by

What’s your gender? Man
How old are you? 64, 31 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

Lovely Rita

How long ago did this hookup happen? 33 years ago

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

How would you best classify this hookup? One-night stand

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? Rita was the Joan (from Mad Men) of our office, the head of the secretarial/support staff and, like Joan, a very attractive very self-assured woman who intimidated even some of the partners. Hell, most of the partners. She wore her hair like Joan but her hair was jet black. She wasn’t very tall but she wore her hair up and she wore high high heels so she seemed much taller. She was late 40ish, I’d say. She was well built but no where near as buxom as her TV counterpart. She wore cherry red lipstick and red nail polish when almost none of the other women in the office did. She was a perfectionist and virtually always right about everything. She dressed professionally but right up to the brink of inappropriate and used her attractiveness and genuine sex appeal as a weapon. She was hell on wheels and would have made a great dominatrix if she were so inclined. She and I had a slightly adversarial relationship. I was the hot shot associate in the office, on the brink of partner, a smart ass who was also very successful in the courtroom. I was tall, muscular and pretty good looking. I wasn’t particularly intimidated by her because she only made my work better and we never really crossed swords. I wasn’t as deferential to her as she may have preferred and even teased her and embarrassed her (in a friendly way), which I think she both liked and hated and which certainly no one else in the office did.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, it was about 6:00pm on Christmas Eve. We’d had the office Christmas party a few days earlier and a lot of both the staff and the attorneys had taken the day off. By that time she and I were the only ones left in the office. I was in the library, writing and researching and pretty oblivious both to the time and to how empty the office was. Rita came into the library and told me it was Christmas Eve and time for me to go home. She was actually just being nice but I was on a roll and was irritated both by her breaking my concentration and by her acting like she was my boss and could order me home. She was carrying an open bottle of wine someone had left in the break room on her sweep through the office. I had an empty coffee cup, which had only had water in it, so I held it out to her to pour some wine, which she grudgingly did. I then took the bottle from her and pressed the mug into her hand. “A Christmas toast.” I clicked the mug with the neck of the bottle and took a hit, she reluctantly followed suit with a small polite sip from the mug. Then before she could say anything, I told her she was the most beautiful woman in the office and we should drink again, to her beauty. Now, she probably WAS the most beautiful woman in the office, even though most of the staff and even the female attorneys were younger than she was. For example, that day she had a tight black skirt that came just above her knee, which would have been business-inappropriate except she also had opaque black tights/stockings on, so she was showing the shape of her leg, not skin. She had a pressed white blouse with a fitted winter white jacket over it and a black ribbon tied in a floppy bow at her neck. And of course her perfect as always hair and make up and those high high heels, black patent leather. As always, she looked great. As always, she looked hot. She was surprised and blushed attractively. She was so intimidating, I doubt she was ever much complimented on how great she always looked. She thanked me for the compliment and took a more serious swallow of wine. With the compliment and us being alone like that, her usual officiousness kind of drained away and she smiled, not in her normal hard way, but graciously. Then I said, “And I’m not just saying that, Rita, you are really really beautiful.” I meant it and she could see I meant it and because she was having marital problems at home (which I did not know) and because she was so seldom complimented on her beauty despite how attractive she was and because she was feeling older and because it was a lonely Christmas for her and a lonely house with her there but not her husband awaiting her, I think she was on the brink of tears, though she fought against them and won. I took her hand and led her to a library couch, where I sat. Then I pulled her so she sat in my lap, where she perched imperiously, surprised, I think, as if she were still in control. “Felix”, she said. “No talking,” I said, pulling her to me, kissing her. She didn’t kiss me back, sitting up again, more firmly, “Felix!” “What?” I said, pulling her to me again. But she pushed me off before I could kiss her again and she asked me what I thought I was doing. I told her, “I’m doing what I would otherwise regret for the rest of my life if I didn’t do it. What are you doing?” That really gave her pause. She was speechless. I paused myself for a moment and we just looked at each other. Then I pulled her closer to me, slowly. We kind of stared into each others’ eyes. When she was close enough, I leaned forward and kissed her again, which she kind of resisted, then didn’t, then finally kissed me back. When the kiss was over, she said, “Oh my god.” and she hugged me. I could feel her trembling. It’s funny, almost predictable. When they break, when they give in, they almost always say “Oh my god.” It’s wonderful to hear. We kissed for a bit. She relaxed more and more and got into it. There was no one else in the office, a cold home was waiting for her, it was Christmas and I was young, willing, and handsome, and who would know? Who would care? I was Rita’s Christmas present to herself.

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? Well, we kissed for a good little bit. She was grinding her chest into me and her nipples got so hard I could feel them. I got an erection, which she could feel because she was sitting on my lap. She kind of rubbed against it with her hip and said, “Oh, what’s this?” “What’s that? Do you want to see?” She blushed and her eyes got wide and she was clearly embarrassed. “No, I mean…” “Stand up.” I held her hand, helping her up out of my lap. At some point, she’d lost her jacket. It was nearby, on the floor. I reached around her and began unfastening her skirt. She grabbed my hands and said, “What are you doing?” I looked up at her and said, “What am I doing??? Isn’t it obvious what I’m doing, you have to ask?” I had unzipped and unhooked her skirt by this time but she grabbed the waist band and said, “No, I mean–” I grabbed her wrists gently and said, “I know what you mean,” and again stared into her eyes. She was silent. I pulled her hands away from her skirt and it fell to the floor around her. The first thing I perceived was how shapely her legs and thighs were. I mean, the stockings were opaque and that’s what you could see, shape. But the other thing was, the tails of her blouse were tucked into the top of her panty hose and that looked silly. “What’s this?” I said, smiling. I could see she was a little embarrassed and she said, “All women do this, your wife does this, it makes everything lie flatter.” I laughed and she blushed again. “What’s so funny?” “Get me a pair of scissors.” In the library on the tables were various supplies, scissors, staple removers, markers, post-it notes, and so on. “Why?” “Just get me a pair of scissors.” She was not used to being ordered around at all. She looked at me for a moment, seemingly forgetting she was now standing there skirtless, and she went to the nearest table and got me a pair of scissors. “Now pull your blouse out of your stockings.” She did, unquestioningly, which was a surprise. Finally she was beginning to understand how things worked. I pulled her to me. She had no idea what I was doing. I reached under the tails of her blouse and pulled her tights halfway down her ass. Her skin was so translucently white! With her tights pulled down like that, I could reach under her blouse and snip the side of her panties. “What are you doing???” She couldn’t see because of the angle and because her blouse was in the way. I quickly snipped the other side. She started twisting in my arms, saying, “What are you doing?” I reached behind her and pulled her panties out of her stockings. “What did you do???” I held the cut ends of the panties together so I could see them. “Wow, these were really pretty panties.” She was totally confused, I think. She said, “Thank you, I think.” I began unbuttoning her blouse but in unbuttoning it I could see for the first time her uppermost pubic hair, which I had exposed by pulling down the band of her pantyhose to snip off her panties. It was beautiful, thick and black and glossy, like the hair on her head. And I’m a guy who prefers his women shaved! I stopped unbuttoning her blouse and tugged her panties down more, exposing more of her bush, almost all of it. I began rubbing and fondling her. She gave up all pretense of resistance at that point. She finished unbuttoning her blouse for me and dropped it to the floor with her skirt. Her bra was really.pretty too. She just dressed beautifully! I tugged her pantyhose down a little further so they were bunched up just below her ass. I was playing with her, diddling her, she was pretty wet by this time. She was standing, holding onto my arm, her eyes half closed, just basking in the attention. I picked up the scissors again and snipped the crotch out of her pantyhose. “Oh my god, what did you do?” I pulled her pantyhose back up. “How many times are you going to ask me questions you already obviously know the answers to?” Again she stopped talking. I dropped trousers and pulled down my tighty-whiteys and sat back down on the couch. I spread the tails of my shirt to reveal my inviting cock. She looked and didn’t say anything (finally!) and after a moment she crawled onto it. We spent probably the next 20 minutes or so playing and stroking and teasing and I eventually came inside of her. We had moved around a little on the couch, for a time she was on the bottom and for a time we were nearly on the floor but when I came she was back on top of me. I relaxed back on the couch and she kind of crumpled into me and my arms. We sat there like that on the couch for a few minutes, her head on my chest. She was very beautiful, very comforting. I was feeling really good about everything, as, I think, was she.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? Afterward, when she got dressed, she was embarrassed, angered, flustered–but not at me. Her panties were destroyed, by the time we were done her pantyhose were also history. She had pantyhose in her desk, which she actually kept for staff emergencies more than herself, but none of the stockings were black and all of them were sheer. She said those stockings with her high skirt made her look like a whore. I told her, perhaps, but a very expensive one if so. She smiled and called me an asshole. I walked her to her car in the parking garage and she shivered, saying how cold her legs were. “Just your legs?,” I said and she smiled and told me again I was an asshole. She had a great smile, a perfect smile. She really was beautiful, even for her age in our youth-centric society. I had never seen her so relaxed and loose, so…normal! I kissed her when we got to her car and I thought everything was great. She drove away. It turns out everything wasn’t great. Once she got out of the parking garage, she started crying. Apparently her makeup was a mess when she got home. Her hair wasn’t a mess, believe me, but to her it was. So she walked in, her makeup a mess, her hair (according to her) a mess, sheer brown stockings on instead of opaque black ones, she walked in to her house, her husband looked her up and down, then asked when dinner would be ready. She went into the bedroom and told him to make his own goddamned dinner. And I guess she cried a little more. And then after Christmas she got a divorce attorney and filed for divorce. At work she mostly avoided me. She was distantly nice to me when she couldn’t avoid me, distant but not cold or mean or anything like that. And given our respective positions, it wasn’t that hard to avoid me. She wouldn’t go to lunch with me, she eventually had a discreet drink with me one night after work. She had a coke. I asked her if she was OK and she said yes. I asked her what was going on and she said she’d had an epiphany. She said, “Honestly, I like you, but I don’t even consider us friends.”, which was a little harsh and off-putting, but I could see where she was coming from. I told her I was sorry and she said, “Don’t be.” I wouldn’t say the conversation went terribly but neither would I say it went well. She didn’t feel the need to be particularly nice and she was a strong woman. She got her divorce but even before the proceedings were over she left the firm and moved back to Minneapolis, Minnesota, where she was from originally. I never talked with her much after that night in the bar and nothing of substance was said. I never saw her again after she left the firm. I like and respect her still but I feel guilty about the memory. Not so much about the sex, which was great, but on the disparate impact on each of us. I have no idea how she might now feel about me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, She was medically unable to conceive. She had no children. I don’t know what was wrong with her.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Power / Dominance, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? A little bit

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one. I never talked to anyone about most of my hook-ups. I didn’t want to embarrass either my partner nor my wife.

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? For me it was just play, but it ended up making a huge difference in her life in almost every aspect. I certainly didn’t expect or intend that.

What was the BEST thing about this hookup? The best thing was feeling a momentary special closeness to this strong beautiful woman. Immediately afterward I thought it had been a great hook up and was very happy about it and about how she seemed to have enjoyed it as well. I was smiling on the ride home and looked forward to seeing Rita again after Christmas, whether we hooked up again or not.

What was the WORST thing about this hookup? Discovering over time afterward the fall out for Rita.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This was my first hook up where I wasn’t sure I had done a good thing, that I realized I may have done a bad thing. I tried to be more aware of circumstance and to do a little less steering with my potential partner and undertake a little more listening and laying of groundwork.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Rita was really a fine person. I’m sure she still is.

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? Casual sex has been an important outlet in my life. It’s been a mostly good thing for me throughout my life. I guess I just wish people had a more relaxed and accepting attitude toward it.

What do you think about the Casual Sex Project? Hopefully it will help people’s understanding and help morals to evolve.

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