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Rick's Embarrassing Adventures Ch. 01

By: trenchantone



Chapter One -- Rick Takes A Chance

"That's it?" she asked. "You want me to embarrass you?"

I attempted to read her voice for judgments or incredulity, but neither was there. It was more matter-of-fact, as if she were asking for clarity, to make sure she understood.

"Yes," I answered. This was the tricky part. Rachel was a good friend, what the young people today would call a friend with benefits. She and I had been dating for a couple of years. Neither of us wanted to get married again. We were both in our Fifties and in reasonable shape for our ages. I'm no hunk at 53, but I'm not ugly either. I find Rachel attractive at 55, though I know she has a few (not many) more pounds than she did 30 years ago. She's in good shape. And we've both been sexually adventurous in our lives, both before and after we met.

Rachel broke the silence that followed my 'yes' answer. "What do you mean by being embarrassed?"

I shifted in my chair. We were sitting in her breakfast nook. It was late at night and we'd just finished a nice lovemaking session and were taking a break with a glass of wine and some leftover pizza.

"I'm a little embarrassed just to say it, but that's not exactly what I mean. For as long as I can remember, I've wanted to be compelled by someone else to do things that would embarrass me."

"Like what?" she asked. She leaned forward and took a slice of pepperoni and some attached cheese from the leavings on the platter. She looked interested.

"Like having to undress wherever I am or having to wear a stuffed bra under my shirt so that it's obvious I'm a guy wearing a bra in public or having to allow someone to have sex with me whenever or wherever they want or to have sex with someone they loaned me out to or having to hold my urine until I'm bursting then having to pee myself publicly."

I stopped. I tried to make my statements matter of fact, but I could feel myself blushing, and I had to look away in embarrassment. Mostly, I needed to hear some feedback from Rachel. Had I turned her off the idea or, perhaps turned her on? I could feel that I was quite erect myself, but she couldn't see it.

She chewed her pepperoni and cheese, swallowed, and took a sip of wine. "Stand up," she said. I stood. Given that I was wearing a loose robe that wasn't tied, as was Rachel, as soon as I stood my erection was apparent. "Well," she said with a slight smile, "you're certainly turned on by the idea," with a nod to my cock.

"Sit back down, Rick. I have some more questions." I sat.

"How do I compel you to do something that you don't want to do. I mean lots of people have fantasies and daydreams. That doesn't mean that at the drop of a hat they'll indulge themselves. If, for example, I told you to pee yourself in public, what would compel you to do as I said? I'm not strong enough to make you. Besides, others might intervene if they thought I was manhandling you."

I didn't have to take time to answer this one. "I had that question myself for a long time, which is why it stayed a fantasy. But recently I read a story series on the Internet about a woman who did a contract with a guy to use her like a slut. She wanted it, and he was interested. But he asked the same question you did. Her solution was to give him blackmail material to use on her if she chickened out. We could work out something similar to ensure that I followed through on this."

"Rick, honey, I don't want to blackmail you. I don't want to ruin you in the community. That would be cruel."

"Rachel, I don't want to be ruined, as you put it. I want to do this. I have a whole list of things back at my place that I want to do but that I've been kind of chicken to do. For years I've just put them aside as some things I would try if I got the chance but either they never came up or I passed on the opportunities when they offered. I chickened out. But they won't go away, and I want to do them. I need to be responsible to someone else, accountable to them. I'm sure that if I gave you some compromising photos of me, or you took some yourself, and you had to threat of releasing them to my email address list if I didn't follow through, just the threat would be enough to make me do what I was told to do."

Rachel sat back in her chair, obviously thinking. After a long minute, she said, "Be a dear and get me some wine," holding up her glass. I took it to the fridge. "Take that robe off for me, Rick. I like to look." I set the glass down and shrugged off the robe. Yes, I was still hard. Then I took the bottle out of the fridge, filled her glass and brought both glass and bottle back to the table.

I gave her the glass and started to refill my own when she put a hand out and grabbed my cock. "Just set the bottle down, Rick and stand facing me with your hands behind your back and your legs spread." I was surprised, but I did as she said. I stood there looking at her while she looked me up and down slowly as if seeing me for the first time, or at least in a new light. I began to find her gaze and my position, standing naked and open to her with my cock bobbing ever so slightly embarrassing. I was glad she had me hold my hands behind my back, because I was having this urge to cover my erection.

Her gaze apparently took all this in. "You're embarrassed, aren't you?"

I felt my face flush. "Yes, ma'am."

She smiled. "Ma'am? I like that, but then you have always been a polite boy." I found myself feeling more and more embarrassed, and I felt my cock getting harder and harder.

She continued to sip her wine and look at me. At one point, I looked away; the staring was making me more uncomfortable. "No, no, my pet. Look at me. Look at me and think about all of the humiliating and embarrassing things I could do to you."

God but this was embarrassing. She wasn't doing anything provocative, just sitting there, examining me and sipping her wine, like she was at an art show appreciatively regarding a sculpture. I felt mesmerized by her gaze, and I realized that she could make my wildest fantasies come true. I also realized that she might possibly have me do things I hadn't thought of doing or had shied away from in my own imaginings.

After some time of this, Rachel seemed to make up her mind about it all. "Come with me," she said, putting down her wine glass. She rose, and without a backward glance to see if I was following, walked through the living room and into her study. I followed keeping my hands clasped behind my back.

Once in her study, she opened a desk drawer and rummaged in her purse, pulling out her cell phone/camera. "I'm going to take some pictures of you to use as blackmail material. If you agree, then I'll play your game, and we'll see how far you'll go with it."

I stood still in the open door. "I agree, ma'am."

She looked at me for a few more seconds, as if giving me a chance to back out. When I didn't, she calmly pointed the camera and shot off a flash picture, which she then examined. "That's a keeper," she said. "Now, take a hand and stroke yourself lightly while I take another picture." Soon the flash went off again.

Satisfied with this second picture, she had me stop while she sat down at her computer and powered it up. Shortly, I saw her downloading her pictures from the camera and looking at them critically on the screen. "Good," she said as she closed up the picture folder, "those will do for a start."

She turned back to me with camera still in hand. "I'm creating a blackmail file on you that I will use if I have to. Now, masturbate for me and catch all of your cum when you orgasm. I don't want anything on my carpet. I just had it cleaned."

Wow. That was my first thought. She was going to do this. I suddenly felt a little queasy even as I reached for my cock to do as she wished. This had gotten very real very quickly.

She stopped me as I started to stroke. "Wait, you haven't thanked me. You must always thank me for whatever task I give you."

"Thank you, ma'am," I said numbly.

"Good. And you must always address me as 'Ma'am.' I find I like that."

"Yes, ma'am. Thank you, ma'am."

"Now get started," she said holding her camera up to catch the action.

I began to stroke myself with my right hand while keeping my left ready to catch my cum when I came. It took a few minutes because I had so much to process. She was actually going to do it, and I knew Rachel well enough to know that she would keep her end of the bargain, at least far enough to make me give up the whole thing. But what if she didn't? What if she would actually post these pictures? That made me hard again--I had flagged a bit as the realization that she was going to do it flashed through my mind--and I began imagining her parading me naked through her neighborhood or sucking the cock of some stranger she picked up for the purpose or wetting myself in the food court of a mall.

And then I came, and I my eyes flew open to catch the spurts. Even though we had just finished a satisfying sex session maybe an hour ago, I came harder than I have in years, decades maybe. I had to be quick to catch potential drippings, but I managed to keep everything off the carpet even as I staggered from the force of the orgasm.

When I looked at her again, both my hands rather cum covered, she had a devilish smile on her face. "I'm videoing all of this, and I think it looks great. Now, eat your cum. All of it. Lick it up slowly and swallow it. Every drop." I gulped. That was terribly humiliating! I'd never thought to actually do that before.

She saw my hesitation. "I'm waiting."

"I, uh, thank you, ma'am," I finally stammered out. I could feel my face redden as I brought my hands up to my mouth and began to lick my salty ejaculate. (I had a vasectomy about 20 years ago when I realized I didn't want to father any children, so I can't call it sperm.) Over my hands, I could see her holding her camera catching every movement, every lick, every swallow. I realized this was NOT something I wanted my friends or family to see. Ever. I was into it now. I would have to do whatever she wanted for as long as she wanted. And it was my own doing. She would only be doing what I had asked her to do.

When I finished, Rachel shut off her cell phone camera and put it on her desk. Then she got up and came over to me, put her arms around me, and said, "That was a good boy. I'm proud of you." Then she kissed me. When she pulled back, she was licking her lips. "You do taste good," she said with a smile. "Now lets go get you some wine."

We went back into the kitchen. I sat down while she filled my glass. I didn't bother with the robe. Somehow I knew that my days of being clothed in her presence were now at her discretion, not mine.

"So," she asked after sitting down and taking a sip, "how did that feel? Was it what you expected and wanted?"

"Yes and no. I mean it was great, and I hadn't expected you to move so quickly or decisively. Not that I'm complaining. In the sense that it was both exciting and humiliating, I loved it. But you moving so quickly caught me off guard."

"Well, I wanted to see if you would be responsive and how you'd react to something both real and safe." She leaned forward and took my free hand. I find I'm excited by this turn in our relationship. You've shown me a lot of trust just telling me this. I want you to trust me. And I find I liked what I saw, what I felt."

She leaned back in her chair, letting go of my hand. "Now, let's talk practicalities."

"Practicalities?"

"Yes. Right now it's all kind of nebulous and open-ended. How long do you want to do this? Forever? For a couple of days? And what, specifically, do you think you want to do? What we just did; was that an idea you had? And what other ideas do you have?" I took a sip and thought, but not for long. The stories I had read gave me some clues as to how to proceed. "How about if we draw up a contract for, say, a month? During that time, I'm completely in your power. You may do with me what you want."

"Okay," Rachel answered, "I can do a month. But I still don't know what all you want. You've given this a lot more thought than I have. Frankly, when I think of embarrassing a man, I'm usually thinking of how not to, since most men hate to be embarrassed, especially in front of women."

Specifics, I thought. I closed my eyes and started talking. "Well, I mentioned the peeing in public thing and the stuffed bra. Then there's having oral or anal sex with someone when commanded to do so." I opened my eyes. "So that would have to be someone you trusted. I would have no say in the matter."

"Are you bi, Rick?"

I thought about it. "Not really. I've never had, or tried to have, a romantic relationship with another man. I have sucked a couple of cocks, and I found it excitingly humiliating, but guys don't turn me on like women do. I guess it's the situation that turns me on."

Rachel frowned. "This is beside the point, Rick, but do you feel like you're humiliating a woman when she sucks your cock?"

I choked on my wine. "No! I mean I never thought in terms of humiliating someone else this way. Only being humiliated."

Rachel nodded approvingly. "I'm glad to hear it. Obviously, I haven't always known what was going on in your mind when we've had sex, but I found it disconcerting to think that you might have thought you were humiliating me when I serviced you orally. Speaking of which, do you feel humiliated when you eat me out?"

I wasn't shocked at the question this time. It seemed a natural follow-on to the previous one. "No. I enjoy pleasing you, that way or any way. It would be humiliating if I were called over here when you had another person present--man or woman--and I was told to strip and service them. It would be even worse if I knew the person."

"So," Rachel asked, "anything else specific you can think of?"

I shook my head. "Not that I can think of right now, though I'm sure there are other ways to embarrass me that I'm just not thinking of."

"You mean like making a masturbation video, including licking up your spunk?" She asked with a wicked smile. I wondered how quickly I would come to dread that smile.

I nodded. "Yes, ma'am." I felt myself flushing at the recent memory.

Rachel stood. "Okay, here's what we're going to do. I have a bra I want to try on you. We're going to have to go shopping for clothes." She stopped. "Unless you have some already?"

I flushed. "Yes, I have a couple of mail order that I bought some time ago, but I never had the courage to fill them. Under a t-shirt and a dress shirt and coat, no one could tell what I was wearing."

"We'll have to fix that. Anyway, I'm gonna put this bra on you and we're gonna come down here, you in your bra, and you're gonna eat me on the couch. You've had your seconds, but I have not, and I find I'm hungry, I am.

"Then, when I'm satisfied, you will dress and go to your home. Don't worry, your bra will be visible if anyone stops you to talk." There was that devilish grin again. "Tomorrow, when you come back, you'll be wearing one of your own bras under a sleeveless tee, tight shorts--I think that pair of bicycle shorts will do; they show your assets off nicely--and a pair of running shoes. Nothing else. Bring my bra and your other one back with you along with everything else you have that we might play with.

"For my part, I want to do two things overnight. One, I want to read the stories that set you off on this journey. So give me the links I need. Second, I'm going to draw up a contract for you to review and sign. If you think of anything that should be added to such a contract, send me an email. If I like it, I'll put it in. But I want to have it printed out when you get here, which will be at noon sharp. We'll review it, sign it, and start the fun and games."

Then we went off and followed her plan for the evening. 

Rick's Embarrassing Adventures Ch. 02



Chapter Two--Contract And Adventure

Rachel's bra did fit. She put a couple of pair of her sport socks in each cup "to fill it out" she said. In the mirror, I looked like a guy with a striking pair of boobs. They wouldn't stand up to close inspection, of course, but I felt very embarrassed wearing a filled out bra. Of course, Rachel took a couple of pictures of the guy with the hard dick and full bra.

Then she led me downstairs to the living room. She put a towel on her sofa and sat back with her legs spread while I knelt before her and ate her out while she played with her tits and nipples. As she got closer to climax, she grabbed the back of my head and pressed my face into her pussy, humping my nose and tongue while I tried to breathe while continuing to tongue fuck her. She had quite a climax and was a few minutes regaining her full senses.

She finished off the evening with a couple more pictures of me, with her juices all over my face and a hard, untouched cock all in plain view. Once she was happy with her pictures, I dressed in my casual shirt and slacks, socks and shoes. I had to carry my underwear. "None of that man stuff for you," she declared. "Go commando until I get you some nice panties." A couple of more pictures, and I was out the door while she scurried off to visit the story site I had told her about.

I went home with instructions to drive the speed limit and obey all traffic laws and undress completely once I got home. "But under no circumstances are you to cum outside of my presence without my express permission." I, of course, agreed with a "Yes, ma'am. Thank you, ma'am." Once home, I fell asleep and dreamed of horribly embarrassing, yet highly erotic situations in which I was shown off to all sorts of people.

Of course, I woke up with a raging hard on, but I remembered my instructions and willed it down so I could pee and get a shower and shave for the day ahead. The day ahead. What did Rachel have in store for me today? I'm already feeling randier than I can remember since I was a teenager. How long would THAT last? Not that I was complaining. I wondered if I had discovered the fountain of youth in my weird fantasies.

I didn't have much to do that Saturday morning. When I left for work the day before, I knew I was meeting Rachel for dinner and ... after work, and I expected to wake up in her bed this morning. Yes, we actually called our trysts "dinner and..." We weren't a couple exactly. We were friends. Then one day we decided to sleep together. So we became friends with benefits. But we dated others; we slept with others. We had our own lives. But we were first and foremost friends.

Now we were...what, exactly? I didn't know, but I was excited to find out how this was gonna work out. I was also, I admit, scared. Could I go as far as I wanted? Could I go as far as she might push me? Might she give up because it just wasn't something she wanted to do? Or had I unleashed a tigress? What I saw last night in her resolve made me wonder what I had gotten myself into.

I started to think about what I wanted in a contract with Rachel. I honestly wanted the experiences I had told her about. One one level they terrified me; on another level they excited me like nothing has in a long time. I wanted it to last at least a month. Frankly, I figured that with our work schedules, we probably couldn't do much other than on weekends. So, counting this one, we had four weekends. That meant a lot of work for Rachel to schedule my activities, which I fully expected her to be around for. She was both my security blanket--someone who would be there with me when I was scared or got into trouble--and my taskmaster (mistress?) who would insist I not wimp out but complete the embarrassing challenge ahead of me. I began thinking maybe we would need to spread this out over a couple of months to account for real like.

I was still thinking in this vein at ten o'clock when Rachel called. She wanted to know if I had anything I wanted to add to what I had said last night. I told her that I was worried about how little time we'd actually have, given our hectic schedules.

She cut me short. "Scheduling is not your concern. I've laid out a program that should fit both of our needs and schedules, unless you have something coming up you haven't told me about."

"No, ma'am," I answered. "You have access to my schedule, and I have nothing coming up that I am aware of. Of course something might come up, but I'm not expecting anything."

"Neither am I," she answered. "If something changes, we'll discuss it at that time. Now, if you have nothing else, I'll email the contract I've drawn up. You will send me your address books, both work and social. Once you get here, we'll discuss any changes that you feel need to be made. Do keep in mind that I read those stories you pointed me to. They were fascinating and gave me some wonderfully wicked ideas."

My heart sank a little even as my cock rose. There were parts of those stories that I didn't think I could do. The stories were about a woman who wanted to be used as a slut. She would suck and/or fuck anyone anytime for the man she had given herself to. He, in turn, would tell her to find strangers and blow them or fuck them in public or semi-public places. I'm willing to believe a woman can pull that off, but how many guys will let another guy blow them, even in private? And women who are strangers? Well, I'll concede it's remotely possible, occasionally, in exceptional circumstances. Routinely? No way. I'll be lucky if I'm not arrested and with most guys I'm likely to get beaten up.

Still, I trusted Rachel. She knew all the things I knew. I didn't think she wanted me to get arrested or beaten to a pulp. So I just said, "Yes, ma'am. Thank you, ma'am. I'll send my address books right away."

She hung up with a lilt in her voice as she said, "See you at noon, Richard."

I went into my office and fired up my computer, which immediately told me I had mail. Among the usual pieces of this and that was Rachel's with attachment. I resisted the urge to open it until after I had downloaded my address books to a text file and sent them to her in a separate email. Then I opened her email.

Hi Rick,

When you open the attachment, be sure to put

your full legal name in the blank at the top.

You will see my full legal name in the

appropriate spot after your name. In addition

to the other items you are supposed to bring,

print out two copies of this agreement

and bring them with you.

Rachel

I opened the attachment and saved it to a file on my computer. Then I read it.

"Personal Services Contract Between ___ and Rachel Irene Marie Simpson (Rachel)"

No, I hadn't known her two middle names, and I must admit that I laughed when I saw what the initials spelled.

I added my own, rather more mundane, name: Richard Thomas Thornton III (Rick). Then I read on.

"Rick grants Rachel access to his body for any and all sexual services she may require of him with herself or with anyone else who she may designate. Rachel agrees to make any and all sexual activities with Rick as embarrassing and humiliating as possible consonant with keeping Rick safe from permanent bodily harm.

"Rachel further agrees to find ways to humiliate and/or embarrass Rick both privately and in public provided Rick is not exposed to legal arrest or imprisonment. Rick has requested this service of Rachel and she agrees to provide it. Rick further agrees to allow Rachel to photograph and/or video any of his activities for her exclusive use.

"Should Rick fail to attempt any task set for him to perform, he grants Rachel permission to reveal to any or all of Rick's friends this contract and any pictures or videos she chooses to release. Should Rick complete all assigned tasks, Rachel agrees to give him all copies of this document and any pictures or videos of his activities or to destroy them in his presence.

"This agreement is in effect from today, 25 June until 25 July and can only be modified by mutual consent of the undersigned."

Well, I thought, that's pretty succinct...and pretty sweeping. I printed out the two copies. I could think of a lot of qualifiers and disclaimers I might want in this document, but I decided to go with it as written. Rachel knew that I wanted to live some experiences that were in those stories we had now shared. I knew I would be very uncomfortable, but that I had asked for it. So I had no kick coming. As I drove off to Rachel's, I wondered briefly what lay at the end of this road. There was no telling, but I was sure it would be exciting.



Rick's Embarrassing Adventures Ch. 03



Chapter Three--The Journey Begins Embarrassingly

Once the contract was printed out, I began getting ready for my day. I went to the closet in my office and got down my box of goodies. I didn't have much in it: two bra/panty sets, one dark blue and a full wire C-cup support bra that I'd never had the guts to wear outside my home and one bright red relatively flat bra that I'd never had the guts to stuff like Rachel had with her white cotton bra I'd worn home last night. I had worn the red one once, but I just felt stupid in them without anyone to notice and maybe harass me about what I was wearing.

The rest of the box contained two butt plugs, a set of nipple clips with connecting chain, and a vibrating dildo. Neither of the plugs was particularly large: inch, inch and a half diameter at the largest. I got them to get a sense of what it felt like to walk around or sit with something stuffed in me. The dildo wasn't large either. I got it with the thought that the vibrations on my prostate might produce interesting effects. Didn't work out, though. It wasn't strong enough to vibrate inside me. The nipple clips produced interesting effects, but they could be pulled off easily. I guess they were more like jewelry than anything else.

I took the whole box up to my bedroom; it was time to dress. I have three sleeveless tees; all are relatively snug, as Rachel knew since she'd seen me in them in the past. And one pair of bike shorts that were indeed snug. I put the shorts on then turned to my box. I decided to wear the blue bra. I expected it to produce noticeable bulges without any padding, but when I put the shirt on it sort of flattened the cups. I guess the wire supports are pretty flimsy without something to support. So I put Rachel's socks back in the cups and slipped the tee back on. That worked as I knew she would want, but I shivered as I looked at myself in the mirror. I was definitely a man with C-cup breasts. I couldn't help wondering why I hadn't chosen B-cups or even A's, but there was nothing for it.

There was nothing for any of it, not once I sign that contract, and given the way I was dressed as I picked up my box, there was nothing to do but follow through. Rachel was the provocateur I needed, but I knew this was my own doing.

Practical matters. I came home in the dark of night. Nobody saw me when I parked my car on the street. I don't have a garage or carport. So I had to walk out to my car dressed as I was carrying my box, which wasn't very big, in plain sight of anyone in the neighborhood who was looking. Okay, I told myself. Just act as if everything is normal.

And everything went fine. There were a few people doing their usual weekend yard work, but they were all engrossed in their own activities. I don't know my neighbors very well, not much more than a wave or a nod. Still, I was glad no one seemed to be paying attention as I got into my car and put my box in the passenger seat. All normal, except that I'm sitting in my car wearing a stuffed bra, and I'm obviously a guy. The drive to Rachel's was equally uneventful. Stopping at traffic lights, nobody noticed. Driving, nobody noticed. Pedestrians crossing at the crosswalk, nobody noticed. It was rather stunning to realize how little anyone pays attention to what's in the cars on the road.

I pulled into Rachel's driveway about five minutes to noon, feeling that I'd timed it right. As with my own neighborhood, there were a few people out doing yard work. It was a pleasant, sunny day, perfect for all sorts of outdoor activities. I knocked at the door and waited. And waited. And waited. I checked the time, 11:58. Then I realized she was making me wait until noon exactly. So I waited til noon and knocked again. This time the door opened promptly.

"Anxious, were you?" Rachel asked through the screen door.

"No, ma'am, not particularly," I said opening the door.

She held her ground. "Oh? Well I have a task for you. Give me the box and your shirt. Then I want you to move your car out onto the street. I want to take my car shopping. Take your time. I'll wait."

I could feel myself blushing as I handed her the box. Then I took off my shirt and felt very exposed. Anybody looking was going to see me wearing a C-cup blue bra and nothing else above the waist. My cock stirred in my tight shorts.

"Yes, ma'am. Thank you, ma'am," I said. I turned and headed back to the car. Nothing had changed on the street other than I was feeling very embarrassed walking back to my car. I backed it out of her drive and put it by the curb in front of her house, got out, and walked up her drive back to her front door. I didn't race, but I didn't look around, either. Her front yard and driveway are about twice as deep as my own front yard, but it felt like forever walking back to her front door. Rachel was standing there with her camera phone out videoing it all.

"Very good, Richard. You may follow me in, now."

"Thank you, ma'am," I answered, grateful to be out of whatever spotlight might have focused on me. Even if I couldn't see anyone paying attention to me, I could feel a dozen eyes on me as I slipped into Rachel's house.

My gratitude was short-lived as she led me into her study. The blinds were up, the curtains and windows open. I could see out, which meant to me that people could see in.

Rachel took a seat at her desk, on which my box sat. "Remove your shorts and shoes," she said. I did so, and my cock sprang out of my tight-fitting shorts as I did so.

She held up the contract. "Are you ready to sign?"

"Yes, ma'am."

She laid the contract on the corner of her desk along with a pen. I stepped forward and signed. Then she signed.

Then she picked up the camera and pointed it at me. "Read the contract to the camera and then say that this was all your idea, that you do this of your own free will, and that you insist that I send any compromising photos and videos to your employers, friends, and family if you fail to fulfill any tasks you are given by me or by anyone I designate with power over you for the next month."

"Thank you, ma'am," I said, taking the paper. As I began to read the finality of the words hit me. I was both excited and terrified at the same time. Rachel was being very stern, very matter of fact, and very, very determined. I felt my blush becoming permanent.

When I finished, Rachel stopped her camera and downloaded more video to her computer. Once that was started, she took the paper back from me and placed it in a travel folder on her desk. "Good, we'll get that notarized while we're out."

"You mean a stranger is going to see this?" Stupid as it now sounds, I was incredulous. I should have known better.

"Rick, I have the address books loaded onto my email program. It won't take me but a few minutes to start sending materials out. Are you wimping out now?"

"No, ma'am. I'm sorry, ma'am."

"Not as sorry as you will be, I suspect. Now, let me lay down some basic ground rules.

"First, in the future, when you come to my house, you will park on the street as you did just now. You will get out of your car and remove anything you are wearing that covers your bra. You will also be wearing matching panties or thong, and you will remove any covering shorts or pants and any shoes or sandals at the car. Then you will walk slowly to my front door, knock, and patiently wait for someone to open it."

I paused before replying. This was as real as could be. "Yes, ma'am. I wonder what the neighbors will say, or do. Might they call the police?"

"They might, but I don't see where you are breaking any laws. You will be as decently dressed as most of the women lounging in their yards getting some sun, and you won't be accosting anyone." She stopped to smile. "Though some of them may accost you. If anyone talks to you or stops you on your way to the door, you will turn to them and engage them in conversation, if they wish."

Of course, I thought. I am the male version of the slut who cannot say No to anyone. "Yes, ma'am. Thank you, ma'am."

Rachel smiled at my quick capitulation. "You want to be embarrassed, Rick. I'm just giving you what you want. I'm finding this quite enjoyable.

"Now to continue. Once you are inside, you will immediately remove your panties. Do not stop to look around at who might be present; just drop them by the door. Then, you will come find me and kneel before me. I may be anywhere in the house at that point; I won't always be answering the door. You will not move quickly. You will be deliberate. You will not hide any part of your body. Hands at your side or clasped behind you. You will stop and display yourself to anyone who asks for a better, less hurried look, but you may not engage in any sexual activity with anyone before you present yourself to me."

Rachel turned to the box. "Now let's see what's in here. Oooh, matching panties. Very good. And another slutty set, this in red. Very good. Of course, we will get you more. I can't have my slut walking around in dirty underwear."

She held up the two plugs and the dildo. "What have we here? Toys? Well, they're woefully inadequate, but we'll remedy that soon enough. I'm going to want you open to the possibilities, and these won't open you much at all." She tossed them back into the box. "Oh, and a little jewelry, I see. Nothing much, but I bet they could provide a bit of distraction. They look cheap, though." She regarded the clips--they were cheap, I had to admit--thoughtfully, as if mulling the possibilities. "Perhaps," she said, as if half to herself, "I'll get his nipples pierced. That might be fun." Then she looked at me. "Wouldn't that be fun, Rick?"

"Thank you, ma'am. Whatever would please you, ma'am." I didn't think she'd actually do it, but I thought I'd better just go along.

She dropped the clips back in the box and stood up. "Yes, whatever pleases me and embarrasses you. Right, Rick?"

I nodded my head. I could feel myself blushing; I don't think I'd stopped since I'd gotten here. "Yes, ma'am. Thank you, ma'am."

"Come with me," she said, leaving her study. "I need to take the edge off." I followed her through her house to her sun porch. It's on the back of her home, taking up part of your small back yard. She has neighbors on three sides, and though they are seldom seen, they can easily see in if they wish.

Rachel hiked up her skirt and pulled off her panties and sat down.

"What are you doing?" I asked rather stupidly.

"I'm advertising," she answered, "and you are kneeling down and giving me the pleasure of your tongue. Now get to work."

"Yes, ma'am. Thank you ma'am."

A casual look around showed no one looking, but I had no way of knowing what would happen while I was busy. She had her back to the wall and could look out. I was faced the opposite way as I knelt down and would see nothing but Rachel's sex. I knelt down. 

"Did you cum since you left last night?" she asked.

"No, ma'am."

"Good. Don't cum now. You may proceed." She lay back, legs splayed, and closed her eyes. I put everything out of my mind but bringing Rachel to an orgasm.

Rachel is generally a vocal woman during sex. She says, and I agree, that a man appreciates applause for a job well done. But as I worked her inexorably to her climax, I could have wished for a more discreet reaction. I should have known better. She realized that any embarrassment she might feel at being discovered en flagrante would be quickly overwhelmed when her audience, if she had one, saw me in all my current glory.

She came with a great cry, pressing my face against her pussy and rubbing her juices over me. Once she'd caught her breath, she smiled down at me. "That was good, Rick. I do believe you are the best I've ever had at that. Now be a dear and get me a clean, damp washcloth and a hand towel. You know where they are."

I went to the guest bathroom to do as she wished and was soon back between her legs, this time washing and drying her before putting her panties back on her and helping her to her feet and smoothing out her skirt. She looked like the demure, competent woman of fifty she always looked to the public. No one had apparently noticed our activities, though I can't imagine how. Perhaps the immediate neighbors weren't home. I didn't know.

"Now, put those things in the laundry and go clean yourself up. Then meet me in my study."

In the study, she had me put on the panties that matched my blue bra, my shorts, shoes, and shirt.

"Let's go shopping, shall we?" she said, and she led me to her car in the garage.



Rick's Embarrassing Adventures Ch. 04



Chapter Four--A Humiliating Shopping Trip

It took about half an hour to drive to the mall Rachel had selected. As with my trip to her house, no one seemed to notice me sitting in the car wearing a bra under my t-shirt. Initially, there was no conversation between us. The car was quiet, and Rachel was busy navigating the roads to the outer loop interstate she wanted. This took only about ten minutes of the trip.

Once we were on the highway, she asked, "Are you excited?"

I thought about it. "Yes, ma'am. I'm excited. I'm also scared. I'm realizing that you're going to parade me through this mall and into shops." It was true. I was thinking about that and feeling very uneasy about what could happen: the stares, the smirks, the laughter, and even the ridicule I might be in for.

"That's absolutely right, Rick. And you are going to act like this is a normal part of your life. For the next month, it will be a normal part of your life to be exposed in this fashion to the reactions of others. I don't want any holding back on your part. This is what you asked for. I'm looking forward to taking you to some stores that should be able to fit you in some decent, or indecent, clothes.

"When I park, you are to get out and follow me into the mall and into any shops I choose to enter. You will stay with me at all times unless I turn you over to one of the shop assistants. If one of them will see you alone, you will go with her for your fitting, and you will do whatever she tells you to do as if I were telling you. If anyone doesn't want to work with us on your clothes, we will leave together and find another store. But you will always smile and be polite and courteous."

"Yes, ma'am. Thank you, ma'am." This was going to be awful. I just knew it would be. Just as I knew that I was rock hard with no foreseeable way to calm myself down. I just hoped any of the helpers I was given over to would not scream at the sight of a hard cock.

Rachel parked at a center door of one of the largest malls in the area, one that had three huge anchor stores and dozens of smaller establishments in between. We got out, and she locked the car while I scanned around to see who was noticing.

"Come along, boy," she said as she started for the door. I scurried to catch up. We made a disparate pair: she was dressed like a respectable woman in light blouse, beige skirt, hose, and sensible but fashionable shoes. I looked like ... I'm not sure; I think an aging dyke, at least from a distance. Up close, I'm sure I looked like a poor excuse for a transvestite. No self-respecting cross-dressing man would look like so incompletely transformed.

She stopped at the door, and I knew it was for me to open for her, which I did. She breezed past me to stop at one of those large information maps, which she proceeded to study as if looking intently for the way to her destination. I suspected she was just showing me off, and I fully expected to be slow-walked the length of this place and back, as well as stopping at as many places as she wanted to stop.

Meanwhile, I had to stand by her side as if everything was normal. There were people around, walking to and from their cars or going in or out of the small shops in this entrance area of the mall. There was a games arcade with younger people congregating around it, and across the way there was an ice cream shop that sold cones and shakes and such. Many people of various ages and no one seemed to have noticed me at all.

Wait, there was a woman of about thirty. I saw her casual glance, then I saw the double-take look. Our eyes met, and she looked away as if ashamed for looking. That was a surprise. Was she embarrassed for me? Or was she embarrassed that I saw her looking? 

Yet aside from her momentary reaction, I was getting nothing. From a distance, no one seemed to see anything out of the ordinary. I was relieved.

Then, to my surprise, I felt disappointed. I had feared just this situation of being out in public and being ridiculed for my attire. Now I wasn't getting more than the occasional, well rare actually, second glance. It felt like a come down, a big time downer.

"Rick, come with me." Rachel's voice brought me out of my reverie and back to the reality that Rachel was going to embarrass me here, and it had been my idea.

I moved to catch up with her. "Yes, ma'am. Thank you, ma'am." She surprised me with her walking speed. I had expected a long drawn out leisurely stroll, but Rachel was moving with purpose toward a specific destination.

About halfway down the center corridor of the mall, we came to the place Rachel was looking for, a fair sized women's clothing store advertising "Fashions For the Full Figured Woman." At 6' 1" and 210 lbs., I think I'm an average size American male, but I guess that would make me more of a large woman than otherwise. So the choice made sense. I would soon find out how people here would feel about me being here. I didn't even have to guess that this would be embarrassing.

Rachel made straight for the lingerie desk. We had to pass most of the displays for bras, panties, slips, and such. Mostly I saw light shades: white, beige, light blue, but there were some bright colors, too.

"Anna," Rachel said to the plump woman behind the counter, "How's business?"

Anna had been watching us approach, and I thought I saw the hint of a smile on a rather pleasant face. She was wearing a nicely styled blue business suit, no doubt from the store's stock, and she had an ample bosom to hold up her nameplate that identified her. But it was obvious to me that Rachel knew her.

"I can't complain, Rachel honey." Anna had a rather brassy voice that carried easily. "Well, I could complain, but who would listen?" Then in a louder voice, "Is this the gentleman you were telling me about this morning?"

Uh oh. They had this setup already. I felt myself blush and my cock stir.

"Yes. Anna, this is Rick. He needs some bras and panties that fit him appropriately. As you can see, he fancies himself well-endowed in the rack."

Anna looked me up and down slowly. "Yes, I can see that." She pointed at her own bosom. "I'm sure we can find some items that will work. And you say he wants to be embarrassed as we do this?" The way her voice carried, I wished I could just melt into the floor. There were other customers in the store on this Saturday afternoon, and I was sure they were looking our way now even though I dared not look. I tried to smile sheepishly through my increasing blush. I was feeling hot, blushing so much.

Rachel smiled at both of us. "Yes, that would add to his enjoyment..and mine. I'm finding I like his coloring."

Anna came around the counter chuckling to herself. "Rachel, you wouldn't believe the men who come in here 'shopping for their wives'," she added air quotes. They blush so nicely. Funny that all of them have 'wives' who are about their size in the chest." She turned me to face her directly, staring into my eyes. I tried to stare back, but broke easily. "Does he have a special name for this excursion?"

"Special name?" Rachel asked. I stayed silent.

"Yes, many of our male clients have female names for when they're playing dress up. Oh, and I forgot to ask, are we doing a full outfit or just the under garments?"

Rachel thought for a bit. "No, Rick is a different case, I believe. He doesn't want to dress as a woman completely. He just wants to look like a guy wearing a bra in public. It turns him on. I suppose we could call him 'boy' while he's here so there's no confusion about what he is."

Anna nodded. "Okay, boy it is." Then to me, "So, boy, what are you?"

"Ma'am?" I wasn't sure what she wanted me to say.

"Well, are you a slut boy who can't say no? A queen? A tease? How do you see yourself at this moment? It makes a difference how I dress you."

How did I want to describe myself? I hadn't considered that. After thinking for a bit, I turned to Rachel. "Ma'am, how would you describe me? I think that would be most appropriate, if you agree." Rachel smiled. "Very good answer, Rick. Anna, he's a slut boy who can't say no."

"Oooh, good," Anna said, clapping her hands. "I like slut boys who can't say no." She turned to Rachel with her own version of the wicked smile. "Does that apply to me?"

"Of course, dear Anna. I can't expect special service without offering an appropriate gratuity."

Oh shit, I thought. I was going to be servicing Anna, at least. And here in the store, no doubt. But before that, I was going to be very embarrassed. Oh, God, what have I gotten myself into?

Anna turned back to me. "Okay, slut boy Rick, let's see what I have to work with. Take off your shirt."

I was aghast. I thought I would do that in a fitting room. "Here?" I said, in a most unsubmissive way.

Anna took a step back, surprised by the loudness of my voice. Rachel stepped in. "Who are you to question anything? You agreed to do whatever I or anyone else said. You will NOT embarrass me. You WILL do as you are told, or else, and you know what that means."

I hung my head in shame and embarrassment. It didn't seem possible, but I had just made my situation worse. Just how much worse I didn't yet know.

"I'm sorry, ma'am. I lost my head."

"You don't HAVE a head," Rachel said. She was righteously furious with me. "Now get on your knees and apologize to my friend here. Then do as you are told."

"Yes, ma'am. Thank you, ma'am." I knelt before Anna and looked up at the woman towering above me.

"I'm sorry, ma'am." I started to take off my t-shirt. Anna stopped me.

"Stand up, slut boy. Now sit up on this counter facing out at the store."

I climbed up on the counter and faced out toward the store. Damn, I had attracted a crowd or curious onlookers.

"Now take off your shirt."

All eyes were on me as I pulled my shirt over my head, revealing my stuffed blue bra for all to see. Even before I got the shirt all the way over my head, I heard the applause and the laughter. I was mortified. I didn't think it could get any worse, when it did.

Rachel stepped forward. "For being disrespectful, you will now stand on the counter and take off your shorts."

I could feel my jaw drop. I thought I might pass out, but I got myself together quickly and said, "Yes, ma'am. Thank you, ma'am. I'm sorry, ma'am," as I scrambled to my feet on top of the counter for all to see.

The applause rose once again. I turned and began tugging my bike shorts down, stopping a couple of times to keep the panties from coming down with them. The applause turned to cheers and raucous comments from the various women in the shop. I could also see people coming in from the mall to see what all the shouting was about. There I stood in my deep blue bra and matching panties with my shorts around my feet. Oh, and of course my cock was poking my panties out obscenely. Everything was in play.

Rachel hollered at me above the crowd noise. "Smile and wave to the crowd, slut boy. Enjoy your humiliation."

I did as I was told. That's when I saw the camera flashes from all around as everyone wanted to be the first to post my shame to the Internet. Well, I may have just screwed myself over royally, and I had no one to blame but myself. As I stood there waving like a idiot, I resolved to keep my mouth shut unless it was required to be open.

Somewhere between two minutes and a week later, I was allowed to climb down from my perch. Anna turned to the crowd and said, "Show's over, folks. Hope you enjoyed it. Feel free to look around, but no more picture, okay?" She turned to Rachel. "I hadn't expected all of that. I hope it doesn't screw up your plans."

Rachel hugged the larger woman. "Oh, Anna, I couldn't have asked for more. He tried to embarrass both of us. He deserved what he got."

I stood silently as the women embraced. Women were wandering the racks close by, actually sneaking a look at me, but there were no more pictures. Well, I don't know that, but I didn't see any more flashes.

"Now," said Anna turning back to me, "Let's take a look at what we have to work with. Stand up straight and proud, slut boy. We should always be proud of how we look." I straightened my shoulders. "That's better."

She began examining my bra, turning me this way and that and away from her, slipping her fingers between the fabric and my skin. All the while, she was either tsking or shaking her head.

Finally, she turned me back to face her and Rachel. "Typical male. Even though it's a C-cup, it's too tight, both around the torso and in the shoulders. The shoulders are easy to fix, but it takes an extender to fix the other problem, and I hate to waste good extenders on such crummy fabric. I do like the color, though. It shows a little more imagination than the average male, whose tastes seem to run only to red or occasionally black. And the socks! Goodness men are so unimaginative." Of course, the socks were Rachel's doing, but I couldn't have done better. Besides, I knew this was a good time to be quiet and take it.

"But you can take care of him?" Rachel asked. She didn't really seem to doubt it, though.

"You know I can, dear. One question: Are you going to get him breast forms? You really should. Nothing fills cups out better if you don't really have the goods."

"That's why I came to you, Anna. I knew you'd know the best approach. I suppose I can get them on the Internet?"

"Yes, you can do that, if you want. But I sell them, you know. Come, let me show you."

They went behind the counter. Anna said, "I keep this section back here mostly for our ladies who have had mastectomies. It's so hard for them to get fitted properly after their surgeries, and even though the medical people will give them something I find I can help many of them with something of a higher quality than they might otherwise get.

"That's especially true of us fuller figured types." Anna turned her head to look at me, then turned back to Rachel. "Honey, I've got a set that will be perfect for what you want to do to your slut boy, here." She moved to whisper in Rachel's ear. I saw Rachel's eyes go wide, and I knew I didn't like it (and would no doubt love the humiliation of it).

"Yes!" cried Rachel. "That's perfect. I'll need six bras and matching panties. He'll try on each to make sure you're satisfied with fit and finish."

Anna smiled. "Take him to the room behind this wall. I'll bring your stuff to you, shortly." Before she left, she handed Rachel a rather large box. Rachel walked along the wall, and I followed, grabbing my shirt and shorts. I followed her through a curtain into a small room with a bench and a hanger for clothes along one wall and full-length wall mirrors on the other two wall, so one could see oneself front and side without doing more than turning the head. Despite the mirrors, in which I could not avoid seeing myself, I felt relieved to be out of the public eye.

"Toss your clothes over there and strip." As I did what she wanted, quickly being completely nude except for shoes (somehow that felt more humiliating than being barefoot. Meanwhile, Rachel opened the box, took out two large breast forms and what had to be an instruction sheet. As I stood near one of the mirrored walls, she read the sheet front and back. Then she looked back into the box and took out a tube of something.

"I think you're going to want to shave after we get back to the house. This adhesive will take some hair off when these come off for the night."

"Yes, ma'am. Thank you, ma'am," I said, automatically. I was looking at the forms. They were huge! Double D's at least. Geez but I was going to have a rack on me.

Rachel came over and applied the adhesive liberally. "With all that hair, I need to make sure your tits will stick." Then she very carefully lined up a breast form and pressed it on my left breast, holding it firmly and counting silently. she stepped back to look. Apparently satisfied, she did the same on the right, and stepped back again to admire her handiwork.

"Face the mirror," she indicated the one to my left, "And look at your new boobs."

I was amazed. If you didn't pay attention to the hair around the rest of my chest, they looked real; they even had nipples with brown aureola. Despite my predicament, I was impressed. And they were still huge!

"Anna thought that since you liked having a large pair, you should have an obscenely large pair." She looked down. "I can see that little ricki likes them, too." She grinned up at me. "Now somebody could fuck your tits and cum on your face." That thought made me burn with humiliation.

"You've really gotten into this."

"Rick, I'm having more fun than I thought I would. Those stories really got me going, and I realized you wanted to be the 'slut boy who couldn't say no.' So I thought I'd go for it and see how much I liked it. And I'm loving it!" Her face turned serious. "I'm having so much fun, I have to ask if this is meeting your expectations. This is a serious question. You've had an awful lot. Is it too much?"

"Ma'am, is this a trick question?"

"No, Rick. But your answer might modify some of my wilder thinking. Do you want it toned down, or am I meeting your needs."

"Gawd, I've never been so embarrassed in my life. Not even in my wildest dreams. But...but...no, dammit. I want your full treatment. Look at little ricki. I've been hard all day, well mostly. And I'm so horny I could probably shoot a quart!" I paused to take a breath. I knew I was speaking the truth. I am a slut who craves this, and I didn't want it to stop. "Thank you, ma'am."

Anna came bustling in at that moment and stopped dead in the curtain. "Well done, Rachel. That's one impressive set you got there. That should have him blushing for a long time. And that's not a bad looking pecker there, If I may say so. Is he any good with it?"

"He's quite good," Rachel assured her. "In fact, for a man with this sort of hang up, he's surprisingly good." (What the hell did that mean? I wondered, as my cock bobbed and my blush colored my neck and the top of my chest.)

Anna dumped her load of lingerie on the bench. "Well, there's no accounting for taste, I always say. Now, where shall we start?"

They spent the next half hour trying on every set of lingerie, Anna brought, all six of them. All of the bras fit, and even though I was now much better endowed than I could ever have imagined, I had to admit that the bras felt more comfortable than what I had bought on the Internet.

The panties were not so much fun because I kept poking out. Rachel made crude comments about how I would be arrested for indecent exposure if I walked around with my dick sticking out, which only served to further embarrass, and harden, me. I was remembering my instructions for when I came to her house for the next month. Anna thought it was all hilarious, which further embarrassed me.

Eventually, they had worked their way through all six sets. I ended up wearing a hot pink set that look ridiculous on a man in his fifties with a slight paunch. Looking at myself in the mirror, I watched my cock shrivel. Perhaps I had gotten used to the situation and was no longer turned on by it. Perhaps I was used to them and their comments. Whatever the case, I tucked that once proud bit of flesh into my panties.

"Well, Anna, I guess my slut boy is getting tired. Would you like your gratuity now?" We all knew what she meant.

"Rachel, I do admit I'm more than a bit keyed up, but I've been away from the store proper just about as long as I dare. Can I take a rain check?"

"Of course you can. Maybe you can swing by the house tonight?"

"I don't know, Rachel. I'm usually dog tired by the end of the day, and I have to open tomorrow. No rest for the wicked."

"Well, anytime you want to get some relief, I'll make Rick available." I felt numb to this talk by now. Rachel turned to me. "Get your shirt and shorts, but don't put them on till we pay." She grabbed the other new sets while I got dressed and picked up my blue bra and panties and Rachel's socks. Then we followed Anna back out into the main store and to the desk where we first met her.




Rick's Embarrassing Adventures Ch. 04



At the desk, Anna quickly snipped the tags off the bra and panties I was now wearing. "You can dress now," she said as she turned away to process the other sets of lingerie. I put my shorts on first, because I was starting to grow erect again at being outside of the small room where anyone could see me. Then I put on my t-shirt and discovered that with my new 'endowments' my shirt was somewhat shorter and hung a bit away from my body at the waist. I didn't have an exposed midriff, but I could feel something of a gap between tight biker shorts and the bottom of the shirt.

Rachel finished up with Anna and turned to me. "I need your credit card, Rick. Unless you want a store card instead." She had an impish smile on her face.

I fished my wallet out of my shorts. "If it's all the same with you, ma'am, I'll use my own card."

After we finished the transaction, Anna handed me a store bag with my new purchases inside as well as the undergarments I'd come in wearing. She thanked me for my business, in a rather louder than normal voice I thought, and told me she looked forward to seeing me again. All very normal from a sales person but full of double entendre to me.

As Rachel and I turned to go to whatever embarrassment she had for me next, I saw a couple coming toward the desk. The man did a double take as the woman looked away in disgust. We passed close together in the narrow aisle, and I distinctly heard him say in a quiet voice, "Nice rack, dude." I could feel my face flush instantly and my cock harden fully. So much for becoming used to the situation. 



Rick's Embarrassing Adventures Ch. 05



Chapter Five--Food Court & More Shopping

We got out of the store without further incident. "I'm famished," Rachel announced. "Are you?"

I should have been. I hadn't had that much breakfast because I was so keyed up. But I hadn't thought about food at all, and I didn't feel particularly hungry. My mind was, obviously, elsewhere. Walking along I felt very conspicuous, very top-heavy. What I said was, "Ma'am, I'm ready to eat when you are." There really wasn't much else to say.

"You've got to keep your strength up, Rick. Let's go to the food court." So off we went at the same determined pace she'd used when we went to Anna's store earlier. The food court was back the way we had come in. It was a large open space with tables and an arc of fast food places. Since it was past the lunch hour, it wasn't bustling, but since it was a Saturday afternoon, there was a fairly constant stream of people coming and going. Rachel picked out a table and sat down.

"Rick, be a dear and get me a chicken sandwich and some water. And get something for yourself from a different vendor. Make sure you have a large cola drink."

I set down my bag next to her seat. "Yes, ma'am. Thank you, ma'am." She wanted me to go to two different sellers. Okay. I looked around for the chicken sandwich vendor. "There are several kinds of sandwiches, Ma'am," I said. What do you want?"

Rachel thought. "Grilled chicken w/lite mayo, no tomato or lettuce."

"Yes ma'am."

I had to stand behind three other people. As I waited my turn to order, I could see most people around were sneaking peeks at me, trying to figure out exactly what I was, but no one said anything.

When I got to the front of the line, I saw it was a teenaged girl taking the orders. She turned from her register to face me, and her jaw dropped open. She stared at me in shock for a long time, and I felt my face getting redder and redder.

Finally, I said, "May I order?"

That closed her mouth, but she obviously didn't trust herself to speak. She nodded her head, never taking her eyes off my bosom. It didn't help that my voice sounded shaky to me. I wanted to sound comfortable, but her staring unsettled me. I felt all eyes on me, not just the teenager staring uncomfortably at me. She looked like a guppy out of water.

I spoke again, in a more confident voice. "I need a grilled chicken sandwich with lite mayonnaise, no lettuce or tomato and a bottled water."

That seemed to wake her from her trance as she made an entry into her register/computer. "Anything else?" she asked automatically. She was focused on her register, not looking at me. I answered No. She gave me the price, and I swiped my card. Without looking at me, she handed me the water and my receipt. "You'll have to wait for your sandwich." She motioned me vaguely off to the side, still without looking.

I moved away from the register and tried to figure out what I would do while waiting. Normally, I would just look around. I would sort of watch people, not staring or gawking but just scanning, thinking of nothing or perhaps something work-related or related to what else I was doing that day. But then normally I felt pretty inconspicuous. Right now I did NOT feel inconspicuous. Then a thought popped into my head. This was what I wanted. I was feeling conspicuous. I was feeling embarrassed. I was getting what I wanted, with the promise, the very near promise I was sure, of being further embarrassed. Right there I decided to enjoy it. So I casually turned around, just as I normally would. I wanted to see who was looking and how they were reacting.

I was surprised at how few people noticed. There were several people walking purposefully from one place to another. I saw people waiting in line at the various food vendors, studying menus, talking on their phones, and generally ignoring everyone around them. In the line I had just vacated, I did see a few people look at me and quickly look away. I also saw a man and woman, a couple by the look of it, staring intently at me. I continued scanning and my eyes rested on Rachel. To my surprise, she was chatting with a man who was sitting with her. From their body language, they obviously knew each other. That didn't surprise me; Rachel knows a lot of people, as do I. Then I saw Rachel look over at me. Her friend looked over, his eyes following hers. And they both smiled, as if sharing a private joke. I had the suspicion it involved me, and I felt my face flush.

"Excuse me. Excuse me!" I turned to the sound of the voice; it was coming from the sandwich stand. "Here's your order." It was a different girl than the one who took my order. 

I smiled. "Thanks," I said as I took the sandwich. I noticed that she was looking at me in wonder while at the same time trying to act as if she saw nothing out of the ordinary. I turned away and walked over to Rachel with her sandwich and water.

As I set her order down, Rachel said, "Rick, this is Brant Carlson." Brant stood up and offered me his hand. We shook and said we were happy to meet each other. He held my hand a little bit longer while he looked me over.

Then his eyes came back to mine. "You look interesting," he said. I looked up into his eyes and answered, "I suppose I do." He turned to Rachel, releasing my hand as he did so. "Well, I've got a couple of more errands to run. I think I'll take you up on your offer. Until then?" He bent down and kissed Rachel on the cheek. 

Rachel pressed his hand and returned to cheek peck. "Yes, until then." And Brant was off down the main corridor. She turned to me. "What are you having?"

"I think I'll get a slice of pizza and a cola."

"Okay. See you shortly."

I headed over to the pizza stand wondering what Rachel had in store for me with Brant. Then I was at the vendor. This order went without incident. No one seemed to pay me any attention as I ordered, paid, and returned to the table and sat down to eat. 

"How are you feeling, Rick?" Rachel asked.

"Honestly, I'm not sure. It has been both thrilling and embarrassing by turns, especially in the place where we bought these." I glanced down at my boobs.

"But?"

I thought for a bit. "I'm surprised," I answered, "by how little people pay attention to me. I've seen a couple of stares, and the people at the store certainly paid attention when I was on display. But in general, I'm surprised at how little attention I'm getting."

Rachel thought about that while I ate. "Are you disappointed?" she asked.

"No, no," I answered hastily. "I'm surprised, I guess, that I'm not more the center of attention with people laughing, pointing, snapping pictures, and giving me a hard time. And there has been some of that. But like now, walking across the food court, twice, nobody paid much attention."

Rachel nodded. "Well, I'm going to have to ratchet things up a bit as we go along, I guess. I, too, am surprised at how little overt attention you've gotten, but I have been watching and people are noticing. Mostly, they see you and then look quickly away."

"Finish up your drink. We need to move along." I was about halfway through my drink, though I had finished my pizza. I started sipping. "No, take the top off and drink it all down now. I don't have time to wait." It was a 32 oz. cola; so it was gonna fill me up pretty fast, but I did as instructed and swallowed it all down. And burped. Drunk fast, cola always has that effect on me. I took the remains of lunch to the trash and came back to pick up our package.

"Follow me," Rachel commanded. I did so as we headed back out into the mall. Shortly we entered another women's clothing store. Rachel strolled the aisles and displays, stopping now and again to look at various items but completely ignoring me as I trailed behind carrying my bags. I looked around and saw several women looking at me at different times, but as my gaze came to each, she looked away. No one said anything near us. No salesperson came near. The three I saw were all busy with other customers. I might have heard some whispering, but I couldn't be sure. All I knew was that I was not inconspicuous.

After maybe ten minutes of looking around, we left and headed back the way we had come. We passed the food court and the first store we had shopped in. We stopped at one of those standalone kiosks that sat in the middle of the wide mall aisles. This one sold insurance. I thought it was an odd choice until the salesman came around to us.

"May I help you?" he asked looking from Rachel to me. His gaze lingered on me, and I shifted my gaze to the back of Rachel's head. His look was appraising and made me uncomfortable.

"Yes," Rachel answered. "I believe you do notary work?"

"Yes, we do."

Rachel pulled our contract out. "Would you notarize this? I realize that we've already signed it. We are the signatories, but we would like it officially witnessed." She slid the paper to him.

He picked the paper up, a frown on his face. Then he started reading. Shortly he stopped and looked at me. "Well, well, well," he said. He went back to reading. 

When he finished, he slid the paper back to Rachel. "This is most irregular. First, signatures must be affixed to a notarized document in the presence of the notary. Second, " he looked at Rachel, "I don't think this is a legally binding document. Having it notarized would not make it in any way official."

"We understand both points, Mr. Appleton," Rachel answered calmly. "The act of coming here and submitting it to you fits with my friend's request to me that he be humiliated. Is there any way you could stretch a point in this case?" He started to shake his head. "Please consider that we'll double your usual notary fee, and this document won't ever be used in a legal proceeding. And," she paused for emphasis, "Rick will do anything you ask in return for this favor." Again she paused for emphasis. "Anything."

Mr. Appleton looked at me, and I felt myself flush, wondering what he might want me to do for him, knowing that I had no choice, and already feeling terribly embarrassed by this whole thing. He stared at me thoughtfully for a long time. "Does she speak for you?" he asked eventually.

I nodded. I could not find my voice.

"No, no. That will not do. You must tell me that you want to do this and that you will do whatever I ask in order for me to notarize this." He pointed at the contract. "Speak up, man ... or whatever you are."

That last stung. I felt my self control slipping away. I took a deep breath and was conscious of the heaving of my chest. He noticed it, too. A man's eyes naturally gravitate to a heaving bosom. The breath, and his reaction to it, steadied me.

I found my voice. "Yes, sir. I will do whatever you ask if you will notarize our contract. I do this of my own free will."

He cocked an eyebrow skeptically. "Really? As I read this, you are under threat of blackmail. That doesn't sound like free will to me. I suppose she already has some evidence to use against you."

"Yes, she does," I answered, "but I gave that evidence to her of my own free will. I really do want to do this."

I could feel my knees shaking. I knew what he would want, and I had only sucked a cock twice before. And I was drunk and did it on a dare. But I hadn't done it with a stranger, and I hadn't asked to do it. This was slutty behavior indeed. I knew he would want his cock sucked, though it hadn't been mentioned yet. Unless he wanted my ass! I'd thought of that possibility, of course, but now it was different. I was finding that there was a difference between thinking about something and actually doing it.

"I see," Mr. Appleton said. He turned his gaze to Rachel. "I want him naked, and I want both of his holes. I'm off work at six. How will we do this?" 

I heard Rachel talking to him, but what she said hardly registered with me. He was not only matter of fact about it, he seemed to me to have a predatory gleam in his eye. His demeanor seemed to me to have changed from affable salesman to something more sinister. He had a victim, and he was going to enjoy him. 



Rick's Embarrassing Adventures Ch. 06



While I was marinating in a trance of shame, Rachel made the arrangements. At least I think she did. She left the counter, and I hurried to catch up. Soon we were back out in the parking lot and into her car with my bags in the back seat.

"Rick," she said as I sat down, "before you put your seatbelt on, take off your shirt and shorts. You won't need them for the rest of the evening."

I looked at her in surprise but said, "Yes, Ma'am," and proceeded to peel my shorts down. I had to stop part way to pull my panties back up as I was exposing myself. "No," she said once she saw what I was doing. "Leave it out." I finished pulling my shorts off. "Toss them in back." I did then removed my shirt. Of course, my cock was hard. I looked around as I buckled my seatbelt around my now ample chest. "Put your hands under your buttocks and leave them there until I say otherwise. Now sit back and enjoy the ride."

I have never felt so exposed in my life. It seemed to me that anybody looking in could see the situation, and I could not cover myself in any way. My cock was rock hard, maybe as hard as I could remember since I was a horny teenager. I closed my eyes. Foolish, I know, but it was the only control I had. That soon changed.

I felt the usual motions of the car moving through the parking lot and out onto the road. Once Rachel was settled on her course, she turned to me. "Open your eyes, Rick. I want you to look around and act as normally as you can. I do hope we don't get stopped by a police officer. That would be very embarrassing for you, I'm sure." 

I groaned as I opened my eyes. Here I had been worried about people seeing in, and she was adding to my worry with this humiliation. But worse was to come. Once she had the car settled in for the drive--she was not using the freeway for the return trip!--she reached over and began to stroke my cock. God it felt good. Despite everything, I was horny as could be.

"Be careful, Rick. You don't want to make a mess."

I groaned. "If you do that for much longer, Ma'am, I won't be able to control myself. Oh, God that feels good."

"Goodie," she said gleefully. "Then you'll have to clean it up while I'm driving. That will be such fun." Then shortly she said, "Oh, look. There's a pickup truck coming along side on your side of the car. Look over there and smile while I try to match speeds with the driver for a bit."

I looked over at the mirror. Would I rather see a man driving or a woman? Then what? I couldn't cover myself. I couldn't stop what Rachel was doing. I was about to shoot my wad. I couldn't tell what was driving. Rachel was slowly stroking me. I realized that she wasn't going to get me off stroking that way and part of me wanted to get off, badly, but not here, not now. 

Just as the truck was passing us, Rachel had to slow down for other traffic in our lane. I caught a glimpse of the driver, a woman, but I couldn't get a lot of detail. She didn't look our way, so my forced smile was wasted.

"Oh, such a pity," Rachel said pleasantly. Maybe we'll have better luck at the light up ahead.

I looked ahead. Sure enough, there was a traffic light changing from yellow to red. We came to a stop behind another sedan-type car. As yet, no one in the right lane had stopped next to us.

Rachel's grip on my cock was suddenly firmer, and her strokes more purposeful. "Watch to the right, Rick. Tell me if anyone stops next to us. Oh, and you may cum if you dare to be even further embarrassed. I'm feeling generous."

I groaned under her ministrations. I could feel my orgasm building, and I was having trouble deciding what I wanted to have happen. I felt like I should try to hold off, but I didn't know if I could. It was harder and harder to concentrate on anything outside the car. I did know that the next car to stop in the lane to my right would be next to our car.

Then I could see a car coming. "Car!" I shouted. Then, "Oh, God!" as I started to cum. 

I tried to smile, but I'm sure my expression was more pained with that glorious pain that happens at orgasm. I knew my face was flushed. The car came to a stop, but the driver--a man it looked like in the mirror--was talking to a passenger and not looking our way, though I don't think he would have seen anything from half a car length back. Meanwhile, I felt like I was squirting like a fountain!

The light must have changed at some point, because I felt the car start moving forward. "Oh what a pity," Rachel said with false sympathy. "You've made a mess and no one but me saw it." Her hand let go of my cock and came up to my mouth. "Clean me up, Rick. Lick my fingers clean." I did so, but I was conscious that some of my cum had dribbled down my cock. Looking down, I saw that some was on my new bra. I could also feel some on my stomach. I was sure there was more I could not feel. But I kept my hands under my butt. I'm sure my face stayed red on its own.

After a few minutes, Rachel was satisfied that I had cleaned her hand, then she wiped her fingers on my face and neck until they were dry. All the while we were driving in the same clump of traffic we had left the light with. If the car to our right saw anything, I wasn't aware of it. Since they weren't directly across from us, were perhaps a car length back now, I assumed that they hadn't seen anything or weren't interested if they had. Rachel was just going with the flow of traffic, neither trying to drop back nor to speed up.

She didn't say anything for a few minutes and drove with both hands on the wheel. Finally, she spoke. "You can move your hands now. I want you to clean all of your spunk up. Get every bit and put it in your mouth and swallow it all."

I did as instructed, my cock now limp in my lap. It took a bit, and I wished I had some water to sip to get the taste out. By the time I was finished, we were turning onto her street.



Rick's Embarrassing Adventures Ch. 07



Chapter 7: A Climactic Encounter

"Pull your panties up. Once I park, you are to take your purchases and the clothes you no longer need to your car and lock them in. Remember your instructions. No running. Hands at your sides. Oh, and take your shoes off at the car, too. You won't need those either."

With that, she pulled into her driveway and went into her house. I felt very exposed while getting my bags and clothes out of the back seat, but when I looked around I couldn't see anyone looking back. I grabbed my keys out of my shorts pocket and began walking to my car, shopping bags in one hand, keys and clothes in the other. I saw no one on the way, but I couldn't tell who might be watching from inside their homes.

I put everything in the car and kicked my shoes off, conscious of the show I was putting on the whole time. Once I locked the car, I did a slow walk on the hot concrete to her door. I could feel my face flushing as red as I felt my feet feeling on the warm walk. Was that someone peeking out from behind curtains? I couldn't tell, but the thought had a predictable effect on my cock, which rose and strained against the panties.

At the door, I knocked and waited, per my instructions. Rachel didn't keep me long.

"Very good, Rick," she said as she stood at the door and gave me an appraising look up and down. When she saw my cock straining against the panties, she added, "Well, I don't need to ask you how you liked it." Then she opened the storm door and let me in. As soon as I was inside, I took off my panties, again per her instructions, and laid them by the door. Since she was there, I didn't need to find her, so I wanted for what would come next.

Rachel closed the door. "Come with me to the bathroom. You have a busy evening ahead of you, so I need to get you cleaned up."

Once in the bathroom, she said, "Take off the bra and forms and stand in the bath tub." The bra was not much of a problem, but the forms were glued on over my man hair and breasts. "Go on," she said when I hesitated, " it won't be any easier if you wait." So I took a deep breath and yanked on one breast.

Damn, but that hurt! I got the breast off with that big yank, along with quite a bit of hair. It brought tears to my eyes it stung so much.

"Do the other one," she said after letting me gasp for a short bit. "It won't get any easier."

It wasn't. In fact, I couldn't get it off with the first tug, but it did sting as bad as the first one had, plus I still had part of the breast form clinging to my chest hair. All I could do was take another breath and pull it the rest of the way off. It stung some more and my eyes teared up.

"Oh don't be a baby. Give me those and get into the tub." I did so, and she began to spray this yellow foam on my body. Soon I was covered from neck to ankles, and my body was tingling all over except on my chest where it burned like fire where the hairs had been pulled out. She even did my arms, and, yes, she did my cock and balls. My cock didn't much like this tingling sensation. It drooped.

"Stay right there until I come back. It will be a bit."

I don't know how long it was before she came back, but it was quite a while. I spent the time thinking about what had happened so far and wondering what would happen in this busy evening Rachel promised me. I was honest with myself. This was what I wanted. I wasn't sure I could take whatever she could dish out, but I was still game to find out.

And then I remembered that I had given her addresses and emails for everyone I knew: business contacts, friends, family, passing acquaintances, even enemies, because once you put someone in your email list, they generally stay even if you don't like them anymore. At any rate, I had to go through with it. And I was just as glad it was set up so I couldn't back out. I've dreamt of doing stuff like this for all of my sexual life, and now I was doing it.

Eventually, she did come back and supervised my taking a shower to get all of the foam with hair off. She left me to dry myself with instructions to come find her when I was done. I was not to dress.

I walked around her house feeling more naked than I ever had with no hair on my body below my head. Rachel was in her living room, and she was not alone. It was Mr. Appleton. He must have closed up shop early just to get at me.

"Rick, you remember Mr. Appleton, don't you?" Rachel asked, a mischevious smile on her face. 

"Yes, ma'am," I answered, reddening. I could feel my cock stirring just being naked in front of both of them. I was not attracted to Mr. Appleton; I'm not attracted to men at all. But the situation, my embarrassment, and my realization of what was coming had me getting hard. I wanted to cover myself, but I knew better. Instead I just stood in the entrance to the living room.

Mr. Appleton looked at me with an appraising eye, as if he were examining something he valued. I couldn't meet his gaze even as I could feel myself becoming very hard. 

"Come here, Rick," he said. I took a breath and walked over to where they were seated -- he in an easy chair and she on he couch. I stopped near the coffee table, facing them both but looking at neither. Instead, I was looking down at my now bobbing cock.

"It seems you are happy to see me," Mr. Appleton said. I didn't answer. 

"You are happy to see him, aren't you, Rick?" Rachel asked.

I hesitated but only briefly. I knew what I was supposed to say. "Yes, ma'am."

"Then tell Mr. Appleton that you are happy to see him. And tell him that you are happy to do whatever he wants."

I took a deep breath and let it out. "Yes, ma'am." Then to Mr. Appleton, "I'm happy to - to see you again, sir, and I am happy to do whatever you want me to do for you."

Mr. Appleton smiled and stood up. "Very good. Get on your knees. Good, now take my cock out of my pants."

I had knelt in front of him, so I reached up to find his zipper and pull it down. I fumbled a bit getting it down. I hadn't done this before, and I was conscious of his hardness behind the zipper. At the touch of my hand on his zipper, I both saw and felt his hardness. Then I reached in and pulled his cock out through the opening. 

Other than my own, this was the first cock I'd ever felt. It felt warm, as warm as my face felt. It seemed to get harder as I pulled it out of his trousers. It seemed thicker than mine but probably the same length. I knelt there looking at it grow in my hand until it felt as hard as a length of pipe. I felt mesmerized by it.

Rachel spoke, "Rick, look at me and smile." Her voice shocked me out of my trance, and I looked at her and saw her pointing her camera at me. She had to remind me to smile, and when I did, she snapped off a picture, momentarily dazzling me with the flash. More blackmail material, I thought, and I did it to myself. I knew at that moment that I would do anything, really and truly, not to have these pictures and videos get out onto the Internet.

"Now you go ahead and give Mr. Appleton some nice head. Don't mind me taking more pictures of you doing it."

Mr. Appleton spoke up. "I'd better not feel any teeth, and I want you to look at me while you're sucking me. Understand?"

"Y-y-yes, sir," I answered with a stutter. I was mortified. Whatever pictures Rachel had of me before were nothing to what she had now and would have. I was so embarrassed at the visual picture I had of what I looked like, and the picture made me so horny that I thought I might shoot without any touch at all. I felt like I was vibrating: with fear, excitement, and sexual tension.

I licked my lips and wrapped them around his cock, making sure to keep my mouth open so my teeth didn't touch him. I started slowly, wetting him as I slid him deeper into my mouth. He didn't taste of anything but skin; he must have cleaned himself up before he came over. I was surprised by how easy this was: just get him wet and slide my mouth up and down.

While the mechanics of the blow job seemed easy enough, looking at Mr. Appleton while it did it was humiliating. He had a smirk on his face that said I was acknowledging his superiority as a man, that he was the dominant male in the room, and I was nothing but his fuck toy. That he was right didn't make me feel better. And yet it turned me on like nothing I had done before.

"You like that, boy," he said, openly smiling now. "Don't even think of denying it. I can see it in your cock. Have you ever been as stiff as you are right now, kneeling in front of your lady friend and sucking my cock?"

Holding onto his cock with my mouth, I shook my head slightly. I could tell I was hard, and he would never believe it wasn't because of him, that it was because of the situation. But it didn't matter in any case. I was past the point of any return now.

Every once in awhile I would see a flash from Rachel's camera, and I could feel my face flush redder and redder as I imagined what I looked like in those pictures looking up into his eyes with what anyone would say was adoration and excitement, though I felt like it was embarrassing and humiliating.

I don't know how long this went on. Then Mr. Appleton said, "Go faster, bitch."

I dutifully sped up, holding onto his legs for balance as I kept looking at his face while bobbing on his dick and sucking. Mr. Appleton seemed to like me going faster. He moaned and groaned. Then he grabbed my head and began fucking my face. There was nothing for me to do but keep my mouth open and hope I didn't choke. He started driving and driving and then he pulled my face away just as I felt him start to shoot his load. He shot it right into my mouth as he pumped his cock with his own hand. 

Then he let go of my head altogether and said, "Clean me up with your tongue.." So I licked up what was dribbling from him, trying to be careful not to hurt him. (I'm always sensitive immediately after I've cum, so I assumed he would be, too. It wasn't that I felt something for him; I was just doing what I thought was expected of me in pleasing him while humiliating myself.

Once he was satisfied that I had cleaned him up, Mr. Appleton sat down and took a hand towel from the chair arm, dried himself, then put his cock back in his pants. Meanwhile, Rachel stepped in and snapped a few shots of my cum splattered face. When she stepped back, he tossed the towel at me. "Clean yourself up, boy. You look a mess."