Rylie Ch. 01 - My First Blowjob

Usual Disclaimer Time: All the characters in this story are 18 years old or older

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I've always been the skinny girl. Back when I was 18 (I'm 26 now), my senior year of High School, even though I didn't have the curvy body some of the other girls had, I was still seductive enough to get attention from pretty much any boy I wanted to. And even though I had been quiet and shy up until senior year, I made sure I rewarded the attention I was starting to get by giving focused, sexually charged, eye contact. I thought of them as staring contests.

I have curly, dirty blonde hair. When I was a teenager I used to straighten it but when I got to college I let it stay curly. I tan easily and my boyfriend likes to trace the freckles on my skin when we're lying in bed.

But what was it the boys really started to notice?

I'm told I have pouty, sultry lips. I remember learning I could communicate with them, very subtly, even in class. At my desk, I would catch boys' eyes, pout my lips and tilt my chin down with my eyes looking up at them and inevitably they would come up to talk to me after class. Usually it was an awkward question about homework and I'd pretend to not know what I had done. I tried to practice the pout and look at every guy in class. This is when I had complete senior-itis. I made it into kind of a game. One of the popular boys, Jared, who I thought was really an asshole, was the most direct with me after class. He told me I have "dsl" and only later found out that meant "dick sucking lips."

And even though I gave lots of guys that kind of classroom attention, I only ever tried out my "dsl" on one guy, because I felt he was the only one who really dissevered it. His name was Corey. He was shy, but cute and rode the bus to school with me. We had practically grown up together. When we were little we'd have play dates and go to each others' birthday parties but starting in middle school didn't hang out anymore. That kind of thing. We'd talk sometimes on the bus and I could tell he had a little crush on me.

Senior year we were in English class together and I started going over to Corey's house to do our homework together. It was the day that other jerk told me I had "dsl" that I suddenly decided, while going over an essay with the cute, shy boy who had a crush on me for years but never told me, that I was going to suck his cock. We were sitting on his bed looking at his laptop. Out of nowhere I took his laptop and put it on his desk. He looked at me like "why'd you do that?" And I pouted at him. He blushed. I put my hand on his zipper and pressed down into his pants. I could feel his boner and I squeezed it. He looked shocked but very happy. I fumbled with his zipper - I had never unzipped someone's pants before - and he helped me bring his dick through the hole in his boxers.

Thinking back on it his penis wasn't that big but I think that's kind of cute. And at the time I was just so excited. I leaned over and placed my head on his lap, gave him one more sultry look, and started to suck my first cock. I remember we both had to be completely silent since his family was down the hall. Since his dick wasn't particularly big I could easily fit it all in my mouth. I can still remember the feeling of the hair on his balls brushing my lips. It's actually a sweet thought. And back then, I didn't realize I should be bobbing up and down like I do now. I even tried to keep swallowing my spit so it wouldn't drool, though now I know guys love that. So I kind of just kept my mouth pressed down on him and he sort of humped my throat. He was very sweet and rubbed my curly hair. His thrusting wasn't smooth, but more like overexcited spazzing into me. He stifled grunts. I loved it.

The funny thing was that we went for so long. Like two hours, just like that. I didn't know at the time that's a ridiculously long time to just deep-throat a guy (remember, not even moving up and down) but I had nothing to compare it to. My lips were numb for the rest of the night after but I liked that, I thought that was part of it. Eventually, he started humping faster. For the last half hour or so I had started licking his shaft, while completely submerged on him and clearly liked that. I felt a stream of liquid spilling out of him and I wondered if this was what cum was. I quickly swallowed that up too so none could escape. But soon after, he gave an extra big thrust, actually pretty aggressively, like desperately, and for the first time ever I learned what it was like to take a load. Corey's cum was thick and sticky and a little sour. I choked a little swallowing it all. We both giggled. Even after that I dedicatedly held my mouth all the way down his cock, the tip of his head slowly moving up from the back of my throat as it got soft. He had to lift my head off his lap and I realized we did it.

This was like a month before graduation and we went our separate ways but I must have given him head like 4-5 more times. We never had sex.

My pouts to other boys in class only got more intense since I felt so confident but I never acted on it with any of them. Even though I know Jared, the asshole, most of all wanted it. It's weird, even though I didn't like him at all, I teased him the most. Maybe 'cause I know he wanted to so badly. I would make eyes at him in class. He would stare right back at me. I wondered if I made him get a boner. One time things got out of hand and I licked my lips while staring back at him. I could see him practically convulse in his seat, his face so red and sweaty. I don't think anyone else noticed. But after class when he'd approach me I'd always pretend nothing had happened and enjoy his frustration. This guy was such a bully to so many kids, especially Corey, he didn't deserve anything. But he was also the one who first taught me I had a great ass, even back when I was totally skinny and my breasts were small.

I was bent over at the water fountain after class and I could hear Jared come up behind me and say "you have a really good butt too." I know that sounds so stupid and it was but I guess that was as good as high school game got. I know other girls in my year were having sex with him. Truly, he repulsed me. But I liked that he wanted me. As he said it he kept approaching the water fountain and kind of brushed his crotch up on me before I moved away. I acted like it was gross and totally uncalled for, and it was, but also I had literally licked my lips at him 15 minutes before. I was wearing leggings that day and could feel his boner through his pants, only for a second. I had no interest in him or his boner but it turned me on.

I took it out on Corey after school. Instead of sitting next to him on his bed and going down on him like we'd done a few times, this time I sat on his lap and rubbed my ass on him while he humped me just like he did my mouth. I turned around and straddled him while we made out and moved his hands to grab my ass. Up till then I had actually never taken off any of my clothes with him - my body was still so skinny and curveless then - but that day I bent over his desk (more exaggeratedly than I had at the water fountain) across from the bed, pulled down my leggings just so my ass was exposed. I think at first he didn't know what to do. This wasn't our usual routine and we were both still virgins. But I wanted to see what he'd do. If it would be anything like Jared.

Soon I heard Corey get off the bed behind me, move towards me, and press his crouch into my bare ass. This is what Jared had wanted. But this time instead of moving away I just murmured "yeah" and let Corey dry hump my ass cheeks, while I sort moved my nonexistent hips around. After a bit, I turned around, pressed Corey back against the bed while he was standing, got on my knees (for the first time), pulled down his pants, and sucked his dick like my lips were magnetically pulled to his balls. I remember he lasted less than two hours that time.