Where it happened: Sister's house
Like most guys, when I hit puberty I was burning to get laid, touch some breasts, kiss even, but I must admit that I was absolutely terrified of women and the possibility of rejection. When I was 14 or so, there was a girl who was interested in me, despite the fact that I was quite a nerd, but I was so nervous about it and at such a loss as to what to even say to this girl, much less grab her ass, that I just avoided her. I regret that, it would have been fun.
When I was a senior in high school, I unwittingly went on a blind date with a freshman girl, and when I was alone with her for the first time, you could see the lust in this girl’s eyes. I mean, she was 100% ready to go, all I had to do was make the first move and she would’ve been pulling down my zipper, but I didn’t go for it. I wasn’t really scared like when I was 14; rather, she was barely 15 and plus, she had fallen out of the ugly tree and hit every branch on the way down. Her body was OK, but I really had trouble with her face and lack of style. Plus, I didn’t like her at all, and it didn’t seem right to use her like that. It’s odd to think that I could’ve fucked her no problem in the back seat of my friend’s Dad’s Buick, but I knew I could do better. And I did, but it took about 3 years.
When I got in college I figured, “Ah, the promised land! I’ll be fucking in no time.” But the first year came and went and no action, despite my best efforts. Then my second year started, and things started looking up.
Samantha (not her real name) stumbled into class on the first day late, looking terrified and overdressed. She was about 5’3″, a dyed-blonde bob haircut, very petite and quite toned, like a ballet dancer, and her breasts were a little bit small for her body. She wore glasses, which seemed to be an in for me, as I wear them as well. She sat down behind me and from that day on, she became quite friendly, maybe even more than I wanted. I found her a bit irritating, but she was shoving herself into my life and I thought, “It’s high time you got laid, she’s making it easy for you. Go with this for a while, see what happens. Don’t lose this opportunity.” I felt that as long as I didn’t lead her on, no one would get hurt.
I used to get to school early, and she figured this out, and she found out where I would relax before class and would sit and talk to me. Turns out she was breaking up with her boyfriend of 5 years and although it didn’t hit me then, in retrospect she was obviously on the rebound and looking for some companionship. That’s the thing about her, she was very needy and delicate; I knew pretty much from the start that she was looking for someone to take care of her. I knew that that person wasn’t me, but I tried to help her how I could. But honestly, I was just hanging around for some sex, you know?
The first time I took her out, she showed up in a hot little dress. I drove her to the movies, parked the car, and we started kissing, which was pretty weird, since I’d never really done that. I remember that she smoked, and I could really taste it. Not very nice. I unbuttoned her shirt and grabbed her tits and licked her chest. True to form as I would eventually realize, she was very passive in sex and preferred for the man to take the initiative. My dick was not touched.
After the movie, I took her home and dropped her off. She didn’t make any moves, and I went home frustrated. I think I whacked off in the car just for relief, I can’t quite remember.
Anyways, a week later my sister asked if I would watch her house while she was in Hawaii, so I said yes and told Samantha about it. She said that she’d like to stay with me. Out of the blue, just like that. It was weird. I think she wanted to get away from her mom for awhile. So I said yes, and I thought, “Well, you’re gonna get fucked, good or bad, my dear.”
When I picked her up, I think we were both thinking that when we got to my sister’s house, the sex would begin. And it did. I remember her sitting on my lap next to the kitchen table, facing me, and kissing me. Then we went into the bedroom where she stripped off, and I did too. It was pretty damned weird being naked in front of each other, and I had a difficult time getting it up, it was so alien and tense. I remember sucking on her pert little tits and thinking how different they tasted and smelled than I thought they would — not flowery and sweet, but a bit musky and salty. Then I went down on her, and that was really strange as well. She was clean, but the smell was very strong due to my inexperience. I had expected, again, for her pussy to smell sweet and rosy, but it was very musky, like a woman’s arm pits. She was a bit hairy too, which was odd for me to see since I’d cut my teeth on Playboy and such, where the women trim their bushes. The taste was the strangest thing, since I’d expected it to be honeyish, but in fact it was quite bitter. I’ve since learned that pussy juice varies from day to day in a woman; sometimes sweet and fragrant, sometimes tasteless, sometimes salty and bitter, and sometimes just plain bad.
I licked her for ages, but my technique was clumsy, and she wasn’t really that lubed. Either that, or I had licked her too much and she was beginning to dry out. I remember wishing so much that she would suck my cock, and she did, for about 15 seconds, and then she stopped. She was one of those “I don’t want to be demeaned” types and I think she found giving head degrading. But she sure didn’t mind receiving it. But when she sucked me she was in a 69 and it was a bit gruesome to be headfirst into a woman’s snatch and ass for the first time. I clearly remember seeing her pink asshole looming over me and I thought, “It looks so weird!”
My cock was semi-hard but she didn’t seem intent on helping me out, so I figured I’d try to put it inside her. But she was so dry that it just wasn’t working. But I was determined. I got down and pretty much put as much spit as I could on her pussy and then slowly started pushing into her. It was laborious, as my cock wasn’t very hard. But it finally worked, and I was stiff inside of her. It was a strange feeling as I lay on top of her trying to set up a rhythm and make her feel good, but it was a bit of a mess. I remember that my cock felt really hot, like her body heat was heating it up. I remember really going fast, not pacing myself or slowing down to make things last, and I felt rumblings in about 1 minute. I remember she wasn’t on the pill so I pulled out and dropped a bunch of glops of my goo on her belly and on my sister’s blanket. I think she was irritated that I came on her, as she went to the bathroom and hopped in the shower really quick.
I dated her for another 6 months and improved my technique markedly. I never really loved or liked her, and she was a terrible lover, very, very passive, but she was there and I was hard, and I worked out 20 years of sexual repression with her. The best was one night where I was very horny and she wasn’t, and she said, “Well, you can still fuck me.” So I did, as she lay there, staring at the wall. It wasn’t the best sex, but it was really unusual, like fucking a prostitute or something, or masturbating inside a woman. We eventually hit a wall because I wanted more sexually in terms of variety. She didn’t like giving head, and wouldn’t suck me until I came, and God forbid I come in her mouth. She also wouldn’t let me fuck her doggy-style, so I thought, “Not much left here, time to go.” We broke up over the phone. I remember her saying, “I love you, I’ll let you fuck me doggy-style if you stay,” but I couldn’t care less. Someday I’ll tell you about my first wife. Now THAT was a girl who could fuck, I’ll tell you!