This post is sponsored by The T Bar.
by Felix the Cat
What’s your gender? Man
How old are you? 64 now, 25 at time of story
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland, Ohio
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? happily retired
What’s your current relationship status? I am involved with three women, each of whom I sleep with at least once a week. Two are “friends with benefits”, close to my own age, who occasionally accompany me to family and/or social events. The third is about twenty years younger and is happily and enthusiastically in my sexual service, so to speak. She would love to move in with me and serve me 24/7 but I don’t think that will ever happen. I would be open to a more traditional relationship with the right woman but am not holding my breath waiting for that to happen.
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I’m into light bondage, spanking, corsets, high high heels, and so on. All three women have to some degree been trained. In general, I dominate, particularly with the younger woman in my service.
How many sexual partners have you had in your life (including oral sex)? I would guess between 60 and 80, perhaps. Perhaps slightly more. Less than 100, surely. I don’t know for sure, I don’t “keep score”.
How many hookup stories have you here posted before? 0
Partner A, Partner B
How long ago did this hookup happen? 39 years ago
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? Partner A was quite beautiful, out of my league, actually, a willowy blonde. Partner B was attractive but not nearly so much as Partner A, darker and fuller figured, though not fat. I met Partner A at an optometrist appointment. She was a technician there who set me up for the doctor before my appointment and who ran me through a few pre-tests. Partner B was Partner A’s roommate. The divorce from my first wife had just been finalized. It was a friendly divorce and, in fact, my first wife had set up the optometrist’s appointment (though she knew nothing of Partner A). At that point my first wife was the only woman I had ever dated or had sex with and the sex was exclusively of the insert-Tab-A-into-Slot-B or occasionally Slot C, but never NEVER Slot D, which I in my naivete would have never then considered anyway. Partner A “inadvertently” brushed her lovely body against me again and again in setting me up for the various tests. She aroused me to the degree that I threw caution to the wind and asked her out for dinner, knowing she was far far out of my league. I was stunned when she said yes. To be honest, I found her beauty a little intimidating given my own dating and sexual inexperience. I had no great expectations of anything sexual, I just wanted a nice night out with a very friendly and attractive young woman. Over time, who knows? Maybe I would somehow get lucky. But initially, i was happy to be going on a date but I had no expectations. Again, I was both naive and inexperienced.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had a very nice date, dinner and a movie, she had been delightful and we had established a nice rapport. I had become comfortable with her. I took her back to her apartment building debating with myself whether to try and kiss her or to just say good bye and hope for another date. I was surprised when she asked me up for coffee and even more surprised when she pressed me to come up, not that it required any great amount of effort on her part. As I said, she was quite attractive. We went upstairs and her roommate was on the couch, watching TV. She seemed nice, though not being alone with Partner A was a little bit of a downer. Of course, then again, it was only for coffee, right? And when Partner A suggested going into her bedroom, well, it was a small apartment and it afforded us a little bit of privacy to drink our coffee. In the bedroom partner A shed some of her clothing, a little risque perhaps, but we had hit it off pretty well, I thought. She kept pressing against me, she was inadvertently touching me, it was getting me aroused, I finally stepped beyond the bounds of respectability and Partner A not only accepted my advance, she seemed to enjoy it. Soon enough, somehow, we were naked and in her bed. I was in an odd position because I didn’t have a condom, I had never expected to be so successful, and I certainly didn’t want to make this new friend pregnant. But, boy, once we got naked there was no doubt I wanted to risk it. She was really hot and she knew it.
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? We were kissing and hugging, I was really getting into it all, we were rubbing each other the right ways, when Partner B not only came into the room but got into bed. She was naked, too. This made me totally flustered. What was going on? Two women? Remember, this was our first date and downstairs I wasn’t even sure I should ask for a kiss and now this??? I had no idea how to proceed, what was expected of me, where the lines were if there were any. I had little idea of how threesomes worked and had never fantasized about them. I had zero experience and no idea what to do, what the etiquette was, presuming there was any. Was I supposed to suddenly turn into a sexual beast or a suave sexual sophisticate? I really had no idea how to be either. But they kind of took over. Partner A began stroking my penis while Partner B kissed me and guided my hand to her pussy. I was just going with the flow, I played with Partner B’s pussy, kissing her back, while Partner A kept stroking me and began kissing and sucking on my penis and it soon there wasn’t much to think about, it was all just kind of happening. And then Partner B climbed onto my chest and shoulders and began rubbing her wet pussy against my chin and nose, inviting my attentions while Partner A had mounted my erection and was beginning a good hard ride. So I was sloppily attending to Partner B until, it happened, until I came in hard spluges in Partner A, but because of Partner B, I didn’t see anything but Partner B’s pussy and thighs. I kind of turned my head and pressed my lips to Partner B’s thigh, I was suddenly out of it, and both of them dismounted me, Partner B bouncing down to join Partner A at my cock. In a post-coital daze I looked down as Partner A removed a condom that had somehow at some point materialized on my cock, and then Partner A kind of wrung the contents of the condom onto my thigh, where they both licked and slurped my cum up, laughing, kind of playing, being affectionate with each other. And then Partner B went down on Partner A, Partner A grinding on Partner B’s face until Partner A quite visibly orgasmed. I was watching all this in a daze. It was like I was watching some porno movie. and in a bit more they both crawled up on me. smiling and carrying on, just happy, and they nestled in around me and we all eventually fell asleep. In the morning I had to get up early because I had to go to work. The girls were happy and nice in their morning lethargy, I kissed them both and left, wondering what had happened and if it would happen again and if I wanted it to happen again. It was like no sexual experience I had ever had or ever even contemplated having. I was happy enough when I left but confused by it all.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
Did your partner have an orgasm? Yes, one
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? I don’t really know if partner B had an orgasm but Partner A had had at least one. I felt strange the next day, what had happened was quite beyond my ken. I eventually called Partner A, not sure what to expect, and she was sweet and nice and very happy about our date. We ended up going out for several months and I slept with Partner A a couple of times a week after that, Partner B joining us many times. I never had any particular expectations, I never knew what to expect with those two. Eventually we drifted apart, nothing bad, nothing dramatic, it was simply that our song had been sung. I don’t think any of us ever expected anything serious to come out of our consignations. It was just sex–but very good and satisfying sex. Today those two are fond memories. I hope they each remember me the same way.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant, IUD (Intrauterine device), Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Didn’t want to disappoint my partner, It was easy / convenient
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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’
How wanted was this hookup for your partner at the time? Very
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 never really talked with anyone about this hookup until many years later. I think at least one friend didn’t believe me, which is of no consequence, but most of the very few others whom I’ve told seemed to react positively. The few times I’ve spoken of it were in the presence of alcohol, high spirits, and bonhomie. I never told another woman about it, though, not even the three I’m keep company with currently. It just didn’t/doesn’t feel right.
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? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It gave me a totally different perspective on sex and sexuality, terrifically broadening my horizons. It made me feel better about myself and I got to meet two truly delightful people who became good long-time friends.
What was the WORST thing about this hookup? I think I was about 15 minutes late to work that first time, not that that was a big deal.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This hook up TOTALLY changed the way I thought about sex. Before I was a good Catholic boy who expected missionary sex within the context of marriage. The girls taught me SO much. Before our relationship, I was immature sexually in so many ways and a little sexually repressed. Afterward, wow, it was such a different, such a more beguiling world! And I did feel much better about myself, more self-confident, and so on.
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? Before this hookup I regarded sex solely as how a committed married couple expressed and celebrated the love between them. Afterward (together with subsequent experience that I tried because this experience was so positive) I came to understand sex as joy and sharing and as a positive expression of our humanity. It changed my life and I am very grateful for that.
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 regard casual sex as a wonderful thing and have encouraged my children to experiment responsibly with it. My children were the fruit of my second marriage, which was long term. Through most of my marriage I engaged in extramarital casual sex. My wife knew about it and didn’t particularly care as long as our marriage wasn’t unduly affected. I was careful it was not. I came to develop tastes in sex my wife didn’t share. She was happy that I pursued these interests outside our marriage. She was a wonderful spouse who I loved very much. I doubtless would still be married to her had she not died. Quite frankly, casual sex made our marriage work. As for its role in society, it is a shame that society has so many things so screwed up about sex. More casual sex would make the world and life in general so much happier and better.
What do you think about the Casual Sex Project? I don’t know. If I can share things that will help people and change minds, I would like to do that. If people just visit this site to brag to the world or get their jollies, well, there’s nothing wrong with that but it seems like just another sex site then. If sharing stories and opinions would help, I would be happy to do that. I am not much interested in sex “experiments”, however, or in being any sort of sexual “subject”. I’m just too old now, too satisfied, too set in my ways.
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