The cold November wind was blowing hard into Jay’s face on his long walk to work that Saturday morning. Making his eyes water so much you would have thought he was crying. He pulled the short, and somewhat inadequate, fleece jacket a little tighter around his chest and trudged on. He had no idea that today his life was going to take a big change of direction. Behind him a car gave a little beep beep as it went by, the driver assuming the cute little ass wiggling along the pavement was a girl’s. Jay didn’t react, he was used to it. His slight frame and long (for a boy) dark wavy hair made him look quite feminine. The ponytail and the black skin tight stretch denim jeans wrapped around his pert shapely bottom didn’t help much either. Jay had even been told he was “pretty” before, so being mistaken for a girl was nothing new.
“Dick head” he muttered to himself, but deep down inside he felt a little thrill of excitement, just at getting the attention. It was quite a long walk to work, Jay lived with his mum in the less desirable part of town. But the shop he worked at was on the high street in a rather more affluent area. Jay had worked for Mr Evans in the shop for a few years now, on and off, he started when he was 15, delivering papers, it was more of a newsagent back then. But, around the time Jay started college, Mr Evans stopped delivering papers, except for a few special cases, it just wasn’t worth the effort any more he said, and the shop became more of a convenience store. Some time later he called Jay, out of the blue, and asked if he wanted to work in the shop weekends. Jay was glad of the chance to earn some money, but didn’t really enjoy the work. Being shy and socially awkward he was uncomfortable with the customers, but tried his best to be friendly and was always polite.
“Morning… you okay?” Mr Evans asked, noticing Jay and the tears streaming down his rosy cheeks as soon as he walked in the door.
“Just the wind.” Jay replied, nodding and wiping the tears away. Jay liked Mr Evans, he was a serious and stern looking old man, in his late fifties or early 60s who, like Jay, also seemed to take on another persona specially for the customers. Usually Mr Evans (he told Jay to call him Dave but Jay felt very uncomfortable doing that), was a more reserved person who kept himself to himself, he was always kind and pleasant to Jay though. Mrs Evans however, was the opposite. She she was loud and a bit cude, she lived to chat and gossip with the customers and was in her element in a busy shop like theirs. She nodded hello at Jay as he entered the store and continued chatting behind the counter with Megan, a cousin or niece or something, who also worked there part-time.
The day went as usual, by ten the shop was starting to fill with customers and everyone was busy. Mr Evans was in the tiny office at the back of the store doing some paperwork while the girls manned the sales counter and got Jay to do the odd jobs, like making a brew. He knocked softly on the slightly open office door then walked in with a coffee in his hand.
“Coffee?” he inquired, and Mr Evans nodded, peering over his reading glasses. Jay leaned across the old man sat at the desk in the very small room, to place the hot cup on the mat on the far side of the desk. Dave leaned back in his chair a little to give Jay more room, and he momentarily admired the shapely bottom of the young man as he stretched over the desk. Jay left the room and a moment later Dave watched, through the small two-way mirror that looked out into the store, as Jay walked to the counter with coffees for the girls. There was something about that boy, was it the way he moved, or the small T-shirts he always seemed to wear, Or maybe his long slender legs and curve of his bottom in those tight jeans? He stood and leaned closer to the little window, watching as Jay reached up high to get something off a top shelf for a customer. Jay’s T-shirt lifted as he raised his arms displaying his smooth slender waist and bellybutton. Dave shook himself mentally and looked away, picking up his coffee and getting back to work. He was a happily married man and there was no way he would get involved in that sort of carry on, but still, he enjoyed looking.
At lunchtime everyone other than Mr Evans alternated a half hour break. By mid-afternoon things would start to quiet down. Mr Evans would leave for a couple of hours at about three, then come back in time to lock up. Mrs Evans and Meg would gossip behind the sales counter, and Jay, as usual, made his way down stairs into the basement storeroom.
The main storeroom was about half the size of the shop above and was somehow always warm and a bit stuffy. The walls were bright white and the room was well lit by a single, long strip light on the ceiling. The walls were lined with shelves and the floor was strewn with stock that needed sorting. Jay got to work eagerly, working as fast as he could, because it was getting close to his favourite part of the working day. When he was almost done he stood for a moment at the bottom of the nevşehir escort bayan stairs, listening. He could hear the girls upstairs chatting, as usual, so felt confident he wouldn’t be disturbed. In all the time he had worked in that shop, he had never seen Mrs Jones or Meg go anywhere near the basement, too many spiders for them.
Feeling excited now, Jay moved quietly to the back of the cellar store room, where a step up, led through a small arch, into a dark and spooky second room at the back of the main storeroom. Lit only by one small weak bulb, mounted on the wall separating the two rooms, this room was much smaller with a low ceiling and five rows of old wooden shelves that went from floor to ceiling and from the back of the dark room up nearly to the front, leaving just a narrow walkway by the lit wall, so you could get to each row. Most of the shelves were filled with stuff that wasn’t used much, like Christmas decorations and old shop fittings. But a couple of months ago, while having a little nose around, Jay had found a large cardboard box that looked a bit out of place. He had opened it and found inside a number of large brown envelopes. Some sealed, some not. Each envelope had a name on it and contained at least one, specialist adult magazine.
These were not your standard top shelf offerings. These were magazines for all manner of sexual kink and perversion, BDSM, pregnant, gay, hardcore, cross-dressing, mature, even some with animals. Jay quickly, but carefully, rifled through the envelopes and found one that tickled his fancy. He lay the magazine on a shelf, the dim light shining over his slender shoulder just about managing to illuminate the pages. Jay flipped through the magazine, enjoying the photos and reading the stories. It didn’t take long for his tight trousers to bulge uncomfortably. So Jay unfastened the button at the waist, pulled down the zip. As he eased his tight black jeans down over his hips his excited boy clit popped free and, with his trousers around the top of his thighs, Jay started to pleasure himself.
Dave usually had some lunch, then relaxed for a while before going back to the shop to lock up. But today the missus was going out with some friends and wanted to leave the shop in time to get her hair done. So Dave got back to the shop earlier than usual.
“Jay downstairs?” he asked the girls after he had put his coat in the office, they nodded and Dave headed to the basement to see how Jay was doing. Dave made his way down the stairs and into the basement quietly. But Jay was nowhere to be seen in the stockroom. He stood for a moment, a little confused, and was about to go back upstairs when he heard a shuffling sort of noise from the dark archway that led to the back room. He suddenly began to feel suspicious, so he crept across the storeroom and peeped carefully through the small archway, expecting to find Jay playing on his phone or something.
Through the shelving Dave could see Jay quite clearly, the smooth pale skin of his bottom almost glowing against the dark background of the old stockroom. Jay was stood with his back to the door between the farthest shelving units. His jeans were pulled down just under his bottom, and his little T-shirt only just came down to his waist. Dave could see one arm moving as it turned the pages of a magazine on the shelf, and the other arm close by Jay’s side as he rubbed his hand between his legs. Shocked, Dave took a while to process what he was seeing. He struggled to decide what, if anything, he should do. His mind racing as he watched the young man masturbating.
After much debate, Dave decided he would just let it go, for now. He was just about to turn away when Jay hooked both his thumbs into his jeans and pulled them down to his knees. Ducking carefully under the shelf above, Jay bent forward, resting one arm on the shelf and opening his legs as wide as his jeans allowed, he arched his back and thrust his bottom up and back. Dave halted his retreat and stared at the young man’s smooth round ass and the cute little pink sack between his slender thighs. He felt his cock throb in his trousers and thought to himself, he really should go now.
Jay reached one hand round and grabbed a big handful of his own ass. He squeezed and groped the soft round flesh before running his fingers between the cheeks and gently fingering the tight little hole within. Suddenly he lifted his hand and brought it down with a light smack on his own bottom. He spanked himself again, then again. Then pushed his hand through his legs from the front and up between his squirming ass cheeks, before slipping a finger inside his tight boy pussy.
Dave watched, transfixed, unable to turn away though he knew he should, the front of his trousers starting to bulge. Then he lifted his foot, and quietly stepped up into the little dark room. He edged closer, no clue as to what he was going to do wen e got where he was going, but longing to see more, have more. He was so close now he could almost touch Jay, he resisted nevşehir escort the urge to reach out and grab the young man’s wriggling ass. But as he took a step closer, that step took him between Jay and the dim little light on the wall, casting a large dark shadow over Jay and the magazine.
Jay jumped upright, turning to face the source of the shadow, a look of fear and panic on his face. He clamped both his hands over his groin and backed away from the old man further into the shadows at the back of the dark room. A long awkward moment followed, the most awkward either of them had ever experienced. Mr Evans looked Jay up and down, Jay stared with wide-eyed panic back at Mr Evans, totally petrified and unable to move or speak. Mr Evans looked Jay in the eyes, but the young man couldn’t hold his gaze and dropped his head in shame.
Dave took a step forward and turned to look at the open magazine, curious about what got the young man so excited. The pages were mostly covered by pictures of a cute young lady boy, dressed as a maid, being groped, spanked and fucked by her elderly boss. On this particular page the sissy was bent over a desk in an office and the boss was having his way. Clearly this was the position Jay had been imitating when he was interrupted. Dave turned and looked down at Jay, the young man still stood in the corner covering his privates with both hands and trying not to look in the old man’s direction at all.
“Dave… I need to get going…” came the voice of Mrs Evans from the top of the stairs.
“OK… just a sec.” Dave called back, then he turned and left Jay standing in the dark corner of the basement. By the time Jay had sorted his clothes out, put away the magazine and finished tidying up in the stockroom, Mrs Evans had left. Jay felt like simply getting his coat and leaving. But he was too timid to make such a statement, so instead he crept back upstairs into the shop and began sweeping the floor, just like he did at the end of every Saturday. Meg was stood at the counter and Mr Evans was not in sight, probably in his office.
Dave sat in the small office, mulling over the problem with Jay. He thought about sacking him, but Jay was a good worker, and Dave liked having him around. Not to mention that he had seen the young man’s secret and his hot little ass. Jay also now knew the names and addresses of some of Dave’s special customers. He decided, he would need to assess the damage, then give Jay a stern talking to. He left the office and went back to the basement to get the box Jay had found. As he came back from the stockroom he saw Jay sweeping the floor. Jay glanced up at him, but couldn’t look him in the eye and turned away. Dave took the box into his office.
Jay felt his face flush red as Mr Evans gave him, what Jay felt was, a very disappointed look. He had the box in his hands and took it into the office, Jay couldn’t help feeling he was about to be sacked. The last fifteen minutes of the day seemed to last hours until, at last, Mr Evans came out of his office.
“Can I have a quick word before you go please Jay.” Dave asked as he made his way to the shop door and locked it. Jay and Meg went to the staff area at the back of the shop and got their stuff. Then Meg walked back through the shop and Dave let her out, saying goodbye, before locking the door again and heading back to his office. Jay was stood by the office door, holding his jacket and looking very sheepish. Dave punched the code into the door lock and stepped inside. He opened the box, took the magazine out, placed it on the desk and opened it at the page Jay had found so exciting.
“Come in please Jay…” Dave said sitting down “shut the door please.” he added as Jay slipped nervously into the room. Jay spotted the open magazine right away, his head dropped, he held his jacket in both hands and stared down at his trembling fingers.
“I’ve been in this business a long time Jay…” Mr Evans began after a long uncomfortable pause “I have built up a relationship with customers…” he went on and lectured Jay for a few minutes about honesty, betraying trust and customer service. Jay kind of listened, but his mind was all over the place, panicking about what Mr Evans now knew about him, his tastes, his ability to control himself and his most intimate sexual fantasies. They were laid open on display on the desk right next to him. After imagining the worst and half listening for a while, Jay realized his boss had stopped talking and seemed to be waiting for some sort of response.
“I’m so sorry…” Jay blurted out, his emotions getting the better of him and honest desperation taking over, “it won’t happen again, please don’t sack me…” tears welling up in his eyes, “please don’t tell anyone, I’ll do anything to make up for it.”
“What I need to know Jay, is whether or not you can be discreet, be honest and you can do as you are told?” Mr Evans asked looking the trembling teenager up and down and remembering how smooth and perfect his bottom was, he longed escort nevşehir to see it again, to touch it, squeeze it, have it.
“Things have changed between us Jay, I don’t think we can go back to how things were. But I think we have corresponding interests, and I believe you are very discreet, so all we need to find out is if you can do as you are told?” Dave leaned back in his small chair.
“I can Mr Evans, you won’t regret it” Jay responded eagerly, seeing light at the end of the tunnel already. He didn’t really know where his boss was going with this, but anything seemed better than the torture he was currently putting himself through.
“And we will, of course, have to sort out some kind of punishment for this afternoon…” Jay looked up at Mr Evans, concerned and confused, but before he could say anything the old man continued, “so let’s see if you can hold up your end of the deal.” As he spoke Dave got to his feet, pushing his chair back, and took Jays coat.
“Hands on the desk please.” he insisted as he reached over Jay’s shoulder to hang his coat on the hook behind the door. Jay looked up at him, a look of utter confusion on his face.
“Well that isn’t the best start is it Jay?” Mr Evans asked, not expecting or waiting for a reply, “now place your hands on the desk” As he spoke Dave took hold of Jay’s upper arm and firmly, but gently, turned him to face the desk. Jay had no idea what was going on right now so, unable to make sense of anything, he went along with it and did as he was told. With his thighs against the edge of the desk, Jay bent forward, placed his hands flat on the top of the desk and found himself looking down at the open magazine and pictures of the young sissy maid being spanked. He flinched a little as Mr Evans moved close behind him, but kept his hands on the desk, slowly starting to understand what all that stuff about doing what he was told and being discreet was actually about.
Dave felt the young man’s body tense as he moved in close behind him in the cramped little office, but Jay kept his hands on the table and said nothing. So Dave reached around Jays waist and unfastened the button on his jeans, then eased the zip down carefully. Still, there was no reaction from Jay, other than a bit of heavy breathing. Dave slid a hand into each side of Jay’s pants. Feeling him tremble as he held the young man’s hips for a moment, before easing the tight-fitting trousers all the way down Jay’s legs to his ankles.
Jay gasped as the old man pulled his trousers down, stood bent over a desk with his bottom exposed, he couldn’t believe this was actually happening. Yes, it was something he had fantasized about for a while now, but to actually do it! With Mr Evans! He stared down at the magazine before him, and felt his excitement growing. Mr Evans took his time and manoeuvred Jay backwards a little, away from the desk then stepped to one side. Jay saw Mr Evans out the corner of one eye, moving beside him, there was a long pause, then.
“aaaaoooooooooo…” Jay squealed as Mr Evans brought the flat of his hand down hard, five times in quick succession, on his right cheek. Jay stood up, grabbing hold of his stinging bottom and wriggling the pain away. He looked up at Mr Evans, but Mr Evans didn’t notice, he was looking down at Jay’s groin. The youngster’s little T-shirt only just covered his belly button, so there, on display as he wriggled in pain, was Jay’s already fully erect boyclitt. It was by no means a magnificent example of manhood, but was without doubt the prettiest cock Dave had ever seen. It’s skin was the same pure, smooth, white as the rest of Jay’s body. The tight little sack underneath it was a darker shade of pink, just like the perfectly proportioned round pink head at the tip. There was not a hair in sight and the excited member stood up straight and jiggled about enticingly as Jay wriggled in pain. Suddenly Jay noticed what the old man was looking at and, feeling embarrassed at his obvious excitement, he covered his groin with both hands.
“Both hands on the desk please.” Mr Evans insisted, and after just a moment’s hesitation, Jay complied, leaning forward onto his hands. Dave moved close to Jay again, and took a moment to admire the red hand prints that were now showing on the youngster’s right cheek. Then he repositioned himself carefully and brought his hand down hard and fast, five times on Jays left cheek. Jay squealed again and stood upright, but this time he didn’t move away from the desk, and after a moment of wriggling his stinging bottom, he bent forward placing his hands on the desk again.
“Good boy” Dave heard someone say, then was shocked to realize it was himself. He could feel his own cock swelling in his trousers and took a moment to reposition it, so he wasn’t so uncomfortable. Then he moved close again and quickly spanked Jay’s right ass cheek five more times. Again Jay squealed, his body tensed and pulled his hips forward. Then he stood for a moment, hands still firmly planted on the desk, squirming and wiggling his bottom as the pain eased. Dave watched the young man’s hot pink ass moving and his cock grew harder and harder. He wanted so much to stand behind him, pull those cheeks apart and bury his big hard cock inside. Jay, stopped wriggling, so Dave smacked his left cheek five more times and watched hungrily as Jay set off squirming again.