Saturday, June 6, 2009

A Bit of My Sexual History part one-I start dating

This is a post I started, that was going to be about one thing, ended up being about something entirely different. It's long, so it'll be two parts, this one, about my early experiences dating, and the second, about my discovery of masturbation.

Not very many people I know in real life know about my visiting of sex chat rooms or on-line playing; it's not a question that a lot of people think to ask, and it's not exactly information I feel the need to volunteer. A couple of my closest friends know, and of course, I've told GF (I've had partners in the past who I didn't tell- leaving me feeling dirty and like I've betrayed their trust). Because the people who mean the most to me are not people likely to be disgusted or even concerned about this, their reaction is more one of amused confusion. I've never really been someone looking to have a lot of sex partners...I did the math yesterday, and I average one new sex partner a year since I lost my virginity (junior year of college). Everyone I've ever had sex with could fit comfortably in a mini-van...what a horrible road trip that would make!

No one I've ever known has thought of me as particularly promiscuous (with the noted exception of my sister- who thinks I'm a scandalous libertine); the town I grew up in was small and dull and remote enough that a lot (maybe most) of girls I went to high school with had sex early. It wasn't because there was some aphrodisiac in the town well that made everybody crazy with desire, but really because everything was so boring, so predictable cut off from the rest of the world that there really wasn't anything else to do but drink and smoke pot and hook up. And while I did some of the first, and a bit of the second, I didn't really find the third particularly appealing. The boys in my town were either sweetly dull Christians who talked about having children on the first date or they were terrifying redneck jocks with rape in their eyes. There were a few boys I liked a lot, but they were even more shy than I was; when I saw them at the mall or parties we both would stand there looking at each other pained, too afraid to be the first one to speak. Ah, memories.

There certainly were girls I went to school with that I crushed on to the point of despair- friends I would have to clench my fists around to resist the desire to touch them. And even though that was the era of lesbian chic, where high school girls across America were asserting their sexual liberation, it never reached us. Maybe public school girls can play with gender boundaries, but the assumption of rampant lesbianism in girls' Catholic schools (thank you, male pornographic fantasies) made it a distinctly taboo. Boys and public schoolers would constantly tease us about it, enough so that dyke become the ultimate insult my classmates could hurl at each other. Anything even remotely butch was viewed as genuinely threatening, to the point where a lot of the girls at my school became almost a parody of femininity- lathering on the make-up and adopting the giggling, semi-retarded demeanor that I guess boys find cute.

I did date a few boys in high school; they mostly tended to be from the sweetly dull Christian camp-mainly since those were the only ones who asked me out (it should be pointed out, in fairness, that I did also date a couple of those sensitive shy boys I mentioned liking). Sweetly dull Christians made for passable boyfriends when you're 15, 16, 17 years old; they drive you everywhere, make safe companions on church trips, are gentlemanly to the point of making you feel like a crippled child, they impress parents and they clean up nicely for school dances. True, you have to avoid any conversations about politics, religion or anything else the least bit interesting, and they always brought up their interest in getting married after a month of dating, but they were by and large easily managed, and even when, invariably after you have to dump them because they are crowding into every square inch of your life and they weep and wail about how much they love you and they've never met anyone like you, they eventually move on, finding and marrying a sweetly dull Christian wife, with whom they can have a litter of sweetly dull Christian children. Good for them!

But no matter how sweetly dull they may be in their devotion to the lord, they are still teenage boys...who take every opportunity to press their erection into your hip or thigh. I remember one sdC i dated sophomore year, who more than once acted as though he was just casually standing behind me, his arms over his shoulder, with his obvious erection pressing painfully into my lower back. It was like getting a spinal tap with a (comparatively) thick needle. This particular sdC boyfriend espoused at great length how wonderful it was that we were waiting until our wedding night to give the gift of sex to each other blah blah blah-he never actually bothered to ask me if I wanted to spend the rest of my unmarried life sitting on my virginity or if I gave one shit about all this purity nonsense. But for all of his vows of chastity, when we kissed, went to the movies, sat in his basement talking or even went for a walk holding hands, he was doubled over from the weight of his hard-on.

After a lot of fumbling and mixed signals and confusion, I eventually found myself with that hard-on clutched in my hand. Thus began my career as a high school handjobber. It's not that I was particularly talented at it- I probably caused as much pain and irritation as I did pleasure as I tried to figure out how it worked- but the fact that I was willing to even hold it in my hand was pretty much all that was needed to bring about a quick resolution. Merely the act of lowering their zipper, reaching inside their pants and pulling it out and holding it in my hand seemed to be nearly enough to produce an orgasm, and even when it wasn't, I eventually mastered the mechanics of giving a handjob enough to quickly finish it off. And what's weird is, to my surprise, I found I really, really liked doing it, having him lay there helpless under my touch, visibly shaking with excitement to have another human being pulling on his penis. The look of penises themselves struck me as more alien than erotic, and I quickly discovered what would be a life-long disgust at the sight, smell or especially touch of semen, but the weight of an erection in my palm, its moist heat, the way it felt so solid yet was completely and totally fascinating to me.

Most of the boys I satisfied this way were perfectly happy to limit our sexual contact to the rise and fall of their erections, the very idea of female arousal wholly foreign to them, I guess. What touching of me there was limited to a hand thrust under my shirt, awkwardly kneading and pushing at my breasts while I fondled him. By summer before senior year, my most recent boyfriend (who was not a sdC, but one of the shy, arty boys I had bullied into asking me out), made a concerted effort to repay the favor by sticking his hand down the front of my pants in search of the much point of female pleasure. Let me say I absolutely applaud this effort; it was the first time it even occurred to a boy friend that I might enjoy some attention as well. And it was intensely exciting the first time he touched between the was the first time someone other than a medical professional or myself came in direct contact with my flower. But...

He seemed to operating under the impression that the place to touch me to give me pleasure was located deep inside of my vagina, and required a lot of digging around to find it, regardless of whether or not I was wet enough for penetration. I don't in any way blame him (or the couple of subsequent boyfriends who labored under same impression) for the jabbing invasions that were his attempts at giving me an orgasm; I'm not seriously anti-pornography or anything, but I do think it gives inexperienced boys really, really incorrect information about sex and womens' bodies (all those bubble gum pink and hairless buttholes come to mind).
you know how they get those pink anuses in porn? it's called anal bleaching...why don't you go bleach your anus

And of course, the real blame ultimately falls on me. Had I communicated specifically how I wanted to be touched I would have saved myself a lot of serious discomfort and maybe even experienced some much craved for pleasure. But I just couldn't get up the courage, just couldn't tell him (or even guide his hand to) what would have made me feel good. Like far too many things, I feel a lot of guilt about this now, both for robbing myself but also because he so wanted me to enjoy it, he tried so hard to make me orgasm, he so wanted to see me climax, but instead got to see me lying there, gritting my teeth and clenching my fists at my sides as his finger violently pounded in and out of me.

But I'm getting better every day...

to be continued

I went overboard on the chastity belt pictures...this is the last one


  1. I must say that I'm rather enjoying this little trip down memory lane. Looking foward to the next post :-)


  2. Thank you! The second part is much better (at least I think so) but I spent so much time today goofing around with the stupid play list thing that I didn't finish it. There IS a good reason I'm a sub...

  3. i enjoyed reading that. oh, female arousal, i'm a guy with a lot to learn still! :)

  4. LOL! I think they have books for men now about where everything is located and how it works. And it never hurts to ask;I think a lot of guys treat it like they do with asking directions-like it's a loss of manhood to ask where to go. I'd much rather be just be asked than lay there dry and raw.



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