I decided to write another post for my Straight Punishment web serials as they seem so popular. This post has a lad exploring a part of himself he has never dared touch before. Enjoy.
Gary had been in the stranger’s bedroom in his white socks for the last two hours and was almost done. He was pretty proud of his work and was looking forward to eating. Through the open windows, he is enjoying the warm sunny day and the radio is blasting out great tunes. He loves decorating and prefers it when his customers leave him alone to get on with his painting. The older guy who he is working for today had offered a hot drink and biscuits and then vanished to work on his laptop in the living room. This was an ideal job for the twenty-four-year-old.
He picks up his phone and taps open Hinge. One of the advantages of working in different locations is he can chat up women from all over the place and his girlfriend is less likely to find out. He has learnt from experience that shagging her friends is a bad idea as they always ended up finding out. The women would get drunk over wine and end up confessing to the infidelity like some bad episode of a TV soap opera. He knows it’s better to sow his seed far from home.
One of the big advantages of working in people’s homes is the chance of meeting a bored housewife is high. He has fucked quite a few older birds. He doesn’t really mind the age gap and they are always grateful of a younger guy pounding them. Most of the time he didn’t even get undressed. He’d pull up his tee-shirt and push his pants down and then bangs them. They would moan and groan and he would empty his balls. The older rich ones would include a generous cash tip, which the taxman would never find out about. He often got recommended to their friends who he would also fuck the brains out of. As a young, good looking lad this was an ideal job.
The job today wasn’t going to get him sex from the customer, but he might get it from a neighbour. The guy he’s working for is older than him and said he didn’t allow outdoor shoes in the flat, which is why Gary is standing in his white socks. The man is taller than him and by pulling off his Nikes Gary felt even smaller. He never liked being around taller men. He wasn’t sure why but he just felt their height gave them some power he couldn’t possess.
Today he is wearing grey jogging shorts and a white tee shirt. His white Calvin Kelvin underwear are a brief design and with his cock tucked down he creates a visible bulge in the shorts. His cock is uncut, slightly longer than average but he’d like a bit more girth. Still, he never had any complaints and he always cums. His orgasm is all that matters to him. He sometimes wonders if he has any kids he doesn’t know about as he never wears a condom. He’s happy not to know, though.
“How’s it going?”
The house owner comes in just as Gary is on his knees painting the skirting board. Gary cranes his neck and feels a bit weird looking at the man from this angle. He can’t help but notice the bigger bulge that is clearly in view from here.
“Yes, all going well. I just need to move the bed back and I’m pretty much finished.”
“Oh, that’s great. It would have taken me much longer and there would be paint everywhere.”
“It’s a nice colour.”
Gary doesn’t care about the colour but he always says it to customers to reassure them they made the right decision. He doesn’t listen to the reply as he just wants to get out into to sun. Plus if there’s a neighbour free he really wants to fuck her. Sunny day sex is the best.
“Right, I’ll leave you to finish off. Let me know if you need anything.”
As the man walks out Gary wonders if the guy would let him use the room to fuck a woman. It’s a weird request but no man should get in the way of another one having sex.
This makes him smile as he thinks of the times he has stolen a girl off a mate at the end of a night out. He is the best looking of his group of friends and despite girls saying it’s all about personality he finds he can easily take a girl with a bit of charm. His mates hate him for it, but it makes him happy.
Gary keeps thinking about asking to use the room and maybe the prospect of the two of them sharing. Obviously, no touching but taking a hole each. He is strangely intrigued about the guy’s bulge and would like to see how big he is. He has banged a few women while a mate gets a blowjob. It’s a bit weird but kind of fun, too. One of his mates really regrets sharing as the other guy saw how tiny his penis was. He even took photos. Everyone laughed their heads off when they saw the picture. The guy just sat there turning bright red. They have given him the nickname Little Willy and they tell all the girls he tries to chat up. The guy is now the one they all boss around and they get him to do stuff. If someone needs help moving house or gardening it is Little Willy that gets a call and he does as he’s told. They all find it bizarre that he lets them use him and he buys extra drinks for them. Little Willy seems to enjoy being the group’s bitch and serving the real men. Sometimes it feels a bit cruel but it feels so natural. It’s just the pecking order of life.
Gary starts to tidy up and put the room back to how it was when he arrived. The paint will take the rest of the day to dry but the warmth of the day will speed that up. As he moves the bed back his foot kicks something which gives off a metallic ring. Hoping he hasn’t broken anything he looks under the bed. The wooden floor is completely dust-free under there and there is just a silver box stored underneath. He thinks of the mess underneath his bed and is impressed with the tidiness of this man who lives alone. He is pleased nothing looks damaged and continues to clear away his work tools.
Even as he cleans up the silver box continues to play on his mind. It is almost like the metallic ring is still in his head and is drawing him to return. He pushes the thought out of his mind.
It is not unheard of for him to have a nosey around the places he paints. He has looked in women’s underwear drawers while he has been left alone before and never been caught. Sometimes he even rubs his cock on things as a way to mark his presence. This box feels different, though, and he feels it is best to leave it alone.
Like a mythical Siren singing to sailors to lure ships onto dangerous rocks, the box continues to play on his mind. It seems to call out to be opened. Whatever it contains he feels he needs to know.
To distract himself he moves his equipment to near the front door and checks on his apps in their hidden folder. His girlfriend often checks his phone so he has to make sure nothing can be found. He is always deleting his cock photos and then recovering them from the Deleted folder.
While he is near the front door, he sees the homeowner is on a conference call with a headset on. His mind is pulled back to the silver box under the bed. If the guy is busy now would be an ideal time to investigate what the box contains. He goes through the logic that it might be something illegal and therefore his job as a good citizen to report it to the police.
Once back in the bedroom he tries to act quickly and pulls the object out from under the bed. The scraping on the wooden floor immediately sends him back to check the hallway. He is convinced the owner will be heading towards him, but the corridor remains empty.
He stands perfectly still waiting for at least two minutes. Still, the hallway remains empty.
Returning to the box he kneels and places a hand on the top. It is cold to the touch. It takes the heat of his body away from him to keep itself warm. He slowly flips open two clasps and then lifts the metal arm which would allow a padlock to be fixed. Luckily for his curiosity, there is no padlock fitted.
At this point, he could open the thing, but instead, he stands and returns to the hallway. He can now hear the man talking and that convinces Gary he still has time to explore. He goes back and knees before the object and with great reverence opens it.
As the hinged lid opens he has a terrible dread the thing will be empty or filled with some old toys from the guy’s childhood. That worry evaporates as he gazes down at the contents of the silver box. He has seen a few of these items before but never so many at the same time. A feeling of Christmas Day rushes through his body as his eyes greedily move over all the items. He has no idea what to concentrate on first.
The box is a treasure trove of sex toys. Things like dildos he has used on previous lovers but most of the things in this box look very kinky. There are ropes, straps, cuffs and chains. All these are aimed at a love of bondage. There are also claps, gags, collars and a paddle. These are about control and pain. As well as the sex toys there are BDSM magazines and DVDs which he sees are about a man having power over another male.
He’s not fully sure why, but his cock is rock hard and pushing to escape his underwear.
His hand moves over the treats like a mechanical claw in an arcade game. Questions flood his mind and making the decision of what to pick up first seems impossible. He sees a metal ring attached to leather straps and he wonders what it is like to have no choice but to accept a cock into your mouth. He has always enjoyed having his nipples squeezed and he sees some items which he assumes are designed for that task.
In the end, he picks up a fat butt plug which he cannot believe fits inside anyone’s arse. As he holds the black object he feels it is not as firm as it looks and there’s a bit of give. He cautiously sniffs it and is pleased when it smells of plastic. Holding it before him he doubts he could even fit it in his mouth never mind his virgin bum hole. He’s glad he’s a straight boy if this is the sort of thing that the gays stick inside themselves. He can’t help but wonder how anyone gets pleasure from having that violate them.
He is still considering the anal toy when he sees another one in the box and as he picks it up he spots a third. He also sees a red butt plug shaped like a fat cock. He lines up the three black objects in a row and realises they are make a set: small, medium and large. He keeps thinking about how many guys they have been inside. He is assuming the homeowner is gay as the BDSM magazines are all about men submitting to other men. Gary and his mates have discussed daring each other to pay to visit a dominatrix, but they never went through with it. As straight lads, they were all worried their arses would be involved in her punishment. Just the mention of having their back door smashed in was enough to put the straight lads off. Well, apart from the mate Andy. Everyone was convinced he went along and got the full treatment. They call him Anal Andy as whenever he gets drunk he talks about anal sex.
He realises having access to these toys makes the prospect of using them very tempting. If no one will ever know he is certainly emboldened to try one out. The little one looks like it could do no real harm and there’s a lube dispenser in the box. Part of the reason he holds back is what happens if he enjoys it too much. He doesn’t want a butt plug to turn him gay. That and the idea the owner may walk in and catch him, but he has been left alone for a while now. In his mind, he feels he has been forgotten and the guy is too busy with his Zoom meetings.
He is surprised by how light the little plug is when he finally picks it back up. Again he sniffs it and it pleased it seems clean. Some strange convulsion comes over him and he slides the plug into his mouth. the cold plastic warms up quickly as his tongue slides over it. He feels like he is sucking on a baby’s dummy (pacifier).
The whole thing is getting too horny for him and he has to release his cock. His member needs to stand up and has been trapped for too long. As he pulls at his clothing he checks the hallway again.
Once his shorts and underwear are around his ankles he knees back in front of the box. He notices he has spread his legs more and his arse feels more exposed. Without wasting time contemplating his actions he dispenses a few squirts of lube on his fingers and then moves his hands to his arse. He pulls one arse cheek away with his left hand and rubs his arsehole with his lubed right hand. All the time he sucks on the small butt plug.
It feels strange to touch himself down there but the lube makes the experience pretty pleasant. Usually, he just wipes and moves on but he is beginning to realise just how many nerve endings are hiding in his arse. His plucked up sphincter actually seems to enjoy being touched and running a fingernail lightly over it sends waves of pleasure around his body.
Letting out a gasp of air he closes his eyes and pushes the tip of his finger through his ring. He assumes it will hurt too much and his exploration will end immediately but he is surprised to find the feeling isn’t so terrible. He even pushes a little further in and begins to enjoy playing against the tightness of his ring.
Once he has decided the pain is tolerable he removes the small butt plug from his mouth and gives it a layer of lube. In no time the end is pushing against his ring and begins to slide inside him. After being in his mouth for so long it doesn’t feel cold and he welcomes the foreign object inside.
It is less than an inch inside when he begins to wonder if he has gone far enough. He doesn’t want to be gay and is worried this experience isn’t as bad as he thought it would be. If he stops now he can say he tried but didn’t like it. Even as he thinks of pulling the plug out he continues to push it deeper inside. It is a classic case of an angel and a devil. The angel tells him he’s straight and his arse is not for pleasure, while the demon encourages him to push it in and sees what happens. The devil’s voice tells him it can’t be gay if he’s alone. Touching his cock doesn’t mean he wants to touch other guys’ bits. This is just like wanking. It’s his body and he can touch himself all over.
The butt plug continues to slide in.
Gary lets go of his arse cheek and pops the medium plug into his mouth. He actually loves the sensation of a plug in both his holes. He dispenses some lube on his hand and starts to play with his erection. He notices he has a raging hard-on and his cock is aching from the blood pumping into it. He is now reaching the thicker end of the plug and he’s glad there was a small one in the box. He doubts he could take anything bigger than this.
His breathing is getting louder as the plug expands his ring and he firmly wanks himself off. He can’t cum in the guy’s bedroom but he wants to get as close as possible. The plug continues to slide in and he begins to think about how long it is. When he saw it he was sure it wasn’t this length. He is almost convinced it will be in his stomach soon.
He is taken by surprise when the plug suddenly gets sucked inside him as he reaches the tapered end and his ring grips tightly on the thinnest section of the toy. He only just about manages to stop himself cumming as the plug finally slots inside him.
Once it is inside he stands up and walks around a little, kicking away his shorts and underwear. He thought it would feel stranger but he guesses the thing is too small to have much of an impact. His hand never leaves his cock as he is loving what he is doing. Once he has checked the hallway he returns to his kneeling position just like a man at an altar. Accept this place is full of sex toys rather than religious relics.
The device is slippery with his lube covered hand, but he manages to get a grip of it again ready to take it out. As he begins to pull he is a little worried when the thing will not budge. He applies more pressure but still, it refuses to come out. He begins to wonder if there is a method to remove due to a vacuum being formed. As he looks around for his phone to Google ‘how to remove a butt plug’ the thing finally comes out.
The removal also almost causes an orgasm and he smiles at just how much fun his arse is.
As pulls and pushes the toy in and out he finds moving from the thickest to the thinnest parts causes the most pleasure. His eyes roll back as this discovery drives him wild. He can’t believe he’s never played with his ring before.
All this time he has been sucking on the medium butt plug and now his thoughts turn to that. He wonders if the increase in size will cause an increase in pleasure and whether he will even be able to take it. Of course, he knows there’s only one way to find out. A battle rages in his mind, though. If he keeps going is he ever going to be able to stop. He has enjoyed fucking girls since he was 15-years-old and he doesn’t want to turn gay. That logic is losing due to the amount of pleasure he’s getting from the plug in his butt. As long as no one knows he convinces himself to continue.
Placing the small plug next to him he is pleased to see how clean it is. He removes the medium-sized one from his mouth, still uncertain why he wanted to suck on it, and smothers it in lube. He adds extra lube to ease its journey.
Once he has made himself comfortable he begins to gently push the tip into himself. At first, it slides in easily and he’s pleased he warmed himself up with the small one. Soon he is at the point he is used to but he knows there’s more to come. The plug’s push through his ring slows down as it begins to stretch him.
He pulls strange faces as he strains and the thought of his friends seeing him now comes into his head. They would laugh their heads off at him as he crouches on a stranger’s floor in socks and tee-shirt, wanking furiously while sticking a butt plug up his arse. He imagines even Little Willy joining in and suddenly he is the butt of all their jokes. He is the go to person to pick on when they are bored and need to show off their masculinity. Even Anal Andy would get a break from his usual jokes.
All those thoughts don’t stop him, though. If anything they encourage him to push the toy in deeper. Taking it up the arse is humiliating for a straight guy, so he would expect his friends to abuse him for getting off on doing it. He deserves it. The feeling of something sliding through his ring is so horny, though. He doesn’t want to stop.
The sensation is driving him wild and he’s becoming less cautious about the noise he is making. He has always been noisy during sex and he can’t help himself. His base instincts are taking over and pleasure is the only thing on his mind. With this carefree attitude, his groans are drifting down the hallway.
He still isn’t over how big the butt plug feels compared to how it looked. He feels like a blimp is going inside him yet he knows there is still the large plug sitting in front of him. He can only admire a guy who can take that thing.
The first clue that the plug is almost home is his fingers brushing against his arse cheeks. In the next moment, the plug gets sucked inside as he finally reaches the thinnest part. The final moment as the thickest section sat in his ring stretching him was so intense. He has to stop wanking and control his breathing. His ring is now gripping the plug so tight that he wonders if he’ll be able to get it out.
Cautiously he stands. He has to place a hand on the bed as his legs have become wobbly. He can certainly feel the plug inside him this time. As he stands it begins to rub his prostate and he feels a whole new level of pleasure. At first, he thinks the massage of this hidden, secret place deep inside him must be damaging something as it is so intense. Despite his concern, he continues to gyrate his arse just so he can experience it. He has stopped wanking as he feels so close to an explosion inside his ball-sack. He can’t believe guys don’t talk about how much pleasure this is.
He leans against the wardrobe to steady himself as he gyrates and gently pulls at the plug which sits firmly inside him. His virgin hole is truly being stretched. There’s no need to touch his cock now as his arse is providing all the pleasure he needs. He opens the wardrobe door and looks at himself in the full-length mirror. He can’t believe what he is seeing. He is a straight guy having the best wank of his life because there’s a butt plug inside his arse.
He knows he will not be able to stop himself cumming soon but he can’t worry about that. He has been taken by the moment and will deal with the consequences later. All he wants now is pleasure and release. He imagines this anal-gasm is going to blow his socks off. He noisily gasps for air as he gets off on the thing he never thought he would do.
To stretch his ring he pulls the plug out one more time, but it is too much for his body. His balls shift position and his spunk explodes out of him. As it does the plug goes back in and milks his prostate. He drops to his knees as the cum shoots out of him. His cum has even landed on the wardrobe mirror and the lines of white jizz run downwards. His cum has also landed on the floor and he feels like he has marked the room as his property. As he gasps for air his seed is leaking out of him and he anally squeezes the plug to get all the pleasure he can from it. He can’t believe how much man-milk is coming out of him. His seed is everywhere.
Sitting on the floor in a sweaty, spunk drenched mess he can hardly believe what he has done.
“Well, well. What’s been going on here?”
Gary looks up in the mirror and stood behind is the owner of the house. He had been so caught up in his amazing orgasm that he hasn’t heard the guy enter the room.
“It’s not how it looks?”
“It looks like a naughty boy has played with my toys without permission and loved having his arse stretched.”
Gary realises it is exactly how it looks. The words that fall out of his mouth surprised even him, though.
“But I’m straight!”