Roy's First Business Transaction

Once he was sufficiently slick, Cyrus pushed in, getting first dibs in popping Roy's proverbial cherry. It wasn't too hard, there was minimal resistance thanks to the amount of prep and how eager Roy was to take him. But then Vincent lined his own cock up and began to push in beside his boss. Getting fingered with three fingers wasn't enough to prepare Roy for this amount of stretching regardless of the amount of lube involved. Vincent wasn't a patient man, either, so the only thing keeping him from just going for it despite his earlier want to not hurt Roy was the firm look Cyrus was giving him over Roy's shoulder warning him not to.

Still, the going was steady, and with minimal tears and pained whines on Roy's part, both men were soon fully hilted inside him. He gasped lightly when all the pushing and stretching finally stopped, the fullness like nothing he could've ever imagined. It was almost enough to overshadow the discomfort of being stretched so wide. And then Cyrus grabbed his hips and Vincent grabbed his thighs and both men started moving him and it finally was enough to overshadow the discomfort.

Keeping up his usual stoic expression despite his hungry eyes watching his cock moving in and out of Roy, Cyrus was very much enjoying himself. Roy was already nice and tight and with Vincent also taking up space, he was even tighter. Not to mention the twitching and throbbing from Vincent's cock added a little something extra to the experience.

Having exactly none of Cyrus' self-control or stoic image to uphold, Vincent was grinning broadly as he craned his neck up to watch his and Cyrus' cocks disappearing into Roy. He'd expected to get some head and maybe sloppy seconds if he was lucky, he wouldn't have ever guessed Cyrus would be in a sharing mood. Vincent wasn't complaining, of course, this was a definite upgrade over head and maybe sloppy seconds.

Eventually getting to the point where he was comfortable enough to help, Roy began to move on his own, neither man releasing him and instead continuing to help him along. Now that the pain and discomfort was out of the way, all Roy felt was bliss. Moaning loudly as one cock brushed against his prostate, Roy chanced speeding things up and found the two men inside of him all too eager to oblige. Soon Roy was moaning loudly and regularly, joined by the occasional moan or groan from Vincent and the soft growls and groans from Cyrus. Mix all that with the wet sounds of sex and it was quite the chorus coming from Roy's room.

Speeding up and adding more pressure regularly, Roy soon found himself practically bouncing on the cocks inside of him. He was so focused on the action going on inside of himself that he was completely neglecting his own cock, both of his hands planted firmly on Vincent's chest for leverage. Neither of the older men seemed interested in jerking Roy off either as both of their hands stayed busy making sure Roy kept up his pace.

Stimulation to his cock proved unnecessary however, as Roy suddenly came with his loudest moan yet, hips jerking erratically, the only thing keeping him moving with any regularity being Cyrus and Vincent's hands. With Roy clenching and spasming around them, Cyrus and Vincent didn't stand a chance and came within seconds of eachother, both men ceasing in moving Roy at the same time so he simply sat on their cocks, taking their loads deep.

Recovering first, Cyrus pulled out and got off the bed, beginning to clean himself off. Vincent soon joined him, after helping Roy get off of his cock and laying the younger man on the bed so he could pant and come down from his high properly. After they had cleaned up, Cyrus and Vincent put their clothes back on and smoothed themselves out, leaving the room after they looked presentable once more. Miss Ivy stood waiting at the end of the hall and smiled when the two men approached.

"I trust you gentlemen had fun?" She asked, even with having heard everything from her spot in the hall.

"Indeed." Cyrus replied, offering Miss Ivy a light smile. "You've raised a very talented young man."

"I'll say." Vincent snickered, lacking any of Cyrus' tact.

"Well, thank you kindly, Mr. Fears." Miss Ivy said happily, not bothered in the least by Vincent's comment. "Does that mean I can expect another date in the future?" She asked, walking the two men downstairs.

Casually pushing Vincent out of the door when he looked at him hopefully, Cyrus smiled evenly at Miss Ivy. "Certainly. I'll be in contact."

"Fantastic." Miss Ivy chimed, waving at the men as they exited her shop. She closed the door and quickly locked up before hurrying back upstairs. Even after giving two courtesy knocks, Miss Ivy still managed to surprise Roy by coming into his room, her son gasping lightly and covering himself. "Calm down, darlin', it ain't nothin' I haven't seen before." Miss Ivy said, walking over to Roy and pulling him off the bed carefully. He wobbled a bit, no doubt feeling sore but didn't bother covering back up as Miss Ivy looked him over.

"They weren't too hard on you, were they, darlin'?" She asked, lightly cupping Roy's cheeks and looking at his face.

"No, ma'am." He croaked hoarsely, blushing a bit at the wrecked state of his voice and shifting a little uncomfortably as semen began to leak down his thighs.

"Good." Miss Ivy said, swiping at the tear trails on his cheeks with her thumbs. "You cried?"

Flushing a bit more and averting his eyes in embarrassment, Roy nodded softly. "It hurt some." He admitted, shifting again and clearing his throat to get his voice to come out more even. "But it also felt really good."

"That's m'boy." Miss Ivy said happily, swiping at his cheeks some more before releasing Roy. "I'm so proud of you, darlin'." She said sincerely, moving past Roy to get at his bed sheets. "Now you go and take yourself a nice, warm bath and when you get out, you come right back in here and rest up. I'll bring you some lunch and then come get you when dinner is ready." She ordered, stripping Roy's bed with practiced ease and looking at Roy expectantly.

"Yes, ma'am." Roy replied, hesitating before giving Miss Ivy a kiss on the cheek. He then quickly walked to the bathroom and closed the door softly.

Miss Ivy touched her cheek in surprise as she heard the water start running from the bathroom. She smiled to herself and set the bundled, dirty sheets aside so she could get the clean sheets on Roy's bed. Her and Roy's relationship wasn't really built on conventional affection so the kiss had been a bit surprising, but Miss Ivy hadn't minded it. She hummed to herself as she smoothed out the sheets and then picked up the dirty ones, depositing them in the washing machine for laundry day on her way to the kitchen.

In her subtle, manipulative way, Miss Ivy had been encouraging more touching between herself and Roy, holding his face more often and giving him more physical signs of approval in addition to the usual verbal ones. If Roy was going to be selling his body with any regularity, Miss Ivy figured he'd need to get the physical affection that that tended to lack elsewhere. She would be his outlet for all the hugs and kisses and reassuring pats he needed and the men Roy serviced would take care of his other needs. The way Miss Ivy saw it, it was a perfect system.

Of course, Miss Ivy lacked the need for romantic affection, having found early in her life that romance and relationships simply weren't for her. She was dominant, independent, and a generally unpleasant person wrapped up in kind smiles and sweet words and Roy simply wasn't any of that. One day he might decide he needed more than the life she was giving him, but for now, Miss Ivy was content to use her son for as long as she could.

Oblivious to the depths of Miss Ivy's manipulative cunning, Roy sat in the bathtub, smiling to himself as he washed off. He was sore all over but he'd never felt so satisfied. He'd gotten tag-teamed by two men he'd found attractive for a very long time, Miss Ivy was as pleased with him as she'd ever been, and now he was going to get to relax all evening. Feeling pampered despite the situation he was in, Roy sunk down a bit into the bubbles of his bath and allowed himself a moment to simply relax. Maybe being a prostitute really wouldn't be so bad.