I Taught My Two Best Friends

The apartment smelled of vanilla candles and the sharp tang of spilled vodka as Portia settled deeper into the worn leather couch, her third martini sweating in her hand. Sienna sprawled beside her, long blonde hair cascading over one bare shoulder, green eyes already bright with that familiar drunken curiosity that always circled back to the same filthy subject. Outside the rain tapped against the windows of the quiet suburban street, but inside the air hummed with something electric and unspoken.

“Tell me again why you like it so much,” Sienna said, voice low and teasing. “Taking it up the arse. First time anal training for women always sounds so intense when you describe it.”

Portia laughed, the sound throaty. She was twenty-six, dark-haired, athletic from years of running, with full tits that strained against her tight black top and an ass she had trained herself to open for thick cocks since she was nineteen. “Because when a guy knows what he’s doing—slow, patient, lots of lube—it feels like being split open in the best way. That pressure, that burn that turns into pure heat. My first time was rough. Hamish just shoved it in the back seat of his shitty car. Hurt like hell. But after a few more tries with better partners, I got addicted. Now I can take almost anything if I’m relaxed enough.”

Sienna’s cheeks flushed. She shifted, thighs pressing together under her short skirt. “I’ve never done it. Not even a finger. But I keep thinking about it. Lesbian strap-on anal initiation keeps popping into my head when I masturbate. Maybe you could show me. Teach me. I trust you more than any guy.”

Portia’s pussy clenched at the words. She had never touched another woman sexually beyond a few drunken kisses, but the idea of coaching Sienna through her first anal stretch made her nipples harden instantly. “Alright. Coaching session. Right now. No going out.”

The buzzer rang before Sienna could answer. Cushla arrived looking polished and ready for the club—sleek black dress, long dark hair, full lips painted red. She froze when Sienna announced the change of plans with zero filter.

“Portia is going to show us how to take it up the arse,” Sienna said, bouncing on the balls of her feet. “First time anal training for women, right here. You can watch if you want.”

Cushla’s eyes widened. “You’re both insane. I’m not sticking anything in my shit hole.”

But she stayed. Curiosity kept her planted on the armchair while Sienna dragged a plastic bag from her bedroom and dumped its contents onto the coffee table: three dildos of increasing size, a thick purple strap-on cock that looked wrist-thick, a bottle of thick water-based lube, a small remote-controlled butt plug, and a packet of latex gloves. The sight alone made Portia’s cunt drip.

Sienna stripped first, peeling off her top and skirt until she stood in only a white lace thong that disappeared between her round, firm cheeks. Her body was soft in the right places—full tits with pale pink nipples, narrow waist, hips that flared wide. She hooked her thumbs in the thong and pushed it down, stepping out naked. Her pussy was already shiny, lips plump and shaved smooth except for a thin landing strip.

“Get on all fours,” Portia ordered, voice steady even as her heart hammered. “Ass up. Reach back and spread yourself for me.”

Sienna obeyed without hesitation, knees on the rug, back arched, hands gripping her own ass cheeks and pulling them wide. The tight pink rosebud between them looked impossibly small, a perfect closed pucker that twitched under Portia’s stare. Cushla made a soft noise from the chair but said nothing.

Portia knelt behind her friend. She started slow, running both palms over the smooth globes of Sienna’s ass, squeezing, separating, watching the hole wink. Then she leaned in and dragged the flat of her tongue from the base of Sienna’s dripping cunt straight up over the tight ring of muscle. The taste was clean and musky. Sienna gasped and pushed back.

“Oh fuck. No one’s ever licked my asshole before.”

Portia did it again, slower, circling the rim with the tip of her tongue, pressing harder until the muscle softened just enough to let the tip slip inside. She fucked the tiny opening with her tongue while one hand slid under to rub Sienna’s swollen clit in tight circles. Sienna moaned continuously, hips rocking.

When Portia finally pulled back, the hole was glossy and slightly open. She squeezed a thick rope of lube directly onto it, watching the clear gel drip down over the puckered skin. Two fingers massaged it in, pressing, circling, never forcing. Sienna’s breathing grew ragged.

“Ready for the first finger?” Portia asked.

“Yes. Do it. Stretch me.”

Portia pressed the pad of her index finger against the center of the ring and pushed steadily. The muscle resisted, then yielded with a soft pop. Heat and tightness enveloped the digit up to the first knuckle, then deeper. Sienna’s ass clenched hard around the intrusion.

“Breathe out. Push back like you’re trying to push me out. That’s how you open.”

Sienna did. The finger slid the rest of the way in until Portia’s knuckles pressed against the soft cheeks. She stayed still for a long moment, letting the virgin channel adjust, then began to fuck the hole slowly—in and out, curling, scissoring gently when she added a second finger. The stretch made Sienna whimper, but her pussy was pouring juice onto the rug.

“Two fingers already,” Portia murmured. “You’re taking it so well. Such a good girl for your first time anal training.”

Cushla had leaned forward without realizing it, dress hiked up, one hand pressed between her own thighs. Portia noticed and smirked but said nothing. She worked Sienna’s ass for several minutes until the two fingers moved easily, then reached for the smallest dildo—a slim pink silicone shaft about six inches long and as thick as two fingers.

More lube. The tapered head pressed against the stretched ring. Portia pushed. Sienna cried out as the toy sank in, inch by inch, until the base nestled against her cheeks. Portia fucked her with it in long, steady strokes, twisting on the out stroke, watching the hole cling and stretch.

“Talk to me,” Portia said. “Tell me how it feels having your ass filled for the first time.”

“Full. Burning. But good. So fucking good. Harder.”

Portia gave her harder. The wet slap of the toy and the wetter sounds of Sienna’s cunt filled the room. When Sienna’s thighs started shaking, Portia reached under and rubbed her clit roughly. Sienna came with a sharp cry, ass spasming around the dildo, cunt pulsing.

Portia left the toy buried and turned to Cushla. “Your turn to watch closer. Or participate. Your choice.”

Cushla’s face was flushed. She stood, peeled the dress off in one motion, and stepped out of her thong. Her body was fuller than Sienna’s—heavy tits, soft belly, thick thighs, and a dark bush above a fat-lipped pussy. She dropped to her knees beside Sienna without a word.

Portia pulled the dildo from Sienna’s gaping hole and handed it to Cushla. “Lick it clean. Taste her ass.”

Cushla hesitated only a second before wrapping her lips around the shiny shaft and sucking. The sight made Portia’s own ass clench with need. She stripped quickly—top, jeans, panties—until she was naked too, her trimmed dark bush already soaked, nipples tight.

She strapped on the purple cock next. The harness settled against her hips, the thick realistic shaft jutting from her pelvis like a real erection. She coated it generously with lube until it gleamed.

“Sienna first,” she said. “I’m going to fuck your ass with this. Tell me if it’s too much.”

Sienna, still trembling from her orgasm, spread her cheeks wider. Portia lined up the blunt head and pushed. The tight ring stretched obscenely around the thick crown, then swallowed it. Portia kept feeding the cock in until her hips met Sienna’s ass. The heat and pressure around the base of the strap-on made Portia’s clit throb against the harness pad.

She fucked her in deep, measured thrusts at first, watching every inch disappear and reappear, the hole stretched white around the purple shaft. Sienna’s moans turned into continuous broken sounds. Portia reached around and pinched her nipples hard while she pounded.

“Take it. Take that cock in your virgin ass. You’re doing so fucking well.”

When Sienna came again, harder this time, her whole body shaking, Portia pulled out slowly. The hole stayed open, a dark tunnel that clenched and released. Cushla stared, mouth open.

“My turn,” Cushla said, voice rough. “No more watching. Stretch me.”

Portia didn’t bother with fingers. She pressed the still-slick purple head against Cushla’s smaller, tighter pucker and pushed hard. Cushla’s head snapped back as the thick cock forced its way inside in one continuous thrust until it was buried to the hilt. A long, guttural moan tore from her throat.

“Fuck—oh fuck it’s so big—don’t stop—”

Portia grabbed a fistful of dark hair and used it as a handle while she railed Cushla’s ass. The sounds were filthy—wet squelching, skin slapping, Cushla’s broken curses. Sienna crawled underneath and sucked on Cushla’s hanging tits, then slid lower to lick her clit while Portia fucked the ass above.

Cushla came screaming, ass clamping so hard around the strap-on that Portia almost couldn’t pull out. When she finally did, both holes were open and glistening.

They switched positions repeatedly. Portia lay on her back with the strap-on still attached while Sienna rode it reverse-cowgirl, bouncing on the thick shaft while Cushla sat on Portia’s face, grinding her wet cunt and open ass against Portia’s tongue. Portia licked and sucked both holes, tasting lube and musk and the residual flavor of her own earlier work.

Later they used the larger toys. The thick black dildo went into Sienna first while she was on her back, legs folded to her chest, hole forced wide. Portia and Cushla took turns pushing it in and out, talking dirty the entire time.

“Look at that greedy asshole swallowing it. You’re going to be an anal slut after tonight. Both of you.”

Cushla took the remote-controlled plug next, the widest base forcing her open while the vibrations made her thighs shake. Portia fucked Sienna’s ass with the strap-on again while Cushla rode Sienna’s face, smothering her with wet cunt and open hole.

Hours blurred. They moved to the bedroom eventually, bodies slick with sweat and lube. Portia had both women on their knees side by side, asses presented, and alternated fucking them—three hard thrusts into Sienna’s stretched hole, then three into Cushla’s, back and forth until both were babbling and dripping.

Sienna recovered a thick corn cob from the kitchen in a moment of pure filthy inspiration and worked it slowly into Portia’s own ass while Portia continued pounding Cushla. The ribbed surface dragged against every sensitive nerve. Portia came hard, grinding back onto the vegetable while her strap-on stayed buried in Cushla.

They kept going until the first gray light of dawn crept through the curtains. By then every ass had been stretched, licked, fingered, and fucked multiple times. Toys lay scattered and shiny across the sheets. The air reeked of sex and lube.

Sienna lay on her stomach, fingers lazily probing her own still-loose hole. “I can still feel it open. Like I could take another cock right now.”

Cushla, sprawled on her back with one leg bent, laughed weakly. “Same. I thought I’d hate it. Now all I want is something thicker next time.”

Portia removed the harness at last, her clit swollen and sensitive from hours of pressure. She crawled between them, kissing each woman deeply, tasting everything they had shared. “School’s not over. We’ll practice. Regular sessions. Bigger toys. Maybe bring a real cock into the mix later if you both want it.”

They dozed in a tangled heap, bodies still connected by wandering fingers that occasionally slipped back into wet, open asses just to feel the stretch again. Outside the rain had stopped. Inside, the three of them had rewritten what pleasure felt like—raw, stretching, endless.

Portia woke first an hour later to the sensation of two mouths working her body. Sienna’s tongue circled her clit while Cushla’s fingers pushed deep into her ass, scissoring her open again. She came quickly, then rolled over and returned the favor, burying her face between Cushla’s cheeks and tongue-fucking the well-used hole while Sienna sat on Cushla’s face.

Round after round followed. They ordered delivery later and ate naked on the bed, feeding each other bites between more fingering and toy play. The large purple cock went into Portia next while the other two watched and directed, telling her exactly how deep and how hard to take it. She did, moaning around a mouthful of Sienna’s cunt as the thick shaft reamed her open.

By late afternoon the apartment was a wreck of discarded clothes, empty lube bottles, and the lingering smell of thoroughly fucked asses. They showered together eventually, soaping each other’s bodies with deliberate, lingering hands that inevitably found their way back between cheeks and into holes that no longer resisted.

Standing under the hot spray, Portia pressed two fingers into Sienna’s ass and two into Cushla’s at the same time, fucking both holes in slow rhythm while the women kissed over her shoulder. “Next session we bring the bigger set,” she said. “The ones that look like they shouldn’t fit. You’ll take them. Both of you. And you’ll thank me while you do.”

Sienna and Cushla answered by grinding back harder onto the invading fingers, already hungry for the next lesson.

The night stretched into another full round after they dried off. Portia had them both bent over the bathroom counter, side by side in the mirror, while she fucked them alternately with the strap-on again—watching their faces contort in the reflection every time the thick head forced past the ring and sank deep. She made them describe every sensation out loud: the stretch, the fullness, the way their cunts clenched empty and jealous, the way their holes fluttered and tried to milk the cock.

When both women were shaking and dripping, Portia pulled out and ordered them to the floor. She sat on the closed toilet lid, legs spread, and had them take turns sucking the strap-on clean while the other licked her real cunt and asshole. The dual sensation of tongue on her clit and tongue in her ass while a wet mouth worked the silicone shaft pushed her over the edge again.

They collapsed into the living room afterward, limbs heavy, holes pleasantly sore and still slightly open. Sienna rested her head on Portia’s thigh, fingers idly tracing the swollen lips of Portia’s pussy. Cushla lay on the other side, one hand cupping her own ass as if measuring the remaining stretch.

“I want to do this every weekend,” Sienna whispered. “Serious training. Make our asses capable of taking anything.”

Cushla nodded against Portia’s hip. “Agreed. No more hesitation. Just open and take it.”

Portia stroked both women’s hair, already planning the next collection of toys, the next positions, the next filthy goals. The school of anal had officially begun, and none of them intended to graduate anytime soon.

Evening came. They ordered more food, drank more wine, and the cycle started again with slower, more deliberate stretching. Portia used only her hands at first—three fingers in Sienna while four worked into Cushla—scissoring and twisting until both holes gaped wide enough to see inside. Then the largest dildo yet, the one that had seemed impossible hours earlier, slid into each of them in turn with only mild resistance.

They finished the night with Portia on her back, the strap-on still harnessed, while Sienna and Cushla took turns riding it—facing her so she could watch their faces, then facing away so she could spread their cheeks and stare at the stretched rings swallowing every inch. When they finally stopped, exhausted and satisfied, the three of them fell asleep in a pile of warm skin and lingering lube, asses still twitching with aftershocks.

Morning light found them still tangled. Portia woke to the soft sound of Sienna and Cushla kissing while their fingers played lazily in each other’s open holes. She joined without words, tongue and hands continuing the education that had only just begun. The apartment would smell of sex for days. Their bodies would remember the stretch for longer. And every time one of them clenched around nothing in the coming weeks, they would think of this night—the night three friends learned exactly how deep and how wide pleasure could go when they stopped being afraid of the dark, tight places that begged to be filled.