It took a while before I decided I wanted to do anal again, but I ran a few ads, and finally found someone who talked me into meeting him who didn't sound crazy or whatnot, and turned me on with his emails, talking dirty about how he'd slowly seduce me and "make me his bitch". I'd arranged to meet him at a condo in Honolulu. I didn't have a picture, just a general physical description about him being in pretty good shape, and described himself as a "total top".
I nervously walked up to the condo, wondering if I'd even be able to spot him, but then he made eye contact and I could tell by the appraising, knowing look in his eye that it was him, that he recognized me from my picture and liked what he saw. He was stocky and muscular and had a crew cut, really butch looking.
Anyway, I said his name, with just a hint of a question mark in case I was horribly mistaken, and he nodded and held out his hand and we shook. A little small talk, then he asked me -- well, more like told me -- to follow him up to a friend's place he had for a few hours that morning. We rode the elevator up in silence, got in the room, and there was this weird awkward moment where I wondered if I wanted to go through with getting fucked by a total stranger who I had barely talked with.
But then he squeezed my ass and said he liked my body, and looked me in the eye and asked me if I wanted to do what I'd mentioned in our exchange of emails, maybe start by getting on my knees and sucking his cock, and god help me I did want his cock in my mouth. So I knelt down before him while he dropped his shorts, revealing white briefs with the start of a bulge in them, and I reached out and started kneading his cock and balls through the fabric while he got harder. Then he pulled his shorts off too and his hard prick sprang free, and he asked me if I had any fantasies. I said I liked the thought of being a schoolgirl getting roughly seduced, and he took the hint and told me I was a bad girl and he wanted me to be his bitch and take his cock in my mouth. I kinda demurred, feigning reluctance, but he said he knew I really wanted it, and pushed his cockhead against my lips. When I pretended to struggle and resist a bit, he put a hand on the back of my head and pressed his cockhead inside my mouth.
I started to lick and suck his cockhead, and he called me his good little bitch cocksucker, and then suggested we undress and get on the bed. He laid on his back and I knelt down beside him, facing away from his with my butt near his head, and I gave him some really good head while he squeezed my ass and stroked my cock and balls and said I was doing a good job for such an innocent schoolgirl. He cooed at me and asked, did I like it?
I said, it's kind of dirty and wrong, but yeah, I liked sucking him off. Then he grabbed my hair and pushed down, and I gagged a bit and deepthroated him while he guided my head. All the while he was groaning and talking dirty, calling me a slut and a whore and his bitch to do whatever he wanted to.
Then he asked me if I was ready to get fucked, since that is what happens to bad girls, and I said no, I wasn't ready to do that, but in a tone of voice that said yes I am, because I was getting turned on and leaking some precum by then. So he got behind me while I was on all fours, and took the bottle of lube he'd left out on the nightstand, along with a couple of rubbers, and started pushing his cock between my cheeks just a little bit, teasing me, and telling me I was a bad girl, yeah bitch, didn't I want that cock inside me?
