Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Relationship status: Sort of Seeing Someone
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? One
How long ago did this hookup happen? 10 Years
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short/Rebound Fling
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 first met “Iris” about a year before we hooked up. She is a pretty Latina, back then she had shoulder length curly hair, about five two and thin with a small chest and glasses and also about thirty. She wasn’t really physically my type. She was the head of our IT department and had come to my office to fix my computer. I found her intelligent and charming if a bit shy and was instantly attracted to her. We would end up going on to spending a lot of time together but when we first met I was still married.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When I first met Iris it was during the twilight of my first marriage, about a year before my wife and I split up. The last eighteen months of it was the worst time of my life. When I first met Iris she was a welcome distraction.
As I said I found her intelligent and charming, and we ended up spending a lot of time together. We met for drinks, had dinner, and hung out at her place quite a bit. Once I had her out of her shell she was a lot of fun to be around. I started thinking about what it would be like to be intimate with her and at our office Christmas party (which are infamous for hookups between coworkers) we ended up making out in a closet and Iris said she wanted to be with me. Now I am a lot of things including a complete womanizer but I am not a cheater, and told her as long as I was still married I couldn’t be with her. Thinking back and knowing what I know now though Iris and I were having an emotional affair.
At home things were pretty bad. Now my wife and I were having a lot of sex, the most I have ever had in my life often two and three times a day, but beyond our fucking my wife and I were barley speaking and could barley stand to be in the same room. We separated in March.
It was supposed to be a trial separation but I knew my marriage was over. I had moved into a hotel while I was looking for an apartment (My wife had kept the house as we had a young son at home). I had asked Iris to meet me for drinks in the hotel bar about a week after I separated from my wife. We talked for a while, things were a little awkward between us since our make out session. I told Iris I had split from my wife and wanted to be with her. She was pretty excited at the prospect but I also warned her if we hooked up now it would be very short lived as I was on the rebound and I left the decision up to her.
Two days later she came to my hotel room. We had ordered room service for dinner, had some wine, and ended up on the couch where we had started kissing. I was not in the best of moods, a little depressed.
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? Iris said she was going to cheer me up, took my belt off and pulled my pants down. She began to suck my cock, and lick my balls a little. My wife hadn’t given me oral since before we were married so it felt amazing to be having it again. Iris was orally quite talented and overall was a lot more sexually experienced than I thought. It took me about ten minutes to come, and I exploded in her mouth. Iris was quite pleased with herself and went to the bathroom to rinse her mouth out.
She returned having removed her pants and unbuttoned her shirt. We ended up on the bed talking, I was nude at this point, where Iris told me she had wanted to be with me since we had first met and she hadn’t been with anyone in nearly a year.
We ended up going again, I pulled her bra and panties off and we had sex in missionary. I alternated between kissing her and sucking her breasts which she really liked. We both orgasamed in near unison and fell asleep soon after.
In the morning I awoke and Iris had mounted me and was riding me. I was quite hard and finished inside her quickly and Iris said she thought it would be a fun way to wake me up. We took a shower together and she dressed and left shortly after as she had plans. I had a lot of fun that night and it felt great to connect with someone.
Did you have an orgasm? Did your partner(s)? I did all three times, Iris from just the once when we did missionary.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None and we barley discussed it and I finished inside her twice, and a bunch more times during the short time we were together. It was no wonder she ended up pregnant.
What were your REASONS for having this hookup? I was depressed and lonely and was looking to connect with someone, and Iris was someone I had thought about being with for a while.
Were alcohol or drugs involved? If so, how much? Iris and I shared a bottle of wine, not sure how many glasses each that was.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Iris and I had sex every night for about three weeks and in my office a few times. Honestly looking back I felt next to nothing, I was pretty detached during this time. On the same day I served my wife with divorce papers, I ended things with Iris who was upset a little but I had warned her. Initially I chalked Iris up as one of many short flings and one night stands I had during and shortly after my divorce. Iris transferred to another office about six hours away.
She got in contact with me to tell me she was pregnant a few months later. For me it was a huge blow, as my ex-wife was also pregnant from all the sex we had been having before separating. Without going into a lot of details, my second and third children were born about three weeks apart and I have tried to be there for both kids.
It’s been ten years since Iris and I were together, but since both she and our daughter live six hours away I don’t get to see them much. We talk on the phone some and Iris and I are quite friendly and get along well. We talked a few times about trying to date, quite a bit after my second divorce but it never happened. Now last summer during a visit I saw Iris in the pool in a bikini, she is about thirty ponds heavier than when we were tougher and a lot curvier and I was nearly overwhelmed with lust. I made a pass at her but she did not pick up on it, and because I was and still am sort of seeing someone I decided not to pursue it further.
To whom did you talk about the hookup? How did they react? Told one friend I was rebounding with someone after my wife and I separated, he thought it was a good idea but he never liked my first wife
Was this a consensual and/or wanted experience for you? For your partner? Yes for us both
Do you regret this hookup? If so, why? Quite a bit actually, nothing to do with my daughter, but I feel Iris is someone I could have had a real relationship with had I waited and been in a better place and not dealing with the end of my marriage.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I would say it was that blow job, it’s something that is burned in my mind. I think the worst part is the realization that I could have had a real relationship with Iris. This hookup did change a few things, I have gotten better at telling if someone is a one night stand, short fling, or potential relationship material. I also hadn’t been with anyone other than my ex-wife in about seven years or so, this opened me back up to the world of dating.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? Somewhat negative
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