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Introduction:

My sultry stepmom receives a lesson in extreme ass-stretching

I was right in the middle of finals week at Reed College, and I wasn’t in a good mood. The spring weather was glorious for a Portland campus; the flora was intensely green and in full bloom, and girls were dressed in light summer clothing, which meant that as I drove out of the parking lot, it was hard to miss the legs, cleavage, and everything else that gets a 19-year-old guy’s hormones flowing. I was horny but pissed that I couldn’t stay. I had to drive 30 minutes back home to walk the dog. I’d opted to live at home with my dad and stepmom because I just couldn’t keep up with living expenses anymore, and I often regretted the decision. My stepmom, Cassandra, was a lovely and petite Irish woman, brimming with good intentions, but she never ceased to get on my nerves. I always felt some kind of inexplicable tension between us.

When I arrived home, I noticed that Cassandra’s car was parked in the driveway, which was odd because she typically worked until late in the evening. It was only 2:00 in the afternoon. I sat in my car for a few minutes, unsure, before I finally made my way to the front steps of my stepmom’s house. As I peered through the living room window, I spotted my stepmother dancing by the stereo and really getting into it. The mushy, lazy sounds of Jack Johnson wafted from the speakers. She never seemed to stop playing this album… With the stereo turned up, no less.

When I walked in, Cassandra seemed embarrassed. I could tell she was blushing despite her already rosy, sun-kissed complexion. She swiftly turned off the music so she could greet me: “Hey there. How was your day?”

“Just great, Cassie. What brings you home so early?”

“Oh, I took a sick day,” she responded, beaming coyly. “I’m not actually sick. I just felt a little tired today, that’s all.”

I didn’t respond. I was still in a rotten mood. However, seeing my stepmom had pushed my libido over the edge. I needed to bust a nut, badly. As Cassandra left for the master bedroom to fold laundry, I couldn’t help but stare. I’d always been mesmerized by her body, which was the only thing that made my dad’s marriage understandable. My gaze automatically shifted down… Past her slender waist, hugged by a sheer summer t-shirt before rounding out into a pair of youthful hips. She loved long runs, and it showed; she was in astonishingly good shape for a woman who had recently celebrated her 44th birthday.

My attention settled on what I thought was easily her best trait: her rear. Cassandra had a caboose like a pair of plump honey hams. Even through her fitted blue jeans, I could see her cheeks slide against each other with impossible fluidity, jiggling up and down with each step. She bent over when she reached the laundry basket, giving me an even better view of her pear shaped silhouette. A blue G-string was visible above her beltline, barely obscured by her shirt. My eyes followed the string, leading down until it disappeared between the crescents of her ass cheeks.

Keen to avoid suspicion, I averted my gaze and started upstairs towards my room, located directly above the master bedroom. I already had a semi pressing against my briefs, which felt all too hot and tight after the long day. As soon as I shut the door and took a seat, I grabbed a handful of lotion and started stroking myself. “Oh yeah,” I said out loud, surprising even myself. I stopped for a moment and just listened, worried my stepmom might have overheard. But I heard something else instead: a faint moaning noise coming from somewhere. I half-assedly pulled my briefs back up and peeked out my window, but no one was in sight. It was then that I realized that the sound was coming from directly below, and it was getting louder. I scarcely made out something that sounded like, “Stretch me… Stretch me… Open me, ooooh!”

My dick sprang from my waistband and I felt the hot sensation of pre-cum. I couldn’t believe my ears. Then I realized that I’d left my phone downstairs. Perhaps, I thought, I accidentally left some porn playing… Oh no! I slipped on a pair of sweatpants, then made my way back down. Every step I took seemed to produce an inordinate amount of creaking. But as I approached my backpack, I realized that the sound was, in fact, coming directly from the master bedroom just 10 feet away. My heart was pounding. The noises could still be heard, daintier and more delicate now. “Oh… Ooooohhhhhh… Ahh…”

I kept my hand placed on my crotch to hide my massive boner. If Cassandra were to walk out right now, this would be damning for both of us, I thought. The laundry room was adjacent to the master bedroom, separated only by a thin wall. It was dirty and I could feel a hot draft coming from the dryer, but I had to release myself somehow. I went in and started edging next to the sink. Just as I was about to climax, the noises stopped. I slipped my sweats back on and froze with anticipation.

To my horror, second later the bathroom door opened and there stood my stepmom, arms wrapped around a bundle of laundry. She had changed into a floral spring dress. She slowly looked up at me with a pair of big blue eyes. The laundry dropped and so did her mouth. I was towering over her, at least a foot above her petite 5’3” stature. The laundry room light cast a beam of light that perfectly illuminated the enormous tent pole protruding from my thin sweat pants, casting a penis shadow that filled up most of the laundry room.

Cassandra looked and her eyes grew even wider. “Oh... wow, you're in here, ” she said slowly, in shock. “Um...”

I didn’t know what to do. I expected a slap, or for my stepmother to simply flee. But instead, she surprised me by taking a few cautious steps forward. Her face was oily and hot and filled with mixed emotions. She hesitantly reached forward and her fingers slipped around my dick, causing me to tense. She could have easily fit three or four hands around my shaft. The head was nearly as big as her fist. She stopped and bit her lip. Unexpectedly, without a moment’s hesitation, she tugged my sweatpants all the way down, revealing my cock at its full glory, throbbing, vascular, and projecting a full 12 inches.

“Oh my god! It's just huge... I had no idea, James,” she exclaimed uneasily. A look of excitement flickered across her face.

I gave her a shy grin. "It's not actually completely hard now. Not that it matters, haha... But yeah... I mean, this is a little awk--!"

She put her finger to my lips to cut me off, and I was glad she did. I was clearly the largest my stepmom had ever seen. In fact, I was the largest I’d ever seen too. My dick was truly excessive in size, so large that it had always served as more of a predicament than an advantage. I had yet to meet a girl my age who could take much more than the tip, and most refused to touch it at all. I could understand why. I had the girth of a soda can. Most women enjoy sex, not internal damage.

While I stroked my cock, Cassandra pressed up against my chest without another word and began to kiss me. I had to stoop and she had to stand on her toes just to reach. I returned the favor and I swirled my tongue around hers. I slid my hands up her smooth thighs and supple waist and removed her bra from underneath her spring dress. She reached down and began stroking. I was absolutely rock hard from edging, and I pushed her hand away. My stepmom understood immediately and crouched down, taking the head into her mouth. It barely fit, and her lips grotesquely stretched around the rim and turned pale before it popped back out. She licked my shaft and took the balls into her mouth, slurping. Saliva dripped down onto my feet. As her enthrallment grew, drool drop from her chin and flowed down her toned belly. I pulled her dress up, revealing perky breasts and small pink nipples. She couldn’t have been more than a B cup, but they were bigger than I’d expected given her little frame. She lifted her arms as I finally slipped the dress off, revealing her lithe body and a blue G-string wedged into her wet, hairless pussy.

“Mmm... Mmh... Hehe. Want to go to my room?” my stepmom said fervently, getting up.

"Sounds like a good idea to me." I reached around and squeezed one of her butt cheeks tightly. It was surprisingly soft and spongy like fresh dough, and her skin was dewy and perfectly smooth... Far better than I'd ever expected a middle-aged woman's ass to feel like.

Cassandra grabbed my hand, or rather my fingers since I my hands were so much bigger, and led me back to her room. I watched her ass move, hypnotized by its perfect shape and the way it wobbled and rubbed against the G-string. She let go of me and climbed seductively into the middle of the king size bed. Her vibrator was still running next to the pillows. The room smelled floral, like soap. She propped herself on her elbows with her face resting on the sheets and arched her ass high into the air. Her buttcheeks glistened with sweat under the muted bedroom lighting.

A wave of guilt rushed over me. This was my dad’s soul mate, his life partner. He would be home in just a few hours. He might even find out. And yet… this thinking made everything seem even dirtier. Now the temptation was irresistible. I came behind Cassandra and massaged her shoulders before traveling down the crease of her lightly freckled back. Cassie let out a faint moan. She swayed her hips gently from side to side and her orb-like buns swayed with her. I slid a finger into her pussy, but she grabbed my hand and pushed me away. Confused, I latched onto her wrist to stop her and spanked her ass cheeks hard with my free hand. Her skin was extremely soft and delicate in contrast with the thick, calloused skin of my hands.

“Oh! Ah, oh… Ah! Shit! Ow!”

“Now you’ve really asked for it,” I responded, completely engulfed in passion; in response, she reached back to stroke me. She was loving it. I took both of her big soft mounds, now rosy from the spanking, in a tight grip to keep her still. Then I pried the G-string back with almost enough force to snap it and dug my tongue into Cassie’s perfect asshole. It was tight, but I could feel her breathing slow. Her ass started to unwind. Without warning I let go of the string and snapped it back down onto her relaxed anus. She let out a yelp but took it without complaint.

My stepmother’s pussy was soaking wet and the G-string was now drenched, yet as I slid two fingers in, she once again tried to push my hand away. “No, not there! He’ll know, he’ll find out. I want you somewhere else, big guy… Hehe.”

I almost jizzed on the spot. This woman wasn’t offering me her pussy like I’d assumed. She truly wanted to give me her ass… That tight, beautiful asshole I’d fantasized about for years despite my certainty that I’d never have my way with her. Cassandra spread out and I pulled her wet G-string down her long freckly legs. She then assumed the position again: face down, ass up, with her chest pressed flat against the mattress. My stepmom seemed to know exactly what I liked and wagged her butt friskily, as if to invite me in.

“One second, let me get some lube. We'll definitely need it... A lot of it,” I told her. I hurried to the kitchen to see what I could fine.

The events that had occurred seemed surreal as I returned to the bedroom again. Cassandra was still in the same teasing position, ass in the air. She looked back and exclaimed, “Is that vegetable oil? And wait… Where did you get that huge cucumber?”

“Yep, straight from the fridge. And you’ll see what I have in mind for the cucumber.” She gulped. The oil was cold and thick, perfect for anal lube. I just so happened to find the cucumber next to it. I popped open the bottle of vegetable oil and lubed up my index finger, then slowly slid it up my stepmom’s ready asshole. It was smooth and slick, the kind of butt that simply stayed clean, no doubt thanks to her vegan diet. She had told me before that she never had to wipe, and now I guess I believed her. Once again, I could feel her body relax and her asshole widen, making it easy to accommodate two fingers, then three… Then 4. But it was going to take more than just fingers to really get her open. I poured some oil on the bumpy cucumber and rubbed it all over, then positioned the large end it at the entrance of my stepmom’s waiting ass. As I slowly applied pressure, and her sphincter was forced to expand around the tip. Then it went in.

“Oooooooooooh! Oh my gosh! That is… huge! And cold!” Cassandra’s ass spasmed and squeezed desperately around the end of the huge foreign object. I got beside her and kept her steady so that it would stay lodged in her rectum.

“The cold will make your ass numb. Just relax, keep it in, and your hole will get used to it.” I hoped I was right. This particular cucumber was bigger than my stepmom’s forearm and looked rather unnatural going into someone so slight. Keeping static pressure on one end of the vegetable, her tension eased after about a minute. She let out a long groan as the cucumber slowly slid deeper down into her ass. I let go. The weight of the object alone caused it to sink deeper into my stepmom’s butthole until it came to a solid halt, completely stuffing her rectum. Oil dribbled down her pussy. She grabbed the vibrator and rubbed her clit while the huge cucumber remained lodged deep in her tight ass. She cried out and lurched forward repeatedly, her back flexing and arching. She squirted and tightened up, and then relaxed again and continued to groan with her face in the blankets.

“Oh fuck…”

“Are you enjoying this?” I said. She timidly nodded and sighed, spreading her cheeks. With that, I grabbed one end of the big greasy cucumber and tugged it straight out. Cassandra’s ass promptly opened with. Her bowels released a huge fart and her rectum slurped loudly, gaping as wide if not wider than the cucumber itself and revealing her hollow rectum.

“Holy shit. Your asshole is really open, Cassie.” She reached back and circled her anus with a couple fingers, and then repeated this action as if to make sure. Then she balled her hand and plunged it directly into her hole past the wrist.

“Oh god… I’ve never been stretched this much before. Please give me your dick, please, please, please. I want you deep inside me. Mmmm…”

My stepmom pulled her hand back out of her dilated hole and squeezed herself shut again before letting out a noisy whoosh of air. Bizarrely, it smelled like a mixture of soap and flowers rather than what you’d expect. Her ass was clean enough to eat out of.

“Do you want me balls deep in that butt?” I hoped her answer would be yes.

“Please! Please, give it to me. I’m so empty now and I need to be filled. Just fuck me!” she cried, spreading her cheeks zealously.

I was harder than ever now and happily consented. Perhaps Cassandra didn’t know what she was getting herself into, but my libido no longer cared. I needed to fuck something hard and deep after edging for so long. The bed sheets were already soiled with vegetable oil, so I poured it straight out of the bottle onto my throbbing cock. Then I stuck the opening of the bottle into Cassandra’s expecting arsehole and squeezed the rest (several cups’ worth) into her bowels. My stepmom would need all the lubrication she could get. Her deep ass gurgled as the oil traveled down her rectum and into her colon.

I plopped my dick down between my stepmom’s ass cheeks so that the shaft trailed down my stepmother’s back. It looked comically large, reaching all the way from her ass to her diaphragm. Oil dripped from dick and went down her neck. She moaned and arched her back with enthusiasm as the oil dripped onto the pillows she was resting on. I provocatively propped the well-lubricated head of my dick on her twitching anus. Even though my member was thicker than the cucumber, Cassie’s hungry ass accepted the head readily, almost greedily. Her stretched sphincter felt like a vice grip, and even her rectum was totally filled by my girth. But her relaxation techniques were working, and her ass slowly accommodated the first 5 inches with a lot of cursing and whining. But I had 7 inches to go before I’d be balls deep. To keep my stepmother from pulling away, I seized her satiny hips and pushed hard, causing her to cry out. Her cries became groans again as the next two inches slid into her tight butthole.

My dick was halfway in, but that wasn’t deep enough. I felt the head pressing against the 90-degree turn at the beginning of her sigmoid colon. I was more flexible than the cucumber; I knew I could get into the tight space. I pulled out, then slid myself all the way back inside her warm cave, gaining a fraction of an inch of depth. I drove in as deeply as I could until I had almost 8 inches submerged in her slick hole. With every thrust, my stepmom groaned, but now she was pushing back against me instead of pulling away. “It’s so good!” she cried out. “Oh fuck, it’s so good, please fill me all the way! Do it!”

As the puddle of oil and ass and pussy juice grew around her, Cassandra’s desirous butthole loosened to the point that her ass ring slid freely along my cock, gripping it willingly as I pushed in.

“Okay Cassie, you need to relax. Keep doing your breathing techniques.”

My stepmom nodded with her face hidden in the bed sheets, and I stopped ramming her rectum. Keeping a firm grip on her hips so that she would stay put, I angled myself slightly to the left and relentlessly pushed forward against the entrance of her colon. What felt like a brick wall at first became a tight sphincter wrapping around the head. Suddenly, all 12 inches sank into Cassandra’s ass. My balls slapped against her vagina. She was groaning louder than ever and stuck fingers in her ass alongside my cock to make herself even looser. I grabbed her waist and felt a strange sensation in her stomach. When I began to fuck her colon gently, the lump moved.

“Ohh... Mmm... Oohhhh...” Cassie moaned. “I can feel… I can see your dick in my stomach. I can see it moving! How is that even possible? Oh god oh god oh god!”

I took a look and sure enough, I could see the outline of my penis sliding through my stepmother’s waistline. I enveloped her lean waist with both hands, as though she were nothing more than a sleeve toy, and pulled my cock out until only the head remained inside, then plunged back in again until her asshole was flush against my balls. She responded with grunts and whimpers. Her intestines grumbled as they straightened and relaxed, and her soft, muscular colon massaged me with every deep 12-inch stroke.

“Please, just give it to me! Give it all to me!” my stepmom cried out, spreading her silky ass cheeks and pushing back against every bottomless thrust. I slapped her ass so hard that she squealed and her body swayed to the side. Still buried in her wet tunnel, I got up from my knees and fully mounted her. I drove straight down to the hilt with every thrust, forcing the piss out of her bladder and causing her pussy to dribble and queef. My stepmom’s complexion was flushed and sweaty as she looked back at me, slack-jawed. The deep pounding caused her bellybutton to distend by several inches. Now she seemed to be enjoying herself, releasing deep moans, screams, and spirited cries (instead of making uncomfortable-sounding grunts). Not only did she thrust her athletic hips back at me, causing her butt cheeks to clap against my abs, but she gyrated and pivoted her body, causing her belly to bulge out in random places.

“I want you to come! Please come for me! I need your cum!” she yowled, massaging her own belly, still staring back with a look of wonderment and awe. She’d given her ass to me completely. I pried her butthole wide open with my fingers and pulled out. Her ass made a big slurping sound and left her anal cavity cavernous and open, the rings of her straightened colon compliant and exposed. Her asshole winked at me.

“Oh no… You think it’s over? Don’t you shut your elastic hole just yet, slut.” With that, I laid on my back on the bed and lifted my stepmother’s slender, exhausted body, grinding her ass back down to my balls with little effort. Now I had a clear view of my cock inside of her, the head clearly visible just below her ribcage. “Time for you to fuck me. Then you can have my cum.”

Cassandra began sluggishly fucking, my cock remaining deeply embedded in her guts. In need of something faster-paced, I slid her off and spread her on her back without resistance. I sucked and bit her soft pink nipples and wrapped my arms around her freckled body, then went back to pounding her relentlessly with long, deep strokes. Cassandra didn’t make a sound; she just stared at me with a bewildered look on her face. Finally she let out a wet little moan which then became loud, then raucous. I felt myself nearing climax and I withdrew all but the head, then rammed back in with enough force to jolt her entire body. I shuddered as I finally climaxed like I’d never climaxed before. My stepmother’s guts bulged with cum for a moment. Fluids hit me in the crotch as my she reached her climax at the same time. She furiously rubbed her clit and her thin body shook violently. Her colon clenched tightly onto me with surprising strength and my own cum was forced back out of her ass and onto the blankets. Her body trembled once more, and then she let out a long sigh before collapsing down on the bed next to me, leaving me inside of her warm, flawless ass.

“Did you enjoy yourself?” I asked disparagingly.

“Oh yeah… You know, I’d never had anal sex before. I didn’t know it could be so good!” Cassandra grinned broadly and patted the huge bulge in her stomach. “You know what we found out? I’m an anal whore!”

THE END...
...Until Cassandra learns how to take a fist. And this time, someone new gets involved in the action!

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