A Blast From the Past & a Surprise

by Nathan
Gender: Male

Age: 44
Race/ethnicity: Black – African American
Location: Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Finance
Religious affiliation: Spiritual, not religious
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0


A Blast From the Past & a Surprise

How long ago did this hookup happen? 4 years ago

How would you best classify this hookup? Friends-with-benefits

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? She’s beautiful. We’ll call her G.G. She had/has chestnut brown hair that hangs below her shoulders. Greenish-brown eyes with very kissable lips. Great smile and a fantastic personality and body. She’s one of those women that you would think would be really stuck up but she’s incredibly down to earth. I knew her in college. She ran with a group of Jewish girls from the general NY metro/CT area. I called her the undercover hottie. IMO she was the hottest of the girls she hung out with but for some reason she never really made the effort to stand out. She was cool grungy before it was cool to be grungy. (I later learned why some of this was, BTW.  Stay tuned…) We knew each other in college and hung out. Two years in, it was pretty well known that I had the hots for her but she came from a strict Italian family. Nevertheless, on the first day of school for Jr. year, there was a note on my door from her saying she was looking forward to seeing me and asking me to come by her place that night. Well that never happened. That Summer I met a girl on Cape Cod and we were hot and heavy by the time I got back to school. I was in school in Boston so my GF was there all the time even though she still lived at home on the Cape. I would see her on campus all the time and our relationship was not the same. Even some of her friends were cool to me but we were still attracted to one another.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After college, somehow we remained friends. She was living in New England and with me still being in Boston, we met up a couple of times and just hung out. She moved to NYC and we continued to stay in touch. We began talking a lot, texting, talking on the phone and I learned some interesting things about her. Like in college she was gender confused and considered herself to be bi. Now years later when we were speaking and texting on a regular basis, she was in a long term relationship with a woman who she loved. I was living with my current girlfriend and was engaged to be married. Two years later I was married and G.G. and I continued to talk once in a while. She was still in the relationship with her GF but it was clear that there were unresolved feelings between the two of us that went all the way back to college. She admitted that she wanted to cross “sleeping with a black man or woman” off of her bucket list. I had business in NY and we met for dinner. This was our second time having dinner together in the city and this time we went for drinks afterwards. We hung out at a bar downtown and by midnight we were out on the corner kissing each other like I hadn’t kissed anyone in forever, it felt. I have to admit, I was VERY turned on by the fact that she hadn’t been with a man in over 13 years and that this was something that was long overdue.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We ended up back at my hotel, where we got out of our clothes and I went down on her right away. It was phenomenal. I imagined that it was what it must be like to go down on a virgin. I love to give oral but I just wanted to dive all the way in. She climaxed and I just kept going. I was so turned on but at that point she pushed me off and went down on me. It was if she had tasted sugar or something for the first time. She was slow and deliberate and really enjoyed licking and holding me in her mouth. I came and she never considered removing me. We had sex three times that night. The positions were mostly face to face and we kissed during lots of it but she was really into positions that allowed me to get as deep inside her as possible. She said it hurt a couple of times but that it was a “good hurt”.  We didn’t use protection. That was VERY stupid but she was certain that she wasn’t ovulating. She came each time and I came twice during sex and once during oral. She was good. Passionate and physical and open.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We had discussed history and neither of us had anything in our pasts.

What were your REASONS for having this hookup? Unfinished business and mutual continued attraction.

Were alcohol or drugs involved? If so, how much? Some drinking but we were nowhere near drunk. We knew what we wanted to do before we finished dinner that night.

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 continued to speak for a bit but we haven’t hooked up again. I felt good and bad about it. I love my wife very much so there is guilt regarding that but it doesn’t haunt me. I would probably do it again if she would too, mostly because we both believe that there could be no future “us”. She is still with her GF.

To whom did you talk about the hookup? How did they react? I told a couple of friends. Being typical guys they were hyper focused on the fact that I slept with a woman who is/was bi but describes herself as a lesbian.

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

Do you regret this hookup? If so, why? Yes and no for the reasons explained above.

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 thing about this hookup was that it was everything I wanted it to be when we were in college. This hook up did confirm for me that casual sex is not going to blow up my marriage in any way. I guess as long as my wife doesn’t know…. 🙂 But I guess if my wife had the same experience and it was a one time thing, I could have a level of understanding about it.

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

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

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