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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? Virginia, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? retired/ self-employed
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Pansexual
Any other term(s) that describe your sexuality or sexual identity? horny, haha.
How many sexual partners have you had in your life (including oral sex)? 23
How many hookup stories have you here posted before? 1

It’s All About The Money

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Coersion

How long did you know the person before this hookup? For more than 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 is the friend of an old client. I have driven her to the airport over two hours away several times and to events in DC. Though I am retired and do not have a transportation business any longer, she continues to call and pay for transportation. She is 82 years old, German-born, but a widow of a former senior government official and later CEO of a major company. She always treated me nicely and respectfully. Most of the other people she pays for services don’t like her, but I find her harmless and engaging.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A month ago, she called me and told me she needed a ride to the airport. She agreed to the usual fee and gave me the dates and times. I drove her to the airport and she departed for her vacation. Yesterday I went to pick her up and brought her home. Once I got her home, I took her bags inside and waited as is usual for her to write a check for the trips. I stood patiently in the living room of her villa in the retirement community admiring her many lovely pieces of art and sculpture. I had just noticed what seemed to be a rather obscene sculpture when she came back with my check.

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? When I turned around to get the check, I was stunned to find her standing there completely naked. She is a small woman and had always struck me as being in pretty decent shape. I tried not to look at her naked body but she spoke to me rather sharply and told me she would be deeply offended if I did not get a good look at what she had to offer and that would affect my check. My retirement is tighter than I had planned for, and any money helps, besides I had had to fill up the car for the trip so I was already out that money if I left. I looked down and discovered she had probably once had a very nice rack, but now had what looked like two tennis balls in a pair of wrinkled socks hanging down to her belly. At least her belly was pretty flat, and she did have a nice thick, furry, bush. I like a good old fashioned bush and much to my surprise, checking her out had aroused me a little. She turned around and bent over, grabbing her ass cheeks and showing me her wrinkled old asshole, and some very thick, very low hanging, lips. By now I was completely flustered. After a second or two she stood up and headed down the hall to the back of the villa, calling me to follow her or there would be no check. I stood there for a minute trying to decide what to do. The fact that I now had a pretty serious hard-on made things even more confusing. Finally, I took a deep breath and headed down the hall. She called out to me from a bedroom at the end of the hall and I went into it. She was laying on a queen sized bed, her legs spread, knees up, rubbing herself. Her lips were now swollen and her bush glistened with wetness. She spread her lips and gave me a good look at her grayish, pink, pussy. I could not believe this was happening.

She rather sternly ordered me to strip for her, and I began to take off my clothes. When I had gotten down to my shorts, I hesitated, thinking I should leave them on. She grinned at me rather oddly and informed me that if I chickened out now, she would simply call the guard station and have them stop me. She said she would tell them I had tried to rape her and with her reputation and political connections everyone would believe it. That scared the hell out of me and I took off my shorts. I felt so exposed and dirty standing there with my hard-on. She cooed and giggled like a schoolgirl, then told me to climb up and bring her my lovely cock. I swallowed hard and climbed onto the bed. She lifted her legs and ordered me to begin giving her oral sex. I stared down at her old, strange smelling pussy, then did as I was told. I have always loved giving a woman oral sex, and have gotten pretty good at it over the years. Her pussy didn’t taste too bad after all, and I was able to bring her to climax pretty quickly. I decided that if I was going to do this, then I was going to do what I usually do and kept torturing her pussy until she climaxed again. I ignored her pleas to stop and just fuck her. She managed to bear it for five more climaxes, then demanded I put my damned cock into her pussy. I did as she demanded. Once I was inside her she wrapped her legs around me. I was afraid at first to go hard, but she growled at me that she wasn’t made of glass and not to worry about breaking her. So after that, I started pumping into her as hard as I could. She grunted and chirped at me in German. I told her I was nearing climax, but she tightened her legs around me, so I had no choice but to climax inside her. The intensity surprised me.

After a few moments of my shuddering and shaking, she released her legs and told me to lay down with her. I did. she turned to face me and began kissing me. At first, I was turned off, but the fuzziness of my recent climax took the edge off a little and I finally kissed her back. She fondled me as she kept kissing me, I felt a bit used and taken advantage of, but there was a tiny part of me that figured this was karma for the few times I had had sex with a girl that thought I liked but all I wanted was sex. After a few minutes, I began to get erect again. That surprised me as it was a bit sooner than normal for me. She grinned at me and slipped off the bed. She told me to follow her and she led me back down the hall to another bedroom. When we were inside I realized the room had been set up as a sexual playroom of sorts. There were two different contraptions hanging from the ceiling, a weird sawhorse thing that honestly scared me, and a small mattress on the floor. Just as I was finishing my visual inventory a rather large middle eastern looking man entered the room wearing nothing but a loincloth. That did scare me. I am pansexual and enjoy sex with men but this situation was very different from anything I had ever experienced.

She gave the man some orders in German and he approached me as I started to object. She told me to shut up and do what he told me to. He took my arm and pulled me into one of the corners with the hanging contraption. He helped me get into what turned out to be a sex swing thing. When he had finished, I was strapped in and hanging with my legs in the air, with my ass exposed clearly for sex. I waited for him to do his worst but was astonished when this petite, grandmotherly, woman suddenly appeared wearing a rather serious looking strap on rig. The large gentleman rather roughly reached down and slathered my exposed ass with a generous quantity of lube. Without any hesitation or further preparation, she popped the thick strap-on into me. The pain was intense and filled me fully. I tried to adjust but there was nothing to do about it. She began to very aggressively pound me. I enjoy a good ass pounding usually but this felt very different and just a little bit wrong. But at the same time, the kinkiness of it all began to make me more than just a tiny bit hornier. Just as I was beginning to get adjusted to it and like it ever so slightly, I felt the man reach down and begin to jerk me off. I stared up at him and he stared back with no expression at all. With her strap-on pounding into my prostate, and his rather large but surprisingly soft hands stroking my dick, it was not long at all until I exploded in one of the biggest orgasms I have ever had.

After my orgasm, she pulled out of me, he let go of me, and then she took his hand and they started to leave the room. She stopped long enough to tell me my money was on the small table just inside the foyer, and she thanked me for the ride. I wasn’t sure if she was talking about the airport or being sarcastic. Either way, I got busy getting out of the crazy swing contraption. Once I had freed myself I saw my clothes had been neatly stacked on a small shelf near the door. I wasted very little time getting dressed, feeling a little dirty and very used. I could hear them having sex down the hall and I could still taste and smell her essence on my face. I grabbed the envelope with my payment and bolted out the door. Sitting in the van, my sore ass still recovering from its trauma, I opened the envelope to discover she had paid me three times my usual fee. There was also a note that simply had a date, a time, and instructions to let myself into the villa and strap myself into my hanging swing thing. The PS simply stated that “you know what happens if you fail to appear.” I still can’t believe she expects me back and I don’t know exactly what to do. Honestly, there is a fairly substantial part of me that enjoyed it all, and though I feel like a piece of meat, I will probably do as she asks.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, more than 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? Today I feel a little less apprehensive about the whole event. In fact, once again, if I’m honest, I enjoyed most of the experience. Something about being controlled and managed by her and her “friend” was nice. When I close my eyes, I can still see her wrinkled old body and I actually get hard. Her orgasms were surprisingly intense and easy to bring about. I think with time I’ll get over the initial shock and learn to like the way her domination feels.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Material rewards (gifts, money, drinks, dinner…), Just happened, I don’t know why just went along with it, I didn’t want it but was unable to stop it

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

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

Did you consent to this hookup at the time? I did not give consent, however, I did not stop it and her threats were pretty powerful incentive to just let it happen.

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? Clearly, she wanted it, even demanded it.

To whom did you talk about the hookup? How did they react? I have told no one.

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? A little bit

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

Do you regret this hookup? A little bit

Why do you regret this hookup? I have no control over it and it has raised my normal anxiety level. I worry about her telling my wife.

What was the BEST thing about this hookup? A lot of the actual sex was pretty intense and pleasant. I have always wanted to try most of what happened, just more on my terms.

What was the WORST thing about this hookup? The surprise of it

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The whole experience has actually made me feel more effeminate.

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

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

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? Since my wife has lost interest in sex, I now only have casual sex. I wish people wouldn’t judge me for it so that I could just come out and be who/what I really am.

What do you think about the Casual Sex Project? love it

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