by elgonzo

Gender: Male
Age: 57
Race/ethnicity: Hispanic
Current location: Texas
Highest education received: Some college (not currently in college)
Occupation: Sales
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? A little kinky
How many sexual partners have you had in your life (including oral sex)? Over 50
How many hookup stories have you here posted before? 5

Revisiting Charlie

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Sex with an ex

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? Charlie was a very sweet lady I lived with for a short while in the late 80’s. We were both in the same profession (radio). She was a pretty, green eyed light brunette with great tits and lovely ass. We first met when I stopped by the station where she worked, and she was the first person I met. I thought she was pretty hot, since most ladies in radio are anything but. I knew I was eventually going to fuck her. One way or the other. It didn’t take very long. A couple of months actually. We moved to a smaller town, and took over the operation of a small market station. We were pretty happy, and fucked a lot. She became very jealous of one of the office girls, and it eventually led to us splitting up. I couldn’t stand the jealousy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Over the course of time, we went to other partners. We would keep in touch from time to time. Then one day, she called me at work, and asked if I could help her with a project with a non-profit group she was involved with. Sure, I said, anything for you. We ended up talking for nearly an hour, and during that time she complained about her husband, who was about 15 years older than her. He didn’t want to have sex with her, and she said she had occasionally gone to bars from time to time, and picked up a guy. I told her she should’ve called me, and I would gladly give her what she needed. Then she admitted she thought about it, but would gladly make up for lost time. We made plans for her to visit me at home, but she would have to wear stockings and heels for me. Anything I wanted, she said

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? Charlie stopped by my house on our designated night, and she still looked great. She had a mommy/MILF body now, but still very fuckable. Her hair was red now, and I told her I love red heads. She was also wearing a kind of tight black dress, with black stockings and black heels. We had a couple shots of tequila to calm our nerves, but not too much. We got into it right away, and I started stripping Charlie on my sofa. She looked great in her stockings, something we had never really explored before, but she went with it. I sucked her tasty tits, which made her crazy. We went to my bedroom, where she sucked my dick good, just like she had before. She couldn’t get enough, and then I started fucking Charlie. It was better than I had imagined, and way better than when we were younger. Fucking her in stockings and heels was icing on the cake.

Did you have an orgasm? Did your partner(s)? We both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No precautions.

What were your REASONS for having this hookup? She was lonely, and wanted a familiar sex partner.

Were alcohol or drugs involved? If so, how much? Tequila.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We both felt really good about it. She didn’t feel bad about cheating on her husband, since he had pretty much checked out in the sex game. We fucked a few more times, then I moved.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Consensual

Do you regret this hookup? If so, why? No regrets.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best was the intense sex. The worst was having to stop. It hasn’t changed my mind at all.

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

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

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