Pillow Princess Club Ch. 10

Story Info
Pussy 12 Cock 1: Meredith discovers the joys of a transwoman.
5.5k words
4.68
13.9k
44

Part 10 of the 14 part series

Updated 01/04/2024
Created 08/31/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Pillow Princess Club Ch. 10

Summary: Pussy 12 Cock 1: Meredith discovers the joys of a transwoman.

Note: This is dedicated to Stephen, who requested the series.

Note 2: Thanks to Tex Beethoven for editing yet another wicked series.

Note 3: This is Chapter Ten of an ongoing series. (I'm still brimming with hot ideas, so who knows how long this series will eventually become.)

In Chapter One, a housewife in her mid-forties, Meredith, is spending a lot of time at home alone with her eight-month-old baby daughter while her husband is constantly away and neglecting her sexual needs. She sees from her bedroom window her 18-year-old female neighbour getting sexually pleasured by another woman, then another, and then even more. This increases the flame inside her for her growing curiosity to explore her same sex desires. She discovers a secret Pillow Princess Club, where older women sign up, and are then regularly summoned by younger women to pleasure them sexually. She signs up out of lust and curiosity, and is instantly summoned by her beautiful next door neighbour Bianca. Whereupon she services her, which begins her journey into submissive lesbianism.

In Chapter Two, Meredith is spied during her short walk of shame home, so she goes across the street to MILF Miranda Bellencourt's house to service her stocking-clad feet, eat her pussy, and get her own pussy fucked for the first time in a year and a half.

In Chapter Three, Meredith goes to her former high school bully's house, where she is greeted by a naked Miranda, who is being punished for using her before the other, apparently more important, younger pillow princesses... her punishment includes being spanked, and being required to fuck herself in the ass with a cucumber. Meredith services her third pussy, her high school bully's daughter, when said bully walks in and ends up fucking her pussy... although sadly not long enough to get her off... before she heads out for her scheduled pussy number four.

In Chapter Four, Meredith drives to a stranger's house... a cute Swedish young lady... where she discovers the joys of face sitting.

In Chapter Five, a phone call from her mother gives her more time to explore her newfound submissive love for pussy, when her Mom offers to take her daughter home for the weekend. Meredith drives to the next address, and learns it's a yoga establishment. After a brief hesitation, she goes into the business and hides behind a counter, where she services a young girl while she continues working and interacting with people.

In Chapter Six, Meredith continues her pussy pleasing tour, when she is ordered to go to a house, where she services two young women, and discovers the orgasmic bliss of being fisted.

In Chapter Seven, Meredith goes to meet a girl to eat her first ass, and she discovers her best friend is already there. Together, they worship the teen's pussy and ass. She also learns her best friend has had sex with Meredith's eighteen-year-old daughter. With all her tasks completed, she drives to a Hooters to go pee, and...

In Chapter Eight, Meredith has two wild adventures. An under the table foot job from a Hooters waitress, who gifts her a pair of her soiled Hooters pantyhose, and a promise to give her a night of unlimited coed pussy at her sorority. Meredith then drives to her first tribbing encounter, with a very cute Japanese girl. Up next: Big Rosie.

In Chapter Nine, Meredith goes to a black woman's house, where she pleases not one, but two black women, and she discovers the joy of chocolate cunt.

And now, continuing immediately after the end of Chapter Nine....

Pillow Princess Club Ch. 10

I arrived at the location... three minutes ahead of schedule, thanks to encountering an unusually generous number of green lights, speeding slightly, and barely squeaking through a yellow light.

Reaching the address, which was an apartment building, a nice one, fairly close to the Hooters I'd visited earlier, I checked my phone.

Two new messages in the app, and one from my Mom.

Before I checked them, I sent a message to IFUCKMILFS.

MERMILF: Parking.

Mom: She is down for the night. Enjoy yourself.

I didn't text Mom back at first, but then realized I should, or she'd start to worry.

Me: Thanks again, Mom. I am having a great night.

I checked the two messages from the app: one from FOOTSIES, and another new girl or woman, this one calling herself PILLOWP3.

FOOTSIES: I'm home all night now watching my younger sister so send a message when you're available. BTW, I live close to you, and your daughter used to come over to eat my pussy at all hours whenever I wanted her.

This one made me tremble. She again referenced my daughter, and this time with some very intimate details. I wasn't sure what to say yet, although I knew I'd have to report to her to 'eat at the Y', since she knew who I was, she'd had sex with my daughter, so I absolutely had to find out who she was!

I clicked on the new girl's message.

PILLOWP3: Could use a new Mommy to please me and my friends. We are having a slumber party and you would get to please five ripe just graduated from high school eighteen-year-old pussies.

This one made my pussy tingle. Five teen pussies! This wasn't quite as exciting as a chance at an entire sorority of pussy, but it was indeed maybe a great final stop to this long day's sexual activities... well... followed by a final-final stop at Footsies, since apparently, she lived near me.

I responded to PILLOWP3 first.

MERMILF: Hi, I just arrived at another Pillow Princess. If you can wait thirty minutes or so, depending on how long this next appointment takes and how far away you are, I would love to be your Mommy.

Just using the word Mommy made my pussy tingle. I then replied to Footsies.

MERMILF: I have two stops left and I sense one of them will be quite lengthy. So if you can wait a couple of hours I can stop by and service you like my daughter did.

I tapped Send, and then wondered why I'd added the part about my daughter.

IFUCKMILFS: Buzz 222. Hurry up!

I put my phone away and headed to the apartment building. I pressed 222, and was instantly buzzed in.

I walked up a flight of stairs, encountered a woman walking downstairs without incident, and then went down a hallway.

I'd gone into so many strangers' homes today that this didn't faze me at all. I reached the door and knocked.

"Come in," a voice called out.

I walked in, and directly into a large living room... although that isn't quite accurate, since the room seemed to be the entire apartment, except for the bathroom. A bed was in the middle of the room with bedside cabinets on either side, which looked quite odd (the placement, not the cabinets). A large flat screen TV on the wall. A kitchen area in one corner. Two girls apparently in their early twenties were on the bed, watching 'Dazed and Confused'.

"Hot!" the redhead remarked upon seeing me.

"Yeah, she'll do," the blonde replied.

"Come over here," the redhead ordered me.

I went over to her, and she swiped a few fingers through a jar of some lotion or other sitting on the nearest cabinet, reached her hand under my skirt, and noticed, "No panties. Nice!"

"It's just easier today," I somewhat joked, as her hand went to my pussy and she rubbed the lotion onto and into it. "Ooooooooh," I moaned; the substance was cold!

"Trust me, this stuff will get you ready for the fuck of your life," she said.

"Okay," I said, wondering what the lotion was... was it just lube? I was so horny from everything, even after my six orgasms today, especially immediately following the double helping of black pussy I'd just devoured.

"Give me some of that too," the blonde requested.

The redhead handed her the lube as she told me, "I'm Fran, and my bestie here is Brandi."

"Brandi with an I," the blonde mentioned, as she slipped off her shorts and panties.

"I'm Meredith," I said, "it's nice to meet you both."

The lotion takes some time to start working, so why don't you get out of that dress, and you can come and suck my cock while we wait," Fran said, standing up and shimmying out of her jeans.

I watched Brandi slathering the lotion on her pussy, and then fingering herself with some lotion still on her hand. "You're in for a real treat!" she told me.

"What is it?" I asked.

"Cannabis lube," Fran said. I then saw a bulge in her panties, and my eyes went wide with startlement upon experiencing two sudden revelations.

One: I'd been drugged, or at least my pussy had been canna-bissed.

Two: Fran had an actual dick to fuck me with... not just a strap-on.

Fran chuckled as she pulled her panties down to reveal her six-inch cock, "You didn't figure this out from my handle or my messages?"

As she stroked her hard cock, I stammered, a little overwhelmed by the dual surprises, "N-n-no."

"Disappointed?" she asked, as she came over to me while taking off her t-shirt.

"Not at all," I said, that cock pointing right at me suddenly looking very appealing on her pretty, feminine body. She was slim, with great curves, and perky breasts. They weren't particularly large, but not tine either... what many would call a nice handful.

She placed her hands on my shoulders, and I very willingly lowered myself down to her lovely cock. As I admired her erection and brought my hand to it, I wondered if sucking or fucking... or sucking and fucking a transwoman counted as cheating on my husband. Early during the course of the day, I'd convinced myself that eating pussy didn't, and getting fucked by a strap-on didn't... but this phallus made of flesh and blood really complicated things!

Regardless, I pushed away the semantics of cheating... it wasn't my fault my husband hadn't fucked me in a year and a half, leaving me absolutely desperate for some action... and I took her cock into my mouth. After all the pussy I'd serviced today, this was a welcome change!

I was slowly bobbing as Fran said, "Just so you know, we didn't drug you. We only drugged your pussy."

I'd almost forgotten about the drugging, since I was distracted by this cock. I backed away and asked, "You drugged my pussy, but not me?"

"Yes, you'll notice your head is perfectly clear, but your snatch is probably tingling very nicely about now. It's a lube that gets your pussy high, and thus it gives you orgasms that are out of this world!" she explained as she grabbed her cock and traced it around my lips. "It doesn't impact your cognitive thinking or your physical actions. You yourself aren't high, only your pussy is."

"And your ass, if you lube that up too," Brandi interjected.

"Yes, but that wouldn't be a first-time exploration," Fran said, sliding her cock back into my mouth.

"God, I love it when you get sucked off by older women, baby," Brandi said, as I slowly sucked on the trans woman's cock. Although the shift from licking pussy to sucking cock wasn't a difficult one, it had been a while since I'd had a real cock in my mouth. I couldn't deny it... I loved the feeling of a hard, throbbing cock between my lips. I enjoyed the movements of bobbing. I'd always loved sucking cock... loved the idea of teasing and pleasing... liked the power I had in that role... I was the one who controlled his... or in this case... her pleasure.

"Yeah, I know you do," Fran moaned softly.

"Fuck her face," Brandi encouraged, while she moaned.

"You love when I dominate an older MILF slut, don't you?"

"Oh yeah, you know I do," Brandi moaned again. I couldn't see, but I assumed she was rubbing herself while she watched me suck her girlfriend's cock. (I assumed they were dating.)

"I don't want to come yet," Fran said. "We've got to wait until the pot lube has gotten her all revved up."

With no place to go, I thought to myself... the lyrics of the old Meatloaf song popping into my head. I'd been about to start bobbing faster, but hearing Fran say what she said, I changed my plans and instead, I took her cock out of my mouth and slithered my tongue down her shaft to her hairless balls.

"Oh, shit, that's it! Suck those big balls," Brandi urged.

"Yeah, MILF slut! Wake up that big load waiting to be unleashed for you," Fran moaned, as I sucked on one ball while I licked her ball sac.

"Mmmmmmmm," I responded. I felt my pussy beginning to tingle in a strange and intense way, and with a little more sparkle than usual... was this because of the spiked lube, or was it just from the anticipation of getting fucked?

"You want my load, slut?" Fran asked.

"Yes, I do," I answered, as I rummaged my tongue around searching for the other ball, and when I found it, I replicated the dedicated lips and tongue attention I'd lavished on the previous one.

"Yeah, do you want this big load?" she asked again.

"I do, I really do," I moaned, the prospect of her erupting onto my face, or even inside my pussy was very appealing... although I really shouldn't allow my unprotected womb to host a load of active sperm.

"Then get my cock nice and wet for that pussy of yours," she ordered.

"Yes, ma'am," I agreed happily, eagerly skimming my tongue back up the shaft and taking the cock back into my mouth. Using my tongue to swirl around the cock head and create extra saliva, while using my left hand to stroke her cock as I sucked, I soon had her moaning. And I also had Brandi moaning. Actually, I even had myself moaning!

After a couple of minutes, she pulled out and ordered, "Crawl between Brandi's legs."

"Yes, ma'am," I agreed, getting off my knees, and climbing onto the bed and between the blonde's widespread legs... as she slowly rubbed her shaved pussy... only a tussle of hair perched above it like pubic mistletoe.

"You hungry for more pussy?" Brandi asked, as Fran got onto the bed behind me.

"As of this morning, I can't ever get enough pussy," I admitted, inching ever closer to hers... admiring it like I had all the others. There's just something so sexy about a pussy. Each one is unique in its appearance, even though they all have the same basic setup.

"Are you ready to eat pussy and get fucked at the same time?" Fran asked, her soft hands on my hips. Now that I knew she was trans, it occurred to me that from the arrogance apparent in all of her texts to me earlier, I should have thought she'd look butch. But although in person her arrogance was still very present, her physical appearance was petite and very pretty.

"Yes, ma'am," I agreed, as I inhaled Brandi's feminine scent. I then joked, my own pussy on fire, "I bet my husband would love to watch this."

"Does he know you're a pussy munching slut for young pussy?" Brandi asked, as she continued slowly rubbing herself.

"No, he hasn't a clue," I moaned loudly as Fran's cock teased my pussy lips... which now felt super sensitive. "I only discovered today that I liked pussy at all!"

"So you never ate any pussy before today?" Brandi asked, as I leaned forward and licked between her pussy lips.

"Not one," I answered.

"And I'm assuming you've never had a trans cock?" Fran asked, continuing to tease my burning pussy.

"Never even seen one before yours," I moaned, as I tasted Brandi's delicious pussy, while dying to feel that dick slide into my own pussy.

"Tell me what you want to happen," Fran said. She was driving me wild with temptation!

"I want you to fuck me," I answered between licks. "Pound my pussy and use me as your slut."

"Good answer," she said, and she slammed into me hard.

"Mother fucker!" I screamed as her dick filled me completely.

"That I am," Fran smirked, as she began fucking me.

"Oh my God," I gasped, as the pleasure of her dick inside me was unlike anything I'd ever felt. One would think there couldn't be anything as inherently male as a dick, but that would be wrong. Wielded by a woman, Fran's dick was sensitive... intense... rapturous... nothing at all like a man fucking me! Although granted, the pot lube Brandi had rubbed on my pussy and slid inside me was creating sensations I hadn't even known existed.

"I think the pot is kicking in," Brandi giggled as I tried to lick her pussy, but was overwhelmed and totally distracted by the intensity of the pleasure Fran and her cannabinoid helper was giving me.

"Oh, this is so intense," I moaned and trembled, as the slow fucking was making my head go light, and my body burn with desire.

"I think she likes it," Brandi giggled again, as she placed her hand on the back of my head.

"I fucking love it," I declared, as I began slowly bouncing back on Fran's cock... needing to be fucked hard... needing that cock inside me as deep as possible. Never in my life had I wanted to be pounded more... or harder.

"Oh, you want it harder?" Fran asked as I bounced back on her dick.

"Oh, fuck yes! Fuck me, pound me, give me all that dick," I babbled. I wasn't even trying to lick Brandi's pussy anymore... the pot lube had transformed me into a ravenous, desperate slut, needing to come.

"Fuck her, baby, give her all that dick," Brandi said, as she took over my job and began rubbing herself.

Fran bucked hard into me.

"Fuuuck yes!" I screamed... the intensity reaching even newer heights of pleasure.... Hoping the neighbours above, below, to the left, to the right, and across the hall couldn't hear my euphoric screaming.

"Get back to eating, slut," Fran ordered, pushing my head back to her girlfriend's pussy, then leaning forward, her dick reaching new depths inside me.

"Yes," I babbled mindlessly as I lapped the tangy twat before me, and Fran bucked her hips into me. "Oooooh!"

Again.

"Fuck!"

Again.

"Please, harder!"

Again.

"More," I pleaded as I licked the best I could, each deep thrust forcing my face into the wet pussy I was attempting to please.

Again... three fast, deep thrusts.

"Yes! Yes, fuck!" I babbled, an orgasm rising above the horizon.

Again... three fast, deep thrusts.

"Oh God, don't tease me, just pound my fucking wet cunt with your lovely lady dick," I begged with an urgency that sounded as desperate as I felt, as I gazed beseechingly back at her.

"Then get ready to come," Fran warned me. Her hands were on my hips, and she began slamming into me... her body crashing into me with each deep thrust, while my tongue licked Brandi only haphazardly, and my body burned with undeniable lust.

"Oh yes, fuck! Oh yes, fuck me! Jesus Christ, more! Harder! Deeper! Oh, fuck yes, you big-dicked mother fucker!" I spouted nonsense over a good, long minute of her deep, hard thrusts, while I did a terrible job of trying to lick Brandi as well.

"Come now, slut! Come on my dick, and declare yourself my cum slut!" Fran demanded, her hand on my head pushing it into her friend's pussy, while she kept hammering me from behind.

"Oh fuck, fuuuuuuuck!" I screamed into Brandi's pussy, my orgasm coming just seconds after being told to... an orgasm that was unlike any I'd ever had before... discovering an intensity I hadn't known existed. I trembled uncontrollably as my orgasm hit every part of my body like a billion tiny pleasure tornados.

Fran pulled out, my own cum gushed out of me like a broken faucet, and she grabbed my hips and flipped me onto my back.

She then pulled me to the edge of the bed and slid right back into my pussy, which was still leaking.

"Oh my God," I moaned, not sure I could take much more. The pleasure was just too intense.

"Come and sit on her face, baby," Fran said, as she slowly pumped her dick in and out of me.

12