by elgrangonzo

Gender: Male
Age: 57
Race/ethnicity: Hispanic
Current location: Houston
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? Straight with a bit of kink
How many sexual partners have you had in your life (including oral sex)? Over 50
How many hookup stories have you here posted before? 6

Something About Her Heels

How long ago did this hookup happen? 4 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…)? Friend with benefits

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? I had previously posted a story about Darcy, a school teacher I had met online, and had an on and off relationship with. She and I had reconnected, and found some more things about her, and me as well. Darcy had a great body, which wasn’t bad for a 50 year old woman with two grown children. It was because of her swimming that kept her in shape. Her legs were awesome! Soft yet muscular, and when she wore a skirt, she looked great!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were texting each other one night about our next hook up, when I mentioned her legs and how great it would be to fuck her while she wore heels. She excitedly texted back, and said it would be very cool and sexy. Then I told her I would love to rub my cock on her feet as she wore her heels. This really set her off, and she wanted to know how soon we could do this. The sooner, the better I told her, which meant tomorrow night.

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? Darcy got to my house after her swimming workout wearing a very skimpy skirt, and a bag with her heels in it. We had a couple of drinks, and started making out. Before we knew it, we were in my bedroom, where I removed her clothes. She broke out her heels, and slipped them on. “Like what you see?”, she asked. What could I say? Of course! She sat down on the edge of the bed, where I slipped one of her heels off about halfway exposing the sole of her foot, rubbing my cock on it. She moaned like she was having an orgasm. I kept rubbing my cock on her feet, and legs. All I could hear was Darcy’s moaning. Then she told me to fuck her. I fucked her hard while she was wearing her heels, which had been an odd little porn fantasy of mine.

Did you have an orgasm? Did your partner(s)? Yes, we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.

What were your REASONS for having this hookup? We wanted to experiment a bit, and just find another reason to fuck.

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

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 great! She thought the idea of me rubbing my cock on her feet while she wore heels was very erotic.

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, other than the fact we stopped seeing each other not too long afterwards.

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? All good, no bad.

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 or anything else? I wish I had the chance to fuck Darcy again.

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

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