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The Ribbons For years I have been trying to deal with this, and according to him, I haven't done very well. To be brutally honest, I don't like it, and I wish it would just go away. But, I'm even more tired of the problems that avoiding it seems to cause, so I have decided to give it to him in a big way. She invited me into the bedroom and closed the door. "I have a gift for you," she said indicating a number of packages with different colored bows. "Actually, it's a series of gifts." "Have I forgotten a gift-giving opportunity? It's not my birthday, it's not Christmas, it's not our anniversary and it's not even groundhog day. All of these are for me?" She smiled and said, "They're all for you, but you don't get to open them all now. For now, you just get to pick one. The others will come at another time. There's no special occasion, it's just because I love you." "So, which one do I open?" "You have to decide," she replied. "I will tell you that they are all related to your personal proclivities, and that the color of the bow is related to the contents of the package." I looked over the packages. They were various sizes, and the bows were in many different colors. My mind was racing. I had been trying to get her to be an active and dominant partner in my 'personal proclivities' for a long time, but at best she had been passive in her reaction to my quirks. Was she really going to take this kind of lead? My instinct was to pick the package with the pink bow, but I thought that might be too pushy. Likewise the black or the red. Thinking it would seem to be somewhat neutral, I picked the package with the blue bow. This is too funny. I thought sure he would go for the pink, or maybe the black. He probably doesn't really believe I'm serious. I think this will work out very well. Her smiled broadened as she handed me the package with the blue bow. "A very good pick. Under the circumstances, I think this will be quite appropriate. " I slowly opened the package, hoping for the best, but expecting far less. As it turned out, my hopes were far short of reality, but at that time, I saw only that the box contained a blue garter and an envelope. I looked to her, and she told me to open the envelope. It read: 'Something old, something new, something borrowed, and something blue. Congratulations, you are going to be a bride! I will arrange for everything; time, place, transportation, photographer, reception and honeymoon. Based on your tastes, you will want your gown to be very short, but white of course. We will make that along with a veil, and they will be your something new. You have a garter belt that you can wear, so that can be your something old. For something borrowed, I will loan you a slip and panties. We'll also have to get shoes and stockings. Here comes the bride! I was floored! "Are you serious? We're really going to do this?" "It's about time," she said. "You've been wanting to put a few painted toenails outside the closet for years, and I'm ready to push you out the door." Again the big smile. "Just like a real honeymoon, when it's over, you won't be a virgin anymore."
True to her word, we got started right away. Picking out a pattern for a dress, selecting material, buying shoes and stockings. All the while she refused to give me any more details about what was going to happen or when. I put myself completely in her hands. This was literally true during fittings. She cut and hemmed the dress so that it was only a deep breath away from indecent, and she took numerous opportunities to slide her hands under the dress and to fondle me. During these fittings I was required to wear strictly the appropriate undergarments, namely white slip, white satin thong panties, stockings, garter belt and white pumps. Needless to say, my body responded to the clothing and her fondling. Another important feature of the fittings was the video camera. She told me that part of the fun would be keeping a visual record of the whole event. At first she just set up the camera to record once I was dressed. But then she started bringing the camera into the room where I was getting dressed and recorded everything from stripping down to dressing up. It was embarrassing. The big day finally came. On Friday, after work, she began filming as soon as I came in the door. Following her direction, and under the constant eye of the video camera, I shed my clothes, took a bath, shaved my legs and face, applied make-up, wig, garter belt, stockings, panties, slip, dress and shoes. To finish off the look, I put on my veil and slid the blue garter up to the very top of my thigh. Since my dress was so short, it still peaked out, but it was a nice touch. With the camera off for a while, I waited while she got ready. Alone for the first time in these pretty, feminine clothes, I looked at myself in the mirror. I practiced walking and sitting. I found that it was impossible to sit without exposing myself to anyone who cared to look. Naturally, this gave me a real thrill. "So, how do I look?" She walked into the room wearing a tux, and looking quite handsome I thought. "It's time to get going so we don't keep our guests waiting." "Guests? You intend to let someone see me like this? Where are we going?" A dark cloud passed over her face at my questions. "You have been whining and moaning to me for years about how you wanted to dress like a woman, to be treated like a woman, even to be seduced like a woman. Well baby, tonight you are queen for a day, so stop pretending that this isn't what you want and get your sweet little ass in the car." What could I say. She was right of course, but I never thought it would really happen! The car was in the garage, so I didn't have to go outside, yet. She held the door for me, and I could see the smirk on her face when I sat down, swung my legs into the car and she got a nice look at my crotch. The "ceremony" turned out to be a private affair held in a secluded corner of a local forest preserve. The guests were forest creatures and stars. The moon officiated, and she was my groom. Even though there was no one around, that we know of, it was still very exciting to out in a public place dressed the way I was. At the end of the ceremony, she leaned me back and gave me a long, deep kiss. Breaking with tradition, she also felt me up. He was very cute in his mini-wedding dress. He carried a bouquet that I brought for him. I had found a tree stump to use as an alter. I arranged the video camera with lights to record the ceremony. He marched in while I waited at the alter. It was sexy and fun, but it was also moving. At the end, I was ready to have him right there, but I settled for dipping him and giving him a good feel. Our honeymoon consisted of a night at a motel where she was able to pull the car close to the door. Even so, there was still that thrill of having to walk in public to get into the room. We toasted our marriage, and my coming out, with champagne, and she admired the view when I sat down. Before we got down to the fun of consummating our union, she brought in the packages with the colored bows and told me to pick out my wedding present. With the first gift being just about concluded, I wondered which of the remaining ones would attract his attention. We now both knew that I was not only serious, but capable of pulling off a fantasy recreation for him. What would be next? The packages were the same as before. Looking back, I would have expected the bride fantasy to be identified with the white bow, not the blue. So what would be in the white? For that matter, the black, red, pink, etc? I took a deep breath and pointed to the silver, just because. With the return of the knowing smile, she said, "A fine counterpoint to your last pick. Go ahead and open it." The package was a bit heavier and made a metallic sound when I moved it. Inside, I found a pair of handcuffs and an envelope. The note in the envelope read: Bound hand and foot you will be, "Doesn't that sound like fun," she asked with her wry smile. "I'll bet you can hardly wait. But that's for later. Now I want to get my hands into your panties." We made wonderful, glorious love that night. Later, while she slept, I thought about how lucky I was. And I thought about the next gift. This one should be fun too. I'll have to think of some ways to make it a bit more than what he is expecting. It wouldn't do for it to be totally expected.
The next few weeks passed uneventfully, and no mention was made of the next gift. She asked me about my thoughts about the wedding. It was difficult to express my thoughts and feelings out loud, but I eventually told her how feminine and sexy I had felt. I tried to explain how there was a very special sexual thrill at being in public in a dress, and how the possibility of being caught was exquisite. I eventually was able to tell her that I fantasized being discovered by a couple of men. In my fantasy, I would be forced to perform fellatio on them and then they would rape me (gently and with a lubricant of course). Preparing for the next session was not too difficult, but I did want to let enough time pass so that he could enjoy the anticipation. I also wanted to learn more about his fantasies, so I questioned him about his reactions to the wedding. The things I learned were perfect for the upcoming bondage session. As an added bonus, they eliminated the need to invest in new costuming! About a month after the wedding, I came home after dark and found a note on the wall: Welcome home darling, it's playtime. Get yourself dressed up just like you were for the wedding, then meet me in the back yard. My body responded immediately and very positively. Needing no further encouragement, I did as I was instructed. It was wonderful to again slide the silky, sexy things onto my body. Only when I was dressed and made up did I give much thought to what was going to happen. God I was excited! I went to the back door and flipped the switch for the outside lights. Nothing happened, so I figured the light must be burned out. I got a new bulb and stepped outside to the light fixture. Fortunately, the area by the back door was shielded from view by the neighbors, so while I was jazzed to be again outside in drag, I didn't have to worry too much about being seen. As I reached above my head to remove the old bulb, I realized that my motion was pulling my dress way up exposing garters and thong panties. "Don't move an inch. Keep your hands up where they are and don't turn around" she ordered from behind me. I stood still with my hands above my head. A blindfold was placed over my eyes. She grabbed my wrists one by one and locked handcuffs onto them behind my back. Something silky like panties was shoved into my mouth preventing me from speaking. Unexpectedly I then heard a male voice, "Did you see the ass on this chick!" Before I could react, she whispered in my ear, "don't resist or you may be hurt. This is only what you wanted." She now spoke aloud, "O.K., just as we agreed, she's all yours. You kids have fun." I heard footsteps and then the back door open and close. Hands grabbed my arms, and the male voice said, "oh yeah, we're going to have a real good time now." The hands slowly slid down from my arms, to my hips, and to my thighs clad only in sheer nylon. Then they reversed their downward motion, and I could feel the hands go under my dress as they climbed. They quickly fond my crotch and I could feel the startled reaction as my true gender was found. The male voice sounded menacing, "shit, you're not a girl." In spite of the discovery, the hands continued to roam and fondle. "Oh well, I expected to get laid, so I'm gonna get laid. Come on sissy, let's go into the house where I can be comfortable." With that, he opened the door and pushed me inside. I was anxious, but not too scared since I knew she had set this up. My feelings were jumbled between extreme embarrassment at being seen dressed like this by a man, and extreme excitement for the same reason. I was pushed into what I think was the family room. It was much warmer and through the material of my blindfold I could sense that the light was much brighter. Hands on my arms stopped me and seemed to indicate I should stand still, although nothing was said. After a moment, I felt a hand on left ankle. The then felt something being tied around the ankle. Next, hands grabbed my right ankle and began pulling it to the right. I was forced to shift my weight to my left foot, but then my right foot was pulled so far out that my weight shifted again, leaving me standing with my feet about a yard apart. The hands holding my right ankle quickly tied something around it as well. The hands were then removed from my ankle. Being in high heels, I was a bit wobbly, but when I tried to bring my legs back together, I found that whatever was tied to my ankles made this impossible. Soon, the hands were back on me. They started at my shoulders and worked their way down. They slid all the way down my legs and gently stroked my thighs, coming closer and closer to my crotch. I felt totally helpless and vulnerable. I could do nothing to cover or protect myself. Just as I was sure the hands were going to grab my genitals, the hands stopped and left me. I was then pushed gently forward onto my knees. The gag was then pulled out. No sooner had a licked my lips and gotten some moisture back in my mouth, when something was pushed against my lips. Suddenly, the male voice was back, "Open up sissy boy, you know you want it!" What followed was like being in a dream. I was violated in all possible ways. I felt totally depraved because I enjoyed it so much. When it was done, the restraints were removed, and only then was the blindfold taken off. After blinking a few moments because of the bright lights, I noticed several things. First, she was the only person there. Second, the bright lights that I had sensed were floodlights that had been positioned around the room. Finally, I noticed that the video camera was recording. This one was really exciting to arrange. When I started with these fantasies I didn't realize how much I would get into them. A little part of me was getting back at him for the emotional difficulties his peculiarity had caused over the years. Plus, it was just so sexy! She turned off the camera and the lights, and then she asked, "ready for the instant replay?" Without waiting for my reply she urged me to sit in front of the television, and the show began. The television showed me standing in the middle of the room, resplendent in short white dress and high heels, blindfolded and handcuffed. She entered the picture and I watched and learned that it had been her who bound my ankles to a board that held them apart. The position had forced my dress to ride up a bit, and the front of my panties was now visible on the screen. She left the screen for a few moments, and when she returned she had taken off her outer clothing. She was now dressed in black corset, stockings and boots. She had also strapped on a realistic looking dildo that stood out erectly in front of her. She winked at the camera. I watched as she ran her hands over my body and legs. She then pushed me down onto my knees. The camera view was now from the side and slightly behind me. She maneuvered the dildo to my lips, then she activated a handheld tape recorder, "Open up sissy boy, you know you want it!" So that's where the male voice came from. I saw myself slowly part my lips and her pushing the dildo into my mouth with a movement of her hips. I remembered the feelings on my tongue and lips, and being sure that this was a penis that I was being forced to suck on. The television showed the dildo being pulled most of the way out and then thrust in again time after time. Eventually, she pulled it out of my mouth and activated the recorder, "I know you're disappointed that I'm not going to come in your mouth, but I want to save that for your other end." Next my left hand was momentarily uncuffed, both hands were pulled to the front and the handcuffs replaced. I was then bent forward at the waist so that I was now on my hands and knees, with the ankle restraints causing my knees and thighs to be spread apart. The camera angle now provided a very clear picture of my dress rising up to fully expose my ass. The tiny strip of the white thong panties could be seen separating my cheeks. She knelt down between my legs and began to caress me. She stopped for a moment to apply some lubricant to one hand, she then pulled aside the thong. Turning to the camera, she smiled and winked, then she slid her finger into my ass. Pleasure was quite evident in my moaning and squirming. After a time, she removed her finger and lubricated the dildo. This time she pulled my panties down as far as she could on my thighs. With another smile and wink at the camera, she moved her hips to very slowly slide the dildo up my ass. She established a slow rhythm of in and out strokes that had me squirming my ass back against her crotch. She reached one hand around my hip and began to stroke my cock. I remembered feeling like I had never been so excited in my life, and seeing it on screen was getting me excited all over again. It didn't take very long before I saw myself come with convulsions that shook my whole body. She quickly pulled back and out of me. She pulled the panties back up and then she left the screen. When she returned, the dildo was gone and she was dressed again. She then removed my restraints and the blindfold. I watched myself adjust to the lights and notice the video camera, and then the video ended. "Was it as enjoyable the second time as it so obviously was the first?" she asked with her big smile. I couldn't even respond, so she leaned over and kissed me while running her hand up under my dress. Finding my member that was again throbbing, she said, "I thought so, you enjoyed watching as much as you enjoyed being raped." She then lowered her head to my crotch and once again relieved the tension that had built up. After I recovered somewhat, she took me into the bedroom where the packages were again spread out. She directed me to make another selection. I selected the package with the yellow polka dot ribbon. Inside was a very small, lycra, yellow polka dot bikini. The note read: This will be so much fun. You get to go swimming while wearing this bikini. You will be just so cute. However, if you remember the song, you will also remember that the girl in the bikini lost it while swimming. I hope no one sees you!
She was pretty sly on this one. First she had me try on the bikini. The bottoms were barely big enough to cover my genitals. She arranged the top so that it covered little more than my nipples. Then she told me that we would be going to a public pool where I would be required to wear the bikini sitting around the pool deck and into the water. On the appointed day, I was instructed to put on the bikini, plus a short terrycloth robe that barely came below my butt. While in the car, she made sure that I was properly aroused by feeling me up and talking about how cute I would be sitting by the pool in my "pretty little bikini". We pulled into the parking lot for a motel I wasn't familiar with, and she insisted that I come in with her to register. I thought the desk clerk looked at me strangely, but he didn't say anything. Back in the car, she said, "I think the clerk may have wondered about your bra." I looked down, and sure enough, the cross strap of the bikini bra was showing where the robe was loosened. We drove to our room. On the way we passed the pool. There were 10 to 12 people sitting around in the sun. "There's the pool," she said. "I think you're going to enjoy it." I didn't say a word, but I wondered just what I had gotten myself into. When we entered our room, I was surprised to smell chlorine. You guessed it, there was a pool in the room! She just laughed and unpacked the video camera. There was a photo opportunity while I followed directions to remove my robe and lay down on a chaise lounge for "sunbathing". Then it was into the pool for fun and games. Not surprisingly. I did loose my bikini while in the water, and so did she. Having anticipated the need to make the choice, I quickly decided on the package with the pink ribbon. She picked up the package and told me to open it. Inside, I found a pair of pink, thong panties. The note read: It has been said that the brain is the sexiest part of the body, and while the brain may be "gray" matter, it is connected to various pink parts for expressing its sexiness. The key pink parts in this exercise will be your tongue and your lips. No, not like that. You will use those parts to tell me about your fantasies and to answer with complete honesty the questions that I will put to you. The pink panties are to help make the session more personal. You will wear only these while you talk. I will listen, ask questions, and fondle your other pink parts while you talk (particularly those covered by your pink panties). This was not at all what I expected, but it might be fun. On the other hand, being totally honest about fantasies could be risky, and embarrassing. We'll see. I was hoping he would take the pink first as it should help to refine some of the other "gifts". No matter, I plan to really make him squirm with my questions, and with my fondling.
It was a Saturday evening, about a month later. She had me prepare myself by taking a hot bath, putting on the pink panties and laying down on the bed. Wearing a sexy nightgown, she lit some candles, turned off the room lights and sat down beside me. She told me to close my eyes, then began to gently run her fingers across my chest. She wasted no time getting right to the "nitty gritty" in her questioning. Q Do you ever masturbate? A Sometimes. Q Tell me about how you do that. What do you do first? A Well I don't just start in furious stroking if that's what you mean. In fact, I usually build up to the physical stimulation with a period of mental stimulation. It's like self foreplay. Q I would like you to be much more specific now. What kind of mental stimulation are you talking about? A It is almost always visual. Most often it involves pictures, but sometimes it's a story or something on videotape. Sometimes it's me. Q You? What do you mean you? A You know, sometimes I dress up. Q Details sweetie, I want details. Imagine that you are going to get dressed up now. Picture it happening in your mind, and tell me exactly what you're doing. A OK. First I take off all of my clothes. Then I put on a bustier. It has hooks up the back and it takes a while to get it on. Next I sit on the floor and put on stockings. Q Tell me about the stockings. What color are they, what do they look like, how to they feel? A They're black with floral trim around the top. They are very silky to the touch. They hug my legs very tightly as I slide them on. The tops come just to the tops of my thighs. Q Whats next? And don't leave out the details. A I stand up and then move to connect the garters to the stockings. I look at myself in the mirror as I do this because the body position necessary is one that is totally female. I find it very stimulating to see myself doing it. I also think about how someone could be watching me. Perhaps through a one-way mirror or through a hidden camera. Q So you are excited by the idea of being watched while you dress up in women's clothes. Very interesting. Go on. A Next I put on a dress. It is very tight, short and clingy. It has long sleeves and a mock turtle collar to hide some of my body hair and to emphasize the shortness of the skirt. Then I put on high heels with a little ankle strap. Q So now you're all dressed up in sexy clothes. What do you do? A Mostly I look at myself as I move around. I imagine someone seeing me in different positions, and I look in the mirror to see how it looks. I am especially interested in what happens to my skirt as I move, so I will bend over in front of the mirror to see how much shows. I particularly like to see what happens when I sit down, so I'll put a chair in front of the mirror. I fantasize about someone looking up my skirt, and being helpless to prevent this violation of my privacy. Q It sounds like you're having a great time. Are you touching yourself while all this is going on? A I run my hands over myself, both to see how it looks while I am doing it and to feel the sensations of the various materials I am wearing. But, I don't get into serious touching yet. Q So what does it feel like? A Soft and silky, and very sexy. Its all very un-masculine. Q [she begins to caress my bulging panties] Then what do you do? A I move to the bed and lay down. I'm still completely dressed, and I begin to look through a magazine. Q Tell me about the magazine. Is it always the same, or do you look at different ones? A I have a number of different things I may look at. Magazines, individual pictures or pages from magazines, newspapers even some text stories. Q What is it you like to see? A I like to see people in short skirts or dresses, preferrably also wearing stockings. It is especially nice if the picture is somewhat revealing. You know, a shot up the skirt, a stocking top or a garter showing. Q You said people in short skirts, not women in short skirts. Was that a slip of the tongue? A No. I do like to see crossdressers dressed like that as well. Q Tell me about your favorite picture of a man in a dress that you like to look at to excite yourself. A He is on a bed on his hands and knees. He's wearing a short dress that has hiked up to expose the panties that he's wearing underneath. Q OK, you are all dressed up in women's clothes, you're laying on the bed, and you're looking at this picture of a man in a dress with his panties showing. Do you start to play with yourself now? A Yes. I first fondle myself through my clothes, and then I slide my hand inside my panties to tease myself. As things get more serious, I pull my panties to the side so that my genitals are exposed, and I begin to stroke. Q [she pulls my panties to the side, and begins to stroke my cock] Do you continue to look at the picture while this is happening? A Yes. I keep looking at the picture until the end. Q What are you thinking while this is happening? What goes through your mind as you lay there playing with yourself while wearing women's clothes and looking at a picture of a man in a dress with his panties showing? A I think about being the one in the picture and having others see me that way. Q Do you also look at pictures of women? A Yes, in fact, that is much, much more common for me. Q And what do you think about when looking at a woman? A Pretty much the same thing. I think about being the one in the picture and having others see me that way. However, I may also think about how I would look wearing the outfit that she has on in the picture. Q So you keep looking at the picture until you come. What do you think about just as you're about to climax? A At that point I sort of mentally "give" my climax to the person in the picture. I will think about how nice it would be to be coming inside the person. Q It sounds lovely. She continued to stoke my cock until I came with a gush. After a short rest, she brought forth the packages again. I selected the package with the red ribbon. Inside was a short, black, "wet-look" leather skirt and a knit blouse with red and white horizontal stripes. The note read: Red is the traditional color for prostitutes. Red lights and red clothes, red lipstick and red polish. All bring to mind the availability of sex for money, generally in the seedy shadows. Now it's your turn to be a part of this life. Properly dressed as a female hooker, you will go out onto the street to sell yourself. You won't be done until you've given a blowjob and been buggered out there on the street. Have a swell time. I no longer had any doubts that she was serious, and that another of my fantasies was going to be brought to life. This will have to be done carefully, otherwise he could get hurt or thrown in jail. Although that might enhance the fantasy. It would certainly increase the realism.
On the appointed day, she laid out clothes for me on the bed. In addition to the skirt and blouse, there was a well-padded bra, a garter belt, fishnet stockings, thong panties and zip-up, high heel boots. After I dressed, she applied makeup guaranteed to make me look like a cheap slut. A short, punk, blonde wig finished off the look. She had me walk around the house and pose for the video camera saying that the lighting wouldn't allow for "live action" shots later. She then steered me to the car, and she explained the rules as she drove. She would drop me off at a likely street location. I would be required to "work" that location until I had had one "in the mouth" and one "up the ass". All of the activity had to occur on the sidewalk or in an adjacent doorway. I assumed she had a plan that didn't really involve being out on the street, but she stopped the car in a dark business section and told me to get out and get to work. When I hesitated, she said, "you have told me that it has always been a fantasy to be forced to be a hooker. Well this is it Trixie. Get your ass out there and sell it. Otherwise, there'll be no more fantasy games for you." I got out of the car, and she quickly drove away. I looked around. It was late at night and all of the businesses in the area were closed. It was an upscale area, but the lighting was very dim. There was no traffic in sight. I stepped into a recessed store doorway and I was hidden from the street except for the section right in front of the store. After a few minutes, a car drove by. I could have sworn that the driver did a double take in my direction. I thought about where I was, how I was dressed and what I was doing. I realized that I had a throbbing erection. I heard footsteps coming my way. I couldn't bring myself to step out onto the sidewalk, so I stayed in the doorway. A man walked past without even turning my direction. Soon I heard another set of footsteps. I peeked around the doorway corner. To my relief it was her. Seeing no one else on the street, I stepped out on the sidewalk. I casually leaned against the building and even put one foot against the wall. It looked like she was going to walk right past, so I said, "hey baby, want to party?" She stopped and ran her eyes up and down my body, checking me out. "How much?" she asked. "$20 for half and half", I replied. "Sounds good, but I haven't got much time, so let's get it on." I took her by the hand and led her to the recessed doorway. "Do me baby," she directed. I knelt down in front of her. I rubbed the front of her pants and realized that something extra had been added. I zipped her fly down and was greeted by a dildo she had strapped on. I pulled it out and wrapped my lips around it and started sucking. After a couple of minutes, a car drove by and honked. "That's enough of that doll, it's time for me to do you. Stand up and bend over," she told me. I did as I was told. I bent over and put my hands on the wall beside the door. From the rear, she pushed my skirt up over my hips then pulled my panties down around my knees. I closed my eyes and moaned as she slid her greased dildo into me. She thrust in and out of me for a minute or two. Suddenly she withdrew and said, "oh no, it's the police!" In a panic, I straightened myself up and attempted to get myself covered with my minimal panties and skirt. Only then did I notice the smile on her face. "False alarm," she laughed. "But you were having such a good time, I think you should continue on your own. Get those panties down and work off that unsightly bulge in your skirt." "You want me to masterbate? Here on the street?" "Well, in the doorway actually. Besides, you were just getting fucked here, so what's the difference to a slut like you. Come on, get it on!" I did as I was told. I stood in the doorway dressed as a slut and beat off. She cheered me on, and I left a curious gift for the shopkeeper to find the next day. We walked around the corner to the car and drove home. Later that evening, she brought forth the packages. I selected the package with the orange ribbon. Inside was an orange leotard and tutu. The note read: I just thought this was cute, and I wondered what you would look like in it. I was also curious as to whether you would get excited while wearing it. We'll find out.
There's not too much to say about this one. We didn't make any special plans. It was just a quiet night when she announced that she wanted to see how I looked in my leotard and tutu. She said I looked adorable and she giggled. I tried to dance and she laughed out loud. Big surprise, I did get excited, and this fact was duly recorded on video tape. Later, the bed again had the array of presents arranged on it, and she told me to pick one. I selected the package with the green ribbon. Inside was a book and a green dress. The book was The Story of O. The dress was long, apparently full length, with a halter top. The note read: The heroine (if she can be called that) of this book is taught to be a sexual slave. Like her, you will soon begin a period of training. Until that time, you may wish to read the book to help you anticipate some of what may be expected of you. She wouldn't tell me any more at that time, so I spent the next weeks remembering what I had already done, and wondering what would come next. On a Sunday night she called me into the living room. She was reading a book. Without looking up she handed me a piece of paper and continued reading. The paper read: Your training is now beginning. You will follow all instructions immediately and without question. You will now remove all clothing before you continue reading this note. She continued to ignore me completely. I took off my clothes and continued with the note. If you work hard, your training will last for only 10 days. Otherwise, it could take much longer. You will strictly follow the following rules:
You will now prepare yourself for training. When you are ready, present yourself back here with the book. As directed, I went to put on the gown, garter belt, stockings and high heels. The gown had a halter top, and the back was open to my waist. The skirt was tight and it had a slits running up the front of each leg all the way to my hips. I had a full erection, and it caused the front of the skirt to tent out. As directed, I presented myself to her. She ignored me for a few moments, then she put down her book and looked me up and down. She stood and walked around me. She ran a hand inside one of the slits in my down and grasped my cock. "This is going to be a problem. It is ruining the lines of your gown. Make it go away." I turned toward her and asked, "How am I going to do that if you don't want me wearing any other undergarments?" She smacked me across the butt. "Remember your place! You don't question me. You keep your eyes down. You silly twit, to make this go away, you remove its energy like this." With that she proceeded to pull the front of my gown aside and masturbate me to orgasm while I stood there. She was careful to avoid getting anything on the gown, but there were puddles on the floor. "Quickly now, clean up this mess!" I wiped up the puddles and again stood under her scrutiny. The gown was no longer tented in front, and this seemed to please her. "Very good. Now sit here next to me and read aloud from your book." I sat down next to her being very careful not to cross my legs, however, I apparently had my knees closer together than she wanted them. She grabbed one in each hand and pulled them about six inches apart. "That will do," she said. I then began to read the Story of O to her. After about 20 minutes, she ran her hand up my thigh and under the front of my gown. She began to caress my genitals, and soon I was erect again. "Stand up you tramp!" she yelled at me. I stood up and the front of the gown was again tented. "I told you I didn't want this thing ruining the lines of your gown. Now, make it go away!" She sat looking at me, obviously waiting for me to proceed. I pulled the front of the gown aside and began to masturbate. "I don't want any on the carpet this time. You better use this glass." She handed me an empty glass and watched as I brought myself to orgasm and shot another load into the glass. "Well done. You may drink that now." I hesitated and she stood up and smacked my butt again. "I said, drink it." I drank it down. "I think it's time for bed now, you have to be ready for work tomorrow. Get yourself ready and I will bring along your restraints." Following my instructions, I removed the gown and the high heels. Clad only in garter belt and stockings I awaited her return. She brought in some apparatus in black leather with shiny chains. "This should prevent unauthorized self-fondling," she told me as she secured a leather collar around my throat. She then buckled leather cuffs around my wrists. Finally, my wrists were crossed over my upper chest and short chains were attached between the collar and the cuffs. The effect was to make it impossible for me to lower my hands below my shoulders. "I think you also need some help in keeping your legs apart for me." With that she attached cuffs to my ankles. These were in turn connected to a rigid bar that kept my legs spread several feet apart. This ended up being how I was prepared for bed for rest of the week. However, it would be a mistake to think that going to bed in this outfit was the total of my training. Each night after the light was extinguished, there was an interval of quiet rest. On the first night, this time was filled with general thoughts of what had happened, and what would come the next day. Plus, of course, getting used to being secured as I was. There was also the fact that my mental wanderings stirred me, and being unable to touch myself made this even worse. After a time, I did begin to relax that first night, and I thought I would drift off to sleep. But that was not what she had planned. Her hand began to gently caress my stockinged thigh. She ran her fingertips around the lace top of my stocking, and she snapped my garter. She explored my garter belt and then moved up to tease and pinch my nipples. Her other hand then made its way up my thigh and then dipped between my legs before encountering my genitals. A finger was gently, but firmly, inserted in my ass and then began a rhythmic in and out movement. All the while the other hand continued with my nipples. For my part, this activity had brought me to a fever of excitement. But it was an excitement that I had to bear without being able to do anything about. No hands touched my genitals, not hers and certainly not mine. The teasing went on until I thought I would burst. She then slowly withdrew her hands and left me to deal with my agony. It drove me crazy. And this was obviously the plan, as each night, this "foreplay" was the same. However, what followed was somewhat different each night. On that first night, after a wait that seemed endless, her hands returned, one to my chest and one to my ass. The hand teasing my nipples then moved slowly down my chest and across my stomach. It lingered around my garter belt, so close to my genitals that I thought I would cry out. Finally, her fingertips began to slowly caress my cock and balls. With the other hand still at my ass, I felt that I would soon explode. When she began to stroke my shaft in earnest, I did just that. She continued to stroke until my spasms of pleasure subsided. "You have been quite naughty my little tramp. You neither asked for, nor were granted permission to come. I was kind to you tonight, but you must do better." With that, she rolled over and went to sleep. I was left to try and sleep with my own come cooling and drying on me and the bed around me. The next night, I sought to end the agony of the foreplay early, and I asked permission to come before she even moved to my genitals. She gave my nipple an extra hard tweak and told me that I was in too much of a hurry. Later, when she had begun to seriously stroke my shaft, I asked again. Her response was a simple, "no", and she ceased her stoking and rolled over to go to sleep. I was frantic. I couldn't even roll over to press myself against the bed. It seemed like I laid there for hours that night, unable to do anything to relieve my excitement. On another night, remembering the result of asking permission, I chose not to ask. At the first shudder of my climax, she withdrew her hands and berated me for coming without permission. However, with her help stopped so early, the orgrasm was incomplete and I again was left quite unsatisfied and sleepless. Finally, at the end of the week, I managed to hold off on my orgasm, and I fairly begged her to let me come. Much to my surprise, she released my right hand, and while she continued to tease my nipples and finger-fuck my ass, I was allowed to masturbate under her watchful eye. Daytime had it's own brand of agony and ecstasy. Under my regular clothing, I was forced to wear garter belt and stockings, plus a special slip. This slip covered me from shoulders to knees in silky, feminine material. However, rather than being open at the bottom like a skirt, this garment had legs that ended in elasticized bands around my knees. The diabolical part of this particular garment was the fact that it had no fly of any kind. So, I was unable to use a urinal. Instead, I had to use a stall so that I could remove my shirt, pull down my pants, and remove the top of the slip whenever nature called. This of course meant that I was exposing my garter belt and stockings if anyone should be so inquisitive as to look over the top of stall. The other factor of the slip is that it fit loosely. Being used to wearing jockey shorts, I was constantly aware of hanging loose and of rubbing against the sexy feeling slip. Plus, I could always sense the snugness of the stockings and feel the outline of the garters through my pants. Needless to say, I spent much of the week hiding my almost constant erection. Most of the evenings were devoted to my learning how to pamper and please her. She taught me how to give her maximum pleasure with my hands and my mouth. I was also instructed in how to properly massage and bathe her. Whenever the spirit moved her, she would slide a hand into my gown to fondle my genitals or my ass. At times she would untie the halter top of my gown and tease my nipples. Some time was also spent in learning how to satisfy a man. A realistic dildo with balls attached was employed to allow me to practice giving a man pleasure with my mouth and hands. This same dildo was also employed to teach me various positions to employ when being fucked in the ass. I was never allowed to come during these training sessions. This was saved for bedtime as described earlier. By the way, it should be mentioned that she was careful to record the highlights of my training on videotape, although by now, I almost was unaware of the camera's presence. The next Sunday, she told me that I had done passably in my training. My reward was to be a selection from the dwindling array of gifts. I selected the package with the red, white and blue ribbon. Inside was a Wonder Woman costume. The note read: In this case, the proper title would probably be "Wonder IF it's a Woman". Do you suppose you will have super powers in this outfit? The Red, White and Blue Ribbon Well, I didn't end up having any super powers, but I did have a good time in that outfit. It fit like a glove (one size too small) and was made of a very sexy feeling material. When she ran her hands over me the first time, I nearly came right then. As instructed, I hammed it up for the camera and struck the traditional Wonder Woman pose. This cracked her up, and we had a lot of fun that evening. At the end of the evening, the packages were brought out. But before I selected, she handed me a sealed envelope. "You will open this after making your selection," she said. I then selected the package with the white ribbon. Inside was a small, white, lace apron. The note read: I know you have always wanted to be my French maid, and now's your chance. We will make a cute little maid's outfit for you, and then you will clean the house. Perhaps there will be a party where you can serve to the guests. Won't that be exciting! She began to laugh, then she said, "I think the timing of this is excellent for a couple of reasons. You recently completed your slave training and now you are ready to serve as my maid. Isn't that wonderful! Now open the envelope for the other reason." Surprise! You get a special treat. Since Halloween is coming up, you get to go out to a real, live costume party in whatever outfit you just selected! I sure hope you picked something fun! Still laughing, she said "It looks like you really will get a chance to serve some party guests as an adorable little French maid!"
During the following weeks, we worked on my uniform. It was to consist of a short, black, satin maid's dress; starched petticoats; ruffled panties; corset; suntan pantihose; black, seamed mesh stockings; black heels; white apron; and white lace cap. I was informed that the pantihose were to added to the mesh stockings so that I would be a bit more presentable in public. Much like the "wedding" preparations, getting ready to be a french maid required a number of fittings over a period of time while my uniform was being made. Something that was quite different was that I was expected to do all of the cutting and sewing. I was expected to be "correctly" dressed for the fittings of course, so I was obliged to wear the corset, the mesh stockings and high heels while I worked on the uniform. The petticoats and ruffled panties were to come later, so I wore a pair of black thong panties. Once again, she did not hesitate to stroke and fondle me while I was working and during the fittings. As Halloween got closer, I got more and more nervous and more and more excited. It became difficult for me to concentrate on other things. During the fittings, it appeared that the dress would fall to about mid-thigh, and would cover my garters and the tops of my stockings. Considering that I would actually have to wear this in public, I felt that would be more than revealing enough to be exciting. But then came the final fitting just a few days before the big Halloween party. I was again wearing my "working" gear, but this time I had been instructed to put on the requisite pantihose before putting on the mesh stockings. As required, the pantihose were a suntan color, seamed and sheer to the waist. She told me to strip out of the black panties I was wearing, and she presented me with a pair of white panties with ruffles on the rear. I obediently put these on and found that they went up over my hips to my waist, and that the leg holes were cut all the way up to the waist. They were made of a sexy, shiny, satiny material, and they were very tight across the front. As a result of the tightness of the pantihose together with the tightness of the panties, my bulge from my inevitable erection was noticeable but not excessively so. Next came 2 petticoats. These were a surprise because they were more frilly and full than I expected, and when I put them on, they stood out from my body. She then had me put on the dress, the apron, and the lace cap. Only then was I allowed to look in the mirror. Upon looking at my reflection, I first realized that the petticoats made the dress flair out almost horizontally from my waist. Not only did the dress not come down to mid-thigh as I thought it would, but the petticoats revealed my thighs and my panties! Turning around, the bottom rows of ruffles on the back of the panties were quite visible while I just stood there, and you can imagine how it looked when I bent forward. The view from the front wasn't any more modest. You could see the bottom few inches of my crotch peeking out from under the petticoats. As you are no doubt aware, I was very excited to see myself dressed this way. I continued to turn and admire the way I looked, and then she said, "I think everyone will be quite impressed with how cute you look in that outfit." I had forgotten! I would be seen at the party like this! I looked at my image again, this time trying to think how others would see me. My eyes zeroed in on my exposed crotch and the ruffles on my exposed panties. What would they think? "I'm not sure I can actually go to the party dressed like this," I said with a bit of a whine in my voice. She got a tough look on her face and pointed a finger at mine, "Listen you hussy, there will be no backing out now. You've wanted this forever, and you're going to do it. End of discussion." She then took a couple of polaroid pictures and taped them up in the bedroom. Then she put her hand under my dress and grabbed my crotch. "I want you to think about how you're going to look; how everybody is going to see you. And you know, a lot of them will know just how much you enjoy dressing this way. Maybe they'll be able to see this big bulge you've got in your little panties right now. They'll know what a sissy boy you are. Maybe if you're really lucky, some of the guys might even want you to suck their cocks. Wouldn't that be perfect?" For the next few days, I saw the pictures of myself in the maid outfit every morning and every night. In between, I couldn't get the images out of my mind. I was so excited! I was also made to clean the house while wearing my uniform. She would make a point of coming up behind me and puting her hand between my legs or grabbing my ass. "This is what the guys at the party are going to do to you if you give them a chance. Better watch yourself!" Finally, the big day arrived. Somehow I made it through the day, but all I could think about was that night. After dinner she told me to get dressed. Once I was dressed in my lingerie and uniform, she made up my eyes and put some lipstick on me, but she decided against a wig or heavy makeup. "It would spoil the fun if they didn't recognize you. I want them all to know who it is that's all dressed up like a sissy maid." At that point, I realized that this probably wasn't a great idea after all, and I told her so. She looked kind of sad and said, "I was afraid this would happen. We certainly don't want you to be embarressed, so we'll just play some games at home. I've got an idea, just close your eyes." Feeling relieved, I closed my eyes anticipating some sexy fun. "Now put your hands behind you," she said. I did so, and she slapped handcuffs on my wrists. This should be fun. Then I felt something around my neck. I opened my eyes and moved to look in the mirror. There was a black dog collar around my neck. "I thought you might try to chicken out at the last minute, so I prepared for the contingency. We are going to the party, and now your arrival will be much more dramatic." She ignored my feeble protests and put a long coat over my shoulders and then buttoned it up. Next she attached a leash to the dog collar. Pulling on the leash, she pulled me to the car. So off we went to the party. Pulling me by the leash we walked to the door. As we entered, I saw that the party was in full swing. A number of people immediately surrounded us, intrigued by my situation. She loudly explained, "He was really excited about what he picked to wear tonight, I mean really excited (wink, wink), but he got cold feet at the last minute. So, I had to persuade him to come. Is everybody ready to see his choice of costume?" There was a chorus of cheers, so she unbuttoned the coat and pulled it off of me with a flourish. I don't remember any of the specific comments that were made, but I was certainly the center of attention. Fortunately, while being ribald, and in some cases downright lewd, the comments were all good-natured. Soon, my moment of fame was over and the party went on. At one point later in the evening, I was pressed into service to deliver drinks. By this time, some of the party-goers had reached the "intoxicated and loose" stage. As I made my way through the crowd with a tray of drinks, my ass was patted and pinched several times. One guy (obviously in his cups) suggested that I give him a little bit of "French service". I told him that would not be possible as I was working. As the party wore on, I found her sitting on a couch in the den. The room was darkened, and no one else was there at the time. I sat down next to her, and she asked, "are you having fun?" I admitted to her that I had been very embarrassed, but that I had never been so excited. I told her that I was glad she had made me come to the party. With that, she leaned over and kissed me. She ran her hand up my thigh and over the bulge in my panties. "Oh, you really are packed in there aren't you. We better get you home and do something about that before you are permanently damaged." Much later that night, I selected the package with the brown ribbon. Inside was a brown rabbit's foot. The note read: The little bunny who belonged to this foot wasn't very lucky, but I'm sure you'll get lucky when you're a bunny, a Playboy Bunny that is.
This ended up being another fun romp. I had always wondered what I would look like in a playboy bunny outfit, and it was as bad as you might imagine. Nevertheless, it was fun squeezing into the tight costume that so prominently displayed my ever-present erection. She got a big kick out of my tail and my ears. That night's package selection was the one with the black ribbon. Inside was an old time black & white picture of a saloon girl showing fish net stocking covered legs all the way up to her thighs. The note read: Knowing how much you like to dress up and have your picture taken, we're going to go to an old time photo studio and get your picture taken just like this. What a fine momento you will have. She didn't fake this one in the least. We actually went to one of those old time photo studios in a nearby mall. We laughted while looking through the clothes, and then she said in a voice loud enough for the photographer to hear, "we ought to switch places, you be the saloon girl, and I'll be the sheriff!" The photographer laughed, but said he had no objection. So we took our respective costumes to dressing rooms to get ready. Coming out of the dressing room dressed as a saloon girl, I was surprised to find some other people had come into the shop. They obviously found my costume amusing. I had to keep my hands in front of me because my erection was rather obvious again. It was decided to pose me laying full length on a table with her standing behind me. I had my left elbow on the table and I was supporting my head with my left hand. I had my right hand in front of my crotch in an attempt to keep myself covered, but the picture must have been wrong. The photographer instructed me to put my right hand on my right hip. When I did so, I could see him smile before he took the picture. When we got the picture, the lighting and the material stretched across my crotch was just perfect to show my substantial bulge. No wonder the photographer smiled! At the end of the evening, I saw that there was only one package left. It had a gold ribbon. Inside was a little (very little) gold pleated skirt, a gold sweater with "PB" in blue letters, blue ankle socks and a pair of blue panties. The note read: You like to watch the female cheerleaders more than the games, so I'm willing to bet you'd love to dress like one. So, here's your chance. You get to try out for the girl's cheerleading squad!You'll even get to do a cheer for yourself. To get what she called, "the full effect", she decided to begin videotaping my "tryout" while I was getting dressed. Pantihose were added to the outfit to improve the appearance of my legs, and she gave me a sheet of paper with my "cheer" on it. Give me a P, give me an A, give me an NTY. She made me do the cheer a number of times, instructing me to jump up, spread my legs, bend over and so on. All the while she manuvered the video camera to get the panty shots that I always look for when I'm watching a cheerleader. Rah, rah! At the end of the evening, I didn't expect any more packages since tonight's had been the last one. To my surprise, she brought one out with a purple ribbon. Inside was only a note. The note read: This has turned out to be more fun than I expected. It has also been much more exciting than I imagined. I think that there will be more new packages in the future that we can enjoy together. But next time we're going to have a film festival and remember just how yummy you have looked until now, my little Panty Boy! And so it goes. Go to Top of Page |
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