I never told anyone this but part of me has always been itching to share. About 20 years ago, give or take, the summer before my senior year, I had been with my boyfriend since junior year. I'd known him for a few years and knew every summer his family went away for a couple of weeks to their cabin. This year, when he came back, I surprised him by giving myself to him, telling him I was ready for him to be my first. And this didn't happen in some romantic setting or anything, just one afternoon while my parents weren't home and he was hanging out. I kind of pushed him on the bed and the whole thing was pretty much done in about 5 minutes, but I never complained or anything. It was exactly perfect and what I wanted it to be. We continued dating until we both went away to college, and then we just couldn't make it work. It was the typical high school love story... except I completely lied about him being my first.

If you were to look at pictures of me back then you would probably just picture Sally Sunday School. I was 5'4" and about 100 pounds, brunette, B cup, and no ass to speak of. And to make matters worse I usually wore a headband. I was always goody-goody and never did anything wrong and I kind of always wanted to, but I didn't want to get caught. It was something I wanted just for me, you know??

My boyfriend was away with his family for vacation. One day I was at the store and as I was checking out I noticed in the next lane a tall, older black man. He was in a suit and not bad looking. He caught me checking him out and I just did the bashful looking away, tucking my hair behind my ear thing. I was walking back to my car when I heard someone run up next to me and sure enough it was the guy from the store. I tried not to look at him but I smiled to myself. He introduced himself as Reggie. We made a little small talk and I don't remember exactly what about but I know he asked if I wanted to go someplace for coffee and to get to know each other. I asked him if he lived nearby. He was taken aback but said he did and I followed him to his place. At his place we sat on the couch and I sat close to him and he asked what I was about and I was honest. I told him I was always the dependable, good girl and just for my knowledge I didn't want to be just for once. And the thought of having this secret turned me on (and still does to this day). Reggie said he'd have no problem "assisting" me in that if I wanted and asked how far I wanted to take it. I told him I'd never given a blowjob before and wanted to try. He asked if I was a virgin and I reluctantly admitted I was. He laughed, wondering if I would even be able to handle his cock. I asked if he'd be able to show me how. He told me to go ahead if I wanted, so I got on my knees in front of him and took him out and immediately realized I was in way over my head. He was long and thick and when he was hard it stood straight up. Even today I remember it as the most intimidating cock I would ever see... and it was my first! Obviously I couldn't fit it all in my tiny mouth so I followed his instructions, and I sucked the tip and licked the shaft and stroked until it was fully erect and then really had fun with my lips and tongue. I had to stop and just stroke a couple times because my mouth started getting sore but after about a half hour he started to climax and then he ejaculated heavily into my mouth. I remember only being able to swallow the first spurt before the thick stream caused me to start gagging. Afterwards, he handed me a towel to clean my face up and offered to return the favor and I let him, laying on the couch and pulling up my skirt. He got me pretty close but in my fear and inexperience I stopped him before I climaxed. As I was getting myself in order and ready to leave I asked him if we could do this again tomorrow. He said absolutely.

The next day I drove over there at the agreed time and this time there was a little more flirting and kissing, the making out stuff, actual removal of clothes right down to our underwear. He tried talking me into letting him pop my cherry but I teasingly turned him down and just stroked and sucked his cock, getting more relaxed and into it, asking if I was doing everything right in that flirty way. I was more prepared for his climax and was able to swallow more of it but still not quite all. He licked and fingered me but still I stopped him right before I finished. We set up the same thing for the next day.

It went much the same way, only this time I didn't get dressed and rush out immediately after. I laid there and let him run his hands over my body and try and convince me to let him "just put it in once" because he really wanted to feel that tight pussy on him. I again told him no in that teasing way before going down on him. I didn't have any trouble swallowing him all this time, though it was the second time that day.

The fourth day we started right off with kissing and slowly pulling clothes away and he immediately went down on me and fingered me. He almost made me orgasm but I stopped him again. I laid there catching my breath and suddenly he was on top of me, kissing me. I was caught a little off guard but fell into it and I started to feel the very thick head of his cock poking at me, just starting to part the lips but not quite entering. I was still riding the high of my near orgasm and this felt really good so when he asked if he could put it in once just to feel it I put my hands on his hips and slowly pulled him in while nodding my head. He went really slow, but he was really thick and I was really tight and it was hard to get it in. It almost hurt as much as it felt good, but it felt amazing and I was really turned on so I just muttered "Oh God" and "It's so big". It took a bit but he got it in as far as he could and slowly started to work it in and out. It wasn't long and I was feeling completely lost in how good it felt and soon we were both sitting up and I was on his lap grinding my way to my first orgasm. When it happened I moaned so loud I practically screamed and I was clamped so tight on him and pushed down on him so far that I set off his orgasm. We were locked in a way that he couldn't pull out and he was as deep in me as he could get and he ejaculated everything into me. He immediately started to apologize, but I was stuck in case of the post-orgasm giggles and I cut him off, telling him I didn't care, it felt incredible. I was really sore and couldn't handle him pulling out well we were both throbbing, we just laid there kissing, talking, and laughing for a while. We both knew it was the last time but we were okay with it. I left him my panties as a reminder.

When my boyfriend came home a week later I gave myself to him. I really lucked out that I didn't get pregnant or anything from it all, but I liked the fact that I know I'm not the goody-two-shoes everyone, including my best friend and my husband, think I am.