Oh, that first college summer

College, of course, was a lot of fun. For the first time in my life, after four years at an all-boys high school, I was starting to attract a bit of attention from girls. Though through the end of my freshman year (I still had not had sex, nor even received or given oral sex in any fashion) my sex life was starting to gain traction, it didn’t provide the sort of sexual release that I was truly hoping for. However, with non-stop high speed internet access in my dorm room, I was able to spend a fair amount of time searching for porn.

With respect to school, I failed miserably in my first semester (I think I failed 3 of the 5 classes I took), was forced to take a reduced class load in the spring semester, and after numerous discussions with my parents about how to get back on track, we decided that I would spend the summer living on campus and taking summer classes. Somehow, with luck on my side, I was given a “double” room in one of the dorms, but only I would be living there. So for the summer, I had the room to myself…

Ironically, despite all of my curiosity and exploration while in high school, I don’t remember dressing at all that summer. Looking back, I kind of wish I did because now, I wish I had that kind of alone time to do whatever I wanted. But I do remember masturbating a bunch and watching a lot of porn. It has to have been around that time when I first say videos from ideepthroat.com.

This woman, Heather, has the skills that fascinated me… to deep throat a long cock, to literally fuck it with her mouth, to take it anally, and to swallow huge loads of cum without even batting an eye. I was absolutely fascinated. Still wondering what it would feel like to have my own dick sucked and to see a woman swallow my load, my curiosity leaped a bit further.

And so it was that summer, in the privacy of my dorm room, when I first jerked off and… ate my own cum…! I know some of you are probably thinking that it’s gross, that I’m a freak, or something else like that. But I don’t really care… Watching Heather in those videos was just so awe-inspiring and such an incredible turn on that after a while, I would watch more intently exactly what she was doing, studying her moves and mannerisms.

I haven’t had my own cum that many times since that first night, and most of the times that I have intended to, I end up chickening out. I don’t know why… =/ But I do know this, and this is a thought that I still have to this day, I would absolutely love to suck a big, long cock and take as much cum as I could. It’s an experience that will probably never happen, but I like to think that just from watching Heather, I’d be pretty damn good at it.

Teenage influences

So now I had begun to dress more often and more realistically (perhaps?) with the breasts and hips I had created and access to my sister’s wardrobe. Keep in mind, I was still rather young and nervous, but curious. At that point, there was no way that I was going to go shopping for myself, dress to pass in public, or anything else that might expose my secret hobby. I wasn’t even sure if dressing was something I wanted to continue to do or if it was just a phase. However, I knew that when I was dressed, at home, alone, my mind would race with different thoughts and fantasies.

Looking back to that time of my life, it’s a bit easier for me to identify a few factors which definitely influenced, increased, and encouraged my desire to crossdress and explore further. As a young teenager my friends and I had discovered porn, I was still a virgin and would remain so until I was 19 years old, and I was going to an all-boys high school. Having an older sister living at home facilitated crossdressing rather nicely as well, providing a wardrobe through which I would search for outfits and inspiration.

As my libido grew through high school, I struggled a bit with the fact that I never really had much interaction with girls. There was a “sister school” that we would have mixers with and they provided cheerleaders for our sports teams, but I was often more concerned with doing well in school and working in my spare time rather than chasing girls. Masturbation is just a part of life for teenage boys, but watching porn on occasion allowed me to calm my desires and sort of refocus until the urge came again.

I had gotten my hands on a porn video that I kept at home and that’s when things started to turn in a different direction for me, I think. I had a TV/VCR combination in my room and was able to watch it whenever I wanted after my family went to bed (my parents and sister’s bedrooms were well away from my own). Now, I was able to dress and watch porn at the same time, so that after I’d get my fill of the video I would slip into the bathroom to masturbate. It’s sounds so crude, I know.

As time went by, I became fascinated with the different roles that the man and woman had in the videos. One of the things you observe early on in run-of-the-mill porn is how the strapping guy would pound away at his woman, leaving her wasted but satisfied, sometimes hungry for more. Or, conversely, the woman diligently works on her man, sucking his cock, riding on top of him, or offering herself from behind. Her overall goal, often, is to bring her man to cum, either inside of her, somewhere on her body, or in her mouth. Remember, this is a basic assessment at best; certainly not applicable to all types of porn, merely what I was exposed to early on.

I could have masturbated all I wanted, but at that point in my life, I was never going to know what it would be like to be that man, to fuck a girl. While most teenage boys would watch and masturbate to the fantasy of indeed being that man, I would often fantasize about what it was like to be the woman. The women often derived so much pleasure that I became intensely curious about what it would be like and feel like to have a cock deep inside of me, to have my lips and my tongue all over his cock, or to accept his cum as a gift, a reward to me for my work.

Though I have never been attracted to a man in any way, a lack of exposure to and interaction with girls and crossdressing during all of these fantasies surely heightened my curiosity and desire to know what it felt like to be that woman.