Downtown Hilton, 01/21/15 in Adult Friend Finder

After my previous disappointing experience, I kind of wanted to have a good one right away to make up for it. I also know that I would be getting my period approximately the next weekend so I wanted to do something before then. I had no immediate prospects however, so I started really looking around on the site to see anyone who looked like he would be a good experience.

I finally found a guy who said he was in town on business and staying at the Hilton downtown. It’s a nice hotel right on the waterfront so that sounded promising. I worried I almost sounded too eager when I was messaging him. He said he doesn’t like to have actual sex because that feels like cheating (I hear that a lot actually) but would love to have to come by and we could each give each other oral. I find it funny that he thinks oral sex isn’t cheating, but I’m not making a moral judgment. I know I’m having sex with married men.

He’d made it clear to me that this wasn’t his first time, and that when he travels for business he almost always finds some fun on adult friend finder. I appreciated that we were both experienced in this and figured that would make it go smoothly.

I dressed sexy for him, something I hadn’t really done before.

When I got to his hotel room, he answered in business clothes, probably whatever he had been wearing that day. For some reason I thought that was sexy. He offered me a glass of wine but I know better than to accept drinks. It’s kind of funny when you think about it. I’m perfectly willing to have sex with him, but I still avoid drinks.

He seemed to completely understand. We made small talk for a strangely long time, almost like he would rather talk than anything else. I started flirting with him a bit more and soon was kissing him while he tried to talk to me. I asked him if it was OK if I stripped for him and he said yes but seemed a little nervous about it. I started to wonder if he really had done this before.

I’m not the best at doing sexy strip teases and I was out of my clothes pretty quickly. There was something sexy and simultaneously embarrassing and standing in front of him completely naked while he was still dressed. I laid on the bed and spread my legs for him and he crawled in between and started eating me out, still fully dressed.

He was good at it. And he didn’t stop until I’d had an orgasm. He even propped me up and rimmed me a little bit. It was clear that he was enjoying himself. I was super aroused after he made me cum, and I started peeling off his pants. He didn’t stop me, but seemed a little uncomfortable with it. When I got him underwear down, he was soft and really quite small. I was surprised because I’d gotten the impression he had very much been into the whole experience. I tried to not act surprised.

I started sucking him and he eventually got hard, but not very big. I realized he was probably embarrassed about his size, but I didn’t act like it was a big deal. It really wasn’t. I’m OK with all sizes.

When I could tell he was getting close, I stopped and pulled away. I spread my legs for him and told him I wanted him to fuck me. I know that hadn’t been in our arrangement, but I wanted it. He seemed a little bothered by me saying that and told me he shouldn’t. I said no one would know, and that I really wanted to feel him inside of me. He just looked at me, a little lost. Then he mentioned that he didn’t have a condom.

I really wanted to tell him to fuck me anyway, but that wouldn’t be a good idea. So I finished him off with my mouth like he wanted. When we were done, we laid there in silence for a while. I’d had a great orgasm but was feeling a little disappointed because I’d wanted to be penetrated. He told me that he came into town somewhat regularly and that next time maybe we’d have condom and have sex. I had a feeling he just knew I was disappointed and was trying to say the right thing.

It wasn’t a bad experience, and to be fair we did exactly what we had agreed to do before we met, but I still left feeling empty.