Sexually, I was a bit of a late bloomer. I didn't lose my virginity until the summer after my senior year in high school, when I was almost nineteen, long after all my girlfriends had gained enviable amounts of experience.
I had a boyfriend, Barry. The first thing you should know about Barry was that he was gorgeous. He was on the swim team, one of the best swimmers at the school. His body was muscular, but sleek instead of bulky. The sight of him in a pair of wet Speedos was enough to make any girl damp in the panties. Plus, he knew how to dress and groom himself, skills in which most guys at my school were sorely lacking. Barry wore the best clothes, the best colognes, had the best haircuts. He always looked good and we looked good together.
The second thing you should know about Barry was he was the nicest guy I had ever met. He was kind, considerate and fun to be around. He treated me real nice. We were literally best friends. When I saw some of the jerks and lunkheads my girlfriends ended up with, I considered myself lucky, despite the third thing you should know about Barry which was, he never touched me.
We had been going together since the start of Junior year and in those two years we had three "real" kisses, he'd felt my tits up two times, and I'd touched his cock once. (It wasn't even hard at the time.) We had even slept in the same bed on many occasions, but still nothing. I tried everything I could think of. I got him drunk, I dressed like a hooker, I literally begged for it. Barry just said that he didn't want to do anything until we were married, an event which he promised was looming on our horizon. He even bought me one of those "promise rings," a very nice one.
I was dubious about this excuse because Barry seemed to have no moral qualms about anything else. He drank, he smoked cigarettes and pot, he swore like a sailor. Barry didn't have any religious convictions that I could identify, and he even sometimes made fun of the Christian kids at our school.
Still, when I saw some of the agonies that my girlfriends went through because of their sex lives, I almost considered myself better off. The pregnancy scares, the guys who "played" them, the stories about getting caught by their parents and being grounded for months. Who needed all that? Barry and I had been together for two years, more than twice as long as any of my girlfriend's longest relationships, and I thought that perhaps this was because we didn't have sex to ruin things. Maybe all those sanctimonious weirdos trying to sell us on abstinence had a point.
The problem was, I was horny as a minx. Someone had bought me a vibrator as a "gag" gift for my birthday. I'd laughed at the time, but eventually went through hundreds of dollars worth of batteries. Dates with Barry could get me so worked up, and since he wouldn't do anything about it, I'd have to take the matter into my own hands. I became an avid and creative masturbator, experimenting with water jets, anal stimulation and assorted fruits and vegetables. I could get myself off a dozen different ways, but I knew they were all just poor substitutes for the real thing.
Finally, at our Senior prom, I decided that I wasn't going to wait any longer. I wore a strapless sex goddess dress and made a point of slipping my panties into the pocket of his tux jacket, folded up like a handkerchief. (He looked like James Bond in his tux, by the way.) We slow danced all night and I whispered incredibly dirty things into his ear the whole time. After the dance, as a surprise, I'd booked a suite at the most expensive hotel in town. Hot-tub, champagne on ice, box of condoms in the bedside drawer. I'd even gone on a Mom's-credit-card spree at Victoria's Secret and bought some really high-class frilly slut-wear. I could have seduced the Pope that night. But not Barry.
That was the night that Barry told me his big secret, which I found out later everybody in the world knew but me. He was, of course, gay.
I was utterly shocked. Call me naive, but I had no idea. Whenever I'd tearfully spill the secret to a friend, they'd always say they'd known for months. Even my Mom knew. Upon learning that Barry and I had broken up, she said that it was for the best because I'd never get a real boyfriend if I hung around queers. Of course, nobody had thought to tell me.
Barry and I didn't speak for several weeks and I was in tears for my high school graduation. I missed him so much. Finally, swallowing my pride, I gave him a call. He said he missed me too, and that his fondest hope was that we could still be friends, like we were before.
Of course, it could never be as it was before, not with this between us, but I thought that maybe we could develop a new kind of friendship. Plus, even then, in the back of my mind there was the thought that I could somehow "turn him," win him over to the right side of The Force.
But then I met Barry's new boyfriend, Terry. Barry and Terry. How goddamn cute is that? They had been seeing each other for a while, even when Barry and I were supposedly together, but I elected to overlook this fact. It was important to Barry that Terry and I got along. "The two most important people in my life," he said. Whatever.
The thing was, Terry was remarkably easy to get along with. Plus, he was almost as hot as Barry. He was into track and field, and so had a whole different set of muscles from Barry's swimmer's body. Dark-haired where Barry was sandy brown. More boyish, whereas Barry had this kind of mature look that had always driven me wild.
We ended hanging out a lot. I liked going out with these two hot guys, being seen with them. The thing about gay guys is, they're almost just like girls, so it was a lot of fun. They both liked to shop, both liked to dance. The best part was, Terry's parents were in Europe for the summer, so we had this huge house on the lake to hang out in. I spent most of my nights there. Of course, when bedtime came around, the two of them went into Terry's room and shut the door, leaving me to cry and/or masturbate myself to sleep in the guest bedroom.
With his parents gone, Terry was also able to display his huge collection of gay porn. Pornos, straight porn that is, had never appealed to me before. Ugly, hairy guys with big cocks plugging silicone-injected Barbie dolls and coming all over their faces. That was supposed to be sexy? But gay porn got me hot. The pretty boys were almost always the "bottoms," sucking cock or getting fucked, and I would always identify with them, imagining myself being taken by some big-cocked manly man. Plus, I may be wrong here, but it seemed like the gay pornos had better production values. Better camera work, better sound, better acting, all that. That may seem like a small thing, but I was never able to get past the over-lit, cheapo video of regular porn.
Sometimes the three of us would sit around Terry's living room watching these things on his parent's big-screen TV. I know we were all getting turned on. Barry and Terry would sometimes retire into the bedroom halfway through the video, and then I could finally stick my hand down my shorts and stroke myself off. Still, it didn't seem fair.
One night, we were watching one of the videos after hitting Terry's parent's liquor cabinet pretty hard. I was more than a little drunk and so horny I was almost delirious. I looked over and noticed that Terry was stroking Barry's hard cock through his pants. Barry kept swatting Terry's hand away, embarrassed I guess to do anything in front of me.
"Don't stop," I said. "I want to see."
"No," Barry said, blushing.
"Why not?" I pressed.
"It'd be like my sister watching me," Barry said.
"I'm not your sister," I reminded him. "I was your girlfriend, remember?"
"Yeah, but . . ."
"If you won't do anything with me, the least you can do is let me watch you guys fuck."
"Yeah, right," Barry said.
"I'm completely serious," I said, and I was.
Terry started laughing hard. I could tell he was excited by the idea. Barry kept hemming and hawing, but with me and Terry both working on him and him already worked up with the liquor and the porn, eventually he gave in.
Terry undid Barry's pants and pulled his cock out. I literally gasped when I saw it. Barry's cock was huge. I'd known it was big, but I'd never seen it erect before. In fact, that was only the second time I'd seen an erect penis in real life. The first time was when I accidentally walked in on my step-father when he was masturbating years before. Barry was even bigger than Donald.
Terry stroked it lovingly. "It's a monster, isn't it?"
