Another successful casual encounter [25m/28f]

Alright, so I'm back again. Another guy, another story. It starts similarly to the others:

Last week I had been trawling internet classifieds again for casual encounters. Found another ad offering a ludicrous amount of money. 15k, from an inheritance. So I did what any girl would do.. Sent him a message telling him to not blow it on women and invest it instead. But in case he insisted on spending it on someone, I also attached some photos and info about myself.

We exchanged several messages and had a fairly honest, open and normal conversation about what we were expecting/offering. Also a little small talk about how our days were going. He seemed to think I was pretty awesome ^{.^} I said that he hardly knew me! He countered that he talked to people online often and that it was clear when someone was articulate, possessed a good sense of humour etc. My, I was flattered. While I was beginning to dig the attention he was giving me, I didn't expect things to really progress; there would be plenty of women attracted by the prospect of so much money, and undoubtedly way hotter than me. Conversation was nice but wound up. I didn't message him again because I figured he had better prospects. Over the weekend I was busy anyway, but come Monday I received a long message from him about how the inheritance had been taken away temporarily for an emergency blahblah and he was now offering a lower amount (a paltry $500!, heh). Bait and switch yeah? I said that I had done worse for less, which intrigued him. He wanted to know more.. It's a long story (see my previous posts) so I said I'd tell him over Skype. He gave me his skype and I added him but we didn't voice chat, I just typed out my story.

He was an avid listener; loved the story, ate it up, gave hilarious running commentary. I was on fire, too, being a bit of a flirt, letting my own sense of humour shine. It was a riot! We were both having loads of fun, and also opening up to one another. I joked that the money on offer was just a ploy to draw women in, then he won them over with personality. I honestly clicked with him quite well and it seemed the feeling was mutual.. then we had a small awkward exchange where he decided he liked me enough that he wanted to also be friends! Friends with benefits, with additional financial incentive. I was open to the idea, cause I was starting to really dig him. Then we had much less awkward exchanges about all sorts of things, past relationships, pets, puns.. the conversation stretched on. It was way past my bed time and I have a cold, but we kept talking. The conversation turned sexual but also light hearted and just plain hilarious at times.. we were just getting along like a house on fire. So I let my emotions get the better of me and told him we could meet, no strings attached, no money exchanged. He was a little shocked (he's paid for sex plenty of times and practically felt bad) but I assured him I felt like I would get something out of it too. We made plans to meet the next night.

Work was horrible.. I was definitely coming down with a cold, plus pre-period body rebellion, and reluctant to meet him while I was sick and gross. But he said he didn't mind! He had a dinner thing on, but would be free at 8:30. I was starting to be full-blown sick, but I took some cold medicine and headed over to his workplace which had some kind of studio apartment above it (not his usual residence but it did have a bed and bathroom). I couldn't find it at first, and had to give him a call.. I was on the wrong side of the street. He waved at someone that was totally not me. We both saw the same white cat run across the street, so I was at least headed in the right direction. Finally we met. Nothing was exchanged at first, though I was tempted to go in for a hug or quick kiss. He lead me into the building and gave me a brief tour as we headed upstairs. He was concerned about the state of the room but it didn't bother me; a little cluttered with stuff but clean, dimly (flatteringly!) lit. It was warm, which is my main requirement for comfort. I shed my outer layers and climbed onto the bed. We started with some more small talk about work, while I got a bit more comfortable with having just met a complete stranger. He had sent a photo along with a video that he was in, so I knew what he looked like, but he was more attractive in person. Quite a cutie, in fact. Mixed subcontinent-caucasian, something I hadn't experienced yet, and not my usual MO but I liked it. A little taller than me, not too tall. Perfect for kissing and cuddling, really. Wider and meatier than my other partners, which was a good thing. I was tired of lean, bony men. While I talked to him I took off his ridiculous belt. It was just going to get in the way. He lay on top of the quilt but I burrowed underneath, though I was still clothed. I continued to talk while I began to unbutton his shirt. His chest was nice and broad, very smooth and hairless. I don't even remember what we were talking about, but then I looked at him, he looked at me, and we started to kiss. It was charged, very hot, hungry kissing for a couple of long minutes before I started talking again. Then there was talking and kissing, then less talking, more kissing. Grinding. It was quite intense as we acted on the tension, chemistry and attraction between us. There was also moments of fun. I tried the "running my tongue along gumline/between lip and teeth" thing that the other guy had done. It took a few attempts: I'd look at him and tell him I was going to do it.. then I'd just start laughing uncontrollably which set him off laughing. Just couldn't be serious about it! But finally I pulled myself together and did it to him. I concluded that "giving" it was alright and a touch above being on the receiving end. More clothes came off as we got back on topic, making out passionately.. whoo, it was hot. Definite chemistry. His skin was so smooth.. I hadn't been with anyone younger before, and this was a nice change. His hair was also super soft. And the amusing part was that his pubes were also very soft and fine hahaha. Not wirey and dry. I enjoyed roaming my hands all over him. He kissed my neck which drove me wild. I was losing my mind a little.. couldn't get enough and neither could he. I got down between his legs to check out his equipment. He was cut, on the smaller side of average, not particularly hard. Took him into my mouth and did my thing. He recalled that I like guys to make a little noise. He seemed to like what I was doing.. thrust his hips towards me, held me a little as he fucked my mouth, made some sounds of appreciation, but wasn't getting super hard. I was a little concerned (was it me?!) but just brushed it aside. Got on top of him and started grinding away. He played with my breasts.

Things were coming up.. and I should have gone for a condom at this point, but we made the perhaps unwise decision to not.. and I slid down on his cock. Mmm.. it felt amazing. And once he was in, it was no holds barred and we began to buck and fuck wildly. I rode him, he fucked back. He rolled me over and got on top and pounded me nice and hard, leaning in for some kissing. A few minutes later, he came inside me, breathing hard and groaning. It was delicious. I was incredibly turned on by the whole thing, risk be damned. Then came that awkward moment where you collect your genitals in your hand and make a break for the bathroom for post-sex clean up. Came back to the bed shortly and shared smiles and chuckles of amazement at how good it had been.

More pillow talked followed, cuddling and kissing, laughing and exchange of more stories. He decided he wanted to make me cum. It's not something I care whether it happens or not whenever I have sex. He tried fingering first, which was nice and I got close but not over the edge. I had told him to hold off on oral because I didn't feel meticulously clean (had used the bathroom, plus he had cum in me).. and he did at first, but then he just dove in.. and I came twice within a few minutes. Which lead to another round of fucking, him on top at first, then I don't know what to call it, but like doggy but I was on my side. He came again inside me. After clean up and another snuggle he nervously asked me about birth control and I laughed and assured him I was on the pill. We spent some more time just enjoying each other's company, mainly admiring one another and being amazed at how well everything had gone. He drove me home and we had a good chat and got to know one another even more. I'll admit (here but not to his face!) that I'm a little smitten. Sure I had had good sex with others lately, but this experience went to the top of the list thanks to a connection on several wavelengths.. intellectually, physically (so much affection which I crave), sexually. We are both looking forward to seeing one another again.. and to be honest, I told him I didn't care about the money. Wow, I'm really dickwhipped hey? Hah.

He said if he gets sick and catches my cold, it would have totally been worth it, aww. :3 I had a day off today (RDO coincided to give me a good day to rest) and we texted each other quite a bit. Unfortunately my period came along so I won't be having any relations for a while. But I've lost interest in browsing personals for casual encounters. I have a lot on my plate right now! This latest guy should turn into an on-going casual thing, hopefully. :)

Source: reddit.com/r/gonewildstories/comments/33gz7o/another_successful_casual_encounter_25m28f