How Jack Lost His Virginity

Let’s call her Amy.

I saw her every day. She was this cruel, beautiful, petulant, bossy little thing. I went over her house every day after school with my cousin.

Amy was my cousin’s best friend and she tolerated having me in her home because I told amusing jokes and because I was smart enough to figure things out that she and my cousin couldn’t. I could do things like talk people’s parents into things and fix their computers and so on.

Amy, of course, would never be seen with a chubby geeky boy like me. Plus we were the same age and obviously she could only date seniors, if not college boys. Still, I had some things she wanted, music, better notes from classes we shared, money to buy the silly things kids like, so she occasionally put on a smile and cuddled up to me and asked me nicely for things. That’s the way kids are.

I would basically do anything for her. There were a variety of reasons for this, her looks, her attitude, her coolness, her casual sexiness.

Eventually my cousin got a boyfriend and didn’t want to go over Amy’s house after school. It was closing in on summer and I wondered who I would hang out with. At lunch Amy passed me a note that I should still come over. She also told me not to tell anyone.

Thus the game started.

I went over Amy’s house every day for two months. We were alone from 3pm to about 5pm when her father got home from work. He was, to this day, one of the scariest men I’ve ever met. Tall, white hair, bulging arms, a scar across his cheek, a incomprehensible Baltic accent of some kind. Still that added to the thrill of it.

When you are a fifteen year old boy you aren’t alone with a girl very often. She saw my nervousness and my attraction and it gave her a taste for power. She would boss me around, she would tease me unmercifully, occasionally she would corner me in her room and ask me if I wanted to see her breasts. I shook my head like an idiot.

She showed me, watching my face, watching how I drank in the first taste of a real girls breasts. A week later she let me touch them. A week after that she let me put my hand down her pants.

We didn’t know what we were doing exactly, but we had good instincts. She let me explore a little, moving my fingers around until I hit a spot that made her gasp. Everything was suddenly wet and those teasing eyes were changing to pleading.

She shifted and I got spooked, pulling my arm away. She told me I didn’t have to stop. My mind was racing, my skin was tingling and I felt this rush I’d never known.

I told her I wanted to see, but she was embarrassed. She turned off the lights and took off her pants. She kneeled on her bed in underwear, twisting and turning to take off her bra without taking off her thin cotton shirt.

The gray light of a Spring afternoon barely came through her windows, but it was enough. She laid down and I laid next to her, she didn’t like to kiss usually, but we fell our lips awkwardly touched. Then my mouth was on her neck and she was cooing and pulling at my arm, pushing my hand back to where it was supposed to be.

I pulled the scrap of panty to the side and felt her soft hair, then the wetness of this unspeakably amazing thing. I played, toyed, watched her responses. I wanted to kiss her every where, take her, fuck her, I didn’t know what to do. I just rubbed. I rubbed and rubbed until her hips were pushed up at me and she pushed her head into my neck and made little bird cries.

Then she pushed me away, half laughing but half scared. She made me leave. She wouldn’t look at me.

The next week we went back to watch television and doing homework. By that Friday we were back in her room, back on the bed.

“Let me see yours,” she said, which was new. She never cared about my body or my pleasure.

She grabbed it hard, too hard, when I protested she laughed and then touched it gently. She looked closely but didn’t really do anything to it.

“Make it hard,” she commanded, but I was far too scared.

She kissed me, though she hated kissing or at least hated kissing me. She whispered warmly into my ear. “Make it hard, I want to see,” and it was done.

She pulled the curtains closed and then I felt her next to me in the bed, the room now pitch black. She climbed on me and I felt her naked hip brush my leg. She pulled off my boxers and grabbed my hand, pulling it to her naked crotch. She was wetter than last time, wetter than anything I’d felt.

She held my hand against her, grinding against it. I kissed her neck and she gasped so loudly it scared me. Then she was pulling me on top of her, we were rolling around on the bed, I was hard and scared.

“Do it. Do you know how?” it was a mocking joke, but also a serious question.

“Yeah, but we need… I mean we shouldn’t,” I didn’t know what I was saying, but looking back I am impressed I could even manage a protest.

“I’m on the pill. Do it,” she wrapped her arms around me.

I knew somewhere in my head it was still a bad idea, but then she shifted and the tip of my cock brushed against the wet heat of her. I moved and tried different angles, different positions and then it was suddenly half in her.

She grunted and clawed at my back.

“Do it!” she growled.

I pushed it in, now that it was wet it moved slowly in and all I could think was how hot it was, how I’d never felt anything so hot. It was this hypnotic burning and throbbing.

I pushed it in and out and I moved down to kiss her, but I got her neck. I pushed it all the way in and howled at the pleasure. My body didn’t know what to do, every nerve was overloading.

It went on, not long, but it seemed like hours. When I started to come I tried to say something and she pushed me off of her. I tried to hold it and ended up coming into my hand, the sudden change from fucking her to crouching on the floor next to the bed confusing me.

“Gross,” she laughed, but her voice was darker now.

I stood up and looked around.

“Bathroom,” she said flatly.

I went to the bathroom, giddy, confused, wet with her. I washed my hands and my dick and my face. I heard a flop and then a door slam. I looked in the hallway and saw my clothes.

“Get out,” she said from behind her door. She laughed and then locked her door.

I dressed, a cold numbness suddenly filling my veins. All the adrenaline and hormones and lust all shut down at once. I felt stupid and ugly and fat.

She didn’t speak to me at school after that. Not unless other people were around and then she would tease me. I never asked her about it or tried to go over there again. That summer she went away with her family. The next year we moved on to other friends.

Sometimes though she would run into me and say something cruel. Not the normal insults teenagers say to each other, but something really personal and mean. It was a message. I wasn’t even supposed to think about telling anyone. I was to learn my place and be thankful for the scraps I got.

Frankly I was thankful. It was years before I ever even thought about how cruel and strange the whole thing was.

17 thoughts on “How Jack Lost His Virginity

  1. Do you know how many males I know who’d give their left nut for an experience like that? When you’re 15, that’s sexy as hell. At 35, it’s just pathetic. Great story, thanks for sharing.

  2. Do you know how many males I know who’d give their left nut for an experience like that? When you’re 15, that’s sexy as hell. At 35, it’s just pathetic. Great story, thanks for sharing.

  3. Why are first times so fucking strange? I don’t know of anyone who has had a normal or satisfactory one.

  4. Why are first times so fucking strange? I don’t know of anyone who has had a normal or satisfactory one.

  5. Not quite sure how to respond – I’ve been thinking about it for a while, and can’t come up with a good response. I agree that it was sad; sad in a way that I find really upsetting.

  6. Not quite sure how to respond – I’ve been thinking about it for a while, and can’t come up with a good response. I agree that it was sad; sad in a way that I find really upsetting.

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