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What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
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)? 50, 55-60 counting oral
How many hookup stories have you here posted before? quite a collection now

Ex-Fuck Buddy Turns Adulterous MILF

How long ago did this hookup happen? probably around 8 years ago

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? “Jenna,” who I’ve written other stories about was 5’2″, athletic and toned (a surfer), and extremely top heavy. Her boobs would spill out of a 34 DD bra and she had incredibly perkiness. She was Cuban, from Miami, but entirely “white American” when it came to her cultural upbrining. She had gorgeous green eyes, long, dark brown hair, tanned skin, and big, full lips.

We met online while I was a freshman at college. There’s a whole story about that which you can find if you click my user name and read my story about the “3 girls I never met who drove 8 hours for me.”

Our entire relationship was based on fucking each other. We were extremely sexually compatible and extremely comfortable with one another. We just clicked in every way imaginable. And although I never let her know, I thought the world of her. I considered her marriage material except for the one character flaw she had: having me as a fuck buddy. I always pictured myself settling with a “wholsome” girl, and the fact that she even had me as a fuck buddy sort of made me label her negatively. It also didn’t help that at the point in time our lives were connected, my primary concern in life was to sleep around as much as possible. So I never even entertained the thought of attempting a relationship with her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jenna and I hooked up all throughout my four years of college. She always lived 8 hours away (near my hometown) but she’d drive up to see me and I’d drive to Miami to see her when I was home on various vacations. We would fuck in my car, her car, hotel rooms, public places, and just about anywhere we wanted to.

Sometime after college, however, Jenna moved away to Louisiana.I’m not certain about the details, but she met a guy, fell in love, got married, and had a child with him. I was happy for her and not the least bit jealous. My life had also moved on and I had been in various serious relationships, attempting to “settle down” on my own.

At some point, Jenna and I began talking again. It was entirely platonic, as we were more than capable of having a friendship without needing to have sex. She let me know that she was pregnant again, going to be coming back to Miami in a few months, for a few weeks, to watch her parents house while they were away going off somewhere. She wanted us to get lunch, catch up, and sex wasn’t even in the equation. With her being pregnant, I was fine with her not allowing me to fuck up her marriage. So I agreed to meet her, but fully intended to try and seduce her anyway. The idea of making her cheat on her husband with me turned me on. The idea that she was now a mom and pregnant also turned me on, as she would potentially be my first official “milf.”

As the days went by, problems started to develop between Jenna and her husband. Her husband was doing a lot of traveling to California (his home state) for his job and Jenna was noticing that he was making a lot of phone calls to his ex-girlfriend. While he was still away on business, Jenna called him and confronted him. He admit that he was cheating on her, begged for forgiveness, and she took it surprisingly well. She later told me that her reply to him was more or less, “I won’t forgive you, but we can work it out. Just don’t expect me not to do the same thing.” At that point it became totally clear that when Jenna came down to Miami, we were going to fuck like rabbits.

When Jenna finally made her way to Miami with her toddler-aged daughter, I was visiting her almost right away. She got an old friend to babysit for her, we saw a movie, and I treated her like royalty. Rather than just going after her lustfully, I attempted to give her a boyfriend/husband approach to appeal to her emotions. It worked. She was melting in my arms. She was telling me how she wishes I behaved this way back when we were fucking all the time, because she thought I was being really sweet, kind, and attentive.

Half of me truly was trying to make her fall in love with me. Not because I wanted to be with her (her having a kid was baggage I refused to accept from any potential long term partner), but just because I like to be sought after. And the idea of making her think I was better for her than her husband was appealing to me.

After the movie, we drove together to pick up her daughter and headed back to her parents house where she was staying.

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? When we got to her parents’ house, it was time for Jenna’s daughter to take a nap. She put her down in one of the back bedrooms and joined me in the living room. In absolutely no time at all, we were making out, removing clothes, and falling back into old rhythms. The one thing that changed about Jenna, physically, was the size of her boobs. Being pregnant, her breasts grew from a 34 DD to something much, much, much larger. I’m usually spot on when guessing bra sizes, but I can’t even begin to pretend to know what size her tits became. They were absolutely gargantuan. Each one being the size of a large watermelon is the closest reference I can think of that comes close.

After getting ourselves hot and worked up, I laid down on the couch, she climbed on top of me, and started riding me in a slow hypnotic fashion, grinding forward and backward. The best part about sleeping with Jenna was how she would hover her body just over mine when she rode me, so that her enormous breasts would slide up and down my body each time she rocked her hips. It was like two amazing pendulums grazing across my body continuously driving me wild.

For the first time in our long “relationship,” she made me cum. Normally, I had to be in control to make myself cum- something that always made her feel disappointed in herself. But this time, she had me. She built me up and I came inside of her. When I felt the orgasm coming, I grabbed each side of her ass/hips, made sure that she continued to hit the right spot on the head of my dick, and just exploded into her. Her face quickly went from shock to total ecstasy. We had always relied on the pull-out method, so it was instinctual for her to freak out for a second before remembering that she couldn’t get pregnant when she already WAS pregnant. She immediately began enjoying the moment, realizing that she made me cum, and we both enjoyed that special connection you only get when you’re cumming into the depths of an unprotected pussy.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? When she climbed off of me, she just kept exclaiming, “I made you cum! Oh my god, I made you cum…” like it was me who had made her day.

For the duration of her stay, Jenna and I spent a ton of time together. I played with her daughter, we ate meals together, and had a ton of sex during nap times. During one eventful day, I brought along my HD camcorder and recorded us having sex in all kinds of different positions. I was able to capture the magic of her huge breasts bouncing every which way while fucking her, the look on her face while she enjoyed every orgasm I gave her, and – my favorite – making her hold up her wedding ring to the camera while on her knees as I jerked myself off and shot my cum all over her tongue and face.

When it was finally time for her to go back home, she told me how she was planning on telling her husband what we had done. I was against it, but couldn’t stop her. Later on, she told me about how she told him, got the painful reaction from him that she was looking for, and they each agreed not to cheat on each other from there on out.

Because of my own strictly-monogamous marriage, Jenna and I lost contact. From a bit of Facebook stalking, I saw that she went on to have a total of four kids with her husband, but just recently got a divorce. I wish her the best. In another life, her and I could have been something more. But, as it is, I’m incredibly grateful for every moment we shared and wouldn’t change a thing.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, She was already pregnant!

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Power / Dominance

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? My relationship with Jenna has always been entirely secret. None of my friends ever met her.

Did you get emotionally hurt as a result of this hookup? Not at all

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? I got a very beautiful girl to cheat on her husband with me. I simultaneously checked off the boxes for sleeping with a milf, committing adultery, and sleeping with a woman who was pregnant.

What was the WORST thing about this hookup? I very briefly began to imagine what my life would have been like if I had taken Jenna more seriously and attempted something serious with her before she went off, got married, and had kids.

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

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

Anything else you want to add about this hookup? If I’m not mistaken, this was the last time Jenna and I had sex.

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

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