Age: 29/19 Then
Location: Medford, OR
Highest education received: College degree (eg., BA, BS)
Occupation: Regional Manager
Relationship status: In a Committed one
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? None
How long ago did this hookup happen? 10 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…)? Employee 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? Tanya was an older woman, at least to me then since she was 35 and I was 19. She was a leggy blonde, fit and with a big chest. She was a manager at the store I worked, one of several I actually reported to. I thought she was decent looking but with the age difference I had no sexual interest or attraction to her, and she was married with two kids.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In college I worked a stint at a supermarket in town to cover my bills, full time in the summer and part time when I had classes. I had worked there about a year when we started, and had been involved with two other coworkers. First was a girl my own age who worked the soda counter (ironically enough we got back together two years ago and are currently involved and living together) and a checker in her thirties who was single.
Tanya was having some marital problems, that was no secret. I would later learn her husband was on a medication that killed his sex drive and he hadn’t touched her in more than a year. One afternoon Tanya called me to her office to discuss an issue I was having with another coworker, one I had gone out with a few times but had broken it off but who was pretty much sexually harassing me.
Tanya asked what she had been doing, and I told her she had flicked my cock a bit. Tanya did the same, and then stuck her hand down my pants and stroked it a bit. I ended up kissing her, and clearing off some space on her desk and putting her on there. I started unbuttoning her shirt, feeling some major lust, but Tanya stopped me and told me not here.
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 the house where I was living at the time after work. We were in my bedroom and Tanya asked if I wanted to undress her. We started making out and I did slowly, taking her shirt and bra off. Her body was near perfect, toned with c cup breasts. I licked and played with her boobs a bit and then took her pants off and laid her down on the bed. She gave me oral for a bit. I penetrated and rode her, she actually orgasamed first and then I did. We made out a bit more and then cuddled for a while until we fell asleep.
Next morning Taya was gone when I woke up but she left a note with a lip stick impression and said to call her.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t discuss it but I used a condom that first time
What were your REASONS for having this hookup? Pure lust that first time
Were alcohol or drugs involved? If so, how much? Not at all
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? Tanya and I were together for about eight months. During lunch we would sneak to a nearby hotel and she would come over nights once and a while or during the day on our days off. We also fucked in her office a few times. Keeping it secret was kind of hot and I will admit I developed some very intense feelings for Tanya and I think I was in love with her. For her though it was an affair and she would never leave her husband no matter how she felt about me. Part of me felt guilty and always has for going near a married woman.
Her husband went off that medication and his sex drive returned and Tanya broke things off with me. I ended up quitting my job, as a better opportunity came along anyway and having nailed three women at the same store was making things very awkward. I saw Tanya recently and we were polite but there are still some issues between us.
To whom did you talk about the hookup? How did they react? As Tanya was married and still is I have always kept this quiet. My roommate knew, as it was his house. He judged me a bit for the age difference but other than that never really said anything. My current girlfriend also knows about us, she had suspected back then as we still worked at the same place after we broke up. She was a little surprised that it was actually true as there were rumors apparently but she understands we both have history we are not proud of.
Was this a consensual and/or wanted experience for you? For your partner? Yes for both of us.
Do you regret this hookup? If so, why? Two big regrets here, first is going near a married woman. To me that has always felt wrong and not a mistake I have repeated. My other big regret is Tanya had a daughter about seven months after we split up. She insisted that she is her husband’s but I have never been so convinced as they were not sleeping together then. Back then I was very young and did not want to deal with having a child so I did not peruse it but when I ran into Tanya recently I thought about how much the girl looks like my sister had at nine.
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 sex with Tanya was great and often, worst part is the guilt I have always felt about fucking a married woman and the possible kid out there. Past few months I have been strongly reconsidering forcing the issue of a paternity test even if it would end Tanya’s marriage. My girlfriend has actually been very supportive of the idea, she says I need to know.
After Tanya and I split up I quit my job. As rules now I stay away from married woman and coworkers, neither of which is worth it. However without my relationship with Tanya I think there were others I never would have perused or even approached the idea with.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? Somewhat negative
You have a hookup story to share? Submit it here!