tagTranssexuals & CrossdressersThe Office Halloween Party Ch. 01

The Office Halloween Party Ch. 01

byBebopJet©

It had all started innocently enough. At the Pro-Biotics regional office the crew always launched a rather rowdy Halloween party with loads of alcohol and "medicinal" marijuana. Steven always enjoyed the festivities even though he wasn't old enough to drink yet.

'Just one more year,' he thought, 'and then I'll be able to party with the rest of them.'

For a rather boring old office environment, there were loads of nice people who were all entertaining in their own right. Jessica was the office hotty with a nice round rump and long dark hair. Ben was Steven's best friend, another intern who was a year older than Steven and would be enjoying the booze for the first time at the party. Ben was a little taller than Steven and broader of shoulder, a guy who spent time in the gym but not a complete muscle head. Their boss Eric was a fair man who explained their duties clearly and had proper expectations of what they should and should not be doing as interns. And then there was Stephanie, the office slut. About the same height as Steven but with and amazing rack and long blonde hair, She'd pretty much slept with all the single guys in the office (and even some of the married ones), but she had a thing against sleeping with interns, which pretty much left Steven and Ben hung out to dry when it came to getting any from her.

The boys were always trying to one up each other, and the Halloween party wasn't going to be any different. Both had been boasting about their costumes for weeks, and tonight was the night of the great unveil.

That is, it would have been if Steven hadn't been late for the party by about 2 hours. Really, it wasn't his fault, he just didn't know his costume would take so long to put on. Going for realism over laughs, Steven had dressed up like Stephanie, including super slutty mini-skirt, loose sexy white blouse and red lipstick. What he didn't know was how creepy it looked without shaving his chest and legs first, which ate up a lot of time at home. He had to borrow the panties from his sister, which was another level of weirdness. But Steven was willing to go the extra length for a joke. He was just hoping his costume would be better than Ben's.

Entering the office earned him a lot of wolf calls from his co-workers, most of which were doing so because they thought he was actually Stephanie. He'd never realized it but he and her had very similar builds. Her hips were larger than his, and of course she had tits, but with the skirt on and the fake silicone breasts implants in the bra (something he borrowed from his dad's home office, a plastic surgeon by trade) he was able to be a fairly accurate double for the office bicycle.

After passing the front desk Steven entered the main floor of the office where all the cubicles were. There people were already fairly plastered as they drank and flirted back and forth with each other, feeling more free and rambunctious than ever. People were dressed in all manner of costumes, from The Hulk, to Edward from Twilight, to a woman in all body paint with a few key pieces of scales placed in various locations to keep her modest. He loved it when someone did Mystique.

Steven lingered around the punch bowl, wishing he could partake, and had to keep some drunken hands off him from the more slobbered of his co-workers. It was embarrassing and flattering all the same time, and Steven felt more than awkward with all the attention. If it was some ladies flirting with him, that would be one thing, but all the attention was from other men, which was odd and confusing to Steven all at the same time. He couldn't look that much like Stephanie, could he?

"Hey there sexy, need some saving from a real barbarian?" Came a husky voice from behind Steven.

He turned around slowly, already knowing who the voice belonged to. Ben stood there in a leather cod piece with a broad sword strapped to his back, bracers on his arms, and a leather bandana on his brow. Normally this would look campy on anyone else, but apparently Ben had been spending more time in the gym to really make the image look authentic. Muscles bulged all around his body, with veins lingering under the skin revealing how low his body fat was. It was intimidating to say the least, but also very impressive. Steven found himself blushing slightly having never seen his friend like this before.

"What makes you think I need saving from a half naked man?" Steven responded in his best Stephanie voice. It wasn't extremely feminine, but Ben already looked fairly plastered so it would probably work on him.

"You need saving from my pal Steven, who would like nothing but to get in your panties..." Ben slightly slurred and he leaned over Steven.

Smiling to himself, Steven decided to take this game a little further, just so he could really embarrass Ben later.

"Oh, and you're saying you don't want in my panties?" Steven teased.

"I'm just saying I'm willing to earn it is all." Ben cooed, the booze thick on his breath.

"Oh I'm sure Steven would be willing to earn it as well." Steven teased his friend, finding it funny that Ben still hadn't figured it out.

"Yeah, but Steven isn't packing 9 thick inches beneath his cod-piece." Ben whispered into Steven's ear, sending shivers down his spine. Steven had always been proud of his 7 inch cock, but if Ben really had a 9 incher then that truly put him to shame.

"Men always say their packing 9 inches, but few rarely prove it." Steven purred nervously. He was worried he might have been taking this a little too far, but he felt a need to see if his friend really had such a large cock.

"Tell you what gorgeous, I'll prove it to you if you promise to help finish it off once it's nice and hard for you." Ben whispered further in Steven's ear while playing with the small of her back. The situation was starting to become more and more confusing to her, and Steven's felt her reactions shift and Ben became more lustful for her.

"We're in the middle of a crowded party, you gonna just whip it out here hot stuff?" Stephanie...Steven teased, thinking his buddy was out of options for a private location.

"I just so happen to have a key Mary's office. No windows on the door or any of the walls, and she's been out on maternity leave for a month now." Ben revealed with a smirk, already grabbing Stephanie's hand and leading her through the crowd.

This was getting out of hand Steven though, his cheeks fully flushed, his mini skirt tenting as his obvious excitement. It was also obvious that Ben meant business as his cod piece was having a more and more difficult time keeping him contained. Steven thought he should pull his hand away and reveal to Ben that he wasn't Stephanie, but something inside him stopped him from doing that. Instead, he just followed his muscled friend through the back offices until he reached a corner one. Pull the keys out of a leather pouch that hung to his side, Ben swiftly opened the door and led Steven in, closing it quietly and locking the door. Suddenly the music died a mere hum along with the laughter and hollering of the party.

"There we go, alone at last." Ben said strongly with a wicked smile on his face.

"Yes, alone. Just you...and me." Steven continued, trying to think fast.

Ben slowly untied his belt and dropped the sword tied to his back. Unfastening various belts and buckles, eventually Ben dropped the cod piece to the ground, revealing a semi-rigid cock pulsing beneath. Steven gasped slightly and sub-consciously licked his red lips. He thought Ben might have been exaggerating about the size of his member, but it wasn't even hard yet and Steven was willing to bet it would be larger than 9 inches. It was evenly thick, growing larger with each second, the hair trimmed short and Ben's large balls hanging low. Steven was surprised the cod piece was able to keep all that man-meat in to be honest.

"What do you think honey, nice and large isn't it?" Ben said proudly.

Steven licked his lips again, and gulped slightly. "I don't know, it seems awfully...flaccid." Steven teased, preparing to drop the facade any moment.

Then Ben did something that shocked Steven more. He gripped his cock in one hand, and started stroking himself in front of her, growing thicker and larger with each stroke.

"Oh it gets bigger baby, trust me. Want to look at it a different way?" Ben asked in a very husky and lustful tone.

Steven could only nod, feeling herself weak in her legs.

"Get on the ground babe, on your knees." Ben almost commanded. What was even more odd was Steven almost instantly obeyed, getting on her knees before her best friend. Ben walked forward and stood over her, stroking his now fully erect 9.5 inch cock above her face.

"Lick my shaft babe." Ben commanded again.

It was now or never, Steven could either be Stephanie, the office slut, or he could be Ben's best friend and let him in on the goof.

In answer to her own question, Stephanie stuck her tongue out and licked the salty balls handing between Ben's legs. She engulfed them into her mouth and rolled them around, feeling their size and weight with her tongue. It was her first time sucking balls, having never thought she'd ever do it before, but Stephanie found she loved the taste of Ben's balls in her mouth. Ben continued to jack himself off and moaned heavily as he felt Stephanie take him in her mouth.

She continued to lick up his shaft and town the crown of his cock into her mouth, sucking him deeply and loudly. Stephanie sucked Ben like she'd want someone to suck her cock, slowly and with lots of saliva, avoiding teeth and going down as deep as possible, which was difficult with Ben's huge cock.

"Oh damn, I heard you gave good head, but I had no idea." Ben moaned, his hips rocking slowly into Stephanie's mouth.

Stephanie started rolling Ben's balls around in her hand while sucking his engorged member, trying to stuff as much of Ben's cock into her wanting mouth as she could. Stephanie felt Ben's hands running through her wig, giving her worry that he'd find out she was an imposter, but instead Ben just pushed on the back of her head trying to force more of his cock down her throat. She gagged loudly, having to pull away to catch her breath momentarily, but once she had recovered she engulfed his cock again, like it was as important to her as air.

Stephanie had a maze of questions running through her head, having given into a desire she never knew existed in her. She was on her knees, feeling extremely feminine and having her mouth used a fuck hole by her best friend. What had started as a joke had taken a very odd turn to say the least, and the oddest part of all was how much Stephanie was loving it. Her cock strained against her panties, causing her skirt to tent, but luckily Ben's attention wasn't there...yet.

Ben continued to push her head on his cock, riding her face like he would her non-existent pussy. Maybe he'd be happy enough with a blowjob and once he blew his load in her mouth, they'd stop and Stephanie could run away and figure out what to do next. But just the thought of swallowing Ben's load sent shivers up her back again, causing her to moan loudly into Ben's dick as it rubbing back and forth against the back of her throat.

"Oh yeah baby, you are something special, I need to be inside more of you." Ben said hungrily, popping his drenched cock out of her mouth. He lifted her up and forcefully bent her over the ouch, tugging her panties down and spreading her ass.

It was all happening so fast that Stephanie hardly had time to even properly freak out about Ben finding out that Stephanie was actually Steven. She had her ass cheeks exposed, her head pressed into the pillows of the couch in Mary's office. Stephanie started trying to lean up and get out of the shameful position she found herself in, when suddenly she felt Ben's wet tongue pressed against her asshole. She moan loudly and lustfully, displaying how much of a whore she really was as she ground his ass against Ben's face while he rimmed her properly. She didn't think it could get any better until she felt a hand wrap around her engorged cock and begin jerking her off while her asshole was eaten.

"Holy crap! Ben, do you know I'm Steven?!" Stephanie asked in exclamation while still maintaining her Stephanie voice.

"I knew when I first saw you, but that doesn't change how fucking sexy you look. Does this mean you don't want me to fuck you." Ben responded quickly, disturbing his ass eating for a moment while he continued to jerk her off.

Stephanie continued to moan in deep pleasure, pressing her ass against Ben's face. Finally, in a low and erotic tone she whispered "Fuck me Ben, take my cherry..."

That was all it took and Ben stood up and took position behind Stephanie. He spit on his cock and rubbed the saliva into Stephanie's rosebud hole. For her part Stephanie was equal parts scared and excited, not sure if she could survive a proper fucking by Ben's huge cock. She still wasn't completely over the fact that Ben knew she was Steven the entire time, but the cock pressed against her asshole was pushing those concerns out quickly as she felt Ben start to enter her.

His cock head felt enormous as Stephanie felt her hole expand to fit Ben's crown. She breathed slowly and steadily, biting her lower lip and gripping the couch tightly as Ben eased into Stephanie slowly. After he was about two inches in, Ben stopped pressing into her ass and just let his cock rest in her shallow opening. Stephanie was about to protest, wanting to feel more of his girth inside her, but Ben just stroked her ass affectionately, indicating that this was for her own good. She needed to relax and accept him inside her before he could continue.

Focusing on her breathing again, Stephanie took a moment to really enjoy how wonderful it felt to have her asshole stretched out by her best friend. She never could have imagined tonight would have led to this, nor did she want it to mere hours ago, but now that it did she realized that somewhere deep down inside she'd always wanted this. It was just something she couldn't have ever openly admitted to herself. Maybe that was the real reason she dressed up as Stephanie, not to play a joke but to be who she always wanted to be. A cock hungry whore with her best friend's dick plunger deeper into her asshole. Stephanie perked up, feeling Ben's renewed movements behind her. He roughly grabbed her hips and pulled her ass back, forcing more of his cock into her ass.

This was the final stretch, so to speak, as Ben plunged the rest of his 9.5 inches all the way into Stephanie's ass. Her eyes went wide and her cock jumped up as the crown of Ben's cock rubbed her prostate. Each stroke Ben took into her rubbed her prostate more and more, keeping her erection hard and bringing to light new pleasures she'd never experienced before.

And before she knew it, Ben was entirely inside her, his balls resting firmly on her ass cheeks. Once all of Ben had been shoved deep inside her, he started fucking her with a slowly and purposeful stroke, make sure she felt each inch of his cock pull out of her and then invade her all over again. Each time his cock pushed back in it rubbed lovingly against her prostate, forcing pre-cum to ooze out of her cock and stain her panties. But she didn't care at all and just sat there, ass high in the air, enjoying the feeling of being well fucked by her horse-hung friend.

Suddenly Ben slapped her ass as he fucked her hard, causing Stephanie to jump a little and moan out loud again, revealing her true slutty nature even more.

"Is this what you've been wanting, your best friend to fuck your slutty ass?" Ben asked, his voice full of sexual hunger.

"...yes..." Stephanie managed weakly.

"Yes what?" Ben asked, slapping her ass again.

"...yes, sir." Stephanie answered, starting to realize just how the dynamics of their relationship were shifting.

"Do you like the feel of a huge cock rubbing inside your asshole slut?" Ben demanded to know with a slap of her other ass cheek.

"Yes, sir, I love the feeling of your cock inside me." Stephanie explained with a moan, as Ben sharply slammed his cock into her again.

"Do you me to breed you slut?" Ben asked, humping her fast and with more purpose.

The question confused her at first, but then she realized what he meant. "Oh god yes please, spill your seed inside me. Make me a true slut and cum in me with your unprotected cock." Stephanie truly begged from her new master.

That was all Ben could take and he drove his cock back into her hole one final time before it erupted inside her, cum pouring out of him in waves of sexual delight. The last plunge pushed Stephanie over her limits as well, rubbing her prostate just the right way to cause her to cum also, filling her panties with her seed. Together they bucked and rubbed their bodies together as their sexual highs peeked. And just as fast as they climaxed, they came down and realty sunk in.

Ben had his cock shoved up his best friend's ass who was dressed up to the nine's looking a lot like the resident office slut. Steven was bent over the couch, ass spread wide open with Ben's cock buried deep inside him, his asshole and his panties soaked in cum. The two start to untangle from each other and Ben sat on the leather chair across from the sofa while Steven gingerly sat down on the couch, his rear a little sore from the recent attention.

"Well that was...unexpected." Ben admitted with a blush.

"So you knew it was me the entire time?" Steven asked, shock returning to his system.

"Well yeah, I already saw and got shot down by the real Stephanie an hour ago. She dressed up as a cheerleader, how unoriginal." Ben admitted with a roll of his eyes.

"And despite knowing it was me, you continued to flirt, then fuck me?" Steven continued.

"You seemed to rather enjoy it." Ben returned with a smirk.

Steven blushed, returning momentarily to Stephanie mode. "Well yeah, I wasn't expecting that I would, but you just took charge and you knew what you wanted, and what you wanted was me. That's powerfully erotic." Steven explained, his cheeks crimson.

"And what if I want is still you?" Ben asked, his eyes dark and his tone heavy.

Steven blushed deeply again, squirming in his seat.

"Come here slut, and sit on my lap." Ben commanded in a tone Stephanie couldn't resist.

Steven may have sat on the couch, but Stephanie was the one who rose from it and walked to across to the chair Ben was recliner on. She straddled him and lowered her still exposed ass onto his recovering cock, letting it slide past her cheeks and press back into her. She moaned heavily and held onto Ben's shoulders as she forced herself down onto his cock more.

Then Ben did the truly unexpected. He reached up and pulled her head down to kiss her deeply and passionately. His tongue forced its way into her mouth and rolled around her own tongue, invading her much the same way he invaded her earlier. She groaned heavily into his mouth, enjoying him taking her forcefully again and she ran her hands along his muscled body, delighting in how feminine she felt and how masculine he felt.

Ben broke the kiss and looked her deep in her eyes as he started fucking her again, his cock now fully erect again. "I think Stephanie and I need to hang out a lot more from now on." He announced boldly.

Stephanie just grinned and moaned again as she felt his cock plunge back into her. "I think so too...master."

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by Anonymous

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by Anonymous04/16/14

The Office Halloween Party - Chapter 01

I am a classy, mature crossdresser and enjoyed the story very much. I am looking forward to someone taking my anal cherry soon. That sounds like a very enjoyable experience, and hopefully, once it happens,more...

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by BrendaNW02/19/14

so hot

I need to be Stephanie and be fucked just like that..

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