Beginning Of A Years Long Affair



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10ish
How many hookup stories have you here posted before? 0

Beginning Of A Years Long Affair

How long ago did this hookup happen? 6 years

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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 had worked with Karen a few years professionally. I thought she was cute but there was nothing sexual between us. I thought she was a bit overweight, frumpy and could have done better for herself. We were both married (and still have the same spouses to this day) and she had a second child then began really taking care of herself and looking incredibly sexy, hitting the gym, eating clean, etc. She had that Southern Belle charm, sweet, innocent, motherly. We worked closely together and she had this vibe that told me she found me attractive. She would smile at me with these amazing big brown eyes and her figure that morphed into a smoking hot body. She would stand close to me when she had a question and our bodies would touch and it drove me nuts. I was very nervous to have the chat with her about our mutual attraction since we worked so closely together and I didn’t want to ruin what we had. She actually seemed surprised at first when I sat her down privately in my office and asked her if she felt we had become attracted to each other, probably since we were both married. She didn’t really know what to say but came back to my office the next day and admitted she was really attracted to me and that her husband just didn’t know how to satisfy her and we should give this a try.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to meet up after work one day in the back of her minivan since we had no place else to go. We work in a suburban area, it was dark early evening during in the winter, so we drove to find a secluded parking spot at a nearby apartment complex. We parked next to each other and I hopped in the back of her van where she joined me. We were both nervous as hell to start but we couldn’t wait to play with each other.

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? We sat on the back seat of her minivan and finally got to hold and kiss each other. She was an amazing kisser and we both relaxed with each other right away since it felt like there was so much chemistry between us. At first I was reluctant to explore her with my hands- didn’t want to go too fast for her but she encouraged me by telling me it was OK to touch her. I unbuttoned her sweater and raised her shirt while sliding my hand under her bra. Her petite breasts loved to be touched and her nipples were hard already. Lightly rubbing and pinching them nearly brought Karen to her first orgasm. She was wearing a knee length wool skirt with black tall leather boots which itself was a turn on to me. I hiked up her skirt and revealed a lacy purple thong which was already soaked. I slid the front of the thong to the side and easily slid my finger inside her. She arched her back and moaned with her eyes closed and mouth wide open. After circling her hard clit for awhile she was so turned on that she grabbed my hard cock through my pants and told me she had to have me. She slowly unzipped my pants and got on her knees between the seats and proceeded to slowly and erotically lick the shaft of my cock while looking directly into my eyes. She took as much of me in as she could a few times then practically begged me to fuck her. I switched spots with her, having her sit in the middle of the back row of her van, legs spread open. She help me slide on a condom and I was on my knees facing her between the second row of seats while I gently slid my rock hard cock into her soaking wet pussy. We went slow at first, I open her sweater more so I could pinch her nipples and at times lean forward to kiss her and suck her breasts which she loved. She asked me to take her from behind so she got on all fours facing the back corner of the van. I easily slid deep inside her and began fucking her harder. She has a perfectly round ass with a really narrow waist and cute, perky tits with lively nipples. My left hand was right where her thin waist meets her ass and I loved the side of that ripple in her ass moving forward as I thrust harder. Her shoulder length brown hair was getting in her eyes so I took that hand to hold it back for her and found myself gently tugging on her hair. She yelled out “Harder, pull my hair harder!” which I had never done to anyone before but loved the look of pure ecstasy on her face as I pulled her head back a bit. As I did this my right hand instinctively gave her right ass cheek a gentle slap as I grabbed a handful of the most perfect ass I have ever had in my hand. “Harder! Slap my ass harder!” she screamed. I was definitely in uncharted territory so I was hesitant but with each slap with an open hand on her right butt cheek she moaned yes and asked for more so I escalated a few ass slaps until it seemed like any more would really sting. At this point I was fucking her deep and hard while being completely turned on by sight and sounds of her being taken. We both got louder and totally in sync as I told her I was cumming and I think she did multiple times during the meetup. We collapsed in the backseat together for awhile, cuddling and laughing a bit about how we did not know how incredible of a lover the other was.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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’ve never felt so alive in my life. We both felt the same way and became lovers, sneaking off when we had the chance, sometimes in the back of her van, other times in one of our homes when families were away. Sometimes she would walk into my office during work, close the door, get on her knees and blow me right there. As crazy as it sounds, her husband thought it was gross to cum in her mouth and my wife won’t let me cum anywhere near her mouth. Karen was always eager to have me blow a load in her mouth so it satisfied both of our cravings. Within months, she declared us sexual soulmates. Our sexual relationship though turned into a loving relationship over a couple years which complicated things so we eventually ended things since it became too difficult for us to handle. We both remain married to our original spouses to this day, we now longer work together, but Karen and I still catch up with each other a few times a year to stay in touch.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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? Nobody. I never felt safe sharing this with even my closest friends since they know my wife although I came very close to telling them at times.

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? This lead to a several years long sexual (and eventually emotional) relationship with Karen. We both felt we had good family lives but were not satisfied sexually so Karen and I over the years explored every aspect of our sexuality together that we were curious about. One could, and maybe will, write many other stories of our times together. We were able to fill the void that wasn’t getting satisfied by our respective spouses. It was incredibly fun and liberating.

What was the WORST thing about this hookup? What started as a FWB situation but it became emotional and after a couple years we truly fell in love with each other. Neither wanted to hurt our respective families so we ultimately called it quits at least sexually and now just chat a time or two each year. It was painful emotionally for both to disconnect since we both feel so connected to each other.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I wish I had the opportunity to have more casual sex with more partners but my wife isn’t into that scene which I respect. Karen and I have discussed if we were together would we be swingers or have more open relationships with others- probably so.

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? While we no longer say it out loud, Karen and I developed deep feelings for each other and both know that it is possible far down the road, maybe even decades later, that we could possibly end up together again.

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? I wish it was acceptable for people to explore their sexuality with others without having to hide it.

What do you think about the Casual Sex Project? It’s brilliant. I have enjoyed reading and relating to other peoples stories and this was almost therapeutic for me to be able share my experience with others for the first time.

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