The Traveling Crossdresser Ch. 03

The Colonel stepped out and lit a cigarette. He stood guard by the driver side door as the Brony got in. Like a true simp the Brony reached underneath Lily and tried to finger fuck her through her panties.

Lily moaned. This was the first contact her little dick had all night. The contrast between the pain made it feel incredible. She began humping his hand until she had a little three inch hard on poking through her panties.

"Find it?" the Colonel asked sarcastically. When the Brony shook his head no the Colonel replied, " Well either suck out my cum and fuck that cute little ass or get out so someone else can."

Disappointment of not being able to finally fuck a girl wasn't going to stop the Brony from getting off. He had swallowed many of loads at Fiesta. Tonight he would swallow a load from a cute little ass instead of a hairy old cock. Then the bonus was he was going to get to fuck an extremely girl-like ass. It wasn't perfect but it was better than usual.

Lilly felt a soft tongue massaging her inflamed asshole. It gently prodded its way in. The cool relief from getting rimmed had Lilly dripping pre-cum. As the Brony swirled his tongue in Lily's ass began to open up. She could feel the cum being hungrily sucked out of her. It felt so good. She wanted to reach back and rub her dick till she came. Unfortunately she needed her arms to support her upper body so the window wouldn't choke her. So instead of getting off; she agonizingly enjoyed the sensation of her butt being cleaned out.

Once the Brony got every last drop out. He undid his pants and pulled out his dick. Like most fat guys, his dick was a little on the short side. His belly fat absorbed a few inches. However his dick was as fat as he was. He had an upside down stubby baseball bat shaped dick. He had a little head that ballooned in to a big round shaft.

The Brony eased the tip in. Being stuck in the window meant Lily was not able to turn around. As she felt the tip slid in she thanked God that he was just another fat guy with a little cock.

"Fuck that slut! Don't make love to her." the Colonel barked as he put his cigarette out on the attendeant's ass. The Brony slammed his full weight into Lilly's ass the second the cigarette touched his. Lilly's ass went from being an inch open from the tip to being ripped 5 inches wide as the stumpy cock slammed into her.

Screaming at the sudden girth was all the motivation the Fiesta attendant needed to go wild. He began riding Lilly's ass like Rainbow Dash with a strap-on. Lily once again was immobilized by pain. The crowd outside her window cheered at her new found misery.

Lily had already sucked off most the guys outside her window. Most guys got tired of waiting and ended up fucking each other. Then when they were about to nut they would force their way to the front of the line and shove their dirty dick in Lilly's mouth. After they popped they would let whoever was face fucking her go back to his business. This allowed Lilly to finish off more guys with her mouth than with her ass. That and Daddy took forever to cum.

Now with fat dick fat guy up her, it seemed like the mob was getting a second wind. Lilly began crying uncontrollably and begging to go home.

The Colonel shut the driver side door and walked around to Lilly. "You want to go home? You want to quit? Then the deals off. Do you understand? Now tell me what you want."

"I want to stay, Daddy. Please let me stay. I'll be good. I promise." Lilly sobbed. The crowd almost seemed sympathetic to Lilly's plight... almost.

Cooler guy apparently got his second wind and got right back up on the cooler. Slapping Lilly hard against the face, he fed Lilly his cock until snot ran out her nose. The crowd went wild. A drunk guy with an empty fifth of Jack wanted to shove the bottle up Lilly's ass. A group of other guys wanted Lilly to come down so they could see how many cocks they could shove in her at once. Then some guy walked up to the the side of the truck and pissed straight up into Lilly's eye and all over the side of the truck. It was getting to be an uncontrolled mob and the Colonel knew it.

Walking back around to his side of the truck the Colonel opened the door and threw fat boy out. He unlocked the window and let Lilly bring her head back in.

"Tomorrow come to my office you'll get the contract from my Aide. I don't want to see you again. Do you understand?"

"Yes Daddy," Lilly replied. She had finally done enough to earn the contract. She was going to go back to her hotel room. Her head was dizzy as oxygen rushed back to her brain. She felt light headed and happy. She scooted over on the bench seat to be next to the Colonel. He wrapped his arm around her and told her she was a good girl. Lily was floating.

The Colonel told Lilly to spread her legs. Lilly nuzzled into his side and dutifully opened her legs. Grabbing the binky from the dashboard he licked it and then gently put it in Lilly's ass. It was a strange heartfelt gesture, that somehow comforted Lilly.

Lilly dozed off as the Colonel drove her home.

The next morning Will woke up early. His ass was on fire. An angry red line from the window adorned his neck. He quickly got dressed, packed and drove to the Colonel's office.

When Will arrived, the Colonel had yet to arrive. His Aide was at her desk.

"Congratulations, you got the contract. Colonel Hall is running late today. He told me to have your documents ready. Here you go. I have to admit, I didn't think you'd survive the Colonel's Forge, but you did. You are a tough little homo, but you're still a homo." Smiling she handed Will his paperwork and a tube of monkey butt paste.

Will took both and decided to make the drive home a non stop trip. He has had more than enough cock this trip.