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Cheating Boyfriend By Tiffany Parker The following story is a work of fiction and is copyright property of the author. Please don't repost it without permission. But most importantly, I hope you enjoy reading it. Chapter 1 Nathan woke up on Saturday morning. It was the second round of the NCAA basketball tournament in March and his friends were coming over to watch the games, have pizza, wings, and beer. They had all placed bets on the game which added to the excitement. He had even talked his wife Denise into serving them drinks weeks ago when he and his friends were planning the weekend. In reality, he had begged her on his knees to do it. Denise had relented because she knew how important that kind of silly thing was to the male ego and that Nathan would feel good looking like a big shot in front of his friends. That, plus Nathan had promised to take her on a weekend getaway to the beach the following weekend. It had been a long winter and the hectic work schedules of both Nathan and Denise had prevented them from getting away the last couple of months. "So who is Angela?" Nathan heard Denise's voice call out to him as he struggled to gain his bearings after a few too many beers the prior evening. Looking up, he saw Denise already fully dressed in a sweater and jeans with her arms crossed under her breasts and the sternest look on her face that he had ever seen from her. Nathan knew full well who Angela was. She was the pretty buxom blonde who provided certain oral services that Denise only provided these days when she was on her monthly menses or had a couple too many beverages. Even if Denise did provide that more often, Nathan wasn't a strong enough man to turn down the women who had all but come on to him. Stammering, Nathan lied, "I don't know who that is. What makes you think I know someone named Angela?" Denise's glare got even more menacing at her husband lying to her. Pulling his phone from her pocket, she punched the passcode on it, and pulled up the nude picture in his messages from the 23 year old tart titled Angela in Nathan's contacts and flipped the phone so Nathan could see. Nathan was flabbergasted and trapped. He knew it had been stupid to use his birthday month and date as the passcode on his phone. Denise had cracked it on the second try after initially inputting 1-2-3-4. "Oh, her," was all he could stammer out in response. "Yes her," Denise answered. "I can't believe you." "I'm sorry," he muttered. "More likely you're sorry you got caught," Denise countered. "But not as sorry as you're going to be." Chapter 2 Nathan climbed in the shower. After sending Angela a message that he didn't want to see her anymore and deleting the contact in his phone, Denise instructed him to climb in the shower and shave every hair below his neck. Grunting as he got in the shower, Nathan cleaned his body, rubbed shaving cream over his legs and arms, and used his disposable razors to shave all the hair off of his body. He wasn't a particularly hairy guy, but the total surface area required the use of three separate razors. Getting out of the shower, he heard Denise call in directing him to use her body lotion to prevent his skin from getting irritated or drying. Looking at himself in the full length mirror, he noticed his pale arms and legs seemed to be slimmer and frailer without any hair on them. Reluctantly, he rubbed lotion over his arms and legs noting the sweet smell of lilacs coming from it. Walking out of the bathroom, he noticed that Denise had a traditional french maid outfit laid out on the bed. Nathan gasped when he saw the outfit figuring out what Denise had planned for him. He noticed the dress still had its tags on it "I can't wear this," he stammered. "Well, not yet, "Denise commented. "We need to get you in your lingerie first." "I don't want to wear this or any lingerie," Nathan whined. "It's either do what I say today, or I go back to the divorce lawyer I contacted this week. You should have seen his eyes light up with dollar signs in them when I told him I had proof of a cheating husband with no prenuptial agreement. Nathan gasped at the thought of paying years of burdensome alimony to Denise for his indiscretions. A day of humiliation seemed like a better proposition to him. Tomorrow, he and her would be even and could start over he figured. He promised to himself that he would be a better husband to Denise going forward. Hanging his head in shame, Denise correctly surmised that he had given into her demands. Pulling out a black silk bra, Denise fastened it to his chest, and instructed him to slowly pull the black thigh high stockings up his smooth legs. After that she gave him a garter belt to wear and fastened that around his waist, Denise attached the black straps of the garters to the tops of the stockings. Reluctantly he pulled up the black thong that Denise handed him, noting how his package fit neatly in the front of it, and it felt like it was flossing his buttcheeks. Denise pulled out a set of breast forms and applied adhesive to the back of them and placed them in the bra cups with the instruction that Nathan should hold them against his chest for the next 15 minutes until the adhesive set. Nathan was left alone in the room for the next 15 minutes as Denise got a cup of coffee. With the breast forms in his hands, he noted they seemed to be approximately the same size as Angela's D-cups tits. Looking at the rest of his body in the mirror, he noted that his pale white skin contrasted well with the dark lingerie he was wearing. Denise returned at that moment and giggled at the sight of Nathan's member expanding in the tight thong. Nathan, looking down, blushed realizing that he was getting hard from checking himself out in the mirror. "Let's get you in your dress girlie," Denise joked. Dropping his hands from his tits, Nathan nodded in assent to his request. Denise pulled it over his head, while Nathan worked his arms through it, before Denise zipped it up in the back and smoothed it out over his petite frame. Reaching for the apron, she tied it out her husband's waist and double- knotted it in the back. Handing Nathan a petticoat, he pulled it up under his dress noting it made his skirt flare out and the outlines of the white lace trim could clearly be seen beneath the hem of his dress. He frowned knowing how effeminate he looked in it. "Time for makeup," Denise gleefully noted. Sitting him at the vanity, she got to work applying foundation, contouring his face for maximum effect, applying heavy eye shadow, liquid eyeliner, mascara and wet looking apple red lipstick. On his hands, Denise used red press-on nails to match his nails to his lips. Denise even gave Nathan blue contacts to wear, to obscure his naturally hazel eyes from his friends. Looking at himself in the mirror, Nathan could barely recognize his face. Denise had done a wonderful job feminizing his face. "Okay, here is the deal, Nathan," Denise started. "You are going to serve your friends today in your pretty little dress. You can either serve them as you are dressed now, or I can give you a blonde wig to wear, but in return, you have to wear a chastity cage for the next month. Nathan panicked. It was either have his best buddies see him dressed like a slutty submissive maid, or give up his ability to orgasm for the next month. He knew they would never stop deriding him over his outfit and makeup. Wearing a chastity cage would comparatively be private between him and Denise and over in a month. The choice was clear at that moment. "I want the wig please," Nathan pleaded. "First the cage," Denise giggled, producing an impossibly small metal cage that she manipulated behind Nathan's balls and over his penis, before locking it shut. The cage had an internal lock and fit extremely snugly over his decent sized dick. Going to the closet, Denise retrieved a platinum blonde wig with large curls that was parted on the left side. Nathan noticed the curls resembled the look when Denise got her hair permed several months back. Looking at himself in the mirror, Nathan was actually relieved to see a pretty woman instead of himself looking back in the mirror. Maybe he could pull this off, Nathan hoped. "How am I going to disguise my voice?" Nathan whined, realizing the one thing that he couldn't adequately feminize. "I'll tell your buddies that you are a recent immigrant from eastern Europe and don't speak English very well," Denise offered. "Well we both speak a little bit of Polish, which we each learned from our grandparents. That will allow me to relay their orders to you in Polish. Of course, you'll have to smile and do whatever I tell you like a good little maid, but I'm sure you were going to do that anyway." Nathan merely gulped and nodded in response to Denise's plan. It would work and let him be silent for the day which relieved him. "Time for your heels girl," Denise cheered, producing a pair of 5-inch stiletto strappy heels from the closet" Nathan was shocked by the size of the heels, "I can't wear those!" he stammered. "You mean you need to practice in them," Denise countered. Nathan simply nodded, and slipped them on his stocking covered feet and laced up the straps on the shoes. Standing up, he wobbled in his heels but maintained his balance. Smiling at her husband's plight, Denise had one more thing for Nathan "Oh, I have one more thing for you, sweetie." "What's that?" Nathan asked apprehensively. "The receipt for the french maid dress," Denise said, placing it in Nathan's hand. "Look at the date. I bought it the week you asked me to serve you and your friends for the basketball tournament. I figured it would help you score points with your friends. I guess the dress will still help you score points with them, just with you wearing it." Looking at the receipt, Nathan's wet red lips parted in shock at seeing what Denise was saying was true. Denise was going to bounce around like a little flirty french maid for him and his friends, but thanks to his indiscretions, it would now be him taking her place. He pouted at the plight of his own doing. Denise smirked at the internal plight of her husband. Whispering in his ear she taunted him, "Fortunately, we're both 5'6" and slim, when I found out you were cheating, I just knew this was the perfect way to get back at you. You look fabulous, I must say." Nathan was crestfallen, knowing Denise was absolutely correct, about everything. "Well you better get cleaning and cooking before your friends get here sweetie," she directed. Chapter 3 Nathan spent the next three hours cleaning the downstairs and preparing food. His feet were killing him. The red acrylic nails on his hands made it difficult to grip things. And the thong was riding his ass. He wanted to wallow in his plight, but it was 11:45 and his friends were due to arrive at any minute for the noon start of the games. A couple minutes later, from the kitchen, Nathan heard the doorbell ring and Denise greeted the men as they arrived all at once. "Now guys," Denise started, "Nathan got called into work on some last minute business deal, so he sends his regrets, but he also left you a nice little surprise." The men's eyes all lit up at the potential surprise. "Calling out in Polish, Denise yelled "Natasha, get your cute butt in here!" Nathan scampered into the living room of the house, his heart racing and his fake boobs bouncing in his silk bra. Arriving there, he curtsyed upon seeing his friends. He was terrified they were going to make out who he really was, but the lustful looks in their eyes terrified him just as much, maybe even more so. In English, Denise continued. "Guys this is Natasha. She's a recent immigrant from Poland. She doesn't speak English, but she is very submissive and eager to please. Just tell me what you want from her, and I can give her any order you want." Nathan stood there with a dumb look and forced smile on his face. Looking out at his friends, Nathan felt very vulnerable in his little dress around his friends. They were all over 6 feet in height, which Nathan was just short of that height, thanks to his heels. Paul and Maurice were very muscular, while Dennis had more of a wiry frame that contrasted sharply with his comparatively diminutive and dainty frame. Nathan was humiliated that he was so easily feminized and bigger men like them would never look like he did now. Nathan's internal thoughts were broken by an order called out in Polish by Denise, "Natasha, go get the guys beers! Quickly!" Nathan scampered off to the kitchen and cracked three beers and quickly returned, serving them to the men. After that, Nathan followed Denise's orders to serve the initial spread of food which consisted of buffalo chicken dip, sausage and cheese platter, and nachos. Around 1 pm things had settled down and Nathan was relieved he was able to sit down, albeit between Maurice and Dennis on the love seat. He felt cramped between the two men, and his stocking covered legs were pressed up against the coarse fabric of the men's jeans. Out of the corners of his eyes, he could clearly see the crotches of his friend's pants clearly tenting. On the couch, Denise was pressed up against Dennis. She had always found him attractive and was taking the chance to come on to him. Nathan pouted at the situation he was in, which only made him look more attractive to his friends. He was barely able to focus on the games. Had he been focused, he would have realized that his bracket was doing the best of any of his friends. Instead he was focused on the tight constricting bra he was wearing, his thong flossing his ass, the metal encasing his dick, and the tight pinch of his heels. Chapter 4 By 4 pm, the men were getting good and drunk from the steady stream of beer that Nathan had been steadily serving them in his Natasha persona. Denise figured the men were drunk enough for her to implement the next stage of Nathan's humiliation. "So, Dennis and Maurice, do you like the pretty little girl that Nathan arranged to serve for the afternoon?" They both nodded in assent. Denise knew that both of them were single and would have no problem coming onto her feminized husband. "Anyway, Nathan paid for all you guys to get blowjobs from the little slut." Nathan's eyes opened wide, at the thought of orally servicing his friends. Yelling out in Polish again, Denise directed Nathan to service Dennis or face the consequences. Nathan knew what those were, humiliation before his friends and a harsh settlement in divorce court. With the same forced smile as before, he sank off the love seat and to his knees looking up at Dennis and struggled to undo the belt and zipper on Dennis' pants with his red acrylic nails. Finally he was able to get them undone. Pulling down Dennis' pants, his erect cock popped out. While it was only about 6 inches in length, Dennis noted it was approximately the circumference of a red bull can. He blankly stared at it, not believing what he was about to do. He heard a familiar yell in Polish from Denise telling him to get to it, but an admonishment to Dennis to not touch Natasha's hair as she just had it permed. It was Denise's way of helping Nathan not get found out by his friends. Parting his red lips, he wrapped them around his friend's cock, looking up into Dennis' brown eyes with his crystal blue eyes from the contacts he was wearing. Working his tongue on the thick cock, Nathan bobbed up and down on it, the best he could. While he was working Dennis' cock like a runway, Nathan heard Denise excuse herself to the bedroom with Paul explaining that her and Nathan had an open relationship, and that Nathan would be fucking the slutty maid later that evening. Paul always had a crush on Denise as well and readily agreed to go upstairs with Denise. At the top of the steps, Denise lingered, watching her husband continue to suck Dennis' dick. Taunting she said, "You know Maurice, little Natasha has never had black dick, and she's really looking forward to sucking your cock. Enjoy." A wave of humiliation ran through Nathan's body at Denise's taunt, but he also felt a twitch of his dick in the chastity cage at the thought of looking forward to sucking black dick which confused him. He would have continued to contemplate that, but at that moment, Dennis exploded into Nathan's pretty mouth, cumming like a flood. Nathan struggled to swallow the large volume of fluid but managed to swallow it all. Nathan stole the last swig of Dennis's beer to wash the nasty taste out of his mouth before going to the kitchen, his ass sashaying more than he intended on the heels to retrieve another round of beers for his friends. He returned to the kitchen a minute later with another round of beers and could clearly hear moans from Denise and the sound of rhythmic slapping coming from upstairs. Nathan correctly concluded that Paul was fucking Denise doggystyle something that she rarely did with him, which slightly infuriated him. Hearing the doorbell ring, Nathan answered the door and curtseyed before the pizza guy who was wide eyed at the blonde buxom beauty in the maid dress standing before him. Nathan took the order of 2 large pizzas and wings, kicked the door shut behind him and returned to the men, and placed them down on the coffee table. Nathan had already prearranged and paid for the order, including tip, earlier that day. The pizza guy walked back to his beater Honda Civic with a telephone pole in his pants. Still hearing his wife's moans from upstairs, Nathan wanted to get angry with her. But instead of getting angry, he put the same forced smile on his face, and kneeled before Maurice. Something about the large size discrepancy between him and his friend was appealing on a certain level to him. Maurice looked down on him with a confident smirk on his face, knowing he was about to be the first black man this slutty girl ever experienced. He should have been upset at this slutty little minx treating his dick like some kind of fetish, but instead he greatly enjoyed breaking white girls into black dick, and he was going to enjoy pumping his seed down her eager throat. Fumbling again with the belt and zipper, Nathan struggled to get his friend's pants undone. Finally, he got the fly of Maurice's pants open, and he audibly gasped when Maurice's thick 9 inch cock flopped out of his pants, thinking it resembled a one eyed anaconda. The large mushroom head of Maurice's cock was taunting Nathan, as was his own dick trying to get hard in his little chastity cage. Submissively, he wrapped his red lips around the large head of Maurice's dick, savoring the taste in his mouth and licking the head with his tongue. Opening his mouth more, he took more of it in his mouth fighting to get it past his gag reflex and take it in his throat. Maurice smirked at the slutty maid kneeling before him serving him like a common slut. She really was trying to take his whole cock in her whore mouth. Nathan was taking it as a challenge to see how much dick he could fit in his mouth as his eyes bulged at the large member in his throat making it difficult for him to breathe. He found he could only take about 6 inches of the oversized dick in his throat before he had to break off gasping for air. Looking down at the slutty eastern european import, Maurice was impressed with her vigorous effort and figured she wouldn't be the last black man this slut sucked off. Quickly Nathan went back to work, wrapping his petite right hand around the base of the large shaft, as he enveloped the head again with his now surprisingly eager mouth, and started slurping again. Working in concert, he used his right hand to jack off Maurice while his lips and tongue worked the head and top of the shaft. The effects of Nathan's efforts were readily apparent as Maurice was moaning in pleasure. The moans elicited from Maurice encouraged Nathan to suck Maurice off more vigorously. Loud gagging noises emitted from Nathan's mouth as his vigorous bobbing on Maurice's large cock kept hitting his gag reflex. . Nathan's cock strained even more in his cage as Maurice kept moaning the name Natasha in pleasure. Nathan felt the large dick twitch in his mouth and prepared for the inevitable flood of cum. Maurice came like a geyser, with a large forceful grunt, as his large cock twitched and spurted five times unloading a massive flood of cum in Nathan's eager mouth. He struggled to swallow it all but it was just too much, and a fair amount leaked out of his mouth and down his chin. Looking up at Maurice, Nathan felt shame in failing to swallow his friend's cum load. Undeterred, Maurice scraped his cum off of the slutty girl's chin with two fingers and offered it to the slutty bimbo kneeling before him. Without breaking eye contact with the large man, Nathan closed his red coated lips around the base of Maurice's meaty fingers, and sucked them clean. By that time, Paul had finished with Denise and she had come to the top of the steps dressed in a white silk robe to watch Nathan finish off Maurice. She smirked at the effort he had put in to suck off his large friend. "Natasha," Denise called out in Polish once again, "Upstairs. Now." Nathan rose to his feet, the taste of male sperm ever present in his mouth, smiled wryly at Maurice while smoothing out his dress and walked toward the stairwell, his cute butt sashaying as his petticoats swung back and forth with each step. His dick was pressing hard against the cage as he felt his friend's eyes laser focusing on his ass. Chapter 5 Nathan dutifully followed his wife into the bedroom and kneeled on the floor by the bed as she ordered. Sitting on the bed in front of her humiliated husband, she disrobed and spread her legs revealing her messy pussy and cum streaked thighs which elicited a wide eyed stare from Nathan. Denise issued a simple order, "Lick." Nathan brought his smeared lips to his wife's slick messy region and submissively licked Paul's creamy cum off of her milky thighs. Satisfied that her legs were clean, he turned his attention to her messy vagina. Licking his wife, he noted the taste of Paul's cum mixed with his wife's vaginal juices. He quickly had his wife on the edge of orgasm. Downstairs the three friends were eating the pizza and wings that had just arrived and heard the loud moans coming from Denise and correctly surmised what was going on. They were surprised that Nathan and Denise were apparently swingers as Nathan always came off as the conservative type when it came to sex. Now that they thought otherwise, they couldn't believe he would miss such an amazing party, at his house no less. They truly had no idea their good friend was feminized as the lovely Natasha and had been serving them all afternoon. About 15 minutes later, Denise was fully satiated and had directed Nathan to repair his lipstick. Sitting at the vanity, she giggled at her husband painting his lips apple red like a common street whole while he sat there in his dress with his legs crossed in a ladylike fashion at the knee. That was the moment that she knew for sure that her and Natasha would have many more slutty experiences together over the coming months. Noting his lipstick was repaired, she smiled and said, "Back downstairs sweetie. Time for the grand finale." Nathan nodded and rose to his feet and walked toward the steps with his hips once again swaying with each step. Carefully, Nathan made his way down the steps feeling the eyes of his friends on him with every step of his pointed heels on each step. At the bottom of the steps, Denise commented, once again in Polish, "You have one more blowjob left to give, Paul hasn't had a chance to sample your slutty cocksucker lips yet." Paul's ears perked up at the sound of his name, as the pretty girl he knew as Natasha walked before him and sank to her knees. Just like before, Nathan struggled to get his jeans undone. He felt humiliated knowing he had to suck off the man, a friend, who had just fucked his wife minutes ago. Even more humiliating, was the feeling of his restrained cock twitching in its cage at being cuckolded. That thought was interrupted by Paul's cock popping out of his pants. While it was nowhere as big as Maurice's dick it was still 7 solid inches, which was larger than his dick, even when it was unrestrained. Blushing at having the smallest dick in his friend group, Nathan parted his freshly coated lips and took Paul's member in his mouth. Nathan and Paul had always had a bit of a friendly rivalry between them and it had extended to chasing women, playing golf, and making money. More often than not, Nathan had the upper hand on Paul, but today wasn't one of those days. It was degrading for Nathan to have to be bobbing on Paul's dick while dressed like a bimbo after Paul had just fucked his wife. In reality, Denise had chosen to fuck Paul because she too had correctly sensed the tension and friendly rivalry between them at times. It was the cherry on top for her scheme at getting back at her cheating husband. Standing there with her arms crossed, she watched intently as her husband sucked off the man she had fucked minutes ago. Her pussy still tingled from the fucking and the licking slutty Natasha had given it. Nathan continued sucking on Paul's cock working feverishly just because he wanted it to be over. Paul, having cum not even a half hour earlier, had more staying power than usual. By now, Nathan's poor jaw was aching after a long afternoon of oral servitude. After 15 minutes of grueling and humiliating cock sucking, Denise sensed that Paul was getting close and ordered Natasha to stop in Polish. Denise, kneeling next to her feminized husband, took Paul's cock in her mouth and proceeded to work it. Nathan's painted lips parted in shock at his wife sucking off Paul. She worked his cock, using methods he hadn't seen her use since their dating days and within two minutes Paul had exploded his second cum load of the day into Denise's eager mouth. Turning to her husband, she grabbed his dress and forcibly pulled him toward her offering him an open mouth kiss while her breasts pressed into his fake breast forms. The men roared in cheers at the lesbian makeout and snowball session, as Denise continued her forceful oral assault of her husband's mouth with her lips and tongue. After a minute, Denise broke the kiss, and slowly pulled away from Nathan, a faint string of cum connecting their lips. Nathan wished the world would swallow him whole at that moment as his friends eyes were fixated on him thinking he was the sluttiest recent import from eastern Europe. Still kneeling, in a state of shock, Denise took control and rose to her feet, thanked the men for coming and asked them to get ready to go, as Natasha had fulfilled her obligation to them. Paul, Maurice, and Dennis saw no reason to stay longer. They had their fun, were spent, a little buzzed, and they could each return home and finish watching the rest of their games that day. In truth, they hadn't paid much attention to them for a while as Natasha and Denise had diverted their attention elsewhere. Denise saw them all out, and planted a kiss on Paul's cheek as he left. Seeing this caused Nathan's dick to twitch once again in his pants. Denise walked over to her still kneeling husband and whispered in his ear, "You were wonderful today babe and well on your way to making up for your past indiscretions. I don't think we've seen the last of Natasha though. I'm going upstairs to lay down. You clean up down here, then you can change out of your pretty outfit." Denise headed upstairs while Nathan worked for the next hour to make the downstairs as spotless as it had been before his friend's had stopped over. Afterward he was thankful to get out of his overly feminine outfit. Aftermath The next day Nathan showed up to Dennis' house for the 4th day of the opening weekend. All his friends wanted to do was talk about the great experience they had yesterday at his house. Instead of revealing the truth, Nathan went along with the fiction that he and his wife had an open relationship and often took other partners into their bedroom activities. He regaled his friend with a story how he took slutty Natasha in all three of her eager holes and had her begging for more. In reality, Nathan was still extremely horny from his time as the slutty Natasha and craved an orgasm, one that was sure to elude him for the foreseeable future thanks to the cage tightly constraining his dick. Maurice in particular seemed most enthused at Nathan's story about screwing Natasha and asked if the group of them could see her again. Poor Nathan's dick throbbed in the cage and even leaked a little at the thought of servicing his large friend again. In truth, part of him looked forward to dressing as Natasha again. Eventually Nathan was able to steer the conversation back toward the games on television and the current wrecked states of each of the guy's brackets. Still though, as Nathan sat next to Maurice, he was unable to focus on the games as his mind kept drifting back to the events of yesterday and the thought of what was currently resting comfortably in Maurice's jeans. The End (for now, Natasha may return in a future story) I hope you enjoyed this story. I appreciate any comments or feedback that you have. - Tiffany