Chapter 14: MILF was Too Tight

I pushed.

Nothing.

Just that tiny pink ring kissing my tip, clenching like it was trying to push me out before I even got in. I grabbed her hips harder, pulled her back, and leaned my weight in slow. The head flattened against her hole, spreading it a little, but still no give.

“Fuck,” I hissed through my teeth. “This asshole is fighting me.”

Lily whimpered, face buried in the pillow, fists twisting the sheets. “Keep going… please…”

I spat again, thick and messy, let it drip down her crack, rubbed it around the rim with my thumb until it was sloppy. Then I pressed again, harder. The very tip sank in maybe half an inch and her whole body locked up.

“AHH—Alex—fuck—it’s too big—” she cried, voice cracking, but her hips still pushed back like she couldn’t help it.

I held her there, locked on that half-inch, letting her feel how wide I was stretching her already. My cock looked obscene against that tiny hole, the rim turned white from the pressure.

“Breathe, baby,” I growled, reaching under her to rub her clit through the soaked nylon. She jolted, moaned loud, and the second she relaxed, pop. The head slipped in.

We both groaned at the same time.

Her ring clamped down so hard I saw stars. Hot, velvet, impossible. I couldn’t move. One inch in and I was already fighting for my life.

“Holy shit,” I rasped, sweat dripping down my chest. “Your ass is trying to choke my dick.”

She was panting, shaking, tears streaking the sheets. “It’s so big…”

I slid my hands up to her tits, squeezed hard, used them like handles and pulled her back while I rocked forward. Another inch. Then another. Every tiny bit was a war. Her asshole fluttered and squeezed like it was trying to push me out and suck me in at the same time.

I leaned over her back, bit her shoulder, and started playing dirty: one hand snaking around to pinch her clit, twisting it slow, the other reaching up to shove two fingers in her mouth. She sucked them like a lifeline, drooling, moaning around them while I fed her another thick inch.

“Look at this,” I snarled, pulling her head back by her hair so she could see us in the mirror across the room. “Look how your tiny virgin asshole is eating my cock. You’re never gonna be the same after this.”

She stared at our reflection, eyes blown wide, lipstick smeared, ass stretched lewd and obscene around me.

I tried one last savage thrust, hips slamming forward, balls slapping the torn nylon, but her asshole clamped down like a fist and shoved me right back out with a filthy, wet pop.

My cock sprang free, angry-red, glistening, throbbing in the air. Her little pink hole gaped for half a second, then snapped shut again, winking at me like it was laughing.

“Motherfucker,” I panted, chest heaving. “This ass is literally unbreakable.”

Lily was shaking, drool on her chin, tears streaking her cheeks, but she still reached back with one trembling hand and spread herself open for me.

“Top drawer,” she gasped, voice wrecked. “Vaseline… please… I bought it for tonight… just use it… I need you all the way in…”

I damn near ripped the drawer out. The little tin was right there, lid already loose like she’d been fingering it earlier thinking about this exact moment. I scooped out a fat glob, smeared it up and down my shaft until I was dripping, then shoved two greasy fingers straight into her hole.

She screamed into the mattress, back arching, ass trying to suck my fingers deeper. I twisted them, scissored them, opened her up while she sobbed and begged.

“More… more…”

I pulled my fingers out with a nasty squelch, slathered another thick load of Vaseline right over her twitching ring, then lined my cock up again, head shining like a fucking weapon.

“Hold yourself open,” I snarled.

She obeyed instantly, both hands spreading her cheeks so wide the torn pantyhose ripped even more. Her greasy, pink hole glistened under the light, begging.

I pushed.

This time the head popped in with one slick, brutal slide. No resistance. Just hot, greasy heaven swallowing me whole.

“Fuuuck yes,” she wailed, voice breaking as I kept going, slow, relentless, feeding her every inch while the Vaseline made the filthiest wet sounds. I didn’t stop until my balls pressed flush against the shredded nylon, cock buried so deep I could feel her heartbeat pulsing around me.

I leaned over her, chest to her back, and licked a tear off her cheek.

“That’s it, baby,” I growled, pulling out slow until just the head stayed in, then slamming balls-deep again. “Now I’m gonna fuck this married, virgin asshole raw while your husband’s on the other side of the planet.”

She screamed, loud enough that I know Autumn heard.

And I started pounding.

I kept fucking her ass slow, deep, filthy strokes, feeling every inch of that virgin ring choke my cock. The Vaseline made it sloppy, wet squelching sounds every time I pulled back and slid home. Lily was bent over in front of me, that perfect fat ass still framed by the torn pantyhose, looking even better naked than it did in that day in the bikini by the pool.

Dream come true.

“Ahhh… ahhhh… Alex… yes…” she moaned, voice high and broken, pushing back to meet every thrust like she was born for it. First time taking dick in her ass and she was already addicted.

I looked down, watched my cock disappear into that tiny red hole over and over, her pussy underneath leaking like a faucet just from the ass-fucking. Clear strings dripping off her clit onto the sheets.

My mind flashed to Autumn outside on the balcony, cigarette glowing, tiny shorts riding up her fat ass, office skirt hugging that criminal waist. One day I’m gonna bend her over her own desk and make her scream louder than this.

But right now? Lily was getting all of me.

I pulled out slow, her hole gaping, winking, begging to be filled again.

“Turn around,” I growled. “Suck your ass off my cock.”

She hesitated one second, cheeks red, then dropped to her knees like a good girl. My cock was shining with Vaseline and her ass, dripping. She looked up at me, eyes watery, then leaned in and licked the head slow, tasting herself.

“Fuck… just like that.”

She moaned, opened wide, took me deep, gagging a little but not stopping. Sucked me clean, tongue swirling, drooling down my shaft like she loved the taste of her own ass on me.

I couldn’t take it anymore.

I pulled her up, ripped the bra off, tore the garter belt and thong clean away, yanked the stockings down and threw everything across the room.

Now she was fully naked. Skin flushed, nipples hard, pussy swollen and dripping. A fucking goddess.

I laid back on the bed, cock straight up, rock-hard and shining.

“Get on me. Reverse. I wanna watch that ass bounce.”

She climbed up, turned around, that perfect fat ass right in my face, and lined my cock with her soaked pussy.

Tried to sink down.

“Fuck… it’s too tight…” she whimpered, circling her hips, trying again.

I grabbed her cheeks, spread her wide. “You haven’t been fucked in months, have you?”

She shook her head, biting her lip. “Not like this… never like this…”

She pushed down again, slow, and this time the head popped in.

Both of us groaned.

She sank lower, inch by inch, moaning louder with every bit, until her ass finally rested on my hips, my cock buried to the root in that starving, velvet pussy.

“Ride me, Lily. Show me how bad you needed this dick.”

She started grinding first, slow circles, ass rolling like a stripper, then up and down, bouncing harder, tits jiggling, head thrown back.

“Alex… oh my god… it’s so deep…”

Her pussy was creaming down my shaft, white and thick, dripping off my balls. Every bounce made her ruined asshole wink at me, still leaking Vaseline and cum.

I slapped her ass hard. “Faster.”

She lost it, bouncing wild, ass clapping loud, moaning like a pornstar, pussy gushing every time she slammed down.

I reached around, rubbed her clit fast, and she screamed, whole body shaking, squirting hard all over my stomach and chest.

Didn’t stop her. She kept riding through it, crying, begging, completely gone.

I grabbed her hips, thrust up hard, meeting every bounce, pounding up into her while she slammed down.

“Yes—please—breed me—fill me—”

One final deep thrust and I exploded, pumping thick ropes straight into her womb while she came again, pussy milking me dry, ass bouncing, toes curling, voice gone raw from screaming.

She collapsed forward, still impaled, trembling, cum already leaking out around my cock.

I pulled her back against my chest, kissed her neck, bit her ear.

I kept that slow, filthy grind going inside her soaked pussy, my cock stirring my own cum deep while she trembled on my chest.

I bit her ear and whispered, “What if I fucked you right in front of your husband?”

Her walls clamped down so hard I almost came again.

She pulled back just enough to look at me, eyes wide, lips swollen. “Huh… what are you saying, Alex?”

I smirked, thrust up slow and deep. “What if he walked in right now… watched me split his wife’s ass open on this dick?”

She moaned loud, way louder than before, pussy gushing fresh cream around me. Her hips started rolling on their own, chasing it.

“Alex… fuck…” she gasped, kissing me hard, tongue sloppy and desperate, nails digging into my shoulders.

I grabbed her ass, spread her cheeks, and ground deeper. “You like that, don’t you? Him seeing how easy you spread these holes for me.”

She whimpered into my mouth, nodding fast, kissing me like she was drowning.

“Yes… oh god yes… I want him to see… want him to know how you own me now…”

Her pussy clenched again, milking me, another orgasm already building just from the thought.

Then a knock came at her door.

We both froze.

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