Janet's Closet Forum

Full Version: My first time
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My first time cross dressing was when i was 12. I was home alone and i was looking at all the beautiful underwear in our house. I thought how nice it would be to put that on. My mother was a seamstress and she had quite a few satin slips that needed repair. (Maggie May was on the radio, and every time i hear that song i get real horny) Literally as soon as i got that slip on i came, hard. the smell of cum was everywhere. I loved it. I couldn't wait for it again. So i upped my game with a wig, lipstick, stockings. I would do it several times a week. I had to do quite a bit of washing or the smell of cum would give me away. I started upping my game by going to stores to purchase more wardrobe.  I would plan days when i knew everyone would be gone and i could have a whole afternoon of dress up and sex. Eventually my cross dressing gave way to wanting sex with a girl. I had started ballroom dance classes and being locked in a sweaty embrace for a girl with hours took away the urge to dress up. Being a healthy young man in puberty i usually had a hard on the whole time. I quickly learned i was not gay because the gay instructors would notice my hardon as i danced and then wanted to work on a step. However the minute we went pelvis to pelvis i went flaccid. Some of the teachers found this to be very insulting. and looking back i can see why. I can also see how they wanted a free feel from a 13 year old and that was definitely not cool. I could care less at the time because i was surrounded by beautiful women. Then when i was 14 a hot girl came into the studio, She was busty and blonde and a little trashy. She was one of the teachers girlfriend. I thought she was so hot. My mother and a few other girls were making fun of her and i said i thought she was pretty. They told me"well she used to be a boy" I said i didn't care she was beautiful. I excused myself and went upstairs to the mens room. Just then she came out of the women's. I had not even kissed a girl up to now but i wanted to kiss her so bad. I just said "i think you are so beautiful and i would like to kiss you, is that ok" She smiles and says "oh honey yes, and so i give her a big hug and start kissing her passionately" we come up for air eventually but are still locked in an embrace. I can feel my hardon up against her cock as it gets hard too. We are both pretty excited and she asks me my age as i grind away cock to cock. "14". The look on her face was total shock(i looked 16) "Oh My God. no i could go to jail!" She pulled away a little but my grinding was wearing her down and she was reciprocating albeit reluctantly. We dry humped and kissed for a good 10 minutes before she finally told me no and she had to go. I never saw her again but have been with alot of women and ts since. Everyone always says they feel very comfortable with me. This is the first time i ever talked to anyone about this. I counted once that i had been with over 50 ts, alot of porn stars and never once did i have the urge to tell them about my cross dressing. But it seems like underneath my clothes( i was an athlete and quite masculine)Women sense that i am a little bit like them. I had a girlfriend in college. I went to her professors office and the assistant who worked their came on to me hard. I thanked her but went on my way. That night i told my girlfriend "that girl you think is a lesbian? She isn't. The next day before my GF could say anything the "lesbian" apologizes for being attracted to me, she said she didn't know why but she was.  I could go on and on about some girls i dated who told me that they had been going out with  women exclusively before going out with me. So i kind of stopped dating and would go instead to strip joints. The same thing would happen there. The girls all say the same thing, that there is something different about me. Part of me wants to say"it's because i am a lesbian trapped in a man's body, really." But for some reason the ts seem to know who i am because they are very forward. I was on a job in new orleans and this beautiful creole girl was the night manager. Most all of my co workers asked her out and she turned them down. Then she comes up to me, and whispers "i could get fired if i was caught dating a guest but meet me down the street in an hour" Of course she was a TS and we had a great time. A few years later i am at baggage claim with my sister and i see a ts porn star at the next carousel. I was looking straight at my sister and this girl drops her leggings down mid thigh and does a quick helicopter. I was the only one there besides my sister and her. I just kept nodding my head and talking to my sister not looking. I am perfectly comfortable as a man but it seems that women and ts see me as different. Not sure if i should ever share this as it is quite long winded. I was with a beautiful ts escort about 10 years ago. It was pretty passionate. She was the first girl to try to top me, she was huge and my body just would not let her stay in for more than a second before pushing her out. We made love all over her apt and when i was getting dressed to leave she begged me to spend the night(it was about noon)no  charge. She said she felt so safe with me she just wanted to wake up with me all the time. When i said i couldn't she got a copy of a trans magazine where her best friend had won a big beauty contest. "I can get her over here and we can play all afternoon, she would love to meet you too" I felt bad having to turn her down. After that experience i really wanted to be topped so i called a porn star who also escorted. She was just my size and we had a great time. Later she asked me if i had ever considered escorting. I told her i just was not attracted to guys.I liked women and some of those women have cocks.  She seemed a little confused but to me it is the woman who is attractive and some just have different parts. There is just nothing like a beautiful busty girl getting undressed and then the noise when the cock comes out of her panties and slaps her leg. Then she rubs those boobs against your chest and asks if she can fill up your pussy. .
Oh i almost forgot.One of the funniest moments i ever had was with another ts pornstar/escort, i went inside her apt, she did the LE check by pulling my cock out of my jeans and telling me to jerk off while she did the same. After a couple of tugs she said"ok" and we went at each other on the floor with only our cocks out of our clothes. I came really quick and went to the bathroom as she was my first ts escort and i figured no freebie. When i  started to leave she said for me to wait so she could walk me to the door. We she came out of the other room my knees buckled. She had on a cut out leather bustier, with garter belt and stockings and thigh high stilletto boots. and of course a raging hard on. She smiled and said "do you like it"? I kind of mumbled yes but what i was thinking was "that is my favorite outfit at home, let me go get it" She walked me to the door and opened it, I looked down at that gorgeous outfit and that pulsating cock and it took everything i had to walk away. She followed me into the hall and i thought, this is my dream i love public sex i want her to drain that cock deep down my throat while her neighbors watch me swallow it all. If i hadn't walked away i think i would have never left that hallway.
Wow, what an amazing life you've had so far! So many women and ts's to have had sex with.
So, what about you, are you living and dressing up more as a woman?
Amy
Welcome to the forums Lizzieaz! Hope you make lots of friends here and continue to share your story.