The Affair



What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Mid Atlantic USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 1

The Affair

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? Abby had been working for me for about 6 months. She was younger then me, very pretty, and had a nice body. I was 35 years old and she was 25. She worked for me, but in a different part of the building. In a normal circumstance, our positions should only see each other 1 or 2 times a day, but Abby would often end up in my office or at my end of the building multiple times a day. She was great at her job and I thought she had potential to grow with the company. As time went on, we began to get to know one another a little. I knew she was single but that she dated occasionally. She was very open about herself and was always willing to talk. She also asked a lot of questions about me and my life outside of work. She knew I was married with one kid and two dogs. She knew I liked sports, camping, and fishing. We became very friendly with each other but I kept it professional for the most part. I say for the most part because we did joke around a little and did talk about some personal stuff at times, even sex. Come to think of it, maybe not all that professional.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After she had been working for me for about 3 months, a project came up that put us working side by side for about a week. Most days we had to work into the evening a little bit. My wife was used to it and came to expect it. I let her know I would be late coming home all week. Abby and I were often the only ones left in the office after 5pm with the exception of maybe one or two other people, but they were busy on their own projects and not in the rooms we were in. This is when we really began to get to know each other. Work was going on, but it’s the type of work that didn’t require a lot of thought, so we could talk pretty freely and still get done what was needed. She was younger and so pretty she could have any guy she wanted. I didn’t think for a second she would be interested in me, especially with the complications of me being married with a kid and 10 years older. The last couple nights of the week she began to ask probing questions. She brought up sex, often in a joking or flirty way. Again, I wasn’t really picking up on these signals she was sending. Not even when she began touching me frequently on my hands, arms, back, even at one point pinching my ass. I was oblivious to anything other than this being good natured fun, trying to pass the time away until we finished the project.

On the last day of our project she asked if we could break for dinner as most of the office cleared out for the day. We hadn’t done that and usually just worked through. I agreed and we went to a place right down the street. During our meal she asked me if I had ever been unfaithful to me wife. When I said I hadn’t she asked if the chance presented it self would I? It started to hit me… She wants something to happen between us. We continued to talk but I was still trying to come to grips with where this was leading. I replayed some of the things that had happened during the week. I thougth to myself maybe, but then again maybe I am misreading this. I tried to play it off. I told her that I wasn’t interested in being unfaithful to my wife. Yet I couldn’t think of anything else now except what it would be like to be with her. We managed through dinner and went back to work. At work we wrapped up the project quickly. We continued to talk but she was a little different. She was not as eager to talk as before, but we still managed to carry on a little conversation. I couldn’t stop thinking about her and I was definitly beginning to look at her in a different light. She was smoking hot and I wanted her in a bad way, but I couldn’t. As we finished and were walking out to our cars. I was relucant to say goodnight so I tried to keep the conversation going. Small talk was getting old and soon we were just standing there looking at each other. Finally, I said I wasn’t sure what was going on between us. She said she wasn’t either, but it didn’t matter because I am married and nothing can happen. She said maybe if things were different. We said good night and left for home.

All weekend I couln’t stop thinking about her. The following Monday I found myself making excuses to be at her end of the building. She seemed pleased that I was starting to show interest in her. A couple of weeks went by with some days seeing each other fairly regularly and other days work keeping us at opposite ends of the building until one day we had a chance encounter behind the building. She was coming in from putting something in the storage building and I was checking one of the company trucks. She met me with a huge smile as she turned the corner and saw me. I was excited to see her also. We talked for a minute between two of the parked company trucks. We stood closely to each other. Then I kissed her. My heart raced. She kissed me back passionately and eagerly. It was fairly short, but at that point I knew where it was going. It was midmorning. She asked if I wanted to meet for lunch. I agreed instantly. Time could not move fast enough. At 11am I nervously pulled out of our lot to make the 5 minute trip to where we were meeting. I pulled next to her. She rolled the window down and told me to get in. As I did she pulled off driving us to a nearby park that always has people walking or jogging but also has some secluded places where we could park in realitive privacy.

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? As soon as we parked, we had our hands all over each other. We kissed deeply. Within a couple of minutes I had my hands on her breast over her shirt. I squeezed them and caressed them. She placed her hand in my lap feeling my fully erect cock straining against my pants. Pulling away for a second, she unzipped my pants and freed my cock. Quickly, she leaned in taking my entire lenght in her mouth. She worked up and down my cock until I felt ready to explode. I stopped her, leaning her back in her seat, unbuttoning her pants,, and pulling them down enough to get my hand between her legs. I could feel the heat before I touched her. She was dripping wet. I rapidly found her clit and began to tease it with my finger. Very quickly she began to shudder and moan as I brought her to a climax. She then opened her door, said come on, and moved to the back seat. I followed and before I could shut the door behind me, she had her pants off and was pulling me between her open legs. I wasted no time finding her hot wet pussy with my cock. I thrust into her several times. It felt almost like I was a virgin again as I came very quickly, pulling out and shooting my cum on her stomach and chest. I hadn’t seen that much cum come out of me in years. We had not talked about birth control so I had no idea if she was on the pill or not, but I didn’t want to take a chance. I came so quickly I almost didn’t even think about it.

We quickly got dressed and looked around and realized that people may have seen us, but we didn’t really care either. We quickly made it back to my car and back to work. After work, we met again, but this time we went to her place and fucked on her bed. It was wildly passionate. I lied to my wife telling her something came up and work so I would be a little late. So began my year long affair. It was full of amazing sex, painful guilt, exciting encounters, and heart breaking loss. My marriage, which was starting to crack before this, began to disintergrate. Fastforward 2 years later I was going through a divorce. Fastforward another 2 years and Abby and I were living together. We have now been married for 8 years and are deeply in love.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I was excited and scared. I didn’t know what this meant; if it was a one time thing, if it would affect my marriage, work, or turn into something else. I was on an emotional rollacoaster for well over a year. It did end up affecting my marriage and work. I eventually I got a divorce. Rumors began at work eventually causing Abby to take another job. I am not proud of what I did to my family. It was hurtful and damaging to my daughter. At the same time, it did lead to something good. Once the divorce was final, I was able to have a normal relationship with Abby and we fell in love. We are happliy married now and have a great relationship. I don’t blame my ex wife for the failure of my marriage, that was on me, but I don’t think either of us were truly happy at the time. Perhaps we would have worked through it, but that was not the path we took. She has remarried and we have a pretty decent relationship now. She knows that I cheated on her, but not who I cheated with. My ex and my current wife have very little contact or relationship. It’s not a negative relationship, they just don’t interact much. My daughter adapted well, but it was difficult on her at the time. We have a very good relationship now and she does with her mom as well. She doesn’t talk about that time of her life much. She gets along well with Abby, I wouldn’t say they are close but they get along fine.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, To feel more confident

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Initially no one. Durning my seperation I confided in my best friend and his wife. They were supportive. They cautioned me about what could happen, but at the same time they didn’t care for my wife at the time so they didn’t judge me for it.

I also have an older brother and sister that I have talked to about this. They also didn’t like my ex wife so they weren’t surprised. They love Abby and really can see the positive impact she has had on me.

Oddly enough, my ex father-in-law. We always had a good relationship. He flat out asked me once right after I seperated with his daughter if I was seeing someone else. I confessed to the affair. He was a little angry at me but was also not surprised. He had several marriages including affairs so he wasn’t going to hold it against me. He told me it wasn’t his place to tell anyone. He encouraged me to continue to talk to him because I would always be family to him. I don’t see him often anymore, but when I do it is as if nothing ever happened.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Somewhat

Why do you regret this hookup? My biggest regret is how it hurt my daughter. She was 12 when it happened. Our divorce was hard on her. I also regret hurting my ex wife. While we were starting to have problems before this happened I don’t blame her for it. It was my doing. I don’t think we would have made it much longer either way but it was still hard seeing her hurt. I did still care for her.

What was the BEST thing about this hookup? I found my current wife and the love of my life. She has helped me find peace and happiness. The sex was amazing. It was like my first time again with the passion and excitement.

What was the WORST thing about this hookup? As I already said… the break up of my family, paricularly my daughter having to go through it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I would never cheat on a partner again. Of course before this I probably would have said that as well. But having lived through it, seen the hurt and damage it caused, I couldn’t do it again.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Abby and I are really happy to have found each other. We have a great, loving relationship. We also know that we didn’t do it the right way. We both have regrets and are ashamed of our beginnings. We typically don’t tell people the truth about how we met or got together. Our closest friends know but that’s all. We try not to talk about it even with each other.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? There is nothing wrong with two (or more) people engaging in what ever consentual sex they want. I will never judge. I just think everyone should really think about consequences before they act.

What do you think about the Casual Sex Project? Great place to share.

You have a hookup story to share? Submit it here!