What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sr. VP
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 156
How many hookup stories have you here posted before? Many

Two Damsels in Distress

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Group sex

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 was gassing my car at a busy interstate highway gas station/convenience store. The place with lots of cars and trucks and hotels. I was approached by two very attractive young women, mid-20s who appeared upset. They started talking to me, telling me how they got into a heated argument with a relative, who dropped them off at a hotel next door. They didn’t have enough money beyond today. Sensing either a scam or fear of being robbed, I told them I’d talk to them after I finished at the gas pump. I told them to meet them in the parking lot. I enjoyed the view as these two attractive women in tight shorts strolled to the edge of the parking lot. After gassing up, I locked away my valuables in the car and drove over to hear their story. They were heading to Boston from the South and were driving with a relative, who flipped out over something. At any rate, they were stuck and wanted some money. They must have picked me because of my nice car and suit. The taller of the two, with long flowing blonde hair, thin frame, sexy legs and tight ass, was quite a bit more flirtatious than her traveling companion, also mid-20s, about 5 inches shorter but with a great body and larger chest. My little head was thinking here so I suggested I could help them out if we could have sex. I would pay them enough to get them to Boston. At first they were surprised but the taller one immediately lit up and said sure. The other one was a bit more unsure. I wanted to make sure this was consensual so we chatted a bit more. I told them I would be back in one hour and meet them back at their hotel. I really don’t know what I was thinking but it would be a win-win for everyone.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I got to the back door of the hotel. The taller one (we’ll call her Sue) met me and led me to the room while holding my hand. The other one (we’ll call her Barb) was inside tending to their small dog, said hello but clearly wasn’t into this at all. After handing over the cash, Sue and I sat down on the bed. She put her hands all over me, saying, “Damn, you’re hot.” We started kissing and it got heated very quickly. Barb, meanwhile, started to watch and sat on the side of the bed. Sue and I were taking clothes off each other. What a gorgeous body — strong, lean legs, shaved pussy, tight ass and abs and perky breasts with inverted nipples. What a joy it was to explore that body. The other lady didn’t participate — yet.

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? Sue was giving me a blowjob when Barb finally started to join the fun. Though still fully clothed she also took my cock in her mouth and I was alternating between them. I reciprocated by going down on Sue, continuing until she came. At that point Barb finally started to get into it. I helped her out of her clothes. I had to spend some time on her breasts — they were considerably larger than Sue’s and I needed to take it all in. Eventually Barb welcomed my advances and enjoyed my tongue on her clit. Then the condoms came out. I started inside Sue — she rode me at first, then I picked her up and moved her to missionary so that I could make out with Barb and feel her breasts. Soon I started to take off my condom to get another one because I wanted inside Barb. They said it was OK — that they play together often. Kinky. So I entered Barb, who at that point changed from passive participant to full-blown screamer. I did her in a few positions while kissing Sue. Then I moved them both to doggie so I could go back and forth and enjoy the sites of those tight asses. I came inside Sue. We collapsed in a heap and rested for a while. They eventually started to play with my dick a bit more but I was spent.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 got dressed. They checked out of the hotel. I drove them to the nearest bus station so they could get tickets to Boston. I kissed them both in the car, they grabbed their stuff and went inside the bus station. Would never see them again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The in-the-moment aspect of it.

What was the WORST thing about this hookup? I didn’t want to come across as disrespectful. I made sure they were in consent and not on drugs.

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

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