The Bet that changed my life.

[HumiliationLover423]

Selina walks forward slowly swaying her hips, “Well we had to start you out with an easy question…I figured you’d get it right since I send you the closing report every…single…day…”

She slowly teasingly plays with the top button on her shirt, “After all it’s in my email, my ending signature….”

She leans down to whisper, “…and you STILL got it wrong.”

At that you feel a vibrating sensation begin in your crotch as all of the ladies laugh. Rachel now her fist unclenched waving the remote at you. Veronica laughs, “Every time you miss a question we turn that vibrator up a notch…ready for the next question?…Don’t care! When is my birthday?”

[Sissytiff17]

In all honesty this was not much of a punishment it actually felt pretty good. I was starting to enjoy it and got hard again. Dam this is a tough question. I really have no clue. 
 

“I guess it is March 5th”

[HumiliationLover423]

Veronica rolls her eyes as Rachel hits the button and the vibrating intensifies. Veronica laughs, “You must really want to cum in your diapees in front of all the prettiest women you know huh?”

[Sissytiff17]

She is definitely correct I am close to that. I feel myself about to lose control. I am trying hard not to lose control.

”no I don’t. I am trying bring on the next question”

[HumiliationLover423]

She snickers, “Really?” as the vibration continues she slowly moves forward, “I bet you’d cream your diapee at the smallest tease…”

All of the other women laugh as Rachel walks forward, “I’ve got the next question…would you cream your diaper at the sight of Veronica’s panties?”

[Sissytiff17]

They must be joking that would not make me cum. I feel the vibration stop.

”of course I would not I am a man and can control myself

i see Veronica strip down and stand in front of me. She was so hot in her panties. They were cute silk bikini style thong. Her front and ass looked perfect. I felt myself get excited. I started to twitch and my eyes rolled back and I exploded. I was so defeated now.

[HumiliationLover423]

All of the women laughed as Veronica redressed herself. Rachel saunters up, “How does it feel knowing that you are surrounded by the most beautiful women you know…and they’re all laughing at you…because you jizzed yourself from the sight of a woman in her panties….all while wearing a bunch of fluffy ass diapees!!”

She sends three forceful swats to your butt as the laughter just becomes louder. Rachel doesn’t even wait for a response before she circles you, grabbing you, making sure your butt faces all of the women, bends you over, and pulls the diapers down just enough to reveal your butt, “I’m going to spank your pathetic ass and with each one you’re going to count and admit something embarrassing…if I don’t consider it embarrassing enough you’ll have to start over…this will end when we reach 25…or until you piss those diapees to the sagging point…if that happens it’s going to get SO much worse for you, Eeny Teeny Timmy..”

[Sissytiff17]

I felt the 1st spank hit me I knew I was doomed and had to admit 25 of my deepest secrets.

” The carebear panties were mine. I bought them myself. I thought they looked cute”

ouch the 2nd swat hit.

”I have a fantasy of being cuckolded”

damm she hits hard I said as spank three came.

”I have never once satisfied a woman with intercourse only with my oral. They all said my dick is too small.”

Spank 4 “I have a bedwetting problem”

spank 5 caused a tear “ I was jealous of my prom dates dress in high school”

spank 6 “ I have ate my cum”

spank 7 “ I get turned on when people make fun of my small penis”

spank 8 “ I wanted to be a cheerleader when I was younger”

Spank 9 “ I am not smart at all I cheated through college and get by because my secretaries help me”

spank 10 “ the 1st time I had sex I could not figure out which hole was which.”

spank 11 caused more tears “ when I was 17 I got beat up by a 12 yr old girl”

spank 12 “ I cannot grow pubic hair”

spank 13 “ my penis is so small I have to pee sitting down”

spank 14 “ my high school girl friend use to make me wear her panties”

spank 15 more tears are coming “ I read cosmo every month”

spank 16 “I like to finger my asshole”

spank 17 “ I often wonder what sex as a girl is like”

spank 18 “ I wish gender roles were reversed”

spank 19 “ I believe I am more fit to be a secretary than the job I have now”

spank 20 I am full on balling my eyes out and kicking my legs. I am peeing too. “ I find women super attractive but get scared and cry many times when I try to have sex”

spank 21 “ I wore diapers until I was in 5th grade”

spank 22. “ I once got a prostitute and she spanked me for being so bad in bed”

spank 23”  I even cum too fast when jerking off”

spank 24” I pooped myself while at work the other day. That is why I had to leave early”

spank 25 “ I often wonder what it would be like to be treated like a baby”

[HumiliationLover423]

All of the women are laughing uncontrollably as Rachel stands you up, “While those were definitely embarrassing enough…you didn’t count once little sissy….so I’m going to give you a choice since this day is coming to a close….you can either take your punishment now and get it over with…or we can start it first thing tomorrow morning…and maybe drag it throughout the day…what will it be?”

[Sissytiff17]

She was correct those statements were super embarrassing. I cannot believe I admitted all that. I am just so intimidated by these women. To make manners worse I did not even do it right. I thought about it and while I needed this day over, it would be better to get the punishment over with.

“ok you are correct I did mess that up. I am sorry. I guess I will take the punishment now. This way tomorrow can be a better day”

[HumiliationLover423]

Rachel giggles, “Ok then…Tara go get the rope from your car..” she flashes a most sinister grin.

All of the women begin laughing as Rachel circles Tim, “While we wait…you’re going to answer every question I ask…and answer it honestly…those diapees are looking pretty heavy…did you pee again?”

[Sissytiff17]

Did she really say rope? That scared me a lot. These women already had a high amount of control over me. I cannot imagine what they would do with rope. I know one thing. I am screwed and there is nothing I can do about it. For a second I start to jump up and run. I then realize how could I run. I am not even sure I could walk in all these diapers. Plus what can I do, she basically owns me now. When she mentioned pee, that caused concern. My diaper was wet but I did not release I wet it.

“yes I did pee again”

[HumiliationLover423]

All of the women laugh as she continues to circle, “Are you…(she forcefully grabs your diapered crotch)…stiff again Timmy….I can’t tell because the diapee is way too thick…”

[Sissytiff17]

I see them circling me, they look like lions going in for a kill. I feel one grab my diapers. She is correct. They are so thick I cannot feel a thing.

”yes I am wet. I got scared and wet some more. So now I am very wet.”

[HumiliationLover423]

Rachel goes around to your butt and grabs hold of the diaper, “I didn’t ask if it was thick…I asked if you had a stiffy…if you don’t want to answer the question, I have other ways of finding out..”

[Sissytiff17]

“Stop being so mean. Yes I am stiff again.” I can’t take this anymore and started to cry. Like ball my eyes out.

[HumiliationLover423]

Rachel shoves a pacifier in Tim’s mouth and roughly grabs him by his cheeks for his lips to pooch out, “Oh the little bitch can’t handle some teasing…you’re so fucking pathetic. I should fuck you like the useless bitch you are…but you’re not ready for that yet…do you think we cried and whined like itty bitty babies whenever you would call us worthless…whenever you said we would be useless without our ass and tits…no because we knew you had a small ass dick and someday you would slip up and we would make you feel every ounce of humiliation we felt…and baby we haven’t even scratched the surface…so shut the fuck up unless you want me to yank that paci out and replace it with my 12 in. dildo…and I give you the face fucking you deserve…” 

She then shoved him down on his overly padded ass. The thick diapers keep him from being able to sit proper so he anytime he would try to properly sit up he would just roll around a bit before falling back onto his back. Rachel would then lean down, “I was going to be nice and give you a diapee change, but now I think I’ll let you stew in it…”

Tara walks back in flaunting the rope and teasingly shaking it.

[Sissytiff17]

(I am so sorry. I did not even know you responded this got pushed so far down)

Wait she said I am not ready to be fucked yet. What does she mean by yet. Well I have always wanted to sleep with them. So, maybe this won’t wind up being all bad. Once I heard their comments and what I said, I knew I was screwed. Those were just things I said to the guys, I did not know anyone heard me.

I was thinking about all these things as I rolled around on the floor. The diapers were so thick I could not sit up. Now they are saying I won’t get a diaper change. This is bad because my stomach is starting to rumble. They must have put something in those bottles. I try to hold it but I lose focus when I see the rope. What is she doing with the rope? That second loss of focus causes me to explode. I lost all control.

[HumiliationLover423]

Tara slowly saunters up, “Time to get this…little lady all tied up!” Tara then sets about putting Tim in a hog tie.

Rachel walks over and leans down, “You’ll stay like that the rest of the day diaper bitch…and when you come in tomorrow…you better be wearing a fresh diapee…”

As all of the surrounding women laugh.

[Sissytiff17]

And I did stay that way the rest of the day. I really had no choice. I could not get myself undone. I must have wet myself multiple times through out the day. Thoughts went through my head like how will I change my diaper and how am I going to get home. I mean I am tied up. Finally I saw the door and them standing in the doorway.

“ please let me out. You said I need to change but how can I change if I am tied up? How am I even going to get home like this? Please show some mercy. “

[HumiliationLover423]

Tara walks up to Tim slowly. Her eyes filled with joy as she walks over and leans down, “You would’ve gotten changed…had you not been such a whiny little bitch when I tried to give my little instructional….so you get to stay in that all the ride home..”

 

She then slams a diaper down in front of Tim, “That is the only thing you will be wearing when you walk in tomorrow..come to my office to get your new outfit…don’t be late…”

 

Rachel then unties Tim as all of the women get one last laugh at the diapered cheerleader.

[Sissytiff17]

I could not help but cry over what Tara said. She actually wants me to walk into the office wearing just a diaper. How will I do this? I am going to be exposed to everyone. However I have no choice but to do what they say. I am basically owned by them now.

Once untied I took the diapers and sprinted out of the office to my car. I am not sure if anyone noticed but I had no choice. I got in my car and drove home. Unfortunately I needed gas. I drove to a station in a different part of town where no one knew me. I got out and filled the tank. Multiple men laughed at me and a few women yelled that I was cute. Finally I got the gas I needed and drove home.

once home I changed my diaper and went right to bed. It was shocking but I slept well. I woke up and got ready for work only in my diaper. Thankfully it was dark when I left. This meant no one saw me. At least I think. I pulled into work and sprinted into the office. All the girls were there as I sprinted in. I knocked on Tara’s door. The door that use to be mine. “Ma’am may I come in”