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Chicago By Suzi (Johnson) Thomas I was in Chicago, but I really didn't want to be there. My company was a sponsor of an investment seminar that was being given as a fund raising event for the university that our chairman had attended, and as my boss had explained to me, the company had to send representatives to "show the flag." As though a $50,000 contribution weren't enough, the chairman had decided that two portfolio managers had to show up as well. I was selected to represent the equity side and an attractive young woman by the name of Mindy was representing the fixed income department. We had sat next to each other on the flight out from New York, complaining about our fates; each of us would have preferred to stay in the office managing the portfolios assigned to us, but when the chairman speaks... My boss had told me that I didn't have to attend the sessions, since they were designed to instruct less sophisticated investors in various investment techniques, but that I would be expected to attend the social functions planned over the course of the three- day event to mingle with the attendees. Mindy had been given the same marching orders by her superiors, so we both faced three days and nights in the Windy City in early March, with only a series of lunches, dinners and cocktail receptions on our schedules. I had only met Mindy at a few meetings at the office, and didn't really know her well at all. As the plane headed west, we chatted for a while, and found that our backgrounds were fairly similar. We had both attended good colleges before joining the company and had been working there for about four years. I am single, and unattached, but we didn't discuss our personal lives at all, just mostly talking about the waste of time the next three days would be. We grabbed a cab from the airport to the hotel and checked in. Mindy was taken care of immediately, but there was some mix-up with my reservation, and it took a few minutes to straighten out before I was able to head upstairs. I had told her that I would meet her at the cocktail reception that was the opening event later that evening. I unpacked my suitcase, grumbling to myself about the inauspicious start of the trip. I had a few hours to kill before the reception, and, when I turned on the TV, I was glad to see that at least I would have cable to watch to fill up the better part of the three days. I knew that I wasn't going to be doing any sightseeing, given the cold, windy weather outside. I watched some college basketball on ESPN, and then changed into a suit for the reception. As I left the room, Mindy was just closing the door of the room next to mine. The hotel had assigned us to rooms that were next to each other, and I realized that the extra door in my room led to her adjoining room. A brief fantasy crossed my mind about the two of us, but in today's world of sexual harassment, I immediately dismissed it. Not that I would have minded getting to know Mindy better: she was an attractive redhead, as tall as I was in her heels, and in her black cocktail dress, I could see that she had a dynamite figure. She had worn jeans and an oversized sweatshirt for traveling that had hidden her body, and in the office, she wore suits, which disguised her curves. I told her that she looked very nice, and she thanked me, but my comment was really out of politeness, not a come on. We rode down in the elevator and she said, "God, I hope this is not as boring as I'm afraid it will be," and I agreed with her. Unfortunately, when we walked into the room, putting on our nametags, it didn't look very promising. Everyone was standing in stiff little groups, as was often the case at these affairs, clustered around the bars and food tables. We walked over and got ourselves drinks and started walking around the room. We ran into the University president, and the professor who was in charge of the seminar, and we introduced ourselves. They were very happy to meet us, since our company had made such a large contribution, and talked about what was planned for the next few days. In a few minutes, however, they said that they had to "mingle" and invited us to do the same. When they had walked away, I said to Mindy, "right, just what I feel like doing for the next hour and a half - introducing myself to total strangers and discussing the lousy weather." She laughed in agreement, and after we got some food, we moved into a corner of the room, out of the flow of people. We stood there talking in a little twosome and had several drinks. After we had exhausted small talk, the liquor loosened us up a bit, and we started discussing more personal things. I told her that I had dated a number of women, but no lasting relationships had resulted, and she volunteered that she had been dating one man for about three months, but they had recently broken up, because "we were headed in different directions." She didn't go into what those directions were, but I guess we came to the same basic conclusion - that we were both free and we'd be spending the next three days in each other's company. The reception began to break up, and we decided to head to the hotel bar for another drink. It turned out to be a few drinks, and I was decidedly starting to get turned on by her. We had continued talking, and I could tell that she wasn't happy that she had broken up with her boyfriend. She still didn't elaborate on the reason, but I was getting signals that she found me as attractive as I found her. "I've had about enough of this bar," she said, "I think I'll head upstairs." "Me, too," I said, and we headed to the elevators. When we reached our doors, she said, "I feel like a nightcap, would you like to join me?" When I said, "Sure." she opened the door and we walked in. The university had arranged for a small suite for her, with a living room plus the regular bedroom. I thought to myself this was pretty comfortable, and told her so. "I guess the mix-up in the reservations cost me one of these. I just have a regular room, unfortunately." She went over to the minibar, got out two Grand Marniers and poured them into glasses over ice. We sat down on the couch, and she invited me to take off my jacket and get comfortable. When I did, she moved over next to me, and, looking me straight in the eyes, gave me a kiss. By this time, we were both high from the drinks we'd had, and I found myself kissing her back passionately. I tasted her lipstick, and her tongue probed between my lips. I was completely aroused by this point, and my hands started caressing her, touching her breasts, which pushed forward through the silky material of her cocktail dress. Suddenly, she broke free from my embrace, and said, "I-I'm sorry, but maybe you'd better go now. I don't think you want to go any further." This comment puzzled me, because by this point, I really did want to go a lot further. "What do you mean," I asked, "that I wouldn't want to go on?" "I'm sorry," she responded, "I don't mean to be a cockteaser, but I-I'm a little weird about having sex. That's why my last boyfriend and I broke up. He didn't like what I liked, so he left." I didn't know what she might mean by weird, but I was so horny that I really didn't care either. "Listen, whatever you want is okay with me, I'm open-minded, Mindy." She said, "No, I don't think so, it's just too strange, really." By this point, I truly didn't care what was on her mind; I just wanted to get laid! "Mindy, listen to what I am saying. No matter what it is, I'll go along - just tell me what you want- anything at all, and I'll do it." "Are you sure that you're game for anything," she asked, "Whatever I want?" When I told her yes, she explained that she wanted her lover to dress a certain way, not saying what that was. "I'll lay out the things I want you to wear on the bed. You go in and look, and if you're still willing to go along, come back out here with them on. If you don't, just say goodnight and go back to your room, and we'll forget this ever happened." By this time, I was well past high, and I agreed. She went into the other room for a few minutes, and then reappeared. "O... Okay, you can go in now." As I walked into the bedroom, I heard her sobbing softly to herself on the couch. Although I thought to myself, this is one strange girl; it was not until I looked at the clothes she had laid out for me that I realized just how strange. Laid out on the bed were women's clothes! I saw panties, bra, garter belt and stockings, all black. Next to them were a sheer robe and a pair of black high-heeled shoes. I knew that if I walked out without putting these things on, I was going back to my room alone and unlaid. "Oh, well, what the hell," I mumbled to myself. "I don't care what I wear - it's the panties she's wearing I want to get into!" I stripped off my clothes and put my arms through the bra straps. I struggled to hook up the back, making sure that everything was flat against my body. Having the elastic around me certainly felt different, but when I pulled the lacy panties up my legs, I wasn't ready for what I felt. When the material touched my erect cock, I got a tingling sensation unlike anything I had ever felt before. A warm wave of pleasure washed over me as I settled my cock inside the front of the panties. I sat still for a minute, experiencing the new feeling, and then hooked the garter belt around my waist, slipping the hanging tabs beneath my panties. I got an even greater rush as I rolled the first stocking over my leg. This was turning me on even more, as the sheer nylon slid up onto me and I attached the garter tabs. When I had put on the next stocking, I stood up and felt the silken smoothness of all the garments moving against my body. I had never felt anything like this before, and I realized that wearing women's clothes was exciting to me! I managed to squeeze my feet into the high heels, which were much too tight, and struggled to maintain my balance with the unfamiliar height and position they put me in. I slipped into the sheer robe, and the strange sensation covered my entire body. The material of the bra cups flat against my chest tingled my nipples as I walked over to the mirror to see how I looked. Staring back at me was a sexy-looking woman, except for my flat chest and short hair. I walked over to Mindy's suitcase and saw all her other underwear inside, and I stuffed a pair of panties in each bra cup. The nylon of the panties rubbing against my nipples felt even better than the bra material, and formed two fake tits under the robe. Completely dressed, as she wanted me to be, I walked out of the bedroom and stood in front of her on the couch. She jumped up, still fully dressed in her cocktail outfit, and said, "You're really wearing them, you really are!" She took me in her arms and started kissing me again, running her hands all over my body. She turned around so I could unzip her dress, and she quickly removed it. I saw that she was wearing underwear that was very much like what I had on, although her breasts were pushing almost out of her bra, and there was no bulge in the front of her panties. She started rubbing her tits against me, and pressing her pussy against my nylon covered cock. After we had kissed and touched each other for a while, she kneeled down in front of me, and pulled my panties down around my thighs. My cock was fully erect, but when the material that had covered me stopped touching me, I was surprised to find myself missing how it had felt. Her lips replaced the sheer nylon, however, and she began to suck on my cock. "Wait, you'll make me come right now," I told her, but she continued to lick and suck on me anyway. I felt myself begin to come as she deep-throated me, and I shot my cum into her throat. She had her hands behind my ass cheeks, and she pulled me even deeper inside her mouth. She stood up a minute later, and taking my hand, she led me into the bedroom. "Thank you," she started to say, but I put my finger to her lips to silence her. "I said I'd do anything, there's no need to thank me." We lay down next to each other, and her hands continued to roam over my nylon-covered body. The sensation was thrilling to me, and I felt my cock getting hard again. Meanwhile, I was touching her all over, and when I put my hand on her panty-covered pussy, I felt how soaked the material was from her cunt juices. I moved my mouth to her tits, removed them from the bra cups that covered them and began to lick and suck on her erect nipples. After just a short moment, her body began to spasm in climax. I moved further down, and I could taste her juices through the material covering her pussy. I pulled down her panties, and covered her sweetness with my mouth. My tongue probed her clit, and she came again and again, her wetness covering my face. I moved back up her body, positioning my cock to enter her waiting pussy. "Wait," she said, "please be gentle, I-I'm a virgin." That was the last thing I had expected her to say, and I hesitated, still poised above her. "No, it's all right, please, come inside me," she urged, and I felt her pulling me toward her. The tip of my cock began to slide into her wet cunt, and I felt the sheer nylons I wore rubbing against hers. When I was about halfway inside her, I met resistance, and hesitated again. She gave a strong pull on me, and my cock broke through the resistance, plunging deep inside her. Mindy gave a gasp from the pain, and lay still for a minute, then her body started to move up and down under me. I couldn't hold back any longer, and I started pumping in and out of her in long, deep thrusts. Her hands continued rubbing all over my nylon-clad body, first feeling the bra under my sheer robe, then running down to my stockinged thighs. I realized that I was just as excited from the feel of her clothes on my body as I was from her touching and being inside her, and, with a final thrust, I felt myself coming inside her as she also orgasmed around my cock. We lay there in silence together for a few minutes, and when I started to say something, it was her turn to quiet me with a finger on my lips. "Please, don't say anything now. We can talk in the morning if that's okay with you." I said, "Sure, that's all right with me," because between the liquor I had drunk, our lovemaking, and the strange sensations I was experiencing from the women's clothing I was wearing, I didn't really trust myself to be able to speak coherently. I did know that I liked how these clothes felt on my body, though, and that was the most puzzling thing of all. Mindy asked me if I wanted to take them off, and when I said that I really didn't - that I liked how they felt, she just smiled at me. After a while, she got up and went into the bathroom to wash off the small amount of blood that stained her thighs. When she returned, she took off her clothes, changing into a sheer pink nightgown. "You'll probably be uncomfortable in those things later on, Jim, why don't I lend you a nightgown to sleep in?" The thought excited me, and even though I was reluctant to take off the bra, garter belt and stockings, I also wanted to see how a nightgown would feel against my body. Mindy helped me to remove my outfit, and to put on a silky white gown. The feelings I got as it slid over my body were the same tingling, exciting sensations I had felt when I was wearing her underthings. "Would... would you like panties to wear underneath the gown," she asked shyly, and when I nodded "yes", not trusting my voice, she knelt in front of me to pull up a pair of sheer white panties over my legs. My cock stirred as it felt their smooth touch, and she arranged the nylon around my cock and balls. She got into bed next to me, and we cuddled for a few minutes, nightgowned bodies close together, and in a few minutes I felt her drift off to sleep. I knew I should have felt silly, laying there in a woman's panties and gown, but the wonderful sensations they were causing me to have made that unimportant. With a bunch of mixed-up thoughts running through my head, the liquor and exhaustion finally overwhelmed me, and I also fell asleep. When I woke up the next morning, I knew I was in a strange bed, and when I opened my eyes, I saw Mindy in bed next to me. I had a raging hard-on, and I realized what I was wearing. The events of last night came back to me then, and I remembered how much I had liked wearing Mindy's clothes. The wonderful sensations of last night, feeling the silken embrace of the nylon around me, were just as strong this morning, I found, and as I shifted in bed, the nylon rubbed my cock in a sweet caress. I still was trying to sort out these strange feelings I had when Mindy woke up. I gave her a little kiss and said good morning, a little tentatively, not knowing how she would react to seeing me wearing her things now that she was sober. She smiled and ran her hands over me, though, feeling my body through the nightgown. Her eyes widened when she found my erection, and she directed her touches there, saying, "would you like to make love to me?" Of course I wanted to, and I held her in my arms, feeling the smoothness of her body under her gown. Almost before I knew what was happening, she had freed my cock from their nylon prison, sliding down but not removing the panties, and she pulled me over on top of her. She was wet and ready for me to enter her, and I slid myself inside, plunging deep, this time without any resistance. I found myself coming too quickly, before she was ready to come, but I couldn't stop myself, and I shot my cum into her. I knew she was as excited as I had been, and I withdrew from her and moved down to eat her. This was a change for me, as I had always been more concerned about my own pleasure than that of my partner. Some overwhelming feeling gripped me, making her pleasure important to me, though, and I licked on her pussy. Her juices mingled with the salty taste of my cum on my lips and tongue as I tasted what it was like for the first time. Her hands held me tight against her mound, and she was soon overcome by her passion. After we lay next to each other for a while recovering from our lovemaking, she started to speak, "Jim, thank you for putting up with my weirdness." When I started to respond, she said, "No, please, let me finish." I waited for her, and she told me the reason she had wanted me to dress as a woman. Her college roommate had been a lesbian, but had never made a pass at her until one night late in their senior year when they had both been to a party and came back to their room drunk. She said that they had made love, but when she woke up the next morning, and she realized what had happened, she was horribly upset. Her feelings were all confused, and had remained that way ever since. She and her roommate had been lovers for the month or so that was left in the semester, but when they graduated, she knew that she was not really a lesbian. She wanted to make love only with men, but the feelings she had experienced with her roommate persisted in that she wanted to feel her lover wearing women's clothes. "I told you I was screwed up last night," she said, "and when I told my boyfriend about this he got disgusted and broke up with me. You probably feel the same way now," she finished, bursting into tears. I held her in my arms, comforting her for a while, until I could no longer hold in my own confession, "Mindy, I-I can't explain it, but... I'll admit that I decided to do as you asked because I was so horny; all I could think about was getting laid. But when I started to put on your clothes, I knew that I had never felt anything as wonderful as how they felt on me. I got even more excited than I had been, more than ever before. I had always liked how women's underwear felt on my hands when I had made love before, and how they felt rubbing against me when I held them. I- I just never realized that I would want to wear them, too." "Are you telling me the truth, Jim, or just trying to be nice to a sick-o," she asked. "No, it's the truth," I answered, "I've never felt anything so wonderful." She hugged me tightly to her, and whether we were two weirdoes, or perverts, or whatever didn't matter. Our mutual desires had come together into a relationship. By this time it was midmorning, but we didn't have anything scheduled until a luncheon later on, since we weren't attending the seminar sessions. I said that I wanted to take a shower, and I took off my nightgown and panties. I realized then that I didn't have any clean clothes, since I was in her suite, so I put back on my own things to go back to my room. I was unsure when I got there what to do, so I walked over and opened the door that led to her room. She was standing there, having opened the door on her side, and I gave her a hug. "I'll just take a minute," I said, and when she said, "Okay", I went into my bathroom, stripped off my own things, and stepped into the shower. As I soaped myself up, the glass door slid open, and Mindy came into the shower with me. She took the soap from me, and continued soaping me all over, spending extra time when she reached my groin. Her touch gave me an erection, and taking the soap back, I started to lather her body. For the first time, I took a good look at her magnificent body, and saw that she was a natural redhead. The water cascaded down over her firm, perfectly proportioned breasts, running down her length and off her long, smooth legs. As I played with her nipples with my wet, soapy fingers, I felt them get harder and longer, and she pressed her body up against mine. She took hold of my rod, and guided me toward her pussy. As the water poured over us, we came together with strong orgasms. The water washed off the soap, so I shut off the water and we stepped out of the stall. We dried each other off with big fluffy bath towels and we began to get cold standing there. So we ran back to her room and jumped into bed, huddling together for warmth. We talked for a while, realizing that she had made love to me when I was naked, and we knew that, having done so, her hang-up about what her lover wore might have been overcome. "I feel so... so normal," she said, "now that I know I can make love to you without your wearing women's clothes." "Yes," I answered, "and it was wonderful, but..." "But what?" she asked. "But I liked how they felt on me," I blurted out, and she laughed. "I didn't say that I don't want to make love when you're dressed anymore, and I was thinking about how you looked when we were doing it. Just that you don't HAVE to be dressed up in women's clothes!" We held each other for a while until it was time to get ready for lunch. "C-can I borrow a pair of your panties to wear under my suit," I asked in a quiet voice, "I would really like to." She giggled and said, "Can't stay out of my pants, can you?" She handed me a pair of lacy pink panties, saying that we would have to do some shopping that afternoon, or else she would run out of clothes. I went into my room to dress, feeling her panties rubbing against me as I walked. I would have to work on controlling myself, I thought, or I would be hard all through the luncheon. We went downstairs, and sat through the lunch and the speech that followed, and as we looked at each other, I knew that neither of us could wait until it was over. When it finally was, we practically ran back to our rooms, and we began to talk excitedly. "Would you like to go shopping for some things now," she asked, "or would you rather make love first?" "That's a hard choice in more ways than one," I said, taking her into my arms, "but stores stay open pretty late, don't they?" She practically ripped off my suit, stripping me down until I was only wearing her pink panties. Her dress disappeared in a flash, and she came into my arms, wearing her bra, panties and panty hose. When we had fondled each other for a while, I was ready for bed, and so was she. She nibbled on my cock through the panties, and then pulled them part way down, so she could climb on top of me. She raised herself over my shaft, and in one smooth motion, impaled her pussy on me. We made tender love, caressing each other's body, until we reached a mutual climax. She asked me, after we had rested for a while, if I really wanted to buy women's clothes of my own. I told her that I honestly didn't know if this was just a temporary phenomenon, caused by last night or not, but that I really did want to have them, at least for now. When I said that, she leaned over and kissed me. We got dressed quickly and hurried out of the hotel to shop. The hotel was in downtown Chicago, and there were all kinds of stores in the immediate vicinity. As we looked around, she asked me whether I wanted to dress up entirely as a woman to see what it felt like. I only had to think for a split-second before saying that I would like to try it, and she took me by the hand leading me into a Payless discount shoe store. "They don't have clerks to fit you in here," she explained, "all the shoes are out on shelves to try on." She asked me what size men's shoe I wore, and she mentally translated into women's size. I looked around at all the women's shoes that lined the shelves, and she asked me what color I wanted. I spotted a pair of red patent leather heels that looked very sexy, about three inches high, and I pointed them out to her. She looked for the right size and width, and we brought them to the front to pay. I took the package and we walked out of the store; I was thrilled to own my very first item of female clothing! We went into a large department store next, and headed straight for the lingerie. "Oh, isn't this sexy," Mindy said, holding up a red satin and lace garment that had bra cups on top, extending down for twelve inches or so, with garters attached to the frilly bottom. "This is called a bustier," she whispered, "do you like it?" "Yes, very much," I told her. She picked out a pair of panties to match, red, with ruffles of lace all around. "I spotted a beautiful dress for you as we walked in," Mindy said, "and these will be perfect underneath it." I had an erection from thinking about wearing these dainties, and my cock rubbed against the pink panties I had on under my suit. Fortunately, I was wearing a raincoat because of the cold weather, so nothing was visible in the crowded store. Mindy picked out some bras, panties and other goodies including several pairs of sheer stockings for me, and we paid for my new frillies. When we walked into the dress department, Mindy headed for the cocktail dresses, and I followed along behind her. She pulled a strapless red gown off the rack and looked at me for approval. I was speechless as I looked at the satiny material with the abbreviated top and full flared skirt. She held it against herself, measuring it by eye to make sure it would fit me. "Dear, would you hold this up for me," she asked, "So I can see how it hangs?" Like a befuddled husband, I took the dress from her, holding it in front of me for her inspection. "This will be perfect," she said. After we had paid, we walked out of the store, loaded up with the packages. She told me to wait for her with the packages while she went into a drug store. I spotted her moving up and down the aisles through the window, and she rejoined me in a few minutes, carrying yet another bag. "One more stop to make," Mindy said, halting in front of a wig store, "do you want to be a blonde or a brunette?" "Uh, a blonde, I guess," I said as we walked in. "How about this one," she whispered, pointing to a curly shoulder length wig in a honey blond color. "Looks fine to me," I said, as she tried it on to show me how it would look. We walked over to the cashier who said, "that's a big change from your regular color, dear, but it should look fine on you." Mindy laughed, pointing to me, saying, "He wants to show me that blondes have more fun." We all laughed, and we hurried out of the store and back to the hotel. Unfortunately, we had to get ready for the dinner that was scheduled for less than half an hour from then, so I could only look at my new clothes quickly, before changing into a different suit. I kept on Mindy's panties, however, underneath, not wanting to miss how they felt on me. We were dressing in our own rooms, and I heard Mindy walk through the connecting door. I had just finished combing my hair, and was all ready for the dinner. When I walked out of the bathroom, I thought for a minute that Mindy had put on my things - she had on high red heels and a red cocktail dress. I realized that these were hers, since the dress was a sheath that hugged every one of her curves. "You look beautiful," I said, "absolutely gorgeous!" "Thank you, kind sir," she said, "I wore this so we could be twins later on." The thought excited me, and she saw the front of my pants pushed out by my erection. "That will never do," she said, and walking across the room, she knelt down in front of me. She unzipped my fly, and giggled when she saw the panties underneath. "Oh, pink goes so well with your navy suit," she kidded, and then taking out my cock, she began to suck on me. I had been so excited by buying all my new clothes that it didn't take more than a minute or two before I began to spurt cum deep down her throat. She licked every last drop off me, and I raised her up to kiss her lips. I could taste the flavor of my cock in her mouth as we kissed. "I have to fix my lipstick," she breathed, and I followed her back into her room. With a quick, steady hand she reapplied the bright red gloss to her lips, and we were ready for dinner. The dinner was good, but the speeches following dragged on. Before they were finished, I said to her, "let's get out of here, I can't wait any longer." She nodded in agreement, and we walked out of the darkened ballroom unseen, along with some others who had apparently also been bored. We hurried back to the room and I took off everything except my panties. Mindy sat me down at the dressing table, facing away from the mirror, and started putting makeup on me. Her hands seemed to fly as she softly touched different areas of my face. She smoothed a velvety liquid all over my face, and then softly touched a powder puff over that. I felt her putting false eyelashes on my eyelids, then applying eye shadow with a soft brushing motion. She rubbed blush on my cheeks and then applied lipstick to my mouth. When she stepped back to look at me, she gave a small gasp, and said, "Beautiful, you're just beautiful!" She wouldn't let me look in the mirror, though, saying she wanted me to see everything at once. She attached false fingernails over my own nails, and when I looked at my hands, it was so strange to see the long red nails on the ends of my fingers. I was a little excited by all this, though not seeing what I looked like took a little bit away from the thrill. "Time to get dressed now, and I immediately got very excited thinking about what was to come. Mindy pulled down my panties, and I stepped out of them. She handed me the bustier, and I held it against my chest as she went behind me to hook it up. It drew my body in tightly, restraining lace, elastic and me inside the satin. I had to adjust my breathing for the confined space I had to work with, and in a minute, when she saw that I was okay she led me to a chair. As I sat down, she said, "Sorry that's so tight, but that's the price we women pay for fashion." She stuffed the bra with two pairs of panties in each cup, and then knelt down in front of me. She was beginning to put on a stocking when she said, "You're legs aren't very hairy, but everything will show through these sheers." "I-I guess we'll have to shave my legs then, won't we?" I asked. "But won't people see you, in a gym, or something," she said. "No, I workout at home, not in a health club, and it's March so I won't be wearing shorts for months." "All right, if you're sure," she said. I knew that I wanted to look perfect in my female attire, and that was all that mattered right now. I stood in the tub, and she used her razor to remove my leg hair. I am very fair-skinned, and had very little hair on my legs and none on my chest. She shyly asked if I wanted her to shave my underarms as well, and remembering the strapless gown, I said sure. When that was done, I sat back down in the chair, and she pulled the stockings over my sleek smooth legs. The sensation I felt was ten times better than last night, as the sheer nylon hugged my legs. I rubbed my thighs together as I sat there, delighting in the feel of nylon against nylon. Mindy attached the stocking tops to the garters that hung down from the bustier, then slipped the ruffled red panties up my legs. I stood to pull them up around my cock and balls, thrilling to the sensations that shot through me when the silk touched my flesh, and I looked down at my long red nails holding the elastic top of the panties. I stepped into the red heels that Mindy placed in front of my feet, and I was amazed by how wonderful they felt, and the change they made in my legs and butt. She quickly got the dress and slipped it over my upraised arms. Inside the skirt was crinoline, which flared out the bottom of the dress, and I felt the stiff material as it slid down my body, then the sensuous feel of the satin top around me. Mindy positioned it properly over my fake titties, and zipped me up the back. The feel of the skirt around my legs was fantastic, and I swirled around, making it rub back and forth against me. The strapless top hugged close around me, and I felt the pull of the waistline tugging me into the proper shape. "Just one more thing, and you'll be all ready," Mindy said, and I noticed that she seemed to be out of breath herself from excitement. She placed the wig over my hair, and I turned my head so the ends of the hair brushed against my bare shoulders. I started to walk over to look at myself, but she stopped me, saying, "just a second." She went to her dresser, and came back with a beautiful necklace, which she fastened around my neck. "Now you're done, go look at yourself." I hurried to the mirror, adjusting my steps to the unfamiliar high heels. I had closed my eyes in anticipation, and when I was in front of the mirror, I opened them. I couldn't believe what I saw. There was a total stranger looking back at me. I couldn't recognize myself at all. Mindy's skillful makeup job had transformed me into a beautiful woman that even my own mother wouldn't have recognized. Long blond hair surrounded my face with shiny curls, and my body had been shaped into femininity by my undergarments and dress. My bare shoulders swept down to my white chest from which my breasts pushed out at my reflection. The dress hugged my breasts tightly, narrowing at the waist, then flared out, stopping just above my knees in a silken swirl of red satin. I could see the sheer stockings on my hairless legs, embracing me down to my high red pumps. Mindy walked over to me and asked, "What do you think?" "I can't recognize myself," I said, "you've made me beautiful, and I love you." This was the first time I had said anything like that to her, and I realized after I said it that I really meant it. "I-I love you, too," she said, putting her arms around me and kissing me on the lips. We looked at the mirror together, seeing the two beautiful women reflected back at us, more alike than different, only my flared skirt and her sheath, her red hair and my blond differentiating us. I didn't know what the rest of my life would bring, but I knew that dressing like this would be part of it.

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Cookies Cream Ch 08

‘Mallow Cup’ Now, in this chapter, I want to focus on Eleanor and her fantasy man, Father Alexander O’Sheehan. Now this was a humorous story and at the same time very cute. Now to exception to it, there were some bits that were really sexy to me. The thing about the story was this is a two-sided story…sort of. Eleanor told me most of her ordeal. On the other hand, Father O’Sheehan thought nothing of the attraction until they met. So, with this in mind, this is their first meeting… The day...

4 years ago
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Dad Teaches Me

Sunday morning, I woke up with a huge boner again. These days, I just cannot control myself with those, I just keep having boners. Whether it is in class, or at the mall, I just keep having to go to the bathroom to jerk off. My only problem is that I cannot watch any porn at home. My mom always uses my computer at night, and during the day she is at home, I don't even have internet on my phone. I was rather new to the universe of porn, so I would instead satisfy my sexual hunger by jerking off...

3 years ago
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Sharing the wife for the first timeShe let him

The wife and I had been talking dirty during sex for years about her getting fucked by another guy, it always made us extra wild in bed too. She had been hanging out with an old friend of mine on the weekends which got us thinking. We both trusted him I could tell he thought she was hot and we knew he was D free. We stated our plan she was friends with his sister and would often catch a ride to her house with him. I had her start being flirty and wear tighter than normal clothes whenever he was...

2 years ago
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When Red Is Golden

Yeah, I have to admit that I grew up being pretty naïve about girls — and women, in general — when it comes to talking with them, being around them, kissing, or — heaven forbid — having sex with one. I had only one sibling, an older sister, but she was four years older than me and we lived in different worlds, for all practical purposes. She struggled with schoolwork; I breezed through mine. She had lots of friends; I had very few. She was close to my parents; I tried to stay out of their way....

3 years ago
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Typical Hollywood types

I’d never visited such a big city like Los Angeles before. It was huge and full of life. People were everywhere and traffic was horrendous. It was like I was surrounded by these concrete buildings that were continually growing high up into the sky. Their shadows rained down on me wherever I turned. People were everywhere but almost seemed to look right through me as we passed. At least almost every one did except for the occasional sleazy jerk that would never fail to practically accost me....

2 years ago
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Soiled Panties

Wendy and Bill had been married almost seven years now and Wendy loved Bill with all her heart.   He was everything she wanted in a man.   He provided well for her, they had a nice home and he earned a good living.   This allowed her work only part time.   Bill worked very long hours and in return Wendy happily took care of the house.   She viewed her ten hour a week job as mostly fun and a way to get out and see people.   They had close friends that they enjoyed seeing...

Spanking
4 years ago
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Walos MistressChapter 7

Eagerly, Lynn squirmed into position in front of them with her voluptuous white thighs opened wide apart enflaming Virgin's desire flushed face, her gilded-hair fringed cunt splayed like a delectable, butterflied fillet before her, its sensitive pink flesh moist with the passionate heat of her own prurient desire. Virgin marveled at it, her eyes momentarily fixed on the vibrant, tense clitoris that peeked out at her from its glistening shrine, the coral petals of her inner lips seeming to...

2 years ago
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Birthright

James Silver let out a yawn. He was nearing the end of his eight hour drive home from college. He had just wrapped up his sophomore year at Port Charlotte State University. As a second year student, he still hadn’t taken many classes in his psychology major yet, but the intro classes he took were interesting enough, if a bit basic. James was eager to get deeper into the subject over the next few years. The prospect of spending the summer at home did not excite him, however. James had chosen...

Mind Control
4 years ago
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Awakening Mother In Law

My mother-in-law, Margaret, officially, but Marge or Margie to most people, and I always got along fairly well. I treated her decent and liked her cooking and her daughter was happy with me and I guess that was what she cared most about. She had a small apartment on the first floor of the same building occupied by the family business. There were two bedrooms and a smaller apartment on the second floor and a quite large loft area on the third floor. When my wife, Glynda, and I were there we...

4 years ago
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Satisfying One Another

Hi friends nice to meet you all i love this ISS site very much i know about this site from one of my friend. Thanks to him i like reading all stories this in this site and now i am gona tell you my real story which happened 6 months ago let me tell you about myself first my name is rakesh working as software engineer in hyderabad i am tall with 183cms and had good physic as i daily go to gym with 23 years That’s all about me now coming into my story it all happened when i was still looking for...

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