by MidAgeGuy

Gender: Male
Age: 56
Race/ethnicity: Caucasian
Current location: USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Technology Manager
Relationship status: Married
Religious affiliation: Non Practicing Catholic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 0

Company Friends

How long ago did this hookup happen? 2 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…)? 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? I worked with this women in my company mostly via teleconferencing since she was at another office location in another state. I liked her voice on our teleconferences. Funny thing is that is the same with many women that I eventually developed relationships with. We finally met at company conference that was at a location away from both of our home locations. When I first saw her she was very friendly, I was a little flirty but more friendly, she asked if I had plans for dinner, that I should join her group of people for dinner. I agreed and she said to meet her in the hotel lobby at 7pm. When I met her in the lobby she was alone, I asked her about her other colleagues and she said that they were tired and changed their minds. Looking at her she had completely change her outfit to a tight pair of jeans, sweater an high heel shoes. She was tall statuesque and dressed this way I could tell that she had a very nice set of breasts probably C or D cups. My wife is smaller with an athletic build with small breasts and a nice heart shaped bottom. I normally prefer average to petite women, I find them more feminine.  I am not a prude by any stretch of the imagination. I have been married twice with many girlfriends and lovers in between but as we started walking outside to the restaurant, I started to realized that this was not just a business dinner, there was sexual tension in the air. We waited outside a restaurant on the patio for a table. it was cold so we huddled around an outdoor heater and started to talk. I asked her what she wanted to talk about, she said that did not want to talk about work, that is when I knew that I was the prey :-)! She explained that she had been married young and was now divorced and did not have any children. She was about 10 years younger than me. She had an older boyfriend but had no plans to get married again. I explained to her that I was married for second time, for the most part happy but my wife could be emotionally distant at times, especially when she pre-menopausal. I did not discuss this at time to this women but my wife likes pretty strait sex, she will give me oral but won’t let me finish in her mouth. She also doesn’t like any ass play. We finished dinner and in the cab ride back to the hotel I could tell that she wanted me to initiate something but because we were heading back to a hotel full of our colleagues I was concerned that someone would see us and did not want the controversy. We said good night with a handshake and I think I said something like if I was not married this might have ended differently.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to keep in touch and then I had a meeting at her home office and we met again for dinner. We talked even more openly and she then disclosed to me that her current boyfriend wasn’t meeting her needs. After dinner we went to her car and started kissing. I normally try to get to a women’s breasts first, but with outfit she had one it was a non-starter. Since she was wearing a skirt I slipped my hand up her skirt between her panties into a very wet vagina. I then was able to slip one of my other fingers in her bottom at the same time and she really like it. I asked her to come back to my hotel room, she said that she wanted but her boyfriend was at home waiting for her.

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? The first time we met in a hotel room and started kissing on the bed. She walked in the door and we went strait to business. I unbuttoned her blouse, she unclasped her bra and these large beautiful breasts popped out, D cup with big aureoles, my favorite. I like big aureoles. We undressed and she started kissing my body starting at my face and she worked her way down to my penis. She said that she wanted to perform oral but I had to put on a condom. This was a first, while I have used condoms many times including with my wife but not for oral. As this decreased stimulation it took a little for me to get hard. To be honest I did not like it at all. While she was performing oral on me I was sliding one finger in her vagina and another in her anus. I knew that she really liked this and this helped to get me going.  I eventually got hard and then she climbed on top and inserted me inside of her. I sucked on her pendulous breasts and she rocked up and down until she orgasmed and then I did. She was much more verbal and was more enthusiastic than my wife.  We took a break had a glass of wine and then we cuddled naked, this is when I realized that I was missing this affection with my wife. We talked and she explained that her current boyfriend that she lived with was not as sexually adventurous as I appeared to be and only had sex maybe once a week which was not enough for her. She said that like anal sex and that if I wanted we could do that next. I said that I was tired and probably could not perform again. After a while she started kissing me and took my penis back in her hand. I performed oral on her sticking my fingers in her vagina and anus. She moved down took my penis in her mouth without a condom and started sucking on it. She was very sexy, she wrapped her pendulous breasts around my penis and sucked on me at the same time. I did not get fully hard but still she eventually sucked me to an orgasm and I shot in her mouth and swallowed my load, I liked that.  She had to go home to her boyfriend, so she rinsed off in the shower got dresses and left.

The second time about a year later I was traveling for work again. We met at my hotel. Since this was the second time we were more relaxed sexually, except that she was more concerned that her boyfriend would find out so we did not have a lot of time. She kissed me all over my naked body again ending up at my penis and sucked on me without a condom this time. She climbed on top again and rode me with vigor. We switched to the missionary position, I asked her where she wanted me to come. She said that I could come in her vagina, anus or mouth, whatever I wanted. I told her that I didn’t want to have anal sex today, I have done it before. I prefer coming inside a women’s vagina but I was concerned about her getting pregnant. She again reminded me that she was not capable of getting pregnant, this was verified by her Doctor and years of sex with ex-husband and current boyfriend without getting pregnant. So I pounded into her hard, that is what she wanted, she had her arms and legs wrapped around me pulling me into her she orgasmed and then I did. We rested a little and then she performed oral on me again. I didn’t think that I could come again, but she did the breasts thing again and was very enthusiastic. I shot my load in her mouth and she swallowed all of it again, I liked that. Again she had to hurry home to her live in boyfriend.

Did you have an orgasm? Did your partner(s)? yes and yes

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She was very concerned for our first meeting. I had a job where I had a medical exam every year including HIV because I travel internationally, so I knew I was clean. She insisted that we use condoms the first time including when she performed oral on me, that was a first. The second time we didn’t use anything, I was more concerned about pregnancy but she said that she was incapable of having children. She had unprotected sex with her ex-husband and now boyfriend for years without getting pregnant.

What were your REASONS for having this hookup? I like sex, I like sex with my wife and I like sex with other women that I find attractive. To me it is like eating steak every night for dinner. It is great but you might want something different from time to time. This other woman is also much more physically affectionate than my wife. I did not realize this until after our hook-ups. This is probably why I did it more than once. While it may seem selfish, overall I love my wife and I wouldn’t leave her for another women.

Were alcohol or drugs involved? If so, how much? No drugs, a couple of glasses of wine at dinner, we were not impaired.

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 like this person, she is affectionate, intelligent and worldly as well as liking the things that I like sexually. We live pretty far apart so we can only get together on rare occasions. if we could meet again without risking our current relationships or jobs, yes I would do it again.

To whom did you talk about the hookup? How did they react? No, I don’t have many close friends or family. It is also best kept secret.

Was this a consensual and/or wanted experience for you? For your partner? Yes it was 100% consensual.

Do you regret this hookup? If so, why? The only thing I would regret is for either of our partners to find out.

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 the hook-up is that there is someone else besides my wife that finds me sexually attractive. My sexuality has always been a big part of my life. While I am healthy and in good shape for my age, I work out every day and am in better shape than many men 25 years younger, I know that I am not a young man anymore.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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