Cassia, My Girlfriend's Best Friend

NOTE: This is a work of fantasy containing elements of cheating and unprotected sex. Do not do these things in real life, folks.

###

"I don't understand why they can't just have a party somewhere inside."

"Don't be boring. It's a beautiful night out."

Mona was right. It was the summer before our freshman year of college, and the weather in Northern California was beautiful. Dry, hot days and cool, crisp nights, perfect for a bonfire.

"I thought bonfires were a relic of high school," I said. I was lying on Mona's bed, flicking through my phone, when Mona came back into her room.

"I think you need an attitude adjustment."

Seeing her was attitude adjustment enough. My girlfriend of about two years (we'd started dating junior year) was completely naked. She was beautiful, tall with curves hardened from years of playing sports, and her large, firm breasts stood out perfectly from her chest. They were capped by puffy pink nipples, and though I'd heard people ask more than once whether they were fake, a look at them up close revealed nothing but natural bounce.

As she approached me, my eyes traveled down her stomach, toned from regular exercise, to the patch of dark pubic hair above her full pussy lips.

"My eyes are up here, you know," she said with a smile, climbing onto the bed over me.

She had big brown eyes and freckles dotting her face, as well as wavy, dark hair.

As she pressed her body to mine, kissing me, she felt my erection through my boxers.

"Looking for a bit of a pre-game yourself?" She felt my cock through my pants. Crawling back down the bed, she unbuttoned my pants and pulled them down, along with my boxers. My cock sprang out, sticking straight up in the air.

Mona didn't hesitate, opening her full lips and engulfing my cock in her mouth. Her tongue encircled my tip, and I let out a sigh of pleasure. We'd lost our virginities to each other, so neither of us had been very experienced, but she was a quick study and her blowjob technique was incredible. She brought her mouth up and down on my cock, a perfect tight seal around me. I reached down to feel her breasts, which swung back and forth as she repeatedly buried my cock in her mouth. My cock grew, throbbing, between her lips.

If I'm honest, I preferred it when Mona sucked my cock. Sex with her was incredible, but she preferred I wear a condom. I completely understood, but I had fantasies of letting go and coming inside her bare pussy, so in times like these I had to settle for...

"Fuck, I'm coming," I moaned. Mona kept doing what she was doing, that tight seal of her lips bringing me quickly to orgasm. "Can I cum in your mouth?" She hummed her assent, not stopping.

I looked down at her, red lips on a freckled face, her eyes closed. God, I loved filling that mouth. Closing my eyes, I focused on the sensation of her wet mouth and tongue on my cock, until my orgasm hit hard. I looked down to watch my cock jerk and spasm, shooting cum hard into Mona's mouth. She kept sucking, working every spurt out of me and into her waiting mouth, until I could cum no longer. She paused, my cock in her mouth, and tried to swallow it all, unsuccessfully. A dribble came out and dripped back down my cock as she lifted off me. She quickly licked my cock clean.

Mona looked up at me, a small drop of cum on her bottom lip. She smiled, getting the last of it with her tongue.

"NOW are you excited for the bonfire?"

###

The bonfire was down by a pond, far enough away from town that there would be no one to shut us down. In a clearing, a makeshift party had been set up: beer pong tables, a folding table stacked with cheap liquor, and a crackling fire. Standing by the fire, drinking from a red solo cup and being talked at by a couple guys, was a slender woman with honey-gold hair who I recognized as Cassia.

Cassia was Mona's best friend, a sweet, quiet girl who'd moved here from Vermont a few years back. She spotted us, and her face light up. She, like Mona, had a light dusting of freckles on her fair skin, which went well with her hippie look. Tonight she wore a choker and a crop top with a floral print on it, which, I noticed with a slight twinge, accentuated her smaller breasts beautifully. Clearly the top wasn't conducive to a bra, because her nipples pushed through the fabric in the cool night air. I looked away, scolding myself. Cassia was Mona's best friend, and though I had always thought she was stunningly beautiful in a wood nymph kind of way, I loved Mona and was content to admire Cassia only in stolen glances.

"Thank god you're here," Cassia said, hugging us. "I was worried I'd have to make other friends."

"I'm not sure that would be a problem," Mona said. "Looks like a good amount of guys trying to talk to you around the fire."

Cassia scrunched her face up in mock distaste. "Not interested," she said, and I could have sworn she looked at me while she said it.

"You're gonna have to date at some point," Mona said. It was something she'd talked to me about before, this beautiful friend of hers who didn't seem to want to return anyone's advances. We'd tried setting her up with some of my friends, but she'd always shot them down.

Cassia shrugged. "Let's focus on the task at hand, okay?" She raised her cup and finished the last of her drink. "Getting completely tanked."

###

The drinking part wasn't difficult. We took shots together, matched each other drink for drink, and Mona and Cassia played beer pong together, losing at an almost inhuman speed. As they came back up to me from the beer pong table, I was struck by how beautiful they both were -- Mona dark and tall and curvy, Cassia fair and small and slender. Clearly the alcohol was having an effect on me.

"Look, those two heading off into the woods for a bit of fun." Cassia grinned and pointed at the retreating figure of two people who had been in our class.

"Hope they brought protection," Mona said.

"For their sake, I hope not," Cassia said. Mona shot her a surprised look, but Cassia shrugged. "I just mean it's gonna feel so much fucking better for them if they're not using a condom. At least, that's been my experience."

"Your experience?! I thought you said you didn't have any."

"Just a couple times, a guy last summer." Cassia took a sip of her drink. She looked beautiful in the dim firelight, and I thought I saw her blush. "Unprotected was always better. The feeling of having someone cum inside you is just... amazing."

I'd never heard shy, sweet Cassia say something that explicit, and nearly choked on my drink. I was instantly hard, and very grateful for the darkness of an outdoor party, where no one would notice.

"Wow, Cassia," Mona said. "That's a lot of detail."

"Sorry," she said, shrugging. "But it's true. Sure, there's risks, but it feels more like the real deal. Have -- have you guys ever done it raw?"

I was too distracted by the mental image of Cassia on her back, legs spread, pussy open and dripping with cum, to answer. Mona did for me.

"I mean... no. We haven't."

Before I could think of what the hell to contribute to this conversation, a friend of mine waved me over for a beer pong game. I went over to him, glad for a reason to leave the conversation.

At the beer pong table, I looked over at Cassia and Mona. Cassia was whispering something in Mona's ear. Mona raised her eyebrows, as if considering something, and Cassia looked directly at me. We held each other's gaze for a beat too long, before I looked away.

That image of Cassia having unprotected sex, I knew, would be burned into my mind for a long time.

###

By the time we got to Mona's house, we were all feeling the effects of hours upon hours of drinking. Though I had thought we matched each other drink for drink, Cassia wasn't as drunk as we were. Cassia was a petite woman, but she could clearly hold her liquor.

"Don't walk all the way back to your house," Mona said to Cassia, her words a little slanted from the alcohol. "You can sleep here."

"I don't want to third wheel any more than I have to," Cassia said.

"No, you're welcome to stay," I said. "It'd be nice to have you."

Cassia looked at me strangely. Before I could clarify the wording on my comment, Mona turned and headed to her room, pulling her dress up and off herself, until she was only in her underwear in front of me and Cassia. She was wearing a g-string, and her ass was incredible -- round, bouncy, tight. Mona turned around to face me and Cassia, her tits jiggling in her bra.

"Come here," she said to me in a sultry voice. I looked to Cassia, a little embarrassed. Clearly Mona was plastered.

"Goodnight," I said to Cassia.

"Night."

In Mona's room, she fell back onto her bed. I could make out her pussy through her lace underwear, wet and inviting.

"C'mere."

I knew Mona enough to knew she'd wish she'd drunk more water tonight, so I ran my hand up her leg and told her I'd be right back. Despite her protests, I went back out into the kitchen.

As I stood at the sink, filling up a cup, I looked into the living room. My stomach clenched. There, facing the window, her back to me, was Cassia, peeling off her crop top.

I wish I could say I turned away, filled my cup, and went back to my girlfriend. But I stayed there, watching. She had to know I was there in the kitchen. Why wasn't she turning?

In the angled reflection of the window, I saw the faint outline of her tits. Though they were small, they fit her frame perfectly, with small, upturned nipples.

"You gonna turn off the sink?" Cassia asked, without turning.

Startled, I looked down: my cup was overflowing. I turned the sink off, embarrassed, then cleared my throat. She was watching me in the reflection, smiling wryly but not moving to cover herself.

"Sorry. I was just..." I trailed off. We both knew what I'd been doing. I was rock hard. After a horribly awkward, silent moment, I walked back towards Mona's room. When I was almost at the door, Cassia spoke again.

"You're welcome, by the way."

"Sorry?" My heart was beating rapidly.

"I said you're welcome," she said, her voice low. She turned to face me, still topless. I tried my hardest not to look at her incredible breasts. "I told Mona you guys have been dating for long enough. It's time to do it for real."

She bent down and pulled on an oversized T-shirt. I recognized it as one of my own that I'd left here. When Mona wore it, her breasts swayed hypnotically under the fabric. Cassia's weren't as big, and they were so firm they hardly moved, but I could still see her hard nipples through the shirt.

"Do it for real?"

She gave me a mischievous smile that made my cock twitch.

"Fuck her without a condom."

###

When I entered Mona's room, she was already naked. Even on her back, her breasts stood out incredibly from her chest. She was shimmying out of her panties, revealing her pussy: two tight lips that created a neat symmetrical seal, beneath a triangle of pubic hair. She spread her legs on the bed, and I watched as the lips were pulled apart, the seal breaking open to offer me a peek into her depths.

Setting down the glass of water, I dropped to my knees and pressed my lips into her pussy. She smelled and tasted amazing, a womanly scent that I lapped away at. Mona loved it when I formed a seal over her upper pussy and sucked her clit while playing at it with my tongue.

"Ohhhhh..." she moaned.

I stuck two fingers inside her, facing upward, and made the "come hither" motion on her G-spot. I was rewarded with her thighs closing tightly on either side of my head, her hands threading through my hair. When she was done writhing around my fingers, she pulled my face up to look at her.

"Get up here."

As I climbed the bed towards her, she pulled off my boxers. My cock fell out, trailing pre-cum on her leg. I bent down to kiss her.

"Mmm," she whispered. "I love tasting myself on your lips." Then she did something I was expecting, but still set my heart beating fast: she grabbed my cock and slotted me into the wet crevice between her lips. I looked down at her.

"You sure you don't want to --?"

She shook her head. "I want you inside me. I want your bare cock in my pussy. And I don't want there to be anything between us."

I didn't need to be told twice. Pushing forward, through her slick folds, I felt my cock make the familiar trip into her pussy -- only now, with no rubber separating us, I could feel every part of her. She was always unbelievably tight, but with the added wetness it was an entirely new experience.

"Oh my fucking god," she said, feeling me bottom out in her. "This is incredible."

I began to thrust inside her, her wetness lubricating me perfectly. Her tits bounced in my face, and I leaned down to capture a nipple in my mouth. Where it normally took a while to bring me to the brink of an orgasm, the raw feeling of her pussy took me there in a minute or two. Now I wouldn't just be the man who had taken her virginity, I'd be the first man to cum inside her.

Mona could feel my cock growing inside her, signaling my impending orgasm. She clutched me tighter.

"Cum inside me," she said, louder than I expected considering Cassia was in the other room. "I want you to cum inside my pussy. I want you to fill me up. Please, please, please..."

This was all I needed to hear. Looking down at my cock sawing in and out of her, her breasts bouncing with every stroke, I shut my eyes hard.

"Cum inside me..."

"I'm going to," I moaned.

Coming inside Mona for the first time was incredible. I drove into her, pushing myself as far in as I could go, and felt my cum release in a torrent, splashing into her pussy and filling her up completely. Mona groaned at the pleasure of her pussy filled with the warmth of my cum.

When we were done, I pulled out slowly. Mona dipped her fingers into her pussy with wonder, holding them up covered in cum.

"I can't believe we waited so long to do that."

"Me neither," I said. "That was... amazing."

"We'll have to thank Cassia for the idea."

###

We held each other for a long time, until her breathing slowed and she fell asleep in my arms. I checked the clock. I still had to brush my teeth.

I slipped on boxers, then opened the door and peeked out. The apartment was dark.

I padded to the bathroom. I brushed my teeth, admiring myself in the mirror. I was flushed and a little sweaty. I looked like a guy who'd just been fucked.

There was a soft knock at the door, then a voice:

"Are you decent?"

"In here --"

The door opened anyway. In the doorway stood Cassia, wearing only the sheer, oversized T-shirt. I wondered whether she was wearing panties underneath. She was even still wearing the choker.

"Sorry. I just wanted to brush my teeth."

Not knowing what to do, I nodded. She came to the sink and began to brush her teeth next to me.

We looked at each other in the mirror. Her hair was up in a messy bun. She looked unbelievably beautiful.

"So how'd it go?" She asked softly, through a mouthful of toothpaste.

I waited, brushing slowly. What was happening? How much should I tell her? She leaned down to spit into the sink. As she did, the shirt rode up her perfect ass, which I'd admired for years. She wasn't wearing underwear. I looked back at her in the mirror, then spit.

"I guess I should be thanking you."

"Mona liked it?"

I nodded.

"I knew she would. Love the girl, but she has trouble doing anything unless you give her a bit of a push."

Cassia bent down again, splashing water on her face. I thought I could make out the barest hint of her pussy between her legs. She caught me looking, but didn't straighten up right away.

Even in my semi-drunken state, I knew this was quickly headed somewhere it shouldn't be.

"Well," I said, "it was a welcome push."

Leave, a voice inside me screamed. Get out of here. Go back to Mona's room. She's your girlfriend.

But I stood there. Both of us had stopped pretending we still had anything to do in the bathroom.

"Did you cum inside her?"

"Yes."

"And it felt good?"

"It was -- it was amazing."

She took a step closer to me, then looked down. The outline of my throbbing erection was visible through my boxers.

"I -- I could hear you, you know."

"You were listening?" It sounded stupid even as I said it, but she nodded, biting her lip. "What did you hear?"

"I heard her begging you to fill up her pussy. You groaning as you came."

"Jesus."

"I touched myself to it." Cassia's hand snaked under the shirt. I heard a slick sound as she ran a finger through her pussy lips, then held it up to me, shiny and wet. Slowly, she reached out to me. Her finger came to my mouth, and I opened it, tasting her pussy on her finger. It tasted incredible; tangy and sweet. With her other hand, Cassia caressed my cock through my shorts.

"This is a bad idea," I said, not moving to stop her.

"Mona's asleep."

"Still," I said, "we shouldn't." With great effort, I took her hand off my cock.

"You know what we were talking about while you were playing beer pong? Besides me convincing her to fuck you bareback. I was saying that we should have a threesome." I could feel my heart beating through my chest. "I know you've been looking to make things more interesting, something exciting before we all go off to college. Who better than me?"

"And she said yes?"

"Maybe it was just the alcohol, but I don't think so. We've kissed before. She's been wanting to experiment for a while."

This was all too much for me. My head spun. "Mona said yes to a threesome?"

"She said she'd talk to you." Cassia was silent for a moment. "The only problem is, I haven't done it before."

"None of us have," I said.

"I don't mean I haven't had a threesome. I mean I haven't had sex."

"But I thought --"

"I lied." That adorable blush had crept back into her cheeks. "I'm a virgin. And I've heard Mona talk about how amazing you are, so I thought -- I thought maybe you could help me practice. I can't lose my virginity in a threesome."

All I could do was gaze at her in open-mouthed wonder. Was this really happening? Cassia wanted me to take her virginity? She got on her knees, tugging my boxers down. My cock sprang up straight, almost hitting her in the face. In the bathroom light, I realized I still glistened with Mona's slick wetness, combined with my own cum. I almost said something, offered to rinse off, but she stopped me, grabbing my cock.

"That's the whole point of a threesome, isn't it? I want to taste her pussy on you."

She gave my cock a tentative lick, then opened her mouth and sank her lips around it. Whether her skills were actually superior to Mona's, or whether it was just the intensely erotic experience of watching your girlfriend's best friend lick her pussy juice off your cock, I don't know. All I knew is that as she bobbed up and down on my cock, energetically sucking me deeper into her mouth, the pleasure made me weak in the knees.

"God," she moaned around my shaft, "her pussy tastes so good on your cock."

Despite having just had the best sex of my life only twenty minutes ago, I was somehow close to coming again. Cassia's mouth felt amazing around me, licking and sucking Mona's pussy off of me until my dick was clean and shiny with her spit. I ran my fingers through her hair as she blew me.

"Cassia, I'm close --" I said, not wanting to cum in her mouth without warning.

She pulled my dick from her mouth, breathing hard. My cock jumped in her hand, backing off the edge.

"You'll cum in my mouth later. For now..." She stood, moved to the counter, and sat up on it.

As she spread her legs, I got my first good look at her pussy. Cassia had the best fucking pussy I'd ever seen in my life, two tight, neat lips covered with close-trimmed hair, a honey color that matched the hair on her head. I carefully slid a finger into her -- she was so tight, practically dripping with arousal. My cock rested right above her pussy.