This post is sponsored by The T Bar.
What’s your gender? Man
How old are you? 64, around 38 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 have a submissive who I allow to serve me four or so days a week, a married mistress who is a granny in a sexless marriage, and an interracial friendship with expansive benefits.
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 am a dominant with spanking, corset, and leather fetishes
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? 3
Dancing on Lughnasadh
How long ago did this hookup happen? 1990
What was your relationship status at the time? Engaged/Married (open)
How would you best classify this hookup? Fuck-buddies / Booty call
How long did you know the person before this hookup? For 1 to 3 years
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? She was tall and thin, married, red hair (but the carpet turned out not to match the drapes), late 30’s, a high school grad legal secretary. Smallish breasts, narrow hips. She wasn’t particularly pretty but neither was she bad looking. She had a small limp when she walked, I think from some hip problem. She was long married, with children. We worked at the same law firm and she often had to do projects or typing for me. We’d never hooked up before but it was obvious to several of us that she had a crush on me. I amused myself by feeding her crush. I would brush up against her, jostling her tits with my chest accidentally. Or if I was explaining to her what I wanted done, I might stand beside her with my hand on the small of her back, which would unconsciously slip down to her ass as we discussed whatever. She would get distracted, excited, but she wouldn’t say why to me or call me on anything. She would blush and stutter and smile. It happened enough that she had to wonder. She began standing inappropriately close to me when she could. I would always act as if I didn’t notice and then accidentally touch her a little or, sometimes, more than a little inappropriately. She never called me on that, either. I didn’t feel much about her in any way. She was competent, efficient, she always put my work at the head of the line, which was one big reason I fed her with those little inappropriate touches. Most mornings she brought me my coffee because she was getting herself a cup anyway and she knew how I took it and hey, we were friends, right? And, yeah, we were certainly that.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The night began in a bar downtown people in our firm frequented. It was a spur of the moment party that came about because we were bored at the office that day and because it was summer and it was hot outside. Collectively, we were cats on a hot tin roof that day. Someone in the office discovered it was Lughnasadh, a major pagan holiday, and all of a sudden we had a reason to celebrate and a reason to act pagan. What a great combination, don’t you think? Anyway, I had a pretty regular sex hook-up with another secretary in the office but she was on vacation that day and I wasn’t able to reach her on the phone to have her meet us there. I think she went to an amusement park with her asshole boyfriend. At my firm secretaries were assigned by area of practice, not by attorney. Each area of practice had its own staff secretaries. I was going to have sex with one of the secretaries, I just didn’t know which one. Deb was in business bankruptcy and didn’t often go out with the office’s reprobates–that is, me and my friends. She turned out to be the only business bankruptcy secretary there, I didn’t think she knew of my sex relationship with the other secretary, I didn’t think a hookup with Deb would likely be noticed by the other secretaries, who knew Deb only collaterally, and I knew Deb had that crush on me which I had been feeding. I didn’t particularly care that she was married. Plus, it was clear to me from knowing her that Deb would be submissive for me, which I always liked. So Deb was my target for the evening. Anyway, there were maybe 5 attorneys there that night, all male, and half a dozen or maybe 8 staff people, all women. We had a couple of rounds of drinks, everyone was loosened up and feeling pretty good, this bar had loud music. We danced. Most of the songs were upbeat and we all played and danced crazily. About every 5th or 6th song was slow, though. Hold your partner in your arms slow. And every slow dance I made sure Deb was my partner. At the beginning of the night we kept drinking and I could see Deb was feeling it. Every dance I pulled her closer, my hand on her ass. “Cmon Deb, closer!” by the middle of the evening she was all but pressed to me, her tits brushing my chest, my erection firmly pressed against her midriff, my erection only growing bigger and harder from the contact, then shrinking back to normal when we sat down. Deb was moaning a little but not acknowledging my impinging masculinity against her midriff. I told her she had to switch to cokes,which she did. The next time out on the floor, I took her to a dark part of the dance floor and pressed my erection into her again, cupping her ass in my hand. I whispered in her ear, “Do you feel anything you like, Baby?” She sighed but didn’t answer. I said again, “Do you feel anything you like, baby? Yes or no?” Silence. “Yes or no?” Quietly, “Yes.” “Are you going to help me deal with that, Baby?” She looked up to me andt looked me in my eyes. “Yes,” she finally said. “How?” She was flummoxed for a moment and then said, “I don’t know how. How should I?” “You have four kids and you don’t know how?” I said, smiling. “Every which way, Baby. Are you in for that?” She pressed up against me very firmly and told me yes. I said, “OK, when this dance is over I’m saying my goodbyes and leaving. How about you?” Of course,” she said. “Why would I stay if you were leaving?” When we got out to the parking lot, I asked her if she could drive. She said, “I think so.” I said, “You think so or you know so?” She didn’t answer, she just looked at me. I said, “OK, get in my car.” We got into my car, locking the doors. “Are we going to do it here?” she asked. I smiled. “No.” I drove us to a motel near the freeway and got us a room, the room I usually used with the other secretary.
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 got in the room and she put her purse on the dresser, looking around and then at herself in the mirror over the dresser. Then, through the mirror, at me. I looked back at her through the mirror. “Are you still drunk?” I said. “I don’t think so,” she said. “Mostly not. hearing the motel room door close behind us was actually a very sobering sound. Did you want me drunk?” “No, actually I didn’t. Do you still want to be here? I can still take you back to your car. No hard feelings.” “Are you trying to be a nice guy now?” “Trying? I have my flaws but I thought I’m usually a pretty nice guy.” She turned from the mirror and faced me. “No, you’re a very nice guy.” Then, “I’m nervous but I want to be here. I WANT to be here at this exact moment and I’m not drunk. Is this some lawyer test of consent???” “It’s friendly consideration,” I said. “I don’t want to feel you’re being taken advantage of now or later.” “See,” she said, “You’re being a nice guy and a lawyer both. I knew that.” “I’m not always a nice guy, Deb.” What’s that supposed to mean???” “Just what I said. And you can say no or leave at any time, do you understand?” “Can we please just do this??? All this legal talking shit is making me nervous now. I’m not drunk, I want to do this. How much do we have to talk?” “No more, Deb. You don’t have to talk anymore. And you can always leave.” I sat on the bed and pointed at a spot on the carpet directly in front of me, about two feet away. “Step up to where I’m pointing, your toes pointing toward me and your heels together.” “Why?” “No, why, SIR?” She never called me “sir”, not even at the office. She stepped to the spot, toes pointed toward me, heels together. “Why, Sir?” she said, her voice weakening. “Because I told you to, that should always be enough reason for you. Do you understand? Now take off your blouse.” “Are you getting undressed?” “Debby, are you getting undressed, SIR!” Much weaker, even more quietly, “Are you getting undressed, sir?” “That’s a stupid question, isn’t it, Debby? Think why we’re here. Think about how good it will be if you just do as you’re told. Take off your blouse.” She paused for just a moment, then began unbuttoning her blouse, removing it and draping it over the chair at the near by desk. She stepped back to her spot, pointed her toes and put her heels together. She had a cheap bra on. “Very good, now take off your bra.” She looked at me for a moment, looked down, and unhooked her bra, lying it across her blouse, and stepped back to her mark. She didn’t say anything. She just looked at me, then down again. I stepped up from the bed up to her and gave her a sweet kiss. “Very good, Debby, VERY good. I’m the boss here and as long as you respect that, you will have a very nice night.” She crossed her arms across her chest, grasping her elbows in her hands. “Yes, Sir.” I leaned in again, pulling her arms apart and putting them back down at her sides. I kissed her again, then I gently kissed each of her nipples. “Very very good, Sweet Baby. You’re learning, you’re learning how I like it, how to make it very nice for both of us. Thank you. Now, remove your skirt.” Finally, she was learning the drill. She was soon naked in her high heels, standing on her spot. I stood up and inspected her, touching her so lightly as to almost not touch her, her shoulders and upper arms, her back, her ass, her thighs. I stepped in front of her and kissed her and as I kissed her, I fingered her pussy. She was wet almost immediately and she kind of sank/fell into me, almost swooning into my arms. I caught her and pulled her back upright, onto her spot. Her eyes were open very wide and she stared at me. I lifted my pussy fingers to my mouth and sucked them off while she watched. “It’s good when you’re good, when you listen and obey, isn’t it Baby?” “Yes, sir.” We fell to the bed in each other’s arms, kissing, hugging, stroking. It was so nice. I knew she would get it, I knew she would be respectful and obedient and love it. After a long moment we paused in each others arms there on the bed. “Now, I’m going to use every hole you have, your ass, your mouth, your cunt. What do you say to that, Dear?” She looked at me for a moment, considering. “Thank you, Sir.” I kept my promise, she kept her poise, even when I did her ass. And when I finished with her ass, where I came, she was crying a little, I know it hurt her a little, but she still said, “Thank you, Sir.”
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? Afterwards she was a little teary-eyed because her ass hurt but she was snuggly. I told her I know she had no idea what was going on or how to act but it was always her right to insist on a prophylactic or to otherwise protect herself. I told her I had a vasectomy and was disease-free but it was her right to ask and to stop things for that reason or any reason, and that that was true for me or any other partners she might have. She asked me how I knew she didn’t have any diseases and that stopped me dead and I laughed. I said, “You caught me. Sometimes I’m an asshole. You’re right, I didn’t know if you had any diseases.” We kissed a little bit and got dressed and I took her back to her car and we each went home. the next day I felt elated. It had gone better than I had expected. I hadn’t expected to have sex with her again after that night because she was kind of pinch-hitting in my mind for my regular little squeeze, but we ended up meeting at that motel another 6 or 7 times. Then I got tired of her and of sex with her, both. I haven’t seen her in more than 20 years but I still think fondly of our shared adventures and I hope she remembers me the same way.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization
What were your motives for this hookup? Fun, pleasure, horniness, Power / Dominance, Boredom, It was easy / convenient
How intoxicated were you? A little tipsy/high
What substances did you consume? Alcohol
How intoxicated was your partner? Drunk/high but not wasted
What substances did your partner(s) consume? Alcohol
How wanted was this hookup for you at the time? Somewhat
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 never talk about these things. It’s a respect thing and she was married.
How would you best summarize people’s reactions about this hookup? I didn’t tell anyone
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? The sexual release. It was all about the sex for both of us, I think.
What was the WORST thing about this hookup? Nothing, really.
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? No. there is really nothing more to say.
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 have very much enjoyed casual sex for most of my adult life. But by the same token, I have always tried to act responsibly and it is in my nature to always be in control of the situation. I am very controlling sexually, as perhaps you picked up in this story. I wish people had a more positive view of casual sex but I also think the negativity relates to all the stories of irresponsible and even hurtful casual sex with bad consequences for families as well as the individuals involved.
What do you think about the Casual Sex Project? I hope people find it to be a helpful resource and not just titillation.
You have a hookup story to share? Submit it here!