I don't know why I always attract these angry, perpetually pissed off women. Back in my college days, I struck up a friendship with one such specimen in History 202, Dr. Longstrom's class. It's probably because I grew up in a hostile, contentious family with two warring parents who should have never gotten married in the first place. But this was marriage number two for both of them, and because they were raised in such a strong religious setting, family members pushed them together. Both of my parents had children from their first marriage and so I was their common denominator.
Sophomore year, aged nineteen, my girlfriend was named Jenny, and she came from money. That's why she lived in the newest, most expensive dorm on campus. She was, as I reflected, a lot like my freshman year ex-girlfriend, whose parents were so wealthy that they set her up on her own in an apartment in the old money part of town. Sex with her had been like two cats fighting. At first, she made a great to do of even letting me into her room, so I always had to make do with the couch in the den.
We watched one of my patented snooty art films, a slowly paced Italian film from the mid-sixties. I loved it. The most she could say in response was a defiant and confused, "why do none of the women in this film wear a bra?" I had to admit the thought had never crossed my mind. Probably because it wasn't necessary, because the entire female cast would have worn at best an A cup.
Halfway through, that first date, as we had been seated side by side until that point, she leaned her head against my right shoulder. Then she pushed me sideways across the length of the couch, cuddling me. And then she said it.
"You are quickly becoming the perfect man." A heady compliment, one that would soon prove totally false but at the time it was one of the most powerful ego strokes I'd ever received. If anyone ever told it to me now I'd have to laugh. Me? Perfect? Hardly.
She would go no farther. No kissing. Just her body cradled next to me. And now, the movie over, so was our date. I was dropped off back at my apartment around 11 in her expensive SUV. It never really went any further than that for a very long time. I felt like Holden Caufield's description of trying to remove a reluctant girl's brassiere, circa 1949. By the time I was done with it, she looked like she wanted to claw my eyes out.
That was primarily the reason we had broken up. Much of it was that I couldn't take all the negativity anymore. I understood it. I knew how to work around it, but it didn't make for great chemistry. Still, let me return to what became a one-night-stand with another perpetually sour woman. I didn't know it at the time, but she had an agenda. I was in place to try to get back at her own ex, who had thrown her over for reasons she never explained to me, and I never asked.
She asked me to stay. We sat astride her desktop computer, which she turned on, and then logged into Skype. A man eventually appeared, with a woman sitting astride him just as I was sitting astride her. They glared at each other. One didn't have to guess that they'd once been a couple.
"See what you threw away, Jason!" She was white hot now. "You could have had me. You could have had this pussy any time you wanted, but you had to be with her!"
Sensing my opportunity, I began massaging Jenny's shoulders. She encouraged me to keep it up, as the two of them continued to snarl at each other. The man on the screen deeply kissed what was apparently his new squeeze, and I reenacted that same act on Jenny.
Then he got really nasty. "You're still a fat bitch. You know that? I don't care who you're fucking now."
The sheer cruelty of that remark knocked her off course a second. But she quickly recovered. "Fuck you, you prick."
The two avatars on screen got up simultaneously, leaving the camera on and their room empty. Then he abruptly turned Skype off.
She was so pissed that she could spit nails. But I liked a good revenge fuck and knew precisely what role I was to play in this elaborate and now obvious charade. It occurs to me that I haven't described her to you. She was a brunette, brown eyed, about average height for a woman, and probably fifty pounds overweight. But she carried it well. I have a thing for that type in the first place, so no complaints from this department.
We started making out as the two of us walked slowly backwards into her bedroom. Naturally, she had no roommate and a ton of space. I didn't have to fight to remove clothing this time, pulling down panties that quickly revealed one of the largest asses I've ever seen in my life. The sight was accentuated by the fact that she was wearing a Layne Bryant purple solid color thong. I rubbed my hands up and down each ass cheek as she let out an appreciative sigh.
"You are going to pull out, aren't you?"
I nodded in the affirmative. I was on medications that, while they did not destroy my libido and my erection, did greatly reduce the amount of semen I could produce. I know it only takes one and yes, I was playing Russian roulette, but I felt like I was owed this act. She climbed on top of me and began to straddle me. Her huge stomach rubbed against mine.
Strangely, her breasts were relatively small for a woman her size, maybe only B cups, and they were perfectly cylindrical, as though they'd been mass produced in a factory. They looked a little like Lena Dunham's tits, if you've ever seen them.
Her pussy hair was brown and not copious, but as I motioned to turn her over, I noticed it rimmed the outside of her anus. "You can take me up the ass if you want," I heard her say. "But," and she added a crucial caveat, "you gotta wear a condom for that hole. Too many germs."
The concept was novel for me. I'd never engaged in anal before, much less any woman who had asked for it directly. She kept a box of Trojans astride her bedside table, and with skill, ripped one open, and then slid it down the base of my erect shaft in one resolute motion. Then she pulled out a tiny bottle of lube in a clear plastic bottle with a red top and began to use her right index finger to poke in and out.
I felt like being a formal virgin again, all full of nerves. What if I couldn't get this to work? She leaned over on all fours, the ass chub drooping slightly downward in between two huge thighs. I began tentatively at first. Good lord she was tight. I didn't want to hurt her, so I pushed very slowly and deliberately, aiming for an inch at a time. At first not much happened, but then I somehow managed to push the whole head of my cock inside her, soliciting a satiated moan.
"Keep going," she panted. "Don't stop. Don't stop."
Her wish was my command. I kept pushing and pushing until all of me was inside her. I'm an average sized guy with a decent amount of girth and had never been a problem for any woman's vagina before. Her anal sphincter closed tightly around me once I was totally inside and for a second I froze. Was I sure I wasn't hurting her? Apparently not.
I pushed out slightly with my hips and began to work into a slow, workmanlike, tentative rhythm. And as I kept it up, I noticed she was so wet that she'd soaked herself. I'd never seen a woman that way before and I haven't since. Still fucking her ass, I slid my index and middle finger of my right hand, upside down, into her cunt. I was granted immediate access all the way inside.
"Fuck yeah," she screamed. "Fill that pussy good. I want you in my other hole next."
I realized fairly quickly that if I wanted that to happen, I needed to begin immediately. So I slid out of her ass, snapped the rubber off, threw it haphazardly onto the left side of the bed, and flipped her big body over.
Usually I would push against a woman's thighs for support when I was penetrating her, but she was dripping so wet that I simply could not get any traction. I'd slid easily into her, but kept fighting for leverage, grabbing higher and higher up her legs to find any place that wasn't so juicy that I couldn't grab hold of it in my hand and hold it there. Eventually, I grabbed her by the ankles and thrust hard and deep into her.
Her eyes rolled back into her head as I continued. She took huge breaths of air, shuddering on the exhale as she took me, over and over. "Huhhh. Huhhh. Make me come, you bastard. Make me come all over your cock. Oh, you're so beautiful."
A compliment from the previously furious one? Where had that come from?
But then a quick return to form. "You fucker. You think you can take me?"
Yes, yes, I did. And was, in fact.
I'd kept silent for the most part during these proceedings until the very end. "Oh yeah," I said, feeling my orgasm. It was almost here. She had one final request. "Come on my stomach."
So I masturbated myself furiously, maniacally, until eventually I squirted a tiny bit about halfway up her abdomen.
"Aw, that's so cute."
I certainly hadn't wanted to be cute about it. I'd wanted to be as masculine and massive as possible, but the meds just wouldn't let me. Yet, I'd gotten what I wanted. I'd served my duty as a college student, and along with that chemistry class you have to take, you also sign up for a whole lot of totally meaningless sex. We never slept together again. We were acquaintances who shared a few classes and exchanged pleasantries, but somehow what happened that afternoon never needed to be repeated again. We were on to other experiences with other people. But I will admit to you that my goal is to make the next woman I go to bed with as sopping wet as she was.