Sex With Delivery Guy/drivers/plumbers/hotel Staff/electrician Etc

Recently was staying at a 4-star hotel and I had set up a hook up with a guy from Grindr. Bought a bottle from a liquor store and needed some ice, there was no bucket in the room and no ice machine. So I had to call room service and order some, and my hook up had gotten there a little early. Some time after a young early 20s guy showed up with a small bowl of ice, maybe enough for like 3 drinks. I asked for a bucket and he said hotel policy doesn’t allow that unless I order a bottle. I showed some disappointment, tipped him and let him go. Me and my hook up got into it after downing a couple of shots and there was a knock at the door while he was fucking me. I put on a robe and answer the door and it’s the room service guy with a bucket of ice. He clearly heard what we were doing but apologized for interpreting, took out a small bucket of ice he was hiding in his jacket and gave it to me. He also wrote his phone number and told me to text him if I needed anything. Thanked him and he left us to keep fucking. After my hook up left, I decided to text the room service guy for more ice. I decided to shower and wait for him with a medium towel wrapped around my waist showing my thighs and almost the bottom of my ass. So he came up with a small bucket and I invited him into the room and I pretended to look for my wallet so I can tip him. It was clear what I was doing by the state of the room. He awkwardly asked if I was enjoying my stay and remember saying that it could be better in a very flirtatious way. I left my wallet in my bag on the floor so I bent over to get it so more of my ass can show. As I got up I purposely dropped the towel and was naked in front of him. Gave him a tip and a look hoping he’d make a move. He was clearly a little awkward about the situation but asked if there was anything else I needed and I asked what did he think I needed as I got closer to him. He didn’t kiss me but felt me up and grabbed my ass. I touch his cock and it was hard so I offered him a drink but he didn’t drink. I turned around and poured myself one while asking if there was anything else he wanted. He was still a little awkward so I just asked if he wanted my ass and he started feeling it up. He felt up my hole and asked about the other guy, it definitely felt like I just got fucked. I told him I wasn’t satisfied. I undid his zipper and pulled his cock out and lubed myself up. He then took his pants off and started fucking me right there bent over on the tv counter. He didn’t last long until he pulled out and came on my ass. He then quietly left. Unfortunately he wasn’t working the second night there
 
Cruise liners offer a good selection of cock and ass. Started on my first afternoon with a guy from the engine room who just wanted to unload so I provided the perfect mouth for his nice juicy cock. I gave him a blow job a few times if our paths crossed and he was always happy to lob one down my throat. After that a variety of crew members offered various services so most nights I was entertained giving or taking. So on that side the cruise was really good. Tended not to mix with the gay set, a little to flamboyant for me. The best job was when I managed to get some room service really late and this cute young lad from the kitchen arrived with the tray. I was just in casual shorts, it was warm and his blue eyes popped as so did his dick. My legs opened as he put the tray down, his eyes went straight to my crotch which was displaying well and said "did sir want anything else", so, "if you'er offering to share my supper?" His tight ass tasted good and he rode with a vengeance, then we finished the supper tray and I gave him a parting blow job and sniffed his fair haired bush at the same time. Next day I disembarked, regretfully.

Surprised. I've heard that cruise crew are fired instantly for any sexual behaviour with passengers. I guess some take the risk.
 
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Surprised. I've heard that cruise crew are fired instantly for any sexual behaviour with passengers. I guess some take the risk.

They do take the risk. I spent the night down on the lower deck where their cabins are. He mentioned that it was a huge risk but in this case the 'squeeze was worth the juice'. lol
 
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no i was never that lucky and i am too shy to flirt with guys who i hire to help me with something. i have no idea how you guys do it, i really don't know what to do.

i clearly remember when i was younger my father hired a team to clean our new house and one of the guys looked like a Calvin Klein models, tall blond athletic mid 20s i was finding reasons to be at he same rooms he was cleaning as him all the time, when he finished work i remember jerking off alone in my room thinking about him. then i had the stupid idea to test him on his work phone but apparently his wife read those messages (had no idea he was married) and sent me an angry message back, not a fun situation.

a few years later we hired a plumber to fix some broken pipes in our house, early 30s tall blond and had the sexy bad guy look, he was really hot, i also remember being alone in the house with him, helping him fix what was broken and i kept thinking how much i wanted to suck him off. i still had no idea how to approach him sexualy but he didn't seem any interested anyway, he's str8 and actually married now. i did jerk off alone in my room thinking about him.

sometimes when i order food the delivery guy is really cute, i have no idea how you can approach these guys since they only stay for a few moments until they get paid and leave.

i clearly need some advice on how to approach them.
 
Mate, look at it this way, even if the guys you fancied didn't play ball you had some amazing wanks! Sometimes it takes a while till the vibes work - or not, just don't think its hello and bang.
Like you one time I fancied the guys in whose house I was working and had loads of fantasy wanks. One day I had to go in his room and he'd left some dirty underwear about. In my element when I found a jock full of nearly dry spunk - that was the closest I got to him and me enjoying and orgasm together
 
It was more than a few years ago but a young man knocked on my door--a college student working his way through school who had started his own pool cleaning/maintenance service. I had always done it myself but liked his attitude and decided to support his business. One morning I climbed out of the pool so he could do his work. His eyes locked on my bulge in a speedo undressing me unabashedly. I smiled watching him. He smiled back unable to keep. his eyes off it. When he came in to be paid he smiled and said wow you are really big. I said do you like it? He said yeah I like it! So I said do you want to see it? He said is it okay if feel it? I said go ahead.

He felt my package through the thin fabric. My erection bowed it out. His fingers traced. He asked if he could hold it. I said yes. His warm hands took it out. These are in the way he smiled pulling speedo down over my thighs. It's beautiful he said. Want to suck it? He nodded and blew me where I stood and swallowed my seed. It became a weekly thing--quick bjs before he rushed off to his next customer. That young man sucked a lot of seed out of me.

As time went on we spent more time together when his schedule allowed. I gave him full body massages on the table. Eventually he wanted it in him. I showed him the ropes--his beautiful brown body dancing on my cock. He had a girlfriend. I'm not gay he said but I am gay for you.
 
This story is quite arousing. So is your correct use of regretful vs regrettable.
Oh I regretted leaving the ship having had such a good unexpected time. Times change as do ships, later trips a few years down the line were down to indulging with other passengers as crew very much not wanting to become the subjects of botchy bar talk.
 
One of my fantasies is to hook up with a delivery guy: pizza delivery, Uber Eats, DHL, UPS, etc.
But from my experience, company delivery people usually have tight schedules and Uber Eats guys just give me my food and leave.
Anyone have any tips on what to do with Uber Eats and other independent delivery service guys? :)

I've sucked off several taxi drivers. I'm a crossdresser and I go out dressed up at night to go to bars and clubs, so it's much easier for me to attract these guys. I make my move when I see them looking at me in the rearview mirror. Most of the time they say yes. If I see that they're interested, I tell them that I wanna suck their dick. Most say yes. I've had a few decline though :)

My hotel staff story: It was 2012 in Amsterdam. As I was leaving my room, I noticed one of the workers looking at me and smiling and kinda talking to me a bit. I think I gave him the "I'm interested" look. When I came back, we talked a bit again. I was in my room relaxing playing on my phone and I heard somebody trying to open the door. I knew it was him. He unlocked my door and just walked in and asked if I need any towels or anything. I gave him the "come to my bed" look and he came over, I pulled down his pants, and sucked on his dick. He pulled down my pants and licked my ass (good thing I took a shower 30 minutes prior!). He eventually shot his load and left. It was an interesting and hot experience :)
 
My Barber just out of the blue he said, I've enjoy working on you lovely head for so long when do I get to work on your other?
I said whenever you like. He locked the shop door and put on the "out to lunch sign".
 
One of my fantasies is to hook up with a delivery guy: pizza delivery, Uber Eats, DHL, UPS, etc.
But from my experience, company delivery people usually have tight schedules and Uber Eats guys just give me my food and leave.
Anyone have any tips on what to do with Uber Eats and other independent delivery service guys? :)

I've sucked off several taxi drivers. I'm a crossdresser and I go out dressed up at night to go to bars and clubs, so it's much easier for me to attract these guys. I make my move when I see them looking at me in the rearview mirror. Most of the time they say yes. If I see that they're interested, I tell them that I wanna suck their dick. Most say yes. I've had a few decline though :)

My hotel staff story: It was 2012 in Amsterdam. As I was leaving my room, I noticed one of the workers looking at me and smiling and kinda talking to me a bit. I think I gave him the "I'm interested" look. When I came back, we talked a bit again. I was in my room relaxing playing on my phone and I heard somebody trying to open the door. I knew it was him. He unlocked my door and just walked in and asked if I need any towels or anything. I gave him the "come to my bed" look and he came over, I pulled down his pants, and sucked on his dick. He pulled down my pants and licked my ass (good thing I took a shower 30 minutes prior!). He eventually shot his load and left. It was an interesting and hot experience :)

Hot story

Anyway the key with delivery drivers is probably just to find out when they are done working usually. They do usually keep a tight schedule when working especially a busy time
 
So far it is only near the end of March and this 2022 year I have literally fucked, sucked, been sucked, jerked, or have jerked 14 different Uber drivers.

Just 2 nights ago I answered the door for my pizza delivery bulging in some fresh tighty whiteys just to see what would happen. And BOOM... got my big slab of meat sucked off and shot thick ropes all over him. Hopefully he didn't get questioned about the stains left on his shirt

I don't cum often from getting blown but dude, who at first seemed really straight, was an oral master and I literally drenched him with my seed before he had to jet off
 
Hot story

Anyway the key with delivery drivers is probably just to find out when they are done working usually. They do usually keep a tight schedule when working especially a busy time
I always order my food about half an hour before the restaurant or pizza place closes. I've had guys just stay and others that come right back after they turn in the money.
 
I got fucked by the front desk clerk at a gay hotel in Fort Lauderdale. Despite being clothing optional and very frisky, it was against hotel policy for staff to play with the guests and I had to sneak him in the side door and up to my room.
 
So far it is only near the end of March and this 2022 year I have literally fucked, sucked, been sucked, jerked, or have jerked 14 different Uber drivers.

Just 2 nights ago I answered the door for my pizza delivery bulging in some fresh tighty whiteys just to see what would happen. And BOOM... got my big slab of meat sucked off and shot thick ropes all over him. Hopefully he didn't get questioned about the stains left on his shirt

I don't cum often from getting blown but dude, who at first seemed really straight, was an oral master and I literally drenched him with my seed before he had to jet off
what's your address!!! lol
 
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