by Ian

Gender: Male
Age: 51
Race/ethnicity: Caucasian
Location: US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Educator
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? Dozens
How many hookup stories have you here posted before? 0

Serendipity

How long ago did this hookup happen? 16 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…)? 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? She was/is a co-worker, but not one I see every day. We worked in different buildings, so I had never met her until we both attended an after-work social function, where we discovered we had some strong interests in common. We became Facebook friends, and occasionally my wife and I would join her and her husband for drinks at their house. She is good-looking, but it is her personality that is the real attraction. She is the life of the party and the center of attention wherever she goes. At first, I was just intrigued to learn I had a co-worker that had so much in common with me, but the more time I spent around her, the more I wanted to imagine other possibilities developing between us. She exudes a latent sexuality without even trying. It would be fair to say I had developed a crush on her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I knew from a FB post that her husband was out of town for the week. I didn’t really expect anything, but on a whim emailed her about dropping over to their house for a drink after work, not revealing that I was aware she was solo. We’d done this several times as couples, so it was not an out-of-line suggestion. To my surprise, she agreed almost immediately and suggested a time to arrive. I had no serious expectations that it would involve anything other than a couple of drinks and some conversation, but of course harbored the fantasy that it might go further.

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? When I arrived at her house, she had obviously just gotten out of the shower (her hair was still wet), and she had changed into casual clothes. As I followed her downstairs to their basement bar, her tight jeans, wet hair, and bare feet had my imagination revved up.

Predictably, a few drinks loosened our inhibitions and the flirting began, but I wasn’t really picking up some of the obvious signals. We soon were on the sofa, exchanging foot rubs, and it finally dawned on me this might be going somewhere. She asked me to rub her back and shoulders, and lay down with her face in my lap. When she sat back up, I threw caution to the wind and moved in for a kiss. Neither one of us had spoken about what we wanted, afraid it might not be reciprocated, so it was something of a risk. But she responded hungrily, our tongues deep in each other’s mouths. That was all I needed. In an instant, I had her pants off (no underwear!) and was going down on her, kneeling on the floor in front of the couch. After she came, still kneeling on the floor, I pulled her hips forward and slid my cock into her. The passion between us was incredible. We reversed positions, with me sitting on the couch and her straddling my cock, sliding up and down. She came again and dismounted, kneeling to take me into her mouth. Best oral I ever had, she had mad skills. I quickly came, and she swallowed it all. We cuddled for a bit on the sofa, discussing our mutual surprise and delight at the developments. Ironically, she had been harboring the same fantasies about me; if I had only known, I would moved much sooner. Soon recovered, we fucked in several more positions on the sofa and floor. It ended when my phone beeped with a text from my wife asking when I was getting home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We never discussed STIs. We’re both married, and I haven’t been with anyone else in a long time, so I knew I was safe; I just assumed she was too. As I was getting ready to enter her the first time, she cautioned that she wasn’t using birth control and offered to get me a condom. When I explained I’d had a vasectomy, she relaxed.

What were your REASONS for having this hookup? A virtually sexless marriage, a raging libido, and we were mutually attracted. Completely coincidentally, her reasons were exactly the same.

Were alcohol or drugs involved? If so, how much? Yes. I had a few beers, and she was drinking shots of whiskey, but we were just buzzed, not wasted. I would say the alcohol lowered our inhibitions enough to embolden us to make the first moves, but we both wanted to long before the first drink was taken.

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? This part is complicated. She is, she admitted later, promiscuous by nature and in practice. She travels occasionally by herself or with girlfriends to sporting events she participates in, and often hooks up for one-night stands while she’s away. (Had I known this, I would have insisted on the condom.) We agreed to continue as fuck-buddies when the opportunity arose, but she made it clear she intended to continue hooking up when she’s out of town. This had led to no small amount of jealously on my part, which she does not tolerate, so I have to stifle those feelings around her. I’m deeply attracted to her, but forced to maintain a fairly shallow relationship. When she wants sex, we get together, but otherwise we’re just friends and co-workers, and she continues to hook up with others when she pleases.
Despite these shortcomings, it’s worth it for the hottest sex you can imagine. About once a month, we arrange a real “play-date”, borrowing her friend’s house. With a dose of Viagra, we can fuck for literally hours, and do. She seems to have no limits on the number of orgasms she can have. Other times, it’s completely spontaneous and impulsive. We’ve fucked in the woods at a park, in the corn field behind my office, in the supply closet at her office, in the bathroom at a restaurant. When she’s in the mood, she’s insatiable.

To whom did you talk about the hookup? How did they react? No one. I have no one to whom I could confide this. Finding this site, allowing me to finally share this story is a huge relief.

Was this a consensual and/or wanted experience for you? For your partner? Completely and mutually consensual

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? The quality of the sex, and the opportunity to be with someone to whom I’m so completely attracted.

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

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

Anything else you want to add about this hookup or anything else? The only negative was learning she had, and continues to have, other partners.

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