Peeping Tom And The Gay Neighbors

I had been on the ladder cleaning out the gutters on my house. It was kinda high, maybe 20 feet off the ground. It was starting to get dark but this was the last gutter to clean. I didn't want to have to drag the extension ladder out another time to finish so I pressed on even though it was starting to get dark.

I saw the light in a second floor window on my neighbors house come on. I glanced over and saw right into the window since the drapes were open. There was a sling hanging from the ceiling. I saw my neighbor, Rick, step into view. He was naked and had no hair on him aside from his head. Even his cock was hairless. It was pretty big, probably 8 inches and thick too. It made my 6 inches look small.

He hopped up in the sling and leaned back, as it swung slowly back and forth. There were loops attached to the straps that he stuck his feet in, after pulling his knees back towards his armpits, exposing himself to the other naked guy that just stepped into view.

I had no idea that my neighbor was gay, but I didnt know much about him either. He had moved in a month ago and when I saw him carrying boxes into the house I went over to introduce myself and welcome him to the neighborhood. He said his name was Rick and he was single. I told him my name was Tom and I lived next door with my girlfriend, Anna. After that it was just a wave when we saw each other.

Yea, I know, It's a cliché I never expected to live out: becoming a literal Peeping Tom simply by being named Tom and standing on a ladder. I was just trying to finish the gutters, but the universe clearly has a sense of humor, turning my mundane chore into a punchline that fits my birth certificate a little too well.

Anyway, when the other guy turned, I saw that his cock was even bigger than Rick's. The guy handed Rick some shiny black material. I saw that it was a hood when Rick stretched it over his head. There were no eyeholes, just a hole for his mouth. Rick reached his arms up and the guy wrapped some straps attached to the sling around his wrists, holding him in place. Then he pulled on a pair of tight latex gloves, the shiny black material stretching over his big hands.

The big dick guy pulled a thick buttplug out of my neighbor's asshole, making him moan loudly. I heard it from my perch on my roof, making me realize the window was cracked open. He held the plug up and I saw how big it was. It was pretty big, definitely thicker than that guy's massive cock.

The guy picked up a tub of lube and dipped his fingers into it before pushing them into Rick's ass. After twisting them around for a minute, inside his hole, he scooped up more lube and pushed his fingers back in. Then the guy lubed his cock up and I watched as he slowly pushed his big dick into Rick's ass, making the hooded man moan like he was loving it.

While I wasn't gay and had only been with women, my girlfriend had been pegging me for the past couple months. What started out as a drunken night when she licked my asshole in the shower, then worked her finger into my ass while she was sucking my dick, soon led to her pushing a vibrator into my ass while we were fucking. We found out that I came harder when the vibrator was in my ass rubbing my prostate.

Our experimenting soon led to her buying a strapon harness and a dildo slightly bigger than my dick. She loved to use it to fuck my ass, and she really got off on dominating me.

I also found out that Anna liked to have her pussy stretched. She admitted that she had used the vibrator and the dildo together to double penetrate her pussy while masturbating. I got her to show me after a bunch of pleading. I watched her work the vibrator into her pussy, next to the dildo already buried inside herself, stretching her hole more than I had ever seen. Soon she was making herself cum, as I watched wide eyed.

I crawled between her spread legs as she layed back against the pillows, catching her breath, her big tits rising and falling as she sucked in air. I reached for the toys and she told me to leave the dildo inside her and push my cock in beside it.

I quickly pulled the vibrator out. I was reaching over to put it on the nightstand when she told me to push it into my ass. She gave me a naughty smile as I did it. Then she said I could DP her pussy. I moved the dildo up and flipped it upside down so the attached balls were on top, out of the way. Then I pushed my dick into her beneath it. She gasped as I sank into her wet pussy, pushing the dildo deep into her as well.

I had never felt her so tight. The dildo and my cock together were a tight fit. She must have felt the same by the way she was moaning. We both came quickly, with her pussy getting stretched as I pounded into her. The vibrator was shaking mercilessly against my prostate, driving me towards an intense orgasm.

Afterwards Anna licked my cock clean while she made me deepthroat the dildo. That night opened the door for more kinky stuff but I was still kinda shocked as I watched my neighbor get buttfucked by this guy with a huge cock.

That guy was slamming his huge cock into Rick's ass, while he moaned and his hooded head flopped from side to side. The guy was fucking my neighbors ass with long strokes, moving faster with every stroke, his thighs slapping loudly against Rick's cheeks. The big man grunted loudly as he slammed against Rick one final time as he came and Rick moaned loudly.

I stared through the window, mesmerized by what I was seeing. The guy pulled his big dick out of Rick's asshole and picked up the tub of lube. He dipped his thick gloved fingers in it then started pushing them into the restrained man's ass. He dipped his fingers back in the lube and pushed four fingers into Rick's ass, twisting his hand back and forth. He was stretching the hole and Rick was groaning loudly.

I stood there, frozen on the top rung of that ladder, my fingers gripping the aluminum sides so hard they went numb. The cold evening air bit at my neck, but I barely felt it. My heart was thudding against my ribs, watching what was happening in that room through the window.

Part of me was saying to get down before I got caught peeping, the other, much more twisted part of me was saying that this was fucking hot and I should open my pants and jerk off. I couldnt bring myself to do either so I just kept watching.

The guy with the big hands didn't stop at four fingers. He kept at it, his movements methodical and deliberate as Rick's hole stretched around his gloved hand. Rick's moans had shifted from sharp cries to a low, guttural drone that vibrated through the air.

He was completely helpless, suspended in that sling with his head covered, totally unaware that his neighbor was watching him from the dark.

I knew I should move. I should have finished that last stretch of gutter and climbed down. But I couldn't look away. Seeing the way Rick's body reacted--the way he leaned into the sensation even as he was being pushed to his limit--had me more excited than anything else I had ever seen.

Inside the room, the guy pulled his hand out. The sound was wet and heavy. He coated it in a fresh layer of lube and pressed it back against Rick's opening. "Please," I heard Rick rasp through the mouth hole of the hood. It wasn't a plea to stop; it was a desperate urge for more.

The guy didn't say a word. He just leaned his weight into it, slowly driving his hand into Rick, as his legs shook in the stirrups, his toes curling tight. My own breath was coming fast as I watched intently. The ladder creaked slightly under my weight as I shifted, and for a terrifying second, I thought I'd lost my balance. I steadied myself, my pulse racing, but my eyes never left the window.

Rick's body buckled as the man's hand continued its slow progress. The "Please" I heard him utter seemed to hang in the air, thick and heavy, answered only by the sound of the latex sliding against his skin. From my vantage point, I could see the muscles in Rick's thighs twitching, his body vibrating with the strain of being stretched so wide.

The man with the gloves wasn't rushing. He seemed to be savoring the way Rick's hole gripped his hand, testing the limits of how much the hooded man could take. Every time he pushed a bit deeper, Rick's hips lurched upward, the sling swaying violently in response.

The guy withdrew his hand slightly, then drove it back in with a firm, steady pressure, finally burying his fist up to the wrist. Rick's back arched off the sling, his head snapping back as a loud cry tore from his throat. He was completely filled, his body forced to accommodate every inch of the man's hand.

I stood there watching, feeling a strange mix of adrenaline and arousal. The thought of Anna waiting for me inside, and the kinky boundaries we'd already pushed together, made the scene in front of me feel even more intense. For a moment I pictured myself in there, pushing my fist into the masked man's stretched hole and it excited me....a lot.

The man inside the room began to move his fist in slow, deliberate circles, churning inside Rick. Rick's moans turned into a frantic panting. He was lost in it, totally surrendered to the sensation, not like he had a choice since he was restrained, while I remained frozen in the shadows, witness to a side of my neighbor I never could have imagined.

The man was fist fucking Rick's stretched asshole, the muscles in his arm and hack flexing with every shove. He was twisting his arm as he drove it deeper, then pulled back, before shoving it in again.

Rick was lifting his ass out of the sling, his thigh muscles twitching and his cries getting louder. Then the man bent over and wrapped his lips around Rick's cock, getting a mouthful of cum a moment later. He stood up and wiped his lips with the back of his arm when Rick finally stopped thrusting his hips.

Then the man slowly began to withdraw his fist. The sound was distinct, a wet, suctioning noise that seemed to echo in the quiet evening air. Rick slumped back into the sling, his chest heaving, his body slick with sweat that glistened under the bedroom lights.

The air felt thinner as I watched the man finally ease his fist out of Rick's body. The silence that followed was heavy, broken only by the muffled sounds of Rick's ragged breathing coming through the cracked window. Rick looked completely spent, his body limp in the sling as the guy began to unbuckle the wrist straps.

It was a total sensory overload. One minute I'm thinking about leaf buildup and downspouts, and the next, I'm witnessing the kinkiest thing I've ever seen. Seeing that level of total surrender--the hood, the restraints, the sheer scale of what his body just accepted--it changes how you look at a person. Rick wasn't just the quiet new guy next door anymore.

I finally forced my hands to loosen their grip on the ladder. My knuckles were white and my fingers felt like lead from the cold and the tension. I knew if I stayed a second longer, I'd risk getting caught or, worse, losing my footing.

As I carefully began my descent, my mind was on Anna. Thinking about the way we'd started experimenting--the vibrators, the pegging, that night she had me DP her with the dildo--it all felt heightened now. There's a specific kind of adrenaline that hits when you realize the world is a lot kinkier than it looks on the surface.

I climbed down the last few rungs, my boots hitting the grass with a dull thud that felt louder than it actually was. My legs were a little shaky--half from the height and half from the sheer intensity of what I'd just watched. I collapsed the extension ladder, the metal sliding together with a series of sharp clacks that made me wince, worried the sound might draw Rick or his guest to the window.

I hurried to the garage, shoved the ladder into its spot, and clicked the door shut. The silence of the garage felt heavy. I stood there for a second in the dark, my breath visible in the chilly air, trying to shake the image of that black latex hood and the sight of Rick being stretched so completely.

My thoughts went to myself hanging in Rick's place, wearing the latex hood as Anna pounded her strapon into me.

When I finally walked through the door into the kitchen, Anna was waiting. "You were out there forever. I was about to come out with a flashlight to make sure you hadn't fallen," she said as I walked into the room, still pulling off my heavy work jacket.

She was wearing one of my oversized hoodies and a pair of tiny lace undies. Her hair was messy, and she looked soft, comfortable, and completely oblivious to the chaos currently happening twenty feet away in the neighbor's bedroom.

"Yeah, just... the last bit was stubborn," I said, my voice sounding a bit raspier than usual.

She looked up, her eyes narrowing slightly as she studied my face. Anna's always been sharp; she can tell when my heart rate hasn't settled down. "You look like you've seen a ghost. Or had a run-in with a very scary squirrel."

She slid her arms around my waist, pressing her body against mine. Even through my clothes, I could feel the heat radiating off her. After seeing Rick suspended and helpless, the feeling of Anna's hands on me sent a fresh spark of electricity straight to my gut.

"Your heart is racing," she whispered, her hands sliding down to rest on my ass, her fingers hooking into my back pockets. She looked up at me, her eyes narrowing with that look that meant I was already in trouble. "Cleaning gutters shouldn't be that exciting, Tom. What really happened out there?"

I looked at her, thinking about the dildo on the nightstand, the vibrator, and the way she'd looked when I joined her in bed that night when we gave her a DP. The secret of what I saw was burning a hole in my tongue, but the physical urge to recreate that level of intensity with her was winning.

I leaned down to catch her earlobe between my teeth. "I think," I said, my voice dropping, "you're going to want to hear all about it."

Anna let out a low, ragged sound, pulling me closer. "Is that so? Why don't you go jump in the shower and get the literal filth off you? Then you can show me exactly what you have in mind. But you better hurry--I'm not known for my patience, I might just start without you."

When I finished cleaning myself, I went in the bedroom and Anna wasn't there. I found her in the living room. She was on the couch, slouched down, her sexy high heels spread wide, resting on the coffee table. She was fucking her pussy with the dildo while she held the vibrator to her clit, through the open crotch of her fishnet bodysuit. The material was stretched over her big tits and her curvy hips. She looked hot as fuck.

"Sorry babe," she said with a big smile, " I couldn't wait."

I felt the same voyeuristic energy that had held me captive on the ladder. Seeing Anna like that--totally uninhibited, her body straining while she worked those familiar toys--merged perfectly with the raw scene I'd just witnessed at Rick's.

"Don't be sorry," I said, my voice low and my cock hard as I watched her. "Actually, keep doing exactly that. Don't stop."

Anna's eyes widened slightly at the intensity in my tone. She didn't slow down; instead, she arched her back, as she pushed the dildo deep into her pussy as the vibrator rattled against her clit. "You're different tonight, Tom. Something about being on that roof really revved your engine."

I walked over to the couch, the carpet soft under my feet, and stood right at the edge of the coffee table. From this angle, I could see the way the fishnet cut into her thighs and the way her pussy was stretched wide by the dildo--just like I'd seen Rick's hole stretched by that gloved hand. The mental image of the black latex hood flashed in my mind.

"I saw something," I admitted, my gaze locked on the way the toys moved inside her. "The neighbor. Rick. His drapes were open."

Anna paused for a fraction of a second, her hand stilled on the vibrator, but she didn't pull the dildo out. A slow grin spread across her face. "Oh? And what is our new neighbor into?"

I reached down, taking the vibrator from her hand but keeping it pressed firmly where it needed to be. "Kinky shit, Anna.... wilder than anything I've ever seen. He was hanging in a sling. He was strapped in, restrained. Rick was wearing a black latex hood with no eye holes. I watched a guy with a huge cock fuck his ass, then fist him until he was screaming."

As I spoke, I watched Anna's pupils dilate. The shock was still there, but it was being overtaken by a dark, buzzing curiosity.

"Black latex?" she repeated, her voice trembling as she slowly began to move the dildo again, her pace tentative but heavier. "And you just... stood there? Watching?"

"I couldn't look away," I admitted, my thumb brushing over her lower lip. "And seeing you like this now... knowing what's happening just across the way... it's making me want things I didn't know I wanted. I want to feel that kind of limit."

Anna's expression shifted from playful to predatory. She dropped the dildo, letting it fall onto the couch cushions with a wet thud, and reached for my wrists. "You want to be opened up like that? You want to see if you can take as much as Rick?"

She didn't wait for an answer. She stood up, her heels clicking on the floor, and grabbed my hard cock, leading me to the bedroom by it.. "I hope you're ready, Tom. You got yourself all excited watching the neighbors. Then you told me and now I'm excited, so you'd better be prepared for what I'm going to do to you. Tonight, I'm going to see exactly how much room there is inside you."

The atmosphere in the bedroom had shifted from its usual playful experimentation to something much darker and more intense. The voyeuristic thrill of watching Rick's total surrender had stripped away any lingering hesitation I had. As Anna pushed me onto the bed, the image of that black latex hood and the sounds coming from Rick as he hung in that sling was all I could think about.

"You said you wanted to feel the limit," she said, her voice dropping to a low, velvet rasp. "But once we start this, the limit is wherever I decide it is. You understand?"

I nodded, my heart hammering against my ribs.

"Then let's see how much you can take," she said with a smile. She leaned down, her lips brushing my ear, her breath hot and steady.

Anna didn't go for the small vibrator this time. She went straight for the thickest dildo in her collection--one she'd bought as a goal, somthing to work up to, but we hadn't quite mastered yet. She put it in the strapon harness, then stepped into the leg loops. She pulled it up her legs and tightened the strap around her waist. Then she cinched the other buckles tight.

"If you want to play like the big boys next door," she whispered, her voice thick with a sudden, commanding edge, "you're going to have to learn how to stay still while I stretch you out. And if you start to cry, I want you to remember--you're the one who asked to be opened up."

I rolled onto my stomach, my heart hammering against the mattress just like it had against the rungs of the ladder. I felt the cold shock of the lube hit my skin, followed by Anna's fingers. She wasn't being gentle; she was mimicking the methodical, firm pressure I'd described.

Every time I tried to tense up, she'd lean her weight into me, reminding me that I was the one who asked for this. I kept my eyes shut, and in the darkness of my own mind, I was back on that ladder. I could see the man's gloved hand disappearing into Rick, and suddenly, I understood the "Please" I'd heard Rick gasp. It wasn't about pain--it was about the incredible, overwhelming feeling of being completely filled.

When Anna finally swapped her fingers for the dildo, I felt a stretch that made my breath hitch. It was more than I'd ever taken, but the memory of Rick in that sling, his hole getting stretched, was all I could think about.

"You're doing so good, Tom," she whispered, her tone a mix of praise and malice as she began to drive the fat dildo home with long, relentless strokes. "Is this what you imagined it would feel like?

The intensity in the room was stifling, the air thick with the scent of silicone lube and the sound of the toy sliding into my stretched hole. Every inch Anna gained felt like a revelation, a physical echo of the scene I'd witnessed through Rick's window.

"Talk to me," Anna commanded, her voice dropping an octave as she increased the pressure. She leaned over my back, her breasts pressing into my shoulder blades, her breath hot against my ear. "Tell me what you're seeing right now. Is it the neighbor? Or is it me?"

"Both," I managed to choke out, my face buried in the pillow. "I can still see the hood... the way his body buckled. I want to feel that... I want to feel like I'm coming apart."

Anna let out a predatory growl. She reached down and grabbed my hair, pulling my head back and twisting my neck so I had to look at her. Her eyes were dark, reflecting a version of herself she usually kept under wraps. "If you want to come apart, you have to give up control. Completely."

She reached into the bedside drawer and pulled out a soft silk scarf. Without a word, she pulled my hands behind my back and began to bind my wrists. The sensation of being restrained, coupled with the relentless stretching behind me, sent my arousal into overdrive. I was becoming the image I had coveted--vulnerable, filled, and entirely at her mercy.

She didn't stop with the dildo. As I lay there bound, she reached for the vibrator I'd been using earlier. She didn't put it in my ass; instead, she pressed the humming head against my balls while the dildo continued its slow, punishing work. The dual sensation was overwhelming. My prostate was being hammered from the inside while the vibrations sent electric shocks through my entire groin.

"You're shaking, Tom," she whispered, her tone shifting to that of a scientist observing a fascinating experiment. "You're so close to the edge, aren't you? Just like Rick was."

She moved the massive silicone shaft with a sudden, forceful thrust that made me cry out--a sound that was half-sob, half-groan. It was the same guttural noise I'd heard coming through Rick's cracked window.

"Now," she said, her voice a low vibration of intent. "Let's see if we can get you as wide as that neighbor of ours."

Being bound and filled like this, the world had shrunk down to the sensation of the silk cutting into my wrists and the unrelenting pressure of the massive dildo Anna was driving into me. I was no longer the guy on the ladder; I was the one in the room.

"Look at me," Anna commanded, her voice a sharp contrast to the low hum of the vibrator.

I strained to turn my head, my neck muscles cording with the effort. She looked powerful, standing over me with her hair wild and her eyes locked on mine. She wasn't just my girlfriend anymore; she was the architect of this sensory overload.

"I can feel you pulsing around it," she whispered, her hands moving to my hips to anchor me as she began to pick up the pace. The rhythmic amacking sound of the harness hitting my skin was the only sound in the room, a perfect mimicry of the sounds I'd heard from Rick's house.

The stretch was intense--a dull ache that felt like it was reaching right up into my gut. I was fighting between the feelings of pleasure and overstimulation. I thought of Rick's hooded head swaying from side to side, the way he had completely surrendered to the man with the black gloves. I let my own head fall down into the pillow, my body finally going limp as I stopped fighting the sensation and started riding it.

"That's it," Anna urged, her voice softening just a fraction. "Give it to me, Tom. Let it happen."

She leaned forward, her weight pressing me further into the mattress, and reached down to turn the vibrator to its highest setting. The buzzing intensified until it felt like my entire lower body was made of static. Between the internal pressure of the dildo and the external frenzy of the vibrator, my nervous system was screaming.

I felt the orgasm building--not the usual quick spark, but a slow, tectonic shift. It felt like I was being hollowed out and filled with light all at once.

"Anna--" I gasped, my voice breaking.

"Don't you dare hold back," she replied, her thrusts becoming shorter, faster, and more deliberate.

The dam finally broke. A loud, primal shout tore from my throat as my body bucked against the silk restraints. I came so hard I saw stars, my muscles seizing as the dildo continued to slide in and out of me, milking every last drop of sensation from my prostate.

The friction was immense as Anna slowly drew the thick silicone back, only to pause when the head was still crowning. I felt something smaller against the rim of my opening, and then the sharp, incredible pressure of her fingertip forced its way into me beside the dildo.

My vision swam as she began to wedge her finger deeper, the dual intrusion stretching my skin to a point I didn't think possible. The sensation of being filled by two distinct objects--the unyielding girth of the toy and the shifting, living pressure of her digit--pushed my body into a state of total, trembling surrender.

"What the fuck are you doing?" I choked out, my voice muffled by the pillow as her finger dug in deeper beside the silicone. The pressure was agonizing and electric all at once, forcing my hips to stutter against the mattress.

Anna didn't let up. She leaned over me, her hair brushing my neck, and whispered with a jagged, predatory edge. "I have to stretch you more, Tom. I've gotta stretch your hole so Rick and that other guy can fuck you with their fat cocks."

The thought of Rick and his guest fucking me--of being the one in the sling while Anna watched--sent a fresh wave of heat crashing through me. I didn't say no. I couldn't. I just clenched my teeth as she began to work her second finger in, determined to make me as wide as my neighbor.

Then, with a sudden, wet suctioning sound, she pulled everything out at once. My body buckled, the sudden emptiness feeling almost as intense as the intrusion. I gasped for air, my muscles twitching in the sudden void, but she didn't give me a second to recover.

"Look at this, Tom," she commanded.

I rolled my head to the side, my eyes straining to focus. In her hand, gleaming under the bedroom light, was a butt plug that dwarfed everything we had used so far. It was massive--thicker than the dildo and both her fingers combined, with a wide, flared base that looked intimidatingly large.

She held the plug right in front of my face, a wicked, knowing smile playing on her lips. "If you're going to take a massive cock like Rick did, you need to be ready. This is going to get you there. I want to see this buried inside you until there's no room left for anything but the thought of what's coming next."

I stared at the massive, glistening toy in her hand, my heart hammering a frantic rhythm against my ribs. It looked less like a sex toy and more like a structural piling.

"You're nuts," I choked out, my voice cracking with genuine disbelief. "There's no way that's going to fit in my ass."

Anna's smile didn't flicker; if anything, it sharpened, her eyes dark with a challenge that made my stomach flip. She stepped closer, the weight of the harness shifting with her movement, and held the wide head of the plug just inches from my face.

"If I let me work this into your ass," she whispered, her tone dropping into a low, velvet command, "I'll let you do whatever you want to me."

The offer hung in the air, heavy and dangerous. My mind flashed to the image of Rick suspended in that sling, the total surrender I'd witnessed through the window, and the raw, primal need to see just how far I could be pushed. The fear was still there, but the desire to conquer that kind of limit--and the reward she was dangling--was starting to win.

"Anything?" I asked, my gaze locked on hers.

"Abyything," she promised, reaching for the bottle of lube. "Now, stay still. I'm going to make sure you're ready for this."

The thick silicone head pressed against my entrance, and with a firm, low grunt, Anna drove the dildo back into me. She didn't let me adjust; she immediately began fucking me with long, agonizingly slow strokes that made my vision swim. Every time she bottomed out, I felt my internals shift, my body trying to wrap itself around the massive girth.

After a few relentless passes, she stalled the toy halfway deep and held it there. I felt the sharp, focused pressure of her fingertip hooking into the rim of my hole beside the shaft. She wedged it in, stretching the skin to a white-knuckled limit, before forcing a second finger into the gap. The dual sensation of the unyielding toy and her shifting, living fingers felt like I was being split wide open.

"Stay still, Tom," Anna growled as she anchored her fingers to one side, pinning my entrance open to create a jagged, widened gap. Then, she began to hammer the dildo into me again. It was a brutal, uneven rhythm--the toy sliding against the friction of her gloved fingers while my hole was forced to stay dilated.

The pressure was immense, a heavy, dull ache that reached deep into my gut. Just as I thought I couldn't take another inch, I felt a third finger begin to pry its way into my stretched out hole. She was desperate to see just how much more of me she could claim.

The friction was raw and heavy as Anna anchored three fingers deep inside me, hooking them against the rim of my anus and prying it open to the side. With my hole dilated into a jagged, vulnerable shape, she began to hammer the thick dildo back into the gap. Every thrust was a collision of agony and electricity; I could feel the silicone sliding against the back of her gloved fingers, stretching my internal walls to a point that felt like I was being split in two.

My moans were guttural, vibrating through the mattress as the sheer scale of the intrusion pushed my arousal into a frantic, mindless territory. After a few more relentless, gut-punching strokes, Anna pulled it out with a wet, suctioning pop.

She didn't let my muscles retract; and kept those three fingers hooked, pulling the skin of my opening taut and wide, leaving me gaping and exposed. Through the haze of overstimulation, I felt the massive, cold head of the insanely thick plug press firmly against the center of that stretched-out void.

"Here it comes, Tom," she whispered, her voice dropping into a low, commanding growl. She didn't hesitate. As she began to drive the enormous plug forward, she slowly slid her fingers out, replacing their pressure with the unyielding, terrifying girth of the silicone bulb.

The sensation was overwhelming--a slow-motion landslide of pressure that filled every last millimeter of space inside my ass. I pressed my face into the pillow and screamed in agony as my body was forced to accommodate the largest thing I had ever felt, burying the thought of everything else beneath the singular, crushing reality of being completely opened.

The pressure was absolute, a heavy, dull ache that felt like it was displacing my very bones. I could feel every ridge of that silicone monster as Anna's weight bore down on me, her breath hitching in my ear with a jagged, triumphant sound. When that final, widest curve of the bulb forced its way past my sphincter, my vision didn't just blur--it fractured into white sparks against the dark fabric of the pillow.

"There," she whispered, her hands trembling slightly as she maintained the downward pressure. "You're open, Tom. You're completely open for me."

The reprieve was relative. While the sharp, tearing sensation of the initial stretch had faded into a deep, throbbing pulse, the "neck" of the plug was still massive, keeping my muscles pinned at their absolute limit. I lay there, panting, my chest heaving against the mattress, feeling more vulnerable than I ever had on that ladder. I was no longer an observer; I was the one being claimed, my body forced into a state of hollowed-out submission that made my previous experiments feel like child's play.

Anna didn't let me settle for long. She reached down, her fingers slick with the excess lube that had been squeezed out by the plug's entry, and began to rhythmically tug at the flared base. Each small movement sent a fresh wave of pressure deep into my gut, a reminder that she wasn't just filling space--she was testing the structural integrity of my self-control.

"Now," she said, her voice dropping into that predatory velvet again as she leaned over to unbind my wrists. "Since you took it all, it's time to see what you're going to do to me. But don't even think about taking that out yet. I want you to feel it stretching you for a while."

The dull, heavy ache was pulsating through my entire lower body, a rhythmic throb that made it impossible to focus on anything else. My teeth were clenched so tight my jaw ached, and the sweat on my skin felt cold as the initial rush of adrenaline began to ebb, replaced by the raw reality of being pinned at my absolute limit.

"It hurts too much, Anna," I managed to ground out, my voice muffled and strained against the pillow. "I can't even think straight with this thing in me. I need a minute to breathe... I need you to take it out, or I'm not going to be able to do anything for you tonight."

I felt the mattress shift as she leaned back, her weight lifting off my shoulders but the predatory stillness in the room remaining. I expected her to reach down and ease the pressure, to offer some of that aftercare we usually practiced, but instead, I heard a low, sharp laugh that didn't sound like the woman I knew.

"Well, it's staying in," she said, her voice dropping into a cold, challenging edge that made my heart hammer for a completely different reason. She walked toward the window, the heels of her shoes clicking with a deliberate, haunting precision on the hardwood. "If you can't handle being opened up, maybe you aren't the one I should be playing with tonight."

She pulled the curtain back just an inch, staring out toward the neighbor's house where the light in the second-floor window was still burning bright. "Maybe I'll just head over there. Maybe Rick and his friend would like some pussy as a change of pace, and if not, I have an asshole too and you can bet that I wouldn't be complaining about the stretch."

I knelt on the mattress, my breath hitching as the massive plug pulsed inside me, a heavy, unyielding weight that anchored my focus to the raw stretch of my own body. The silence of the bedroom was deafening after the slam of the door, broken only by the rhythmic throb in my gut and the click of heels getting quieter as Anna walked down the stairs.

It was a few moments later when I heard the front door slam shut. I struggled to my knees, the silk bindings biting into my wrists as I lurched toward the window, my balance precarious and my stretched hole screaming at the sudden movement.

Through the glass, I saw her--a silhouette in a trench coat and high heels, as she cut across the dark lawn toward Rick's house. The sight of her approaching that glowing second-floor window, knowing the kink and the raw power currently unfolding inside, sent a chill through me that fought with the lingering heat of my own arousal. I was trapped, filled to my limit and bound, forced to watch from the shadows as she walked right into the world I had only dared to peek at from a ladder.

The massive plug felt like a lead weight, stretching my sphincter to a point that made my legs tremble as I pressed my forehead against the cold windowpane. I watched Anna's silhouette reach Rick's porch, the dull, rhythmic throb in my gut syncing with the frantic beat of my heart. My mind was a storm of agonizing "what-ifs"--would I hear her moans drifting back across the lawn, or would the front door swing open to reveal her leading those two massive men toward our bedroom?

The silk bit into my wrists as I struggled for a better view, the humiliation of being bound and filled warring with a dark, desperate need to know her fate. Every second she stayed over there felt like an hour, the pressure inside me serving as a constant, pulsing reminder that I was no longer the one in control. I was a tethered witness, caught between the terror of being replaced and the perverse, electrifying hope that she'd return with the very shadows I'd been spying on.

The cold glass was the only thing keeping me upright as I lost sight of her when she reached the edge of Rick's porch. My reflection in the window looked like a stranger--eyes wide, face flushed, my body trembling from the massive plug that felt like it was expanding with every frantic pulse of my heart. I tried to pull at the silk bindings, but the movement only forced the silicone deeper into my gut, a sickeningly sweet ache that made my knees buckle.

Through the darkness of the yard, I saw the porch light at Rick's house flicker on and then a couple minutes later, the porch light went dark. My heart hammered against my ribs so hard it felt like it might bruise. I was trapped in the very vulnerability I had envied from the ladder, while Anna had crossed the threshold into the lion's den.

Minutes crawled by. I strained my ears, trying to catch a stray moan or a scream but the night was unnervingly still. The only sound was my own ragged breathing and the occasional creak of the house settling. My muscles began to cramp from the strain of being bound, and the dull ache in my core shifted from a thrill to a demanding, heavy presence that begged for release.

Then, I saw it. The light in the second-floor window--the room with the sling--dimmed, then flared bright again. Three shadows moved across the drapes. One was unmistakable: the soft, curvy outline of Anna. She was standing between the two men. Then they moved away from the window, the silhouettes fading till I couldnt see anything.

The sight sent a jolt through me that nearly made my knees give out. The massive plug inside me felt like it was vibrating with the sheer intensity of the betrayal and the arousal. I was watching my life merge with the secret world of my neighbor, and the boundary between "observer" and "participant" had completely dissolved.

It was a little while later, when I heard the faint, unmistakable sound of my own front door opening. I had been leaning against the windowframe, daydreaming and missed her coming back.

The click of heels on the hardwood downstairs was slow--deliberate. I froze, my breath hitching. I looked at the clock and saw Anna had been over there for almost an hour. The footsteps began to ascend the stairs, getting louder as she got closer.

When the bedroom door pushed open, Anna was flushed, her hair even messier than before, and she was holding something in her hand that glinted in the low light: a black latex hood, identical to the one Rick was wearing.

"Brian, that's the other guy that you saw with Rick, said you looked lonely on that ladder, Tom," she whispered, her voice a low, jagged vibration that cut through the room. She walked toward me, the trenchcoat rustling as she took it off. "I showed them a couple pictures I took And they agreed... you aren't nearly open enough yet."

She reached out, her fingers cold as they brushed my cheek, before she slid the hood over my head, plunging me into total, silent darkness. The last thing I saw before the world disappeared was the cum on her cheek.

The rubber mask swallowed my vision, turning the room into a silent, suffocating void where only the fire in my gut existed. As Anna shoved me back, the mattress offered no cushion--only the lever that forced that massive silicone bulb deeper into my bowels, drawing a strangled, rhythmic sob from my throat.

I lay there, pinned by my own weight against my bound wrists, feeling the plug's wide flare grind against my tailbone. Then, the mattress dipped. Anna's tits pressed into my chest, her hands holding my hooded head as she claimed my mouth. The kiss was aggressive and slick; as her tongue tangled with mine, the sharp, salty tang of another man's cum coated my palate, a visceral brand of the threshold she had just crossed.

When Anna finally pulled her tongue from my mouth, the sudden void was quickly filled as she straddled my head, dropping her wet pussy directly over my nose and lips. I tried to ask which one of them had left their mark, but she cut me off by grinding her pussy against my tongue with a frantic desperation.

The sliding friction against my face was unmistakable; she was slick with more than just her own arousal. As I tasted the sharp, unmistakable tang of fresh cum coating her skin, the reality hit me like a physical blow. They hadn't just used their hands or toys on her--they had claimed her completely.

I was pinned beneath her, my vision a black rubber void, while the evidence of the neighbors' conquest was forced into my mouth, merging my voyeuristic fantasies with a raw, undeniable betrayal that sent my heart into a terminal race.

The thick, airless silence inside the latex hood made the sound of my own pulse roar in my ears. I felt Anna's weight shift on top of me, her skin slick and hot against my chest. Her voice came through the rubber, muffled but clear, vibrating with a jagged, breathless energy I'd never heard from her before.

"Can you hear me through the hood, Tom?" she whispered, her fingers tracing the seam of the mask over my jaw. I managed a tight, frantic nod, the rubber dragging against the pillowcase. My breath was coming in short, humid hitches inside the mask, the smell of talcum and sweat filling my nose.

"Good," she said, her voice dropping into a low, predatory purr. "Then I'll tell you exactly what happened when I got over there."

I lay there, bound and filled, the massive plug a constant, pulsing intrusion in my gut as she began to narrate her walk across the lawn.

"Rick answered the door," she said, her hands moving to my shoulders, pinning me down as she spoke. "He didn't even look surprised to see me. I started to tell him what you saw but he just smiled, took my hand, and led me straight up to that room--the one you were watching. Brian was already there, Tom. His cock was huge, just like you said. Seeing it in person... it was even bigger than you described."

A jolt of pure, electric jealousy fought with the raw arousal spiking in my blood. I pictured them in that room, the light from the second floor spilling out into the dark where I had been standing earlier.

"After Rick introduced us," Anna continued, "Brian didn't waste any time. He picked me up like I was nothing and put me right in that sling. He pushed my legs back, hooking my feet into the stirrups, spreading my legs open wide, before pushing his fat cock into me and then he started fucking my pussy relentlessly. He was slamming into me, Tom.

Every thrust felt like it was hitting my soul. I could see the window from the sling... I pictured you out there on top of your ladder in the dark, and it made me come so hard I thought I was going to black out."

I let out a muffled groan into the mask, my body bucking instinctively against the mattress. The image of her in that sling, being taken by the man I'd been spying on made my cock so fucking hard.

"Rick didn't just watch, either," she whispered, her fingers sliding down to the base of the plug still buried inside me, giving it a sharp, authoritative tug. "He lowered the head of the sling, dumping my head backwards and then he pushed his hard cock into my mouth while Brian was buried deep in my pussy.

They were spitroasting me. I wish you were there to see it. I was picturing them doing the same thing to you and it made me cum again.... well maybe it was cause of their big cocks too," she laughed.

"They didn't give me a second to catch my breath," Anna whispered, her voice trembling with the memory. "Brian stayed buried deep in my pussy, his massive weight pinning me into the sling while he hammered away with those long strokes that felt like they were reaching my throat.

At the same time, Rick was fucking my mouth, his cock pressing into the back of my throat, making me gag. His hands were holding my head as he relentlessly used my mouth, both of them moving in a frantic rhythm that ignored everything but their desire to cum. They both groaned and emptied themselves at nearly the same time, filling me with a staggering amount of cum as I hung there, totally spent and ruined."

Anna reached back and twisted the massive plug lodged in my stretched hole, making me groan loudly into her pussy. "After we all caught our breath, Brian told me something... he told me he saw you, Tom. He saw you gripping that ladder, watched you watching them. He said he liked the way you looked, all desperate and frozen in the dark. He said he wanted to see if you could handle being the one in the sling next time."

The air inside the hood felt like it was running out. My heart was thudding a frantic rhythm against my ribs, the boundary between my voyeuristic fantasies and this new, terrifying reality completely dissolving. I was trapped in the dark, my body opened and claimed, while my girlfriend told me about the men next door who were already planning my total surrender.

"Brian said he wanted to watch me fist Rick. Then tommorow, after they both fuck your asshole, he wants to watch me fist you. He is a natural leader, Tom," she whispered, her fingers tracing the seam of the latex over my jaw. "He looked over at Rick, and gave him a single, sharp command: 'Get back up there.'"

I let out a muffled groan, my body bucking instinctively against the mattress. In the silent void of the hood, I could almost hear the rhythmic creak of the neighbor's sling and the wet sounds of the encounter I had only caught glimpses of from the ladder.

"Rick didn't even hesitate," Anna continued, her voice dropping to a jagged rasp. "He climbed back into those stirrups, his body yielding to the leather straps all over again. Then Brian reached into a drawer and pulled out a pair of shiny black latex gloves--the same kind you saw him wearing earlier. Then he handed them to me."

I felt the smooth latex against my bare chest as Anna pressed her hands down on me. The sterile, thin material felt electric against my skin, a physical echo of what she was describing.

"I stretched them over my hands, Tom. The snap of the rubber was so loud in that quiet room. Brian grabbed a bottle of heavy-duty lube and squeezed a massive pool of it right into my gloved palm. He looked at me and said, 'Fist his hole. Be relentless."

I squeezed my eyes shut behind the mask, my heart hammering a frantic rhythm. The image of Anna--my Anna--standing between the neighbor's spread legs was almost too much to bear.

"I bunched my fingers into a tight point," she whispered, her hand sliding down to the base of the plug still buried inside me. "I pressed my hand against Rick's opening and felt him shudder. I watched his hole stretch around my knuckles, Tom. It was incredible. He was groaning, his head thrashing in that hood just like yours is now. I pushed, slowly and firmly, until my entire hand was buried inside him, his asshole gripping my wrist."

A jolt of pure, agonizing arousal spiked in my blood. I could feel the plug in my own stretched-out hole pulsing, my prostate hammered by the mental image of her fisting the man next door.

"I could feel his pulse against my palm," she said, her voice sounded like she was narrarating a dream. She gave the plug inside me a slow, authoritative twist that made me cry out. "I was opening him up, stretching him, while Brian watched and guided my movements. Brian said Rick had a greedy hole and he wants to see if you do too."

"Brian didn't just want me to push my hand in and leave it there," Anna whispered, her breath hitching as she leaned over my hooded face. "He wanted me to understand the mechanics of it. He told me to start with my right hand, bunched into a tight, narrow wedge. I watched Rick's hole stretch as I pressed past the initial resistance. I could feel the heat of his insides through the latex as my knuckles disappeared, then my thumb, until my entire fist was buried up to the wrist."

She shifted her weight, and I felt the massive plug inside me shift with her, a blunt-force reminder of my own capacity.

"But Brian wasn't satisfied," she continued, He reached over, grabbed a handful of Rick's hair, and pulled his head back until his throat was exposed. 'Now the other one,' he commanded. I didn't even hesitate. I slicked up my left glove, bunched it tight, and began to pry my way in beside the first one."

I let out a muffled, strangled cry into the mask. The mental image of Anna--my soft, Anna--operating with that level of intensity was more overwhelming than the silicone bulb currently stretching my own limits.

I pictured her two fists side-by-side, a massive, living wedge of muscle and latex expanding Rick's hole into a wide, dark void.

I could almost hear the wet, suctioning friction she was describing--the sound of skin being pushed to its structural limit.

"I had both hands inside him, Tom," Anna whispered, her voice trembling with a dark, buzzing energy. "I could feel his pulse fluttering against my palms. Brian told me to start twisting. I began to rotate my wrists in opposite directions, a slow, grinding churn that made the sling sway violently.

Rick wasn't just moaning anymore; he was making this high, thin sound, like a tea kettle about to boil over. He was completely hollowed out, his entire existence reduced to the feeling of my hands moving inside his gut."

Anna's hand moved from my chest to the flared base of the plug, giving it a sharp, rhythmic tug that mimicked the "churning" she was describing.

"Brian leaned in close to Rick's ear," she said, her own lips brushing the latex over my ear. "'I love what she's doing to you,' he told him. 'She's opening you up for everyone to see.' Then he told me to pull out. Not slow, but with a firm, steady draw.

As I slid my hands back, the suction was incredible. The moment my wrists cleared his opening, Rick's body went rigid. His back arched off the sling."

"He didn't even touch himself, Tom. The sheer internal friction--the way my fists had been hammering his prostate--sent him over the edge. It was a pure, hands-free prostate orgasm. He came in huge, frantic spurts that coated the floor, his body twitching in the stirrups long after he was empty. He looked ruined. He looked... perfectly destroyed."

Anna leaned her full weight onto me, the massive plug was bottomed out but it felt like she was trying to push the base of the plug into me too.

"And Brian looked at me, then looked back at our house," she whispered. "He said, 'Now go home and see if Tom can handle half as much. Because tomorrow night, you're coming back here to give your boyfriend's ass to me."

I was licking her pussy, trying to make her cum, eager to show her that I could give her what she needed, She came with a loud moan and when she did, I got a bunch more of Brian's cum that was trapped up in her stretched pussy. She finally got off my face and let me roll onto my stomach, then she untied my hands. I reached for the hood but she slapped my hand away.

"The hood stays on, Tom," She said loudly. "I will tell you when it can come off, got it?"

"Yea, ok." I said softly.

"Brian wanted to make sure you were properly prepared, Tom," she whispered, the mattress dipping as she leaned her weight into me. "I know you can't see, but he gave me this. It's an inflatable buttplug. He said if you want to be ready for them, you have to be stretched out."

I felt her fingers wrap around the base of the plug and slowly pull it out of my ass. My hole stretched around the thickest part of the plug, tearing a scream of anguish out of my throat. Before I had a chance to rest, she guided a long, slender silicone shaft into my gaping hole.

It slipped in easily compared to the massive plug, but the relief was short-lived. I heard the first rhythmic click-hiss of the pump. Inside me, the bulb began to expand, a slow, relentless blossoming of pressure.

"He told me to take my time," she purred, her thumb rubbing down my taint to the backside of my balls. "To see exactly where your limit is, then push right past it."

Every pump sent a fresh wave of fullness through my core, stretching the walls of my rectum until the dull ache sharpened into a white-hot bloom of overstimulation. I was trapped in the dark, my body being hollowed out by a gift from the neighbor I had been spying on just a few hours ago.

The rhythmic hiss-click of the pump echoed inside the latex hood, each squeeze of the bulb forcing the inflatable deeper into my guts. Anna leaned over, her breath hot against the rubber of my mask, her voice a jagged whisper of intent.

"We're going to find your limit, Tom," she purred, her fingers tracing the tight seal of my entrance. "I'm going to pump you up until you're begging, then I'll deflate it and slide that massive plug back in. If it doesn't slip in like it belongs there, we go right back to the inflatable and pump you up some more."

She gave the bulb a double squeeze, and I buckled against the mattress, a muffled cry trapped in the mask as my internals were forced to accommodate the blossoming pressure. The stretch was absolute, a heavy, throbbing ache that felt like it was rewriting the anatomy of my body.

"You better hope you're a quick study," she added, "Because we have a date at Rick's tomorrow night at 8:00 PM. Brian and Rick are expecting you to be ready for that sling, and if you aren't stretched out enough to take them both, I might just have to leave you here in the dark while I go over there alone."

The threat was more intoxicating than the physical pressure. I was being prepped like a piece of equipment, refined and expanded under Anna's command to meet the standards of the men next door. With every rhythmic pump, the boundary between my old life and this new, hollowed-out reality drifted further away, replaced by the singular, crushing need to be wide enough for whatever waited for me across the lawn.

"That's it, Tom," Anna whispered, her voice a low vibration against the rubber of my hood. "Feel that? That's the space Brian and Rick are going to fill tomorrow. If you think this is a lot, just wait until you're hanging in that sling and they're both testing how much you can take. Rick told me to get you used to sucking cock, but Brian said no. He said they were going to take turns fucking your throat, teaching you to deepthroat their cocks."

She gave the pump two more deliberate squeezes. I buckled, my forehead pressing into the mattress as a strangled groan tore from my throat. The fullness was agonizing, a white-hot bloom of overstimulation that made my entire lower body throb. I felt completely hollowed out, my muscles forced to accommodate a girth that felt impossible.

"You're shaking," she noted, her hand sliding down to the base of the inflatable, her fingers tracing the tight, white-knuckled stretch of my opening. "Good. That means you're starting to understand. Rick didn't get that wide overnight, and neither will you. But by 8:00 PM tomorrow, you're going to be exactly what they're expecting."

She reached for the release valve. With a sharp hiss, the pressure vanished, the sudden emptiness feeling almost as intense as the intrusion. I slumped against the pillows, gasping for air inside the humid heat of the hood, my muscles twitching in the sudden void. But the reprieve was momentary. I heard the wet, heavy slide of the massive silicone plug being coated in a fresh layer of lube.

"Now," Anna commanded, her tone dropping into a cold, predatory edge. "Let's see if all that pumping worked. If this doesn't slide in like it belongs there, we start the pump all over again. And Tom? If you want to be in that room tomorrow instead of watching from a ladder, you better not fight me."

I felt the blunt, wide head of the plug press against my entrance. It didn't hesitate. With a firm, downward surge of her weight, Anna drove the massive toy back home. This time, there was no sharp, tearing resistance--only a deep, sliding fullness that felt like a revelation. My body, prepped and expanded by the neighbor's gift, accepted the intrusion with a heavy, pulsing thud.

"There," she breathed, her hands anchoring on my hips as she began a slow, rhythmic grind. "You're ready. Tomorrow night, we're going across the lawn, and I'm going to watch Brian and Rick turn you into exactly what you saw through that window."

"Anna," I rasped, my voice sounding distant and metallic inside the mask. "The plug... the widest part of it. It's almost exactly the same size as your hand when you bunch it into a fist."

"You're right, Tom," Anna whispered, her gloved hand wrapping around the base of the plug. "It is the same size. You want me to try it, don't you?" I slowly nodded my head yes.

"You've been thinking about it since you were on that ladder, haven't you?" Anna's voice was a low, predatory purr. "Watching that guy's gloved hand disappear into Rick. Wondering if your body could actually stretch that far."

She didn't wait for an answer. I felt the sudden, cool slip of her removing the massive plug. For a heartbeat, there was a vacuum of pressure, a hollow ache where the silicone had been--but she didn't give my muscles a second to retract.

"Stay still, Tom," she commanded, her tone dropping into a cold, clinical edge. I felt her slick, gloved fingers press against my entrance. She wasn't using a single finger this time; she bunched her hand into a tight, narrow wedge, exactly like she'd described doing to Rick. The pressure was immediate and immense. It wasn't the blunt, static fullness of the plug; it was the shifting, living force of her knuckles prying their way past my sphincter.

A strangled cry tore from my throat, muffled by the rubber mask. My back arched instinctively, but Anna leaned her full weight into my shoulder blades, pinning me to the mattress.

"Don't fight it," she hissed. Slowly, agonizingly, I felt the widest part of her hand--the line of her knuckles--force its way inside. The stretch was absolute. It felt like my skin was being pulled to the structural limit of what a human body could endure. But then, finally, the resistance gave way. I felt her thumb tuck in, and suddenly, her entire fist was buried deep within me, up to the wrist.

The sensation was unlike anything I'd ever felt. The heat of her hand through the thin latex was intense, a throbbing, internal presence.

"Look at you," she whispered, her voice trembling with a dark, buzzing energy. "You're taking it. You're just as greedy as Rick." She began to rotate her wrist, a slow, grinding churn that made my vision swim.

"Anna, get video. Please, I want to see you filling me." I choked out. My request hung in the room, a desperate plea to bridge the gap between being the voyeur on the ladder and the center of the scene.

"Video?" Anna's voice came from above me, sounding both amused and dangerously sharp. I felt her fist--still buried deep within me--shift in a slow, calculated circle, the latex of her glove creaking against my internal walls. "You want to see what I'm doing to you? You want to watch yourself being ruined?"

I managed a frantic nod, the mask dragging against the pillow. The pressure of her hand was absolute, a blunt-force presence that made my pulse thrum against her knuckles.

"Fine," she whispered. I heard the rustle of her trench coat on the floor as she reached for her phone. "But if I'm filming this, Tom, you don't get to hide. I want you to arch your back. I want the camera to catch exactly how wide I'm stretching you."

"Allright babe, I'm recording," she said quietly. Then she started narrarating for the video. "Look at this, Tom," she commanded, though she knew I couldn't see. "My entire wrist is disappearing into you. You're gaping around my gloved hand just like Rick did in that sling."

She began to move her hand in a rhythmic, prying motion. Each time she drove her fist deeper, I heard the wet, suctioning sound of the lube--a sound that was now being recorded for us to watch later. The knowledge that this was being captured, that I would be able to see the literal limit of my own body being pushed, sent a fresh wave of electricity through my gut.

"Tomorrow night," Anna said, her voice dropping as she adjusted the angle of the phone, "when we're at Rick's, I'm going to show this to them. I'm going to show them how well I've prepped you. They're going to see that you're not just a peeping Tom--you're a filthy stretched out buttslut, just like Rick."

She gave my prostate a firm, deliberate shove with her knuckles. I cried out, a muffled, guttural sound that I knew the phone's microphone was picking up perfectly.

Anna twisted her hand back and forth, the latex of her glove creaking as her knuckles bore down directly against my prostate with a heavy, rhythmic friction. Every rotation sent what felt like spikes of electricity through my gut, forcing my breath into short gasps inside the suffocating heat of the hood. I was pinned down by her fist, hollowed out and helpless, as she churned inside me until the pressure reached a breaking point.

The dam finally burst. A primal, muffled shout tore from my throat as my body bucked violently against the mattress. I came in frantic spurts, shooting all over the blanket underneath me as my whole body twitched and shook.

The suction was intense, it felt like my insides were being dragged out with her hand, when Anna finally withdrew her fist, My muscles twitched uncontrollably, unable to close the gap she'd left behind, while the cool air hit my internal walls for the first time in what felt like hours. I lay there, hollowed and heaving, as she ran a finger around the rim of my gaping hole, laughing at the sight of my ruined hole.

"Look at you," she whispered, her voice a mix of awe and cold authority, "You're still gaping. If I didn't know better, I'd say you were built for this, Tom. Brian was right--you're a natural."

She didn't offer me a towel or a moment to recover. Instead, I felt the massive plug again, pressed against my slack hole. With a slow, merciless pressure, she buried it back into me, the flared base sitting flush against my skin, ensuring I stayed open.

"You're sleeping with that in tonight. I want you ready for tomorrow night. You aren't even gonna flinch when Rick and Brian start their work on this hole."

I was too spent to even offer a response. I just lay there, heavy and still in a cooling puddle of my own cum. I fell into a deep, dreamless sleep almost instantly.