This is the first chapter of a multi-part story that will detail the pansexual adventures of cute young couple Tommy and Karlee. This chapter involves m/f and m/m. As playful Karlee leads her suggestive boyfriend down the rabbit hole of bi-bottoming fun, there will be a lot of raucous sex to be had by all. If this isn’t your cup of tea, please move on. If it is, please enjoy and leave your comments! This is my first publication on Literotica. I hope you like it!

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“I’d like you to be more adventurous,” Karlee told Tommy one night, after a hurried sexual encounter in her bedroom. She lay on her back, her pert breasts triumphantly pointing at the ceiling. He lay on his stomach next to her in her bed.

“What?”

“Like, more adventurous. I wanna try new things. And I want you to try new things.”

Tommy hadn’t seen anything particularly wrong with the way they had been doing things. In fact, he’d been quite pleased with his relationship with Karlee. From time to time, one of them had been able to sneak over to the other’s place when a roommate had been scheduled to be out. Like the horny college kids that they were, they’d tear each other’s clothes off and get to rutting like farm animals. With their class itineraries and respective work schedules, it was hard to find time, but they made up for frequency with intensity.

Tommy loved Karlee’s bright girlish smile, her long brown hair, and her large perky breasts. As far as he’d been able to tell, she’d always enjoyed their sex. She loved it when he took her from behind, especially, or when he’d pin her legs up over her shoulders and slam her into the mattress from above.

“I thought you liked what we were doing,” Tommy said sheepishly.

“I do,” assured Karlee. “I like you. You’re a great boyfriend.”

“Really?” Tommy wasn’t so sure right now.

“Of course. I like how kind you are, and how much you want to make me happy. I like your eyes. I like your nice big dick. I like that bubble butt of yours.” She playfully spanked him.

“Okay. But it’s not enough?”

“It’s not that you’re not enough, Tommy. I just… I want us to be more adventurous. Play a little more. We always do the same thing.”

Tommy frowned. “I thought it was a good thing. Sorry.”

“It’s a great thing. It really is. You make me cum. You make me happy. I’m just interested in, ya know, branching out a bit. Trying new things.”

Tommy propped himself up on his forearms. “You mean, like, other people?”

“No, no. Well, I mean maybe. I’m not breaking up with you. This isn’t a ‘we should see other people’ thing.”

“Okay.” That made him feel a little better.

“We’re young, and I kinda wanna experiment with stuff.”

“You mean, like, positions?”

“That could be part of it.”

He thought. “You mean, like, toys, then?”

She giggled. “I have toys, silly.” She reached over to her nightstand and opened the top drawer. She pulled out a pair of dildos. One was a small and thin recreation of a penis. Smaller than him, he thought with relief. The other was long and thick, but straight and smooth, with a flared tip and a black knob at the other end.

“Oh!” said Tommy. “I… didn’t know you had those.”

“When you’re working late or I’m working late, and I’ve got a few minutes when my roommate’s in the shower or at class… well, a girl’s got needs.”

“Um. Okay.”

Karlee looked at her toys and got a mischievous grin. She leaned in to Tommy and kissed him on the mouth. Then she kissed him again. “You know I really like you, right?”

“Uh, yeah.” He was just pleased to be the object of her affection and liked her kisses.

“Are you okay with what I’m asking?”

“You mean, to be more adventurous?”

“Uh-huh.” Her eyes sparkled.

“Yeah. I mean, sure. I want you to be happy.”

She nodded with intent. “I want you to be happy, too, Tommy.”

“Thanks.”

“I’ve been doing a little bit of research. I’ve found a few things I wanna try with you. They really turn me on.”

That sounded good to Tommy. He couldn’t conceive of a down-side to Karlee’s being really turned on.

“It’s gonna take a bit of openmindedness, but I’m really excited to make you happy, Tommy.”

Tommy felt like there was a bit of a trap being laid for him, but everything sounded good so far. “Happy sounds, uh, good.”

“Good,” confirmed Karlee. “Happy is good. And feeling good will make us happy. Agreed?” She seemed intent to lead him on. He could find no fault in her logic, though, so he nodded.

“I wanna try something right now. Just a little thing. Something adventurous. Do you trust me?”

He squinted at her with suspicion. She just batted her eyes and squeezed her ample tits together. That won him over.

“I guess. Sure.”

She giggled in glee, popped up onto her knees, and clapped her hands. “Okay. Just… trust me, okay?”

“Uh, okay?” The fact that she had to keep asking for his trust made him more wary. His worry, though, started to wane when she straddled his thighs and he could feel her pussy hair rubbing Escort against his butt.

Karlee giggled and propped herself up, hands on his shoulder blades. Her lithe young hips ground forward and backward. pulling her pretty pink pussy up his buttocks and back down his thighs.

He found this a bit strange. He was usually turned over when she rode him this way, but it wasn’t unpleasant.

She spread her legs wide and slowly rubbed herself up and down, up and down over his mounds.

“Mmmm. This is so hot,” she murmured.

Tommy liked that she liked it. His penis started to chub again because of her excitement.

Karlee’s hands moved down his muscular back, her thumbs digging deeply into him as she pulled down toward his waist. She lifted her hands again to his shoulder blades and descended again, this time with her fingernails, slowly tracing them down to the small of his back.

“You’ve got such a great ass, baby,” said Karlee. Her fingers started to massage the small of his back and the upward slope as it rose into his substantial glutes.

Her fingers felt nice on his cheeks. Her pussy felt nice, too, as her outer lips rubbed back and forth in the furrow between his cheeks.

Karlee slid her crotch back down his upper thighs. She pulled one knee up and inserted it between his. Pushing back out, she opened his leg outward. Then she did the same with her other knee, until she was perched between his spread legs. Her hands now roamed openly over his ass-cheeks, squeezing, scratching, tracing shapes, and molding them as though she were kneading bread.

“This feels strange,” Tommy said, face down on the bed.

“But it’s new, right?” grinned Karlee. “And does it feel good?” She let her thumbs dip between his spread legs over his perineum and massage just above his scrotum.

Now that felt good. “Ooooooh,” Tommy couldn’t help but groaning.

“Mmmm.” Karlee hummed her approval. Her thumbs traced deep circles in the space under his scrotum. Tommy had never been touched here before. It felt really good, but kinda strange. He was used to what he considered the standard “right” way to have sex: boy inserts penis in girl, makes girl cum, then boy cums where she lets him. It had worked for him, he’d thought. That his pretty brown-haired girlfriend wanted to do this with him had never entered his imagination.

Karlee leaned down and planted a kiss on his right ass cheek.

“Are you… are you literally kissing my ass right now?” Tommy asked.

“Mm-hmmm.” Karlee seductively placed a kiss on his other cheek too, her thumbs still working over his perineum.

“it just… it feels so strange,” Tommy panted into the pillow.

“Strange bad?” She kissed his cheek again, lower and closer to his sweet anus. “Or strange goooood?” She moved to the other cheek, again even closer to his rosebud.

“Oh my god,” he panted.

Her thumbs rubbed out the bottom of his scrotum and teased the skin pulled tight over his large testicles.

“I’m gonna take that as a ‘good,'” giggled Karlee.

With the other four fingers of each hand, she dug up under his abdomen until she had hooked around his penis. She pulled it down and outward so that, definitely erect, it was no longer pinned between his lower belly and the sheets, but stuck out the back, between his legs.

“Mmmm. There’s my friend,” she said. She moved herself even lower, lining up her face to his penis and, extending her tongue, took a long loving swipe up its length to his balls.

“Oh my GOD,” moaned Tommy.

Karlee’s fingers now massaged his inner ass cheeks: pressing, squeezing, pulling, drawing deep lines parallel to, and then in toward, his opening. Her mouth lavished kisses along the lower length of his penis and then took his balls into her mouth one at a time.

“Mmmmmmm,” she moaned. “I love your cock. I love your balls. I love your ass, baby.”

“Oh fuck,” whimpered Tommy. She was working him over in ways he’d never even imagined. The only thing his mind could register beside the pleasure was an almost instinctive spreading of his legs even further. He didn’t know what these sensations were, but his body was absolutely reacting to them.

Her tongue bathed every inch of his ballsack and then moved upward. Her hands now took a firm grip on either of his impressive buttcheeks and pulled them apart. There it was.

Her tongue snaked its way up, up, and then made contact with his puckered rosebud.

“OH FUCK!” Tommy shouted. His hands clutched the sheets under him. His muscles contracted and his knees pushed down into the mattress, trying to elevate his butt into his girlfriend’s mouth.

Karlee swiped long and slowly over his hole. Then did it again. “Mmmmm, I knew you’d taste fantastic,” she cooed.

“Oh my GAWD!” groaned Tommy into the pillow as Karlee inserted her tongue into his anus. The pretty brunette giggled and cooed as she felt him shudder and heard him moan beneath her.

“Fuck, what an ass you have, Tommy.” Slurping and kissing, licking and probing, the girl spent the next several Bayan Escort minutes eating out her shocked and submissive boyfriend.

“I had no… no idea….” he gasped.

“Mm-hmmmmm,” she groaned into his opening.

“Oh my gawd,” he whimpered again. Karlee pushed Tommy’s knees further up and apart. Then her hands found his balls and cock protruding lewdly along the sheets beneath her.

“Mmmmm. You’re so sexy, Tommy,” she muttered into his spit-slicked butthole.

“Oh my gawd,” he whimpered again. The feel of her eating his ass out was indescribable: new, scary, amazing, and absolutely overriding any other feeling or choice. Whatever he might have wanted to do, he couldn’t help letting her have her way with him.

“Oh fuck. Oh fuck. Oh fuck,” he almost chanted.

“Mmmm. Mmmmm.” Karlee chewed on Tommy’s anus voraciously. Quickly swiping her tongue over her palm before diving back into his ass, her hand closed around his erect penis and jerked him off while she tongue-fucked him.

“Oh my god!” Tommy moaned.

“Pull your cheeks apart for me,” Karlee’s muffled voice spoke into his bunghole.

Tommy reached back and filled his hands with his round cheeks. He’d never done anything like this, part of his brain insisted. It felt too damn good, the rest of his brain screamed at him.

He inched up on his knees and popped his butt up as best he could. This gave Karlee fantastic access to his protruding posterior, and also let her tug up on down with greatest facility on his hard cock.

“Oh, Karlee….” he moaned.

“Uh-huh?” she smiled into his ass.

“Oh my god, keep stroking me.”

“You gonna cum for me, baby?”

His thighs started to tremble. She smiled.

“Oooh, baby. Cum all over my bed while I eat your ass.”

“Ooooh, Karlee. It feels so… so….”

Her hand whipped up and down his now twitching penis. “Do it, baby.” She rutted into his sweet hole with insatiable gusto.

“Oh my god, Karleeeeeee.”

“Yes! Cum for me, baby!”

“Oh my god, Karlee. I’m gonna… I’m gonna….” His voice rose in pitch and volume.

“Cum for me, baby!”

“Aaah! Aaaah!! Aaaaaaah!”

Her hand was a blur on his cock as it began to convulse and spasm.

“OHMYGOD, I’M CUMMMIINNNG!!!” Tommy screamed into the pillow. Ass lewdly in the air, his whole body convulsed as his cock spasmed down into Karlee’s hand and spewed rope after rope of hot white jizz onto her bedspread. Karlee kept licking his ass as he cried and came, and came and cried.

Finally, the boy let out a throat-scratching groan and collapsed into the puddle of his own semen.

Karlee sat back on her naked haunches and licked her cum-covered palm.

“Mmmmm, Tommy, you taste so good.”

“Aacck,” was all Tommy could muster.

A devious smile crossed Karlee’s face. She took a big swipe of cum onto her tongue and then leaned over her spent boyfriend and kissed him deeply. Shoving her tongue in his mouth, she pushed as much of his semen into his mouth as she could.

“Gggggh.” Tommy acquiesced to his girlfriend’s fervent kiss at first. Once he realized what she had pushed into his mouth, though, his eyes flew open and he tried to pull his head back.

Karlee grabbed the back of his head and held him in place. She cooed contentedly, letting him know that this turned her on. It couldn’t be so wrong, his brain told him, if it turned on his smoking-hot girlfriend. Gradually, he stopped fighting her. She swirled her tongue around his and hummed her pleasure into his mouth.

He registered the tangy saltiness of his own jizz. It wasn’t bad. It was different, though. And Karlee definitely liked the taste of it, so it couldn’t be so gross. She was mind-numbingly gorgeous to him, so what she liked had to be good, right?

As she made out with her boyfriend, and shared his delicious cum with him, her hand came off the back of his head and groped its way down to his upturned butt cheeks again. She kissed him ferociously and traced her finger over his wet asshole.

“See? Adventurous can be good.” She smiled and kissed him a few more times on the lips.

“Uh-huh,” he panted, nearly incoherent in his post-orgasmic stupor.

“Adventurous can be very good.” She slipped the tip of her finger just inside the outer ring of his bunghole.

“Oooooooooooooh!” Tommy’s brow crinkled in a mix of pleasure and discomfort.

A voice behind them, husky and feminine, broke the mood. “That is so fucking hot.”

Eyes flying open, both Tommy and Karlee flipped over onto their backs and tried to pull the cum-stained sheets on top of them, but succeeded only in smearing themselves with semen.

Karlee’s intrusive roommate stood in the doorway scarfing on a pint of ice cream, seemingly unapologetic for her intrusion. How long she had been watching, neither of them could guess.

“No, seriously,” she grinned, mouth full of food. “That was crazy hot.”

…….

Tommy was too mortified to return to Karlee’s dorm room after that. He tried once to visit his girlfriend there, Escort Bayan but when Karlee’s roommate passed him in the hallway, the grin that stretched the voyeur’s face from ear to ear was enough to turn Tommy’s cheeks beet red and his feet fumbling for the exit.

“We didn’t do anything wrong,” Karlee told him. “Didn’t you like it?”

“Well, I mean….”

“I really liked it,” she rubbed herself against him.

He liked that she liked it.

“I like being adventurous with you.” Her voice was low and husky. “I want you to be adventurous. The more adventurous the better.”

He felt torn. He loved his girlfriend, and he loved making her feel happy and pleased with him.

“I just… maybe without an audience for now.”

They could try his place, she offered. Sometimes there was privacy. Sometimes.

Part of the problem was their respective work schedules. He was interning at a law office and often had to work late when the lawyers did. She was learning the ropes at the nurse’s desk at the local ER and often had to work nights. It was sometimes difficult to coordinate their schedules.

At least a week passed before they could eek out an hour’s time together at his place without any roommates lurking around. It didn’t help that two of his apartment-mates seemed to be full-time recluses these days, growing roots into the common-room sofa and playing video games.

The quick hour that Tommy and Karlee had was spent with clothes flung to the floor and Tommy’s cock sawing frantically in and out of Karlee’s curly-haired pussy. A week’s pent-up frustration got taken out on each other.

“Tommy, your cock! Oh my god, I love your cock so much!”

“Oh, Karlee! Karlee! Fuck! Fucking hell! Feels so good! Your pussy feels SO GOOD!”

“Fuck me, baby. I love it. I love it! I love getting fucked! I wanna get fucked all the time!”

Tommy smiled. “All the time?”

Karlee hooked her legs around his back. “All the time, baby! I can’t get enough!”

Tommy grinned and deep-dicked her with powerful strokes.

“Oh my god, baby, I’m gonna cum!” she shrieked. Tommy grunted and kept his pace up.

“Oh, so good! So good, baby! I’m gonna cum all over your big cock!”

Tommy liked the sound of that. “Yeah,” he grunted.

“Oh fuck! I’m cumming, baby! I’m cumming on your big cock! Don’t stop! Give it to me! Give it to meeeeeeee!” Karlee squealed and clutched her boyfriend. Her body convulsed and her eyes crossed.

Tommy kept plunging her all the way through her orgasm. Finally, eyes uncrossed and she giggled at him.

“You gonna cum for me, baby? You close?”

Tommy wasn’t particularly close. He enjoyed having sexual stamina and was enjoying the feeling of his girlfriend’s pussy around his cock.

“Uh,… I’ll get there….” he said.

Karlee gave him a pouty look. “But I want my boyfriend’s delicious cum.”

He kept plunging into her. “I’ll… get there.” He watched her wonderful natural tits bouncing with every thrust. This was nice. This was hot. He liked this.

She noticed him staring. “You like my titties, baby?”

“Uh-huh,” he grunted.

“Mmmm. I can feel you getting harder. You DO like my pretty titties.” She giggled again. “But I want Tommy’s yummy cummies, and I want them now.”

“I’m… I’m trying….” he grunted.

Then an incredibly mischievous grin came over Karlee’s face. “I think I can help you, baby.”

“Okay,” he kept thrusting, watching her breasts.

Karlee stuck a finger lewdly in her mouth and sucked on it as though it was a little cock. “Mmmmmmm,” she moaned performatively.

“That’s hot,” he said, still thrusting into her.

“Mmmm-hmmmm.” She pulled it, spit-soaked from her mouth. “Just you wait, baby.”

Tommy didn’t know what his gorgeous girlfriend was talking about, and he hardly noticed, focused as he was on her breasts, that she’d reached around behind him with her hands.

“Adventurous, okay, baby?”

“Huh?”

With one hand, Karlee grabbed one of Tommy’s muscular ass-cheeks and pulled it aside, exposing his asshole. The wet finger from the other hand found the entrance to his man-channel and, applying pressure to its tight opening, wriggled its tip inside.

Tommy’s eyes flew open and he buried himself as deeply inside Karlee’s tight pussy as he could.

“Oh my god!” he yelped.

“Mmmmm. That’s a good boy,” Karlee purred.

“Oh my god, Karlee.”

“Uh-huh?” She pushed more of her spit-slicked finger up his tight opening, now up to the first knuckle.

“What are you doing?” he gasped.

“Being adventurous,” she grinned. “Mmmm, you should see your face right now, baby. It’s so hot.”

“I…” Tommy didn’t have words, but as more of her finger pushed inside of him, his cock began to twitch.

“Ooooh! You like this!” Karlee was giddy. “Yay! I can feel you inside me!”

“Oh my god,” Tommy moaned. His eyes fluttered as she pushed even more of her finger into him, now up to the second knuckle.

“Mmmm. I think my sexy boyfriend is gonna cum for me soon,” she tittered.

“Ooh! Ooh!” Tommy’s brain was barely functioning.

“Mmmm, such a sensitive, perfect butt you have, baby.”

Karlee started to swirl her finger around in a circle, tantalizing the nerve endings all around the pucker of Tommy’s anus.

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