Many Bets That Backfired!

[TheTaskMaster]

This is my third attempt at a story but I have lots of ideas...
The school system is the British one if your american or something like that!

Chapter 1

It was 4:15 and Holly was going to arrive in five minutes. She was coming over for a couple of days because we had some time off school. I still couldn't believe it as she was easily the prettiest and most wanted girl in our year, maybe the whole school, however she was very shy and didn't talk to many boys or people out of her friendship group. She was about average height for a thirteen year old girl and was extremely fit. The only reason I stayed after school to go to the gym was because i got to see her in her tight fitted blue top and her black short shorts. Her brown hair dropped just bellow her shoulder. She had smaller breasts than most other girls in our year, but they were just the right size in my opinion, I saw them a lot through her blue sports top as she didn't wear a bra in the gym. Most of my friends tried to stay over as well but I backed them down so that me and Holly could be alone. I had a crush on her since she moved to our primary school in year 6.

My Mum wasn't home yet and my Dad was away on business in France so we would be alone for a few hours. I was running out of time trying to choose what to wear but I eventually decided on my black and red, stripy boxer briefs, a navy Adidas t-shirt, and a pair of black shorts. It was summer so I wasn't going to freeze to death. I was just lying on my king sized bed when I heard the doorbell wring. I rushed downstairs to open the door but when I did it turned out to be my neighbour asking me to throw his ball back over the fence. After I had given the ball back, I slowly plodded back up to my room. With one quick look at my room I decided that I should probably tidy it up quickly so that all my dirty underwear and clothes weren't on show to Holly. It took me ten minutes to finish tidying my bedroom but once I had, I heard the doorbell wring once again. I walked down stairs, less eager this time, to open the door to Holly. At last she arrived!

"Hey there!" I said,
"Hi Will, could you help me with my back its overflowing a bit?" She asked me pulling behind her a full bag that i recognised from the gym. I reached for her bag and lugged it upstairs closing the door behind me. I showed her to my room and put her bag on my bed.
"So, what do you want to do?" I asked,
"How about we just chill downstairs for a while and have a drink or something?" She replied pointing towards my bedroom door.
"Um sure why not" We sat down in the living room and I got us a can of diet coke each. After talking for a while we decided that we would do a bit of a betting sort of game. We would play a game, like blackjack and whoever lost would have to do what the other person wants. We started off playing a game of higher or lower, we would take it in turns guessing weather the next card in the pack would be higher or lower than the previous one, aces were high.

"If I win, I want you to give me a back massage for ten minutes!" I offered
"Ok then, if I win, which I will, you have to let me give you a wedgie!"
We agreed on the rules and the conditions, it started of in my favour and by most of the pack it was 24-19 to me. Holly pulled it back to 24-22 but then I won another meaning if I won 1 more than I would win. the starting card was a three this time and Holly called higher, she got the point as the next card was a four. Then I called higher but it ended up being a two. Holly was equal on points as she rightly called higher and got a queen. I called higher as I knew the last card was the ace of hearts and won a ten minute massage. I lay on my bed and set a ten minute timer. When the ten minute timer finished, I started to get a semi-boner so quickly covered up with a pillow so Holly didn't notice. I don't think it worked though because she let out a slight giggle.

The next game we chose to play was a simple staring competition. I decided that I wanted Holly to take a shot of lemon juice and she decided that I still deserved a wedgie. I was exited when she told me that we should do a staring competition because I was sort of the master at school. As soon as we started she burst into laughter and I had won the second challenge. She downed the shot of lemon juice and sat back down.

"What next then?" I asked
"How about a game of Fifa?" She replied so I set up the PS4 and loaded Fifa 17. I thought that this would be the easiest game of my life but I didn't expect what followed. I chose Bayern Munich and she chose Manchester City.
"What do I do if you win?" Asked Holly,
"Um, down a can of coke?" I suggested
"Easy, you have to do what I want for the next fifteen minutes"
"Deal"

We started to play and I knew instantly that I made a mistake. She got kick and scored a spectacular goal with Sergio Aguero in the opening minutes. She dominated the whole game and ended up thrashing me 13-4.
"So what do you want me to do then?"
"Well, I want you to..."

To Be Continued!

[Sydney_sub]

Awesome first chapter. Looking forward to the next one.

[TheTaskMaster]

Chapter 2

"Well, I want you to go and get a bottle of icy water from the fridge." Replied Holly "Get the biggest you can find, i'm thirsty!"
I left the room to go down stairs trying to be as slow as possible so I would have to do less. When I opened the fridge I took out a 2 litre bottle of water and took it to my room. I opened the door and saw Holly waiting for me.
"Are you ready for your next task?" She asked
"I guess I have no choice do I"
"Good point, First I want you to take out all your clothes from your wardrobe and put them on your bed. Same with your drawers."
I emptied my drawers first and then my clothes from my wardrobe.
"Good, now I want you to put all of my clothes from my bag where your clothes were"
This wasn't the worst part as I got to see her bra's and panties, she even had a red thong with a matching bra! Once i had finished doing that she told me to put all of my clothes in her bag. It was an even tighter squeeze to fit my clothes in but I just managed it with a bit of manpower.
"What's that over there?" Asked Holly
I looked at the drawers thinking that I dropped something when I felt something freezing cold trickle down the back of my head and my neck. Turning round immediately I saw Holly pouring the bottle of water on my head.
"Bitch" She laughed
"You're the fucking bitch" I replied angrily "Ah fuck that's cold"
"I still have half left! You know where this half is going!" She glanced at my slightly hard crotch "Lets see how small it goes!"
"No please you cant!"
"Too late, you agreed. I'll let you pour it, but if you miss on purpose it won't be fun!"
She handed me the bottle of water and it froze my hands just touching it. I started to pour it slowly and nervously hoping she'd let me go. No chance! I continued pouring it until it seeped out. I felt my dick retract into me like a snail as the water dribbled from my waist band of my stripey boxers to the tip of my dick. I realised it would be better to do it quickly so I tipped the bottle 180 degrees and poured it all in. It started to burn my balls.
"Lucky you, were out of time!" She said to my relief.
"I grabbed the bag to get a fresh pair of shorts and boxers to change into but Holly had put a lock on the zip and was dangling the keys in front of me.

"Bitch!" I screamed clutching my freezing balls
"You can put clothes on, they just have to be the ones in your wardrobe!"
"What, there yours"
"I know, you'd suit them though!"
"No!"
"Ok, you need to win them then!"
"Fine, what do I have to do?"
"You have to strip naked and run into the back garden!"
"No way!"
"You freeze to death then!"
"Fuck, fine"
"Go on then!"
We left my room to got to the kitchen were the back door was. Luckily, there were 3 high hedges blocking the neighbours view so I would have some privacy.
"Wait, you can't look!"
"But how will I know when you have been there and back?"
"I know, Why don't I bring back that tennis ball as proof?" I suggested "You could close your eyes and i'll strip naked and get the ball, when I get back i'll put my clothes back on and give you the ball!"
"How will I know your naked though?"
"I'll give you my clothes"
"Ok one sec!"
She ran upstairs and came down holding something
"Whats that?"
"Your clothes to put on!"
"Ok, You promise not to look!"
"Sure!"
I took of my shirt, then shoes, socks, shorts. I was stood there in my boxers with the hottest girl in the school next to me. I put my fingers in my waist band and then reluctantly removed them putting them in front of Holly.
"Good, now go!"
I opened the door and ran outside. We had a large garden and it took me a good 10 seconds to get there. I retrieved the ball and turned back. I saw Holly, with her phone pointing at me, with my tiny cock trying to become erect, and waving another set of keys in the air. I recognised these ones, they were the back door keys, I quickly ran to the door to find it locked. Holly was just laughing. She stuck her hand out the widow and dropped a smaller bag on the ground. I picked it up and read the note.

Dear Will,
Ha, your dick's so small! Its cute seeing you running around like that, your knob flapping about. Anyway, you need to do 3 things before you can open the bag and retrieve 'your' clothes, otherwise I wont open the door.

1. You must do 10 push ups and 20 sit ups,

2. Scream "I'm naked in my back garden!" 3 times,

3. Wank but don't cum!

Good luck!

The first challenge was easy, I had a lot of experience from trying to impress Holly, and now I was doing it naked! The second task was a lot harder and I was worried. The final task scared me after the 2nd one because I had attracted a lot of attention. I hid myself and started to wank, it took me a while to get hard after the water but I did it in the end and edge successfully.
Forgetting i was naked, and extremely horny, I rushed to the bag and found it completely empty. I heard the door open and rushed inside. Holly had stayed true to her word and gave me new clothes. She put my old ones in the wash.

Just as we got upstairs, my mum pulled in at the drive. I was safe for now!

[Sydney_sub]

Great. Update. I hope Holly has a lot more in store in the next chapter.

[Memories for Life]

Originally Posted by TheTaskMaster

Chapter 2

I retrieved the ball and turned back. I saw Holly, with her phone pointing at me, with my tiny cock trying to become erect...

I suspect that Holly just got some good blackmail pics that will let her control you as long as she wishes!

[deltavoyager]

Please add more, this was getting interesting

[Forestslut]

Loving the story can't wait for the next installment

[scouseslut]

I would happily do this to a guy friend of mine!

Can't wait for the next part to give me done more ideas!

XxX

[cj07]

Great story would love to be the guy

[TheTaskMaster]

He guys, i'm sorry that its been ages since i last posted. i sort of forgot about the story and couldn't be bothered continuing but i will now!

Chapter 3

"I'm home" shouted my mum from the kitchen as she got back from work.
"I'm going out again after dinner to a friends for a bit so i'll be back around midnight" she said
"Ok mum!" I shouted back.
"Perfect" said Holly
"Why?"
"It means that we can do more fun stuff later because we'll be alone"
"Oh great"
"Are you not enjoying it?"
"I guess its kinda fun"
"I wont blackmail you with the video i took to make it fair"
"Can I see the video?"
"Later"
"K"
"The only thing you need to do though is at dinner, i want you to take off your shorts and boxers, give me your boxers and then put your shorts back on"
"What, no. What if my mum sees?"
"It's my choice not to black mail you!"
"Well, your sort of blackmailing me in saying that if i don't do it you'll blackmail me"
"True"
"I guess i have no choice than do I"
"No"
"Fine"
"Holly, Will, i picked up some KFC for dinner because its quick so can you come down?"
"Coming!"
"Don't forget what I said" reminded Holly
We left my bedroom and entered the dining room. i made sure i sat oposite my mum so she had less chance of seeing me.
"How's your day been?" She asked
"Good, we played a couple of games." Replied Holly
"Sounds fun!"
We ate for a few minutes and then i decided to do what Holly had asked. I reached my waist band of my shorts and pulled them don to my ankles. then i did the same with my boxers before stepping out of them both. I lifted my boxers up with my foot and tapped holly on her knee. She grabbed the boxers and placed them in her short shorts pocket before giving me a look of approval. I stepped back into my shorts and lifted them to my knees. Suddenly, my mum dropped her knife on the floor and reached under the table to get it. She bent lower and lower so that her head was under the table. I quickly Pulled on my shorts and hoped she didn't see me. I looked at holly and she waved my boxers in the air whilst my mum wasn't looking.

Dinner finally ended and my mum kissed me goodbye and left for her friends house. Me and holly cleaned away the dishes before heading back to my room. She lead the way. I was only wearing a pair of thin shorts and i was staring at her perfectly round ass. I started to get a hard on and it poked into my shorts making it obvious i had an erection. We got to my room and I sat down on my bed. I placed my hands over my crotch to protect myself.
"It's not like i haven't seen yours before" She said
"How do you know?"
"It's obvious!"
"Is it?"
"Yes, if you show me your erect penis again, ill give you back your boxers!"
"Umm"
"You can also pick our next game!"
"Ok then"
I stood up releasing my hands and gave her a good side on view before putting my hands into my pockets and yanking down my shorts. She giggled and then gave me back my red boxers.
"So, what do you want to play?"
"Lets play TorD"
"Are you sure?"
"In the garden!"
"Ok then"

Sorry if its a bit short but the main thing is it's back!

[Forestslut]

Loved at again looking foward to the next installment

[TheTaskMaster]

Hey guys, i think that you deserve another update so here it is. I was wondering whether you guys would prefer more regular but shorter updates, e.g 2-3 times a week. Or longer once a week updates?

Chapter 4

"Ok then"
We left my room and walked out into the garden.
"Truth or dare?" Asked Holly pulling up a garden chair.
"Truth" I replied
"Who do you have a crush on in our year?"
"Umm, Well, You I guess!"
"Seriously?"
"Yeah, like everybody does!"
"I've been missing out then!"
"True. Truth or dare?"
"Truth!"
"Who do you have a crush on?"
"Jack!"
"You're not serious, him, the ginger one!"
"Ok, its you!"
I blushed.
"Cool?"
"Anyway truth or dare?"
"Dare!"
"Ok, strip completely naked!"
"No, I have a better idea, why don't we have a sort of fight were we wear only our socks and underwear!"
"Whats the fun in that?"
"Well, the aim is to take each others socks off."
"And?"
"Each sock will correspond to an item of underwear. So your right sock will be your bra, and your left will be whatever your wearing underneath. But for me you have to take both socks of to make me take my boxers off!"
"I don't know!"
"Why not?"
"Well, i'm not wearing a bra" She mumbled
"What!"
"I'm not wearing a bra!"
"You haven't been wearing a bra the whole time?"
"No, I guess not."
"Well, neither am I so its fair, we just wear one sock each."
"But you don't have tits do you!"
"True, Just wear your tank top and take that off!"
"OK"
We started to strip to our underwear and got ready to fight. I shouted go and immediately tackled Holly to the floor. She wriggled around as I tried to take of her first sock. It only took me about 10 seconds to take her first sock of but she paused.
"It's not fair, your obviously going to win!"
"True, lets restart and you only have to take one sock off to make me strip."
"Deal, Lets add a rule that the other person strips you if you loose!"
"Sure"
I tried the same tactic as last time but it didn't work. She stepped out of it and I went flying past her. Managing to stay on my feet, I approached her slowly. I tripped her up and took of her right sock.
"Hah, take off your top!"
"Are you forgetting something?"
"Oh yes, I have to do it!"
I stood up and she followed, I found the bottom of her tank top and slid it up slowly, so that I could make the moment last. I got it to the base of her boobs and moved my hands to the front of her top. I continued to lift it but as I did I cupped her warm boobs. I could feel all my blood rushing to my crotch. I wasn't bothered anymore. I pulled Holly's top over her hard nipples and over her head. Her small breasts bounced slightly as I did so. I stared straight at her boobs for a minute before Holly lent forward and hit me in the face with them.
"Second round?"
"OK"
This time she took instant control punching me in the balls below my fully erect dick. I dropped to the ground winded, and she whipped my sock of with ease.
"Ouch" I groaned lying on the floor
"Looks like I win!"
I couldn't be bothered to argue, my balls hurt so much. After several minutes i stood up and Holly yanked my boxers down from the front before I could think. She was face to face with my dick and she...

[TheTaskMaster]

Any replies?
Might post again in the either tonight or on wednesday.

[deltavoyager]

Nice! Keep going! Hoping that the dares get more intense!

[TheTaskMaster]

I give up
I'm sorry but i can't be bothered. I might write a story in the future but i wont post on this section.