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What’s your gender? Woman
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (open)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? hundreds
How many hookup stories have you here posted before? 0

Fisting Fun

How long ago did this hookup happen? Two years

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

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a month

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? Sean and I met on Tinder. He was a very ruggedly handsome, fit guy around 30 years old. When we matched and started chatting, it was clear that there was an instant connection. Sean was looking for a little fun outside his LTR and likes older women. As we chatted a bit more, it became clear that he also had a strong desire to try fisting, something he couldn’t do with his girlfriend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It took a little while, but we finally made plans for Sean to come to my house one morning, as I occasionally work from home.

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? I was excited to meet Sean, but not totally sure what to expect. We both knew this was purely sexual, but it’s still a little funny to make small talk with a stranger who’s about to shove his hand in your pussy. My husband wasn’t aware of my relationship with Sean and I didn’t feel comfortable being in our bedroom, so I took him down to our basement, where it was a more neutral territory. We were both a little nervous, I think, but also excited. For it to go well, we both needed to be at ease, so I tried to be warm and calm and reassuring. He had a confidence about him that was very sexy, so it was easy for me to relax. We have a pool table in our basement and, when we got down there, I walked over and leaned back against it, just chatting a bit, not totally sure of the next step. To my surprise, Sean leaned into me and gently lifted me up on it. As I moved back a bit, he deftly took ahold of my leggings and peeled them off, followed by my panties. As a submissive, I was relieved that he took control of the situation, and very turned on. As he started rubbing and exploring my pussy, it was so hot to watch his face, he was clearly enjoying the exploration and how wet it was making me. We’d discussed how all we’d be doing was fisting, but I suggested he take his shirt off so it didn’t get messy. As I got wetter, he started inserting more fingers in me – two at first, then a third, then all four. I laid back and breathed and melted into the sensation of his hand going in until he finally got it all and I exploded with the fullness. The look in his face while he did it was priceless, pure joy. Not to mention how hard it was making his dick, as I could clearly see it outlined in his jeans. In the midst of this, he asked if we could move to the couch, which we did. I sat on it with him on his knees between my legs. We started up again and, as we did, he totally took me by surprise and said, “I really want to fuck you. Is that ok?” I had already wrapped my head around the pure transactionality of the situation but was thrilled he wanted to take it further and said yes. He stripped down to his beautiful naked self, with a rock hard cock, and I was in heaven. He got back on his knees in front of me and gently worked his hand back into my pussy. Then took that amazing cock and slid it in my ass, filling me up completely. Watching the pleasure on his face and feeling the pulsing of his cock in me was ecstasy. It didn’t take long for him to cum and when he did, he exploded with grunts that felt like they came from the most primal part of his being.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? Immediately afterward, we got dressed and I gave him a tour of my house. We chuckled about how things turned out a little differently than we’d expected, but in a good way. We said goodbye and I assumed that was the end of it. I was pleasantly surprised to hear from him a few months later. I happened to be at my office on the weekend and he was nearby, he ended up coming by and fisting me on my conference table. It was fun, but he seemed a little sad. I didn’t hear from him after that. I was curious about him a few months ago and was saddened to learn, by putting pieces together through Facebook, that he died a few months after our last meeting, at the age of 30. I’m not totally sure, but I think it may have been a drug overdose. It still haunts me to this day.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, Submission / Relinquishing power

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

To whom did you talk about the hookup? How did they react? A few friends – they thought it was hot

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Helping someone try something he’d never done and was craving.

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? It was a beautiful experience and I’m so glad I could do this for him.

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 live for casual sex and wish it was a more accepted part of life.

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