Daddy’s Boys

Nic P. Ramsies

It was three days until his rent was due and Kevin was $500 short. He thought about asking one of his roommates to front him the cash, but they weren’t too happy with him and he was pretty sure that would be the last straw. He also thought about going to the Fenway where on the paths in the neatly manicured community gardens gay men, married bisexuals, closeted guys, and those in denial for many reasons hooked up for fun or pay, or both. In the tall reeds that lined the garden and bordered the winding river, a blowjob could net him $20 each. He did the math: twenty-five blowjobs or eight a night and he could have rent. But he ruled the idea out. It wasn’t that he minded giving so many; he hated that awkward moment that happened every seven or so guys when the john, some desperate man or some married guy, usually wanted to start a conversation or exchange numbers. And frankly, spending three nights in the Fenway despite how much he liked to suck cock seemed unbearable. There had to be a quicker, more interesting way for him to make $500.

He’d been lazy this month, spending too much time and money taking the ferry to P-town, hanging out at bars, buying drinks and fancy dinners instead of working the streets or play parties. He’d lost track of how much cash he had left. He’d been at Copley Square ready to go out for the night yet again for fun not work when he went to the ATM and got the shocking news that he was out of cash.

He shook his head at his foolishness. He was smarter than this. Then he remembered the guy he’d met two nights before in P-town, Steve. Steve was a street boy like Kevin, only he had a great setup with a Daddy who paid him to work fancy parties in his big house in Arlington, outside Boston. Kevin had taken Steve’s number but hadn’t planned on calling. Steve had been a lot of fun and had told Kevin his Daddy would hire him in a second. But Kevin hated the idea of anyone owning him—for more than fifteen minutes, anyway. The thought of Steve’s Daddy’s cash made Kevin sort through the pile of discarded numbers written on slips of paper napkins and mixed in with grocery and to-do lists next to his bed.

After finding it, Kevin called Steve. “Hey, it’s Kevin, we met at…”

“Yeah, Kevin, I remember. What’s up?” Steve’s voice sounded deep and smooth. Kevin hadn’t remembered it that way.

“Nothing. Well, sorry I haven’t called sooner. I’ve been busy, I meant to. I…”

“You need some quick cash?”

“Yeah, I was wondering if maybe your Daddy had an opening, not full time but for the weekend.” Kevin felt awkward, something that didn’t happen often, and wondered in the pause that followed if going to the Fenway wasn’t a better idea after all.

“Sure,” Steve’s voice came back reassuring over the phone line, “he’s having a party tonight, in fact. It pays five hundred dollars. You know, if he likes you—”

“Yeah,” Kevin cut him off before he could finish, “just this once, really. I’m in a spot.”

Steve gave him the address, told him to wear something hot in leather, and to be there at nine p.m. The guests wouldn’t arrive until ten, but Daddy liked to have a drink and try out the new boys before anyone arrived.

Kevin showered, shaved, and put on a black muscle shirt and tight leather pants that showed off his package. He arrived promptly at nine p.m., not wanting to take any chances at pissing off Daddy. He pulled into the long tree-lined drive way and stopped behind the last parked car. A manicured lawn led to marble steps with topiaries on either side and a large mahogany door. Kevin rang the bell and a few seconds later Steve answered it dressed in an outfit almost identical to his. Steve’s blue eyes pierced Kevin’s. His dark wavy hair framed his face. Kevin ran a hand over his own short brown hair.

“Welcome,” Steve said, holding the door wide open and stepping to the side to allow Kevin into the entryway. “Daddy’s in here.” Steve continued before Kevin could say anything. “He’s waiting to meet you.” He led the way to a sitting room with a hardwood floor practically covered by a red and beige oriental rug. A love seat and two matching wing-back chairs in red velvet were placed in the center of the room facing each other. Wooden bookcases full of leather-bound tomes lined the outer walls, broken by the four windows and two doors.

“Daddy, this is Kevin. Isn’t he yummy?”

Daddy, a middle-aged man with graying temples, was much more attractive than Kevin had expected. His dark brown eyes seemed to spark as they moved about and his jaw was firm and strong. He wore linen pants and a light green summer-weight sweater with a V-neck that clung to his chest. He was fit, but not buff, a softness that suited him. He moved as if he had been a dancer—smooth and gracefully—although he was very masculine in his movements—sharp and defined. “Pleasure to meet you, Kevin,” he said as he extended his hand toward him. “So glad you could join us tonight. Do call me Daddy, if you will.”

Kevin shook Daddy’s firm grip, nodding. “Pleasure.”

Steve appeared with a tray with two identical cocktails on it. “Please,” Daddy said, indicting the tray, “make yourself comfortable.”

Both of them took a drink, then sat in the wing-back chairs. “My rules are simple, Kevin. Five hundred an evening. I provide food, clothing for the party, and drinks. You make my guests comfortable, be friendly, don’t get drunk, chat with them, and if they are interested, take them upstairs for some entertainment. Tips are acceptable, but not expected. The important thing is that everyone has a good time.” Daddy’s eyes seemed to be searching Kevin for some unspoken information, so he nodded. “If you enjoy yourself, if my guests enjoy you, we can speak about future party invitations. I host these twice a week.”

“Sounds great.” Kevin knew this would be his only party, but the arrangement seemed like heaven and Daddy seemed reasonable. Kevin had learned long ago that when a deal sounded too good to be true, it most likely was.

“There’s dinner and snacks, and Steve will show you around,” Daddy said as he set his drink down on the table next to him, “but first, I need to ensure quality entertainment for my guests.” Daddy rested his head against the back of the chair and spread his legs slightly. Kevin almost missed the instruction; Daddy had put it so neatly and politely.

Kevin put his drink down and walked over to Daddy, confident he’d pass the test. Kevin knelt between his legs, pushing his face against his crotch, breathing in his scent—Daddy smelled of bay rum—and ran his hand over the outline of his semi-hard cock and balls through the rich cloth. Kevin undid the zipper and reached his hand delicately into the pants to pull Daddy’s smooth cock out. His hand encircled the shaft and the tip of his tongue made contact with the crown. Kevin’s tongue worked its way around Daddy’s cock head in a slow circle before his lips closed around the now hard cock and his tongue continued to lick at the crown. Kevin looked up to see Daddy looking down at him. He was gazing at his cock in Kevin’s mouth with the same desire Kevin suddenly felt inside—a desire to please Daddy, like he’d never felt with a trick before.

Kevin’s lips sealed around his cock and he started to work his way up and down just the first few inches of Daddy’s shaft, pressing firmly on the underside of it with his tongue. Daddy didn’t resist the urge to thrust his hips forward. Kevin let out an audible moan as Daddy firmly grasped the back of his head. Kevin removed his hand from his cock so his mouth could take in more of the shaft and slipped his now free hand onto Daddy’s balls and gently touched the sensitive skin between his fingers and thumb, rubbing it, then kneading at it.