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Teaching Trent (Adult Content)

Submitted by Jane B Night.

Trent blinked as he tried to open his eyes. Where was he? Had he been drugged?
He remembered the Funky Monkey’s bartender serving him his first beer of the night. He had only had one. He was sure of that. He didn’t feel drunk anyways. He just felt odd. Like he had fallen asleep and was now just waking up. Except that he had no idea where he was or who the man standing in front of him was.
“Bout time,” the man said.
“Where am I?” Trent asked.
“It doesn’t matter.”
“Who are you?” Trent asked. Had this man been at the bar? Maybe. He looked a little familiar.
“You can call me Apollo.”
“You’re joking.”
“It doesn’t matter what my name is now does it?” Apollo said. Trent guessed not. He looked around the room. Was he in an attic? He could see a skylight overhead but no other windows. The spot where he and Apollo stood was lit by a reading lamp but the rest of the room stretched out in darkness. Where was the door?
He looked around for anything he could use as a weapon if he needed it but the room was sparse. There was only the lamp and the lazy boy chair he was seated in. A large freestanding mirror that showed his disheveled complexion stood across from him.
“I’m not going to hurt you,” Apollo said.
“What do you want with me?” Trent asked.
Apollo smiled.
“Put this on.” Apollo handed Trent a blond wig, a red chemise, and a pair of high healed red ladies shoes.
Trent could feel his face paling. How had this man known his fantasy? A fantasy he had never told anyone in his life. A fantasy he imagined while his dick was monotonously fucking the chit of the week?
“Just do it,” Apollo ordered.
Trent peeled off his black polo and blue jeans hesitating over his boxers.
“Those too.”
Trent’s eyes never left the mirror as he put on the chemise first. His chest hair peeked over the lace around his chest and his traitorous dick saluted against the silk fabric.
He put on the wig which felt as if it was made from real human hair. And then finally the shoes, surprised they fit.
“Now suck my dick,” Apollo said undoing his fly and freeing a rather oversized cock. He took a seat in the chair Trent had previously occupied.
Hesitating Trent got down on his knees before Apollo and pulled the cock into his mouth. He began to suck on it.
“It’s a dick not a tit,” Apollo said giving his bared ass a slap.
Trent took the dick in one hand and slowly began moving his mouth up and down over the shaft. Was he really doing this? Was he really sucking this man’s dick? And, why did he like the taste so much. And the smell that filled his nose as his lips moved up and down on the hard shaft. It was a masculine smell. A pleasant musk. And the feel of the enormous cock in his mouth was a mixture of the hardness of the cock and the softness of the skin.
“Stop,” Apollo said. Trent wanted to keep going.
“Stop,” Apollo said again gently pushing Trent away. Trent was disappointed. Had he done it poorly?
“We aren’t through. But I wanna finish in your ass,” Apollo said.
He pulled Trent to his feet and bent him over the chair.
Trent felt Apollo spread him until his asshole was exposed. Apollo spit on his ass before he felt the cock slowly pushing through the opening.
Trent suddenly felt overcome with pleasure. Not the kind of pleasure he usually felt when fucking. This was a pleasure that made the room fade and stopped time. He felt a sudden hint of annoyance as Apollo gently turned his face. Then Trent understood.
He looked in the mirror and saw himself bent over the chair. His legs ended in the red heels spread around Apollo’s. His red chemise pulled up so that his ass cheeks were exposed. He saw Apollo’s hands on his ass cheeks kneading them. And he watched as Apollo fucked him.
The sight brought him nearly to the edge. He could see his dick jerking in the space between his chest and the chair cushion and he could feel the tingling start in his balls and steadily flow through his body.
Then, he watched as Apollo reached around and grabbed his dick and began to pump it fiercely in stride with his thrusts.
That was the end of what Trent could take and he let go then. He felt the hot fire that had filled his body burst out of his cock. He felt himself let out a sound somewhere between a guttural animal groan and a scream of pleasure. He fell forward against the chair in exhaustion and watched as Apollo stiffened with his own moan. And then he felt the hot cum filling up his ass.

Once Trent’s clothes were on he realized that he still had more questions then answers but he wasn’t sure how to voice them.
“You are free to go now,” Apollo said before he had even formed the question fully in his mind.
“Not yet.”
“Trent,  now you are free to be who you are.” He said in the tone of a weary teacher speaking to a stubborn student.
“Free to be who I am?”
“I was born with a gift. The gift to see into the mind of others. I was in the bar and saw your fantasy. Saw your uncertainty about it. Knew that the only way you would ever be happy is to see that the man in the fantasy is who you are. And I brought you here to prove it.”
“Will I ever see you again?” Trent asked. It seemed like the most logical question he could muster.
“Perhaps. But there are a great deal more people who need my help. A great deal more who need me to show them who they really are. And you know now. You know who you are.”

About Charles Yallowitz

Charles E. Yallowitz was born, raised, and educated in New York. Then he spent a few years in Florida, realized his fear of alligators, and moved back to the Empire State. When he isn't working hard on his epic fantasy stories, Charles can be found cooking or going on whatever adventure his son has planned for the day. 'Legends of Windemere' is his first series, but it certainly won't be his last.

2 comments on “Teaching Trent (Adult Content)

  1. Good night Ms. Night. The story was intriguing and well written. Hot too!

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