Sex Confessions, Sex with Strangers

Sex Confession #14: Hooking up with a Guy

I live in a big city and there are always a lot of posts for my area. It’s always a lot of fun to fantasize about meeting up with someone, but it’s not something I ever really intend to do. I’ll message, flirt, and sext a little and that will kind of be that.

A few months ago I sent a response to a guy who was visiting my city for business who had posted on an online site. We didn’t end up getting together, so I was surprised when he messaged me saying he would be back this past weekend and wanted to see if we could get together. I had thought his picture was cute, so we started chatting.

I was still kind of feeling noncommittal about the whole thing (I mean, meeting up with a strange man for sex just sounds like the beginning of a Dateline episode), but I really liked that he didn’t jump right into trying to sext and that he seemed cool and respectful. But I wasn’t fully convinced until we inevitably did start sexting and he sent me a video of him jerking off because, wow… his cock was amazing and I wanted it so badly.

We agreed to meet up for a drink near his hotel. When I got to the bar, I was pleasantly surprised because he was even cuter than his pictures and was, again, just really cool and respectful. We were both clearly feeling simultaneously awkward and excited so after I finished my drink he asked what I wanted to do and we decided to go back to his hotel.

When we got to his room, he said he couldn’t believe hot hot it was that he posted an ad and now we were here doing this. I couldn’t wait any longer so I kissed him. He was a great kisser and I was so relieved because the chemistry I had felt over our sexting was definitely there. We laid down on his bed and started making out; I was so turned on already.

He pulled my shirt off and started stroking my breasts. I took off my black bra and seconds later he had his mouth against my nipples, licking and sucking. I moaned and started kissing his neck. He pulled my jeans off and started playing with my pussy through my panties. I pulled him closer into a really passionate kiss and reached down to touch his hard cock for the first time through his pants. He felt so amazing and I couldn’t wait to have it in my mouth.

He had told me a lot about how much he loved eating pussy and given he had originally posted on RAOMD, I wasn’t going to stop him from what he was looking for. He kissed his way down my body, really taking his time. One of the things that turned me on the most was how enthusiastic and into my body he seemed.

When he got between my legs, he started slow, teasing me with his tongue. He ran his tongue up and down my bare outer pussy lips, driving me wild. As he delved deeper into me, making contact with my clit, I ran my fingers through his hair. I was in heaven. He tongued my clit so amazingly and slipped a finger in my tight pussy. I was moaning uncontrollably (gotta love hotel sex and not having to be quiet).

It was so good, but I still wanted that cock, so I pulled him up to me, kissing him deeply and tasting myself on his lips, which always turns me on. When I said that, he slipped his fingers covered in my pussy juices in my mouth and I licked them clean.

I started stroking his hard cock and kissed my way down until I got to his cock, I started licking his cock and balls and finally started sucking him, working his shaft with my hand. His moaning and reaction was so fucking hot. I sucked and licked his balls, eliciting gasps of pleasure from him. I love making a man moan and this was so good.

I went down on him for a little while, before we switched back to him eating me out. I was enjoying it, but he had mentioned that he wanted to 69 at some point, and I needed that cock again, so I suggested he get on top of me. He started fucking my face as he ate my pussy. I was in sensory overload and it was so incredible. He pulled off me, saying he was about to cum, but didn’t want to yet, not before fucking me.

I asked him to get a condom and he did. He got on top of me and starting teasing his hard cock against my tight, drenched pussy. He finally slid inside of me and I gasped. He was so big and completely stretching me. He started fucking me and I couldn’t even hold back my moaning. He was pounding me hard and I kept telling him how fucking amazing he felt.

I was grinding my hips against him as he slammed his cock into me over and over again. He eventually asked me where I wanted him to cum, so I told him to cum in my mouth. He pulled out and tore the condom off. I started sucking his cock until he exploded, spurt after spurt into my hot mouth. I swallowed every drop and kissed him deeply. He moaned in appreciation.

We collapsed onto the bed and talked for a little bit. I started kissing him again and very shortly thereafter his cock was rock hard again. I stroked him a little while we made out, but he very quickly got between my legs again.

I was unbelievably turned on, and I really was loving that he was almost holding my legs down and open when he was going down on me. I felt completely at the mercy of him and his amazing tongue. Normally, like most woman, I have to really focus and work to cum, but I was shocked when a huge orgasm overtook me without warning. I could barely even gasp to him that I was cumming. I don’t know if I’ve ever cum harder than I did right then. He tried to keep licking me, but I made him stop for a second while I caught my breath.

He then asked me to ride him, like I had told him I wanted to when we had been chatting. He said that was what he was thinking about when he sent me the video of him jerking off and I was so turned on by the thought of that.

I got on top of him and slid onto his thick cock, moaning deeply. I started grinding on him, feeling every inch of him in my tight pussy. I started bouncing, enjoying his reaction and loving his cock working in and out of me. After a few minutes of this, he grabbed my hips and started absolutely pounding into me without mercy. I was literally screaming at time point. The sensations were overwhelming, it was incredible. I finally couldn’t take all that pleasure and he got back on top.

He was pounding me so hard and I started begging for him to cum for me. He asked if he could cum inside me (wearing a condom, because safe sex is the best sex) and I said of course. I begged for him to cum inside my tight pussy and he thrust into me with a huge moan and I could feel his cock throbbing inside of me, as he filled the condom with his second load.

We collapsed after that for a few minutes. Cuddled and chatted a little bit, and I headed out. I was completely convinced that had been one of my absolute best sexual encounters. Well… until the next night when we got together again…


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