Weekend Work Pt. 03

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The boss sets Jay up with one of his friends, surprise!
8.9k words
4.62
9.8k
8

Part 3 of the 7 part series

Updated 06/11/2023
Created 12/06/2021
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1otty
1otty
81 Followers

The day had passed uneventfully at work, despite the excitement and thrills of the previous day. Mr Evans kept his distance and almost seemed to ignore Jay, making him feel a little bit like it had all been a big mistake. The delicate skin on his bottom was still tender and his wrists were red, with little marks forming where the restraints had rubbed the skin raw. When they closed up the shop for the day Jay looked for some sign or recognition from Mr Evans that things were still okay between them. He had been certain it was Mr Evans who came to him in the basement yesterday. But now Mr Evans seemed to be blanking him, Jay wasn't so sure anymore.

"See you next week Jay," Mr Evans said as Jay left the shop.

"Bye," Jay replied meekly, and walked home feeling he had done something wrong and pissed his boss off. That evening Jay sat in his room alone, his mum had a friend round, so he stayed out of the way. As usual he started up his laptop and logged in to some of his favorite sites to chat with people on there. An hour or so went by and Jay made himself horny role playing and exchanging fantasies with strangers online. Then he got a friend request from another user. He clicked on the users profile to find out more, like he always did. The profile contained next to no information, but the account username was "TheBasement" and the little avatar picture next to it looked like someone stood spreadeagled, in a dark room. Jay felt a shiver run through his body and his hands started to tremble as he clicked on the small image to see a larger version. It wasn't a good quality picture, it was blurred and a bit too dark. The person in the photo was stood between two old looking shelving units in a small dimly lit room. Their hair was tied in two bunches either side of their head and they wore nothing more than, a bra, small panties,white lacy socks and little red canvas trainers. With a thrill of excitement and fear, in equal measure, Jay realized the person tied up in the photograph, was him.

Jay instantly assumed it was his boss, Mr Evans who had made the profile, and he accepted the friend request eagerly. Then he sent a new chat message to the member. "Hi," he typed, "did you take your avatar photo?" He waited for a reply, a long time past and Jay was just about to start typing again when the other user replied.

"No, a friend took it," then a moment later another message arrived, "Do you like to be used like that?" Jay giggled to himself, feeling naughty and replied "Yes."

The stranger continued, "By men you don't know, one after the other, taking their turn with you?"

This got Jay quite excited, still thinking he was chatting with his boss, playing a game of fantasies, he answered, "mmm oh yes, anyone you say can have their turn with me!" Jay was stroking himself now and getting really turned on.

After a minute or so the stranger typed, "If a total stranger showed you his cock, would you suck it?"

Jay replied quickly, a little too quickly "Oh yes," and perhaps a little too eagerly.

"Would you let him fuck you?" The mystery website member asked.

"I would let him do whatever he wanted," boasted Jay naughtily, playing with himself and feeling like a little slut.

There was a long pause, Jay thought the other user had gone, then at last a final message arrived, "what is your email?" Jay was confused, he didn't know for sure who he was talking to now, he felt pretty sure it was his boss, at least, he thought it was, but his boss already knew his email address. After just a moments hesitation, he obediently typed his email address into a message back to the other user, who promptly left the chat session.

Jay waited for a long time, checking his inbox regularly, but nothing arrived. An hour or so later, feeling unsettled and a bit nervous now, he switched off his laptop and went to bed. In the morning Jay heard his Mum leave for work and he got out of bed. Still no email from the stranger, but Jay knew he couldn't just sit around waiting for an email all day. Outside it was cold but bright, so he went for a walk, thinking about the stranger's account, emails and his boss the whole time. When he got home a couple of hours later there was an email waiting for him. The sender's address was the same as the strangers account name, Jay opened the email, it read.

"I liked the cute underwear in your photos very much, you can wear that again sometime. But this Saturday you are to wear something a bit more sexy."

Then there was a link, Jay clicked on it and a folder on a cloud storage site opened. The folder was full of images of Jay. Tied between shelves, in his bra and panties, with red ass cheeks, his clit hard and upright, his ass dripping cum. Jay clicked through the images, becoming instantly aroused. He downloaded all the photos still not sure who had taken them. Then in reply to the strangers email he wrote, "Those photos make me so excited, I can't wait for Saturday, I'll find something sexy for you, Boss."

Jay spent the rest of the week checking his emails but got no reply. He searched his big sisters and his mum's underwear, old and new, for something discrete enough to wear under his work clothes. But sexy enough to turn Mr Evans on. After lots of experimenting, Jay settled on a pair of hold ups he found in his sisters room. They were black stockings that stretched to the top of his thighs. Around the top of each there was a wide lace band and inside the lace section grippy rubber held the stockings in place without the need of a garter belt. Jay wanted to wear a garter belt, but was scared to, as it would show above the waist of his trousers. He also found a little black thong, that held his clit nicely in a triangle of soft lace at the front, with another little triangle of lace at the rear, which sat just at the top of his cheeks while a thin strip of black lace squeezed between them and connected the two. The delicate little panties were held in place by a broad strip of elasticated lace that ran around Jay's hips. The little black bra he found was largely mesh and pretty much see through. The lace trimmed cups, though small, were still to big for Jay so were lose and empty, but otherwise it fit nicely.

The walk to work that Saturday was almost a jog, Jay was just so excited and nervous. All the way he could feel the unusual sensation of the stockings under his sweat pants and the thong between his cheeks. It made him wiggle his bottom even more than usual as he walked and he had to force himself to think of something else to avoid getting too excited. He arrived at the shop a little breathless and, being the timid little thing he was, started to blush even before he was at the door.

"Hi Jay..." Mrs Evans greeted him as he walked in, "you feeling OK, you look a bit flushed".

"Hi..." he replied, "I'm fine, just been running a bit".

"Well that explains why you are so early I suppose" she went on, then turned back to the other girl who worked there, Meg, who nodded hello at Jay as he walked by. There was no sign of Mr Evans anywhere, so Jay got to work as usual. Mr Evans appeared about an hour later and, as he had done the Sunday before, Mr Evans treated Jay as if nothing had happened between them, if anything he seemed even more distant and hardly even looked at Jay. The day crawled by and poor Jay felt confused and unsure about everything, especially when Mr Evans left at lunchtime with not so much as a see you later. Mid afternoon Jay went into the basement storeroom and sorted the stock. He wondered if his boss would join him again, as he had the prewious week. But when Mr Evans hadn't shown by the time Jay had finished sorting the stock, he reluctantly made his way back upstairs. It was getting late now and Jay was about to start sweeping the floor of the almost empty shop, when Mr Evans stepped out of his office.

"Jay," he said in a loud voice that made the young man jump "I need you to run an errand for me," he held a small brown envelope out to Jay "Take this for me, you need to hand it to him, don't just put it through the letterbox. When you are done you can go straight home, okay?" Then without waiting for an answer he turned and went back into his office. "See you tomorrow," he called over his shoulder as he went.

Jay stood for a moment, stunned. It wasn't by any means the first time he had delivered a bill like this, but to be dismissed like that when he had got dressed up for him and was expecting so much more really hurt. Jay was surprised how much it hurt and as his eyes started to water, he grabbed his jacket and left the shop.

Jay knew the address he was going to quite well, he didn't recognize the name though, a Mr Parkes? It was a block of flats in the very well off part of town and was about twenty minutes walk, in the opposite direction to where he lived.

"Thanks for nothing Mr Evans." he muttered to himself sulkily as he trudged uphill along the dark cold street. The clear, star filled, winter sky meant that it was cold. Jays breath wafted in front of him on the breeze and the chill from the pavement penetrated the thin soles of his little red canvas shoes. Jay pulled the hood of his sweatshirt up over his short ponytail, then closed the zip all the way to the top before fastening his short jacket and pulling it tight around his chest. By the time he reached the large building Jays fingers and toes were frozen and his cheeks and nose were red.

He had delivered papers here before, these flats were old, built in a time when homes were made to impress, and though Jay had never actually been inside one of these flats, he knew from the tiles, the brass work, the wood paneling and the huge stained glass windows in the communal areas, that these flats were special.

Jay walked down the drive that lead to the parking area at the rear of the building. There were three small doors there, about fifty feet apart, one for each of three sets of flats, the tradesman's entrance. Inside there was a lift and two doors, two flats per floor, one either side of a central staircase. The flat Jay wanted was on the top floor, of course it was. He got into the lift, pressed the top button, and waited as the rickety old contraption made it's way up through the building. All that walking had made Jays stockings slip a little under his sweatpants, so he pulled them back into place through the stretchy cotton trousers. The lift arrived with a ting from a little bell somewhere and Jay stepped out onto the deep, plush carpet in the hallway.

He walked up to the large, dark, wooden door of the flat in question and pressed the button just to the side of it. Inside the flat a distant brrrring could be heard and Jay waited. There was absolute silence, so quiet all Jay could hear was his heart beating. A sudden loud click behind him, made Jay jump and look around. But it was just the lift, it made a humming whirring noise as it returned to the ground floor. Jay turned back to the door and rang the bell again. Still nothing seemed to happen. He waited patiently, knowing some of the occupants of these flats were elderly and not so fast on their feet. A minute or two later, he decided to give it one last try, brrrrrrrring he heard as he pushed the button again.

"Alright alright..." came a voice from deep inside the flat, "can't I even take a shower in peace?" The voice got louder as it got closer and with the last word the door swung open suddenly. In the doorway, towering over Jay, stood a tall, striking looking old man. He was probably on his sixties and had a completely bald head apart from the almost white, very neatly trimmed goatee on his chin. He was heavily tanned, wore a large very cozy looking white bathrobe and was soaking wet. He glared down at Jay.

"Mr Parkes?" Jay asked in a timid little voice.

"Yes, what?" the man replied impatiently. Jay raised one trembling arm, offering Mr Parkes the small brown envelope.

"Mr Evans said I was to hand this to you," he mumbled. Mr Parkes seemed to relax a little and took the little envelope out of Jay's hand. Jay had done this many times before for other customers and usually had to wait for a cheque to take back with him. He looked up at Mr Parkes, watching as he tore the envelope open carefully and pulled a folded slip of paper from inside. A look of shock flashed across the old mans face for just a moment, then he turned his cool blue eyes onto the young man. Jay couldn't hold his stare and dropped his eyes to the floor, noticing the stranger's bare feet were just as tanned as his head and face. There was a long uncomfortable silence in which Mr Parkes looked Jay up and down.

"You better come in for a moment," the old man said suddenly, making Jay jump "hang your coat," he continued, stepping out of the way to let Jay inside, "It's pretty warm in here." It was indeed very warm and after his walk in the cold weather Jay had now started to sweat and his chilly fingers were getting hot and red. He stepped inside and turned to face the tall wooden coat hanger by the door, the heavy door slammed shut behind him as he unzipped his coat and hoodie. Mr Parkes watched from behind as Jay took his hood down and slipped his jacket and hoody together, off his shoulders. He hung them on one of the curvy wooden hooks and turned to face Mr Parkes.

"Come with me," the old man said, and set off down the long wide corridor. A soft dark red carpet ran down the middle of the corridor, with angular blocks of wooden flooring visible down either side. Large old furniture and picture frames lined the walls and they walked by several closed doors as they made their way to the far end of the corridor. Mr Parkes opened the last door on the left and went inside, flicking a switch to turn on the wall lights. Jay followed him through the door, but not all the way into the room, for some reason he felt he should wait. It was a very large dimly lit room, with tall leather chairs and a quilted leather sofa arranged around the fireplace. There was a huge old fashioned desk and various small tables and cabinets around the walls. The old man walked over to the tall leather chair facing the door and sat down with a big sigh, leaning back in the chair and opening his legs wide.

Jay gazed around the impressive room from the doorway for a moment, there was a rich smell of tobacco and the air was hazy. Two large windows went almost from floor to ceiling in the wall opposite the fireplace, the curtains were wide open and outside there was an orange glow from the streetlights below. Between the windows sat the imposing desk it was covered in books and papers. The sofa was between the desk and the fireplace and sat in a tall chair next to the sofa, facing Jay, was Mr Parkes.

The old man was slumped back in the chair, his bathrobe bright white in the dimly lit room, contrasting his dark heavily tanned skin. Jay could see his golden brown legs clearly, wide open as they were. But what really got Jays attention, was Mr Parkes cock. The old mans bathrobe had fallen open almost up to his waist and his long member lay on the white robe between the strangers thick brown thighs. It wasn't the length that made Jay stare though, and it wasn't the hair free, clean shaven, evenly tanned skin all around it. It wasn't even the sturdy looking piece of black rubber strapped around the base of Mr Parkes' cock and saggy balls, which made all his junk seem to stand out in some way. No, what caught Jay's eye was the thick silver ring, that glinted in the soft warm light, and seemed to be attached somehow to the head of the old man's cock.

Jay just stood and stared, the old man watched him but didn't say anything, he just let the lad have a good long look. Jay felt his little panties stretching and the front of his sweat pants start to bulge. Suddenly he remembered where he was and tore his gaze away from Mr Parkes' open gown and up to his face. Jay flinched a little, he hadn't realized he was being watched. He knew right away that he had been caught staring. He blushed with embarrassment, though you wouldn't know it as his cheeks were still rosy from the cold weather. Instinctively he clasped his hands together over the front of his pants to hide his excitement. Though he knew it was already too late for that.

"Come over here," Mr Parkes requested in a calm deep voice that seemed to rumble around the silent room, "it's OK, I won't bite," he encouraged a moment later, seeing the young mans hesitation. Jay didn't decide to move closer, somehow he just found himself a few feet from the front of the old man's chair, between the fireplace and a low coffee table that was surrounded by the sofa and chairs. Jay didn't know where to look, he couldn't look the stranger in the eye, and though he wanted to, he felt he shouldn't look down at his lap. He tried to look at a painting on the far wall behind Mr Parkes, but ended up with his eyes pinging nervously around between all three. There was another long, uncomfortable silence.

"It's OK," Mr Parkes said again, still in a low calm deep voice, "you can look all you want." A little startled by this revelation, Jay glanced down at the old man's face which wore a subtle, confident smile. Then he looked a little further down at his lap. The old mans cock had grown and had lifted itself off the chair cushion. It hung now in a long graceful arc from the thick black rubber band around it's base to the silver ring at its tip that hovered above the soft fluffy bathrobe. Jay watched it as it grew longer and raised itself higher with every throb and pulse. The strangers hands moved slowly at his waist as he untied the knot in the chord that fastened his bathrobe together. Then he pulled the two pieces of thick, fluffy, white fabric apart and lay them over the quilted leather arms of the chair.

Jay gazed down at the old man's golden brown body, not a centimeter of it had been missed by the sun. There was a dusting of gray or sun bleached hairs on his chest, belly and legs, which were almost a stark white against his skin. Though he clearly kept himself in shape, he had a bit of a belly and his large pecs seemed to slope off to the sides a little more than maybe they used to. His large nipples stood upright with a silver bar through each one and he reclined in his chair, totally at ease, letting Jay leer at him. As Jay watched, the old mans cock grew stiffer until it raised itself up enough to roll to one side and lay against his thick brown thigh. Licking his lips nervously, Jay glanced up at the strangers face, longing to take things further but unsure what, if anything, he should do now.

"Why don't you show me yours?" the old man asked looking Jay in the eye, almost sensing the young mans insecurity and doubt. After a moments hesitation and almost without realizing he was doing it, Jay's feet moved, placing the toe of one on the heel of the other and slipping off his battered old red trainers. His fingers pulled at the string around the waist of his sweat pants as he kicked off his other shoe. Then, he took a deep breath and slid his pants down over his hips.

"Oh fuck," the old man hissed, sitting upright in his chair suddenly, as Jay's pants fell to the floor and his little black lacy panties and stockings were revealed, "Oh fuck," he said again "come here, come here," he beckoned Jay closer, clearly excited by her choice of underwear. Jay pulled her feet out of the sweat pants around her ankles and, in a couple of steps, crossed the gap between herself and Mr Parkes to stand between his wide open knees. Jay's pale skin almost glowed in the soft warm light, contrasting and showing through the skimpy black lace underwear and as the old mans dark skinned hands took hold of her waist Jay crossed her arms over, took hold of the hem of her T shirt and lifted it off over her head.

Mr Parkes studied the youngster closely, his face just inches away from her smooth, pale, slender body. His hands roamed up and down eagerly, holding and caressing her stocking clad legs and her smooth bare bottom, toying with the strip of the thin lace between her soft round cheeks. Exploring the curve of her shapely waist, the gentle undulations her ribs made on her slim chest and the firm, tight, dark nipples hidden beneath her little black lace bra.

1otty
1otty
81 Followers