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Motel Fun for College Crossdresser

A young college student enjoys a girly getaway at a nearby motel.
Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and the other facing the pool/park area. 

Thursday night, most college students are getting ready to party, Jeff on the other hand was packing a duffle bag, bookbag, and changing into sweatpants and a hoodie. He calls a taxi to pick him up in front of his dorm and take him to a nearby motel. The front desk attendant is helpful and quickly rents the room to the boy.

He walks in and is not surprised to find a somewhat depressing room, but he knew what he was getting into. You get what you pay for, and if you pay 70 a night then you better not expect a lot, but the best he could afford as a college student. So he makes the most of it, and prepares for his night.

Jeff is 5'5, tan, and skinny. But not in the way that most boys are skinny and lanky, just skinny. He considered this lucky because it helped him create the illusion of a woman.

So he starts by rolling a blunt, and playing some girly music on his laptop. It gets him in the mood, he quickly smokes the blunt and jumps in the shower. He shaves every part of his body. Legs, armpits, everything...he jumps out, still high, and covers his body in lotion to make himself silky smooth. He opens the bag to reveal the stash of girl clothes he's bought over the past months. Jeff's style is very sexy but fashionable, he is after all a young trendy lady.

He puts on his black Victoria's Secret bra and a cheetah print v-string with a hot pink lace trim. Usually it would be hard for him to control his erection, but the weed helps him relax. He pulls out a large bottle of rum and a mixer he got his hands on, even though he is a couple of years under the drinking limit. Jeff quickly makes himself a drink and slowly sips as he starts applying his makeup. He figures "why not go trashy?"

He goes for a smokey eye look, heavy lining under the eye, and puts on fake lashes, and some nude lipstick to keep it a little classy.

He slips on his new cheetah print dress, he's been looking forward to this. And a pair of black 5 inch pumps.

Finally he slips on the black straight wig...

Ashley has arrived.

She feels like the bad bitch she really is. She quickly gulps the last of her drink before serving herself another. After the long process is done Ashley is finally ready to get the fun started. She starts rolling up her next blunt and calls for a pizza to be delivered. She opens up the blinds to her room almost halfway, by now the sun has already gone down, but anyone can clearly see into the room through the large windows, but that's exactly what Ashley wants.

She hears a knock at the door as she is about to light the second blunt. Startled, Ashley almost falls, she nervously walks to the door and opens it to find the delivery boy carrying her pizza. He is not ugly but not handsome either, probably some boy from her college trying to make a couple of extra bucks.

Although Ashley has practiced her makeup, movement, and voice for a while now it is still clear to see she is a boy. 

He is startled, she grabs the pie. "Let me get the money." She goes over to her bookbag and grabs a tweny. In a burst of spontaneity she notices the notepad and pen on the bedside table and feels amazingly bold.

Quickly she scribbles:

"If you want another tip come after work, Ashley XO"

She wraps it around the bill to make it obvious and quickly goes to hand it to the delivery boy. "Thanks so much."

The boy, still in shock, says, "Uhh...no problem enjoy your meal," as he walks away in awe.

She enjoys her pie, blunt, and booze. An hour or so later she starts to get bored being alone and feels bold. She grabs a pack of cigarettes from the bag, her keys, her phone (just to be safe) and her lighter, and walks out the door into the center of the motel. She lights the cigarette and begins to walk around. Most of the rooms look empty, some of them are vacated, most people have their blinds closed and no one sees the sexy girl.

As she is reaching the end of her journey she sees a man walking in her direction. Immediately she freezes, maybe she was all talk, but before she can turn around and try to escape being seen she hears, "Excuse me!"

"Me?"

"Yeah, sorry young lady, do you happen to have a lighter I can borrow?"

"Yeah."

He comes closer, a 5'8 man fair skin with some stubble, and she gives him the lighter. He lights his cigarette and inspects her, realizing she's not your average girl, as he hands her back the lighter.

"You look a little too young to be out here walking alone, specially dressed like that."

"Well, I'm all alone and I got bored so I decided to go out for a walk," Ashley says, or at least tries, but her nerves are getting to her and her voice is breaking.

"Oh I see, yeah I know how boring it can get, I was with my wife but she knocked out so I decided to go out for a smoke, maybe I can keep you some company."

Ashley smells the whiskey in his breath. "Sure, my room is just around the corner."

They walk to the room as Ashley's heels click and echo through the open space. She closes the door behind them, but doesn't lock it. 

"Been smoking some mary jane?"

"Yeah I love it, it relaxes me." Ashley turns up the music. "Uh want some pizza or a drink?"

"Listen little girl, I'm not here to play games, you're obviously a motel slut, get to it." He drops his pants to reveal a 5 inch semi hard cock.

"Ok let me get ready." Ashley's heart drops in fear and excitement, this is the first time any of this happened to her. Before it was just playing dressup, but now it was a whole nother level. She grabs her bag and goes into the bathroom. In one of the pockets she grabs a small baggy with white powder. She thinks to herself "This is the only way I'll have the courage to do this." Quickly she does 3 lines and immediately feels the rush. As she comes up she looks in the mirror and realizes "Holy shit, right now I'm not Jeff at all, I am ASHLEY, I am a bad bitch, I am a motel slut, and I'm gonna do what motel sluts do."

She walks out of the bathroom.
"What took you so long little girl?"

"Sorry I had to keep you waiting daddy."

"It's ok, how much is this gonna cost me?"

Ashley just realized what was happening and she loved it. "100."

He took the money and placed it on top of the pizza box. Immediately Ashley dropped her dress and spun around so he could see her entire body. 

"Damn youre sexy."

"Thanks, baby."

He started feeling her up, Ashley loved the feelings of his rugged hands on her delicate body. She turned around and bent over putting her ass in front of his face. "I taste like candy," she said as she looked back.

"I bet you do, baby." He groped her ass and smacked it quick before digging his face in her hole.

The feeling was amazing, like nothing she'd ever felt. His tongue darted in and out of her pussy and the slobber started dripping down Ashley's leg, she loved it. But she felt she was about to cum so she turned around and dropped to her knees.

"I'm so thirsty baby, are you gonna give me what I need?" the words came naturally to her.

"Yeah baby, do what youre best at."

She started by licking his balls, and worked her tongue up his shaft until she reached the tip. There she played with the head a little by twirling her tongue. All while she looked at him with the hungry eyes of a slut.

He moaned and as soon as he did she thrust her head down as far as she could to try to take in the now 7 inch thick rod. She bobbed up and down, slobbering, spitting, occasionally teasing. Jeff had watched so much porn he knew what the perfect blowjob was like. It was Ashley's time to use this knowledge. And as everyone knows: the best type of blowjob is a sloppy blowjob. His moans got harder and harder until he exploded in her mouth.

The first shot went straight down her throat. But this was her first time and it caught her by surprise so she backed away. This caused the rest of the cum to cover her face and drip down her mouth.

They both smiled at each other.

When suddenly they both heard a loud knock at the door.

This is my first try at writing a story, I hope you all enjoy it. Please comment.




Also if you guys enjoyed it and want me to continue, pick which door the knock came from: The main door or the door to the center of the motel. 


XO.

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