mind worked. I thought she was the hottest woman I have ever met. I admitted that I dated a woman my age, many years ago, that was close to the way her mind worked, but I thought she (Claire) even beat her. I then said "Hun, we will see where this goes, but, the least we can do is have a great friendship, and have some unbelievable sex with each other." She smiled and said "You think so? Think you can keep up with my distorted thoughts?" I said "I can't wait to see how distorted they are." She said "You will now be naked for the next hour. Take off your panties." I thought it was interesting that she changed the word "boyshorts" to "panties." But, I thought it sounded rather sexy. I slowly slid them down and off. My cock was fully hard, and dripping precum. She then said "Very good! I will be experiencing, with you, every sexy and sensual thought I have ever had, if you will let me. My hope is that you will be dripping precum everywhere, and will be able to cum more than once a day." I said "Well, I usually can't, unless it is about 5 hrs apart and the sex is totally different than the previous time I came?" "It will be," she said. Then she continued with "Let's just see what all you can handle. In two weeks time, I want to do everything possible with you, sexually. You will fulfill all my fantasies, and I will make sure you are happy. I hope my fantasies, will become your fantasies." Then she said "It is time for your first cum of the day. I think I have made you too excited to go much further. Besides it will be my next challenge to get you excited again." Then she said "Sit back down, (I had been standing from when I took off the boyshorts) spread your legs as wide as you can, and call me your slut and tell me what you want me to do." Now that was a new twist on things. I immediately responded with "Stand up slut, and take off that skirt. I want to see what is underneath." She immediately obeyed me by reaching behind and unzipping the rear of her skirt, and letting it fall down. She was stunning. She was standing there in a black thong! Plus, she had on black thigh highs. I then said "Turn around my sex slut, and let me see your ass." She immediately obeyed. Did she have the perfect ass of a 30 year old? No. But, her 62 year old ass looked incredibly good ,nevertheless. It was not flabby, just slightly wide, but not bad at all. And, the thong looked awesome on her. I was practically drooling. I then said "Wow. You are incredibly hot." I then said "Bend over slut, so I can see your ass and pussy with that thong on." She immediately obeyed. I let her stay that way for about a minute, then I said "Turn around now and slide down your thong to your thighs and show me your pussy." She immediately obeyed. She was shaved smooth. I said "Wow, very nice." Then I said "You want to fuuuccckkk me (I drew out the word when I said it) really bad, don't you?" She said "oh, yessss." "Tell me how bad " "I can't wait to fuck you," she said. Then she went on with "What I want to do is have you give me the next two weeks of your life so I can suck and fuck you every day. I want to live out my fantasies with you. Would you do that for me? If today is enjoyable, will you let me play with you each day for two weeks?" I was stunned, but totally excited. I said "I will tell you later today. But, you will probably get your entire wish." She said "Starting with tonight. I want to sleep naked with you in my bed tonight, all night long and wake up to you." Then changing the subject slightly, she said "So, what do you want your slut to do next?" I said "Suck my dick for 2 minutes, lick my balls for another minute, then sit on my cock and ride it while I play with your tits until I cum." She obeyed perfectly. After she sucked me and licked my balls, I fucked her sweet pussy as she wiggled on my cock like a sensual stripper. I made it, maybe, 5-6 minutes, then exploded cum into her pussy. After I came, she stayed straddled across my legs and layed her head down against me, with her tits all the way against my chest. She just held me close for a good 10 minutes or so. Then she said "Gosh, I am going to love this. Where have you been all my life?" Then she got off of me, layed down on the floor and said "My turn to be in control. Lick my pussy with your cum in it, until I cum." I had never done that before, but it had been a fantasy of mine. I got down between her legs and obeyed, eating her pussy. It was different for me, but the more I ate her pussy, and the more she squirmed toward an orgasm, the more turned on I got. I started liking it, and ate her until she came, and until her pussy was clean. I layed down beside her and held her for about 10 more minutes. Then she said "Let's go outside naked for awhile and enjoy the sun and light wind on our bodies." Then she added "We got a lot more of the day left. Let's just keep getting to know each other, having fun, and enjoying incredible sex." "Sounds good to me," I said. To be continued ....