Dan grew up in Philadelphia, Pennsylvania under his mother's roof in the Northeast section of the city. Growing up, he wasn't' that bad of a kid; he listened to a mix of punk rock and grunge and loved to skateboard and play video games.
Even now, at twenty' five years old he still loved playing video games as often as possible. Around the age of twenty' three years old, he joined the sort of family business of working as a mechanic at his cousin Mike's garage. Cars were not exactly his kind of thing, but he had been in desperate need of a job and so his cousin took him in and taught him everything he knew about fixing vehicles of almost every kind.
He had never really had much in common with his father's side of the family at all growing up, but he was happy to have gotten to know a few of the people since he started working at the garage. One thing he did have in common with pretty much everyone on that side of the family was his love for alcohol.
He would openly call himself a functioning alcoholic, though he would go through brief periods of time in which he became bored with it and would slow down quite a bit for a few months before picking up again.
He loved everything from beer to vodka to rum to whiskey, whiskey and beer being his two favorite choices.
It was Christmas Eve; Dan had just woken up in his bed in the basement of his mother's house with a slight hangover.
"Great," he thought. "Christmas Eve and no one to spend it with,"
Sure' he had family, and it wasn't' that he did not love his family, but he had gotten tired of spending every Christmas without someone to hold. He had been single for three years now since his last girlfriend Melissa cheated on him after five years of going steady together.
Some felt that this one incident had really been what pushed Dan over the edge into his alcoholism, though no one really knew for sure what the real reason was.
He glanced at the clock noticing it was actually really' late, 3:30pm to be exact. He did not get very much time off from work, so when he did get it he liked to take advantage and sleep in as long as possible. Groaning, he rolled out of bed and stepped into the bathroom turning on the shower and then moving towards the toilet.
He emptied his bladder before turning back to the shower stall and climbing inside, letting the hot water wash over his body.
After cleaning up real good, he dried off and threw on some clothes before heading out the door to the bar across the street from his house. He stopped in the pizza shop right next door to the bar and got himself something to eat, before heading next door and starting his day of drinking with a glass of Jack Daniels.
By about 7:00, he was starting to feel pretty' drunk and' also a little on the horny side as well.
There were a few chicks inside the bar, one or two of which had been flirting with him on and off since they first arrived. He could probably hook up with one or even both of them if he actually started flirting' a little heavier back with them, but he was in the mood for something a little different.
There was thing that nobody knew about Dan; he wasn't' exactly the straightest Guy on the face of the planet. Sure, he loved women, he loved the way their skin felt the way they smelled the things that the right one could do to make you feel good; he loved pussy most of all.
What people did not know about Dan though, was that he also happened to like a nice hot chick with a big fat dick from time to time.
He had become interested in transsexual women when he was only a teenager, by freak accident really. He had been on the computer in math class at school, just turned the PC on to find the screen saver had been set as a picture of a beautiful blonde' with a huge boner.
Whoever used the PC in the class before him must have set it up as some sort of practical joke or something.
He had never quite been the same since that day, Since that occurred though, Dan had only ever been with one real transsexual when he was eighteen years old. He had called one of the numbers in the City Papers sex ad's' and met up with a gorgeous transsexual who had gone by the name of Samantha; they had really hit it off.
Samantha had known how to give one hell of a blowjob, and when she slipped her index finger into his ass and massaged his prostate at the same time that she was sucking his dick, that was more than enough to shove him over the edge.
It had been a little awkward at first when he realized that she happened to have a bigger than his, but it quickly became a bit of a turn-on. It had been so long since that encounter, and he had never done anything like it after that. He met Melissa and fell in love and that was that he was all hers and nobody else's and he liked it that way until she cheated on him.
He stumbled out of the bar and into the pizza shop again, swiping one of their free City Papers and walked back outside into the cold December air. He flipped through the pages and found one transsexual who called herself Daisy. She had short blonde hair and beautiful blue eyes and was actually really convincing to his surprise.
He pulled out his cell phone, dialing the number and after only three rings' he heard a click followed by a soft and very feminine sexy voice.
"Hi...is this Daisy?"
"Yes it is," she replied. "Who's calling?"
He cleared his throat, leaning back against the wall behind him,
"I'm Dan...I read your ad in the City Paper. Are you available right now?"
She chuckled and answered with a simple yes and the conversation progressed from there. They agreed to meet up at the motel right down the street from where Tom lived; it wasn't' very expensive for just one night. He went there right away to get the room, paid for it himself and told the guy at the desk if a woman named Daisy asked for him to just give her the room number and send her his way.
Once inside the tiny room, Dan sat down at the small table in the corner next to the window. He had brought with him a bottle of rum for them to split if she wanted some that is, and he was really looking forward to her arrival.
Finally, at 9:00 on the dot there was a soft knock at the door. He stood up and pulled it open to find the beautiful Daisy smiling at him; she walked right in and wrapped her arms around him, kissing him passionately.
"Your' actually pretty sexy," she said smiling.
"Thanks...I'm glad to meet you."
She shut the door and' locked it and glanced over at the table noticing the bottle of Captain Morgan spiced rum. She laughed and took a seat motioning for him to sit down as well. He sat across from her and smiled, as he poured two glasses of rum and handed one to her.
"So, I usually prefer my clients to pay up front...if you don't mind,"
"Sure, not a problem,"
He reached for his wallet and pulled out a $100 bill handing it to her. She slipped it into her purse, and took another sip of her rum, and the two started talking a little as they continued drinking. It wasn't' long before she had gotten up from her seat and planted herself on his lap with her arms draped around his neck. She leaned in and stole a sweet kiss and he groaned as he slid his tongue into her mouth tasting the alcohol on her breath.
Their kissing became much more passionate and soon she was sliding off' of his lap and undoing his belt and zipper, pulling his cock free from its' restraints and swallowing it whole. He moaned in pleasure as she took him straight to the back of her throat, bobbing her head up and down and flicking the head of his shaft with her warm wet tongue.
She was doing an incredible job, Daisy was very straight forward, not really finishing the blowjob as she pulled him off the chair and proceeded to tear off his clothing on article at a time.
She followed with her own clothes, tossing them all to the floor before giving him a light shove onto the mattress behind him and jumping on top. Their lips crashed together and he could feel the friction from their cocks pressing against one another as he groaned.
She straightened her back just a little and he leaned up, taking one of her tits in his mouth and sucking on it for a few moments while reaching down to stroke her cock at the same time.
She pulled away from him, turning around and moving into 69 position shoving her ass and cock right in his face as she continued sucking his dick. He leaned up, taking her into his mouth as well and now they were going down on each other at the same time. It had been so long since he had tasted a beautiful tranny cock, and he was' impressed by her size and the taste to.
She slid down some, releasing him from her mouth and grinding her ass against his cock for a few moments and he expected her to impale herself on him; he was anxiously waiting for her to do so. He wanted so badly to fuck her now, to shove his cock right up her ass and pound the hell out of her.
That wasn't' quite what she had in mind though; she intended to spend some time teasing him, making him want it even more. She would do so by pleasing herself first, and making him wait for his turn to have his way with her.
Dan groaned in frustration as she rolled off' of him and suddenly flipped him over onto his stomach, grabbing the lube off the nightstand and climbing on top of him.
She pinned him down with all of her weight, pouring a huge glob of lube all over his ass and rubbing it in nice and good.
Daisy grabbed hold of her massive prick and started rubbing it against his ass crack, she let go of it and started probing him while pinning him by the arms with both of her hands.
He groaned, pushing his ass up against her begging him to just put it in and fuck him instead of torturing him this way. Finally, she did just that, slamming all eight and a half inches of her thick rod straight up his hot tight asshole.
He gasped, digging his nails into the pillow and moaned as she started to pound him.
She moved so forcefully, the entire bed shook underneath of them as she pushed him into the mattress leaving a bit of an indent.
He could feel sweat dripping from her forehead onto his back as she fucked him like a wild animal, and he could feel that familiar sensation in the tip of his dick indicating that his orgasm was fast approaching.
He welcomed the intense explosion of pleasure as it finally overcame him and he could feel the warm sticky cum flowing out of his dick all over the sheets beneath him as his entire body trembled from the orgasm. Daisy continued pounding his ass, breathing heavy and sweating profusely as she began to near her own explosion.
"Ohhh fuck you're so god damn tight,"
He grunted as she began pushing deeper and deeper and he could tell she was getting close; just a few more seconds and she would be right there with him.
Sure enough, several more hard strokes and Daisy let out a squeal followed by a very low moan that almost made Dan want to laugh. He could feel her cock pulsating deep inside of him and he could feel the warm fluid pumping into him, filling him up and running out of his asshole and down his balls. She collapsed, exhausted on top of him and lay there for a few seconds, their bodies sticking together from a combination of their sweat.
Once she recovered from her orgasm, Daisy lifted herself up off' of him, pulling her dick out of his ass. Before she could get' out of bed though Dan rolled over and' grabbed her by the hips and flipped her over onto her back. She squealed again and started laughing as he leaned in and started kissing her all over the neck, the breasts and her belly.
She knew exactly what he wanted and she was more than willing to give it to him. He grabbed the bottle of lube and lifted her legs, pouring the liquid all over his throbbing erection and running his hand up and down the length.
He applied some extra to her asshole and set the bottle down on the floor before lifting her legs once again. He pressed the tip of his cock against her asshole and she reached both arms up wrapping them around him and smiling up at him as he shoved his cock right into her with one swift thrust.
She groaned, his cock pushing all the way in to the balls in one move and she dug her nails into his back digging and leaving scratch marks. He began thrusting, pounding her ass, the sound of sweaty flesh against flesh echoed through the motel room as she begged him to fuck her harder.
He did just as she asked, picking up the pace little by little, while sucking and biting at her neck leaving a pretty' big hickey in the place of his lips.
She was starting to get close, but she didn't' want it to end this soon and she knew that Dan did not want it to end this soon either. So' she pushed him off' of her, his dick sliding out of her ass and she rolled over onto her hands and knees sticking her ass up in the air for him. He wasted no time, mounting her and slamming straight back in, fucking the living hell out of her.
She made sure to get nice and loud; she wanted everyone in the motel to know that she was having some really' good sex right now, and it wasn't' exaggerated in the least bit.
As Dan felt his cock beginning to swell up his orgasm quickly approaching, he pulled out in a desperate attempt to hold it off a little while longer. To buy some time, he moved down some and buried his face between her ass checks, running his tongue up and down against her gaping asshole.
She gasped and moaned so loud he was positive whoever was in the room next door would hear. As he continued to eat her ass, he reached around grabbing hold of her cock and started stroking it nice and slow at first. Then he picked it up a bit,
He flipped her over and lay down on the bed pulling her on top of him and she got the message.
Sitting on his chest, she started stroking her huge cock right in front of him for a few moments, before sliding forward and shoving it down his throat making him gag. He swallowed every inch of it and savored the taste, inhaling the musky aroma as his own cock throbbed and ached, begging him to continue what he had been doing earlier.
She throat fucked him for about a minute and a half before pulling her dick free from his gullet and slid down, positioning her ass right above his own member and lowering herself down onto him. She loved the feeling of his dick sliding back into her where it had been earlier, where it truly belonged.
She began bouncing up and down on him now, holding her tits as she did and moaning and calling out his name in pleasure.
"Oh shit, yeah, fuck my ass Dan, fuck' my ass,"
He cock was flopping around, slapping against his stomach and her own as she moved up and down on him and he reached up taking it back in his hand and started jerking it once again.
She groaned, leaned in and bit his neck, sucking on it forcefully for a few moments before moving to his chest and repeating the same action leaving a huge hickey. That was enough to throw him over and he grabbed her hips, his entire body tensing up as he clung to her.
They managed to cum at the same time, both of them screaming in pleasure their bodies trembling and shaking fiercely. Her cock erupted, shooting a stream of thick white hot cum all over his chest and' face and only about three seconds later his own dick fired off deep inside of her asshole.
When it was over, she collapsed on top of him once again as she had done earlier, both of them drenched in sweat. The booze we're' beginning to wear off and they were both exhausted, worn out and ready to pass out at just about any given second.
Daisy rolled off' of him and collapsed by his side, he turned over and wrapped his arms around her and she pulled the covers over them both. They lay there, quiet and still for a few seconds before she reached over and clicked off the lamp on the nightstand, blanketing the room in pitch black.
Within minutes, Daisy had fallen asleep in Dan's arms and he was beginning to drift as well. The last thing on his mind as he slipped into a deep slumber was how great it had felt to do what he had just done with Daisy; he almost wished she wasn't an escort. He almost wished that by some miracle, they could actually be together in a serious romantic relationship.
He knew better though, this was her job even if she enjoyed doing it it was still nothing more than a job. They couldn't' be in a relationship while she continued sleeping with other men for money without him feeling some type of jealousy over it all.
He shrugged these thoughts off, pulling her closer to him and closing his eyes; he decided to just' enjoy what he had right now. Even if it was only for one night, he had found someone that he felt comfortable with; he wasn't' alone on Christmas eve for the first time in a very long time and that felt good enough as it was.