tagTranssexuals & CrossdressersTeaching My Boss a Lesson

Teaching My Boss a Lesson


Jessica, or Jess to her friends had just graduated from college. She was a wide-eyed optimistic twenty-something determined to change the world. She was not as naïve as everyone thought, even had a little bit of a dark side that she hid very well. She was about 5'6", average build with long dancer's legs, blue eyes and long straight dark hair that was the envy of all of her friends. The only job she could find in the job market when she graduated was a glorified intern on a senator's re-election campaign. She loved the work, canvassing constituents, listening to their concerns, figuring out how to help people, she believed in what she was doing.

One night she was out canvassing and got caught in a rainstorm. She ducked into a restaurant to wait out the rain, but after a few hours it became clear that the rain wasn't going to stop. It was getting late and she knew her roommate would be worried about her. Braving the rain she left the restaurant, she was about a block from the restaurant when she realized that she had left her car keys at the office. Frustrated with herself she turned around and headed back to the office. She got back to the office, everyone had already left and all the lights were off. She opened the door and walked back towards her desk, looking down at her white shirt and silently gave thanks that no one was there to see the hot pink bra now almost clearly showing through her button down. She picked her keys up off the desk and as she looked up she saw a light on. Knowing some of the information was sensitive she crept towards the light determined to catch the intruder.

She reached the door to the office and looked around it very carefully not sure what she was going to find. Standing with her back to the door, Jess saw shoulder length platinum blonde hair, that gave way to porcelain shoulders, with only black lace straps. A black and red lace dress ended just below the tight ass. Thigh high boots sat below the black and red, and fishnets held in place with red garters peeked out from under the little clothes that she had on. Jess was intrigued by what she saw and leaned further around the door to get a better look at this slut. While she did this she accidentally hit the door, and it creaked. Both Jess and the slut jumped at the noise, and as the slut became aware that there was someone else in the room. She whipped around to face the door as Jess moved out from her hiding place.

As she stepped out from behind the door to face the unknown slut in front of me she turns towards me in shock that she has been discovered. Hands moved fruitlessly to cover up the outfit, her face anything and everything. Jess's hand flew to her mouth as she got a full front view of the slut, the front of her skirt flipped up and her cock out erect and throbbing. Confusion flooded Jess's face as the slut stepped forward and she finally saw her face. It was him, her boss the chief of staff. The first word out of his mouth was shit, as Jess tried to pick her jaw up of the ground from this new information, the wheels in her head began to turn and at the same time something in her began to twinge. She felt herself getting wet as she stood there and stared at him. He began to move towards her, tucking himself back in as he crossed the room. As he moved towards her Jess took a step back and fell back into the wall. "Jess please. Wait stop. It's not what you think I swear. I can explain."

Jess looked him up and down, straightened herself up and took a step back towards him. "Alright Cameron, explain yourself"

"I...I...I had all my clothes taken from me at the office gym...and.and...This was all I could find. I swear...And I...I didn't want to look like a ...you know. A guy in drag...so...So...I wanted to look passable so I could. You know make it home...if I was recognized it would be...bad...for the senator."

"I don't believe you, you make too sexy of a slut. You need to tell me the truth Cam. And I don't enjoy being lied to. You need to tell me the truth" Jess began to move towards him her aqua eyes looking him up and down. As she moved towards he began to step back and backed up into the desk. She placed her hand on his chest, felt the false boob under the tight low cut top and pushed him so he was sitting on the desk. She reached her hand under his skirt to touch him. She felt him react and heard him moan softly as her hand found his now neatly tucked away cock. She used her hand for a few minutes the pulled it away and looked him straight in the eyes. "Tell me the truth Cameron"

"I don't know what you want to hear Jess...I...I did tell you the truth ...I...I just wanted to protect the senator. I...I wanted to look realistic so I could make it home...I...I swear. His hand slipped to the keyboard and a webpage pops up...it's a MySpace account for tiffany slave...and another for fictionmania... "Please Jessica. Please help me get home safe... please can't you drive me home... I will do whatever you ask if you help me save our boss...I mean that IS why I am doing this. I SWEAR."

Jess looked at him again, she still didn't believe him but she was going to play along for a little bit see how much he could take. "Alright Cameron if you say that is what you are doing then I believe you. Now where was I?" Cameron looked at her as if he wasn't sure he could trust her but after a second decided that he could. Still sitting on the desk Jess standing between his fishnet clad legs, Cameron reached up and placed his hand behind her head his thumb brushing against her cheek. Her hands went around his neck as they leaned in to kiss. Cameron's other hand reached to take one of her hands from around his neck he placed it back on his tucked cock. Jess began to rub through the silky red thong, working her way under the material to take a hold of the erection. Moving her hand up and down and in small circles she brought him almost to the edge of his orgasm. He managed to gasp out the words "I'm so close" and as soon as he did Jess removed her hand.

"You wanted a ride home didn't you? Let's go, I have to get home." Jess stepped away from him and adjusted her hair and the clothes that had had been pushed out of place in the moment. Cameron still sat on the desk unable to move as Jess walked away. She walked out of the office door, paused and leaned her head back in. " Are you coming or not?"

"Yea yea I am" Cameron jumped off the desk and went around to close down his computer. His MySpace page was still up on the screen, split screen with fictionmania. He closed down the computer and looked up towards the door. Jess was standing there, still wet from being caught in the rain watching him.

"Hurry up boss I have to get home. My roommate is waiting up for me I'm sure she is worried about me being this late" He closed down the laptop and placed it in the case. He slung it and his purse with his wallet and keys in it over his shoulder. His heart was pounding, so nervous to being caught and thinking that he may have pulled one over on the silly wide eyed girl that he forgot that it is odd that he has a purse and worse that he walked effortlessly in the 5 inch heels towards you...his hips and ass swaying slightly as he played up the tarty outfit he had on.. Cameron struts out the door and out through the office walking next to Jess. They get to the elevator and as they stand there waiting for it to rise to them Cameron looks over at Jess overly confident that his secret is still safe, she feels him watching her and smiles to herself. As the elevator doors open and they step inside they make eye contact. When the door closes Jess found herself up against the door Cameron's hands on either side of her as he kisses her. His lips move to her neck and his hands stray down and begin to hike up her skirt. His hand drifts up her thigh and just before it can reach its destination Jess breaks the kiss and grabs his hand.

"No not yet, wait please. I'm not ready" He takes his hand away and leans away from her as the elevator doors open.

"Alright alright, I'm stopping. Just a ride home then" They walked out of the elevator Cameron taking the lead, Jess followed behind him watching as his hips swayed a little to confidently and comfortably in the sky high heels that he had on. Her eyes strayed to his ass and admired the tightness and the way it moved. She had always been a sucker for a good ass. They got to the car, but Jess didn't unlock the door. The rain had slowed to just a drizzle now, Cameron went to the passengers side door and tried to open door. It was still locked. He looked up at Jess, "Are you going to open the door?"

She looked back at him and walked towards him. "Maybe. I noticed you were checking out my skirt, I would have thought you would want me to get even wetter. Plus you were checking me out I think I am entitled to check you out in this sexy little outfit"

She moved towards Cameron standing in front of him, as she leaned in slowly to kiss him. She placed her on either side of him on the car. He deepened the kiss, trying to take control of the situation. He tried to slide up a hand up her skirt again and she smacked his hand away. He pulled away to look at her. "If you are going to let me touch you, then maybe you should just touch me"

She stood back from him and crossed her arms looking him straight in the eye. "You are dressed as the slut so you get to be the slut tonight. I am not the slut, and I will not be manipulated by an older man who thinks he has pulled one over on this 'naive' little girl. If you are going to dress the part I'm going to treat you like the slut I know you are. You are going to come home with me Tiffany and I will show you what it really means to be my little slut"

She unlocked the door, opened it and blocked Cameron's way to escape by standing in front of the door. He looked at her trying to judge if she was bluffing or not. Seeing no way out of this he climbed into the car. Jess closed the door behind him, smiled to herself and walked around the car to climb into the driver's seat. She closed the door then locked the doors. She turned to look at Cameron, "Go ahead I know you want to ask me."

He lifted his eyes from his lap to look at her. "You know the truth? How did you figure it out?"

"You know how to walk in heels far too well, and your wardrobe is too well designed for this to be an accident. Plus I saw the MySpace page." Jess put the car in drive and pulled out of her parking space. "You do make one sexy woman though I will give you that."

Cameron smiled at her, feeling a little more confident that even though she knew the truth she would keep his secret. "Thank you Jess,"

Jess cut him off. "You will refer to me as Mistress, slut. You will do exactly as I say, or you will be punished. You are my little slut now and I will treat you however I want to. And before you protest our new agreement, remember that I know your secret and can let that fun little tidbit of information slip anytime I want if you do not please me. Are we clear slut?"

Cameron looked at her and his jaw dropped. Part of him thought she was bluffing, but there was something about what she was saying, what she was threatening him with had him getting very hard underneath his short skirt. He tried to gauge how committed to this she was. The car stopped at a red light and Jess turned to look at him. "I said are we clear slut?"

She wasn't bluffing. The question was stern, rough and to the point. Cameron's cock tucked tight into his red thong and garter belt snapped to attention, he had never been so turned on. His eyes dropped back to his lap in submission. "Yes Mistress, very clear."

"Then we have an agreement Tiffany. Are you going to be a good girl and please your mistress? Or is mistress going to have to punish you?"

"Whatever you say Mistress, anything to please you. I live to please you Mistress." Cameron was so turned on, he was so hard, he couldn't help but reach down to touch his throbbing cock, trying to relieve some of the incredible pressure.

"Good girl." Jess turned her head to look at her newly willing slave and noticed him touching himself. "Did I say you could touch yourself slut? Remove your hand; you will learn how to wait until your mistress is ready for you."

And with that she reached over took his hand away from his rock hard tucked cock and in one swift movement captured his wrists tightly.

"Yes Mistress, I am sorry. I live only to please you Mistress. Please forgive me."

Jess turned back to the road, hit the gas and smiled. This was going to be fun.

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