Stepmom Gets a Deep Anal Plundering

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 ...

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