The Bet that changed my life.

[Sissytiff17]

I walked into the office and saw all the females sitting in there. They were all laugh8ng and asking about my cheer. I could try and run but it was no use.

”Rachel Rachel Rachel she is the best, are office loves her more than the rest, with her in charge we will be the best, I should know since she beat better than the rest. Go Rachel”

I did my cheer and I even danced.

[HumiliationLover423]

All of the girls laugh, but Rachel looks at Tim disapprovingly, “I said to cheer about how much of a loser sissy you are too…” 

She leans in and whispers, “You better think quick, or you’re going to be wetting that diapee fas..and I’ll be giving all the ladies a diaper changing instructional..”

[Sissytiff17]

“Ladies now for my 2nd cheer this time about me. Timmy Timmy Timmy thought he was the best but he lost just like the rest. He thought his sails were huge but in the end they were like his pee pee tiny tiny tiny”

[HumiliationLover423]

Again all the women laugh, but Rachel doesn’t look pleased, she leans in and whispers, “No second chance on this one Eeny Teeny Timmy…I said cheer about being a sissy loser…not a teeny weenied loser…”

She turns to the women and pulls out a massive baby bottle filled with water and shouts, “Who wants to feed the baby!!!” 

Hands shoot up all over and Rachel selects the beautiful blonde Lindsey. She walks up, “Ah what a pathetic little loser…remember when you said I only had a job because I had a nice ass…now the only reason you have a job is because of your eeny…teeny…weenie!”

The women all laugh as she shoves the nipple into Tim’s mouth, “Bottoms up baby!!!”

[Sissytiff17]

I look at the bottle and stare in horror. The bottle is huge but looks just like a baby bottle. To make matters worse she selects the blond secretary named Lindsey to feed me. I have been horrible to her. I do feel secretaries are beneath me and I do have a crush on her to be honest. She always showed zero interest in me. I feel her lay me back in her arms like a real baby. I try and fight but the nipple is shoved in my mouth. It tastes horrible but I finish the whole thing.

[HumiliationLover423]

Lindsay laughs as Tim’s face contorts as he finishes, “Oh looks like it’s all gone.” Rachel steps forward pulling another one for her bag, “Time for another baba then!”

She hands it to Lindsey who then shoves it in Tim’s mouth, “Oh that diapee is going to be soaked when these hit!” All of the women laugh watching as Tim drains another bottle.

[Sissytiff17]

Oh god they are shoving another bottle in my mouth. I feel so full. The taste is horrible. I have no idea what it actually is. Oh god not now. I am getting hard from this treatment. I hope they don’t notice. That will only make things worse. I continue sucking and finish that bottle.

”please no more bottles. I am so full”

[HumiliationLover423]

Lindsay looks Tim over, “Is your diapee wet?…”, before Tim can think a proper response, “No…”, she grabs another bottle and shoves it in his mouth, “Then another baba it is!!”

Rachel laughs standing behind Lindsey, “Once that diapee is FULL from pee-pee…we’ll stop giving you bottles…”

[Sissytiff17]

I feel the other bottle being shoved in my mouth. I continue to suck. I cannot take anymore. I am so full so I just start to wet. I wet again and again. “My diaper is soaked please stop”

[HumiliationLover423]

Lindsey feigns shock, “Is it?@ she then lifts up your skirt seeing your Care Bear underwear for the first time, “Oh my word look at these silly little undies, Rachel where did you get them?”

Rachel laughs at that, “Oh no…droopy diapee aside that ensemble is completely the work of Eeny Teen Timmy!”

Lindsey laughs in Tim’s face, “That is completely pathetic! What you knew you’d never see a girls panties because of your pathetic little wee-wee that you decided to wear them?”

[Sissytiff17]

“I have seen lots of girls. They all love me. I yelled. Even though we all knew it was not true.” As the were mocking me I peed again and then got hard again.

[HumiliationLover423]

Lindsay scoffs, “Yeah whatever, lay down in your little Care Bear undies..”, as Lindsey and Rachel would both lay Tim down.

Rachel would look around, “Alright while Lindsay has been wonderful! We can’t let her have all the fun…so who wants to help change the little sissy’s diapee? I’ll need to volunteers since I’ll be giving a step by step instructional!”

Every single hand shoots up, but she ultimately decides on the gorgeous duo of Selina and Veronica.

Rachel looks down at Tim, “Are you ready…Eeny Teeny Timmy?”

[Sissytiff17]

I feel myself being laid down on the ground and stripped. I hear the sound of the tape of the diapers being untaped. Then I look up and I see Selina and Veronica. They were both beautiful.  Veronica was a secretary who I treated terribly. I told her secretaries are basically servants. Now she is standing over. To top it all off I got hard.

” no I don’t need you to change me. I can change myself. Don’t worry about it.”

[HumiliationLover423]

Rachel kneels down by Tim, “Oh you can change yourself?!?!…Please you couldn’t even undress yourself earlier!!! You had me do that!…Now because of that you have two options….either you beg them to change your diapee because you’re just a worthless little baby with an eeny teeny weeny that can’t do anything!!!…or….you can jerk off in your diapee…because we both know how diapees make you feel! Isn’t that right Eeny Teeny Timmy?”

Selina gets a confused look, “Wait..do…do diapers turn him on or something?”, Veronica narrows her eyes focusing on your crotch, “Nah there’s no way. I know Rachel said he had the smallest dick she’s ever seen, but surely if he were hard we’d see some kind of bulge at this point…right?”

[Sissytiff17]

“No way there is no way that I am going to jerk off in front of everyone I cried”

as much as I was turned on there was no way I could do that. I wanted to yell at her but I knew that would get me no where. So I got on my knees and crawled over to both.

” Please change my diapee because I am a worthless little baby with an eeny teeny weeny that can’t do anything!!!.”

I kept repeating that over and over again. I felt so submissive and humiliated but I had no choice. I need to get out of this diaper.

[HumiliationLover423]

Both of them laugh as Selina finally relents, “Ok since your so pathetic…we’ll change you.”

They lay you back as Rachel turns to the audience, “Now the first thing to do when changing a wittle pathetic baby’s diapee is to undo the tapes.”

With that each side is slowly unfastened. Rachel’s smile grows knowing what’s coming next, “ Now lift up the soaking wet diaper to allow air to make it’s way to the baby’s itty bitty pee-pee..” 

Selina slowly lifts unfolds it as Tim’s rock hard small penis becomes visible to the entire room as it is filled with neat deafening laughter.

Veronica is the only one not laughing, her jaw on the floor, “There’s no way you weeny is that teeny!!!!” She says shrilly sending another wave of laughter through the room. She holds her hand over her mouth, “And it is…it’s hard…y’all he is like standing at FULL ATTENTION!!!”, the laughter getting louder as Selina chimes in, “Veronica cut it out! You’re going to make all of us pee instead of just the teeny weeny baby over here.”

 Veronica just points down, “BUT LOOK AT IT!!! IT’S SO TINY!!!”, the loudest wave echoes in the room.

[Sissytiff17]

I honestly felt relieved to hear the diaper being untapped. Yes it was humiliating but sitting in this wet diaper was no fun either. That relief was quickly tkae. Away once I remembered I was rock hard. I heard Veronica try and make fun of me. It was horrible. I actually started to cry.

”Veronica please stop making fun of me. I cannot help it. I am very self-conscious of it. Please be nice and stop teasing me.”

 

[HumiliationLover423]

They all laugh at your begging, before Veronica can respond Rachel chimes in, “Oh if you can’t handle a little itty bitty pee-pee teasing Eeny Teeny Timmy…then we’ll just go ahead and tape that diapee right back up!”

Veronica smiles at hearing that fastening it up before placing the palm of her hand right on your rock hard dick, “There you go…now we can’t see your…(begins wiggling her pinky)…wittle bitty wee-wee!”

The women again begin to laugh as Rachel looks down at you smiling, “Well Veronica and Selina…since Eeny Teeny Timmy took away your activity…what would y’all like to do to the wittle baby?”

They begin pondering as they circle you mischievous look on their faces as they don’t say anything. Just circling nonstop.

Finally the two stop, sharing a look as Veronica pins Tim on the ground, mounting him, “Alright Timmy…pick a number between 1 and 10…if you guess right I’ll give you a…(grabs her shirt to accentuate her cleavage)…give you a reward…guess wrong…and you’re going to regret it..”

She leans down close to your ear and whispers, “So what’s it gonna be…diaper dick?”

[Sissytiff17]

It was a tough choice but I really had no choice. If I said no they would probably do it anyway. So I might as well play along.

”ok ok the game actually sounds fun. You know I do love to gamble. So, why not? Ok I will guess the number 7.”

I so hope I am right and that they are honest about it. I looked at all of them and there faces gave nothing away. There was silence too. It seemed like forever but Veronica and Rachel finally started to speak.

[HumiliationLover423]

Veronica slowly leans in her cleavage inches away from Tim’s face. As she leans further down getting a breath away from his ear she whispers, “So close…”

Before standing up, turning around and quickly sitting down on his face, “I hope you enjoy this blindfold more than your smelly Care Bear undies!!”

As she grinds and shakes her butt all over Tim’s face, he would feel his lower body lifted up and a new tightening sensation around his waist every now and then.

It’s hard to do use on what that is especially as he soon feels something shoved down the front of the diaper, as Veronica continues to grind on his face, “You ready for your punishment, my teeny weeny toy?”

[Sissytiff17]

I felt her butt grinding on my face. I have to say it was a beautiful butt. In most circumstances I would love to have this sitting on me. I was in complete bliss. Until I felt something going in the front of my diaper. I saw the girls laughing and I knew it must not be good.

”what are you doing to me? What is going in me?
 

then I realized what was happening. 
 

“wait is that what I think it is? It can’t be”

[HumiliationLover423]

She giggles, “None of your concerns Mr. Teeny Weeny Wee-Wee!” the ladies again laugh as she stands up. Tim would immediately be surprised at the newfound bill between his legs as he is now wearing SEVEN diapers.

Giggle surge throughout the room as Tim struggles with his current situation as Veronica comes up, “All right now for your punishment! We’re going to play a trivia game…for every question you get right each of us will take off one article of clothing…for each one you get wrong…well we get to punish you how we see fit. The questions will be about each one of us to prove that you at least know something about us besides our cup sizes….the game ends when either we’re naked…or your teeny weeny cums in your diapees…ready diaper dork?!?!”

[Sissytiff17]

I looked down and saw all the diapers on me. There had to be at least 7. I tried to stand up but could not the bulk was way too much. All I could do was sit up. I am not sure how I will walk but I will figure that out in time. Then they sprung this idea of a trivia game on me. How could I say no. I love betting and getting to se them naked was so worth the risk.

”ok you are on. Bring on the trivia questions.”

[HumiliationLover423]

Veronica laughs at the confidence, “Let’s start with Selina….what is her last name?”

She stares awaiting a response as Rachel noticeably has her hand tightly clinched in a fist around something.

[Sissytiff17]

Oh god they really asked this. This is turning out to be a dumb bet. I have no clue but I better guess.

” I am going to say it is franklin”