Real Life Adventures of a Sissy Girl

Adventures of a Sissy Girl is a series of vignettes by Cherie Amor, each a “real life” story of sissification as she was growing up. I hope you enjoy them as much as I do.

Halloween Party at Age 14

Cheri Halloween age 14

All the kids at school were going to meet for a Halloween party at one of the kid’s houses. I told a girl that was my close friend that I thought about going as a girl. She said that would be great and she would let me borrow a skirt and sweater and I could just wear them over my boy underwear and she could even let me use her wig. I said that would be great she told me that after I put her skirt and sweater on she would put some makeup on me too and I told her that would be great.

The next day was the day of the party and it was a Friday night but I had my own girlie underwear so I decided to wear that instead of my boy underwear. I put on a silky bra and panties and a full slip under my boy clothes and went to Mary Ann’s house to put finish my costume. She gave me a brown plaid wrap skirt and a pink sweater then told me to put them on in the bathroom. They felt good over my silky underwear and no one would even know I was wearing them. I went out to see Mary Ann and she put some makeup on my face then the wig and I looked great too.

We went to the party together and no one had a clue who I was she told everyone I was her cousin from another town. We mingled and were having a great time then they decided to have a costume judging contest so Mary Ann told them who I really was so I could be in the contest. She told them I was wearing her skirt and sweater over my boy underwear. Everyone liked my costume and I won a prize.

Later some of boys thought they would have some fun showing what was under my skirt so one of them got on their hands and knees behind me and another pushed me over him. Naturally my skirt flew up and my slip flew up and it exposed my panties to everyone and even Mary Ann was so surprised to see I was wearing a white lace trimmed full slip and pink silky panties trimmed in lace.

Since it was a setup one of the boys had a camera ready to snap photos and he took several of them showing everything. Another boy held me down so he could take more photos. I was so embarrassed I even started to cry but they held me down longer. When they finally let me up I ran into the bathroom and locked the door.

The girl’s all told the boys to behave or leave this was just a party. About thirty minutes later I came out and went to the boy who took the photos. His name was Paul and I begged him not to show anyone the photos. Then he told me to follow him and he took me out to the garage so we could be alone. He said why should  he do that for me. He didn’t know me that well and I told him I would do anything he wanted. He told me to let him take me home so I said okay. He was an older boy and had his driver’s license so we went to his car and started to go home but he took me to a dark area, then started to put his hand up under my skirt. I said what are you doing. Then he said you told me you would do anything but I guess if you want me to post the photos on the bulletin board at school that is fine too.

He told me I would have dress like a girl whenever he wanted and I would have to act like his girlfriend whenever he wanted me too. I told him I can’t do that this is not even my skirt and sweater. He asked me “whose underwear are you wearing?” I told them they were actually mine so he said see you like it too. He told me to lift my skirt up and let him see it better and I did as he asked and he turned his dome light on so he could see my pretty slip. He moved his hand over across my crotch and up under my slip and started to fondle me through my panties.  He told me I wear pretty underwear and I was beginning to really enjoy his fondling me and he leaned over and kissed me on the lips while he continued to fondle me.

My cock was starting to grow and he could tell I liked it. I even started to kiss him back as he continued to fondle me and faster and faster until I spurted into my panties and he loved it and I loved it too. After he finished I knew we would become really close friends and meet quite often in secret too. He even started buying me pretty dresses and skirts to wear when I was with him.

 Friend Discovers My Secret

Cherie discovered by friend in her 20s

When I was in my mid 20’s I kept my lingerie and frilliest things locked in a dresser drawer with a padlock that would lock all the drawers. One day I forgot to lock that chest of drawers and I had a friend over visiting me. I had asked him to get something for me out of the cabinet as we were working on a project together. Apparently he thought I meant out of the chest of drawers as he opened them up and saw some slips and panties along with some Polaroid pictures of me dressed up in them as a girl. He came over to me with some of the pictures in his hand and said what’s this.

It was a picture of me wearing a dress, heel, wig, makeup, and the dress was hiked up exposing my lacy slip and he was holding it in his hands. I turned beat red and explained that my landlord had caught me dressed up one day and took some pictures of me. I said he discovered my secret life that I am a transvestite and now you know it too. He looked through some of the other pictures and saw one where I was showing him my panties then he said man, you are really into this. I asked him please don’t tell anyone else please. He said, ” Well I don’t know. That sure would be something the guys would have fun with”. I begged him, I will do anything you want.

Then he said well I want to tell everyone we are going on a camping trip next weekend but you and I will go out to a different town and I want to see you dress up for me. I had no choice but to do as he asked so I said what do you want me to wear and he said everything: complete outfits with wigs and makeup and slips and panties, the works. I packed my stuff in two suitcases and took some skirts and blouses and dresses too and we were going in his car so I put them in his trunk. We left around noon on Friday and said we would be back late Sunday night.

First Time Caught By Other Than Family  (Age 10)

cherie in pink dress and white slip

I had already been cross-dressing for over three years and cross-dressed whenever I got the chance. I had stolen my aunt’s satin slip and pink satin tap panties and wore them to bed as it was Friday night and I knew everyone would sleep in the next morning.

I awoke to a tapping as three of my playmates were standing at my bedroom window trying to get me to come out and play. I know they saw what I was wearing as the covers were all off of me and the slip and panties were plainly visible. I quickly pulled the covers up and told then I couldn’t meet them this morning but would meet them at noon so we could all go to the movie show as we did every Saturday afternoon. They said okay and didn’t mention anything else so I thought it was okay and maybe they didn’t see me. 

I went to one of the friend’s houses and they were all there and told me to come in for a minute as they wanted to show me something. There was no one else home and they took me into my friend’s sister’s room and there lying on the bed was a pink dress, a white taffeta slip and silky pink lacy trimmed panties. I looked at them and they looked back at me and told me to put on these clothes.  I said no and tried to run but they had the door shut and blocked my way. I said no, no and they grabbed me and started to take my clothes off then held me down while one of them put the panties on me. They said we saw how you like to dress.

One held my hands as they put the taffeta slip on me then the dress and a big pink ribbon in my hair. I was crying and whimpering just like a little girl too. They put his sister’s Mary Jane shoes and girly socks on my feet while they held me down. They let me go after I was totally dressed. They took my boy clothes and told me I would get them back if I was a good little girl at the movie show. I said what do you mean,  I can’t go to the movies dressed like this and they said well you are going to do it or we will never give your boy clothes back and make you go to school like that too. I was crying and whimpering while I said it too.

Two of them were pulling me and one was behind me pushing as I was crying and carrying on. Then one of them said, hey Kenny go get your camera I think the kids at school will like this. I said okay I’ll go with you but no pictures. We had to ride the bus to get there so I sat between two of them at the very back of the bus hoping no one else would see me. One of them got the tickets for all of us and again I sat between them. We saw other kids from school there too but luckily no one recognized me. The kids I was with told me I better not act up or they would show some of the kids my pretty panties. After we got back home from the movies they didn’t let me change back to my boy clothes until nighttime.

Shortly after this incident we moved away and I started going to a different school.

 A Very Early Slip Adventure

sissy woman in black slipI actually started dressing at age 7 but I can remember a time when I was about 10 years old and I was over my friend’s house and we had to play inside because it was raining out. We were in the living room playing and the TV was on and I remember the movie playing was Lucille Ball in The Fuller Brush Girl. There was a scene where some guys were chasing Lucy on the stage and they ripped off her dress and she was running around in a black satin slip while they kept chasing her around the stage then she jumped off the stage into the arms of her boyfriend in the audience.

 I was paying attention to this entire scene and my classmate friend knew I liked to wear girl’s clothes and he saw how much I enjoyed this scene in the movie. He made me come to his mother’s bedroom and told me to take off all of my clothes and he took a black satin full slip and panties out of his mom’s dresser and told me to put them on and to pretend I was Lucy and act like she did in the movie.

I did as he asked and he chased me around the house pretending to be the other guys. Then when he sat down I came and jumped into his lap on the couch. He started to tickle me all over and I was giggling just like a little girl and wiggling all over and I remember how wonderful it felt as he touched the satin and it touched my body. He kept doing it for a long time too. This was the beginning of many play times like this too. Every time we saw a movie where it showed the girl in just her slip we acted it out including the tickling too.

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