by TM

Gender: Male
Age: 43
Race/ethnicity: White English
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Own a PR Firm
Relationship status: Married
Religious affiliation: Catholic
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? Several

White Russian

How long ago did this hookup happen? Six Years or So

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…)? Friends With Benefits/Casual Relationship

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? Osanka was in her mid-twenties, tall with long black hair and thin with a nice medium chest.  She worked as live-in help for a family in the building where I lived.  I met her in the laundry room one day, waiting on my clothes I thought I might chat up the pretty woman also there.  Back then Osanka didn’t speak much English and I quickly learned she was from Russia.  However this was not a huge issue as I spoke fluent if somewhat rusty Russian which she said was really bad and laughed a little.  I found her charming and she was surprisingly well educated but her degree was useless here in the US.  Neither of us is American we had that in common.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met Osanka in the laundry room about a month before we first hooked up.  I talked to her and was friendly with her when I saw her in the laundry room or in the park a few times and she was an excuse to practice my Russian and Osanka liked talking with someone.
Now I was a little hesitant to hook up with Osanka, mostly because I was dealing with a recent breakup with someone I had been seeing a year.  She was the first relationship that had approached serious since my divorce so I was hurting a little. 
One day we passed in the hall, started talking and I don’t remember what we said but I ended up kissing her and we ended up in my apartment.

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? This was all pretty standard, we made out on my bed for a while. Clothes came off and I played with her breasts for a bit and sucked on them.  I penetrated her and rode her until I orgasmed.  The sex was decent, good even but nothing spectacular.  We fell asleep after as it was late.
I awoke the next morning somewhat groggy and Osanka had mounted me and was riding me, I put my hands on her hips and let her finish until she orgasmed.  We cuddled for a little bit, I kissed her and she then left around five in the morning.

Did you have an orgasm? Did your partner(s)? Yes we did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None which was quite foolish, but Osanka did go on birth control about a month later.  I did find it interesting that she never liked condoms or wanted to use them.

What were your REASONS for having this hookup? I was lonely and horny.

Were alcohol or drugs involved? If so, how much? None which was very different for me at the time.

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? Osanka and I were friends with benefits for about a year. She would knock on my door a few nights a week and we would have sex and she would often stay over and leave early.  Some nights I would make her dinner and once in a while we would watch a movie.  We never went out, and to this day I wonder if she was here legally.  She also had me teach her English and she often had me teach her new words when we were in bed.  Looking back I would say we were a couple and I was using Osanka to not have any sort of relationship.
I broke things off a year later and Osanka moved to a different family shortly after, I knew the husband of the family she was working for had become quite inappropriate with her.  I have wondered a few times about what happened to her, I haven’t seen her since shortly after we broke up.

To whom did you talk about the hookup? How did they react? I have never told anyone about this one which was part of the reason I wanted to share it.

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? Not at all

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? Good sex on a regular basis, worst part was part of me always felt like I was taking advantage of Osanka even though she always assured me I wasn’t.   Not sure this changed how I feel about casual sex or sexuality.  However I did use this relationship to avoid having one for a year.

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

All things considered, how NEGATIVE was this experience? A little negative

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