tagTranssexuals & CrossdressersDriving for a Change

Driving for a Change


This may well be the start of an on going series. So I hope you all enjoy it, as with any of my stories feedback and e-mails are always welcome.


Sam sat his desk working over the spreadsheets for the past couple of days when the call came in. He grabbed the phone at the other end it was Mister Sanderson, the head of the company, and he wanted to see him right away. Standing up Sam stepped over to the mirror on the back of his door. Everything was as it should be his hair was still the way he'd groomed it that morning. His suit was a nice black knock off of a expensive one he liked.

His office was six floors below Carl Sanderson's he walked on to the elevator and pressed the top button then waited. The whole while his mind raced trying to figure out just what he had been summoned for. He hadn't done anything outstanding, and to the best of his knowledge he hadn't a mistake so large that he'd be called up for some type of punishment. The whole thought process had turned to nothing but worry and second guessing by the time the doors beeped and slide open.

The top floor lobby was designed to impress and intimidate it was the first thing most people saw when they arrived for a meeting. Everything was polished steel, glass, marble and glistened in the light through the windows. Sam stepped off and glanced around a few Asian men in suits sat patiently waiting for their scheduled meeting. A woman, he recognized as the head of the Middle East division, was shaking hands with a couple of Arabic men.

Behind the front desk the receptionist, Gloria, sat with her blonde hair hanging down in ringlets. He was surprised by just how much her hair matched his own both in colour and texture, all he lacked was her length. She smiled up at him it felt like a plastic smile the same one she used to greet everyone who walked through the doors. "Hello Sam, Mister Sanderson is in a meeting take a seat."

"Thanks" He answered and stepped over to the waiting area and took seat opposite the Asian men.

A few minutes went by and the Asians disappeared into a conference room led there by the Gloria. Her computer chimed as she returned, "He'll see you know second door on the left." she pointed down a hallway.

Sam stood up and followed her directions the door was frosted glass with Carl Sanderson, President North American Operations etched into it. He tapped lightly on the door and a deep baritone voice called out from the other side "Come in Sam." So he pushed open the door and walked inside.

The design from the lobby continued into his office and projected a sense of power and authority on to Mister Sanderson. He sat behind the one thing in the room that felt out of place a heavy antique oak desk. On second glance he realized it wasn't an antique only designed to look like one, a computer monitor had been inset into the desk along with a phone as well. Behind the desk sat Carl Sanderson who was a large muscular man with short dark hair in a suit that didn't look all that different from Sam's on the surface.

"You asked to see me Sir."

"Yes, Yes I did please have a seat Sam and be comfortable."

"Thank you Sir," He sat down in the seat opposite his desk although he wasn't all that comfortable.

"Can I get you a drink?" he twirled around some amber liquid in his own glass.

"No thank you."

"Alright, lets get right down to it then shall we. You're apart of Adam's team working over the third quarter numbers for North American."

"That's right sir."

"Good I have a new assignment for you then. Adam's has a big enough team to do what he's doing that you won't be missed. I'm sure he will still find someone else to triple check all the numbers anyways."

Sam didn't like the feeling he got from someone describing his job as triple checking someone numbers. He swallowed the feeling and didn't comment on it, "Certainly Sir. What do you need me for?"

"I've had a little problem with my wife as of late. You see she has a thing for large muscular men like myself. In the past six months I've found her with her bodyguard, then later with my driver and most recently with her new guard. You look nothing like any of them, so you should be a safe choice. Now I love this woman dearly. Now since she's never turned me down when I'm horny I haven't really said or done much about it. But I want to take away the temptation for her and make things a little easier. I want you to be her new bodyguard and driver."

Sam was floored he couldn't believe his ears he was an accountant. "I'm sorry Sir, maybe you miss understand I'm just an accountant I've never fought anyone. I'm not trained to do anything like what you're asking me."

"Fair enough, I'll contact our security department to make sure you get some training in that respect. Think of your new promotion as more a variation on the old if you'd prefer. You can help me to keep track of her spending as well as protecting her. That would take a full time accountant by itself so it will keep you busy with math." He slide a sealed envelope across the desk to Sam who reached for it, and tore it open Mister Sanderson continued. "I'll be doubling your pay plus providing you with a clothing allowance so you can fit in wherever she drags you. Try it out for 6 weeks and we can decide where to go after that. The keys, a credit card, codes, and everything else you'll need is in there." he pointed at the envelope.

After Sam swallowed some choice words he started to give the whole offer some serious thought. Double pay, plus doing a favour for Mister Sanderson would be a huge career boost. In the end the real question was did he want to be some sluts babysitter? However he knew Carl Sanderson wasn't a man one refused lightly. "I'll do it but only for the six week trail. After that while see what happens."

"Fair enough. You can pick her up 10 tomorrow morning you've got the address. Pass along any leftover work and the rest of the day is yours. I'll let HR know about the promotion and we'll talk again in six months."

It was dismissal if Sam had ever heard one "Thank you for this opportunity." He was out of the office a few seconds later with the envelope tucked under his arm. The elevator chimed as he approached and he got on. Then half an hour and a couple of e-mails later he was out of the building. The rest of the night flashed by in a blur.

The next morning Sam woke up to the sound rain beating against the window. He groaned inwardly that wasn't going to make his first day any easier. Across from him the clock radio blared out soft music as a reminder that it was time to get out of bed. Everything seemed like it was taking forever mostly because he wanted very little to what he would be doing for the rest of the day. At the same time he also knew that if he didn't do his best over the next six months it could cost him his job as well.

The pick up address was an upscale condo across from Central Park. Double parking in front of it he stepped out as the his watched beeped to announce the hour, he was right on time. He opened his umbrella as he walked around the limo, ignoring the horns and shouts that came from the drivers in cars behind him.

She stood just inside the doorway red hair cascaded down around her pale face. Her make-up was immaculate nothing was out of place. Sam recognized the outfit she wore, he'd seen it on a celebrity gossip shows, Angelina Joile was wearing it. The pants were a loose fitting pin stripped plazo pants and a matched draped top hung very loosely over her ample chest to form a U of exposed flesh.

Sam closed the small gap to reach the protective awning of the condo and gave the umbrella a shake . A doormen held open the door for his new boss, there was no doubt in his mind as to why Mister Sanderson was having such a problem with bodyguards he felt a stirring himself as he greeted her. "Good morning Mrs Sanderson."

She stepped outside and gave him a once over "So you his latest attempt are you. You look more like a girl then a bodyguard. I hope you've got it where it counts." As she walked past her hand reached out and brushed across his semi erect shaft. He did his best to focus on the job and hurried along at her side lifting the umbrella up to keep her dry.

The next several hours were spent shuffling from one function to another. Sam couldn't believe how busy an unemployed rich woman could be. Apparently she was a part of a number of different volunteer boards and the head of several charities. The whole time he just stood in the background listening, in his head he ran the various number he heard and found himself surprised again by just how much this volunteer groups had to work with, and how much the raised. Mrs Sanderson never referred to him and hardly ever spoke to him at all, other then to be derogatory about his stature or to tell him where to go next.

After they left lunch at the Ritz Downtown, where Mrs Sanderson had visited with several girlfriends while he sat at the bar, she gave him a new address one that hadn't been pre-planned. Sam glanced up questioningly but she didn't add anything other then to seal the divider and cut him off. A few minutes later he pulled into a parking spot in front of an upscale clothing shop. The rain had let up along the way and the sun was starting to poke through the clouds so he could dispense with the umbrella. He pulled open the door for her and she climbed out slapping her purse into his hands she headed straight into the store leaving him to trail behind her.

Inside smelled like a sweet mixture of perfumes and flowers. At the door a gentleman in a suit kissed Mrs Sanderson on the cheeks greeting her like an old friend as he walked in behind her. Sam waited just inside the store's door. Everything inside was covered in ruffles and lace designed as high-end woman's under garments. Sam couldn't believe his eyes, a whole store devoted to nothings but panties and bras. The one things that seemed to be missing from anywhere in the store was a price tag. Apparently if you had to know the price in advance then you likely couldn't afford it.

The man who'd greeted Mrs Sanderson and an attractive dark haired skinny woman were both busy helping her. She wore a near transparent dress that hung down to her knees under it her underwear was there for the world to see. A white lacy thong and matching bra stood out like a beacon against her dark skin. Their discussion seemed quiet animated from where he stood. The man would point off in one direction or another and the sales girl would hurry off to collect whatever was needed. Sam found the show quiet enjoyable, and the girl was certainly pleasing to the eye.

"Oh Sammi come here!" Mrs Sanderson voice called out.

He headed back to her catching one last glimpse of the girl as she reached up to put something way on one of the upper shelves. The firm cheeks of her ass where there for the world to see as she stretched out to put it back in place. I rounding the corner and found Mrs. Sanderson alone with a bundle of underwear set out on a velvet bench before her. A large dual fold mirror was the man feature of the wall beside the bench. "Yes?"

"I'm buying a gift for a dear friend and I'm having some difficulty deciding. My first though had been to just buy them all for her, then I realized how impersonally that was. That was when it hit me, you have same girlish figure as her. So put these on so I can decide which would be best for her. Just tuck that little dicky of yours up and out of the way."

Sam looked her in the face trying to tell if she was joking or serious. "Pardon me?"

"Try those on so I can decide which ones to buy. Come on I don't have all day."

Sam couldn't believe what he was hearing "No, I draw the line at this. I'm a professional accountant not your freaking barbie doll."

"Fine, I'll take a cab home and you can find a new job tomorrow after my husband hears about how you tried to force yourself on me." her voice was cold and deadpan.

It had taken Sam well over a year just to land the job at the firm and that had been with the help of a friend. She had him by the balls and could completely fuck him over if he didn't do exactly what she said. Slowly his thumb flicked open the button of his pants, and the pulled down his zipper.

"A smart decision Sammi."

Sam dropped his pants down around his ankles and stepped out of them his boxer briefs offering only a little bit of modesty to him. He picked up and pair of the panties from the bench and started to pull them on.

"Take those off, they'll be far to distracting."

He sighed and dropped the briefs as well. There he was naked from the waste down in front of his new boss who stood there looking on with passing interest. He reached forward nervously picked up a red thong from the pile in front of him. The material was a silk that felt smooth and soft under his fingers. He held them out and tucked a finger in the waist band. Nearly did he put them on sides but at the last second he caught his mistake and stopped himself.

Then he stepped in to them pulling them up his leg. All through his live he had had relatively hair free legs, it was just a part of who he was and he'd never given it much thought. Now first time ever he felt very self-aware of that fact and how it made him that little bit more feminine. He pulled them up the rest of the way and his soft cock was cupped by the fabric. The lace pattern in the fabric formed a little heart right in the middle of his crotch and framed him with it.

"You forgot to tuck Sammi and although its pretty small it does seem to be getting bigger. So get it out of the way before it's to hard of a problem to deal with."

Sam reached down and pushed his shaft down between his legs and it only got harder. His own body fought back and it flipped forward poking up towards the ceiling. The more he tried to push it down the more it fought back and the harder it got. He raised an eyebrow at Mrs. Sanderson who yawned and yet couldn't take her eyes off it. "Deal with that while I'm gone." with that she stepped out in to the store.

There Sam stood a pair of panties around his waist and his cock pocking out of the top of them. Thoughts of large strong football players raced through his mind in hope of calming his raging hard-on, they had no affect. The curtain was pushed open a couple of moments later and she walked back in with the dark skinned clerk in tow behind her. "Not finished huh? Deal with that will you the tip will be well worth your while."

"Certainly Mrs." the store girl said. Sam hadn't noticed earlier but the whole dress she was wearing was held up by a single tie that ran around the collar. She gave a cord a tug and the whole thing slide down her body. Moving closer she kissed him full on the lips her tongue pushing its way in to his mouth. He felt her hand grip him and wrap around his full width. Slowly she started to pump him up and down, her tongue matching the rhythm in his mouth.

His arms moved of their own accord around her waist and pulled her body tight against his. It stopped her hand but put him back in at least some control of the situation. Her tongue felt so good in his mouth, its velvet touch brushing against his lips as it pushed in and out. He thrust forward grinding himself against her until he heard her moan. His fingers dug under the band of her thong and pushed them down over the curves of her ass. He could feel her hands as the brushed against him while she pushed down the front as well, seconds later they where both naked from the waist down.

Out of the corner of his eye he caught sight of Mrs. Sanderson who stood there watching with hidden interest in there every move. He wasn't a hundred percent certain but he thought he could see her nipples poking excitedly against the draped fabric. When their eyes met for a brief moment she just frowned at him.

Sam guided the girl to turn around and pushed her forward bending her over the plush red velvet bench. Her lips squeezed out from between her legs and he pushed a finger in exploring her depths. She was wet and grew more excited by his touch. Apparently not at all shy about what they where doing she thrust back against his hand. He added another finger on his next thrust and then another. she cried out in pleasure as he pushed in the third finger. Her volume he was certain could be heard through out the store but no one ran into break them up or anything. So he pushed in another one as she rocked back against him.

From where Mrs Sanderson was standing all she would have been able to his was the back of his ass and his arm pumping in and out of her. So Sam decided to move things around a little bit and make sure that she had a full view of everything that she had arranged for him. After turning the girl 90 degrees he slipped his fingers out and replaced them with him. She gasped and Mrs. Sanderson looked at least somewhat interested in what was happening.

She was wet with pleasure and he slide in ease. The two of them rocked back and forth for a several seconds as they worked together getting him in all the way up to the base. Sam could see her fingers digging in to the fabric of the bench leaving trails of lighter red behind them as she brushed against its pile. Her breathing was still ragged from the fingering she he'd just received and she was struggling to catch her breath.

Sam decided that he couldn't let that happen and he slowly slide himself out to the point where he nearly fell from between her lips and then he rammed himself back in. She had already started to stand up thinking he was pulling out. Then his sudden thrust rocked her forward and she had to steady herself against the sofa to keep from falling over. By the second thrust she was able to enjoy every bit of his rock hard cock. Neither of them lasted as long as they might have liked. Her body tensed and then convulsed for a moment or two as she climaxed. Screams of her pleasure echoed around the change-room. Sam didn't last much longer than her, he could feel the slickness of juices being pushed out between where their flesh met. He grasped her hips and pulled them tight against him holding his cock deep inside her as he gasped and spurted out his load into her.

When he was done he let up on his grip she collapsed forward on to the bench panting. He leaned back against the cool mirror taking long slow breaths trying to recover. The thong felt strangely nice between his cheeks. Mrs. Sanderson offered both of them a short round of applause before talking again. "Thank you dear. Now if you could get him wiped up so we can finish here and be on our way."

The woman nodded her head as she got up. With a hand against the wall apparently to steady herself she stepped back into a storeroom and pulled out a couple of towels and matching wash clothes. She reached forward to wipe him up but was interrupted before she could touch him. "Best you let him hand that dear. We don't need a repeat performance just now do we."

Sam guessed from the barely hidden look of disappointment on the girls face that had been exactly what she wanted. He took the towels from her and cleaned himself up while she disappeared back into the storeroom. This time he was able to tuck things back the way she wanted and pulled on several different pairs of the panties. The fourth pair was the one that she went with and collected them and the ones that had gone before and left Sam to get dressed.

By the time he left the change room she'd paid for what she wanted and held the bag in her hand and was waiting by the door. The dark skinned clerk stood behind the counter with a big smile on her face, and the male manager, he guessed, was talking with Mrs. Sanderson at the door. Sam made his way to the front of the store passing the counter on the way, the girl slide a company card across the counter to him. It was face down and had a hand written number on the back of it which he pocketed with only the briefest hint of smile to her.

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