Skip to content It was summer break, and I didn’t have any real plans, except for spending time with my girlfriend. We had just started dating during spring break. She was gorgeous, slim, firm, and always attractive. But one thing always left me disappointed. She wouldn’t do anal.
She kept saying I was too big, that it would just hurt. No matter how much I hinted or asked, she wasn’t having it. Anal had always been one of my biggest fantasies. The only thing that topped it was the thought of my mother, a forty-year-old, drop-dead gorgeous MILF. Although those fantasies were something I was ashamed of, and not something I’d like to talk about to anyone.
I was sitting at my desk, still half-distracted after browsing some stepmom anal porn, when I glanced out the window. There she was, out in the yard. You couldn’t blame me for my incest fantasies. My mother wasn’t just attractive. She was magnetic. Everything about her pulled me in. She was a personal trainer, so her body was a walking advertisement for what she did. Her breasts were a modest B-cup, not too saggy from what I could tell, and she loved wearing push-up bras. They always gave her that extra lift that made it hard not to stare.
She had dark blonde hair that still held its youthful color. At five foot eleven, she was only two inches shorter than me. But her ass was what really stole the spotlight. It was perfectly shaped, high and round, the kind of ass made for tight leggings. Every movement made it bounce just enough to make me lose focus and pitch a tent. Her face was sweet and womanly, but that body, especially her lower half, was a work of art.
Right now, she was going through her stretching routine. She bent forward, legs straight, palms flat on the grass. Her leggings pulled tight across her ass, and the position gave me a full view of her mesmerizing curves. I could even make out the faint outline of a thong beneath the fabric, and also, her camel toe. My cock stiffened almost instantly.
I imagined walking out there, grabbing her by the hips, and pulling those leggings down to expose that perfect rear. I pictured myself easing into her, watching her arch her back and moan as she adjusted to my size. My hand had drifted to my waistband without even realizing it. Everything was wrong about this, but despite having a girlfriend, I still felt sexually deprived.
I had never dared to say a word to my mother. I didn’t want to make it awkward. Still, some part of me believed she wouldn’t judge me. She might actually listen. My mother wasn’t the judgemental type, and we were quite open about sex and relationships.
She suddenly turned around mid-stretch and caught me staring. My eyes widened, and I quickly looked away, cheeks burning with shame. She smirked, that playful curve to her lips making it even worse.
“Leo, could you grab me a towel from the bathroom?” Mom asked as if nothing had happened.
“Yeah, sure,” I said, my voice cracking slightly from nerves.
I stepped inside her bathroom, and the moment I stepped in, I was hit by the clean scent of citrus and flowers. Everything was glistening clean like a showroom, towels folded perfectly, not a hair in sight and even a little potted plant near the mirror.
I opened the cabinet to look for the towel, but something else caught my eye first. A pink diamond butt plug, sitting next to a purple dildo. They weren’t hidden, just tucked casually behind some bath salts and lotion. I blinked, not sure if I was seeing it right. But I was.
She’d been single for years, so I wasn’t sure why she needed a butt plug. But seeing her toys now lit a fire inside me. I pictured her bent over this very counter, slowly sliding that plug in, teasing herself and preparing for raw anal sex. My cock twitched again, stiffening in my shorts.
Did she have an anal fetish too? Was that why she kept herself in such shape? For her own pleasure and her own routines? I’d heard her masturbate a couple of times during the night, but I’d never imagined she’d like it in the backdoor as well.
I shook off the perverted thought and grabbed the towel before I embarrassed myself by getting lost in the fantasy too long.
Back outside, she was wiping sweat from her brow with the back of her arm. Her top clung to her, just enough to show the outline of her toned body. She looked hotter than ever, her dark blonde hair cascading down her back as she’d just untied her ponytail.
“Thanks,” she said, taking the towel from my hand.
“No problem,” I muttered, trying not to sound like I’d just fantasized about her seconds ago.
She dabbed at her face, then looked up at me again. “Heading over to see your girlfriend later?”
“Nah, I’ll see her tomorrow.”
Her smile grew just a little. “That’s nice. I’m happy for you two.” She slung the towel over her shoulder and stretched her arms behind her back. “I should start making dinner.”
Then she turned around and walked toward the door, and I couldn’t help watching her ass sway as she went.
*****
The next day, I got back home late in the evening. I had spent the afternoon with my girlfriend, hoping she’d finally change her mind. I’d tried everything, gentle persuasion, touching her intimately, even showing her some tutorials, but when I brought up anal again, she shut it down right away, just like before.
The rejection clung to me like humidity. I was frustrated, my lust unresolved. As I neared my driveway, I slowed down, the heat of the day finally giving way to the cool stillness of evening.
That’s when I heard it.
I stopped walking. There it was again. A sensual moan as if a woman was masturbating. I stood right in front of my house, it was coming from my mother’s bedroom.
I looked over and saw her bedroom window cracked open, the thin curtains pulled shut which she rarely did. The light inside was dim, and I suspected she was masturbating.
I quietly entered and then headed upstairs, the sounds of her moans rising. Her bedroom door was open just enough, the frame offering a perfect view into her world.
She was lying back on the bed, legs spread and completely naked.
Her body looked sculpted by a goddamn artist. Toned thighs, long legs, a flat stomach with a subtle four-pack, and those gorgeous B-cup breasts, soft but high topped with thick, peachy nipples. Her skin had a healthy glow, a light sheen of sweat across her chest and brow.
But it wasn’t just her body that made me look in awe. The butt plug lay discarded by her side, glinting faintly of lube.
She had a purple vibrator buzzing inside her soaked pussy, and in her other hand, she was sliding a thick dildo in and out of her ass.
I popped wood instantly as I watched in disbelief. My eyes fixed on her gorgeous butthole, and the lucky dildo disappeared and reappeared inside her ass. It was almost the exact size of mine. Maybe a hair shorter, but just as thick. And she was taking it with ease and pleasure. Fucking herself deeply without hesitation.
So all this time, she had an anal fetish. And she could take a cock like mine. I wasn’t doomed after all. Anal sex was possible.
That thought alone nearly made me lose it.
She moaned again, louder now. Her thighs clenched, back arching as she brought herself closer to the peak. Her hips bucked slightly, and she flipped a switch on the vibrator so it became stronger, the sound muffled inside her pussy. She threw her head back and squirmed in pleasure. Then it happened. She came. She let out a deep, drawn-out moan as her orgasm tore through her. Her legs trembled, toes curled and she slid the dildo into the depths of her rosebud. She was loud but it was completely authentic. The kind of climax that leaves you shaking and not rolling your eyes because of bad acting.
I stepped back immediately, suddenly aware of my presence. I made my way down the stairs as fast as I could without making noise and then I pretended I’d just arrived. “Mom, I’m home!”
“Give me a minute!” she called back, her voice slightly panicked.
I heard quick footsteps upstairs, followed by the sound of the bathroom door closing. She moved fast, probably trying to clean herself up after what I had just witnessed. I kept my expression neutral, pretending I hadn’t heard or seen a thing. But scenes of her masturbating were seared into my horny mind.
A few minutes later, she came down the stairs dressed in a light summer dress. Wearing her hair loose, she wore perfume, something feminine and floral, but it wasn’t enough to hide the other scent lingering faintly in the air. It was the scent of her arousal, still fresh and warm, blending with the perfume like something that made me even hornier.
She glanced at me with a frown. “You okay? You look a little … off.”
I scratched my neck. “Yeah. Just tired, I guess.”
She sat down next to me on the couch, close enough for our legs to touch. Her hand rested gently on my thigh, and I glanced between her legs, thinking of her pussy that was most likely still wet and swollen. “You know we can talk about anything, right?”
I nodded, swallowing the lump in my throat. “I know.”
“Did the date go okay?”
“Yeah,” I said quickly. “It was fine.”
Her hand stayed on my thigh. “Have you two … been intimate yet?”
My cheeks flushed. I nodded. “Yeah, we have. A couple times.”
She smiled proudly. “That’s good.”
I looked down, then added, “But she’s been complaining about pain.”
“Hmm,” she murmured, squeezing my leg just a little. “If she’s new to it, it can hurt at first. Especially if she’s a virgin, or hasn’t tried much.”
Her voice was calm, matter-of-fact, but the way she said it made me aroused. I loved having this close relationship with her even if I wanted to come closer. “It’s just a bit clumsy.”
“She’ll get used to it,” she added. “The body just needs time to adjust.”
I looked at her again and smiled. She was so open and so easy to talk to. It felt good to say it out loud, to not be judged.
“Thanks,” I said quietly.
She leaned in and kissed my forehead, leaving a damp patch of her sweet skin behind. “Don’t mention it. I’ll go start dinner.”
As she stood up and walked into the kitchen, her dress swayed behind her, and I sat there for a moment, not sure what to do with my raging hard-on.
*****
After dinner, I couldn’t take it anymore. I had tried to stay calm and act normal, but the fresh memory of her moaning, her naked body stretched across the bed and the way she took that dildo like it was nothing. It was burned into my mind. Every little glance and every intimate touch during dinner only added fuel to the fire. She was so close, so casual like none of it ever happened. But I’d seen everything.
I rushed up to my room, closed the door, and sat down on my bed with my laptop. My hand was already in my pants before the screen loaded. I searched quickly, “stepmom anal porn,” and hit play.
The video started. A curvy woman, close in age and build to Mom, bent over with her ass in the air, moaning as she took it deep. It was too perfect. I stroked myself fast, the images mixing with what I’d seen the night before. I moaned, body tensing, my orgasm building hard and fast.
Just as I reached the edge, the door creaked open.
“Leo—”
I gasped and scrambled to cover myself.
Mom stood frozen in the doorway, eyes wide. “Oh my God, sorry!”
She turned, trying to step back, but the damage was already done. My face was on fire.
“I—I thought you were downstairs,” I mumbled, pulling the blanket over my lap.
She lingered just outside the room, not quite shutting the door. “I didn’t mean to walk in on you. I’m really sorry.”
“It’s fine,” I muttered, though I felt like I wanted to disappear.
“Is it safe to come in?”
“Sure,” I said.
Slowly, she stepped back in, eyes avoiding mine for a moment. “Can I ask you something?”
I nodded.
She sat down carefully at the edge of the bed, still keeping her eyes gentle. “Why are you watching porn like that? I mean … you have a girlfriend, right?”
The moment stretched too long. I figured I might as well be honest now. “I have an anal fetish,” I admitted. “And she won’t do it. She says it hurts and refuses every time.”
Mom looked at me thoughtfully, her fingers brushing a loose strand of hair behind her ear. “So you’re left … wanting.”
I nodded again, still embarrassed but also relieved to finally say it out loud.
She sighed, eyes on her hands for a moment. “I get it. Actually… I really get it.”
I looked at her.
She smiled a little like she was admitting a secret. “I’ve always loved anal. Not everyone does, but for me, it’s special, deep and intense in a different way. I miss it, a lot. And hearing you say that… Well, I feel bad for you. Wanting something so badly and not being able to explore it, even though you’re trying.”
“Yeah, that’s my situation,” I said.
Mom bit her lower lip, giving me a curious yet horny look. “I’m wondering… is it possible your size is the issue? That maybe she’s right about it being too much for her?”
I blinked at the unexpected question. “I … I don’t know. Maybe?”
“Would you mind if I …” she looked for the right words, her voice dropping lower. “Would you let me see it? Just so I can tell if that’s really the problem?”
This was crossing a line, but I couldn’t deny how much I wanted it. “Are you sure?”
She nodded, her eyes holding mine. “I’m just trying to help, Leo. You’re my son and I want the best for you.”
After a moment’s hesitation, I slowly pulled back the blanket. My shorts were still unzipped from before, and with trembling hands, I revealed myself to her. My cock rose like a snake and hardened like a sword. It pointed right at her, throbbing and achingly hard.
Her eyes widened slightly, and she leaned in closer. “May I?” she asked, her hand hovering right above the purple tip.
I nodded, barely breathing. When her fingers wrapped around me, I nearly jumped. Her touch was soft and caring, exploring my length like a sex teacher.
“It’s beautiful,” she whispered, her thumb tracing a vein.
The taboo thrill of my mother’s hand on me was overwhelming. I should have felt guilt or shame, but instead, I felt only pleasure and a strange sense of rightness.
“So,” I asked, my voice strained as she lovingly stroked me. “Is it … is it too big?”
Her hand reached the sensitive head, stopping there. “For a young virgin? Yes, I can see why she’s hesitant.” Her hand then slid down to the base. “But for an experienced woman? Not at all.”
“Could you…” I swallowed hard and gathered my wits. “Could you show me?”
A slow grin spread across her face as if she’d been waiting for that question herself. “Are you sure that’s what you want?”
“Yes.”
She mulled it over while stroking me slowly. “This stays between us, Leo. Just you and me. No one else can ever know.”
“I promise,” I said immediately.
“Come, let’s go to my bedroom.” She rose to her feet, took my hand, and led me across the hall to her bedroom. The same room where hours earlier I’d watched her masturbate.
As she closed the door behind us, I couldn’t hold it in anymore. “Mom, I need to tell you something. Earlier, I saw you. When I came home. Your door was open, and I saw you masturbating.”
Her cheeks flushed pink, and she gave me a look that was both embarrassed and aroused. “You watched me?”
“Yes,” I said.
She smiled. “It’s okay. It’s natural to be curious.” She stepped closer. “Did you like what you saw?”
“God, yes,” I admitted. “I was a bit surprised you used a dildo in your ass though.”
“It’s because I love anal, and I have to touch myself there to fully orgasm.”
“Wow, that’s hot.”
“I’m glad you like it,” she said with a grin. She moved to her nightstand and pulled out a bottle of clear gel. “Anal lube,” she explained, showing me the bottle. “Specially formulated for this kind of pleasure.”
She set it on the bed and reached for the hem of her dress. She pulled it over her head, revealing her naked body underneath. She hadn’t bothered with underwear after her earlier activities.
“You’re… perfect,” I whispered, taking in every curve and every line of her athletic form. Her breasts were perky and firm, her stomach flat with defined muscles, and her thighs strong and shapely.
“Thank you, sweetie,” she smiled, turning around slowly. “I work hard for this body.”
“I know.”
She climbed onto the bed and got on all fours, her perfect ass presented to me. I stood frozen, mesmerized by the sight. I found it hard to believe. Not only would my anal fantasy be fulfilled but my incest fantasy as well.
“Hand me the lube,” she instructed.
I passed her the bottle. She squeezed a generous amount onto her fingers and reached behind herself. I watched, mesmerized, as she circled her puckered entrance, massaging the gel around and then slowly pressing a finger inside.
“God, Mom, that’s the sexiest thing I’ve ever seen,” I murmured.
She looked back at me over her shoulder. “Come here, you need lube on your cock too.”
I came closer, my cock briefly slapping her right thigh. She filled her right hand and massaged it onto my cock in slow, sensual strokes.
“Try to push a finger into my ass, see if it slides well.”
I did as she said, gently pushing my finger into her butthole, parting her rosebud and sliding inside her warm backdoor. “Wow … you feel amazing.”
“That means I’m ready,” she said with a giggle.
I positioned myself behind her, my hands shaking as I gripped her hips.
“Press the tip against me,” she instructed. “Don’t push yet, just let me feel you there.”
I did as she said, the head of my cock nudging against her lubricated entrance. She pushed back slightly, allowing just the tip to enter.
“Oh,” she gasped. “That’s it. Now wait.”
I held still, fighting every instinct to thrust forward. Her body gradually relaxed around me.
“A little more now,” she whispered.
Inch by inch, she guided me deeper, teaching me with quiet words and soft moans about how to enter her without causing pain. The tight heat engulfing me was unlike anything I’d ever felt.
“You’re doing so well,” she praised, her voice breaking with pleasure. “Now you can move. Slowly at first.”
I began to thrust, gentle, shallow movements that gradually deepened as her body accepted more of me. The sensation was indescribable, tighter than any pussy plus the taboo of it all heightening every sensation.
“Harder now,” she urged, pushing back against me. “I can take it. In fact, I want it all.”
I increased my pace, my hands digging into her hips as I drove into her.
Her moans grew louder as I thrust deeper, the ring of her ass gripping me perfectly. The lube made everything slick and perfect, my cock sliding in and out with just the right amount of resistance.
“Oh god, Leo,” she cried out, her fingers digging into the sheets. “You’re so deep … fuck me harder, baby.”
I obeyed, increasing my pace until I was pounding into her, the taboo thrill of fucking my mother’s ass heightened the pleasure. Her perfect ass jiggled with each impact.
“I’m getting close,” I groaned, feeling the pressure building.
“It’s fine sweetie, come inside me,” she urged, looking back at me with lust-filled eyes. “I want to feel you fill me up.”
With a final thrust, I buried myself to the hilt and exploded, pumping rope after rope of hot cum deep into her ass. The orgasm was unlike anything I’d ever experienced, intense waves of pleasure that seemed to go on forever, making my entire body shake.
“Fuck, Mom,” I gasped, collapsing against her back with my cock still stuffed inside her. “I could barely even last a minute.”
“That’s fine.” She smiled, reaching back to stroke my hair. “Let me clean you up.”
I pulled out from her slick butthole. She turned around and her eyes were hungry as she took my still-hard cock into her mouth. The sight of my mother sucking me clean after I’d just been inside her ass was almost enough to make me hard again immediately. Her tongue swirled around my shaft, removing every trace of lube and cum.
“There,” she said, releasing me with a pop. “All clean … Can you please clean my butt? That was one hell of a load.”
I smiled, still dazed from the intensity of what we’d just done. I grabbed a washcloth from her nightstand. I gently cleaned her, marveling at how her body had accommodated me so perfectly.
“Thank you,” I told her. “That was the most amazing experience of my life.”
“It felt just as good for me, Leo. You have no idea how long I’ve wanted this.”
“Really?” I asked, surprised.
She nodded. “I’m so grateful I could fulfill one of your fantasies. And mine too, if I’m being honest. If your girlfriend doesn’t want anal sex. You can always do it with me.”
“Thank you, Mom.”
She pulled me in a warm, nude hug, mashing her breasts against my chest. “I love you, Leo.”
“I love you too, Mom.”
The end.
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