Shave and a Haircut - 750

Eric had slipped out just before 2:30pm when his appointment was scheduled. He had raced downstairs just to circle the retail concourse in the basement of his office tower. This date had been circled on his calendar for a year. Why couldn't he bring himself to go in?

"Peterson! How've you been son?" Brent McGregor was a senior VP in mortgages. Eric could only wish to have five minutes with this guy on any other day, just not today. He could feel the sweat beading on his forehead.

"I'm great sir - you know how it is in foreclosures-"

"Yes, yes- been a couple decades since I've manned those phones, I'm sure you've got a great career ahead of you- say, were you going to Jerry's? I was heading in there myself, just a hot towel and shave,"

The older man had slung his arm around Eric's shoulder and steered him into the barber shop where he'd been stalled for the last few minutes. This was NOT happening, he screamed internally.

"Jerry! Sorry for the surprise, I brought a friend-"

"Yes, Eric, you're late for your appointment, come get in this chair," Eric stared at the handsome stylist, begging for some reprieve.

"Uh, well know what Jer' - Mr McGregor's a real busy guy, why not let him take my spot and I'll come back later,"

"Nonsense Peterson, I'm good for a nap anyhow- I'm sure Jerry won't mind double teaming us, if you give him moment to get me started. How bout it Jerry?"

Eric tried to silently express his panic to the barber while still appearing business casual. Jerry stood there, his bald head shining in the track lights as he considered the two men. He stroked his finely trimmed grey beard and nodded.

"I think I can accommodate both of you fine gentlemen, if you will," Jerry motioned for Mr. McGregor to take a chair in the shampoo area behind a row of mirrors. Normally, the barber shop would be bustling with cutters, but Thursdays Jerry worked alone.

Once the executive was settled in with a hot towel over his face, Eric surrendered his suit jacket and was waved into a chair. Jerry walked over to the entrance, pulling the shade down and locking the door. His face turning to one of annoyance as he neared his customer. He glared at Eric, willing him to unbuckle his belt and undo his zipper.

Ever so quietly, Eric removed his belt and opened his pants- looking up at Jerry for approval before continuing. He lifted his ass up as he drug his slacks and underwear mid thigh, exposing his caged cock to his keymaster.

It had been a year.

Displeased, Jerry took hold of Eric's pants and forced them down to his ankles, causing the young man to panic. The boss of his boss' boss was a mere ten feet away.

But if he didn't want another year with his penis locked up, this had to happen now.

The barber gave his groin a look, barely turning to grab his shaver while muttering the word "nipples".

Eric checked Mr. McGregor's slumber in the mirror and began to unbutton his shirt as Jerry started to buzz the mess of pubic hair that had grown around his cage. In no time he was as smooth as a baby, with the vibrations causing his cock to push at its boundaries. He was so close to release, he could taste it.

The two men startled at McGregor's sudden snoring but returned their focus to the task at hand. Jerry's clippers moved up Eric's belly and sheared the patch of hair between his nipples. The skilled barber removed all trace of manliness from Eric's body from knees to neck before cuffing his arms behind the chair and removing the sharp blade from the clippers.

Jerry wrapped the head of the shaver in a hand towel, flipping it on and jamming it under Eric's sack before oiling his hands and taking his spot behind him. He worked the boy's nipples while whispering belittling insults as the vibrations caused Eric to shake and whimper. With a single twist of his fingers, Jerry sent a jolt to Eric's balls, causing his trapped dick to spit and leak. The cum oozing through the cage and onto his thighs.

"Another year then?" Jerry whispered. Noooo! Eric was dying inside.

"Maybe you should take it off," Mr. McGregor suddenly appeared in the mirror. "I'd like to see how small it got."