Vacation Hookup Stories & Tips

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On a Disney cruise, no less. It was the first afternoon, during the Set Sail Party. I ducked into a mens room. While I was peeing at a urinal, I heard somebody come in and go into a stall. I was washing my hands and saw the stall door open in the mirror. He was okay looking, sitting down, stroking his cock. I turned around and fed him.

Merely hours later, my family and I go to dinner. We are being escorted to our table and I spot him sitting with his wife and two children. We were seated at the table RIGHT NEXT to them. He turned bright red and whipped his head toward his wife and started talking to her animatedly. I sat facing their table and enjoyed watching the squirming.

I never saw him again; they must have changed their dining plan.

I'm old so this is going back to the Sombrero Club on Kensington High Street during its heyday back in the mid-70s. A boy stopped by and saw my Parliament cigs on the table. "Parliament? Why that's our form of government." We went back to his place and he fell asleep while I was on top of him. His front door locked with a key from the inside so I was stuck there all night and had no idea where I was. I remember seeing a big round building out his window which I later realized was Albert Hall.

Most of my hookups have been in hotel bars, when I'm traveling. There's always at least one other guy in the bar who's gay. I tend to stick to guys my own age. I'm in my mid-fifties now. When I was in my thirties, I stuck to guys my age or older. I avoid now (and avoided then) guys who looked to be in their early twenties. Didn't want to be rolled, and I figured any guy in their twenties in a hotel bar was a hustler. Make sure, if you hook up, that someone knows. For me, I would make sure that the bartender or waiter knew that I was leaving with another guy. Just be aware of the risks and your surroundings.

One of my most memorable adventures involved a guy I met in a hotel bar in Munich. Beefy, bearish guy...made eye contact across the bar. Made sure my gaze stayed with him, as I left. While I waited at the elevator to go up to my room, he appeared alongside me. Once in the elevator, it was just the two of us. Without saying a word, we started making out. Continued to make out on what I assumed was his floor. By the time we were in his room, we were all over each other. Ah, the memories...!!

Both times, I was in the cruise show. One inguy picked me up in the casino bathroom. He was French, on his honeymoon.

The best thing her time, it was at the sauna. After he was wiping the cum of his moth he told me the little girl I had picked for the audience participation portion of the show was his daughter.

Oh yes there was another time at the sauna, but they were a gay couple. Times had changed, and by the time they came along, not only were they popular and out and open, but they turned out to be amazing salsa dancers, were allowed to enter a dance competition as a couple and won.

I was hiking by myself outside of San Francisco in 2002 (visiting from NYC). One of the beaches just across the Golden Gate Bridge. It was a super-hot day with no cloud in the sky or breeze in the air. I eventually came to a clearing near a parking lot and took a rest to catch my breath. I was a sweaty mess. That's when I noticed a strapping, shirtless daddy hanging out there as well, sweating and guzzling water. The guy was kind of a giant. A Clint Walker type. So sexy and just glistening in the sun. He checked me out, saw I had no water and then walked over and gave me his bottle and winked at me. I guzzled some of it and said thanks. We started talking and he eventually asked if I wanted a ride back into the city (I had taken a bus). I was hesitant at first, but he just said "cmon" and I followed.

25 minutes later we were back at his Pacific Heights apartment, tearing each others clothes off. The guy was an absolute stud and basically turned me out (not much of a bottom here). I ended up staying with him for the next 3 days until he had to leave on a business trip. My friends were like "Where the fuck are you!!??" the whole time.

I stayed in touch with him for awhile, we even planned a trip for him to visit me in NYC. But on our last phone call he admitted he met someone and couldn't do it. I was DEVASTATED. But man, that first connection we had was insanely hot.

Long story. It was my Junior Year of High School and I was in San Diego form a SDSU college visit. My fight got in 4 hours before my dad’s (divorced parents), so while taxiing to the gate I put out a CL ad (RIP) and caught the interests of a decent looking early 30s postal worker. His email address put his real name instead of his account and (thanks Yahoo) so I checked out his Facebook and found out he was married with two kids and an overweight wife.

When I got to my motel (dad was cheap) I gave the guy my room number. I was so horny that I played like I was interested in bottoming despite zero experience (I aways topped). I definitely wanted to give him oral. When he arrived we made out and he wanted me on my stomach as he tried fingering me but I was really tight. He tried slipping his dick in and it was the most painful thing I ever felt. I thought I’d pass out from the pain. After the pain subsided I told him I can still blow him. He straddled my chest as I gave him oral. Before he blew his load I told him I didn’t want it on my face. He said I’m taking it on my face in a sexy dominate way, given his weight I couldn’t move from under him. I really didn’t want it on me. He shot a massive load on my face, the pillows, up to the headboard. It was a sight!

Was a dangerous situation looking back on this after a decade, but was so hot. He had a beautiful cock and his cum shot was top 5 in my life. Funny noticing a dried cum stain on the head board after my dad arrived. If only he know what his 17 year old was up to.

^ on my phone. Sorry for the typos

A Venetian guy picked me up at Piazza St Mark near the lion statue and took me back to his palazzo. He was a sweet gentleman and a lawyer by profession.

I saw this hot forty year old dad on my Grindr while in Hawaii. We were staying at the same resort and I ran into him while he was coming up from the beach with his family. He I both did a did a double take when we walked past each other.

He sent me a message asking why I didn’t say hello. I was shocked because usually you are invisible to hook ups, but I think he liked the danger. He fucked me for a good half hour the next afternoon while the family was doing some wale watching.

First of all, you need a caftan.

[quote] I was shocked because usually you are invisible to hook ups, but I think he liked the danger.

What does this mean, R10?

Means that you act like complete strangers. Most strangers are basically invisible to each other. He probably liked the danger of a potential hookup interacting with him, I don’t know. Seemed a little off. I just focused on the sex.

Hooked up with a hot Canadian couple on their honeymoon in Mexico. They said they had been their for 10 days and were bored as fuck. We hooked up twice before they left.

there, not their

r13 my friend chuck had a rule: if we’ve had our dicks in one anothers’ mouths, we’re going to speak.

R4 you are an expert and you don't sound overly whorish about it. Kudos to you.

[quote]Please teach a young gayling how it’s done.

Wouldn't you rather I teach an octogenarian, such as yourself?

I initially read this as Vatican hookups...

I thought this said [italic]Vatican Hookups...!