After Holly and I decided to take a break from seeing each other (the second time, not this current one), I decided to explore some other options. She and I had agreed to have an open relationship even when we were still seeing other, but I'm not sure either of us was all that excited about the prospect of the other person actually having sex with someone else. Polyamory is so much easier in theory than in practice. I've blogged a little bit about this before, but it was interesting to me that our decision to be open with our relationship resulted in bringing us closer together and thus made me not interested in meeting anyone else.
But now, things were different. I still felt a little weird about seeing anyone else and I was pretty sad about having to end things with Holly so I specifically decided to look for a couple to play with. It seemed "safer" in some ways - little to no concern about developing any emotional attachments. I figured that it would just be about the sex and that was all I was looking for anyway. I had played with a couple once before and enjoyed it. There's just something extra hot about seeing a sexy woman taking on two cocks at once. On the other hand, as I'm straight, the MMF threesome doesn't really offer any different options than just meeting a woman alone. But hey, it's something different and it can still offer the opportunity to fuck a hot woman.
So, I answered an ad on CL for a couple that was looking for another guy to give the wife a sensual massage and possibly more. I got a reply the next day and began chatting and trading pics with "Annie". She seemed really cool, smart, laid back and easy to talk to. Plus, her pics were hot. She's tall and thin with nice legs and a great butt. We talked on the phone the next day and made plans to meet up a couple of days later. She and her husband, "Alan" were apparently planning a little local getaway consisting of a couple of nights at a nice hotel. We picked a bar nearby to meet for a drink and I arrived a bit early and went inside and ordered a drink. Whenever I meet someone new, I'm always a least a little bit nervous, but in this case, where two new people are involved, I figured I definitely needed a drink.
I had texted a bit with Annie as I was getting into town (they live about an hour away) and she told me that she and Alan had gone for a walk to enjoy the nice weather and that they'd join me in the bar shortly. She also told me that she was wearing a red dress, but I really wasn't worried about spotting her since the bar was fairly empty and I'd studied her pics pretty carefully. In any case, they walked in a few minutes after I arrived and Annie looked really sexy in her little red dress. She has pretty small tits, but they are nice and perky and, from what I could tell, she didn't appear to be wearing a bra under that dress. It was my first time even talking to her husband and he also seemed really nice and laid back. They ordered their drinks and we had a good chat. I had chatted with Annie enough prior to meeting to know that there was a good chance we'd hit it off and so, at this point, I was more interested in making sure that Alan and I were going to get along. I mean, after all, if things went as planned, I hoped to have my way with his hot wife soon.
So, we sipped our drinks and got to know each other and then decided that we all felt comfortable and that it was time to head back to the hotel. After a very short walk back, we were waiting for the elevator and I noticed that I could kind of see through Annie's dress. It was fairly easy to see that she had on some skimpy black panties. I was getting excited already! We got up to the room and Alan asked Annie if we should wait in the hall while she got "massage ready". So, we stepped outside and chatted for a couple of minutes. He assured me that he was fine with whatever happened as long as Annie wanted it. He also told me that he just planned to watch that day and asked if it was ok if he took some pics. I told him I was fine with that as long as he didn't get my face in the pics. I felt totally comfortable with both of them by this point and felt that I could trust them to honor my wishes.
We heard a faint call from the room and walked back in to find Annie lying crosswise on the bed with only a towel draped over her ass. Alan had actually gone out the day before and bought some real massage oil so he handed me the bottle and told me to get started. I poured a little in the palm of my hand and began rubbing Annie's shoulders. Alan sat in a chair next to the bed and watched intently as I rubbed his sexy wife down. I used plenty of oil and enjoyed feeling her firm, toned body in my hands. I made some nervous chit-chat with both of them as I worked. Annie seemed to be really enjoying the attention (she told me later that she loved the fact that my hands felt strong and "confident" on her body). I wasn't aware that hands could be confident, but...whatever.
Anyway, I worked on her arms, then her hands, and then slowly moved down her back. I drizzled a little more oil on the small of her back and removed that pesky towel. Mmm...Annie really did have a nice ass and I got a little peek between her legs too. Her pussy was waxed smooth (except for a thin "landing strip" that I got to see a little later). I let my hands wander over her butt, giving it a good massage in it's own right. I poured some more oil in my hand and rubbed the backs of her thighs. In the process, I slid my fingers down lower and "accidentally" brushed her swollen pussy lips. Annie let out a little moan as I did so and squirmed a little bit beneath me. I moved on down her sexy legs and continued the massage.
I was feeling more comfortable by now and I don't know if it was the fact that I was getting really aroused or the work I was doing on Annie, but I was getting hot so I decided it was time to take off some clothes. I quickly stripped down to my white boxer briefs and resumed the massage. Annie and I had chatted about how our first meeting might go and I was looking forward to getting down to my boxers to see how she'd react. Well, she reacted pretty much the way we'd talked about when we were chatting - in other words, she reached out and gave my hard cock a squeeze through my underwear.
I immediately straddled her on the bed - positioning myself over her terrific ass - and began massaging her butt and legs again. I finally got up the nerve to slip my hand down between her legs to cup that sweet-looking pussy. Annie let out a sexy moan. I glanced at Alan and he seemed totally comfortable with what was happening so I slipped a finger inside Annie's pussy. She was sopping wet and I loved it! I am not sure of the exact sequence of events after this, but I do remember flipping her over and working on her front side a bit. As I mentioned before, Annie has small breasts but really nice, very sensitive nipples. I had fun pinching them and seeing her reaction. In short, she loved it! I don't know why exactly, but for some reason, I get more nervous about kissing a woman in front of her husband than I do about fucking her. It was the same with the other couple I'd met previously. Again, a quick glance at Alan told me that he was cool with what was happening so I got off the bed and walked over to the side where Annie's head was and bent down and gave her a nice kiss. When I stood back up, she reached out and rubbed my cock some more through my underwear. I decided it was time for them to come off.
I stripped down next to the bed and then positioned myself near Annie's head again. I dangled my dick in her face and she opened her mouth. She hungrily sucked the head. It was my turn to moan :) I played with Annie's tits and nipples some more and forced my dick in a little deeper until she was gagging on it. Alan started snapping some pics of the action. I asked him if he thought his wife looked good with a dick in her mouth and he nodded his approval. Her mouth felt really, really good on my cock and I enjoyed the oral attention a bit longer before resuming the massage.
I moved back around to the other side of the bed and climbed up so that I was between her legs. I spread them a bit wider and lowered myself over her to suck Annie's nipples. As I did so, I let my cock brush up against her pussy. She let out a low moan as I ground it gently against her and kissed her deeply. I slowly worked my way down her delicious body until I my face was squarely between her legs. I slowly began licking at her swollen box, lightly flicking her clit and probing the fleshy folds with my tongue. She tasted good and I had her cumming in no time. My dick was throbbing and aching to be inside her so I got up to grab a condom from my jeans. As I fumbled with the wrapper, I stuck my dick back in front of her face and Annie took the hint and sucked me some more. Damn, it felt good but I was REALLY ready to fuck so I pulled out somewhat reluctantly from her warm, sexy mouth and rolled the condom on.
I positioned myself between her legs again and eased into her. I sank in balls-deep and fucked her slowly. Her pussy was tight and felt great on my cock. Annie is very vocal and was letting me know how much she liked the feeling of me filling her with my aching dick. I picked up the pace and fucked her harder, putting her legs up over my shoulders and driving into her as Alan enjoyed the show from his seat next to the bed. She enjoyed it too and came a couple more times. One thing I learned about Annie is that she is pretty easy to get off - at least with me. After a bit, I rolled her onto her side and fucked her that way for a bit before rolling her all the way over and getting behind her.
Annie really does have a great ass and I savored the sight of my dick sliding in and out of her sopping wet pussy. She was loving it and making plenty of noise to let me know how much she was enjoying having me pound her doggy style. I was getting into it but also a bit nervous still and I guess I had some "performance anxiety" too. Sometimes, if I fight off the urge to cum, it takes me a while to complete the mission, so to speak. So, when I felt an orgasm coming on, I resisted the urge to slow down and make it last and instead, grabbed Annie's hips and fucked her harder and faster. I could feel my balls slapping her pussy with each deep stroke until I finally came hard while ramming it in as deep as I could get.
I pulled out and went to clean up a bit before rejoining the two of them in the bedroom. I got dressed and sat down and chatted with them for a bit. Annie was still naked and lying with Alan on the bed now. They were talking about how hot it was and hinting around that Alan would soon have his turn. I really wasn't sure if they wanted me to stay or not. Annie told me later that it would have been totally cool for me to hang out a bit longer but I had a somewhat long drive ahead of me and just wasn't sure what to do.
I've seen them a few more times since then and each time has been super hot. I'll save our other adventures for future posts so...stay tuned!
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