by Sky

Gender: Female
Age: 38/31 Then
Race/ethnicity: White
Current location: Columbus, OH
Highest education received: College degree (eg., BA, BS)
Occupation: Personal Trainer/Physical Therapyst
Relationship status: Committed
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? A Few

Been a While

How long ago did this hookup happen? Seven 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…)? 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? Abe was a tall African American man, muscular with a goatee and very dark skin.  He was in his mid twenties, the younger brother of a woman I was working with at  a bank.  We had met at her birthday party a few weeks prior.  We had started talking and I found him a little shy but quite charming and he really seemed to listen when I talked.  I didn’t think he had too much experience when it came to the opposite sex.  I found myself quite attracted to him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A little background, I had broken up with my girlfriend of over six years Brandi (see Brandi) a few months prior.  It had been quite brutal and difficult for both me and my son so I was hesitant to go near anyone for a while.
I liked Abe when I met him and we had gone out to dinner a few days before on what I consider a date.  There was a lot of talking and some flirting and we did kiss, but I could tell he was really nervous.  He asked me to meet him for drinks that Saturday.
Now when I want someone I tend to be quite forward and even a bit aggressive about it.  I went to the spa and got waxed, put on a thong and a lace bra.  I selected a tight pair of jeans and a buttoned shirt and left enough buttons down that I showed plenty of cleavage.  I went there that night with every intention of sleeping with Abe.
He was a little surprised by how I was dressed but we went in the bar and ordered our drinks and went to a booth in the back. As I said he was shy so I had to put the moves on him, some casual touching and whispering in his hear and some kissing.  I got a little more forward and stuck my hand down his pants and stroked his cock a bit, god did he look shocked.  I brought his hand to my breast, he had been staring at them all night, and asked if he liked what he felt and he said yes. I leaned forward and whispered in his ear “I want to fuck tonight.”
We ended up in the back seat of his car where we started to make out.  My shirt was open and he had his hands on my waist, we would have fucked right there but another couple came out of the bar and spooked us.  We were both quite horny and made the decision to go back to his place as it was only about ten minutes away.  I remember he was all over the road since I had my hand down his pants the entire time.

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 can remember being very nervous, I hadn’t been with a man in nearly seven years.  As aggressive as I was with Abe I may have been overcompensating a bit.  We ended up in his bedroom and making out on his bed and there was a lot of foreplay.
He slowly took my clothes off, touching and kissing me all over as he went.  He asked about my tattoos as each came with a story.  He struggled with my bra a bit but I talked him through it.  He had me naked and I pulled his pants off and we made out naked for a while.  He was quite fascinated with my breasts and played with them quite a bit and sucked on them.  I got tired of waiting and mounted him, and rode him in cowgirl until he finished inside me.
We cuddled for a while and I told him that I was bisexual and hadn’t been with a man in a long time, he was a little weirded out by that.  He told me that he had only ever been with one other woman, a girlfriend he had split up with over a year before confirming my thoughts that he was not very experienced and he said the sex had been pretty mild.  We chatted for about an hour before going again.
Second time Abe was on top.  It took some coaching and instructing from me, but he was eager and willing to learn and we both orgasmed in near unison.  I was a little surprised and Abe said he had never had a woman orgasm.  We fell asleep soon after.
In the morning I woke Abe up with a blow job.  My oral skills on a man were a little rusty, still I sucked his cock and licked his balls a little and was able to get some loud moans from him.  Abe finished in my mouth.
I rinsed my mouth out and Abe and I showered together, a lot of kissing and touching but no sex.  I got dressed and kissed Abe goodbye.  He said he had no idea women could be that into sex as I was leaving and I told him I had quite enjoyed myself.

Did you have an orgasm? Did your partner(s)? I did the once, Abe did all three times.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Now I let Abe finish inside me twice but I had just gotten out of a monogamous relationship and Abe had only been with one other person so we did discuss it.  I also had gone back on birth control shortly after my breakup with Brandi.

What were your REASONS for having this hookup? Mostly I wanted to and was really horny.

Were alcohol or drugs involved? If so, how much? I had one scotch and Abe one bourbon, not much each.

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? Abe and I casually dated for about six months, nothing too serious as I was not ready.  We went to dinner, the movies, normal couple stuff.  We also had a lot of sex and Abe got very proficient at pleasing me and the next woman owes me big time.
Now Abe really liked me, thinking back he was probably in love with me.  He wanted to get serious but I was just not ready and we split up.  It would be several more years before I was in a serious relationship.  I did however really enjoy my time with Abe.
As for a future with Abe, we split up over six years ago and I have been seeing the same guy for more than two years.  I am still in contact with Abe’s sister and heard he is now married with two young children.

To whom did you talk about the hookup? How did they react? I never really told anyone about this, however Abe’s sister caught us in bed a few weeks later.  I don’t think she was too surprised with me but she was shocked at Abe’s behavior.

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? Very enjoyable sex with someone I really liked, as for the worst part I would have to say it was my unwillingness to allow this to become any sort of serious relationship.  I don’t think this changed how I think about casual sex or sexuality, other than Abe was the first man I was with in seven years.

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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