Pillow Princess Club

Summary: A MILF spies on her teenage neighbor getting pleasured and....

Note 1: This is a 2022 Summer Contest Story so please vote.

Note 2: Thanks to Steven for suggesting the idea.

Note 3: Thanks to Tex Beethoven for editing.

Pillow Princess Club

Our new next door neighbours were a very good looking family who'd recently moved into our upscale gated community from Italy.

Angelo and Francesca Ricci were expanding their Italian restaurant and hotel chains to various locations in America. They had two kids: Lorenzo, who was primed to run their East Coast chain, and Bianca, who was spending the Holidays with her family in America before returning to Milan for a few months to complete her studies at a private school. Then next fall she'd be attending college in America.

They arrived during the winter, and Bianca and my daughter Catherine hit it off exceptionally well. This was a little surprising, considering that all my daughter's courses were advanced placement ones, while Bianca was a Twitter influencer (which I'd never heard of until my daughter explained it to me, and then I wondered how that could seriously be a thing).

They attended a New Year's Party together, which was the first time my daughter had been to a party outside of our home (she'd always attended her own birthday parties, of course), and they kept in contact online for the next few months before ironically, Bianca arrived for the summer at the same time Catherine headed off to her summer job at a camp for children with disabilities.

So as the summer arrived, I was alone... except for my baby daughter, born eight months previously...a surprise daughter when I was forty-five, eighteen years after my eldest daughter was born. My son was in London (England, not Ontario), spending a year abroad. My husband was in Washington, DC, working with the government on a major trade deal with Canada, or something like that.

So perhaps it was my loneliness that led me to all that happened.

....

It was early afternoon, and I was re-organizing my bedroom, when I glanced out my window, which had a good view of the neighbours' backyard and swimming pool. I was just looking outside to see if the clouds had left, since the forecast had predicted they'd do by early afternoon... and for once, the Weather Channel was correct. The sun had come out, and the day looked beautiful. I was about to turn away, when I glanced down to the neighbours' yard, and I gasped... Bianca was lying on a recliner near the fence, wearing just a bikini top, and there was a large black woman between her tanned legs.

I'd never witnessed a lesbian act in real life before, although I'd be lying if I claimed I hadn't had some lesbian fantasies during the past few months... enhanced by my husband's refusal to have sex with me once he learned I was pregnant, and then he'd been in DC for the eight months since I'd given birth. So I'd been an unwilling and resentful celibate for the past year and a fucking half, and still counting.

So like many neglected women, I went online.

Watching porn.

Reading erotica.

Sometimes it was gangbangs or orgies... the idea of being fucked by two men at a time, or a bunch of them in a row, was an exciting, if taboo, fantasy.

Sometimes I ogled anal... which I'd never seriously considered in real life... but in fantasy, it was hot... there was something about a woman being bent over in porn and drilled anally that I found a major turn-on.

Sometimes I went for mature sex... or better yet, MILFs with young studs, since the idea of being seduced by a young man with a big cock and lots of stamina was super stimulating. I fantasized about getting fucked by a young man who found me attractive, and who could also shoot multiple loads inside and onto me in rapid order (picturing a bukkake followed by a cum walk, so I could go somewhere else and take part in even more kinky fetishes, really made my pussy wet).

But more often than not, I read and watched lesbian porn... and also more often than not, it was younger girls seducing, and sometimes even dominating, older women.

In short, I'd become obsessed by various sexual scenarios, all of which got me off, so long as they centered around a woman I could pretend was myself.

I blamed Bianca Ricci for my preoccupation, since from the first time we met until she stopped by yesterday with some Italian wine she'd brought back for me, she was always so touchy-feely and complimentary (both of them sweet attentions my husband never gave me). Her soft hands touching me always sent warm sensations up and down my back that I found confusing, but vastly pleasurable.

So visions of Bianca seducing me gradually entered my fantasies... and my dreams. She also seemed a lot like Bree, the main character in my favourite erotica series, Lesbian MILF Seductress... both in looks and persona...

So (back to the present day), although I shouldn't have remained staring out my window and watching... I did.

In awe.

To make it even crazier, Bianca was on her phone for the entire time this large black woman was between her legs.

I felt so dirty to be watching this lesbian act like some voyeur... like some peeping Tom. I wasn't some teenage boy like George from Back to the Future, climbing the tree with binoculars to spy on some girl.

I was a mid-forties woman.

A married one.

With a sleeping baby in the next room.

Again, I should have turned away.

Yet instead, I stuck my left hand inside my shorts and panties, and slowly rubbed myself.

The black woman licked Bianca for a good ten more minutes, making me wonder how long she'd been there, before she stood up and simply walked away.

No words were spoken.

No gestures of thanks or farewell.

I was so close, and I kept staring at the half-naked Bianca, even though I couldn't see her pussy from this angle.

I was about to come, when my infant daughter Hannah woke up crying.

I sighed.

I Ignored the burning inferno inside me, and went to feed and change Hannah.

Almost an hour later, with Hannah now fed, changed and content, I brought her to my room so I could finish what I'd been doing (re-organizing the bedroom, not masturbating) before she'd woken up... and before the lesbian act I'd accidentally witnessed had distracted me.

I didn't mean to (okay, I did mean to), and I knew I shouldn't (but I did anyway), but my curiosity got the better of me, and I peeked outside and into the Ricci's backyard again.

And I was surprised again.

This time a thin, tanned brunette (I couldn't tell if she was a teenager or an adult) was between Bianca's legs, and Bianca had what looked like a glass of lemonade in her left hand.

This was crazy.

I watched as Bianca lifted the glass to her lips and leisurely sipped it. I couldn't explain why, since sipping lemonade is hardly a sensual act, yet on this occasion it seemed sensual to me. My long-neglected pussy burned, and I wanted to finish what Hanna had interrupted earlier (this time it was masturbating instead of re-organizing), but I couldn't do that with my daughter nearby on the floor playing with her toys... no matter that she wouldn't have a clue what I was doing... I just couldn't.

So reluctantly I turned away, picked up Hannah, and went downstairs. I needed to do some laundry anyway.

Two and a half hours later, Hannah was back in her crib sleeping, and I was back in my room peering out my window... disappointed to see that Bianca was no longer out there.

I couldn't believe how disappointed I was!

Nevertheless, with a little time on my hands, I got on my bed, iPad in one hand and my other hand between my legs, and I re-read the original Lesbian MILF Seductress story (called Neighbour). The story was about a teenage seductress seducing her best friend's Mom... which greatly turned me on... the only major difference between myself and Nadine (the woman in the story) was that in the story, the seductress had also seduced and turned into her lesbian pet Nadine's daughter... which I knew would never happen with Catherine, since she'd kept the same boyfriend since their freshman year of high school. They were even going to attend Harvard together in the fall.

Two orgasms later, I got out of my bed... feeling refreshed, but also a little embarrassed by how horny I'd gotten from watching a woman, or more precisely two women in a row, going down on my eighteen-year-old neighbour.

This time I didn't even glance out the window as I headed downstairs to make supper for myself.

.....

The next morning I woke up, feeling tired after not so great of a sleep. Little Hannah had gotten me up more often than usual. I got out of bed and glanced out the window. It was seven-thirty in the morning, so of course no one was there.

Every half hour I went back to my bedroom to look out the window. I don't know why. I mean I'd found Bianca's dalliances hot, but it wasn't like she'd be doing that every day.

At eleven, just after putting Hannah down for a nap, I looked out my bedroom window and saw that Bianca was once again tanning... this time with her sunglasses on... but also with yet another woman between her legs... this one wearing a coloured sundress. Maybe she did do this every day?!

My baby asleep, I stood by the window and watched. I still couldn't explain why, but there was something so erotic and taboo about watching a woman occupying herself between the legs of another woman. I'd read stories about it... I'd watched videos of it happening... I'd even fantasized about doing it, but nothing felt quite as raw and real as watching your young real life neighbour being pleasured orally by another woman.

To my surprise, as I slowly rubbed myself, the younger looking woman remained busy between Bianca's legs for more than twenty minutes... before I noticed Bianca's legs stiffening, and then her head stretching back slightly as she assumedly came.

My assumption was proven correct when a couple minutes later the girl, who was now revealed as a woman probably in her forties, stood up and walked away. Again there was no interaction or even any communication between the two, the woman simply finished her task, then immediately got up and left.

I hadn't come yet, having deliberately only done a slow burn while I enjoyed the unknowingly exhibitionistic act... wondering who the woman had been between Bianca's legs this time, and what had led to her to begin serving between those lovely, tanned legs.

As I admired this beautiful eighteen-year-old girl, still imagining myself being next in line to explore my lesbian side by servicing her, I began rubbing myself a little faster. I stared at her long legs; I admired her firm breasts held up so perfectly in her blue bikini top, and I longed to see her pussy close up while I was between her legs.

My orgasm was still rising when I was surprised again. Another woman entered her backyard. But unlike the previous three women, I knew this one. It was our mutual neighbour across the street, the wife of a congressman, a stuck-up bitch named Miranda Bellencourt.

I couldn't believe it!

Nor could I believe what I was seeing when the pretentious bitch, dressed in an elegant red dress, nylons and heels, approached Bianca, and seemingly without saying a word, she knelt between Bianca's legs, which were still parted to accommodate her prior supplicant.

My hand froze between my legs as I continued watching in fascinated shock. While a string of women paraded in and out of a backyard to service a hot eighteen-year-old was crazy and unbelievable, someone I knew being one of them was surreal, and it made this taboo collection of sex acts I was spying on even hotter.

Again, I slowed down my own self-pleasuring, wanting to fully enjoy this additional wicked lesbian act.

A few minutes into the licking, my phone rang. I knew it was my Mom, since I had a ring tone just for her. I needed to answer it, since if I didn't, she would worry... that was just the way she was.

I removed my hand from my fevered pussy, and went to grab my phone. "Hi, Mom," I greeted, returning to the window.

For the next fifteen minutes we chatted about inconsequentials, and the entire time I continued watching the lesbian activity through my window. As Miranda licked Bianca's pussy, Bianca flipped through her phone as if the uppity older woman wasn't even there. Bianca's offhandedness while being serviced by a woman who was completely at home in high society was fascinating. Again, how had this pairing originated? What had convinced Miranda to willingly walk across the street to service a teenager? It just didn't make sense... even though I wished I was the one crawling between those long, tanned legs... but I knew I'd never really do such a thing... fantasy is very different from reality... although right now I was watching some astonishing reality!

Hannah woke up, so I reluctantly needed to stop watching the lesbian act... although I really wanted to see Bianca come again. I said goodbye to my Mom, fetched Hannah, brought her to my room, and breastfed her while I resumed watching Miranda licking Bianca.

It lasted another few minutes before Bianca's legs again stiffened, and she came.

God, watching these lesbian acts was turning me on so much!

I watched as Miranda got up a minute later, spoke briefly with Bianca, then turned and walked away. As she did, she glanced upwards... and right into my window!

I quickly darted away, but not before I saw her smile... which made it pretty clear she'd spotted me.

Rattled, I went downstairs and made myself some lunch.

When the doorbell rang a minute later, I was terrified. I assumed it was Miranda. What would I say to her? I went to the door and peeked through the peephole, and saw it was only a delivery from Amazon.

I carried in the package, a sigh of relief coursing through me. Maybe she hadn't seen me after all.

I ate my lunch while watching the View, and once Hannah was back down for a nap, I went back up to my bedroom and looked outside. At first I was disappointed... Bianca wasn't sitting in her usual lawn chair.

But as I started to turn away, I saw she was sitting on the edge of the pool, in a position where if she looked up, she'd easily see me, and she had yet another woman between her legs... except this time the woman was in the pool... up to her shoulders... and oddly... she seemed to be fully dressed... with her hair in a ponytail.

I went to the very edge of the window and peeked out to watch. I certainly didn't want Bianca to figure I was some pervert watching her, even though I guess I was one.

Bianca braced her hands behind her and looked up... right toward my window. I urgently backed away.

Terrified of getting caught, I returned downstairs to my living room. Horny and desperately needing to get fucked, I tried something I'd read about in an erotic story. I grabbed a cucumber and used it to fuck myself to a few orgasms.

The wet, limp cucumber no longer useful for its original purpose, I tossed it out.

A couple hours later, I took Hannah for a walk in her baby stroller like I usually did around 3:30, although I hadn't done so yesterday.

I was returning to the house around thirty minutes later, when I saw Miranda walking towards her car. I tried to pretend I didn't see her, but she called out, "Meredith, got a second?"

"Yeah, sure," I replied, sighing to myself as she came towards me.

As she reached me, she looked down at Hannah and said, "She's so cute."

"Thanks," I said, not used to receiving compliments from this woman.

"I can't imagine starting a new family at your age," she said, countering her compliment with a criticism.

"Yeah," I laughed, "Sometimes I can't imagine it either."

"Well, you got a good one," she complimented me again.

"Thanks," I said. "She keeps me pretty busy."

"I bet she does,"

"Yeah," I said, feeling a little awkward about this chitchat, still worried that she'd seen me watching her. It was only then that I realized I shouldn't be nervous. I wasn't the one who'd been licking a teenage girl's pussy!

"It must be lonely with Jack being away so much," she said.

"Oh, it's not much different when he's around." I joked, although sadly, there was plenty of truth to that statement.

"Yeah, I get it," she nodded.

Hannah started to make noises, which I used as an opportunity to say, "I'd better get Hannah inside."

"Good idea. But one more thing... if you ever want to talk about what you saw, just let me know," she said.

"What I saw?" I asked, trying to act innocent, as if I had no idea what she was talking about.

"I know you saw me eating Bianca's sweet pussy," she said bluntly, and with no sign of shame.

"Oh, that. Well, what you do for fun is your own business, not mine."

"Except you seemed to be making it your business."

"Not really, I just looked out the window at the wrong time."

"Oh, are you saying you didn't watch us for very long?" she asked. "I could have sworn you watched for quite a while, wishing you could be me. Which, actually, isn't an impossibility."

"I've got to go," I said, pushing the baby stroller towards my house.

"Whenever you get hungry for a snack, just let me know," she called after me.

I kept walking, my face flushed, and then I cursed myself, since all my kneejerk defensive responses likely had made her think she was right, and that I was obviously guilty as charged.

That night I called Jack, just to have a normal adult conversation.

I also pledged to myself no more looking out the window.

.....

The next morning, I was up early and looked out the window just to see what the weather was like, since it was six-thirty in the morning, and there was no way Bianca would be out there yet. But I found another major surprise.

Lorenzo Ricci was sitting by the fence in the same lawn chair Bianca usually sat in... and apparently maintaining a family tradition, he had a chubby woman sucking his cock... wearing a robe... and possibly nothing else.

She pulled back at one point, and I got a great glimpse of his cock... it was huge!

As she pushed her hair back, I also realized who she was: Debbie Conners. She lived on the other side of Bianca's house. She was in real estate, and she'd brokered the sale of pretty much every house in this gated community. And of course she was married. Her husband was in the music industry in some capacity. He'd met Taylor Swift, Aerosmith, Keith Urban and many other music celebrities.

She resumed sucking his cock... really bobbing.

He wasn't close enough for me to be able to assess his size accurately, but it seemed to be around double the size of my husband's.

My mouth watered, and my pussy burned.

God, I'd love to play with a cock that big. I hadn't been fucked by a sizeable cock since college, and none of those had been nearly this big.

I know it was wrong, but I dashed into my husband's office and filched his binoculars. I returned, and as the sun rose, I saw Lorenzo was now standing up with his hands on Debbie's hips, and she was bent over the chair with Lorenzo fucking her from behind. She'd now discarded the robe, and sure enough, that's all she'd been wearing.

I silently opened my window, wanting to listen in on them, hoping that would work from this distance.

"Oh fuck, fuck me harder," Debbie moaned, and he was fucking her so hard that all the way from my window, I could hear the slaps of their bodies crashing together.

"Do you like it hard, slut?" Lorenzo asked, reaching his left hand out to her ponytail and yanking on it.

"You know I love it hard when it's your big fucking dick," Debbie responded with a lust you wouldn't even find believable in most porn films. Although I'd heard Debbie swear before, especially when we played bridge, this was a different level of filthy language... making my pussy burn, as I brought my left hand to it, while I raised the binoculars to my eyes with my right hand.