Mom's hot friend let me fuck her during a sleepover ... next night, we did anal (part 2) [F41/M20] [MILF] [raw anal] [Age gap]
Part 1: Mom's hot friend let me fuck her during a sleepover.
The next morning, I woke up with my face buried in a floral pillow and the mother of all morning wood pressed hard against a warm, jiggly wall of ass. Tori had somehow migrated backwards in her sleep, and her body molded against mine, her nightie hiked up until nothing but smooth, bare thigh and a sliver of pink ran across my horizon. My cock was caught in the perfect slot between her cheeks, and when I shifted, she moaned quietly but didn’t move away.
For a second, I stayed like that, not sure if it was safer to fake sleep or try to escape before I came right in her crack. But then Tori shifted, pushing her hips back. She wiggled, just enough to really wedge me in, and then whispered, “You awake, baby boy?”
I was very awake. “Can’t sleep with all this going on,” I whispered back, bumping my hips into her for emphasis.
She giggled, deep and sleepy. “Mmm. Naughty.” Then, quieter, “If your mom’s still out, we could do a quickie?”
I became so excited, I grabbed her cheeks and couldn’t wait to push back into her pussy … but then the sound of footsteps and the soft clink of dishes told me that was not the case. I rolled away just in time for Mom to knock and pop the door open.
“Morning!” she called. “Breakfast’s in half an hour. Hope you two slept okay. Tori, you need anything? Aspirin?”
Tori rolled onto her back, giving Mom a full view of her nightie and most of a nipple. “I’m perfect, Sarah. Noah gave me the best massage last night,” she lied with a wink, “slept like a log.”
Mom beamed. “That’s my boy. He’s got the magic hands.” Then to me, “Come down when you’re up. I’ll make eggs.”
She closed the door and left me rock hard.
Tori turned to me, eyes still heavy with sleep and lust. She stretched, then pulled her knees up, spreading the nightie so it bunched around her hips. The pink thong was gone, and her ass, even lying down, was insane. She patted the curve of it.
I crawled over, not fully believing I was awake, and ran my hand up her thigh to her hip, squeezing gently. She arched her back and spread her legs a little wider, letting me slide my fingers between her cheeks. Her skin was so warm, almost fever-hot.
She whispered, “You ever want to try the other hole?” She said it like she was offering me a stick of gum.
I froze. “You’d… let me?”
She smiled, eyes shining. “Why not? You’ve got the hands and cock for it. But not now, baby. We don’t have time.” She grabbed my wrist and guided my finger to her asshole, circling, teasing, making herself shiver. “Tonight, maybe. Would you like that?”
My brain locked up. “Fuck yes.”
She sucked my index finger, then pressed it back, letting me rub the tight ring and wishing it was my erection instead. She closed her eyes, enjoying it for a minute, then pushed my hand away and sat up. “No jerking off today, okay? I want you pent up for me. Promise?”
She must have read the yes on my face, because she grinned and slapped my thigh. “Good. Go shower, your mom will know if you take too long, so don’t even think about it.”
She was right. I got out of bed, and I went to the shower, but it took all my energy to not break my promise. My dick was red and angry, leaking, and every time I thought about Tori’s offer, I nearly blew.
*****
Breakfast happened quickly, and thank god, I just wanted it to be night again. Mom set up a little station on the terrace, fresh fruit and yogurt and eggs, and went back inside to make a group text about brunch plans with her yoga friends. It was just me and Tori on the deck, sun slicing through the slats.
Tori wore a new bikini, electric blue, with straps that crisscrossed her chest like duct tape on a watermelon. She pretended to ignore me, scrolling her phone and eating grapes, but every time I looked away, she’d catch me and do a little shimmy, making the fabric dig in deeper.
By noon, I had to get away from her or risk humiliation. I grabbed a book and tried to read on the terrace, but Tori found me, plopping down next to me.
She swung one leg over mine, then, “Whoops, didn’t see you there,” and settled her ass directly onto my lap. The book nearly flew out of my hands.
She ground her hips in a slow, sensual circle, like she was making herself comfortable on a chair … or a strip tease. “Sorry. Didn’t mean to squish you.”
“It’s fine,” I said, voice cracking.
She leaned in so her lips grazed my ear. “I’m going to make it so hard for you today, Noah. Think you can handle it?”
I wanted to say yes, but my cock was making its own argument. Tori pressed down, my cock finding the crack in her ass, then got up and stretched, flashing me a full view of her round, jiggly ass. “Me and your mom are doing yoga out here in an hour. If you want to watch, I’ll do extra downward dog for you.”
I was dying. “I’ll… I’ll be upstairs.”
She gave me a look that said, “You better be.”
I tried to read, but Tori and Mom came out for yoga and the show was better than any book. Mom did her usual routine, lithe and strong, but Tori went all out—every pose designed to flaunt. She bent low for downward dog, spreading her feet wide, her ass in the air, vibrating as she bounced on the balls of her feet. The bikini bottom disappeared between her cheeks, and she kept glancing back at me through her legs, making a show of adjusting the strap every time it slipped. When she did warrior pose, her hips canted and the top nearly popped off.
Mom caught me staring more than once and just smiled. “It’s okay, hon, Tori’s always been a show-off.”
I almost came right there.
The rest of the day was more of the same. Every time I passed Tori in the house, she’d manage to “accidentally” brush her chest against me, or bend over in the fridge so I caught a full view of her ass. By dinnertime, my head was spinning and my balls felt like overfilled water balloons.
After dinner, we watched some comedy till Mom announced, “I’m beat. Early bedtime for me.” She kissed my cheek, hugged Tori, and padded off in her slippers. Tori and I cleaned up the kitchen together, which mostly meant she watched me load the dishwasher while sipping wine and leaning against the counter, her ass making a perfect perch.
When the last glass was away, she tilted her head. “I think your mom likes me,” she said.
“I think she trusts you,” I replied, which, in retrospect, was maybe the funniest thing I’d ever said.
Tori licked her lips. “Let’s not abuse that trust. You should go to your room and wait for me. I need a shower.”
I did as told, nervous and excited, my hands shaking as I closed my door behind me. I stripped down to boxers, sat on the bed, and waited, cock already stirring. My phone buzzed, a DM from Tori.
Be a good boy. Don’t touch yourself till I get there.
I squeezed my eyes shut and chucked the phone away, lying back and hoping I didn’t leak pre all over my sheets. When the door finally opened, Tori came inside in a short purple bathrobe, her wet hair piled up in a towel, face glowing clean. She carried a plastic bag, and set it on my desk.
She closed the door behind her, twisted the lock, and turned to me, eyes burning. “So. Are you ready to be a little bad?”
I nodded. Gosh that woman was such a MILF.
She dropped the robe. Nothing underneath. Her skin, scrubbed clean, looked even darker and softer in the lamplight. Her hips and thighs were thick and strong, her huge ass gleaming. Her tits hung heavy like two bells, nipples already hard and suckable.
She crossed the room in three steps and straddled me, hands on my shoulders. “Tell me, have you ever fucked a woman in the ass?”
I shook my head.
She grinned. “Perfect. I’ll teach you.” She opened the bag and pulled out a box of lube. “You’re going to make this ass shine.”
She kneeled on my bed, ass up, and spread her cheeks with both hands. I got behind her, my hands trembling. She passed me the bottle.
“Go slow. Use a lot. Warm it up first.” Her tone was clinical, almost maternal, which made my cock twitch even harder.
I squeezed a puddle into my palm and rubbed my hands together, then slid them up the backs of her thighs to her ass. I kneaded the soft, heavy globes, spreading the slick around, then up and down the crack. Her asshole winked at me, a dark, perfect pucker. I circled it with my thumb, and she shivered and pushed back, making a low, satisfied noise.
“Good boy. Don’t be afraid to get in there.”
I applied more lube, working it gently into the ring. Tori moaned and arched her back, her cheeks rippled and twitched. I couldn’t help myself. I bent in and brushed my lips around the rim, then flicked my tongue across it.
She shuddered, her hands tightening on the sheets, hissing, “God, yes, eat it.” So I did. I worked her with my tongue, slow circles at first, then deeper, pushing in and out while my slicked hands groped and squished her cheeks. Her ass was so soft and strong at once, a living thing. I buried my face in it, licking and sucking.
When I finally came up for air, she looked back at me, eyes glazed, mouth open. “Now stroke that cock for me, get it all nice and shiny.” I did, glopping a double handful of lube over my shaft, stroking until I was slippery and veiny and hard as stone. Tori’s eyes went wide. “Jesus, okay. You’re gonna have to go slow.” She grabbed the pillow and hugged it, settling her hips just so, her ass high and ready.
I pressed the swollen, lubed head of my cock against her tight little asshole and started pushing. The ring resisted at first, clenched and hot, but I kept steady pressure until it slowly gave way. Inch by inch, her ass swallowed me. The feeling was insane, scorching hot, tight, gripping every ridge of my shaft. Tori let out a long, deep groan into the pillow as I sank deeper.
“Fuuuck… slow, baby. Let me feel all of you,” she moaned, her voice husky and strained.
I watched in stunned awe as her massive cheeks spread around my cock. The sight of her thick, tanned ass taking every inch was better than any porn I’d ever seen. When my hips finally pressed flush against her soft, heavy cheeks, I was buried to the balls inside her. Her asshole fluttered and squeezed around the base of my cock.
I stayed there for a moment, letting her adjust, my hands gripping the soft flesh of her hips. Then I started fucking, slow, careful strokes at first, pulling back until just the head stretched her ring before sliding back in. Each thrust made her enormous ass ripple and jiggle. The lube made wet, filthy sounds as I fucked her.
Tori pushed back to meet me. “That’s it… fuck my ass. Harder, Noah. I can take it.”
I picked up the pace, my hips slapping against her cheeks louder now. The way her beautiful ass bounced and clapped with every thrust was hypnotic. I spanked her right cheek hard, watching the red print bloom across the soft skin. She cried out in pleasure and shoved back even harder.
“Again! Spank my ass while you fuck it!”
I alternated cheeks, smacking them as I drove into her deeper. Her moans grew louder, muffled by the pillow.
“Tell me how it feels,” I groaned.
“So fucking full… your cock is stretching my asshole so good, baby. Don’t stop, wreck it.”
I lost myself in the rhythm. I fucked her harder, watching her massive ass shake and wobble wildly with every impact. The sight of my slick cock disappearing between those perfect, jiggling cheeks again and again pushed me closer to the edge. I reached under her and rubbed her swollen clit while I pounded her ass.
Tori started shaking. “I’m gonna cum… oh fuck, I’m cumming with your cock in my ass!”
Her asshole clenched violently around me as she came, squeezing and pulsing in powerful waves. The pressure was too much. I buried myself as deep as I could go, my balls pressed tight against her dripping pussy, and exploded.
I came hard, pulsing rope after thick rope of cum deep inside her raw ass. The orgasm hit me hard, my hips jerking as I flooded her asshole with everything I had. I kept thrusting through it, grinding deep, pumping every last drop into her until my balls were empty.
When I finally pulled out, her asshole stayed open for a second, red and glistening, before slowly contracting. A thick white trickle of my cum leaked out of her wrecked hole and ran down over her pussy lips. Tori reached back with one hand, spread her cheek, and pushed, forcing more of my load to drip out.
She looked back at me over her shoulder, flushed and satisfied, a wicked smile on her face.
“Mmm… good boy. You really filled Mommy’s friend’s ass up.” She wiggled her hips, making the cum leak even more. “I can feel it sloshing inside me.”
I collapsed beside her, breathing hard, my cock still twitching. Tori rolled onto her side and pulled me close, pressing her cum-filled ass against my spent dick. She kissed me softly, then whispered in my ear.
“Five more nights, baby… and I’m nowhere near done with you.”
I knew I was in Heaven.
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