The Bet that changed my life.

[HumiliationLover423]

Rachel just shakes her head, “Yeah right…I want you to say…no shout that you LOVE your girly care bear panties…come on shout it!”

She sends a powerful spank into Tim’s butt unleashing a terrifying smack.

[Sissytiff17]

“ this was not part of the bet. I only am suppose to be wearing what you say. That is not fair. Ouch that hurts”

[HumiliationLover423]

She grabs the waistband of Tim’s underwear with one hand, launching them into a wedgie and leaving him dangling in the air. She walks over and hangs him on a hook.

She gets in his face with an unnerving grin, “You want to earn time off your 10,000 days of dress up…then you better get to shouting…depending on how well you do I’ll take days off your sentence…now shout for me bitch…”

[Sissytiff17]

Holy shit she was able to,left me up and now I have a wedgie. I feel the underwear digging up my ass. Wait she just said time off. It may be humiliating but I got to shout it.

”ok you win I love my girly care bear panties,i love my girly care bear panties”

I yelled that over and over again,

[HumiliationLover423]

She laughs, “Good job Tiny Timmy…I’d say that reduced your sentence by…an hour seems fair!”

She then let’s Tim off the coat hook, “Don’t want to rip those panties that you love so much!”

She looks down at Tim holding his hands over his crotch, “Hands behind your head!”

Not even waiting she grabs his hands forcing them up before yanking the underwear down to Tim’s knees, “Oh my!”

 

Her laughter echoes in the room, “I guess I shouldn’t be calling you Tiny Timmy, but rather..(lift her fingers up making the small penis size moving forward with each word for emphasis)…Eeny….Teeny…Timmy!”, her giggling resumes.

[Sissytiff17]

You got to be kidding I did that for an hour. I feel myself being pulled from the hook I pick the wedgie out and she immediately starts to pull down my panties. I was told to hold my hands above my head so I cannot fight this. I notice how she starts to laugh and call me tiny Timmy. The worst is I get hard when she touches it. It is still super small even hard.

”that is not fair it is not small. It is average. It is a real big penis. I try and yell but I know that I am wrong”

[HumiliationLover423]

She keeps laughing, “and now you’re throwing a tantrum….between your behavior and that itty bitty wee-wee…you’re not even worthy of those panties..”

She then shoves Tim to the ground and pulls the Care Bear panties from his ankles placing them over his head making sure the backside was over his face.

”Take those off and this gets so much worse.”

Tim would then feel his legs lifted up, something soft placed under his butt, a powder sprinkled over his crotch, before having something soft folded over his crotch. It tightens around his waist.

”Alright, stand up Eeny Teeny Timmy..”

[Sissytiff17]

The sad thing is she is correct I am not worthy of them. I have always been ashamed of my cock. The panties are placed over my head. I now cannot see what is going on. I decide I will not try to fight. It is pointless, I cannot win. I feel myself being laid down and something slide under me. It is soft and feel comfortable. It is almost like a pillow. I can handle that I do love comfortable things. I am confused when I hear tapes being closed and something tight around me. I am stood up and the panties are removed. I look down and I am shocked. I want to say something but I am speechless.

 

 

 

 

 

 

 

 

 

 

 

 

[HumiliationLover423]

Tim would be greeted to the sight of a thick white diaper around his waist covered in unicorns. Rachel leans down over him dangling his underwear, “Do you want your undies back?” She dangles them in front of him like some sort of toy.

[Sissytiff17]

I am wearing a diaper. It is super thick and it is hard to move. This is the diaper I bought for her.

”of course I want my panties back.”

I try to snatch them but cannot grab the, from her.

[HumiliationLover423]

She then grabs Tim and put him over her shoulder, pulling and shimmying the underwear up until they are a hilariously too small diaper cover. She sets him down, “Well Eeny Teeny Timmy…what do you say?”

[Sissytiff17]

“ please I will do anything but just don’t make me wear only this diaper. People will laugh at me”

[HumiliationLover423]

“Oh you’re not just wearing a diaper…you have your favorite pair of panties too!” Her laughter is louder than ever.

[Sissytiff17]

“But please can’t I put clothes over it. I mean I have the clothes I was wearing. Please let me wear something over it . I will do anything”

[HumiliationLover423]

“Hmmm…so you just don’t want anyone seeing you in just a diapee…and you will do anything to cover it up….ok you’re going to do a few things…first…thank me for giving you a diapee to cover up your eeny teeny weeny…then ask me for something to cover your dumb diapee hiney and reiterate you’ll do anything for me…

[Sissytiff17]

“ Rachel, I want to thank you for giving me a diaper to cover up my tiny penis. The diaper is very comfortable and my tiny penis needed to be covered. May I please have something to cover my diaper though. Please Rachel, I will do anything and I mean anything, pleas Rachel give me something to cover my diaper.

[HumiliationLover423]

“Hmm…nope you’re talking like a man…you need to beg me like a bitch…unless you really want to just show off your diapee..” she flashes a sadistic grin to show she means business.

[Sissytiff17]

I got down on my knees and kissed her feet” Rachel thank you for allowing me to wear the diaper. I know I have a tiny penis and I needed it covered. May I please have something to cover my diaper. I will do anything. Pretty please I will do anything.”

I then kissed her feet again,

[HumiliationLover423]

“Strike two diaper bitch….I want you to implement the words I told you to…but now I want you to punctuate it by saying, Uh oh my itty bitty wee-wee is all stiffy…”she pulls out her phone and points it at you, “Oh and stick your thumb in your mouth after you say it..” 

[Sissytiff17]

“Rachel thank you so much for giving me a diaper to cover my eeny teeny weeny. May I now please have something to cover my dumb diapee hiney. My itty bitty wee-wee is stuffy from it so I don’t want people to see. I will do anything if you cover it. I mean anything, please Rachel”

I say that and stick my thumb in my mouth and start sucking.

[HumiliationLover423]

Her head falls back laughing as she stops the video she begins circling Tim, “Oh my word!!! I wasn’t expecting you to admit that diapees turn you on! I’ll be sure to have fun with that later, but for now..”

She turns around and grabs the sissy looking cheerleader uniform and tosses it to Tim, “Put this on…diaper bitch..”

[Sissytiff17]

I listened to her mock me. I want to fight it but it was no use. She had a video of me admitting that.I am real scared by what she means by fun with that. Oh god, I saw the cheer uniform. I can fight but I will lose. I guess I will get it over and put it on,

”yes Rachel but I may need your help with the bow”

I put the top on and then slid the skirt up over my diaper. I then zipped the skirt.

[HumiliationLover423]

She fixes the bow for you, “This is just too great…let’s go to my new office…while we walk there you can think of a little cheer routine to perform talking about how great I am and how much of a pathetic sissy you are!”

She forcefully grabs Tim’s hand and slowly begins leading him.

[Sissytiff17]

I feel myself being walked to the office. The problem is I have to walk through the main hallway. Everyone is looking at me and laughing. 
 

“I have never cheered before I don’t know how to do cheers”

[HumiliationLover423]

Rachel cocks a wicked grin, “Well you better learn fast…” she reaches for the doorknob to her office, “…because it‘s showtime diaper bitch!”

She opens the door and Tim sees all of his most attractive female co-workers sitting in Rachel’s office. Every single one of them lose it at seeing him and laugh uncontrollably.