The Traveling Crossdresser Ch. 02

Will was exhausted after the fuck session he had with Maribelle in the bushes. (The Traveling Crossdresser 1) After ditching her, Will found a truck stop with a Motel next door, got a room and called it a night.

The next morning Will woke up early hoping to fuck a trucker or two before he checked out. Whenever he was in a strange city looking for stranger sex, Will always took the opportunity to get dressed.

Today he was going to be Lilli the Lot Lizard. He wanted to get fucked again. If he made a few bucks in the process, then awesome. If not hopefully he'd at least get fucked.

Will went through his dressing ritual. It was a sequence of events, but the process was everything. He hated rushing it. Sure he could throw on a girly outfit and a little bit of makeup, but then he looked and felt like a man in drag. The ritual was sacred. Shower, enemas, shower, shave, facial moisturizer, body lotion, liquid foundation, panties, tuck, bra, falsies, fake lashes, eyes liner, contouring, powder, concealer, lips, blush, eye make up, finish dressing, perfume, wig, pose. Maybe the sequence wasn't the best but this was his process. He had been working on it since he was old enough to steal his sister's panties and his mothers make-up. Over the years he added steps but this is what he liked.

At the end of the ritual Will looked and felt right. His small frame and attention to detail meant he was passable and seldom got clocked. He was a fashion train wreck today. Slutty is one thing. Slutty in a white trash, pay me for sex is a fashion genre all its own. He wore white cotton girl boxers with pink hearts. These were almost covered by a black vinyl skirt that hung just over his ass cheeks. On top he went juggy. DD falsies in a dark red bra. A pink hello kitty belly shirt stretched tightly over the bra not even coming close to concealing the bra's color. He styled his wig into a high ponytail. Slipped on some heels and looked at himself in the mirror, instant hard-on.

Will could pass for an attractive athletic 30 year old woman. BUT a 30 year old woman in this outfit would reek of desperation. What trucker could turn that down? Will bent over and smiled as he looked back at himself in the mirror. He was going to get laid today. No, Lilli was going to get laid.

Fully dressed, Will grabbed his clutch and left his motel room. As he crossed the street to the truckstop he scanned the lot. He walked by several men. Unfortunately he got a lot of stares, a few cat-calls but no one approached him. Dejected he started to walk to the mini-mart to get a soda.

He was almost to the door, when a woman came trolliping over to him. She was a beast of a woman. She had leathery wrinkled skin, stringy blonde hair, thin lips with smeared red lipsticks, and clear empty green eyes. Her low cut blue dress hung loosely. It barely concealed her pancake flat breasts. At one time she probably had a spectacular bust, now two deflated balloons dangled off her chest. Her cheeks were collapsed giving her jawline a muppet like appearance. When she spoke her toothless mouth was explanation enough to her sunken face and appearance. Crack or meth had taken a serious toll on her appearance.

Her voice was raspy when she threatened Will, "Listen lady this lot is mine. If you have a problem with that you can talk to my boyfriend." Her boyfriend was standing a few feet behind her, dirty jeans and a t-shirt filled with holes and stains adorned his skinny frame. Although slight in build he looked strong and dangerous.

Happy about being mistaken as a lady, Will took an instant liking to the real lot lizard despite her threat. Smiling, Will replied in his normal voice, "I'm sorry, I didn't mean to disrespect you. In fact I was just looking for a little company. I got a room across the street. "

Her eyes lit up. "You're a dude! Well whatever gets you going. I'm Candy, because I'm so sweet. $40 gets you a quick blow or $100 if you want to fuck. Extras are negotiable, but you need to let me know what you want. We agree on a price before I go anywhere with you. "

"I was more interested in your boyfriend, than you... what's his rates?" Will inquired.

"Chad isn't a fag. He would never fuck a man. that's my job. So how about it? $100 and I'll finger fuck your ass while I blow you. You obviously want something shoved up there. "

"Tell Chad, I'll give him 300 to bend me over and fuck me. $400 if you watch. As soon as I cum you both can leave. "

Candy looked revolted, but $400 was a lot to walk away from. She wasn't exactly pulling in the clients, and it wasn't like Chad really did anything besides take her money. It be a nice change of pace for him to actually work. Still she approached him cautiously, with the request.

"Baby, see that girl over there? She offered to give us $400, but there is a small little thing... see... she is really a he, and he wants you to fuck him... He's kinda cute dressed like that, and I would be with you so it wouldn't be that gay. Plus you would be fucking him and everyone knows that only the person getting fucked is gay. "

"What the fuck bitch, I'm not a homo!" screamed Chad as he violently pushed Candy to the ground. He kicked her a few times for good measure and stormed towards Will. Will ducked into the store, hoping the store clerk would intervene or call someone if he started to get his ass kicked.

Chad was pissed. He had been passed around in prison to pay off his drug debt. He wasn't a fag then and he wasn't a fag now. Still he had been checking that girl out when he thought he was a girl. He even got a little hard thinking about that tight little ass. It was nothing like Candy's fat cellulite pock marked ass. Seriously, if a guy could ass fuck him in prison and not be gay, then he should be able to do the same and not be gay. Fuck it why not?

Chad opened the door to the convenience store and hollered, "You got a deal, let's go and get it done. "

Will walked out of the store and demurely greeted him. Chad tried his best to act nonchalant about getting to fuck Will. As he and Will walked towards the motel, Candy limped along a few paces behind them.

To break the ice, Will introduced himself, "I'm Lilli, by the way. Thank you for accepting my offer. I'm really ex..."

"I don't care what your name is faggot. I'm just doing this to get paid. I don't need to know whatever princess origin story you came up with, because the reality is your just a crossdressing fag, so shut up." Chad sneered. "Another thing keep your dick to yourself understand? I'm not touching it, sucking it, or fucking it. I'm not a homo. When we get to the room you're just going to be my fuck doll. Lay there and take it until I finish. "

Arriving at his room, Will opened the door and everyone came in. The three stood awkwardly at the foot of the bed. Chad already had a very visible outline of an erection on his jeans. For a straight homophobe Chad was awfully excited about fucking a man, Will thought.

Candy was feeling out of place, almost like a third wheel. Being uncomfortable, and wanting to break the silence she spoke, "All right we're all here. So before we get started how about that $400?"

Reaching into his purse, Will pulled out a wad of $20's, and placed it on the nightstand, "Its all there, you can take it when we are done." Will said. It is always risky paying a trick in full upfront. They could take the money and run. Still,it was a non issue; if they wanted to rob him, Will really couldn't stop them. He wasn't going to call the cops and explain the guy he hired to fuck him while dressed as a woman robbed him. Candy seemed to be thinking the same thing. Grabbing the money, she darted for the door.

To her surprise, Chad didn't follow. He was the one who taught her to grab and go from dumb Johns. Time is money and most Johns at a truck stop are just passing through; one time tricks. But there Chad was pants around his ankles, waiting to get blown by some dude in a dress. Did he really want to fuck this guy? What is he some kind of homo?

"Where are you going?" Chad hollered at her, "Come strip and dance for me. I'm going to need some motivation if I'm going to fuck this fag." Motivation, what a joke, Candy thought. Chad was already rock hard and dripping pre-cum. What a fucking homo. Still not wanting to get beat, Candy rejoined the group.

Pulling her floppy tits over the bust line of her dress, Candy began to sway to imaginary music. She turned around and lifted her dress and began to twerk. Her fat ass tightened as she bent over. Her cellulite dimples smoothing out making her ass seem a little less revolting as it bounced. Looking back at Chad, Candy realized he wasn't even paying attention to her. His eyes were fixed on the little fag boy in front of him. Unbelievable, Candy thought as she stopped and sat down on a chair by the bed. She couldn't believe that Chad was so into this guy.

By this point Will had been pushed to his knees in front of Chad. Chad's erection was right in front of Will's nose. It stank. Will was already gagging and the cock wasn't even in his mouth. Reaching into his purse, he pulled out a baby wipe and wiped down the narrow shaft. Next he worked on cleaning the bulbous mushroom tip. It looked comically large on the slender shaft, almost like an open umbrella. Will looked at the baby wipe it was dark brown with some yellow crust... maybe another wipe down with a fresh wipe, Will thought.

"Quit, playing around and stick it in your mouth slut!" Chad commanded. "You can clean it with your tongue, I haven't got all day, Candy needs to get back to work."

Having lost himself in cleaning, Will was startled. He looked up at Chad with a surprised look on his face, and dutifully opened his mouth. His jaw stretched as he tried to get the tip in. The tip must have been 6 inches in diameter at the widest point, Will's eye watered as he tried to fit it all in. Once the tip was in things were easier, Will could relax his jaw quite a bit. The shaft was at most only 3 inches around. Chad began using his cock like a plunger. His tip scraped the saliva from every part of Will's mouth adding much needed lubricant to the face fucking. When pushed all the way in, Chad's bulbous tip just reached the back of Will's throat.

Will fought the urge to gag as his uvula bounced on the tip of Chad's dick. The throat tickle was too much tough, and he pulled off gasping for breath. Not pleased, Chad slapped Will hard across the face, and rammed his cock back into Will's throat. Chad held Will's head down on his crotch, Will began to flail his arms trying to push off and create space to breathe. Will did his best to maintain eye contact while choking on Chad's dick. Tears streamed down Will's face. Laughing, Chad just pushed down harder on Will's head. Long strings of drool oozed out of Will's mouth as he tried to open it wider to breathe. Finally Chad pushed him away. Splayed out on the hotel's floor, Will's little nub could be seen poking through his panties.

"You liked that didn't you faggot? Candy, look the little faggot has a little hard-on, " Candy glanced up disgustedly from her phone at Chad's remark, and thought to herself, "And so do you."

"Hurry up and fuck him so we can go, baby," Candy implored. Chad looked at Candy's disgusted face and realized the full impact of the situation hit him. He was fucking a dude in front of a crack whore, and the bitch thought she was better then him. She needed to be put in her place.

Walking over to her, Chad grabbed a fist full of her hair and dragged her screaming to the bed. He threw her face down onto the bed. Grabbing the edge of the sheet he wiped any spit Will night have left on his dick. Spreading her legs, he unceremoniously rammed his dry cock into her flabby ass as hard as he could. Candy screamed louder as his unlubricated cock ripped into her asshole. Chad pushed her head down into the mattress to muffle her screams. Pumping away mercilessly he whispered in her ear," This is pleasure. I'm straight. Fucking girls and making girls scream is pleasure. That faggot over there is business. Business! Do you fucking understand?

Candy muffled a yes into the mattress between sobs. Once Chad got his answer he pulled his dick out of Candy so he could get to work. Turning his attention to Will, Chad grabbed him from the floor and placed him on his back by Candy.

Chad looked down at Will, and something changed. The body before him looked very feminine, if you ignored the little dick that was just poking out of the top of his panties. Will's balls even pressed up against his body created the illusion of a camel toe. He looked much hotter than Candy. His tear streamed eyes looked up at Chad waiting for what was next. It reminded Chad of the way his first girlfriend looked his first time...

Chad's first girlfriend was a quiet girl. She didn't like giving head, but since she didn't put out it was a necessary evil. Chad had been with her for a few months and was growing tired of the endless blowjobs. He wanted pussy. One day he face fucked her hard. Crying she begged him to stop whenever she could pull away. The only way he would stop he told her was if she gave him something else to fuck. She gave in and told him to at least be gentle. Chad remembered her teary eyes looking up at him innocently as he ears into her. He lost his virginity to that day. Will's eyes reminded him of her. Will really did have beautiful eyes.

Will eyes were looking demurely up at Chad. His point of view was very different then Chad's. Chad's just dry fucked a crack whore up the ass. His penis was now glistening with whatever body fluids Candy's ass had torn out of it. "C...C...Condom," Will stuttered.

"No way, I'm going to breed you, fag boy. But don't worry. I'll be gentle and treat you like a lady. Candy! Come clean up this mess you made on my cock. "

Candy plopped off the bed onto her knees. She dutifully began swallowing Chad's dick and all the vile excrement on it. While she worked, Chad leaned over her head and pulled Will's panties down to his knees. Lifting Will's legs up have Chad a perfect view of a tight ass with an even tighter hole. It looked delicious.

Chad couldn't help himself. He dove in tongue first. He licked the edge of the sphincter, which soon turned into tongue fucking Will's tight hole. Then he slipped in one finger, then two. Chad was so turned on, he could feel himself preparing to nut inside Candy's mouth. Irritated at the thought of finishing before he could fuck such a nice ass, Chad pulled his dick out of Candy's mouth and slapped her hard across the face. "Bitch, that's enough. Rub my shoulders and nibble on my neck while I fuck this slut."

As Candy stood up to comply, Chad began lining his mushroom tip up to the plate. He eased it in and stopped. seeing the discomfort on Will's pretty face, Chad spit on Will's asshole for a little extra lube. Slowly working it in and out, he gave Will time to get used to his size.

"Hurry up and fuck that fag!" Candy begged. Her hands were cramping up and Chad was acting like he was making love to this guy. He was never this gentle with her. Shit minutes ago he a ripping her a new one.

"Shut up bitch!" Then looking at Will he asked, "Do you like that, girl? I can go slower if you need me too. Lilli...right?"

"No harder please. You feel amazing." Lilli cooed in her most feminine voice. Rolling her eyes Candy sarcastically echoed Will, "harder please." Chad looked back and shot her a threatening look. Candy looked away and resumed rubbing Chad's lower back. Did he just call Will...Lilli?

Picking up the pace, Chad lifted Lilli's slender legs over his head and placed them on his shoulders. Her panties bounced off his neck with every thrust. Now that his hands were free he reached down and placed them on her hips. His thrusts became more forceful as he pulled Lilli's hips in to meet his. Lilli began to ooze pre cum all over her belly. Chad gingerly wiped it up with a finger and brought it to Lilli's lips. She leaned forward never breaking eye contact with Chad, and licked her pre cum from his finger. A strand of cum trailed from his finger to her lips.

Chad leaned forward and licked the cum off Lilli's lips before passionately kissing her. Lilli grabbed his ass to pull him in closer and began swirling her finger just outside his anus. When Chad began thrusting again, Lilly maintained pressure right on top of his hole. With every back stroke Chad began to impale himself on her finger. At first it wasn't much penetration, but each time he pulled out he pulled out a little bit further and her finger went in a little bit more.

Getting finger fucked reminded Chad how much he actually loved getting passed around in prison. He had been incarcerated on a minor felony, so he was assigned to a run instead of a cell. When his debt and subsequent stealing to pay the debt became too much, the other inmates on his run made him run a cock gauntlet. He serviced 13 cocks on his run that night. Every single one of them fucked him hard in the ass. At first it hurt, but after a few loads got dumped in him he began to enjoy it. The last two guys even double penetrated his ass. After that night he was nothing more than a prison bitch. Anyone on his run could fuck him. He couldn't sell his ass to pay his debts anymore, it was officially free. Fortunately being a prison bitch has perks. Every straight inmate would give him gifts, drugs and commissary to get him to come around. He was a pampered slut without a care in the world. He grew his hair out, used drink mix powder for lipstick and blush, shaved his body, and went to work. He loved his time in prison after that. Now he loved Lilli's finger in his ass.

Candy noticed Lilli's finger as well. She noticed Chad thrusting harder coming out onto Lilli's finger then when he was pushing in. Chad was a bitch and after tonight he would be her bitch.

Candy stopped rubbing his back, instead she reached down and spread his ass checks apart. Lilli's finger slipped out in the process. Chad looked back to see what happened right as Candy slipped two of her fingers into him. She hooked her fingers and found his prostate before he could say anything... This wasn't her first rodeo after all.

Chad moaned with pleasure. Not a masculine moan, a girly moan from being penetrated. Candy stood up and whispered in his ear, "Do you like that baby?" Chad moaned again in response and began grinding on her fingers.

"Say you like it baby... Say you like my fingers... Say you like my fingers in your ass... Say you like things in your ass..." Chad did his best to repeat what Candy had said but between fucking Lilli and getting finger fucked himself he was having a hard time forming words.

Candy took her free arm and slipped it around his neck into a chokehold. This pulled him down to her height and forced him down harder onto her fingers. "Play time is over Hun. Tell me what you want me to do with these two fingers." Candy demanded as she wiggled them inside of him.

"I want you to fuck me with those fingers. I want you to fuck me in the ass with those fingers!" Chad exclaimed as he gave up fucking Lilli and began fucking Candy's hand for all he was worth.

"Two fingers don't seem like enough for you. I bet you want more. Do you want me to give you more? If you want more tell me what you really are. Tell me how many inches you want." Candy teased.

"I want more. I want more. I'm a size queen loving Cheetos ass bitch. Please give me more Candy." Chad exclaimed.

Pushing Chad's head down towards Lilli's cock. Chad opened his mouth without being told. He eagerly began sucking Lilli off. Her tiny little dick being taken in by Chad's mouth easily. Lilli smiled at the change of events.

"Both you boys be good. I'll be right back." Candy said as she disappeared into the bathroom. in only a few minutes she emerged from the bathroom holding a toilet plunger who's handle was covered in lotion.