Category: sexystories

He wakes up bright and early (as they say) and rips the covers off. He is almost naked except for a bright red thong that he slept in. It arrived in the mail just yesterday and he was trying to break it in, like how some people will wear new shoes to break them in and make them feel more comfortable faster. He lies still for a second after uncovering himself, staring at his own bulge. He was not horny, but he still had a small erection, like how some people are when they first wake up in the morning. The thong is just big enough to fully cover his penis, which eventually begins to soften again after only a few minutes. He reaches down and adjusts it so it is in a neat package again; it was starting to crawl up towards his belly, but that is not as comfortable as placed over and between his testicles like how it would sit if he wasn’t wearing something that was tightly over it. Finally he swings his legs over and stands up. The thong is such that it lets his whole ass hang out. A thin elastic waistband goes around and into the back, where a thin piece of cloth rests against his lower back before forming another thin stretch of cloth that sinks into the crack of his butt. He stretches his butt cheeks and lets the string of the thong rest in the middle again; even with something so small, it still wiggles around while he sleeps. Before doing anything else, he turns around and quickly makes his bed, like how some people will have other kinds of habits when they first wake up, this is his. Last night he was alone, so there was nobody else to get up before the daily ritual. As he walks out his room and towards his kitchen, his belly jiggles along with his ass cheeks while he walks. He puts on his glasses that were on a small table in the middle of the studio apartment and scratches his beard, which obviously needs a trim. Today was another day of work. He makes some coffee and grabs some fruit and bread. No point in doing anything complicated when he was feeling so lazy. He sits at a chair against the table in the middle, and his ass sits comfortably against the bare plastic chair. Although he isn’t thin, he isn’t fat; he has mostly been described as plump. The fat of the stomach only goes over his crotch a little bit. There is still enough revealed that there is a clear bulge pressing out from the crimson cloth. Pretty soon he is off to go to work. As part of the usual routine of breaking into his new clothes, he puts on his business suit while still wearing the thong. He knows that the cologne he uses is strong enough to hide any sweaty smell that might permeate from wearing an undergarment for so long. Walking downstairs from his apartment, he can feel the insides of his pants against his bare thighs and ass, and it feels very good. The usual bus ride. The usual morning greetings. He has a meeting this morning: he loves being around people while wearing sleazy underwear. As he sits down, he can feel the cloth tighten against his asshole and groin, which makes his dick raise a little bit like somebody moving after they have been moved while sleeping. His boss starts the meeting, upset that he was late yet again, but the anger feels very insincere since this is almost always the case for him. As the boss speaks, he can’t help but check him out. The boss is thin, with a muscular neck and face, brilliantly colored eyes, and he always seems to have the perfect hair when everybody else’s looks rushed. Halfway through the presentation the boss itches his stomach. The boss speaks confidently and with authority, answering questions quickly without hesitation. He finds himself catching looks of the boss’s belt buckle; there is nothing special about the buckle itself, but like how some people will look at a women’s clothes with a certain intent, he will look at the boss’s clothes with his own. Before anybody realizes it, the meeting is over. He has written down plenty of quality, accurate notes, yet he has honestly forgotten exactly what the point of the meeting was supposed to be. The boss heads back to his office, and he chats with the others about what they talked about, always only half listening until he recovers from his daydreams and gets fully back into reality. The day is long but productive. Sometimes at work he likes to listen to porn. He never watches videos, because that is too risky, but he just plays the audio and imagines the rest for himself. When nobody is watching, he occasionally rubs his own crotch underneath his desk before returning his hand to its proper place. Towards the end of the day, he gets an email from his boss. He wants him to come to his office before the day is over. Minutes later, he is in front of his boss’s office, knocks, and is instructed to enter. His heart rate jumps a few beats per minute. His heart pounded like anybody’s would when they speak to their bosses, only his chest pounded for a different reason. When he enters, his boss’s suit jacket was hung over the chair at his desk, and he had slightly loosened his tie. He was standing up and looking out the window, which was wide open, exposing the cityscape that extended out beyond the great lake. The boss asked him to take a seat, and he obliged. His boss still looked out the window, and he could look at his boss’s ass during his whole walk to the chair in front of his desk. It is perfection. He sits down. The boss turns around. He notices a framed picture of a woman on the boss’s desk. He looks back up at his boss, who has now sat down at his own chair facing him. A moment passes, and the boss finally begins speaking business with him. How the department is doing. How he is doing. He is doing good. The boss says that he has noticed he has been working extra hard recently, and he thanks the boss for noticing. The boss nods and asks him to do a few extra things tomorrow. He agrees enthusiastically. The boss smiles. As he heads back to his desk, he feels strangely disappointed. He heads home and finally takes off his thong. His dick flops freely down to the floor, as if it was gasping for air after drowning. He puts on normal underwear and goes back to bed, thinking about his boss and stroking his erection. Tomorrow is a new day, and he goes back to work as usual. This time he made sure to bring some food, only he accidentally brought too much. Deciding to thank his boss for the opportunities he was given yesterday, he heads to his office and offers him the extras. The boss gladly accepts it and thanks him. They have some more small talk and the boss asks him in person to visit his office again before going home. Naturally he agrees. Another productive day, despite him listening to more sex than usual through the security of his headphones. He goes into the boss’s office, this time feeling slightly more comfortable. He sits down again. This time his boss did not loosen his tie, but he still let his jacket rest against his chair. The boss was facing him when he walked into the door, which slightly upsets him. They talk about a little bit of business, until the boss mentions offhandedly that their IT department tracks what employees do on their computers. His face goes red. He quickly glimpses at the framed picture again before his eyes dart back to his boss. The boss grins. Their company has a strong focus on diversity, the boss says. You have nothing to worry about, just don’t let anything stop you from doing the great job that you’re doing. He nods silently and heads home, feeling strangely relieved. The next morning he decides to wear his red thong from the day before; it was still fairly new, so it couldn’t be that dirty, right? Tomorrow is yet another meeting. Once again he comes in late, only this time the boss doesn’t say anything about it. The boss just smiles softly at him and proceeds with the meeting. another productive day, only this time he didn’t listen to anything erotic. He was fully focused on work, and got more done than he had ever done before. Another email from his boss invited him to his office again, only this time a much later in the day. He stayed later than usual, looking at the clock every several minutes until the appointed time. Most of the office was empty. He felt his penis shifting underneath his tight thong while he walked to his boss’s office. Again the boss was facing the wide open window. Lightened windows were dotted across the dark cityscape like stars in the sky. The boss’s jacket was against his chair. This time when he sat down in front of his desk, he didn’t see any picture frames. The boss faced him and sat down at his desk. His heart pounded. The boss could sense his emotions. The boss gave a soft smile just like the one he had given that morning and asked him to stand up. He stood up quickly. The boss pointed to a coat rack in the corner, and asked him to place both his jacket and the boss’s jacket against it. While he did, the boss stood up, the open window looking almost black from the night outside. The boss took off his tie, then asked him to take off his own tie and shirt. He quickly pulled off his tie and unbuttoned his dress shirt. His dick was throbbing. The boss, still dressed, asked him to then pull his pants down. He unbuckled his belt and dropped his pants, taking off his own shoes and socks as well to take it off. He was wearing nothing but his glasses and his sweaty red thong. The top of his dick was almost poking out from the top of the thong near his pubic hair. The boss nodded and smiled. He slowly moved towards the boss. The boss began to unbuckle his own pants. Without a word, he then kneeled down in front of his boss, his face now directly in front of the fly of his pants. He put his hands against his boss’s crotch, feeling an erect penis behind his underwear. He pulled down his pants more with one hand while rubbing with the other. He boss sighed as he stroked. The boss pulled down his own underwear, revealing his dick which bounced upwards as soon as it was freed. He started to slowly jerk him off as his mouth began to salivate. He smelled his boss’s sweaty balls and chest. He gently placed its tip against his tongue and began to lick all around his shaft, gently jerking it with one of his free hands closer to his testicles. A few moments passed, and he finally wrapped his lips around it. As he sucked and bobbed his head, the soft tip would sometimes rub against the roof of his mouth and the back of his tongue. His quiet moans were greeted with his boss’s gasps and grunts as he went to work. The blood in his boss’s penis pumped and he could feel his boss’s heartbeat around his wet lips. He tasted amazing. He pulled more of the boss’s pants down as the boss slowly unbuttoned his own shirt. As the boss’s ass was revealed, he slid his hands back around the thighs and gripped his ass cheeks as he continued to suck his dick. The boss gently thrusted his pelvis back and forth in rhythm with him bopping his head. The boss gently rubbed and scratched his head as he continued to massage his boss’s ass. After some time, the boss urged him to stand and they began to make out, rubbing their hard penises against one another. He continued to stroke his boss while his boss lowered his thong and began to jerk him off as too. The boss lead him to his desk and he leaned back until he was laying on the desk. They never stopped making out. They let out soft groans and moans and continued to kiss and rub their dicks against each other. He felt his boss’s balls and thighs rub against and near his asshole. He couldn’t wait any longer and begged his boss to do it. The boss jerked his dick off a bit and covered it in his saliva. The boss gently pressed his thumb into his asshole, and as it gently slid in he sighed seductively. The next time he put in his index finger, then his index finger and his middle finger, until he finally slid his cock in, slowly pressing it further and further into his asshole until finally his balls were practically touching his ass. He moaned as he slowly pulled his hard dick out and then back in. Faster and faster he moved and louder and louder they got. He let his arms rest out on his sides. The boss rubbed his stomach, his thighs, and his ass as he went faster and faster. Smacking sounds echoed across the room alongside cries of passion and excitement. The boss gasped and held his legs tight against his chest. Just as his boss finished, so did he, and his whole chest was covered in white oozy goodness. The boss kept his dick inside him as he bent down to clean his stomach with his own tongue, making loud slurping sounds and making him laugh. They both were soft once against and spent a few minutes cuddling on one of the chairs, letting their heart rates sink down to normal. They got dressed again, laughing and smiling as they exchanged a few jokes. He left his boss’s office to go home, but before he left he noticed the boss once again placing the picture frame against the table. With one last look, the boss smiled at him as he let the office door close. He went back home yet again, admiring the city lights through the windows of the late night bus. He couldn’t wait to go back to work tomorrow.