Grandma Plays Cupid

Summary: Fucking his BBW Grandma leads to a black nerd finding The One.

Note 1: This is a Literotica Valentine's Day Contest 2021 so please vote. PS... even though it takes place at Christmas, this is another silkstockingslover twisted love story.

Note 2: Thanks to Tex Beethoven and Robert for editing this twisted story.

Grandma Plays Cupid

"Yes, eat my asshole, you sexy bride," my Grandma ordered. A few members of our two newly joined families were in our hotel room, making excellent use of the time between the wedding and the reception.

"Keep sucking my cock," I ordered my Grandma, as I watched my pretty bride, still in her wedding dress, with her face buried between my Grandma's big black ass cheeks.

"I can't believe I get to use this cock before your new wife even does," Grandma gloated, before she devoured my cock like she had so many times before.

"Why shouldn't you?" I shrugged, as I watched her hungrily bob on my cock. "You sucked it before she ever did."

"And you fucked it before I did too," my sexy bride added cheerfully, as she probed my Grandma's asshole with her tongue.

"Touché," I laughed.

"When do I get some dick?" my bride's mom whined, as she was 'only' being licked by her other daughter.

"Whenever I'm finished with it, and quit your bellyaching, " Grandma said tersely, both my bride and her mom having been white submissives to my Grandma and my mother long before I became sexually involved with any of them.

"Sorry, Mistress," Mrs. Hamilton apologised, as I reminisced back to Christmas 2020, three years ago, and how a simple visit to cheer up my lonely Grandma during that fucked up COVID crisis had led me to love... a very kinky love... but love, nonetheless.

.....

But before you begin reading about how I first met and fell in love with my new wife, please allow me to educate you about my fetishes because my story, and in particular my motivation for making various decisions, pretty much hangs on them. I've learned that while these fetishes aren't individually as rare as I once thought, having them all at once is pretty much impossible to find in porn or erotica.

1. I love older women. I don't mean MILFS, I mean GILFS, as in Grandmas. Women under forty don't do much for me, and gals my own age have always done very little to turn me on.
2. I love chubby women. Not excessively obese, but noticeably chubby. I like huge tits (I know, who doesn't), but I also love huge asses). I don't know what it is, but chubby gals are just so sexy, and since I was a virgin when this story begins it wasn't from actual experience, but I believed they would try harder. What I mean by that is I expected they'd be willing to do things skinny gals wouldn't. Or at least that's what I'd gathered from online reading and some chat groups. I'd also found in porn that chubby gals (and of course downright fat gals as well) seem so much more authentic in their moans and their enjoyment of sucking dick, getting fucked, taking it in the ass and eating pussy.
3. I love nylons. I love the feel of them (I've worn them many times while pleasuring myself, and both of the girlfriends I'd had prior to the events in this story wore them on occasion), and I love the look of them. They literally transform a pair of legs and feet, and they seem to be the ultimate fashion accessory for women, coming in such a wide variety of colours and even patterns.
4. I love incest. At one time I couldn't fathom ever actually committing the act, although if even one percent of the people who say they do it aren't lying, then the number of people breaking the law and keeping it in the family would be staggering. I did jerk off while visualising my mother however, pretty much ever since I began masturbating. She was delightfully chubby, and since she was a nurse, she wore nylons regularly. She was forty-two back in 2020, which fit her into my older woman criterion by a tiny amount. I also jerked off to my sixty-two-year-old Grandma, who fit perfectly into all my fetishes. And although I read a lot of incest erotica, I'd never seriously considered the possibility of doing it for real.

So my predicament was that you can find websites catering to many fetishes, such as incest, BBC, lesbian, bi, and nylon, just to name a few of my favourites, but it's nearly impossible to find any sites featuring Grandmas getting fucked or chubby gals getting drilled. On Pornhub you can find a few scenes, which definitely got me going, but never enough of them to fuel my frequent jerk-off sessions.

So if you're still with me, I'll now tell you how I found the perfect woman... the one who fit into all of my kinks... my very own Grandma May... and how she guided me into discovering the perfect woman to marry.

.....

COVID CHRISTMAS 2020.

Mom said to me, "Because of work, your Dad and I can't go see her and then need to quarantine ourselves for two weeks, but if you wanted to, you certainly could."

"Sure," I agreed without hesitation. I loved my Grandma, and I hadn't seen her in months, due to COVID. And since our school break was for three weeks followed by online learning anyway, I could easily isolate myself while still keeping up with my high school classes. Plus with grandpa passing a couple years ago, I knew the old dear had to be lonely. And especially since we hadn't been able to get together for Thanksgiving (which was right before I was moved into online schooling, and was still working my ass off to win myself a full ride scholarship next year), there was no way I was going to make her spend Christmas all by her lonesome.

"You're an amazingly generous young man," my mother said, giving me a big hug, her huge tits pressing against me.

"You raised me to be that way," I returned the compliment.

"Well, I'm an awesome mother," she admitted, as she let me go.

"The best," I agreed, as I glanced down at her nylon-clad toes... my hard cock flinching in my pants, which prompted a jerk off session in my bedroom a few minutes later.

.....

A long day of driving, then a sketchy motel followed by fourteen more hours on the highway later, I arrived at my Grandma's house on December 23.

She hadn't known I was coming.

I was looking forward to surprising her, since we'd told her due to COVID, none of us could make it. She said she understood, although the obvious disappointment in her voice over the phone was heartbreaking.

Yet I was the one who was the most surprised... or I suppose we were equally so.

Mom had given me a key so I could let myself in if I arrived too late in the evening, which due to Christmas traffic and slowdowns from encountering three accident scenes, I arrived a good three hours later than I'd anticipated when I got back onto the road following a leisurely breakfast that morning.

It was after eleven, so of course all the lights were off... at least so it appeared from the front of the farmhouse. Oddly, there was a second vehicle parked next to her old pickup truck in the driveway, but I didn't put much thought into it. I knew she'd occasionally had people stay for a day or so before COVID, to help the local hockey team, or families who needed a place to stay during big football games... but with all sports on hold and college on break, it didn't really explain the car at all.

I grabbed my suitcase, unlocked the door, my Grandma didn't have a security system, I suppose because she trusted people, and because she lived on a farm a ten-minute drive along a rural road away from the nearby town, and I walked in.

I sang out, "Grandma," but as anticipated, I didn't receive an answer. She was likely in bed and fast asleep already.

I sighed. I should have called so I wouldn't wake her up, startle her or worse, yet I was really looking forward to seeing the surprised look on her face.

As I walked into the dark living room, I stumbled over a pair of red heels (which I discovered after turning on a light) that couldn't possibly be my Grandma's... not with four inches on them. Still, I didn't even begin to put two and two together, or to anticipate the surprise I was about to receive.

I proceeded through the room and down the hallway, when I saw a light on through the mostly closed door at the end, which was Grandma's bedroom.

I set down my suitcase in the spare bedroom I always slept in, and then quietly approached my Grandma's room. I could hear Jimmy Kimmel on the television as I quietly peeked into the room to see if she was awake... not expecting to find her in any kind of inappropriate act at all... but... that's exactly what I was suddenly witnessing.

"That's it, eat Big Momma's box," my Grandma urged as she sat on the edge of the bed, almost completely naked except for a black garter-belt and stockings, and someone kneeling between her legs.

As I looked closer, I had a side view so I could see her large sagging left tit, her chubby leg and foot in sexy nylons, and a blonde ponytail waving back and forth between her widespread legs.

There was a gal between Grandma's legs!

Some white gal was eating my Grandma's pussy!

The blonde responded, "I love eating your pussy so much, Big Momma."

"So much that you left your boyfriend behind at a Christmas party to drive twenty minutes here just to eat Big Momma's cunt?" Grandma asked, using the most shocking word I could possibly imagine leaving her mouth! I'd never once even heard the Christian soul say 'damn'. She'd even cuffed Dad on the back of his head when he swore the prior Thanksgiving (back in 2019, if you're keeping track) when his Lions gave up a winning touchdown to the Bears in the last two minutes. Plus, cunt isn't a word we black people use... we say pussy; cunt is a white man's word.

"I did exactly that, Big Momma," the blonde admitted. "You know how I can't resist your delicious cunt. Every time you text me, I drop whatever I'm doing and drive right over to service you."

This was beyond unbelievable!

The entire scene.

The gal's voice, which sounded young...like she was around my age.

My Grandma wearing lingerie... that wasn't something I'd ever imagined her doing, even though she was always wearing nylons when I saw her.

Her dirty talk.

Grandma texting a gal to come over and eat her pussy, so she comes right over. This is shit you read in erotica or see in porn... definitely not anything you find in real life, and doubly definitely not anything you see happening to your sixty-two-year-old Grandma.

My cock was raging in my pants as I watched a scene way hotter than anything I'd ever downloaded or watched online. And better tailored to my own kinks than I'd ever imagined encountering.

Older woman... check... although the gal between her legs was definitely younger... as I said, her voice sounding like she still might be in high school.

Chubby woman... check... although the gal between her legs definitely wasn't chubby, but skinny like most of the anorexic-looking gals trying to look hot in my school.

Wearing nylons... check... although I couldn't see for sure if the gal was wearing them too, but it looked like she might be.

And as for incest... she had no relatives living around here so this wasn't incest, but my being here was watching my own flesh and blood, the woman who'd given birth to my mother having sex was kind of second-hand incest.

"Because Big Momma's cunt is so much better than college cock, isn't it, my high school cheerleading slut?" Grandma continued, as if she were deliberately giving me more and more information as I processed what was occurring right before my eyes.

"Yes, Big Momma, you know we all prefer your cunt over any high school or college boy's dick," the gal said, this just continuing to get hotter and hotter, while also getting more and more shocking.

She'd said we? How many gals was she talking about?

"Yes, Jenny had dinner here today," Grandma said, adding one more twisted kink to an already twisted reveal, "and your mother dropped by for some coffee and pie."

"My mom does love your special homemade dessert," the gal said, not at all shocked by this news.

"Like mother, like daughter," Grandma said, as she leaned back onto the bed, giving me a better look at her body... her huge fat tits dropping haphazardly to her sides. God, I wanted to walk in and just cup them.

I should note I was eighteen at the time.

And unfortunately a virgin.

Other than some kissing, a little under the shirt cupping, a hand job in my car once, and eating my most recent girlfriend's pussy a couple of times (also in my car and in the dark, so I'd never even seen it), I had no sexual experience. I hadn't ever seen a real tit up close and personal either.

Yes I know, it's pathetic for an eighteen-year-old, but I was home schooled until I was fourteen, and being a geek and a nerd, I've always been a little awkward socially. Thus I focused on my studies and on getting high nineties so I could get into an elite school and make a fresh start, where I wasn't the guy everybody knew as the smart geeky home schooled kid.

"That's it, my cunt-licking cheerleader pet," Grandma moaned, as she cupped her own breasts.

"You have the best-tasting cunt in the community," the cheerleader declared, as her head was really moving up and down.

"I know," Grandma moaned louder, her sounds of growing pleasure so fucking exotic. I'd overheard my mom getting fucked by Dad on multiple occasions, and they each had similarly increasing moans when they were close... although my mom wasn't very talkative while she was getting fucked. Grandma, in many ways, spoke and acted like many of the dominant mistresses I read about... which was so surreal and unbelievable... I wasn't sure I believed what I was witnessing, even though I was witnessing it.

"Now get Big Momma off," Grandma ordered, "and drink down your early Christmas treat."

"Mmmmmmm, yes Big Momma," the cheerleader moaned, seeming to be as turned on from licking as my Grandma was from receiving.

"That it slut, right there, right fucking THERE!" she screamed, as her legs straightened and she shook the entire bed while she came.

The cheerleader remained busy between Grandma's stocking-clad legs, seeming to be hungrily lapping up my Grandma's cum.

"Such a good slut," Grandma moaned, as she enjoyed the afterglow of her intense orgasm.

"Such a perfect pussy," the cheerleader responded.

I knew I should slip away, then drive away and come back later, yet I needed to see what this cheerleader looked like. Somehow I just knew she had to be pretty... and the idea of a hot cheerleader being used by a chubby older woman was so hot... quadrupled times infinity hot when the chubby older woman was my very own Grandma!

"Come here and give Big Momma a kiss," Grandma said. I backed away a bit and looked through the small crack as the blonde, an absolute stunner, actually wearing a red dress and beige nylons, climbed onto the bed, kneeling to kiss my Grandma.

The kiss lasted a full minute before Grandma broke it and said, "Thanks for coming over."

"You know I'll come over here any time of day or night," the cheerleader replied.

"I know," Grandma smiled. "You proved that when you snuck away from the football game you were cheering to come eat me in my truck."

"Or when I ate your pussy for an hour, leaving my family's Thanksgiving dinner while you visited with your family."

My eyes went wide as I recalled Grandma actually seeming a little flushed and making some odd sounds throughout our lengthy Skype call. Now it made sense. Unbelievable, but true.

"I was thankful for both you and them," Grandma said playfully, always quick with a pun.

"I'm very thankful you let me eat your pussy so much," the cheerleader said.

"You're always my first choice," Grandma said.

"Really?" The blonde gasped, seeming genuinely surprised and flattered.

"Yes, it'll be a shame when you head off to college in the fall."

"I'll come visit you every time I'm home," she promised.

"I know you will," Grandma said.

"You sure you'll be okay alone for Christmas?" The cheerleader asked caringly... now sounding more like a grandchild than her pussy pleasing pet.

"Yes," Grandma said, although her tone revealed she'd be sad to be alone.

"I'll sneak out at some point to bring you some Christmas cheer," the cheerleader offered, kissing my Grandma again.

"You don't have to," Grandma said, adding, "Christmas is about family."

"First, you are like family to me," the cheerleader said, as she began slowly grinding her pussy on Grandma's leg. "And second, nobody should be alone on Christmas."

"Well, if you did drop by, I certainly wouldn't refuse your face in my pussy."

"Then I'll be here," the cheerleader said. "Maybe I'll even come all wrapped up."

"I see you're horny, my little slut," Grandma said, watching the cheerleader grind on her leg.

"Eating your cunt always gets me all fired up," she admitted. "Plus, Mom fingered me under the table during dinner, but not quite long enough."

"Your mother is also quite the slut," Grandma said, as she gently pushed the cheerleader away from her.

"Ever since you gave her her very first taste of pussy, she's become insatiable," the blonde admitted. "She's eaten every friend I have, and a couple of my teachers. She's really taken a liking to Mrs. Walker."

"Aaaaaah," Grandma said, as she got up and went into her closet, still talking. "Yes, Mrs. Walker is one dirty teacher. She can eat pussy like a porn star, and fuck a student like a stud."

"Yes, her bending me over her desk is my second favourite position," the blonde said, as still on the bed, she got onto all fours.

"Right after being between my legs," Grandma said, as she walked out carrying a strap-on, making my eyes go wide again.

"Exactly," the blonde said.

"Get out of that dress, I don't want to wreck it while I drill that cunt of yours," Grandma said, drawing the harness up her thick nylon-clad legs. There weren't a lot of online scenes showing chubby gals fucking anyone with a strap-on, so this was a literal dream come true... my cock throbbing in my pants.

"Yes, Big Momma," the blonde said, getting off the bed, unzipping her dress and letting it slide off her body. Any regular guy would blow a load just looking at this perfect teen figure, but I was more in lust with the one triple her age and triple her body size standing beside her.

"Fuck, you really are one hot thing," Grandma said, having a bit of trouble getting the strap-on around her wide waist.

"Thanks, Big Momma," the blonde said, as she got back onto the bed, now wearing only a pair of thigh high stockings.

"This is your Christmas gift, Sandra," Grandma said, finally getting it on properly. "Do you want it in that pussy of yours, or your cute asshole?"

My eyes once again went wide. My cock once again flinched desperately, trying to attract the manual attention it so desperately needed. But I resisted touching myself, knowing I'd spew a load in my pants within seconds if I did.

"You haven't fucked my asshole in a couple weeks," Sandra said. "Why don't you bang that?"

"I do love hearing you talk so nasty," Grandma said, as she walked to her table beside her bed, opened a drawer, and brought out what was obviously lube.

"You bring out the submissive slut in me, Big Momma," Sandra said, looking hungrily at my Grandma the same way I was doing. It was crazy to see a gal as pretty as Sandra, a gal I assumed wasn't only head cheerleader, but the ringleader of just about everything at her school, completely enamored by my Grandma's pussy and her body.