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Caught Crossdressing By Mom

I started crossdressing when i was 6 yrs old. My Mom and Dad were divorced and my Mother worked all the time. By the age of twelve I uded to get dressed up after school and would do my makeup. I had long hair down to my sholders. I looked really good. I would dream about what it would be like to be with boys. I would ********** and pretend it was someone else. Sometimes even licking my fingers when finished.
I would borrow my mom's nightgown, panties and bra at night to sleep in. It was fantastic. We'll one night i fell asleep with the t.v. on and my Mom got up to use the bathroom and herd the t.v. so she came in turn it off and saw what I was wearing.
The next day when i got home from school she was sitting at the kitchen table. She poured me a soda and walked behind me and started brushing my hair. She did this all the time. She made comments like, you would be a pretty girl. I like this style on you, don't you. Then she asked me if I would like to be a girl? I kind of giggled and said why do you ask? She told me about last night and how she had noticed some of her stuff at times were in disarray.I told her that i was confused, that I didn't know. I told her about my being confused about boys and I wondered what it would like to be a girl with a boy. She told me that it is a wonderful experience. And she told me that she would support me if thats what i wanted. So I told her that i would like to try it. She said I knew you would say that, so she said she bought me some clothes and they were on my bed. She also said that she noticed that I liked lace panties so she bought me several pairs of those with matching bra's. All of my mothers lingerie matced colors, and she made sure all of mine matched. So she told me to go and try on my new stuff and model it for her. So in the bedroom i went. Everything fit great. She enen bought me someĀ silicone breastsĀ in a c cup. She said that she would like to do see what i lookes like in make up so she started to apply my make up. I couldn't believe what a fantastic job she did. Tomorrow was Saturday we got up and she did my makeup again. I wore a light yellow sundress. After a while her and I went for a ride. She told me how pretty i looked. We stopped for lunch and headed home.Later that night i told her that there was going to be a halloween party at school, and that i would like tot go as a witch. Later the next week she bought me a costume.We talked a lot about sex and what to expect. The day of the party was here. She did my makeup and helped me into my costume. I couldn't beleive how good I looked. She then gave me a black almost satin panty girdle. She said if I was planing on dancing with a boy then I would need to keep from getting too excited and giving away my secret. So I put it on and tucked myself in.
She took me to the dance and dropped me off. She gave me all the cautions and make sure I hade tissue in my purse. I went in and sat with other girls but really didn't talk to any. After a couple of hours a boy came ofer and asked me to dance. It was a fast dance so I didn't give it a thought. Then came the slow dance he was kind of awkward, and getting very hard. He started rubbing his **** into me, he seamed like he was really getting into it. I couldn't believe how hard he was getting. After that dance was over he wanted to go outside. We were talking and he leaned ofer and started kissing me. What a turn on. His hands were starting to roam. It was fine when he was rubbing my breasts, but when he tried to go south, I know why Mom gave me that girdle. I told him that i started my period and he couldn't do that. He was rubbing his **** against me and I told him I would give him a blow job. I dropped to my knees and unzipped his pants,and pulled his **** out, he was hard as a rock and had some precum on the end of his ****. I asked him if he ever had a blow job before? and he said no. I was living out my most private fantasy, i couldn't beleive it, i licked the end, he shuddered with excitement. Then I took all of him in and started sucking, it didn't take very long when i felt him pumping all that hot *** in my mouth, it tasted like mine, i swallowed every drop and licked his **** clean. I wanted more. I finally put it back in his pants and zipped up his zipper.We had lost time and realized that the dance was over. So i gave him a kiss and said goodby. We walked out front and my mother was waiting. So i got in the car and my mom said,I want all the details. So i told her that i finally got what i wanted and she said I can tell by the way you look that you enjoyed it. I told yes. She said I told you that it was a wonderful experience. About that time we were home. I went in and my mother said you got white stuff on your costume and we both laughed. Then I told her thanks for the girdle it saved me from getting caught. I told her i got so excited that i came, she told to go shower and we would talk later. So we sat around talking for hours like mother and daughter in our nightgows.
jamiecd2726 jamiecd2726 31-35, T 12 Responses Aug 27, 2010

Your Response


You have one of the best moms in the world

That was a great story. I only wish I could have been that lucky. You must really like your femininity. I k ow I do.

What a lucky girl you were, to have a mother like that!

What a beautiful story, such a wonderful mother

That is so sexy and wonderful! Lovely that your Mother is sharing and supportive of your desires!

What a cool story. You're so lucky!!! My mother found her things (panties, bras, slips, breast enhancers) many times in my room, usually hidden under my bed, and would just take them back without saying anything. I'm so happy for that and for her not telling my father!<br />
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Thanks for sharing!<br />

love your story. would like to be your ep cd friend. thanks stephaniea xoxo

Thanks for sharing girl.<br />
Louise CD

Such a wonderful, fulfilling beginning with such a loving and supportive mother. I'm in awe.

Nice of your mother to be so supportive. When my mother noticed her things were in disarray she just told me to stay out of her drawers. I'm not sure if she thought I was just looking at her lingerie or if I was wearing her things, but at least she didn't tell my father. That would have resulted in a serious beating I'm sure.

Wonderful story, thanks for sharing. Bring back memories foe me too.

Wow what a story. I wish I had a mother that understood my crossdressing. I wish my mom would have encouraged me to dress up and go out as a girl. I would have done the same thing you did. You are so LUCKY to have an experience like this. Most of us "girls" only dream and fantasize about having this kind of experience. How lucky can a guy get ot have a mom that encouraged him to dress up and let him go out as a girl and have sex like one to.