Gym Sissy free porn video

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Gym Sissy By Sssydiane I was a few years out of college, with a good job at a corporate accounting firm. I worked long hours, but the pay was very good. My boss liked me, and my prospects were good. I didn't yet have customer contact, but I was primarily responsible for several important clients. I was never athletic. In fact, I was a bit of a weakling growing up. I've always been slender, or I should say I used to be slender. Since I now lived a pretty sedentary life, sitting at a desk for long hours every day, I lost the trim appearance I had through college. One Sunday stepping out of the shower, I caught sight of myself in the mirror and got quite upset. I was getting flabby, and I had no muscle tone at all. I decided to join a nearby gym and get back in shape. I was also several months overdue for a haircut. I had always worn my hair down over my ears, but it was well past my ears now, and it was looking pretty shaggy. Since my job never requires customer contact, it hasn't been much of an issue at work. My boss figures that he would rather have me at my desk six days a week than taking time off to get a haircut. I decided that I would get a nice short cut on Saturday, to look more professional. I was moving on up the corporate ladder. Monday after work I drove right past my apartment and went to the gym about a mile down the road. It was a bit daunting, going in to talk to the staff and fill out the health questionnaire and the application. I figured I'd sign in and go exercise, but it was over an hour before I finished with the forms and ID card. The staff consisted of lean, healthy looking young men and women. Heather, the cute young lady who helped me was so bouncy and peppy, I got tired just following her around. She gave me the tour and showed me the pool, sauna, steam room, the locker rooms and all the other amenities. The free-weight room was intimidating, with all of the muscular guys lifting way more weight than I could ever imagine lifting. The cardio room was full of treadmills, elliptical trainers, stair- steppers, stationary bicycles and a wide variety of weight machines. There was a range of people working out, from teenagers to senior citizens, and an equally wide range of waistlines. After showing me the facility, Heather said that I was free to get changed and work out. I didn't have workout clothes, since I hadn't done any exercise in years. I was wearing the t-shirt I had worn under my shirt and tie, a pair of jeans that were a bit snug in the waist, and a pair of very old sneakers. It was the best I could do without going shopping. So, I just walked into the cardio room and looked around for some piece of equipment that could give me my flat belly back. I walked over to one of the stair-steppers and stood staring at it, trying to figure out the buttons. I decided to just step up on it, but the steps slowly sank to the floor. I was hopeless. "Push the quick-start button and just start climbing." I turned and saw the most gorgeous woman I had ever seen. Long, dark, shiny hair pulled back in a casual ponytail, dazzling smile, and I didn't know eyes could be so blue. She had an awesome body; and she was dressed like she knew it. She had firm, muscular legs coming down from her spandex shorts, and her sculpted abs peeked out from under a short belly- shirt. Her shoulders and arms were muscular, without losing that glorious femininity. I just stared, dumb-struck until she put her hand on my shoulder and said, "Push the quick-start button and just start climbing." I regained a bit of sense and did as she instructed. She told me to just keep climbing until I was tired. She got on the machine next to me and put out her hand and said her name was Denise. I told her my name was Dan, and we chatted while we worked out. Rather, she chatted. I could barely talk after a few minutes of climbing. On the other hand, she had her machine set at its highest level, and was talking as if she were sitting in an easy chair. She was obviously in phenomenal shape. After only five minutes, I had to stop and rest. Denise asked if this was my first time in the gym. I confessed that I was in terrible shape and that I really needed help. She said she would be glad to help me. She helped me on a couple other machines, until I told her I was wiped out. She had me do some stretching exercises to finish up. As I was getting ready to leave, she said she'd walk out with me, and told me that I needed some proper workout clothes. She offered to take me to the sporting goods mega-store just off the highway. She told me to get in her car. The drive was only five minutes, and I followed her into the store. She walked straight to the women's section and picked out a few pairs of tights and a couple t-shirts. She led me to the fitting room and told me to go in and try them on. I said that these were women's tights, and that I just needed some gym shorts. Denise said, "Who's the trainer here? Get in there and try these on, and come out to let me see." I meekly complied. In the dressing room, I pulled off my sneakers and jeans and pulled on a pair of tights. They were black spandex and came to just below my knees. I dutifully went out to show Denise. She chuckled and said that I had to take off my underwear to wear tights. I went back into the dressing room, took off my underwear, pulled the tights back on and walked out. Denise walked right up to me, pulled the waistband with one hand, deftly slipped her other hand in and with one quick motion tucked my balls up into my belly and pushed my cock between my legs. She then pulled them up tight and said, "You have to tuck when you wear tights. Now, turn around for me. Wow, what a gorgeous ass!" I was both mortified and aroused that she had handled my penis that way, but the fact that she thought I had a gorgeous ass made me feel almost giddy. Denise just carried on as if nothing out of the ordinary had happened. She told me to try on all of the other tights just to make sure they fit, and to model the tops she picked out. I did as instructed and she was very happy, saying that the outfits and the colors looked very good on me. I changed back into my jeans and carried the new outfits out to her. She was smiling at me and said, "These outfits fit you perfectly and you are so cute in them, I think you'll be very happy with them." She took one look at my feet and led me to the shoe department. She asked what size I am, and I told her I'm a size 7. She looked at the women's cross-training sneakers and pulled out a size 8.5 and told me to try them on. They were not girly-looking, but the fact that she picked out girls shoes for me was odd. They fit well, and Denise picked up a package of low white cotton socks. We went to the checkout and I paid for all of my new things. We left the store and I thought she was going to drive me back to my car, but she stopped at a large drugstore and led me in. I assumed she was stopping to pick up something for herself since we were passing by. She picked up shave gel, a woman's razor, depilatory cream, and some moisturizing lotion. At the register, she looked at me and I paid for the items since I assumed she left her wallet in the car. We walked to the car and she drove me back to the gym to pick up my car. At the car, she helped me transfer the new gym outfits from her car, and she handed me the bag from the drugstore. I asked what this stuff was for and she said, "Well, you can't wear tights with hairy legs, can you? Just follow the instructions on the depilatory cream, and use the razor to remove what doesn't come off. Be careful under your arms, you don't want to nick yourself. The lotion is to make your skin feel soft after shaving." Shave my legs? And my underarms? What was she thinking? I said, "I can't shave my whole body!" She said, "Why not? I like my sex partners smooth." When she put it like that, I would have shaved my head if she asked. She gave me a peck on the cheek and said she'd see me tomorrow night at the gym. "Don't forget to tuck!" I went home with my head swimming. I almost forgot about my aching body and the fact that I was exhausted. I headed to the bathroom and read the directions on the depilatory cream. I followed the directions and decided on a whim to do my pubic area, figuring she would like it if I was totally smooth. The cream started to burn, so I got into the shower and washed all of my body hair away. There was still some small spots that weren't smooth, but I got them with the razor. I went very slowly to avoid nicking myself ? it took forever. When I finally got out of the shower, I dried off and put on the lotion. I looked at myself in the mirror and became completely aroused. My skin felt wonderful, and I figured I would be having sex with Denise very soon. I laid on my bed and masturbated to a powerful orgasm and then fell into a deep sleep. The next day, work dragged. I was anxious to go to the gym to meet with Denise. I laughed as I realized that I hadn't even thought about going to the gym in years, and now I couldn't wait to go. Fortunately, I had to pass my place on my way from work to the gym. I know I couldn't have changed into one of those outfits at work, and I don't think I could change in the men's locker room either. I put on the tights, t-shirt, socks and sneakers, and then I tucked my penis between my legs. I couldn't believe I was going through with this. I walked into the gym, expecting people to point and laugh, but no one noticed me. I saw Denise and walked over to her. She threw me a huge smile and said, "You look great!" Then she whispered in my ear, "Your legs look very smooth and you remembered to tuck!" I lifted my arms, and she said, "Good job!" Her affirmation made me feel very good about myself. Denise had me do ten minutes on each of the machines. She gave me instructions and cheered me on when I started to fade. As I huffed and puffed, Denise told me a little about herself and asked about me. Unfortunately, I couldn't do more than one or two word responses. It turned out that Denise had just opened her fourth full-service beauty salon. She said that business was great and she was thinking of getting into the beauty supply business too. The only thing keeping her back was all of the paperwork ? rents, taxes, payroll. I told her she needed a good business accountant, and that my company could probably help her out. After four machines, my limbs were pretty rubbery and I was just about spent. Denise said that we could do some stretching exercises to cool down. She told me that it was important to stretch to keep from getting too sore. When I was done stretching, Denise told me to wear the yellow shirt tomorrow and as I left, she went off to finish her workout. This was the routine for the rest of the week. I learned a lot about her, and between exercises I told her about myself. She was very interested in my job. On Friday evening, she asked if I could help her out at the salon. If I could just take an hour or two to discuss the business and to give her some ideas of how she should proceed. She had been so good to me, I said, "Sure, anytime!" She said, "How about tomorrow morning at 10AM, at my salon on Oak Street. I think I can even find someone to take care of your shaggy hair. Wear your workout outfit and we'll do a power-walk afterwards." I showed up at the salon on Saturday morning, wearing my workout outfit. Denise grabbed my hand and said she had to deal with a customer, and that it would be best if I had my hair styled first. She led me over to a very pretty blonde stylist and introduced her as Catherine and said that Catherine would give me a style that would bring out the real me. Catherine led me to her chair and said, "You have beautiful hair! Those natural blonde highlights are very pretty." Catherine fussed with my hair in her chair for a few minutes, pulling it this way and that, looking at me in the mirror. When she had decided what to do (she never even asked me), she led me to the sink and gave me a wonderful scalp massage while washing and conditioning my hair. It was so relaxing and the warm fragrance was so nice, I could have drifted off right there. However, she squeezed the excess water from my hair, wrapped a towel around my head and led me back to her chair. She combed my wet hair and pinned sections up on the top of my head as she worked her way around in layers. She cut my hair all one length, in a blunt bob, parted in the middle, to just below my ear lobes. I was very worried that the look would be too feminine. Catherine proceeded to style my hair with a dryer and a round brush. She took her time, and when she was finished drying my hair, she brushed it until it was smooth and shiny. As she finished, Denise came over and gushed, "Catherine, you're amazing! That's the perfect style for him! It looks fantastic! Dan, I knew that shaggy mess was hiding great hair, but you look great!" My worries about my hair being too feminine disappeared when Denise went on about how great it looked and how it was perfect for my face. I really did like it, and it felt great; so smooth and shiny! When I thought we were done, Denise asked Catherine to neaten up my eyebrows a little bit. "A great style like that shouldn't have messy brows." Catherine led me to another salon station and proceeded to wax my eyebrows. It hurt, and I was scared of what I would look like. However, when she was done, my brows looked very neat and my eyes looked bigger. Denise was happy with the result too, "I told you Catherine would take care of you! Great job Catherine, he looks great!" I shook Catherine's hand and said it was very nice to meet her, and that I hoped to keep coming back to see her. Catherine said it was all taken care of, Denise had set me up with a standing appointment to see Catherine every Saturday at 10AM. She looked at my hand and said, "Don't cut your nails this week, I'll take care of them next Saturday." I followed Denise back to her office and she showed me her system for keeping four salons running profitably. She really knew the salon business, and her salons were all profitable, but her accounting left a bit to be desired. I looked things over for a couple of hours and gave her some ideas to lighten her paperwork load. She ordered in some salads for lunch and peppered me with questions. I found her a couple real cost- saving measures, and she was over-paying some of her taxes too. I told her she needed a good accountant to spend a couple weeks going over her books and that my company could help her a lot. It was past 3PM when we went for our power-walk. Denise said that the sunshine brought out the most beautiful highlights in my hair. She said she really liked the style that Catherine had given me. I agreed and said I really liked it. When we got back to the salon, I half expected Denise to invite me back to her place, but she gave me a peck on the cheek and said, "Thanks for all your wonderful help. I'll see you at the gym on Monday." We met at the gym every evening, and Denise added a few exercises to my routine. She tried to have me do some pushups, but I couldn't even do one. She said that I could do "girl pushups', where I put my knees on the floor and do easy pushups. I could only do a few, but it was a start. The following Saturday, I showed up in my workout clothes at 10AM with my body freshly shaved, hoping I'd get to be naked with Denise. Catherine took me right back to the eyebrow station and neatened me up. She made my brows just a bit thinner, but they looked good. Then she brought me to the nail station trimmed my cuticles, filed my nails, buffed them and put on a coat of clear polish. I thought the polish was a bit much, but Catherine had done such a great job with everything else, I just let her do what she thought best. She gave my toes the same treatment as my fingers and as I sat there waiting for the polish to dry, Denise came over to inspect. She beamed and told Catherine that she was the best, and told me I looked great. Denise and I power-walked and talked easily about everything. I found that the more time I spent with her, the more I liked and admired her as a person. At first, it was just a sexual attraction, but after a couple weeks I really liked her and wanted to spend time with her. It didn't even bother me when she gave me a peck on the cheek and said she'd see me at the gym Our training sessions at the gym were getting better for me. A couple weeks of regular exercise and I started to feel better about myself. I was still a few pounds overweight, but my pants fit better and I could take more punishment on the cardio machines. I still had to do girl pushups, but I was working at it. The following Saturday, I came to see Catherine at my appointed time. This time my body was freshly shaved, not so much because I wanted to have sex with Denise, but because I felt really sexy when I was smooth. Catherine removed the old polish from my nails and worked on my cuticles. She then filed my nails in to ovals. I said that they were too long for a guy, and that I'd like her to cut them shorter. She said that they really looked nice a bit longer, and that if I really wanted them shorter, she would cut them next Saturday. I don't know why, but I agreed. She put on a coat of clear polish and they really shined. I found that I really did like my nails longer, they looked nice. She did my eyebrows again, and I got the feeling that she was purposely making them thinner each time. She told me to buy a good pair of tweezers to get the stray hairs in between visits. Denise then suggested to Catherine that earrings would look good on me. I said I didn't think I could wear earrings and Catherine said that lots of guys wear earrings. Besides, if I didn't like them, I could just pull them out and the holes would close up. I acquiesced and Catherine pierced my ears and put in little pearl studs. I said, "Why pearls?" Catherine replied, "Because pearls go perfectly with your beautiful blonde hair." Apparently, it made perfect sense. I did like them though. After the third week, I really started to notice a difference at the gym. I was beginning to look forward to my workouts almost as much as seeing Denise. Though I didn't lay awake at night dreaming of workouts, I lay there with thoughts of Denise on top of me, using me as her sex toy. During my fourth visit to Catherine, she did my eyebrows and they were really starting to look feminine. I resolved to tell her so next week if she did it again. She again removed my clear polish from my fingers and toes and worked on my cuticles. My finger nails were way too long for a guy, and I don't know why I didn't ask her to cut them shorter. She put a coat of polish on my nails, and as it dried, I noticed that while it was still clear, it had a pink tint to it. I asked Catherine about it and she said, "I just thought you'd like something a little different." On the next appointment, I was scheduled for a hair trim. Catherine took her time and did a terrific job neatening up my ends. When I thought she was going to start to dry my hair, she started to put me up in rollers. I didn't know what to do! I told her not to use rollers, and she said that the curls would wash out and that I should just relax and enjoy it. When my head was full of rollers, she waxed my eyebrows and this time they were definitely very feminine. I was starting to get upset. I had enjoyed my past appointments, but now Catherine was going overboard. Denise came by to check on me and I told her that I didn't want to be put in rollers and that my eyebrows were way too feminine. She leaned down and whispered in my ear, "If you let Catherine make you beautiful, I'll take you home and fuck your brains out." I couldn't believe my ears! I was finally going to have sex with Denise! All I had to do was let Catherine have her way with me. From that point on, I just relaxed and enjoyed Catherine's attention. Catherine again removed my old nail polish, filed my nails and painted my finger and toe nails with a pearly pink color. I thought it was quite a pretty color, but had intentions of removing it as soon as I got home. While my nails were drying, Catherine put me under a hair dryer and said she would be back in a bit. Twenty minutes later, Catherine led me to her station and began to put foundation on my face. I initially pulled back, but remembered what Denise said. Catherine smoothed the foundation on and followed with a light powder. She put some blush on my cheekbones and smoothed everything out with a soft brush. Next, she put eyeliner on me, "Oohing" and "Aahhing" about the effect. She curled my eyelashes and used several shades of eye shadow to get the lustrous effect she was after. Then she put mascara on my lashes. She said I had long lashes like a girl. She lined my lips with a deep pink liner, and said that I had nice full lips like a girl. She used a pearly pink lipstick that matched my nails and said that she knew I'd be beautiful. After my makeup, which she wouldn't let me see, she started to take the rollers out of my hair. Long curls were bouncing in front of my face as she pulled the rollers out. She used a wide-toothed comb to shape my style into a mass of shiny curls framing my face. I gently shook my head and the curls bounced and tickled my ears and neck. At this point, Denise came back and said to Catherine, "Oh, Catherine! You've outdone yourself! I knew he'd be a pretty girl, but you've made her gorgeous! She's going to have to fight the boys off!" Denise spun the chair around so I could see myself in the mirror. I was stunned! I was a girl! I thought I'd be upset about it, but I was enthralled by my reflection. I was completely aroused. Denise said, "Come on Diane, let's get you dressed." She took me back to her office and handed me a bag. She said to put on the clothes and shoes in the bag, and wear the dress that was hanging behind the door. With that, she walked out. I looked in the bag and saw silky, feminine under things. I took off my clothes and put on a pair of black bikini panties. It was extremely difficult to tuck myself between my legs as I was getting hard. I put on a matching bra and B-cup breast forms. The breasts felt strange on my chest. Next I put on "nude" stay- up stockings ? it took me a while to figure out to roll them up my legs, especially with my long nails ? they felt very sexy. Next came a lacey black slip. My breathing was becoming labored, and I had to breathe deeply to calm down. There was also a small box in the bag that contained a three-strand faux pearl necklace with a matching bracelet and dangly earrings. I put them all on. Then I took the dress out of the garment bag hanging on the door. It was a very pretty black dress with a jewel neckline that accentuated my pearls. It was sleeveless and had a silky skirt that came down to a few inches above my knees. I twirled around several times just to feel the skirt brush my thighs. I sat down to put on the black patent leather strappy sandals with a three-inch heel. The shoes showed off my perfect toenails. The shoes also made my legs look very sexy and pushed my ass out. There was no mirror in the office, so I couldn't see what I looked like. I felt sexier than I ever could have imagined. I took a deep breath and opened the door. There was a flash, and Denise had taken a picture of my debut. Both Denise and Catherine complimented me over and over about what a pretty girl I was and how great I looked in that dress. After a few minutes, Denise took my hand and said, "Come home with me." We left the salon and got in her car. I was so excited about my new look, I was a chatterbox in the car. Denise told me to use a girl voice. I did my best. It was easy to find my girl voice, since I really felt like a girl and could never be mistaken for a guy dressed as I was. After a very short drive, Denise turned into a restaurant parking lot and parked. I said, "I thought we were going to your place." She replied, "After I show you off a bit." I was scared to get out of the car and she came around, opened my door and took my hand. She led me into the bar area and we took stools at the end. It was a bit late for lunch, but there were still quite a few patrons. Denise ordered Cosmopolitans for us and then leaned in to whisper, "Sit with your back straight and your knees together." When our drinks came, she made a toast, "Happy Birthday, Diane!" We drank our drinks, and because I was so nervous, I downed mine pretty quickly. The bartender brought me another. I drank that one too. I felt an alcohol buzz and realized that I was drinking martinis on an empty stomach. I didn't want to suggest going into the restaurant and eating, but if we stayed in the bar much longer I would be drunk. Meanwhile, Denise was looking at all of the men in the bar and asked which ones were my type. "My type?" "Yeah, which of these guys excites a girl like you?" I replied, "None of them, I'm not gay. I like beautiful women like you." "Come on, play along. If a guy came up and asked if he could buy you a drink, which one would you want it to be? How about the guy in the booth by the door? No? Then how about those two blonde college boys? Maybe? Hey, what about that cute guy sitting alone in the back over there?" I had replied "No" to all of them, but I hesitated at the last one. I don't know why I hesitated. He was a very good-looking man, but I'm not gay. Denise pounced, "So, you like them cute, well groomed and athletic? Nice choice. I think he's checking you out, he keeps looking this way." I looked over at him and our eyes met. I quickly looked away. Denise saw the whole thing. She was smiling like the cat that got the bird. She ribbed me about him for a little while longer. Suddenly, she handed me my lipstick and a compact mirror. "He's coming over. Quick, fix your lipstick!" I looked in the mirror and quickly fixed my lipstick. I capped the lipstick, closed the mirror and looked up just as he approached. I smiled at him and he smiled back. He continued walking to the door where he hugged his date who had just walked in and gave her a kiss on the cheek. The two of them then went into the restaurant area to sit down. I was very confused ? why did it bother me that he wasn't coming to ask me out? Then I realized what had just happened. Denise was giving me a very self- satisfied grin. "Not interested in men, huh? Who was the girl fixing her lipstick to be more appealing to that hot guy?" She picked on me for a bit and then she felt bad for me. "I didn't mean to make fun of you. You're just too cute." I gave her a small smile and blushed. She said, "Now let's really go back to my place." Denise lived just outside of town in a nice suburban neighborhood. She had a very nice house, with a pool in the back yard. She parked in the driveway and led me into the house. Once inside, she was an animal. She grabbed me and kissed me hard, pushing her tongue into my mouth. She ran her hands all over me, grabbed both cheeks of my ass and ground her hips into me. She said, "Let's go upstairs and fuck." I was taken completely by surprise by her attack and her forward language. She ushered me up the stairs in front of her and kept rubbing my ass all the way up. "You have a gorgeous ass, I can't wait to get a piece of it." In her room, she threw me down on the bed and straddled me. She pressed my arms over my head and kissed me hard again, shoving her tongue into my mouth. I responded as best as I could, given that I was helpless. I quickly realized that Denise was way stronger than I was. My penis was bursting out of my panties and creating a huge bulge in my skirt. She ravaged me while I was pinned for quite a while. I had never been with an aggressive woman before and it was thrilling. She got up and said, "Be right back, don't go anywhere." She peeled off her clothes and dropped them on her way into her walk-in closet. Her naked ass was exquisite. She was so lithe and athletic, her muscles gave her a fantastic shape, more like a goddess than a woman. She came out a minute later with a huge, realistic dildo strapped around her waist. It bobbed and waved as she walked toward me. I was mesmerized by it. "What are you doing?" "Just what I promised in the salon. I brought you home, now I'm going to fuck your brains out." "You can't be serious! You can't stick that in me! I'm not gay!" She walked over to me, pulled me off the bed, kissed me hard and pushed me down to my knees. "Open up, sissy-girl!" I didn't know what to do. She said, "You were fixing your lipstick in the bar to suck that guy's cock, now suck mine!" I looked up at her and opened my mouth to protest. She grabbed a handful of curls in one hand and with the other she guided the dildo into my mouth. She put both hands on my head and started to slowly rock her hips back and forth, using a piston motion to shove the cock into my mouth. Each time she thrust forward, she shoved just a tiny bit more cock into my mouth. After my saliva lubricated the dildo, it became easier and I could take more. After about ten minutes of face-fucking me, Denise pulled out so just the head of the cock was in my mouth and I saw a flash! She had taken a picture of me with her cock in my mouth. I tried to tell her not to, but she just shoved it back into my throat. Flash...Flash...Flash. She was taking pictures as I rubbed my lipstick off on her cock. After a few more pictures I resigned myself to doing her bidding. I tried my best to swallow the dildo; breathing on the out- stroke and relaxing my throat on the in-stroke. After a while, I had the entire cock in my throat and I was able to suppress my gag reflex. She said, "That's a good girl! You're a natural cock sucker!" As always, a few complimentary words from Denise, and all of my worries went away. I started to enjoy sucking her cock and wanted to do a good job to please her. After a few more minutes she pulled it out of my mouth and said, "Now for that fucking I promised you!" I panicked. I knew I couldn't take that huge thing in my virgin hole. I begged her not to fuck me. She grabbed me by my upper arms, lifted me off my knees and then sat on the bed and pulled me over her knees. She pulled up my skirt and yanked my panties down. She began to spank me ? hard! In no time I was struggling and squirming to get away. It was no use, she was that much stronger than me. I begged her to stop spanking me, it was really beginning to hurt. She said, in between smacks, "Use...your...girl...voice!" I pleaded in my girl voice for her to stop spanking me. She said she'd stop if she could fuck me. I finally said, "OK, you can fuck me, just stop spanking me!" She spanked me even harder, "Use...your...girl...voice! Now...beg...me...to...fuck...you!" I squirmed all around, but she just kept spanking me. Finally, in my girl voice, I said, "Please fuck me. I need your big cock in my pussy!" She stopped spanking me. She caressed my burning ass and ran her hand along my crack and down between my legs. "You're hard as a rock! Little sissy- girl likes to be spanked! We'll have to explore that more fully a little later ? but right now, I need to fuck you." She stood me up and told me to take off my dress and slip. She pushed me back on the bed and pulled off my panties. She squeezed some lube onto her fingers and started to lube my ass. She bent down and took my cock in her mouth as she slid first one, then two, then three, then four fingers in and out of my hole. When I was loose and lubed, she got up on her knees and lubed the dildo. It was a very sexy sight, her stroking her massive cock with lubricant between my legs. She grabbed my ankles and lifted my legs high. She set my ankles on her shoulders and guided the dildo into me. She started slowly, just like when she fucked my mouth. It was so big, I didn't think there was any way it could fit inside me. After a few minutes, the head of the dildo popped past my sphincter and I gasped. She just continued her slow, gentle, insistent assault on my virginity. As she pushed more and more of the dildo into me, she picked up her pace. I was moaning with pleasure because it felt so incredibly good. Soon, her thighs pressed against mine and it was all the way in. Denise leaned down to kiss me and said, "You're my girl now!" Then she started to fuck my brains out. She pounded that dildo into me like a jackhammer, with her thighs slapping against mine in fast cadence. I was beside myself, moaning and urging her on, begging her to fuck my pussy. She didn't need any further encouragement. Before long she was bucking and moaning, saying, "Here it comes baby! I'm going to fill your pussy with cum!" As she said those words, huge spurts of cum squirted from my cock, hitting my chin, neck, chest and belly. Then she came in great heaving spasms, her breath catching as she screamed out. When she came back to Earth, she scooped my cum up with her fingers and fed it to me. Then she had me lick her fingers clean. "Good girl!" She leaned down and kissed me again, much more gently this time, and said, "Did my sissy-girl like that?" I said, "That was the most wonderful experience of my life! I never thought sex could be that amazing! Thank you for feminizing me." She said, "It was my pleasure. I knew from the first time I laid eyes on you that you were really a girl. I'm glad you enjoy it, because you're going to be a full-time girl from now on." I thought about that while she slowly pulled her cock from my pussy. "I can't go to work as a girl! I'll get fired!" Denise just smiled and said, "Well, someone very close to me told me I should hire a good accountant..."

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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

2 years ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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