1950s: Munching the Cheerleaders

For example, Courtney, a cheerleader from a nearby town, got to use me for a whole weekend on her 18th birthday, including me going down on her at least a dozen times, her mother half that many times, and her experimenting on both my cunt and ass with a variety of objects from candles, to a wooden spoon, a cucumber, a fist and some lego toys that belonged to her kid brother.

Except for my lack of time with Eleanor, my senior year was fine as I came to accept my weaknesses and revel in my natural role of obedient submission.

I still got good grades, I still spent time with my boyfriend (who somehow was oblivious to the turmoil of my life so long as I sucked his cock and swallowed his load on almost every date) and I still served a couple dozen women as the school year continued... but no matter what I did, my pride in my submissive role was compromised, I still felt lost...as if I weren't fulfilling my true role... I wasn't fulfilling my purpose.

And I realized for certain that things had changed between Eleanor and me when she called me the day before graduation and said, after my not serving her or spending any time with her the past two weeks, "I have a task for you."

"I can't wait," I answered, eager to be between her legs again... her pussy was one of the ones I missed the most... but I also missed our close friendship.

"Great, go to Valerie's house now," she ordered. "She wants a pet for the night."

"Oh," I said deflated, covering quickly, not wanting to show her my disappointment, "Okay, sounds great."

"Love ya, bye," she said, hanging up without our actually having a conversation... which hurt, as we had been best friends forever... often talking on the phone for hours at a time... and now we'd just concluded, without a doubt, our shortest conversation ever.

I sighed... tears filled my eyes... as I realized not only was I losing my best friend... she had just pimped me out.

Reluctantly, not at all excited to be going over to the girl who had stolen my best friend from me and replaced me between her legs, I trudged to Valerie's house like the obedient submissive I was. Talk about spineless! I used to consider Valerie the most submissive girl I knew!

When I got to her house, Valerie smiled and said, "You really just do whatever you're told, don't you?"

My face went red at the question, "I don't know."

"Come inside," she ordered.

I did, realizing that by doing so I had obeyed yet another order.

"Knees," she ordered.

Again I obeyed... unable to stand up for myself... back then, my need to obey being all I knew.

"Shit, the girls are going to love you," she laughed, as she snapped her fingers and ordered, "Crawl and follow."

My cheeks burned red as I wondered who the 'girls' were, yet as always, I followed.

As soon as I entered her living room I saw two other cheerleaders, Sarah and Pam, sitting on the couch... and Sarah was my fantasy cheerleader. Sometimes I even had dreams about her where she did me the unimaginable favour of actually liking me.

Sarah gasped, "Eleanor wasn't lying."

"Nope," Valerie said. "We have our very own pet for the night."

My face burned at Valerie's words and Eleanor's betrayal. Being a pet for the night wasn't a big deal... I would probably actually enjoy it... being a cheerleader's pet a pretty big fantasy. But to be treated as nothing more than a disposable plaything by my best friend... just given away as a bimbo to be used... that hurt.

"Get naked, Becca," Sarah ordered, but not in a bitchy way.

I stood up and got undressed.

Sarah said, once I was naked, "Wow, you have quite the body behind that conservative attire."

"Thank you," I said, flattered by the compliment.

Pam added, "Apparently nerds can hide some pretty good secrets behind their goody-goody exteriors."

Suddenly deciding to enjoy the evening, the fantasy, I smiled back, "Yeah, for instance we can be great pussy munchers."

"Oh my," Sarah laughed, shocked at my words.

"Let's see if that's true," Pam said, patting a spot on the couch for me.

I went over like a good pet, and sat between them. "Such nice tits," Sarah purred, as she cupped them and leaned in and kissed me.

I had been expecting to be used... but the kiss was a tender and welcome surprise... her lips were soft and caring.

I, of course, kissed her back gratefully as I felt Pam leave the couch, followed by my knees being spread open.

I wanted to look down, but I was completely intoxicated by the kiss even as I felt fingers sliding inside me... making me moan into Sarah's mouth.

Sarah broke the kiss and explained, "Pam has been our pussy licker all year, and she's become an addict."

"I see," I moaned, as I felt Pam's tongue begin licking me. I added, wanting to make it clear I wanted to eat Sarah's cunt too, "I've been told I'm a pretty good pussy pleasing plaything too."

"Oh, I look forward to confirming that," Sarah smiled, as she resumed kissing me.

I kissed her back for several minutes as she gently cupped my tits, tweaked my nipples, all while Pam licked my cunt hungrily and slowly fingered me.

Suddenly I felt my pussy stretched to its limit as Pam slid her entire fist in me... I moaned loudly, breaking the kiss. I didn't want to, Sarah's lips against mine felt so good, so warm and soft. But a fist in my pussy commanded all my attention, sending erotic lightning bolts shooting through my entire body!

Sarah explained matter-of-factly, "She also likes fisting us."

"So I seeeeee!" I moaned, my orgasm building quickly.

Sarah leaned in and kissed me again as Pam, still fisting me, resumed licking me. "Ooooohh!" I moaned into Sarah's open mouth just before her tongue began passionately exploring mine.

Not surprisingly, in under two minutes of being fisted and having my clit attacked, I again had to break Sarah's kiss as I moaned, "Oh God, yes, Pam, fist fuck my slit, I'm going to come!"

"Come Becca, come, you sexy nerd slut," Sarah purred, moving to my ear and tugging on it with her teeth.

Her hot breath and soft order was the final straw that made me burst, and I screamed, "Yesssssssss!"

"So sexy," Sarah whispered, her open lips again pressed against mine, as I came.

Pam kept fucking me throughout my orgasm until my body stopped twitching, and she pulled her hand out and my cum leaked out of me.

Sarah sat up on the edge of the couch and smiled warmly, "Becca, I think it's time to take you up on your generous offer."

"My pleasure," I smiled, my body still trembling as I leaned over and buried my face in her trimmed pussy.

"Oh yes, sweetheart, lick me," Sarah moaned,

And I did... for minutes. I licked... I probed... I fingered... enjoying her sweet taste... her honey nectar... her intoxicating scent.

God, I wanted to get her off... to taste her come... to prove I was a good pet... to show that I was worthy....

Sarah finally begged, "Fist fuck me, Becca, I want you to pound my pussy."

I obeyed, so intoxicated by her that I didn't even hesitate, slowly sliding my extended fingers and thumb inside her, then bunching my hand into a fist and jerking it back and forth.

"Fuuuuuuuuck!" she screamed, as half my forearm disappeared inside her pretty pussy.

I copied what Pam had done to me minutes ago, moving to her slit and furiously licking and tugging on it.

"Oh my, oh my, fuck, yes, fuck, yes, yes, fuck!" Sarah babbled, before her body shook intensely and she came. I quickly pulled my fist out, wanting to savour as much of her honeydew as I could possibly devour. I hungrily lapped up her flooding sweetness throughout her entire orgasm.

Until she pushed me away, "Stop or I'm going to pee on you."

So in lust at the moment, I shrugged, "If you want."

Sarah shook her head, "Not on the couch, and besides, you don't deserve that," and hurried to the bathroom.

Pam laughed, "You really are a kinky little slut, aren't you?"

I shrugged, "Says the girl who loves fist fucking people."

"Fair enough," she agreed, as she said, "I also like tribbing."

"What's that?" I asked, as she got undressed.

"Oh, you haven't lived until you've tribbed," Pam enthused, not actually answering the question.

Once naked, she took me to the bedroom, where books were strewn about... obviously they'd been studying and I was the break (a very lengthy break). She ordered, "Lie on your back."

I did.

She moved and joined me on the bed.

I watched, confused, as she moved her legs toward me and ordered, "Lift your ass up."

I did.

Her one leg went under my leg, her other leg went over my thigh and suddenly our pussies were kissing each other. I moaned on contact.

Pam explained, "This is tribbing."

"Oh," I moaned, as Pam began grinding on me... pussy to pussy. "Very acrobatic."

"You could be a cheerleader," Sarah said, watching us from behind.

I laughed, "Those are words I never thought I'd hear."

Valerie, who, I just realized, had disappeared for quite a while, added, "Eleanor said the same thing."

"Focus on me, Becca," Pam ordered, "grind with me. Pay attention and I'll really make it worth your while."

I closed my eyes, concentrating on the delicious sensations of our wet cunts making out with each other, forgetting I was being watched by two cheerleaders, and began to grind my ass as our pussies tribbed together faster and faster... deeper and harder... creating a new unique stimulation I had never felt before. Not as amazing as a tongue on my cunt, but it definitely stimulated me, and quickly my second orgasm of the night grew.

"So hot," Valerie said.

"Indeed," Sarah agreed.

Pam's breathing got heavier and mine did too, and both of us began grinding more aggressively... each using the other to get off.

And as rare as it happens... it's happened in less than one percent of my hundreds of sexual encounters... we came simultaneously.

Pam screamed, "Yessssss," just as my orgasm hit too... but I just collapsed and allowed the pleasure to cascade through me.

I was still orgasming, my eyes closed, when I felt wetness on my face. I opened my eyes to a close-up of a pussy and heard Valerie order, "Get licking, Becca... I'm the only one you haven't got off yet."

I extended my tongue and licked Valerie for the first time... the several times she and I had served Eleanor, we'd served only Eleanor and not each other. But now I discovered that her cunt, like the others, was sweet and heavenly, and once I started licking I wanted more.

"Oh yes," she moaned. "Eat my cunt, you eager nerd."

I was already doing that, so her words were redundant, but it was obvious she was trying to make it clear she was above me (at the moment physically as well as hierarchically).

I licked for a few minutes, Pam eventually moving away until Valerie suddenly grabbed the back of my head and began grinding on my face... coming a minute later.

After silently sharing some refreshments, we ended up in a four way daisy chain... where my face was buried in Sarah's sweet snatch again, while Pam munched on mine, Sarah on Valerie and Valerie on Pam... before I headed home in the wee hours exhilarated by my night with the cheerleaders... a fantasy coming true. I didn't have to dream about Sarah's liking me, she had treated me with respect and caring from start to finish!

I would go down on Sarah at graduation (before the ceremony) and into the summer... before she went away for camp the last two weeks of summer and then to a college up north... which made me sad and ended an ever so brief period in my life where I thought I might find romantic love with another woman. Sarah was sweet... tender... and even loving. All the while, I kept dating my boyfriend... who would end up being your great-grandfather, Kimmy. It was a confusing time... one I always go back to and wonder what if...

By the way, when I returned to my house, Mom was on her knees in my bedroom licking Eleanor... my dad out bowling.

Eleanor asked, "Did you enjoy your present?"

"My present?" I asked, watching her grab Mom's head and pull it deeper into her pussy.

"Yes, I knew you had a crush on Sarah and I thought I'd make your fantasy come true," she explained.

"Oh," I said, everything suddenly making sense.

Eleanor moaned, multitasking as she asked concerned, "Did you not like it?"

"Oh yes, it was awesome," I nodded, as I realized Eleanor hadn't sent me there as a submissive slut to be used and tossed away, but for my own pleasure. Wow!

"I knew you'd love it," she moaned again.

"I learned about tribbing," I said.

"From Pam?"

"Yes."

"It's her favourite way to get off," Eleanor moaned, before adding, "and this is mine."

I watched Mom get my best friend off.

Once she was done, Mom stood up and smiled and asked casually, "How was your night, honey?"

"Great," I answered. "And yours?"

"Boring until Eleanor got here," Mom answered.

I laughed, "I'm happy my best friend can keep you entertained."

Mom shrugged as she left us alone, "She's very entertaining."

Eleanor explained, "Isn't Sarah delicious?"

"To look at or eat?" I smiled wickedly.

"Well both, of course," Eleanor smiled.

"Both indeed," I said, as I gave her a hug... thankful that my best friend was still my best friend. Sure she had other friends now... but as I would soon learn... so did I.

The summer was great... Eleanor and I returned to being besties... one night I shared with her about my insecurities. She apologized sincerely and held me in her arms while I cried, admitting that the sudden power trip had gone to her head. Of course, she used that power trip for a nice lesbian orgy for July 4th weekend.

Sarah and I played A LOT, often with her college sister watching and ordering us both around. She loved to make Sarah fuck herself with items including pop bottles. Her sister also loved to have me eat her cunt while Sarah ate her ass.

Also... my life changed forever when I succumbed to a moment of weakness and your great-grandfather took my hetero virginity (I'd already had dozens of fake cocks and other items in my cunt) at the drive-in ... a moment of weakness that led to the birth of your grandmother (which was a blessing in disguise... otherwise there would be no you... but at the time I was devastated... as it changed all my plans for a self-sufficient future.

.....

Great-grandmother had had sex with a guy only once, and immediately gotten pregnant.

That would suck.

I'd already known that great-grandmother never went to college because she got pregnant so young, but I had never put much thought into it. I also knew that they rushed the wedding so my grandma wouldn't end up being called a bastard.

For the first time I didn't want to masturbate after reading the journal. Truthfully, it made me reflect. For one thing, I realized how it took only one mistake (or fate, depending on how you looked at it), and everything had changed. For the second, I realized I hadn't been spending much time with my best friend Julia.

So I closed the journal and called Julia, deciding I needed to work on my friendship... Julia my present-day Eleanor... although she was definitely the submissive one in our relationship.

I smiled as I recalled some of our crazy adventures, including having her go down on me at lunch in our advanced calculus classroom a couple Saturdays ago when we were participating in a United Nations competition. We snuck away to have lunch... and then I offered Julia dessert.

As she lapped away at me, Mrs. Walker walked in on us and we gave her the shock of her life.

Mrs. Walker was shocked, but recovered quickly and just ordered us to get dressed and return to the competition.

Once she was gone, I ordered, as Julia stood back up, "No, no, finish what you started."

"What about Mrs. Walker?" she asked.

"Maybe she will be our next target," I said, guiding her face back into my pussy.

I texted Julia: Hungry?

She texted back a moment later: Famished.

Half an hour later, I was in her bedroom and she was between my legs... I smiled as I pondered great-grandmother's lessons (don't allow your friendships to fade... and stay really close to your intimate friends... really, really close).

I closed my eyes and enjoyed Julia's unique pussy pleasing style... so teasing... long burning... until I begged her to suck on my clit.

She wasn't my submissive; I wasn't her Mistress.

We just loved to play with each other... although she mostly loved to lick me and I mostly liked to be licked... it was perfect... and I would have to make sure I didn't allow us to drift apart once high school was done.

But for now... I had two seductions to ponder... one being Mrs. Walker and the other being Mom.

Mom... I still couldn't fathom her as a submissive... that said, there was no doubt I planned to make her my pet in the very near future.... a gift bequeathed to me by my wonderful great-grandmother Rebecca.

As I went to close the book... I saw one more picture and a note.

I was bored one day and envisioned by a kissing booth in modern times... with an inspiration piece with you as the submissive and me as the seductress.

I hope you don't judge me... but God my biggest regret is the reality I ever got to taste your sweet kitty, fuck your tight twat or have you munching on great grand-mother's cherry pie.

I hope you enjoy....

The end of 1950s: Munching the Cheerleaders

Up next: 1950s: NAUGHTY BRIDE

If you enjoyed Rebecca's artwork and this story, please feel free to check out my other Rebecca collaborations:

Straight Housewife Blackmailed

"Moms & Daughters": A Family Affair

Summer of Slut: MILF Challenge

Coming Out in Costume

New Family Tradition: Lezmas Eve

MILF's Teen Craved Cunt Fantasy