My Papi

“This picture is of my wife and one year-old daughter” said Chad, a good looking 25-year-old white guy on the short side who was at my place. “I’m totally straight and have never been with a guy or every had any interest, which is why I’m here.”

“I was charged with embezzlement. I’ve taken a plea deal for a four year sentence. I go away in two weeks. It’s maximum security.” It was where my uncle did three years for cocaine possession. “After legal fees and fines there’s not much left. My wife has taken a job. I don’t have the funds to pay for protection and I’m going in without any connections. Considering my age and what I look like I have a good idea what to expect. I feel if I enter mentally and physically prepared, I’ll have a much better chance of making it. You were recommended to me as someone who could be of help.” Hmmm.

“Okay. This is going to be overwhelming for you but feasible, as I believe you’re capable of adapting as you’ve thought this through. I propose two private sessions and two group sessions with additional participants to be paid $200 each. I really think we could accomplish the goals you’ve set.” “I can swing that.”

“Great.” I said as I stood up and unzipped. “You can start by getting on your knees and I’ll talk you through sucking my dick. Clear your head. Focus and concentrate on nothing else but bringing pleasure with your lips, tongue and throat.”

He was wearing khakis and a light blue long sleeve shirt. He got on his knees and raised his head and looked up at me. “It’s important to make eye contact. Open your mouth wide. Do your best to keep your lips over your teeth. Put it in your mouth. Nice. Now lick me all over and watch the teeth. Play with my balls. Use your tongue on them. Suckle the head and use your tongue under it.” We went on with the tutorial and he was a fast learner but needed a lot practice to get the hang of smoothly deepthroating.

“Take off your clothes and leave your underwear on.  Get in the bed on all fours and pull your briefs down to expose your hole.” I lubed up his ass and went to the front. “Lube up my dick.” I went behind. I fingered him. They don’t use condoms in prison, so I put the bare head of my cock in his hole and very slowly began edging it in. He was grunting. I got it in and fucked him tenderly at first and then with more force. “Oh God my God!” he howled as he shot off in his underwear. “I never came like that before.” “You’ll get used to it and live for it.”

I pulled out and told him to get on his back. I grabbed his legs and rammed into him and fucked him for a while. He was crying more from the shame of liking it than the pain. I pulled out and cleaned off my dick. “You’re going to suck me off and it’s very important that you learn to swallow.” Now, he looked disgusted and his eyes were red from crying. He opened wide and got to work. I held his head as I blasted, and he was gagging and choking as he swallowed me. “That went very well. You have the basics down…” He took a shower and left.

“Fucking punk! Take my mother fucking dick you piece of shit maricon!” Chad was on his knees only wearing a black jockstrap  and I was fucking his teary face rough. This second session was by design more intense then the first. “Watch your fucking teeth bitch!” I fucked him standing up, on the floor ass up and several other positions to get him used to taking it anyway any guy might like. I only used spit these times as you couldn’t always count on lube inside. I was getting close, so I pulled out and had him suck me off. He was like going to throw up because I hadn’t cleaned my dick. It had spit and had been in his ass.

“Now peel back the skin and suck it like usual…” For the third session I brought over an older cousin who is uncut. Chad needed to learn to deal with that because he’d be working with that a lot inside. He did good then and my cousin and I got him used to taking it at both ends with a lot of slapping around and dirty talk.

“Hey, bitch use your hands on them you dumb faggot!” Chad was in on his knees in a black jock sucking my cock and was now stroking my father and uncle’s hard cocks. He was clumsy at first, but he got the hang of giving hand jobs while sucking. I’m proud to say that I made Chad into a first-class sword swallower. He made love to my, my father and uncle’s great dicks with his sweet mouth. They were happy to help me and also happy to get $200 each. We let loose on Chad. After Chad had been seeded, stretched open and sprayed with our cum all over, he took a shower.

“Damn you get paid to fuck! Living the life!” said my uncle. “I’m proud of you son. You got a great set up.” “We taught you good said my uncle.” I basked in their affirmation. Chad returned dressed and shiny. We all sat on the couch. My uncle spoke.

“Look, some guys are naturally tough and are able not end up as a punk. You’re not one of them. This was a good idea of yours. From what I see, you’ll do okay. You take orders. You don’t talk back. You’re a great cocksucker and take a hard fuck all the ways there is. The main thing is you got to clear your head. Forget about your big job, money and the country club. That life is over. Your life for the next couple of years is knowing your place. Seven days a week, day and night you’ll be doing what you’re told, getting cons off.”

“It’s important the first time you’re hit on to act like it’s your first time. Your first guy will like you better if he thinks his dick is the first you ever sucked and brag about it. Talk about your wife and kid. It’s a big turn on to make a straight guy a punk. Good luck to you.” “Thanks” Chad left. We hung out for a while drinking beers and catching up. “Of course, he won’t be the same after said my uncle.” “He’s not the same now as he was when I started training him” I said.

There was one more exercise for Chad. We took an Uber to Flushing for a private thug gay sex party in a warehouse. Chad paid our entrance fees as well as my standard rate. The quota was 80% black and Latin and 20% screened whites under 30. Chad had to send nude pics to get approved. We took of our clothes and put them in lockers. Chad was in his black jock. I wore red Calvin Klein boxer briefs. We walked around, me as a proud Latin top with swagger, my big dick and juicy balls swinging in my underwear and Chad as a pussy bottom with his ass up for grabs. To get used to it was going to be, I had instructed him that he was to put out for anyone who was interested in him.

In no time Chad was sucking his first big black cock from a chiseled body builder in his late 20’s, before getting his hole rammed with all nine inches of it. Then a posse of young Latin bros took turns on him with their pingas that Chad expertly took care of in every way. Then there were two skinny black tops with dreadlocks who had him. This multicultural experience was to get him fully acclimated to what and who he would be dealing with on the inside as a prison bitch.

I got sucked by a few white boys and fucked a hot white jock. Chad and I were both fucked out and got dressed. We ran into the black body builder. “Hey, my name is Derrick.” “Chad.” “Nice to meet you Chad. You are one hot bottom. Not many guys can take me so well, I want you again.” “Uh, thanks but I’m moving away in three days.” “Then we better hook up again before you go. What’s your number?” Chad was shocked but recited his number, which Derrick entered into his phone. “I’ll text you tomorrow. I’m a trainer at Equinox at 50th and Broadway and live close by. I get off at 2:00 PM.” “Cool.” “Would you be up for a threesome with my manager? He’s a fun hung Guido.” “Uh, sure.” “Great! See you tomorrow.” 

We each got an Uber. Me to my place and him to his house on Long Island. “Have a nice time” I laughed. The next night, Chad called me and recounted his hot afternoon with his new gym buddies. Two days after that he went away.