He paced nervously inside his hotel room. He was nervous and scared but determined to see this through. All through school he had been bullied and humiliated for being the shy runt, and since this was his first year at college, he wanted to break away and be a man.
When he answered the knock on the door, he was pleasantly surprised but even more nervous. She was really pretty but dressed conservatively in a pullover sweater and slacks. She entered the room before he could even greet her. The sweet scent of her perfume intimidated him even more.
She seemed to be a few years older then him, confident in her demeanor. He handed her the envelope, as she had instructed him over the phone.
"Get undressed," she said as she reached into the envelope.
Before she could count the cash, she noticed a small folded up note in the envelope, which she read out loud.
"Blow job until I come
Fuck me until I come
Let me play with your tits
Sit on my face
Let me lick your ass
Maybe let me taste your pee"
"What's all this?" She asked, tossing the list aside.
"Things I've never done. I'm a virgin and I didn't want to forget anything."
She laughed for a minute and then decided to play with him.
"What about a hand job? You didn't list that."
"I've jerked off lots of times, so I know already what that feels like."
"But have you ever had a girl do it for you?"
"No, but it would feel the same, wouldn't it?"
"How long does it take you to come when you masturbate?"
"It depends on the porn I'm watching, maybe ten or fifteen minutes?"
"A girl can make you come faster than that."
"Really? I don't see how."
She stepped close and put her lips up to his ear and whispered.
"I could jerk your cock while I sit on your face and piss in your mouth and you'd come in less than a minute."
He grabbed his cock through his pants. "Holy shit!"
"Are you gonna come in your pants?" She asked with a smile.
"No, but, Jesus, take it easy!"
"Looking at this list, I'd say you'll need me at least an hour and a half. My rate is $500 an hour, so do you have $750?"
"Oh..." he mumbled, "I, um, I guess I should have asked how much, because I only have $423, and I put it all in the envelope thinking part of it would be a nice tip for you afterwards."
She silently counted the cash in the envelope. $423 exactly. She wasn't about to get this kid off twice for less than her regular fee, but she had an idea. He was cute, shy, and she didn't have anything better to do for a couple of hours.
"I usually have costumes and do a nice strip tease, but since you're short of cash, I'll skip that and make an exception for you, but with two restrictions.
"Okay," he said eagerly.