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Darren was guiding him towards the lower bunk. “Lay face down, buddy.”
Kevin gulped, all full of fear again, “Please, no, please man?”
Darren laughed, “Relax! I’m gonna give you a good back rub. We’re gonna talk and
get to know each other a little. We got time for that, before any thing
happens.”
Kevin laid down, Darren sat on Kevin’s ass, hairy legs spread on either side of
Kevin. He rubbed some lotion into the soft teen skin and begin rubbing his
shoulders and neck.
Kevin felt the man’s weight and hairiness against him. He felt the man’s warm
balls and leaking hard cock touching his skin. He felt the strength in Darren’s
hands as they worked his shoulders.
Darren did most of the talking, but he was learning everything he needed to know
about Kevin. He was also teaching Kevin. Kevin learned that most men behind bars
mess around, some do the fucking, some get fucked, a few both. He listened to
Darren explain that there was a small amount of bisex boys in every man, whether
they admitted it or not. Kevin learned that most men don’t admit what they did
behind bars, forgetting it once they were free.
The two were on a first name basis when Darren’s massaged had reached the small
of the teen’s back. Kevin got goose bumps as the man’s strong hands gently
touched his butt cheeks. Darren’s fingers trailed gently over the boy’s smooth
ass, tracing patterns that meant nothing.
Kevin felt the fingers touching the crack of his ass. His fear caused him to
tense up, his muscles froze, waiting for the penetration.
Darren laughed, “Relax, Kev! You’re not even douched!”
Kevin looked at Darren confused, not understanding what was meant.
“Get up, Kev!” Darren took his spot on the lower bunk. “It’s your turn to
massage me now!”
Kevin felt even stranger as he climbed on the man’s butt. It was hairy, firm,
dimples on the side. The man’s waist was small, veeing up to large, broad
shoulders, muscular neck.
As Darren felt the teen’s horse cock and bull nuts rest against him, he laughed,
“Watch what you do with that thing, buddy!”
Kevin relaxed enough to laugh back. He begin to massage the man’s strong
shoulders as his had been done. More time passed as Kevin’s hands worked
Darren’s muscles.
Darren had continued to talk, building the teen’s confidence. He told Kevin
strange things, how if he had a cock Kevin’s size, he’d sell it on the street.
Kevin learned about men on the outside that would gladly pay to suck a cock his
size or to even get fucked by it. Kevin learned that his age and looks made the
price even higher. This amazed Kevin, as he couldn’t understand the reason
someone would pay for his dick.
Darren was actually enjoying schooling the kid, he liked sharing street smarts,
but there was another lesson Kevin needed to learn.
“Okay, Kev, get off me,” Darren said as Kevin’s massage had reached his lower
back. Darren stood, and walked to the cell’s toilet, he reached behind it and
pulled out a shampoo bottle. He ran the water in the sink, adjusting it to warm.
He filled the bottle with water, and rubbed lotion around it’s top.
“Now bend over and spread you cheeks apart,” Darren instructed. “I’m gonna
squirt this water in your ass, then you hold it as long as you can, then shit it
out.”
Kevin’s heart raced, he felt total humiliation as he got in the position that
Darren had ordered. He gasp as the bottle neck was forced inside him. Warm water
was squeezed from the bottle into his body. It was uncomfortable but not as
painful as he had first believed.
He flinched as he was forced to let the water out in front of the man. Over and
over, this was repeated, Darren now filling the bottle twice. “Good,” Darren
smiled. “You’re all clean, buddy!”
Kevin stood, not knowing what to do next.
“Bend back over,” Darren said, “I’m gonna get you lubed up and ready. I don’t
want this to hurt you, buddy, I know it’s your first time.”
Kevin felt Darren’s fingers against his ass hole. He couldn’t believe this was
happening, why, he wondered. Darren rubbed lotion into the teen hole, then
worked a finger in, applying lotion inside. He massaged the tight ring, getting
it to relax. Another finger and more lotion were added. Finally, the third
finger.
Kevin had felt stuffed, but really felt no pain. Darren had expertly relaxed his
ass hole, and did it so well, the teen wasn’t hurt at all.
Darren handed the lotion to Kevin, “Sit on the bunk buddy, you gotta get me
ready now.”
Kevin walked towards the bunk, his ass felt strange, he could feel the lotion,
he felt different back there.
As Kevin sat down, Darren said, “Lube up my cock now, body, get it nice and
slick. Feel it, get to know it!”
Kevin’s hands shook as he rubbed the lotion in. Darren’s cock was about 8
inches, it was very hard, thick, the head an deep purple. It leaked as Kevin
massaged the lotion into it’s vein covered surface.
Darren held the three fingers that had been inside Kevin’s ass together. “My
cock is thicker then these fingers, buddy. It’s gonna hurt you some. When I
start putting my dick inside you, I want you to push out, like you’re taking a
dump. That’ll help with the pain. I want you to take as much pain as you can,
but when it gets too rough, you tell me, buddy, okay?”
Kevin looked at the fingers, he looked at the hard cock. He was truly scared and
nervous. He wished the floor would split open and suck him in!
Darren said, “Now lay on the bed, face down, and spread your legs open. Put your
pillow under your belly, and here’s my pillow for under your head. You can bite
into my pillow if the pain gets bad. Now, remember, it’s only gonna hurt a few
minutes. The quicker I get all the way in, and get you opened up, the quicker it
goes away. You got it, buddy?”
Kevin had no voice, he nodded his head, taking one last look at what would soon
be entering his body, he got into position.
He flinched as Darren climbed on him. “Relax, buddy,” Darren said, kissing the
teen’s smooth neck, Darren simply rested against Kevin, the front of his body
against the smooth back of the teens. He held the kid tight, kissing his neck,
getting the tension to leave.
He was going to be as easy with this kid as he knew how!
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