Making it Work
For years, I've battled low self-esteem. I simply can't look at things objectively; I analyze everyone's actions, looking for some indication that they don't like me. Or maybe I'm looking for evidence that, behind my back, they're making fun of me. I don't know, really.
Rationally, I knew that Amy liked me, that my...lack of development wasn't a big deal to her, but in the back of my mind, I was always waiting on the other shoe to drop. I knew I was lucky to be with her, and I was always just waiting on her to realize it.
Those pent-up emotions culminated on the night I lost my virginity.
It was in the fall of my freshman year of college. The freedom of living away from home, the challenging course work...it was all so new to me. And then, on top of that, Amy had begun to become...friskier. I knew what she wanted, but I was so scared. What if I couldn't perform? What if, when I put it in, she asked, "Is it in yet?" Why couldn't we just keep going like we were? I mean, we were happy, right?
I guess I should backtrack a little. After that first time, Amy wasn't shy about going down on me. Nor was she particularly reticent about having me do the same. And I got pretty good at it, too. It was gratifying to be able to please her.
But she wanted more. So did I, if I'm honest, but...you know, size matters. People say it doesn't, and normally I'd agree. But there's a cut-off point. If you're normal sized or even a little below average, everything is fine. But when you're absolutely tiny...
Amy knew this, of course. She didn't say anything, but she knew. So she set us up for success.
It was in her dorm room. Her roomate was out, and we were all alone. We talked about it; I don't remember what was said, exactly. All I really remember was that I was near panic. But what was I going to do? Run away? I told myself that Amy didn't care. I even halfway believed it.
She pulled off her pants. Then came her panties. She got onto the bed, and spread her legs. I started to get in between them, but she stopped me. She didn't want my mouth. She wanted me inside of her.
I took off my pants and underwear. I could see the hunger in her eyes. Was that for me? Did she really think I could satisfy her?
I climbed on top of her. We kissed.
"It's okay," she said. I remember it so vividly. That look in her eyes. Those words. It was all so comforting.
I reached down, and between two fingers, I grabbed my penis. With the other hand, I explored her...you know. And without preamble, I guided myself into her. I had done it. I was inside.
And then I started to thrust, thinking I could go in and out like I had seen on the internet. But each time, I popped out. I couldn't do it; I was too small.
I almost cried in frustration. I couldn't even have sex with my girlfriend properly.
But Amy, as always, was so supportive. After some experimentation, we found something that sort of worked. She spread her legs, and I spread mine. I was on my side while she was on her back. And we pushed together, with me inside. There was no thrusting...just a kind of grinding motion. But it worked. It wasn't perfect, but it worked.
Rationally, I knew that Amy liked me, that my...lack of development wasn't a big deal to her, but in the back of my mind, I was always waiting on the other shoe to drop. I knew I was lucky to be with her, and I was always just waiting on her to realize it.
Those pent-up emotions culminated on the night I lost my virginity.
It was in the fall of my freshman year of college. The freedom of living away from home, the challenging course work...it was all so new to me. And then, on top of that, Amy had begun to become...friskier. I knew what she wanted, but I was so scared. What if I couldn't perform? What if, when I put it in, she asked, "Is it in yet?" Why couldn't we just keep going like we were? I mean, we were happy, right?
I guess I should backtrack a little. After that first time, Amy wasn't shy about going down on me. Nor was she particularly reticent about having me do the same. And I got pretty good at it, too. It was gratifying to be able to please her.
But she wanted more. So did I, if I'm honest, but...you know, size matters. People say it doesn't, and normally I'd agree. But there's a cut-off point. If you're normal sized or even a little below average, everything is fine. But when you're absolutely tiny...
Amy knew this, of course. She didn't say anything, but she knew. So she set us up for success.
It was in her dorm room. Her roomate was out, and we were all alone. We talked about it; I don't remember what was said, exactly. All I really remember was that I was near panic. But what was I going to do? Run away? I told myself that Amy didn't care. I even halfway believed it.
She pulled off her pants. Then came her panties. She got onto the bed, and spread her legs. I started to get in between them, but she stopped me. She didn't want my mouth. She wanted me inside of her.
I took off my pants and underwear. I could see the hunger in her eyes. Was that for me? Did she really think I could satisfy her?
I climbed on top of her. We kissed.
"It's okay," she said. I remember it so vividly. That look in her eyes. Those words. It was all so comforting.
I reached down, and between two fingers, I grabbed my penis. With the other hand, I explored her...you know. And without preamble, I guided myself into her. I had done it. I was inside.
And then I started to thrust, thinking I could go in and out like I had seen on the internet. But each time, I popped out. I couldn't do it; I was too small.
I almost cried in frustration. I couldn't even have sex with my girlfriend properly.
But Amy, as always, was so supportive. After some experimentation, we found something that sort of worked. She spread her legs, and I spread mine. I was on my side while she was on her back. And we pushed together, with me inside. There was no thrusting...just a kind of grinding motion. But it worked. It wasn't perfect, but it worked.
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