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The Boss' Tailor
I'm in shock. I have just been given a promotion at work, I will now be reporting directly to the global CEO. I leave my old boss in the meeting room we were in and head over to the CEO's office.
I knock on the door.
"Come in." His voice booms from behind the door.
I open the door and see the CEO sitting at his desk.
"James, congratulations!"
"Thanks, Rob. I appreciate the opportunity."
I walk in, close the door and take a seat opposite him.
"I've had my eye on you for sometime. After the way you handled that merger, I knew I had to bring you in a little closer to me."
"That's a few months of my life I'll never get back. The wife barely saw me!"
"How is your wife?"
"She's doing well. I don't know how she manages her job and the kids, but she never complains about the long hours I do."
"Sounds a bit like my wife. You better hold onto that one!"
"Don't worry, I will."
"James, I have complete confidence you're up to working with my team, but you're going to be dealing a lot more with the media and as part of your new contract there are some expectations on maintaining your appearance. Are you comfortable with that?"
"I'm willing to do anything it takes for you, Rob."
"Good. I'll have Janet book you in to see our stylist and set you up with a membership to the gym in our building, including your own personal trainer - don't worry, it's all covered by us and you even have time allocated in your schedule to go."
"Wow, you're really serious about this thing."
"I am James. Now there is another thing and I don't normally do this..."
Rob reaches over to his desk drawer and pulls out a tattered old business card and hands it to me. I look down and read the card - Mark Jones, tailor, by appointment only - with the address and phone number below.
"This is my personal tailor, he only takes on clients by recommendation. Make an appointment to see him and get him to make you a new suit, if you're happy with it, he can make anything else you would like, and it's all covered by the company."
"That's very generous of you Rob."
"Not a problem. We take care of our best and brightest. Now fuck off and sort your shit out, you have two weeks to settle in before I throw you in the deep end."
"I won't let you down Rob."
I stand and leave the office and head back to my desk. I sit down, pick up the phone and dial the number on the card.
"Mark Jones."
"Uhhh... Hi, I'd like to make and appointment to get a new suit."
"I can fit you in at 2pm today, how's that sound?"
"Sure, I can do that."
"See you at 2."
The call ends, so I hang up the phone. Not exactly a cheery person. He better be good.
The tailor is located near the office. It's in an old heritage building sandwiched between two skyscrapers. I open the door and enter the store. Down each side of the store are racks of men's clothing. Everything is neatly arranged by style and colour. At the other end of the store is the service desk. I walk up and a young male sales assistant greets me.
"How can I help you sir?"
"I'm here for my 2pm appointment."
The sales assistant nods and picks up the phone.
"Your 2pm is here, Mark."
He hangs up the phone and smiles at me.
"He'll just be one moment."
To the side of the service desk, a door opens and a tall, solid man enters the room. I gulp as I see his body - muscular and hairy, stuffed inside well fitted trousers and a shirt, the sleeves rolled up to reveal thick, hairy forearms, two shirt buttons undone at the top to reveal a broad, hairy chest. I glance at his face, grey hair, blue eyes, moustache, angular jaw covered in grey stubble. He extends a large hand.
"Mark Jones."
I shake his hand.
"James Walker."
"Come through, I'll measure you up."
The sales assistant smiles at me as I follow Mark through the door. The back room is filled with more racks of clothes, at the back is a small platform with mirrors behind it, a curtain is pushed to one side.
"Strip down to your underwear and stand on the platform."
Mark closes the door and locks it.
"Don't worry, no one is going to come in."
I step up onto the platform and take off my clothes, fold them and place them on the large chair beside the platform. Mark walks over to a cabinet on the other side and takes out a notepad, pen and tape measure.
"Stand up straight."
He places his hands and the tape measure at the back of my neck and brings his hands around to the front, his fingers gently brush over my neck as he does. The hair on my arms stand on end. He pulls the tape measure tight, almost like he is going to choke me, looks at it, then releases it, I breath in as he does. He writes the measurement down on the pad. Next he takes the tape measure and holds one end to my neck, he slowly guides the tape across my shoulders with his fingertips, holds it at the edge of my shoulder, then drops it down my arm swiftly, his hands brushing over my hairy arms. He pulls the tape away and measures around my wrist, his hands cup my hands and he holds them firmly for a moment before releasing me from his grip. He bends down and takes more notes.
"Raise your arms."
He places the tape inside my hairy arm pit (I hope I'm not sweaty) and drags his hand down my side to my hip. He then wraps the tape around my bicep and releases it, I start to wonder how many things he is going to measure. He takes more notes. He stands in front of me and we are eye to eye, he reaches around under my arms, pulling me into a bear hug, I can feel the heat of his body against mine, I can smell him, a mix of musky cologne and that earthy smell I get after I go for a run. He pulls back and drags his hands around my chest, his hands slow as he passes my nipples, I feel them harden and my cock twitches in my briefs. He pulls the tape measure tight, then quickly releasing it.
"Turn around."
I turn around and his hands feel across the top of my back, then from the base of my neck, down my spine, he pauses at the top of my butt, then pulls his hands over my butt and stops at the top of my legs.
"Turn."
I turn to see him taking more notes on the floor. He looks up at me and positions his face in front of my cock. He reaches behind me and pulls his hands around my waist, then releases the tape and brings it down to measure around my hips. I can feel his fingers graze over my cock and I look down and I can see his face next to my firm bulge. I can feel myself getting harder. He runs his hands from my waist down the side of my legs to my ankle.
"Spread your legs."
I step my legs open and he reaches around my thigh, his hand brushing past my balls. I look down to see him placing the measuring tape at my ankle, then he slowly pulls his hand up inside my leg and rests it firmly against my balls, this pushes my cock forward and I can see it's almost touching his face. It throbs in my briefs. He takes in a deep breath through his nostrils before releasing the tape measure to make more notes in his pad. He stands up and looks me in the eyes.
"Let's try on some things to see what you like."
He heads over to a rack and picks up a few items. He returns and hands me a pair of trousers.
"Try these, don't worry about the colour, I want you to see if you like the style."
I pull them on and he kneels back down in front of me. He pulls up the waistband which pulls the trousers tighter around my crotch. I can see my hard cock push out further, the fabric defining the shape. He rubs his hand down my sides and slowly around each leg, giving a quick tug at each cuff at my ankle.
"Turn around."
I turn my back to him and he brushes his hands firmly over my butt to smooth out the trousers at the back.
"Turn around."
I turn back to look at him.
"How do they feel?"
"Uhhhh... good I guess."
"You look great in these, go for a walk around and see how they feel."
I step off the platform and do a loop of the room.
"No pinching in the crotch? I can let it out a bit for you if it's too tight."
"Seems fine, I've never worn trousers this fitted before."
"The ones I make for you will fit like a glove."
He reaches over and picks up a shirt and hands it to me. I take it and slip it on. He reaches forward and slowly does up the buttons for me, then tugs at the sleeves and shirt tails to smooth it all out. He then unbuttons my trousers and proceeds to tuck in my shirt. First the back, his hands push firmly over my butt multiple times to ensure everything is in place. I can feel my cock throb more, what do I do, he's going to tuck this shirt in over my hard cock. His hands move forward and he tucks in the front of my shirt, his hands gliding firmly over my hard cock as he does. I let out a shuddered breath. He pauses, his face at my crotch, inhales deeply through his nostrils again before doing up my trousers. He brushes his hands over the front before standing up and looking directly in my eyes. I can feel my face is red and hot.
He turns around and grabs a jacket.
"Turn around, arms up."
He slides the jacket onto my arms, I move to allow him to put it on for me.
"Turn."
I turn around and face him again. Still blushing, my cock still hard and throbbing.
"You look smart. How do you feel?"
"Great." I lie.
"Let's select some fabrics and colours."
He takes my hand and leads me to a table with various fabric swatches covering it. He hands me some and gets me to feel the texture of the fabric. He holds them up to my hands and face and tells me which ones look great on my skin. All the time I can still feel my cock throbbing in my trousers.
We decide on the colours, a charcoal suit and white shirt, we can select a tie once it's finished, he tells me we can be more adventurous with our colour choices next time, before winking at me.
"Get changed, we're done."
I strip off the suit and shirt and get back into my own clothes. He opens the door to the shop and guides me through.
"Come back this time next week and I'll check the fit and make any final alterations."
"OK, see you then."
He waves and walks back into the back room, closing the door behind him. The shop assistant smiles at me as I walk out the store.
"Have a nice day!" He calls out behind me.
I return to work and sit at my desk. I try to process what just happened. This large solid man took my measurements and touched my body and it made me rock hard. I haven't thought about men like this in a long time. I remember as a teenager I would sometimes get hard when seeing the guys in pornos fucking the women. Once I started dating, it was always girls, and any thoughts of men disappeared by the time I met my wife and we started a family. I was shocked and a little confused. My cock throbs in my trousers when I think about Mark and his hands touching me. I quickly walk to the men's toilet and lock myself in a cubicle. I take out my cock and start jerking off. All I can think about are Mark's firm hands and thick, hairy forearms and how he seemed to touch almost every inch of my body. Within moments I start to shoot a huge load of cum into the toilet bowl. I grab some toilet paper and clean myself up. I stand for a moment and calm down. The thoughts in my mind subside. I flush the toilet, wash my hands, then go back to my desk.
The next day at work the CEO calls me into his office.
"How did you go with Mark?"
"Huh?" I'm confused.
"The tailor!"
"Ohhhh... really well."
"He's very... thorough..."
"Yeah, you could say that."
"He's also very discreet. He has many long-term clients. I've been going to him for almost 20 years!"
"Wow!"
"When do you pick up the suit?"
"I've got a fitting next week, so I guess some time after that."
"Excellent. You should keep an open mind with him. He has a good eye and knows exactly what you need."
Rob smiles at me and winks.
"Now get out of here, I have to make a phone call."
I leave his office and go back to my desk.
The rest of the week is busy with appointments with the stylist and personal trainer, not to mention getting my head around the new accounts I've been put in charge of. Before I know it I'm back at the tailors for my fitting. I'm actually feeling nervous. I'm worried I'll get hard again. Mark didn't seem to mind though, he behaved like it wasn't there, but the sensation of his strong hands all over my body did drive me wild. I ended up jerking off a few times during the week while thinking about him measuring me up.
"Good afternoon sir, Mark will be out in a moment."
I snap out of my daydream and the sales assistant is smiling at me. The door beside him opens.
"James, please come through."
I walk through the door and Mark closes and locks it behind me.
"Strip down to your underwear and stand on the platform."
I do as I'm told and strip down and place my clothes neatly on the chair beside the platform. Mark hands me a pair of trousers. I pull them on and do up the fly and buttons. The fit is amazing. I look down to see how it hugs my bulge. It's impressive and makes me slightly aroused.
"Turn."
I turn around and Mark pulls at the waistband and smooths the trousers down around my butt and legs. He pulls at the cuffs and I can feel him rolling up the fabric. I look down to see him pin them in place.
"Turn."
I turn and he hands me a shirt. I pull it onto my arms and he grabs the front and does the buttons up for me. He tugs at the cuffs and tails and places some pins at the end where the hem should be.
"Turn."
He pulls at the back and carefully adds more pins.
"Turn."
He opens my trousers and tucks in the shirt. His hands rub over my butt, more than it seems necessary, I can feel my cock getting hard. He brings his hands forward and tucks my shirt in the front and cups his hand around my bulge as he does. This makes my cock throb while his hand is still touching it. He removes his hands and does up my trousers, and with my cock straining at the fabric he brushes his hand over it to smooth it out. He turns around and grabs the jacket, this looks more unfinished than the shirt and trousers, there are threads hanging off it all over the place.
"Turn. Arms out."
He slides the jacket on and I can feel his hands running over my back and arms. I can feel him marking and pinning in different places.
"Turn."
He pulls the jacket closed and marks where the buttons should go. He adds more pins before taking a step back.
"Do you want me to let out the front of the trousers?"
"No, I don't mind how they look."
"They do look good on you."
"Thanks."
"Get changed. I'm done."
I carefully take off the suit and shirt and hand the pieces back to Mark, he carefully hangs them up while I put my clothes back on.
"Do you always wear briefs James?"
"Yeah, why?"
"You might want to consider some other options. Do you mind if I provide you with some options during your next appointment?"
"Sure, why not."
"Great!"
Mark opens the door and guides me out to the shop.
"2pm Friday OK with you?"
"OK."
Mark walks away and closes the door behind him.
"Have a nice day!" The sales assistant calls behind me as I leave the store.
The rest of the week flies by. I find myself jerking off multiple times a day thinking about Mark. I can't get him out of my head. I even find myself thinking about him as a fuck my wife. She comments on how horny I've become. She likes it.
It's 2pm on Friday and I'm standing in front of the sales assistant again. He looks at me and smiles. The door beside me opens and Mark gestures to come in. He closes the door behind me and locks it.
"Your suit is ready, but before we try it on, I have some underwear for your consideration."
"Sure."
"Get naked and stand on the platform."
I strip off and stand naked in front of Mark. I can feel myself getting hard and my face starts to flush. He hands me some white underwear and I go to put them on. I look down and look at the straps. Awkwardly I step into them and pull them up.
"It's a jockstrap."
"Yeah, I know what that is."
"More men wear them than you might think. They are quite popular these days."
He kneels down in front of me and pulls at the waistband.
"Turn."
I turn and he pulls at the straps, making sure they are sitting right on my butt. I look down and I can see my cock is poking out in the mesh pouch and pre-cum is starting to soak through.
"Turn."
I slowly turn around and look down at Mark.
"Sorry."
Mark looks up at me.
"Why are you sorry?"
"Look, I'm not gay, I have a wife and kids."
"Why would I think you are gay?"
I point at my cock and Mark laughs.
"Getting a boner in front of me doesn't make you gay James."
"But Why do I keep getting hard?"
Mark stands up and looks into my eyes.
"Most of my clients pop a boner when they come here. It happens all the time. The last thing I want to do is make you uncomfortable. Are you feeling uncomfortable James?"
"No."
"Good. If you ever do, we can stop and you can take a break or leave. If I ever feel uncomfortable I'll do the same. So far I haven't had a problem at all."
"So you're not bothered by my cock leaking through this jockstrap?"
"Not at all, you're free to do whatever you like here, I'm not going to judge."
Without thinking, I reach forward and put my arms around Mark. He puts his arms around me and holds me tightly. I bury my face into his neck and sniff. He smells so good. My cock throbs against his. I can feel his cock throb too. I pull away from him and look down at the hard bulge in his trousers. He smiles.
"I'm only human James."
I smile back.
"What's my wife going to say about this jockstrap?"
"I have a feeling she will like it. Like I said, many men wear them, and all their wives love seeing them in one."
"Really?"
"Never had one complaint."
"I'll take your word for it."
"Let's get you into this suit."
He hands me the trousers and I put them on. I leave them undone, he hands me the shirt and I put it on, he reaches over and does the buttons up and tucks my shirt in. He gives my cock a gentle squeeze before doing up my trousers.
"Turn."
He slides the jacket on me.
"Turn."
He does the top two buttons of the jacket up then proceeds to brush his hands all over me to smooth down the suit.
"You look great."
"Thanks. This is the best suit I've ever worn."
"Let's choose a tie."
We walk over to where the ties are and he holds up a few. I pick out the red one and he ties it around my neck for me.
"One more thing!"
Mark walks over to the table and picks up a shoe box and pair of socks.
"You'll need these too."
He gestures towards the seat and I sit down. He gently lifts each foot to put on the socks, then he carefully slips on the new shoes. They fit perfectly.
"Now you're ready to head back to work."
"I'll have to lose this boner before I do."
"I'll pop your clothes in some bags you can hold in front of you as you walk back to work, how does that sound?"
"Sounds like a plan."
Mark grabs a few large paper bags and places my shoes and clothes inside them.
"Now James, you're welcome to come here at any time for any reason, just make sure you make an appointment first."
"Yes Mark."
"And you're welcome to do anything you like when you're here. Anything."
Mark smiles at me and hands me the bag.
"Let's get you back to work."
He opens the door and guides me out to the store.
"Call me any time."
"I will."
He leaves and closes the door behind him.
I race out the store and back to work, I go straight into the toilets and open my trousers. The pouch of the jock is soaked in precum. I pull the pouch to one side and release my rock hard cock. I start to stroke it and immediately shoot a huge load into the toilet bowl. I lean against the wall and try to calm down. I grab some toilet paper and clean myself up, then stuff my cock back inside the damp pouch. I tuck my shirt in and do up my trousers. I stand up straight and close my eyes and compose myself before leaving the cubicle, washing my hands and returning back to my desk.
I pick up my phone and dial.
"Mark Jones."
"Mark, it's James. When are you available next?"
"Monday, 4pm."
"I'll see you then."
He hangs up the phone. I'll have to wait all weekend before I get to feel those hands on me again.