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58 stories

  • I grew up as a crossdresser from an early age. It was always a secret passion of mine. This story is about my junior year in high school.

    Things had got a little strange when my fa orite aunt came to stay with us. She was given my room for her stay and I moved in with my brother. Her name was Ellen and she was a divorced woman, very beautiful and sexy. Unfortunately, Ellen died in a rafting accident and the family was left grieving. It took several months before we got over it and I was finally allowed back in my room.

    My bed still smelled of her perfume and a sexy nightie was still on the night stand. The first night, I found myself drawn to it. It was a blue babydoll with lots of lace. I slipped into it and the matching panties I new she had worn. I missed her a lot. But, my enjoyment at wearing her sexy outfit soon turned into a hard cock which I stroked until I came in her panties.

    Ellen’s clothing was still in the closet, so I spent the summer dressing in her things. But my biggest treasure find was a medium sized case jammed under my bed. I pulled it out and nervously opened it. There was an assortment of sex toys. I was so turned on y knowing my aunt had used these on herself.

    I found myself smelling and tasting the large penus shaped vibrators. I I sucked them and eventually started fucking myself at night. I really enjoyed pretending that I was a woman, being fucked or sucking cock.

    By the time school started, I was really good at pleasing myself. School started as usual. My favorite class was French III, where I was the only guy. There were about 12 of the hottest senior girls in the class. Sometime during the first month, one of the girls, Sue Cunningham got nailed for cheating on an exam. Somebody, probably to divert the blame, told her I did it. Sue was pissed, really pissed. She told me to watch my back. I tried to tell her I didnt do it but she didnt believe me.

    In French class she always glared at me. I was a quiet boy, small and thin, almost feminine with large brown eyes and fairly long brown hair.

    The class had to do a skit for an assembly and the girls had decided that they should do an act with French maids. They practiced with the help of our teacher as i sat in the bleachers and secretly stole looks at their in their sexy short maid dresses, thigh high heels, pretty black 4 inch heels. There were 5 dancers and they were gorgeous.

    A few days before the event, one of the girls broke her ankle and they were short one. Since the girl that was out was my size and none of the girls in class could wear it, Sue suggested I could fill in. I was terribly embarrassed but secretly, I wished I could. I tried to resist but my teacher asked me if I could do it. After some persuading, I agreed.

    The day of the skit, the girls did my makeup and hair. They gave me my outfit and told me to go get dressed. My cock was rock hard as I went to the gymnastic room to dress. I slipped into the thigh high nylons and garter belt and then the cute frilly panties, followed by the sexy French maid dress and high heels.

    My cock was rock hard as I walked back to the girls locker room. I was afraid they would see how turned on I was, but they seemed more interested in looking at me and telling each other how pretty I was.

    I dont remember much about the skit a d I guess I did OK. Afterwards, I went back to the gymnastic room where I had left my clothes. But I couldnt find them and immediately got scared. How was I going to get home, dressed like a girl. As I was looking, Sue walked in with her boyfriend and and 4 other guys. Sue told me it was payback time. I was grabbed and pushed over the leather covered “horse”. My feet were spread and tied to the frame and my hands were tied o er the other side. I was helpless as Sue took some scissors and cut off my panties, exposing my ass to the group. Somebody poured something cold and slippery down the crack of my ass. Sue knelt down next to my face and said i should get ready to get fucked, like she got fucked when she was ratted out. I tried to tell her it wasnt me, but she pushed the panties into my mouth.

    Just then, a hard cock slid into my ass. I felt fantastic, better than my vibrators. Whoever was behind me began furiously fucking me as Sue continue to harass me, asking me how I liked being fucked by a real man.

    Oh, I wanted to say I was loving it, but apparently my hard cock gave things away as Sue noticed. She said I was a real faggot as my cock was throbbing. The first guy finished and another took his place. Sue told on of the guys to go spread the word that there was a slut in the gymnastic room fucking all comers. Secretly, I was thrilled and I suddenly came on the floor without touching myself. Sue told me I was really a pervert.

    Sue pulled the panties out of my mouth and said maybe I needed a nice hard cock fucking it while my ass was being fucked. I soon found a hard cock being offered. I didnt need an invitation, and opened my mouth to let the cock slide over my tongue and into my mouth. I dont know how many guys fucked me or how many cocks I sucked. The embarrassment was gone. I wanted to suck cock and be fucked.

    We had one foreign exchange student, a large black guy from the Sudan. Somebody brought him over and he dropped his pants, exposing about 10 inches of hard black cock. I reached out with my lips and kissed it before I began sucking it. It seemed the room was full of students watching as he moved around behind me and sold his enormous cock into my cum-filled butt. My cock hardened again and stayed that way as he fucked me like a wild man. I could hear cheers and laughter as he fucked my faggot ass. As he tensed and I knew he was getting ready to shoot his hot cum into me, I came again. The watchers seemed to be in awe as my cum shot onto the floor.

    The room slowly emptied and Sue again told me I was a fucking gross faggot. Soon, I was alone and still tied to the leather exercise horse. Then, a guy came in and untied me. He was one of a group of gay guys at the school. He said he was sorry, and he left.

    School was out and i returned to searching for my clothes. I found them behind some weights. Sue had but them to an unwearable pile of rags. My only choice was to walk home, still wearing the sexy French maid outfit. I tried to stay on deserted streets but sometimes I couldnt manage that. I had guys stopping to try to pick me up, but I just kept walking. I could feel cum sleeping from my ass, which went on to excite me.

    I took a shortcut that ran behind the fairgrounds, thinking I would be away from people. But, as I reached a small park by the river, there was a group of guys from the government training center. They were mostly minorities and not really welcome in our all white town.

    A few of them walked out to meet me, checking me out and telling me how pretty I was. They slowly surrounded me and I ft hand under my short dress, feeling my bottom. I told them I wasnt really a girl and one of them said I looked like one, so it didnt matter.

    Someone asked if I fucked guys and another hand slipped between the cheeks of my ass and a finger slid into my butt. He said that I was wet and ready to fuck. They picked me up and carried me to a picnic table and I saw a huge cock escape from his pants. He pushed it into me and began fucking. He didnt last long and soon dumped more cum into me. Another guy followed until all of them had a turn. Afterwards, I sat on the picnic table bench and found myself asking if anybody wanted a blowjob. I sucked several of them, knowing that those cocks had been in my cum-filled ass. But I was turned on and i sucked the guys in line.

    I had the guys walk me the rest of the way home, thanked them for the fun time. They asked if i would be out in the future and i smiled and told them it was possible. I climbed in my bedroom window, slipped into my favorite nightie and fucked myself to sleep with Aunt Ellen’s vibrator. It was a good day and evening.

    Dani Allen
  • I started dressing when I was in college. But, I still enjoy it now. I only like married men. I wear short skirts, stockings, and heels. IT is fun at hotel, or at their house. They always seem like they are straight. But, they are always erect. They like my panties. And always hang on to my heels, as they enter.

    Eric
  • I started wearing my mothers bras panties and dresses when I was 5 yo my mother caught me many times. one day when my father was on a trip overseas my mother asked me to come to her room. she asked me to sit on the bed that she needed to ask me a few things.my mother was a very beautiful woman and very sexy. she started to ask me about dressing in her sexy things she asked if I like doing that and I said very much. she smiled at me and gave me a wonderful kiss on my mouth. she asked me if I would like to become a girl I looked down and said yes she said she will help me to do that. I asked about dad she said that she and my dad were splitting up and that he was moving overseas I started to cry my mother said no to cry that we will be ok. I asked her if my father was leaving because of me she said of course not. she told me to go get a shower and that she would be right in to help me. when she came in she was naked and she washed me all over and she let me suck on her 36dd boobs I came all over her she kissed me and said she loved that she told me to lick it off of her and then we got out and she dried me of and wrapped a towel around her and she led le back to her room. when we got there my eyes lit up for on the bed was the sexiest lingerie I had ever seen. their was a sexy black bra and pantie set a very sexy crimson corset with attached garters and sexy black stockings. she dropped her towel and proceded to help me dress. after she made sure every thing was perfect she said she had something else for me she opened her bra drawer and broght out silicone beast forms in dd size I came so hard in my panties she lowerd my panties and sucked my little boy clitty clean wow. she told me that I would be her daughter from now on. she also said she invited her best friend over in the morning to start teaching me how to be a good submissive lesbian. mom asked if that is what I really wanted and I said yes! the next morning before I even woke up after a night of my mother making love to me her friend showed up i heard some noise in the base ment so I got up and when I did to my surprise some time in the night my mom had glued my breast forms on me and tucked my little clit back between my legs and glued it there. I was dressed in some very sexy submissive lingerie. I went down stairs and my mom said good morning my little sub leabian daughter are you ready for what terry and I have instore for you in the basement. I looked down and said yes. More to come later!!!

    debbie
  • Loving the feel of ladies clothes as long as I can remember left with feelings of shame and not being the man I should be. I like many others have had gfs and wives that at first was ok with what I was doing. But they need very were able to let others know or go out into public with me. I probably have had three or four closets full of clothes and shoes only to purge it all trying to hold on to a relationship that was not going to work out. I’m not into men in a bit in a dress and when I’m dressed heels dress make up I feel so open and creative like on another world. Until I did years ago when I finally stupid up for me and told the woman that loves then and still loves me today I was going to live to be happy and of people don’t approve of that then they aren’t my friends she was hesitant at first but she stands beside me today about 75% of the time I am wearing a dress or skirt still I have not been able to find but one friend that accepted this life style so today I am in search for a friend who also enjoys the same life style not a serial partner or lover I all ready have the best one I could ask for just someone to hang out or go out and have a drink. Any ideas all help will be appreciated

    Deana
  • Well in Wal-Mart’s yesterday and I was shopping for more tops and I kept seeing this older guy watching me so I just on shopping I didn’t have anything on sexy just a pair of leggings and heels and a top and then he bumped into me I should say bumped into my ass he said he was sorry and we got to talking and out of the blue he ask me if I would give him a bj I said sure I ask where when so he said in my car in the parking lot and now I sure he let me find my wife she wants to watch I was in shock when he said that I waited for them at the door and they come walking up to me we went their car he move to corner parking spot so me and got in back seat he pulled his pants down and I started sucking away and then his wife pulls my leggings down and sticks two fingers in my ass and to finger fuck my ass it was so great I had so much fun with them after we were finish they said we to do this at our home in the back yard I would like that so we made a date to have some more fun this weekend come to find out he 62 his has a very hard 8 inch cock and she is 61 and loves sex so I can’t wait until this weekend these two were so much fun in a car I hope it more fun at there home

    Cassie Harsh

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