by Mikiael


Gender: Male
Age: 32
Race/ethnicity: Russian
Current location: Manhattan
Highest education received: College degree (eg., BA, BS)
Occupation: Investment Banker
Relationship status: Sort of Single
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? None

Something Unexpected

How long ago did this hookup happen? A Year/Ongoing

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…)? 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? Her name is Kayla, she has long black hair and is covered in tattoos.  She is in her late twenties, a few years younger than me.  I had seen her around the building where I worked, she works for one of the other companies in my building, but with all the tattoos and black lipstick and nail polish she was not really someone I would even talk to or even consider as a sexual partner, I thought she was some biker chick (turns out she was when she was younger).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I would like to start that I am a relationship type guy.  I grew up in a strict religious background where sex outside of marriage was strongly frowned on.  My views are a little different, I really enjoy sex but usually only really with someone I am dating.  In the last ten years I have only had four sexual partners, two of which were serious long term relationships that lasted three and five years respectively.
Now the second relationship ended about a year before this, she had cheated and the breakup had been difficult for me and I was not looking to get right into another one.  I had not dated anyone nor had sex in a year.
My friends thought I was getting too pent up and on edge because I needed to get laid.  My roommate and a friend from work took me to a bar.  A few women came up to me, my friends brought a few over as well but no one I really liked.  In an example of the worst wingman ever, my friend went off with a blonde he met.
I had finished my first drink and gone to the bar for a second and Kayla was there too.  She was complaining about her friends a bit, apparently she was at the bar for the same reason.
As I said above, I did not consider her a sexual partner right away.  We started chatting, work at first and Kayla said she had seen me around my building.  She was quite intelligent and educated, and unlike most people understood what I did for a living.  Intellectually we really clicked and we started flirting a bit, and I asked if she wanted to go back to my place.  
We got back to my place and I asked if she wanted something to drink, and Kayla declined.  We sat on the couch and talked for a bit, we were both nervous and it had also been a while for both of us.  I considered asking if she wanted to leave and we could go out again, but decided not to.  We ended up starting to kiss and Kayla stuck her hand down my pants and grabbed my cock and stroked it.  Kayla said she really liked me and she wanted to sleep with me.

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 I am not one to normally fuck a woman within hours of meeting her.  Kayla and I moved to the bedroom and ended up making out on my bed.  Clothes came off and my theory she was confirmed, she was tattooed from the neck down.  She was fit with a big chest but still a little curvy and physically a lot more my type than I thought.  She asked me to sit back and began to blow me, I had considered asking for oral but had not worked up the nerve.  She licked and sucked, and deep throated me a bit, orally Kayla was quite talented and it took me a while to come but I did in her mouth.  Afterwards she got up and went to the bathroom to rinse her mouth out, and she returned and wanted to cuddle.
We chatted a bit, about our kids since we both had them from past relationships and about work a bit, she was working towards a PhD.  I asked about some of her tattoos, most came with some sort of story. We had sex again, I initiated by rubbing her thigh a bit and then climbing on top of her and kissing her.  I sucked on her breasts and penetrated her and rode Kayla for a while.  She got quite loud when she had her orgasm and I finished again as well.
After Kayla asked if I wanted her to go and I said no, and wrapped an arm around her waist and fell asleep soon after.  In the morning we had sex two more times, first was standard missionary and the second was cowgirl which Kayla was really into.  She took a shower and left around noon.

Did you have an orgasm? Did your partner(s)? I did several times, and Kayla did twice.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? For the oral no and we used condoms for any penetration.  Kayla also said she was clean and on the pill.

What were your REASONS for having this hookup? I was really horny and it had been a while for me and I did feel an intellectual attraction to Kayla.

Were alcohol or drugs involved? If so, how much? I had two Scotches, Kayla didn’t have any.  She doesn’t drink.

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? I had black lipstick marks all over the place.  Kayla and I have been sleeping together a year, a few times a week when we can.  We both work a lot and have kids, and Kayla is also trying to finish college.  We have been out to dinner and the movies, a few art shows as well.  We have met each other’s kids as well.  I would say we are in a relationship just not something serious.  I really like Kayla and enjoy her both in and out of the bedroom and am considering if she would like to see if this could turn serious.

To whom did you talk about the hookup? How did they react? My roommate found out right away, Kayla was still there in the morning when he got home that first day.  He was impressed.  Most people make the same assumption I do that Kayla was not my type until they meet her.

Was this a consensual and/or wanted experience for you? For your partner? Yes for both of us

Do you regret this hookup? If so, why? No

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? Great sex and connecting with someone on an intellectual level.  I think the worst part was assuming that because of the lipstick and tattoos I assumed Kayla was not my type, I feel I was a little prejudiced.  Kayla however was very understanding when I confessed this to her.  As for casual sex, reading some other posts on here and thinking about my own history I would be one of those who argue there is no such thing as casual sex.  There is nothing casual about what Kayla and I did or what has gone on between us.  However I would say I have changed my views and hopefully will be a little less shallow and prejudiced with future partners, should things not work out between me and Kayla.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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