What’s your gender? Man
How old are you? 50s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 2
Other Dessert Plans
How long ago did this hookup happen? 10 years ago
What was your relationship status at the time? Single
How would you best classify this hookup? Short fling
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? While attending a business meeting in Baltimore, I met a woman one evening at a local bar. She was out casually drinking with friends and we struck up a conversation. Several drinks later she volunteered her phone number and said that if I was visiting town again to give her a call. About a month later, I was back for an overnight business trip so we arranged a date.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The date was dinner at a well-known, high-end steakhouse, adjacent to the hotel where I chose to stay. After checking into the hotel, I headed down to the restaurant. Securing a spot at the bar, I waited for her arrival, and about 20 minutes later she showed up.
Nancy was a divorced, curvy, cute blond, in her late 40s, with beautiful green eyes, and a sparkling smile. Dressed in a fur lined ski parka with high leather boots, she had cougar written all over her. Settling into a bar seat, Nancy’s opening line was, “You are even more handsome than I remember.” This was going to be a fun evening.
When we sat down to eat, Nancy insisted on sitting beside me. That warm glow set in as we talked, ate, and shared a nice bottle of wine. Shortly after finishing the main course, her hand drifted into my lap and brushed my crotch. “Oh my,” she said, “What do we have here?”
Just then the waiter came by to take our dessert order, “We have other plans for dessert,” I replied as I quickly paid the bill, grabbed Nancy’s hand, and led her out of the restaurant and into the hotel elevator.
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? The elevator could not get to my floor fast enough. We opened the door to my room and immediately started making out – standing up against the mirror in the foyer. My hands explored under her shirt and off it came. Nancy had an athletic body, with full, perky tits – I’d say 36D or so – with wonderful, nipples and wide, dark areolae. Off came her pants to reveal a completely shaved pussy.
At this point she unbuckled my pants, took my cock in her hand, and led me to bed. There I spread her legs, and began kissing the inside of her thighs until she begged me to fuck her, but not until I licked her to orgasm. Totally delicious!
I proceeded to fuck her (bareback) in a number of positions for a quite a long time until she came for me again. The session ended with a fabulous blowjob – with me on my back – where I sprayed into the back of her mouth and she swallowed every last drop.
How sexually satisfying was this hookup? Very
Did your partner have an orgasm? Yes, multiple
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? Relaxing afterwards, I commented on how much I enjoyed her body. It was then that I noticed some scars on her breasts and across her abdomen.
Nancy somewhat shyly told me that she had undergone breast reduction surgery, that the abdominal scar was from a caesarian birth, and that she was very self-conscious of both. I assured her that the surgeons did a fine job and that she was certainly very desirable in my book!
I saw Nancy several times afterwards and the terrific sex only got better. She was always a tiger in bed and I think she enjoyed fucking even more than I did.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have
How intoxicated were you? A little tipsy/high
What substances did you consume? Alcohol
How intoxicated was your partner? A little tipsy/high
What substances did your partner(s) consume? Alcohol
Did you consent to this hookup at the time? I gave enthusiastic consent
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
Do you regret this hookup? Not at all
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