by D

Gender: Male
Age: 30
Race/ethnicity: White
Current location: Portland Oregon
Highest education received: College degree (eg., BA, BS)
Occupation: Business
Relationship status: Seeing Someone
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? A Few

She Went After Me

How long ago did this hookup happen? Two Months

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…)? Other

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 B eight years ago.  She hired me right out of college to work at the same company she does.  For many years she was my direct supervisor but now she is my boss’s boss.  She is an attractive blonde in her mid-forties and is fit with a big chest.  I knew her pretty well, as I said we had worked closely together for many years but not the past two.  I also knew she had gotten divorced about five years back.  Honestly she was not even on my radar as a sex partner.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was working one evening and dropped some paperwork in her office.  I was going to leave when I asked if she was having a hard day and she said yes.  We started talking a bit, I offered to rub her shoulders.  That turned quickly to kissing and sex.

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? Without even realizing it next thing I know her dress is off and I am sitting on her couch while she pleasured me orally.  Having been single a few months I went with it.  She gave me oral for a  while before asking me to lay back and then B mounted me.  I put my hands on her waist and she bounced up and down in cowgirl.  I grabbed her breasts a few times.  She never had kids, and while she was older her pussy still fit me good and everything on her was firm.  She was eager and quite aggressive and even a bit loud, but the office was deserted.  We didn’t really talk much.  I finished and so did she and she asked me to leave and go home for the night.

Did you have an orgasm? Did your partner(s)? We both did very close together

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Didn’t discuss it and we did not use a condom, and I finished inside her.  B told me she took a morning after pill.

What were your REASONS for having this hookup? It had been a while since I had been with anyone, and I had never had a woman come onto me that strong.

Were alcohol or drugs involved? If so, how much? Not one bit

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? We ended up hooking up twice more that week.  First time I went by her office to talk about what had happened and that quickly turned into sex.  Second time she came by my place that Saturday and she spent the night and we had sex several times.  We discussed it and decided it wasn’t a good idea for us to continue.  Both of us have had bad experiences in the past with workplace romances, and B is sixteen years older than me.  We have also both started seeing other people since this happened.  However I have not looked at her the same since but I only cross paths with her a few times a week at work, and it hasn’t even really been that awkward.

To whom did you talk about the hookup? How did they react? No one, this was a private thing between me and B.  She would also not like me to tell anyone.

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? Honestly not one bit

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? The best part was the sex, it was very good.  I think the worst part was that it could never go anywhere.  This was a bit different for me as well.  I have had women come into me in the past, and horny girlfriends that wanted to have sex, but never had a woman come onto me as strong or aggressively as B did.  I don’t think this changed how I feel about casual sex or sexuality, but I felt a lot better about myself after this happened.  Being honest I had moped around for a few months since my last girlfriend had dumped me and it was only after I had sex with B that I really was ready to start seeing someone else.

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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