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What’s your gender? Woman
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA (California)
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? attorney
What’s your current relationship status? Mid-stream in a divorce currently after long-term spouse suffered a massive stroke 3 years ago
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I’m alive again and could have sex all day every day after years of thinking I was over that
How many sexual partners have you had in your life (including oral sex)? 10ish
How many hookup stories have you here posted before? 2

I left a lake on the guy’s mattress

How long ago did this hookup happen? 3 days ago

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

How would you best classify this hookup? Short fling

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

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? I met T on the men seeking women section of Craigslist. I live in a big city center and every day there are lots and lots of ads on CL, but at my age and for the kind of thing I’m searching for there isn’t usually much. T. posted an ad about a month ago with a series of questions to answer about myself (ie what I read, what kind of undies I wear, other stuff I forgot). I answered and we emailed for a week or so before we met up in a large city park to take a walk through the botanical gardens. T. is 55. He’s got dark hair, is slightly balding on top, he’s 5’9 and about 170 pounds. Fairly fit. He has a gorgeous full chest of hair. When we first met, we walked and talked and I thought he was nice. He is an unusual person. Quirky is the best way to describe him. He didn’t grab my attention right away, but I thought he was nice enough. He was easy to talk to. He gave me a great neck massage on a bench in the park and it was a bit sensual, but very nice and easy. It didn’t make me jump out of my skin, which tends to happen with me. At the end of our walk he asked if I would go to his house the following week for dinner. I ageed, knowing full well that it would likely lead to sex which given the neck massage I figured would be good. His apartment, I later found out when I arrived for our dinner a week later, was tiny and crammed with all sorts of baseball memorabilia. He doesn’t own a cell phone but he has a computer. He put on nice music, he made me dinner, followed by mediocre awkward first-time sex. I left about 11 to go home to my kids and figured I’d never see him again. But damn if I didn’t leave my favorite earrings there! He says those things happen for a reason and although I tried to get out of seeing him again he wouldn’t let me go so easily.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The week after the first hook up which was such a dud, I went to Chicago and Indianapolis for work and for my kid’s volleyball team. I emailed T and said I didn’t think we had much future, too different, and I didn’t want anything serious. Plus he is seeing a married woman and has been for many years. I’ve recently written about being involved with married men and how hard it has been on me. So I had a handy excuse to get out of seeing T again. Only he had my earrings. At first he didn’t write me back. Then he wrote back a hurt message. Then he ignored me. When I got back I told him I really wanted my earrings back, and he responded that he wanted me, he had to see me, he wanted me in his bed, he wanted to taste me … I don’t know. It sounded like a good idea to have his lips locked on my pussy, even if I didn’t like him overall that much.

I also had a vacation planned to Maui. Between Chicago/Indy and Maui, it was like 5 weeks before we could meet up again. We agreed to meet at a place near my house that overlooks the ocean. I figured it would probably end back at his place since I live with a couple of teenagers and there is no way I’m bringing men back here to have sex with them. Within about 5 minutes of picking him up at the meeting spot he asked if I would go to his place to drink wine. I said yes, and within about 5 minutes of walking in his door we were in his bed and I had no clothes on.

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? Now that I’m older I really notice how hormonal changes all month affect my sex drive. Three nights ago I was about a week past my period and at an all time sexual high. T. first just made out with me naked on his bed. He has a really big, thick cock and it felt so good pressed into my stomach, thigh and pussy. We rolled around on his bed for a while and he went down on me. I really enjoyed it since the first time he didn’t do that because it was the end of my period. This time he took his time getting down there, ran his tongue along the whole of my pussy before going inside me with his tongue and fingers. He spent some time doing that while I was rocking my hips and hoping that he’d make his way to my clit sooner rather than later. I was so wet and I could feel my juices running out of me. Plus I really had to pee badly. Normally I don’t like to have sex or orgasm when I have to pee because it makes peeing afterwards so hard. But that night the pressure from needing to pee plus the pleasure I was feeling from T’s tongue really felt great. I can’t explain it but all sensation seemed to be heightened. T was very good at putting me at ease when it took longer than usual to come. I was getting so excited and breathing hard and moaning and finally I just blurted out “I need you inside me. I want you to fuck me!” I said that several times. He crawled up my belly with his cock in my face so I could suck him while he got a condom and then went inside me. The first few thrusts when I’m that excited feel so god damned good. It is really an amazing feeling to be so filled up. T kept saying softly in my ear “slow down, I’m filling you up, this is for you so you’re full and you can feel me” and then he just rammed himself inside me so it took my breath away and I moaned and loved it. He had to stop a few times to prevent himself from coming too fast. I never come from intercourse but the feeling is so great. He eventually had me get on top of him and suck him until he came quickly.

We took a short break and talked and kissed for a while longer. Then he went back to giving me oral. This time I felt like I was going to come for a good 10 minutes or so. I was right at the edge. I have a new shower head at home that I’m in love with. It goes straight to my clit and gives me the best orgasms I have ever had. T’s tongue felt like that on Wednesday night. All I felt was the intense pleasure in my whole clit and the warm tingly feeling of just about tipping over the edge the whole time he was licking and sucking me. And he never made me feel bad about it taking so long. Finally I just needed to come and I put my own hands to my clit and rubbed for just a few seconds while T ran his fingers gently in and out of me and had a very powerful orgasm. T’s cock is so beautiful. I had to suck him some more after I finished and we ended with me grinding on his cock and him under me sucking my nipples for another orgasm for him. When I finally rolled off of him and started moving around to find my clothes I realized I left a wet spot the size of the Pacific Ocean on his mattress. Oops! I don’t think I have ever been so wet. My underwear, even though they came off of me fairly early in the evening, were still soaking wet. I felt kind of bad about the wet spot on the mattress. “Wet spot” doesn’t even begin to describe how wet it was. I don’t think it was pee. I’m sure of it. I didn’t leak and I don’t squirt as far as I know. Which means it was all just from me and how excited I was with T’s fantastic oral skills.

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? I got up and got dressed fairly soon after T came for the second time and went home to my kids. Since then T has emailed me a bunch and he’s been a bit too insistent that I see him again. We met up last night for drinks near my office and he brought me flowers. I don’t know why, but I went a bit cold at that. And he’s gotten me to agree to dinner back at his place in 2 weeks. I am not sure I want all of that. I’m ok with seeing him for sex once a month or so. But I don’t want or need more than that, and I feel like T is pushing me to be closer to him than I want to be.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have

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? I told my friend D and it has increased the likelihood that D and I will hook up soon. He is a good friend who has wanted more for about a year now. The more experiences I have with people I really like and the more I learn about sex and my body after so many years in a monogamous relationship, the more open I am to have a sexual relationship with someone like D who is a good guy and a good friend.

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? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? I am not sure if “regret” is the right word. Although I really wanted sex with him, I don’t think T and I are right for each other. He’s just so not my type and I don’t enjoy sitting and talking to him for hours like I have with other men I have known recently. I think T will be fairly hurt when he realizes I don’t want to be his girlfriend and I maybe took intimacy from him without much expectation of having anything last longer term.

What was the BEST thing about this hookup? T’s beautiful, big, smooth penis and the fact that I was so excited and so wet.

What was the WORST thing about this hookup? That T wants more from me than I want to give.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s awkward when the partners don’t see eye to eye on what the purpose of the hook up is. I am not someone to use other people. I don’t throw people away after using them. This hook up makes me feel a little callous and like I don’t know myself well. Plus I don’t know how to get out of seeing more of T when I’m not yet ready. I don’t want to go to his house for dinner in two weeks. I want him to be a bit more like me, and less insistent that I act like his girlfriend.

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

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

Anything else you want to add about this hookup? I’m trying to be a decent person and leave T feeling empowered by knowing me and fucking me. He has said repeatedly how good it was and how much he enjoyed it. I just have to keep him focused on that, and not hurt or pissed off that I am feeling claustrophobic.

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 all for casual sex. In a healthy way. I don’t want random hookups with people I just met, never to see them again. I want a friendship with someone I like and respect, and then I want to sleep with them and have fun with them and hang out. Then go back to my real life. Casual sex is great for that when I meet the right people. So far I have yet to find the actual formula that works for me, but I’m continuing to look. I have met the most amazing men in the past year since deciding to leave my marriage.

What do you think about the Casual Sex Project? It’s awesome. A good outlet. A learning experience for me. I have one story about a bad sexual experience (while I was traveling recently for work) that I will post later. It seems sometimes here that everyone else but me has these amazing casual hook ups with life altering sex. And that can’t be true all the time. I realize that it is important to post about the awkward, not so stellar stories too, even if the incredible stories are more fun to read. My bad experience wasn’t hurtful for me at all. It was just the worst sexual encounter I think I have ever had.

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

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