The Bet that changed my life.

[Sissytiff17]

My name is Tim is I am 28 and kinda small but very good looking. I am very smart. I graduated from an lvy league school with my MBA. I literally had the perfect life. I lived in a pent house apartment. I made a ton of money but also inherited a lot too. To top it all off I drove an amazing sports car. I had an awesome job too. I was in sales and was the top salesman in the company. I was destined for great things. In fact I will be running the company someday.

That someday may be real soon. We were all summoned into a meeting today. Our boss was retiring and they would be hiring from within. In fact they announced it was down to Rachel Wells and myself. They would decide soon. Rachel was my arch enemy. She thought she had a big head and did not understand a woman’s place. She does not understand that men still run things. She may be tall and beautiful but I am smarter and better at my job. There is no way I will lose out on this promotion to her. I cannot wait to be the boss and have her working for me. Maybe I will demote her to secretary.

[HumiliationLover423]

With the new opening announced also came the new quarter, meaning everyone starts with a clean slate. Rachel knew exactly what they were looking for in a new sales lead. With her numbers she would be a lock. All she needs to do is make a statement.

 

Something to show everyone without a doubt she was on top and to show she would not tolerate insubordination once she’s in charge. What better way to show that….than by humiliating her rival. She sees his cocky smug grin, “Oh Timmy!!!”, she calls out in a high pitch voice.

[Sissytiff17]

“What do you want Rachel?. Some of us are trying to work. That is probably why my numbers are so much better than yours. I cannot wait to I get this promotion and am in charge. You will be calling me sir then and not Timmy.”

I laughed as I said it. The thought of her being subservient to me made my day. I think she will take to that role. Deep down she knows that is the role of a woman.

[HumiliationLover423]

Rachel’s blood boils under her skin hearing that, “Oh is that so? How confident are you in that…Timmy?”

As a sly grin creeps across her face.

[Sissytiff17]

“ Rachel I have never been so confident. There is no way I won’t get this promotion. This is a man’s job not a little girls job. I will bet anything that I come out on top. “

[HumiliationLover423]

Her grin grows even wider, “Anything you say?…what do you have in mind….Tiny Timmy?”

She punctuates her question with a condescending giggle.

[Sissytiff17]

“ well they said the person with the highest sales total will get the job. So how about the winner, which will be me picks whatever the loser wears for a day per unit they win by. I cannot wait to see you dressed how I like.”

[HumiliationLover423]

Her smile grows even more, “You have yourself a bet there Timmy…soon enough we’ll see whose the real MAN of the office…and whose the little bitch..”

She saunters off confident that her victory is guaranteed. 

[Sissytiff17]

“ perfect I cannot wait to show you I am the man of the office. Maybe we will get you a necklace that says bitch. Great idea yiu had.”

I went back to my computer and started looking up outfit ideas for her.

[HumiliationLover423]

Time moves along as Tim and Rachel each make sales and progress towards the promotion. Finally the day arrives where the numbers are tallied. An email was sent out giving everyone the results for most clients sold to and sure enough Tim was at the top of the list.

[Sissytiff17]

I opened my email and saw my name at the top of the list. I was so excited I was going to get the promotion. I won the bet. I am the man of the office.

”oh Rachel come here. Did you see the results of the bet. You are going to look so cute I have some ideas for you. Maybe a cheer uniform with  cute bow, maybe a maid costume. Maybe I will make you wear diapers. So many possibilities.”

 

[HumiliationLover423]

Rachel smiled sadistically, “Oh really?…did you read the second email..of course you didn’t it just came out…Tiny Timmy..”

[Sissytiff17]

“What email and what did you call me? That is sir to you.”

I pulled up the email. Oh shit I lost. How did this happen? 
 

“this can’t be true. I should have won I am the man. What happens now?”

[HumiliationLover423]

Rachel grins taking on a baby talk voice, “Let’s take a look at how you lost Tiny Timmy…well you did have more clients that anyone…but they didn’t buy a whole lot…”

Her giggle echoes throughout the room, “Now let’s see why I won…oh…my clients bought a TON…that didn’t just give me enough to beat you, but put me at the tippy top of the list…now where are you on the list…Aw looks like “The Man” is at the sad bottom of the barrel….”

She leans down placing an elbow on Timmy’s head, “and it was one day per unit we win by…it looks like I beat you by…10,000 units there little Timmy!”

[Sissytiff17]

I looked at the computer in complete shock. She was correct. She did win and I finished in dead last. I had a ton of clients but they did not buy enough. She had a few big clients that put her way ahead of everyone. Not only did I lose but I got crushed. I was so humiliated. She cannot really expect me to pay off this get. I mean 10,000 days that is just not right.

” look I guess I got unlucky and lost but I was just joking about the bet. You cannot really expect me to pay this off. What if I refuse to? There has to be some way out”

[HumiliationLover423]

She looks at Tim, smile still plastered on her face, “Oh Timmy…Timmy…Timmy…you could refuse the bet…but we both know that being the top of this sales quarter guarantees me to be the lead of sales…which means I’m your boss…and with your abysmal numbers I have more than enough grounds to release you on performance alone…that doesn’t even factor you’re a misogynistic asshole and I don’t like you..”

[Sissytiff17]

She had me by the balls so to speak. If she fired me, I would be screwed. I signed an iron clad non compete and she could easily black ball me to other companies.

”ok I will pay off the bet you are correct. Is there anything we could do about the time please.“

[HumiliationLover423]

Rachel giggles, “Maybe…but for now let’s get you in your first outfit!…What little costume did I see you bringing into work earlier…Tiny Timmy..”

[Sissytiff17]

“You can’t expect me to wear that. It is for girls and I am a man. It was a cheerleading uniform. Complete with a bow. However, it will never fit a man like me.”

[HumiliationLover423]

Rachel’s grabs Timmy by his throat and pulls him in so close that he can feel her breath. All playful expression has left her face, “Go get the outfit bitch..”

[Sissytiff17]

I felt her pull me in. I was being manhandled. I was actually petrified. I actually peed a touch out of fright. Thank god no one can notice.

“yes Rachel of course.”

i ran to the car and grabbed the outfit.

[HumiliationLover423]

She circles Tim looking him over, “Come on…hurry up!” She looks at him very impatiently.

[Sissytiff17]

I see that she was losing patience. So I am real scared now. I run over to her with the outfit and hand it to her. “Here you go ma'am”

[HumiliationLover423]

Rachel’s thoughts her head back and scoffs, “Really!…so typical of a little boy!”

She sets the uniform down and rips off Tim’s shirt, “Tiny Timmy can’t even dress or undress himself!”

She then shoves Tim onto his butt first removing his shoes, then his socks. She grabs a hold of his waistband, “Alright let’s get you into your undies..”

She yanks them down, but nothing could have prepared her for what she would see, “Oh…my…WORD!!”

A pair of whit briefs with a pink waistband and pink lining the leg holes, crotch flap would also be highlighted with pink. That would be bad enough, but also on the crotch of the briefs was a picture of the pink Care Bear standing under a rainbow.

She quickly flips Tim over onto his stomach show the same image was blown up and the print of “Care 🩷Bear” written in the butt with the letter in pink under the image.

”Care Bear undies!!!”

[Sissytiff17]

Oh no she is stripping me. She is going to see my undies. They are comfortable that is why I wear them. She will not understand that though. I tried to hide the undies with my hands but it was not really working. I also had to hide my small penis. I did not want her seeing how tiny it was.

”yes I am wearing them. A friend bought them for me as a joke. I forgot to do wash so they were all that I had left.”

I hope she buys my lie.