In Penelope's Shadow (Working Title) - Ch 1 (Patreon)

Mike

A threesome had been at the top of my fantasy list since I was a teenager.  When I finally got the courage to bring it up to my girlfriend Jenn, I was surprised at how positive her response was.  I couldn’t believe I’d wasted all that time being too afraid to ask! One of Jenn’s conditions was that she would be the one to choose the woman we’d invite over, which I was more than fine with. The other condition was a focus on both of our pleasure…no problems there either.  And by that point in the discussion, my mind was already swimming with the possibilities; I think Jenn may have brought up the idea of a safe word but I couldn’t remember it nor would I care.  Who needs a safeword during a threesome??

A week passed with no discussion on the matter.  I wanted to nudge our conversations toward the topic but at the same time I knew that if I pressured Jenn too hard it’d scare her away from the idea.  And then one evening while we were eating dinner, Jenn was telling me about her day.  She’d been at one of the local department stores looking to buy a gift for someone’s baby shower.  

I loved Jenn but she had a way of rambling on about the most boring things sometimes. I swear, she could make a trip to the grocery store sound like a novel. Maybe it’s my own fault for having the attention span of a goldfish, but I was just waiting for her to wrap it up so we could talk about something more interesting.

Then she dropped a bombshell. 

She ran into her old friend Penelope Sanders while she was out. 

That got my attention real quick. 

“Oh, which one was she? From the old days, I'm guessing?” I asked, pretending like I didn’t already know exactly who she was.

Penelope Sanders... Man, how could anyone ever forget someone like her? That girl was a total knockout, through and through. Gorgeous flowing hair, piercing blue eyes, and pouty lips that looked like red velvet pillows.  And speaking of pillows..good lord, that ass. No joking at all, I really think that I became an ass man the day I first saw Penelope.  Not only was it huge, but her slender waist made it look even bigger. I could barely keep my eyes off it whenever she was around. It was like two perfect, round globes that I couldn’t possibly ignore. I always made sure to sneak glances when Jenn wasn’t looking. Didn’t want to get caught drooling, you know?

I remembered the first time I saw Penelope at a mutual friend’s party a few years back.  Up until then, I’d only seen her a few times at Jenn’s restaurant but Penelope was always dressed in her work uniform.. On this night at this party, she most definitely was not wearing her work uniform.

…and holy shit…

As hot as she already was at work, I couldn’t believe how much Penelope’s boring, baggy waitress uniform had restricted her hotness.  There were no restrictions now. 

Her ass was just... god…is there a word for something that’s bigger than ‘massive’?  If there is, then that’s it. Every step she took made it bounce and jiggle, and yet her super snug jeans were hugging her ass tight enough to accentuate that sexy dip inward between her huge cheeks.  I couldn’t help but imagine what it would feel like in my hands…or maybe even pressed against my face. All it’d take would be one to take me out…and what a way to go that would be. 

Her body was a masterpiece–a work of art that demanded worship. And it was a struggle to stay cool and not let my jaw hit the floor, especially with Jenn by my side! She arrived alone but instantly owned the room, as I’m sure she was used to doing. 

It was a blessing and a curse that Jenn and Penelope were friendly. On one hand, it would have been nice for my psyche to try and ignore her and that giant booty…but on the other hand, I was beyond excited when Penelope eagerly waved Jenn to come over from across the room and I got to be pulled along.

Penelope was polite when I talked to her, but she didn’t seem all that interested in chatting with me. She’d answer my questions with slightly more than bare-minimum effort but then she’d move on to conversing with Jenn or someone else entirely. It was like she was just being nice because I was Jenn’s boyfriend. I couldn’t blame her. I was just some guy to her. 

And it’s not like I was looking to cheat or anything!  Let me be crystal clear here, by the way.  I adore Jenn with all my heart. If given the chance between Penelope and my relationship Jenn, I would pick Jenn one thousand times out of a thousand. Sure, Penelope was drop-dead gorgeous with an ass to die for but Jenn was my girl.

So anyway, Jenn and Penelope were super close; that party wasn’t the last time I would see her.  Never without Jenn of course and when the two would get together, I’d see them laughing, sharing secrets and inside jokes like giggling school girls. Even as she got to know me more, Penelope didn’t really pay me much attention, but that didn’t stop me from watching her every chance I got. Her body was just so perfect, and that ass... God, I couldn’t get enough of it.

And then, I’m not sure what happened, but they sort of just stopped talking.  I don’t think there were any fallings-out or anything like that.  I sort of just chalked it up to people growing up and growing apart.

So when Jenn mentioned that she’d run into Penelope my mind went wild with possibilities. Were her and Jenn friends still? Would I get to see her again? I tried to play it cool. "That must have been nice catching up.  What’s she been up to?" I asked, hoping I didn’t sound too eager.

Jenn smiled, clearly happy that I was interested. "She works for this awesome cosmetics company.  That’s how I ran into her, actually. She was there checking out the store to see how they were performing.”

“That’s cool.” I said, trying to sound nonchalant.  “You guys gonna get some dinner?”

“Actually, I invited her over here for dinner next weekend…and then some dessert.”

I didn’t pick up on it right away. My dumb ass actually asked Jenn what she was cooking and it wasn’t until she raised an eyebrow and smiled that I realized what she was talking about. When I did, I just about had a heart attack!  

I was finally going to have a threesome!!!

And not just with any random third…it was going to be with Penelope freaking Sanders! Of all the girls Jenn could have asked, never in my wildest dreams would I have thought Penelope! Actually, that’s not true.  Of course somewhere in my mind I’d dreamed of getting to rail that thicc, stunning girl from behind or have her park that massive ass on my face all with Jenn’s approval but the idea of it actually happening was so outlandish that I didn’t even allow myself to consider it a possibility! 

And yet here we were, on the brink of making my wildest fantasies a reality. It was surreal to think that Penelope had actually agreed to join us, especially considering how little attention she had ever paid me in the past. But I wasn't about to question my luck…no freaking way. Jenn was enthusiastic and judging from her description of their conversation at the store, Penelope seemed equally excited.  

Three agonizing days later, I randomly stirred from my sleep. I groggily blinked away the remnants of a dream that I hoped would soon be a reality and became aware of the subtle movement around me. The sheets were fluttering and rustling over on Jenn’s side.  Rubbing my eyes, I turned my head and expected to see darkness..but I had to shield my dark-vision adjusted eyes from the blinding light.

At first, I thought she was simply shifting in her sleep, but as my eyes adjusted to the light of her phone screen, I noticed something else. Her breathing was quickened, shallow, and there was a tension in the air that I couldn't quite place. There was sweat on her brow..had she just come out of a nightmare and was now on her phone?

My curiosity piqued, I shifted closer, my hand reaching out to touch her shoulder. "Jenn?"

She looked over at me with a smile and turned her phone toward me, showing the bright white background.  They were text messages.

“Who you talkin’ to, babe?” I slurred, my lips and tongue dry.

Jenn grinned, locking her phone and setting it down on her nightstand just as my sleepy eyes had fully focused. The comforter shifted down near her hips as she adjusted her lying position.  “Oh, just Penelope. She’s really excited for this weekend.”

Even just hearing that name now had an effect on me I couldn’t control. I immediately felt my briefs stretching to accommodate my stiffening cock.  Hell, I may have cum right then and there if Jenn hadn’t been so insistent on me holding it until the big night.  A threesome with my girlfriend..and Penelope Sanders.  I seriously couldn’t wait.

* * * * * * * * * * *

Jenn

Dinner was a blur. My mind barely registered the food in front of me. Goodness…there were times when I forgot that Mike was even seated there with us. All I could focus on was Penelope, sitting adjacent to me at the table. She was the epitome of raw, undeniable, unhideable sensuality. I’d known her for years but I was now admiring her beauty through the lens of carnal lust. Her ocean-deep eyes held a twinkle of mischief as she occasionally glanced my way, sending shivers down my spine.

“This hummus is seriously to die for, Jenn.” Her cleavage swelled as she leaned forward, taking her sweet time to steal another scoop from the center of the table. The way her top dipped down and her breasts pressed against my dining room table, threatening to spill…it left me breathless. Never in my life had I been so jealous of jewelry as I was now, watching the glittering gold of her necklace drape over the curvature of her displaced breasts.  And between them, interlocked at the end of the golden necklace, there was a pink jewel or stone nestled in her cleavage. It caught a glimmer of the overhead light fixture before being re-consumed by Penelope’s chest.  My mind wandered to the feel of her skin. 

I had been graced with a hug when Penelope arrived and while it wasn’t our first hug, there was something very different about this one.  Let’s just say it was the closest together our hearts had ever been. The softness of those voluptuous curves pressed against me was more exciting than anything in my recent memory.  I would have wondered if Mike felt the same way, but she only offered him a polite handshake.

“Did you make it?”

Penelope caught me admiring the deep valley of cleavage and she grinned–a reaction much different from how she handled Mike’s gawking, which was to mostly ignore it.  

I was rocked back to reality. “Hm?”

“Distracted much?” Penelope . “The hummus, silly-pants.  Did you make it?”

I had barely opened my mouth to give credit where credit was due, but Mike’s pressurized response had already exploded with a little too much enthusiasm. “The hummus? No, no..she didn’t make it.  It was me!  I mean, I bought it!  At the supermarket! You like it?”

“Not too bad.” Penelope said, tracing a small floret of broccoli through her fresh scoop. “Maybe I’ll look for it next time I’m out.”

“You definitely should!” Mike said, all of the sudden a hummus enthusiast. “I can’t remember the brand name but I can see if we kept the receipt. It might have–”

Penelope raised a hand to calm Mike down who was just starting to press his palms into the arm rests of his chair. “--no, no.  It’s fine, don’t worry about it.”

The light, idle chat continued buzzing, mostly sustained by Penelope and I as she slowly picked away at her dinner, but with less interest in the hummus than before.

“So, Penelope, how’s work been treating you? Still rocking it at the corporate cosmetics job?”

Penelope’s face lit up, her eyes sparkling with genuine interest. “Oh, it’s been great! Busy, as always, but you know how much I love it. We’re about to launch this killer new line.”

Mike chimed in, “What kind of stuff are you working on?”

Penelope glanced at him briefly, offering a polite but curt smile before turning her attention back to me. “We’re launching a new line of eco-friendly skincare products. It’s a huge project, but I think it’s going to be a game-changer for us.”

“That sounds amazing!” I said, genuinely intrigued. “I’d love to hear more about it. Are you involved in the marketing side too?”

“Oh, absolutely,” Penelope replied, her enthusiasm unwavering.“I get to work with the marketing team to make sure everything’s on point and I check the stores to make sure everything’s set up right. It’s a lot of juggle, but seeing the final product out there? So worth it.”

Mike tried to squeeze into the conversation again. “Do you get to test the products yourself?”

Penelope nodded, “If we want to, sure.” She turned back to me. “You should come by the office sometime, Jenn. I can show you around, give you the VIP tour–maybe even let you try some samples.”

I felt a thrill at the idea. “I’d love that!”

“It really is,” Penelope said, her voice softening as she gazed at me. “I’m lucky to be doing something I’m passionate about.”

“It’s really cool that you moved up so much. How’d you pull off getting to where you are now 

Penelope’s eyes flickered to Mike for a moment before she answered, her tone was friendly but still slightly distant. “Just gotta put the hours in.  Network like crazy, stay on top of trends, all that stuff.”

She then shifted back to me, her expression warm and inviting. “But enough about me and work. What about you, Jenn? Any exciting projects on the horizon?”

I felt a surge of gratitude for her effortless ability to make me feel special. “Well, I’ve been thinking about starting a blog. It’s something I’ve always wanted to do, and I think it could be a fun way to share my interests and connect with others.”

Penelope’s smile widened. “That sounds awesome! You take really good pictures too, you know. I’ll bet you could do a photo thing along with the blog entries. 

Mike smiled, his enthusiasm undiminished. “Yeah, I’ve been telling her she should do it for a while now; I think Jenn would be great at it too.”

Penelope nodded, her eyes remaining fixed on mine. They channeled into me a confidence and power that made me feel like anything was possible. “Absolutely. You have a lot to offer, Jenn. You should definitely go for it. I’d be your first subscriber.””

“Thanks, guys.” My hand rushed to cover my blushing cheeks and my gaze fell from Penelope’s smiling eyes to something a lot less wholesome.  

Tight, stretchy, blue jeans hugged Penelope’s body in all the right places, reminding me just how curvaceous she was. Her thighs were thick and powerful, straining against the faded blue denim with each subtle shift in her seat. As I took another sip of wine, my gaze lingered on her hips, flaring out poetically before leading to her magnificent derriere. It was massive and round, the kind that seemed almost too perfect to be real. And yet there it was, splayed out on one of my late grandmother’s dining room chairs–and practically overflowing around the edges. How could someone so fit have a booty that big? I’d gotten an eyeful after we hugged at the door when she arrived; those jeans clung to that booty so snug, hugging it as tightly as I wanted to, I could see the outline of her cheeky panties. It was all I could do to keep my hands to myself.

Even Penelope’s feet, resting atop simple cheap flip flops, were irresistibly cute. Her toes were painted a frisky shade of periwinkle purple, perfectly pedicured and playfully pittering against the spongy polka-dotted sole. 

As Penelope shifted in her chair and switched the crossing of her legs, the fabric of her jeans stretched even tighter over her thighs and ass, and I had to bite my lip to keep from gasping.

“Looks like you’re almost empty again, Jenn.” Penelope leaned forward, reaching for the wine she’d brought. The movement made her breasts press together even more, creating an enticing valley of cleavage that drew my eyes irresistibly. 

Penelope caught my gawk once again–and once again she smirked a knowing, sultry smile that made my heart race. It was as if she could read every thought running through my mind, every forbidden desire I had harbored. Her beauty was hypnotic and I felt like with each passing second of looking into her eyes, I was learning more about myself.

I glanced at Mike, who was similarly entranced, his eyes wide with anticipation. But unlike him, my feelings were tinged with a deeper, more complex longing. I loved Mike, but my attraction to Penelope was undeniable. The thought of touching her, of exploring her body, sent a thrill through me that I didn’t fully recognize and couldn't even partially ignore.

“Did you want some more hummus, Penelope?” Mike asked.  

He was struggling to find something with her.  A connection…maybe like the one she and I had. When Penelope politely declined, I felt a tinge of pity for him.  But Mike’s obliviousness served as a shield, protecting his feelings from how comparatively dismissive she’d been toward him.  

I found his eagerness endearing in a clumsy-charmful sort of way. It was cute how smitten he was with her. He talked a big game in the past week about how he was going to rock both of our worlds, but now he was acting like a shy, nervous little puppy.  In all fairness, I may have been even more enamored by our gorgeous guest, but I clearly had more control over my jitters.  Poor Mike seemed enslaved by them. 

Maybe it was a man thing but then again, there was a lot on the line for him. Not only was Penelope ridiculously attractive, but she held the key to his ultimate fantasy.  At any time, she could have gotten up from the table and said nevermind…and then that would be that.  She’d strut out that door, taking that big, shaking booty that he couldn’t stop drooling for and it would be over before it even began. But it wasn’t just Penelope who had this power; I could have done the same thing.  Looked like we were both holders of his key!

Mike had somehow steered the conversation to his job, and with a little too much detail and jargon to keep either of us interested. I stole another glance at Penelope, silently checking in with her.  When I did, I saw that she was already looking at me. And then I felt those cute, chubby toes of hers nuzzle up against my bare calf. My heart skipped a beat, and a flush creeped up my neck. Mike’s words faded into a fuzzy buzz as the sound of blood rushing through my temples became deafening. She knew exactly what she was doing, and it only made me more excited for what was to come.

“Dinner was delicious, Jenn,” Penelope said, dabbing the corners of her pouty lips with her cloth napkin. “But I think it’s time for dessert, don’t you?”

I glanced at Mike, whose face lit up with anticipation. He looked like a kid in a candy store, and it made me smile to see him so happy. "Absolutely," I replied, trying to keep my voice steady despite the butterflies in my stomach. "Let’s move to the living room."

Mike led the way, and I felt Penelope's hand brush against mine. The brief contact along with the pleasant aura of lavender and vanilla radiating from her presence sent a jolt of electricity through me. Once in our living room, Penelope gracefully stepped out of her flip-flops, I glanced at Mike. He was already seated on our two-cushion loveseat as I took a seat next to him on the other cushion. He probably thought that I didn’t notice his gawking like a hormone-soaked teenage boy but of course I did, and Penelope probably noticed, too. His eyes were wide with excitement–and a nervousness that was far more evident than he probably realized; I enjoyed the spectacle of it; the audible gasp he made when Penelope bent over to align her flip flops neatly next to the couch before parking her epic booty on the two-cushion loveseat, right between Mike and I.

"Uh-oh…” Penelope said with a soft disapproval as she caressed my knee. “Mike, it looks like Jenn is getting low on wine again. Be a dear and fill her up?” 

Her request was sweet-toned and polite, but there was a hint of condescension…as if she were speaking to a maid or waiter. It went either unnoticed or unconsidered as Mike, bless his heart, and he jumped up to oblige. I knew that Mike would have gotten the wine for me had I made the request, but something about Penelope doing it on my behalf made me feel so special. For a moment, as I watched Mike rush off to get what Penelope had asked for, I allowed myself to imagine that I was Penelope’s date–that I was the girl on her arm…and she was going to make sure the waitstaff was taking care of her girl.  

The second that Mike rounded the corner and disappeared into the kitchen, Penelope bounced up, tucking a bare foot in under her plump ass. She turned her hips and shoulders to face me and leaned in close. "Jenn, there's something we need to chat about before we go any further," Her warm breath tickled my ear and it felt like I was melting into the excitement.  

“What is it, Penelope?

Penelope's sparkling eyes scanned to the empty hallway one final time before she continued. "I know we’ve got a special night planned, but Mike wants something even more...special.”

I raised an eyebrow, intrigued. "What do you mean?"

“Remember when you went to get the hummus from the kitchen?  Right before we started eating?” Penelope leaned in, her lips brushing against my ear as she spoke. "...right before you came back in, he admitted something to me; he was too shy to tell you about it for some reason but it was pretty cute, actually.”

“Ohh…” The warmth of her breath in my ear made my knees weak. It was a good thing I was sitting down! “...what did he say?”

“Mike has this fantasy of being shrunken down and completely at our mercy.  And the best part? He wants to watch us together."

The idea was strangely exhilarating but it seemed pretty different from what Mike had been talking about this past week.  Doggy style, facesitting, Penelope and I giving him head at the same time–a lot of topics came up…maybe too many…but submission wasn’t one of them.  Maybe it was the wine catching up with me, but the way Penelope described it, with such confidence and allure, made it sound incredibly appealing. "Are you sure that's what he wants?

Penelope nodded cheerfully, her eyes never leaving mine. "Oh, Absolutely; are you kidding me?  I wasn’t even surprised when he told me.  It’s a guy thing, seriously. He'll love being our little toy, I promise. Just trust me."

I hesitated for a moment.  Why hadn’t Mike told me about this?  Was he really too embarrassed? Too ashamed?  Did he think that I’d think less of him?  Whatever the reason, at least he somehow mustered the courage to tell Penelope.  The desire in her eyes and the thrill of the unknown pushed me over the edge. That and the alcohol. 

I needed not an ounce more convincing. "Alright. Let's do it."

Penelope smiled bigger than she had the entire evening. "Good. Now, let's make this a night he'll never forget."

* * * * * * * * * *

Mike returned with my wine and Penelope thanked him.  I laughed to myself as I let my little fantasy from earlier go wild. I imagined her tipping him, ‘there you go, kid.  A fresh five for taking care of my princess here.’ and he’d run off with a smile on his face, giving us the privacy we needed as she draped an arm over my shoulder.

I sipped the wine and then took a deep breath, ready for whatever came next. I was in love with Mike, but tonight, I was ready to explore my desires with Penelope. And with Penelope leading the way, I felt comfortable just to be the girl on her arm as she made the decisions.

"Mike," Penelope said, "Jenna and I have a little surprise for you." 

He looked caught off guard by her tone.  It was much sweeter and more friendly than usual.  Before he could respond, she reached into her cleavage and pulled out a small vial. "Isn’t it pretty?," she explained, holding it up for both of us to see.  The vial contained no more than several drops of a bright pink, sparkling fluid. "This’ll make you even more fun to play with."

Mike looked at me, confusion and curiosity in his eyes. "What is it?"

Penelope's hand appeared under Mike’s chin and gently turned his face toward her. "Remember what we talked about earlier?” 

Mike was melting into her gaze but still his brow remained wrinkled in uncertainty. 

"This is the thing that’ll make you even more fun to play with."  I watched Mike’s expression morph from confusion to embarrassment as blood rushed to his cheeks.  

‘Wow…’ I thought. ‘He really does want to shrink.  Kind of strange but I can be supportive.’

“It’s okay, Mike.” I said, reaching over Penelope’s wide lap to squeeze Mike’s hand.  “I’m glad you told her.  I want this to be fun for all of us.”

“Oh, trust me.  It will.”  For the first time, Penelope stroked Mike’s thigh and he looked like he might explode right then and there.  I’m not proud of it, but the sight of her hand on his lap made me a little jealous.

But the strange part?  It wasn’t that I was jealous of or angry with Penelope for touching my boyfriend.

I was jealous of Mike..for siphoning off even an ounce of Penelope’s attention. 

As Penelope gently snapped the tiny lid off the vial and handed it to Mike, he glanced at me.  He was seeking my approval…my sign-off.  But not in a ‘can I fuck your friend’ kind of approval.  It was a ‘do you think this is safe?’ kind of approval. I nodded without hesitation, trusting Penelope whole-heartedly.

Mike hesitated just for just a moment before downing the sparkling liquid. Almost immediately, his muscles began to twitch and a look of surprise crossed his face. Penelope and I watched intently as he started to shrink, his clothes becoming increasingly oversized on his diminishing frame.

The process was fascinating, and I couldn't tear my eyes away. Penelope’s interest seemed to peak as well, her eyes sparkling with a mix of excitement and curiosity. She was more engaged now than I had ever seen her with Mike before. “This feels…funny.” Mike moaned, reaching out toward Penelope. His fingers couldn’t even curl around her forearm.  Just as quickly as he realized, that same forearm was twice as big and out of reach as he slowly sank toward the cushion, half occupied by Penelope’s splayed ass. He continued to dwindle down, and Penelope was lifting his clothing–his shirt, socks, jeans, and finally his underwear, ensuring he didn’t get lost in the fabric but essentially stripping him down until he was stark naked. 

He continued to shrink as Penelope and I watched in fascination, the couch cushion seeming to grow out in all directions around his tiny body. As his weight on the couch decreased, the cushion took back its rounded shape–the half that wasn’t compressed by Penelope’s weight, that is.

The convex curve of the cushion proved too curvy for Mike, and he tumbled forward toward Penelope’s hip, rolled down the length of her thigh, and then plummeted off the edge of the couch.

~