Weekend Work Pt. 01

This time Dave let his open hand rest on the youngster's bottom as he squirmed, the old man's dark wrinkly hands looking almost dirty against the young man's fresh skin. He closed his fingers a little cupping Jay's round pink cheek, feeling the soft yielding flesh hot in his hand. His fingers roamed over Jay's bottom, caressing, stroking, squeezing, groping, before slipping down between his cheeks and teasing his most intimate place.

Jay bent over the desk, panting and squirming while the old man's hand roamed at will over his hot, stinging ass. Without even realizing he was doing it, Jay moved his feet apart, opened his legs as wide as he could and arched his back pushing his bottom out, as Mr Evans' finger slid between his cheeks and teased his tight little hole. Jay continued to squirm and wriggle as the old man fingered him over the desk, moaning and whimpering softly as his boss groped him. The old man's hand pushed between Jay's legs, his fingers gently caressing, squeezing and pulling on his tight little pink sack.

Mr Evans moved closer, putting his other hand up under Jay's T-shirt, running his rough wrinkly fingers over the young man's milky smooth tummy and up to his chest. His large hand brushed over Jay's hard nipple, then stopped, took hold of it and started squeezing and pulling on it as Jay squirmed. The fat weathered fingers of Dave's other hand still cupped the young man's sack, but now his thumb worked up and down between Jay's ass cheeks, teasing and probing before pushing inside. Jay gasped as the old man pushed his thumb inside, holding onto the desk, arching his back and pushing back onto the hand groping him. Dave let go of the youngster's tortured nipple and slid his hand down over the lads slender tummy and between his legs. He wrapped his fingers around the young man's excited pole and took a firm hold.

Jay whimpered and panted, hands still firmly planted on the desk as his hips squirmed, wriggling his ass on the thumb pushed deep inside, and rubbing his stiff clitt in and out of the old man's big strong hand. It didn't take long, and Jay started to gasp and shudder as his boyclitt throbbed in Dave's clenched fist. Dave kept hold of Jay's throbbing, trembling body until his orgasm had passed, and he could feel the young man's excitement easing in his hand. Then he gently milked the last few drops of Jays juice from him, squeezing it out onto the office floor, before he released his hold on Jay and moved away.

Jay stood up straight and turned to face the old man, his cock and his ass hot and throbbing. He still couldn't look Mr Evans in the eye, so dropped his eyes and found himself staring at the large bulge in his boss' trousers. Suddenly he was on autopilot. Jay dropped to his knees before Mr Evans and in a hurry, with excited trembling hands, he unfastened the old man's trousers and pulled them down eagerly. As Dave's hard cock thrust from the front of his shirt, Jay gasped, the old man's cock was about the same size as his own 6 inches, perhaps a bit longer. But where Jay's cock was slender, pale and smooth, Mr Evans' cock was thick, dark, covered in big lumpy veins, surrounded by thick grey hair and had the biggest, roundest head Jay had ever seen. It was like a great big mushroom or lollipop. Jay didn't hesitate, he leaned forward and sank his soft wet lips down over the old man's big fat cock head.

Dave let out a long low sigh that rumbled up from deep inside as the young man's hot wet mouth slid over his cock. It had been decades since anyone had done this for him and it felt amazing. Dave's cock throbbed, his whole body tingled and his knees went weak. He pulled away from Jay, dropped his trousers to his ankles and sat down in his office chair, opening his legs wide and leaning back. Jay wriggled along the floor on his knees, until he was between the old man's hairy legs. Mr Evans' thick mushroom cock stood upright, the bumpy, veiny, gnarly pole poking from his shirt, the fat round head glistening wet with Jay's saliva.

Jay was still feeling nervous and a little too excited, but was starting to settle into the role he had fantasized about for so long. He felt this was not the time to rush things, so once he had wriggled into position between his bosses knees, he placed his slender hands on the insides of the old man's thick hairy thighs. He ran his fingers gently up toward Mr Evans' groin, around his fat balls and stiff cock, then up onto his round potbelly, lifting his shirt out of the way. Then his fingers caressed their way back down, around the base of the stiff gnarly cock and gently took hold of the big hairy sack. Cupping the old man's balls and lifting them softly, Jay leaned forward, pushing his face into the old man's groin. The soft, warm, musty smell of a man who had been at work all day was intoxicating, and he breathed in deeply through his nose as his mouth went to work, kissing, licking and sucking every inch of his bosses groin. Then, when he felt he had played long enough, Jay pulled gently on the old man's balls, making his cock stand upright. He ran his tongue up the length of Mr Evans' cock and around the big fat mushroom head.

Dave's cock twitched and throbbed as the young man's tongue teased and toyed with the rim of his fat cock head. He tried to lean back and relax in his chair, but he couldn't stop his hips pushing up each time Jay's lips came close to the tip of his dick. His large hands gripped the arms of his chair, and he grunted as he squirmed, longing for the young man's mouth, feeling his throbbing cock would pop if it became any more engorged.

"Aaaaaarrgh... fffffuck..." Dave gasped as he watched Jay, at long last, slide his soft wet lips down over the huge throbbing cock head. The young man's head moved up and down as he slowly and sensually sucked on his boss' thick dick. Still caressing and tugging gently on his big floppy balls as he took the old man's cock deep into his hot wet mouth. His head moved faster and faster, one hand moving up, fingers wrapping around the base of the stiff lumpy shaft, Jay began to stroke the old man's cock as he sucked it. Jay was getting excited himself now, the moans and grunts of his boss making him whimper softly as he sucked on his cock.

"I'm cumming" Dave whispered, expecting Jay to stop sucking his cock. But he didn't, if anything this seemed to encourage Jay, and he lifted himself a little so that he could get the old man's fat cock even further down his throat. Breathing heavily and moaning with pleasure, Dave leaned his head back and groaned aloud. The muscles in his thighs, hips and belly flexing again and again as his gnarly old cock gushed wave after wave of his cum into the young man's eager mouth.

Jay's squeals of excitement as his boss came in his mouth were muffled by the old man's big fat cock head. He choked down mouthfull after mouthfull of thick sticky juice as best he could until, at last, he had to pull away to catch his breath. Gasping and panting, Jay slowly milked the last drops of Mr Evans' orgasm from him, licking cum from his lips as he watched the milky liquid gather on the big fat cock head. He could feel his boss' erection starting to ease as he gently squeezed all of its milk up to the tip. Then he moved close and softly took the floppy cock in his hot mouth again, sucking and swallowing every last drop from it. Feeling as horny as ever, but satisfied with his work, Jay moved away, sitting back on his heels as he knelt on the floor. Without even realizing he was doing it, Jay's hand began to play with his boy clit, that once again poked up stiff and excited from between his smooth milky thighs.

"I'm sorry Jay..." Dave said, noticing the youngster was still eager for more, but suddenly feeling guilty, as if he had done something wrong, "I think we had better go". Jay blushed, suddenly feeling embarrassed by his obvious excitement. Mr Evans got to his feet and started to pull up his trousers, so Jay did the same. They watched each other nervously, suddenly feeling uncomfortable. Once dressed, Dave led Jay to the front of the shop and let him out.

"See you in the morning Jay" he said as he opened the door.

"Yes Mr Evans" Jay replied, looking his boss in the eye for just a moment as he walked by, before blushing and looking away. Jay ran through what happened in his head all night. Thinking about what he should have done, fantasizing about what he wanted to have happened. And wondering what work would bring the next day.

Mr Evans thought about Jay all evening as well. He thought about those red cheeks and how he longed to slide his cock between them. He also thought about the magazine Jay was looking at and the clothes the young sissy was wearing. He imagined Jay in those clothes and his cock grew hard. He couldn't stop thinking about it, he went to bed early as he had to be up early for work, but couldn't sleep. Images of Jay in stockings and suspenders stuck in his head. He was still awake, and his cock was still hard when his wife got in just before midnight. She tried to sneak into bed, but had obviously had a little too much wine with her meal. Dave watched through half closed eyes as she got undressed and pulled her nighty on over her head before falling into bed, laying on her side with her back to Dave.

He still couldn't sleep, his stiff cock nagging him and keeping him awake as thoughts of Jay filled his head. Dave moved closer to his wife, resting one hand on her hip he began to caress her, lifting her nighty as his hand moved over her body. His hand moved round onto her tummy, slowly working it's way up to her ample breasts, lifting and caressing the soft flesh. His fingers found her nipple and gently pinched making it grow and harden. He rolled the stiff sensitive nipple between his thumb and forefinger and was encouraged to hear a soft moan from his tipsy and playful wife. He worked his hand down onto his wife's hip again, then over her bottom onto the back of her thigh. She responded by moving her leg, raising her knee up toward her chest, giving Dave easy access to her pussy. His hand moved between her legs, gently caressing the soft lips within. His fingertip rubbing her clit for a moment before moving over her lips again, gently caressing them open, probing the warm wet hole before returning to her clit.

Mrs Evans began to moan softly, wriggling her hips on Dave's hand, just as Jay had done. Her moans growing more and more intense as he caressed her until, panting softly, she whimpered and clamped her thighs on Dave's hand. A moment later she rolled over onto her yummy and lifted herself up onto her knees and elbows, offering her ass to Dave. He quickly threw the covers back and got on his knees behind her. Dave's tortured fat cock head rubbed against his wife's warm wet lips for a moment before he buried his member deep inside her for the first time in, he couldn't remember how long.

She gasped as he entered her and pushed back onto him. Dave started to fuck her, harder and harder, faster and faster. Gripping her hips tight in his clenched fists as her ass cheeks slapped against him. He kept going, his stiff gnarly old cock pounding in and out of her wet pussy over and over again.

"Oh my god... oh my god.. oh my..." His wife whimpered and moaned as Dave fucked her hard like he hadn't done for years. She buried her face in the pillows, moaning and squirming. Dave was gasping for breath, working hard, ramming his aching cock into his wife again and again. He closed his eyes and pictured Jay, bent over his desk at work, his soft round cheeks hot and red after a good spanking. He imagined himself ramming his hard cock into Jays hot little ass, over and over again, and with a loud groan his cock throbbed hard in his wife's pussy, pumping load after load of his cum into her, emptying his big fat wrinkly old balls completely.

The next day at work was even more awkward than Jay had expected. Not only did Mr Evans behave like nothing had happened the day before. But for some reason his wife seemed to be all over him, laughing and flirting with him like a little girl. The weather outside was bad, cold and wet, so the shop was quieter than usual. Late in the morning Jay found himself alone behind the sales counter, Meg was out the back making a brew and Mrs Evans had popped out. Jay eyed the little mirrored window that he knew Mr Evans was sat behind, wondering what if anything would happen between them now. He was reaching up, stretching on his tiptoes, to tidy up the top shelf on the wall behind the counter, when Mr Evans came out of his office and joined him. They smiled at each other, there was an awkward silence, at last Dave spoke.

"So..." he asked in a low voice, "do you dress up like that yourself?" Jay knew exactly what he meant, even though the question seemed totally random. He was of course referring to the magazine Jay had found the day before. He felt his face start to flush pink with embarrassment, which seemed to be happening a lot recently, and looked away.

"Yes" Jay whispered with an effort, admitting out loud for the first time that he liked to wear women's clothes. Dave looked around for a moment, making sure there was no one else around, then he moved close to Jay.

"Perhaps..." Dave continued, placing one hand on the young man's tight jean clad bottom, "perhaps you could wear something into work next week?" he asked. As he spoke, Dave's hand moved up Jay's back, under his T-shirt, then squeezed down inside the waist of his jeans. Jay didn't react, he just let his boss force his hand down the back of his tight trousers.

"Unfasten your jeans" Dave whispered into Jay's ear, Jay glanced quickly around the shop, then quickly unbuttoned his jeans and pulled down the zip. Dave's hand immediately pushed deep inside, groping Jay's soft cheeks and pushing his fingers between them. Jay gasped, his cheeks still a little tingly from yesterdays spanking, and took hold of the counter to steady himself as his boss groped his ass. Then Mr Evans pushed his other hand down the open front of Jay's jeans and pulled out his already semi hard and excited boy clit. Mr Evans continued to finger and stroke the young man, groping him right there in the middle of the shop. There was a noise by the back room and as the door opened Mr Evans moved away from the panting, squirming youngster and the sales counter. Jay quickly tidied himself up as Meg appeared with the coffees.

"Okay Jay" Mr Evans said in a suddenly loud voice that made Jay jump, "don't forget, next week," taking his coffee and returning to the office.