Office Casual


"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office.

"Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail for me."

"Will do," Karen said as she tried to look busy behind her computer.

Karen continued to type, trying to justify her place on the payroll until she heard the sound of Ms. Anderson' door slamming shut. It wasn't that Karen disliked her boss. No, far from it. Danielle Anderson – CEO of Odysseus Industries and one of the most up and coming businesswomen in America – was probably the best employer she ever had. She never made unreasonable demands, gave her whatever days off she requested, and gave raises every Christmas.

Plus, it was a relief to finally be working for another woman for a change! Karen didn't like the way that some of her previous employers had looked at her and made sexual innuendos; her last boss actually had the audacity to expect she would give him a blowjob after hours! At least now she didn't have to worry about that sort of chauvinistic crap with Danielle.

But what made her uncomfortable was the fact that Ms. Anderson was just so... so... gorgeous. She was a beautiful woman - a tall, stunning brunette, with long auburn hair and absolutely perfect mascara and eyelashes'. Her hair and make-up always looked like it was professionally done, and to make matters worse, she always wore sleek, designer suits that showed off her feminine form. Karen was even jealous of the way that Ms. Anderson walked in heels. She was so graceful, it was almost as if she was born in them!

'God,' Karen thought to herself, 'I wish I could pull that off.'

Not that Karen was unattractive herself. Although standing just a little over five feet, Karen was a petite and curvy redhead, with thick, full lips and deep green eyes. However, she always felt nervous around men. Her last few relationships had ended badly, and since then, her confidence had been shattered. Now Karen was meek and timid; and unfortunately, that only made her office co-workers try and hit on her that much more.

But at least back here in Ms. Anderson' private reception area, she didn't have to worry about that. It gave her a lot of time to get her work done, but it also gave her a lot of time to think and do things for herself. As long as she didn't get too far behind on her paperwork, Karen was usually free to do almost anything that she wanted. And so, she spent a couple of hours surfing the internet, reading articles on various websites and occasionally checking her e-mail to see if there was anything good or interesting in her in-box. Most of it was just spam.

Karen hardly even noticed when the mail courier got off the elevator. She looked up from the computer, and saw that it was Ray, the young Jamaican guy. She recognized him immediately from the dreadlocks and handsome dark skin; what she wouldn't have done to get his attention!

She also noticed that he was carrying a couple of small manila envelopes, presumably for Ms. Anderson.

"Hey Ray," Karen said as she smiled and tried to look sexy, "How have you been? Are those packages for Ms. Anderson?"

"Yep," he said flashing her a broad grin that showed off his pearly white teeth.

Karen blushed a little.

"All right," she said, "I'll sign for those."

"Thanks," he said as he handed her the packages.

He smiled, and then hesitated for a minute, as if he wanted to say something, but he didn't. Instead, he just turned and walked back over to the elevator.

"I guess I'll see you tomorrow," he said as the door closed.

"All right," Karen chirped as she got up from her seat, "See you tomorrow."

She looked at the packages. These had to be the delivery that Ms. Anderson was expecting. Karen walked over to give them to her boss when she thought she heard something coming from the office. She listened closer, putting her ear up to the door, and then she heard it again. It was faint – very faint, in fact – but she could definitely hear what sounding like panting or heavy breathing coming from the office.

Karen was a little confused by this. It didn't sound like Ms. Anderson was in any trouble or anything, but why was she panting? Could she have been masturbating? At work? That certainly didn't seem like something that the CEO of a major corporation would be dumb enough to do. Karen thought about knocking, but instead decided to just announce herself. It would be less embarrassing that way.

"Ms. Anderson," Karen said loudly, hoping to get her bosses attention.

She paused and there was an awkward stretched of silence.

"Ms. Anderson," she said again, "Are you all right? I just got that package you were expecting?"

When no reply came, Karen finally worked up the nerve to open the door. She was quite surprised by what she found on the other side, because the package that had come in the mail wasn't the only one in the room. Standing up in the office was Ms. – or perhaps Mr. - Anderson, her/his skirt and pantyhose pulled down to his/her ankles, and with an astonishingly large and erect penis standing at full attention between her/his legs.

Yes, much to Karen's shock, it seemed like the successful and beautiful up-and-coming businesswoman was actually a business man! And a businessman in full drag at that! He looked up at her, his eyes wide and full of shock and terror, as his still erect penis dribbled a trail of cum. It was an odd and embarrassing sight, the vulnerable transvestite businessman decked out in full woman's attire in the middle of his/her office.

Karen didn't know what to do. She dropped the manila-colored envelops to the floor and stood there in abject terror for a moment... a moment that, for both of them, seemed to stretch out for an eternity. And then she slammed the door shut and ran back to her computer, scared.... Scared of her boss, scared of what he/she was going to do to her, scared of everything.

"Karen," he cried out.

She could hear her boss through the door.

"Wait," he/she said, "It... it's not what it looks like..."

Karen didn't respond. She just sobbed meekly.

After a while, her boss came back out of his/her office, the skirt and pantyhose pulled back up. Mr. Anderson, or whoever it was, looked no different than normal. His/her hair and make-up and clothing was all flawless. And yet, it was still creepy for Karen, because she now knew that underneath all of that 'she' was really a he!

"Look Karen," he/she said, "I'm sorry... I never really wanted you to see me like that."

"How long has this been going on," she said somewhat angrily.

Mr. Anderson looked at her calmly.

"Forever," he/she said, "I've always been a woman trapped in a man's body."


"No but," he said shaking his head, "This whole time that you've known me, I've been the same person. I've been living as a woman for years now... since college, in fact."

"But," she said as she still tried to come to terms with it, "Why? Why did you lie to me.... To everyone?"

He/she sighed.

"I didn't want to," Mr. Anderson said, "But... it just became so natural to me, and after a while, everyone believed it."

"You don't understand," Karen said with tears in her eyes, "I believed in you! I looked up to you! And now it turns out that you were just lying to me all this time!"

Mr. Anderson reached into his/her blouse and took out a small handkerchief, using it to wipe away Karen's tears. And then hugged her.

"I'm sorry," he/she said, "So very sorry... But please, don't tell anyone."

And then he/she did something that Karen never expected... he/she kissed her! Gently and on the forehead, but it was a definite kiss.

"I... don't understand," Karen said, "I thought you were a woman trapped in a man's body... how can you..."

"I am silly," he/she said after planting another kiss, "But that doesn't mean that I can't also be a lesbian, now does it."

"I guess not," Karen said.

"I know that you've always hated men. Remember what you told me about your old boss? I've never cared much for a bunch of macho, chauvinistic pigs myself. Those same people bullied me my entire life just because I was 'different.' I just sort of hoped that maybe, just maybe, someone like you would understand me."

Slowly, his/her hands slid down Karen's well-endowed chest, slowly undoing the first two buttons of the secretary's blouse.

"More than you could ever know," Karen said.

She finished the job herself, unfastening the last few buttons and pulling off her blouse. She wasn't even wearing a bra underneath, and her large breasts were now fully exposed. She grabbed her boss's hands and slowly guided them over her melons. He/she squeezed them firmly, sending a wave of pleasure through the secretary's soft, curvy body.

"Oh yes," she cried out, "Yes! Do me here!"

Karen had nearly forgotten how good sex was. It had been so long, but finally she found the perfect man for her... he just happened to like dressing as a woman. But at least he didn't make her feel uncomfortable with herself.

For his part, Mr. Anderson didn't need much encouragement at all. He/she dropped his/her miniskirt and pantyhose, once again exposing his very male (and very big) member. Karen grabbed it and began to stroke it lovingly. Mr. Anderson just stood there, smiling as his secretary began to work on his/her cock. As it started to dribble a trail of cum, Karen sat back down and popped it into her mouth.

Mr. Anderson grunted in pleasure as his/her secretary tried her best to deepthroat the entire length of his/her cock. It was a valiant effort, but there was no way the petite redhead was going to fit the entire cock down her throat. Mr. Anderson stroked her head and ran his/her fingers through the secretary's long red hair. He would have to ask her what she did to make it look so red, after the sex of course.

Not wanting her efforts to go unrewarded, Mr. Anderson hiked up his/her secretary's skirt and slowly began to finger her cunt. Karen was already very wet down there, so there was plenty of lubrication for him/her to work with. Slowly, Mr. Anderson worked his/her fingers up into Karen's pussy. It was a tight fit – he/she could only get two or three fingers in at a time – and he/she wondered how she would be able to accommodate his/her massive cock.

"Mmmm," Karen moaned, her sounds of pleasure being muffled by the cock in her mouth.

Mr. Anderson pulled out of her mouth, the cock leaving a sticky trail of cum dripping down from Karen's chin and onto her neck.

"Wow," Karen said, "That was really amazing. I haven't done that in sooo long."

"Neither have I," Mr. Anderson replied.

It was true, obviously, though Karen hadn't immediately thought of it. Mr. Anderson had spent the past few years living as Ms. Anderson; he/she couldn't have had sex, because it would have blown his/her false identity. All of that pent up sex... no wonder he/she was masturbating back there in his/her office.

"Say," Mr. Anderson said looking down at his/her sexy little secretary, "I don't suppose that you would be interested in some sex... some real hot and dirty sex..."

His/her words trailing seductively as he/she ran his/her hands over Karen's.

The secretary hesitated for a moment before replying.

"No," she said meekly, "I mean... not without protection or anything. You don't happen to have any condoms with you, do you?"

Mr. Anderson stopped, seeming a little disappointed.


Karen felt bad. She didn't want to make Mr. Anderson feel bad; she just didn't want to wind up with an unplanned pregnancy or anything. And then, an idea came over her.

"Well," she said grinning enigmatically, "I think I know something else we could do instead..."

Karen reached down and squeezed her ample breasts together.

"How would you like to fuck my tits instead," she asked as she waved them in front of Mr. Anderson's huge dick.

"That sounds quite temping actually..."

Mr. Anderson slowly slid his/her cock in between the secretary's huge round breasts, the mixture of drool and semen proving to be quite useful as a lubricant. Grabbing the secretary's breasts for support, he/she squeezed them together and began to thrust up and down with his/her hips.

The rock hard cock slid quite quickly between her breasts, pumping as if the two oddly matched partners were actually having sex. Karen closed her eyes as she felt him groping her ample bosom, a think sheen of sweat building up from their vigorous lovemaking. She could hear her boss grunting... the same noises that she heard back in the office. His/her breathing began to become ragged... panting in fact...

And then it came. Mr. Anderson shot a load of hot, sticky juice on her. It hit her square in the face, a few drops even going in her mouth, and then slid down her chin and neck. Mr. Anderson backed off and Karen slowly reached onto her desk to get a tissue. Finally opening her eyes, she was surprised to see just how much jizz now covered her body.

"Geez," she said wiping it off, "Somebody has been a naughty boy..."

She thought about it for a moment.

"Or should I say naughty girl."

Mr. Anderson just grinned sheepishly.

"I suppose I'll have to buy some condoms for tomorrow," he/she said.

"Maybe," Karen replied, "And maybe tomorrow Ray could join us..."

"The Jamaican guy," Mr. Anderson said, "Oh yes, he's pretty cute. I suppose we could try talking him into it. That would be pretty hot..."

And so it was. So it was...

Report Story

byal_Ussa© 3 comments/ 75464 views/ 12 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartKitsune92, juliahoutx and 10 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous05/24/18

Has Karn got a strap-on ? if so she should wear it to work

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 3 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: