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How I lost My Virginity in LA Gay Cross Dressing Hotel sex

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Having already been stationed in Southern California and mid way into my second year of enlistment, I had already been to L.A. a couple of times and stayed in a cheap hotel not far from the Greyhound Bus Station. I applied for and got a thirty day leave and the anticipation of leaving and going to L.A. had me feeling terribly horny. My plans were to go and find a thrift store so that I could buy some girly things, go to the nearby Adult Bookstore and buy some Cross Dressing magazines and novels and pleasure myself. I knew that the walls of the hotel rooms had peep holes and I was hoping someone would see me dressing and would want to come over and fuck me. As luck would have it, a handsome looking older man took the room next to me. I made enough noise to let him know someone was there. I was pleasuring myself when I heard a light tapping on my door. I looked out and there stood a very pretty dark haired beauty. She had on a very sexy black dress and heels. I didn't quite know what to say, since I was dressed as a girl. I finally said,

"Ah, Yes, can I help you?"

"Hi sweetie," she said. "I'm your neighbor from next door. My I come in?"

My mind was clicking, so he too liked to dress. Maybe this wasn't such a bad idea after all. I opened the door and led her (I'll refer to him in the feminine) to the small couch in my room. We sat on opposite ends facing each other. I made sure to show a lot of leg and thigh. We talked about our desire to be girls and wearing sexy clothes and the such. I recall the conversation going like this.

"So sweetie how long have you been dressing and have you ever dressed with someone else?"

"I started at an early age but then quit when I joined the service. No, I've never been with anyone, did you ask that? Oh well, no I've never dressed with anyone."

"So sweetie, let me get this straight, You've never been with anyone, correct? Hmm, that makes you a virgin right? never sucked a cock or had a cock in your pussy?"

"Yes, I mean no, I mean yes, You could say I'm a virgin because although I dreamed of sucking a cock, I haven't. And I've dreamed of having a cock inside me, I' haven't had one as yet but I'd like to feel a cock inside me some day."

"Well sweetie, would you like to try right now? We can start by some slow kissing and such, then to some real fucking and sucking."

"Oh god yes, yes," I told her as she slid over next to me and began to shower me with kisses. I wasn't long before I opened my mouth to receive her exploring tongue. I pulled her hard into me as her hands explored under my dress. Her hands felt hot as she grabbed my hardened cock. She led me to the bed and laid herself down on me kissing me and whispering in my ear to roll over. She raised my skirt and fully prepared mu pussy to be fucked. She fucked me two more times before we said goodbye the next morning. I invited her to breakfast and we ended up making plans for her and I too spend my leave time fucking and sucking. After I went back to base I lost her number with her address and couldn't remember exactly where her house was. Since that time I've never had anyone else fuck my pussy. It's been years but as of late I have began to feel a little twinge back there. I may just have to see if some day the wild wind sex blows a cock my way.

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