Unhappy New Queer free porn video

Unhappy New Queer by Peg Thebois "So do you have a name when you're dressed up?" Jim cleared his throat nervously. "Carol." "I guess this is a special time of year for you. Are you going to a New Years Party tonight?" "Sort of." Jim left it at that and resisted the make-up artist's further attempts at small talk while she worked on him, eventually she just stopped talking to him except to give him directions of where to look or how to hold his face. Jim didn't want to talk at all about his situation, the last week had been something he never could have imagined. It had started when he had been fired from his job in early November. When he still hadn't found new work by Christmas his roommate Wayne had given him an ultimatum, move out of the apartment or start paying his rent in sex. Jim was definitely not gay, in fact his habit of commenting on a beautiful lady co-worker had been a big part of how he lost his job. He didn't think Wayne was gay either which was why in order for Jim to start paying in trade Wayne had insisted he dress and conduct himself as a woman, who was dubbed Carol. That was why Jim was right now sitting in a chair at a make-up salon in his curly blonde wig getting his face made-up. His instructions had been to make it dramatic, so the artist was doing what she called a smokey eye on him. He hadn't wanted to appear ignorant so he hadn't questioned it, the only thing he had said was that he wanted red lips, that was something else wayne had been specific about. While he was sitting here having these paints and powders smeared on his face there was a new roommate moving into what had previously been his room, since Carol now shared Wayne's bed Wayne had arranged someone new to take over. Jim hadn't even met the new roommate, the day after Christmas when the new guy had come by to check the place out Jim had been sent out by Wayne to pick up some new clothes for Carol since the only thing Wayne had given Jim was a ridiculous "sexy santa" type dress. Now he had about a half dozen outfits, all purchased at a thrift store, including the one he was wearing right now, which consisted of a pleated denim skirt and a black top that had one shoulder strap and left the other one bare. Wayne had also told him to make sure that he bought a sexy new nightie, he said he liked looking down at a sexily dressed girl sucking his cock. And that was what Carol was doing, every night since Christmas she'd had her lips wrapped around Wayne's cock, he'd been fondling and grinding on Carol's ass but hadn't pushed that limit yet. "Alright Carol, we are all done, here take a look." She handed Jim a hand mirror and he looked at what she had done. He could only stare in shock and a bit of dismay, she had made him look gorgeous. The effect of what she had done on his eyes, including the overly large false eyelashes and makeup made his eyes look dark and mysterious, he couldn't help but think of the term bedroom eyes. He turned his face from side to side examining how she had used different colours of makeup to soften the shape of his face, making the whole thing look more feminine, and then of course there was the bright red lips as he'd been forced to ask for. They looked wet and slick, even Jim couldn't help but think what lips like that could do to his cock, but that notion was tempered with the knowledge that it was not his cock they would be sucking. "Is something wrong?" Obviously the artist could see the dismay on Jim' face and was misunderstanding the reason for it. It wasn't that she didn't do a good job, in fact he was dismayed that she had done such a good job of making him into a babe. Jim forced himself to look happy. "No, no absolutely not." "You just didn't look happy, are you sure there isn't anything wrong?" "Oh I..." He paused for a moment, and brought his hand near his face, as though he was composing himself. "I've just never seen myself look this beautiful." That part was certainly true. "I was just disappointed that I can't get results like this." "Oh that is okay, you just need to keep practising. But don't get too good, okay, I would hate to not get the opportunity to do your makeup again." Perhaps she might even get her wish to do it again sometime, but Jim had no doubt that he would get plenty of practice if Wayne had his way, at least until he managed to find himself a new job. He didn't want to get good at making himself look like a girl though, he would just have to keep looking for a job. Wayne had locked up all his male clothing, but hopefully if he could tell Wayne he had a job interview Wayne would give him back something appropriate. He would have a long ride home to think about all those things though right now he had one other instruction from Wayne. "Could you do me a favor?" he asked the girl, while taking his cell phone out of his purse. "Could you take a picture?" "Oh of course." Jim forced himself to think like Carol, an easy thing now that he had seen how feminine he looked, and Carol would be happy about that, so she smiled for the camera. After she texted the picture to Wayne, Carol went to the counter to pay and put her heavy winter coat back on. She started getting strange looks from people almost as soon as she left the make-up salon, but fortunately this was one of the less heavily trafficked malls in the city so there were not that many people out and about today, but almost every one of them was staring at her. She realised she didn't look like a woman, not really. You could tell she was a man, but a man making a damn good effort to look like a woman, at least the coat hid her chest, since the top she was wearing only had one shoulder it couldn't really be worn with a bra, so it was obvious Carol had no breasts. As she made her way across the mall parking lot to the city transit station Carol sucked in hard between her teeth, it was bitterly cold, probably about twenty below and even with pantyhose on she still wished she was wearing pants, but that was against Wayne's instructions. "I want to be able to grab my bitch's pantied ass anytime I please." Or even better than wearing pants would be to not have to take the bus at all, but Wayne had the car, and Carol certainly didn't have the money for a taxi, fortunately it was only one bus home, no transfers, even if it was most of the way across town. While she waited for the right bus Carol got a text back from Wayne in response to the photo. "Holy shit! Don't you look like a proper little fuckdoll." No question mark, there was no question, no denying it, Carol did look like a doll with her dark eyes and red lips. When the bus arrived Carol got on and paid her fare, she had to give the driver credit, he cocked an eyebrow in surprise sure, but compared to some of the other reactions she was getting that was downright subdued. Carol took a seat at the back of the bus, hopefully she could avoid notice as much as possible. As more and more people started to file on the bus started to fill up, most people preferring to sit as close as possible to the front or the second set of doors halfway down the bus. Unfortunately that luck would not hold as a group of boys, probably late teens, maybe even early twenties who had not matured enough to stop carrying themselves with teenage swagger were headed right for the back. There was no question they saw Carol as she could hear one of the exclaim "What the fuck?" before they were even onto the raised rear portion of the bus. They started laughing and making comments amongst themselves which Carol tried very hard not to hear. She would just keep her head down and pretend she was not here, pretend she was not riding a bus full of people. They didn't make it easy to ignore them though, because they took a seat one row in front of her and across the aisle, she could hear them whispering, trying not to hear just spared her hearing what they were saying. Several very long minutes went by before Carol heard one of them calling out to her "Hey, Hey." She didn't answer but she raised her head to look at the one who was talking, she thought it was probably the same one who had exclaimed upon first seeing her. She looked him directly in the face, addressing him without speaking. "What are you, some kind of faggot?" They didn't wait for a response, all three of them turned to each other and burst out laughing. After a few moments the one with a voice turned back. "No, no, serious, do you just ride the bus looking for dicks to suck?" Carol wanted to tell him to go away, wanted to defend herself but she found a lump sticking in her throat. It seemed silly to be intimidated by children, barely old enough to shave but in her current state she found it impossible to speak. As she swallowed the lump of fear he continued with his tirade. "Do you want to suck my dick?" He started fondling his crotch suggestively through his jeans. "You want to suck all three of us off right here on the bus?" Finally Carol found her voice. "Please leave me alone." It shocked her just how quiet and meek it was, She had wanted it to sound calm and even a bit dismissive, as though they weren't worth her time but it came out as a terrified squeak. "What was that? I didn't hear you fag." Carol took a breath to steady her nerves. "Please..." "I'm talking to you, you fucking Queer!" he shouted overtop of her trying to repeat her request. "Cool it down back there or get off my bus." the driver shouted back at them, but he was all the way up there, nothing he could really do without stopping. He stood up and his two friends stood up behind him. Looking Carol right in the eyes he cupped his crotch and thrust his hips a bit, grinding on his own hand. "You want to suck this cock right here faggot?" One of his friends pulled the cord to signal for the bus to stop. "Too bad for you this is our stop, maybe we'll see you around and let you suck off all our friends." As he and his friends got off the bus Carol could hear them cackling with laughter. That whole scene had been one big joke to them, just like Carol herself, a ridiculous joke. Something inside Carol wanted to break, to just cry but she had seen enough movies to know what crying does to a woman's make-up, besides she did enough of that in the bedroom as of late, she would not let herself do it in public. Her eyes welled a tiny bit but she dared not even blink the tears away, she just let them sit there a moment until the natural reflex to blink overpowered her conscious control. By the time she had composed herself Carol saw it was not too much farther to the safety of home. She passed the last couple of stops looking around at the rest of the bus, she didn't hear any whispers anymore, no-one was glancing back at her, not even out of the corner of their eyes, everyone on the bus seemed very interested in either their laps or the passing houses out their windows. It was clear if she'd had to defend herself none of them would have involved themselves. But the bus pulled to stop at the nearest stop to Carol's house, which was about a block from the front door of her building, but at least there were no people to catcall or harass her along the way. The only issue was the cold wind blowing on her legs and up her skirt. Carol was relieved when she finally reached the security of home, free from judgements, at least except for her own, and from Wayne, and the new roommate who if he was here must be in his room, but Wayne was back already and sitting in the living room, watching TV. "Is that you Carol?" "Yeah, I'm back." "I bought you a special outfit for tonight, it is on our bed. Why don't you go put it on and come out here so I can see how it looks on you." Deep down Carol was still Jim and Jim could not be happy about wearing a dress, even if it wasn't going to be that sexy santa dress Wayne had made him wear Christmas Day, but once she got a look at the outfit itself even the part of him that answered to her and to Carol was dismayed, this was even worse than the sexy santa dress. Carol started by stripping naked and putting on the change in underwear she'd been left, this set of bra, panties and garter belt were sheer white fabric covered with layer after layer of black lace ruffles. The panties were not a thong but they didn't quite cover Carol's bottom completely, they crept just a little up her butt crack, leaving the underside of her cheeks showing. The garter belt was nearly identical to the white one she wore with her sexy santa dress but with black lace highlights, and the fishnet stockings she had been left to match it were also black as opposed to white this time, and while Carol had not worn a bra that first night she had worn one since and so she knew to put it on backwards and then turn it around. She had found that information online, as well as finding out how to make a reasonable set of fake breasts out of nylons and bird seed, triple layering the nylons so no seeds poked through. Once Carol was in her underwear with her breasts in place she glanced at the same two white fluffy petticoats she had worn that first day, the ones that had made her dress stick nearly straight out, she decided to leave those until after her shoes were on. The shoes, while they were still high heels were no-where near as extreme as that first pair of heels which Carol had found out were five inches tall, these were maybe three inches, but what concerned her more was that the ankle straps came with miniature padlocks, clearly once she put them on only Wayne could remove them. Still after everything else she had done she only hesitated over locking these heels on her feet for a moment before resigning herself and pushing the locks closed with a click. Now she put on the petticoats, followed by the dress itself. Black with white lace, in exact contrast to her underwear, Carol had never seen anyone wear a french maid's dress, except in movies. This style had a surprisingly modest neckline, it certainly would not show the lack of cleavage to indicate that Carol's breasts were not real but that was about the only encouraging thing about it, the sleeves were puffed up like balloons of black satin and the skirt was the worst. Just like the Santa dress it stood almost straight out on her petticoat and sat very high on the thigh, maybe two or three inches below her bottom. She struggled a little getting it zipped up in the back and even more tying the wide ribbons of the lap apron, that was purely decorative in nature, into a bow, that when she saw it in photos later would seem cartoonishly oversized. The last step was putting on the little accessories, the fingerless lace gloves the bit of white lace that tied around her neck like a collar, and bobby pinning the black and white lace headband to her wig, she was physically ready to go show Wayne, unfortunately her stomach felt like it was down around her knees. How could she let herself be seen in this ridiculous get-up? Not just by Wayne, after having to give him a nightly blowjob he couldn't possibly think any less of her but also by who knows how many people at a party? Wayne still worked at the same office where Jim had worked, surely he would have invited some of their colleagues. What would they think of Carol? It was easier walking in these shoes than the other ones, something Carol was grateful for as she made her way to the living room for Wayne's appraisal of her final appearance. He turned his head as she walked in and she could see his eyes widen. "Ooh la la." He grinned. "You clean up okay doll. One might almost not realize you are supposedly a man." Jim couldn't help but frown as the backhanded compliment jerked him out of his Carol headspace. "Thank you," he replied sardonically. "So where is our new roommate?" "Returning the moving van, but don't worry your pretty little head about that. We have to talk about tonight. I told all our guests you would be helping out at my party tonight but more importantly I didn't tell them about other aspects of our arrangement." Thank God, Jim thought. "I don't expect you will want to mention anything about it but don't expect a kiss at midnight, besides, I know where your mouth has been." He ended with a teasing wink. Jim hadn't really expected Wayne to make him suffer through a midnight kiss, he had never tried to kiss Carol, that would be Gay. It was clear in all of Wayne's mannerisms that Carol was just a receptacle, a warm hole to stick his dick in. Jim couldn't really tell if this made their arrangements more humiliating or less. "Now I want to make sure all my guests are greeted properly so you can go online and find a video instructing you how to curtsy properly. I want you in the bathroom practicing until our new roommate gets back." Curtsying? Really? Wayne seemed dedicated to making this as humiliating as possible for Jim, at least as much as he could without risking catching himself in the fallout. "Do you have a problem with with your orders Carol?" Wayne questioned although his tone made it clear he would accept no challenges to his authority. "No." Carol mumbled demurely. None I think you would care about, she thought to herself. "Tonight you can call me Master Wayne. And any of my guests are to be addressed as Master or Mistress before their name." "Yes Master Wayne." "Good, one last thing." Wayne rose from the couch where he was sitting and strode over to her. He wrapped his arms around her and both hands went up the back of her skirt, grabbing a cheek apiece feeling her flesh and frilly lingerie. "Mmmmm," he grunted lecherously. "I am looking forward to tonight after everyone else has gone home." He squeezed firmly with both hands for emphasis. "I've left one more surprise in the bathroom before you start practising your curtsey." When Carol saw the purple butt plug sitting on the bathroom counter, next to a bottle of lube she had to fight to contain her tears for the second time today; this was it, he was clear in his intent, he was going to take Carol in the ass tonight. Couldn't he be satisfied with blowjobs? Of course he couldn't, what man would ever be satisfied with just head, eventually he would need to fuck and eventually was tonight. Not seeing a point in delaying she took off her panties and squirted some lube onto the plug. Just handling it and thinking about what was about to happen made her feel nervous, to the point of wanting to throw up, but she just looked down at the nasty little thing. At its widest it was about as thick as two fingers, but a bit longer. When she was done procrastinating she set to the awkward task of inserting it. Thanks to a good amount of lube it slipped into her ass with some discomfort but no actual pain. Carol couldn't say it hurt per se but it felt weird, definitely not enjoyable. Then, as much to take her mind off her situation as from any desire to follow orders, Carol put her panties back on and brought her laptop from their bedroom to the bathroom to practice in front of the full length mirror. Before discussing the technique she explained the history of the curtsy and how grace was the most important part. She finished her explanation by saying. "A curtsy is for girls only. Guys bow, girls curtsy." Carol thought about showing this to Master Wayne but decided he would not care about the distinction. Besides, in this dress, doing a formal bow from the waist would be worse. The woman in the video did a good job of explaining the proper technique once she got down to it. Right foot behind left, back straight, steady down, steady up. Carol gave it a try and lost her balance, almost falling down just trying to stand on one high heeled foot to move her other foot behind her. She paused the video while she practiced a dozen or so times, it was enough to get the transition right although her descent was not smooth, not like the instructor. She started the video again and Carol curtseyed along with the instructor who was discussing how to curtsy differently depending on the length of your skirt. Most importantly she stressed if your skirt is above your knees do not lift it or hold it out to the side. Carol had been lifting her skirt a bit, which revealed her petticoats but was glad to make the adjustment and continued to practice again and again in front of the mirror. The video had talked about bowing your head when you curtseyed to someone of higher status but Carol would save that part for when she was actually greeting guests. Right now it was more important to watch in the mirror when she curtseyed and make sure she was doing it correctly. Carol didn't keep track of how many times she curtseyed before she heard a knock at the apartment door. "Carol!" Master Wayne shouted from the living room. Carol took a deep breath and stepped out of the bathroom. "Go greet our new roommate." With a deep breath Carol readied herself as she opened the door and dropped into a curtsey, bowing her head before she even had a chance to register who was on the other side of the door. Beth cackled with laughter upon seeing Carol. "Oh my god! I can't believe you actually got him to do it." She strode past Carol as Carol numbly closed the door, Beth was their new roommate? This was the woman who had been, inadvertently, as much a part of his firing as the manager he had offended. Beth had been Jim's office crush and he had never tired of complimenting her on her ravishing good looks. He'd always been respectful and hadn't realised she minded until he was brought into his manager's office for a complaint of sexual harassment. For her to see him like this and refer to Jim as him immediately pulled him out of his Carol headspace. He closed the door and found that Beth was already walking into the living room to talk to Master Wayne. "I know you had told me that you got him to agree to this, but I couldn't believe it until I saw him." "I know, Carol has been quite surprising. To be honest I am amazed at how pretty she turned out." "Yeah, you wouldn't quite mistake him for a woman, but he's one of the prettiest guys I've ever seen. I mean what do you even call someone like him? He's definitely not a man." Master Wayne just shrugged. "I just refer to her as Carol, I don't really think too much about gendering her." "Maybe this is why he was always hitting on me, maybe he was really just jealous of the pretty clothes I wear." Of course nothing could have been farther from the truth, Jim had never wanted any of this, not the clothes and certainly not the way that Carol had to service Master Wayne in bed. Master Wayne got up. "Since Carol is through using the bathroom to practice curtseying I'm going to go take a shower and shave before you start getting ready for the party." Jim couldn't bring himself to say much to Beth or Mistress Beth as he would be calling her tonight. As he stood there, swaying side to side, feeling the petticoats brush against his naked thighs and trying to drop back into Carol headspace Beth had started to take a look around the apartment. She was right now eying the calendar on the kitchen wall, the one with two sharpies attached to it by string, a red one and a black one. "What's this?" She ran her finger along the series of red x marks along the last 6 days since Christmas. "That is tracking my rent payments, I have to contribute at least $200 a week. Plus making up what I owe for backrent." "I see, but what do these red X's represent?" Jim had a strong suspicion that Beth was well aware of what Jim's arrangement with Wayne was, she just wanted to force him to tell her about it himself. "Every red X is worth $50, I get to put an X up every day that I give Wayne..." Just talking about this he was defensively going back into his Carol mindset, but she still had trouble saying it, she had to stop because she wanted to cry. Carol took a steadying breath before she finished. "Give Master Wayne head." "I see," Mistress Beth was clearly trying not to laugh. "And what is the black marker for?" "It is for when I..." Carol choked on the words. "When he..." She couldn't say it, especially knowing it was going to happen tonight, it was just too embarrassing to mention. "When you let him in the back door?" Mistress Beth offered. Carol just nodded. "And how much do you get for that?" "$150" "I don't see any black marks on the calendar yet." Carol shook her head, she was trying very hard not to start weeping in humiliation standing here, made-up like a woman, and a particularly easy woman at that, dressed like a slutty french maid with a plug up her ass, talking with the girl who had been her crush for quite some time, but talking about Carol sucking cock and potentially taking it up the ass. "I'm sure Wayne will eventually break you into that." Carol knew Master Wayne would, the evidence of his intent was getting her ass ready even as they spoke but unless Master Jim had told Mistress Beth that Carol was not going to make things worse for herself by volunteering that. After their conversation Carol busied herself in the kitchen, uncorking a bottle of red wine to let it breath and taking hors d'oeuvres from the fridge and putting them on a serving tray and otherwise trying not to think any further ahead than she needed to. Over the next couple hours, while Master Wayne and Mistress Beth got ready for the party Carol gave the whole apartment a once over, dusting the blinds, vacuuming the carpets, mopping the kitchen floor, since the bathroom was in use, practically the whole time there wasn't much she could do in there, but by the time Mistress Beth was done she could be sure their home was presentable. Mistress Beth on the other hand, looked far above presentable, she looked more beautiful than anyone Carol had ever seen. She had curled her hair into long spiral curls that hung just past her shoulders and she was wearing a dark blue strapless dress that pushed her breasts up and out but somehow came off looking as classy as it did sexy. The skirt of the dress was tight fitted but had a side slit all the way up to her thigh that as she walked down the hallway gave tantalizing flashes of her thigh. As much as Carol was spellbound she didn't dare say anything, after all if Jim hadn't had that harassment on his file he probably couldn't have been fired for that misunderstanding with the office manager. Master Wayne on the other hand had no such reservation and gave her a wolf whistle. "If I didn't know you were taken I would ask you to trade rooms with Carol, you look gorgeous." "Oh I wouldn't dream of displacing your pretty maid from your bed." "Hmm, about that," Wayne said, adjusting the tie he was wearing with his suit. "No-one else coming to this knows that I have fallen so low as to let a guy, even one who turns out of pretty as Carol, suck my cock. I would appreciate it if you didn't tell anyone." "Well I have already told my..." She paused, finger finger on her chin as she felt for the right word. "my plus one. But you don't have to worry, we are both the very definition of discretion." Carol only had to endure one more trying situation before the first guest arrived, as Master Jim came up behind her, put his hand up her skirt and pressed his fingers between her butt cheeks, feeling for the base of the butt plug. "Good girl," he whispered in her ear before slipping away. Once people did start arriving Carol settled into a bit of a routine: greet the guest at the door with a curtsey, take their coats to the bedroom where they would be quickly but neatly layed out on the bed, then back to the living room to make a round with the tray full of hors d'evours and glasses of wine. Although there was one or two of Master Wayne's friends from school days most of the guests were from his work, which of course had also been Jim's work, and not a single one of them failed to laugh when they saw what had become of their former colleague. Oddly as more people arrived, Carol started feeling less self-conscious about her attire, everyone was in formal attire so it sort of made sense to have a french maid, and as revealing as this uniform felt, it was better than some of the glorified lingerie that passed for a maid uniform around Halloween every year. As the evening progressed more than a couple of the guests had enjoyed a few too many glasses of Master Wayne's wine, Master Willard in particular had taken to swatting Carol's ass every time she walked by. It got to the point where after he had grabbed what he wanted from her tray Carol would try to scurry out of range before his hand landed. As she retreated she was always treated to his guffaws, he fancied himself hilarious with this treatment of her. What was worse though was as she walked away from one of these encounters, her backside smarting from a particularly good blow, she heard a few of the ladies talking to Mistress Beth titter at her. "Isn't it remarkable how well Jim handles though heels?" Mistress Amanda commented. "Yeah, look at that little ass swish," Mistress Louise added. "I guess some girls just take naturally to heels." Mistress Beth offered, even though she knew full well, Carol had been practicing in higher heels than these for the last week. As Carol walked away from them the phone rang. Mistress Beth answered it and buzzed the person into the building after commenting. "Fashionably late, as always." Carol put her tray down in the kitchen and went to the door ready to greet the new guest, who certainly was late as Mistress Beth had commented, there was barely more than an hour left before midnight. As she opened the door Carol froze halfway into her curtsey, of all the people that could have been invited why her? Standing there in the doorway, dressed in a suit and tie, was the woman who had fired Jim. "Well, are you going to welcome me in, or at least get out of my way?" Her tone was as frosty as ever but it did jar Carol out of his shock to abandon her curtsey and step aside. "Of course, Mistress Sheila, I beg your pardon." "Don't call me that. A Mistress is a married man's plaything on the side. What are you calling the men at this party, Master?" "Yes..." Carol managed to choke off the response that was becoming instinct to call her Mistress. "Then call me that. And take my coat." "Of course, Master Sheila." As she took Master Sheila's coat to the bedroom with all the others Carol heard her comment. "As useless as ever." Useless? Jim had been very good at his job, the reasons he had been fired had nothing to do with his performance and really were a couple of big misunderstandings. Carol took a moment to straighten her apron and fluff out her skirt, she was going to show that Sheila just who was useless. She then proceeded immediately to the kitchen for her tray and into the living room looking for Master Sheila to offer her a drink, there would be no way she could claim Carol was neglectful of her serving duties. When she found the newest arrival Carol demonstrated a perfect curtsey without spilling any of the wine glasses on her tray. That earned her a raised eyebrow but not much else. Try as she might nothing Carol did seemed to impress her former manager, and before too long it was time to prepare for midnight. Carol uncorked the champagne and set about filling her serving tray with nothing but glasses of champagne for everyone, everyone had their glass of champagne for the toast a minute before twelve. The Television was tuned in just waiting for the final countdown, as it began Carol could only focus on her wish for the new year, finding a real job, no more sex for rent, no more being Carol. She would probably have to move once she found a new job, notwithstanding the lack of her own bed space, she would never be able to look at Master Wayne or Mistress Beth the same once she returned to being Jim. Out of the corner of her eye she was watching Wayne to see if he would be granting any of the ladies he had invited a new year's eve kiss, but as the count went into single digits he seemed to be standing by himself. She looked around for Mistress Beth and just as everyone cheered Happy New Year, in unison she found her, just in time for the rather surprising sight of Mistress Beth and Master Sheila passionately sharing a New Years Eve kiss. This was not a chaste little peck between two women who were comfortable with each other, this was the sort of kiss Jim had always wanted to give Beth. Their arms were wrapped around each other and their mouths were held in such a way Carol imagined there was a fair bit of tongue being shared between them. As surprising as it was it explained a good deal, that had been why Sheila had seemed to have it out for Jim, the woman he was continuously flirting with was the her girlfriend! After a chorus of Auld Lang Syne which Carol was frankly too stunned to participate in many of the guests finished their champagne and made ready to leave. Many of them took a moment to congratulate Jim, since they had no idea about his Carol persona, on being a good sport about this. A number of the women, also complimented him on how beautiful he looked and then of course there was Willard; before he left he came up to Jim and held his arms open. "Give Master Willard a hug now." Hesitantly Jim played along, even though he knew this was a bad idea, after all, he wouldn't want to insult one of Wayne's guests, especially given the compromising position he was going to be in later that night. It was fairly predictable as Willard wrapped his arms around Jim and his hands went immediately up his skirt to grab his ass. The smell of wine washed over Jim as Willard breathed in his face. "You got a sweet ass girlie, how about you come home with me, see if your pussy is as pretty?" Did he really think Jim was a real girl? Was he that drunk that he couldn't tell? And more importantly what could Jim say to him? Who knew how he would react to being told the ass he had been grabbing at and swatting all night belonged to a man? Fortunately he was saved by Amanda. "I don't think your wife would appreciate that Willard." He took his hands off of Jim's ass and stepped back, looking deep in thought. "You're probably right, well have a good night." As Willard walked away he gave Jim one last swat on the ass. "Thanks for coming to my rescue." Jim turned to Amanda with a curtsey. "No problem, word is Willard's wife doesn't go out to public events like this with him because she was tired of seeing him get drunk and act like an ass." After tonight's performance Jim considered that likely. "No problem, I can't wait to tell all the girls at the office about this." She must have seen Jim' face sink. "Oh I won't tell them who it was just that he is such a lecher that when he's been drinking he'll even go for a guy in a dress." Jim curtseyed. "Thanks again." Amanda giggled at that as she walked away. Soon afterward the only people left were Jim, Wayne, Beth and Sheila. "So am I going to be staying the night?" Sheila asked, running her fingers along Beth's cheek. "Why don't we go to your place? Carol was too busy to unpack my boxes and besides." Mistress Beth's voice slipped into a stage whisper. "I have a feeling it'll be pretty loud around here tonight." That was two unexpected things, Jim hadn't thought he was going to be unpacking Mistress Beth's belongings but also that even she knew what Carol was going to be doing tonight. The two women shared another kiss before Master Sheila said, "I'll go get our coats, we can call a taxi from the lobby." Mistress Beth turned to Jim. "I've already unpacked my intimates so you don't need to go rummaging through them when you start unpacking tomorrow. They are in the top and bottom drawer of my dresser, so you have absolutely no need to go into those drawers." Jim curtseyed. "Yes Mistress Beth." it was true he had been excited by the thought of handling Beth's delicate lingerie. "Now I know I didn't miss anything but I don't want you having any excuses, should you find anything that should go in those two drawers just leave it on my bed when you are done." Another curtsey punctuated with the familiar refrain. "Yes Mistress Beth." Jim hesitated. "Mistress?" "Yes Carol?" "How did you know what is going to be happening tonight?" "When you finished in the bathroom you left your bottle of lube out, I put it under the bathroom sink, there was something else there that I think you should see before you go to the bedroom tonight." Mistress Beth was, of course, correct in that. Master Wayne insisted Carol make use of the enema bag that she found there, but at least he had also left her the key to remove her high heels. Fortunately the internet knows everything including how to administer an enema, it had been uncomfortable and the less Carol thought about it the better. In fact even the idea of why she'd had to take an enema in the first place was a more appealing thought. She was dressed in her maid's uniform again when she walked into their bedroom and found Master Wayne looking at his laptop. She knelt down on the floor beside his desk and glanced up at the screen, it was a picture from the party, Carol was clearly the focus of the picture but she was standing beside someone, Carol knew it was Master Sheila from her suit and tie, but it was no longer obvious as Master Wayne was using some photo tool to blur out her face. He had done so with everyone else at the party, everyone that is except Carol, her madeup face was left unblemished and exposed, but anyone else in the picture was granted anonymity. After saving Master Wayne clicked ahead to the next picture but there were no faces in this picture, apparently Carol had been so engrossed in her duties she had not even noticed someone slipping a camera, or more likely a phone, beneath her and capturing a photograph of her panties nestled in the middle of her petticoats. Wayne moved to lay down on the bed and undid his pyjama pants, Carol knew well enough what to do by this point and knelt between his legs feeling an increasingly familiar sinking feeling of shame in her stomach as she lowered her head and started to lick at the head of Wayne's penis, which was already semi-hard. It didn't take long for that to turn to fully hard as Carol took him in her mouth and started sucking, swirling her tongue around the head of his cock, the way Wayne had taught her. "Ohh yeah," Wayne groaned as Carol took as much as she could on each stroke. "You are just a natural cocksucker, you know that slut?" Carol groaned with embarrassment at the supposed praise. "Did you bring the lube back from the bathroom?" Carol stopped in mid stroke realizing she had forgotten to do so. Wayne knew she hadn't but she still took his cock out of her mouth to answer. "No, I forgot it." "Well go get it and I'll want a beer after we are done so bring me one from the kitchen while you are at it." "Alright." Carol ran back to the bathroom, she had used the lube to prepare the enema nozzle but then just left it sitting on the counter. Then it was a quick trip to the kitchen to grab the beer, it might not be as cold by the time they were done, but the last thing she wanted to do was question Wayne's instructions immediately before he popped her ass. Wayne was in the same position as she had left him although he had tucked his cock back into his pyjama pants in the meantime. She put the beer and the lube on the nightstand, and then looked to Wayne for direction. "I want to watch you take my cock out again." Carol got back on her hands and knees between Wayne's legs and unbuttoned the fly of his pyjamas and took his cock out, it hadn't lost any of its strength while she was away so she set back to licking it. "Ohh yeah, my slut is such a natural cocksucker." He'd said it again, this time it was a little less embarrassing, given that he'd said it not even five minutes before. "Open your mouth up for me slut." Carol pulled her mouth off his cock and just held it open. "tongue out," Wayne instructed, and then when she complied he took his cock in his hand and started slapping her tongue with it. "You want this cock bitch?" She really didn't but Carol knew the role she was deemed to play. "Yes Master." Wayne slapped her face a couple more times as Carol stared down at the bright red streaks her lipstick had left on his cock. "May I please suck your cock some more?" "Hmmmm, I think I'm done getting a blowjob for now. It's time to break you in another way." Master Wayne swung his leg up and over Carol so he could get up without her having to move at all, but staying in the same position on all fours. "I'll bet a slut like you has been fucked all the time haven't you?" "No Master, never." What kind of fucking mindgame was this? Wayne should know damn well that Carol had never been fucked, he had just created her a week before. "You're not trying to tell me a hot piece of ass like you is a virgin are you?" "Yes Master, I've never taken anything like that." "Taken it where?" Carol swallowed in shame. "In my ass Master, I have never taken a cock in my ass." She felt him grab hold of the base of the butt plug protruding from her ass with cross between a gasp and a moan Carol felt the plug open her asshole momentarily before it was pulled free. "I see you have been preparing for it though." Wayne put the plug down on the nightstand and Carol was relieved to see it was still clean, it hadn't been entirely so when she had taken it out for her enema. "Let's see how nice and loose you are Carol." She heard the top to the bottle of lube pop open and then a moment later felt a finger thrust inside her, slick and just a bit cold. It was certainly thinner than the plug, barely bigger than the enema nozzle but as soon as it was in it was drawn back out. Wayne finger fucked her for a few strokes, it certainly didn't feel horrible, it was not the painful miserable indignity she had been expecting, at least not yet, in fact there was something inside which actually felt good. When Master Wayne curled his finger a bit on some of the instrokes it brushed against something inside her ass, that must have been her prostate. It felt good but Carol focused on controlling her reactions, she did not want Wayne hearing her, she did not want to have to admit it felt good. The feeling of being stretched open grew more intense as Wayne eventually added a second finger, then a third. Once he was able to pump three fingers at a good pace in Carol's ass without an undue amount of resistance he pulled them out and Carol felt him wipe his hand on her ass. Then she felt Wayne slapping his hard cock against her ass. "Are you ready Carol?" "Yes Master Wayne." As ready as she would ever be. "Ready for what?" Carol sighed, Wayne was really going to make her say it. She hesitated, could she really say it, wasn't it enough that she was kneeling here on his bed, still dressed in the French Maid's outfit ready to let him have his way with her, did she really need to say it out loud? "If you want me to lube my cock first then you better answer me. What are you ready for?" Doing it was going to be bad enough, there was no way Carol wanted him putting it in without lubing himself up first. "Yes Master Wayne, I'm ready for you to put your cock in my ass." "Fuck your ass you mean," Master Wayne corrected, still slapping his cock on Carol's ass. "I want you to beg me to fuck your ass." Carol felt like she was going to throw up for a moment but knew better than to fight Master Wayne on this matter, she was going to do it anyway, how could it be that much worse to ask for it? She tried to think of any other way out of this abysmal situation, but it was pointless, if there had been another way out she would have taken it in the first place, she wouldn't be in this situation if she didn't have to. Master Wayne seemed to get impatient with her stalling because he stopped slapping his cock against her asscheeks and spread them with his hands instead. "Beg me to do it now, or I am putting it in dry." Carol couldn't help but give a single sob before she reigned herself in, she had to do this, it was what he expected of her and he clearly intended to fuck her ass one way or another. "Please Master Wayne. Please fuck me in the ass." Slapped her ass a couple more times with his cock, clearly he wanted better than that. "Pleeeeeeease Master, take your big fat cock and fuck me hard, fuck me in my tight virgin asshole." "Well since my little slut asked me so nice, I'll give you what you want." She heard another pop of the cap from the lube bottle and after a moment she could feel him pressed against the tight pucker of her asshole. She felt her body give as he pushed inside, this was it, now she was about to get fucked by a man. It was uncomfortable for sure, it just felt so weird as he pushed more and more of his cock into her. He was barely bigger in girth than the three fingers before him but it just kept going deeper and deeper. "Mmmmmm I like watching your soft little ass eat my great big cock. Such a hungry little slut you are it just keeps taking it all the way down." Finally Carol felt Master Wayne's pelvis brush against her ass, he was finally all the way in and then he started to ease himself back out again. He started thrusting in and out, back and forth, building up to a decent pace. As he got back to a steady pace that good feeling Carol had felt earlier from Master Wayne fingering her prostate started to come back. He fell into a rhythm fucking her at a steady regular speed, grabbing her by her hips and pulling her back into him as he fucked her. It felt so good Carol found herself unable to completely stay in control and she started panting in time to his thrusts, every jolt through her prostate was a little gasp, which soon became small, moans, she tried to muffle them but without actually being able to cover her mouth it didn't take long for Master Wayne to hear her. "That is good my little slut, I want to hear you moan like a whore. I want to hear your dirty talk, tell me how it feels for me to fuck you like this." Carol started simple, just letting herself moan in pleasure as she felt the electric tingle deep inside her ass, but shortly her wordless cries became single syllables, the first and most common of which was "Yes!" Somehow vocalizing it made her feel less ashamed about what was happening to her, every word made her want to say more. "Yes!" Soon turned into pleading cries of "Fuck me, oh, oh yes, fuck me." She knew what Master Wayne wanted and every moment of crying out in pleasure made it easier to say more and more. "Oh God, yes. Fuck me, show me what a slut I am for you Master, fuck me so hard in my ass." As she said more Master Wayne's strokes started to come slower in pace but harder in impact and he pounded himself against her until he grabbed two fist full of her skirt, slammed himself against her and just held himself there as she felt him start to shoot his cum inside her ass. This was it, it was done. As Master Wayne stopped thrusting the friction against her prostate stopped and the pleasure she had been feeling simmered off. Slowly Master Wayne pulled out and slapped her on the ass. "Go on now slut, get yourself cleaned up." "Cleaned up Master?" "Yeah, wash off your makeup and douche your pussy, The last thing I want is you leaking my cum out of your ass all over the bed." As Carol attended to that in the bathroom she found the Carol mindset retreating and Jim was coming back into focus, and with Jim came shame. What the hell had he just done. No matter the reason, he had begged and pleaded and panted for a man to fuck him in the ass. What the fuck was wrong with his life that he had just allowed himself to get fucked in the ass. He'd had to wash another man's cum out of his asshole for Christ's sake. Not even really sure how to deal with his he let himself slump into a seated position in the bathtub, letting the shower spray him in the face, washing away the remnants of makeup that had not already faded with the day and losing his tears among the water streaming down his cheeks.