by elgrangonzo

Gender: Male
Age: 57
Race/ethnicity: Hispanic
Current location: Texas
Highest education received: Not graduated from high-school
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 little 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? 5

The Online Bet

How long ago did this hookup happen? 2010

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…)? Fuck buddies

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 met Lisa in an online site for mature people. At the time, she was just about to turn 50. Her photos and personality were great. She was petite, about 5′ 3”, short brown hair, bright blue eyes and what looked like a great set of tits. The one problem was she lived about 7 hours from me. I wasn’t even sure I would get her attention, but she did contact me, and we started texting each other not too long after that. Eventually we started skyping, to hear and see each other. We were both a bit reserved on Skype, but then we would cut loose with some hot sexting. Since we both liked sports, and the national college basketball championship was coming up, we decided to place a bet. The winner would pay for an entire weekend in San Antonio.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? To make a long story short, her team won the title so I had to ante up. Anything to hook up with Lisa. Once we set our weekend date, everything was in motion. I made all the arrangements for our hotel, and met her in person finally after a couple of months of skyping and texting.

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 took our luggage to our room, and it didn’t take long for the two of us to start with each other. We started kissing, and her tongue tasted wonderful. I stripped her slowly, undoing her bra and letting her fabulous tits out. I sucked on them for a long time, then went down on her. Lisa returned the favor and sucked my dick for a long time. I lay her down on the huge bed in our room, spread her legs and impaled myself in her wet pussy. I fucked her the whole day in just about every position. Lisa couldn’t get enough, and neither could I. Our second night was great because she let me fuck her anally.

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? No precautions. Her husband had passed away about 8 months earlier, and she hadn’t had any sex in months before he died.

What were your REASONS for having this hookup? Was interested in enjoying a woman from another location.

Were alcohol or drugs involved? If so, how much? No

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, but distance and careers were big factors in not pursuing a relationship.

To whom did you talk about the hookup? How did they react? A friend at work

Was this a consensual and/or wanted experience for you? For your partner? It was consensual.

Do you regret this hookup? If so, why? I regret not being able to follow up. Would be worthwhile

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? Hot sex was the best, along with sharing with Lisa. She was good at that. The worst was having to leave her.

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

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

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

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