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Shopping for Underwear -- Part 1
"Can I help you with anything?" I hear in a deep, husky voice.
I turn to see a solid, middle-aged male, shop assistant standing behind me. He smiles.
"Uhhh, I was looking to buy some underwear, some boxer shorts, maybe, I think..."
"Looking to try something new?"
He smiles again. I start to blush.
"Uhhhh, yeah, I guess so."
I've never been good at shopping for clothes, my wife tends to do most of the shopping for me. Since I've started going to the gym, I've lost a fair amount of weight, so my clothes are getting a bit loose. With my wife away for the weekend, I thought I should take the chance to find some new things to wear.
"What do you normally wear?"
"Uhhhh, y-fronts or boxer shorts."
"OK, maybe we can try on a few things."
He takes my arm and leads me towards a door in the corner. He swipes a card near the lock, it clicks and he pushes it open. Inside is an ordinary looking change room with separate cubicles and a curtain for privacy. He opens one of the curtains.
"Step in here and take your trousers off, I need to measure your waist."
I enter the cubicle and kick off my shoes and drop down my trousers, placing them neatly on the chair in the corner.
"Face me."
He gets down on his knees, his head near my bulging briefs, wraps a measuring tape around my waist, takes my measurement and quickly stands up.
"Wait here, I'll be back soon. You can keep your trousers off, only I have access to the door."
I stand there, alone, in my shirt, socks and y-fronts. A few minutes later, the door clicks and he comes back in, holding various items.
"Try these first."
I step into the cubicle and slip off my briefs. I step into the red underwear and I start to feel a little bit excited. I tuck my cock down and it creates an impressive bulge. Suddenly, the curtain opens.
"Well they look good, turn around, show me."
I turn around and face the shop assistant.
"Those are Calvin Klein boxer briefs."
He leans over and pulls up on the waistband, then tugs down on the legs.
"Much better, perfect fit."
He hands me another pair of underwear.
"Now try these."
I close the curtain, pull down the boxer briefs and my cock bounces back up. I slide on the white briefs, these look like they are Calvin Klein too. The curtain opens again.
"Classic Calvin Klein briefs. A little more smarter than your y-fronts."
"But I like my y-fronts"
"Don't worry, I like your y-fronts too, but these look a little more... professional."
He gets back down on his knees and tugs at the waistband again. His fingers flick under the leg holes at the back and slide across my butt, he removes his fingers causing the elastic to snap back. He reaches between my legs and tucks the leg elastic up higher, his hands brushing against my bulge, my cock throbs slightly. He stands up and looks at me.
"Very impressive. Take your shirt off and look at yourself in the mirror."
I do as he says and have a look at myself. The fit is good and I like what it does with my butt and bulge.
He hands me another pair of underwear, lime green, smooth feeling.
"These might be more suitable for the gym, but you can wear them everyday too."
I close the curtain again and slide off the briefs, my cock is hard now. I slide on the boxer briefs and they feel amazing against my skin. I like the colour too, it really stands out. I look down and notice my cock is rock hard in them, poking out at an angle. The curtain opens again.
"Well, it looks like you love those ones. Under Armour, everyone is wearing them these days."
"Do you wear them?"
"Sometimes."
"What do you normally wear?"
He opens his belt, unzips his fly and drops his trousers.
"I prefer to wear jockstraps. This is a Jack Adams one."
It's red and black. He turns around and there are straps hugging his exposed butt. I can see his cock is hard and straining against the pouch.
"Wow... C-can I try it on?" I stammer.
"Sure!"
He pulls off the jockstrap and stands up, his large uncut cock bounces up, at the base is a metal ring.
"What's that?" I point at his cock.
"A cockring, it makes your cock harder."
I slide off the boxer briefs and he hands me the jock. I hold onto the waistband and step in carefully to make sure the straps are at the back. The shop assistant steps forward and makes adjustments to the straps and stuffs my cock into the pouch. He holds his hand around my bulge and grabs it. He sticks his face into my crotch and sniffs deeply. He moves his hand away and starts to lick the pouch, his hands move to my butt, his fingers teasing the straps and my hairy crack.
"You're going to make me cum."
He pulls his head away and looks up at me.
"Good"
His mouth finds the head of my cock and he sucks through the fabric. This sends me over the edge and I start to moan and convulse. He grabs my butt and sucks harder, cum shooting into the pouch, he licks the outside clean.
I get my breath back, slide off the jock and hand it back to him.
"Sorry, I made a mess."
"Not at all."
He puts the dirty jock back on and rubs his sticky bulge.
"Your cum feels good against my cock, thanks for shooting in it."
"Thanks for making me cum, I've never done that with a guy before."
"So is there anything else you would like to try on?"
"No, I'll just take the ones you gave me."
"OK, let's get dressed and I'll put these through for you."
We put our clothes back on and walk out of the change room. At the register, he scans the underwear, neatly folds them up and places them in a bag. I hand him my credit card to pay.
"Thank you, Simon"
He hands back my credit card and I realise how he knows my name.
"Uhhh, thanks..."
He points to his name badge, which I didn't even notice before.
"John."
"Thanks again, John."
I take the bag and turn to walk away.
"Simon, come back anytime you need some more."