Weekend Work Pt. 04

Jay didn't sleep much that Saturday night, his back was painful which kept him awake and he was dwelling on the previous evenings events. There was a part of him that was convinced what he was doing was wrong, and that he needed to stop this thing that was developing with his boss. But, as usual, these guilty feelings would fade away over the days that followed, and be forgotten. Leaving only the need and hunger for the thrill and excitement he had felt at the time. It felt so natural to just go along with what his boss said, and Jay knew very well it would happen again. But today, he wasn't going anywhere. Jay had hobbled downstairs in the early hours and found some painkillers. He lay flat on his back and sent his boss a text while he waited for them to kick in.

"My back is killing me, thnx 2 your friend, can't work today," he sent at 5am. He knew Mr Evans would be up already, he started early to get the shop up and running. He was still unsure how he felt about Mr Evans setting him up with one of his friends, or even worse, one of his customers, the day before. But was it Mr Evans he was angry at, or himself for allowing it to happen, for going along with it and even enjoying it. Who was he kidding though, he loved it and deep down, he was already looking forward to the next time his boss got him alone. Jay thought about what his boss would have him do next time, while he lay on his back, touching himself gently as the painkillers kicked in and he drifted off to sleep.

Jay's mum woke him at about 10, wondering why he wasn't at work. He told her he had slipped on an icy curb on his way home the night before, and landed on his back. He got out of bed carefully and they both checked out the impressive bruise in the mirror, it was about the size of a Milky-way chocolate bar and was right above his bum crack. A bit later Jay checked his phone, he had several messages from his boss. Mr Evans wanted to know what had happened. He told Jay to check his emails, and when he did, Jay found an email from the mystery man, asking if he was OK and what happened. Jay replied, still believing he was emailing his boss. They exchanged a few short emails and Jay explained that Mr Parkes had pushed him and he had fallen against a table. He didn't mention however, that Mr Parkes had then rubbed that very same spot on his back, against the edge of his big wooden desk, over and over again as he fucked him.

Over the next few days Jay forgave his boss, even admitting in an email to the mystery man that being offered to someone like that had really turned him on. By midweek Jay was feeling better, the bruise was fading, and he was starting to feel more and more horny at the prospect of seeing Mr Evans again. He felt like he needed to for Mr Evans, to make up for his behavior, even though it was Mr Evans who had arranged the whole thing. Jay was supposed to be doing college work at home, but he spent much of his time digging through his Mum's clothes and stuff his sister had left behind when she moved out. Trying on different outfits and getting himself worked up all over again.

That Friday Jay's mum left for work early as usual, she would be gone all day. Jay woke mid morning, and was wondering what he would do with the day, knowing already he was about to get dressed up again. When his phone beeped, there was a message from Mr Evans.

"Hi Jay you home today? I need to see you got something for you can I pop round?" The idea was right there, straight away, it didn't pop into his head, it had been there all along, just waiting for an opportunity like this. Jay's heart rate almost doubled with excitement, this was Jay's chance to show Mr Evans he was still his, and get his own back by giving his boss a little surprise of his own. So trying to sound as casual as possible he replied, "sure how about lunchtime?" Almost right away Mr Evans answered, "ok see you then," and Jay giggled with nervous excitement.

Jay almost ran to the bathroom,he was so eager to make sure he was as clean and as smooth as possible everywhere. After showering he ran naked into his mum's room and used her drier and brush to style his soft wavy brown hair into a messy sort of bob, a bit like the girl in the movie Passengers, but dark brown instead of blonde, obviously. Then he raided his Mum's makeup and perfume, a little black eyeliner and shadow, red lipstick and a dab of No5. After that he went to his sisters, now unused, bedroom and took some items from her drawers and wardrobe before heading back up to his room in the converted loft. He lay all the clothes out on his bed, then moved the small chest of drawers in his room to one side, revealing the hatch into the loft storage space. His mum was too scared of spiders to ever go in the loft, so Jay had free access to all the old clothes she hoarded there, and there were a lot. He grabbed a couple of his favorite items and put them on the bed with the rest, before placing his secret box, the one with his toy in it, next to the clothes.

First Jay put on his mum's old white satin suspender belt. It was nice and tight fitting, very stretchy and deep, Jay loved the way it squeezed his slim tummy all the way from just below his ribs to his hips. He fastened it with four hooks high on his tummy before spinning the hooks round to the back. Then he slipped on a pair of smooth, sheer, black stockings with a delicate black seam up the back, and attached them to the elasticated straps of the suspender belt. He stepped into a tiny pair of plain white cotton panties from a pack found at the back of his sisters knicker drawer, adjusting them carefully so they hugged his bottom tightly and made a firm little bulge of his boyclit. He wrapped the little white training bra his sister wore years ago, around his slender body, fastening it on his chest before spinning it round and slipping the thin straps up to his shoulders. Next came his sisters old school blouse, it was white and tailored at the waist with little cap sleeves. He tucked the blouse into her gray school skirt, which he fastened with a small zip and hook at the hip, the top part was smooth and hugged Jay's waist and hips, the bottom half was pleated and just about covered her stocking tops. Jay even put on the school tie her sister used to wear, loosely tied hanging around the collar of the unbuttoned blouse. Then the black school blazer, it was a bit small, but the sleeves were rolled up anyway and Jay didn't try to fasten it, so the size wasn't an issue. Last of all Jay stepped into her mum's black 4" heels and stood in front of the mirror to check the uniform, she was ready.

Back in her mum's bedroom, Jay leaned on the front windowsill, kicking up her heels as she rocked backwards and forwards nervously, waiting for Mr Evans. It wasn't even midday, so her boss would be a while yet. She had never been with anyone like this before, and she never thought her first time would be in her own house. She hoped Mr Evans would like how she looked, that he would be turned on and that he would want her. Jay was eager to repair the imaginary rift she felt was opening between them.

Her mind raced unable to calm down and just wait, what am I doing she thought, he wouldn't be there for ages yet. Jay dragged herself away from the window, pausing momentarily to check her outfit again in her mum's mirror, before pacing nervously around the house. Passing her big sister's bedroom door she suddenly had a great idea. She hadn't thought about where or how she was going to seduce the old man at all until now. But her sister's bedroom was perfect, it was tidy, no one used it and there was a double bed, albeit a small one. Jay moved a few things out of the way in the bedroom, then trotted excitedly back up to her room and grabbed a tube of lube from her special box. She left the tube in a drawer by her sisters bed and returned to the windowsill in her mum's room to look for Mr Evans again, her hand trembling with nerves as she held the net curtain to one side and peeped out.

After a long agonizing wait, at last Jay spotted Mr Evans' car coming along the road toward her. She held herself back, longing to run downstairs and let him in, but trying be cool. He got out of his car and looked up at the house. Jay hid, even though she couldn't be seen behind the net curtain, then she peeped out again and watched as her boss walked up the path to the front door. Bing bong, the doorbell rang, and Jay hurried downstairs as fast as she could in her heels. She could see his large dark shadow through the small blurry glass window in the front door and as she approached it her courage left her. Jay stood trembling behind the door, too scared and nervous to move, her hands clasped at her chest. Bing Bong the doorbell rang again a moment later, followed by three knocks on the door. Suddenly Jay wrenched her hands apart, raising one to the door and quickly opening it.

"Hi..." Jay said in a soft trembling voice, Mr Evans stood open mouthed in the doorway and looked her up and down slowly "come in" she offered, stepping back in the narrow hallway and opening the door wide. Mr Evans stepped inside and, as Jay retreated to the living room doorway, he turned and shut the door behind himself.

"Here let me take your coat..." Jay suggested, grabbing the lapels of the old mans overcoat and lifting it off his shoulders. Mr Evans let her take his coat off, and Jay stood close to him, her heels making her almost the same height. Her hair brushed his gray whiskered chin as the heavy garment slipped down his arms. He breathed in deeply, enjoying the heady mix of her perfume and her freshly washed hair as Jay gathered his coat up and hung it over her arm. She looked up at the old man and saw him grinning down at her.

"Are... are you laughing at me?" she stammered, feeling suddenly very silly and loosing all her confidence again.

"No no no" he replied enthusiastically "Just smiling at how perfect you are, the perfect hostess". Mr Evans was loving every minute, the initial shock of seeing his young assistant dressed as a schoolgirl quickly passed and he quickly became aroused. Jay smiled back, feeling much better about herself in the blink of an eye, and raised one arm, gesturing to the living room.

"Please take a seat," she offered "I'll just hang your coat". There wasn't actually anywhere too hang the coat in that narrow hallway, so Jay just folded it over the back of a chair in the dining room and joined Mr Evans in the living room.

"Can I get you something to drink?" she asked standing in the doorway. Mr Evans was sat on the small sofa just by the door, facing the window on the opposite side of the little room. He turned his head and looked her up and down. She stood with one knee bent a little, her hands clasped together behind her back, swinging slightly from side to side, just enough to make her short pleated skirt move. He gazed at her long smooth stocking clad legs and felt himself getting hard.

"No thank you, I can't, I'm afraid I have to get going soon" he looked genuinely sorry "I have to talk to you though". Jay entered the room properly, walking slowly right in front of her boss. She turned and sat down on the sofa next to him, folding one leg over the other and leaning back in the seat, her stocking tops just peeking from under her skirt.

"Okay..." she said leaning her knees against his, "what did you want to talk about?" she asked, one foot waving back and forth gently in the air as she tried to act as cool as possible. Mr Evans struggled to concentrate, he told Jay he was sorry for setting her up like that, he was sure she would enjoy it. He told her how it was a sort of test, that they wanted to see how she would handle it. Jay sat quietly, not really listening and leaned her legs against his, gently rubbing her foot on his shin. She was trying to figure out how she was going to get her boss upstairs and into bed with her. Working really hard to stay focused, Mr Evans looked Jay in the eye, knowing his wife would be expecting him back soon and if he looked at Jay's legs he was lost. Then he began to explain how sorry Mr Parkes was, and that he would have been here as well, to apologize in person, if he hadn't been out of the country.

"He gave me a bruise" Jay blurted out "a big bruise" and before Mr Evans could respond she was getting to her feet "do you want to see it?" she asked, not waiting for, or expecting a reply. Jay turned her back on her boss and lifted the rear of her skirt high on her waist, displaying her stocking tops, white cotton clad bottom and satin suspender belt. And there, in between her panties and suspenders, right in the small of her back, was a thumb sized smudge of purple and yellow.

"It's going away now, but it was quite big" she went on enthusiastically, " can you see it... can you see it." she urged, pushing her bottom out at him. Well, just as Jay had intended, this was more than Mr Evans could cope with and still keep on task. Reaching out with both hands he took hold of Jay's hips and maneuvered her closer between his open legs. Jay allowed herself to be positioned and stood holding her skirt at her waist, with her legs straight and feet together, leaning forward slightly, sticking her bottom out at her boss. The old man's large hands began to caress her, roaming up and down her legs, gripping and squeezing the bare skin above her stockings with his strong fingers. Mr Evans leaned forward slightly, his nose just brushing the soft white cotton panties, and took a deep breath. Jay smelled wonderful, of clean laundry, soap, perfume and just a soft warm hint of her. A moment later the old man pushed his cold face deep into her hot yielding bottom, squashing her cheeks together with his hands as he smothered himself.

Jay could feel and hear her boss enjoying himself and her own excitement grew rapidly in response, pushing at the front of her panties urgently as it throbbed. Eventually the old man sat back in the sofa, but he didn't release Jay, he kept hold of her hips and sat her cotton clad bottom down on his lap, her skirt spread out around her. Jay quickly turned herself, folded her legs up next to his and clasping her hands together behind his neck. She had fantasized for so long about this very thing that she was now responding instinctively, naturally playing the cute girl. She looked Mr Evans in the eye and moved her mouth towards his.

"I really can't stay long" The old man protested very unconvincingly, and leaned his head back a little, pulling away from her "I need to ask if you are up for a get together next week?" Jay looked away, a little disappointed. Her boss' hand was resting on her knee, she picked it up, then, looking him in the eye again, she slowly pushed it up under her skirt, onto her hot thighs and bulging panties.

"Please stay" she whispered "I'll do whatever you want" and she pressed her soft warm lips onto his, kissing him slowly and sensually. A moment later he responded and with a hand behind her head pushed his mouth onto hers, there tongues teasing each other. His hand moved under her skirt, groping, squeezing and caressing and Jay slid one foot to the floor, opening her legs wide for her boss' hand. Soon she was whimpering and squirming on the old mans lap as he held her tight, kissing and groping her. Suddenly she placed her hands on his broad chest and pushed herself away, panting with excitement.

"Lets go upstairs" she said in a whisper, and got to her feet, catching hold of Mr Evans' hand as she went, pulling him from the sofa and leading him up the stairs. He watched her little pleated shirt flap and sway as she wiggled her bottom up the stairs in front of him. She lead him into a bedroom, clearly a girls room, there were posters of boys and pink items everywhere. Jay guided her boss to the bed, sat him down and lifted his legs. He got the idea and slid himself up the bed until he was laying back with his head on the soft sweet smelling pillows. Jay kicked off her shoes and climbed onto her knees on the bed over the boss' legs. Moving quickly she unfastened his trousers and pulled them down eagerly.

The old mans fat cock popped free, already erect and hard it flicked up and slapped against his round belly. His big gray haired balls sat on his thick thighs and Jay placed her hands on the bed either side of his hips, leaned forward, and pushed her face into his groin gently. She quickly ran her lips and her tongue up and down the length of the old mans junk, kissing, licking and sucking all of him. She could feel him twitching and throbbing as she worshiped his big wonderful cock. Rubbing her tongue around his fat cock head she slipped the fingers of one hand under the thick shaft and lifted him upright. Mr Evans moaned softly as she stroked him gently for a moment before pulling the veiny bumpy skin of his fat dick back, standing his cock upright, and sliding her soft wet lips all the way down over the fully engorged head.

"Uuuuuuurgh" her boss grunted with pleasure as Jay took him as far down her throat as she could, again and again, sucking and stroking him slowly. One thing she had learned from her evening with Mr Parkes was that, no matter how far she thought she could take a cock, she could actually take it further. So she pushed her mouth down on him hard, jamming him into her throat until she choked. Over and over, taking more and more of him, her nose pushing into his round belly and his curly gray hairs tickling her lips. Her delicate fingers cupped and tugged gently on the old mans fat hairy balls as she sucked him eagerly, her head bobbing up and down faster and faster as her boss' groans excited her.

"I'm going to cum..." Mr Evans gasped, warning Jay. For a moment she wanted to keep going, to let his cock erupt into her throat, feel his seed flowing in great gushing torrents into her mouth so she could swallow it all. But she also longed to sit on his fat cock, feel him penetrating her tight little hole again, to fuck him like the little slut she was. Jay sat upright, leaning back on her heels as she knelt on the bed and pulled off her school blazer. The old mans fat cock hovered just above his belly, glistening with her saliva, throbbing and twitching as his orgasm subsided.

"Where do you want to do it?" Jay asked throwing her jacket on the floor and kneeling up over the old man.

"in my mouth..." she continued, lifting her skirt, taking hold of her panties and pulling them down, "or in my ass?" She leaned to one side and pulled her leg up and out of the little white panties, then knelt over her boss again, waiting for an answer.

"Sit on my cock!" he replied, Jay leaned forward over him, opening the drawer by the bed and taking out the tube she had put there earlier. She squeezed a big blob of the slippery gel onto fingers and reaching round pushed them between her soft round cheeks and into her tight little hole. She pushed more and more of the gel between her cheeks, knowing she would need to be as wet as possible for her boss' thick cock, until at last she was ready. She squeezed another big blob of the slippery gel onto her palm, closing her fingers on it and spreading it all over the inside of her hand. Then she wrapped her gel covered fingers around his cock head and covered his fat lumpy shaft with lube.

She looked up at the old man reclined at ease on the bed beneath her, smiling at him a little nervously as she worked her way up the bed on her knees until she was kneeling over his waist. He raised his arms, placing them behind his head, signaling that she was to do all the work. Jay was only to happy to oblige, she reached round under her bottom, took hold of his stiff slippery shaft, holding him upright, and lowered herself onto him. His fat swollen cock head pushed against the tight little rosebud between her cheeks. She sat back onto him, wriggling and easing his dick inside. Whimpering in pain as his fat head opened her and popped inside, followed by his thick veiny shaft. Mr Evans lay back and watched the youngsters face as she impaled herself on him. The pain and pleasure merged in her changing expressions as she squirmed on him. Wriggling, whimpering and moaning Jay worked her hot little ass down onto the old mans big thick cock, she felt his strong thighs against her bottom and she lifted her self up a little, then pushed back down hard. Again and again she lifted herself and drove down hard on him, forcing his big cock deep inside.