Chapter Five — Riley part II
Blake Hamilton is waiting for his ‘friend’ to arrive at his penthouse. It’s about half past three in the afternoon, and according to his most recent text message he’s on his way now.
So he orders Tara to wait in her room, quietly, until she’s summoned again. Of course, she does as instructed.
Then, the doorman texts to say Riley’s entered the building, and is heading up.
Riley walks in awkwardly on tall needle heels, in a tight, short black dress. His things in a purse, his hair dolled up, his eyebrows neatly plucked, his lashes worked long. He’s in make up, his nails are done on both hands and both feet, and his lips are shiny with black glossy lipstick.
As he enters, he puts his brand new designer purse down on the coffee table and somewhat clumsily walks over to Blake. “I’ve... had a very strange afternoon.”
“Tell me about it.” Blake smiles, patting the seat next to him.
Fuck, Blake thinks, Riley’s looking incredible all girled up.
He tries to surreptitiously adjust himself, so his throbbing erection wouldn’t be as evident as it could be, now that he’s catching a whiff of Riley’s new, sweet strawberry perfume.
“I’m... I just didn’t feel happy in my clothes anymore. So I went out and I... kept drifting into the women’s sections of stores. And then I thought, well, why shouldn’t I wear a dress, if I like it? I’ve been dressing and acting like my dad for so long, I thought, is that what I wanna be? A copy of my old man?”
“It looks good on you.” Blake grins, licking his lips. “You should wear a dress more often.”
“You know... I think I will. And this lipstick is so cute! I love it!” Riley blinks, spotting Blake eye him up and forming a bulge. “Oh, God, are you checking me out? Do you... Holy shit, are you hard?”
“Yup.” Blake chuckles. “Can’t help it, you’re hot.”
“Pervert.” Riley huffs. “So, anyway, for the last four hours I’ve been trying on dresses, I got my hair done, found someone to put on some make up and... man, I can’t tell you how relaxed and content I feel looking like this. I feel so... confident!” Then he blinks. “Thank God I live alone. I don’t think I could explain this to my parents. My dad especially...”
“I went shopping too. Got a few things I desperately needed.” Blake grins, tapping a little shopping bag on the coffee table.
Riley takes a moment, trying to gather his thoughts, then blinks. “You know, uh... I was gonna prepare some things for you... because of, you know, what we talked about, but... I really did nothing else but shop. That’s... so unlike me.”
“It’s fine. Just let me get a good look at you.” Blake chuckles, to which Riley gets up and spins slowly, showing off his hairless, slender body in that tight dress.
He raises his arms, striking a few flirty poses, and smiling. He looks quite happy now, albeit slightly confused, and a little embarrassed.
“Now show me that ass, girl!” he teases.
Riley turns and leans over, showing off that round butt under that short dress, in nothing but a black thong. “Wait... why am I...?” he blinks, finally realizing something strange is going on.
“Why are you acting strange?” Blake asks for Riley. “It’s because you’re my slave. Aren’t you, girl?”
“Yes, master.” Riley replies, then blinks, and yelps “Oh, shit! Why did I say that?”
“Because I’ve magically brainwashed you... just a little.” Blake admits. “To not only be my servant... but to dress and act girly, too!”
“That’s fucked up! That can’t be true!”
Blake snaps his fingers and Riley gets rock hard.
“Wh-Whoa! S-Stop it!” he moans, starting to pant and blush.
Blake snaps his fingers again, and Riley’s erection subsides. But now he moves to get on his knees between Blake’s legs.
Riley is terrified. How is he not in control of himself?
“How the fuck did you do this? And why?”
“Because I like you... and because I want to own you.” Blake admits. “The how is a magic ring, that I’ve inherited from my grandfather. The why... hah! Look at you! You look like one of your dad’s sugar babies.”
“Fuck you!” Riley spits, managing to get himself back on his feet, then immediately dropping himself on the couch next to Blake, his arms crossed, looking upset.
“The reason I put you under my power... is because I want to use your talents. You’ll be my business manager. And with you under my control, I know you won’t deceive me or steal from me.” Blake explains. “I only want the money. The actual work and know-how I’ll leave to you.”
Then, with a wicked grin, he picks a bottle of high grade lubricant out of the little shopping bag and puts it on the little table next to the couch.
“What’s the squirt bottle for?” Riley asks nervously.
Blake grins. “Because I’m gonna fuck your ass later.”
Riley gasps in shock. “W-What? ... No. Please, no!”
Blake puts his hand on Riley’s bare thigh and licks his lips. “You heard me. If you’d paid attention during what passed for our friendship, you’ll know I’m bi, and I like feminine twinks. I’ve been fantasizing about having you doll up and bending you over since I met you.” he admits, grinning. “And yeah, at some point I’m gonna bend you over and fill your guts with my loads! Very, very soon... probably today.”
Riley looks quite worried, trying to think up a way out of this situation.
Of course, it’s obvious he’s not gonna get anywhere. He’s no longer in control, after all.
So he does what he’s been trained to do. Negotiate. “Then... at least promise me one thing?”
“Depends.” Blake grins.
“If you’re gonna fuck my ass...” Riley starts, rolling his eyes and puffing. He’s obviously quite nervous. “You’re not... gonna make me enjoy it, are you?”
“Wouldn’t you rather enjoy it than hate it?”
“I don’t want you to change me that much.” Riley says, biting his lipstick coated lip. “If you change me too much, it’s like you’re killing me, and replacing me with someone else. Don’t... change me that much.”
“It’s not that bad, but... I promise.” Blake nods. “And how’s about this? I know you’re into my stepsisters. Once I subjugate them... I’ll let you have your way with them.”
“That’s... Fuck, I’m not gonna lie, that sounds hot.” Riley groans, his erection obvious in that tiny thong. “I can’t do a ‘holier than thou’, if I had a magic ring that could brainwash and control people I’d do exactly what you’re doing.”
Blake grins, “I know.” Then he snaps his fingers, and makes Riley get on his knees before his master.
“F-Fuck... it’s... a strange sensation, for sure.” Riley starts. “My body longs to suck your cock... but I’m sure I’m gonna hate it. Every second of it.”
“Are you going to hate me?” Blake asks. He’s never thought about it until now.
“Probably. Well, maybe a little. But if you use that magic to make both of us rich and powerful, and I get my pick of your harem... I’m confident I can live with it. Eventually.”
“Even sodomy?” Blake licks his lips.
“I’m not looking forward to that.” he sighs nervously. “But I’ll be getting a lot of money and beautiful women, right?”
“Yeah. But I’ll make you spends part of it on slutty dresses to wear around me.” Blake explains. “Your life will revolve around pleasing your master, of course.”
Riley smirks and shrugs. “Figures. Now, master, may I please suck your cock?” Then he groans. “Fuck, why did I say that?”
Blake unbuttons his pants and shows off his large, throbbing erection. “Not until I say.” he teases, making Riley wait.
And Riley does wait, dutifully, hypnotized by that huge cock, drooling a little bit.
“F-Fuck. This is like... standing at a cliff, and you get that feeling about wanting to jump in, even though you know it’d kill you... Except... I can’t resist it... It’s so strong!” he groans, his body trembling, aching to leap forward, grab that dick and stuff it whole down his throat. “Fuck, master... you’re so... big...” he groans, his eyes locked on that cock. He can’t tear his gaze from it.
“Tell me... have you ever sucked cock before?” Blake chuckles.
“Four times...” Riley admits, biting his lip. “For an internship... Same guy each time, though.”
“Did you hate it?”
“I hated every second of it, each time...” he admits. “But I’d do it again if I had to... get ahead of all the others.”
“You’re doing this to get ahead of everyone else. No-one but me has this power to control people...”
“Y-Yeah... but... that doesn’t mean I’m gonna enjoy it.”
“Well, I don’t need you to enjoy it.” Blake winks cheekily. “I just need you to do your best. Work your girly ass off for your owner!”
“Absolutely, master! I won’t disappoint you!” Riley promises cheerfully, then groans. “Asshole.”
With a snap of his fingers, Blake makes Riley start sucking his dick. Those soft, plush lips wrap around the throbbing totem and slowly work their way down, slurping and sucking, with Riley making dutiful eye contact as he works that pole. Indeed... he’s done this before.
And he’s damn good at it.
“So, do you like it? Blink once for yes, twice for no.” Blake chuckles.
Immediately, Riley blinks twice, then twice again, and twice yet again.
“Your mouth feels great on my cock.” he teases.
“Thank you, master.” Riley says, before returning to suck on that fat dick and grumbling to himself.
A wave of the hand. Riley suddenly switches from sucking on the shaft to dragging the back of his tongue across those large balls, gripping the cock with one hand and pumping it hard and fast.
Riley’s cute face rubs up against the length of that fat dick, his tongue coating it in his saliva as he works his way up back to the tip, sucking his lips on it.
He lowers his head onto the pole, gagging himself as the cock reaches into his gullet, stuffing his esophagus for a moment.
“Damn...” Blake groans, leaning back onto the couch, clutching the seat cushions. “You’re a pro...”
If Riley didn’t complain and grumble, he’d appear fully into master’s massive dick.
The girly boy asks a question, but Blake can’t understand.
“Don’t talk with your mouth full.” he teases, before putting his hand on Riley’s forehead and pushing him off that huge dick to breathe and speak.
“You’re not gonna whore me out to your friends, are you?”
“I’m not that mean.” Blake replies, then grins. “But if I did, you’d make me a lot of money.”
“Can this stay between us?”
“I’ll probably tell some people I get to pound you on the regular.” Blake teases. “Why would I keep my conquests a secret? Bragging is part of the fun.”
“I don’t want other guys to come after me.”
“As long as you’re on my team, you’ll have the wealth and influence to tell anyone to go fuck themselves.” Blake grins. “Nobody’s gonna be so dumb that they’ll make a move on you.”
Blake lets go of Riley’s head and immediately the boy starts gagging himself on that fat throbbing cock again. He can’t help himself.
With slow, controlled motions, Riley swallows the tip and lets it ride through his tight throat, stretching his esophagus and temporarily choking him as he deepthroats his rival. His master. His owner.
On one of the descents down that big pole, Blake holds him down in place, making him choke for a while, before letting off.
“Fuck... you’re talented.” he groans. “I could have you suck me off for hours...”
Riley rolls his eyes at Blake.
“Well, if you don’t want to be here all day, you better make me cum, don’t you?” Blake winks.
On that, Riley starts to furiously bob up and down that shaft, swallowing the tip into his gullet and working hard to pleasure master.
For five long, agonizing minutes, Riley makes Blake feel like he’s in heaven, giving his master the best head in Fylth City.
At last, he can’t hold it in anymore, he has to erupt!
Blake groans, pumping a hot load into Riley’s mouth, which he tastes for a moment, then swallows like a good girl.
The effeminate boy gasps and squeaks “Thank you, master!” with a sweet smile, before groaning and exclaiming “Fuck! That was horrible.”
“It felt great. You got an amazing mouth for sucking cock.” Blake teases, but then looks down at his latest victim. “Do you... hate me?”
“I do hate you, sorta... Well, no. I resent you for doing this, but I don’t ‘hate’ you. Like I said, I understand. If I had that power... but I also respect you a lot for not being afraid to take what you want, now that you can.” Riley admits.
“Good girl.” Blake grins.
“Did you have to make me swallow?”
“I didn’t make you do that. You did that yourself.”
“Fuck.” Riley complains. “...Fuck! I could have spat?”
“Go rinse.” Blake says, pumping his cock, playing with it a bit. “You know where the drinks are.”
Riley jumps to his feet and wobbles over on those high heels towards the kitchen, getting the carton of orange juice and rinsing his mouth with a big swig.
“You’re the one that asked me not to make you enjoy it.” Blake reminds his rival-turned-servant.
“Yeah, I know. But you could have, perhaps, not made me suck you off.”
“If our roles were reversed, would you subjugate someone and then not make them work your dick?” Blake asks.
“... Yeah, you’re right. Just, please... don’t fuck my ass.” Riley says, returning to the couch.
Before he can sit down, Blake pats his lap, and Riley sits his big round girly butt on there, the cheeks rubbing against that rod.
“Oh, come on...” Riley groans.
“Such a nice butt. I’m gonna enjoy fucking you.” Blake grins, his hands on his newest servant’s hips, and rubs that ass.
He raises Riley’s skirt and pulls at the lad’s thong.
“For fuck’s sake...” Riley groans, as he rubs his ass back against Blake’s cock. “You just came in my mouth. You can’t be horny again.”
“What can I say? I’m a frisky fucker.” Blake grins, his hands sliding up and down Riley’s body in that skintight dress. “Just a blowjob isn’t enough to wear me out. You have to earn your place by my side if you want to make millions off my new powers.”
Riley gets up and peels down his thong, exposing his ass to Blake. “Please. Don’t do this...”
Blake gets up and shoves Riley face down onto the couch, his ass up in the air, and gets right behind him.
“Please, man... Please!” he tries, even though his ass is wiggling seductively at his owner. “Master, please! No!”
Blake slaps this fat dick down between Riley’s round buns, their sacks rubbing together.
“I told you...” Blake starts, “I’ve been fantasizing about mounting you since the first time we met. I’d fuck you all day if those three stupid bitches weren’t coming home tonight...”
A couple of tears run down Riley’s face as he gets emotional. “Please. I don’t wanna be a... a...” he says, but doesn’t finish the sentence.
Riley refuses to answer. “Please. Just... don’t...”
“Look, just try to enjoy it.” Blake says, picking up the squirt bottle and lubing up his own cock and Riley’s ass, even slipping a few fingers into him with lubricant.
“Fuck you and your huge dick.” Riley whimpers defiantly, clutching the pillow from the side of the couch tightly. “If I walk weird after this I’ll... I’ll...” he starts, but doesn’t finish. It’s not like he can do anything about any of this.
“Just let me get this out of my system...” Blake says, petting Riley’s ass. It’s so soft and round. “Think about how you’ll be pounding my stepsisters by the end of the day.”
Riley looks back over his shoulder, quite nervous. “B-Be gentle, okay?”
Blake smiles sweetly, petting Riley’s head. “Of course.”
The tip pushes against Riley’s tight hole.
“Try to relax. Struggling will only make it hurt you more.”
Riley takes a few deep breaths, as he tries to calm down. His ring is clenched shut, but slowly it starts to loosen up.
“Right. Now, think pleasant thoughts. Think about all the money we’ll make, all the hot bitches you’ll screw, all the big business we’ll influence...” Blake says, gripping Riley’s hips as he slowly pushes inwards.
Riley whimpers, trying very hard not to clench. “Money... and bitches... and power...” he whispers to himself.
The large tip enters his tight hole, and Riley lets out a pained, long groan. Tears trickle down his flushed cheeks. It’s pretty bad... but nowhere near as bad as he was worried it’d be.
Blake bites his lip, moaning. “Fuck... you’re amazing...”
Riley winces “Thank you, master...” before panting and squeaking out “You’re too big. Pull out... Come on, man, I can’t take a cock this big!”
Both boys pant and groan loudly, as Blake slowly slides deeper into Riley. Even with the quality lube, Riley is still in a great deal of discomfort.
“Master... please... you’re huge... have mercy...”
“No mercy for you today.” Blake chuckles. “All you’re getting is cock.”
Riley squeaks “Yes, master. Thank you, master.”
Blake playfully covers Riley’s mouth with his hand, if only to signal him to be quiet, as he thrusts into that tight ass with a few powerful lunges.
Riley bucks and arches with every push inwards. He lets out a groan, and drools profusely into Blake’s hand, who removes it from his mouth.
The girly boy reaches out for the remote on the coffee table, nearly out of reach.
“What’re you doing?”
“It hurts too much... I need distraction.” he groans, his ass filling slowly with his owner’s long, fat, throbbing cock. He manages to get hold of the remote with the ends of his fingers and quickly turns on the television, tuning in to some boring news show for financial reports and stock market info.
But, against Blake’s expectations, he can feel Riley relax.
“I’m gonna make so much money...” Riley says to himself, mostly calm if still in great discomfort. “You better make me a shitload of money...”
Blake leans down on top of Riley and whispers into his ear as he firmly pumps that tight ass. “We’re gonna make millions. You’re gonna metaphorically fuck bankers as easy as I’m literally fucking you. Fuck ’em hard, and fuck ’em deep. They won’t be able to resist...”
It actually starts to get Riley’s motor running, and he bites his lip, his eyes fluttering. “A merger of Peyton Industries and ToPex pharmaceutical...”
That big cock pumping that tight ass starts moving faster and faster, and the complaints die down completely.
Riley has to turn up the volume to hear anything over the sound of Blake’s fat sack slapping against his own plums with every thrust into that tight hole.
Blake grins. “No. Not a merger. An acquisition...”
That’s what Riley loves to hear. He moans out, squirming in delight around the massive malaise of that cock stirring in his guts. Now both of them are rock hard.
Blake’s large sack slaps against Riley’s tiny plums. He puts his hand over Riley’s and holds it, their fingers clutching.
Riley lets out a little strand of drool, his mouth wide open and his eyes crossing. “It’s... not so bad... as long as you hold up your promise...”
Blake leans in to kiss Riley on the lips, both of their hearts racing, as they passionately embrace. It’s quite pleasant, and Riley even kisses back. They find themselves fully wrapped up on their intimate encounter. Blake out of lust, Riley out of greed. He thrusts hard and deep, keeping a strong, fast pace up, until finally he holds, deep inside his latest prey, and fills Riley up with his hot, thick load.
The kiss lasts, and Blake’s hands greedily feel every bit of Riley they can reach.
When their lips part, Riley whispers “Thank you, master...” and leaves it at that. No complaints. The more he’s exposed to Blake’s magic, the more certain he is he’ll make a killing. Plus, Riley’s always been attracted to power.
“What does baby want?” Blake asks softly, looking into Riley’s eyes, playing with his hair. His cock’s still rock hard, throbbing deep in his servant’s ass.
“I want to be the CEO of Peyton Industries... and acquire ToPex, and the Shingumi group...” Riley says, biting his lip. “... to start.”
“Is it worth your ass?” Blake asks, kissing Riley on the cheek. He’s so girly, Blake can’t tell he’s actually a young man. He’s soft, just like Julie...
Blake isn’t making Riley say anything.
Riley thinks about it, then sighs through a weak smile, and plants his lips on Blake’s, kissing him firmly. “Yes... master. Whatever you please.”