Full Circle

by TW

What’s your gender? Man
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? Midwest USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Education
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation:
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)? 70 +
How many hookup stories have you here posted before? 1

Full Circle

How long ago did this hookup happen? 5 years

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

How would you best classify this hookup? Sex with an ex

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? N is of South Asian descent, is in good shape, works out regularly, has c-cup breasts, long black hair, light brown skin, has had two children, and a very pretty face.
I have known her since we were kids and we were friends since junior high. We made out in junior high and dated for a year in high school.
When we were in junior high we made out after a dance and I fingered her, but at school, nobody knew that anything had happened between us, and when we were dating in high school we used to do lots of making out that usually ended up with me fingering her very wet pussy. She would make these moaning/sobbing noises and at first, I thought I was hurting her. Looking back she was probably cumming or getting close to cumming every time she would make those noises.
We dated for almost a year before we first fucked which we only did twice in high school. The first time was awkward and it didn’t last long but the second time was a different story. That time we both were really getting into it when the condom broke which ended our session.
I was in love with this girl and was crushed when we broke up. Even though she got married a few years after high school I didn’t get over her for years.
Eventually, I moved away, got married, and put her out of my mind.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup happened after I moved back to where I was from with my family. She was still married and I would run into her and her husband about once or twice a year around town.
She was still beautiful and being in her mid-forties made her even more so for me. That being said I wasn’t looking to get with her and didn’t think she would be interested even if I did. She looked happy with her husband and I was happy for her. She had had her kids earlier so she was getting ready to be an empty nester as I was just getting into the thick of family life with young kids.
I heard that she had gotten divorced and gotten a loft apartment downtown near where I lived. Eventually, I ran into her and some of her friends when I was out drinking with some of our high school friends. She confirmed it was true and I and one of my buddies actually walked her home that night.
A similar scene played several more times over the next few years until one night after a mini high school reunion of sorts, I walked her home alone. Along the way we stopped and started making out. I don’t know what prompted it and at the time it seemed sort of innocent and fun. Reliving some old times kind of thing. I rubbed her breasts through her jacket but that was about as far as it went. The night ended when she told me if I came up to her apartment I wasn’t leaving.
I went home and my wife had no idea, my friends had no idea, and I felt sort of guilty, but also sort of energized.
Over the next few months, I thought about it quite a bit. I did not want to harm my marriage but I definitely wanted to be with N.
After going back and forth a few times on Facebook messenger we decided to take a walk one evening. I take walks at night regularly so this would not have raised suspicion with anyone at home. The walk went well and ended with a kiss goodnight. We repeated this a few more times until one time she invited me up.

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 had a glass of wine and I was standing behind her in the kitchen. She just kind of leaned back into me. I wrapped my arms around her. I smelled her hair and just held her tight against my body living right in that moment. We both got very turned on very quickly after 2 months of foreplay. She rubbed my legs and I rubbed her hips and breasts and pulled her into my body. She broke the ice by saying, “are we gonna fuck or what?”
We slowly undressed each other in her kitchen and I distinctly remember smelling her wetness through her running tight as I was pulling off her fleece top. Her breasts were much more fuller than they had been in high school and her big brown nipples were very much a turn on.
We eventually ended up in her bedroom; she was naked and I had no pants on as she pinned against the wall, got on her knees and hungrily took me in her mouth. This was new for me as she had never given me head in high school. That lasted for a few minutes before we finally made it to her bed. We went slowly at first but once I was fully inside her I couldn’t hold back and blew my load way too early.
She, however, was unfazed and told me to keep going which I did even my dick was getting soft. She kept telling me to give her a little more and kept pulling me into her. I was a little put off by this because no other lover had ever been so direct about what they needed and I kind of felt like I was just a tool. I went with it though and eventually got semi hard again and her orgasm started to build; after about 20 minutes her eyes rolled back in her head and she had a very strong orgasm.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 had mixed feelings when I left her apartment. I felt very guilty that I had cheated on my wife and was worried about getting caught, and felt like N had been more worried about her pleasure than mine. I also was very turned on by her naked forty-something body, the blowjob, the foreplay, the excitement of fingering her again after almost 30 years.
I did not know if I would go back but after a few weeks of course I did and continued to do so once or twice a month for close to a year.
I learned that her telling me exactly what she needed actually got to be a huge turn-on. We got really good at fucking and would literally fuck for hours at a time where would have two or three very explosive orgasms and many little ones.
After the second time, my friend gave me some viagra which enhanced things even more.
It was always sad when I had to go as she never wanted me to leave. She always said, “fuck me one more time” as I was about to leave, which I always did.
The attachment was one of many reasons that I had to put an end to things as I did not want to mess up my marriage. The guilt actually was messing up my head which I am sure, had an effect on my marriage.
I loved N very much which enhanced the lovemaking but also made it an untenable situation. It was becoming a non-casual sex situation.
About a year after I broke things off she texted me and told me she was moving to another state. I went to visit her that night and she gave me the best blowjob of my life for old times sake. She got very turned on giving head and told me she got a craving of wanting to suck all of me as I was getting close to coming. She sucked every drop of my cum.
I still think about her all the time and have heard she is doing really well.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel more desirable, I was feeling lonely

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

What substances did you consume? Alcohol, Marijuana, hashish

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

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? One friend who lives in another state.

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? Very

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

Do you regret this hookup? Not at all

What was the WORST thing about this hookup? I was married so we couldn’t be in public together.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It taught me a lot about myself sexually and probably improved my sex life with my wife.

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

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 is great and I do not think all humans are meant to be monogamous.

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

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