What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
What’s your current relationship status? Widowed
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Anticipatory. Experienced. Adventurous.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 12

Their 1st…

How long ago did this hookup happen? Summer 1993

What was your relationship status at the time? Single

How would you best classify this hookup? Group sex

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? R. was working at the one of the wholesale clubs where I did product demonstrations on a semi-weekly basis. She was 23 years old, had a beautiful face; dark brunette, upper-mid-back length, wavy hair; dark green eyes, full lips, and a full figure, with B-cup breasts that set perfectly and perky. R. always smiled and was quite flirtatious but made it known that she was married but frustrated. By “quite flirtatious,” I mean that we talked about sex and what we liked and disliked when having it; about some of the partners each of us had been with and how; etc., etc., etc. We talked sometimes when we could take a break together about all sorts of things, and I made it a point to ask about her husband nearly every time we were able to have a real conversation. I thought it strange that she would be willing to flirt so heavily yet constantly bring up her husband. I wondered, if she were so committed to her husband, even though frustrated, why she would talk so freely with me (and another, older gentleman) about sex. So, I made it my goal to find out how far she was willing to go.

One Saturday evening I walked her out to her car, which was at the opposite corner of the parking lot from mine. When we got to her car I told her where my car was and asked if she would mind giving me a lift over to it. She smiled and said, “Sure.” So, I opened her door, which surprised her because she said her husband had never done that for her in the 8 years that they had been together. After I got into the passenger seat, I started asking her more questions about her husband and their relationship. She began to start the car but stopped, turned the key all the way off, and turned to look at me while we continued talking. We talked for probably 15-20 minutes before I took hold of her hand and told her that I had been wanting to kiss her since I first saw her nearly 2 months earlier. She reiterated that she was married and that she would probably feel guilty for cheating on him. I reminded her that she told me that he had cheated on her once and told her about it, and that she said that it didn’t hurt as much as she thought it would; then asked her why she would feel guilty for kissing me. She looked at me for a moment while she thought, then said, “What the hell. I don’t think it would hurt him any more than it did me.” But she didn’t move. So, I gently pulled her hand toward me, indicating that I wanted her to slide over to the middle of the bench seat (mid-80s sedan). She moved over closer to me, leaned on my shoulder and said, “I don’t know if I should really be doing this but…” then placed her hand on my thigh about 5 inches or so above my knee. So I responded by putting my arm around her shoulders, taking her chin in my right hand so I could look her in her eyes, then gave her a starter kiss. We started making out for a little while when I indicated that I wanted her to move her hand closer to my crotch, which she did but not quite onto my hardening member.

Sorry, but I digress from the hookup that this story is supposed to be about. Suffice to say that I gave her oral sex but that was the extent for that night. We went on to hooking up several times over the next couple of months, usually she would come and spend the night at my house. What surprised me is that she told her husband every time about our hookups. It turned out to be a good thing.

The hookup I am writing about in this post was the second time I met her husband. The first time he showed up at my regular, full-time job one evening and introduced himself, and it was obvious that he was hurting emotionally. The odd thing is that I didn’t put two and two together about who he was until after he walked out of the store. I was at once glad to have met him but kinda felt sorry for him at the same time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was scheduled to work at the wholesale club the next weekend, R. was scheduled to work that weekend as well, and we had already planned that she would spend the night with me that Saturday. We started talking about my meeting B. (her husband) when she got to my place around 9:30 that evening. She said he told her about it, and that he would like for me to come out to their place for a visit some time. So we set it up that I would go out to their place the following Thursday evening.

When I arrived, B. already had the grill hot, and put on the burgers for dinner. We chatted about whatnot for probably an hour over dinner and while we all shared in doing the dishes, then sat down in the living room, with B. sitting in a lounge chair across from R. and me – we sat on the sofa. We chatted for probably another hour before B. said he was going to bed. R. said that she was going to stay up with me for a little bit. B. and I shook hands, and he went into the bedroom. R. and I talked a little and made out a little. I started touching her but she said that she wanted to ask B. if it was okay with him if we got busy. I suggested that she ask him if he would like to have a threesome. She said she didn’t know if she could ask him that. To which I said, “Well, if you’re going to ask him to let you have sex with me in your house with him here too, why not just ask him if he’d like to join us?”

She agreed, then went into the bedroom for a few minutes. When she came out, she looked somewhat sad and said, “He said you have to leave now.”

I said, “Okay. I’m okay with that. I understand. You’re his wife and this is his house. His rules.” And I started to get up to leave.

Then she surprised me and said that she was only joking, that he was up for a threesome.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? R. and I entered the bedroom, where B. was already under the covers with the lights off, but there was enough moonlight coming into the window that I could see the chair in the corner. After R. closed the door, we began kissing before I backed her up to the bed, where she sat down next to her husband. B. started rubbing her sides, then her shoulders, then began kissing her shoulders and neck after sitting up. I directed R. to turn around and kiss B. while I finished stripping, although she grabbed my stiffening cock while kissing her husband, to which he said, “I never thought I’d ever want to see her do this but she’s beautiful.” B. leaned around in front of her and started kissing and sucking on her tits, and continued sucking and watching as I stood up and R. leaned over and took my cock into her mouth. I stood there and watched as B. moved his hands to her legs, and up to her pussy, which he commented was wetter than he’d ever seen before. R. leaned back and tongue kissed B., so I got onto the bed with them and started eating her pussy while he was still fingering her. They made out for probably 10 minutes or so while I ate her pussy. Then B. laid onto his back as I climbed on top of R. and started fucking her slowly. They were still making out when I suggested that she suck his cock, which was surprisingly still in his underwear. I continued to fuck her slowly but with several powerful slams while she gave him head, until I said, “Let’s switch.”

Both of them were happy to switch positions, and B. dived into her pussy and ate her to several more orgasms before sliding into in the spoon position while she still sucked my cock. He seemed intrigued by the sight of her sucking my cock in the moonlit room because he kept his head next to hers while watching my dick slide in and out of her sweet lips.

We switched positions several times over the next couple of hours before she was on top of B. face to face. I decided that I wanted to see if both of our cocks could fit into her pussy at the same time, so I climbed up between both of their legs and started rubbing her asshole and taint with my cock. Then, when I felt her relax a little I started working it into her pussy along side his. We fucked in this position, both cocks stretching her pussy at the same time for the next 15 minutes or so until I came inside her, which put B. over the edge, and he shot his load inside her, our sperm mixing together inside his wife. We all rolled over onto our sides, with R. between us, still making out with her husband while reaching back and stroking my deflating pole and his at the same time.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We all laid together on the bed, and every once in awhile one of us would say something along the lines of, “That was great!” R. made out with both of us for probably another 20 minutes or so until we all started to fall asleep.

R. and I woke up the next morning, me holding her in the spoon position, and realized that B. had gone out to finish sleeping on the couch. She and I had talked several times about anal, which she had never even thought of before me, and decided that we were going to try it that morning. I asked if we should get B. back into the bedroom for the fun, but she said, “No. I want you to fuck my ass alone the first time.” So, we started making out while I fingered her pussy enough to get her very wet again, and used her pussy juices to lubricate her asshole. She had an amazingly smooth and tight asshole, which was not really surprising as I was the first person to ever touch it. She was surprised that she actually had an orgasm with me in her ass, but I told her that it was probably because I was also reaching around and playing with her pussy.

R. continued coming to spend the night with me about twice a week, then I visited them again a month or so later, and we enjoyed one more threesome, which was just as nice as the first but without the DVP, although we did DP her with B. in her ass for the first time ever. They both said they loved it.

After about another couple of months, R.’s overnight visits slowed down, and she eventually stopped coming over altogether, and would not answer or return my calls. B. never talked on the phone with anybody, even his own mother – he just didn’t like talking on the phone. Anyway, the relationship seemed to just fizzle out and dry up.

I really liked R., and B. was a really nice guy. We were both straight, which was a good thing for both of us because neither one of us ever tried to touch the other except when our cocks were both in R.’s pussy in that first threesome, but we enjoyed watching her as each of us slid in and out of each of her holes – she made the best sex faces, especially when she would have her orgasms.

I have thought about them many times over the last couple of decades – how their health is; are they still married; have they enjoyed threesomes or more with other people; or did they decide to be monogamous? I saw them one time in early 1997, while my wife at the time and I were out furniture shopping. I didn’t approach them, and don’t know if they even noticed me. I was content to let them live their lives however they saw fit. I told my wife about them after we left the furniture store, and she asked why I didn’t say anything to them. That surprised me. ‘Nuff said.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I only ever told my first wife. I was rather surprised when she asked why I didn’t approach them when we saw them in a furniture store a few years later. Then I was really surprised about a year later when she suggested that we have another man over for a threesome, which was a result of the thoughts she had from me telling her about my threesomes with R. and B. (Sounds odd when I put it like that, eh? R. and B.? Never thought of that before just now. LOL.)

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I was part of their first threesome experience, which went very well for all of us, and each of us had our first DVP experience together, which was amazing. (DVP is one of my favorite things to do in a MFM situation, as long as all are in agreement.) Also, while I had enjoyed several MFM threesomes prior to this one, I had never been with a married couple at that point. It was cool to see a married couple enjoy something like this for their first time.

What was the WORST thing about this hookup? This particular hookup went nearly perfectly. I don’t think I can say anything was bad about it. On the other hand, I do wish that our relationship had continued for several years rather than just a handful of months. But, as the old saying goes, “All good things must come to an end.”

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? It was beautiful.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I enjoy sex. I have been enjoying a wide and varied sex life for more than 4 decades, except for the few times that I have been in a committed, monogamous relationship. I think my next relationship will be with a woman who is willing to have it open, preferably being open to bringing another person and/or couple into the bed. One of my favorite things sexually is to watch and be with a woman who is truly enjoying herself, freely experiencing and expressing her sexuality. I love bringing a woman to multiple orgasms. One of the most empowering experiences I have had in a social situation is bringing a wanton woman to orgasm in a crowded room after she asked me to do that for her. The enjoyment on her face and the faces of the people present was priceless (maybe I’ll write about that someday). I think that a free society is one in which people have the liberty to express themselves however they wish, as long as they are cognizant of and avoid offending the sensibilities of others who do not hold to their beliefs.

I would like to see a world where we can hookup on a street corner or in a restaurant booth without risking arrest or being looked down upon by someone who does not hold to the same values. Women are beautiful, and the female body should be celebrated, not simply as an object of base, animalistic desire but as the expression of the beautiful woman who lives in that body.

What do you think about the Casual Sex Project? I enjoy reading most of the stories. I especially enjoy the ones in which the author talks about how the felt and what they went away from the experience with, and how they feel about that partner(s) after the fact. While I enjoy a good porn-style romping story now and then, I think this site is geared more toward the thinking and emotional side of the various types of hookup experiences; and I like that about the CSP.

You have a hookup story to share? Submit it here!