Olivia sat cross legged on the floor next to her bed. Her best friend Jackie, lay across the bed on her back, her head hanging upside down next to Olivia’s. They had been arguing for the past hour.
“Look, we got cheated, that’s all there is to it. ” Jackie’s voice was full of passion. “With Covid 19 and this damn pandemic bullshit… we got cheated out of our senior year.”
“Well yeah, I feel cheated too… but that doesn’t mean we should break quarantine just for the hell of it.” Olivia said, “besides, nothing would have changed if we had physically gone to school. We would still just graduate and move on.”
“I might have gotten laid…” Jackie said, sticking her lower lip out and pouting.
“It’s not like you’re going to die a virgin…” Olivia giggled, “you’ll get laid in college.”
“That’s easy for you to say, you didn’t ‘glow up’ during the pandemic.” Jackie pushed Olivia over, who was still giggling.
Olivia gasped for air, and untangled her legs so she could sit back up. “Glow up… you’re so cute.” Over the summer Jackie had changed her hair style, and more. She was a bombshell now with her blonde hair cut in a bob. She had gotten her braces out, and was now a force to be reckoned with. Jackie had gone from nerdy and gangly, to super hot over a single summer, and she’d never gotten to strut her stuff.
Olivia had always felt bad, the boys had just ignored Jackie. She was always Olivia’s sidekick, or that girl with Olivia. They had both turned 18 over the summer, and neither of them had gotten to experience any of the perks of being an adult. The pandemic had ruined everything, and here they were in their senior year, still suffering its effects.
Olivia let out a heavy sigh. “Okay… maybe you’re right…”
Jackie squealed in delight. “I could just kiss you!” She rolled over and onto her stomach. She then launched herself at Olivia, showering her with kisses.
“Stop it! You’re fucking up my makeup!” Olivia giggled, struggling to escape.
Olivia and Jackie lived in the same neighborhood their entire lives. They grew up together, and were tight like sisters. Jackie’s parents were strict, but Olivia’s parents were cool. They were old hippies, and very accepting of the girls. The girls spent a lot of time at Olivia’s.
High school graduation was around the corner, and the two of them weren’t alone in their feelings of isolation. Their friends were going stir crazy, and their friend John had hatched a plan for this weekend.
John was adorable, charismatic and outgoing. Both of the girls had been crushing on him as long as they could remember. He also happened to be rich, and his parents traveled a lot. This weekend he had invited a few *********** people to his house for a private celebration. It would literally be the party of the year. Olivia had been invited, but was hesitant to go, and Olivia was Jackie’s ticket in.
“You won’t regret this Olivia!” Jackie exclaimed.
“The things I do for you…” Olivia murmured. She looked at Jackie and smiled, “what are we going to wear?” She watched as Jackie tripped over herself, and laughed at her.
“Let’s look!” Jackie clapped her hands together bouncing up and down.
Olivia loved to shop at thrift stores, it was one of the things she missed the most. She had boxes of vintage clothing everywhere. The closet was overflowing, as were the mobile hanging racks, her parents had gifted her. Olivia was an addict, and her parents were enablers. She often thought her dream job would be to own a vintage clothing shop. Certainly, she had the clothes for it, I doubt I could actually part with any of them though, she thought.
Olivia watched as her best friend began rooting through the closet. She flopped down on her bed exasperated. I really don’t want to go to this party, she thought. Jackie was only worried about getting laid, but Olivia knew that there was likely to be more than just boys. There would probably be alcohol, it was one thing she had avoided like the plague. The idea of not being in absolute control of herself terrified her, but she also wanted to fit in.
I’m not carefree like her, Olivia thought as she watched her best friend strip naked so she could try on a dress. Jackie put it all out there. She would dance and jump around, and enjoy herself. Olivia just couldn’t relax enough to put herself all out there.
“How about this?” Jackie asked, twirling around the pleated skirt billowing around her. Olivia watched as Jackie’s bare ass peaked out beneath the hem.
“It’s adorable, of course…” Olivia got up and went over to her dresser, here try this, she said.
Jackie took the strapless bra from her and pulled down the shoulder straps of the dress. Olivia tried not to stare. Jackie’s breasts were larger than hers, and she always found herself staring like a creep.
Olivia was only 5’3″ and was pretty small, she wore size zero, which translated well for Jackie. On Jackie her clothes still fit, they just looked super slutty on her.
“I wish I was able to just let go like you.” Olivia said with a sigh.
“If you’d of spent half your highschool years as ugly as I was, you wouldn’t give a fuck either.” Jackie said in a patronizing voice.
“Oh stop… you were never ugly-“
“I wasn’t pretty like you.” Jackie said interrupting, she had stopped and was staring at Olivia.
Olivia looked away, “I just feel so uptight all the time. I don’t know if I can dance, because I’ve never tried, I’m just too self conscious.”
“Biiitch… this is what you need then! One last opportunity to get it right before we graduate.” Jackie grabbed Olivia’s hands and swung her around. “Whatever you do tonight, just say YES!”
Olivia laughed, “just say yes?”
“Yessss…” Jackie pulled her in and looked into her eyes. “If someone asks you to dance, you say YES. If someone says let’s fuck! You say?” Jackie paused and waited for Olivia.
“Yes?” Olivia said weakly.
“Yes! You got it bitch!” Jackie kissed her on the forehead, then spun away and began air drumming and singing. Singing, was another thing that Olivia was too self conscious to try. She admired her friends self confidence and managed a weak smile.
“Yes!” She said out loud and began to laugh at Jackie’s antics.
“That’s right! Just say Yes!”
“So what’s the plan?” Olivia asked, concerned how they would pull this off.
“Easy… our parents hate each other, we just tell them that we are spending the night at each other’s house.” Jackie had a smug look on her face.
“That’s good… except that means we have nowhere to spend the night.” Olivia countered.
“You know he’ll let us spend the night.” Jackie said, “hopefully in his bed.”
“Oooh you nasty girl!” Olivia said giggling.
It was settled, and they had a plan. Olivia was starting to feel excited, maybe she’d get laid too. She was past caring about love and compatibility. Olivia didn’t want to go to college as a virgin either.
Olivia hardly slept that night, and found she had little appetite the next day. Every minute of each hour seemed to scrape by. She and Jackie had pulled it off, and their parents believed they would be at one another’s house for the night. It wasn’t much later that Olivia found herself walking down the street.
“Boo!” Jackie said as she jumped out from behind a fence.
“Holy fuck.” Olivia cried out, and held her hands to her chest.
“Why so jumpy?” You’re nervous huh?” Jackie said poking Olivia in the ribs.
“Ouch! Why are you so wound up?” Olivia shot back at her with a scowl.
“YOU KNOW WHY!” Jackie called over her shoulder, “Come on hurry.”
Olivia trailed along feeling overdressed in her 50’s style halter top dress. It billowed out a lot, which she found unnerving. Olivia hoped she didn’t look foolish. Her hair was pulled up in a 50s style bun, matching her dress, and she had tied it off with a ribbon.
They joked around as they made the walk to John’s house, but as his large house became visible, their voices grew hushed. The lights were on and there were no cars in the driveway, and this time it was Jackie who was nervous.
“What if he won’t let me in?” Jackie asked in a nervous whisper, clutching at Olivia.
“Why wouldn’t he?” Olivia asked.
“Cause… he invited you, not me.” Jackie pulled on Olivia to stop.
Olivia pulled back, dragging Jackie behind her. “They know inviting me is inviting you, I never go anywhere without you… Come on!”
A few more steps and Olivia was on the doorstep, ready to ring the bell. Jackie was right on her heels. She always stood close when she was anxious, and Olivia could feel the heat of her as she stood pressed against her.
“Once I ring this bell, there’s no going back” Olivia said in a whisper.
At that moment, the front door opened, and light burst into the gloomy night. John stood on the other side of the door, his face beaming with excitement.
“Come in!” John announced, “I made dinner!” He gestured into the house behind him, and Olivia carefully entered with Jackie in tow. The entryway was enormous. Large black tiles decorated the floor, and sculpted wood formed every edge in the house. A crystal chandelier hung in the entryway and sparkled with hundreds of tiny lights.
Olivia followed John, and she heard Jackie whisper into her ear, “He cooked? HE COOKS?” but she ignored her. Instead, she smiled at John and tried not to gush out nonsensical words.
“So, what’s for dinner then?” Olivia asked, almost having to skip to keep up with John. Where’s the fucking kitchen? This house is HUGE! Olivia thought to herself.
Instead of the kitchen, John led them onto the back patio, where there was an outdoor kitchen. Olivia smelled hamburgers right away, and Jackie pushed past her, nervousness forgotten.
“I’m starving!” Jackie cried out, as she rushed over and helped herself to the food.
“She’s always starving” Olivia said apologetically, John just stared at her grinning.
“Oh” he said, almost jumping in place, “Alyson, and Mike are coming as well.”
“Who else is coming?” Jackie said around a mouthful of chips.
“That’s it, I thought i’d keep it small.” He said as he cocked his head to the side. “I think I hear them now” as if on queue, the doorbell chimed.
He excused himself, and Olivia stared after him. He was wearing jeans that accented his perfect behind. He wore no socks, and obviously worked out. His white tank top hugged a perfectly sculpted upper body. Olivia felt herself tingle at the thought of losing her virginity to that.
“Hey” Jackie said harshly, “If you’re done daydreaming about him naked, we have a major problem.”
“What’s that?” Olivia whispered back. “Why are we whispering?”
“There’s going to be three girls and only two boys” Jackie said, panic showing on her face. “That’s not enough to go around!”
“We can share!” Olivia said jokingly.
“Alright deal.” Jackie said, turning away and going back to her food.
“I was jo-” Olivia had to cut herself off as Alyson opened the sliding glass door and walked out onto the patio. She was tall, almost six foot Olivia guessed. Alyson wore a short dress that contoured every curve of her gorgeous body. She’s got her fuck me dress on, Olivia almost giggled at the thought. Alyson greeted Olivia warmly, and gave her a hug. Olivia felt super short when Alyson bent over to hug her.
“Olivia! It’s been so long since I’ve seen you, oh my god is that Jackie?” Alyson was bubbling with excitement. “Jackie you look fabulous, I love that fucking hair!”
Olivia watched as Jackie blushed, wiping ketchup off her chin. “Thanks” she mumbled around her mouthful of food. She stood there and awkwardly accepted a hug. Olivia swallowed hard as she realized something. FUCK! They hadn’t expected Jackie, John had invited me, that’s why there were more girls than boys.
“Okay” John announced, and everyone turned to look at him. He opened a cabinet on the outside kitchen and took out a bottle of amber liquor. “No getting shit faced drunk, if you drink, you have to stay, no going home drunk.” Everyone readily agreed, and Olivia felt her heart start to speed up. I actually have a shot at getting laid! She thought.
John proceeded to pour a little of the liquid into each glass, and handed it out. Olivia watched as Jackie took the first sip, then she did the same. The vapors from it took her breath away, and she choked on it when she tried to swallow. More of the liquid ran down her chin than her throat. What did run down her throat burned and made her eyes water. It felt good. She looked around and nobody seemed to notice the hole in her lip.
“We should play a drinking game!” Jackie called out, excited as always.
John chuckled “No drinking games, not fun if we get too hammered.”
“Well we should play some kind of game” Mike chimed in.
Alyson punched him in the shoulder, “I’m down for a game.”
They proceeded to argue a bit amongst the five of them, nobody could agree.
“Okay okay…” John said, “I got an idea” he left, and when he returned , he had post-it notes and pens. “Write down a game you want to play , we’ll fold it in half, and draw from a hat”
Everyone eagerly agreed, and did as instructed. John upended a bowl of fruit, and used it, instead of a hat.
“You draw Jackie!” John announced.
Jackie did so, and unfolded the paper. “Truth or Dare” she announced.
“That’s a pretty childish game” Olivia said. She wasn’t very keen on the idea of truth and dare. “Maybe we could pick another.”
“It doesn’t have to be childish” Jackie scowled.
What is she doing? Olivia’s thoughts felt muddy. She tried to stare at Jackie to get her attention, but she was sure Jackie was pointedly ignoring her.
“How so?” Mike asked, everyone stared at Jackie.
“Well…” Jackie blushed a little, but went on. “We could play an adult truth or dare… You know… with more… adult… stuff…”
“Like sexy stuff?” John tittered.
“Yeah!” Jackie said, “Adult topics for truths, and anything goes for dares. ANYTHING GOES” she said emphatically.
“Everyone would have to agree 100% beforehand.” Alyson said, as she pulled her long brown hair back into a bun and tied it up. “Everyone.” she said everyone the second time, and Olivia realised she was staring straight at her.
“Well… Yeah, of course” Olivia stammered, “If everyone agrees.”
“And,” John chimed in, “Everyone has to turn over their phones too.”
“Yeah” Mike said in agreement, “No embarrassing pictures or videos, and no interruptions.”
“What happens if someone lies? Or refuses to do a dare?” Jackie chimed in.
Olivia felt like that was directed at her, so she did the best she could to add something. “If a dare is too fucked up, it needs to be voted on, and all have to agree. If one of the 4 vote it down, then you have to make a new dare.”
“Agreed” everyone said in unison
“If you get caught in a lie, or refuse a dare, then you have to turn over your phone to the group.” Alyson chimed in, looking at Mike, “And provide passwords, so everyone can look at or post under your name.”
“Done!” Jackie announced, everyone else was a little reluctant, but eventually agreed.
Mike was the last to agree, and he seemed really reluctant. Olivia noticed some tension between him and Alyson and wondered what it was about. With everyone in agreement, phones were turned off and placed in the bowl.
“Who goes first then?” John asked, looking around the group, there was a long pause, and then he continued. “I guess i’ll go first!” He looked from face to face, and asked “Olivia, Truth… Or… Dare?” He said each word with emphasis, and Olivia’s heart nearly exploded from her chest. She was scared.
“Truth” she almost squeaked.
“What do you think is the sexiest body part?” He asked, grinning.
Olivia held out her glass, hoping to get some more alcohol, he obliged. She took a sip, and noticed everyone was staring at her. She wanted to say Eyes, cause it was safe, but she didn’t want anyone going through her phone either. She opened her mouth to speak, closed it, and opened it again. “Butt” she said, swallowing hard.
“And it begins!” Mike shouted, his cheeks flushed from drink. “Olivia, your turn!” he added.
Olivia hadn’t thought of any questions, but she knew who she wanted to ask. “John” she announced, “Truth or Dare.”
“Dare” he said, his blue eyes glinting like steel.
“Oh.” she said, trying to think. Olivia could think of nothing, so on a whim she said “I dare you to take your shirt off!” Olivia felt the blood rush to her cheeks, and she quickly looked away.
“My pleasure!” John said, peeling off his tank top.
Olivia deliberately didn’t look, until she heard him say “Jackie, Truth or dare!”
Jackie had her response loaded and ready to fire, “DARE!” she announced.
Everyone laughed, and Olivia looked up, her eyes darting towards John. He was built like a Michelangelo sculpture, narrow at the waist, and perfectly muscled and toned. She felt a tingle between her legs, maybe this was going to be more fun than she had thought. Olivia took a big gulp of her liquor.
“Jackie, I dare you to… Kiss Alyson!” John announced.
“How’d I get dragged into this dare?” Alyson said laughingly. She broke off mid laugh, when Jackie placed a quick peck on her cheek.
“Foul!” John cried, “Foul! You just kissed her cheek!”
Olivia and the rest called out “FAIR!”
Jackie chimed in, “It’s fair, you should be more careful how you word your dares!” she smirked and sat back down, smoothing her dress down around her legs. She looked around, and spotted Mike. “Mike, Truth or dare?”
Mike looked around, and smiled “Truth”
Jackie put her hand to her chin as she thought hard, “What’s your favorite type of porn?” she asked.
Mike, blushed a little, and glanced at Alyson before answering. “I uh… I like…” his shoulders slumped and his face grew super red. “Bi-sexual Porn”
Olivia saw Alyson break out in a smile, so he told the truth. She thought.
Jackie made an O with her mouth, “Mike, you’re bi?”
“It’s not your turn! He answered quickly, and looked around, “Alyson!”
“Truth” she said smugly, “I got nothing to hide!”
“Were you disappointed, when Jackie didn’t give you a full kiss?” he asked.
Olivia guessed that he must have already had the question ready, as the color left Alyson’s face a little.
“I’m not sure now that I like this game.” Alyson pouted, “Yes okay? I was kind of disappointed.”
Olivia sat there stunned, as did the rest of the group. So, Alyson and Mike might be bi? So many questions. Olivia was starting to look forward to her turn to ask.
Alyson looked at each person, then with a grin breaking out on her face, she looked at Mike. “Mike” she said tauntingly.
“Dare” he said smugly.
“Rats!” Alyson said, she looked around, and noticing John shirtless, “I dare you to take off your shirts.”
“Wait can she do that?” Mike asked? “She said Shirts, Plural”
“Yeah she actually worded things correctly.” Jackie said, sticking her tongue out at John.
“Alright, alright.” Mike said, standing up, he unbuttoned his shirt, and then pulled off his undershirt as well.
Olivia couldn’t help but stare, Mike was hairy, and very white, but he was massive and muscled. She would have never guessed, he always wore loose clothing. He had an entirely different allure than John. Olivia knew she was totally soaking her panties. She wanted to squirm and adjust them, but was too embarrassed.
“Okay” Mike said, “Olivia.” He smiled.
“Truth.” Olivia said, smiling shyly.
“Have you ever fantasized about anyone here tonight, when you masturbate?” Mike asked, his voice sounded a little deeper than normal.
Olivia flushed, her cheeks felt like they were burning, and she knew her neck and ears must be bright red as well.
“She has! Look at her!” Alyson blurted out pointing.
“What if… what if… you don’t want to answer a question?” Olivia asked meekly without looking up at Mike.
“Then you have to do a dare I guess?” Mike said unsure, looking around.
Olivia looked up to see people nodding in agreement. “Dare?” She said, making a face and trying to smile.
Mike grinned from ear to ear. “Kiss that person, full on, tongue and everything, french kiss them.”
Olivia groaned, still bright red.
“Well?” Mike said, “what are you waiting for? ” he sounded smug.
Olivia felt tears well up in her eyes, but she fought down the panic. Tonight was a YES! night. So she stood, smoothing the front of her dress down, and walked over to Jackie. She was mortified, and so near tears she couldn’t even look Jackie in the eyes. Instead, she stared hard at the ground. Jackie must have sensed Olivia’s embarrassment. With great showmanship, Jackie leapt to her feet, and grabbed Olivia by the face. Jackie placed her lips on Olivia’s and kissed her.
Olivia began to relax, and taking a shuddering breath, Olivia went for it. She parted her lips and thrust her tongue forward. Jackie’s tongue eagerly met Olivia’s and sparks flew. Electricity seemed to shoot through Olivia, and she found herself clinging to Jackie with desperation. Without even realizing it, Olivia began to grind her crotch into Jackie.
A low peeling whistle brought Olivia back to her senses, and she disengaged. Wiping her mouth, Olivia blushed, the heat of it burning her cheeks. Jackie stood there with a sheepish grin on her face. Olivia went back to her seat and sat down. She kicked off her flats and stared down at her painted toes.
“Ah… Olivia, your turn…” John said.
“Oh yeah” She said, “John”
“Dare, of course.” He said grinning boldly.
“Take off your pants!” Olivia said, This is going to be good, she thought.
“How come us guys are the only one getting naked?!” John protested.
“Cause we’re smarter than you.” Alyson said smiling.
“Okay okay…” John said standing up, “but we should go inside, its getting fucking cold out here with no clothes!”
Everyone agreed, and they all pushed their way inside, following John. Once inside they arranged themselves in the living room. John poured them all another drink, and everyone thanked him.
“I think you’re stalling.” Jackie pointed out boldly.
“Alright alright…” John stood, and as if he were a magician performing a trick. He unbuttoned his jeans letting them drop to the floor. His blue boxers covered little of his muscular thighs. He grinned at Olivia, it was an evil grin, and she grinned back ferociously. Olivia realized in that moment that she was all in.
John made a show of surveying the room. “Olivia… truth… or dare?”
She wasn’t going to fall for this one, smugly she said “truth.” The alcohol had her feeling pretty good, and she was certain he couldn’t find anything embarrassing to ask her.
“What’s the weirdest thing you’ve ever done, while masturbating?” He grinned, delighted with himself.
Olivia stamped her bare foot on the ground, “goddammit John.” She whined. “Ughhh!”
Olivia looked around the group, she knew she couldn’t lie because she and Jackie talked about these things. Jackie would call her bullshit too, she knew it. She felt the blood rushing to her cheeks again, and bit her lower lip in resolve. Jackie grinned at her knowingly.
“I… like to put things… in me.” Olivia said, embarrassed.
“If that’s weird for masturbating then I’m the weirdest person alive!” Alyson howled with laughter.
“She means in her butt ” Jackie informed everyone in a sing-song voice, with obvious enjoyment.
Olivia continued to blush furiously. She was incredibly turned on and could feel how wet she was. She had never told anyone except Jackie, and for some reason talking about such a salacious subject was a huge turn on. Now she needed to get even. Jackie had outed her, and despite Olivia’s arousal she wanted revenge.
Olivia smiled at her best friend with glee. “Jackie… truth or dare?” She knew Jackie would avoid truth and pick dare.
“Dare!” Jackie said. She smirked and stuck out her tongue at Olivia.
“I dare you to take off your dress!” Olivia couldn’t get the words out quick enough.
“For being the shy one, you sure are getting people naked fast!” Mike howled with laughter.
Olivia smiled sweetly at him, and turned her attention back to Jackie.
Jackie stood, and curtseyed. She pulled her arms out from the dresses shoulder straps, and scrunched it down over her breasts. With a shove downward, the dress piled around her ankles. She wore Olivia’s strapless bra, and a pink thong. Jackie’s large breasts spilling out of the bra, which was too small. Olivia eyed her appraisingly, noticing the glow in Jackie’s face. She was fucking loving the attention.
Jackie looked at John and smiled. “Dare?”
He looked around the room, knowing he only had his boxers left. “Truth…” he sighed.
“Are you turned on right now?” Jackie asked smiling sexily.
“Very” John said and blushed.
Jackie jumped up and clapped her hands, and everyone watched her considerable breasts bounce. “Yay” she announced “this is fun!”
“Well we all know where this is going.” John said thoughtfully. “Alyson truth or dare.”
“Dare.” She said her eyes sparkling.
Olivia wasn’t surprised, Alyson was built like a model, she probably wore less clothes to the beach than what she had on under her dress.
“Off with your clothes then!” John said grinning.
“I have to warn you.” Alyson said casually, as she reached behind to undo the buttons. “I’m kinda not wearing any underwear.” With that she let her dress drop around her feet.
Olivia couldn’t help but stare, Alyson was fucking gorgeous. She had every curve in all the right places, she was slender and tall. Her breasts were much smaller than Jackie’s, but they were perfectly round the size of softballs. Her tiny pink nipples were hard and erect. Olivia’s eyes wandered down the tight perfect skin, and rested between Alyson’s legs. She was shaved, and her labia was pink and engorged, like flower petals splayed open between her legs. She fucking sparkled between her legs with moisture.
Olivia wanted to taste her, she wanted to touch her, she wanted to… she looked away quickly when Alyson’s eyes moved to her. Shit she thought, well might as well get it over with, she finished off her drink, and felt a little tipsy
“Olivia… oh Olivia your turn!” Alyson said in song. Even her singing voice was perfect.
“Dare.” Olivia said, she just couldn’t stop blushing tonight.
“Remove thine dress princess!” Alyson said bursting into laughter.
Olivia was glad she wore her underwear. She noticed the guys squirming in their seats, and drew courage from their discomfort. Reaching up, she undid the tie from around the back of her neck. The front of her dress fell away revealing her bralette. Reaching behind she undid the buttons bow her bare back, and let her dress fall to the floor. She stood there, awkwardly and realized that she’d never been this naked in front of a boy before.
John called out. “Holy shit… you’re fucking soaked.”
Olivia gasped and looked down, sure enough her light blue panties were dark blue between her legs. She panicked, and was about to run from the room and hide when Alyson took her by the elbow.
“So?” Alyson said wrapping Olivia in her arms, pushing her naked flesh up against Olivia’s.
“I’m wet too, and you’ve got a boner, we can all see it.” Alyson scolded. “Don’t have to be so rude anyways.”
“Uh… sorry my bad.” John said sullenly as he adjusted to hide his boner.
“You’re turn darlin.” Alyson said to Olivia, winking at her.
“Mike.” Olivia said, pointedly ignoring John.
“Dare” he said smiling widely.
“I dare you to take off all your clothes!” Olivia said beginning to relax again. Mike was staring at her and grinning. She hurried up and sat down, and was glad she hadn’t stuffed her bra like she usually did.
Mike stood up, and dropped his drawers, completely exposing himself. Jackie gasped, and Alyson gave him a thumbs up of approval. Olivia stared, mesmerized. He was a big guy, broad across the shoulders, and taller than six foot. His cock stood out like a flag pole, huge and magnificent. Olivia choked on her spit and began to cough. Alyson came over while giggling and pounded her on the back. Then Mike began to laugh and his gigantic cock sprang up and down with each laugh. It swelled, and spasmed with a life of it’s own. Olivia had trouble catching her breath.
“My turn” Mike said, sitting back down, his cock still standing at attention. He turned to John, “you might as well join us.”
John laughed nervously. “Well not now!” He motioned at Mike’s lap. “I can’t compete with that… anaconda.”
“Don’t be a prude John!” Jackie called out laughing.
John relented, and stood up, letting his boxers fall to the ground. His cock sprang up against his abdomen, it was finely sculpted same as the rest of him. What he lacked in size, he made up for in pure perfection. John and Alyson were a perfect match with their model like physiques. Olivia sighed inwardly, worried about her competition. She watched John tried to wipe his precum off without being noticed, and smiled.
“Alyson” John said, eyeing her appraisingly. “Truth or Dare?”
“I’m going to pick truth, cause I’m scared whats next for dares!” Alyson did sound nervous. Olivia watched as her breasts shook with her nervous laughter.
“Alyson, what’s going on between you and Mike? Are you two fucking?” John asked.
“Oh geez.” She looked over at Mike nervously, and he raised his hands as if to say whatever.
“Uhh… well, it turns out we were fucking the same dude.” Alyson said quietly.
“Wait, tell them everything.” Mike’s voice had a hint of tension in it.
“Well he’s a she… we were both dating a girl, that used to be a guy.” Alyson blushed a little. “I met her at the coffee stand I work at.”
“Wait you got that bikini barista job?” John said. “I can’t believe you didn’t tell me!”
“You didn’t ask!” Alyson shot back.
“Girls” Jackie said laughing, “lets not get into all of that now.”
Alyson smiled, “You’re right, truth or dare?”
Jackie’s face lit up with excitement. “Dare!”
“Jackie I dare you to… strip for us, then remove Olivia’s underwear with only your teeth!”
Olivia sucked in her breath, oh god it’s actually happening. She thought, fighting panic. She tried to sit there and look cool. Part of her was still wondering about Alyson, Mike and a transsexual.
Jackie all but jumped up, she reached behind and un-clipped her bra. Her large breasts popped out physically bouncing from being so restrained. The clip released with such force, her tits sent the bra flying. She grinned ear to ear and cupped her tits, hefting them with pride.
“These girls have been begging to be let free for awhile, that thing was tiny” She said laughing. Olivia could see through the bravado though, Jackie was covering her embarrassment with jokes.
Jackie hooked her thumbs in her thong, and pulled it to her knees, letting it drop the rest of the way. When she stood up, she hesitated a little, and for the first time she appeared a little awkward.
Olivia stole a glance at the boys, they both had their hands on their thighs, inches from their dicks. They stared at Jackie, and Olivia imagined that they were probably drooling.
Jackie walked to Olivia, her big breasts swaying, her nipples looked hard enough to cut glass. Olivia stared, she was so turned on that it fucking hurt. How had she ended up here, she was so fucking embarrassed. She watched as Jackie dropped to her hands and knees thrusting her ass in the air behind her. Her butt swayed in the air behind her like a womanly flag. She crawled to Olivia deliberately teasing her, and the boys. Alyson laughed and whistled.
Olivia sat frozen as Jackie crawled up her legs.
“No hands!” John called out.
“Oh yeah!’ Jackie said. “You gotta stand up Olivia!”
Olivia stood and held her breath in anticipation. Behind her, Jackie’s mouth closed over her bra clasp. Olivia could feel the wet head of Jackie’s mouth. Jackie struggled and snarled between her teeth. She cussed and finally got it loose. The bralette fell away and Olivia stood bare chested in front of everyone. She felt tears roll down her cheeks.
“Are you okay hon, should we stop?” Alyson asked her, concern written all over her face.
“No…” Olivia whispered, “tonight is a yes night, anything goes! Don’t mind me.”
Alyson smiled and sat back down. The boys began hooting and hollering and cheering both Jackie and Olivia on.
Jackie’s teeth dug into her hip, and pulled the strap to her panties down. She had to circle and do the same with the other side. Giving up on that method, Jackie got down on her knees in front of Olivia. She pushed her face between Olivia’s thighs, and bit, none to gently.
Olivia jumped back in surprise, “You bit my cooter!”
Everyone burst out laughing, including Jackie who had a mouthful of Olivia’s panties in her mouth. Jackie refused to let go. She gave a tug, twisting, and pulling got them down to Olivia’s knees, where they fell away on their own. Olivia stepped out of them, looking at Jackie on all fours.
Jackie licked her lips and smiled, “you taste great by the way.”
Olivia couldn’t help but laugh, and wiped her cheeks dry. Now all five of them were naked, and Olivia wondered what could possibly be next.
“Olivia, truth or dare?”
“Dare!” Olivia cried out laughing as she wiped her eyes. She couldn’t wait, god I am so fucking turned on. Her thoughts ran wild and she had to clamp her legs together as she felt a trickle run down her inner thigh. “Oh shit, hold on! First, I need to pee!” She exclaimed.
“That’s it!” Jackie exclaimed, “pee on…-“
“Oh come on, no water sports!” Mike called out laughing, “I vote no.”
“Okay okay…” Jackie said as Olivia got up and darted towards the hallway.
“Second door on the left.” John called out.
When Olivia returned, she returned to absolute silence. “What?” She demanded, holding her hands over her breasts. She had the smallest breasts out of everyone, and felt a little self conscious. I’m tiny and I have tiny titties she thought to herself. She often stuffed her bra, without the added buffer her tits were no larger than apples. She had discovered as well, that she had bigger nipples than the other girls. She thought it made her look awkward naked, but nobody had poked fun at her yet.
“Well…” Jackie said, we discussed your dare while you were gone.” She grinned sheepishly. “I got vetoed a couple of times, but they didn’t veto this one.” She said it gesturing at Alyson who blushed a little. “I dare you…” Jackie said. “To eat out Alyson for a full minute. “
Olivia almost tripped on her way into the room. This is it, fuck fuck fuck. Its finally happening. They had finally crossed the threshold to sex. She and Jackie would finally lose their virginity.
“Okay…” Olivia said fighting her embarrassment, she wanted this. She made her way to Alyson, who sat back a little and let her legs relax. “I… I’ve never done this before…” Olivia said. Her heart was pounding in her chest.
“Just do what you’d like done to you!” Jackie said in encouragement.
“Hold on” the boys said in unison, as they got up, Jackie came with them, and they all stood around Alyson, ready to watch.
“For christs sake” Alyson said, “go sit the fuck back down.”
They stayed, and Olivia laughed feeling nervous. She got down on her knees as Alyson spread her legs for her. She stared between Alyson’s legs as she scooted out towards the edge of the couch. She’s as wet as I am. Olivia thought to herself, she bent down and placed her sweaty hands on Alyson’s thighs. A thrill ran through her entire body, and she squeezed her own thighs together anxiously.
She couldn’t hear if anyone else was talking or not, her own blood was rushing in her ears. Alyson spread her legs eagerly and the scent of her was intoxicating. Olivia lowered her face, all the while greedily taking in the site of her. Alyson’s pink lips were swollen and engorged, she looked wet and sticky, like the nectar on the petal of a flower.
“John, I dare you to… ” Olivia giggled and hiccuped, she continued to hiccup, and so she giggled some more. She was having trouble getting the words out. Olivia stood there naked in front of everyone, she was going to go for it. This was her moment. “I dare you to have ” Olivia’s hiccups interrupted her. “Dammit” she said. “Fuck me! I want you to fuck me.”g. She pushed with her tongue, and it gave, letting her in.
Alyson’s juices flooded Olivia’s mouth. She fought her drool and tried to swallow it all. Olivia was unsuccessful, and she could feel Alyson’s juices running down her chin. She tried to lick at her chin, but she didn’t really care anymore. Olivia was excited now, she only wanted to please Alyson. The excitement Alyson showed mixed with her sounds of pleasure pushed Olivia on. She began to lap at Alyson, penetrating her as far as she could with her tongue. She found Alyson’s hood with her lips, and sucked on it. She probed with her tongue and hit the jackpot. Alyson cried out so loud that Olivia pulled away, scared that she had hurt her.
In response to Olivia’s withdrawal, Alyson wrapped her legs around Olivia’s shoulders and dug her heels into her. Using her bare feet, and her hands she pulled Olivia’s back to her, forcing her mouth back where it had been. Olivia eagerly sucked Alyson’s hood back into her mouth. Near desperation, Alyson pushed her pelvis up and into Olivia.
Olivia teased Alyson’s swollen clit with her tongue. She pushed on Alyson’s little pink love button, and closed her teeth over the hood around it. Alyson cried out, nearly screaming, and this time she began to quake and spasm. She twisted and writhed nearly suffocating Olivia. Olivia felt near orgasm herself, and she lapped at Alyson’s liquid flow like it was honey.
Olivia sat back still kneeling. She watched as Alyson rolled to her side, and pulled her long slender legs up against her chest. She moaned and trembled a little, rocking back and forth. Olivia watched as even the muscles in Alyson’s calves tensed and relaxed.
“I…I” Olivia stumbled over her words. “Sorry” she wiped at her chin “Are you okay?” Olivia took a deep breath “I think that was longer than a minute…” The group began to laugh, and Olivia relaxed a little.
“Ohhh…. ” Alyson moaned, “that was fucking amazing.”
Jackie clapped her hands, and both John and Mike were grinning ear to ear.
“I think both the boys would have rubbed one out if I hadn’t been sitting here to watch. ” Jackie tittered. She went and sat down, and was practically bouncing in her seat. “Your turn!”
“John,” Olivia said quietly.
“Dare” his voice was a rasp, and he had to clear it and say it again “Dare”
“John, I dare you to… ” Olivia giggled and hiccuped, she continued to hiccup, and so she giggled some more. She was having trouble getting the words out. Olivia stood there naked in front of everyone, she was going to go for it. This was her moment. “I dare you to have ” Olivia’s hiccups interrupted her. “Dammit” she said. “Fuck me! I want you to fuck me.”
Olivia sat down next to Alyson, who had finally sat back up. Alyson gently began to rub Olivia’s back, it seemed to help with the hiccups.
John sat with a stupid smile on his face, and Olivia asked “Why are you smiling like that?” She felt panicked, and was worried that she had done something stupid. Oh god, maybe he wanted to fuck Alyson instead. Or Jackie. FUCK! Why didn’t I think of that, fuck me, I’m so stupid. Olivia thought frantically “Did I break the rules?” She squeaked.
John waved his hands, “No No! It’s alright, it’s just… well… I’ve been fantasizing about this since before I can remember.” He blushed furiously.
“Well” Jackie said as she walked over to where Mike was sitting. She crawled into his lap and kissed him on the cheek. “You two love birds going to do it or what?” Jackie giggled and buried her face in Mike’s neck.
“Come here darlin.” Alyson said as she pulled Olivia to the middle of the room. “Show us how it’s done.”
“It’s my first time.” Olivia said. “I don’t think I can show you anything.”
“Mine too.” John offered.
Alyson just smiled, “well lay down John, lets let Olivia run the show.”
John did as Alyson suggested, his dick sticking straight up in the air. He looked super uncomfortable and nervous. Olivia was glad that Alyson, who obviously was way more experienced, had taken charge.
“Mike?” Alyson asked. “This will be fun, come lay down next to John, but the other way.”
Mike did as he was told, he seemed to be happy listening to Alyson as well. He lay down with his head next to John’s feet. For the first time since starting the game, Olivia got to see the two dicks side by side. She was very relieved that she had chosen John. Mike’s cock was much wider, she was sure it wouldn’t have fit. Olivia realized she hadn’t been paying attention.
“This will be fucking hot.” Alyson was saying. “Everybody will be able to see each other.”
Olivia was starting to get the picture, she knelt down on top of John, exalting in the way his cock was trapped between them. Olivia giggled nervously and looked into Johns eyes. He was flushed and blinked nervously as well. She laughed in anticipation.
“Now if you and Olivia sit up straight, you can see each other.” Alyson said triumphantly.
It was true, Olivia saw as she sat up straight, Jackie did as well and they looked each other squarely in the face. They locked eyes for a few seconds, and both of them smiled at the same time. Jackie looked flushed, and breathed hard. Olivia looked between her legs and saw Mike’s massive head and shaft sticking out from under her. Olivia watched as Jackie lifted and laid forward. Alyson jumped in grabbed Mikes cock and put it into position for Jackie,
Olivia forgot about Jackie for the moment, and Alyson helped her to do the same. It turned her on having Alyson’s hands all over her naked body. Olivia instantly forgot about Alyson when John’s cock pushed firmly against her opening. She looked at John’s and realized he was staring at her. She tried to look between her legs, and accidentally pushed down further.
Olivia yelped out loud as the head of John’s cock penetrated her. It was much wider than she had expected. She slowly worked it inside of her, until she was fully seated. It hurt, bad, she felt like she was being split in two. She heard Jackie cry out, and stole a glance. Jackie was laying on Mike, trembling.
Olivia leaned forward, and felt the length of John slide from within her, it felt amazing. She could feel herself stretched around him, and close behind him as he exited. She pushed back down and John moaned. Olivia looked into his eyes, and he looked into hers. She smiled, and kissed him, while arching her back. Their tongues met, and he eagerly explored her mouth. Olivia realized it wasn’t the same. He didn’t kiss like Jackie. She found herself wanting a real kiss, and sat straight up.
Jackie was riding Mike like a bull. She had gotten off her knees, and was crouching on top of him. Olivia found her eyes drawn like the needle of a compass, and stared between Jackie’s legs. Mike was massive, and stretched from thigh to thigh, Olivia felt her pulse skyrocket. She rode John faster, rocking forward and back, forgetting about John entirely.
Olivia imagined Jackie must feel like her best friend was fisting her. Mike’s dick was at least as big around as Olivia’s wrist, if not bigger. Jackie took it like a rodeo star. She traveled up and down, her hands behind her on his bent knees. Olivia watched the full length of him part her pussy lips, stretching her to the max. I’m going to fucking cum, she realized. John was pounding in and out of her, her clit rubbing against his abdomen. She ground into him over and over pushing him as deep as she could. She leaned over and Jackie leaned down to kiss her. When their lips met, Olivia saw stars.
It was an orgasm that rivaled any she had ever had before. It shook her entire body to its core. Olivia screamed, and jerked away from John. His violating manhood ripped from between her legs, and she curled into a ball. Alyson and Jackie were on her in an instant, touching and soothing her. Olivia convulsed her muscles feeling like jelly.
“Whoa…” She rasped hoarsely. “That was fucking intense.”
“I’d say so…” Jackie cooed softly. “Can you sit up?”
Olivia did sit up, and found herself grinning. This had been the best night ever. She felt something unusual between her legs. When she put her hand down there, she found Johns cum leaking out of her.
Olivia looked over at John, he still lay there his chest heaving. She giggled at his steadily shrinking manhood. He had enjoyed himself as well.
The rest of the evening went well after the game, none of them bothered to put on clothes. It felt like they had all become bonded, and when the weight of sleep pressed down on all of them. Olivia found herself curled up with Jackie and Alyson. They slept that way, their legs and arms entangled. Olivia had never been happier. She found herself dreaming about the future. She hoped there was more in store for the five of them.