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Off to the Races Belladonna [Author's Note: Based on a suggestion by Renny Renne] "You can't really think you'd make a better woman than me?" "Oh, I know I can," Christian teased his assistant. "You do know I'm a really girl, right? Just so we're clear," Marissa retorted, bemused by the subject of the conversation she was having with her boss. "Men are always better at being women than women are." "Do you think you're prettier than me?" Marissa asked, placing her hands on her waist as she did so. Christian laughed as he shook his head and replied, "Of course, not. Look at us..." "So, how could you..." "There's a lot more to being a girl than being pretty." "I'll give you that, but not according to men!" "Ah...but according to this man..." Christian replied with his hands held out to the side. "Oh, that's charitable..." Marissa rejoined with a smirk. Christian put his hands on his hips and stared down at Marissa in silence before she continued, "Like a man would really be having this conversation." "I'm just stating facts! There's nothing manlier than that." "There's nothing manlier than stating you'd make a better girl that a real girl?" Marissa retorted, shaking her head at the absurdity of her boss's words. "Well, when you put it like that, you make it seem..." "Queer," Marissa interjected. She grinned at her boss's peeved look before she added, "You know, not in the gay sense, but in the strange sense." Christian laughed before he responded, "Oh, of course. Thanks for clearing that up!" A faint smile came upon Marissa's face as she replied, "I think you would make a convincing little lady." The smile fell from Christian's face while he processed his subordinate's words. He cocked his head and asked, "Why's that?" "Look at you. You're a little shortie with that long hair and cute button nose..." "And two eyes made out of coal." "Not those baby blues," Marissa countered before continuing, "I bet you get confused for a girl all the time." Christian rolled his eyes before she Marissa added, "At least from behind." "There is no way that I could ever be confused with a girl," Christian countered. Marissa laughed at the certainty conveyed by her boss's tone. Christian glared at her in response before she asked, "Is there a way we could prove that?" "I don't see how?" Christian replied, placing his hands back on his hips. "Unless...we get you in the right dress," Marissa responded with a laugh. "Like that would ever happen," Christian said with a shake of his head. "Oh, so, you don't think you could do it?" "No..." "Really, says the man who thinks he makes a better girl than me," Marissa teased. "What do you want me to do?" Christian asked with evident exasperation. "I don't know..." "You can't possibly think I'm going to put on a dress and..." "I didn't say that." "You just did!" "I was just joking." Christian smiled at her as he double downed, "I know, because you know I'd make a better girl. "Oh, really?" "Yup," Christian answered with a grin. "Well, in that case, why don't you prove it?" "I would if I could." "Oh, but you can." "How could I do that?" "By putting on that dress you keep talking about." "You were talking about it," Christian countered. "Whatever," Marissa replied before she added, "I think you could make a passable girl." "Now, that's crazy," Christian replied with a laugh. "No. I'm sure of it. You got potential," Marissa responded, drawing out the last word in the process. "And what are you going to do with it?" Christian inquired. Marissa grinned as she got to her feet. She stood up and stepped towards Christian. Christian stared up to meet her green eyes. Marissa clasped his long blonde ponytail and pulled it from behind his head to rest it on his shoulder. She smiled as she said, "I could do a lot with that, Blondie." Christian squirmed at her words before he inquired, "Like what?" "I could tease it up. Make it look real pretty, just like your pretty blue eyes." "Jealous?" Christian joked. "Like a green eyed monster," Marissa replied with a laugh as she tilted her head. "It takes more than hair to make a girl," Christian responded. "No doubt, but with your soft features, you could definitely pull it off." "Are you calling me dainty?" Christian countered. Marissa laughed while she answered, "I never said that." "You certainly implied..." "You started this conversation," Marissa countered. Christian nodded in admission before he said, "It doesn't seem like a fruitful area of discussion." "I suppose," Marissa replied as she gripped his ponytail and pushed it back to its familiar place behind his head. Christian shook his head at her and added, "It's not like there would be a way to prove it." "Prove what?" Marissa asked. "Nothing," Christian replied, turning away from her as he said the single word response. "That you'd make the better girl? No, that's a matter of opinion." "I think I'd be the consensus choice," Christian replied, stopping and turning to look at his assistant as he did so. "Why don't you man up and prove you could even be considered a girl?" Marissa replied, feeling challenged by her boss's declarations. "And how would I do that?" "Let me take a crack at you." "Oh, you'd just love that." "I do like a challenge." "But how would it prove anything."' "We need to get an impartial judge." "I wouldn't want anybody to know that I'm a guy in drag." "We wouldn't tell them." "Then, how would they know?" "So, you agree with me." "Huh?" "I told you could make a convincing girl." "Oh, come on." "You said, how would they know?" "Are you talking about showing me off to strangers?" Christian inquired with a tilt of his head. "Seems like it could be a lot of fun," Marissa replied with wide eyes and a smile. "It sounds dangerous!" "The bar by my house does a whole Derby Day celebration each year. There's tons of people. The men are all betting and drinking and most of the girls just drink and focus on the hats. Nobody's going to be focusing on you," Marissa replied, trying to jokingly reassure her boss. "I don't know about that..." "Oh, so, you're not so confident, now?" Marissa retorted with a laugh. "I was never confident about looking like a girl." "But you, somehow, think you make a better one than me?" "I meant mentally." "There's more to being a woman than what's up here," Marissa replied as she tapped her temple. "Isn't that the complete opposite of what every woman says?" Christian rejoined. Marissa paused before she nodded with a grin while she answered, "Most men don't challenge us this way though." "What's in it for me?" "The satisfaction of proving you can make a woman, let alone one better than me." "Doesn't seem like something I really want." "Then, why did you bring it up?" Marisa countered. Her words were met by a shrug of Christian's shoulders. Marisa sucked her lips into her mouth for a moment before she said, "Okay. Okay. All right, how about if you are not recognized as a man, you have to spend a month as my secretary." "What?" Christian bellowed before letting out a nervous laugh. "Oh, and in my heels too!" "I still don't see what's in it for me? That seems to be all for you," Christian retorted, blushing at his assistant's words. "I don't know. What do you want from me?" Christian stared blankly at her. Marissa laughed before she added, "And keep the request PG." Christian blushed at her insinuation that he would ask for something inappropriate. He knew well enough that she had no doubt that he would never do so. Christian shrugged again before he said, "I can't think of anything." "Really? So, you're the man that has everything?" "I have enough." "How about a year of maid's service?" "You're really going to clean my house?" Christian asked with a disbelieving shake of his head. "Oh, hell no, but I have a friend who runs a company. I'd pay her to do yours and mine." "That's nice, but it's still not enough to convince me..." "Okay, how about a year of a maid's service, and I dress up as something you think is embarrassing for a day." "What?" "You think you're risking being humiliated, humiliate me if I don't make good on my promise." "And how does a man go about humiliating a pretty, statuesque girl?" "I'm not giving you any ideas! Surprise me," Marissa retorted. Christian laughed before he asked, "Are you serious about this?" Marissa gave him a nod before she inquired, "Are you?" Christian gave her a blank stare before he answered her challenge, "I'll do it." "You will?" "Called your bluff?" Christian retorted in response to his secretary's surprised tone. "No. I'm all in. It's a bet." "It's a bet," Christian said, repeating her words, surprised that she did not back down. Christian's mind raced while he turned and walked back into his office to go back to working. A few days passed before Marissa brought up the subject again. As he entered the office, Marissa asked, "Are you ready for tomorrow?" "For what?" Christian asked. Marissa gave him a disbelieving look before she asked, "You didn't forget our bet?" "You're not really going to hold me to that?" Christian asked, squirming a bit as he did so. "Why not?" "It's going to be humiliating when people realize..." "No one's going to realize. Trust me." "But, if they do..." "You get tit for tat with me..." "It's not the same." "This isn't Cheers, Christian. We're going to a place where, literally, no one knows your name." "But they know you!" "I'm not a regular, Christian. I only go there a handful of times a year." "How can you be so sure that I can make a convincing girl?" "The height is a help, short stuff." "That's not near...ly...enough." "The smallish feet and Donald Trump hands, your smallish nose, that soft chin, those pretty, high cheekbones...Oh, damn it, girl! You could be strutting down the catwalk in Louboutins right now if you were a few inches taller," Marissa cracked. "Oh, come on," Christian replied with blushing cheeks. "Aren't you the least bit curious?" Marissa said. Christian shrugged before he inquired, "Why are you?" "I haven't done a girl's makeup since college. It was a lot of fun." "Are you trying to relive something through me?" "It could be fun," Marissa teased. "You just want to tease me about getting me into a dress." "That'll certainly be a lot of fun," Marissa admitted with a laugh. "So, you just want to humiliate me. Let's be clear about this." "I don't want to humiliate you. I've dealt with that too much." "When were you ever humiliated?" Christian asked in disbelief as he gazed up at his secretary. "Christian, I'm 6' tall." "That's a good thing. Me and the rest of my fellow vertically challenged dwarfs would kill for that." "It's nice. I'll give you that, but it attracts some looks." "Again, most girls would like that..." "I do, sometimes..." Marissa began to respond as she saw Christian crossing his arms with a look of incredulity on his face about her statement. "Okay, more times than not, but, when I was a kid, it wasn't good." "What do you mean?" "I was 5'6" by the time I was ten. I was the tallest kid every year until I was in the 8th grade. Everyone used to tease me and call me a giraffe." "Oh, come on...." "I wasn't the most graceful girl either. I was kind of ungainly." "Has that changed?" Christian joked. Marissa gave him a glare before she added, "As I was saying, I know what it's like to be humiliated." "Try getting your head stuck in a toilet," Christian retorted. "That happened to you?" Marissa asked with a furrowed brow. "No, but it happened to somebody," Christian answered. Marissa shook her head at his response before she said, "I'm just saying, I wouldn't agree to something that would embarrass me that easily because if you get embarrassed, I get embarrassed. That's the deal!" "And exactly how would I embarrass you?" "I really don't want to give you any ideas!" Christian laughed at her before he said, "But what would everyone think if you won?" "Who?" "The people in the building, the attendants..." "You're asking how the garage attendants would feel. They never see you. They never talk to you. I'm the only one of us who talks to any of them." Christian nodded, aware that she was telling the truth. He knew that the employees of his parking garages only dealt with Marissa. He did not like having to bother with them. It was part of the reason that he hired Marissa as he developed and leased more parking garages. He knew that Marissa could do his job too. She had done it before when he felt like off loading his work on her. It was a simple matter of making sure that the amounts that came in added up with the monthly clients, which was augmented by the non-regular users. Payroll was limited to the handful of employees at each site. Paying rents, mortgages, taxes and utilities were something that she already did on his behalf as well. "You're just stalling because you're scared," Marissa teased. Christian shook his head as he said, "All right, I'll do it." "You will?" Marissa replied, taken aback by his words. "Sure, if only to make you suffer by making you wonder what I'm going to have you wear on Monday after some closeted, jerk off clocks me in the face." "Won't happen," Marissa replied with a hint of certainty before she made plans to meet with her boss at her apartment the next day. ----------------------------------------------------------------------- The next afternoon, Christian knocked upon Marissa's door with a knot in his stomach. While part of him was intrigued over how convincing a woman she could make him, another part of him was sure that he would be entirely unconvincing. Marissa drew the door open. She smiled at her boss. She let him in and said, "I've got everything ready for you." "Okay." "I put everything I want you to put on in the bathroom," Marissa responded, her smile growing larger at the sound of the nervousness in her boss's tone. Christian nodded in silence as he followed her through the small apartment and into her bathroom. Christian came to a stop as he saw the panties, tights, bra and socks. "What am I supposed to do with all that?" "You're going to put it all on, and I'm going to hand you a dress." "How am I supposed to do that?" "Well, the panties are just like putting on briefs. Pick one leg up and then the other," Marissa answered. "Ha...ha..., but what about the rest?" Christian asked, surprised by his secretary's expectation that he knew how to put on girls' undergarments. Marissa grabbed the bra and said, "See this hook in the front. Just put your arms through the snaps and hook it up. When you're done, shove in the socks in the cups and, voil?, you've got big girl breasts, girlfriend." "I don't think it's that easy, and what about the tights?" "The tights aren't a big deal." "Do I even need them?" "It's too cool outside for bare legs. You'll freeze on the walk back." "I guess," Christian replied as he picked up the tights and pulled at the waist. "Aren't these delicate?" Christian added, darting his eyes up to Marissa's as he did so. "They're the highest denier they make." "What the hell does that mean?" "They're the least delicate tights they make." "But, they're still delicate!" "Christian, I put some thought into this. It'll be alright." Christian gave her an inquisitive look before he countered, "Well, if you gave it some thought, I'm sold." Marissa rolled her head in response to Christian's sarcasm before she explained, "I froze them so they wouldn't tear as easily." "You can freeze tights?" "Yes. You wet them down and freeze them in a baggie. Once they thaw out, the fibers get tighter and stronger. It makes them harder to tear." "This seems like a lot of work." "It takes a lot of work to be a girl, let alone one better than me," Marissa retorted. Christian nodded before Marissa closed the door to let him get dressed after telling him to roll the tights down before he stepped into them. Christian locked the bathroom door before he removed his clothes. He pulled his boxers off last before he stepped into the black, cotton panties. A grin came upon his face as he felt the softness of the panties as he brought them up his sparsely haired legs. The sight of an erection his panties made Christian blush. Christian shook his head as he thought, 'Why are you blushing? No one can see you!' After he pushed his humiliated thoughts to the back of his mind, he reached for the matching, plain black bra and worked his arms through the straps. While locking the front clasps, Christian's eyes veered down to the white socks that Marissa had left for him. His fingers left the clasps to reach for the socks before he stuffed each cup. Once he finished, Christian cupped his bra cups to check that each stuffed cup was roughly the same size before he took hold of the tights. Following Marissa's instructions, Christian began to roll the black tights down before he placed his toes into them. He grinned at the soft feeling encasing his feet before he unrolled the tights over his ankles and calves. Another erection followed while he brought them up his legs and over his hips before he reached for the doorknob. His hand jerked away from the lock as he caught a glimpse of his noticeable arousal from the feminine undergarments he was wearing. Christian shook his head and muttered, "I can't let her see me like this." Christian tried to think about other things to get his mind to focus on matters that would not excite him. Marissa grew impatient as she waited for Christian to finish dressing. She called to him, through the bathroom door, "Are you okay in there?" "Just finishing up," Christian replied in a near panic. "Well, hurry up!" "I'm trying," Christian muttered before he noticed that his erection had largely subsided. Christian let out a deep breath before he poked his head out the door to call out to Marissa. Marissa smiled as she approached him with a white, poplin dress in her hands. Christian's eyes widened while he examined the dress's eyelet, pinwheel detail, as well as the scalloped trim at its cuffs and hem. The grin on Marissa's face grew as she asked, "It's so pretty, right?" "Sure," Christian replied while he reached his arm out the door to clasp the three-quarter sleeved dress. Marissa laughed at the sight of the bra strap on her boss's exposed shoulder while he took hold of the dress. Christian blushed at her laughter while he closed the door behind him. Marissa walked away from the door with her hands over her mouth, as she tried to muffle her laughter. After locking the door again, Christian put his back to the door. "What the hell are you doing?" He asked himself. He gazed down at the dress. As he examined it, he realized that it was the kind of dress he liked to see on a girl. A smile came across his face while he brought the dress over his head. He pulled the cotton dress down over his body and stared down at the bust line. Christian was relieved that the dress's v-neck ceased its plunge above where his bust should be. Noticing the fit and flare silhouette of the dress, Christian spun in place for a moment, enjoying the feeling of his nylon covered soles moving on the tiled floor as he did so. Christian smiled at his reaction, feeling that the dress's silhouette gave him a more feminine appearance as he reached for the rear zipper. He arched his back as he struggled to zip up the dress. A few fruitless attempts to finish bringing it up his back caused Christian to give up. He drew the bathroom door open before he called out, "Marissa, can you come in here?" Not seeing or hearing her, he stepped out of the bathroom. Christian sensed the feeling soft rug of her hallway while he approached her living room. It felt much better to him than the cold ceramic tile that had been beneath his tights covered feet earlier that day. Hearing him approach, Marissa got up off the couch and grinned at his appearance as she gazed down at him. She shook her head as she said, "You don't think that body can pass itself off for a girls?" "It's not my body I'm worried about," Christian replied honestly before he asked for her help with the zipper. "No problem," Marissa replied as she stepped behind him. Christian could feel her towering over him. He twisted his head and took in the blue and white, halter-top dress that she had put on while he was getting dressed. He felt every inch of Marissa's 6 inch height advantage as she reached for the zipper of his dress. She then asked, "Can you get your hair out of the way?" Christian clasped his ponytail and brought it over his shoulder. Marissa patted his side as she said, "Thank you." "No problem," Christian replied, flustered by being turned on by her too familiar touch. Marissa brought the zipper up his back and took a step away from him. With the dress secured over his body, Marissa told Christian to follow her into her bathroom. Christian followed behind her, struggling to keep his eyes away from her swaying rear, before she sat him down on the toilet lid to style his hair. Marissa reached for the curler that she had left warming for him. "What are you planning on doing?" "I'm just going to give your flat hair a little life," Marissa answered as she ran her fingers through his long blonde hair. She brushed out a few tangles before she put down her brush. After checking the temperature of the curler, Marissa squirted Christian's hair with a heat protection spray before she took hold of a clip. Christian watched her with interest as she clipped his hair into big sections. The clips felt odd in his hair and he felt uncomfortable sporting them, but he sensed that Marissa did not seem to pickup on his unease. Once the last clip was in place, Marissa started curling his hair from an inch before its root before proceeding down with the large barrel that left loose waves of hair in its wake. Marissa moved onto the next section of his hair as she curled it again before she released some of the sections of his hair down from their clips. She moved from one section to the next before she finished curling his hair and ran her fingers through the curls a few times to loosen and separate them. "Can't you use a brush?" Christian asked as Marissa continued running her fingers through his long hair, unknowingly arousing him while she did so. Marissa responded with a shake of her head as she told him the brush would destroy the curls and leave his hair only wavy. Christian's eyes fixed on hers as asked, "Is that really a problem." "It's not the look I'm going for," Marissa countered, disregarding his complaint by continuing to run her fingers through his hair. Once she finished, Marissa set his curls with her hairspray. The flowery scent of the hairspray made Christian's manhood twitch. His eyes darted away from Marissa as she continued to spray his hair. 'Get a hold of yourself,' Christian counseled himself while he fixated his eyes on the grouting of the floor tiles. After finishing spraying his hair, Marissa turned her attention to doing his makeup. Christian watched as she produced a makeup bag and began to take out cosmetic after cosmetic. "Is that all for me?" He asked with some alarm. "Relax. It's all going to look understated. I wouldn't step out the door with you if you looked like a Drag Queen." Christian nodded, hoping that he was in good hands. Marissa started with his foundation before she coated his lips with lipstick. Smacking his lips at his direction, Christian watched as Marissa reached for her eyeliner. Christian winced at the sight. "Don't get that in my eye," Christian whined as Marissa began to apply his eyeliner. "Okay, let's make like I'm Claire and you're that weird girl played by Ally Sheedy. Just close your eyes like this and let me do what I got to do," Marissa countered. Christian complied with his secretary's request as he said, "That scene didn't work..." "Well, it's working for you right now," Marissa replied, cutting him off as she continued to apply his eyeliner. Once she finished with it, Marissa applied his eye shadow. Christian kept his eyes closed as he asked, "Do you really know what you're doing?" "No, I just look this fabulous naturally," Marissa responded, unable to hide her sarcasm before she added, "You can open your eyes now." "I don't look like the weird chick from an 80's movie, do I?" Christian inquired with a smile. "No. That's not my style. I'm more into the make you over as a mall princess so you get the cute jock look," Marissa answered. Christian eyes popped open to flash an angry glare at her. She smiled at him as she told him to keep his eyes open while she did his mascara. Christian flinched as she approached his eyes with the applicator. Marissa scolded him, "Stay still like a big girl." Christian huffed before he managed to keep his eyes open while she coated his lashes with the cosmetic. As she finished, she furrowed her brow. Christian gave her a nervous smile before he asked, "Should I take it you're getting nervous that this might not be as easy as you thought?" A grin came across Marissa's face while she shook her head and replied, "I've got the safest bet of anyone today." "I wouldn't bet on it." "Too late," Marissa replied before she finished with his makeup. With his makeup complete, Christian got up to follow Marissa into her living room. His eyes widened as he stole a glance at his reflection in her vanity and thought, 'Holy shit!' Marissa grinned at the conflicted look on her boss's face before she said, "Wait right here." "Where am I going to go like this?" Christian inquired, holding his hand out to his sides. "I don't want some nice, big, strong dreamboat to come in and swoop you off your feet before I get back," Marissa replied with a wink. Christian rolled his eyes at her as he watched her scurry off into her bedroom. He stared at the pictures of her walls while he waited for her to return. Christian's eyes opened to their widest as he saw the large, pastel green hat in Marissa's hands as she emerged through the doorway. Christian took in the large, white flower ribbon that adorned it above its white trimmed brim with a shake of his head. "Where did you get that?" Christian inquired with his stomach churning over the look of the hat. "I wore it last year," Marissa admitted. "There is nothing that I can dress you up in that is more embarrassing than that," Christian countered. "Let's hope you don't get the chance to find out," Marissa countered as she walked up next to him and placed the hat atop his head. Christian cringed as she yanked it over his head before he caught sight of the pair of white wedges with a crochet lace top and faux cork, beige heel and platform she had selected to pair with his outfit. "Those look pretty high?" Christian replied, flashing his secretary a worried look as he conveyed his concerns. "Would you prefer real heels?" Marissa countered with a grin as the wedges dangled from her fingertips. Christian shook his head as he took the rounded toe wedges from her and worked his contrasting black tight clad feet into them. As he finished putting the second shoe on, Christian stood up and felt taller than he ever had when he stood next to Marissa. The feeling did not last long, as Marissa soon put on a pair of wedges of her own that reasserted her height advantage. "How do you feel?" Marissa asked while she dumped his keys and wallet into a pocketbook that she was lending him for the day. "A little nervous," Christian replied, unable to believe that she did not recognize it on his face while she led him towards the door. "You'll get over it," Marissa responded as she put on a light jacket before she handed one to Christian. "I hope so," Christian responded as he looked over the yellow jacket and wondered if she was trying to make him look like a marshmallow peep. "You better, because you need to give a real performance today." "What's that supposed to mean?" Christian asked as he put his arms through the sleeves of the bright yellow jacket. "You're going to act like a girl through and through." "Why?" "Because we bet that you could make a believable girl. I'm not going to stick with my part of the bet if you're going to go in and there and act like John Wayne." "Did John Wayne wear wedges too?" Christian joked. "No, but he did wear big hats." "Not this big," Christian replied as he clasped at the bright, floppy hat upon his head. Marissa shook her head as she replied, "Well, I'm not going to be humiliated because you choose to act like a guy to give yourself away." Christian shrugged before Marissa inquired, "Are we clear?" Christian gave her a nod before she placed on a small hat and opened the front door for him. Christian shook his head as he said, "Wait a minute!" "What?" "You don't want to me to give myself away, but I'm the one wearing this hat?" Christian inquired. "I can't wear the same thing two years in a row." "Why not?" "A girl needs variety. It's the spice of life." Christian gave her a hat an inquisitive look while he stepped outside before Marissa locked the door to her apartment and led him towards the elevator. As they rode the elevator down, Christian asked, "Okay, what is with the mini-hat?" "What? You wanted to wear it and, now, that I'm wearing it, you don't like it. Is that it?" "No. It's weird looking. It looks undersized." "It's stylish," Marissa rejoined as she clasped the red fascinator that rested on top of her head, which was adorned with matching red feathers and bows. "If you say so...," Christian countered. "I saw Kate Middleton wearing one just like it." "Oh, so, it makes you feel like a princess?" Christian joked. "Exactly. That's why I didn't give it to you. I didn't want you running off with prince charming while I'm stuck with some seedy bettor." Christian smiled at Marissa's kidding while they exited the elevator and left the building. As Christian walked beside her on the sidewalk, Marissa asked, "So, how do your feet feel?" "Fine," Christian countered. Marissa smiled as she said, "Those are comfortable shoes." "Do you have a pair of them?" Christian asked. "You're wearing them," Marissa countered. "Really?" "You didn't know we wear the same size?" Marissa asked. Christian shook his head before Marissa added, "What did you think I meant by saying you'd be wearing my heels." "I thought you meant heels you picked out." "No. I much prefer the literal meaning." Christian's mind raced as he thought about the fact that he was wearing a pair of his secretary's shoes. Marissa grinned at him as she asked, "So, what pair do you want to wear on Monday?" "Let's not get ahead of ourselves." "I'm an optimist," she replied before adding, "I think you always liked that red pair I wear sometimes." "I wouldn't know," Christian lied. "Really, you stare at them enough." Christian blushed in response, prompting a smirk to come across the face of his secretary. He was embarrassed that she noticed the looks he gave her shoes. 'God, I hope she doesn't think I have a shoe fetish,' Christian thought. As they continued down the sidewalk, a man walked past them and turned his head to look them over. A smile came across the man's face as Christian looked over his shoulder and caught the man's glance. "That guy just checked us out," Christian whispered. "Did you think we were going to be inconspicuous with the hats?" Marissa replied, amused by Christian's surprised tone. She smiled as she added, "And that's one for one for me, girlfriend." Christian shook his head before he saw the bar a block a head of them. He could hear a crowd cheering at an outside television that was carrying the broadcast of a late afternoon race. Christian's heart started to race as they approached bar. Marissa clasped his arm and led him through the crowd. Christian sucked his lips into his mouth, tasting his lipstick. He was afraid that one of the bettors would see him for what he was as he passed through them. They made it through the bar doors and looked around the crowded room. Marissa led him towards an open two-seat table and sat down before a waitress came over and took their drink orders. She gave them short compliments about their hats and outfits before she scurried off to place the order with the bartender. Christian's eyes fixated on the waitress's shapely rear that was hugged tight by a pair of skintight, black jeans. The feeling of Marissa's long fingernails digging into his right hand caused Christian's head to jerk towards his secretary. He flinched as he pulled his hand off the table and covered his right hand with his left. Marissa shook her head at him while she leaned over the table to quietly remind him, "Remember, act like a girl! Step one, don't ogle other girls!" "I wasn't..." "I saw you looking at her ass and looking at her tits. Stop it!" "I thought that women looked at other women." "To see what they're wearing, and how they look..." "To judge them," Christian corrected. "Maybe, but not eye hump them," Marissa rejoined as she pointed her finger in his face. "Fine," Christian replied while continuing to rub his hand. The waitress returned a few minutes later with their cocktails and placed them on the table before Christian paid for the drinks. He struggled to keep his eyes away from her cleavage that was spilling out of her snug, black tank top while he waited for his change. After giving her a tip, the waitress walked away and left them to talk. "That's two for two, and one of each sex," Marissa reminded Christian. "Okay. Maybe you'll win," Christian admitted. "I've already won." "How do you know?" "Nobody's said boo. The only way they'll know is if you let them." "I wouldn't be so sure." "I like my coffee with a little cream, no sugar," Marissa replied as she took a sip of her drink, ignoring her boss' alleged doubts. "Don't get ahead of yourself." "You're the one who's out in front of her skis," Marissa retorted. The two continued to talk while the bar grew even more crowded. They watched as more men and women placed bets throughout the place. Their eyes focused more on the dresses and hats of the other girls in the establishment. Marissa would stop girls as they walked by to compliment them. Christian found himself doing the same, struggling to keep up a raspy, higher voice that seemed to throw the girls. Marissa smirked at his voice. It almost seemed like he had practiced a girl's voice to keep up the act. With each girl that walked away from the table without giving any hint of knowing that Christian was a man, Marissa grinned as she whispered another hint of Christian's future. "I expect my secretary's heels to be three inches or higher." "Always give me drafts unstapled." "No starch on my dry cleaning or else." "I expect my secretary to wear hosiery everyday, you know, just for that professional look." Each reminder sent a quiver through Christian's body. While Marissa finished saying another, a man walked over and gave them a compliment. Marissa responded with a thank you that Christian seconded before the man made a clumsy attempt at a joke. Christian laughed in response prompting the man to focus his attention on him. Marissa smirked at the attention the man was giving Christian while they each sipped on their second flirtini of the evening. Her eyes widened as she saw Christian blush and laugh at another comment as the man's body grew closer to Christian's. As she watched her blushing boss, playfully brush his hair to his side while he flirted with the guy, she realized that she had been duped. His hesitation to accept had been act. She knew that there was no two ways about it. The more she thought about it, the more obvious it was that he never would have accepted her bet unless he wanted it all along. She shook her head as she thought back to how the whole thing started. He had started the conversation and led it to the point where she felt challenged enough to make him put up or shut up. 'He fucking played me,' she thought as she stared at him and crossed her arms. Christian's smile left his face while he looked at his secretary and realized that she suspected something was wrong. He separated himself from the man and asked, "What's going on?" "I think I won," Marissa replied, not wishing to state what she felt was obvious in the presence of Christian's would be suitor. "You were right," Christian admitted. "So, a full month of heels for you," Marissa leaned across the table to whisper in his ear. "Uh...Don't remind me," Christian responded, trying his best to feign being upset. "I'm sure I don't have to, girlfriend," Marissa replied with a shake of her head. ----------------------------------------------------------------------- Marissa got to work early on Monday morning. She walked into her boss's office and placed her purse down on Christian's desk. She turned on his computer and logged onto it. She was eager to see what her boss could make of himself with the makeup, outfits and heels she had sent him home with after they returned to her apartment from the bar as she waited. She shook her head, wondering what level of skill he would demonstrate with his self-feminization. She figured that he was probably an expert, but he was likely going to try to make amateurish mistakes in an effort to make her think otherwise. The sound of the door of the office opening brought Marissa's eyes away from the screen and towards the doorway to her new office. She rolled her chair towards the edge of the executive's desk to peer through the doorway, unobstructed. Her eyes widened as she saw her boss standing in a pair of nude colored, three-inch high heels and a pink, faux wrap dress. She got out of her chair and approached him as he took off his jacket that exposed the surplice neckline of the peace palm patterned dress. She never noticed how thin his upper arms were until she saw how they looked as the emerged from beneath the dress's short sleeves. His nude pantyhose covered legs shimmered in the morning light that bathed into the office as he adjusted his feet in his pumps that were adorned with matching grosgrain bows at the vamp. His long hair was styled with waves and his makeup was nearly flawless. She smiled at him as she stood up and said, "Let me take a look at you." Christian stopped at her old desk and let her look him over. He squirmed a little, wondering if she could tell that he was practiced with makeup. He cast a glance up at her eyes before she said, "You look great." Christian shook his head and lied, "I feel like an idiot." 'No, you don't,' Marissa thought before she feigned sympathy for him and gave him a brief hug. Christian thanked her for her kind words while he put his black purse down on the desktop. Marissa realized that the purse was not the same one that she had given him on Saturday. It was a similar design, but the buckles were slightly different. A slight grin came upon Marissa's face as she thought back to the thoughts about Christian that had consumed her since Saturday night. Originally, she had been planning to just to tease him with being a secretary for a month, but, now, she knew that she was going to hold him to his bet. She knew that he wanted it. She also decided that she was going to be a far more demanding boss than he was to see just how much he wanted it. As Christian pulled out his chair, Marissa said, "Chrissie, before you sit down, can you get me a cup of coffee?" "Chrissie?" Christian asked, raising his eyebrows as he did so. "You don't look like a Christian." "What do I look like, an Anti-Christian," he rejoined with a smirk. Marissa gave him a shake of the head, as she replied, "No, but definitely more of a Chrissie." "There are girls named Christian." "Yes, but I don't want anyone confusing you for that old tyrant." "I was a tyrant?" Christian asked with his hands pressing his dress onto his hips. "Chrissie, you were never a boss, how could you be a tyrant?" Marissa countered with a smile. "So, you're just going to pretend I'm two different people?" Christian inquired. "I don't know what you're babbling on about, Chrissie. Can you please just get me my coffee?" "Sure," Christian replied with a resigned sigh before he asked, "How do you like your coffee?" Marissa reminded him before she went back into her new office and waited for him to bring her the cup. Christian hurried towards the kitchenette to make her coffee. Once he was sure that he was out of her view, Christian let a smile come to his face. He reached for Marissa's cup that was on the drying rack and stuck into the coffee maker. He laughed to himself about how ridiculous it was to feel so excited to be doing something as trivial as making Marissa a cup of coffee. The request to do so, however, was making him feel excited that she was really treating him like her secretary. He struggled to force the grin off his face as he approached Marissa's temporary office with her cup in his hands, not wanting to give away that he was in a trap of his own design. Christian walked into his office, holding his head low as he placed the cup on the coaster on the desktop. "Thank you, Chrissie," Marissa replied before she took a sip and said, "Superb work." "Thank you," Christian responded meekly, struggling not to smile at her praise. Receiving the response she desired, Marissa pressed further, "Chrissie, what are you planning on wearing tomorrow?" Christian was confused by the inquiry. He asked, "I'm not quite sure yet." "Have you purchased anything to wear? You can't just keep wearing those same old outfits I sent you home with. Most of them aren't going to be a good fit anyway," Marissa replied before taking another sip of her drink. "I have bought some stuff," Christian replied with an understatement. "And you're choosing to wear what?" Christian shrugged before Marissa continued, "I need to approve your outfits." "What?" Christian replied, horrified and aroused by having to get his clothing choices pre-approved by his boss. "Chrissie, I'm running a professional office here. I know your shoes will be appropriate, but the rest, well, that's an open question." Christian squirmed, feeling his manhood pushing his gusset away from his body before Marissa continued, "I want to be sure that you understand what appropriate attire is for a girl in your position." "I think I got it," Christian replied, humiliated and excited about being talked down to by his former subordinate. "Okay, so what are you going to wear?" "I've got a couple of options." "Name them," Marissa demanded. Christian paused before he said, "I was planning to start with a skirt." "Good choice. You know that I insist that my secretary only wear skirts or dresses." "Why?" Christian asked, delighted by the requirement he was planning to comply with in the absence of any such rule. "It gives a secretary a more proper appearance. Pants should be reserved for management types." "You wore pants..." "I was always a management type, even if I was only an assistant," Marissa replied, cutting Christian off. "Okay." "Now, what are you going to pair your skirt with?" "Probably a blouse." "Nothing too low cut." Christian blushed at the statement before he admitted, "I couldn't really pull that off." "No, you're too flat," Marissa said with a smirk as her eyes darted to his faux bust. "I think I'm pretty big," Christian replied, peeking down at his chest before he patted his padding through his dress. "Big enough. A secretary shouldn't be distracting," Marissa chided. "I'll keep away from the low cut tops," Christian replied. Marissa nodded before she said, "And your legs." "I was going to wear a pair of pantyhose or tights." "Good. I don't have to remind you that a girl must always wear pantyhose or tights with a skirt or dress. Bare legs are simply not professional. I don't care if it's a hot day. Men have to wear pants when it's a 100, secretaries have to wear hosiery. Understood?" "Yes, Marissa," Christian replied, aroused by the order he would have no qualms about complying with. "Now, you know hosiery is a difficult animal." Christian gave her a curious look before Marissa explained herself, "They run! They tear! They're a complete and utter bitch! That's why you always have to carry two things with you." "What's that?" "Clear nail polish to stop runs in their tracks and a change of hosiery in case it's not salvageable," Marissa answered as she counted off each on a finger. Christian nodded before Marissa continued, "I will not tolerate a shabby appearance. I will be giving you a pantyhose inspection everyday to make sure that your hosiery is presentable." Christian's member throbbed at the demand and thin threat his boss was leveling on him. Christian nodded to convey he understood her. Marissa nodded back at him before she told him to ensure that his hair and makeup was done in a neat professional manner as well. Christian asked, "Is what I did today okay?" After a long pause, Marissa answered, "It's acceptable. Just don't let me catch you in pigtails." "I promise that won't be a problem," Christian replied with a laugh. "Good, now, I need you to update the spreadsheets regarding our accounts receivables." "Okay," Christian replied. Marissa stared at Christian's motionless action and asked, "Can you do it now?" Christian nodded in response to her stern tone. He turned and walked away from her office, aroused by the order. He walked over to his new secretarial desk and sat down on the seat. He pulled it away from her desk and observed the plastic, padded arms that were in just as sharp of contrast to the wood and leather arms of his executive chair as the low back was to the high back of the chair that Marissa was now sitting in. Christian sat down in the seat and felt the height difference between himself and Marissa. His feet dangled off the floor as he sat back in the chair, like a child's. Christian reached for the lever but found that the seat would not adjust an inch lower. "What the hell?" Christian wondered aloud as he bounced his rear against the chair hoping that it would lower so that his feet could touch the floor. Marissa stifled her laughter at the sound of Christian's attempts to fix the broken chair before he gave up his futile efforts. Christian pulled the chair under the desk and slid his rear towards the front of the seat until his feet rested on the ground. He began to update the spreadsheet as Marissa had done each morning since she started working for him. He spent most of his morning doing it, pausing only to answer the phone. The first few phone calls were frightening for Christian. He recognized some voices on the phone, even though he had not spoken with most since he hired Marissa. Despite his efforts to throw his voice, he was sure that someone would recognize his. It was only a matter of time in his mind. While the people he spoke with gave no hint that they knew who he was, Christian could tell that some of the people were unsure of his gender. They avoided referring to him in gender pronouns, making him realize that his voice was androgynous at best. Under the circumstances, he was happy with the confusion since it was better than being constantly referred to as a man, which would have been shattered the feminine illusion he was trying to exist within for the month. Shortly before he finished updating the spreadsheet, Marissa stepped out of her new office and smirked at Christian's perched position on the chair. She said, "How are you doing?" "It's going good. I'm almost done." "Good." "Marissa, is your chair broken?" Christian asked. "Well, no, but YOUR chair's been broken for a while," Marissa answered, taking care to correct her boss in the process. "Why didn't you ask for another one?" "It worked for me. It was comfortable." "Well, it's too high for me." "Chrissie, you're only going to be here for a month, so we're not going to replace it. You'll get used to it." "It's uncomfortable," Christian replied as he reached for his lower back that was starting to ache from the lack of support, just like his feet were aching from the arch caused by his shoes. "Being a secretary often means being uncomfortable, besides I like that you're sitting like that." "Why?" Christian asked, upset about having to spend a month with the same ache in his back, even as he was aroused at her executive dismissal of his reasonable request. "You're not sitting back in the chair. If I need to call you, you can snap right up and get into my office quicker." Christian blushed, humiliated to be turned on by her claim. Marissa could sense his arousal as she said, "I need you to place a lunch order for me." Christian nodded as he took down her order before Marissa stepped out of the office to head for the ladies room. Christian reached for his phone and called in the order at a nearby eatery before he placed one for himself as well. He wrote down when he could pick it up before he went back to finishing his spreadsheet. After Marissa walked back into the office, she asked Christian if he had placed her order. After confirming that he had and when it would be ready for pickup, she told Christian to drop off her dry-cleaning on his way to the luncheonette. Christian was surprised by the order, since he never assigned Marissa personal tasks. He knew that she was deliberately pushing him harder than he did with her. He tried to act passively upset about it, but his efforts did not fool Marissa. Marissa gave Christian the money for her lunch and dry cleaning before she sent him out the door with her dirty clothing in hand. Christian walked through the hallway and road the elevator down to the underground parking garage before he remembered that he had given up his reserved spot to Marissa for the month. "Shit," Christian muttered as the doors opened. Christian pressed the button for the ground floor and road the elevator back up a floor. After the doors opened again, Christian headed for the front door of the building and pulled it open. Christian walked out of the building and felt the warm sun on his skin. The breeze up the skirt of his dress was different from anything he had experienced before. Still, he hurried towards his car that was parked not far from the building, not wanting to dawdle with tasks at hand. Christian opened his car with his key fob and got behind the wheel. He slipped his heels off and put on a pair of flats before he started the engine and pulled out of the parking spot. After exiting the parking lot, Christian drove down the street to the dry cleaner that was located a few blocks from the eatery he had placed the lunch order with that afternoon. Christian parked in the shopping center and started towards the dry cleaner with Marissa's clothing in hand and his pocketbook pressed tightly against his side. Christian greeted the old Asian woman behind the counter with a smile as he placed Marissa's clothing down on the counter. The woman examined the clothes as she rang them up before she said with a heavy Korean accent, "These aren't for you?" "Oh, no," Christian admitted, knowing that the woman knew that he was dropping them off for another person. "Who they for?" She asked. "My boss," Christian answered, struggling not to smile at the way his admission sounded. The old woman paid his answer no mind as she told him the amount that was due. Christian paid it from the money that Marissa had sent out the door with before he took the dry cleaning ticket. Christian walked out of the dry cleaner and went back to his car. He then drove over to the luncheonette. Christian got out of the car and walked into the crowded building. Christian looked around, hoping that he would not recognize anyone in the crowd. He was relieved not to before he went to the cashier and waited on line. As he waited, a young woman walked over behind him to stand on the line with her purchases. Christian could see her looking him over. He felt nervous for a second before the girl realized that he had noticed her looking at him. The girl smiled as she said, "I love those shoes. They're so cute." "These. Oh, thanks," Christian replied before he complimented her bag. The girl smiled as she asked where Christian got his shoulder bag. Christian admitted the discount retailer he had placed his online order with to the girl's surprise. The girl shook her head as she said, "I haven't shopped there since I became a CPA." 'Well, aren't you the lucky one,' Christian thought to himself before he responded, "Well, I've got to economize." "What do you do?" The girl inquired. "I'm a secretary," Christian answered. "Oh, that's nice," the girl replied, adopting more than a hint of an air of superiority over him based on their respective job titles. While Christian was slightly upset about the cute girl's attitude, he was also aroused by it. He was also happy enough to be able to turn away from her since the cashier called him forward. Once he stepped up to the cashier, Christian told the woman his order. She called it in from the back as he paid the bill before he stood off to the side waiting for the staff to drop it off for him. Christian thanked the man who dropped it off. The non-English speaking man gave Christian a smile in return before Christian stepped out of the building and went back to his car. Christian drove back to his office and pulled into the parking lot. He drove past the spot he had left and frowned as he saw that the spot had been taken. Christian drove down the next aisle and found no spots. He sighed as he pulled a few rows further away from the building and found a spot. He parked his car in one of the last rows of the parking lot. He then slipped his heels back on before he began the long walk back to the building. Christian was careful to watch for cracks and grates as he walked around the parking lot. He was not used to it in flat shoes, let alone heels. He examined the uneven pavement as he endeavored to maintain his balance before he reached the sidewalk that surrounded the building. Christian used Marissa's key card to enter the building and made his way to the elevator. After entering the office suite, Christian gave Marissa her dry cleaning receipt and lunch. Marissa gave Christian a perfunctory thanks before she told him to eat at his desk. "Why?" Christian asked. "I don't want to miss any calls," Marissa replied. Christian nodded, understanding her request while he went back to his new desk and sat down. He sat towards the front of the seat and hunched over his desk while he ate. He handled three calls while he ate before he cleaned up his desk. As Christian walked back towards his desk, Marissa called out to him. Christian went into his former office and asked, "Yes?" "I need you to clean up this stuff," Marissa said as she stared at the computer monitor and waved her hand in the general direction of what remained of her lunch. Christian was shocked by the order. It was almost as if Marissa knew the role he wanted her to play. Christian nodded while he approached the desk and scooped up the empty wrapper as his manhood swelled. He clustered the garbage with Marissa's empty glass of water and dirtied utensils and carried them out of the room. He never turned to see Marissa's smile as he struggled to hide his until he reached the office's kitchenette and placed the glass and utensils in the sink. After throwing out the wrapper and Marissa's used napkins, Christian turned on the sink and began to wash the glasses and utensils. With each turn and wring of the sponge, Christian felt more like a secretary than ever. Once he finished, Christian started back to his desk. To his surprise, Marissa was waiting for him. Christian looked at her, waiting for her to say something before Marissa decided to see how far she could push him. She furrowed her brow as she said, "Chrissie, my tag in my underwear is chaffing me, I need you to cut it out." Christian's eyes widened at the very personal request that went well beyond professional boundaries. Marissa reached for the pair of scissors on his new desk and handed them over to Christian. Christian took the scissors by the handles and watched as Marissa lowered her pants a little. She pulled the tag out of her panties, which had the effect of drawing her panties away from her body. Christian was unsure if she was trying to turn him on as he clutched the tag and caught sight of the crack that ran between her shapely butt cheeks. His eyes darted away from it, feeling it was inappropriate to gawk as he concentrated on cutting off the tag. Once it was clipped, he let it go and watched the waistband of Marissa's panties cling back to her hips. Marissa smiled at his willingness to lower himself to fixing her underwear while she brought her pants back to her hips. She then assigned him some documents to copy and file, knowing that it would take him until the end of the day. Christian went to the filing cabinet and retrieved some documents that Marissa wanted before he took another file from her and began to make copies. Christian listened to the machine hum as it took in the papers and churned out the copies. His feet ached as he moved around the copier, collecting each bundle and fastening them together to save time. Once he fed through another copy job, Christian scurried over to the file cabinets to make room for the files that Marissa wanted put away. Christian moved files from one drawer to another to make room for the large file set. His back ached as he hunched over the drawers, helping to maintain his balance with one hand on the top of the three drawer high cabinets. After hearing the copier beep to alert that the job was complete, Christian hurried back across the office to feed the next job. Marissa caught sight of Christian's hurried steps and grinned at his eager efforts. On his face, she also recognized the pain in his feet that was being caused by his feet being unaccustomed to her shoes. "At least he's getting the full experience," Marissa chuckled to herself. Christian ran the last set of documents through the copier before he moved back over to the filing cabinets. He then went back to reorganizing them. As the workday ended, Christian said goodbye to Marissa and headed out the door of the building. The warm spring air of the evening felt good on his skin as he walked to his car. The sensations still felt strange to him as his pained feet pressed against the sidewalk. After he drove home, he made the short walk to his apartment building that he had deliberately kept a low profile in since moving there a few weeks earlier. He used his keycard to enter the building before he used it to get the elevator to take him up to his floor. A smile came across his face as he thought about getting out of his heels and into a pair of flats. As he approached his door, the door to his neighbor's apartment swung open. Christian reached for his door and turned his head away from the open door. "Miss?" The girl asked, confused to see a woman trying to enter Christian's apartment. Christian stayed silent, trying to play off that he thought she was speaking to someone else in the empty hallway as he pushed his door open. "Miss," the girl repeated. "Yes," Christian replied with a smile, unable to ignore her any longer. The girl's eyes widened as she recognized Christian's face. "Holy Shit!" "I can explain." "You look great," Sadie said as she looked him over. "Uh...thanks," Christian replied, confused by the praise and the interest that the woman was taking in him. She had never showed any interest in him prior despite his initial attempts to draw her attention after he moved in. "Why are you dressed like that?" "It's a long story." "I have time." "You look like you're going out?" Christian countered." "Oh, I'll make time for this. Why don't you come inside?" Sadie's invitation was one he had been hoping to receive from the moment he meet her. He had not expected to receive it in a dress, however. Still, Christian decided he could not pass up the opportunity to spend a few minutes with the pretty girl. Christian closed his door, followed Sadie into her apartment and looked around. The apartment had the same dimensions as his, but the furnishings and decorations were far more feminine. "This place looks great," Christian said. Sadie accepted his compliment before she asked if he would like something to drink. "Water would be great," he answered. "Trying to purify yourself?" "No." "Trying to stay thin?" Sadie then inquired. Christian responded with a shake of his head before she returned with a glass of water and told him to take a seat. Christian sat down on the couch before Sadie sat down a few inches away to his side. Sadie crossed her legs and asked, "So, are you going to tell me?" Christian nodded his head as he explained the bet that he had lost and the consequences that he faced for losing it. Sadie laughed as she said, "That's an odd bet for a man to make." Christian blushed at her words before he said, "Marissa's convincing." "I'm sure you didn't need a lot of convincing." "No. She talked me into it." Sadie shook her head as she said, "No man gets talked into a bet like that." "What are you talking about?" "The only man who would agree to do something like this wants it." Christian shook his head, trying to defend his masculinity, before Sadie added, "You wanted to lose." Christian shook his head again before Sadie said, "Do you want some wine?" "No. I don't want to be a bother," Christian stammered as his nervous fingers fumbled against one another. "It's no bother, and I insist." "Okay," Christian replied as Sadie got up. He heard her open a bottle before she returned with two glasses. She handed one to him before she sat down and said, "Now, are you ready to stop lying to me?" "I wasn't..." "You still are," Sadie interjected. "I'm not...," Christian started to reply before Sadie brought her hand down upon his nylon-covered knee. She began to stroke it before she raised her eyes to catch Christian's. A smile came across her face as she said, "I like you, but I won't tolerate you lying to me." Christian nodded as a fluttery feeling was stirred up in his stomach. Sadie leaned closer to him and asked, "What's your name?" "You know my name..." "No. What's your name?" "Chrissie," Christian admitted. "Pretty name. So familiar and easy too," Sadie said with a smile before she took a sip of her wine. "You don't think it's strange," Christian replied, dropping back into his practiced feminine voice. Sadie's eyes widened at the sound of it before she said, "We're all a little strange. That's why I stopped going to my shrink." "Why did you go to shr...a psychiatrist," Christian asked. "My father was a cross-dresser and my parents divorced...largely because of it, or so my mom says." "Oh." "That's why I can spot one and tell the difference from a boy in a costume and a boy who knows his way around a makeup bag." Christian's manhood hardened

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I don't know why he convinced me to come to the racetrack with him, but I was feeling generous and decided that watching all those horse muscles and sweat could be interesting for a change. Matt and I had been together for about three months. Before him was a string of lovers that kept me amused and satisfied after my husband divorced me. I was enjoying all of the attention I could receive of the male kind. The sun was shining, and we paid the extra money, well Matt paid, since he had the...

4 years ago
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The Pony Races

THE PONY RACES I led a sheltered childhood. My father died when I was only seven years old, and my mother became what I now know was a recluse, rarely leaving our main home, a large manor house with stables set in around fifty acres of land. The other side of our boundaries were mainly fields and our nearest neighbour, apart from the Estate Manager's cottage, was a farm nearly three miles away. We had other homes, which before I reached double figures in age, I just assumed everyone...

3 years ago
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The Passion of Mother Ethel

Mother Ethel always enjoyed the short walk to the train station. It was beautiful Autumnal morning and Mother Ethel took the opportunity to walk to the train station as she knew that she had a very busy day ahead. Those that saw Mother Ethel along the way bowed reverently,they knew that Mother Ethel was a Nun of the Monastery of Repentance and when a Nun or a Monk walked past it was polite to bow, for many knew what the Nun's and Monk's of the Monastery were capable of. As Mother Ethel strolled...

1 year ago
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Ladies Day at the races

The stables are owned by two brothers, Jack and Max, who are multi millionaires. They are both bachelors and are invited to attend the Ladies Day at the races, which is the most prestigious event of the season. However, they have a problem. They are recently divorced and don't have any female companions to accompany them to the event. So, they come up with an idea. They approach two of their apprentice jockeys, Tom and Alex, who like all jockeys are both very small and slim, but these...

2 years ago
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A Day at the Races

It was the perfect day. Livvy sat in the bleachers, making her butt sore but the bright sunshine on her face soaking into her skin made it worth it. The peaceful day was interrupted by the extremely loud roar of hundreds of car engines, a stadium of excited fans, and the announcer of the loud speakers rambling off the day’s events. It was 5:30 in the afternoon and still 90 degrees outside. Livvy wore her favorite pair of white shorts - a decision she regretted when she remembered how dirty the...

Taboo
2 years ago
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Dot Dorothea and Dick

Dot, Dorothea, and Dick Chapter One Dear sister: I found this letter among some others, scrolled up and tied with purple ribbon, in a chest belonging to our great grandfather. The name Charles has belonged to several in our family line, but I believe I know the one who received and saved this letter, and kept it preserved for so many years. I believe the letter speaks for itself, so I will now offer it up to you. Dearest Charles: I hope this missive finds you in such good...

2 years ago
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My Golden Summer with Blythe Ch 01

Our Last Day of School. I can’t believe it. This is my last day of school, I thought, not sure how I felt now that the long awaited day was here. Stepping out into the beautiful sunny afternoon, heading toward the group of waiting yellow school buses I breathed a sigh of relief. I was glad school was finished. Throughout High School like a ship at sea, I had plotted my course, studying hard. However, the Scholarship that many felt I had rightfully won had somehow ended up going to one of...

2 years ago
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Antheas baby 1

“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

2 years ago
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Another day at the races

Well it was a few weeks after the Derby and it was Royal Ascot, well I had been booked again to take six ladies up to the races on Ladies day by Mrs Smith this time the Ladies where all very posh and I was to keep my chauffer cap on with white gloves and my suit had to be just right. Mrs Smith had not invited Mary on this trip, I’m sure she knew we where having an affair. She was very friendly to me as all the Ladies got into the Limo, I watched as each one showed there stocking tops as they...

3 years ago
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My Golden Summer with Blythe Ch 02

My Golden Summer with Blythe – Part 2 Josh’s childhood dream girl visits him in San Francisco. The Return of Blythe Coming from a small farming community, San Francisco proved to be everything Josh had ever imagined – and then some. He loved the freewheeling atmosphere – the friendliness – in short, he fell in love with the city by the Bay. Because of early retirements, and dedication to his work, he had advanced much quicker than he had ever expected. Arriving at his chic little Apartment...

4 years ago
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Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

3 years ago
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At the Races

Introduction: Peter is looking back on his life, one happy memory from his childhood always springs to mind first! Sitting in his chair, sipping at his tea, he flicked idly over the album. It was times like this which he loved. The afternoon sun cast a mellow light onto the dusty photos lying in his lap. He smiled, his childhood was always so much fun. And it was even better to look back on! One photo stood out for him though. The grainy family photo at the horse race. He couldnt remember this...

4 years ago
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At the Races

One photo stood out for him though. The grainy family photo at the horse race. He couldn’t remember this one before. How could he even forget that day? Looking into his own eyes, he remembered the time the family went to Saratoga. Oh, how much had changed since then. He was fitter, smarter, and more handsome; and yet in the photo, so anonymous. His sisters all bore huge white grins; merely a smile was on his face. He grinned at his own adolescent misery. He closed his eyes and dreamed of...

4 years ago
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Off to the Races

I have a group of friends that get together every Thursday night to play poker. We are also rabid race fans and every ten years for the past ten years we have gotten together on the last Sunday in May to watch the Indy 500. Every year about the time the race starts we make a vow that next year we will go see the race in person. Every year nothing comes of it and we kick ourselves for not doing anything. Every year this happens. Until this year. As usual the adrenalin started to flow as Jim...

4 years ago
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War of 7 Races

The year were 698 in the country of Trygon. All the races of the world are at war for land, the humans, elves, dwarfs, and goblins are lead by their monarchs, the orcs and ogres are lead by a mysterious figure head, and the centaurs works threw a democracy. The Race War begin up when the humans took over acres of orcs realm. The orcs in return murder the 8th Prince of Laarse, the human kingdom. Then the humans made a pact with the dwarfs and goblins that said that they would team up to destroy...

Fantasy
3 years ago
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Fallen Angel Chapter 11 Althea the School Girl

Chapter 11: Althea, the School Girl The infernal screeching of the alarm clock awoke Cal from his reverie. He had been up for about a half-hour, but he had only been lying in bed next to the love of his life. Althea's arms were still clutched about him as he stealthily clicked the snooze button, assuming that it was six o' five in the morning, his usual waking time during the school week. He had been thinking long and hard about the previous two nights. Evan... what have you become? He...

4 years ago
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The Devils Pact Sidestory Miss Blythe Is Hot for Her Students

edited by Master Ken Wednesday, September 4th, 2013 "Hi, I am Miss Blythe," I said to my class, writing my name on the whiteboard with a red dry-erase marker. "I will be your World History teacher." It was the first day of the new school year and, as I launched into the course syllabus, my thoughts kept drifting to that day in June at the end of the last term, when my Living God, the Holy Mark Glassner, walked into this very classroom and changed my very outlook on life. I didn't know...

2 years ago
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Carruthers Bride

The the wind howled around the quayside as I stepped onto terra firma for the first time in weeks, the wind threw sharp shards of ice to sting our faces as we looked up at the sails as they were finally furled and stowed as our captain grinned at our discomfiture, "Au revoir!" he joked as if he knew we should soon be recalled. Those such as were left, and we were few enough, I shuddered. My best uniform packed securely in my Valise, awaited me, and just a few more duties before I...

2 years ago
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Athena Corp Chronicles A Mothers Love

As he approached one of the hall's long mirrors he stopped to inspect himself. It was a familiar sight, the flowing, billowy French maid outfit surrounding his body. His arms and legs were outlined in silky, white stockings and arm-gloves. He wore pearl earrings and the lacy white collar around his neck was adorned with a beautiful pendant. It was a gift from mother that he wore every day, without fail. Jon's painted red lips and neatly applied eyeliner and blush were evidence that he was...

2 years ago
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Sex Therapy 2 The Thert

PREFACE:There are no sex acts in the story but the patient does have an orgasm as a result of the Ther****t’s physical examination. Part 1 is the Sex Therapy appointment from the patient’s point of view and part 2 is the same examination seen through the eyes of the Ther****t. I don’t think it matters which one you read first.I hope you enjoy it and will let me know what you think in any...

2 years ago
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Aunt Katherin and Her SlavesChapter 2 Katherine

Katherine stepped into her elegant living room and took a book from the shelf. She sat in a plush lounge chair, specifically selecting a chair in the back corner of the room next to an old dumbwaiter that was once used to ferry delicious meals from the downstairs kitchen to the dining room table. She planned to read the book for a short while, but she already knew her attention would soon be diverted. Tonight the dumbwaiter would once again be placed into service, except this time it would be...

2 years ago
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Wank races

It seems that as soon a boys got the urge to start wanking they wanted to show to other boys what they could do. There were regular wank races in the urinal at my high school . usually two or three boys rubbing for all they were worth into a large wide steel pissour. They would grunt and watch each other. Seeing if their rivals was getting near to the vinegar strokes and if they suspected they were behind they would rub more furiously. I remember the first time I saw this from the back of the...

1 year ago
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Motherless Vintage

Do you know of the porn site Motherless.com? You should. I’ve reviewed it a few times on my site, The Porn Dude, although it was for different genres every time. This time around, I’m going back to this place and looking at a specific and niche little category many of you are just begging me to cover. We’re looking at vintage porn today. While it doesn’t have the same resolution and quality as the porn you can find today, it’s definitely a genre of porn that has a lot of personality to it and...

Vintage Porn Sites
3 years ago
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Althea

I should have known better. I should have remembered that old saying, "If it looks too good to be true, it is." I was in love. She was damned near all I thought about with the exception of my studies and it didn't make sense to me. I prided myself on my intellect and my ability to think logically, but there wasn't anything logical about the way I felt about Althea. She was beautiful, smart and very popular and I was not. I wasn't a bed looking guy, but I was nothing exceptional. I was...

1 year ago
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Motherless Images

Motherless. A one-word website title that says everything it needs to say. This is a site where the rules are, more or less, completely thrown out the window, morality means absolutely nothing, and there is nobody to save you from it. Hedonism is God here.The site likely is also called this due to the fact that the girls who end up on motherless.com likely have no positive female influence in their lives to keep them from it. Motherless is the place parents spend their whole lives fearing that...

Porn Pictures Sites
1 year ago
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Motherless Amateur

I always considered Motherless the “4chan” of porn. Not only because Motherless was somewhat popularized there, but because Motherless also encourages users to share their own content in a very open way. This means minimal bullshit like moderation and censorship, and a strong “anything goes” attitude that leads to free and extreme content. It encourages people to create and upload their own homegrown content, like videos of their girlfriend pissing or spycam videos of their cousin....

Amateur Porn Sites
1 year ago
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Motherless BBW

What is it about Motherless that makes me fucking cum every time? Maybe it is how raw and amateur the porn on the site comes across as, or the content is just that fucking hot. Perhaps it is the fact that there is an astronomical amount of pornography just waiting for a dumb fuck like you to beat off to! I really don’t know, and frankly, I’m not going to pretend that I do.But what I do know is that if you love BBWs, the Motherless.com homepage will not be of much use! Preferably, head on over...

BBW Porn Sites
1 year ago
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Motherless Voyeur

Have you ever heard about a website called Motherless? Home to all kinds of kinky porn niches, with a side of the mainstream crap? If you are into some questionable fap content, you might want to check this website out. Plus, Motherless is a free porn website, so you can browse as much as you fucking want. Now, I am not really here to talk about the website in general… I am here to tell you about their amazing category, called voyeur porn.The world of voyeur fucking is a rather interesting one....

Voyeur Porn Sites
2 years ago
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Clothesline Leather in Lawnville

Clothesline[This story is part of the Leather in Lawnville series.]   Clothesline By DuskPetersonYou can tell a lot about a guy from where he shops. Take my friends, who have specialized tastes. Some of them spend their time at the hardware store, while others take an interest in our town's fabric shop, which has needles and pins that make them drool. Still others hang out at the department store, eyeing the cutlery collection. Somehow all of us end up rubbing shoulders at the town's jacket...

2 years ago
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Aether Guardians

The Five Kingdoms of Arstoria had been embroiled in the Great Ancient War for centuries. The war came to an end when Kalace, the Wizard King conquered the five lands and brought them under his rule. Kalace, the Wizard King of Arstoria, conquered all of his opponents who were unable to deal with his overpowering magic. When Kalace had united the five kingdoms, he brought peace to the warring kingdoms and was revered and celebrated by his later generation. Kalace, however, had a dark weakness in...

Fantasy
1 year ago
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Motherless Creampie

Woah, did Motherless.com get a facelift? I know I suggested it in my review, so I guess they listened to me! Well, I’m not going to brag too much about it, and instead, I’m going to focus on what I’ve set out to bring you today. We’re looking at an amateur website, and I just know that many of you are begging for amateur creampie content, so that’s what we’re looking at. I know how much you think Motherless can look sickening and pretty gruesome at times, but the creampie content can be quite...

Creampie Porn Sites
1 year ago
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Motherless Cuckold

No matter what type of porn you may be in the market for, Motherless has an ample supply of it, and cucking is no different. Actually, this might help to explain how you ended up being such a pussy little cuck.The journey that brought you to my website reading cuck porn reviews started in your childhood. A fair portion of my readership is actually motherless. Why, you ask? Your guys' moms chose a life of cucking and riding cock instead of raising you fucks properly.Don't worry, gents. I'm in...

Cuckold Porn Sites
1 year ago
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Motherless Horror

I browsed the horror stash at Motherless all morning, and now I don’t know if I should jack off or go hide in the closet until the danger has passed. Then again, hiding out might give me the perfect opportunity to rub one out in the peace and safety of the dark. Who knows who—or what—might be peeping in the windows with nefarious intent if I sit at my desk and shake my dick at the screen. Just like when I masturbate at the local Starbucks, I’ve got to be sure to balance the potential pleasure...

Extreme Porn Websites
1 year ago
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Motherless Incest

Incest porn has been a staple of pornography since the very first incel caveman realized that he couldn’t find fresh pussy out and about. He resorted to sniffing a whiff of his mother’s loincloth when she wasn’t looking, and beating his old cave meat into a leather sock.Now personally I’m not into the whole mommy-son dynamic – I’m a classy guy. But it’s no secret people like to get freaky when the lights go out, and if you’ve got a stiffy in your hand and you’re on Motherless, you gotta go...

Incest Porn Sites
4 years ago
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Thevidiya Thangaiyai Oothen

Hi friends, indru tamil kama kathaiyil en sontha thangaiyai epadi oothen endra kudumba tamil kama kathaiyai ungal idam pagirugiren. Vaarungal tamil kama kathaikul selalam, en peyar prathap vayathu 28 aagugirathu. Enaku oru thangi irukiraal aval peyar mala vayathu 26 aagugirathu, avaluku innum thirumanam seiya vilai Avaluku thirumanam seithu vaikum alavirku engal idam ipozhuthu panam ilai, loan apply seithu atharkaaga kathukondu irukirom. Naan oru kama veriyan eppozhuthu pen kidaikum avargalai...

2 years ago
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The Murder of Sharon Weathers Slut Extraordinaire

My name is Rebecca. Everyone calls me Becca. I entered the police department right out of college. I progressed rapidly, through different divisions and assignments. I always had my eyes set on Robbery-Homicide and after six years of hard word and dedication, I finally made it. At age thirty, I was youngest female in the division for such a coveted assignment, but I was superb at my job. I made it because of my skill not my gender. It was Saturday. Dispatch called our number just after we had...

Taboo
2 years ago
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Absinthe Makes the Heart Grow Fonder

Thanks to my usual cast and crew of Editors and Advance Readers, most of whom prefer to pretend that they don’t know me and wisely wish to take no responsibility for any part of my addled writings... Il n’est rien de réel que le rêve et l’amour - Nothing is real but dreams and love (from Le Coeur innombrable, IV, Chanson du temps opportun by Anna de Noailles) She was my one true mistress and ever faithful lover, my Green Lady and guardian of my dreams and now that I was back home...

4 years ago
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College Pennai Toiletil Vaithu Veritheera Seithen

Hi friends, indru kathaiyil en nanbanai kathal seithu emathiriya pennai ootha kathaiyai ungal idam pagirugiren. En tamil kathaiyai inaiya thalathil pathivu seithatharku nandri, en peyar pradeep vayathu 21 aagugirathu. En nanbanai oru pen kathal seithu matter mudinthathum kayati vitu vitaal, athanaal naan avalai usar seithu hardcore seiyanum endru mudithu seithen. En nanban enaku nanban endru kanbithukolamal aval idam muthal muthalil pesi pazhaga aarambithen. Aval pathini pola en idam nadika...

2 years ago
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Kanavanuku Theriyamal Kala Kathal Seithen

Hi friends, indru tamil kama kathaiyil en kanavanuku theriyamal ilamaiyaana kaal kathalanai eppadi love seithen endra kathaiyai ungal idam pagirugiren. Vaarungal tamil kama kathaikul selalam, enathu peyar jaya vayathu 36 agugirathu. Enaku thirumanam aagi oru paiyan irukiraan pinbu en kanavanuku vayathu 42 agugirathu. Naan santhoshamaaga thaan vaazhnthu vanthukondu irunthen, naan oru teacheraaga velai paarthu varugiren. Naan velai seiyum classku arugil oru veedu irukirathu, antha veetil oru...

2 years ago
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Becoming Anthea

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and blue eyes. Her small beautiful mouth sits beneath a cute button nose. All in all, Zoe is a goddess and I love...

Crossdressing
4 years ago
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Theateril Auntyai Kaai Adithen

Hi friends, indru sex kathaiyil auntyai usar seithu eppadi matter adithen enbathai ungalidam pagirugiren. En peyar Seenu. Vayathu 21 aagugirathu. Naan ithu naal varai entha penaiyum sex seithathu kidaiyaathu. Naan engineering padithu varugiren, enathu nanbargal oru naal theaterku ennai azhaithaargal. Naangal neraga bar seithu saraku adithom, appozhuthu bagubali padam oodi kondu irunthathu. Naangal oru gramathil irukum theaterku sendru irunthom. Angu pothuvaga pengal athigam vara matargal,...

2 years ago
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Thea Chapter Four

When the car with Jake in it became a dot on the horizon, Thea turned to go back in the house. Suddenly Floyd appeared. “Mrs. Thea, how you be?” Smiling, she knew immediately what he wanted. He had that look and a glance at his crotch confirmed it. The imprint of his cock was prominent as it pushed against the material. “Looks like everyone is gone.” Floyd said. His eyes looking out over the farm. “Yes, I am by myself for at least the next few days.” She replied in an...

3 years ago
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Thea and Sam

“Well, hell,” Thea said as she wiped the beads of perspiration from her face. “I guess ‘spring’ is here, huh?” “Yeah. It’s supposed to be cooler at higher elevation,” I replied. We took a few minutes in the shade by the rocks before rejoining our boyfriends. The four of us had driven up into the pass to hike. According to the weather report, the last coolness of a fading winter was supposed to continue through mid-week, but they were wrong. Actually, from our view from Eagle Point, where we’d...

1 year ago
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Motherless

Motherless.com! What an original name for a porn site, don't you think? The title doesn't fuck around: your mother would never allow you to watch the kind of filth they’ve got on tap. They pride themselves on being a moral-free zone for sick fucks, where you can find damn near anything. I’m talking about desperate chicks fucking anything that resembles a dick and crazy bitches literally eating shit. When you’re done fapping to the weird vids, you can even find "normal" porno to pass the time....

Free Porn Tube Sites
1 year ago
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Motherless Interracial

Ah, motherless, here we are again. A site known for offering such a variety, that no matter how fucked up your needs are, there is a high chance that you will fulfill them here. However, I am not here to blab about the site in general; I am here to talk about one particular category, interracial. As for those who want to know more about the site, there is a whole different review on my website instead.As for those who came here to learn more about that interracial lovemaking, I got your back....

Interracial Porn Sites
3 years ago
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Pauline The Slut Part 32 Therese Humiliates Pau

Therese looked at the scene before her. Her father and brother naked, her grandfather’s cock sticking out of his trousers and her grandmother eating her mother’s cunt, both of us naked. Beth with the camera, filming. “God, the slut is only in the door and she’s gone sex mad.” she said referring to me. She went and sat on the arm of her father’s chair putting her arm around him and kissing him on the cheek. My father was now hard again. He pushed my mother out of the way and started to fuck me...

3 years ago
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The BarlowsThea

Three months later, the sound of laughter made Thea Barton look up. The now twenty year -old blond-headed beauty was in the living room reading when she heard it. Recognizing the voice of Uncle Dan, she smiled as she waited to see whom he was going to be with. When the laughter grew louder, she smiled. Ah, yes! It was Irene, her now very good friend! Uncle Dan seemed to prefer her to the others. Her being married seemed to make no difference to all concerned parties. Thea smiled to herself,...

2 years ago
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The United Kingdom of Zoo A fake BBC documentary seriesS10E17 Ashley Mathews 29 from Newcastle Northern Ireland

This week’s show begins with that same old rusty bedstead, and that same old dirty mattress. Pausing to take in the magnificent filthiness of it, then pulling back to reveal the bare concrete floor around it, and to take in the harsh lighting. And then we hear our guest of the week approaching, quick little footsteps ... Light clicks on the studio floor. We pan round to see what we’ve got this week and see a slight, pale, small-boobed lady walking in quick, short strides ... She’s not is a...

2 years ago
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Love Lust For My Aunt Bethesda Part 8211 1

Hi, guys. It’s been a long time on ISS. I was away from the city. I hope you did like my other two stories(true incidents) which I had written. This is the next encounter I had with my aunt who was all alone and needed a little love for her. Her name is Bethesda and lived her whole life alone after her husband married another woman. I do have a lust for her and want her so badly. She is 45 years old and looks bomb. She got a good voluptuous body and looks like a brunette. As for me, I’m six...

Incest
3 years ago
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Becoming Anthea Part 2

My name is Anthony; I am twenty-two years old and live with my beautiful girlfriend Zoe. As you have read I have dark hair and dark eyes and I am clean shaven. Zoe is older than I am by a couple of years and is the driving force of our relationship. I am what many call a cross-dresser: a guy that gets great sexual satisfaction from dressing in women’s clothing.Of course, my girlfriend knows all about my cross-dressing. In fact, she encourages me to cross-dress. Once a week, generally on a...

Toys
4 years ago
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races

I love watching Chase race. I love that the person in that car, rocking the race track, is my husband. It turns me on how he can control the car and weave in and out of traffic and react to accidents with quick reflexes. Tonight has been a good night, its been a hot sticky night but the car has been running great, and Chase won his heat race and we are just waiting for his feature, which is the last race of the night, and its sprint car night at the track, so it will probably be late before...

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