Downtown Hilton, 05/02/15 in Adult Friend Finder

It felt like it’d been a while. I had been playing with some repeat people and then got involved with both Ryan and Jessica. I was having fun, don’t get me wrong, but I was really craving something just random and anonymous. Then I had my period, which put me out of commission for a week. So when the first weekend of May came around, I started diligently looking for partners.

I started talking to a guy that was in town on business and staying at the Hilton. We talked a little bit, and I took all my normal precautions, and then we agreed to meet on Saturday at 8:00. I wanted to find something for Sunday too, so I kept searching. Instead, I found another guy who was staying at the Hilton and wanted to meet on Saturday. I wondered if I could pull that off. I told him I could probably see him at around 10:00 and he was fine with that. I was a little unsure about what I was planning, but I went with it.

The first guy was old and a little disheveled when I got to his room. Not really old, just maybe 15 years older than I am. He was both friendly and shy at the same time, and really just seemed to want to get right to it. I stripped for him and he took off his own clothes. We were both just standing there naked, he was semi-hard, and I wondered if he would touch me. He didn’t. I got on my knees and pleasured him.

Then I got on the bed, helped him put on a condom, and we had sex in the missionary position. The sex wasn’t bad, but wasn’t amazing either. I got the feeling he was fucking me the same way he fucks his wife (I was presuming he was married). I wanted to make it more interesting, so after several minutes of going at it, I asked him if he wanted to fuck my ass.

He seemed shocked. Why are guys surprised that a woman would like anal? I rolled over and he commented that he didn’t have lube. He ended up changing into a fresh condom which at least had the lubrication from the package. He fumbled around a bit, and I wondered if he’d ever fucked an ass before. But he was finally successful.

He felt good in there. I was rubbing my clit while he fucked me and had a nice little anal orgasm. He pulled out and commented that he wanted to cum on my face. I admit my first thought was I didn’t want to show up to the next guy with cum all over my face, but I knew I could clean off. He removed the condom and sprayed all over me.

There were several thank yous, and then I got dressed and left feeling pretty positive. It was just what I had been looking for, random sex with no connection. I never even got the guy’s name.

It was only a little after 9:00 so I went down to the lobby and freshened up in the restroom. I was bored after that so I went up to the other guy’s room and knocked on the door. He opened it, clearly surprised that I was about 45 minutes early, and I asked if it was OK or if I should come back.

He seemed fine. He commented that he hadn’t showered or anything, but that he was clean. He looked like a clean guy. My age, dressed in a suit with a loosened tie. He started telling me how he doesn’t normally do things like this, which is something I hear often and never believe. I told him I do things like this all the time, and that I hoped he was OK with it. He said he thought that was hot that I get around. Then he said it was kind of like getting a prostitute for free.

He was immediately apologetic about saying that. In fact, I was a little bit offended, even though there’s some real truth to what he said. I said that the difference between me and a prostitute is that I really enjoy having sex with random people, and I have a day job.

He said he wanted to fuck me without a condom, and I said no. He promised not to cum in me, but I still said no. He seemed very disappointed, almost like he didn’t want to have sex at all if he had to use a condom.

He kept trying to negotiate. What if we had anal without a condom? What if I he ate me out for a really long time first? I kept telling him that I would be happy to have any kind of kinky nasty sex with him, but if his penis went into my ass or pussy he would have to wear a condom.

Finally he gave up and seemed annoyed. And I was a little annoyed myself. Here I was willing to please him and he was hung up on something that he should have expected from the start. And that coming after the prostitute comment. I kind of just wanted to leave.

He asked if I would just suck him off and I agreed. I helped him out of his pants and out popped this massive cock. He had to be more than 10 inches. I’d never seen something to big outside of a porn video. As soon as I saw it, I said that I’d really like to feel it inside of me.

I got so wet and excited playing with it and sucking it that I finally looked up at him and said, “please put on a condom and fuck me senseless.”

He did. He fucked me hard, like he was angry at me, and I loved it. It was both the roughest sex I’d ever had and the biggest cock I’d ever had. I had two orgasms with him on top of me and then a third one in doggy position. During the third one I kept screaming “harder!” and he kept pounding me with everything he had.

I was bruised and stretched and sore and thoroughly fucked.