Best Friends, Hidden Desires – Part 2: Lesbian First Anal with Friend Anna

Read previous part: Best Friends, Hidden Desires – Part 1: Lesbian First time with Best Friend Anna

The morning light filtered softly through my bedroom curtains, casting a warm glow over our naked, tangled bodies. I woke up first, my arm draped possessively around Anna’s waist. Her head was still resting on my chest, her long dark hair spilled across my skin like silk. At 22, I had never felt more alive than I did in that moment.
Last night had been everything I had secretly fantasized about for years. We didn’t just have sex - we made love, we fucked, we devoured each other. But as I lay there feeling Anna’s steady breathing against me, a new hunger was already stirring deep in my belly. I wanted more. I wanted to claim every single inch of her body. I wanted to push her limits and watch her fall apart in ways she never had before.
Anna stirred, her big brown eyes fluttering open. When she saw me looking down at her, a shy but satisfied smile spread across her face.
“Morning…” she whispered, her voice still husky from all the moaning she did last night.
“Morning, beautiful,” I replied, leaning down to kiss her softly. The kiss quickly deepened. Our tongues met lazily at first, then with growing hunger. Even after hours of sex, we couldn’t get enough of each other.
Anna’s hand slid down my body and cupped my pussy possessively. “I can still feel how wet I made you last night,” she murmured against my lips, her fingers gently stroking my slick folds.
I moaned softly and spread my legs for her. “You destroyed me, baby. But I’m already horny again.”
We kissed harder, grinding slowly against each other’s thighs. The scent of sex still lingered heavily in the air - our combined juices, sweat, and lust. It was intoxicating.
After a long, lazy make-out session, Anna pulled back and looked at me with those vulnerable eyes I loved so much.
“Ricky… last night was the best night of my life. I’ve loved you since we were kids. Even when I was dating those stupid boys, I was always thinking about you. You’ve always made me feel safe… and now you make me feel so fucking wanted.”
Her words hit me straight in the heart, and straight between my legs.
“I’ve been in love with you for years too, Anna,” I confessed, stroking her cheek. “Every time you slept over, I had to stop myself from touching you. I used to finger myself thinking about eating your pussy while you were in the next room.”
Anna’s cheeks flushed deep red, but her eyes darkened with fresh arousal.
“Show me how much you want me today,” she whispered. “I want you to do anything you want to me. I trust you completely.”
That was all the permission I needed.
We spent the next hour in the shower together - soaping each other’s bodies, kissing under the hot water, fingering each other until we both came hard against the tiles. Anna dropped to her knees and ate me out while the water cascaded over us, her tongue working my clit until I was shaking and screaming her name.
After drying off, we moved back to the bed, still naked and dripping with need. I pulled out my laptop again.
“Want to watch something new?” I asked, my voice low.
Anna nodded eagerly. “Something dirtier this time.”
We searched for lesbian anal play videos. As the scenes played - girls rimming each other, slowly working toys into tight asses, moaning in pure ecstasy - I felt Anna’s breathing change. She was squirming beside me, thighs pressing together.
“Does that turn you on?” I asked, kissing her neck.
She bit her lip. “I… I’ve never tried anal before. But watching it… it makes me so wet.”
I smiled and whispered in her ear, “Then let’s try it together. I’ll be gentle at first. I want to make you feel things you’ve never felt.”
Anna looked nervous but incredibly excited. “Okay… but promise you’ll stop if I don’t like it?”
“Always, baby. You’re safe with me.”
I laid her down on her back and kissed her deeply, reassuring her with my lips and hands. I spent a long time warming her up - sucking on her perfect tits, licking her pussy until she was dripping and moaning loudly again. Her juices were running down to her tight little asshole, making everything nice and slick.
I grabbed a bottle of lube from my nightstand and coated my fingers generously.
“Relax for me,” I cooed, kissing the inside of her thigh.
I circled her puckered little hole with one slick finger. Anna gasped at the new sensation. I kept licking her clit slowly while gently pressing my finger against her ass.
“Fuck… that feels weird but good,” she moaned.
I pushed the tip of my finger inside her tight virgin ass. Anna’s eyes widened and she let out a long, shaky moan.
“Oh my god, Ricky…”
I moved slowly, letting her adjust while my tongue worked her swollen clit. Inch by inch, my finger slid deeper into her hot, incredibly tight asshole. The feeling of her ring clenching around my finger was driving me wild.
When I had one full finger buried in her ass, I started moving it gently in and out. Anna’s moans became louder, more animalistic.
“Shit… it’s so intense,” she whimpered. “Don’t stop licking me…”
I added more lube and worked a second finger into her ass. Her pussy was gushing now, dripping onto the sheets. The wet, squelching sounds of my fingers fucking her asshole mixed with the obscene noises of me devouring her cunt.
Anna’s hips started rocking back against my hand. She was starting to enjoy it.
“Faster…” she begged.
I obliged, fingering her ass harder while sucking hard on her clit. Anna’s body began trembling violently.
“I think I’m gonna cum… oh fuck, it feels different… deeper!”
Her orgasm hit her like a tsunami. Her asshole clenched rhythmically around my fingers as she screamed my name, her pussy squirting all over my face. It was one of the most powerful orgasms I had ever seen her have.
I gently pulled my fingers out and climbed up to kiss her. She attacked my mouth hungrily, tasting herself on my tongue.
“Your turn,” she said breathlessly, eyes gleaming with lust. “I want to try on you too.”
We switched positions. Anna was surprisingly eager. She licked my pussy first, getting me soaked, then poured lube all over my ass. Her fingers were tentative at first, but she quickly grew confident.
When she pushed one finger into my asshole while sucking my clit, I moaned loudly. The dual stimulation was incredible. Anna added a second finger, stretching me open, fucking my ass with steady strokes while her tongue flicked rapidly over my clit.
“God, Anna… you’re so good at this,” I groaned, grinding against her face.
She finger-fucked my ass harder, curling her fingers, hitting new sensitive spots inside me. The pressure built fast and intense.
“I’m cumming… fuck, I’m cumming in your mouth!”
My orgasm exploded through me. My asshole pulsed around her fingers as I flooded her tongue with my juices.
We were both panting, covered in sweat and cum, but the hunger was far from satisfied.
I reached for my vibrator again - the thick rabbit one - but this time I had something else in mind too. I had a smaller, smooth anal plug and a strap-on harness I had bought but never used.
“Want to try something even dirtier?” I asked, holding up the toys.
Anna’s eyes lit up with a mix of fear and excitement. “Yes… I want you to fuck me. All of me.”
I spent the next twenty minutes preparing her. I ate her pussy and ass at the same time - rimming her tight hole with my tongue while fingering her cunt. Anna was moaning like a whore now, completely lost in pleasure.
When she was relaxed and dripping, I lubed up the anal plug and slowly worked it into her ass. She gasped and pushed back against it, taking it fully with a deep groan.
Then I put on the strap-on - a realistic 7-inch dildo. I positioned myself between her legs and rubbed the head against her soaked pussy.
“Ready, baby?” I asked.
“Fuck me, Ricky. Please.”
I thrust into her pussy in one smooth stroke. Anna cried out in pleasure. With the plug still buried in her ass, her pussy felt even tighter. I fucked her hard, deep strokes that made her tits bounce. The base of the plug moved with every thrust, stimulating her from both holes.
“Harder!” she begged.
I pounded her relentlessly, our bodies slapping together wetly. Anna’s moans were nonstop.
Then I slowly pulled the plug out of her ass and replaced it with the tip of my strap-on, now slick with her pussy juices.
“Relax… breathe,” I whispered.
I pushed forward very slowly. Anna’s eyes rolled back as the thick head popped past her tight ring.
“Oh fuuuuck… it’s so big…” she whimpered.
I stayed still, letting her adjust, kissing her softly. Then I started moving - gentle thrusts at first, then deeper and faster as she started pushing back to meet me.
Soon I was fucking Anna’s virgin ass with long, steady strokes. The sight of my dildo disappearing into her tight little asshole was the hottest thing I had ever seen. Her pussy was dripping onto the sheets, completely untouched.
“Play with your clit, baby,” I commanded.
Anna obeyed, rubbing her swollen clit furiously while I fucked her ass harder.
Her orgasm built fast and intense.
“I’m gonna cum with your cock in my ass… oh my god, Ricky!”
She exploded. Her asshole clenched so tightly around the dildo that I could barely move it. Anna screamed, her whole body convulsing as a powerful anal orgasm ripped through her. She squirted hard, soaking both of us.
I pulled out gently and we collapsed together, kissing passionately.
But we weren’t finished yet.
I put the strap-on on Anna next. She fucked my pussy first, then, after plenty of lube and patience, she took my ass too. Feeling her thrusting into me while we looked into each other’s eyes was incredibly intimate and filthy at the same time.
We spent the entire day in bed - fucking, licking, fingering, using toys, exploring every hole. We tried scissoring with the anal plug still inside one of us. We 69’d while fingering each other’s asses. We came over and over until our voices were hoarse and our bodies were trembling with exhaustion and pleasure.
As the sun began to set, we finally lay still, wrapped in each other’s arms, bodies sticky and marked with love bites.
Anna traced her fingers over my breasts and whispered, “This feels like the start of something real, Ricky. Not just sex. I want to be with you. Like… girlfriends. I don’t care what anyone thinks. You’ve always been my safe place. Now you’re my everything.”
Tears filled my eyes as I pulled her closer.
“I’ve waited my whole life for you, Anna. You’re mine now. Every part of you - your heart, your pussy, your tight little ass… all mine.”
We kissed slowly, deeply, full of love and raw lust.
That night we fell asleep again tangled together, my fingers lazily resting on her ass, hers cupping my breast.
Two best friends from elementary school had finally crossed every forbidden line. What started as a innocent porn night had turned into the most intense, taboo, and beautiful lesbian love affair either of us could imagine.
And we both knew - this was only the beginning.