The Traveling Crossdresser Ch. 03

Today was the day for Will's big meeting. He felt like garbage. The last two days had been rough. He had traveled from Arizona to El Paso Texas in three days. On his first day of travel he and a hitchhiker had an orgy in the bushes with a trucker and a business man. Afterwards he got a room for the night. The next morning he got fucked by a pimp while his crack whore watched. After that he finished his drive to El Paso and got a room for the night.

Will was exhausted when he woke up. He should have arrived a day earlier and had time to prep for his meeting, but his escapades set him behind. So now with his meeting only a couple of hours away, all he could do was get dressed and travel to COL Hall office.

Will laid out his suit on his hotel bed. Nothing pretentious. It was a basic black suit with a white shirt and a dark red tie to make it pop. After laying out his suit, Will went to the bathroom to shower and get ready.

It had been a few days since Will had removed his body hair, and stubble was starting to show. Prior to jumping in the shower, he applied some depilatory cream to his entire body. Once applied he waited a few minutes before jumping in the shower and wiping it off with a hot wash cloth. Once his body was smooth he finished showering and got out. While he shaved his face he tried to go over reasons why his company should be the vendor COL Hall picked. It was hard to concentrate though. His mind kept going back to yesterday. In a strange turn of events, Chad the pimp he paid to fuck him turned into Candy's cock whore at the end of the day. Maybe every guy just needs a "little deep dicking."

Leaving the bathroom, Will looked at the suit laid out on the bed. He knew he was about to crash and burn. Maybe a little luck would help. going into his duffle bag he pulled out his lucky lingerie. It was a dark red silk thong and bra set. It actually matched his outfits tie quite nicely. He put them on and looked at himself. From behind he looked totally hot. His ass as small but hippy enough to pass for a fit 20 year old's ass. His shoulders were narrow and with the right wig any guy would get hard looking at his silhouette.

The dark red was a problem though it could easily be seen through his white collared shirt. Will slipped on two T-shirts to hide the color. For the most part it did the trick. Will figure he would keep his jacket on during the meeting just to be on the safe side.

Dressed and as ready as he was going to be Will left his room to head to Ft. Bliss. Walking out of the hotel Will was hit by a wall of heat. It was only 9 o'clock and it was 95 degrees outside. He hurried to his car and cranked up the AC.

By the time Will reached Buffalo Soldier gate, he could already feel a pool of sweat on the small of his back. The AC was going full blast but it was still hot. Pulling onto base Will followed the directions given to him. Military bases don't use street numbers. They use block numbers and Will got turned around a couple of times but finally found the building a few minutes before his appointment. Running from his car to the office building to avoid being late Will managed to find the room upstairs with 3 minutes to spare.

He approached a Soldier at a desk positioned near the door. "I'm Will Hamlett. I have a 10 o'clock appointed to see Mr. Hall," Will stated breathlessly. The run from his car into the building had Will pouring sweat from the desert heat.

"You're late. An appointment at 1000 starts at 0945. If you want to work with the military you need to learn military etiquette. Also it is COL Hall, not Mr. Hall. Please be seated. I'll let the Colonel know you have arrived. Also there is no AC in this building! feel free to downgrade and take off your coat if you need too. It is hot. I would hate for you to be late and a heat CAT." the Soldier replied. She was a small short Soldier. Her top was removed because of the heat. Her breasts didn't even make an outline of a bulge on her Army T-shirt. For such a very small girl she had a very big attitude.

Before sitting down, Will started to remove his jacket. Halfway through taking off his jacket he noticed to his horror that his shirts were all sweaty and sticking together. It may have been in his imagination but he could swear he could see the red from the bra staring to peek through his white shirt.

Panicked he decided he would find a bathroom and take off the bra. As he approached the female Soldier to ask where the bathroom was, COL Hall stepped out of his office. "I'll see you now. Please come in."

Hot, sweaty, and completely flustered, Will entered the Colonel's office. Once inside they shook hands and did the normal greetings. The greetings ended with the Colonel ordering Will to take off his jacket and have a seat. Will protested, saying he was fine. The Colonel would have none of it. He went on a rant about it being 100 degrees in this building and he wasn't going to allow a visitor to fall out because of business jacket.

Will removed his jacket and tried to fluff out his white shirt to help conceal the red. He wasn't sure if it worked, but it was the best he could do.

The Colonel started into the meeting as soon as he sat down. Will was barraged with questions in rapid succession. Ranging from estimated costs, to issues and discrepancies with contact terms. Will answered about half of the questions coherently with yes or no answers but faltered on follow-ups. Basically he bombed.

When the Colonel finished his interrogation. He politely thanked Will for his time. He was in consideration for the contract along with two other vendors. The Colonel had already met with the other two vendors and they were more prepared and seemed to have a better grasp on what the military was looking for. Still due to regulations Will's company would still be considered.

Will thanked the Colonel for his time. Gathering his things to leave, the Colonel stopped Will as he bent over to pick up his jacket. Resting his hand on the small of Will's back, the Colonel asked," Well, well what do we have here?" His finger hooked underneath the waistband of Will's thong. Lifting it about an inch, the Colonel let it go with a snap.

Mortified at being discovered, Will froze bent over as the Colonel fingers traced up his spine to his bra. Colonel Hall played with the bra band when he came to it. His free hand now cupping Will's butt cheeks.

Leaning forward to whisper in Will's ear, "Maybe, I should give you a second chance to make a better first impression. Would you like that?" asked Colonel Hall as he squeezed Will's ass. Will looked back at the Colonel trying to come to terms on what was happening.

Colonel Hall was a fit but lanky old man. Easily 6 foot. He wore glasses with round lenses that accented his square jaw line. He probably weighed 170 at most. His uniform t-shirt hung from his broad shoulders. His gray chest hair protruded slightly from the neckline of his t-shirt. His uniform pants were snug and hugged his hips. He was obviously going commando today. The outline of a monster semi erect penis was pulling at his left side pant leg. "I would do anything for a second chance," Will replied as he began to grind his hips on the Colonel's hand.

"Good girl. Put your jacket on and leave your room information with my aide outside. I will pick you up at 2200. Don't be late. Also I have a reputation as a tanker to protect. Don't show up looking like some fag drag queen. If you don't pass, I will. As in I will pass on you, the contract, and any future opportunities. Are you tracking?" the Colonel asked.

"Yes sir!" Will answered.

Will collected his things and left the Colonel's office. As he walked passed the female Soldier's desk he stopped to give her his information.

"You're giving me your hotel information. That can only mean one thing. Listen, I've been the Colonel's aide for a few years now. I don't approve of his extra-curricular activities, but whatever. Just remember you're not the first to go on this rodeo. Word of advice...pre-lube. He likes it dry and won't even spit. Your welcome, fag boy."

"Thanks," Will stammered as his ears turned bright red at the advice. What was going on? It was as if everyone could tell he was a sissy waiting to be used. He walked back to his car and drove to the hotel.

Flopping on his hotel bed, Will though about his day. He completely bombed his meeting with an Army Colonel to secure a government contract. At the end of the meeting the Colonel noticed his red lingerie. That same Colonel offered him the contract if he went on a date with him tonight dressed up. The Colonel's Aide somehow knew what was going on and told him to pre-lube. So far things couldn't be going better.

Will started his dressing ritual at 1900. Three hours to get ready was more then enough time. Actually 2 hours and 45 minutes. After all if you aren't 15 minutes early you're 15 minutes late. Will was really getting into playing Soldier now. He was determined to be ready to blow by 2145.

The outfit Will decided on was passable yet accessible. He put on a high-waist black G-String. He slipped on some back zippered jeans over the panties. A skirt might have been more accessible, but now-a-days more passable is female cut pants. He picked a black bra with b cup falsies. He didn't want anything too big, but he still wanted noticeable and feminine. The top was a crop top softball jersey that exposed his midriff. Then to pull it all together he pulled his wig's long blonde pony tail through the back of a trucker's cap. His pony tail went down to about the bottom of his shoulder blades and swished as much as his falsies jiggled. He loved the look. He looked like a lipstick lesbian about to go get balled out.

Sure enough at 2145 there was a knock at Will's door. Opening the door Will saw the Colonel standing before him in what appeared to be a baggy hoody and some basketball shorts. He was still very obviously going commando. His cock was hanging on the left side and went halfway down his thigh. Impressive, which is why he probably didn't try to hide it. As they both sized each other up, Will invited the Colonel in. "Sir, please come in. We can get out meeting started once you are comfortable."

"No, no, no little girl. We are going out to the drive-in tonight. When we get there you will do whatever I tell you. Failure to follow my orders will result in our re-negotiation of this mornings contract being void. Also I do not want to advertise I am military. Call me Daddy, and do you have a name you want to be called little girl?"

"Oh yes daddy, you can call me Lilly." Lilly replied over-enthusiastically. In reality she was a little disappointed. She was hoping for some freaky Soldier sex with G.I. jewelry to wear and a dominating Officer to serve all night. Instead it sounded like a pretty vanilla night of a giving head in a drive-in.

Daddy led the way to his car. It was actually an extended cab truck with a short bed and tinted windows. The kind of truck that screamed Dad with kids, not cowboy roughneck off-roading thrill seeker. Lilly was getting more disappointed by the second. Oh well, at least she would get the contract.

Sure enough, as soon as Daddy started to drive, his cock came out. It was huge. Halfway down a 6 foot tall man's thigh is about 7 inches flaccid. He had old man balls too. Big kiwi size nuts covered in gray pubic hair. "Get to work" he ordered.

As Lilly began moistening the 7 inch dong with her tongue and thought, "Well at least if he nuts on the way to the drive-in. I'll get to watch the movie. I wonder what's playing. I hope he gets Popcorn and Junior Mints."

Lost in her own thoughts she didn't realize that Daddy wasn't just a shower. He was also a grower as well. Daddy had a big daddy dick of just over 11 inches. He also was in fact a daddy. In between the seats Lilly found a binky. She threw it on the dashboard to get it out of the way.

After about 15 minutes of sucking Daddy off, the truck turned off the road. It hit a bump and the lightening became more prominent. Thinking they were at the drive-in Lily tried to get up out of Daddy's lap so the attendant wouldn't see her sucking dick when they paid the entrance fee.

"Lilly, Did I tell you to stop? I don't think so keep going" Daddy demanded as he forced her head back down. The truck began to slow. Then it stopped underneath a street light. Daddy pulled out a couple twenties in his left hand, and bell rung and then nothing. Daddy held Lilly's head in place with his right hand and began thrusting all 11 inches into her face.

Lilly gagged at the facial assault. Spit and saliva steamed out of her mouth and nose with each thrust. Her eyes watered. Her arms pushed at Daddy's right hand, trying to move it so she could breathe. He was too strong gasping for breaths in between thrusts was all Lilly could do.

During the struggle, the drive-in attendant appeared. Looking in the car the attendant asked "Is she okay? Miss, are you okay?"

"She's fine. Here's $40. Keep the change. Are we good?"

Technically by the theaters standards, they were good to go. The attendant however was a pervert. He wanted to see the whore's face who was getting force fed such a big dick. Once again he repeated, "Miss are you okay?"

Daddy released his grip on her head. Lilly looked up. She saw a fat dirty looking middle aged man wearing a "My Little Pony" shirt, cargo shorts and sandals by the driver side window. With her lipstick smeared, mascara running, and an eye lash falling off, she replied " I'm fine. Really I am."

What the heck was going on? Was the Colonel trying to end his military career by getting them both arrested for indecent exposure? To Lilly's surprise the Brony acknowledged her response and waved them through. The road went forward a for about 20 meters before veering into a sharp left turn. Daddy pulled the truck forward away from the attendant and stopped. Flipping down her mirror visor he told her she had 5 minutes to fix her face and then we go in.

Lilly was confused. Still following orders she began fixing her make-up as fast as she can. While working she managed to ask where they were and what was going on.

"Little girl, you are at El Paso's famous Fiesta drive-in adult theatre. That's right as soon as we make that left you will see huge screen playing porn. If that isn't enough for you they have a gay theatre and a straight theatre inside as well as the standard arcade booths. Here let me turn on the radio so we can listen while you get ready."

Daddy had the station pre-set on his trucks radio. When he turned it on the cab was filled with what sounded like a girl begging for a guy to fuck her harder. Lilly couldn't believe it. Pulling out her phone she got on googled Fiesta's in El Paso. No joke there it was a historical blemish of a landmark. God bless, Texas.

Leaving the cab lights on, the colonel drove a spiral around the drive in parking lot, hugging the right side. This ensured every car he past saw Lilly's pretty little face. Men noticed... Daddy's spiral tightened to the center of the parking lot where he parked. Men from all over the parking lot began swarming his trucks like penis holding zombies from a porn parody of Night of the Living Dead.

Daddy locked the doors. He then ordered Lilly to get on all fours on his bench seat. When she complied her ass was facing him as she looked out off the passenger side window. Dozens of men stood outside her door. The majority had their dicks out and were slowly stroking off to her. The closest ones knocked on the window asking to come in or for her to come out. It was frightening and flattering all at the same time. Lilly knew if she went outside she would get fucked to an inch of her life. At the same time was that so bad?

Lilly heard the zipper from the back of her pants go down. The cool night air tickled her ass. She playfully shook her ass trying to entice Daddy to eat it. Tonight was going to be a fun night after all.

Then it happened...

Searing white hot pain. Lily's faced slammed against her window as she tried to pull away. Her face contorted as she howled in pain. The louder she screamed the louder the men outside cheered.

Pre-lube...should have listened. Lilly just took all 11 inches of Daddy's dick in one single thrust. Then before she could get used to it, Daddy just began jack-hammering away. Every thrust threw Lilly's head into the side of the car as she tried to create space between her ass and the dry dick violating it. She was either going to break the window or knock herself unconscious.

Daddy seemed to anticipate this. He began rolling down Lilly's window. Seeing an escape, Lilly decided a dozen horny guys would be better then a dozen dry inches. As soon as the window was far enough down she began trying to crawl out.

"Not so fast, slut!" Daddy exclaimed. Once Lilly's head was out of the window, he began rolling the window back up. Lilly was trapped in a glass guillotine. She tried in vain to roll the window down, but the bastard turned on the window locks.

Now she was stuck. Lily was terrified that if she struggled the window would break and slice her throat. So she tried to take Daddy's anal assault the best she could without moving. It hurt so much though.

Lily's head was trapped outside of the truck. The window was choking her and she was sobbing uncontrollably due to the pain. This meant to the dozen horny men outside the truck her mouth was looking like was literally salivating for cock.

Human ingenuity is a beautiful thing. Once the guys realized she was too high up to face fuck. They came up with a plan. They needed something to stand on. One guy volunteered his beer cooler. When he came back with it he was given the privilege of fucking Lilly's face first. The other guys formed a horseshoe of a line around the cooler. It was really quite organized of an affair. Guys at the end of the line even sucked off guys near the front just to keep them ready. Teamwork really does make the dream work.

Everyone was having a grand old orgy except Lilly. She liked it rough. She liked humiliation. She liked being used as a fuck doll, but she simply wasn't ready for this level of abuse. Daddy neglected to move her G-string off to the side. Every thrust of his cock tore her up inside while simultaneously giving her a horrible wedgie from the inside out. To make it worse the crowd outside took great delight in gagging her until she threw up. She was at the point of being semi-conscious and dry heaving as a result.

The cooler guy was the first guy to finish. He came right as Lily began to hurl on his dick. He held her mouth shut until she swallowed every burning drop of stomach acid and cum. The next guy had a Cowboy hoody on. He started in as soon as cooler guy got down. He was equally as rough. Fortunately he was soon tapped out by another guy who was ready to nut from getting a blowjob off to the side from a random dude. Before Lilly could swallow his load cowboy fan's cock was already back in her mouth. This rotation went on for about an hour. At which point Daddy finally came.

When Daddy came a torrential amount of cum filled Lilly's asshole. It felt amazing. Finally she had something to lubricate that monster dong going in and out of her. Her ass was raw. Daddy's big dick didn't stretch her out, it tore her open. When he finally pulled his cock out of her every inch seemed to ignite a burning sensation inside of her.

There was a rapping at his window as soon as Daddy pulled out. The pony boy attendant was standing there and wanted to be next. "If you want to fuck this ass you have to slurp all the cum out. This bitch doesn't deserve lube," Daddy told the Brony.

"I just want to fuck her pussy, if that's okay?" the attendant asked.

"If you can find it you can fuck it. Otherwise get a straw." laughed the Colonel.