Pillow Princess Club Ch. 15

Summary: Pussies 24-25: MILF discovers the joys of anal sex.

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 Fifteen of an ongoing series (with at least four more in the works).

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: her growing curiosity to explore her same sex desires. She discovers a secret Pillow Princess Service 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 eats her tasty pussy, 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 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 the girl 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, and 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.

In Chapter Ten, Meredith goes to meet a girl and her friend, and discovers that one of them is a trans woman with a six-inch cock. She discovers the joys of pot lube, which leads to a wild threesome... eating some pussy, and getting fucked to five orgasms. (Yes, five of them, that's not a typo... hurray for cannabis pussy lube!)

In the pivotal Chapter Eleven, Meredith returns to Hooters to pick up a fresh pair of cum coated pantyhose. She goes into a bathroom, eats Carla's pussy through the pantyhose and comes on Carla's pantyhose knee. Things get serious when they both share their feelings with each other, and Meredith agrees to go on a date with the coed the next night. Meredith then goes to a slumber party, where she dines on five teenage pussies and has a few more orgasms herself, in a wild Mommy roleplay scene.

In Chapter Twelve, Meredith visits a coed who has been using her daughter for some time. She worships the girl's stocking-clad sweaty feet, learns more about her daughter, pleases pussy number nineteen, and reaches her own orgasm by humping herself on the girl's shin.

In Chapter Thirteen, Meredith is shocked to find her mother-in-law in her home, with the babysitter between her legs. This leads to more revelations for the first day Pillow Princess Pet, and two more pussies: her mother-in-law's and the babysitter's... and another fucking from a big strap-on cock on the hips of said mother-in-law.

In Chapter Fourteen, Meredith acquires her own supply of pot lube, pays for the delivery by eating a sweet young pussy, and then she gets the surprise of her life! She's pleasuring herself on the washing machine, when she is caught by her eighteen-year-old daughter, who soon convinces her to cross the line into incest, and the mother and daughter share a long and wild sexual morning, which among other things, starts her orgasm count for the day off with a bang.

And now continuing just after Chapter 14...

Pillow Princess Club Ch. 15

So with the taste of my daughter's pussy still lingering on my lips and in my mouth, I left my house and went to the address Olivia had texted to me. It was only a ten-minute drive.

In my head I replayed the wild reality that I'd just had sex with my daughter... wild, unbridled, multiple-orgasm sex. It hadn't even been twenty-four hours since I'd eaten my first pussy ever, and then I'd dined on twenty-three different pussies during the course of the afternoon and evening, and I myself had experienced around the same number of orgasms... give or take... and now I was driving to a stranger's house to get sodomized... my asshole already starting to tingle from the pot lube administered by my daughter's fingers just before I left the house.

I reached the house, and I considered how strange it was just to walk up to a house in the middle of the day to have sex with a stranger... and even stranger that I was going into the house to lose my anal virginity. But the strangest thing was that about an hour ago my daughter had assured me that when Olivia (the stranger I was about to meet) had taken her anal virginity, she'd done a wonderful job!

It was even more awkward and nerve-wracking to be doing this in broad daylight.

Yet when I parked, I didn't hesitate to text BACKDOORBANGER.

HUNGRYMILFMOMMY: I am parked across the street.

I saw a message from TOYGIRL.

TOYGIRL: Great, I'll send you a message the moment I get home.

I responded:

HUNGRYMILFMOMMY: Sounds good. I could use a good fucking and exploring some new toys.

I saw BACKDOORBANGER had responded.

BACKDOORBANGER: Come in the front door. It's unlocked.

I took a deep breath and got out of my car. Thankfully today I was dressed much more conservatively: a cute sundress and white stockings... a lot less risqué than the very revealing maid outfit I'd sauntered around in yesterday throughout the afternoon and night. On the other hand, I was more likely to be noticed going into a stranger's house at lunchtime.

I was crossing the street, when I noticed that an older man walking his dog was coming towards me.

I looked away, perhaps too quickly, and headed up the walkway to Olivia's house. Then when I reached the front door, I looked back and saw the man staring at me. I wasn't certain whether he knew why I was here, or was just checking me out. I knew I looked sexy in my summer attire. As I went into the house, I decided it must be the latter, because how could he possibly know that the woman living here fucked other women in the ass on a regular basis?

I went into the house and down a short hallway into a living room, where I was surprised to see a pretty girl sitting in a rocking chair that must have once been her grandma's. She was a brunette, and her outstretched legs were crossed on a footrest.

As soon as she saw me, she called out with a British accent, "Nana, my friend is here."

"Okay, have fun," an older woman called back, poking her head out of a bedroom door down another hallway and looking in my direction.

"Um, hi," I said, awkwardly.

The girl stood up, went past me, took my hand en passant, and led me up a flight of stairs into an attic bedroom. "Don't worry about her recognising you, she's blind."

"Oh! I'm so sorry," I sympathized, now feeling very awkward to have worried about someone seeing me, but relieved that she hadn't, because she was blind. What kind of jerk was I?

"Don't be," she said. "She's always been blind."

"Okay, thank you," I said as I stood there, unsure of what to do and awaiting instructions, as usual.

"So you've never been fucked in the ass?" she asked, looking at me appraisingly.

"No," I answered, "but a pillow princess stopped by my house this morning. She fingered my pussy for a moment, so she could smear some put pot lube into it."

"Pot lube?" Olivia asked, looking perplexed.

"Yeah, it's a special cannabis lube. It gets your pussy or anus... but not the rest of you... high, which enhances whatever pleasure that orifice receives," I explained. "I know firsthand that it works in the pussy... last night it drove me completely bonkers for hours, while I had a crazy number of orgasms. I've only heard from other people how well it works in the ass, but they tell me it's just as good."

"I've never heard of that before," she said. She then came over to me and helped me out of my sundress. "Oh, nice! a garter-belt and stockings... and you're commando!"

"I like to sex it up for my Pillow Princess Mistresses," I explained. I shifted into my full submissive mode while I looked into this girl's hypnotic hazel eyes.

"Well, you're succeeding," she approved, as she tossed my dress on her dresser and looked me up and down, blatantly admiring my body.

"Do you have any kids?" she asked.

"Two daughters and a son, but he's in England," I replied comfortably. There was no reason for me to hide anything, since she'd already fucked my daughter Catherine in the ass.

"Hold old are they?"

"Eighteen, eight months, and twenty-two."

"No way," she said, her British accent so sexy. "You don't look old enough to have a son that old!"

"Thanks," I said, appreciating the compliment.

"Were you born here?" I asked.

"No, I'm from London. I moved here a couple years ago, when my nana got ill," she explained. "She's better now, but now I love it here."

"Your accent is really sexy."

"Thanks," she said. She went to the nightstand and opened a drawer. "I've been told that before."

"By the way," I said, deciding for reasons unknown to remind her she'd taken my daughter's anal virginity too, "I think you know my daughter."

"Oh? Who is she?" she asked, as she turned around with a couple of small toys in her hand.

"Catherine Hamilton."

"You're Catherine's Mom?" she blurted out in astonishment.

"Yeah. She told me today that you took her anal cherry too."

"Shit, I guess I did," she said, still looking surprised. "That makes doing you even hotter!"

"Yeah," I agreed, the idea of losing my anal virginity to the same girl my daughter had was really hot! I know, I know, yesterday I wouldn't have remotely said that, but Catherine and the five orgasms I'd already experienced today had done some powerful convincing. Perhaps in part it was the pot lube talking, but whatever the reason, this coincidence made my pussy burn. Oddly, the lube Catherine had rubbed into my ass hadn't done anything so far.

"So she just told you that out of the blue?" Olivia asked, as she placed the toys on the bed, then went and took something else from the drawer.

"Pretty much. She was on my phone changing my handle for me, and she saw your message," I explained. "In fact, she's the one who sent the message on my behalf agreeing for me to come over here, while I was trying to talk her out of it. Fortunately, she talked me down, and now I'm very glad to be here. As you can imagine, the past twenty-four hours or so since I joined the Pillow Princess Service Club, have been really crazy."

"Shit, so your daughter Catherine wants you to get arse fucked?"

Hearing the expatriate Brit say 'arse' instead of 'ass', especially with her sexy accent, made my pussy tingle, "Yes, she actually insisted on my doing it, and she rubbed some pot lube in my anus so I'd have a particularly good experience."

"Wild!" she said. She then instructed, "Get onto the bed and on all fours, facing away from me."

"Okay," I said as I got onto the bed. "I should mention I'm feeling very nervous about this."

"I couldn't tell," she said without a hint of sarcasm.

"On the other hand, the pot lube in my pussy is keeping me horny as fuck, which is compelling me to do things that normally I wouldn't be daring enough to try," I added, as I got onto all fours and presented my ass to her for the sodomy we both wanted to happen.

"Such a nice arse," she said, gently caressing it with both hands.

"Thanks," I said, enjoying her massage-like touching.

"I can't believe this pretty arse hasn't ever been fucked," she said. She pulled my ass cheeks apart a minute later, and must have been admiring my rosebud.

"Honestly, I hadn't ever put much thought into it before I joined the Pillow Princess Service Club yesterday."

"Your husband never broached the topic?" she asked, leaning forward and licking my asshole.

"No, he's always respected me as a woman."

"Bad idea. You don't want to be respected, do you?"

"No, I want to be told what to do. I want to please as many women as I can."

"But what about your own pleasure?"

"I get turned on by satisfying other people; by obeying them. And that preference has given me almost two dozen orgasms in the past twenty-four hours," I answered, my body beginning to tremble because of her tongue rolling around the perimeter of my asshole... just like when my daughter ate my ass this morning, it felt soft, sensual and surprisingly relaxing.

"Holy shit! Two dozen?" she gasped.

"The pot lube helped me get most of those orgasms," I said. The pleasure Olivia was giving me right now was increasing markedly.

"I'll have to research this pot lube," she said, continuing to bathe my asshole.

"It's very stimulating," I said, "literally."

She laughed out loud, as she as scooped some lube (the ordinary kind) onto her finger and then smeared it between my ass cheeks. She then placed a different finger against my ass and said, "Now let's see if it also enhances pleasure in your arse."

"Yes, let's," I agreed, as her finger poked against my hole.

"Relax," she said, just like my daughter had advised me earlier.

"I'll do my best," I said cautiously. At least I wasn't as nervous about having my ass fingered as I was the first time!

"God, such a perfect little asshole," she complimented, sliding her finger smoothly inside me.

"Ooooooh," I moaned. The pleasure was more intense this time... likely because of the pot lube.

"Yeah? You like that?" She was now sliding her finger deep inside me.

"It feels really good, in an odd sort of way," I appraised, which was perhaps the best description. It wasn't overly pleasurable, but it was providing me with some subtly soft sensations, and it wasn't at all uncomfortable.

"Just wait until your arse gets used to being really filled up," she assured me. Unlike my daughter, she was wiggling her finger around inside my ass... and the feeling was almost indescribable... weird... yet good... yet kinky... yet also natural somehow. Perhaps having something in my ass was a natural step towards my transition into a new version of myself.

"Oh! That's..." I began speaking, but then couldn't remember what I'd begun to say.

"I've got to gape your tight little arse hole gently and gradually," she explained, her finger continuing to slowly swirl inside a hole I'd had no idea could be swirled inside.

"Gape?" I asked. This wasn't a term I recognized.

"Yes, gape. As in gently stretching your asshole wide open," she explained, "so I can fuck it good without hurting you overmuch. A certain amount of pain is inevitable, but if I'm doing it right, you'll enjoy the pain just as much as the pleasure."

"Oh?" I moaned. Surprisingly, her finger rotating clockwise inside my anus was making my pussy tingle. I'd never thought they were connected, but apparently they were.

"Yes, your arse was made to be eaten, gaped, and then fucked," she said, her finger continuing its blender-like spinning inside me. "And for the best results, it needs to be done in that order."

"I don't know about that theory..." I moaned, "...but this does feel a lot better than I'd expected."

"Oh, it gets a lot better! We're just getting started." She then pushed a second finger into my ass.

"Oooooooh!" I moaned, feeling a surreal mixture of sudden pain, but also growing pleasure.

"Yeah, your arse is just swallowing up my fingers," she encouraged, two fingers now swirling inside me... stretching my ass wider open. The crescendo of feelings kept making my pussy tingle and my head spin.

"It feels..." Once again, when I tried to say something, the growing, burning pleasure inside my ass distracted my focus into nonexistence.

"Feels good, doesn't it?' she suggested, the two fingers swirling inside me delivering numbing pleasure... very different from having my pussy licked or fucked or fisted. This was less intense... yet somehow it was also more intense, given the numbing sensations burning inside my ass.

"Weirdly pleasurable," I described succinctly, as she continued gaping my asshole... or better yet, my 'arse'... while the slow, burning sensations continued growing.

"Yeah, your arse isn't accustomed to feeling pleasure. But as it adjusts to the new sensations of being penetrated, it will start wanting to get fucked... or even pounded... and eventually even hammered."

"Oh yes, that sounds wonderful," I moaned. Her fingers fucking my ass were starting to become more and more all that I wanted to happen!

"You about ready to get arse fucked?" she asked, her fingers now modulating from those constant rotations to slow in-and-out finger fucking... with two fingers.

"Yes!" I moaned, her fingers feeling so good sliding in and out of my ass... which now wasn't enough. I wanted more! I wanted something longer going into my ass, so it would reach deeper! I also wanted something thicker spreading my asshole wide open!

"Start begging for more," she ordered, and she began pumping her fingers in and out me... fast!

"Oh, please ass fuck me! Fuck me with your fingers! Please slam one of those toys inside my arse and sodomize me!" I babbled. Pleasure was now consuming me!

"Don't move," she ordered, pulling her fingers out of me.

"Ooooooh," I moaned, my backdoor now feeling achingly empty.

"Toy or strap-on?" she asked as she stripped out of her dress, leaving her wearing only some thigh highs.

"Strap-on, please," I said without needing to think about it. "I want to feel your body slamming into mine while you take my anal virginity."

"Mmmmmmm, I think you'll turn out to be a great anal slut, just like your daughter," she approved, as she selected a harness with a six-inch cock attached to it.