Jen's Bet

[ValerianXIII]

This is a story I have had on my computer for a little while. If anyone is interested I will probably continue it.......



" I got her!! I got the bimbo bitch!!" Jen, my fiancée, was cheering the moment she walked through the door. "What's going on?" Although I had some idea who she meant. You see Jen's parents moved away and left us with the house she grew up in. The problem was are neighbors did the same thing with their daughter Ashley. Jen absolutely couldn't stand Ashley. While Ashley's older sister Beth and Jen were best friends growing up it was the opposite with the younger sibling.

Jen and I were 24 while Ashley was only 19. Beth and Jen were both bookworms. They dressed very modestly and were more or less on the average side as far as looks went. Jen had shoulder length brown hair with freckles that she covered up with make up. She was on the short side standing only 5'3 and was rather pale. She had a bit of a temper and would get quite jealous especially if a girl, like Ashley, had big breasts. That seemed to be Jen's hot button all the time and I never would mention it out loud but Jen had the tiniest little A-cups I had ever seen. her breasts were the size of marshmallow each capped with a dark nipple.

Honestly at the time I had barely seen Jen without a bra. She kept a bra on padding to almost a C- cup. She kept it on at all times, even in the bedroom. But only the two of us knew about that back then. Anyway so with Beth, her older sister, she used make all these bets with these "crazy" forfeits. Most of the time it was whoever scored higher on whatever test won and the loser had some kind of mildly embarrassing forfeit. Maybe at the worst a silly outfit for a day or so but nothing really that crazy.

Honestly I thought it was all kind of lame at the time and Jen usually won anyway so It rarely mattered. Now apparently she was doing the same kind of bet with Ashley but it was going to be much bigger. I really didn't care at all actually until Jen said those two words.

"BABY MAID"!

That really got my attention!

We all grew up in a college town and local sororities had long standing traditions on how they punished their pledges. Their was a legendary punishment rarely used but often talked about called "Baby Maid". It was a lot like it sounded actually. The pledge would have to spend a certain amount of time working as a maid but at the same time she was treated and dressed as a baby!! The baby maid treatment had very set rules and there was even a book on it and pf course Jen owned a copy. It was for humiliation purposes mainly and most pledges would do anything to avoid that terrible fate.

Usually a week at the most dressed by her sisters in a different baby outfit every day while she had to clean the entire sorority house. What really interested me and probably everyone else was the occasional nudity that was involved. Some of the outfits were not only embarrassing but quite risque.

I remember hearing tales of see through baby dresses or some girls wearing nothing but a diaper! Those stories always drove me crazy but you never actually would see anything like that. The thought of Ashley wearing any of those outfits while cleaning are house made by penis come alive quite suddenly.

If we were to rate these girls on a scale of 1-10 honestly , my fiancée would be a about a 5 and Ashley would be a 10.5. I mean Jen is pretty but Ashley is just beautiful, with long blonde hair and a slight tan. Not to mention her body is pretty much perfect. Natural D cups breasts that defied gravity and a perfect slightly muscular bottom.

Jen's best attribute is her bottom but Ashley blows her away even in that department. Not to sit here and compliment myself but up to this point I did a pretty good job of convincing Jen I wasn't even attracted to Ashley. I claimed to not even like big breasts and she believed me! She had know idea how much the thought of her humiliating Ashley turned me on.

"What happens when you win and she backs out of the deal?!" I ask hoping my fiancée has it figured out. Her smirk told me I was right.

"I brought legal papers into it! She's trapped, this thing is air tight. Any backing out I get the title to her house and her car. We found a notary who is going to monitor everything and got it all official. I can't believe the dumb bimbo actually signed!!"

"What about all the baby stuff? Where are you going to get that?" I asked genuinely curious.

She smiled taking me to what used to be her room growing up and was now just a spare room. It was already starting to look a bit like a nursery with a crib that I had to assemble later and several bags of assorted baby dresses and supplies. I could see she was really set on humiliating Ashley and it was so strange to see her jealous temper flare up.

My penis stiffened again when I noticed a couple of paddles that were probably used to spank the sorority girls over the years. I couldn't help but a imagine Jen spanking Ashley's perfect butt with one of them.

Jen's Boyfriend before me was a couple years younger than her and Ashley managed to steal him after they had been together for nearly two years. She said it was like he became a zombie no longer wanting to talk only interested in going to see Ashley. Once their relationship had been destroyed and Jen had been thoroughly humiliated Ashley suddenly dumped him like he never existed. Now Jen wanted revenge and she planned on embarrassing Ashley ten times more the she had embarrassed her!!

I mostly kept my mouth shut not wanting to reveal to Jen I was at all interested in what happened to Ashley but I did have a couple questions. "So how long is the bet for?" That's when Jen's smile widened.

"A whole month!! I'm going to make that stupid bimbo's life a living hell for a whole month!!!"

I must of looked at Jen with a bit of shock on my face, surprised she was taking this so far.

"Most of it was her idea actually. She got herself in this mess!" Jen explained. "She's the one who mentioned Baby Maid anyway, it wasn't my idea."

I looked down with genuine concern at the time and I couldn't help but ask .

"But what if she wins?" I asked with a little bit of worry in my voice.

Jen looked at me like she had never even considered that possibility. "Well it would be the same for me but that's never going to happen....."

[Casanova]

Going by your Devaintart it's quite clear you enjoy the older cucquean theme. Nice to see you writing a story with it.

A couple questions just to gauge your preferences some more.

1) Are you only into OON?
Or is there a chance someone else like the older sister may find herself on the same situation.

2) Do you not like sibling rivalry?
As in the younger sister would never humiliate her sibling.

Or from the babysitter story Timmy would be a bit more assertive and check Sally.

[ValerianXIII]

Going by your Devaintart it's quite clear you enjoy the older cucquean theme. Nice to see you writing a story with it.

A couple questions just to gauge your preferences some more.

1) Are you only into OON?
Or is there a chance someone else like the older sister may find herself on the same situation.

2) Do you not like sibling rivalry?
As in the younger sister would never humiliate her sibling.

Or from the babysitter story Timmy would be a bit more assertive and check Sally.

Usually into OON but I could see a sister sharing the same fate. Maybe not in this story though. I like the idea of two sisters losing a catfight to another set of younger sisters.

Definitely like sibling Rivalry when its younger sister embarrassing older sister for sure.

[Mikey554]

Can’t wait for more of this story, great setup

[Frank89]

Not sure if that's the original idea, but I do hope Jen's plan backfires and she will be the Baby Maid.

[mars357]

Oh yes, please carry on!!!

[jimmythehand]

This is a story I have had on my computer for a little while. If anyone is interested I will probably continue it.......

Interest activated.

[reviewer]

Not sure if that's the original idea, but I do hope Jen's plan backfires and she will be the Baby Maid.

Great start! Please keep going!
And I would also prefer that the bet fires back on Jen! Maybe she could build up the stack even further and arrange things (like parties or events) just to realize at the end that she has is the one being utterly humiliated!

[Mikey554]

Suggestion Jen loses initial bet, maybe partway through her time as baby she gets offer for another bet double or nothing 2 months as baby or month ends then and there,

[Hooked6]

I would like to add my hearty recommendation that you continue this story. The set-up is most intriguing.