Location: South Central United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Healthcare admin
Religious affiliation: Episcopalian
How religious are you? Very
Sexual orientation: Mostly heterosexual
Sexual orientation/sexuality better/best: Situationally flexible
How many hookup stories have you here posted before? None
Mixing Business with Pleasure
How long ago did this hookup happen? 6 years ago
How would you best classify this hookup? One-night stand
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? This was an adventure with two men. Both were business men, well dressed in higher-end attire. One had brown hair and blue eyes, a combination that makes me absolutely melt and had an athletic build. He was someone that took care of himself and worked out on a regular basis but was not interested in taking on the look of a muscle man. The other was an average build but rather tall. The pair of gentlemen were upper level management at my former employer’s home office. I was tasked with taking them around town to meet some of the local vendors that our division worked with at the time. When they arrived at the office, I was almost instantly attracted but conducted myself in a manner befitting my position with the company.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After the tour, I was invited by the pair to go to dinner with them as a way of saying thank you. The dinner began innocently enough with conversation revolving around work and general small talk. After I had a few glasses of wine and they had enjoyed a couple of beverages each, things turned a little more personal as we had all become a little less inhibited. We talked about our personal lives and it eventually led to a discussion of sexual escapades and encounters. By this point, we were all flushed and getting excited. There was no denying the tension that had built.
I drove the pair back to their hotel and had fully intended to go home but I was invited to the room of one of them for one final drink. I was both excited and nervous about what I anticipated would be the result. I was absolutely right.
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 all went to the room and almost immediately after the door closed, one of them had his hands on my shoulders and began to rub them from behind. He then bent down and began kissing my neck. The other came in front of me and began undressing me from the waist up. His hands and mouth were on my breasts and the sucking on my nipples was the most exquisite feeling that I had ever had. He paid such attention to them that I thought I would orgasm right then. The gentleman behind me unzipped and slid my skirt down and, after undressing himself, started to finger me and rub my clit.
After we were all undressed, I lay down on the bed while one went to work pleasuring me with his mouth and I sucked the other. After I had my first orgasm, he began to fuck me with an amazing vigor while the other sat in the chair and watched. After orgasm, they traded places and I was fucked from behind while sucking the first. The encounter ended with one ejaculating on my ass and the other on my breasts.
I don’t think that I had ever felt so desirable and attractive as I did during that time. They told me how good it felt and how amazing it was. The conversation afterward was very pleasant and not at all awkward. I received a deep kiss from each of them with the promise that they greatly enjoyed the hospitality and an assurance that the next time they were in town I would be requested as their local escort. I dressed, bid them adieu, and went home with a HUGE smile on my face.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t take any specific measures against STI and pregnancy. I lost the ability to have children several years ago so that wasn’t a concern. As far as STIs, I suppose you could say that we simply took it on faith that we were clean.
What were your REASONS for having this hookup? I will openly admit, I was very unhappy in my marriage and my husband had numerous affairs over the years that we had been together but I stayed anyway. I was married at the time to a man who was very emotionally unavailable and seemed to work hard to ignore me. Sex was perfunctory and was not enjoyable. I hadn’t achieved an orgasm in years and the offer of sex with these two men who were attentive and obviously found me attractive was more than I could resist. I’m glad that I didn’t.
Were alcohol or drugs involved? If so, how much? We all had a few drinks but were nowhere near drunk. By the beginning of the actual sexual encounter, I am certain that we were all completely sober.
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? I received a few emails and phone calls from them after the encounter but I eventually left the company and we have completely lost touch. I still get very sentimental about the encounter and remember it with a smile. I had absolutely no guilt about what I had done because I had never felt so good and I honestly didn’t know that it could be that good.
To whom did you talk about the hookup? How did they react? The only person I have told is my current husband. Upon hearing about this encounter he was completely turned on. I suppose knowing that his wife can be so open and relaxed when it comes to sex is exciting.
Was this a consensual and/or wanted experience for you? For your partner? It was absolutely consensual and very apparent that we all wanted it to happen.
Do you regret this hookup? If so, why? I have ZERO regrets about the actual act. My only regret is that I never saw them again.
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 encounter was the way that it made me feel. Prior to this, sex had been something that I had to do and the pleasure was for my partner. I learned that it was okay, and even preferable if sex is pleasurable for everyone involved. Casual sex is now something that isn’t so taboo.
I suppose the worst thing about the encounter is that it didn’t happen again but in reality, that makes the memory sweeter.
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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