Condoms: :/

So I tried masturbating with a condom on the other night, just for the hell of it. I thought about it a few weeks ago and started wanting to know what it felt like to actually wear one of these things. I knew it'd be a while before I got into bed with anyone, and I figured it'd be best to practice putting on one and getting used to the sensation before attempting to actually have sex. That, and I wanted to know if my phimosis would affect either either the fit or the stimulation.

I stalled for a few minutes before opening the wrapper. I still have all twelve condoms that came in the pack cos I had them bought for me for my Year 12 Formal & the subsequent after-party, but never used the one I took with me (my mum got them for me—she was more optimistic than I was :P). I felt awkward about not having the whole set anymore, like I wanted the whole collection to expire together or something :P  I was actually surprised to discover the expiry date is September 2015—these things last four years? Goddamn.

After I got over that, and after I got as hard as I could, I unpacked the condom. It was so weird looking at it; I laughed at least once or twice. They just look so goofy, man. I found the tip and put it on the head of my dick, then rolled it down. It was a tight fit, which made me feel good about my girth (even though I knew full well it was tight only cos I couldn't retract the foreskin), but it was also a little uncomfortable—it really was choking the chicken :P  I got it right the first time, though, without ripping or tearing it or anything, which was an achievement of sorts.

Once it was on, I started to jerk off. I wanted to move my hand without moving the foreskin, seeing as that's what I figure would happen if I was inside a woman: the lube on the condom, along with her natural lubrication and any extra stuff we added in, would have my dick just sliding whole, the condom preventing the foreskin from moving at all. Much to my disappointment, it didn't feel that good. It didn't feel bad; it just felt like nothing. With both the condom and my foreskin between my hands and my shaft, there was almost no pleasure to be had. Had a damn good fantasy going in my head, too, but even the best fantasy in the world couldn't have made this feel any better. I'd read up on having sex with phimosis beforehand, so I'd been warned. hence my disappointment being somewhat expected, but it still kinda sucked that I couldn't feel anything. I'll have to get this shit fixed.

On the other hand, it was kinda good to learn this before having sex with a girl. I mean, let's say I got with one of the chicks I had my eyes on at my Year 12 Formal. Let's say I'd managed not only to walk over and say 'hi', but we talked, we flirted, we kissed, we felt each other up, we got naked, and I got to have sex for the first time with her, only for it all to be ruined by my extended foreskin (whose nature as 'extended' I was unaware of at the time). Not only would it have been an embarrassing buzzkill for me, it would have sucked for her too. She might have felt like she was inadequate because I wasn't as pleasured as I should have been, or not felt what she expected to feel, hence not been pleasured herself. If there's one way that evening could have been ruined any more than it already was, it's that way :P  Saved myself a lot of grief, I suppose.

I eventually gave up and moved the foreskin with the condom on to get the job done. Even that felt kinda crappy. I can't move the foreskin much as it is, and it wasn't as stimulating as it usually is, so it was more about just getting finished than anything else. I eventually came, which felt unusual given I was cumming into a small plastic bag, but still felt good nonetheless. Taking it off was a right bitch: my pubic hairs kept getting caught in it as I rolled it off :P  Gotta do some manscaping; it's a bit unruly down there to say the least. Tied it up, threw it away, went to sleep.

Overall, it was pretty meh. I just want my phimosis gone: it fucking sucks. If I somehow manage to hook up/go out with a girl before I deal with it, all I'm gonna be up for is a handjob, maybe some cunnilingus. That's better than anything I've had/done before, I know, but I want more than that, and she probably will too. I have enough things inhibiting me when it comes to interacting with the ladies, so I don't need this shit making me nervous or unwilling to escalate when the time comes.