The Sugar Mama Milf (Patreon)

Another busy Monday as I clear out the last of the voted stories. A chubby little milf who keeps finding excuses to bang the boy next door as thanks for helping her out.

I’m pleased with how this one came out, but it took me a long time to really settle into it. I try to keep things varied as best I can, and this felt like a straight shot of chubby mom sex. I think I got caught up on that and kept feeling out the exact chemistry I wanted here beyond just writing a sex scene. I honestly came to grasp it when I wrote Marilyn just ramming her butt back to pin our guy to the wall; that she’s hungry and desperate and will do anything she can to get some loving and not let it go. She’ll play the sweet neighbor but is just soaking for a good fuck that she’ll seize at a moment’s notice. So enjoy that, I guess!

“Oh, Franklin! You’re such a sweetheart! And such a big strong boy!”

Marilyn was a sweet, roundly built woman that lived around the corner from me. She was surprisingly neighborly for being a few houses down. She popped by right after I’d moved in, bringing me a tupperware of dinner and a big smiling welcome. She always flagged me down for at least a hi. At most chatting my ear off, fussing over if I was eating alright and asking if I was seeing anybody (“A handsome boy like you…”). She was an older woman with kids that had just moved out and her husband had passed away, so at first I’d assumed she was just lonely.

She was a plump little lady, a little over five feet tall. She carried the weight well, reminding me of a marshmallow with all that pillowy softness. She had a round, always smiling face with her brown hair kept up in a big loose bun. They went with her curves, because looking down at the short woman forced me to acknowledge her huge wobbly tits and wide behind that was so big and meaty that they were impossible to ignore. She had a slight belly to her at her age, but the rest of her intense curves made it effectively an hourglass figure.

It didn’t take much for her to call for me. I’d changed lightbulbs and carried groceries anytime she needed and she was always so vocally grateful.

This time, I had just run into her at the grocery store where she’d gotten me to reach a bag of rice off the top shelf for her. I was making an evening run for some things I’d forgotten after a late shift, and I was surprised to find her out this late. With no other family around to worry about, I guess Marilyn ran some strange hours herself. She was dressed in a simple sundress that was a mixed shade of purple. It kept a tasteful neckline, but the sheer size of her potato sack-sized chest still found a way to stretch them out.

“It’s no problem, Mary,” I assured her.

“Oh nonsense. You’re my hero,” she gushed over my casual reach from being a foot taller than her.

I set it in her shopping cart with a few other items. I noticed that she didn’t have much in there besides the rice itself.

“Doing some light shopping I guess?” I asked,

“Oh, you know how it is,” she chuckled with a warm smile.

“I saw you heading out and that reminded me that I needed a few things myself. And the stores are always so quiet this time of day.”

I looked around and realized she was right. The grocery store was basically empty. The only other person in eyeshot was a distracted clerk who was price scanning fruit halfway across the store. We were effectively all alone.

The chubby milf suddenly pressed her body against me. Marilyn’s big round boobs squished against me, spreading out softly to expand across my chest. She kept up her sweet smile as I could feel the heat of her bosom through our clothes. The gentle pressure had her boobs balloon up so that the soft mountains swelled up through her neckline.

“I really can’t thank you enough for all your help, sweetie. You really should let me repay you.”

I shifted my weight to keep my immediate hardon from poking her in the stomach. I blushed hard and avoided her warm but piercing gaze, but I’m sure she saw how much that had affected me.

“I uh… you don’t need to pay me back, Missus Hodgins. I’m okay on money,” I tried to deflect before realizing the easy setup I’d given the flirty milf.

Marilyn took one of my hands in hers. It wasn’t a strong grip, but it was so warm and confident.

“I wasn’t talking about money, sweetie. You know it’s Miss Hodgins now, and that you can call me Marilyn.”

She purred out the last part as squeezed my hand. She led them right to the side of her breasts, squeezing them from every side. They felt like a dream! They were soft and squishy like overstuffed pillows. My fingers immediately squeezed the ripened with age tits through her dress, feeling their weight and the creases of her bra. The undergarment felt stiff and rigid, clearly needing to be in order to hold up that much breast meat. My understanding of all the stuff I’d mistaken for neighborly sweetness hid me like a tidal wave.

“Let's try something a little naughty, hmm?” Marilyn suggested with a playful giggle.

She withdrew from my touch, but I could still feel the warmth and softness haunting my palms.

“Meet me over in the bread aisle where we can have some privacy.”

She spoke without breaking her round and happy smile. She rolled her cart off to head right there with enough of a sway in her step that I was briefly mesmerized by the bounce of her big round booty. My heart was racing, realizing how much experience she must have had and how long she’d gone without sex, to say nothing of when she last got to flirt with someone.

I didn’t have to consider things for very long before I hurried after Marilyn. I found the short brunette pretending to carefully consider what load of bread to buy. She was bent over far enough to make her breasts dangle temptingly and her ass sticking out halfway across the aisle. It would have been difficult to walk past her even if I’d wanted to, like she was both inviting me to join her and locking me into my decision.

I approached her, uncertain of exactly what she meant to do with me but trusting in my hardon. As soon as I was in reach of her, Marilyn turned and pushed her wide, fat ass back against my lap. It clapped audibly against my crotch, and she let out an amused little purr as she wiggled her ass against me. My cock slid between her ass cheeks, fitting neatly there even through my jeans with how hard I was and how soft her ass was.

“Fancy meeting you here~!” she chimed with a playful innocence.

She started bobbing her booty up and down against my shaft. It wasn’t any expert kind of movement, but she had the sheer mass to make it more than enough to keep me paralyzed with arousal. Her booty wobbled like a wave that seemed to massage my erection from all sides. I was speechless, only able to moan as I reached out to cup her wide behind. The milf down the road immediately purred.

She was always doing things like this. She was even needier than I was for the attention, instigating and always adoring my rubbing hands. They sank in deep on her soft buns, and as I rub around she sighs deeply like it’s a huge relief for her rather than my intensifying need.

“Mmm, there’s mama’s good boy~! My big tall man is so helpful with all those hard to reach places.”

Marilyn was every bit as into it as I was, but even more vocal about it. I was just getting into the pace of her grinding when she thrust back hard enough to push me back against the opposite shelves. I was lucky they were sturdy enough to withstand the impact as Marilyn started bumping back into me, her big ass demanding my attention. Her plump cheeks slapped against my lap as she reached back and lifted her skirt, exposing her lacy black panties. Either she’d been in an especially flirty mood today or she’d worn them specifically knowing she’d run into me.

“Don’t keep me waiting now, sweetie,” she cooed.

Marilyn took my hands and guided them to the waistband of her panties, making sure I got a firm grip on them. I was horny enough to assume what she wanted and pulled them down, exposing her wide ass cheeks. They had a soft sag to them that just made them look even bigger and softer, filling out those child-bearing hips. I quickly unzipped my pants, enough to let my raging hardon out.  didn’t even have to thrust my way inside them before Marilyn threw her booty back, pinning me against the shelves with her dense ass spreading out around my cock. The mushy buns swallowed up my boner on all sides.

“Ohhh. Good boy! That’s what mommy likes,” she grunted, accenting each word of her last sentence with a firm shake of her ass, left to right.

Her plump booty hugged around it, hotdogging me around before she raised her hips higher. I stooped to meet her halfway in sliding my dick up her ass. As loose and soft as most of her was, her hole was plenty tight and she knew how to work her hips to keep tugging and rocking against me. Her fat ass even weighed it down to make her feel even tighter, and she knew what she was doing to bounce in place to keep both of us moaning over it. I had to wonder what kind of kinky shit she’d gotten up to with her husband, or if she’d just learned all this just for me.

“Mmf… I knew we were right to do it in the bread aisle. Mama needed some meat between her buns,” she grunted, biting her lip.

Even the mom pun wouldn’t stop me from plowing deep inside her. I thrust to meet her bumping booty, her warmly clenching asshole jerking me off in return. The plump padding of her cheeks slapped against my lap while I instinctively reached for something to hold onto. My hands settled on Miss Hodgins’ huge flopping tits, pulling her tighter against me so that she made even faster, shorter pushes to get me off even harder. I bent over her, grunting into her ear as the fluffy bun of her hair brushed past my cheek.

“Ooh, you’re almost done, aren’t you? I can feel those big full balls of yours rubbing around back there. It’s alright. You can let it alllll out, darling. Let mama Mary repay you for alllll that hard work… cum in me, sweetie. You can do it~!”

Marilyn’s sweetly dirty encouragement pushed me over the edge into nutting inside her. I grunted hard, squeezing her tits until they fleshed out to fill between my fingers. I pushed myself balls deep up her ass, squirting deep into her bowels. I could feel the squish of my jizz inside her as I gave a few last milking pumps, tiring myself out quickly. I was pumping hard enough that even the chubby little milf was getting rocked by my intense orgasmic thrusts, but she just kept pushing her butt back into place to keep me deep inside her. By the time I was catching my breath and she stepped back to reclaim her panties, she hadn’t even left a mess on the floor. Her ass was just that tight.

“See now? That wasn’t so hard, was it? It’s the least my special little guy deserves.”

“Wow… thanks,” I panted as I yanked up my pants.

“You left quite a big tip yourself there, handsome,” Marilyn giggled as she adjusted her dress.

“But so long as I have you, I do have a few other little things that I could use the help of a big strong boy back home.”

The curvy mama gave an adjusting tug at her bra straps, making her huge tits bounce up and down temptingly. It wasn’t impossible to keep my eyes off the moving mountains of flesh.

“If you weren’t too busy of course.”

“Hey! Is that guy who keeps fucking the bread down there?!” a voice shouted.

I double checked my fly… and also made a mental note to shop somewhere else after what the clerk said. Marilyn hastily trotted in the opposite direction with her shopping cart so I hurried to follow her. I figured I could spare some time for the lonely older lady with more thickness than any other woman my age. If she had a few chores for me to help out with, why not stop by? It wasn’t like I was doing much anyway.

---

The next half hour was a blur as we bought our stuff and went back to Marilyn’s place. I carried her groceries, helped change a lightbulb in her bedroom… and next thing I knew I was laying on my back with her helping me out of my shirt and pants. She pulled my cock back out and threw my jeans aside as she climbed on top of me, peeling her dress off over her head. She undid her bra and let it drop, falling over my chest. It was big enough to block out my vision for a moment, and when I brushed it aside the chubby milf’s huge tits were on full display. Just like her ass, her stomach and bust drooped a bit but she carried it  well. It was a fertile sort of roundness rather than outright saggy, and her wide, dark areolas framed a pair of fat, slightly upturned nipples.

Marilyn glanced down at me as she saw me staring. She ran a hand through her hair, popping loose the hair tie and letting her brown bun fall down around her shoulders. She shook it out and gave me a warm smile.

“What do you think? Anything close to those college girls you age?” she asked, curving her arms inward. It squashed her huge, lightly freckled boobs together until they swelled up like a pair of flesh potato sacks.

“No… you’re way better than them,” I moaned as she scooted closer, rubbing my cock against her thigh and the bottom of her soft belly.

I ran my hands up her sides, riding out the soft curves before cupping her massive tits. They were so soft and heavy, just like the rest of her, feeling like doughy perfection. She gave a loud and hungry moan now that we were in the privacy of her bedroom and not sneaking anal sex in the grocery store. She leaned over me, bracing herself on all fours to pin me to the bed beneath her drooping tits and stomach. Her boobs draped over my face, demanding my attention. All I had to do was open my mouth and her teat fell into my mouth, coddling me at every turn. I slurped loudly as I drew her hard nip into my lips, exploring it with my tongue. She moaned louder, arching her back to press herself harder against me.

There was nothing to hold her back as she grabbed my cock with a gentle but urgent grip that guided it right inside her. I was brushed between her fat thighs, tracing some clear precum across them before her pussy engulfed my dick. She locked her thighs around my hips. It was outlandishly comfortable. Her breasts squashed out over my face while she rested her hands on my chest, consuming me in her pillowy body. Her pussy was soaking wet, having probably gone through an even longer dry spell than me by a long shot. She gave a deep sigh, freezing up as she took me all the way inside. Her pussy connected with my pelvis and held there, leaving me soaking inside her for a solid minute in heaven.

“Ahh… it’s been sooo long. You’re such a good boy, Franklin,” she purred as she finally started to move again.

Marilyn only had to bounce a couple times before she got much more intense. She started slow but quickly built up momentum, her hips thumping into mine as she rode my cock like a pro. She shut her eyes and gasped in delight, running one hand over her chest. The huge orb oozed over her arm like a lump of dough before dropping into place against its double. I bit into her nipple, but she was hard and horny enough that it just got lost in her constant wails and moans. I could thrust up and grope at her, but Marilyn was clearly in control and hungry enough to help herself while she was on top of me. Watching her thrust up and down so intensely while her chubby curves bobbed a half-second after the rest of her was a thing of fertile beauty as she rode me like a force of nature.

“Good boy~! Just like that! Keep it going~! More for mama! I forgot what it was like being with a nice young man like you with a nice young cock~! Give it alllll to me, sweetie~!”

Marilyn’s almost drunken praise spilled out her lips, that hot mix of sweet praise and dirty encouragement. I couldn’t imagine doing anything else besides thrusting up to keep making her happy, ramming into her as hard as she humped me back to assure her I found it just as hot as she did. I sucked and kissed at her breast until I started tasting some sweet milk oozing out from her pudgy nipple. It only encouraged me more.

My eyes fluttered as I ended up progressing to the perfect stroke. Her slick pussy rode my dick perfectly, sliding all the way down until it connected with my pelvis like a sloppy wet kiss. I felt the intimate ridges and folds of her inner pussy until my firm head brushed against the outline of her clit, pressing against the softness of her g-spot. My head spun while I saw Marilyn form a perfect O with her mouth, arching her back to pop her breast from my mouth. A thin spray of milk washed over my face and chest as she sat up straight, arching her back to thrust her tits out and align her crotch as close as it could with my own. She let out a deep, guttural howl as I felt her pussy clench around me, hugging my cock with a sudden tightness beyond what she’d shown before. It was like I was inside her ass all over again, only dripping with pussy juice. It only got wetter as my cock pulsed, cumming deep into her pussy while it shuddered with its own orgasm. As I shot my seed into her, her womanhood opened right up to take it and release her own wave of warm cum.

With a wistful sigh, Marilyn came crashing down on top of me. Her breasts blocked out everything from view while, leaving me swimming in ecstasy. I let myself catch my breath, huffing down the warm flesh of the milfy body and letting time and her constantly shifting and squishy body wash over me. Whenever she was done cooling down, the short brunette raised her head and kissed me full on the mouth. I parted my lips and let her tongue push its way inside, glad to let her help herself as long as she wanted. A long french kiss later and she slowly withdrew.

“Oh, Franky… I haven’t felt this young in ages,” she mused, running her painted nails through my hair.

“Maybe I should hang out with kids like you more often,” she chuckled.

I laughed back, definitely not thinking of myself as a fresh out of college “kid.” But I could see her being nostalgic and lonely and needy… and horny as hell being left alone like this.

“I wouldn’t mind at all,” I downplayed it, wrapping my arms around her neck.

The mellow milf smiled softly at me and planted another little kiss on my nose.

“Then I think that would be lovely. There’s plenty of little odds and ends a helpless old lady like me could use a hand with. And I’m sure I’ll find some way to thank you for each and every little chore you do for me.”

Her smiled widened, a bit more impish and hungry this time. The kind that said she was going to invent every little problem she could, just to get me to help out and fuck my brains out as a reward.

“Happy to help!” I agreed as soon as it dawned on me.