Almost caught up

I’ve almost taken you through all of the hows and whens (I’m still trying to figure out the “whys” myself) of my crossdressing, from the start as a young teenager through college, but I’m not quite up to today just yet. From the previous story, you may have noticed that crossdressing had taken a decidedly different turn for me: it was no longer about just dressing as a woman for my own gratification, but I was starting to have some serious sexual desires and fantasies where I play the role of the woman, dressed my best of course.

Through college, I had dated steadily, going very short periods of time without a girlfriend. Over the past ten years ranging up to this day, I’ve had three very long-term relationships with very little single time in between. Shortly after my sophomore year began, I had sex with my then-girlfriend for the first time, and I was off and running in that respect. So needless to say, being in the dorms in college and having a girlfriend almost constantly, I did not get to dress that often (pretty much never I guess); and looking back now, I almost feel as though I had kicked the habit for quite some time.

Summers at home, starting the summer after my sophomore year, were often rather busy; I was working two jobs, an office job during the day and waiting tables at night, seeing my girlfriend (the second of the three long-term relationships at that time) whenever I could, and after that, seeing my old high school crew in the remainder. Being at home did, however, take me back to when I was a teenager peering through my sister’s closet trying to find a dress or a pair of panties and a bra that I could wear.

Ironically, and with no sort of premeditation about it, before I left for college I had stowed one of my sister’s bras and a pair panties deep in the closet in my bedroom where no one, not even my mom, would find them; it was just where I always hid them back in high school so I didn’t have to go into her room every day. This was especially convenient at that time because my sister had moved out of the house. So in the little free time that I had those summers, I at least had something I could slip on late at night while I watched television in bed or to wear while sleeping. There were a few items left in the closet in her old bedroom which I had tried on, I think a few old dresses or blouses, but I had grown considerably since high school and nothing fit.

So for a while, I was left with just the two basics that I needed to rekindle my desire to dress every summer. Good enough for the time being, but that would change.

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.