The story continues with a trip to New York for Tim to get sized up by a pervy tailor and more
Disclaimer: This story involves sex between men and teens, and teens and teens. It will eventually contain some pretty severe humiliation and punishment scenes and probably some bondage. If you don't like it, you don't have to read it. It is just a story. None of the characters are based on anyone real and none of this ever happened.
Tim slowly opened his eyes, and was momentarily confused by the unfamiliar surroundings. Then he smiled to himself and luxuriated in the feel of the smooth firm body he was spooned up against. He couldn’t believe he was sleeping in the same bed as another boy.
He didn’t even remember going to sleep.
After the incredible punishment and sex session from the night before, he had let Rich lead him upstairs to his bedroom, where the two boys shared a very sensual shower, with the two boys soaping each others smooth bodies up and taking turns scrubbing each other with Rich’s fancy sponges and soap that he had never imagined could smell or feel so good. Rich had some kind of cream that they applied to each other’s still tender asses, making the sting of their punishment far less painful. He couldn’t help stare at Rich’s amazing body, especially his crotch with its well trimmed bush and amazing uncut cock, along with everything else that he had only imagined looking at on another boy up close.
After drying off, Rich loaned Tim a pair of his briefs from his huge collection. Rich giggled as the plain white briefs that fit him skin tight kind of sagged a bit on Tim’s tiny frame.
“We will get you all set up tomorrow little dude. Saul with fix everything, he’s a genius at tailoring.”
Thinking tailored underwear was kind of silly, but not wanting to argue, Tim asked, “Why don’t we just sleep naked. I do at home all the time. These fit weird.”
“Naked is great for having sex lil bro, but another one of Dad’s many rules in no sleeping naked.” (If you’re not in bed with him, he didn’t add.) “He is a firm believer that clothes make the boy, even if that means only the tiniest skimpiest pair of undies, or whatever. Clothing accentuates your body, making you even more desirable to a lot of people than if you were just naked. That’s why you always see those chicks in Playboy or Penthouse wearing garter belts, stockings and high heels. The clothes can draw attention to you or to parts of you. We are in the business of modeling clothes that people want to see good looking boys like you wearing.” Rich was pulling on a yellow square cut brief that Tim could see the outline of his cock and balls through as he lectured him. “Again buddy, when one of us tells you to wear something, you need to learn that it is not just a polite request, but a requirement, OK? You need to trust me Dad, and we can make you a lot of money and have lots of fun doing it, as well as teaching you a lot about yourself, but one of things you need to learn is absolute obedience. You are going to wear a LOT of things that you don’t want to, but you will wear them because that is your job. Tell me that you understand this Timmy.”
Afraid he had done something wrong, Tim quickly agreed, “Sure Rich, I’m sorry, I wasn’t trying to do anything wrong.” He tried to adjust the funny feeling briefs as best he could to try and look as sexy to Rich as possible and change the subject.
“So where am I going to sleep?”
Rich laughed, “With me silly, here, get on the bed and lets watch a movie!” Rich propped up a bunch of huge pillows against the headboard of his king sized bed, and motioned for Tim to climb on. They ended up with Tim sitting in front of Rich, wrapped in the arms and legs of the bigger boy, feeling his cock pressing into his crack as Rich used the remote to start “Transformers” on his entertainment system. Tim leaned back as the opening credits started on the large plasma TV, and that’s the last thing he remembered until waking up wrapped In Rich’s arms the following morning.
While he loved the feeling of being in bed with Rich, he also realized he needed to pee badly, so he carefully undid himself from Rich, trying not to wake him, and padded to the bathroom. He pulled the blue and gold striped waistband of the old school ill fitting briefs Rich had given him under his cock and balls, aimed his cock down and let loose.
He had his eyes closed and was half dozing while he pissed and was startled when he heard a second stream hitting the toilet. He opened his eyes and was startled to see Rich right there pissing along with him. He momentarily lost his aim and almost hit Rich, causing the older boy to laugh.
“Easy there big fella, no use wasting water,” said Rich as he grabbed Tim’s cock and aimed it back at the toilet.
Tim blushed bright red, as he was not used to doing his business in front of someone, much less Rich. He normally even used the stalls at school, not just because he was afraid of accidently looking at the other boy’s dicks, but he couldn’t pee in front of others easily. Now his already half hard cock was stiffening as he squeezed out the last bit of pee with Rich’s hand grasping him.
“Since your up buddy, let’s take a quick shower, and then go get something to eat before we leave.” He dropped his briefs, and then pulled Tim’s down and led the still shy boy by his cock into the shower. After turning the water on and making sure the temperature was set, Rich smiled at Tim and said, “I think I need a snack right now” and to Tim’s utter astonishment, Rich dropped to his knees right there in the shower and took his cock into his mouth!
“Oooh,” he muttered as he let the sensation of the warm water mix with the sensation of the warm wet mouth engulfing his modest sized hard on. He had to place one hand on the wall and spread his legs while Rich expertly sucked him to full hardness. Rich stood back up and looked Tim in the eyes as the water cascaded over both of them. “Your turn Timmy, get your older bro hard. Suck me!”
“Yes Rich,” Tim croaked and dropped to his knees and stared at the wet foreskin covered dick close up before taking the first tentative lick.
“Get your tongue in there buddy, get it inside and lick my cock head, taste me Timmy.” Rich instructed while soaping up his hands.
Tim did as told and started working his tongue inside Rich’s foreskin. His own cock throbbed when he felt the older boy’s cock swell inside his mouth.
“That’s it Timmy, lick it like the little schoolboy slut that you are.”
The dirty talk coming from Rich caused Tim to suck even harder not to mention the affect it had on his own penis. He was finding more and more that he loved being told what to do, even if he was reluctant, which at the moment he certainly was not as he licked and slurped on Rich’s fully hard cock with gusto. Pausing for a breath he noticed how the foreskin was completely retracted and Rich’s cock now looked similar to his own, if not slightly larger.
“Good job Timmy, you got me all sexed up like a good little slut,” Rich pulled Tim back to his feet and spun him around so that he was facing the rear of the shower away from him. He soaped up his cock and pulled Tim up against him positioning his cock in between Tim’s velvety smooth cheeks. His buns were just slightly pink from the beating they took the night before Rich noticed as he started slowly rubbing his cock up and down Tim’s crack. He could feel Tim’s whole body shudder at the contact and he leaned forward and whispered, “You like the feeling of a big boy’s cock back here Timmy?”
“Oh fuck yes Sir I do!” Tim whispered, not even realizing he called Rich “Sir”. Still his response made Rich slap Tim’s tender ass, causing the boy to wince slightly.
“Little boys don’t use words like fuck Timmy, those words are for your betters, understand?” Rich took a soaped finger and started running it up and down Tim’s crack, pausing at his anal entrance as it passed by and making small circles. “Every time I hear you curse, I am going to report it to Dad, and it will add to your punishment on Friday’s”
“I, I’m sorry Sir, I mean Rich, I mean… Oooohhh.”
Rich was pressing at Tim’s hole. “It’s OK Timmy, your learning. It will be quite a while before you’re trained properly.” Rich was whispering in his ear, barely audible over the shower. “Relax Timmy; open up your pussy for me. Let me feel your tight boy cunt”
“AAaahhh”, Tim whimpered as he tried to relax. He had never had the courage to put his own finger where Rich’s was now going, and it frightened and excited him at the same time. He had never thought of his ass as a “pussy” or a “boy cunt” but those words made him feel more like he belonged to the boy fingering him in his most private spot. He let out a gasp as Rich got his finger in to the first knuckle.
“That’s it little bro, let me in. Get used to it buddy, you are going to learn to enjoy it.” He wiggled his finger around inside Tim’s tight hole, making the smaller teen shudder. “Ask me for more Timmy. Ask for it deeper.”
Tim was going wild. He had never experienced such feelings before and cold barely pant, “Yes please…”
“Please what Timmy? What do you want?”
I, I want you…deeper sir, Please Rich, oh man…more.”
Rich inserted his middle finger further up Tim’s virgin hole and Tim started to really moan and shudder. He felt that familiar feeling boiling up in his balls, and his cock was sticking almost straight up and his balls were drawn up tight, so that when he erupted, the cum flew out in an arc across the space between himself and the back wall of the shower before splattering there and starting to run down the wall. He had never touched his cock, the orgasm being caused by nothing but the stimulation of his virginal pussy being fingered.
Rich allowed him to recover for a minute before putting his hand on the back of Tim’s neck and pressing his wet head toward the spot on wall he had just deposited his seed on. “Lick it up Timmy, you came without permission and need to clean up after yourself. I wanna see that tongue on the wall kiddo.”
Tim was so wired up after the powerful cum he didn’t hesitate for a second to follow the orders of who he now thought of as his older brother. He started licking the wall with gusto, and just when there was no trace of cum left on the wall, he felt another blast of fresh cum land on his face and tongue. He looked up just in time to see Rich Jerking his cock in his direction, pumping out a fresh load all over the wall and his face.
“Keep licking slut. Taste my jizz too” Rich scooped a wad of his cum off the wall and fed it to Tim, using the finger that had just been in his ass. Tim didin’t hesitate, making Rich smile. “Good boy little bro, you are gonna make me and Dad proud.”
The praise made Tim beam with pride. His new idol praising him felt almost as good as the orgasm he just had. He felt like he finally had someone who understood him.
“Come on now Timmy; let’s get cleaned up before Dad blows a gasket. We don’t want to be late for breakfast.” With that Rich quickly started soaping up Tim, and he did the same to Rich. He could really get used to showering with another guy, he thought to himself. He was amazed at how quick Rich could turn from being so sexy and dirty, back to being just friendly older brother type Rich, scrubbing him clean, and then helping him towel off with more of the huge fluffy towels, before he led him naked, back out of the bathroom into his bed room.
Apparently James had been in the bedroom while they were in the shower. Laid out on the bed were two outfits for the boys to wear for the trip to New York. For Rich, a nice pair of chino slacks and a Bateman photography polo shirt were laid out, and much to Tim’s chagrin, the shorts he wore the night before were neatly folded on top of another Bateman shirt, obviously intended for him. They appeared to have been freshly laundered. There was also a brand new package of underwear laying on his pile as well as a white tank type undershirt and a pair of gray socks with the sandals from the night before.
“Looks like Dad had some shopping done in anticipation.” Rich said examining the package of white briefs. They were old school type with a red dashed line around the waistband, like boys wore in the states in 70’s from Sears or Penny’s. “Hehe, boys sized 14, these ought to fit you nice and tight buddy, perfect for getting measured by Saul.”
Tim blushed bright red looking at the boy’s briefs.
“Hey buddy, at least you don’t have to wear the granny panties I gave you last night!” Rich said brightly. “Now hurry up and get dressed.”
Slightly jealous of the stylish look Rich had when he got dressed; Tim pulled the snug briefs up and then put on the undershirt. Rich made him tuck it into the pants, giving him a catalog model look, before pulling the shorts on and tucking the black shirt into them. He cinched the shorts up with a belt and sat down on the bed to put on the socks. The turned out to be only ankle length, and after donning the sandals and looking in the mirror, he confirmed his thoughts that he looked like a complete dork. He was dressed like a little kid he thought, especially standing next to Rich, who by now had put on a sport coat, and looked like a sophisticated young man.
Rich smiled at their own reflections in the mirror. Tim did in fact look like he was about 12 or 13 thought Rich, but he didn’t rub it into Tim. He knew he had for more embarrassing moments to come that day, and besides, he looked very sexy to him and new heads would turn in the city.
“Come on buddy, let’s go eat.”
Resigned to his fate, Tim followed Rich downstairs, with his thoughts returning to the shower as well as the spanking the night before. He had to adjust his cock as he walked down the stairs to the breakfast table.
James Bateman was putting out some fresh fruit and yogurt on the table to go with the omelets he had made for breakfast. “Good morning boys, I see you found what I put out for you, good. Timothy, I apologize for the ill fitting clothes, but it’s been a while since Richard was that small so we don’t have anything lying around, and I couldn’t let you be seen with me in your own clothes, no offense. I am known in the area where we are going, and my models have to be dressed nicely. We will take care of that today. Now eat up, the car will be here in fifteen minutes.” He was dressed casually, but impeccably in slacks, a sport shirt and jacket.
“No offense sir, I wanted this job to learn how to dress right I guess. Thanks for making breakfast too,” always polite, Tim answered the imposing figure.
They all ate quickly and then waited outside in the huge driveway for the car service that James had arranged to take them to Union Station. Rich explained to Tim that parking was impossible in the city and it was much easier to take the train.
Tim was amazed when he saw the shiny black limousine pull up. It wasn’t one of the ridiculous things you see on TV, but it was still slightly stretched, so that when they got in, James was facing the two boys seated next to each other. The driver loaded some gear for James in the trunk, got in and whisked them away, and soon they were at the train station. Tim had ridden the metro subway his whole life, but he had never been on the Acela Express before, so he was excited. The train would whisk them from DC to New York City in just under 3 hours.
Standing on the platform however, Tim was keenly aware of people staring at him and the way he was dressed, standing between the two Batemans who looked like TV stars. He tried not to think about it, but the cool autumn wind reminded him that he was wearing short pants while everyone else was in long pants. He was grateful for the boarding call.
He was surprised that they boarded a first class car. He had never hung around people that could afford such things, and was thrilled at the luxury of it all. The car was arranged with two seats on one side and one on the other, so acting like the little kid he was dressed as he begged Rich for the window seat, and Rich giggled and said sure. James sat across from the two boys, and got a Bloody Mary for himself and cokes for the boys, then opened his laptop and told the boys to enjoy the trip while he took care of some business.
The scenery flew by and before Tim knew it, the train was slowing down and pulling in to Penn Station in New York City. He was in the Big Apple for the first time! They exited the train and Tim was amazed at the crowds in the station. He thought DC was big, but this was unbelievable to him. He stuck close to the Batemans so he didn’t get lost in the crowd as they headed outside.
James led the boys out to 7th Avenue, where he had arranged another car to pick them up. While this was not as large as the limo in Washington, it was still a big back Lincoln. Tim ended up sitting in the middle of the back seat between the two Batemans, and James told the driver what address to head for. He felt very small in between the man and his son in the back seat, especially with his bony bare legs sticking up due to him having to rest his feet on the hump in the middle of the car. James pulled out his cell.
“Hello Rick? Hi James Bateman here, we just arrived in the city and have some time before Saul will be ready for us, any chance you can squeeze my new boy in?” Pause. “Great, we’re heading there now, see you in a few.” He placed the phone back in his coat pocket and squeezed Tim’s bare knee. “Since we have some time before the tailor, we are going to take care of that mop on your head first.”
While he thought his hair was just fine the way it was, he wasn’t about to argue with James. His hand on his knee was giving him goose bumps. He just oozed authority somehow and Tim would never think to defy him. He concentrated on looking at the huge crowds everywhere as the driver managed to steer the huge car through the maze of traffic. He about jumped out of his skin when he felt a hand on his crotch. He looked over and saw that the loose shorts he was wearing had ridden up while he scrunched in the seat and Rich had snuck his up the open leg and copped a feel. The look on Tim’s face caused the older boy to giggle. He winked at Tim and pulled his hand out. Between the feel though and James’ hand on his bare knee, he felt his cock stiffening. His cheeks were turning red as the car pulled up outside on non-descript storefront, with a barber pole on the wall. The curtains were drawn shut though, and it looked closed.
They got out of the car and while James tipped the driver, Tim read the sign on the wall. “Rick’s Tonsorial – By Appointment Only” Tim had no idea what Tonsorial meant, but the barber pole made it pretty obvious. He flicked his bangs out of his eyes and looked at Rich with a pleading look. “I usually just go to Supercuts, what’s wrong with my hair anyways? I thought models had long hair?”
“Some do Timmy, in fact, you will probably have to wear a wig sometimes, but for what we have in mind, you definitely need a trim,” Rich replied putting his hand on Tim’s head and messing up his hair. “We have plenty of girl models anyway.”
Tim wasn’t to sure he wanted to wear a wig and couldn’t figure out why he would have to, but he didn’t have time to protest. James pushed a small doorbell, and a few seconds later, the curtain was pulled aside briefly and then the door opened to admit them.
James pushed Tim in first, and Rich brought up the rear. After the three entered the shop, the owner, Rick, locked the door behind them. Rick was a large Italian looking man, wearing black pants and old fashioned white barber’s shirt that wrapped over a dress shirt. Tim could see that he was actually wearing a tie underneath! Tim looked around. It wasn’t a very big shop. Just one barber chair and a few waiting chairs around the walls, but what surprised Tim the most is that the chair was occupied.
“Have a seat gentlemen, I’m almost through here, I believe you know this young man here.” Rick said.
Sitting in the chair was a boy or young man around 18 years old Tim guessed. He had lots of freckles and bright red hair, that Rick was currently applying a wad crew wax too, and working it into a flat top style. Tim couldn’t see the rest of him as a white cape covered in red hair was draped over the guy, but it looked like he had come from a soccer game or something because Tim noticed the very expensive indoor soccer sneakers he was wearing and bright blue socks.
The kid in the chair smiled at seeing Rich and James and said, “Hi Rich, Uncle James. My dad said you would be at the shop today. That’s probably why he insisted I get prettied up for such important clients!”
James and Rich laughed and James spoke, “You are always pretty Robert, Saul didn’t say you would be in town. How’s NYU treating you?”
“Great sir, although it’s a lot more work than high school was.” The boy who Tim now figured out was named Robert replied.
“Hey Rob, this is Timmy, our new photo assistant and model. He’s going to be on the special client list. Timmy, Rob here is our tailor Saul’s son” Rich introduced them.
Robert laughed, “I figured he was special if you’re bringing to the shop, hi Timmy.” Robert stuck a bare arm out from under the cape.
Tim, not really appreciating being introduced as “Timmy” still took the offered hand and replied, “Nice to meet you Rob.”
“Have a seat gentleman I will be through in a minute. Timothy, why don’t you take your shirt off so it doesn’t get full of hair, you can hang it up next to Robert’s over there.
Slightly baffled as he had never heard of taking a shirt off for a hair cut, he did as he was told, as he figured it made sort of sense. It didn’t look like Rick was a man to argue with. “Yes sir,” he replied and started to un tuck his polo shirt while the rest of the men in the shop chatted away. Once stripped down to his tank undershirt, he grabbed a hanger hanging next to a blue soccer jersey and placed it there. That’s when he noticed that there was a pair of blue soccer shorts hanging with the jersey.
Puzzled he turned around just as Rick was finishing up Rob’s hair cut and pulling off the cape. Tim’s jaw about hit the floor when there in front of him in the barber chair was Rob, stark naked except for the bright blue soccer socks and shoes he was wearing. The socks were pulled all the way up his long slender legs over his knees stopping mid thigh, but as Tim’s gaze followed the socks up the creamy white freckled legs, he noticed Rob’s bright red pubic hairs. Not only had Tim never seen red pubic hair, he had also never seen a guy’s bush shaved into a downward pointing triangle, like a big sign pointing at his large even while flaccid circumcised cock dangling down between those thighs.
Rich giggled, “Got the full trim eh Robbie?”
Rob didn’t seem fazed a bit as he got out of the chair, “You know my dad; he likes me well groomed, especially if I am helping out in the shop.” He winked at Tim, who was still speechless and Rob walked nonchalantly over to the hangers and retrieved his shorts and shirt. He pulled a black jockstrap out of the shorts and pulled it up, stuffing his teen meat inside it and adjusting himself before grabbing his shorts. The soft white skin contrasted very sexily with the black ribbed jock, Tim thought. Tim’s shorts started to tent. Rob’s shiny blue soccer shorts were long enough that no skin was visible between where they ended midway down his legs and his extra long soccer socks were pulled up. He noticed Rob make sure the black Puma emblems on the socks were perfectly aligned at the front. Tim thought the look was very hot, especially with the bright red soccer shoes he was wearing.
“Hey I will see you guys in a bit. Timmy can’t wait to get a tape on you; you’re a real cutie pie. Looks like you will have fun too” Rob winked again at Tim, and grabbed the young teen’s bulging crotch. Tim didn’t even realize until then that watching the naked red head teen saunter across the shop and casually get dressed had caused him to sport a very obvious erection, which caused him to blush profusely as he watched the older boy step out of the shop.
“Ok then, Next customer,” Rick announced. Tim swallowed, and headed toward the chair. “Wait one second young man,” Rick said when he got close. “You’re a little on the small side, here…”
To Tim’s enormous humiliation he watched as Rick pulled out a booster board for the barber chair. Wearing the clothes he was, and surrounded buy three fully dressed other guys, he felt like a 12 year old as he climbed onto the raised platform on the barber chair. Even more embarrassing was that now his feet wouldn’t even reach the footrest, so his little ankle sock clad and sandaled feet, hung in the air as Rick placed a fresh cape over Tim’s front side. At least it hides my boner, he thought. He could feel his cock throb as the man placed the cloth around his neck. There was something about a man cutting his hair that made him feel weird. That is why he always went to the girls to get his hair cut; he didn’t want to get an embarrassing erection, which is exactly what was happening now.
“Ok, what are we doing today?” Rick asked.
Tim was about to answer when he realized that Rick was talking to James not him. He felt like he was back in grade school with his grandma taking him to the barber.
“We need a classic boy’s cut. You know Rick, about a 1968 catholic school boy’s cut. High sides and back, no bangs, and I want to easily see his ears,” James ordered.
“Very good Mr. Bateman, I’m always glad to make a boy look like a proper young gentleman. Does he need a trim downstairs too, or does he even have anything to trim?”
James laughed, “No what little he had, Richard here took care of last night. He won’t need any styling down there for quite a while. Just the top of the head for now Rick,” he turned to Rich, “Son, get out the Nikon and let’s document little Timothy’s first real hair cut.”
“Right Dad,” Rich said happily and opened up one of the cases James had brought.
Tim couldn’t figure out what was more humiliating, having everyone talk about him like he wasn’t even in the room, or the fact that they were discussing his scarce pubes or lack thereof. Soon enough though, Rick’s scissors were snipping away and to Tim’s horror, a very large amount of his black hair was falling down around him on the cape.
“Great expressions Timmy, keep it up!” Rich said as he snapped away with the digital SLR camera. Tim tried not to look right at the camera, and for some reason his eyes were tearing up. His cock was also getting harder and harder and there didn’t seem to be anything he could think of to stop it. He felt helpless and weird, and that was before he noticed the giant bulge in Rick’s pants as he worked his away around the chair. His long bangs were combed over his eyes straight down, and the next thing Tim knew, they were gone. Rick snipped across his forehead and his beloved bangs fell on the cape. No more hiding behind his hair!
Tim flinched when the electric clippers came to life. The girl that cut his hair at the mall always just used scissors. His whole body broke out in gooseflesh when the cold blade of the Wahl clippers pressed against the nape of his neck and started their trek across his scalp. He felt completely helpless as James stood by silently approving every cut Rick made and Rich documented it to the camera’s memory card. The worst was he was facing away from the mirror and had no idea what he looked like.
Just when he thought the horrible ordeal was over, he was surprised as Rick applied warm shaving cream over his ears and around the back of his neck. He then gave his straight razor a few swipes over the leather strop that was hanging off the chair, and then carefully shaved a sharp clean line from ear to ear. Only after wiping the last bit of cream away did Rick ask James, is this what you were wanting sir?”
James looked at Richard who smiled back at him. “Just about Rick, but I want that hair to stay in place for the rest of the day.”
“Oh but of course sir,” and Tim heard some fumbling behind him, and the felt a cold wad of goo being worked into his hair. Tim had never heard of Brylcreem, but he was about to see what it did to a boy’s hair. He felt his hair being combed into a style, and was very nervous to actually see what the final result was. He had a raging erection, but was afraid to try and adjust it because he didn’t want to be too obvious, but the more the barber man handled him, the more his little dick throbbed. He couldn’t figure out why getting an unwanted haircut and being under the control of the two grown men made him feel the way he did.
“Oh that’s perfect Rick, can you stand back a sec?”
Rich asked as he snapped away pictures of Tim’s new look. “Timmy you look perfect. Way better than before. Thanks Rick, I’ve got enough.”
“Very good sirs, here you go young man, take a look,” Rick spun the chair around to face the mirror.
Tim gasped. He now really felt like a Timmy again. His hair was now shiny black, slicked down with severe part on the right side, and it stopped way above his ears. He did in fact look like a character from some of those old 50’s or 60’s television shows. His humiliation wasn’t complete though, as when Rick unexpectedly yanked the cape off, the huge tent in his shorts was extremely obvious.
“Well it looks like you enjoyed it as much as I did young Timothy. This cut is on the house Mr. Bateman, as long as I can get some pictures of this fine looking young man!” Tim noticed a wet spot on the barber’s pants.
“Sure thing Rick. Thanks to you he is going to look great once we get him fitted up for some outfits next door. Stop by later for a drink with Saul and me if you like a little later on.” James opened the door to the shop and motioned the boys out.
Tim hopped off the chair and quickly tried to adjust himself before making sure to thank Rick (although for what he wasn’t sure, he was still mortified of the image he saw looking back at him in the mirror. Once on the street he got a chill when the wind ran over his newly exposed scalp areas that used to be covered by a healthy amount of hair. The shorts didn’t help either and he hugged himself and shivered. Rich saw this and pulled Tim close with his arm around his shoulder.
“We’re just going up the street Timmy. You look great by the way. I guarantee you that right now old Rick is in there masturbating just thinking about you!” Rich said laughing.
The statement caused Tim to blush bright red, but also didn’t help the state his cock was in. James though was not amused and cuffed his son on the back of the head. “Watch your mouth son. I don’t need to remind you that you are still not too old for me to remind you of your manners. I could think of a few outfits to get made for you as well today to remind you of that.”
Chastened, and rubbing the back of his head, Rich opened the door of their destination. “Sorry Dad. I didn’t mean anything by it.” He wanted to focus to remain on Tim this weekend.
Tim looked at the sign in the window of the good sized shop. It read “LAMPNER & SON, Fine Clothing for Men and Boys, EST 1882”. Once inside he saw bolts of fine looking materials against one wall, and row after row of suits, pants and all other sorts of clothing including athletic wear. It was eerily quiet inside, and Tim saw several older salesmen talking quietly with customers, mostly older men, but some teenaged boys with their mothers or fathers were present.
“Saul’s store does a lot of custom work for a lot of very important, read loaded people Timmy; they also do the uniforms for quite a few very exclusive prep schools in New England. We’re not buying off the rack for you though” Rich whispered to Tim.
“Off the rack indeed!” A new voice boomed. Tim turned to see a man walking toward them. If you looked in the dictionary for a picture of a tailor Saul could be it. An older middle aged man, with curly black hair and a growing bald spot wearing shirt sleeves and a tie, with a tape measure around his neck was walking toward them. While not fat, Saul definitely had some padding around the middle. The man walked toward James and the two men shook hands. “James, it has been too long my friend!” He turned to Rich, “and little Ritchie, so grown up now, in college even!” Then he turned to Tim, “and this must be the new boy needing something decent to wear by the looks of things, come on, andlet’s go in back.”
Without anyone getting a work in they were ushered through a back door of the shop through a room where Tim saw several older men hunched over sewing machines, silently working at their craft. They ended up in a medium sized room in back, with Saul shutting the door and locking it.
“Hey guys, good to see you again!” Out from behind a screen came Rob, carrying a small four legged step stool. Tim was surprised to see the boy, who was no longer in his soccer uniform, but now looked like an extra from an old movie or something. He was wearing 1930’s style brown corduroy knickerbockers pants that were buckled below his knees. He had on old fashioned lace up ankle length shoes and brown and yellow patterned knee socks. He was also wearing suspenders and a bow tie. “How do you like the outfit? We got the job doing the wardrobe for a depression era play and Pop is trying out the designs on me.”
James studied the boy, doubting that in the 30’s the lad’s trousers would be that tight in the rear, but the effect was not unpleasant. Along with Rob’s bright red flat top, he looked like he could be living in the 30’s he thought. Maybe I will get some of those knickers for Timothy he thought. “Very nice Robert, if you ever need any spending money, I can always get some work for you in front of the camera,” James told him. The kid was 18 now, which meant he could sell some nudes of the youth to legitimate clients. Red heads were always in demand.
Rob set the stool down and then sat down at a desk and turned on his laptop. Saul meanwhile gazed at Tim.
“So young man, I’m Saul and you have already met my son, all of him from what I hear,” he winked at Tim causing the boy to blush.
“Yes sir, at the, the barbershop I guess. I’m Tim sir. Tim Smith.”
“Glad to meet you Tim. My you are a pretty one. How old are you son, 13, 14?”
Tim turned even redder. He knew that with his clothes and his new haircut, that’s exactly what he looked like. “I’m sixteen sir. Since last month.”
“Well don’t be in a hurry to grow up Timothy. Anyhow, let’s get started, you obviously need some clothes. I shouldn’t let you into my shop dressed like that!” he winked at Tim, who was only too aware of what he was dressed like.
“So go ahead and strip down to you underwear and stand up on the stool please and we will get started.” Saul instructed. “Take your sandals off as well please then get up on the stool.”
“What? Oh, ah, OK.” Tim was not expecting this. He had never been to a tailor though, and guessed it must be normal. Still, he was not comfortable being almost naked in front of strangers. He was just getting used to the idea of undressing in front of just Mr. Bateman and Rich.
He unbuckled the sandals and set them aside, pulled his shirt out again and undid the belt holding the baggy shorts up. Saul made a tsk tsk, and grabbed the shorts and threw them to Rob. “Robert, put these with the clothes for the poor, he will leave in something decent!”
Rich laughed, Hey Saul, you made those for me when I was in 8th grade!”
“That was then, and you were a bigger boy than this little man is!”
Tim was humiliated. Again he felt like he was being talked over, and now here he was standing on a stool, surround by two adults and two older and bigger teens, all looking him over as he stood there in just his briefs, socks and undershirt. At least his hard-on was mostly down as for the moment, his penis was behaving.
He got more alarmed though, when Rich and James started getting out some camera gear. They were going to take pictures of this?!
“Hmm”, Saul said taking his tape measure from his shoulders. “Start by spreading your legs Timothy. Let’s get your inseam”
And that was how the session started. Saul measured Tim in every way conceivable, shouting out the measurements to Rob, who recorded them into a program on his laptop. He put Tim through a lot of different poses, not unlike the photo session earlier in the week, except this time he was being touched all over, including some very intimate places.
To Tim’s horror, but not to his surprise, all this attention caused his cock to start to stir. Saul pretended not to notice, but Rich and James were smiling as they snapped away. He thought they were done and was breathing a sigh of relief, when Saul stood and replaced the tape around his neck.
The relief was short lived though, when Saul grabbed the waistband of his briefs, “OK Timothy, time to lose the pants. Please get all the way undressed.”
“What? What for? Haven’t you got everything?” Tim was about to protest more when James cleared his throat and glared at him.
Tim saw the look on Mr. Batemans face and swallowed his next protest. “Sorry sir, I guess I’m just not used to this yet.” Tim stepped off the stool and sat on it to remove his small gray ankle socks.
While Rich snapped away, Tim stood back up, looked at everyone in the room, who were looking back at him, and pulled off his tank, setting it down with his socks and sandals. He now stood in his slightly tented briefs hesitating, trying to think of a way out of this.
“Come on Tim, you don’t have anything we all don’t have, its just a little smaller,” quipped Rich, which garnered him another cuff on the back of the head from his Dad, but brought a snigger from Rich at the computer.
Overcoming all his fear, Tim closed his eyes, hooked his thumbs in his briefs and pulled them down and stepped out of them, now completely naked in front of the other three in the room.
“Ah, no hair yet? Don’t worry son, it will come!” Saul said, winking at Tim.
Wanting to protest that he had been shaved the night before, but being to tongue tied to protest, Tim took his place back up on the stool.
Saul grasped the lad’s cock and started to measure it, barking out more numbers to Rob who input them into the computer. He couldn’t think of a reason why he would need this information, but kept his mouth shut, turning bright red as the old tailor started to rub his cock to hardness.
“We have to leave room in your pants for this young man. Don’t want anything sneaking out!” Saul said cheerfully! When Tim was fully erect, Saul took measurements of his cock’s length and circumference, as well as the size around the base of his cock and his scrotum. “Nice that there is no hair in the way. I can think of a few nice costumes already for this one James, he’s adorable!”
Tim’s eyes were closed and his face was burning bright red!
“Ok Tim, we are done with this, but we need to get a computer image of you against a wall in the other room. It’s a new program Robbie here designed to show customers what they will look like in their choice of outfits before we make them so they know if they want it or not, but now, you need to loose the stiffy!” Saul flicked Tim’s rock hard dick, which was now leaking again much to his horror.
“I can help with that Pop!” Robert cheerfully volunteered, hoping to get his lips around this cute thing standing before him.
“That won’t be necessary Robert,” James announced. “Timothy, go ahead and masturbate into your hand. We need to keep a move on so Saul can get started on your clothes.”
Thinking he surely misunderstood his boss, Tim looked at James? “Excuse me sir? You want me to what?”
I didn’t stutter Timothy and don’t like to repeat myself. Masturbate into your hand and do it quickly!” James commanded.
Startled, Tim grabbed his cock and started rubbing it. Rich had the camera aimed at him, and now Rob came around and sat in a chair along with Saul and James.
Thoroughly embarrassed, Tim proceeded to jerk on his four inch hard on and play with his hairless balls, while the two adult men watched him, chatting casually about other things. He didn’t understand why he was so turned on but he sure was! He was sure he saw a bulge in Saul and Rob’s pants, but couldn’t tell about Mr. Bateman, the man seemed as cool and collected as ever and always in command of his emotions. He figured Rob probably did, but he was busy taking pictures. More pictures of him jerking off! What is someone saw them? The thought of that humiliation set him off, and before he knew it, he was shooting a sizable load of sticky goo into his palm. His cock gave a good five good solid squirts before he started calming down and the orgasm began to subside. Cum was starting to leak through his cupped hands and Rob got up to get him a tissue.
“No need for that Robert,” James announced. “Timothy, please clean up your mess. Lick it up and I expect you to completely clean off your hand.”
“In the meantime Richard, I think you need to use your mouth for something besides talking. Show your Uncle Saul you still now how to please a gentleman.”
Rich put down the camera. “Yes sir” Even thought Saul wasn’t his real uncle, the two men had been friends for years, and each child had spent a lot of time with each others fathers. Rich walked over to where Saul was sitting and got down on his knees between Saul’s legs and started unbuttoning the rotund man’s trousers.
Tim stood there frozen unbelieving as he watched his friend start fishing the tailor’s large cock out of his pants. James broke his trance.
“Timothy, that’s one for the punishment book. I believe I told you to do something!”
Startled, Tim hesitantly brought his cum filled hand to his lips and started lapping up his sperm. It’s not that it tasted bad, but doing it in front of people was so humiliating, and yet so… so what he desired. He was being totally controlled and it was scary but also extremely erotic to him.
“Suck your fingers one at a time boy.” James commanded.
As Tim followed his orders, he saw that Rob was now kneeling at Mr. Batemans crotch, the sleeves of his white shirt were rolled up and the knickerbockers were hugging his ass tightly as he bent over and worked his mouth around his boss’s monster sized cock. He could not believe this. One week ago he was jerking off in his bedroom imagining what it would be like to have sex with another guy, and here he was, naked in front of two middle aged men, sucking his own goo off his fingers while they were getting serviced by their boys, one of whom was dressed like a kid from the 1930’s. His life had turned upside down!
By the time he had cleaned his fingers off; his cock was hard again from watching the blowjobs. Saul came first, giving a loud grunt and grabbing the back of Rich’s head. Tim watched in awe as Rich was able to take the whole load form the tailor without spilling a drop, swallowing Saul’s load and putting the man's hard cock back into his boxers and buttoning up his fly.
A few minutes later, he heard Rob making an effort to swallow the load that Mr. Bateman was feeding him. He almost got it, but when the cute redhead stood, he had a large amount of cum around his lips. He went over to a sink and grabbed a washcloth, soaking it in cold water.
“Sorry Uncle James, your cock is so dang big, I can’t keep my lips all the way around it.” He laughed as he walked over to Tim. Rob wrapped the cold cloth around his hairless genitals causing him to squeal, but also having the desired shrinking effect.
James laughed too. “No worries Robert, it was a great effort. Saul I hope my boy still knows how to please?” He used another washcloth provided by Rob to clean up and button his pants back up.
Saul smiled “Of course he doe. Thank you Richard, the wife doesn’t do it that good!”
Tim couldn’t believe that Saul had a wife, and wondered how he managed to keep this side of his life private, but sure wasn’t going to ask. Rich thanks the tailor and picked the camera back up.
Tim stood there, while the two men stood up, using the wash cloth to clean off the cum residue on his hand while he thought Mr. Bateman wasn’t looking.
Saul said, “OK, break time is over, Tim go over and stand against that graph on the wall.”
Painted on one part of the wall on the side of the room was a large grid. The lines were only a quarter inch apart and it looked like a super huge piece of graph paper.
“James you will love this. Tim, stand against the wall with your arms at your side please.”
Tim did as he was told and Robert came over and set up a special camera on a tripod in front of him. The camera had a cable that ran into a desktop computer on a small desk.
“Ok guys, this is my thing and a project for school that is working pretty well.” Robert announced, clicking on the machine. “Take a look at the TV over there, Timmy; keep looking right at the camera please...”
James and Rich looked at a large plasma TV that was aimed at them out of Tim’s field of view. On the screen was Tim, naked and looking apprehensive, his hands in front of his genitals.
“Hands and your side Timmy!” Rob ordered. Tim reluctantly obeyed. “Ok, say you want to see Tim in a new blue suit.” Rob said typing at his computer. In a second, there on the screen, was a live image of Tim, but superimposed over him was a very good impression of a tailored blue suit.
James whistled. “Robert, I am impressed. What other clothes to you have programmed in there?”
“Pretty much everything your clients would want Uncle James, and ours…” Rob winked at him, and onto the screen popped an image of Tim. This time though he was wearing what appeared to be a traditional British schoolboy uniform, with gray short shorts, long gray socks with blue bands around the top, brown T-bar style sandal shoes, striped blue blazer over a white shirt and tie, topped with a traditional old style school boy cap!
Rich got hard immediately upon seeing this and smiled, and James was amazed at how real it looked, getting a very good idea of what his new model could look like wearing such an outfit. Just with the first outfit on screen he could make twenty thousand dollars with Tim modeling it easily, and even more if the clients got to watch the shoot and meet Tim in person.
“Very nice Rob, what else do you have?”
“Here’s a few more…” In quick succession Rob brought up Tim wearing different style school uniforms, all with shorts and knee socks, scout uniforms, cub uniforms, choirboy outfits, a little Lord Fauntleroy outfit, as well as in different styles of very revealing bikini underwear and euro style swimwear, as well as different sports uniforms.
“And for the high paying customers…” There on screen was Tim as a catholic school girl…Rich burst out laughing. “Just kidding just kidding,” Rob said, but then whispered to James, “Unless you want, of course, we have done it for other special orders.”
Rich thought of making Timmy dress as a school girl and suck him off while he was dressed as a schoolboy. He almost shot his load right there and ran to the bathroom to jerk off before he ruined his pants. He would buy that outfit for Tim himself if his dad wouldn’t!
James was glad they made the trip. This would make ordering the first outfits much easier. He already had three clients lined up for Tim to model as a schoolboy and one as a scout, with this program, the sky was the limit!
“We will see, let’s stick to our normal line for now.” James told Rob. “First things first, let’s pick something your guys can do today so we can go out for lunch and then take some pictures of him around town.”
Tim was miffed that everyone could see what was going on but him, and that he was naked and everyone else, once again, was talking about him like he wasn’t even there. Still, he was getting more attention than he ever had before. He would soon discover that he would be the center of a lot of older wealthy men’s attention as they jerked off to his pictures or to him in person. He was about to become an official Bateman boy model.
End of Chapter 5.
I would like to know if this story is getting people off, so feedback is most welcome and encouraged. The comments section is full of spam, so i have disabled it for unregistered uses. A PM would be would be great, or feel free to email me at Scout65 at live . com. (hopefully you can figure that out :-) ) Seriously, I look forward to any ideas.