Rent Boys Revisited

By Sam Tudor

Published on May 1, 2023

Gay

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Ian's Story -- Part 5

Marty was a rent boy, like me, and we became friends, hanging out on the Meat Rack. He had been kicked out of his family's home as well, and we had a lot in common. It turned out that we were also sexually compatible, both versatile, and laughed a lot together, about our clients, things that had happened, while working, farting in the mouth of a guy who was rimming us, who professed to like it, guys who wanted to be shit on, women who wanted young guys, old guys who could not get it up but if fucked would cum, the whole gamut of sexual experiences.

Marty was, like me, 17, versatile, his father had caught him being fucked by the next door neighbor, who was married, and who had a little cock, which, he knew how to use. First, his father called the cops, but Marty was 16, the age of consent, so what he did was not illegal, and Marty was OK with it, so it was not rape. And there was nothing the police would do about it.

So, his father beat the shit out of the neighbor, and then told Marty that he would get the same treatment if he persisted in being queer so, he might as well just leave. The neighbor felt very sorry for Marty, and helped him out with cash, from time to time, and clothing, since Marty was sent out with just the clothes on his back and his school books.

Marty was living at the YMCA, it was cheap and clean, but in May he was moving to the homeless camp at the river, to save money for the next winter's lodging, and when I got kicked out of Mr. O'Reilly's, at about the same time, because I had started using drugs, more about that later, he invited me to share his tent, where we first had sex with each other.

Marty's tent was down by the river, near the place where a small stream emptied into the it. It was a small homeless encampment; we sort of took care of each other. Marty and I shared a tent, with a blue tarp over the top of it, I accumulated a sleeping bag, and got my summer clothes from Mr. O'Reilly's place, and began living there in May. There were usually seven or eight of us there, we took turns guarding the place during the day. The cops did not bother us, at least we were not in a public park out in the open, embarrassing the city with its homeless, and, our little group, which consisted of guys and women, some like us, barely on the wrong side of the law, the mentally challenged, the crazy, and some just on hard times: it was like a family, of sorts, we did help each other out, and "honor among thieves" we did not steal from each other, not that any of us had anything much worth stealing.

The small stream provided us with a place to wash, after about mid-May it was warm enough to get into, so we were clean compared to the people in most homeless camps. We built a temporary dam to make it a little deeper (it would wash out in the winter/spring floods) and most of us would go in naked all summer into the fall.

My plan, and that of the others, was to find a cheap room in the fall to get us through the winter.

Neither of us had gotten into an S&M or B&D scene but expected that we would. We agreed to try to arrange it so that we were together the first time with a client who wanted it to protect each other if need be. We had been warned about the guy in the puffy blue jacket, who got really rough, but paid well, and we had frequently said "No", to his approaches. His name was Gary.

But, one nice May evening, neither of us had been able to score a client, and Blue Puffy Jacket, as we were calling him, (without the jacket, it was May) came over to us, and asked if either of us wanted to go home with him to play. I told him it was a two-fer, both of us or neither of us.

"What's the matter, faggots? You afraid of me?"

"Yes," I said. "I have heard some stuff that is not good."

"It's all bullshit. I never really hurt anyone, they were just sissy boys that could not take it. And, I have some weed, and some stronger stuff if you are interested. And I pay real good."

"How much is "real good?" I asked.

"Well, if it was just one of you, $100 for two hours at my place, but, for two of you, $75 each, two hours."

I looked at Marty and he nodded "yes", so I said, "OK, but you have to bring us back here when you are done."

"You guys drive a hard bargain," he replied, "my car is over there."

So, we went. The car was a reasonably new Chrysler, I got in back, Marty got in front. Gary lived in a single family house in the nicer part of the city, up on a hill on the west side, out of the smoke from the factories most of the time. He took us down into the basement, which was outfitted with a lot of stuff. Right away I could see a sling, a cross against one wall, various ropes hanging from the ceiling, and, mounted on one wall a selection of whips, and dildoes, and harnesses, and other things I could not readily identify.

"OK, guys, you are being paid to do what I say, and, I promise, it may be rough, but no damage, to you, or, to me. The safe word is "Stop," easy to remember, but if you stop at things which are just fantasy play, and not going to hurt you, I will withhold money from your pay.

"Now, strip, and put on a leather jock, here is one for each of you, the waist strap is adjustable."

We all stripped. He had a good body, very muscular, he was about 50, 6', 185 lbs., nice cock, curved downwards, big, big, balls. He put on a leather vest, chaps, cap, high black boots, he looked like something out of the Village People, and had a riding crop, with a tassel like end, with maybe 20, foot long, leather strips, which had the capability of tickling you, or, making you hurt, depending on how it was wielded.

"Over the pommel horse (just like the one in the gym) next to each other. I want to see your holes, spread your cheeks."

We did, so far, so good. Then he began to use the crop on our asses, me then Marty, alternating, and, getting more heavy as time went on.

"Kiss each other." We did, I was getting hard, in fact, so hard that it was uncomfortable in my leather jock. I went to adjust my cock, "No adjusting, get used to it," and I just proceeded to get harder. Somehow the crop beating my ass was turning me on. I didn't understand it, but, knew enough to know it happens to some guys (and women).

"Marty, you getting hard?"

"Fuck yes, you?"

"Yes."

The whipping, if you call it that, was getting harder.

"I am going to fuck both of you, cock in one, fingers in the other, and then switch."

He lubed us up, and did a good job, condom on, lubed well, and, neither of us being virgins, he went in, I clamped down, to make it appear harder to get in than it would be, he commented on how tight I was, and I said, "Not quite a virgin anymore, and neither is Marty, but, we don't have a lot of experience," a lie if I have ever told one.

He pumped us, vigorously, and pulled on our jocks, further making me uncomfortable. He then pulled out completely and told us to 69, which we happily did, since it freed our cocks from the jocks. He stood there next to us and jerked himself.

He then got three dildoes down off the wall, stuck a big one up his ass, and thinner ones in Marty and me.

"OK, jerk off on my cock and balls." We did.

He came when we did, almost all three of us at the same time.

"Now," he directed, "lie down, on your backs, I am going to tie you down and edge you, and see how long you can take it."

We did, he tied our wrists out to the side, and our legs up by our shoulders, with our taint and hole exposed, lubed up his hands, and began to jerk us off. We were both hard again in a very few minutes. He was a very good gage of when we were almost ready to cum, and would let go before we did. He kept us in that state for about 15 minutes, and then backed off. We were lying there, hard as rock, oozing precum. Mine was just dripping in drops on my belly, Marty's was more of a steady stream.

Then Gary decided to suck our cocks, alternately. I really needed to cum, but there was nothing I could do about it. I had heard of guys who could do a "think off" and cum without manual help, but as much as I wanted to, and flexed my ass, on the dildo, I could not do it.

Then, all of a sudden, Gary jerked off faster and came all over the both of us, mostly on our cocks and balls.

"OK, now, I am going to free you up and I want you to jerk off right where you are." We did, it did not take long, maybe 45 seconds for me, and a minute for Marty. He smeared our three loads together, and then bent over and licked them all up. Marty reached for my hand, and held it, as this was happening, and I gave it a squeeze. I looked like we had survived this.

"There is a shower over there, take a quick one, get dressed, and you not only earned your fee, but, I will be happy to pay you more next time, but it will be more extreme, this was a baby step into the culture."

He paid us as agreed, and drove us back to the park, where we called it a night.

Next: Chapter 28


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