Looking For Trouble



What’s your gender? Man
How old are you? 50’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, Ph.D., JD, MD)
What’s your current relationship status? In a serious relationship (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 2

Looking For Trouble

How long ago did this hookup happen? Last Year

What was your relationship status at the time? In a relationship (open)

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

How long did you know the person before this hookup? Just met that day

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? My SO and I have an open relationship. We both have the freedom to experience different partners as long as we are clear and open with each other. She can best be described as a sexual dynamo who wants to experience many things, and when she is in the mood, everything is on the table. This story is about one evening when she was out hunting for a single male for a threesome.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One evening we were sitting around kind of bored when she said to me that she was in the mood for some trouble and wanted to see if she had any luck finding a willing single male for some fun that night. It was relatively early, so she had time to get ready to look her best. One of her rituals is that I have to pick out her clothes for the evening, but I always ask her what she has in mind, so I get a good idea of what to suggest. She indicated to me I had the freedom to pick ANYTHING and she would wear it.

I chose for her a loose fitting extremely low cut top that barely holds her DD breasts. If she leans over too far, they are easily visible. I chose as well, and extremely short skirt that barely went 4 or 5 inches below her pussy so that she had to keep her legs crossed or together or her pussy would be exposed. I chose a sheer thong panty for her in a contrasting color so there would be no questioning whether a potential partner saw what she had on underneath. I told her to shave and oil her legs (she has great legs and ass by the way) and to put on her highest platform stilettos.

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 took off for a bar which is known as a “cougar bar” locally. She went in about 30 minutes before me alone. We did that on purpose, so there was no way anyone could know we were together. There was another bar close by that I went to for a beer or two. We normally keep in contact by text for her to let me know that she had found a “person of interest” and things were heating up and progressing. Usually, a simple thumbs up via text let me know to head over. I love to watch her flirt so as soon as she sees me walk in, she turns it up a bit.

She had met this middle-aged professional man in a business suit who was in town for a meeting. Him having his own hotel room made things much easier, as we don’t like to bring people we don’t know to our home for obvious reasons. Nevertheless, I observed his hand on her thigh, as she leaned over slightly. I knew he got a great view of her DD breasts from that position. I could feel my heart begin to race and my excitement built. She texted me to come over and introduce myself. He was quite personable and was open to a threesome as he indicated he had them before and enjoyed them.

We took an Uber to his hotel which was very nice. I loved the fact that her hands were all over him in the car, and she whispered to me that it seemed he was very well endowed. As we got to his room, she excused herself to the bathroom to freshen up, and we discussed what was allowed. I told him to let her lead the way and whatever he was comfortable with was fine with me. I indicated I liked to watch mostly and then join in later.

She came out of the bathroom and had reapplied her oil, so she was glistening in only her stiletto heels. He then motioned her over to the couch where she knelt between his legs and undid his pants. I think she was surprised that he was as large as he was. Easily 9″ and extremely thick. She tried her best to give him a blowjob but had a hard time getting her mouth around it. I suggested she use her oiled pussy to slide up and down on his cock which she loves to do; she is an unbelievable tease. I could see he was getting pretty worked up and enjoyed it. She then slipped him inside her waiting pussy and let out a soft moan commenting on how it filled her completely. She rocked back and forth for some time until she whispered, “please cum in me.” I think that sent both of them over the edge as he filled her while she orgasmed. As she got up from his lap, it was obvious that he left quite a lot of cum in her.

It was now my turn, and she began sliding her cum soaked pussy on me until she was ready and I slipped in. Doing her after she has been filled is a fetish of mine and it didn’t take long for me to fill her as well. She immediately got up and put her sheer panties on and excused herself to the bathroom. She put her panties on so that the cum would be held in for a little bit. As she emerged from the bathroom, she said to him, “Here is a little souvenir,” and took her panties off and placed them on his nightstand. We then said our goodbyes and grabbed an Uber back to our car with fond memories of a hot night.

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? We always have a good time with nights like that, and it makes for good memories when we are alone.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? 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? Just friends in our circle

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? Fun and excitement over the evening

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? not at all

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

All things considered, how NEGATIVE was this experience? Not at all 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? I think it’s great and as long as people go into it with little if any expectations it’s a wonderful experience.

What do you think about the Casual Sex Project? I love it. I enjoy reading the stories

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