On a cool October afternoon in a quiet suburb lived 12-year-old Adam. He was a normal boy who liked games, sports, and outdoor activities. He stepped out of the bathroom with only a towel around his waist. He was getting ready for the night, as it was the only night out of the year focused on kids: October 31, 1998. This Halloween was especially important to him, though, as he was invited to his first party.
Adam's best friend was a rather popular boy. They've known each other long before he was popular, though. While Adam has never managed to get in with that crowd yet, his best friend, Troy, never left him out of the important things. And so, Adam was invited as Troy's plus one. While this could be a great chance to finally get in with the popular kids, unfortunately the party required masks, as everything was meant to be anonymous.
"Finally, you're done." A young voice spoke as the source of said voice pushed past Adam and into the bathroom. It was Adam's little sister, Ruby. She was a 10-year-old girl. She was beautiful for her age and had blonde hair with blue eyes.
"All yours." Adam said and went to his room. Ruby had plans with her friends tonight, or something. Admittedly, Adam didn't care too much. He was too focused on his own night.
Adam closed his door and threw his towel into the hamper. He looked into his mirror and smiled. He wasn't super attractive or anything, but he's been called handsome from time to time. He had light brown hair, blue eyes, and his body was slightly toned from playing games outside all the time, and his penis looked about average for his age.
After checking himself out for a second, Adam pulled out his Halloween costume. He couldn't help but be excited for tonight, especially with the chance of...certain stuff. While that stuff wasn't guaranteed, Troy had hinted that it was possible. Adam got dressed in his best attempt at a greaser costume. He even styled up his hair as well. It was a convincing outfit with black shoes, denim pants, a white t-shirt with a black leather jacket, and, of course, the styled-up hair. It was all completed with sunglasses, though he held onto a sort of masquerade mask just in case.
He left his room and made his way to the front door. He passed by the bathroom and could still hear the shower running. "I'm heading out." He told his mom, who was watching TV, waiting for the doorbell to ring to hand out candy.
"Alright, Adam, be safe." She replied.
Adam slipped out of the house and went to the end of the street where he would meet up with Troy. It only took his friend a few minutes to show up as well. The boy was the same age as Adam and was dressed up as Austin Powers.
"Nice costume, Adam." Troy smiled.
"Thanks, you too." Adam replied.
The two started walking a few blocks up to slightly wealthier streets. The whole way they chatted and checked out other costumes they saw.
"Now, remember, this is THE party of the popular kids. Anyone who is anyone will be there. That includes Courtney and Travis." Troy started. Courtney was the most popular girl in school, and the hottest, and Travis was the boy equivalent to Courtney.
"Right, I know that. We've been over this." Adam nodded.
"I know, but... well, just keep it in mind. And if we're both lucky, neither of us is heading home still virgins." Troy told him.
"Are you really sure that's possible?" Adam asked.
"I know it is. Dean let it slip that apparently last year there were a few, let's just say, fun events." Troy answered.
"Alright, I hope you're right." Adam nodded.
"Oh, and just in case." Troy stopped them and pulled something out of his pocket and handed it to Adam.
Adam looked at his hand and his eyes widened. "Whoa, dude, how did you get these?" He asked, staring at four condoms in his hand, and from the looks of them, they were probably made specifically for boys their age.
"Let's just say being popular gives you some connections." Troy said, answering no further.
The two carried on for another 15 minutes before arriving on the street. The house was in sight, the place that would likely change his life. They made their way up to the house and knocked on the door. A teen girl answered and smiled at them.
"Cool costumes, boys." She complimented.
Before she could grab candy to hand to them, Troy spoke. "Red Velvet. And thanks, by the way."
The teen grinned. "Enjoy the party, boys." She stepped aside and let them in.
The house was very well decorated. Everywhere Adam looked was Halloween-themed. Walking past the foyer, they entered another room, instantly hearing music as they opened the door and stepped in. The lights were dimmed for mood, and people in all sorts of costumes were all dancing or hanging out. In the far corner was a snack table with a punch bowl.
"Alright, Adam. It's time to get this night started. Remember to have fun and take chances. Everyone here knows the rules and knows that certain fun is also allowed." Troy clapped Adam on the back and then disappeared into the dancing crowd, leaving Adam to fend for himself.
'Well, might as well start with some punch and go from there.' Adam thought to himself. The boy made his way over to the table and filled a cup.
"This is quite a party, huh?" A voice spoke to Adam.
He turned to find the source to find a boy dressed as Michael Jordan. "Uh, yeah, it really is. Though I haven't been here long."
"I'm guessing this is your first time here too, huh?" The boy asked.
"Yeah, it is. Any advice for getting things started?" Adam asked.
"Easy, just talk to people. But if you want to jump into some interesting stuff, games are upstairs." The boy answered. "Enjoy the party, bro." The boy raised his cup and then walked off.
Adam looked out at the party. He was a social person, but this was a lot to take in right away. He then gulped down half his punch and instantly felt something weird spread through his body. It warmed him up a bit and dulled his nerves, but the biggest thing it did was turn him on a bit. What was in this punch? Well, it hardly mattered. He drank the rest and joined the dancing.
It started simple enough, dancing to the music while surrounded by others. Where it got interesting was when a girl dressed as a cheerleader noticed him. They started dancing next to each other, and slowly she moved closer and started grinding her butt up against his crotch. Her outfit was clearly just the school cheer uniform, but it was no less attractive.
Adam quickly felt his pants tighten, and he started to grind her back. He didn't pay much attention to her face at first; this is all anonymous anyway, but her flowing blonde hair and what features he could see were beautiful. Was this... no, he wouldn't get that lucky.
When the current song ended, the girl grabbed him and pulled him away from the dance floor. The second she turned to face him, she pulled him into a kiss, and they quickly started to make out. Adam's hands went to her sides before one hand slid up her soft midriff and moved to her budding chest. The girl moaned into his mouth and grabbed his hand. She moved it down and then pushed up for his fingers to dig under her top.
Taking the hint, Adam entered her top and felt his first real boob. It was budding well, smooth and squishy, with a hard little nipple poking back. Soon his other hand slid under as well, and he was massaging her breasts, much to her pleasure.
However, after a couple of minutes, she broke the kiss and pulled back, Adam taking the hint and pulling out of her top.
"Mm, so enthusiastic." She grinned at him. "I'd love to go further, but I think I need some more punch first." She told him before leaning in. "Come find me in an hour. I'll wait to start more fun until you find me." She pulled away and pulled up her top, revealing her bare chest to him. "Don't be late." She winked before fixing her top and heading off.
'Well, that was...interesting.' Adam thought to himself. 'I wonder how far she plans to go.' He thought and patted his pocket with the condoms in it.
Turning toward the crowd again, he looked out for what to do next. He spotted two younger girls drinking punch and gently moving to the music, giggling. One was dressed as a cat, the other as Alex Mack. Adam decided to head toward them. He filled another cup and then went up to them.
"Hey girls, nice costumes." He started.
Both girls smiled at him. "I told you they'd be interested." The cat girl told Alex. The cat girl had short black hair and green eyes; her face was painted up, and she wore a black outfit that was admittedly a little revealing for a girl so young and a black tail. Alex had blonde hair and blue eyes.
"I guess you were right." Alex agreed. "So, what brings you to us?" She asked Adam.
"Easy mingling, maybe some dancing, and if things go well, we could head upstairs to the games." Adam said confidently.
Cat played with her black choker as she smirked at Alex. "What do you say, girl? Want to hang out with this boy?"
"Yeah, I think so." Alex said as she looked Adam up and down.
The group drank their punch and went to the dance floor again, having fun and laughing, spending maybe 10 minutes dancing before heading toward the stairs and sitting on a couch.
"So how'd you get into the party?" Cat asked.
"I was a plus one, admittedly." Adam answered.
"You too?" Alex asked, looking at Adam.
"She was mine." Cat told him.
"Nice, and you two know about that, uh, other stuff that goes on?" Adam asked.
Alex blushed but nodded.
"Know about them? That's the reason I am popular." Cat admitted. "I was too young last year but was brought anyway. Turns out if you give the cool kids enough fun, they make sure you become popular." She smirked.
"And is that your plan?" Adam asked Alex.
"No way." She blushed. "Though I wouldn't say no to trying some stuff." She blushed.
"She's a virgin." Cat said.
"Hey!" Alex looked at her friend.
"I mean, so am I?" Adam admitted.
"Really?" "Really?!" Alex sounded surprised and happy to not be alone; meanwhile, Cat sounded absolutely shocked, as if it were unheard of that a boy like Adam would be a virgin.
"Yeah." He confirmed.
"Well, we found your first boy." Cat nudged Alex.
"Hey." Alex looked at her, but then looked at Adam with a bit of hope in her eyes.
"How about we head upstairs? See the games?" Adam suggested.
"Great idea!" Cat jumped up.
The group made their way up the stair to the second floor, which was just as decorated. There were many rooms, a few with closed doors with 'No Entry' signs. A few other doors had 'Private Room' signs. The rest were open with games going on.
They entered one room and found spin the bottle and decided to join for a bit. It was rather simple at first. Someone would do something funny or embarrassing when the bottle landed on them. But things got more interesting when it landed on Cat, and she was told to spin the bottle to see who she'd spend 7 minutes in the closet with.
A lucky boy was chosen, and they went in. Not much was heard until suddenly the boy moaned. Time ticked down before the host of the game stopped the timer. "Time's up." She went to the closet and flung it open, and a few kids gasped at the sight.
Inside, Cat was on her knees with the boy's penis throbbing in her mouth, pumping his cum into the younger girl while she swallowed. Cat also had her top pulled up, showing off her flat chest. When the boy finished cumming, she pulled off and fixed her costume. "Thanks for the treat." Cat said and returned to her place. The boy hastily put his boyhood away.
The next few rounds were a mix of the normal stuff and sending people into the closet. Then it landed on Adam, and he had to spin for a girl to go into the closet, and of course it landed on Alex.
The two entered and were enclosed in the dark space. "Wh-what should we do?" The girl asked.
"How about we start with kissing?" He suggested.
"Okay." She nodded.
Adam leaned in and kissed her gently, and then she returned it with a more enthusiastic kiss. Before they knew it, they were making out. They also started to feel each other over their clothes. As the lust slowly grew in the closet, time ran out. The two pulled away from each other as they heard the door open up.
"I think I'm done with the game for now." Alex told Cat.
"Alright. I think I know what you want." She turned to Adam. "Come with us."
Their group left the room, and Cat took them to a private room. They entered, and she locked the door. "Please tell me it's time." Cat bounced as she said that to Alex.
"I..." She looked at Adam and then back to Cat. She then nodded.
"Yes!" She cheered.
"Time for what?" Adam asked.
"S. E. X!" Cat answered. She then pulled her top back up, revealing her flat chest once more. Then she dropped her black skirt and panties, leaving her bold slit in the open as well. "Come on, you too, get ready."
Adam was a bit shocked at seeing his first true slit, and when told to get ready for sex, he couldn't refuse. He undid his pants while kicking off his shoes and dropped both his pants and boxers, letting his erect boyhood spring out. While soft, he looked average, but when hard, his penis was a little over average. He noticed both girls looking hungrily at his penis.
When Alex didn't immediately undress, Cat moved over to her and undid Alex's overalls, letting them drop. Alex took control and stepped out of her overalls. While she was still blushing hard, she pulled up her shirt and kept it up with her chin. Her chest was just as flat. Soon came her blue panties, letting Adam see his second, and arguably most beautiful, slit ever.
Adam dug into his discarded pants and pulled out a condom. "Won't need that, dude." Cat told him.
"But—" He started but was cut off.
"No risk for us." She pointed out. "Besides, the first time must be raw. Nothing better than getting flooded with cum by your first boy." She told him. "If you really want to use it, save it for round two or something."
"Um, yeah, sure, okay!" Adam put the condom away, his penis throbbing as he thought about cumming inside Alex.
Cat had Alex sit on the bed, having him be a bit passive as they talked Alex through this. The first thing they did was Alex touching his penis and stroking it. Adam couldn't hold back a moan. Her small hand felt so nice firmly around his shaft. Then Alex was given instruction on how to suck off a penis. Alex gets a few gentle licks before slowly moving her head up and down on his penis. Then Cat took over and sucked Adam a bit, giving him a clear example between amateur and expert sucking.
After the girls alternated a bit, they pulled back to let Adam calm down so he wouldn't cum instantly inside Alex. Once he was ready, Alex climbed into his lap. Cat grabbed his penis and lined it up for Alex, and she sank down on him. She moved slowly at her own pace. She decided to rip off the bandage, though, and pushed down hard to break her hymen. She sank down fully on Adam, letting him enjoy the vice grip of his first-ever slit while she got used to being stretched and recovered from the slight pain.
Adam decided to make out with Alex as well as play with her nipples while she adjusted to sex. When she was ready, she started to slowly raise up and sink back down. Adam's hands went from her chest to her butt to help her move, moaning into her mouth. Their hands had been great; their mouths were amazing. But sex, sex was perfect. He felt like his penis was where it was meant to be, like it was made for Alex.
Alex moaned into his mouth every time she sunk back down onto him. She was clearly loving it just as much as Adam. He could feel all the details of her vice. Velvety walls sliding up and down his shaft, squeezing him to try and get him to cum, and it was definitely working.
As Adam was ready to cum, he couldn't help but grab her hips and push her down on his boyhood just before he started cumming. He felt as his cum pumped up his shaft and then out into her untouched womb, officially claiming his first girl. While he came, Alex started to cum too, squeezing him tighter and milking him for his cum.
As his orgasm died down, he fell back onto the bed, with Alex collapsing on him as well. Soon her slit loosened, and she slowly pulled off of his still hard penis, and he watched as cum leaked out of her and onto the floor. He did that! He deflowered this young beauty and filled her with cum!
"Still hard? Wow." Cat commented as Alex rolled off of Adam and onto her back on the bed. "My turn then!" Cat stated and jumped on the bed on all fours and pointed her butt at him.
Adam watched her and nodded. He quickly got up on his knees, ready for his second slit. He grabbed Cat's hips and pushed fully into her in one go, both moaning out. Adam kept a hold on Cat while he started thrusting fast into her. He knew she wasn't a virgin, so he worked her faster than he would Alex.
Cat gripped the bed and moaned with each thrust as the sound of skin slapping together filled the room. Having just cum, Adam was able to last longer than the first time. He spent that extra time just enjoying Cat's nice slit for longer. And as they grew near to the end, Cat was actually the one to cum first, and her squeezing tunnel was enough to force Adam to cum. He pulled her back firmly against him, and he pumped his second load into her wanting slit.
As he finished cumming, he withdrew his softening penis and sat back while watching cum leak from Cat. The three of them rested there on the bed for a minute before Adam happened to glance at the clock.
"Shit!" He sat up.
"What?" Cat asked.
"I promised to meet a girl soon." He answered.
"Running off to do another girl?" Cat smirked.
"I promised before I met you two." He explained.
"Are you coming back after?" Alex asked.
"Uh, yeah, I'd like to." He nodded.
"Then go. If she's popular, that's your way in; then you can get your first girl in." Cat told him.
Adam hopped out of the bed and pulled his clothes back on. "Promise I'll be back." He told the two girls and left the room.
Adam only had to look for a little bit before he found the cheerleader waiting at the top of the stairs. "Hey, I'm here." He waved and walked up to her.
"Hey." She smirked at him. "Follow me." She led him into a different room; this one was a no-entry. "Welcome to my room." She said and started to strip right away.
"Your room, huh?" He looked around while pulling off his shoes, pants, and boxers once more.
"Yep." The girl was his age; her budding chest he'd seen already, but it was no less good. And her slit. It was shaven to leave a heart. "Are you a virgin?" She asked.
"Uh, not anymore." He answered, growing hard while looking at her.
"Mm, look at you. Maybe I should've jumped you right away." She grinned and got on her knees. She gave him a few really good sucks. "Is that two girls?" She asked.
"How can you tell?" He asked.
"Two distinct tastes." She answered and then stood up and got on her bed and spread her legs. "Get on top."
Adam pulled out a condom and climbed over her. She grabbed his penis and helped him put on his first condom before she lined him up as he pushed into her desired slit. She wasn't as tight as Cat and definitely not as much as Alex, but it felt great. While he got into the motions of thrusting, the girl taught him about a girl's clit and got him rubbing it and sucking her nipple while thrusting, giving her more pleasure. And again, thanks to cumming twice, he was going to last longer. And this time he really needed it, because this girl also lasted longer.
Adam quickly learned all the ways to pleasure her the best. And while he wasn't the biggest penis she's had, it was surely enthusiastic. "Mmm, you've got a good one. Not sure I only want it once." She moaned.
"Thanks. I aim to, mmm, please." Adam replied.
"Make me cum, and I'll show you who I am." She promised.
"Okay." He accepted and continued to pound her hungry sheath. The sounds of sex filled the room as Adam worked her closer and closer to cumming. And thanks to the condom, he felt less sensitive too. Despite him only having had sex twice and her, who knows how many times, he managed to hold out, even bringing her to orgasm before he was anywhere close.
The girl moaned loudly and tightened around him as she came, feeling amazing, a feeling that not all her partners have given her. As she finished, she had him stop moving. "A promise is a promise." She said and pulled off her mask.
Adam's eyes widened, and his penis twitched inside her as he saw who it was. "Courtney?"
"Surprised?" She smirked.
"I, uh, had a suspicion, but didn't think..." He trailed off.
"Didn't think it would really be me?" She giggled and reached up, pulling his sunglasses off. "What a surprise, Adam." Her slit tightened around him a little. "Well, consider yourself among my top 5 partners."
"Thanks, Courtney, that means a lot." He smiled down at her.
"Hm...what the hell, I'm safe." She shrugged. "Take that condom off."
Adam didn't need to be told twice. He pulled out and pulled the condom right off before thrusting back into her and thrusting even faster.
"There you go, Adam, fill me up. It's a reward for making me cum." She told him.
Adam didn't need long. It only took another minute before sinking fully into her and filling his third womb. He was cumming inside the most beautiful girl in school. He stayed fully inside until his penis softened, and then he pulled out and watched his cum leak out of Courtney.
"That was a good one." She idly rubbed her clit. "Say, how many condoms do you have?"
"Just three more." He answered.
"Want to use them?" She grinned. "One for each girl makes three more girls."
"Are you serious? Yeah, of course!" He told her. "But I did promise to get back to the other girls."
"No problem. Just make them quickies." She pulled on her mask. "I'll collect them." She redressed and left the room. Adam put his sunglasses back on and waited.
Soon enough, the first girl entered. "Nice half of a costume, Adam." She said. She was dressed as a nurse.
It went by rather fast. She tripped, showing off her developing body before putting a condom on him with a blowjob. Then she sat down on his penis and started riding him. He used the tricks he learned from Courtney to pleasure her. He did so well that he managed to make her cum twice quickly. Only after the second one did he cum too, filling up a condom for the first time. She pulled off of him, tied up the used condom, and took it with her after dressing.
The next two girls were about the same. One was a witch, the other surprisingly Lara Croft. Condom would go one; he'd do missionary with the witch and doggy with Lara. Then they'd leave satisfied with his condom.
After that, he was free to return to the younger girls. He got dressed and returned to the room.
"Where's Cat?" He asked Alex.
"She got bored and went to find other boys." She answered.
"Oh, alright. And you?" He asked.
"Waiting for you." She answered and spread her legs.
Adam grinned and stripped. He laid her down, moved over her, and started thrusting. After all the girls tonight, Alex was still the best. It truly did feel like her slit was made for him. He took this round slow. He used his new techniques on her while lovingly thrusting into her amazing tunnel. Her cute little moans only encouraged him even more.
In the process of slowly building up to his orgasm, he managed to make her cum four times. On the fourth time, her squeezing slit forced him to cum. He pushed deep and flooded her little womb with its second load of cum. While he was flooding her, Cat arrived back at the door, and once Adam pulled out of Alex, he opened the door for Cat.
"Wow, she looked very satisfied." Cat commented.
"I did my best for her." He nodded.
"Listen, we need to head out, but this was so fun." Cat told him and handed him a piece of paper. "Call me and we'll set up another meeting." She winked and helped Alex get dressed. Soon enough they were leaving.
Adam returned downstairs and got more punch, slightly regretting it as it made him horny again.
He then spotted Troy heading for the stairs, and he rushed over to his friend. "Hey dude."
Troy turned to him and smiled. "There's the stud. I heard you screwed Courtney and her close friends. You must be one of us, bro."
Adam smiled. "Really? That's awesome."
"Sure is. Oh, and I'm likely going to stay the night. So if you need to head home, don't wait on me." Troy told him.
"Oh, alright." He nodded.
With that, he let Troy head upstairs to probably hook up with a girl. Adam decided to head out. He stopped by the snack table and took a goodie bag before leaving and removing his sunglasses. The walk home was silent, but Adam didn't mind. He was too happy with the night. He didn't just lose his virginity; he obliterated it. He took a girl's virginity, came inside three different girls, and had sex with a total of six girls in one night!
Adam was quiet when entering his house, knowing his parents were asleep. He walked to his room but paused at Ruby's room. The door was wide open. He looked in and first saw Violet, Ruby's friend. She was naked except for a black choker. Ruby was only in her panties and a shirt.
"What'll we do if he calls?" Ruby asked.
"Answer it and set up a time for him to pound us again. I didn't give him my number for no reason." Violet answered.
"I know, but..." Ruby stopped as she realized they were being watched. Both Ruby and Violet looked at the door and froze in shock.
"A-Adam?" Both said at the same time.
"You... at the party?" Adam asked hesitantly. He knew the answer, but didn't want to believe it.
"You're... oh my gosh..." Ruby held her head. "I, we...we gave each other...we did...twice." She stuttered out her frantic thoughts.
Violet rushed to the door and yanked Adam into the room before closing the door. "Okay. So you both went to the party. Neither of you knew the other was there. And you accidentally had sex together." Violet stated the facts.
"My brother took my...he filled me...twice..." Ruby muttered.
"Ruby, come on." Violet shook her. "So you and your brother unknowingly took each other's virginities. And he came in you twice. How did you feel at the time?"
Ruby looked into Violet's eyes. "I—I loved it." She admitted.
"Well, there you go." She smiled.
"But it's inces—" She was cut off.
"But you loved it. Now, are you going to beat yourself up over it, or are you going to spread your legs and keep enjoying it?" Violet asked.
There was silence for a few seconds before she answered. "Spread my legs." She decided.
"Good." Violet turned to Adam. "Screw your sister."
Violet helped the siblings strip completely naked and had Adam move over Ruby.
"Ruby, I... I want this." Adam admitted.
"Me too." She nodded.
Violet lined up his penis, and Adam's incestuous penis slowly sunk into his little sister's loving slit. He made love to Ruby on her bed, and when he flooded her with his incestuous cum, it was the first creampie of many between the siblings. For years to cum, they had sex every day, Ruby getting used to her daily filling. Adam and Ruby would never be able to get enough of making love to each other, every time ending with her womb being flooded by her brother's cum.