Roy's First Business Transaction

Author's Note: This can be read as a stand-alone story, but it's technically a sequel to "Miss Ivy's Boy" so you might consider reading that one first if you wanna fully understand everything that's going on.

***

"Roy, darlin'?" Miss Ivy called, motioning for Roy to come to her when he looked up from his phone. She smiled as he pocketed his phone and hurried out from behind the counter, coming to her side.

"Yes, ma'am?" He asked, smiling at Miss Ivy and taking without question the pruning shears she held out to him.

Stepping aside, Miss Ivy motioned at one of the many ivies littering the shop. "Odessa has a brown leaf that needs tirmmin' and you know how she doesn't like me." She said, smiling as Roy stepped up instantly and easily located the leaf that needed trimming.

Snipping the leaf off easily, Roy then brushed his thumb over the spot. "Sorry about that, Odessa, but it was just a tad unsightly." He said quietly, smiling at the plant. "You look ravishing as ever now."

Laughing softly, Miss Ivy took the shears from Roy and set them on a table so she could cup his cheeks lightly. "I love it when you talk to the ladies." She said, lightly squishing her son's cheeks and smiling more when he laughed softly and blushed.

"You always said if I was nice to the ladies, they'd grow nice for me." Roy said, still smiling when Miss Ivy let his cheeks go.

Smiling warmly, Miss Ivy motioned for Roy to follow her as she picked the shears back up and continued her pruning. "I wanted to ask you somethin' real important, darlin'." She said, glancing at Roy out of the corner of her eyes.

"Alright?" Roy asked uncertainly, a light frown playing his face.

"You think Mr. Fears and Mr. Laurence are handsome, don'tcha?"

Flushing, Roy looked away, only brave enough to do it since Miss Ivy wasn't looking at him. He normally tried to keep his eyes on her face when she spoke to him because that's how she'd taught him. "Yes, ma'am." He said softly, shuffling a bit. "Is this about what I did with Mr. Laurence?" Roy asked, hoping Miss Ivy wasn't upset since it'd been a few days since the incident and she hadn't seemed upset when it happened.

"Mm-hm." Miss Ivy hummed, still pruning away but glancing at Roy occasionally to catch his reaction. He was nervous, maybe a little afraid. Good. The relief when he found out that she wasn't mad would help with getting him to agree. "Say I wanted to arrange a little date between you and Mr. Fears and Mr. Laurence." Miss Ivy started, stopping to look at Roy properly and feeling satisfied when he looked up at her obediently. "How would you feel about somethin' like that?"

"I-I think I'd like that." Roy said cautiously, shifting a bit more. "I- are you asking me if I'll sleep with them?" He peeped, not really believing it and not wanting to upset Miss Ivy if that wasn't where she was going with this.

"I am, darlin'." She confirmed, smile still just as warm as ever and tone sweet as honey.

"Oh." Roy breathed, eyes slowly widening as the idea really sank in. "Oh. I- yes." He said, rather enthusiastically before dialing it back down shyly. "I would like that alot."

Smiling broadly, Miss Ivy pulled Roy into a cushiony hug. "That's m'boy!" She said happily, giving Roy a squeeze and stroking his hair when he slowly hugged her back. "There is one little detail that I hope won't snag you up too bad."

"What is it?" Roy asked, looking up at Miss Ivy inquisitively.

"We'll be getting paid for it." Miss Ivy said, releasing Roy and watching his face with calculating eyes for a reaction.

Flushing, Roy let Miss Ivy go. "We?" He asked, not sure how to feel about this detail.

"Well of course, darlin', it's your body I'm sellin', I wouldn't feel right keepin' all the profits." Miss Ivy said, placing her hands on her hips.

"So- I'd kinda be like-"

"A prostitute, darlin'." Miss Ivy finished, tone still sweet and smile still warm. "And I would be your pimp. I'll pick out your potential clients, you'll get final say on who you fuck, and we'll split the income." When Roy still looked uncertain, Miss Ivy cupped his face and gave him her most motherly smile. "Don't think of it like all that though, darlin'. Think of it like you gettin' to sleep around with as many men as you want in the safest way possible while also makin' a little extra money to treat yourself with."

When she put it like that, it did sound pretty nice. Thinking it over, Roy nodded slowly, Miss Ivy releasing his cheeks with a pleased grin. "Okay. I- it does sound pretty fun, I guess." He admitted, smiling shyly when Miss Ivy stroked his cheek affectionately.

"I knew I could count on you, darlin'." She said softly, smiling affectionately at her son. "You're such a good boy, agreein' to do this for me." When Roy beamed at the praise, Miss Ivy knew for certain she had him. She patted his cheek gently and let him go. "Alright, darlin', that's all I needed. Mr. Fears and Mr. Laurence will be here in three days to break you in so try not to tire your body out before then."

"Yes, ma'am." Roy replied, blushing at the implication and going back to the counter when Miss Ivy went back to pruning. This was still all pretty odd and Roy still didn't really know how he felt about being a prostitute, or about his mother being his pimp, but he knew Miss Ivy would never put him in harm's way and if having sex could bring in income for them, why shouldn't it? Maybe that was just the part of him that wanted to make Miss Ivy happy talking, but it was the part of him that was easy to understand so it was the part he listened to. The part that wasn't sure how to feel could be unsure all it wanted, Roy was just happy that Miss Ivy was happy.

As if she could hear Roy's thoughts, Miss Ivy smiled to herself. It'd been so easy to convince Roy to say yes. Her good little son who always put her before himself had practically jumped at the opportunity to make her happy. If she could've ever found a woman exactly like Roy but more petite, she might not have decided to live her life loveless. As it stood now though, she had her business and she had her boy and that was all she needed.

The rest of the day went by normally and so did the next few days, only Roy's mounting sense of anticipation and nervousness making them any different from any other day. Finally three days were up and when Roy woke up, he realized he'd slept in, his alarm either not having gone off or not having woken him. Getting out of bed quickly, Roy hurried to the kitchen only to find Miss Ivy finishing up cooking breakfast. "Sorry I'm late, ma-"

"No, no, darlin'." Miss Ivy interrupted, plating their breakfast and taking Roy by the shoulders to lead him to his seat at the table. She pushed on his shoulders and he sat, Miss Ivy pushing his plate of food up to him. "I turned your alarm off. You've got a big day ahead of you, so I thought you could use the extra sleep."

"Oh." Roy muttered, taking his fork and looking up at Miss Ivy. "Well, thanks."

"'Course, darlin'." Miss Ivy said, kissing the top of Roy's head and sitting across from him to eat her breakfast.

After breakfast, Miss Ivy stopped Roy from helping her clear the table. "Now you go on and make sure your room is presentable for Mr. Fears and Mr. Laurence and then get nice and clean for 'em." Miss Ivy said, making a shooing motion with her hands. "I'll take care of the dishes." She started piling plates but then looked up at Roy again. "They'll be here by noon, so try to be ready by then, darlin'. It ain't good to keep clients waitin'."

"Yes, ma'am." Roy said, leaving the kitchen obediently and going into his room. He could see what Miss Ivy meant. She was a bit of a neat-freak around the common areas of the house and down in the shop and, Roy imagined, not really knowing as he wasn't allowed in there, her own room, but Miss Ivy allowed him to keep his room however he liked so long as it didn't get too out of hand. Roy was generally neat simply because living with Miss Ivy had rubbed off on him, but his room could definitely use some tidying up.

Getting to work, Roy made his bed first, fixing the blanket and fluffing his pillows. Roy tidied up his dresser drawers where some of his clothes were hanging or poking out and decluttered his nightstand and desk. The whole process didn't take longer than an hour and then Roy did as Miss Ivy said and took a shower. His stomach was fluttering nervously but he was excited for what was to come. Not allowing his excitement to get out of hand, Roy exited the shower and after he was dry and dressed, he realized he still had quite some time to wait before noon rolled around.

Frowning a bit at that, Roy went downstairs and found Miss Ivy flittering around the shop, checking on the plants and straightening up pots and supplies that were probably fine. "Ma'am?" He said, getting Miss Ivy's attention. "I finished cleaning my room and showering." He informed, hoping Miss Ivy would give him something more productive to do than wait in his room or something.

Realizing Roy was too full of nervous energy to simply relax, Miss Ivy smiled warmly at her son. "Alright, darlin'. How about you come downstairs with me and help me with the seedlings?" Miss Ivy called her illegal plants "seedlings" that way they were easier to talk about in public or with other people around.

Smiling in relief at being given something to do, Roy nodded. "Yes, ma'am."

Not worried about a customer coming in while they were downstairs, Miss Ivy led the way to the basement, Roy following behind her. They spent a few hours down there, Miss Ivy only letting Roy do things that wouldn't get him dirty, before it got too close to noon. Five minutes til, Miss Ivy led the way back upstairs and straightened out Roy's clothes and hair a bit before pointing up the stairs.

"Go on, now. Mr. Fears and Mr. Laurence will be here soon. I want you waiting in your room for 'em." Miss Ivy commanded, lowering her hand.

"Yes, ma'am." Roy answered, going upstairs to his room and feeling all of his nervousness and excitement return tenfold. What if he wasn't any good at sex? He'd never had it before and now he was going to have it with two people at once. He'd played with himself, sure, but he doubted taking a real cock was the same as using a dildo. Still, Roy couldn't wait to have Mr. Fears and Mr. Laurence all to himself. He couldn't believe both men were so interested in having sex with him that they'd pay for it.

Smiling at her good, obedient boy behind his back, Miss Ivy kept herself busy. She was also rather nervous. She didn't know for sure that Roy was a virgin since he had friends he went out with, but she suspected strongly that he was. If he didn't perform well, it could put a dent in her relationship with her most powerful client. Miss Ivy felt uncomfortable when she thought about the amount of trust she was putting in Roy, but she tried to reassure herself. Roy had never let her down before and it was just nerves making her think that he would now. Vincent had enjoyed the blow-job he'd gotten from Roy, after all, so maybe her boy was a natural. Either that, or he'd simply had practice in that department.

Not getting any more time to dwell as the bell above the door chimed, Miss Ivy spun around with her practiced honey-sweet smile on her face. When she saw it was Cyrus and Vincent, her greeting died on her lips, and her smile became much more genuine and less saccharine. "Well, just on time! I'd expect nothin' less. Good to see you gentlemen." She called, meeting Cyrus halfway and partaking in their customary la bise greeting. When they pulled away, Vincent got his customary acknowledging smile, Miss Ivy getting her customary smile and nod back.

"I would never keep you waiting, Miss Ivy." Cyrus replied smoothly, smiling at her.

Giving an approving hum, Miss Ivy motioned to the upstairs part of the house. "I'll show you gentlemen up to Roy's room." She said, leading the way. Cyrus had already paid Miss Ivy for Roy's services so all that needed to be done was for both men to collect. Knocking twice on Roy's door more out of courtesy than anything, Miss Ivy opened the door and smiled at her son. "Mr. Fears and Mr. Laurence are here to see you, Roy." She said, her tone reassuring and smile encouraging.

Without waiting for Roy to respond, but giving him a moment to sit up attentively on his bed, Miss Ivy moved aside to let the older men into Roy's room. "I'll leave y'all to it." She said, flashing one last smile before closing the door and walking down the hall. Miss Ivy didn't feel like she could work with how anxious she was, so she simply leaned against the banister of the stairway and waited. Best case scenario, she'd hear everything going well from Roy's room and worst case scenario, she'd be close by to do damage control. The only downside is that she'd have to listen to her own son getting plowed. Not the worst downside ever, not great, but not the worst.

"Hello, Roy." Cyrus greeted calmly, smiling pleasantly at the younger man.

"Hello, Mr. Fears, Mr. Laurence." Roy greeted, still nervous and not really sure what he should be doing.

"You'll call me "sir" for the duration of this transaction." Cyrus replied coldly, smile never fading or growing even at the satisfaction he felt when Roy shivered lightly.

"Yes, sir." Roy replied quietly, looking at Vincent expectantly, hoping for some direction.

"Vincent's fine, kid." He said, decidedly more chill than Cyrus.

"Okay." Roy said, relaxing a bit now that he had some ground rules to follow. Rules were good, rules were structure, rules were familiar.

"Now that we've gotten that out of the way, strip." Cyrus commanded, watching in satisfaction as Roy hurried to obey him, getting off the bed and getting naked quickly before kneeling on the bed again. "Good boy." He praised lightly, smirking now. Miss Ivy certainly knew how to train an obedient little thing.

Flushing at the praise, Roy smiled lightly and then flushed even darker, eyes widening as Cyrus and Vincent stripped in front of him, both men taking the time to fold their discarded clothes and set them aside on a nearby chair. Soon they were both naked and Roy couldn't help but let his eyes travel from one man to the other, his cock beginning to stir at the sight. He was slowly but surely forgetting all about how nervous he'd been.

Stepping up to the bed, Cyrus reached out and lightly carded his fingers through Roy's short hair. "On your hands and knees." He ordered lightly, releasing Roy's hair so he could obey. Glancing over at Vincent, Cyrus moved his head towards the bed. "Prepare him while I give his mouth a try."

"Sure thing, boss." Vincent replied, getting on the bed behind Roy and kneeling there. He grabbed the conveniently placed lube from the nightstand and slathered up three of his fingers before sliding the first one into Roy. He took it easily just like Vincent figured he would.

Looking down at Roy in a way that made him feel small and insignificant, Cyrus held his cock in one hand expectantly. "I've heard good things about your oral talents." He said, releasing himself as Roy eagerly took his cock in one hand and licked the tip slowly. It was only his years of practice that allowed to Cyrus' voice to come out as evenly as it did. "Let's see if you live up to it."

Trying not to feel nervous as this suddenly felt like an evaluation, Roy focused on the task at hand. Taking the head of Cyrus' cock into his mouth, Roy lavished the tip with attention from his tongue, applying a steady amount of suction while he slowly stroked what wasn't in his mouth. He felt Vincent add a second finger to his prep and moaned around the tip of Cyrus' cock as Vincent started finger-fucking him, stretching him out as he thrust the two digits in and out slowly.

Clenching his jaw a bit as the vibrations from Roy's moan sent shocks of pleasure down his cock, Cyrus put an encouraging hand on the back of Roy's head and guided him forward just a bit. The younger man got the hint and kept going on his own, slowly taking Cyrus to the root with minimal difficulty. After the thorough throat-fucking Vincent had given him, which Cyrus had eventually been regaled with, it was no wonder he didn't have a terribly hard time taking a cock that deep gently.

Adding more suction, Roy began to bob his head, endeavoring to take Cyrus to the root every time he moved down. Every now and again he'd look up and catch Cyrus' eyes, a little shiver going through him at the look the older man was giving him. It was thinly veiled hunger and an odd coldness and even though it was incredibly intimidating, Roy found it impossible to keep himself from looking up to catch it again.

Seeing that Cyrus was definitely enjoying himself, Vincent spoke up. "What'd I tell ya, boss?" He asked, fingering Roy slowly as he watched the show from where he was behind him. "He's a grade-A cock slut."

Humming, Cyrus watched Roy swallow his cock repeatedly. "This is only your second time doing this, is that correct, Roy?" He asked, idly carding his fingers through Roy's hair again.

"Yes, sir." Roy answered, only leaving Cyrus' cock unattended long enough to answer before he got back to work.

"Very impressive, indeed." Cyrus murmured, suddenly tightening his grip on Roy's hair and keeping him from moving up off his cock, keeping his shaft hilted in the younger man's eager throat.

Grinning, Vincent added a third finger to Roy's ass, trying to get him as prepped as possible. He'd been on the receiving end of what Cyrus was doing many times. He'd be a filthy fucking liar if he said the calm, casual way Cyrus had of abusing him didn't turn him on more than anything else about his boss. He did everything with the same stoic expression. From conducting business transactions to choking people with his cock. It had a way of making you feel small and worthless but Vincent had found quickly that he was into that when it was Cyrus making him feel that way. If the way Roy's ass was milking his fingers was any indication, he was also into it.

Releasing Roy's hair, Cyrus let the younger man come up for air, gently guiding him off of his cock. "That's enough." He said calmly, unable to keep from smirking at the disappointed sound Roy made. "Don't be like that." He chastised lightly, tone almost playful. "You'll like where I'm going to put it next much better."

Blushing darkly, Roy couldn't help but smile. "Yes, sir." He said softly, making Cyrus hum in approval.

Taking his cue from Cyrus stopping his blow-job, Vincent removed his fingers from Roy and moved aside so his boss could take his place. When Cyrus didn't move, however, Vincent looked at him questioningly. "Somethin' wrong, boss?" He asked, sure Roy hadn't fucked anything up with his amazing mouth and feeling slightly nervous as that meant he was the only candidate for having potentially fucked something up.

"How would you feel about taking Mr. Laurence and myself at the same time?" Cyrus asked, ignoring Vincent and looking down at Roy.

"You-you mean in the same hole?" Roy asked softly, looking a little unsure.

"Indeed." Cyrus confirmed, ready to take no for an answer but also just as ready to accept less-than-enthusiastic consent as a yes.

The idea of taking both men when he'd never even ever had one man made Roy incredibly nervous but also made his cock jerk hard enough that the tip tapped his lower stomach. Biting his lip, Roy gave a nod, his years of conditioning making him give a verbal answer despite the already given non-verbal one. "I'd like to try, sir." He said softly, heart jumping at the way Cyrus smirked at him.

"Fantastic." He breathed, finally looking at Vincent and having to squash the urge to smile affectionately at how excited he clearly was. "Vincent, on your back, if you would." Cyrus ordered, looking at Roy as Vincent quickly complied. "Straddle him." He commanded simply, satisfied to no end when Roy also hurried to obey. "Facing him." Cyrus added, getting behind Roy in between Vincent's spread legs once he was in place. Taking the discarded lube-tube from the bed, Cyrus squirted a generous amount into his hand and then passed it to Vincent. He began to lube up and so did his underling, neither man wanting to hurt Roy anymore than was necessary. Being a virgin and taking two cocks at once was going to be uncomfortable enough let alone if it was two poorly-lubed cocks.