I just love this site and jerk off quite regularly while reading these stories. I hope you enjoy my story.
This is a true story that happened last week while on business in Puerto Rico.
I arrived mid-afternoon, collected my luggage and headed outside the baggage claim area to catch a cab to my hotel. This was my first time in Puerto Rico so I was all wide-eyed observing everything. What struck me immediately was how most of the young men had there eyebrows shaped or sculptured. Where I'm from, this would be considered definitely effeminate and most definitely gay. My cab driver was handsome, appeared masculine and also had his eyebrows shaped. My gaydar was going off every few seconds and had to be tweaked to compensate for this anomaly. I was staying about half an hour outside of San Juan in a resort town called Dorado, which was a bit of a bummer as I wanted to see more of San Juan and sample some of the nightlife there. Anyway, I decided to make the best of it and enjoy all the amenities my hotel had to offer.
My days were long so by the time I got back to my room I was tired and hungry. Since I was alone I didn't feel like sitting by myself in the restaurant downstairs so each night I ordered room service. I got into a routine by ordering room service then jumping into the shower so by the time the food arrived I would be dressed and ready for dinner.
I am in great shape and take advantage of this by the clothing I wear. Each night I would wear a pair of matching designer underwear, they were tight yet loose fitting at the same time, you know the type that leave almost nothing to the imagination. This is normal attire for me so I was totally oblivious to its effects on the staff.
After the second night a different waiter delivered my order. This one was young and gorgeous. After 10 minutes he called to find out if everything was ok with the order and I told him I ordered mash potatoes and received baked instead. In a flash he was up to correct the order. After 10 minutes he called again to see if everything was ok. I found this a bit strange but not totally outside of the norm. I told him yes everything was ok and decided that if he called again then something was definitely up. Another 10 minutes went by and this time he said this was a 30 minute call to see if everything was ok. Well this time I asked him to collect the tray and he said he would be up in a minute.
When he arrived I asked him in and shut the door behind him, he picked up the tray and placed it on his left shoulder, I asked him how old he was (23) and what time he would be off from work, he said 11pm, I said that would be too late. I asked him if he would be interested in a quick mutual jerk off and he said sure, by this time I was obviously hard with my erection straining to the left in my underwear. I reached over and unzipped his fly to reveal a small hard uncut dick with two larger than average balls.
While this took place he was still holding the tray on his shoulder. I asked him to please put the tray down. He did so and went straight to my chest and sucked hard on my now erect nipples as he jerked himself off. I asked if he jerked off everyday and he said yes, I asked if he did it already today and he said no. I undressed and joined in the fun. He told me I was his first black guy and I replied I hope to represent, he said I was huge, but I have seen larger. I am cut with close to 9 fat inches; my balls are average and shaved. He came quickly in copious amounts on the carpet and was dressed and out the door as though nothing happened. I didn't cum, I wanted more time to enjoy a nice long jerk off, which I did later that night in bed.