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This story takes place in 2016, approximately three months after the conclusion of "Southern Chastity". While the previous story does not have to be read to understand and enjoy this text, I encourage you to read it if you are interested in understanding more about the character of John who is referenced here.
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Manhattan Doms - A Southern Chastity Novella - Part 5
Drew awoke the next morning and scratched his ass. His jock was still crusty with cum from the night before and he noticed that his nub had produced some nocturnal emissions. He pulled it off him and stood up and stretched. Bart and Wes looked to be fast asleep and he crept into the bathroom to drain his bladder. When he came back into the room, he noticed Wes looking at him.
"Sorry if I woke you, Sir," Drew whispered.
"You didn't, cubby," Wes replied softly. "I've been laying here for about thirty minutes trying to determine if I was going to get up."
"Can I get you anything?" Drew asked.
"Come over here, boy," Wes said.
Drew walked around the bed and Wes rolled over to face him. Drew got on his knees and Wes reached out and ran his hands gently over the boy's face and beard. He took a sniff and smiled.
"Someone smells like sex and booze," Wes replied.
Drew grinned. "Yes, Sir. I got a load each from Stephen and James before they went to bed."
"Did you sleep with their loads in you?" Wes asked.
"I did, Sir," Drew replied.
"That's a good boy," Wes said. "Do me a favor, though. I know Bart doesn't want you to shower, but please go in and wipe yourself down with a washcloth. I'm not as fond of a smelly pig around the house as he is."
"Yes, Sir!" Drew said.
"After you are done, go and check on our guests," Wes said. "We will be taking them out to breakfast before doing a little sightseeing."
"I can do that," Drew replied. "Will I be going with you all?"
"No," Wes said. "After we leave, I want you to clean up the apartment and put away the pull-out bed for the day. Be sure to clean yourself out well. You will be going over to Bryce's place today and we will join you there after we tour the city."
It had been about two months since Drew had last been over at Bryce's loft. It was a nice open area and he had a small dungeon set up that Drew had experienced on numerous occasions. Bryce was well known for his BDSM parties and he often had boys over to be used in various ways. Drew saw a lot of similarities between him and his original master and trainer, John, in Atlanta.
"I understand, Sir," Drew replied.
"Bryce has requested that you stop by early so he can use you on his own before we arrive," Wes said. "Please text him when you are done cleaning and arrange to be at his place when he requests."
"I will, Sir," Drew replied.
"Ok," Wes said as he lightly tapped Drew's face. "Go get your stank ass in the bathroom."
Drew smiled and leaned over and kissed his master and then walked around the bed again and went into the bathroom. He got a washcloth and soaped it up and ran it over his pits, cage, and ass, and then stepped into the shower and used the attachment to clean himself out for later. Once everything was running clear, he stepped out and dried off and then walked around to the living room to check on the guests.
James was on his back, snoring. His cock was rock hard and pointing towards the ceiling. Stephen was rolled on his side with his face planted in a pillow. Drew walked over next to James and knelt down and gently rocked his shoulder.
"Master James?" Drew called out.
After repeating the call a few times, James stopped snoring and cracked an eye open. His arms came up and he scratched his chest and then ran them down to feel his hard cock.
"Morning, boy," James said with a smile. "Come take care of this for me."
"Yes, Sir!" Drew replied.
James spread his legs and Drew crawled over and laid between them. He grasped the rock-hard cock in front of him and brought his mouth near it. James had a pretty tight foreskin and only a bit of the head was showing. Precum had started to form and as Drew held the shaft in his hands, the liquid pushed up and dribbled down over his fingers. He brought his tongue down and licked it. The taste was salty and sweet and he smiled.
Drew put the head of James's cock in his mouth and licked around the inside of his foreskin for a taste. James groaned as his toes began to curl. As Drew brought his tongue down and around the shaft, he licked the base of James's cock and then ran it around his groin and balls. He could taste and smell James's sweat. He shoved his nose under James's balls and rubbed it around to mark his beard with it.
He brought one of James's testicles into his mouth and rolled it around gently. They were low-hanging, large, and full. He brought his tongue back up the shaft and then started to deep-throat James's cock. He felt as the uncut head ran back into his mouth and he started to bob up and down on it, adding in some gentle sucking motion.
James's groaning grew louder, and he reached up and ran his hands over his chest. Pleasurable waves of energy were pulsing through his body and he closed his eyes and bit his lower lip. He gyrated his hips and then moved them back and forth to get his cock deep within Drew's mouth. He knew he would not last long.
Drew looked up and saw James with his eyes closed and starting to finger his nipples. He reached down and cupped James's balls and started to roll them around with his hands. He let his finger run under them and into James's crack and he felt James's taint as he continued to suck.
"Oh fuck," James groaned as he felt his orgasm hit him suddenly.
Drew started to feel the pulses of cum hit the roof of his mouth and then he tasted it. James's morning load had a strong flavor, likely the result of an evening of boozing. He let it gather in his mouth and then moved it around the head of James's cock before swallowing it and running his tongue through James's foreskin a few times to make sure he got it all.
As Drew came off James's cock, he licked his lips. James let out a long sigh and then looked down and smiled.
"Now, that is a nice wake-up call," James replied.
Drew looked over and Stephen was still fast asleep. James looked over and grinned.
"Don't worry, boy," James said. "He takes forever to wake up. I'll handle him. What is the plan this morning?"
"Master Wes said they would be getting up soon and will be taking you both out for breakfast and some sightseeing," Drew replied. "Then you will be meeting up later at our friend's place. He has a nice dungeon and I will be there for your pleasure."
"Sounds like a plan," James said as he ran his hands over his chest. "Thank you, boy."
"Anytime, Sir," Drew said as he got up from the bed.
As Drew went into the kitchen to grab a drink, Bart came stumbling in from the bedroom. He looked like he had slept rough.
"Start the coffee, boy," Bart said as he pulled out the chair in the kitchen and sat down and put his face in his hands.
"Right away, Sir!" Drew replied.
Wes came in after and had just finished taking a shower. Bright-eyed and awake, he leaned down to kiss Bart.
"Ugh, go away you foul morning person," Bart said as he waved his hands.
"Ha!" Wes replied. "Seems like those hangovers hit you a lot harder these days."
Wes sat next to him and smiled. He saw James come over and stand behind him and rub his shoulders.
"How did you sleep?" Wes asked.
"Not bad," James replied. "Woke up with a raging hard one, but your boy took care of that for me."
"Good," Wes replied with a smile as he watched Drew start the coffee maker.
"Is Stephen up yet?" Wes asked.
"Ughhh," came a muffled response from the bed.
"The hibernating bear is getting there," James said with a laugh. "The coffee will help."
"Well, as soon as you all are awake, we will head out to grab some breakfast and then do some touristy things," Wes said. "The weather should be nice today."
"Sounds like a plan," James replied.
Stephen finally sat up and turned to look at the men at the table. He had one eye slightly cracked and his beard was an absolute mess from being buried in the mattress. He scratched his neck and stumbled as he got to his feet and came over to sit on the other side of Bart. Drew brought some coffee cups over for everyone and once the pot was ready, he filled them all and then brought over the sugar and cream.
"Ugh, I needed that," Bart said as he gulped down half the cup.
After the men were caffeinated, James, Stephen, and Bart took a quick shower and then got dressed for their excursion. As they were putting on their shoes, Drew walked around to fold the bed away into the couch again and started to straighten up the room.
"We will see you this afternoon, boy," Wes said as he stood and grabbed his keys. "Be ready for us."
"I will, Sir," Drew replied. "Have fun out there!"
After Drew ran the vacuum in the living room and mopped the kitchen area, he straightened up the bedroom and bathroom before grabbing some clothes to head over to Bryce's place. He had texted Bryce after the men left and was told to come over by 11 am. Bryce lived in SoHo, so he knew it would take him about thirty minutes to get there.
As Drew stepped outside, he noticed how nice it was out and he wandered over to Columbus Circle to catch the C train to Spring Street. As he rode downtown, he saw some attractive, bearish men sitting across from him. They were obviously from out of town and smiled. Drew could not help but notice one of them had a huge package. He blushed when he was caught looking and the man winked at him.
"Are you in town for Urban Bear, cutie?" the man asked.
"I live here, but I will be going to the Street Fair tomorrow," Drew replied.
"Maybe we will see you there, then," the man said as he put his hand on his crotch and groped it.
Drew smiled. "I'll be sure to look for you!"
When Drew's stop came up, he told the men to have a good day and then started on his walk around to Bryce's building. He pressed the call button when he got to the door and Bryce buzzed him in and he took the elevator up. When the elevator doors opened, Bryce was waiting for him.
"Good to see you again, sexy," Bryce said as he came over and hugged the boy. "Come on in."
Bryce's loft was one large, open room. Drew shuttered to think how much it cost, but it was a gorgeous space. It had exposed brick walls on one side and nice views through large windows. Bryce had one side for his bedroom and living areas and the other was set up as a dungeon area. He had a fuck bench, a Saint Andrew's cross, a sling, and a long shelf that contained various toys and BDSM implements and gear. There were metal eye hooks suspended from the ceiling and the floor was covered in rubber matting.
Bryce was a hairy man. He had gone bald but had a full gray beard which matched the color of his fur on his upper chest and back. It was still dark on his belly and legs, but the white was creeping in quickly. He had broad shoulders, thick legs, and a nice belly on him. He had greeted Drew wearing shorts, but as he closed the front door behind him, he dropped them to the floor, revealing his cock and large balls.
"Go ahead and get undressed, boy," Bryce said as he walked over to the kitchen area. "Do you need any water or anything?"
"I am good, Sir," Drew said as he started to take his pants off.
Bryce had a set of cubicles to the right of his front door that contained wicker baskets. Drew pulled out one and put his clothes in it and then placed his phone on top after he turned it off. He then placed it back in its slot and walked over to the kitchen.
"Did you all have a good night last night?" Bryce asked as he grabbed a bottle of water out of the refrigerator.
"We did," Drew replied. "We stayed out till after 1 am and then headed back. Stephen and James seemed to have had fun. They are out sightseeing now."
"Yeah, Wes told me that was the plan," Bryce said. "So, when was the last time you had a flogging session?"
"Probably the last time I was here, Sir," Drew said.
"Well, let's get you on the cross, then," Bryce said. "Want to warm that back and ass up before I have my fun with you."
Bryce pointed over to the cross and Drew walked over to it. It was made of hefty wood but was padded in black and brown leather. Drew stood beside it and Bryce grabbed some leather arm and ankle cuffs and secured them on him. He then grabbed a blindfold and put it around Drew's head and secured it firmly.
"Can you see anything, boy?" Bryce asked. "Do you have any discomfort from the restraints?"
"No, Sir," Drew replied.
"Good," Bryce said.
He guided Drew over to the cross so he was facing it and pulled his arms up and secured them to the top arms of the cross, using the wrist restraints. He then brought Drew's legs forward and secured them to the bottom arms so Drew's arms and legs were spread and his backside was completely vulnerable. Bryce then grabbed a leather crop with a wide end to it first and walked over and ran his hands over the boy's back and ass.
"You remember your breathing exercises, right, boy?" Bryce asked.
"I do, Sir," Drew replied.
"Just let me know if you have had too much," Bryce said.
Bryce took the crop and hovered over Drew's left ass cheek. He held it there for a moment and then gave it six quick strokes, smacking it against the skin. He then brought the crop across both cheeks and then, with a quick stroke, let it smack hard against the left cheek again. Drew jumped and groaned and Bryce grinned.
Bryce brought the crop over to the right cheek and repeated the procedure. He then delivered three sharp strikes to each cheek in succession and Drew squeezed his ass muscles and jumped forward. Bryce rubbed Drew's ass and then soon continued to deliver quick strikes and then a pause. He watched as the energy of the crop caused the fat on Drew's skin to ripple across his ass cheek.
After a few minutes, he put the crop down and grabbed the leather flogger. He pulled it back and started to swing it in a circle and then brought it forward so the leather straps impacted Drew's ass on the downswing. He was gentle at first but provided more force as time passed by and Drew started to jump and moan. Drew's ass cheeks clenched with each smack and the skin started to slightly redden.
Bryce brought the flogger down hard on one cheek and then the next. The smack of the leather on skin echoed through the room, as did the yelps from the helpless Drew. Bryce paused every so often to run his hands over the bare skin, which intensified the sensation Drew was feeling. The boy's nub started to harden in his cage and his balls were being pushed back as a result.
Bryce grabbed a small wooden paddle next and delivered a blow across the full length of Drew's ass. Drew yanked on his arm restraints and jerked forward as he groaned loudly.
"You still ok, boy?" Bryce asked.
"I'm ok, Sir," Drew replied as he bit his lip.
Another blow came from the paddle, followed by six others, spaced with some time in-between. Bryce reached under Drew's ass and let his palm run over the boy's taint. His fingers reached down and felt his balls that were tight in his cage due to the attempted erection his body was trying to give him. Bryce smiled and put the paddle between the boy's legs and brought it up with a smack against his balls.
"Fuck, Sir!" Drew screamed as he jumped upward.
Had he not been bound, Bryce was quite sure Drew would have leaped off the floor.
"Looks like those balls are nice and tight in that cage," Bryce said as he rubbed them.
Bryce smacked Drew's ass with his hand a few times and then grabbed the crop to repeat the same procedure as before. He was a little harder with his delivery this time and when he swapped to the crop again, he started to bring some more red to Drew's skin. He ran his hands over it and felt the warmth growing.
Bryce pulled back and delivered a large impact with the flogger on Drew's left cheek. The boy squirmed and screamed and when the flogger came down on the right cheek he started to yank on his restraints.
"Calm down there, boy," Bryce said as he ran his hands over Drew's back and sides.
Drew tried to calm himself by taking deep breaths. The pain was not too intense, but he was feeling the sting of the impacts on his ass. Bryce moved to his lower back next and continued the impact play and after several minutes, Drew felt as though his back and ass were on fire.
Bryce grabbed a leather paddle and looked at the boy for a moment. Redness had started to form on his lower back and ass cheeks and you could feel the heat of his skin. He brought the paddle down on the fullness of Drew's ass a few times, letting the sound echo through the room. But, by the fourth swing, Drew could take no more.
"Please stop, Sir!" Drew screamed as he twisted on the cross.
Bryce put the instruments down and came over and embraced the boy. He ran his hands down his sides and then caressed the irritated skin. He blew on it and rubbed it gently. Drew groaned in pleasure as his nerve endings fired intensely.
"You have a good color now, boy," Bryce said. "Can you take three more whippings from me?"
"I can try, Sir," Drew said.
"Do your best," Bryce said. "It will please me."
"Yes, Sir," Drew replied.
Bryce picked up his heavy wooden paddle and lined it up on Drew's ass before bringing it down hard. The impact was loud and the skin rippled as the energy flowed through the boy's body. The pain was intense and Drew could not help but scream out at the top of his lungs.
"Fuck!"
"That's one, boy," Bryce said.
He brought his hand back and then swung hard again. The paddle impacted again with the same intensity and Drew lifted his weight onto his toes and screamed even louder this time.
"Ahhh!"
"That's two," Bryce said.
Drew was in so much pain that tears were starting to form. He knew he could stop this at any time, but he wanted to please the man. It was just one more blow and he took a deep breath and prepared himself. Bryce was swinging the paddle back and as it came down for the last time, the sound was even louder than before.
"Holy fuck!" Drew screamed.
Drew pulled hard on his restraints and started to cry openly. Bryce put the paddle down and brought his hands around Drew and embraced him.
"Shhh," Bryce said as he ran his hands over Drew's sore ass and back. "You did it, boy. No more paddles."
Drew sobbed and then caught his breath. The tears ran down his cheek and Bryce reached around and rubbed his face to wipe them away.
"I'm proud of you," Bryce said. "That is about as far as I have ever gotten you before."
"Thank you, Sir," Drew replied as he took deep breaths.
Bryce ran his hands over Drew's ass cheeks and noticed how red they were. The skin was slightly raised when the impacts were delivered and he knew the boy would have some bruising tomorrow.
"Do you think you can take the fuck bench now?" Bryce asked as he backed away.
"Yes, Sir," Drew replied.
Bryce unhooked Drew from the cross and helped him stand. He guided him over to the fuck bench and let the boy mount it, and then he secured his ankles and wrists to the sides. He ran his hands over Drew's ass. It was red and warm, and he let his fingers slip into Drew's crack and run across his hole.
Drew's ass still hurt, but as he rested on the leather padding on the bench, the sensation he was getting as Bryce's finger entered him was altogether different. Bryce lubed his index finger up and slid it into Drew's hole and gently probed it. He rubbed across Drew's prostate and the boy's legs shuttered.
"I think I found the magic spot," Bryce replied.
Drew smiled and took a deep breath as Bryce started to move in circles around his sensitive organ. His nub started to leak and prostate juices began to slowly drip out. They formed a long string of liquid that extended down from his cage and almost reached the floor. Bryce saw the strand and pulled his finger out and collected it and then rubbed it into Drew's ass.
"I love it when a boy produces his own lube," Bryce said with a chuckle.
Drew was still blindfolded, and as such, his sense of touch was heightened. The prostate massage felt so good, as his aching balls started to release some pressure and he relaxed his limbs and began to zone out. Bryce pulled his finger out and replaced it with his index and middle finger and worked them in till he felt less resistance from the boy's ass. Bryce started to stroke his cock and it began to grow in his left hand.
He pulled his fingers out, moved up, and pointed his rock-hard cock at Drew's red ass, and spread the boy's cheeks with his right hand. He then pushed forward and felt little resistance as his shaft disappeared inside.
"That's a boy," Bryce said.
Once his groin met Drew's warm ass, he grabbed the boy's waist and lifted as he started to fuck. His cock had a slight downward curve to it and as he fucked, it ran across Drew's already sensitive prostate.
"Oh my," Drew groaned as he felt the man fuck him and hit all the right spots.
His nub started draining prostate fluids again and he started to clench his ass to grip Bryce's dick.
"Are you feeling that deep in your nub, boy?" Bryce asked.
"Fuck yes, Sir," Drew replied. "Your cock feels so good."
"So does your ass, boy," Bryce replied.
Bryce started to move faster and pulled his cock almost completely out and shoved it back deeply again. He pulled upward to deliver some more pressure to Drew's g-spot and started to rub the boy's warm, red ass cheeks. The technique was working and Drew felt a sensation building deep behind his balls.
"Oh, Sir," Drew called out.
"Yes, boy?" Bryce asked.
"May I please drain my nub?" Drew replied.
"Yes, boy," Bryce said. "That's your reward for pleasing me."
"Thank you, Sir!" Drew groaned.
Drew clenched down on Bryce's cock as it continued to fuck him. He held his breath and pushed and he felt the sensation grow until it overcame him. He felt his nub pulse and cum started to flow out of it and shoot on the floor.
"Gahhhh!" Drew exclaimed as his caged balls drained.
Bryce started to fuck harder and used the clinching of Drew's ass to bring him near the edge. He shoved inside one last time and felt his cock exploding too.
"Take that load, boy," Bryce groaned as he gripped Drew's waist tightly.
The two both pulsed cum for about a minute until they were both drained. Drew relaxed on the bench padding as Bryce pulled out and ran his hands over the boy's back and leaned down and kissed his ass gently.
"You are such a good boy," Bryce said as he tried to catch his breath.
Bryce went over to the side of the room and grabbed a towel and wiped himself and Drew's ass off. He ran it over the boy's cage too and cleaned the cum that was still dripping from the metal bars.
"That was quite a load there, boy!" Bryce said as he wiped the remains off the floor.
Bryce tossed the towel aside and undid Drew's restraints and lifted him off the bench. He then removed the blindfold from his eyes and Drew blinked to get used to the brightness again.
"Give me a hug, boy," Bryce said.
Drew reached out and grabbed onto the large man's waist. He placed his head on Bryce's sweaty chest and closed his eyes again. Bryce ran his hands down the boy's shoulders and then moved his hand up and rubbed Drew's head.
"I've missed that ass," Bryce said with a smile.
Drew ran his hands over the man's back hair and gave him a strong hug before pulling back and looking at him.
"Well, thanks for breaking me in today," Drew replied.
Bryce laughed. "I guess you probably will have a lot more action back there before the day is over. Do you want some water now?"
"Yes, please!" Drew replied.