Erica's First Time

*All parties are of legal, post-secondary school age*

Thanks to things like AOL and Yahoo Chatrooms, I learned that I wasn’t alone in my desire and attraction toward men. Back then, pictures downloaded at a blistering 56kbps, so while there wasn’t much to see, there was certainly a lot to talk about. And the guys online were, as you’d expect, very eager to share their experiences with me and find out more about me. I grew bored with describing myself the same way over and over, so I started to share some of the things I wished were true about myself… inevitably, describing myself as somewhat of a sissy.

It wasn’t long before I had the attention of a lot of fellow perverts, and one in particular kept encouraging me to “be more adventurous” and “try it for yourself.” He even went so far as to write a story for me, called “Erica’s First Time,” in which he described in detail how he would be the one to send me down the path of debauchery. I read it nearly every day, sometimes multiple times per day, and with his encouragement, I made a plan to try and experience things for myself.

There was a guy, Michael, in one of my classes that played football. Now, the football team usually hung around together, but they couldn’t avoid the locker room. Everyone had to change with everyone else, and one thing stood out: Michael had a really curved penis, moreso than any of the others I was seeing (and I was making a lot of effort to see as many as I could). After a couple of weeks, I realized that he saw me staring, but didn’t do anything to cover himself or turn away. He wasn’t the type to leave his circle of jock friends, so one day while we were waiting in line I asked him if he would ever want to get together and play video games. He lived in a subdivision that backed up to mine, so I knew I could easily get to his house. A few days later, he mentioned a new video game drop and asked if I could come hang out one Friday evening.

I shared what was going on with my friend online. He, of course, encouraged me to go through with it, to not back out, to not worry about what others might think. I was eager, but nervous. I’d read a lot, and seen a few pictures online, but was inexperienced. So, on the evening in question, I wore some white panties (part of the online story was that virgins should wear white). I also had on an old sports bra, and a t-shirt that was one size too small and showed my tummy when I lifted my arms. I wore some regular shorts, hopped in the car, and headed to his house.

Once he was sure we were alone for the evening, he mentioned it was warm and asked if I wanted to swim in his pool. I told him I didn’t have a bathing suit and asked if I could borrow one. He was bigger than I was and deep-belly laughed, saying there was no way any he had would fit me. But, he said we could just skinny dip. It was, after all, dark outside, the pool was fenced in, and no one was home. He confidently threw his shirt off and slipped out of his pants and boxers, revealing that sweet curved penis I’d been awestruck by for a while now. I slowly took my shirt and shorts off, revealing my sissy attire. He told me it was cute, but I wouldn’t need them for swimming. I got naked, followed him outside, and we jumped in the pool.

It was really warm. We swam for a little bit, taking turns jumping off the diving board, shooting baskets in the poolside hoop. When he came over behind me to get the ball, I felt his cock against my leg. I felt butterflies like I’d never experienced before. He backed up and moved away a bit, but in short order, I found myself against him again. This time, I touched it. I felt it, and he twitched. Under the water, I stroked it a little bit. He smiled at me, and put his hand over my hand while backing toward the side of the pool. He turned around and pulled himself out, then sat on the edge of the pool. I moved in closer and got the first real, up-close look at it. It had a bigger head than I remembered seeing. It was swollen, there were little bumps and ridges running the length of this shaft, down to a tight sac of balls that hung below. I rubbed it some more, watching it bounce, hearing his breath catch. He twitched when I got near the head.

I remember tasting it for the first time like it was yesterday. There was a mix of chlorine and precum. I could smell his warm, just-out-of-the-pool skin under my nose. I had no experience giving a blowjob, so I did what I thought might make it feel good for him. I licked around the swollen head, squeezed his shaft. I licked it up and down a few times, put one of his balls in my mouth. I stroked him softly, watching it closely. I put it back in my mouth and nursed on it gently, careful not to use my teeth, while he continued to have precum glisten the head for me. I have no concept of time that night, but when my mouth started to get dried out and my jaw started to hurt, we went inside.

I stood there naked in his basement while he laid the couch cushions on the floor. He told me to lay down on them while he went and got some hand lotion. He squirted it in my hand and had me stroke his cock with it. The chlorine had dried and made his cock dry, but with the lotion, it was slick and I was able to pick up speed. I masturbated him for a few minutes, me sitting on those couch cushions while he stood in front of me. His breathing was kind of ragged, and he asked if I wanted to try to fit it in my butt. I told him yes, I’d try anything.

He told me to lay on my stomach, so I rolled over and laid flat. I could feel his weight as he knelt next to/on top of me and put some lotion on my hole. I could hear him squirt some more on his cock, then I felt his knees on either side of my legs and his hands beside my ribs. He lowered himself down onto me and I felt his bare chest on my back, and then his cock against my crack. He laid like this for a minute, slowly working his cock up and down my crack. I was still as could be, I had no idea what to do, so I let him take the lead. He raised his hips up, moved his hand to his cock, and pushed it down toward my slick hole. I felt an immense amount of pressure against it, then nothing. Then I felt him again, trying to push it in, slipping around, trying again, then nothing. It took him about five minutes of pushing until finally, he popped through.

Holy shit, it burned. I felt so full. No one tells you that first time how it’s gonna go, what it’s going to feel like. I felt a mix of pain, worried that I was going to make a mess. The lotion obviously wasn’t a very good lube (it burned something fierce). I adjusted after a couple minutes, and he slowly started to push into my tight ass. It felt like a hot piece of iron, and I kept asking him to go slower, while he just gradually worked the entire length into me. He started to pull out, and I panicked, and clenched my ass, which made him moan. He pushed back in, making me moan, and we got into a little rhythm.

Imagine with me: Here I was, with an older football player fucking me from behind. I was no longer a virgin. I had a million thoughts running through my head. He fucked me for about ten minutes, maybe? Again, no real sense of time. Because I was pinned against the cushions, the sensations on my little penis were intense, and I had made a wet spot with my own little orgasm at some point. Without warning, he pushed in hard and held it. It burned, and then, it was gone. He pulled his curved dick out of my little ass and I rolled over.

I watched as he got soft. He got in front of me on the cushion and sat down, telling me how that had felt really good and he was glad I came over. I took his dick in my hand again and played with it, then licked it for a bit. No one had warned me about the wild mix of flavors from the chlorine, lotion, cum, and ass. It didn’t get hard again, and I guess he got tired of me, because he stood up and went to the bathroom. He came back and put his clothes back on, but asked me to stay naked for a while. He heard his roommates moving around upstairs, so we scrambled around and got dressed quick. We played a few more video games, but my mind was swirling. I started to have those weird feelings, so I decided not to spend the night. I made the walk of shame home in the dark, a weird mix of fluids leaking in my panties and shorts. I debated, once I got home and settled down, but ultimately decided to shower off the remnants of my night and go to bed.