by Zev

Gender: Male
Age: 43
Race/ethnicity: White
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Business
Relationship status: Sort of seeing someone
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? One

Cindy

How long ago did this hookup happen? Ten 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…)? Fuck Buddies

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? Cindy was a tall brunette, fit but still curvy in her early thirties.  She also had a nice pair of DD breasts.  We had quite the sexual history that went back more than a decade prior.  We had gone to junior high and high school together but back then she had not even been someone on my radar as a sexual partner.
We ended up at the same college, the only two students from my small high school.  I remember talking to Cindy at a party second term of my freshman year, where we both got pretty drunk.  We woke up in my bed naked, clear signs we had fucked and our clothes were nowhere to be found.  I first got a look at her magnificent breasts (back then her boobs were bigger and she was a bit rounder) and she had to borrow some of my sweats to go to her dorm.  To this day we have never figured out where our clothes went.
We had sex sober a few days later and quite enjoyed ourselves.  We tried dating for about two months, but beyond our fucking we didn’t have much in common and we came from very different backgrounds so we just did not work as a couple.  However we remained fuck buddies for most of college and about a year after, we hooked up regularly when we were between relationships and had a fuck buddies type arrangement for years.  Honestly we were together more often than not, and having a reliable and regular sexual partner was great.  About a year after college Cindy moved about ten hours away and I lost contact with her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was dealing with a lot at home.  It was about a year after my first divorce and my ex wife had had our son about three months prior, and the woman I had rebounded with had had our daughter a few weeks later (see Temptation).  Two infants were a lot to deal with at once.  Work was going well though.
There had been a few hookups since my divorce, mostly one or two night stands and a few short flings but nobody I had a real connection to.  I was feeling a little lonely when Cindy reached out.  She was coming to town for an art show, heard I was single and asked if she could stay with me.  I said yes.
Cindy arrived at my place wearing a tight fitting tank top that showed a lot of cleavage and tight jeans.  She had always dressed conservatively in college so this was a big change and her intentions were clear.  We actually talked for about an hour catching up and ate a light meal, before the conversation turned sexual.

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 Cindy and I were hardly two people in their first hookup unfamiliar with each other’s likes and tastes sexually.  We started kissing and undressed, and I admired the changes in her body.  She was fitter and her breasts were smaller but I still said she looked great.  She sat on my couch and I sucked on her breasts for a few minutes before moving on to her pussy.  I ate her out for about fifteen minutes and from the loud moans of pleasure Cindy was quite enjoying herself.  After orgasm Cindy returned the favor on me and we then moved to my bedroom.  We started talking, a change for us. In college we typically fucked and then went to sleep or one of us would leave.  I asked what had happened to her breasts, they had once been the biggest of any woman I had ever been with.  Apparently they had gotten so large they were causing her back problems so she had breast reduction surgery a few years prior.
Cindy mounted me, brought my hands to her hips and rode me.  It took me a while to come this time, and I finished inside her and she to orgasamed.  We fell asleep soon afterwards, we were hardly horny twenty year olds that could fuck all night long anymore.
In the morning we fucked one more time, just in standard missionary but I was pausing to kiss her, until we both orgasamed.  Afterwards we got dressed and I went to work and Cindy to her art show

Did you have an orgasm? Did your partner(s)? We both did several times

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wanted to use condoms, two recent pregnancies with partners had left me quite paranoid but Cindy assured me she was on birth control and was clean.

What were your REASONS for having this hookup? I was lonely and had always had quite a physical attraction to Cindy

Were alcohol or drugs involved? If so, how much? I had some wine but Cindy doesn’t drink.  However she did smoke a joint saying it makes her horny.  Based on my experience with her in college I believed her

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? Cindy stayed at my place for a week and we fucked every night and I quite enjoyed myself.  We decided to resume our previous fuck buddies type relationship as she would be in town every few months for work.  There was one major hurdle, I learned from mutual friends after our week together that she was in a four year relationship.  As I said in my other posts, I like the ladies but I am not a cheater and I called her angrily.  She said she was ending things with him and did so and I decided to let it go.
We resumed our fuck buddies arrangement, sleeping together when she was in town every few months if I wasn’t seeing someone.  We both knew it wouldn’t go anywhere but the sex was great and this went on for years.  I finally broke things off with her when I got involved with the woman who would become my second wife.
I enjoyed my time with Cindy very much.  I tried reaching out to her via email and on Facebook after my second divorce but she didn’t respond.  I think things are over with her.

To whom did you talk about the hookup? How did they react? I told one friend who was a bit jealous I was having regular sex again.

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 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? Best part was I would have to say the great sex, I think the worst part was Cindy lied to me about being single, that took some getting over.  I almost didn’t see her again.  Not sure this hookup changed anything about how I felt about casual sex or sexuality, but I always felt really good after being with Cindy and after that first week with her it was the best I felt about myself following my divorce.

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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