Hookups on the road and business trips.

Jacktrew

Pretty Kinky
Joined
May 19, 2024
Posts
154
When do you start planning? Right away, wing it, or a week or two out?

I rarely get to play anymore, I start planning right away, but the frustrating part is a lot of guys don't want to talk unless you are in town.

I prefer to get to know someone first, lay out the expectations, and sync calendars.

What do you guys prefer?
 
I always start planning as soon as I know about my trip. Im always posting on the local hook up site, mainly doublelist. I want to make sure i have a guy i can play with. Ill be in ashland va the week of the 26th if anybodies interested. Hosting in my hotel.
 
I'm not very experienced, but had a few meetups. I often hang around in the chatroom of Silverdaddies, with my cam on. Many replies, but most from people in the US, which is about 15,000km from here, so not really suitable for a date. My first date was with a guy who was visiting a nearby city. We chatted and mailed a lot, and exchanged photos, which gave me the feeling it was a serious and reliable guy. Finally we met in his hotel on 2 consecutive days.

The second date was in a town I visited when I did a roundrtrip of a few days with some family. I found this guy also on Silverdaddies, and saw he lived in that town. Again we had a few weeks of contact and exchange of information. I met him in his house.

The 3rd meetup was with the same guy as the first one, now in a hotel that rents out rooms per hour, halfway our home towns. Obviously we knew each other already, so no need to find out.

What I always agree on is that we meet in a coffee shop or so, drink a coffee or a beer, and then both are entitled to refrain from further action. It's important that both feel comfortable and safe.
 
When do you start planning? Right away, wing it, or a week or two out?

I rarely get to play anymore, I start planning right away, but the frustrating part is a lot of guys don't want to talk unless you are in town.

I prefer to get to know someone first, lay out the expectations, and sync calendars.

What do you guys prefer?
For me the most frustrating part is guys who pretend to meet but after a first chat completely disappear.

Also a bummer: guys who watch my webcam, that shows almost everyting, and keep begging for full face pics, while they don't even have a pic in their profile.
 
Met a guy online in my city. We first met at local coffee shop at my request. We were both after the same thing, sucking another guy’s cock. We got along well and then met at his house. He was divorced, I wasn’t. He met me at the door with only a robe on and we went to his living room and sat on his couch. He took his robe off and displayed a beautiful pink, hard, circumcised cock. I took my clothes off and did the same. He got on his knees and rubbed my cock gently before putting it in his mouth and sucking on it for a few minutes. I then did the same to him for just a few minutes before we went to a bedroom and he put lubricant on my cock and asked me to fuck him. I did, but I put a condom on first. We fucked until we both came hard, smoked a joint and then I left.
 
I usually prefer to wing it, but most of my hookups are with trans escorts in the cities I travel to. You can't arrange most of those in advance. I do hookup with men on my travels, but those are usually spur-of-moment affairs.
 
You can't arrange most of those in advance.
Really? Why not?

I've never arranged anything with an escort, I don't know anything about how it works. But what prevents these particular ones from arranging in advance?
 
I just use the apps. Logon in the late afternoon as normally get to the hotel about 1700 so if it clicks with a guy and he wants a sweaty quicky that's ok, or dinner, drinks and longer session later.
Quickest hookup ever was when I pulled over in the afternoon, checked the apps and I was right next door to someone. It was a really horny romp too.
 
Really? Why not?

I've never arranged anything with an escort, I don't know anything about how it works. But what prevents these particular ones from arranging in advance?
Some will agree to advance arrangements, usually if you are a repeat customer. But most escorts simply don't do it, and they specify it in their adverts. Too many flakes taking up their time.
 
When I was a regular traveller in Europe I would check out the gay bars and clubs scene online before I went.
 
When do you start planning? Right away, wing it, or a week or two out?

I rarely get to play anymore, I start planning right away, but the frustrating part is a lot of guys don't want to talk unless you are in town.

I prefer to get to know someone first, lay out the expectations, and sync calendars.

What do you guys prefer?
When I've done it, I just found the local pages of hookup sites on my route, and found at least one person per trip.
 
Some will agree to advance arrangements, usually if you are a repeat customer. But most escorts simply don't do it, and they specify it in their adverts. Too many flakes taking up their time.
Still not sure I get it. So… they only see clients “right now”?
 
I was in a hotel working out of town last night. I hooked up with this guy that said he was going to treat me to a hot bj. He was on point!! His cocksucking skills were amazing. He kept me on the edge and boy did my cock ache!! He had a nice cock too around 7”. And I told him i wanted to suck it too. He let me and said he was surprised he wasn’t expecting that. It had been a while since he had an amazing blow job and we treated each other very well. I liked his naked body too and the 2 hours we spent were amazing taking turns sucking each other.
 
I was in a hotel working out of town last night. I hooked up with this guy that said he was going to treat me to a hot bj. He was on point!! His cocksucking skills were amazing. He kept me on the edge and boy did my cock ache!! He had a nice cock too around 7”. And I told him i wanted to suck it too. He let me and said he was surprised he wasn’t expecting that. It had been a while since he had an amazing blow job and we treated each other very well. I liked his naked body too and the 2 hours we spent were amazing taking turns sucking each other.
Damn I miss traveling for work.
 
I'm not very experienced, but had a few meetups. I often hang around in the chatroom of Silverdaddies, with my cam on. Many replies, but most from people in the US, which is about 15,000km from here, so not really suitable for a date. My first date was with a guy who was visiting a nearby city. We chatted and mailed a lot, and exchanged photos, which gave me the feeling it was a serious and reliable guy. Finally we met in his hotel on 2 consecutive days.

The second date was in a town I visited when I did a roundrtrip of a few days with some family. I found this guy also on Silverdaddies, and saw he lived in that town. Again we had a few weeks of contact and exchange of information. I met him in his house.

The 3rd meetup was with the same guy as the first one, now in a hotel that rents out rooms per hour, halfway our home towns. Obviously we knew each other already, so no need to find out.

What I always agree on is that we meet in a coffee shop or so, drink a coffee or a beer, and then both are entitled to refrain from further action. It's important that both feel comfortable and safe.
Agree about SilverDaddies! Have had awesome experiences in town and away!
 
Back
Top