Baby's First Bisexual Awakening



Arven lay on his back across Cassia’s bed, his head dangling off the side of the mattress.  He stared at the twinkling lights that lined the wall above her desk, just enjoying the vibes.  He would have never thought he’d be someone who did this kind of thing recreationally, but here he was, spending another weekend getting high with his girlfriend.

When he got old enough to try alcohol, he did.  A year or so before Cassia moved to Paldea, he bought a bottle of wine… not for purpose of drinking, but for cooking.  After making that meal, he had plenty left over and found himself curious about how it would make him feel.  Deep inside, he had hoped getting drunk might help him forget about everything.  The first glass did just that; the third had him dwelling on his woes.  The next day was miserable on top of that.  He quickly quit that before it became a habit and had no desire to try it again.

He was worried at first that smoking would do the same thing to him, but she had a way of convincing him to try new things he would have never before considered.  Thankfully, he didn’t have that same problem as he did with alcohol.  No, instead of getting depressed, every time he smoked, he got so fucking horny. He doubted it was an effect of the drug, just a by-product of being around Cassia with all his inhibitions lowered each time it happened.  Just thinking about how he always ended up with a boner after smoking with his girlfriend now made him hard.

“Sometimes, I think you have it easy,” he blurted out.

He felt the mattress shifting as Cassia rolled onto her side next to him.

She turned a light, amused expression on him, “Easy?”

“Yeah,” he said.  “You don’t pop a boner every time we hang out like this.”

She snorted, rolling closer into him.

“I mean, I pretty much end up wet every time we hang out,” she admitted.

“That’s not the same, Cass…” He trailed off as he brought his attention back to the lights on the wall.  His thoughts seemed to flow like molasses, slowly yet smoothly into the next. What must have been a few minutes passed before he spoke up again.  “Do you ever wonder what it’s like?”

“What what’s like?”

“What it’s like to have a dick,” he blurted out.

Cassia cracked up, but nodded her head.

“Yeah,” she said.  “I think I’d have a lot of fun with it.”

Arven tried to imagine it for a second.  While he would admit that there had been times he found other guys attractive, he hadn’t exactly considered being with someone with a penis before.   He didn’t know if it was because he was high, but the mental image was kind of hot.

“Would you let me see it?” he asked.

“Of course, I would,” she said.  Her fingertips ghosted over the front of his pants.  “I’d even let you play with it.”

He incorporated that into the mental image, and felt himself grow harder at that suggestion.  He felt a bit strange about it.  Still horny, but a little guilty.

“That wouldn’t be weird, would it?” he asked.

“Why would it be weird?” she said with a giggle.  “I play with yours all the time.”

“Yeah, but this is different.  I’m a boy and you’re my girlfriend… If…”

“Shh…”  She placed a finger over his lips before he could continue. “It’d be fine, Arven.  Especially in this magical, imaginary world where I have a dick.”

His fingers wrapped around her wrist and he pulled her hand away from his mouth so he could speak.

“But I like having sex with you,” he said.  “If we both had dicks, we couldn’t do that.”

“Yeah, we could.  I could just fuck you in the ass,” she said.

His cock twitched and a wave of lust rushed through him.  For someone with no parental supervision during his teenage years, he was pretty sheltered.  He never even considered that it was an option.  As he thought about it, Cassia lay amused beside him, proud that she may have opened her boyfriend’s eyes to the option of further exploring his sexuality. She nudged him over after a moment, and he was so relaxed that he let her roll him over onto his stomach.  When he was lying face down, she smacked his ass and leaned over him.

“You’d like that, wouldn’t you?”  Cassia spoke huskily against his ear.  “You’d love to take it for once.”

Fuck…”

He swallowed hard. His hard cock was now pressed against the mattress and he couldn’t help but rut against it at the thought of her doing that to him.

“Can I tell you a secret, Arven?” she whispered.

“Yeah,” he responded breathlessly.

“I can show you what it feels like if you want,” she said.

He felt his cheeks burn a little as his body tensed.

“How?” he said.  “You don’t… have one…”

“No,” she said with a laugh. “But…  Actually, hold on.  I’ll be right back.”

With that, she crawled off the bed and bounced towards the bathroom.  Arven felt his heart beating faster.  He had no clue what she was up to.  In her absence, he found himself subtly humping the mattress.  He had no idea why the idea of her having a penis to use on him excited him so much, but at this point, he didn’t care.  He could unpack that later.  She returned with something in her hands, but she kept it out of his view.  She sat down beside him again, and he looked up to meet her eyes.

“I don’t have a strap on,” she said.  “But I can use this.”

She held it up.  It was clear purple and shaped like a dick. He stared at it for a moment before looking at her.

“That’s a dildo,” he said in amazement.

Cassia laughed, “Yes. It is.”

He glanced back at it, trying to picture her putting it in him.

“Kinda big, isn’t it?” he sheepishly asked, feeling heat rise to his cheeks.

“No, not really,” she said. “It’s the smallest one I own.”

“That makes it sound like you have a bunch in there,” he frowned.  She leaned down, pushing back his bangs so she could kiss his forehead.

“I have a few,” she admitted.  “A few that I don’t really use anymore because I have a real one to play with that’s bigger than all of them.”

His cock twitched at the idea of her having a collection of toys in there.  Maybe she’d let him use one on her at some point…

“What do you say?” she asked, using the toy to trace the curve of his ass.

“What do I say?” he mumbled.

“Do you want me to show you how it feels?”

God, the thought alone made him want to blow his load.  He didn’t even answer verbally, he sat back on his knees and reached for the button of his pants.

“Shit, you’re more into this than I thought.  I was thinking you’d wimp out,” she laughed, then rose to her feet.  “Get comfortable.  I’m going to grab the lube.”

Cassia disappeared into the bathroom once again and Arven was left in a state of complete anticipation. He pulled down his pants and boxers then kicked them off onto the floor.  Beads of pre were oozing out of him, running down his cock.  He ran his finger up the length of his dick, collecting some of the liquid before rubbing it on his throbbing shaft.  The feeling was so good that he moaned softly.

“Getting started without me?” she teased when she walked back into the room.  Arven shook his head as he yanked his hand away from his cock. “Want another hit before we start?”

He pondered it for a moment, then nodded.  Cassia reached for the bong and took a drag, holding the smoke in her mouth as she brought her lips to his mouth.  She breathed the smoke into their kiss which made him moan.  He much preferred shot-gunning to hitting the bong himself, which was probably part of the reason why he got so damn aroused every time he smoked.  Her lips lingered on his after she exhaled, and she sucked gently on his bottom lip before pulling away.

“Hands and knees, baby boy,” she said when she walked the bong back over to her desk.  “Show me that pretty ass of yours.”

“Yes, ma’am,” he breathed.  The compliment made him blush.  Her ass was pretty, his as was… he didn’t know.  He didn’t think ‘pretty’ would be the word to describe it though. Regardless, he did as he was told.  He re-positioned himself on the bed on all fours, then glanced over his shoulder look back at her.  The idea of what they were about to do caused his heart to skip a beat.  Cassia crawled onto the bed, standing on her knees behind him.

“You might want to hold onto something,” she warned as her hand smoothed over his bare ass.  He reached forward and pulled one of her pillows closer to hold.  She squeezed some lube onto her fingers, then rubbed it on his asshole.  He’d never been touched there before, and it made him tense up.

“Everything okay?”

“Yeah…  Just feels… weird…”

“Bad weird?”

He shook his head.

“Good.  I think I’ll stretch you out with my fingers first.”

What?” he exclaimed. “You’re really gonna stick your fingers in there?”

“Well… yeah,” she said. “You don’t want me to go straight to the dildo, it could tear something.”

“But isn’t that gross?”

She laughed and smacked his ass again.  She then leaned forward, bringing her lips to his ear as she traced his hole.

“Arven, I’d stick my tongue in here if I didn’t think you’d cum so hard you’d wind up in a coma,” she whispered.  He shuddered under her words, and she kissed the base of his neck.  “Trust me, baby.”

He couldn’t force himself to speak up, but he nodded anyway.  She teased his hole a little more before slipping her finger into it. His body tensed again and he gripped the pillow.

“Shh…  Just relax,” she said, rubbing his ass with her free hand. “Tell me if you want me to stop.”

“Nuh-uh…  Go on…”

Her finger slipped further inside of him, and he grunted as it went deeper.  He felt his cock leaking as it bobbed beneath him.

“You’re doing good, baby,” she cooed as she pushed her finger in until it was resting against his prostate.  She pressed down on it gently, causing him to moan out loud.  She smiled to herself as she moved her finger around, massaging that spot.  Arven began to relax, pushing back against her finger, his muscles loosening.  Right as he was seeing stars, he felt the emptiness of her removing her fingers.

Casssss…. Don’t stop now,” he whined.

“I’m not, baby,” Cassia assured him.  He felt his hole stretch as she added a second finger.  Slowly, she rotated them within him.  He moaned loudly as she fucked him slowly, stroking his prostate. He gripped the pillow tighter, trying to control the sensations that were washing over him.

“God, Cass,” he groaned. “What are you doing back there?”

“Just stretching you out,” she replied.  “Be patient. I’ll give you the best orgasm of your life.”

He trembled at the image that painted itself before his eyes— her big dick slamming into him, fucking his brains out.  He arched his back and clenched around her fingers as it did, his orgasm rushing nearer at the thoughts of what her cock would feel like.  Just as he came close to blowing his load, Cassia’s fingers were gone.  He couldn’t hold back the whimper of frustration as the pleasure subsided. Cassia chuckled, grabbing the bottle of lube and the dildo.  

“I think you’re more than ready, big boy.”

Arven looked back over his shoulder just long enough to see Cassia drizzled some lube onto the toy. His cock twitched in anticipation, smearing pre-cum against his abdomen.

“Now this is gonna be fun,” she said, smiling devilishly as she circled his asshole with the tip of the toy.  “Ready?”

Please…”

“Here we go.”

She pushed it into him with a firm push that made him grunt.  Her toy dick went in deep, stretching him wide, making the muscles spasm. His jaw fell slack, his toes curled, and his eyes rolled back as he groaned out in pleasure.  She kept it in place for a moment, allowing him to adjust to the size before drawing it out of him and pressing it back in.  Her ministrations brought whimpers and broken moans out of him.

“You’re doing so good, Arven,” she cooed as she worked the dildo in and out of him.  “For a virgin, you take it like a champ.”

“I-I’m not… a virgin,” he panted out, momentarily gritting his teeth as the toy stimulated his prostate.

“I know,” she chuckled. “But I’m still taking your anal virginity.”

He grunted again in agreement as she thrust the toy deeper into him.  She was picking up speed now, and the bulbous head of the toy was stimulating that spot inside of him in the most perfect way.

“You like that, don’t you, baby boy?”

He bobbed his head, finding it hard to vocalize his thoughts.

“Mm... yeah.  I can tell,” she continued.  He swore he heard her laugh before she spoke up again. “Remind me again, Arven… You wanna have a family, right?”

He groaned at her question. It was one he’d asked her once before in the heat of the moment.  He wasn’t sure what came over him back then, but the thought of making her the mother of his children was the hottest thing imaginable at that time.  She was a good sport and played along.  Seemed like now it was his turn.  He nodded his head fervently.

“Yeah, me too…  It’s a shame I can’t breed this tightpretty… hole of yours, Arven,” she said, emphasizing her words by driving the dildo into him.  “I wish I could be the one fucking babies into you.  You’d be such a good daddy for my babies.”

Arven whimpered at the thought.  This was so fucking hot.  Something about all this felt so perverse, which only made his cock pulse harder. When he closed his eyes, he could picture it.  He imagined that toy in his ass was her actual cock.  She’d fuck him so ruthlessly, yet he’d beg for more.

“Fuck, do it, Cass,” he desperately whined as she fucked his ass harder.  “Fuck me.  Fuck me, harder.  Give it to me, Cassie.  Gimme a baby. I’m begging… Begging you to breed me.  I want a baby.  I want your baby!”

His cock throbbed against his abdomen, the sensations of her deep thrusts sending waves of pleasure through him.

“God, you’re such a little slut,” she laughed.  “A little bit of weed and you made yourself my bitch.  I know that’s the way you like it, pretty boy.  You can’t get enough of my cock, can you, baby?”

Arven was hugging the pillow for dear life, soaking it with drool as he panted heavily and bucked his hips. He felt her grip the base of his dick, stroking firmly.

“You wanna see me become a mommy so bad you’d do the hard work for me?” she asked as she pumped his dick in time with her thrusts.  He whimpered in reply.  “That’s my sweet boy.  Willing to do anything for mommy.  You like knowing your tight asshole is gonna make me a mommy someday?”

Tears pricked his eyes as he nodded frantically at her.

“Let’s do it, Arven. Cum around my cock as it fills your ass. Imagine mommy’s breeding you right… now,” she ordered as she pushed the dildo in deeper than she had previously.  He cried out as thick spurts of cum painted his chest and the blanket beneath him. His knuckles were white as he gripped the pillow.  His ass clenched tight around the toy, milking her dildo as the final bursts of cum shot out of his cock.  His legs felt like jelly, too weak to continue supporting him, so he collapsed into his own puddle of cum.

Cassia tossed her toy to the floor, unconcerned about the mess for the moment.  She grabbed Arven by the shoulder and rolled him over onto his back.  She straddled him to enjoy watching his chest heave and gasp for air as his head rested on the pillow and his eyelids fought to stay open.  Never in her entire life had she ever seen a man in such a state of bliss.  She leaned forward, gently pressing her lips to his.  With his jaw still slack, she was able to ease her tongue into his mouth and kiss him deeply.

“That’s my good boy,” she whispered against his lips, carding her fingers through his perspiration-soaked hair.

“Cassia…”  He had made such noise that his voice was now hoarse. “Fuck… Did we just do that?”

Cassia smiled to herself as she settled by his side.

“Yeah, and you loved every single second of it,” she said.  “Let me know when you feel like you can move again and we’ll get you a shower before bed.”

***

That night, after their shower, Arven drifted off in Cassia’s arms.  At some point over the night, he slipped into a dream.

Cassia was standing before him, wearing her school uniform like she often did.  He wasn’t sure exactly where they were, but it was an open field with the greenest grass he’d ever seen.  There was no one around for miles; just the two of them.  A picnic blanket was spread out beneath her, barely visible amidst the tall grass surrounding it.  She beckoned him closer, and he naturally obeyed.  When he arrived, she threw her arms around him, brought her lips to his, and began to kiss him passionately.  She pressed her body against his as they kissed, and he in turn held her tight.  As the kiss grew more frenzied, he felt something hard growing against his thigh. Arven broke away and glanced down to find her skirt was tented.  His eyes bulged at the sight of her obvious erection.  Rather than questioning it, he found himself on his knees in front of her. He lifted her skirt, to find she was wearing nothing underneath.  Her huge, thick cock stood proudly between her legs.  He licked his lips, then glanced up to meet her gaze.  She gave him a nod to proceed, and he took her cock in his hands. It was hard and smooth to touch. It was so much prettier than his, with a cute, perfect sack to match.

“That’s it, baby boy,” she cooed as he wrapped his lips around it.  The pre-cum that dribbled from it tasted sweet like syrup.  Arven eagerly sucked on it, wanting to taste every inch.  He took it down his throat, until his nose pressed against the base.  He sucked on it for a minute before pulling away, then he licked his lips at how good it felt before going back for more.

After a moment, she pulled him off of her cock by his hair.   Panting, he wiped his mouth with his wrist while looking at her through a heavy-lidded gaze.  Before he could speak, she had him on his back, straddling him as she pulled his pants away and yanked his boxers down.  She spread his legs wide.  She rubbed the slick head of her cock against his hole, making him whimper.  She said not a word as she thrust her length into him. He cried out in pleasure, his own dick bobbing between them with every rough thrust of her hips.

“That’s a good boy,” she cooed.  “Just lay there and let mommy make a baby.”

“Fuck.  Yes, please,” he cried in response.  His hole clenched around her cock, and he pushed back against her.  He wanted her to fuck him harder.  She was so good at this that every thrust made him close to orgasm already.  Cassia laughed, gripping his hips as she quickened her pace.  She pounded him so relentlessly that he felt her balls slap against his thighs with every thrust.  He could tell they were so heavy and full of cum to pump into him.  In fact, it was the thought of her seed that made him moan and whimper as Cassia fucked him.  The thought of being filled by her turned him on so much.

“Such a slut now, aren’t you?” she laughed.  “You wanna have my babies so bad it hurts, don’t you?”

As she spoke, her cock swelled inside of him.  It pushed against his insides, stretching him so tight and making him moan louder.  He couldn’t help it if he was so excited; he wanted her bad.

“You want my babies. Beg me for them.  Beg me to make you a daddy.”

Please…” he breathed.  

Her hand tangled in his hair and tugged it, causing him to moan.

“Beg me like you mean it, baby boy,” her low voice said.  “Beg me.  Or I’ll pull out.”

“Please, please, please, Cassia… Make me a daddy… Let me make you a mommy.”

She moaned in response, and she fucked him faster.

“You’re so close, baby. Make mommy proud.  Beg me to breed you.  Beg me to give you my babies,” she groaned.  Her voice was raspy and raw, her thrusts so wild and fast he could hardly breathe.

“Please…  Fuck, please… Please, I need it.  I need you.”

“Fuck, you’re such a good boy,” Cassia moaned.  “Anything for my needy little baby.”

Arven felt his soul leave his body the moment he felt the torrent of cum gush into his ass.  He could feel the warmth of it filling him, and he sobbed in ecstasy.  Right as his own dick was about to explode…

Arven awoke with a gasp. His heart was beating fast and his body felt like it had just run a marathon.  As he became more lucid, he grimaced at the feel of his soaked boxers. He couldn’t remember the last time he had a wet dream like that, and he also couldn’t remember the last time he had ever woken up so aroused or so needy.  He didn’t think Cassia had made him that much of a slut… but maybe she had. Yeah, there was no doubt about it that she absolutely had.  He wanted to feel embarrassed about his behavior the night before, but the truth was that the only thing he was embarrassed about was how it took him so long to find out about this kind of thing.

He needed to get out of bed to rid himself of his ruined boxers and clean himself up.  He tried to ease out of Cassia’s arms without waking her, but when he moved, she tightened her hold on him.

“Baby…” she mumbled. “Arven…”

“Sorry, Cassie,” he whispered.  “Just need to go to the bathroom.”

“Good luck walking,” she said with a soft, sleepy giggle.  “You really showed your ass last night.”

“Yeah, well… It’s your fault,” he teasingly quipped.  He just knew his cheeks were bright pink at this point.

“How’s it my fault?”

“Because…”  When she opened her eyes and looked at him with a smirk, he stopped to think of a reason.  “Because you and your dumb weed made me so horny, I couldn’t think straight,” he said to her before softly pressing his lips to hers.  

“I’d say you’ll never think straight again,” she said with a chuckle.  “Baby’s first bisexual awakening.”

“Oh, shut up,” he said, rolling his eyes as his cheeks grew even hotter.  “Jokes aside… You really gave me the best night of my life.”

“Glad you enjoyed yourself,” she muttered, easing her hold on him.  “Remind me to order us a strap when I wake up.”

He knit his brows at this statement.

“A strap?”

She giggled, but yawned instead of answering and snuggled closer to her pillow.