- Free Sample
Often at weekends, Will would regularly visit junkyards in search of prized components for his Caddy. These junkyards seemed to Will to be a peculiarly masculine environment full of big men in overalls clambering like mountaineers over the dead cars piled high or lying sideways in pools of muddy oil extracting precious parts. One of the junkyards, in particular, specialized in Cadillac cars, and the two men there seemed happy to let Will know if a much-needed part he needed for his car arrived. In the run-up to the summer holidays, Will had been there almost every weekend and was on good terms with Frankie and Big Joe, who ran it.
He got on so well with these two junk men that they’d often include Will in a round of beers. They would sit around on battered old couches in the portacabin that was both their office and a storeroom, talking cars. Will enjoyed the camaraderie of these older men who shared his love for cars. Even though Big Joe was old enough to be his granddad and Frankie was in his late thirties and already bald, Will realized they quite liked him hanging around. Now and then, the teen caught them casting sneaky glances, checking out his butt or groin. It amused and flattered Will that these ‘older men’ should secretly have the hots for him.
You see, Will was openly gay, which was probably not surprising given his effeminate nature. Even though he could talk and work on cars with the best of the macho cis males, he was always dressed in bright, fashionable clothes. At first, many of the junkyard men dismissed the ‘faggot freak’ out of hand. Still, Will’s knowledge of cars usually won them over. Only the hardened homophobes still treated him with disdain, the men in the MAGA hats. But his warm personality often shone through, and as a result, he was as welcome as any regular to these places of male machismo and ego. Most of the grease monkeys don’t bat an eyelid now if they see young Will walking around in a bright floral shirt or a bright purple suit. And those that do mind, Will stays away from.
The walls of the portacabin at Big Joe’s and Frankie’s yard seemed covered in posters and pages of pinups from various men’s magazines. Naked women were everywhere. They even had an attractive brunette woman in her late twenties called Brenda work there a few days a week. Not that Will ever saw her do any work when he was there. Still, the dirty posters remained, making Will wonder why any girl would work here with so much misogyny on display.
Also, Will always got the feeling these two men were checking him out. Will noticing their attention, often laughingly asked, “Are you guys in the closet or something? I think all these naked women are just a smokescreen, you know.”
They’d laugh. Frankie would say something like, “We ain’t no pillow biter, Will, that you can be sure of. But we don’t hold it against anyone who is—different strokes for different folks and all that.”
*****
On the first weekend of Will’s summer holidays, Big Joe rang to say that a part he had ordered had arrived. He had the phone on speaker at the time, and his older sister heard the call. She gestured for him to mute the call, and he said, “Could you hold the line for a moment,” and he put the call on hold.
She said, “Why don’t you go dressed in some of my clothes and see what happens? It would be funny if they hit on you, and it would confirm your suspicions about them perving on you.”
“I might be queer, Kim, but I’m not one of those crossdressing sissy types,” he said wide-eyed.
“Why not? You’re hung like one, little bother,” she said and laughed, doing the small dick sign. “But it’d just be a joke. You don’t have to do it all the time.”
“I don’t know?”
“Go on, I’ll help you get dressed and put makeup on you. I bet I could make you look like a real girl,” Kim insisted. “I even have a nice wig you can wear. Go on, do it.”
He thought for a moment, then smiling to himself he took his phone off hold. He got on the phone and said, “Hey, sorry about that, Joe. Look, I can’t make it right now as something just came up, but do you mind if I send my sister Liza?”
“Sure, kiddo. Ain’t no problem to me,” Joe said in his deep voice with the southern twang.
“Thanks. Now you treat Liza nice…”
“Don’t worry, kiddo, I’ll put on some fresh coffee for her and give her some homemade chocolate chip cookies,” Joe said.
“You better…” Will warned and ended the call.
Will gazed at his sister and said, “Oh my God, what have I done?”
“You’ll be pissing yourself laughing about it once it’s over,” Kim said with a wicked smile. “Get those old men drooling for you, especially the real homophobic jerks. That’ll teach them to be ignorant assholes.”
Will shivered. He was having doubts. “What if they figure out it’s me in women’s clothes? They’ll probably beat me up.”
“Those dumb morons won’t figure out anything,” she said, rolling her eyes. “They’ll be too busy pants-stroking their huge boners. Come on, let’s get you sissied up.”
‘Now it’s time to have some fun with these dirty old homophobes,’ he thought. ‘God, Kim’s right. What a laugh these old bastards getting boners thinking I’m a girl.’
*****
The preparation didn’t take too long. Will’s sister was great at applying makeup, and she had some sexy clothes. It was almost like she had been planning this for a long time as she gathered everything she needed to turn her little brother into a girl in a flash—from lingerie to clothes to accessories. Going to a junkyard dressed as a girl made him nervous because the men who work at or frequent those places were usually only moderately homophobic but severely transphobic macho types. Still, Kim was adamant that no one would have any suspicion that he was a girl and was adamant the whole experience would be a ‘crack up.’
After applying his makeup and blonde wig, Will changed into a pink g-string/thong, a black mini skirt with knee-high black boots, and a red vest top with a pink bra, taking full advantage of his B-cup man-boobs. He put on perfume and jewelry, then examined his look in the full-length mirror.
“See, you totally look like a girl,” Kim gushed. “They’ll never guess it’s you.”
He had to admit she was right, and the fact he could so easily pass for a female made him feel a little sick. Will may be gay, but he always thought of himself as a man. Seeing the very feminine visage in front of him shook him to his core.
“I don’t know if I can do it,” he said. “It’s too weird.”
Kim suddenly pulled out her phone and snapped several pictures.
“Hey, stop that,” Will whined, grabbing for her phone.
Kim held her phone out of reach. “If you don’t do it, I will send this to all your friends,” she warned.
“That’s blackmail,” he said with a frown. “Besides, I don’t think my friends would care that much. A lot of them dress in drag.”
“Then I’ll send them to everyone in the family.”
“No, not that,” Will whined.
“Do it, and I’ll delete them from my phone.”
“You bitch,” he spat.
“Do it, or else I’ll send them to Mom and Dad and everyone in the family, including Nana James.”
Will gasped. “You wouldn’t!”
“I would. So what’s it to be?” Kim asked with a smirk.
“Please, Kim, this has gone far enough,” he whined.
“Do it or else,” she said adamantly.
He sighed deeply. “Oh, OK, you win. I’ll do it. But you’ll let me delete the photos once I get back, right?”
She nodded. “I will. I promise. Now, go give those dirty old men something to think about,” she said, imagining them trying to ogle ‘Liza’ without being too obvious. “I want all the deets when you get home.”
*****
Parking the car outside the junkyard, Will picked his way around the muddier bits to the portacabin. Big Joe was on his own and, to Will’s surprise, gave a low whistle of appreciation when ‘Liza’ stepped into the cabin.
“Damn, girl, we don’t get women dressed like you coming here too often,” Joe said with a smile and bright eyes. “Might have better to dress in some old clothes, luv. Places like this are very dirty.”
Will glanced at a poster of a naked, busty redhead woman behind Joe and said, “I can see that. But trust me, I would never be caught dead in a dirty place like this out of choice,” Will said in a female voice screwing his nose. “My brother sent me to get some parts.”
The big black man nodded. “Oh, you must be Will’s sister,” he said, standing. “I can see the family resemblance now. People around here call me ‘Joe.’ You’re Liza, right?”
Will nodded. He had a sudden urge to laugh but stopped himself. The old black man held out his hand, and Will shook it limply.
“I don’t have the parts here. I need to go remove them from a Caddy we got in this morning,” he informed Will.
“But my brother said they’d be ready to pick up.”
“Yeah, sorry,” Joe said, shrugging. “I meant to go do it earlier, but the phone hasn’t stopped ringing, and Frankie’s not here.”
“Oh, OK,” Will said and sighed.
“It won’t take too long. Besides, I just made some coffee. Would you like some while you wait? I also have some of my wife’s homemade cookies. They’re delicious.”
“Sure, why not.”
Clearing the couch of girlie mags, Will sits in a ladylike manner. The couch was very low, and he realized that the slightest parting of his knees would offer Joe a good view of his pink G-string/thong panties.
“How do you like your coffee?” Joe asked politely.
“Black, one sugar,” Will replied.
The black man smiled and went through a door to a small kitchen where he poured some coffee and got some cookies. What Will didn’t see was the big man crushing a Lasix pill and also putting it into the coffee. Will had his knees firmly pressed when Joe emerged from the kitchen area behind the office with a tray holding a mug of coffee and homemade chocolate chip cookies.
“This should hold you over while I go get the parts,” Joe said and handed over the goodies. “I won’t be too long, I promise. There’s a toilet in the back if you need to go. Make yourself at home. Oh, and I’ll divert calls to my cell phone so that won’t bother you.”
“Thanks, Joe. I’ll be fine,” Will said and drank some of the coffee.
*****
After finishing his coffee, Will was on his phone when he suddenly got the urge to pee. ‘Damn, coffee,’ he thought and got to his feet and headed toward the bathroom. The teen had been to the bathroom here before, and it always surprised him how spotless it was compared to the rest of the portacabin. He went in and dropped his panties to his ankles and started to piss, standing up.
He heard the sound of shuffling footsteps, which took his attention away from aiming his pee. For some reason, Will started to feel butterflies in his stomach. There was somebody on the other side of the wall, and he gazed at the hole that had the board covering it from outside. He had always thought it was just a hasty repair job and a board nailed over a hole from the outside. To Will’s surprise, the board suddenly disappeared, and the outside sun was shining through the hole.
Then to his utter amazement, a hard black cock poked through. It was the biggest he’d ever seen. As thick as a soda can and covered in large veins. It looked a good ten inches long. It was circumcised, and the chocolate head had a purplish hue as blood rushed through it. The thing throbbed in the air as Will stared wide-eyed at it—his little soft dick still peeing and pink panties around his ankles.
“Suck it, bitch,” a deep voice said from behind the wall. “Come on, don’t make me come in there and rape you.”
He grabbed his phone and texted his sister, ‘Kim, the toilet here has a gloryhole in the bathroom, and some black guy has shoved his cock in it and wants me to suck it. I think it’s Big Joe. What do I do?’
She text back, ‘Suck it then. It’s not the first cock you’ve gobbled, I’m sure, you sissy fag.’
He texted back, ‘But, I’m not into that shit. I like to know the owner of the cock I’m sucking.’
‘Then run out of there and never go back. God, I never thought I’d see a gay guy turn down a nice big cock.’
‘God, you’re a bitch. What did I do in a past life to be landed with a sister like you.’
‘Just suck it and stop whinging like a babydick-sissy. Why get that tongue stud if you’re not going to use it for what it’s for—cocksucking.’
The man suddenly shouted, “Come on, bitch. Suck it or have it ream your pussy.”
Will sighed and thought he might as well get it over with. He turned and sat on the toilet and started to jack off the cock with his hand. It was so hard. Wanting this to be over with as fast as possible, Will started bobbing his head up and down the shaft, swallowing about six inches of the slab of cockmeat into his mouth. It tasted sweaty and pissy and possibly like old cum.
“Mmmm, oh God! Fuck yes, swallow my cock, you eager little slut. If you keep going like that, I have a nice and creamy surprise for you in a few moments,” the man moaned, much to Will’s shock, making him stop for just a moment. “Oh, you’re one of those cockteasers, are you? Well, two can play this game. Judging from how eager you were to start sucking, I can tell you’re just dying for a nice big load of cum. So get back to it, or I’ll come in there and leave it in your pussy.”
It made Will rather uncomfortable, but he didn’t want to risk being ass raped, so he got on with his cocksucking.
“That’s it, baby. I knew you couldn’t turn down this juicy load I’ve been cooking up for you. Just keep going nice and steady, and it’s yours, you cum hungry slut,” the man moaned, his breath slightly sticking in his throat.
From the twitching of the cock in his mouth, Will could tell the stranger was getting off on talking dirty like this.
Several minutes later, the man let out a loud grunt, exclaiming, “Mmmm, here comes your tip, baby. You’ve earned every last drop of it.”
The black cock tensed, and it shot its load into Will’s mouth. Flooding it with his warm salty jizz. Will groaned softly, disgusted by the sticky, strong-tasting mess in his mouth, but at least it meant his ordeal was finally done. He forced himself to swallow the load the man had left. It made him shudder in disgust, but Will didn’t want to leave any evidence of this foul deed behind. While he sat there panting, the rapidly flaccid growing cock retreated through the hole. The rustling sound of clothes followed it, and then only daylight shone through the hole in the wall.
*****
Will was about to get out of there when the urge to pee struck him again. ‘That’s weird,’ he thought. ‘How could I have any piss left in there?’
Since he was sitting, he just let it rip, pissing like a girl. Without another word, the man had just left after depositing his load. Not that he wanted to hear any more from him, but it made Will feel even more used. The stranger really hadn’t lasted long, much to Will’s relief, and the sissy was determined to get out of there as soon as he stopped peeing.
If he ever stopped peeing.
Sitting back, he couldn’t quite come to terms with the fact that he had really done this, yet with his location and the taste of cum still strong in his mouth, it was hard to deny. Then, he gasped as another hard black cock slid through the gloryhole. This one was bigger than the first (Maybe twelve inches), but it was cut with a dark reddish head. It shocked Will way more than that first cock had. For a moment, he considered just leaving and never coming back. But he was a little horny now, and those thoughts took over.
Will turned to the cock and asked, “What do you want?”
“Uhm, oh well, I uhm guess you could just deepthroat it. If you can do that, it would be fucking fantastic. Barely anyone ever does that to me. Well, I guess I can’t blame them,” came a deep rumbling voice from the other side of the wall.
Maybe this process would be less drawn out than he had expected. What this guy requested was pretty much the same thing he had done for the other guy, except that deep-throating this cock would prove a bigger challenge simply because it was, well, bigger.
“As you wish,” Will answered obediently.
The sissy then knelt in front of the cock, which was only semi-erect, and wrapped his lips around it, gently going up and down its length until it grew fully hard. While this black cock was certainly washed as well, it did have a way more distinct smell and taste than the previous one. It was a taste and smell that was even more disturbing to Will than that of the previous cock.
Despite that fact, Will dutifully bobbed his head up and down the length of the shaft, gagging lightly each time he took it all the way down but managing quite well, considering the size of this thing. As far as blowjobs went, this was probably the most enjoyable one he had given in a while. Simply because, apart from a few moans and grunts, it was the least interactive one. It was way better just to be able to suck and get it over with than to have to hear dirty talk or even praise about something he wasn’t proud of at all.
On the downside, this guy lasted way longer. It took a little over ten minutes and a sore jaw before the cock finally tensed up, and the guy deposited a large load of cum in his mouth. Pulling off the cock Will swallowed all the cum down.
“Hot damn, girl, you certainly do know your way around sucking cock. Not many people know how to deepthroat my cock, and that tongue stud also felt just amazing. I certainly do hope to find you on the other side of that wall more often,” the guy said in his deep voice as he zipped up his pants and left.
Will didn’t know how to feel about this. One thing was for sure though pride was not at all what he felt after hearing that he could deepthroat bigger cocks better than most. A pro cocksucker was the last thing he wanted to be called.
A new cock appeared.
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