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 wa
nting 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.