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What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? over 10

Sex With An Ex

How long ago did this hookup happen? 3 days ago

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

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

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? Pat was a lady a few years younger than myself that I had been FWB with several years ago. At that time I was seeing 4 ladies regularly (I would see each of them 2 or 3 times a week) and another 5 that I would see on an occasional basis. Pat had always been suspicious of me seeing others besides her but could never prove it. At one time as I was on top of her drilling her pussy she asked me if I wanted to be with just her and of course I wasn’t going to stop fucking and answer truthfully so I just told her yes and kept on plowing her pussy until I came inside of her. Pat is about 5 foot 6, 130 pounds. She apparently had been much heavier at one time and she had a lot of loose skin left over from her weight loss. Her titties were essentially flaps of skin with a nipple at the end. When I was with Pat before she was always hard to make cum but I always made sure she came at least once when we were together. She always told me that she loved my thick cock and the way it filled her like she had never been filled before.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was on social media and got a message from her which surprised me since I had not seen or heard from her in several years. She said she was in the area for a conference and would like to see me. I agreed to meet her in the bar at the hotel she was staying at. I showed up and we had a few drinks and caught each other up on what had been going on in our lives. She asked if I would take her back to her room as she said she had something she wanted to show me.

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 got up to her room and she closed the door and pushed her self up against me and began kissing me. I of course returned the kissing. She reached down and started rubbing my cock and said, “Mmmm yes, it’s as big as I remember”. I grabbed her ass and pulled her into me, rubbing my cock against her.
She led me to the bed and started taking my clothes off. I helped her out of her clothes. She got down on her knees in front of me and took my cock in her mouth and began to give me a really good blow job. She had never been very good at sucking me off before but she had obviously learned some skills. She was sucking and licking and pulling on my balls, sucking my balls. I told her I was about to cum and she took me deep inside her throat and I shot down her throat. She took it all and swallowed.
She then got up on the bed and told me to come to her so she could suck me some more and get me hard again. I climbed over her and dangled my balls and cock over her face and she began working them over again. I swiveled around and started eating her pussy as she worked on my cock 69 style. She was nice and wet and moaning around my cock when I got hard. I had her straddle me and she slid my throbbing cock into her throughly wet pussy. I told her to use my cock like it were one of her toys and to enjoy herself. I knew I would last a while after shooting in her mouth. She sand all the way down on my cock and began rocking on it. She kept working my cock in and out of her pussy and before I knew it she had essentially bent my cock in half so that the head was in her pussy but my shaft was bent in half rubbing against her clit. She would work my cock against her clit for about 5 minutes and it looked like she was about to cum but didn’t. She repeated this 4 or 5 times and finally I felt her pussy spasm as she screamed out “I’m cumming”. She pushed down hard on my cock and rocked hard against me as she completely soaked my groin with her cum. My cock head was feeling like it had been run through a razor blade with all the work my urethra had been through inside her pussy. I had to cum again so I rolled her over on her back, placed her ankles over my shoulders and began to pound into her. I only lasted another minute or two and blasted the inside of her cunt with my sperm.
After I was done, we laid recovering a few minutes. She reached for my cock and started sucking me again. She had made my urethra so raw from her fucking me that I couldn’t take anymore. I begged off and told her I had to get going. She pleaded with me saying she had to leave in the morning and really wanted some more of my cock but I told her I just couldn’t

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I got dressed and left. I got several text messages from her that night asking that I come back to fuck her some more but again I just begged off. My urethra hurt for almost a week after.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel more desirable, Power / Dominance, Submission / Relinquishing power, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? no one

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? 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? some fresh pussy. She had learned some new skills in her blow job

What was the WORST thing about this hookup? She made me so sore that I couldn’t continue fucking her

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? not at all

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

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

Anything else you want to add about this hookup? She tended to get emotionally attached last time I was with her and probably would have done the same thing this time. I felt guilt cheating on my wife but couldn’t pass up some pussy and probably will do the same thing if the opportunity come up again

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