Misadventures of Karen

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Misadventures of KarenWrote this for someone. Might be a small series, i dunno. Late in the Winter evening, Karen sat down at her computer searching through her email with a glass of wine as she did almost every night after a long day of work at the office. Strolling through her emails Karen noticed a peculiar one from a coworker titled “Busted!”. Karen was curious and opened the email to find picture after picture of her dressed up in super revealing women’s clothes and exposing her ass for the world to see. Normally this would be no problem, but you see Karen, the protaganist of this peculiar tale, was born a man. Flashback to days earlier. Karen decided to stay the night at a remote hotel two towns over where no one would easily recognize her. Stripping out of her business suit from the long work day, Karen carefully opened up her briefcase to reveal an assortment of clothes and wigs and makeup. Karen put on her stockings, mini-skirt and top, fixed a wig atop her head and applied some makeup to complete the look. Karen had been out a few times in public dressed this way to fetish clubs and adult bookstores but most of the time just like to experiment in her hotel room. It was a night Karen had done over and over and over, except this time Karen had one minor slip up. Neil is a coworker of Karen. Tends to tease Karen’s male alter ego relentlessly after receiving the promotion at work over Karen. Neil was tall, dark hair, broad shoulders, and in great physical shape. A real man’s man if you ever saw one. Neil had no real right, but wanted desperately to fire Karen from the company so he could raise his paycheck. Neil tried time and again to get his boss to fire Karen from the company, claiming Karen wasn’t needed by the company, but the boss knew Karen was a hard worker and needed at the company. Neil had been having some difficulties at home and decided to stay a hotel for a few nights. One particular night would turn in his favor however as he glanced out his window to the hotel across the street to see his work rival Karen prancing around in women’s clothes. Karen had accidently left the curtains open for anyone to see what he was doing. Neil with a long distance camera, zoomed in across the way and took picture after picture of his work rival, knowing full well he now had the dirty he needed to get her fired from the company.Back to the story at hand.As Karen scrolled çankaya escort the email, panic began to set in. Not knowing who among her had now found out her secret, Karen dreaded going to work the next day. Fear sank in as Karen walked into work the next day. But so far so good as the last half of the day was now settling. Karen’s boss had called Karen and Neil and select others in for a meeting to discuss the next project. Listening to her boss speak, Karen noticed across the table Neil giving her a sort of evil grin on his chizzled face. Karen once again began to let small panic set in. As the meeting concluded, so too had the work day. Karen was one of the last to leave and thought she was all alone minus the boss who worked on the floor above. But as Karen grabbed her things and made for the door, Neil creeped out of the corner with a smirk on his face. “Quite the show you put on at that hotel the other night, maybe tonight you come back to my new place and do it again. Wouldn’t want these naughty little pics making their way throughout the company would we?” Neil taunted Karen. Karen was sweating, panic and anxiety and made her entire body go numb with fear. Karen hung her head in shame and heard Neil utter “1565 West Maryland Court. 8pm, be there or these pictures go out to the whole company.” Karen slightly nodded. “Oh and wear something sexy for me bitch” Neil said turning to walk out of the door. Karen sped home as quick as she could, it’s amazing she wasn’t pulled over. Karen was nervous and sweating bullets. She wondered if Neil would actually be so cruel as to show the pictures to everyone in the office. It was a risk she couldn’t afford to take. She thought about just leaving town, sending an email to her boss saying she unexpectedly was called ouwt of town and wouldn’t be returning. But Karen couldn’t lose this job and certainly couldn’t just run out on the company knowing it would hurt her professional career going forward. So Karen did what she feared. She changed into a nice outfit consisting of a blonde wig, stockings, a medium length white/silver skirt, and a white blouse. It wouldn’t take Karen long to get to the address Neil mentioned so she made sure she looked as good as she could before going out. Karen had arrived precisely at 8pm with Neil waiting at the door. “Bitches come in on their hands yenimahalle escort and knees” Neil ordered. Karen blushed, but obeyed as she crawled her way throught the entraway and into the living space. Neil’s home was small, a temporary living space while Neil goes through his home issues Karen thought. “I knew there was something off about you since the day I laid my eyes on you. Should’ve known you were one of those crossdressing faggots” Neil laughed, “Imagine my surprise last week at the hotel when I spotted your ass strutting around in your hotel room dressed like some ridiculous looking drag queen.” Karen looked down in shame. “No no, hold you’re head up high bitch, I thought you were waiting for this to happen….Karen” he said. A look of sheer fright struck Karen’s face. “That’s right you tranny. Once I saw what you get up to, I did a little digging on the internet and found some very fascinating little things about Karen the Tranny slut. Well bitch, you’re mine now unless you want these pictures leaking to the whole company, your family, and the whole fucking internet.” Neil laughed right in Karen’s face. “Come over here and take off my pants bitch” he ordered. Karen crawled towards Neil and slowly unzipped his pants making them fall to the ground. Neil’s hard thick 8″ cock stood adamant knowing it was about to claim another whore. “Neil please wait don’t make me do this” Karen begged as if being held at gunpoint. *THWACK!* Neil’s hardened cock struck Karen’s face with such force as to knock her down. “You will call me Master from here on out, even at work you must refer to me as Master. I want everyone to know that I am your superior and you never be higher than me. Now, get to sucking my cock you fucking slut” Neil commanded. “Y-Y-Yess M-M-Mast-er” Karen forced out of her mouth. “Suck it bitch!” Neil ordered. Karen grasped at Neil’s hard cock toward the base, and put her lips around the tip of the tanned cock. Karen slowly parted her lips and took inch by inch of Neil’s cock in her mouth but Neil was growing impatient. He gripped the back of Karen’s head and slammed the rest of his cock down her hungry throat. Karen gagged and tears streamed from her eyes as Neil began to violently face fuck his tranny slave. A few minutes of this and Karen was ready to pass out. But before she could, Neil slid his cock from her mouth. “Turn around now, go over to the couch and stick your ass out.” He ordered. Karen weakly crawled into the postion her newly acquired Master had ordered her too. “Here, take this, inhale deeply. This is the only sentiment you’ll ever receive from me.” Neil said holding the bottle of poppers underneath Karen’s nose. Karen could feel herself ease up, but it was a whole new world when the fat tip of Neil’s cock parted between Karen’s her cheeks. The euphoric explosion of pain and pleasure overtook Karen. She had had dick inside her before but never as thick and long as Neil’s was. Slowly Karen’s ass was able to envelop the entirety of Neil’s cock at was at this moment Neil grinned widely and began thrusting faster and faster inside his new bitch slave. He shortly found his stride as the sensation of the poppers still swam through Karen’s head. Minutes wafted by as Neil ravished his new bitches tight taint. The effects of the poppers were fading and Neil knew this. As Neil neared his climax, the effects of the poppers had nearly worn off and Karen felt every thrust of her new Master’s hard cock. She had dreamed and hoped that this was all some cruel dream, but once the effect wore off she knew she was living in the real world. She could feel a sensation coming through Neil’s hard cock and knew what was about to come. Quickly Neil pulled out and ordered she turn around. “I’m gonna splatter your face with my manly cum you hear me bitch? And when I do you’re gonna go home with it covering your face and you’re gonna take a picture and send it to me so I know you obeyed.” Neil said. “Oh shit here it comes bitch get ready for it!” Neil shouted, “Yeeeeeeeeaaaaah! Fuck you bitch take my fucking cum all over that face!” Neil launched rope after rope of come all over Karen’s face. Once he had recovered from his intense orgasm, he shoved his middle finger in the bitches face and took a picture to further submit her new lifestyle as Neil’s obedient tranny slave. Neil commanded the bitch get dressed and get out of his home and not forget what he had told her to do. Karen now knew she was trapped. Neil had evidence of his Karen identity and now had pictures of him fucking and cumming on Karen. As Karen crawled out the door she heard Neil say to her. “be in contact shortly after you get home bitch. Remember the task I gave and not a soul will see these pictures. Answer as soon as you get the message bitch” He said with viciousness in his voice. As Neil slammed the door shut knocking Karen in the ass, she knew this wouldn’t be the last time, but in the back of her mind, she was excited about what Master Neil would do next.

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