I was always curious about sex from the time I reached puberty. When I realized how good it felt to touch yourself I started to understand why they say boys do it all the time and I spent a lot of late evenings after my parents went to sleep exploring my body and finding objects to insert to pretend it was a penis in me. It wasn't long before I was exploring other areas of my body, too. I started watching porn and before long I had an incredible secret addiction to sexual pleasure. So a few years ago, I knew I wanted to explore this with someone else but I was scared. I heard the stories and didn't want the reputation, but I was horny all the time and it was difficult to contain, but I didn't want it to be someone I knew or who knew me... so I went to Craigslist.

I didn't know the personals had so many images of people showing their stuff but I knew being 4'10 and skinny that I wasn't going to convince anyone I was older than I was so I responded to a few ads that looked interesting but I was honest. One guy responded. He was older, pushing 50, and married, but handsome and really okay with keeping things on the DL and everything. He traveled for work so we were able to Skype while he was away from home. It was interesting, sharing my thoughts and everything and that first night we started emailing we decided to Skype. I just had on booty shorts and a cami top and was laying in bed and he commented on how great my boobs looked (despite my very small frame I have a B cup that pops up nicely depending on what I'm wearing. I teased him with cleavage and joking around but it wasn't even 20 minutes before I was naked with the handle of a hairbrush inside me while he stroked his nice cock that stood straight up. After a few moments he talked me to lay on my side facing my computer and to work the hairbrush into my ass. I did. I laid there one hand working the handle of the hairbrush in and out of my ass, which my other hand rubbed my clit and before long I was seeing him shoot a thick, creamy load and then I started to orgasm.

He asked if I had fun and I panted yes and he asked if I wanted to do it for real and I said yes. It took a couple weeks (and we skyped nearly every night) but my parents went on a camping trip for a weekend and he found some way to "be away for work" that weekend and got a room in my town not far from my house. He picked me up after my parents left but I was already super horny so I tried to convince him to come to my room first but he was nervous so we made it to his hotel and barely inside the room before I started kissing him. He made me slow down, telling me he wanted to admire my gorgeous body in person first. I undressed for him and he touched me all over and then told me to undress him. I got very turned on by him taking charge and did so. I then was ordered to suck his cock and I did and I loved it. It was my first time ever but everything about it was just a great sensation. After that he went down on me for... I don't even remember but it was a long time. I thought I was about to have my first not-self-induced orgasm on his tongue, but just as I said "I'm going to cum" he jumped on top of me and jammed his now-hard-again cock deep inside me and fucked me through my orgasm... and then for a long time after until he finally shot a massive load up into my once-virgin pussy, which triggered another orgasm for me. After I settled down, I suddenly realized what just happened and he must have seen my face because although he was still on top of me (and still in me, I could still feel his cum flowing into my body) he held me down with all his weight and told me to relax, he had a vasectomy and I wouldn't get pregnant. I relaxed and we fucked all weekend. He filled all my holes with his cum (yes, even my ass, which was so tight I could barely take him).

Turns out he lied about the vasectomy. I didn't get pregnant, he just admitted it after I started my next period. We kept up the affair for a couple of years and I'm surprised I didn't get pregnant, even though my obsession with sex made me believe I was in love with him and I kept telling him to put a baby in me. Things eventually ended and thankfully no drama came of it. I probably should have just continued keeping it to myself but I'm alone now, single, and horny and wanted to share this story as I get myself off.

I hope the rest of you enjoyed :)