A New Chapter by FlattopQuestioning

---

John was a 27 year old IT worker who had been working from home since the pandemic hit and was beginning to look like he hadn't surfaced since. Apart from a trim here and there, his hair had reached his shoulders and began to start curling out on its own from sitting on his broad shoulders all day long. With this long hair, John had started to incorporate more and more feminine workwear into his repertoire. First it started with panties and a bra, and eventually ended up with a chastity cage, hip pads, earrings, and some business styled dresses. It became almost a daily ritual to get ready for work, and it all started with the hair! As soon as the sun would be up, John would have the curlers in and styling tools out.

This lifestyle had been going well until John decided to join one of his meetings as he always does, but in a failed attempt to multi-task and do something else, John had forgot to turn his camera off! Luckily, John's coworker Derek had jumped on early and pointed this out. John had instantly felt his stomach drop as his coworker sent him an IM:

"Hey, not that I'm complaining, but your camera is on. You look gorgeous in my opinion, but not sure how comfortable you are with everyone seeing you like that :)"

As John's eyes ran over the message and he turned his camera off, that last part of the message kept repeating inside John's head.

"He thinks I look gorgeous? Really?? He must be kidding, I can never show my face around the office again, let alone run into him there."

A few weeks went by before an issue came up that required John to come into the office the next day. John woke up that morning, putting on a nice fitted pair of jeans with a button down shirt, definitely a bit more masculine of an outfit than John was used to wearing anymore. John tied his hair back into a bun and hopped in the car, having no idea what kind of day he was really about to have.

The morning had gone by quickly and resolved the issue after spending all morning in the network closet by himself, hoping to sneak out of the office around lunch time and head back home. As John was wrapping up his work in the network closet and stepped out, he stepped out and locked eyes with someone he was not hoping to see that day. Derek stood there, a little over 6 feet tall with a grown out bald fade with some length left on top. If John had to guess, Derek was in his late 30's or early 40's.

"John! How's it going buddy, what are you doing in the office today?" Derek asked.

"Go..good. Just wrapping up some issues that came up over night with the firewall." John replied.

"Just wrapping up huh? Sounds like your schedule is clear, doing anything for lunch?" as if the response really mattered to Derek.

"Oh... well... I was planning on heading back home on finishing out the day there. I actually was planning on skipping lunch" John said while rubbing his hand on the back of his neck.

"Really? Look, if you're uncomfortable about what happened yesterday, I totally support you! It's just that, with the pandemic being over and everything, I think you should consider a bit more of a professional look!"

"Oh... no... it's nothing like that. I just-" and before John could even finished his sentence, Derek interrupted.

"Perfect! Well if nothing is wrong, I was actually planning on running down to the barber over lunch. I'm overdue for a trim and I think you should join me. You've got those tight little jeans on, button down shirt, and I think I know just the haircut that would match. Come on, they won't bite your head off down there!"

John started to feel mesmerized by Derek's smooth talking, he was in sales after all. With this talk of tight jeans and my outfit? What could he be thinking?

"Well I don't know, what did you have in mind?" John sheepishly asked Derek, looking for any way out.

Derek put his hands on John's shoulders, looked him right in the eyes and said in a stern voice

"Why don't you leave that up to me. I get the feeling you're the kind who might like to give someone else the keys. So why don't you hand over those keys and go get you a haircut. I'll drive."

John could feel the blood start to flow and began getting as rock hard as he could in his cage. All John could utter out was "Sou... sounds good to me Derek"

Derek and John got buckled in and began driving down to the barbershop. John was extremely nervous, barely even able to make small talk. He felt as though he was under Derek's hypnosis at this point, he was just hoping that Derek was going to be asking anything else anytime soon. After a short drive, Derek had pulled into a parking stall right in front of the barbershop. Outside the door was the classic barber pole, with a massive glass front and incredibly bright light bulbs, putting anyone who was getting a haircut right at the front of the stage for anyone who happened to be walking by.

Derek had ushered John in front of him, probably to make sure there was nowhere he could go as they both walked in. The shop was completely empty, apart from the barber who was just beginning to get up from his chair.

"Hey Derek! Good to see you again. Decide to bring your girlfriend in with you today?" The barber joked.

"Hey Bill! Actually, this is John and he's decided to come in and get a haircut today! But before we get to him, let's make sure the boss is taken care of" Derek said as he walked up and hopped in Bill's chair.

Bill was right around Derek's age, and by the way they conversed with each other, had known one another for years. Bill had a bit more of a slender build than Derek, but still had the mature stature similar to Derek's that intimidated John.

"Ahhh, always been one to put himself first! You going first will be a good chance to get these clippers warmed up before we get to John. Just the usual today?"

John's ears perked up as soon as he heard that word. Clippers. Wait, clippers?? Touching these locks? John could feel the sweat start to build on his forehead and upper lip as he began to readjust himself in his seat.

Bill threw a neck strip and cape around Derek, beginning to make quick work of his bald fade. John just couldn't picture himself up there. It had been almost a decade since John was in a real barbershop, having converted to salons in order to keep up with his long hair.

Before too long, John noticed that Bill was taking the cape away from Derek's neck, and brushing off the remaining stubble from his neck.

"Alright buddy, your turn. Hop on up!" Bill said to John.

John could hardly stand up, his knees and legs felt like jello that was about to collapse underneath him. Not wanting to embaress himself, he put enough coordination together to step up into the classic barber chair and put his feet on the metal foot rest.

"Well young man, what will it be today" Bill asked. John had to be at least 20 years younger than the other two gentleman in the barbershop.

"Actually, I'll be taking care of that decision today. I think John needs something new, something that no one would expect. John just graduated from university not too long ago, and I think this haircut is going to help him start a new chapter of his life." Derek interrupted before John could get a word in.

"You know, why don't want we make a real impression on John and give him a horseshoe flattop."

"Hmmm, you think he could pull it off?" Bill said.

"If you're wanting John here to get a nice horseshoe flattop, let's make sure we do it right and take that landing strip right down the skin. What do you say?" Bill continued.

"That sounds great! If we're talking this sharp of a haircut, it sounds like we might be here a little longer than a normal lunch would take. John, no one will notice you being gone from the office this afternoon with the work you put in this morning." Derek replied.

John had been sitting up in the chair, eyes so wide you would have thought they were going to pop out. Without even thinking twice, John had mustered up the strength to just eek out a "Yes, sir" putting a massive smile on Derek's face.

"Sounds like you've signed your fate John! You're just in luck, horseshoe flattops are my favorite haircut to give! Derek, could you do me a favor and lock the door and flip the sign on it to 'Closed', and I'll lower the blinds? I don't know about you, but I don't think an event like this should have any chance of getting interrupted."

John thought to himself, lower the blinds? Flip the sign to 'Closed'? What was going on here? John was avoiding every urge to jump out of that chair and run out, but something almost ethereal was keeping him in that chair. After Bill had lowered the blinds and Derek flipped the sign and locked the door, John knew there was no going back. He was along for his first ride of many that day, and his main focus now should be relaxing.

"Don't worry, you're going to love this" Bill said as he collected John's hair and moved it all to a single side of his shoulder. Bill reached down and pulled up the pinstripe cape that had slipped down into John's lap, snapping it tight into place. John took one last look in the mirror before Bill spun the chair around and faced John directly into the waiting area where Derek was sitting. It was really about to begin.

John could here a collection of noises going on behind him, nervous and ready to jump at anything that was about to happen. After the clinking, brushing, and squirting noises had subsided, John heard them.

*Click*

The sound of the Oster Classic 76 Clippers whirring up, there was no other sound like them. John felt a comb running through his long, blonde, silky locks for the last time, before he felt Bill tilt his head into his chin, and run those clippers right up the back of his neck. Instantly, John felt the air conditioning and freezing cold that he hadn't experienced in years. Swipe after swipe, more hair came tumbling down, all piling up into John's lap right on top of the cape. John didn't know whether to be ecstatic or to cry. After Bill had worked his way around the sides of John's head, he combed everything left on top all the way forward, temporarily blocking John's view with his own hair.

Bill walked around to the front of John, clippers and comb in hand. He ran the comb against John's forehead and lifted up all the hair in front, running the clippers over the comb and letting out a big *Shiiiiink*. John felt like he was going to burst right out of his chastity cage. With each additional pass Bill made over the top of John's head, he could feel the cool air and the lack of all that weight the clippers had freed him from. With all the extra weight off, Bill could start getting down to the real work of shaping John's new magnificent flattop. Bill switched the clippers off and made a comment.

"Wow John, I haven't had to lop off that much hair in years! You're really starting to look cute, and we still have a long way to go. Can I interest either of you gentleman in a drink? John, might help ease your nerves a little bit! I should let these clippers cool down for a minute anyways."

Bill grabbed three shot glasses and poured up three shots of whiskey. All 3 threw back their shots and felt things start to loosen up.

"I'll grab the good stuff after we're done here. You're in good hands!" Bill said as he put his hand on the back of John's head.

John could still feel the heat from the whiskey in his throat. He heard Bill switch the Oster clippers back on, and before he could even process what was about to happen, saw the clippers come around to the front of his head, and shear right down the center of John's head, leaving a narrow piece of stubble for a landing strip. Not being satisfied, Bill went over the landing strip two more times, widening out and really setting into stone that this man was going to end up with a horseshoe!

"Damn Bill, I don't think I've ever seen you cut a landing strip like that. You're really giving him the platinum treatment." Derek said as he tried to contain his smile.

"Well Derek, when someone like John walks into your barbershop with you close behind, wearing those tight jeans, nice little button down shirt, you need to jump on that opportunity! I always love having a tight ass sit down in this chair." Bill said as he started rubbing some hair wax in his hands and running it through what was left of John's hair. After thoroughly working the wax in, Bill grabbed his blow dryer and began standing John's hair straight up. Bill wasn't going to be satisfied until every one of John's hairs was standing at attention, just like everything else.

Bill fired up his Wahl clippers and started taking the top down as high and tight as he could. John kept looking at Derek, who couldn't take his eyes off John's haircut, like it was something he's never seen before. After Bill was satisfied with his clipper work, he grabbed a pair of freshly steamed, how towels and wrapped John's entire head.

John was partially deafened by the towels and starting to feel his buzz kick from the whiskey kick in. He could hear Bill and John trade some conversation back and forth, sharing a small laugh before the conversation naturally died down. By that time, the towels had cooled off and Bill had grabbed a couple of dollops of shaving cream, spreading it over John's landing strip and head. John could hear the straight razor going back and forth against the leather strop attached to the chair, before being ever so gently scraped against his head, starting at the sideburns before moving around the back.

John felt that Bill could sense his pleasure and that's why he was saving the landing strip for the finale. As the razor met the front of the landing strip and Bill began to pull back, John let out a slight shudder as everything began to leak out of his cage uncontrollably. With each passing scrape, John felt more and more drawn in by the haircut that Derek had brought him there to get.

As Bill finished up his final touches, he spun John around in his chair to face the mirror and show off his work.

John's jaw dropped just from seeing the contrast of the darkly tanned skin from the summer sun, and the absolute white from the skin that had just been sheared all the way down to the skin. Bill put his hand on the back of John's head and tilted it down slightly.

"Check out that landing strip John. How can you not like something like that?" Bill said.

"I... I really like it." John said, barely catching Derek standing up from his chair to come over and inspect. As Derek stood next to the barbers chair, John had noticed the massive bulge in Derek's pants as he was looking closely at Bill's work.

"Damn Bill, you've really outdone yourself. You've given this one of a kind man a one of a kind haircut!" Derek said.

Bill began taking the cape away from John's neck and shaking it out, discarding all that hair that was on John's head not even an hour ago.

As John began to stand up, Derek placed a hand on his shoulder as if to tell him that he wasn't quite done yet. Another hand reached down to the front of John's jeans and began to rub up and down in front of his crotch.

"Well, it looks like there's more to you than meets the eye. Maybe we should take a closer look and learn something else about you John. Bill, why don't you go grab those glasses and scotch?" Derek asked.

Not even having left the barber chair yet, Derek began to undo John's belt and completely remove his pants, leaving him in just his polka dot, bikini cut underwear. Derek instructed John to remove his underwear and shirt. As John removed his clothes and handed them over, Derek grabbed the key to John's chastity cage out of his pants pocket and set his clothes up on the counter.

"Hey, Bill! Looks like John wants to give me the key to his chastity cage! Why don't I leave this here with you so he's incentivized to come keep his shoe up to our standard!"

Bill, walking back with drinks broke out into a big smile as he heard Derek and saw the way things were heading.

"Wow, just when I thought this day couldn't get any better. What a wonderful idea Derek. John has been through a lot today, what do you say we give him a reward for being so good while getting his hair cut today?" Bill asked Derek, winking at John as his question came out.

Both Derek and Bill were now standing in front of John, who was now bare naked sitting in his new barbers chair. Derek walked around behind John and began rubbing his landing strip with one hand and put his other hand down his pants. Bill, began rubbing his hands on John's thighs with deeper and deeper passes. As the three of them kept sipping their drinks, things kept getting more and more sensual.

"Bill, before we keep going, I think John should be a good boy and clean up the mess he's made on the floor with his hair. We can go get prepared while he cleans up. John, after you're done cleaning up, get into the 'Collar Me' position on the floor and don't move a muscle until you're directed to. You seem like you should know those instructions well enough for me to not have to show them." Derek said, handing over a plastic ziplock bag to John.

"Yes, sir." John said as he got out of the chair and onto his knees on the floor. Derek had disappeared into a back room, closing the door behind him, and Bill began to take his barbers smock off and loosen his belt. John used his hands to pile up his hair and place it into the bag. After everything was cleaned up, he set the bag on the counter, and got into position in front of the barber chair. By this time, Bill had removed his pants and barbers smock. Derek came out from the back room with a collar and leash in hand, putting it on John's neck and locking it into place with a tiny master lock, making it unremovable without a key.

As John was being led into the back room on all fours, he saw the leather horse being illuminated under a single light bulb. He climbed onto the horse and Bill and Derek began strapping John down.

"In case you're wondering, this is Bill and I's handiwork. Never been used until today, so hopefully we put enough restraints on here to really keep you in place. Go ahead and place your head here for me" Derek said as he gestured to a metal half moon sticking out from the front of the horse. John placed his neck in, and before he knew what happened, Derek had placed the other half on top of John's neck and placed a couple locks on. John really wasn't going anywhere now.

Bill and Derek had disappeared from view. John was facing the block wall at the back of the room, puckering his little butthole in fear of not knowing what was going to happen next. Before long, John felt a hand rubbing up and down his landing strip again. Derek had appeared in front of him again, bent down and spoke in a low, calming voice.

"I just want you to know that you have been so good today. When I saw you on camera, I just had this gut feeling that you would enjoy this. I'm glad you were able to come along with me and start this journey. Because of that, Bill and I have decided to reward you".

Derek stood up, and the only thing in view of John at this point was Derek's throbbing cock. John could almost feel the pulsation, but really started to feel it as Derek inserted his cock into John's mouth. John was a virgin up until this point, and completely inexperienced when it came to pleasuring his new master.

"I was a little worried you were going to be new to this. Luckily for you, I thought ahead and got you a little present." Derek said as he grabbed a spider gag from off the workbench nearby.

As Derek put the gag on, John could feel the cold leather press tightly against his head. Derek re-inserted his member into John's mouth, with the confidence that he now had complete control over John's mouth. As Derek began going to work, John felt a slight shock at the other end as Bill had begun lubing up his butthole and getting him ready. John had some experience masturbating with dildos, but nothing was going to prepare him for the ride he was about to go on. After warming up with lube, Bill inserted his rather large member into John's rear end, grabbed both shoulders, and began going to work. After switching off a few times, the moment had come. Derek and Bill had appeared in front of John, stroking their cocks and setting their eyes on one thing. John, completely immobilised, could sense what was about to happen. Deciding to fully embrace the moment, he stuck his tongue out and began begging for what was going to cum next.

Bill and Derek seemed almost shocked, like they weren't expecting John to learn this quick. Derek decided to take the top floor and came quickly directly onto John's landing strip. as Cum was dripping down the front of John's face and down his nose, Bill placed his cock gently on top of John's tongue and shot his entire load down John's throat. Without the ability to do anything, John had no choice but to put as much of a smile as he could on his face.

"Well, there's still a couple of hours left in the day and I need to hop on some meetings. John should be okay here for awhile, I can pick him up after work and take him home." Derek said as he lightly slapped John's cheek as if to say good effort, and gave him a firm spank on the way out of the door into the barbershop, making sure to leave a hand imprint.

John was left in place to let the cum dry on his newly christened landing strip, and swallow the load that Bill had given him for a late lunch. John was left on the bench for a few more hours and listened in as Bill cut the hair of a few more customers. After what felt like an eternity, John heard the door to the back room unlock and began to feel the straps loosen and locks taken off.

Derek handed him his clothes and allowed him to get dressed, before walking John out to his car and ushering him in.

"Well, what did you think of today? Didn't think that leaving your camera on would lead to all this would it?" Derek asked.

"No, sir. I definitely didn't expect that, but I think this I could see myself doing this again." John replied.

"Well I sure hope so, I went ahead and scheduled us back to back appointments every couple of weeks for the rest of the year! Hope you're ready to keep that flattop in shape." Derek said, as if he would ever give John the choice again.

---