D/S Tryst



What’s your gender? Woman
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? U.S. — California
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Art curator
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Dark desires; open and experimental …
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

D/s Tryst

How long ago did this hookup happen? 6 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? Met him at a coffee shop. Decent looking. Athletic. Educated. After 14 years of fidelity, 10 of them in a marriage, I was actively looking for something, but wasn’t sure quite what exactly. I suppose I wanted it to be on the anonymous side, purely physical. I wasn’t being particularly picky. I just wanted something — anything! — to happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a coffee shop and had reasonably interesting conversation, though not scintillating. We met again. This time the conversation turned more toward the possibility of getting together in a more intimate setting. We exchanged email addresses. We started emailing. Not being tete-à-tete, we found we could be more unhibited. The email quickly turned to the possibility of a hookup that would be d/s (dominant/submsssive? in nature. He initiated this, but I was game. He would be dominant and tell me what he wanted. I would show up and act accordingly. I found this exchange not only titillating, but thrilling; at least in fantasy. But, I also started to get a little apprehensive. His fantasies expressed in his emails indicated someone who wanted sex a little on the rough side. I did, too, but I wasn’t sure how rough. I social-media stalked him a little bit, and he was very visible and seemed like an okay person. We agreed that the first encounter wouldn’t be so rough. He indicated that he wanted me to fellate him and nothing more.

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? I met him at his apartment. He was very cordial. Offered me something to drink, which I declined. He then took me into a bedroom. The conversation turned sexual. He grabbed me by the hair — not too roughly — and pushed me down to the floor. He indicated very clearly what he wanted. I unbuckled his belt, pulled down his jeans, then his underwear. His cock popped out, very erect, not too imposing. He had a nice lower body from all the gym work that he did. As he held my head down and started talking dirty to me — “I want you to suck me, you little slut” — I took his cock in my hand and then put it in my mouth. After a week of emails and two coffee dates, it was finally happening. All the pent-up fantasies were now being actualized. I liked the fact that I was his “slave” at that moment and he was my master. After 14 years of the same man, countless sexual fantasies of other men, and hours reading erotic literature, it was electrifying to have another man’s cock in my mouth. It lasted about 15 minutes, and then he came in my mouth. When it was over, I had this empty experience that it was all about the fantasy and not the act, if that makes sense. The actual act, though initially thrilling, was kind of physically mechanical in the end, even when he came. I, of course, received no pleasure out of it, other than having my fantasy realized. I suppose there existed some pleasure in the knowledge that after 14 years of the same man that I could still be this desired. I also took pleasure in the fact that I was objectified as a mastubatory toy and turning this man on, whom I had no feelings for. There was a bit of a turn-on in the fact that I was getting him off, doing something naughty on my lunch break, and getting away with it. The fact that it was not a date, not sex that would lead to a relationship, but a dominant/submissive hookup andn nothing more.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

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? Like I wrote, I didn’t think the act lived up to the fantasy. Through email we agreed to another encounter. This time he took me into the bedroom and pushed me down onto the bed. He blindfolded me. Then, he undressed me. I heard him undressing. He got his cock hard and I heard him rolling a prophylactic onto his erection. He fucked me as if I were a blow-up doll. There was no kissing. Only penetration. After he had come he stopped. He made no attempt to bring me to orgasm. In subsequent emails he expressed a problem that I was married. Whether true or not, we broke off communication and never saw each other again. I was glad I did it. I was glad I had a kind of mild d/s experience. I enjoyed fantasizing going over to this guy’s place and being told what to do. I wanted to be taken. I wanted to be ordered to do what he wanted. But, the actual acts of fellation and copulation didn’t live up to the fantasies.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Power / Dominance, Submission / Relinquishing power

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? 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? No one. I didn’t even tell my therapist. Later, I confessed it to a new b.f. He seemed a tad appalled. Then, perhaps even a little jealous. Then, later, after more discussion, he seemed intrigued by the fact that I would consent to have this anonymous d/s experience, though he was never judgmental. Maybe he felt he was missing out b/c he hadn’t had a similar experience, I don’t know. He was very curious why I would want to have an experience like this. I guess my best answer was that I was lonely, I didn’t want a sexual enounter where the guy might develop feelings for me, I’ve always been attracted to sex where there’s a power component — me dominant; me submissive; either way, it can be a turn-on. I prefer it with someone who I’m in a relationship with, but sometimes that’s hard if you don’t communicate your sexual desires, or vice versa. Fortunately, I am now. And, it’s more satisfying, b/c you can go deeper. Then, talk about it afterward, not just have some awkward conversation, then hug and exchange disingenuous promises to get together again. Not that I didn’t like the anonymous sex. It had its moments. But, again, the thrill was really all in the build-up.

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? A little bit

Why do you regret this hookup? I don’t regret it from a moralistic standpoint; i.e., the fact that I was married. The marriage was coming to an end anyway. Shortly thereafter, I began a two-year affair. which then blew up in everyone’s faces. So, things were disintegrating anyway. I regret it a little from the standpoint that it didn’t meet my expectations.

What was the BEST thing about this hookup? How powerful the fantasy was leading up to the hookup. I imagined driving to his place, how it would all happen, the whole narrative as it developed in my imagination. I loved how the initial attraction, the email initiation of it, all started a prairie fire of intense erotic lust. The best part was being in my imagination.

What was the WORST thing about this hookup? After all the build-up, I was on my knees sucking a man’s cock. He came. It was over. I was offered something to drink. I drove away. It didn’t really meet all my expectations. It wasn’t a case of buyer’s remorese. I really enjoyed sucking his cock and then, a week later, being fucked with a blindfold on, but the sex wasn’t that powerful on my end. I didn’t climax. It was all about him. But, then, that was the arrangement. I got to play out my fantasy of a d/s tryst and it was, well, a little underwhelming in the end.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think, at the time, it helped empower me in a way. It liberated me. Okay, it was cheating, and some might judge me negatively for that, but my husband didn’t find out, and new doors were unlocked in my imagination, even if they did set in a motion two powerful affairs that rocked my world and transformed my life forever.

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

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

Anything else you want to add about this hookup? I think if you’re feeling unfulfilled in a relationship — marriage or committedly monogamous — and you’re having sexual fantasies, but you’re not really in the mindset, or the circumstances, to end that relationship, I don’t see anything wrong in testing the waters, as it were, rather than just living in the purgatory of your fantasies. Even if the reality wasn’t really tantamount to the fantasies in the end, at least you played them out, at least you felt sexy and good about yourself for the first time in a long time, and unless you’re some devout religious nutbag who thinks you’re going to pay a price in the afterlife, I truly believe getting fucked, getting fucked hard, or getting fucked anonymously, can be really liberating. At the right point in your life.

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 am not a judgmental person. I have no problem with infidelity. I have no problem with casual sex. I think casual sex can be a way of experimenting with sexual fantasies that, for whatever reason, have gone unfulfilled. Casual sex can open doors in your imagination that might lead you to change your life, as it did mine. Maybe it will close those doors. Everyone has sexual fantasies. Let’s face it, in most relationships we don’t live out those fantasies, we don’t talk out those fantasies, be they d/s or whatnot. Casual sex can bring those fantasies to fruition. It can makes us realize that we need to find someone else. It can open up new neuro-pathways and get us to thinking about how stale and routine our sex life has become in our marriage or committed, monogamous relationship.

What do you think about the Casual Sex Project? I think it’s great that there’s a forum where individuals can share their experiences and inspire others to do the same. Everyone has a story, a sexual history.

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