What’s your gender? Man
How old are you? 50’s`
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? Lost Count
How many hookup stories have you here posted before? 4 or so

Hunting For A Third Or Fourth

How long ago did this hookup happen? Last week

What was your relationship status at the time? In a relationship (open)

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

How long did you know the person before this hookup? Just met that day

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? They were two guys we met at a club. Never seen them before or since

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My SO decided it had been a long time since we had a threesome or more, so it was her idea to go to a club and see what she could find. She is in her 40’s but still has a body that men of all ages drool over. 36DD nicely enhanced boobs, thin legs and tight ass.

She instigated it by calling me earlier in the day while I was golfing saying she was at the mall buying something for tonight as she wanted to go out and have some fun. I never have any issues when she wants to do this and told her to buy what she wanted and I would see her after golf. I got home and took a nap for an hour or so as I knew I would need my energy for tonight. She was in the shower when I woke up. I showered in one of the other bathrooms so I wouldn’t disturb her. I was in the den having a drink and reading the news when she called me saying she was ready.

Boy did she really “slut it up” that night. Skin tight, black miniskirt which barely covered her ass, low cut purple top that if she leaned over her boobs practically fell out of it, and 6 or 7-inch platform stiletto stripper heels and of course the requisite bright lipstick and overdone eye makeup. She bent over and asked me what I thought and if she should wear panties or not. I told her of course not, and besides, they wouldn’t be on too long.

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 arrived at the hotel where there is a hopping club which has a reputation as a cougar bar. I told her to go in and I would be watching from a distance. Nearly immediately two young-ish guys were all over her. They must have been in their late 20’s. As I was watching the scene unfold, one of them nearly immediately had his hand on her leg and the other was feeling her boob under her shirt. The club is pretty dark so its pretty easy to be discreet but you can still tell what was happening. All of this gets me very excited and I love to watch it.

I saw her excuse herself to the bathroom and I received a text from her saying they were ready and she told me they knew I was watching from a distance and were cool with it. I went over and introduced myself. They were extremely polite and bought me a drink to thank me for what was about to happen. They asked if there were any rules, and all I said was she has the pussy so she makes the rules.

They were staying in the hotel which was convenient and we went to their room. They asked her what her rules were and she said simply, “I cum first, and after that, there are none basically except I don’t like pain so nothing too rough”.

With that, they both easily stripped off what little clothing she had on except for her shoes which she always leaves on in situations like this. Guys seem to like the visual and I know I do. They took turns going down on her getting her extremely wet. I know when she is turned on because of the sounds her pussy makes. She calls it “sloshing” Soon she was squirting everywhere and the bed was already soaked. All she had to do at that point is tell her she is a sub and to do with her whatever they wanted and if she was uncomfortable she would let them know.

The rest is a blur including double penetration, airtight, double vaginal, etc. She is a real cum whore when she gets like this and was covered with their cum as well as mine. They are much younger than me so their ability to go multiple rounds were well appreciated by her. All I asked of them was that I was the last one to cum in her which they happily agreed to. After a couple of hours, she was a cum soaked mess and asked to jump in the shower to rinse off. With that, we dressed and left thanking our hosts.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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? We went home and just fell asleep as she was clearly sore and spent. The next day she commented on how sore her pussy and ass were.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? Just a couple of our lifestyle friends but to them, it’s no big deal as they all do it

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Just a night of fun and feeling young again

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? Hookups like this are something I think everyone, male or female, should experience

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