I am not sure why I even went here, but one day I found myself on one of those adult dating sites. I had used them in the past as my marriage had been on the rocks and I was looking for someone – ANYONE who wanted to be with me. During that timeframe I was tired of searching for porn and tired of being rejected by my wife. When the divorce was final, I became very bitter towards women in general.
In the past I had used the sites to find married women or women looking to hook up. I never really upgraded in the pursuit, but the women I found were more than accommodating sexually. In fact, in a lot of ways they reminded me of the way my wife used to be when we were dating. For whatever reason, however, I decided not to put an ad in the section looking for women, but instead, and ad for couples (male/female).
I am not gay, but I had had a threesome with a married woman before. Actually, I had sex with her regularly (she was in an open marriage) but one day I ran into her along with her husband. Drinks were consumed and before I knew it, we were at their house having a threesome. To say it was awkward is an understatement because she and I had sex many times and many ways, but this was the first time we were going to do it in front of her husband (or with him). In fact, she had to tell me that we were supposed to follow certain rules when we had sex and well, we never followed them. The biggie was that I was supposed to wear a condom in vaginal and anal penetration. Well, this sucked. One of my favorite things to do with her was to fuck her for a bit but then make her taste her pussy on my cock. Not quite the same when you have a rubber on. Also, I don't care what Dr. Ruth says, it does NOT feel the same with a rubber on. Maybe when you are 18, but not when you are in your 30s.
This time was different. I was making an ad and it was specifically to have sex with a woman who wanted to do it in front of her husband. I also made sure that I set ground rules in place for myself, and if they didn't want it, well, I wasn't going to meet with them. So, like a lot of people on the board, I took a couple of pictures (without my face) and put them on the website. I made sure, though, that I said things like "Make her my cumslut" and "fill her cunt up." As I said, I was very negative towards women – especially married ones – this was one way to have sex without having to worry about them falling for me.
I am quite certain my ad blended in with thousands of other ads on the website, but I felt rather confident given that – like a lot of divorcees – I had lost weight and really toned up. My ad was up for maybe a week when a couple about my age reached out to me.
Typical middle-aged couple, he was starting to bald and had a bit of a gut on him. She clearly had gained some weight though she had a nice figure and a nice face. We traded messages back and forth and I was pretty direct about things. I am fairly certain I was trading them with the husband and was also pretty sure that things were going to be shut down several different times. Something I said offended him or caused him to chicken out. It was clear this was a first time swinging for this couple and just when I thought they were backing out, they started to pursue it even more. Maybe they were talking about it and having great sex or maybe she was the one, I didn't know. All I know is that after a few weeks of trading emails, one day they asked me to meet them for a drink at one of the nicer hotels in the area.
When we met it was a Friday night. They didn't say for certain, but I gathered that they had kids and it couldn't be on a school night. No biggie for me, but since I was meeting them after work, I came dressed in a nice suit. It wasn't hard to find them because the hotel bar was fairly empty – most are early Friday evenings because the traveling business people usually check out early and the out of town people on trips don't arrive until later. The initial meeting was a tad awkward. I really didn't know whether to shake hands or what. In the end we shook hands and had a seat in a booth.
The pictures were fairly accurate. I was right in that he had a bit of middle aged spread and he didn't really go to any trouble to look presentable. I could tell he didn't work out at all and he was dressed in a plain polo and jeans. Carmen, however, was dressed in a nice cocktail dress and had makeup on. Some of her pictures didn't look all that good, but it is amazing how good a woman can look when they are dressed up. She had a bit of a baby pouch and her legs had a little extra padding, but her top looked great and her ass was nice, too. She had a sparkle in her eyes, but if she was turned on by me, she didn't let on.
I guess I was still in business mode because at some point Carmen said to me something like, "You would never guess you are the guy who was writing those things." It made me realize how harsh they sounded but it also made me realize that I needed to close this deal tonight because she was having second thoughts. We had a few drinks and I was very glad to see that neither of them could hold their alcohol very well. In the conversation they shared that they had thought about threesomes, but had never had one. They also shared that she was going to do a threesome (male female female) with her husband, but told him that the only way she would do it would be if she got one with another male first. It all made sense as to why they were writing and then stopping off and on. I realized they were negotiating with each other and also that they were searching out men and women to meet what they wanted.
After about 30 minutes I headed to the bathroom. It gave me a good opportunity to freshen up and clear my head. I was quite turned on by Carmen, but didn't really care much for her husband, Tom. I was gathering he didn't care much for me so I wanted to give them the opportunity to back out, or at least talk about it among themselves. When I returned, Carmen was alone and I thought maybe she was breaking the news. Instead she said, "My husband is getting a room and using the facilities. He will be back shortly." She could tell I was a bit shocked so she continued, "In the end, his horniness won out over his jealousy. See, he really wants me to go all out in a three way with another woman. I mean, he wants me to go down on her and he wants me to do things I have never done with a woman. I told him that if I was going to do that then I would get to be a total slut for one night."
Wow, it was amazing hearing her talk like this when she seemed so innocent before. I was not sure if it was the alcohol or mere revenge, but it was clear that she wanted it to go a certain way. When Tom returned, I still had the look of shock on my face and he said out loud, "We are in room 1401. It is a suite with two bedrooms, a Jacuzzi and 2 bathrooms. This way you (he pointed at me) can go into another room when we are done. While he smiled, he did not seem at all happy. We rode up the elevator together and Carmen and I really didn't have a chance to chat after that. I had an overnight bag with me and Tom directed me to a room where I would be sleeping. Meanwhile, Carmen headed to the larger bathroom "to freshen up."
There was a knock on my door and Tom entered. It was the first time we were in a room alone together and I could see his look of trepidation on his face. He shared with me that what she wanted went and that if she said she wanted to stop we would. He then finished up with, "and while she may blow you, you cannot cum in her mouth. She hates that and doesn't let me do it."
"Fuck!" I thought. I let him put in a ground rule that was totally against what I wanted. Yeah, I liked Carmen, but when I set out for this, I really wanted to use the woman. Instead, I was somewhat liking her and allowed myself to be controlled by it.
