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Old 07-14-2022, 12:14 PM   #1
dwedgie
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Not sure where this will go so unsure what to name it. Bits based on real events.

When I was about 16 I was friends with rich , same age as me but more athletic and popular, Lisa , a year younger but popular in our year , slim , funny always up for a laugh, Simone , same age as me , very bossy and Jason again same age , very slim and good looking. Me I was average size , not the most popular kid at school but not unpopular.

We often hung out in an old empty farm building of an abandoned farm, chatting , drinking and playing truth or dare . Normally dares were tame like being dared to shout a swear word, lick the person to the lefts shoe etc .

This weekend Simone Messaged all of us saying to bring a complete change of cloths ( shoes socks , underwear , trousers / skirt , top ) that did not matter if they got messy. In a plain white carrier bag and a messy food item for some fun . A few messages back and forth between us all and it was agreed .

I got out my old school trainers , socks ,older pair of tight legged jeans , dark blue boxer briefs, grey t shirt and black sweatshirt all placed in a bag as requested, food item I took 3 tins of spaghetti from the cupboard.

When I got to the building Slmone and Lisa were already there , Some took my bag and aced it with hers and Lisa's, she instructed me to place food in the corner. Already there was a large trifle and ready made lasagna.

Shortly after Jason and Rich arrived together. They handed thier bags to Simone and placed the food with the rest of it . Rich had a large container of mashed potatoes and gravy and Jason a chocolate gateux.

Last edited by dwedgie; 07-16-2022 at 12:23 AM.
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Old 07-14-2022, 02:15 PM   #2
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Simone ( bossy as always ) called us altogether and announced we were going to try something different , pulling a bottle of vodka from a holdall she had, She announced " we are playing spin the bottle, first round , if the bottle points to you then you have to down a shot from it ! Second round will be take the bag of cloths it points to when you spin it , then we will all go to the stable area and change into them in separate stalls, the final round ,each choose a food , take it in turn to spin , where ever it points to , that person will pour the food down the underwear you are wearing from the bag ! "

She obviously saw the look of surprise on our faces and said "that's right , you could well end up wearing cloths of the other sex , including underwear , to keep it fair us girls will keep our bras on , you boys if you get to wear girls cloths there will be a training bra on the bag. "

" Now come on , get in a circle "
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Old 07-15-2022, 02:59 PM   #3
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We all gathered into a circle , Simone placed the vodka in the middle along with a shot glass and a bag of 1p coins . " If the bottle points to you , you have to down a full shot in this glass and take a coin " she said. But why take a coin?" Asked Lisa , " the one with the least coins starts the final 2 rounds and the one with the most is last ! We need a way of deciding the order!" She stated .
" I'll start as it's my idea" says Simone. As she spins the bottle. As it slows down sure it will land on me, it just went past me and pointed at Rich , as I breath a sigh of relief ( I get tipsy really quickly ) Rich say " damn it's always me first " he fills the glass and downs or to a chorus of cheers !
Lisa spins next , and it points straight at her ! " Oh well may as well start then " she said excitedly as she pours and downs her drink in seconds .

After about 45 minutes we are down to the last shot , spun by Jason it lands on me , I fill the glass with every last drop and down it !this is shot 6 for me and I don't feel to bad.

Ps , I'm Dave by the way !!

We each count our coins
Rich 5

Jason. 3

Lisa. 6

Simone 7

Me. 6

Fairly evenly scored" well we have our order , Jason ,rich, Lisa as girls always go first , Dave , then me " says Simone .

"This is going to be fun giggle a tipsy Lisa , there's some I hope gets my bag! "

" Yeah well whoever gets mine is getting off easy " said Jason

I was thinking along the same lines as Jason , let's face it girls often wear boys cloths, how often do boys wear girls cloths !!
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Old 07-16-2022, 12:22 AM   #4
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The next 20 minutes were spent chatting , Rich kept asking everyone what cloths were in thier bags , Simone said firmly " we will have to wait and see , don't keep asking . You may be lucky and get your own bag. Or do you want a girls bag? "
" No I don't want a girls bag " he replied
Jason asked " what if we refuse to put the cloths on ?"
" Then the rest of us will have to decide on a forfeit" replied Simone.

" Ok Lisa , put the bags on a circle " said Simone.
Lisa placed the bags in a circle , all the bags looked the same and you could not make out what was in them .

" You may only look in the bag when you get to a stable to change " ordered Simone .
The bottle was spun in the order of coins. We all took our bags to the stables to change .

I got I to the stable I was changing in, nervously I peered into the bag , this has to be a girls bag, I could see some pink .

The first item was a pale pink training bra with white straps that were decorated with brighter pink flowers.
Next was a pair of black socks with lacy thrills on the top.

I was concentrating so much in my bag I could not hear what else was going on.

I placed the items on a ledge in the wall.

Next was something pale gray, I took it out of the bag. It was a pair of ¾ length leggings , with Nike written down one leg in pink . I'm sure I had seen Lisa wear something similar in the past.

I pull the next item out , it's a pair of pink panties , full brief style , the fabric is a pale pink with lacy thin bright pink elastic . Turning them over , I notice onthe front there is a picture of a unicorn on them with Tuesday above it ! Days of the week knickers , great . I'm sure this was Lisa's bag.
I notice how soft and delicate the fabric appears compared to my normal boxers / boxer briefs.

The next item is a matching gray t shirt to the leggings , again with a pink Nike on the arm.

Then in the bottom of the bag a pair of pale pink ballet shoes , I now knew this was Lisa's bag as she did ballet.

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Old 07-16-2022, 12:25 AM   #5
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Please keep going! I'm totally hooked in
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Old 07-16-2022, 12:27 AM   #6
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Denon 21 I will continue , will try to do a bit each day

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Old 07-16-2022, 02:03 AM   #7
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I look forward to the next part
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Old 07-17-2022, 06:59 AM   #8
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I am stood in the stable looking at my outfit , then I realise if this is Lisa's bag in for a bit of a problem , Lisa is slimmer than me.

I decide to get on with it , I take my t shirt and jumper off in one , I notice there is a slight chill in the air. I unbuckle my belt , pausing for a few seconds, I unbutton my jeans and realise I'm still wearing trainers . I bend over to remove my trainers and socks. My feet are bare on the cold stone floor. I slid my jeans down to my ankles before stepping out of them , suddenly I realize I'm standing here in just my boxer briefs ! Feeling a bit nervous I slide my boxer briefs down my legs to my ankles and step out of them. I feel a gentle cool breeze over my now naked body, it feels odd , I feel free but vulnerable.
I pick up the panties , still surprised at how delicate they feel, I bend over and step into them , pulling them up my legs they feel nice. They are up to my knees and feel good. Pulling them up further , as they go up my thighs I notice tho they are tight on my legs they are stretching to fit.
I pull them all the way up to my waist, they are tight but comfortable, I fit into them , just, my balls and dick are slightly squashed whilst I have a slight wedgie.
I never thought I would wear panties , bit here I am, in an old farm building wearing a pair of days of the week panties, and I quite like it.

" Hurry up , or I'm coming in there and dragging you out in a minute " shouted Simone.

I heard Rich say one minute.
I replied , " coming , just a minute"

Now under pressure I pull the leggings on , followed by socks , ballet shoes ,. Shit I've never taken a bra off someone , let alone put one on. I decided to put it on backwards and do the clips up before twisting it round my body and sliding my arms through the holes.

I slip the t shirt on and realise the outfit is actually a good fit.

As I step out i realise iam the last out, the others clap and wolf whistle , Simone says " not bad at all , you make a pretty little girl. "

" Shame it was not Rich in them tho " says lisa

Rich chuckles , and says " hello babe "

Jason chips in with " I hope yours is more comfortable then mine!"
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