Beyond What I Wanted

by Maximilian

What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Unfulfilled
How many sexual partners have you had in your life (including oral sex)? 14
How many hookup stories have you here posted before? 1

Beyond What I Wanted

How long ago did this hookup happen? 6 years

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

How would you best classify this hookup? Friends-with-benefits

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? Miranda is a white woman who lives on a Caribbean island. She is about 5’8 with brown hair, brown eyes, and a pretty smile. She’s full figured. We first connected on OK Cupid when I was traveling to the island for work. She’s 16 years younger than me and didn’t have a lot of information on her profile. We had spoken once by skype before I made the trip down. She picked me up at my hotel, and we went out for a casual dinner. We played some pool and eventually ended up back at my hotel, walking along the beach.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We kissed on the beach for the first time. She asked me if we should go back to my room. I said sure. We kissed there once again, and she told me to turn off the light. We got undressed and had missionary sex on the bed. I was in a sexless marriage, and this was the first person I had slept with in years, so sadly I didn’t last long. I walked her back out to her car, and we said our good-byes. I thought that would be it.

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? That was 2013. A few years later, we somehow connected on social media, but I didn’t see her again until 2017. She met me at my hotel, and we had dinner. She was nervous at first, but about halfway through dinner, I could see her relax and knew what was coming. We went back to my room and started making out. We were both horny and wanted it, but she was on her period. We fucked anyway. She let me ride her bareback, though she would not let me cum inside of her sadly. She came over the next night for more sex. About a year later, on my next trip, we met up for dinner and sex again. Again, we did not use condoms, though she made me pull out. I cum a lot, and she was not on birth control. She has a really tight pussy (she flexes it regularly to keep it that way). She also has a really high sex drive. She doesn’t often even want foreplay, just sex. She’s one of if not the best partner I have ever had. It feels so incredible to be inside of her, especially without a condom

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? After the first hookup in 2013, I felt badly that I had cheated on my wife. Even though we had a sexless marriage and I have a high sex drive, I still had regrets. But after the 2017 hookups, I was very happy. Between 2017 and 2018, we communicated frequently through social media and sexted often. We started saying I love you to each other, and it was clear she wanted us to be a couple, not just a long distance FWB. She did not know that I was married. I had lied to her and said I was divorced.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To cheer myself up, I was feeling lonely

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? No one.; Because I am married, I cannot discuss my experiences with others

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? I really wanted this to be non-committal sex, but we developed feelings for each other. She really wanted a relationship with me. She really wanted me to marry her. I hurt her because I would not, and I regret it. We eventually stopped communicating, though I miss her a lot and wish I could see her again.

What was the BEST thing about this hookup? She has an amazing pussy and is very skilled in bed. She is also an incredible person

What was the WORST thing about this hookup? Getting too emotionally involved and getting hurt

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I hadn’t dated much before I started dating the woman I married, so this was my first real experience with casual sex. I hated myself the first time for cheating, but then I grew to really enjoy the sex. But the repeated casual sex and long length of our friendship caused us to develop feelings for each other, which I had not planned on happening.

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

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

Anything else you want to add about this hookup? I’m sorry that she got hurt. She doesn’t know it, but I got hurt too. Part of me wishes that we could be together, even married. It just wasn’t in the cards for us. Still, it was worth it for those amazing nights.

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? We should all be having a lot more of it. We’d all be happier

What do you think about the Casual Sex Project? Fantastic. I am inspired by the stories on here

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