Scene 5

Every step of Ramsey’s day had been worse than the last, he had seen what he looked like in a mirror hours ago, he knew what his thoughts were at what he saw and yet he still couldn’t help shifting his gaze almost constantly wanting to see if anyone had noticed the truth. No one had said a word about the Santa’s helper that was a dude in a dress, this was a good thing, he already wanted to crawl into a hole and never come out again with the shame that filled him, but that stroke of luck, if he could call it that, was corrupted. It was like his masculinity didn’t exist. Every time Ramsey noticed someone’s eyes lingering on him too long he tried to brace himself for the fallout to begin, but every time, every single time it turned out to be a guy leering at him. The very idea of being checked out by another guy, being undressed mentally and worse it caused his skin to crawl.

That was only part of the problem, the outfit he had to wear that every girl who worked here had to wear wasn’t exactly made to handle cold. Not that it got cold in California where he lived unless you went up to the mountains, but inside the mall the air conditioning was always pumping out chilled air and the costume he had on did little to protect him from it. ‘No wonder girls are always cold.’ He thought to himself more than once as he moved about or his new role. At one point he was helping children up to Santa, then at another he was replacing one of the bags of presents for the children. Ramsey thought the little gifts were a good idea, adding something a little extra for the kids, the present he had been given he put back into a bag, having no use of some children’s toy, let alone one for a girl. It wasn’t like they were actually free, the cost was covered in the bill the parents paid for the pictures with Santa or so he imagined. Throughout all this he had gotten more and more used to walking in the green high heel pumps he had been **** to wear. Walking around on the balls of his feet, with little support changed the way he had to not just balance but move.

New strain on his legs and feet he wasn’t used to were taking their toll, making him feel awkward and clumsy, just more feelings he didn’t want to throw on the pile. Pain was also something he was having to deal with thanks to his current footwear. It seemed insane to make girls wear heels all day while walking around out here, it wasn’t like they had to wear them when they were acting as waitresses at the restaurant. His calves burned, his toes felt like they were cramping and he didn’t dare bring it up to Sasha, imagining she would say two things to him. To remember his motto and that beauty was pain. Looking over at her now she looked to be having a great time talking to the rugrats in line, no sign she was feeling the same thing. Ramsey knew for a fact she had to be experiencing something similar to him. In the past she had plopped her feet down in his lap, telling him her feet were killing her after a night out.

Swallowing hard he shifted his weight from foot to foot, wishing his lunch break would come about faster, not that it was far off, so he could get off his feet for a while and get some privacy away from being looked at like he was a piece of meat. Twisting slightly he popped his back, able to admit that as time went on the corset wasn’t nearly as bad as it had been at first. It being tightened after makeup was put on him had been worse than when it went on initially, but now it was just a constant pressure, a tight pressure, but not one that felt as cruel as it once did. So many things bothered Ramsey that he felt overloaded, but he was a man and he could take it, or so he told himself. If Sasha could handle being on her feet all day in the sexy but uncomfortable shoes, then so could he. As a girl she had experience, but as a man he could handle more pain than her, he reasoned.

Plastering that big fake cheery smile back on his face he grabbed what he had been looking for, the minute reprieve in the back room of the little fake cabin couldn’t last. Picking up the basket full of three inch candy canes he put the handle of the basket in the crook of his elbow like he had seen other girls did and took a deep breath. The room had an entire shelf of candy canes of different sizes, some were to be given out to kids, some were normal size for the trees and large ones big enough to be used as small clubs were there too and of course all of them were for sale in a display area setup that everyone had to walk past on the way out when they purchased their photos.

With the basket held in a way much like Ramsey had seen girls carry purses he made his way through the line to give out the seasonal treats to kids, passing Sasha as he took over what she was doing. The wink she gave him as they passed one another did little to lift his spirits, while once upon a time it would have easily done so, just not this day. The task he was doing was easy enough, but it was a lot of social interaction and much more than he would like with kids. When he was talking to one child, he wasn’t sure if they were five or eight, he wasn’t the best judge of these things, was when the scale of how bad his day was kicked up a notch.

Ramsey was talking to the child, knees bent slightly and bending at the waist, the corset making it difficult to really bend over other ways, he felt the fabric that covered his rear end move. Turning his head to look, he wasn’t expecting anything specific, moving in a dress was more difficult than he would have thought, at least one as short as the dress he was wearing. The wrong movement could cause it to fly up, moving too close to something sticking out could get it caught. When he saw what was happening though his cheeks turned crimson from the blush that came to his cheeks. The makeup was only able to do so much to cover the physical reaction from the embarrassment he felt as he straightened up with a quickness and stepped away. In the line was a man in shorts and a t-shirt that looked to be in his thirties, in his hand was one of the plastic candy canes and he had used it to lift up the skirt of Ramsey’s dress.

It had only been for a second, but still it felt like the world had seen the underwear he was wearing. The world… or at least some of the people in the mall had seen that he was wearing girl’s panties. It had been the first article of feminine clothing he had put on, since then he had put on so much more, but having them exposed felt like something intimate had been broadcasted to anyone that wanted to see. Dropping the basket of candy to the floor Ramsey used both hands to hold down the dress and cover his rear. His breath caught in his throat, his normal reaction of raising his voice to tell someone off was replaced with wanting to cower, feeling both **** and violated.

The feminized man wished he could say he stood up to the older man, that he beat him up, or at least told him off, but instead Ramsey fled. Not quickly, he was able to walk and mince in the feminine shoes, but running was out of the question. In his haste he didn’t run back to the center of the area and into the cabin, no instead he went past the entire line and ran into the bathroom and shut himself inside a stall. Sitting down on a toilet he closed his eyes tight, they already felt heavy from the eye shadow, eyeliner and mascara, but the emotional weight he felt made the rattled man not want to open them again.

Ramsey wasn’t sure how long he had his eyes closed, but he knew he had powered down from all the stress because he didn’t remember leaning his head against the bathroom stalls' metal wall. Blinking a few times when he heard the soft voice of Sasha calling out to him using his middle name.

“Aster, are you in here? Aster… there you are.” Sasha said, seeing the heels and stockinged feet under the stalls door. “Hon, you can’t stay here.”

He felt so drained and out of place even alone in the bathroom. Without complaint though he got to his feet, his throbbing feet and opened the stall door. For the first time today he saw sympathy on his girlfriend’s face and it just made him want to break down that much more. “Babe… Sasha. I can’t do this.”

“I get it.” Sasha nodded. “You have been through a lot, being a girl is a lot harder than being a boy and you can’t handle it. I get it, I get. Don’t worry, I will pay for an uber for you to go home.”

“No, that isn’t it.” Ramsey shook his head, the long dark haired ponytail practically whipping about. “… maybe it is.” He said feeling defeated.

“Okay, I will walk you out, we shouldn’t linger here in the mens room, not a place for us girls.” Sasha tittered.

Not having the energy to respond to her taunt he took one heeled step after another, the sound of the shoes click, clack, click clack, echoing in the room. A noise that always got his attention, but this time instead of a sexy girl being the cause it was himself. The pair walked mostly in silence as they made their way back to Owls where Sasha kept her purse and for him to change out of the costume. Putting on the dress he came here in wasn’t a great option, but it was a better one.

“You know, I’m surprised.” Sasha said casually as they made their way through the mall.

Glancing to the side Ramsey nodded once. “That I went this far? Yeah me too, something like this never crossed my mind.”

Sasha gave him a puzzled expression, one that was completely fake. “No, I mean that you would quit like this. I guess I shouldn’t be, you practically quit trying to find a job a long time ago. I just thought you wanted to… well at least you wouldn’t want to be kicked out.”

Stopping in his tracks Ramsey fully turned to face his girlfriend. “Wait, what? I thought you said it was okay and that you were going to call me an uber?”

A heavy sigh escaped Sasha’s lipstick covered lips, her rolling her eyes and speaking like she was talking to a particular slow child. “Aster, you need to understand. I put my neck out to get you this job and you doing exactly what I say, when I say it was the condition to keep you staying in the apartment. You earning a steady paycheck and looking your feminine best. Do you think that trip to the salon was free? No, that was money I really didn’t have to spend. Money that you were going to payback, but now you are quitting. Something Ram knew, or should have known would cause his ass to be on the street or crashing at a friend's house, wherever. But you couldn’t suck it up for one damned day. So you going back to the apartment is simply so you can get what little things you have left there and get out. Then you can deal with what your father thinks of all this when I send him the photos.

“Ahhh… what?!”

Sasha pressed her long nailed index finger into his fake boob. “I think you fucking heard me.”

The people around Ramsey didn’t matter, the fact that they were standing in the walkway at the mall while having this conversation didn’t matter at the second, though the memory of this would haunt him, like most of this day. “You can’t do that…'' he said, already knowing she had threatened him with it before and that she would very much follow through. In his despair he had forgotten the cause that had brought him to this moment. Him cheating on her the night before and him accidentally admitting he had done the same in the past. “Never mind… lets ahh, lets get back to work” It took effort, real mental effort but he smiled, the little motto fluttering through his thoughts. “I forgot myself for a moment, but I really do appreciate you… cousin, for getting me this job.”

“Oh, just like that huh? Flipping a switch and all happy again. I don’t think you understand just how fucked you are.” Sasha took a step closer so she could whisper and still be overheard through the noise of the people passing by. “I spoke to Frank, Santa. He let me know how happy he was that I got my cousin hired who had a fantasy, kink as he put it for Santa. That I hadn’t planned, but you know what. I like, no. “ She shook her head. “I love it. That little training session after work isn’t training, god I don’t know what is better, you being slow enough not to catch that or you going along with it knowing the truth. Either way after work you and Frank are going to be very intimate and I promise you Aster if Santa does get his rocks off, then I’m going to make this all so much worse for you.”

Ramsey would like to say he couldn’t believe what he was hearing, but part of him knew things had to get worse. The day had a pattern to it and the hope that had bloomed in his chest, the ability for this to end and go home really only had the option of crashing down, like the very purpose of the hope was to punish him more. “Do, do you really intend for me to have sex with another man?”

“Another man?” Sasha scoffed. “A real man doesn’t go around cheating on his girlfriend, he doesn’t lay about playing video games, go out drinking with his friends when he has no job and really doesn’t do that when he hasn't had a job for a year. Let alone do all of that. No, Ram, that isn’t a man that is a boy that wants to be taken care of by their Mommy.” She poked her finger into him once more. “You though, Aster, you are a pretty girl, one who apparently has a Santa kink. It only makes sense that you would want good old Saint Nick to give you a good fuck. Ramsey was off fucking behind my back, so you are going to do it right where I can see you. I want to see your face when Frank cums inside of you. In your ass, in your mouth, it doesn’t matter. I’m going to be right there. The best part is, you don’t have to do it, not one bit. You can choose to go home right now. So you tell me Aster.” The made sure he saw how intense her feelings were. “Are you going home and all that entails? Or are you going to go back to work? I will tell you one more thing though, if you choose to actually put in a full day's work in god knows how long then you better remember to be cheerful. I will not allow you to ruin Christmas for these kids.”

The rest of the work shift went on, Ramsey mostly checking out mentally. It may have been a new job, but nothing he had to do was difficult. Smile, hand out candy, walk kids up to Santa, help them up, help them down and just keep that smile up and act cheerful as he was told. At one point he had a lunch break and had spent it with his cramped feet free of the high heels, resting them on the cool tiled floor. That time seemed to go by the fastest, not that he needed the opportunity to eat, positive nothing would stay down. Ramsey imagined the fat man holding his head down so that his face was next to his old dick. The day wasn’t bad, it was a walking nightmare and while he hadn’t put himself in this specific bad dream, it had been his actions that led to it. Or as Sasha put it, Ramsey fucked around and now he was going to be fucked.

Come the end of the shift the faux North Pole closed and things cleaned up, Ramsey found himself standing in front of the little wooden cottage with his hand on the doorknob. He had gone with Sasha to the ladies room to touch up his makeup, her acting like a patient teacher instructing him on what to do. That morning he had thought he wanted to get back together with the beautiful girl, but now he just saw her as a cruel bitch. Not that he would ever give that thought life and allow her or anyone to overhear it. The motivation to be with her was gone, in its place just self-preservation, he needed to get through this day so he could make some tough phone calls to get out of the apartment and away from her. ‘Just get through this and then she will delete those photos.’ He told himself, not considering the fact that she had never said such a thing at all.

“Come on Aster, we worked hard, time to play hard or in your case, time to play with something hard.”

Without acknowledging her Ramsey opened the break room door and stepped inside, seeing Santa, or the actor Frank sitting at the table. ‘Speak softly, smile and flirt.’ He told himself, trying to not think about what was going to come after that. “Hi Santa! You said you wanted to look over the naughty or nice list with me?” He said in a chipper voice that didn’t reflect the turmoil inside.

“Hohohoho!” Frank laughed, holding his stomach as he kept up the act. Normally the first thing he would do when he came back here after his shift was change, but not tonight, not with knowing exactly what the dark haired beauty wanted. He was surprised to see her cousin with her though and visions of a three way with two olive skinned, dark haired girls dancing through his mind. “Talking about someone who is naughty, is exactly what we will be doing tonight.” He pushed his chair out more from the table and patted his leg. “Come on over and sit in Santa’s lap.” His eyes then looked over to Aster’s cousin. “What about you Sasha? Are you here to spend time with Santa too? I have plenty of room on my lap.”

The idea of being sexual with the old, overweight man was not even a little appealing to her and the Santa angle alone would have been a big turn off. “I won’t be joining you Frank, that is all you and Aster, but I do come bringing good tidings and I will stay to watch.”

“Watch?” Frank asked, his eyebrows raising. ‘Both of them are kinky.’ He nodded, beckoning over the girl who he was actually going to get lucky with.

“Yeah.” Sasha simply said as she shifted some things around on a bookshelf that was used for storage to find what was hidden behind it. “This is what I mean by good tidings, a bit of eggnog to celebrate the season.”

Feeling unsure of himself in a big way Ramsey sat down on the larger man’s leg, immediately feeling one of his paws wrap around his pinched in waist. Looking to where the girl was that he thought about as his girlfriend, something he was going to have to change once the evidence of all of this was deleted. He wasn’t sure how well that was going to go, but once her leverage was gone it wouldn’t matter, at least so long as he stayed out of her reach. “That isn’t eggnog, that’s whiskey.”

Looking at the bottle in her hands Sasha nodded, turning back to the pair at the table. “So it is! Honey Whiskey to be precise.” She then retrieved a few Styrofoam cups that were used for water and brought them all to the table.

For maybe the first time that day Ramsey was happy with Sasha, unlike the false hope she had given him earlier in the day when his underwear, underwear that once belonged to her, had been exposed. He saw no real downside to downing the alcoholic drink, wishing he had the power to choose to black out instead of it being uncontrolled. Ramsey knew the **** was one of Sasha’s favorites, they didn’t keep too much liquor in the apartment and that made him a little surprised she kept something like this hidden here. Ramsey, having no idea that Sasha had run out on her own lunch break to purchase it just for this very occasion, believing that her dolled up ex-boyfriend still might rebel despite the consequences and that a little drink would help keep him nice and compliant.

“My naughty girl, why don’t you show me how good you can be and poor Santa a cup.” Frank said, using his free hand to run his fingers up the girl's leg.

Feeling a shiver run down his spine from the touch, Ramsey clenched his jaw, still smiling as he followed the man’s instructions. “Here you go, all for you.”

The first sip of the honey whiskey tasted like ambrosia to Ramsey, but the joy of it and the escape he felt with the styrofoam cup pressed to his lips didn’t last. Soon as the cup was away things started to begin.

“That was good, you know I like honey. I wonder…” Frank said, trying to be smooth. “Do you taste like honey?” He asked using the arm that was wrapped around the girl to pull her closer to him so that his lips could press against her own. It was a light kiss and he could feel her entire body grow tense, making him worry for just a second that he had misread this entire situation somehow, at least till he reasoned that this girl was living out a fantasy and he was giving it to her, of course he body was going to grow tense with the anticipation and joy of it all.

Ramsey’s eyes went wide as he was pulled closer to the man, them somehow growing even wider as their lips touched one another. His entire body grew stiff, he didn’t even dare take a breath. The kiss only lasted a split second, it was nothing more than a peck, but when he saw the old man’s eyes open up he was positive he saw a twinkle in the man’s blue eyes before he was pulled in once more for the intimate act to continue.

Seeing Aster’s eyes open wide with excitement gave more confidence to Frank, allowing him to free himself of any worries and to enjoy the moment. He kissed her again, this time her mouth was slightly open, letting him know what she wanted. Frank hadn’t made out with a girl in a long, long time, but he still remembered what it was like to French kiss and was thrilled to reenact those old memories and explore the girl’s mouth with his tongue. While he hadn’t done this in a long time he could tell that while Aster was willing she was inexperienced, but he was happy to teach her.

Ramsey felt like he was going to be sick from the light taste in his mouth from the whiskey, whiskey that he hadn’t had nearly enough of, a sip was not enough to handle what he was going through. His entire body trembled as he felt the man’s bushy face slide and grind against his own, reminding him of what he had lost that morning. That was nothing compared to the wet slimy monster pressing its way into his mouth, past his lips and brushing up against his own tongue.

Sliding the hand that was on the girl’s leg up, under her skirt, Frank took a handful of her ass. While pressing her body to his while they kissed like school kids. He felt the excited shiver run through her body causing his manhood to grow much more interested in the situation he was in. Frank wasn’t normally a lonely man, he didn’t have a girlfriend or wife and it wasn’t like he got a lot of action being in the shape he was in and his age, but he had been content. Still the lack of sexual release that didn’t come from his own hand had his dick quick on the uptick. The second the sexy girl had her ass in his lap it had already started to stir and knew he was ready for much more, but still he tried to restrain himself. Aster was younger and a girl deserved foreplay or so he believed.

The arm around him only seemed to get tighter, forcing Ramsey and the fat man’s bodies to press against one another. Trying to shift in his makeshift seat he was able to put both hands on the actor's chest. Just as Ramsey was about to push to try and get some space he felt that same feeling he had felt before, causing his controlled push to become something more akin to flailing. Still it had the desired effect of the grip disappearing from his side, but between that and his erratic movements Ramsey quickly found himself falling to the floor and on his ass.

A sense of relief came over the feminized man, it was gone seconds later, but it was there, flicking in his consciousness. Looking up, Ramsey saw the man with a wide smile on his face. He may not actually be Saint Nick, but he was incredibly jolly as he unbuckled his pants, causing a spike of dread to move through Ramsey. With a trembling lip he grabbed the cup from the table and tossed its contents back. The cup hadn’t been close to full, but taking all of it down at once made the normally smooth drink burn its way down.

When Frank felt Aster sliding her hands over his chest, pressing into it, his shoulders, his stomach he let go of both her ass and her waist. Thinking something was wrong once more, that confidence he had that everything was going great felt shaken in that second, but when he saw her goal, her looking up at him with that smile on her face he knew what she wanted. She wanted Santa’s cock, and he was going to give it to her. Taking a page from her playbook he gulped down some of his drink while working his pants with his other hand.

The entire scene unfolding in front of her amazed Sasha. She put her elbow down on the table, resting her head in the palm of her hand as she sipped on her drink. She wasn’t going to get drunk, but it was a perfectly fine beverage for the show. It was like the two of them had instantly forgotten she was here, just an arm’s length away and she was loving it. Loving watching the man who cheated on her being manhandled, loved watching him be in complete shock as Frank pulled his dick free. She was even surprised, it wasn’t like she knew what an old man dick should look like, but she wasn’t expecting something so… thick.

“Santa has a present for you Aster, be a good girl and open up.” Frank said, sliding the fingers of one hand across her cheek and then to the back of her head where he got a good grip on her hair. The way she looked mesmerized at his member filled him with confidence, he knew what he looked like and it had been a long time since someone looked at him the way she did now. Pulling her closer he took the base of his member in one hand and ran the tip of it around her open mouth, so that he touched every surface of her inner lips, some of her lipstick rubbing off and forming a circle just at the tip. The sight of it driving himself wild as the sexy creature allowed him to use her.

Feeling paralyzed Ramsey sat there on his knees, he got up just a little to get his drink, but now the cup was on the floor next to him and he just wasn’t sure exactly what he should do next. A man’s dick was right in front of his face, yet he couldn’t turn away and as it got closer or he was pulled closer he couldn’t really tell in his state of mind the only thing he knew was that alarm bells were going off in his mind, yet he hadn’t moved an inch. Soon enough the man’s crotch was close enough to smell his natural musk, causing his own stomach to churn. ‘No, no, no, no, no, no’ The words repeated in his mind as he felt the hand holding his now longer hair in place and the man meat touched his lips, circled his lips before sliding in deeper.

Feeling the girl's warm, wet mouth on his prick felt like a small slice of heaven and using her as a doll had an appeal, Frank was just expecting something more from a girl with her kink, more excitement. Though his heart started to pick up the pace when he noticed her cousin, Sasha, getting down on the floor with Aster. His thoughts from before about having them both rekindled. He smiled down at both of them, happy to see Sasha smile back before whispering in the other girl’s ear.

“Get your shit together, you need to please him or else.” Sasha said as she picked up Ramsey’s now feminine looking hand and placed it at the base of Frank’s cock and helped him start pumping it. “Close your mouth and suck girl.”

“No, no, no, no,no, no!” Ramsey started to say, but those words had come after he thoughtlessly started following Sasha’s instructions. His lips sealed around the dick in his mouth, it felt firm, yet spongy and suckled on it gently, causing his stomach to churn some more and his words to come out muffled and more like a girl enjoying herself. “Oh, oh, oh, oh, oh!”

It was almost immediate that a taste came to Ramsey’s mouth as his head was both pulled down by the old man pushed forward by the girl he used to make love to, forcing the cock to slide across his tongue and deeper into his mouth. The two weren’t perfectly in sync, but together they had him bobbing up and down in the prick at a steady pace. Ramsey hadn’t tasted it before, yet he instantly knew what the slightly salty and creamy substance was that mingled with the task of the flesh and lingering flavor of the whisky. It wasn’t like the man had cum quickly, it was just pre-cum but it caused a feeling of revulsion all the same. ‘Just keep going, just keep going, the old man can’t last long.’ The thought couldn’t be more wrong. While Frank could have blown is wad much quicker than he would have liked, Ramsey’s lack of experience in the task left him mostly just bobbing his head up and down at the others rhythm and doing little else, causing the sexual act to go on long enough that his jaw truly started to move past uncomfortable and to ache.

For Frank the sight of two beautiful raven haired girls kneeling in front of him, one helping guide the other in pleasing him was enough that he wouldn’t have had to use a pill to keep his erection going, even if he had to take the pill. “That’s right, look up at me…” He said breathlessly, wanting to look into the girl’s, either of the girl’s soft brown eyes as he felt Aster’s attention on is cock. “Mmm that’s right, suck Santa’s cock. God you are a perfect little…” His voice trailed off for a second before the perfect name came for her. She wasn’t just a little slut, a ho, she was Santa’s ho. “Perfect, just a perfect little Hohoho.

Not sure how long the face fucking went on Ramsey started to cough the second the cock had been freed from his mouth, him falling down to all fours, ignoring the trail of saliva and pre-cum that trailed from the member to his mouth. He felt Sasha gently rubbing his back, despite himself he took pleasure in the comfort, while at the same time wishing he didn’t know what a dick tasted like, what it felt like, its vains, the spongy head, the slick creamy and salty flavor that clung to his tongue. He hoped against hope that he was done, but when he looked up he saw the old man was still just as rigid as he was before. That was when he heard the girl at his side whisper once more to him.

“If you were a better cocksucker you would be done now, don’t worry, you will get there. For now though, dear ol Santa wants more and I’m thinking it might be a good idea to keep him from finding out your secret, he is a lot bigger than you isn’t he?”

The question had Ramsey focusing more on the dick coming out of the man’s pants, mentally comparing their sizes to one another and then admonishing himself for such a thought, realizing what she had actually meant. The man was fat, but Ramsey hadn’t really considered how much bigger the man was than him. Broad shouldered and stocky, the jolly old man could have once played as a linebacker, or at least one on a semi-pro team when they were younger. It was as he was having those thoughts looking up at Frank the mall Santa when the large man reached down with both arms and pulled him up to his heeled feet. Ramsey thought he might try to kiss him again, but instead he was pressed backwards till his ass hit the table, Frank coming in to press his belling into him.

“Your mouth felt great, but I bet you are ready for the real thing.”

It wasn’t just the man’s body that was pressing into him, it was the hard dick and he wasn’t able to suppress his body from shaking, the instincts to flee coming over him once more, but this time he had nowhere to go. When Ramsey felt one of the man’s hand’s go under the skirt of his dress to tug at the panties he started to panic.

“Frank, do you have a condom?” Sasha asked after snapping her fingers to get the man’s attention and away from his lust.

Holding Aster he was about to start kissing her neck when they were interrupted. “Shit… no. Do either of you?”

Putting her hand on Ramsey’s shoulder she gave the poor man a kiss on the check. “Don’t worry, she loves anal. She likes it when people put the ass in Aster.”

Keeping the hand under the girl’s skirt and rubbing her rear end, Frank’s other came up, sliding along her side, just touching the ends of her breast before cupping the girls cheeks as he looked into her eyes. Eyes that he thought he could fall in love with. That was a young man’s game, this wasn’t about love this was just about sex for her and it would have to be for him too. “Turn around.” He commanded, not wanting to wait anymore or for this to turn into a conversation. If she didn't want to do it then she would say so, the middle of sex was not a time for a deep conversation.

Trembling Ramsey did as he was told, but not before looking his girlfriend in the eye and seeing the firm expression on her face. ‘Just get through this, just get through this. Speak softly, smile and flirt.’ With a whimper he turned fully around and put his palms up on the break room table, leaving his rear up in the air. Wishing he wasn’t thinking about how he had a girl in this same exact position the night before. The smile stayed on his face as he gritted his teeth, the hipster panties pulled down just enough to expose what he didn’t want exposed. He heard fabric and something metal hitting the ground, before he felt something poking at his ass.

Frank’s pants hit the floor, the belt clinking on the ground as he shuffled slightly forward, putting one hand on the girl’s side and the other used to help guide him to her hole. Anal wasn’t something he knew a lot of girl’s liked, but he thought he shouldn’t be surprised that Aster enjoyed it. Just as the tip of his dick felt her sphincter he made a mental note to buy condoms on the way home. He heard the whimper escaping the revved up girl’s mouth, positive she was wet as can be and felt like she needed his cock in her as much as he wanted it in her. His member was already slick from her mouth, still though he wished he had some lube, but if she wanted it, then he wasn’t going to deny her what he wanted to and then thrust his hips forward slightly.

Just the tip, just the tip of the head pressed into Ramsey and already his eyes were bugging out, him gripping the ends of the table. “Please… please, please…” he begged, wanting Sasha to call this off, not really thinking about what she was doing as she climbed atop the table so that she faced him.

“Oh yeah, Santa’s little Hohohoho is going to get what she wants, you don’t need to beg.” Frank said, hoping that she would actually keep going, her soft mewling turning him on more as he pressed himself into her more and more with each slow thrust.

Before climbing on the table Sasha had taken a large candy cane from one of the shelves, the thing was about an inch thick and several inches long. When she was up on the table she slid closer, one leg dangling down the side as she unwrapped the piece of candy. She was full of glee as she watched what was happening. It wasn’t turning her on, but she could admit it was sexy. Again she slid a little closer while the table itself rocked with each thrust of the make believe Santa as he pumped his member into the man she wanted to punish. Moving the piece of candy down she pulled up her dress just a little bit, putting the long straight end of it against her panties, the curved end pointing up into the now feminine Ramsey’s face. “Suck on this girl.”

“MMmm!” Ramsey held in a scream as the cock went deeper and deeper into him and hurt, hurt enough that he knew exactly why Sasha had never been willing to do anal. It made him feel like he was going to be split in half. As the thrusting went on the pain ebbed and flowed, never going away, but changing in intensity, the more the cock went in the more wrong and painful it felt. ‘FUCK!!!!’ he screamed internally even as he surprised a scream out loud and once more giving the wrong impression to the man getting his rocks off. He hardly noticed the piece of candy in his face, all focus on what was happening behind him and even then it was hyper focused, Ramsey having no real idea that the red and white stockings on his legs were slipping down as he was bent over and fucked.

It wasn’t until that holiday treat slapped him in the face that Ramsey realized what Sasha was holding in front of him and even then he didn’t do anything with it till she repeated her command. Closing his eyes tight he slid his tongue across the surface, its flavor vastly superior to what had been in his mouth not long ago and he tried to focus on that. A difficult task as he felt his extensions that had been up in a ponytail come free and be yanked back.

“AHHhh!” Ramsey’s mouth came free of the cane and let out a screen as a few things changed at once. The sound of flesh on flesh changed, the man’s belly had been bouncing on his ass already, but now the cock that never made it fully into his mouth was all the way up his rear end. As horrible as the experience had been it was like someone had flipped a switch. It wasn’t that the pain went away, it was still there with each thrust, but it also felt good, like real good and it caused some sort of internal pressure to rise within him. He didn’t want it to happen, he wanted what was happening to stop, but at the same time his own dick started to come to life. ‘I don’t like this… I don’t like this…’ He told himself as his head was pulled back again as his hair was yanked on.

Ramsey didn’t know how well the extensions were put in his hair, but he did know it took forever and the bill had made Sasha frown. That was of little consequence now as another command came from the girl for him to get back to work on the candy cane and despite his best mental efforts he felt himself push his ass backwards into Frank the Santa as it caused an intense feeling of pleasure.

The three rode like that for a few minutes, Sasha doing little other than holding the piece of candy still, keeping her little doll on point and enjoying the show but she knew what was coming or cumming when Frank tossed his head back.

So caught up in things, Ramsey didn’t know what was about to happen till he felt things change. The cock inside of him grew stiffer and Frank changed from large thrusts to pressing all the way in, holding his cock there before doing a few micro thrusts and then repeating. It was then that a feeling he didn’t know how to quantify happened, not sure exactly how to explain or even think about it other than the cold hard fact that a man had just put cum into his rear end. Despite this Ramsey still felt the old man continue to press himself forward, like he was trying to get every last drop of his cum into him.

Feeling spent and ready for a nap Frank stepped back, a few spurt of cum squirting on his lover's rear end and some of his seed dripping from her ass. He took one breath after another trying to calm his beating heart and bask in the afterglow of an amazing sexual encounter with a girl that wasn’t even half his age. The way she slumped down on the table to told him she was spent too. “Aster, honey. Let's do this again soon. That is if you want to get on the good girl’s list.” With a happy sigh he pulled up his costume pants and made his way to the changing room to get back into his normal clothes leaving the girls to do whatever it is they needed to do.

Slumped on the table Ramsey didn’t even pick up his head, he just looked up at Sasha. His rear felt like it was on fire, nothing truly bad but enough to be uncomfortable and somehow it also felt empty and at the same time like he had to take a shit. Only this time he was sure what would come out would be blood and cum. ‘At least I didn’t get off on this…’ He thought to himself, trying to distance himself from how his freed member had grown hard from being fucked. It was while he was having that thought that he felt Sasha pat his cheek gently.

“You did good Aster, real good. Now we need to get you cleaned up for Roy’s blow job. I’m sure he is wondering where you are at.”

“Where I’m at? Ramsey asked, confused. “Do I have to watch you blow him like did with San… Frank?” He said between gasps for air.

With a smile full of pity Sasha slowly shook her head from side to side. “Hon, I never said I’m going to blow Roy. That is for girls like you who just can’t get enough sex and cock. Don’t worry, I’m sure you will do a better job your second time than your first and if not, there is always tomorrow.”

The End