by

What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? canada
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
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)? 20+
How many hookup stories have you here posted before? 5

Affair With a Married Friend

How long ago did this hookup happen? 5yrs

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For more than 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? She was 24yrs old, brunette hair and blue eyes, 5’1″ average weight, 32F breasts, a nice bum, had one child and was married. I’d known her close to 10 yrs, she had dated my friend back in the day and although we were close nothing ever came of it. After they broke up, she eventually got married at 19 and we lost touch.

Fast forward a few years we run into each other and reconnect, lots of reminiscing led to her asking why I never made a move on a night I remembered very well. I didn’t have a good answer and that’s when she told me she would have let me fuck her if I had made a move. Over the next few months through a lot of texting it was clear we were into each other, she started to tell me she was ready to divorce her husband as the marriage only happened cause she got knocked up and things were not good, she was tired of being treated like shit and worst of all they had no sex life. On the rare occasion they did have sex it was less than enjoyable for her, he was apparently well below average and had a bad case of premature ejaculation, she claimed she hadn’t had an orgasm since before she was married. We were texting all day every day but it was just flirting and bullshit, then out of the blue one day she texts me and asks when I’m off work, I told her and asked why, she said her babysitter lived near me and she was wondering if she could stop by for a quick make-out session, at first I thought she was joking but she wasn’t. I got home and she showed up minutes later, she told me she only had 5-10mins and attacked me, I couldn’t believe it but went with it, she wouldn’t let me go in her pants or up her shirt but she was fine with me rubbing her pussy through her leggings, I couldn’t believe how responsive she was and within minutes she was shaking and had soaked through the thin material, we kissed for a few more minutes, my very obvious erection pressed against her but she had to leave, telling me she’d text me after her husband was in bed. She texted me later that night telling me how badly she wanted me to fuck her, she couldn’t stop thinking about our make-out session or my very obvious and large erection. I kept up what I had been doing and now more than ever wanted to fuck her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been texting all week, mostly all sexual stuff. It was a Friday night and I was just hoping in the shower when she sent me a text asking what I was up to and when I said getting in the shower, she said she wished she could join me, then said I should get hard and send her a pic, I quickly replied only if she sent a pic to help me out, I thought she had bailed but a few minutes later I get a pic of her huge tits in a black lacy bra, so I got hard and with a shampoo bottle for comparison I sent her a pic, her response was immediate and she was ecstatic. I told her to come over but she couldn’t cause her husband was out of town and her parents weren’t home yet [she lived on their property with them] and it was a little late for a sitter. An hour later I get a text that says “Come over, I need to get laid already. Park down the road.” I sent her a text when I was on her street, she lived out in farm land and I met her at the edge of the property, she hit me with a long deep kiss, she grabbed my hand and pushed it in her pants, her pussy was practically dripping, she kissed me again then said if just seeing the picture of my cock had gotten her that wet she couldn’t even imagine how good it would feel inside her, she carefully led me up to the barn avoiding any security lights so when wouldn’t be detected, we grabbed some blankets from a storage room then made our way to a field behind the barn where no one would see us. We laid out the blankets and got down on them and began making out, it was almost a full moon and a clear night so we could see pretty well.

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 started going at each other and I started getting hard, as soon as she felt it press against her leg she began to remove my pants then my boxers then just looked at it in amazement, she began to touch it, hold it and size it up wrapping both hands around it, she had a bit of concern on her face. I asked if everything was alright and she said yes she was just a little nervous because for the past almost 5yrs she had only been with her husband and she could hold his entire cock in one hand compared to mine which she had two hands around and the tip was still poking out not to mention I was substantially thicker. I told her not to worry I’d be gentle and she got up and stripped down to her bra and thong. We laid down and continued making out. We pulled a blanket over us as it was a bit cold, she cut the foreplay short and begged for my cock. When I grabbed the condoms out of my pants she said I could fuck her raw and even cum inside her but I had no interest in knocking up a married woman. I slipped the condom on and as she lay on her back i got on top of her and teased my head against her very wet pussy then pushed in slowly, she gasped and her head and eyes rolled back as I slid in, I began pumping at a slow pace as we kissed, easing more in as she became comfortable with it until I had all seven inches inside her, I asked if she was good and she just responded she forgot sex could feel this good. We kissed and made love more than anything for a while, I needed something a bit faster though so I began to pick up the pace, by now she was taking it with ease as I pounded her hard and fast, she started moaning and pleading for me not to stop cause she was going to cum, we quit kissing and I just hammered my cock into her, she began clawing at my back then wrapped her legs around my waist then pulled me into tight and let out a groan next to my ear, her pussy was trembling and contracting so much i blew my load. We were both speechless, I pulled out and she had cum so much at first i thought maybe the condom had broke, like my entire cock and balls were coated in her creamy juices, when she finally caught her breathe she kissed me and said “My god, I think this needs to be a regular thing, my pussy hasn’t felt this good the entire 5 yrs I’ve been with him” I laughed and told her if she got me hard we could go again in a few minutes, she laughed and said she couldn’t handle another round of that, we got dressed and snuck back to my truck, kissed good night andIi went home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? We couldn’t get enough of each other, our affair was on and off over the next 4 years until she finally divorced her husband, she started dating again all the while we continued to fuck. she eventually found a serious BF and they got engaged and we called it quits, we keep some distance for good reason, given the short period of time they’ve have been together though and knowing what she is like I don’t see this marriage last long either, there’s still the occasional time i get texts at odd hours that feel too much like she is looking to hook up. For the time being though I stay away, if they break up though I’ll gladly pick up where we left off.

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), 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? I told no one for obvious reasons, she let it slip to a friend i was well endowed though saying we had been with each other prior to getting married and that led to me banging her friend

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? led to some of the best sex in my life

What was the WORST thing about this hookup? having to sneak around not always getting it when wanted

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was my first affair which over the years I’ve come to realize if a woman isn’t getting what she wants in a relationship she will find it somewhere else.

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

All things considered, how NEGATIVE was this experience? A little negative

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

Comments