Lost Bet (Patreon)

ArgentParoxysm said the following: Well today wasn't going your way. You made a bet with your friends that you definitely believed you would win. However, a miracle happened, and you lost. Now you were currently driving all the way to the edge of town where your friends wanted to meet you for the dare.

Think-pink1 said the following:

The entire drive was tense. I mean I didn't want to go there knowing whatever I had to was going to be horrible. I had thought about standing them up but I am a man of my word.

ArgentParoxysm said the following:

Plus your friends gave you some leeway and said that if you completed the date, they’ll give you $500 in cash.

Think-pink1 said the following:

I pulled up at the place and saw my friends waiting for me.

ArgentParoxysm said the following:

They were standing in front of a large van.

Think-pink1 said the following:

I walked up to them "Alright, let's get this over with." I said with a tone that conveyed how little I wanted to be there.

ArgentParoxysm said the following:

“Took the words right out of our mouths.” One of your friends said before they went to the back of the van, opening it.

Think-pink1 said the following:

I poked my head over to see and my jaw dropped to the floor at what I saw.

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ArgentParoxysm said the following:

It was by far, the biggest dress you've ever seen, colored in the most girly ultra-pink. It was so big that it filled the entire van to the brim, and then some.

Think-pink1 said the following:

They expected me to wear that. "Hell No," I said. Taking a step back from the van.

ArgentParoxysm said the following:

"Come on, it's not that bad." One of the guys said. "It won't kill you."

Think-pink1 said the following:

"I dunno man. I may be the first person to die from embarrassment if I wear it."

ArgentParoxysm said the following:

"Dude you gotta follow up on the bet." One of the guys said. "We'll force it on you if you don't."

Think-pink1 said the following:

I thought about running but I was reminded about the money. "No one will see me, right. This stays between us." I said. Taking my time to point and look at everyone in the group.

ArgentParoxysm said the following:

The group nodded, before helping you with the gown.

Think-pink1 said the following:

Actually, before they got me into the gown. They first needed to get me out of my own clothes. I was stripped down and stood naked in front of all my friends. I tried to cover my privates to maintain some sort of modesty.

ArgentParoxysm said the following:

"Meh, it's nothing new." One of them said as they handed you the accessories.

Think-pink1 said the following:

First up was the tiny pink panties. When I slipped them on I found that they were almost too small. That's when I was told to tuck myself away.

ArgentParoxysm said the following:

They were tight, but also very comfortable, much more so than your plain old underwear.

Think-pink1 said the following:

"Now that princess has her panties on it's time to put on your stockings," One of my friends told me.

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ArgentParoxysm said the following:

You rolled your eyes at his joke. The stockings had frills at the top. Like with the panties, the stockings were also very comfortable.

Think-pink1 said the following:

Next up was the corset. It was put on me and I was laced into. The laces were pulled so tight it crushed my ribs but it gave me an amazing hourglass figure. The only drawback I could not breathe. "Now you have perfect princess posture."

ArgentParoxysm said the following:

"You'll get used to it."

Next were the petticoats.

Think-pink1 said the following:

"Now it's time for your petticoats, princess." My friends were really laying it on thick now. The only good thing about the petticoats was that they were white, not pink. The bad thing? They were huge. scratchy and heavy.

ArgentParoxysm said the following:

Fortunately a slip was put on before the petticoats to protect your legs from the petticoats. The bad thing about it was that it was rather right around the legs.

Think-pink1 said the following:

"Princess will have to take much smaller steps now"

ArgentParoxysm said the following:

Now for the petticoats. There had to be like, a hundred of them, and each one was incredibly big!

Think-pink1 said the following:

It took all the guys to lift one of them up and over my head. It took forever because they had to repeat the process every time.

ArgentParoxysm said the following:

But eventually, all of the petticoats were put onto your waist. You now had a bell stretching five feet in every direction

Think-pink1 said the following:

Every movement made a loud rustling sound that drowned out any laughter or teasing from my friends but it was also very heavy. It was like having a concrete skirt tied around my waist.

ArgentParoxysm said the following:

Now for the gown itself.

Think-pink1 said the following:

Boy was it a monster of pink lace, taffeta, and silk. It had a bodice that was covered in gaudy details that showed my sucked in Barbie waist. It then exploded out into the skirts. The skirts were layer upon layer of materials with all kinds of bows, lace, and intricate designs. Any embellishments were in a purple hue. Of course, then were the sleaves to giant balls of puff that sat on my shoulders and were the size of my head and a half.

ArgentParoxysm said the following:

The behemoth was slowly lowered onto you, consuming you.

Think-pink1 said the following:

I had to fight my way through. Eventually, I emerged. My head poking through the hole and my arms through the sleeves.

ArgentParoxysm said the following:

The boys then began to fluff out the skirts and petticoats as much as they could, making it look like your skirts were growing.

Think-pink1 said the following:

Once they were satisfied. One went into the van and came back out. With a box in his hand.

ArgentParoxysm said the following:

He then opened the box and pulled something out.

Think-pink1 said the following:

In his hands was a ridiculous wig. "This is your wig, Princess. Do you like it?"

ArgentParoxysm said the following:

It certainly looked realistic, colored a golden blonde.

Think-pink1 said the following:

"It's made of real human hair." I was told as the wig was lowered on me.

ArgentParoxysm said the following:

...well, at least it was clean, and smelled good.

Think-pink1 said the following:

"Now we need to do your makeup. Unfortunately, none of us know how. Luckily we have a special guest. C'mon on." Out popped my girlfriend. I was mortified.

ArgentParoxysm said the following:

Luckily, your girlfriend simply giggled and went over to do your makeup. "You look beautiful..." She whispered into your ears so the others wouldn't hear.

Think-pink1 said the following:

My cheeks reddened at that comment. I was told to close my eyes as my GF did my makeup.

ArgentParoxysm said the following:

You closed your eyes and let your girlfriend do your makeup.

Think-pink1 said the following:

"Open your eyes sweetie." She told me. I opened my eyes in front of me was a handheld mirror. For the first time, I got a look at my reflection.

ArgentParoxysm said the following:

The makeup applied made you look like a genuine girl. Hell you looked like a supermodel!

Think-pink1 said the following:

Indeed. The concealer hid any flaws. The mascara and false eyelashed gave me girly lashes. My eyeshadow was purple as well as my lips which were made very puffy and kissable.

ArgentParoxysm said the following:

Overall, you almost fell in love with your reflection.

Think-pink1 said the following:

It seems that I wasn't the only one who fell in love with the new me.

ArgentParoxysm said the following:

Indeed. Your girlfriend was also awed by how beautiful you were. She was bi, and you were the only one who knew of this.

The boys were just laughing their asses off, but you ignored them.

Think-pink1 said the following:

While the boys laughed. She leaned over and whispered into my ear.

ArgentParoxysm said the following:

"I love the new you." She whispered. "Can you be this all the time?"

Think-pink1 said the following:

Before I could answer one of my mates spoke up. "C'mon girls get in the van. It's time for phase 2."

ArgentParoxysm said the following:

The others got into the van while your girlfriend went over, but stayed out so the boys could explain the next part of the bet.

Think-pink1 said the following:

"You see Princess the next part is you are going to go on a little hike."

ArgentParoxysm said the following:

"Basically you've gotta walk all the way across town to get back home. If you get home before the sun goes down, we'll double the cash. If you don't, then you get no cash, and you'll be stuck with the dress." One of the boys said.

Think-pink1 said the following:

"Wait what. That wasn't part of the deal." I protested.

ArgentParoxysm said the following:

But the boys were listening. Your girlfriend leaned into your ear. "Make it back safely babe. No one will know that you're a man with the makeup and wig. You'll be fine." She said before giving you a deep kiss on the lips.

Think-pink1 said the following:

I nodded, and with that, the van sped off.

ArgentParoxysm said the following:

Leaving you there, as a very beautiful woman, in the biggest dress in existence.

Think-pink1 said the following:

I sighed before setting off. I had to get going if I was to get back in time.

ArgentParoxysm said the following:

Your massive skirts swayed and swished beautifully as you went, rippling as well.

Think-pink1 said the following:

My hair also bounced against my back as I went. Progress was slow as I minced my way through town.

ArgentParoxysm said the following:

Luckily, what the guys didn't know was that you knew a back alley that cut through most of the town. The problem with that? It was narrow.

Think-pink1 said the following:

I decided to risk it and headed over there.

ArgentParoxysm said the following:

It seemed that the alley was just wide enough for your skirts

Think-pink1 said the following:

It turns out that I didn't need to worry about the length of the alley, what I did need to worry about was the drunk homeless man who was sitting down and wide awake.

ArgentParoxysm said the following:

Just stay calm, and just keeping looking ahead. Ignore him, and he won't do anything.

Think-pink1 said the following:

I slowly made my way through the alleyway however my plan was flawed as the man turned as soon as he saw me coming "What's a pretty lady like you doing here" He catcalled.

ArgentParoxysm said the following:

Shit...okay, this can be fixed. Make the drunk believe that you're mute. Since he's drunk, that'll be easy.

Think-pink1 said the following:

I kept my purple lips closed. "Cat got your tongue," he said as he got up. Now blocking my way.

ArgentParoxysm said the following:

Hmm...well, if there was one thing you could do, its to knock that guy out. Maybe you could try and seduce him and making him turn around, so you can base his head with a glass bottle nearby.

Think-pink1 said the following:

I didn't consider myself much of an action hero. So I decided to go a more diplomatic route. "I would just like to go past." But I made a mistake while saying that I spoke in my normal voice.

ArgentParoxysm said the following:

You goddamn idiot...

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Think-pink1 said the following:

"You're a guy," He said. Astonishment clearly in his voice.

ArgentParoxysm said the following:

You need to run, now.

Think-pink1 said the following:

I tried turning around to run the direction I came but disaster struck. My stupid skirts got in the way. I was stuck!

ArgentParoxysm said the following:

Punch that guy in the face!

Think-pink1 said the following:

He got closer and closer to me. I could feel his breath on my neck and suddenly he was gone. I turned my head and saw him passed out in his own vomit. I breathed a loud sigh of pure relief.

ArgentParoxysm said the following:

Well that was close, but you had to get past him, but you didn't want to ruin your pretty dress.

Think-pink1 said the following:

Suddenly I remember Princess Movies they would gather their skirts up to avoid getting their dresses dirty.

ArgentParoxysm said the following:

So you gathered up as much skirts as you could in your arms.

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Think-pink1 said the following:

Skirts in hand, I navigated myself, past the passed out guy and the vomit. Somehow not getting any on my shoes or skirts. I was now through the other side and on Main Street. But it was out of the frying pan and into the fire as the place was completely packed. A Princess in a giant ball gown quickly got a lot of attention.

ArgentParoxysm said the following:

Maybe you could find another way around. The guys didn't say that the path had to be exactly straight.

Think-pink1 said the following:

I looked around trying to find some sort of path. "Mommy, Mommy a Princess" cried a little girl who eyes wide. That set everything off. Lots of pointing and laughing. I was soon blinded by cameras going off. Great! This was going all over social media. So much for this being between me and the guys.

ArgentParoxysm said the following:

But you were safe since your makeup and wig were flawless, making you look like an actual princess. Just don't speak, and everything will be fine.

Think-pink1 said the following:

Just don't talk. I thought to myself repeating it like a mantra in my head. I began making my way through the town. However, the crowd began to follow me begging me for hugs and photos. All sorts of people were coming up to me like sweet little girls and even adults.

ArgentParoxysm said the following:

The young girls were so cute. You couldn't resist giving them hugs.

Think-pink1 said the following:

However, all this stopping and starting was really slowing me down.

ArgentParoxysm said the following:

Maybe you could get a taxi.

Think-pink1 said the following:

That was a good idea! But I didn't have my phone they were in my pockets in my clothes that my friends have.

ArgentParoxysm said the following:

Maybe one of the kind people could give you a ride. They seemed nice enough.

Think-pink1 said the following:

Deciding to do it. I swished over to a nearby stranger.

ArgentParoxysm said the following:

It was a boy around your age. "Hm?" He looked up and saw you. "Oh, hello. Is something wrong?"

Think-pink1 said the following:

"Could I please get a lift with you. I need to get home" I asked him.

ArgentParoxysm said the following:

The man blinked owlishly upon hearing your voice. He breathed in before sighing. "What happened?" He asked as he led you to his car.

Think-pink1 said the following:

I lost a bet. My forfeit was to dress like this and then walk the length of the town. If I don't get home in time they won't let me have my clothes back." I told him.

ArgentParoxysm said the following:

"I see...well, I don't know if you'll fit in the back seat." He said while getting into his car.

Think-pink1 said the following:

"Worth a shot," I told him while I opened the back door.

ArgentParoxysm said the following:

You then tried to squeeze inside.

Think-pink1 said the following:

Unfortunately I couldn't fit inside.

ArgentParoxysm said the following:

You tried shoving as much skirts as you could inside.

Think-pink1 said the following:

There was just too many skirts and not enough space in the back of the guy's car. I could barely fit in the van that the guys brought me down in.

ArgentParoxysm said the following:

The man sighed. "Well that's a bust..."

Think-pink1 said the following:

"Now what am I supposed to do?" I asked helplessly.

ArgentParoxysm said the following:

"Maybe you could ride on top of the car?"

Think-pink1 said the following:

"Isn't that a bit dangerous," I asked.

ArgentParoxysm said the following:

"Well how else are we gonna get home quickly?"

Think-pink1 said the following:

"True," I said. Pilling on to the roof of your car.

ArgentParoxysm said the following:

Your skirts almost completely covered the car. The man went to find something to cover you.

Think-pink1 said the following:

I crossed my arms and waited and waited and waited...

ArgentParoxysm said the following:

He came back with a large tarp.

Think-pink1 said the following:

He chucked it over me and tied it down into place. Tugging on it to make sure it was tight.

ArgentParoxysm said the following:

You lied down on your huge skirts, thankful that it was so poofy that it was comfortable to lay on.

Think-pink1 said the following:

Before long I heard the car door slam and felt the car's engine being started. 

ArgentParoxysm said the following:

Your skirts began to ruffle as the car moved down the street. You gave the man the address for the house before you got onto the car.

Your thoughts began to circulate on your massive gown. Despite how cumbersome it was, you had to admit...you liked wearing it.

Think-pink1 said the following:

Was it something I would wear day to day? Definitely Not. But on occasion, sure. Especially since my girlfriend said she liked me in it. Speaking of which I hope she's home when I get back. I then began to wonder about all the stuff we would do. I started to feel my tuck slip out of my panties.

ArgentParoxysm said the following:

Were you...getting a hard on? From wearing this gown?

Think-pink1 said the following:

Honestly, it was probably a mixture of sexy thoughts and the gown.

ArgentParoxysm said the following:

Either way, you were glad this gown was so big, so no one could see your hard on. And...you admitted you really liked wearing it, since it was so comfy.

Think-pink1 said the following:

With that conclusion reached I found the car come to a stop.

ArgentParoxysm said the following:

The man helped you down from on top of the car. He parked in front of your house.

Think-pink1 said the following:

"Thank you" I said to the man. Looking at the sky I could tell I had arrived just in time.

ArgentParoxysm said the following:

"No problem." He said, before giving you his number. He then drove off.

Think-pink1 said the following:

"Huh" I said to myself. A little bit in shock. I then minced up to the door and knocked.

ArgentParoxysm said the following:

Eventually, your girlfriend answered. She smiled softly upon seeing you. "Hey babe..." She moved forward and brought you into a hug and a kiss.

Think-pink1 said the following:

I both hugged her back and kissed her back as well. I was very happy to see her again.

ArgentParoxysm said the following:

She gently pulled you inside, your skirts wedging you in the doorway for a bit.

Think-pink1 said the following:

"Where we going" I giggled.

ArgentParoxysm said the following:

“Inside, where no one but me can appreciate you...” I said lovingly.

Think-pink1 said the following:

I blushed at that. Following you to where ever it was that you were leading me.

Think-pink1 said the following:

I stood in the bedroom before you in all my princess finery. "S- So no what" I stuttered being uncharacteristically nervous and shy around you.

ArgentParoxysm said the following:

I giggled. “No matter what happens, don’t take off your gown.” I said as I crouched down and began to lift your skirts. I then began to crawl under your skirts. Since they were so big, I completely disappeared.

Think-pink1 said the following:

I was wondering what on earth you were doing when I felt my panties slid down releasing my erect cock from its prison.

ArgentParoxysm said the following:

I then enveloped your cock in my mouth, bobbing it as I sucked it

Think-pink1 said the following:

My mind went completely blank as I all I could think was "Oh my God!"

ArgentParoxysm said the following:

The pleasure hit you like a tidal wave.

Think-pink1 said the following:

You sucked, licked and teased my cock and balls for some time but eventually, I couldn't hold it any longer. "I'm going to cum" I warned you.

ArgentParoxysm said the following:

“Good...” I said muffled as I sucked your cock harder than before.

Think-pink1 said the following:

And with that, I climaxed right into your awaiting mouth.

ArgentParoxysm said the following:

I swallowed ever single bit of your cum. I giggled a bit after I swallowed, before giving your cock some soft kisses.

Think-pink1 said the following:

"Oh, babe your so good," I told you still getting over it.

ArgentParoxysm said the following:

“I know...” I murmured as I cane out from under your skirts. I then guided you to the bed.

Think-pink1 said the following:

"I love you, honey," I told you. You then proceeded to give me a playful push onto the bed. I gave out a little "Yep" as I fell.

ArgentParoxysm said the following:

You collapsed onto the bed, your skirts swallowing you.

Think-pink1 said the following:

"Pff" as I tried to get the hair out of my mouth and my skirts under control.

ArgentParoxysm said the following:

You eventually did. Your skirts were spread out like a tablecloth, completely covering the bed you were sitting on.

Think-pink1 said the following:

"I'm all yours, baby," I told you

ArgentParoxysm said the following:

I giggled. “I know...” I said as I came down on top of you, kissing you while groping your chest.

Think-pink1 said the following:

I cupped your face with my left hand and I squeezed your right breast with my other hand.

ArgentParoxysm said the following:

I moaned into the kiss as I kissed harder.

Think-pink1 said the following:

I moaned as well. I felt myself take a submissive role letting you take the dominant role.

ArgentParoxysm said the following:

As I was making out with you, I reached under your skirts and grabbed your cock, angling it towards my vagina.

Think-pink1 said the following:

You pushed me inside of you. I began to thrust.

ArgentParoxysm said the following:

I began to thrust as well, still taking the dominant role.

Think-pink1 said the following:

Our bodies soon fell into a rhythm, up and down, up and down.

ArgentParoxysm said the following:

Up and down and up and down and down and...wait, no, up and down.

Think-pink1 said the following:

We made love for 7 minutes until both of us reached the big O.

ArgentParoxysm said the following:

And when that happened, we climaxed as hard as we could.

Think-pink1 said the following:

I squirted cum for the 2nd time, however this time it was into your glorious pussy.

ArgentParoxysm said the following:

I moaned gorgeously as I squirted as well.

Think-pink1 said the following:

You then got off me and lay next to me. Both of us were exhausted.

ArgentParoxysm said the following:

I lied on your skirts, panting. “That was amazing...”

Think-pink1 said the following:

"It was, wasn't it. Might be the best we've ever had" I mused, turning my head to glance at you.

ArgentParoxysm said the following:

I glanced at you and smiled. “Yeah. Probably because you’re a pretty prissy princess.” I giggled at the light tease.

Think-pink1 said the following:

I giggled as well, "I'm not a pretty prissy princess, I'm YOUR pretty prissy princess," I mock protested.

ArgentParoxysm said the following:

I smiled before giving you a fat smooch on the lips. “I know...and I love that you are...”

Think-pink1 said the following:

With that, we snuggled up using my dress as both a blanket and a pillow. We fall asleep in each others arms.