When I was a Bellboy
Fresh out of high school I went to live with my Aunt and Uncle, free rent in their spare bedroom while I went to college nearby. I was barely 18, my Uncle was the Bell captain at a major hotel, in Nevada.
He got me a job for the Summer as a bellboy, of course I got the night shift, 11 PM to 7 AM.
It was mostly taking drinks and food up to the rooms, a few people were checking in but not many.
Days went by, nothing out of the ordinary, then I was taking an order up to one of the suites, those were huge rooms with double doors, all sorts of fancy stuff.
The guy was a 40ish balding fellow, a bit heavy, his wife was a blonde about 30 and very pretty.
She also only had on a pair of panties. That was a wow to me, up until then my chances to see bare breasts was very limited.
The 2nd night, they called down and asked for a massage in their room, and asked for me specifically.
The receptionist told me to go up there and give the lady a rubdown, I told her I had no idea how to do that. She told just rub her legs, back, whatever, just go do it, whatever they wanted, they were high roller customers and we had to keep them happy.
So I did, the lady was stretched out on the bed, covered by a sheet, her husband parked himself in a chair, and began to give me directions. I soon got over being embarrassed, I touched her everywhere with his encouragement. At one point her hand came out and she was rubbing my groin, things got rather obvious because the guy was masturbating and she was tugging off my clothes.
My 2nd time for having sex, the other was a fumbling attempt back in high school. They were there two more nights and I got called up each night, by then I was eager. She at one point was sucking me while jacking off her husband's rather tiny little dick. That night I got off in her two times.
I felt pretty proud, I was way bigger than he was.
Each time they gave me a $50 bill, so.. does that make me a prostitute?
But I never saw them again, and the only other stuff that happened was a few answered the door topless.
That Fall I went back to school, never worked there again.