Billy was 18. Well, 17 and a half but who’s counting. Ever since he could remember he wanted to run from this red neck town in the middle of bum fuck no where. The only place with any action in town was the truck stop off the highway. It had your standard diner, road house and facilities for all the drivers passing through to take a load off after a long day on the open road.
Billy knew all he had to do to escape that piss poor town was to walk down the road to the truck stop and hitch a ride going anywhere but here. So, after getting his backside beat one last time by his drunk step daddy, that is exactly what he did.
It was a decent sized place. As Billy walked over the hill he counted at least 50 semi trucks parked all facing the same direction, ready to pull out the minute the law allowed. One of those cabs was his ticket out of here he thought.
Billy was a skinny guy, 130 lbs. soaking wet, but he had a good build from mowing lawns all summer for spending money. In fact that’s how he realized he was attracted to other guys. One of the lawns he took care of was at the home of a smoking hot dilf just recently divorced because he got caught blowing truckers outside the road house by the sheriff.
One day he had invited Billy in for a drink after working all day in the hot sun. Billy couldn’t resist the offer and ended up getting a tall drink of something he hadn’t expected. The sexy older mans load down his throat. It had tasted amazing and ever since that day he had cravings for something more than this hick town could offer.
Billy walked past the handful of women smoking cigarettes by the entrance to the showers. He knew why they were there and it made him more confident in his plan. He slowed his pace and began to walk down the line of cabs, arching his back and craning his neck like he was looking for something.
Not 5 cabs down and Billy heard one of the cabs crack it’s window.
“You looking fer something boy?”
A white guy in his late 40’s with a bushy black beard looked down at Billy from his shining chariot.
“Just a ride out of here.” Said Billy.
The mans eyes narrowed. “Can you pay?”
Billy turned out his pockets and a crumpled up dollar fell on the ground.
The man laughed and asked “How far ya goin?”
“As far away from here as you’ll take me.” Said Billy.
“Well come on up, maybe we can work out a deal.” The man smiled with a big toothy grin.
Billy had always said he would do anything to get out of this town. Now he was getting his chance and he wasn’t going to blow it.
As soon as Billy hoisted himself into the cab he was hit by the smell of cigars and body oder. He liked it. It smelled like men in here. Billy jumped a little in the passenger seat when the curtain of the sleeper slid open and another man stooped into view. He was huge. At least 6’5” 300lbs. with black skin and bright brown eyes.
“That’s Bubba and I’m Ray”
“Who the hell is this?” Said Bubba. Looking down at Billy who was sheepishly taking in his new surroundings.
“Just a kid looking for a ride.” Said Ray.
“Well nobody rides for free” Bubba grunted.
“Don’t worry Bubba. We can teach him to drive stick. What’s your name boy?”
“Billy.” He said somewhat nervously.
“Well Billy, come over here. Your Daddy Ray is gonna teach you something today.”
Billy shifted over towards Ray. Bubba adjusted his sweatpants and made a low, almost inaudible moan. Ray grabbed him by his shoulders and pushed him down between his legs under the steering wheel. Ray turned the ignition and the truck rumbled to life. It made Billy’s whole body tingle feeling the engine’s vibrations. Ray began to pull out of the truck stop while at the same time unzipping his dirty jeans.
Billy already knew what to do but what happened next he did not expect. He tugged on Ray’s jeans and was slapped in the face with the biggest cock Billy had ever seen. It must have been at least 10 inches long with a set of balls the size of Billy’s fist. He could feel the heat radiating of it as it bobbed up and down in front of him with the rhythm of the road. It smelled delicious. Sweet and musky like the smell of the whole cab.
“Are you gunna just stare at it? Get to work. Don’t make me regret pickin’ you up.” Ray said roughly.
Billy held it in his hands and felt it swell. He leaned in close and opened his mouth.
“That’s it Billy boy. Open wide!” Bubba yelled playfully.
Bubba leaned down from the door of the sleeper and palmed the back of Billy’s head. His hands were huge. He forcefully shoved Billy’s head down on Rays cock, making his eyes water.
“That’s it Billy. We’ll teach you to drive stick yet!” Ray said laughing.
Ray’s cock was hard now standing straight up without Billy even holding it. Ray’s balls were right in Billy’s face and he dove in eagerly. Licking and slurping Billy imagined the massive amount of cum built up in Ray’s huge balls. As he sucked the balls he used both hands to pump Ray’s massive cock, squeezing it has hard as he could. Billy moved his mouth back to Ray’s cock. Opening his jaws as wide as he could. He opened his throat and let Bubba guide his head down. His throat stretched. Billy gagged but Bubba held his head down. He looked up at Ray grinning with pleasure and it made Billy feel good to know he was doing a good job. Billy slapped Ray’s thighs as he began to struggle to breath and Bubba let him come up for air. Ray’s cock was covered in slimy saliva as Billy gasped to catch his breath.
“You seem like you have done this before.” Ray praised Billy and Billy felt his skin blush with pride.
“Thank you! This is fun!” Chirped Billy from beneath the steering wheel. Billy happily wrapped his warm mouth around the head of Ray’s cock and began to flit his tongue around and around. The spit leaking out the sides of his mouth lubed Ray’s cock as Billy stroked Ray’s hard shaft. Ray moaned with pleasure.
“That’s it Billy boy, just like that. You’re gonna make me CUUUUMM!!”
Ray’s load shot out with so much force it made Billy flinch. He stroked Ray’s pulsing cock as more and more ropes of hot sticky cum flowed out of the head of his cock. Ray shuttered and moaned as Billy squeezed his shaft to get every last drop out of his cock. Billy’s face was covered in long ropes of cum that began to drip down his face into his eyes, nose, and mouth. It tasted so good, Billy began to use his fingers to wipe the cum into his mouth being careful not to miss a single drop.
“That was amazing!” Billy said excitedly.
“If you liked that, just wait until you take care of Bubba.” Ray and Bubba glanced at each other smirking.
Bubba grabbed Billy roughly by the arm and pulled him back into the sleeping compartment. He tore Billy’s shirt and ripped off his shorts saying. “You won’t be needing these anymore. Put this on.”
“But these are women’s underwear!” Billy said, startled by how quickly Bubba had taken control.
“I know. You’re gunna dress like Ray and I want you to dress from now on.”
Billy stepped into a crotchless leopard print leotard and raised the straps over his shoulders. Stumbling as the sleeper cab rocked and bumped down the road. It felt good. Billy felt his cock begin to harden as he looked around the sleeping quarters. It had padded leather walls with good lighting and a decent sized bed, big enough for two grown men and maybe three if they cuddled up close. At the head of the bed a pair of leather cuffs hung on a chain swinging from a metal loop bolted to the wall.
“Give me you hands.” Bubba said gruntingly.
He shoved Billy against the wall facing him and held both of his wrists with one hand over Billy’s head. One after the other Bubba bound Billy’s hands in the leather cuffs. He wasn’t scared. In fact it was kind of exciting. His mind began to race with ideas about what was about the happen and it made his cock stand at attention in the slutty outfit he was wearing.
“Does kinky stuff get you hard?” Bubba asked.
Billy nodded excitedly.
“Good. Now let’s see what else you are good for.”
Billy’s heart pounded as Bubba knelt in front of him on all fours and took Billy’s whole cock into his mouth, moving his tongue in a circular motion that made Billy’s toes curl and fists clench in the tight leather cuffs
“Ohhhhhhhhh.” Billy moaned. “That’s so good.”
Throwing his head back against the padded wall as Bubba rocked forwards and backwards as he sucked Billy’s rock hard excited cock.
“Your precum tastes sweet.” Bubba said with a smile. “I bet your ass tastes even sweeter.”
He picked Billy up like a rag doll with has muscular arms and flipped him over. Now Billy was on his knees with his hands hanging above his head. Bubba dove his face hard in between Billy’s ass cheeks. His stubble tickled as Bubba tongued Billy’s ass, milking Billy’s cock with his rough hands. As the spit from Bubba’s mouth dripped down Billy’s balls it began to lube his hard cock. It felt heavenly.
As fast as Bubba had turned Billy over he flipped him back again.
“Now it’s my turn.” Bubba said grinning. “Show me what you can do with this.”
Bubba pulled down his sweat pants revealing what Billy could only describe as an absolutely monstrous dick. It had to be the length of Billy’s forearm and at least as thick as his wrist. Bubba slapped Billy’s face playfully saying. “You ever suck a cock like this Billy boy?”
Instinctively becoming submissive in the presence of Bubba’s massive erection, Billy managed to sputter a “No…no sir.”
“Well there’s a first time for everything.” Bubba said bluntly as he grabbed Billy’s head and began to rhythmically push his head up and down on his huge black cock.
Billy opened his mouth as wide as it would go. The head of Bubba’s cock barely fit but he forced it far down Billy’s throat.
“We’re gunna stretch that white boi throat out.” Bubba said with mirth. Over and over Bubba pressed his weight against Billy’s face. His head against the wall, Bubba’s cock had no place to go but down Billy’s tight throat.
“That’s it Billy boy. Get that cock nice and wet because it’s going in your ass next.”
With Bubba’s balls against his chin and cock all the way down his throat Billy looked up at Bubba wide eyed and in awe. Was it possible? Could he really take this massive dick in his ass? I guess I don’t really have a choice, Billy thought. After what seemed liked an eternity, Bubba pulled back and let Billy come up for air. Panting and gasping Billy knew what was coming next. Pulling himself up on the leather cuffs binding his hands, he turned over and presented his skinny tight ass to his new master.
“Please be gentle. I’ve never been fucked before.” Billy pleaded.
Bubba shouted up front. “You hear that Ray. You picked up a sweet piece of virgin ass!”
Billy heard Ray laugh and prepared to learn what it meant to feel like a real woman. Bubba slapped his thick black cock on Billy’s ass and back. It must have reached at least half way up Billy’s spine. Bubba slid his cock under the sheer fabric of Billy’s leotard and jacked it, making it rock hard against Billy’s skin. He spit and used his fingers to massage Billy’s asshole. Bubba slowly slid one of his huge digits into Billy’s ass. “That feels so good!” Billy moaned as Bubba massaged Billy’s prostate. Billy’s toes curled and his cock began to leak with cum as Bubba moved his finger in a circular motion, loosening Billy’s eager hole.
“Here it comes Billy boy.” Bubba pressed the massive head of his cock against Billy’s asshole. Billy instinctively tensed. “Don’t fight it. That’s what makes it hurt.” Bubba said matter of factly. Billy breathed out and Bubba pressed hard. Billy’s head felt like it was going to explode. He was seeing stars as waves of ecstasy washed over his whole body. Bubba began pumping and grunting with the motion of the sleeper rocking down the road. The hum of the engine made the bed vibrate. Hunching and pulling Billy’s ass toward him Bubba’s hulking frame completely over powered any attempt Billy made to resist.
Billy’s hole stretched, his back arched. He felt every inch of Bubba’s cock sliding deep into his ass. Billy felt Bubba’s strokes quicken. His legs tensed against Billy’s thighs.
Bubba threw he head back “Here comes my load boy! Ahhhhhh!” Bubba’s cock pulsed inside Billy’s ass. Billy felt Bubba’s massive cock begin to pump a huge hot load of cum inside of him. It felt amazing to feel so full of cock and cum as Bubba jerked and moaned, balls deep, inside his new sissy whore. Bubba slowly pulled his throbbing black dick from Billy’s twitching ass. He spread Billy’s ass cheeks with has massive rough hands and said.
“Now push that hot seed out, let daddy see what a mess he made in that boi pussy.”
Billy squeezed his abs and felt Bubba’s hot cum drip slowly out of his ass.
“That’s so fucking hot. You loved getting you ass creamed didn’t you.” Bubba said satisfied.
“Yes sir, It felt like I was doing what I was made to do.” Billy said still dripping with Bubba’s load.
“Well from now on you going to do exactly what Ray and I tell you to do.”
“Yes master.” Billy said with a slightly feminine voice not quite his own.
“There’s a nice glory hole at the next truck stop with your name on it Billy boy. We’re gunna see just how much of a whore you really are.”
Billy leaned back against the padded leather wall, hands bound above his head, still in disbelief as to what had just happened. This morning he was just some nobody. Now he was dressed like a sissy whore and filled with cum. His dream had come true and this was just the start of his adventures.
Source: reddit.com/r/eroticliterature/comments/hbje85/truck_stop_fantasy_this_is_my_first_attempt_at