Choose Your Costume WiselybyBethyboo©
Happy fucking Halloween.
That was his thought as the alarm bell clanged this cold autumn morning. A costume, where the hell was he going to find a costume on Halloween day. The memo from the office booster club arrived in his inbox at exactly 5:55 pm last night. It was a lucky thing he even saw it. What the hell were they thinking springing a costume day at work on such short notice. Mandatory, imagine that, a prestigious law firm and they wanted the office dressed as clowns.
There had better be a big fat treat at the end of the day, and it better come in the form of cash. He showered and considered going in naked, costumed in his birthday suit. That would be enough to send the prudish secretaries running for cover, and would certainly cause more than one sexual harassment suit. Would serve them right, a costume on such short notice was enough for a mental harassment suit on his part.
Grumbling over his usual breakfast of a protein shake and a banana, he was dressed in his birthday suit, naked as a jay bird and he should just stay this way. Hang a sign around his neck...NUDIST! Deal with it!
Rinsing his glass and tossing the banana peel, he headed to his bedroom. Rifling his closet, did he actually own anything other then suits, shirts and ties? Inspiration struck, there at the very back of his closet hung a foreign item. The dress he had bought for that no good ex-girlfriend. But could he squeeze into it? Worth a shot I suppose.
He felt his smooth face, freshly shaved and started to smile. He grabbed the dress and slipped it over his head. Hmmmmmmm, not bad, but I need titties. He checked the drawer, the one he had reserved for her things and to his surprise found a bra, panties and stockings, luckily dark stockings, if no one inspected too closely they might not notice his hairy legs.
He pulled the dress on and wrapped the bra around his chest. Why did women wear these things, comfort was definitely not a design demand. Now to find boobs! His girlfriend was rather modest chested, so no need for watermelons. But, a couple of balloons, filled with water and wrapped in socks might just work. He constructed himself some titties and for added effect glued a pair of sawed off golf tees for nipples. He turned to look at his profile in the mirror. Boobies complete with erect nipples. The effect was rather good.
He slipped on the panties, tight enough to hide his cock, as long as he didn't get aroused at work...fat chance of that happening! He had been looking at the same old co-workers for years now and no one had even piqued his interest enough to ask their name let alone stir any sexual desire.
Stockings slid surprisingly easily over his muscled hairy legs. The dress came to mid thigh and the look was complete, except for shoes. Where in the hell would he find a pair of size 10 women's shoes at this time of the morning? And how the hell would he manage to walk in them?
He got down on his hands and knees...scooting to the back of the closet, cell phone held aloft to see if maybe something other than his standard black leather dress shoes might be hiding back there. And sure enough, that rotten ex of his had left a shoe box with sandals in them...tags still attached. She had no sense for money, at least not his money when she went shopping.
But at least they were sandals with no heels. He squeezed his size ten man feet into the size 9 woman's shoe and fastened the strap. Maybe not a fashion statement with the slinky red dress, but better than his shoes. He winced as he stood up, the sandals tight and uncomfortable. It will remind me of how much this pisses me off at least.
But his hair, short and closely cropped, thick eyebrows...what to do about that?
Finding tweezers, surprised that he had some he stood in front of the mirror and quickly plucked his eyebrows into a semblance of womanly appearance. Smiling he found he liked the shaped trim eyebrows. He put the tweezers where he could find them easily next time. Now for hair. What to do for hair?
He started grinning as he remembered his neighbor two floors down had wigs. Lots and lots of wigs. She was a wig designer of all things. And she had borrowed coffee that one morning.
He grabbed his briefcase and headed for the elevator. Punching the 11th floor button he found himself smiling and humming "The Monster Mash," the only Halloweenish song he could think of.
As he knocked on her door, he realized he didn't even know her name, just thought of her as the wig lady, usually adding the adjective crazy to the moniker.
She answered his knock and stood staring at him with such a look of abject horror that he started to laugh. Once the laugh started he couldn't stop. Her look never changed, but she backed away from the door...preparing to shut it, and probably lock every one of the dead bolts he suspected lined the door casing.
Finally catching his breath, he said, "Hi, I'm Thomas, I live upstairs, I am dressed for Halloween, but as you can see, a few key ingredients are missing. I thought maybe you could loan me a wig."
At that point, her horror turned to mirth and she let out a girlish giggle. "Come on in. You need some help if you are going to pull this off."
"I have made as many wigs for men as for women, and I think I have the perfect one for you...also a pair of shoes that just might fit better than those things you have on." She led him into her work room. A mass of wigs, and a rack of clothes, a rack of shoes and a make-up table. "I don't just make wigs, I do complete make-overs as well as the occasional low production movie costuming."
He smiled, he had certainly wished he had known that before he had dressed in this outfit. "Maybe you can find me a costume, instead of this disaster I am wearing. I saw the look of fear on your face when you answered the door."
"No, the look of fear was from thinking I was supposed to have a custom wig ready for a customer that I didn't remember booking an appointment for. Apart from the shoes and the hair...you look pretty good. I am not even going to ask why you own a dress though."
Frowning at the implication he said, "I bought it for an ex-girlfriend, she never came back to wear it. Found a better offer I guess."
"Well that doesn't matter, fixing you up is what we need to do now. So relax and let the expert have her way with you." she winked at him as she went to work.
"Here's a pair of heels, size 10 mens, and before you ask...lots of men dress like you do everyday."
While she rummaged her collection of wigs, he sat down, discarded the too tight sandals and strapped on the black leather shoes. He stood up, wobbling and grabbed a chair to steady himself.
She laughed watching him, "You practice while I prepare the magic."
After just a few minutes he found he could maneuver around the room, without too much wobble. He would sit at his desk and not move for the entire day...just another pretty face.
She sat him at her make-up table and transformed his manly face into a pretty, not quite beautiful, but definitely a pretty girly face. She added the wig and he gasped at the transformation. She added a "Ta-Da!" and announced him ready for Halloween, or a date with a handsome man. This was followed by a fit of giggles as she leaned in and kissed his cheek. "You owe me big time for this, and I want details of how many men hit on you today!"
As he was getting ready to leave, she looked at his briefcase and said, "That just won't do." She disappeared and came back with an over sized purse. "Put all the things you need in here for the day. I'll have supper ready when you get back, I really am interested in how your day goes."
He told her, "Thank you." in the open doorway and her parting suggestion was, "Try not to say anything, just smile and look pretty."
He laughed, then tried a girlish giggle. Raising his voice an octave, "Thanks for the advice."
He arrived at his office on time, barely, and whisked in past his co-workers, everything from batman to Dracula to a fairy princess and a slew of other recognizable outfits. "They must have had advance warning of the costume mandate." he thought.
As he was passing his secretary's desk, he saw a note. It read "Junie called in sick, sorry, we called for a temp but they didn't think they could find one for you today." Inspiration struck. He sat at the desk, and quickly called himself in sick. He would be the temp for the day.
After a few minutes one of the secretaries, dressed in some sort of version of a bunny rabbit, stopped by his desk. "Hi, my name is Wilma, you must be Mr. Rexton's temp for the day. I have good news and bad though. The good news is, he called in sick so you won't have much to do today, and lucky for you because he is a tyrant. Bossy and demanding. The bad news is that you were supposed to wear a costume, but no worries, we understand it was short notice. Thanks for coming in, and just answer the phone, take messages and enjoy the day I'll just hop on about my business."
He managed to stammer out a simple, "Thanks." a little hoarse, but he could always claim he had a cold. He was rather insulted by the implication that he was a tyrant and vowed to look into her upcoming Christmas bonus, to make sure it was of an amount worthy of a tyrant.
The phone was surprisingly quiet and no one approached his desk so he worked on his files, a good day to catch up on paperwork. Lots of glances and a few open stares as he sat working...until lunchtime. One of the newer attorneys came over and sat on the corner of the desk. A large "S" adorned his chest, he apparently fancied himself Superman.
"You must be the temp. I'm glad you didn't wear a costume, because," he leaned in very close, "then I wouldn't have known how beautiful you are. He grinned and continued, "There's cake and treats in the lunchroom, come on and enjoy."
He stood and offered his arm. She stood, placed his hand on the offered arm and followed him into the lunchroom.
There was enough chatter that he found he could just smile, or pretend to be chewing his food and nod. Lunchtime over, day half over and he was smiling, he had pulled this thing off. But damn, how could they believe that he, He was a woman.
By 4:00 most of the staff had gone home and he decided that he could go into his own office and get a couple of hours of real work done before his usual quitting time of 6:00.
A quick trip to the bathroom and call it a done deal for the wig.
There was another woman in the hallway and they stopped and stared at each other. Wow, she is stunning he thought, how come I never saw her before. And why is she not wearing a costume?
She said, "Hi, I'm a temp here today."
He smiled, "Me too."
They walked into the bathroom today making, what he hoped, was girl talk. He stared around the women's washroom. Not so different from the men's, apart from the urinals.
He went into the stall and struggled with the panties, then decided he better sit down to have this piss.
They both emerged from their separate stalls at the same time and stood washing their hands. He felt almost like a pervert, in the ladies can, openly leering at a woman, who thought he was a woman. He felt the stirrings of his cock. Oh no, this could be bad.
She reached over and placed her hand on his arm. "I know we don't know each other, but we are both temps here, will probably never see each other again, and I am attracted to you."
His heart pounded in his chest. He swallowed hard, thought of the law suit in the making, but hey...this was her idea.
He stammered out, "You are beautiful, and I am so attracted to you, I could do you right now."
She giggled and led him into the largest stall and clicked the lock on the door.
She leaned in for a kiss and he kissed her back. Her tongue drove deep in his mouth, thrilling him to the point of no return. He grabbed her shoulders and pulled her closer, grinding his hips to hers. She pulled back, and he thought, "She felt my cock throbbing against her hot pussy and knows I am a man."
But she wasn't shocked or looking afraid at all. She ran her hands over his shoulders, and leaned in to renew the kiss. She reached up to feel his boobs and this time he pulled back. She'll know for sure if she goes squeezing on these water balloons.
She looked at him quizzically and said, "This is rather awkward, but maybe if we each put on a blindfold, we won't feel so self conscious. He readily agreed, just bend her over, fuck her hard and get the hell out of there. "No one even knows who I am."
"OK, good idea."
She bent and removed both of her stockings, handing him one. They tied the make-shift blindfolds over their eyes and promised no peeking. He reached for her but it was too late, she had spun him around backwards, pushed him forward over the toilet and was hiking up his dress in the back. With one hand bracing him forward, she ripped his panties off his body and before he could utter a word of protest there was a hard cock pushing against his ass.
The only thought was "Shit...I am not the only man dressed as a woman today and I am about to get it up the ass. Can't he tell an ass from a pussy?"
The cock kept pushing at his ass and his own cock got harder, thicker and longer, throbbing painfully as it bobbed up and down.
"Stop it you fool...I'm a man too,"
The manly voice from behind said, "I know, I could tell from the first minute you walked in the door Mr. Rexton, but I have been wanting to fuck that tight ass of yours for years."
"Happy fucking Halloween!" and with that he thrust his cock into the tight ass, letting out a grunt, accompanied by a scream. Without letting up he fucked his ass, hard and fast, full strokes.
Mr. Rexton was numb with shock. He was enjoying having his ass forcefully taken. The initial pain actually made his own cock harder. He reached down to stroke himself as his ass was being destroyed by the monster cock that pistoned in and out like a machine.
The bathroom rang with the sound of two men taking pleasure from one another. The smell of musk hanging in the air. His ass on fire, he felt the first jet of cum and almost lost his own as this 'woman' came in his ass. He was still panting, still hard and still needing when the cock slipped from his ass. The other man spun him around again, and dropped to his knees. Mr. Rexton was getting the best blow job he had ever gotten...and from a man.
The man sucked and bit at his cock. He braced both arms on the stall walls and pumped his hips. Throat fucking this heavenly mouth. With a grunt, he felt his balls tighten, drawing up tight to his body and put both hands on the mans head and held him there. His balls resting on his chin while his cock pumped a load of cum right down the throat of another man.
Gasping from the exertion and the pleasure, he felt himself embraced, hugged close to this near naked man...and then the feel of lips on his. He could taste his cum and he licked at the lips eagerly, driving his tongue deep to get more of that taste.
The door opened and he found himself alone, blindfolded in the women's washroom, cum leaking out of his ass and the taste of his own seed still lingering on his tongue.
He slipped off the blindfold, retrieved his panties and pulled them on.
Still shocked at what had happened he packed his purse and decided to call it a day. Who was that woman/man?
He would have to live with knowing that someone in his office knew what he had done. He would have to live with what he had just submitted to, and the knowledge that he had loved it.
But those were thoughts for another day.
This was Halloween and he was going to enjoy the rest of his day. And he still had to return the borrowed items to the crazy wig lady. The cute crazy wig lady.
He rapped sharply at her door. She answered and stepped back to allow him to come in. Once he was inside, she shut the door and locked it. She turned to look at him and then grabbed him and started to kiss him. He was hesitant at first, then eager as her tongue delved deep into his mouth. Her kisses both shocking and arousing. Her hands ran over his chest, dipping lower to rub at his cock through the dress and thin panties. He wasn't sure what to think, but decided that thinking might be a little over rated at this moment.
Two sets of girl clothes hit the floor just inside the entry. She clung to him, his recently sucked cock springing once more to full attention as his thoughts strayed to the feel of that cock in his ass. She grabbed his hand and pulled him to her bedroom where she pushed him onto the bed and climbed on top of him.
"What is with all the sexually aggressive people today?" he pondered. Not that he was complaining though. He lay back while she sucked on his cock. Her skills were amazing. His cock throbbed, harder and longer with each poke of her tongue at his piss slit. Her hand cupping his balls, gently at first, then she increase the pressure until he was ready to scream. She let go and lay down beside him.
"So, tell me, how many men hit on you today?" she laughed as she looked sideways at him, licking her lips, one hand lazily stroking his cock.
"Only one. Just the one man...oh," he grinned, "and one woman."
"Hmmmmm, did you fuck the woman?" she had just a hint of a frown on her face.
"No, I promise you I did not fuck that woman." He laughed and rolled on top of her, "But I am going to fuck you!"
He took her hard, her cunt already wet and slippery. His thick cock sliding all the way in and he nestled deep inside for a moment before pounding her cunt as hard as he could, as hard at that man had taken his ass. When he thought of his own ass getting fucked, his cock twitched inside the warm wet pussy.
He pulled his cock free, kissed her on the lips and said, "What I'd really like to do is fuck your pretty little bum. I want to shove my stiff prick right up your tight brown mouth and see how well you kiss at that end."
She looked deeply into his eyes, "It's about time. I have wanted you since I first borrowed that coffee."
With that she rolled over, raised herself on her hands and knees and waggled her bottom at him. "Do you think you can find it, or do you need a little help?" Without waiting for an answer, she reached back and parted her cheeks, fingers digging in, giving him a clear view of her delightful asshole.
He wasted no time, put his cock at that back door and pushed, it was almost painful, the pressure on the tip of his cock. He thrust his hips forward and leaned his body ahead to let his weight push his cock, and was rewarded with a release of her sphincter muscle. The tiny rose bud blossomed around his cock, kissing it tightly. His head now completely enclosed, he felt her body quiver, the snug fit rippling around the crown of his cock. He wasn't sure if the moans coming out of her were of pain or pleasure but when she pushed back against him he took it as silent permission to drive his cock home.
His balls slapped upwards against her wet cunt, making a delicious sound to accompany the whimpers and moans. He pummeled her ass, hard and fast. His cock a blur as he made full strokes, tip to base, almost letting his cock slip out then driving it back in so that his balls continued the assault on her pussy.
She started to buck underneath him and he fancied himself a rodeo rider trying to stay on the bull. He grabbed a handful of her hair and held on, sealed to her by the tight grip of her asshole on his cock. His own asshole twitched as he felt that familiar and welcome tingle start in his balls. He imagined he could feel the cum surging up and through his cock, felt his little piss hole flare as he shot his load deep in her bowels.
As he emptied his cock, his free hand snaked under her, tweaked at her clit, rubbed hard until he felt her shudder. OMG! when she came, with his cock still in her ass, it felt like she was trying to strangle him. Her ass spasmed and convulsed while her entire body shook with the force of her orgasm. It felt like hours before she stopped moving under him. He pulled his hand free and tasted her sweet girl cum, then untangled his fingers from her hair while his cock reeled itself back in, retracting closer to his body and finally slipping free of the tiny mouth that had tried to devour him.