Truth or Dare - Anna

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Truth or Dare - Anna

Anna’s childhood wasn’t the best, she was an only child and her dad left her mom before she could remember him. They got a new house far away and soon her mom met some guy from work and started going out with him. Before she new it she had a stepbrother. Where as Anna was a short blonde, Jesse was tall with dark hair and seemed really quiet all the time. Tonight, though he was not. Jesse was having a sleepover down in the basement with his friends and Anna could not fall asleep with all the noise they were making. She couldn’t quite hear what they were doing downstairs but it had to be some sort of dumb buy stuff.

Since she was bored, she figured she might as well go down and spy on them to see what they were up too, so she headed downstairs. Once she got downstairs she quietly poked the door open to see what they were up too. Spin the bottle, of course if there was any game dumb enough for them to be playing that was it.

It was Jesse’s turn to spin the old glass bottle. It spun round and round and the top pointed at James or Jimmy as they called him. He was the pitcher for the baseball team and had some very nice arms and probably abs too if she could ever get to look underneath that shirt. The backend pointed at Tim the goalie for the soccer team, he was a tall lanky boy with short cut spiky straight hair.

“Ugh” Tim said “I hate sitting across from you”

“Yah we need and odd number of people for this to work” said Mike the fourth boy



“Ok turn around unless you’re going to quit” said Jesse. So, Tim turned around with not much but a grumble. Jimmy wounded up his arm and slapped Tim in the ass hard making a loud smack. Anna was not prepared for this and let out a squeak. Instantly the four boys turned their heads up to see where the sound game from.

“Hey Anna is that you spying on us” said Jesse “If your gonna watch you have to play too we need a fifth player.” Said Mike

“What no I’m not playing that stupid game” she shot back I don’t want to get slapped. “I dare you to” said James “Unless your scared” “No I’m not she shot back”

“Hey Anna” asked Tim “What if we played truth or dare instead” She thought about that for a second and replied “Ok I guess so, but no daring me to get slapped”

She walked down stairs to join them and sat down between Mike and Tim.

“Ok so here are some base rules” said Tim “We are gonna go clockwise around in the circle and whoever’s turn it is spins the bottle. Whoever it points at gives the truth or dare, if it points at who ever spins the bottle then respin. If you think the dare or truth is too much just say so and the other three will vote. If you can’t do your challenge then your out and last person remaining wins. Also one more, if you give the truth or dare it can’t include you.

He then spun the bottle. It twirled around and pointed at Mike. “Awesome I go first” Mike said So he spun the bottle and it pointed at Jesse

“Truth or dare”. “Dare” he said “I dare you to get slapped by Jimmy”

“Noo, come on really” Mike said “That’s no fair. Fine whatever” He turned around and Jimmy slapped his ass. Not as hard as before, but still hard enough to make her jump watching it.

Now it was Anna’s turn, so she spun the bottle and it pointed at Mike. She was not about to get slapped, she knew what they were up to so she choose truth. Mike asked “Is it true you like Tim”



“What no” she said then quickly glancing at him she said “oh he’s a nice guy I think he’s a nice person.”

“Thanks” said Tim with a frown reaching for the bottle. He gave it a gentle spin and it barely made a full rotation landing back on Mike again “What will it be timbo?” he asked. “I take a dare”

Mike’s face lit up “I dare you to kiss Anna”

“No way dude” said Jimmy “You killed him man.” Before she even was ready to make a protest Tim gave her a quick peck on the cheek.

She just sat there thinking if it was really true did Tim like her. He was a bit off an awkward kid, but nice. She was still trying to figure out what to do about it when it got back around to her. Mike nudged her to spin the bottle knocking her out of her day dream.

She spun the bottle and it landed on Jesse. This time to avoid any more embarrassment she choose dare. “I dare you to let Mike touch your boob”

“What no way” she said “I am not doing that”

“Oh come on they piped in we’ve all touched a boob before it’s no big deal are you really gonna quit from this.”

No she didn’t want to quit first no way that was happening, so she said “Ok” Mike reached over and squeezed her right boob in his hand and said “Wow nice boob” She stuck out her tongue back at him.

Tim and Jesse were just as dumb as you would expect but on Jimmy’s turn it landed on her and he picked dare. This was the perfect time to get what she had been waiting for “I dare you to take off your shirt”

“Haha he said wow that is so easy I was expecting something harder.” Mike went and it landed on Tim and then when she spun the bottle it landed on Jimmy.

She choose dare and as soon as she said it his eyes lit up and she knew she had made a mistake. “I dare you to take off your shirt” She was gonna say no but it seemed like he really wanted to see her body. Since she was wearing a bra still on top of her sweatpants it wasn’t like they were seeing anything more than when they were in the swimming pool. She took off her top and tossed it aside letting them she her nice comfy red bra.

The other boys went around on their turns and Tim dared Jesse to go sit in the corner and she got to dare Mike to lick the floor. When it got back to her turn again, she spun and it landed on Mike and she choose dare He said “I dare you to flash us”

“What no” she said “that’s not fair” Tim spoke up and said “Hey Mike guess what the dare can’t apply to yourself.” Just to spite Mike she decided to go along with it. They made him turn around and as soon as he had turned around she quickly pulled down her bra exposing her round tits and then back up again so that Tim and Jimmy didn’t get much of a chance to look.

On the next turns both Mike and Jesse got to come sit back in the circle. She had her shirt off for a while and said that she was starting to get cold. James said “Oh come on I’m not cold yet and I’ve had my shirt off too” She responded with “Well that’s cause your hot” They all looked at her and she put her hand over her mouth and said “I’m sorry” Jimmy asked “What are you sorry for” She said “Idk I thought I offended you”.

On her next turn it landed on Jesse and when she choose dare he said “I dare you to go put on your volleyball uniform. “Oh thank you, Now I can go put on something warm.” She quickly ran upstairs and tried to do so quietly so as not to wake their parents. When she got to her room she took off her sweatpants and panties and put on a pair of black spandex. Then she took off her bra and put on a nice Calvin Klein sports bra and her uniform top. Then she hurried back downstairs.

When she got down there, they said it was her turn. She went to reach for the bottle but they said hey we dared you to take your shirt off you can’t put it back on again. She protested saying that this was part of her uniform. They out voted her saying that the early dare still stands. She just decided to go along with it and said whatever taking her shirt off again and tossing it next to the other one.

She spun the bottle and it pointed to Jimmy, he asked her what she wanted so she choose a dare. He dared her to lay on the floor in the middle of them. She wasn’t sure why so she asked “What is the point of this?” Jim said “Idk I couldn’t think of anything else you would do that you wouldn’t complain about.”

“What” She said, “I’m not a wimp watch me I can do anything”

Tim then grabbed the bottle and spun it pointing at Jesse who thought about his dare for a second before saying “I dare you to give Anna a massage but only where she isn’t covered by clothes” So to prove Jimmy wrong she said ok and rolled over. Tim came over and straddling her body and started by running his fingers firmly down her spine.

“Relax” he said softly.

Moving his soft hands up to her shoulders he admired her profile, her eyes closed and face relaxed. His fingers roil and push her shoulder blades seeking out any tightness and pushing it to the side. He follows the tightness, pushing it until it dissipates just above her breasts. His fingers now alternately softly between stroking and pressing her body firmly. Following her contours his fingers move back down to the base of her spine and touch the top of her spandex. She was starting to get a little aroused feeling him this close to her.

His fingertips gently move up and down, tracing from her neck down before sweeping around to stroke the small of her back between her hips and stomach again and again.

“Okay there Tim don’t get too carried away” Said Jesse. Tim then stopped and got off her.

“Wow you are surprisingly good at that.” Anna said “Where did you learn that.”

“Oh I just picked it up here and there.” he replied.

Jesse spun the bottle next and It pointed at where Anna was sitting. He choose dare and she said I dare you to give Tim the same message he just gave me.

“Really come on that’s so dumb what am I supposed to do rub his feet since he has pants and a shirt on.”

Tim spoke up and said “Well you better get started you don’t want to lose to your sis.

While Jesse was messaging Tim, Anna was just laying on the floor the whole time and since she was just wearing her spandex and a short jersey she was getting cold. When she looked down she could see her nipples getting hard and poking out through her shirt. She wondered if any of the other boys noticed.

She wasn’t long into her thought and ended up missing the other two boys turns so it was quickly hers again. She spun the bottle and it pointed at Mike like everyone before she picked dare.



“I dare you to put something down your pants” Mike said

“Oh come on man you can’t go crazy” Jimmy exclaimed

“No, its fine” she said “I know he wants me to stick a carrot or something in my pants but I got a one up on him because he didn’t say how” She rolled over to face Mike giving him a quick wink and then stuck her hand down the back of her spandex gilding her hand over her right butt cheek and pulled it out just as quickly.

“What that’s no fair” Mike said “Haha she laughed back at him, too bad.”

Time grabbed the bottle and spun it pointing at Mike again.

“Haha” he said smiling at her, your dead “Tim I dare you to put your hand down Anna’s pants”

“What no” She said looking at the others. They all shook their heads and said “I dunno seems fair to me, guess your just gonna have to quit.”

“No way you know I’m winning this. Ok Tim” she said “No funny business” then she sat up and turned around facing away from him. “You better do this quick”

Tim reached forward sticking his hand down her pants none to quickly. Barely had his wrist made it to her waist line before the tips of his fingers grazed across her butthole. She almost trembled from the feeling. Knowing that if she was to stick her fingers in herself right now they would come out soaking wet. Tim was quick as promised pulling his hand out of her pants almost immediately after.

Jesse was up next and before he spun the bottle he asked “Hey are you guys hungry wanna grab a quick bite to eat before continuing”

“Yes please they almost all said together. I am down for Pizza”

They all headed up stairs together. Once in the kitchen Jesse went over to the fridge and grabbed some of the pizza that was left over from the party earlier. Jimmy of course went straight over to the liquor cabinet and grabbed some tequila out. Mike claimed he had to go to the bathroom and ran off down the hall while Tim just stood there with her. Jimmy came back over with some shot glasses and started to pour a few. Jesse said “Awesome idea I love a round or two.

Meanwhile upstairs Mike was looking for his lean. He knew he had put it somewhere, and had planned to drink it with the guys later but Anna was just being to innocent for his liking and decided that she would love some.

Once he got back downstairs Jim had poured a round for everyone and even had some salt but no limes.

“Cheers” he said to a fun night. Everyone downed their shots. “Egh” was what came out. “That does not taste good without a lime.

“Ok” Said Mike let’s get something better. He reached into the cabinet and grabbed the whiskey.

Jesse shouted out “Hey guys pizza is ready” While everyone was getting their pizza he carefully made sure to pour Anna a drink of all lean. He also poured a chaser of straight vodka just in case someone needed it. He then passed out the shots to everyone.

“Cheers” he said to a fun night. Everyone downed their shots. “Egh” was what came out of Anna’s mouth instantly. “That tastes terrible.” She reached out for the chased and took a swig. Almost gagging when she swallowed. Her eyes widened and she ran over to the sink taking a big swig from under the faucet.

“No more drinks for me, that was terrible.” She said coming back over to join the others finishing their pizza. There were a few jokes made but otherwise they all finished their pizzas quick enough.

When everyone was done they grabbed the plates and shot glasses and when over to the sink to wash everything out. Jesse said “Make sure you clean all this out we don’t want my parents knowing. With all the dishes cleaned up they headed back downstairs.

When Anna went down the stairs, she was could feel the drinks already. It felt like she was floating already and the warm feeling inside told her she was going to crush this truth or dare game. Mike was right behind her going down the stairs and he could see that Anna was feeling the alcohol as well as the drugs he slipped her already. He figured if he could get a few more shots into her she might not even remember the night which is exactly what he was hoping for. James came down next he could tell Anna lusted for him and was sure by the end of the night she would somehow be on his dick since she had no love for any of the others. Tim came down next and like the other two he was focused on Anna because he knew that while she may not like him in her state with his persuasion this would be his best shot at getting in her pants, and hopefully this time from the front. Lastly, was Jesse he knew the four in front of him were all idiots and somehow, he was going to have to help someone get through the night.

End of part 1. This was just the world builder trust me the next part is worth it.

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