Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

... feeling quite mellow and very aroused.”…. And so since I just sucked my first cock as a girl I was hoping maybe you would take my cherry tonite?” ’ Tracey had a grin on about as big as the Cheshire Cat, he leaned forward and took my rednailed hands in has and asked if I was sure, if I wanted I could just crash at his place and he’d go get my stuff in the morning and nobody had to know . I’d had a long time to think about it on the walk over, even though I was freezing the thought of having a man fuck me as a girl got me hotter and hotter the closer I got to Tracey’s apt. But the thought of doing it with Tracey as a guy still repelled me. I didn’t understand the difference and told Tracey this. “That my dear is because you’re a true Sissy” he explained. “Tell me, when Derek was fucking your mouth, did you get an erection?” “No” I replied “But I was totally turned on by it. Getting used and dominated like that. It made me feel like a submissive girly slut. But the thought of doing that as a guy grosses me out. So what gives?” While Tracey worked in the burgeoning field of IT as a systems administrator I also knew he had a Masters in Psychology. “ There isn’t a lot of research in this area,” (It WAS the early eighties)” but I think you have a situational based form of Gender Dysphoria . Basically, put you in the right situation, as in dressed like a girl, and in your mind you become a girl, with all that that implies. In essence, in your mind, you become whatever the clothes ...

... you are wearing dictate according to your expectations based upon societal perceptions. “ It was a bit deep for my 17 year old mind but I got the gist of it. If I was dressed like a slut I would act like a slut. If I was dressed like a guy I would act like a guy. “So I’m not gay then?” I asked with a little too much relief for my comfort. I blushed a bit, my face reddening as I realized the unintended slight to Tracey’s sexuality . “Do you get Hard with women? “ he asked “Hell yeah! Mikki and I have been dating for a few months now!” We had met at one of the Universities home games . I had worked the stadiums concession stands for the last few years. Moving my way up as a “Coke” hawker making 10 cents per Coke to a concession stand Mgr by the time I met Mikki. I was serving up some Nachos When this hot lil blonde girl shows up in front of me and asks for no jalapeños, Really? I give her some skin about it and she responds by giving me a challenge. “Fine, if you can eat a beer cup full of these “lightweight” jalapeños. We’ll go out next weekend.” Well, that was a definite ‘no balls” so I had to take the challenge . I wound up shitting fire for three days but I won the challenge. Mikki and had been dating ever since. Sex with her was incredible and I loved eating her pussy til she came. She was VERY responsive and loved having her pussy licked. She even told me I did as good as her old roommate from last year. Who I eventually figured out was Danni, the petite asian girl. I knew ...