A gay story: Uncle Caught by Niece and Boyfriend An older man is caught in self-bondage by his niece and her boyfriend, a fucking machine reaming his ass.
This story contains self-bondage, crossdressing, MM anal, and non-consensual sex (initially).
If that’s not your thing, thanks for stopping by.
Cheers.
—————
My niece, Audrey, was staring into my terrified eyes.
“You’re gonna love this, Uncle Don,” She purred as she stroked my face around the strap for the 4-inch penis gag lodged in my mouth.
“Jerry has always wanted to fuck a sissy, and it’s obvious you want to get fucked, so this is a win-win, don’t you think?”
The question was rhetorical – I couldn’t speak to answer, even if I wanted to.
Perhaps I should back up and explain how I got into this situation.
———–
I’m 44, retired, and live alone. My wife passed away four years ago, and I really haven’t gotten over the loss. I haven’t moved on or thrown out any of her stuff. The insurance settlement allowed me to retire and withdraw from day-to-day life.
I don’t want anyone new in my life, but I still crave sex daily. So, I turned to online porn and masturbation. Eventually, vanilla porn became boring, and I branched out.
At first, it was bondage videos – they were intense. I didn’t enjoy videos where the Doms inflicted pain. But seeing women bound and restrained – while men fucked the shit out of them or tormented them really excited me. I wondered what it would be like to be tied up and used.
So I looked into male submissives and came across FemDom videos. Wow! Just wow! Men trussed up and used as fuck toys. Teased and denied, over and over.
Then came pegging and strap-on vids. I wondered what it would be like to get fucked in the ass. I started experimenting with my wife’s dildos and vibrators. I was immediately hooked. Anal sex became my new thing.
Sometimes the men in the videos were in lingerie, and I wondered what that would be like. So I started wearing my wife’s panties and stockings. They were pretty dull, so I started buying new sexy stuff online. Stockings and garters. Then panties and bras. Cammies and corsets. Slutty shoes and boots.
Eventually, my wife’s small selection of dildos and vibrators wasn’t enough. I bought new toys. Bigger toys. Then fucking machines. And that’s when I came across bondage gear – which changed everything.
Three years later, I have a basement full of sex toys and paraphernalia. Bondage gear; bondage frames; fucking machines; dildos, vibrators, and butt plugs of every size and description. I converted the meager basement of my rancher into a dungeon – which probably rivals that of a professional Dom.
I learned about self-bondage and time-release restraints. My ass stretched out, and I was able to take massive toys. Anal sex became my go-to – if I didn’t have something in my ass, I couldn’t orgasm.
About a year ago, I came across Sissy Hypno videos, and I became obsessed. Especially with the concept of a sissygasm. I started fucking myself daily, sometimes multiple times, trying to achieve this elusive dream. But, so far, I’ve never had one. Oh, I’ve had anal orgasms, but I’ve never ejaculated from being ass fucked.
I keep myself completely hairless – except for my head, which I’ve let grow out – my hair is now well past my shoulders. Online tutorials have made me relatively competent at applying makeup. I have an extensive lingerie collection. A large assortment of neon wigs and breast forms. And spend the majority of my days prancing around the house dressed as a sissy slut or playing in my dungeon.
Being a recluse and introvert – I don’t get visitors. So it’s safe for me to dance around the house in sexy clothes with a plug in my ass – or should I say ass-pussy. I don’t have to worry about family or friends dropping by unannounced. Most of my friends have moved away or given up on me, and my family lives on the other side of the country.
———-
A couple of weeks ago, I found a new bondage frame on Ali Express and ordered it. It arrived this morning. I met the courier at the door and immediately began setting it up.
It’s called the ‘BDSM K9 Frame Training Shelf’ and is designed to lock someone comfortably in the doggy position. It has built-in ankle and wrist cuffs, a bench to support your torso, and a padded support and restraint system for your head and neck. I didn’t order the optional fucking machine attachment since I already have several of far superior quality.
The only problem for me was the wrist cuffs – they were leather straps, and I couldn’t lock them by myself. So drilled a hole in the right-wrist support and bolted in an eyehook. Then attached one of my time-release restraints to the eyehook. Now I can safely strap my left arm to the frame and lock my right arm with the time-release restraint. This immobilizes me until the time release opens.
Rather than taking it to the basement, as I should have, I set up the frame in my living room. I set it on a large and very sturdy coffee table so I could watch TV. I was gonna lock myself in for two hours and really fuck my man-cunt today. Watching my favorite sissy hypno videos while I got raped.
I covered the coffee table and surrounding floor with towels to catch drool, leaking cum, ass juice, and lube. I laid on the frame multiple times, adjusting the coffee table until it was in the best position to see the TV.
Next, I set up the fucking machine – getting it positioned always took multiple attempts. The best method, I found, was to zip-tie it to the bondage frame and then adjust the arm until the thrust rod, without a dildo, touched my asshole. I’d then move the arm back 2 inches along the thrust angle, attach the dildo, and voilà, perfection! Using the controller, I fully retracted the thrust rod and fastened today’s dildo to the rod.
The final touch was to set up a few wifi security cameras to record my fucking from different angles. The cameras were controlled from my laptop, which I placed on the table by my head. This would allow me to enjoy my performance as it was recorded.
With all the hardware setup, I went about getting ready. I had used wax strips to remove body hair yesterday, so I began with a nice warm enema to douche my ass.
I applied a nice slutty makeup job, but I’m a 44-year-old man of average build, and there’s no point in trying to look like a woman. Dumpy and masculine can’t be turned into a beauty queen.
I often wondered why I bothered with makeup. I never looked feminine or even particularly attractive when wearing it. Eventually, I realized it was the fantasy of being caught wearing slutty makeup or being forced to service a FemDom or her stud while made up like a salacious tart that made makeup exciting – at least for me…
Next came a lovely bright blue shoulder-length wig. Followed by matching blue stockings, garter, and bra. The final touch was the breast forms – a nice set of silicon-filled D cups with huge nipples. I didn’t bother with panties; I wanted my ass on full display for my pending rape.
I inserted a lube applicator into my ass and filled myself twice with a long-lasting water-based lube. That should prevent any issues for my planned marathon fucking.
I knelt on the table, wiggled the tip of the dildo into my eager asshole, and positioned my ankles in the cuffs of the frame. I strapped a cuff around each ankle and tested them to ensure they wouldn’t come loose. For good measure, I put a lock through each restraint. It wasn’t necessary, but it added to the ambiance and looks good on video.
I chose a thin 8-inch dildo because I knew from experience that it was better for long sessions. I made the mistake of getting carried away with a 3-inch by 12-inch dildo once – and tore my asshole.
I lay on the torso bench, and with the tip of the dildo in my pucker hole, I turned the control until the fucking machine – a Black Magic XL – was at full extension. I wiggled and tested the depth, then ran the XL through a couple complete stroke cycles. Perfect!
I wrapped a large leather belt around my waist and another around my upper chest. These weren’t part of the frame, but I wanted to limit my movement as much as possible. I cinched the straps tight, ensuring I was immobile, but could still breathe. My bra and fake boobs squeezed to the side and around the torso bench. It looked pretty convincing in the security cam monitor.
Next, I placed my head and neck on the support and tried to fasten the neck restraint. Shit! It was too tight. In my impatience to get fucked, I hadn’t tested the neck restraint. It would need to be altered before I could use it.
Fuck it! My torso being strapped down would have to suffice. I removed the neck restraint from the frame and positioned my head on the support. It was comfortable – I didn’t foresee two hours being an issue.
I grabbed the TV remote and set it to play the queued-up video clips. The first clip started – Emperor Hypnos Sissymaker – a classic. The music started thumping, and I enjoyed the images and music for a minute.
Time for the finishing touches. I placed my left wrist in the cuff and fastened the buckle with my right hand. I already had the time release cuff on my right wrist – I just needed to press the cylinder into the base of the MagBound – the power source and self-timer were already set up – the countdown of two hours had already started.
I fired up the fucking machine and set it at a steady but reasonably slow pace. I wanted this to be a long slow build – to hopefully – an epic orgasm and maybe, even the elusive sissygasm…
Everything was in place, and all that remained was to secure my right wrist. I looked at the TV and camera feeds. The first video was close to ending. The camera feeds showed fantastic pictures of my ass being raped by my fucking machine.
Feed one showed a closeup of the dildo stroking in and out of my ass-pussy. Feed two showed my ass and part of my body with my stocking tops and garter visible. Feed three was a side view and gave a real sense that I was dressed up as a sissy and getting railed. And the last was a 3/4 view from the front-right, showing my face and the fucking machine – I wanted to catch my look when I finally blew my load.
I had just about locked my right wrist when I noticed the penis gag. I almost forgot about it in my excitement. Shit! I couldn’t put it in with one hand. I unlocked my left wrist, put the gag in my mouth, and fastened the buckle. At 4 inches, the tip of the penis just touched my throat – not enough to obstruct my breathing, but enough to cause excessive spit and drool to accumulate. It also prevented any coherent sounds from coming out of my mouth.
With the gag in place, I reattached my left wrist and then made one final scan of my surroundings. I brought the cylinder of the MagBound in contact with its base, and it snapped into place. I gave a hard tug – it had seated perfectly. I was locked in.
A new video started on the TV. It was a caption-video extolling how I was a sissy faggot that needed to seek out and service big black cock. I sighed around the gag and relaxed, enjoying the sensation of the dildo fucking my sissy pussy.
Heaven – pure heaven. I was about to be fucked for close to two hours, and there was nothing I could do about it. My raging cock was dangling below my hips, my ball sack dangling with it. I tried to wiggle my ass to get my cock and balls to move, but the straps on my body prevented any movement. I sighed in frustration and delight.
After a bit of time, my mind started to wander. What if someone broke in and found me like this? Would they use me like a sissy slut? Would they move the machine and rape my ass? Or would they kick the shit out of me in a homophobic rage?
The doorbell rang, scaring the shit out of me and interrupting my wandering mind. I looked up at the windows and blew a sigh of relief, I had pulled the curtains, so no one could see in if they decided to snoop. I relaxed into the frame again – my entire body had become taught when the doorbell rang.
It rang again. Persistent, I thought. Probably selling something or pedaling religion.
It rang a third time, and then they started pounding on the door. What the fuck? My car was in the garage – no one could tell if I was home. Go the fuck away and leave me to enjoy my fucking.
Then it happened. My worst nightmare. I heard the door unlock and open, followed by “Uncle Don, are you home?”
Fuck! Fuck! Fuck! Fuck! Oh shit! Oh shit! Oh shit!
I started struggling mightly against the restraints – but it was useless. The fucking machine continued to relentlessly stroke in and out of my ass. The video changed – it was about to get worse – ‘Shemale Cock Love Hypnosis’ started. The dialog played loudly and was unmistakable.
Since I hadn’t attached the neck restraint, I could turn my head towards the entry hall. I watched in horror as my niece Audrey walked into view and stopped dead in her tracks. The video voiceover played loud and clear:
“… you love girls with cocks more than anything…”
Audrey stood rooted to the spot. Her eyes were big as saucers. Her mouth hung open in shock. Then a man walked around her and saw me. A huge smile played across his face – he nodded knowingly.
My eyes got wide, and I looked away. I couldn’t bare to look at them. I felt so ashamed and terrified. My entire family was gonna find out about my sissy alter-ego. I’d be disowned. What little contact I had with them would be over. My sister would lose it! My life was officially over. I dropped my head on the support, and tears flowed from my eyes.
“Oh, hell yeah! Now, this looks like a party,” raved the young man. “You didn’t tell me your uncle was a raging sissy, Aud. Holy shit! This is fucking awesome!”
His discourse seemed to revive Audrey from her catatonic state.
“WHAT THE FUCK!” Audrey’s outburst was nearly a scream. I heard her slap him – I’m guessing his arm or chest, but I couldn’t be sure.
“That’s my uncle, you sick fuck!”
“I’m a sick fuck? He’s locked into some bizarre torture device, getting fucked, while watching sissy videos, and I’m the sick fuck?” Countered the excited youth.
“Good point.” Audrey paused, and the house seemed silent, even with the dialog and music from the videos blaring.
After a few seconds – an eternity for me – Audrey spoke again. “Fuck! I can’t watch this. Unlock that fucking perv. I’m going to the kitchen to hopefully purge this from my mind.”
Fuck. Not good. Audrey’s wedge sandals clopped across the tile as she went to the kitchen. I turned my head and looked at the cam feeds, expecting to see the guy moving towards me in the frame, but he was nowhere to be seen. I turned towards the entryway; it was empty; he must have followed her to the kitchen. Why didn’t they leave and let me die of shame in peace?
The video was too loud, and I couldn’t hear anything from the kitchen. Eventually, Audrey and her man had a heated argument then it got quiet again. After about twenty minutes, based on the video clip progression, I heard Audrey’s sandals on the floor again.
I couldn’t look at her, so I looked at the security cam footage. I could see her standing just inside the living room, watching me. The young man’s hands were on her shoulders, rubbing soothingly, and he appeared to be whispering in her ear – or perhaps kissing it – I’m not sure.
His hands moved across her shoulders, wrapped around and cupped her breasts. Her perky, perfect breasts. I could see him pinch her nipples and kiss her neck. She tilted her head to give him better access. They were watching me and making out – enjoying my self-bondage session and rape like I was a cam session on Chaturbate.
One of his hands dropped to her pants and undid the button and zipper. He slipped his hand into her pants and started to massage her pussy. Her mouth opened, and she appeared to moan in pleasure – the video was still far too loud for me to be sure.
The next queued video began to play. This time the voiceover might have been the worst yet:
“… Your eyes are fixated on the dark, veiny, beer-can-sized cock. And those big hungry black balls. You want that black cock. You want to worship that black cock. You want to take it in your hands and feel its weight. Run your hands over the throbbing veins and rock-hard mushroom head and smell that black bull testosterone as it wafts off his body. You want to feel that cock pummel your white virgin asshole. And you want to feel a huge load of superior black cum, unload deep inside you…”
The TV showed a tiny blonde taking a massive black cock in her little pink pussy – it was magnificent, and I couldn’t help myself. My shriveled cock started to get hard again.
I don’t know if it was because Audrey and her guy were watching or if it was a programmed response to all the sissy hypno I consumed – but I moaned in pleasure around the gag and shuddered as the dildo fucked my ass.
Audrey’s guy spoke up. “Look at him. Even now, he’s loving this. His cock is getting hard, and he’s moaning at the thought of a big black cock fucking his sissy asshole. Let’s do this. I promise it’ll be fun. And if it’s not, you can exact some other punishment.”
I looked at the cam feed. I still couldn’t stomach the thought of looking at them directly. His hand rubbed her pussy, and his other hand was under her top, pinching and rubbing her breast.
Audrey was enjoying his ministrations. And they were both enjoying the video, my performance, or perhaps both. I couldn’t tell from the cam feed, but they were definitely looking into the living room.
I saw her shudder on the cam feed and then nod and say something. Her boyfriend retracted his hands, spun her towards him, then kissed her passionately. After a few minutes of pawing and kissing, they broke their embrace, and I watched as Audrey walked across the carpet. Her feet appeared beside the coffee table, and she squatted by my head.
I could see her light blue panties in the opening of her jeans and smell the scent of her pussy. She grabbed my chin between her thumb and index finger and lifted my face; her eyes bore into mine. I tried to look away – to turn my head so I couldn’t see her. I was so fucking embarrassed and ashamed. Tears leaked from my eyes again.
She patted the side of my face lightly and rubbed in small circles. “It’s okay, Uncle Don. Jerry talked to me and made me understand. You’re just masturbating. I may not understand it, but Jerry says it’s not that abnormal. Apparently, lots of guys like anal stimulation. I’m sorry I freaked out on you. And I’m sorry we barged in on you. And I won’t tell Mom. But… Well… Jerry has other plans. And I’ve decided to go along with them – so…”
Because I couldn’t turn my head, I cast my eyes to the floor to avoid her gaze.
She tapped the side of my face. “You need to look at me, Uncle Don.”
I still couldn’t bring myself to look at her. She slapped the side of my face.
“Look at me, damn it! You’re being rude.”
She didn’t slap me hard, but it was still a shock, and I looked at her in reflex.
“There. That’s better.” And she smiled at me. “Now, let me explain what’s gonna happen.”
The fucking machine stopped, and the dildo was retracted from my now well-used ass-pussy. My pucker hole winked and twitched at being empty, and my brows knotted in despair from the loss. Then I felt hands at my crack, spreading my cheeks – it was Jerry. I tried to thrash, but I’d tied myself down too well.
“You’re gonna love this, Uncle Don,” She purred as she stroked my face around the strap for the 4-inch penis gag lodged in my mouth.
“Jerry has always wanted to fuck a sissy, and it’s obvious you want to get fucked, so this is a win-win, don’t you think?”
The question was rhetorical – I couldn’t speak to answer, even if I wanted to.
I tried shaking my head and pleaded with my eyes – I didn’t want her boyfriend to fuck me, did I?
Every fiber of my being was screaming ‘NO’ – but my cock was hard as steel and pulsing at the thought.
My stretched-out asshole twitched as Jerry applied more lube.
“Oh, come on, Uncle Don, if you didn’t want a cock in your ass, why did we find you trussed up in lingerie, a fucking machine raping your ass, and videos extolling your love of cock, playing on the TV. It’s obvious you want a big hard cock to pound that little fuck hole of yours.”
When Audrey first saw me like this, she was disgusted. Now she was taunting me as her boyfriend prepared to fuck my ass.
“I won’t let Jerry fuck my ass – his cock is way too big – so he’s gonna fuck your ass instead. Everyone gets what they want.” She beamed.
I tried to hang my head in shame and look away from her, but I couldn’t. I shuddered and moaned around the gag in my mouth. Jerry had scored a direct hit on my prostrate while lubing my man cunt. Audrey smiled knowingly and patted the side of my face.
“That’s it, Uncle Don. Now you’re getting in the spirit of things. Just relax and let Jerry take care of you.” She laughed and stood up.
This isn’t what I had in mind when I got up this morning – but it looked like my fantasy of being locked in bondage and fucked like a sissy was about to come true. The part of my mind that harbored my homophobia had me pulling at my bonds, trying to break free. My mind screamed – Don’t let him fuck you. While another part of my mind screamed – Fuck yeah! You’re finally getting a real cock.
Audrey kicked off her shoes and slid her jeans down her legs, followed by her very damp blue panties. She turned towards the TV and kicked out of her jeans and panties. I couldn’t help myself – I tilted my head back and looked up. Her fingers reached between her legs and spread her pussy lips apart. One, then two fingers dipped into her pussy and started thrusting. Her knees turned inward slightly, and she furiously frigged her cunt while watching the TV.
“I gotta admit, Uncle Don. This shit you’re watching is hot.” She rasped.
Jerry spoke up from behind me. “So, my little cum slut. I’m assuming you’re a virgin – or you’d be out getting fucked by someone instead of going to these lengths to get your kicks. Please nod if I’m right.”
Fuck that. I’m not about to acknowledge the guy getting ready to rape me.
“You really should answer me. If you don’t, I might decide you’re a pro and can take a real anal pounding. And trust me, sissy. I’m packing a rather impressive package. Audrey won’t let me fuck her ass because she’s afraid I’ll hurt her.”
My eyes shot open, and I immediately nodded so Jerry would know I was a virgin.
“Much better. Okay, so I’ll go slow and use lots of lube, but you seem pretty loose already. Hell, I’ve already got three fingers in you, and you haven’t so much as squirmed in protest. Oh, now it’s four fingers. Fuck, I bet I could get my fist in there. Hey Aud, do you want to watch me fist your sissy uncle?”
I shook my head violently – I didn’t want to be fisted.
“Oh, never mind. Sissy doesn’t want to be fisted.” He chuckled. “Hey babe, come watch me feed Mr. Happy into the sissy’s pussy.”
Audrey pulled her fingers from her pussy and walked out of my view. I turned to the cam feed and watched Audrey lick her fingers clean. Then stared in shock at the scene behind me. Jerry had his cock in his hands and was stroking and lubing it. Massive barely began to describe it. It wasn’t the longest dick I’d ever seen, but it was definitely the thickest. It looked like he was stroking a soup can.
Terrified of Jerry’s gigantic cock, I began to struggle again. Audrey stepped up on the coffee table and sat on my back. Her sopping pussy was warm and wet on my bare skin. She rubbed back and forth a few times, then settled.
“That okay, Uncle Don? Can you breathe with me on your back?” She asked and turned to watch my head.
Her pussy felt amazing on my back. I shuddered involuntarily at the contact and pleasure of having such a delectable young pussy touching my body. I nodded that I could breathe.
“Okay, good. Now try to relax. Jerry’s cock is fucking huge. But if you can take four of his fingers, you should be able to take it. It might hurt a bit, but… well, this is gonna happen, so… I don’t know what else to say, except you really need to relax.”
Jerry spoke up. “You think he might have poppers? I’m not saying he’s some druggie, but, you know, if he’s into this, he might have some.”
“What are poppers?”
“Really? You’ve never heard of poppers, babe?” Jerry seemed surprised, and frankly, so was I.
“No. Why, what are poppers?”
“Gay guys use them. It’s also called ‘Rush’ sometimes. Apparently, it makes them horny but also relaxed. Supposedly it makes anal sex easier.”
“Oh, yeah, I’ve heard of Rush. Uncle Don – do you have any Poppers?”
I nodded yes. Maybe I could get Audrey to remove the damn gag and talk my way out of this.
“He nodded yes. You go check his ensuite and bathrooms. They’re probably in the medicine cabinet or a drawer. I’m gonna sit here and watch some more of his videos. I’m really starting to get off on these things. Some of these chicks with dicks are fucking gorgeous – I’d drop my panties for them in a heartbeat.”
I watched Jerry rocket out of the room in the cam feed and felt Audrey spin on my back and face the TV. I watched as she peeled off her top and tossed it on the sofa, then started playing with her perky little nipples.
The video on the TV was now a strap-on compilation music video, the soundtrack being ‘Closer to the Edge’ by Thirty Seconds to Mars.
“Wow, good tunes, Uncle Don.” She started rocking on my back in time to the music and singing along.
“You know… I can’t keep calling you Uncle Don. Just seems too formal, and well… we’re definitely beyond formal now, aren’t we? So I think I’ll call you Dawn. But spelled as a girl would spell it. Or maybe Sissy. But no more uncle. Okay?”
She ran her fingernails along my back as she finished, and I arched into them and nodded my agreement.
“Fuck me! This video is awesome. I’ve seen strap-on videos before, but it was always just lesbians going at it. I’ve never seen women using them on men before. Maybe I should spend more time looking into kinky shit.”
She was now rubbing her pussy and riding my back, grinding her pussy lips along the ridges of my spine. The video ended with a long list of credits.
“Fuck! Where’s the remote? I wanna watch that again.”
I waved my right hand in the direction of the remote. Audrey picked it up and examined the buttons. She hit the ‘prev track’ button, and the video started over.
“Fuck yeah!”
Jerry came back into the room, “Found them. Medicine cabinet.”
“Gimme your cock!” Audrey barked.
I watched the cam feed as Jerry presented his cock to Audrey; it was still hanging out of his pants but was nearly flaccid. I watched in awe as this small girl opened her mouth like an anaconda and took about three inches of that monster into her mouth. Granted, Jerry’s cock was soft now, but shit, it was still massively fat.
She bobbed and gobbled it and ground her pussy into my spine. Using one hand to play with Jerry’s balls and the other to rub her clit. His dick started to get hard, and Audrey began to struggle.
“Woah, teeth babe.” And Jerry pulled free.
“Damn it! I want a cock to suck! Why’s your dick gotta be so fucking big.” She pouted. “Okay, fuck it! Let’s get that monster up Dawn’s sissy ass. That should be hot to watch.”
“Here,” Jerry handed her the popper bottle. “Take the top off and stick it under his nose. Hold one nostril closed while he inhales, then do the other side. I don’t know how powerful that shit is or how much he takes. Work with him and figure it out. I’ll finger his ass while you do it and see if he feels looser.”
Audrey leaned forward and laid on my back, her blazing hot, rock-hard nipples pressing into the skin between my shoulder blades. It felt amazing. She held the open bottle under my left nostril.
“Inhale, Dawn.”
I’d seen the size of Jerry’s cock – I wasted no time and took a big, long hit and held it.
“And the other side.” Audrey chimed.
I repeated the inhale on the other nostril. My head expanded like a balloon, and my stress evaporated. Audrey and Jerry were here playing with me. Jerry was about to make my fantasy come true and fuck my sissy cunt. Audrey was naked and lying on my back, lightly kissing my neck. Jerry’s fingers were buried deep in my ass, stretching me to glorious new limits. Yeah, things were good.
“Need any more before Jerry rapes your ass, Sissy?”
I thought about it for a second and nodded yes. Audrey repeated the process, and I took two more big hits. My head was swimming. Fucking awesome. My cock swelled, and I felt Jerry insert his thumb into my cunt. Woah, that was new – his fingers and thumb expanded like an anal dilator – working my sphincter.
My head pulled back and rolled around as I moaned in ecstasy around the gag.
“Fuck babe, I’ve nearly got my fist in him. I’m gonna put my cock in while he’s all loosened up. Wanna watch?”
“Of course.” Audrey sat up and spun on my back, her pussy never losing contact with my skin.
I felt the head of Jerry’s cock press up against my stretched-out pussy. He pushed. Slowly, steadily. My sphincter parted and allowed his head to begin penetrating. Fuck! I’d had some big stuff in my ass before, but this felt really wild. It was massive but also pliable and really, really warm.
He pulled back and started again. Repeating the process again and again. Each time managing to get his head a little deeper into my sphincter. Audrey had her fingers in my ass crack, trying to stretch my hole wider.
“Fuck, he’s getting tighter again. Give him a couple more hits of the poppers, Aud.”
Audrey spun around and laid on my back again, presenting the bottle to my nose. Three hits to each nostril. I was completely fucked up and nearly begging to be fucked. I tried twerking my ass at Jerry, but between the straps holding me down and Audrey laying on my back, I didn’t move much, but I think Jerry got the idea.
“Okay, babe. I think he’s ready. Let’s fuck this slut.”
Audrey spun back again and pried my cheeks apart. Jerry pressed his cock head against my stretched-out hole, and one of them spit on my ass multiple times. I felt the spit run down and pool around the top of Jerry’s cock. This time he held it in place and bucked forward over and over. Each forward thrust nudged his head into my cunt a little more.
I screamed into the gag. “Harder! Harder! Harder!” hoping he’d understand I needed him to ram it home.
“I think he wants you to slam it in, babe. Push hard and pop his fucking cherry!” Audrey, bless her heart, understood.
Jerry gave a mighty thrust, and the head popped in. He stopped and held it there.
I screamed into the gag. Fuck, it burned and stung. It didn’t really hurt – it was like someone had hit me with a cane – a spike of pain – followed by a burning sensation.
I shuddered under Audrey and moaned blissfully into the gag. Once the burn subsided, I yelled into my gag.
“Fuck me! Fuck me hard!”
Jerry understood my cry and started to slide that fat fucking monster into my bowels.
I shuddered. I vibrated. I mewled and moaned and nearly lost my fucking mind as Jerry sank that massive meat stick into me.
“Fuck, that’s so fucking cool.” Audrey gushed. “We should be filming this.”
“He’s already filming it, babe. Didn’t you notice the camera feeds on the laptop?”
“What?”
“Yeah, he had two cameras pointed at his ass. I had to move one of them, but the other is right there.”
Jerry’s cock bottomed out, and he held it there and ground in a circle for a minute.
“Fucking hell! He took the whole thing.” Audrey was clearly impressed. “Where’s the camera you moved? I’m gonna get some closeups when you start thrusting.”
“It’s behind me on the floor. It appears to be wifi and battery powered – it doesn’t have any wires.”
Audrey popped off my back, and I felt lube running down my crack – Jerry was apparently adding more lube before pulling back out.
I watched the cam feed, and Audrey was now holding the camera directly above my crack and Jerry’s cock. But it was too close, and the image was out of focus.
I grunted and torqued my head towards the laptop, hoping they’d get the idea.
Jerry was a pretty quick study, “I think he’s trying to tell us something, Aud. Maybe the camera’s not working or isn’t in focus. Maybe check the laptop.”
I nodded vigorously. Way to go, dude.
Audrey padded over to the laptop and pointed the camera at the floor. She moved it down until it started to go fuzzy, then pulled back. Repeating the process several times, working out the focal distance. Satisfied, she moved back behind me.
“Is it clear now, Dawn?”
I nodded.
“Awesome. Okay, babe, start sliding that monster out of her cunt, and I’ll film it, but go slow – I want a real show.”
Jerry started pulling back out, slowly, inch by agonizing inch. My sphincter skin pulled along his shaft like a foreskin.
“Fuck, look at his ass stretching and clinging to your cock. It’s like he has pussy lips. That’s the hottest fucking thing I’ve ever seen. Pull it all the way out! I want to see if he gapes.”
“Nah, if I pull out now, we might not get it back in. But later, when the bitch is loosened up, we’ll go for the gape, K?”
“Sure, that works. So get to it, rail the sissy cunt, babe. Fuck the shit out of her!” Audrey was really getting into referring to me as a girl.
Jerry had pulled out until just the head was in, and now he changed direction and slowly started pushing his magnificent cock back into my ass. Slowly, steadily, each bump and vein rubbed across my overloaded nerve endings. I didn’t know if he was a master at this, but he was doing exactly what I needed. His movements allowed me to bask in the glory of his cock. I would gladly bow down and worship this monster.
“Fuck, babe, you were right. He really loves this.” Audrey exclaimed
Audrey was still holding the camera over my ass, giving me an incredible view of Jerry’s cock attempting to split my boi-pussy open.
“Shit, he’s so fucking tight. It feels awesome. Are you sure you don’t wanna try this sometime? I’d rather fuck your ass, you know that, right?”
“Nice try Romeo. Not fucking happening. I don’t want my asshole torn up and leaking shit.” Audrey chastised.
I saw Jerry shrug in the cam feed. Nice try, indeed. I would have laughed if I wasn’t so consumed with fucking pleasure.
Jerry started to pick up the pace, slowly but surely, building up speed. Adding more lube as he went. Audrey continued to film while I moaned and mewled into the gag. Great gobs of drool ran around it and pooled on the towel below my chin. My brain was on fire from the action, and I would have loved another hit or two from the poppers bottle to amp it up even more.
I must have lost focus for a time, Audrey’s legs were in front of me, and the sound of the video had disappeared.
Audrey squatted in front of me, knees spread wide, her dripping pussy splayed open before my face, it was a glorious sight, and I stared lustfully.
Her finger came under my chin and lifted my face slowly toward hers. I took in her amazing twenty-year-old body in all its glory as my view panned up her body, my eyes finally focusing on hers.
“Enjoying the view, Sissy?”
I nodded enthusiastically and moaned as Jerry spanked my ass. “Stop staring at my girlfriend’s pussy you perv.”
I tried to smile, but that’s tough to do with a gag in your mouth. But I think Audrey noticed as she smiled back at me.
“If I remove the gag, do you promise to behave and not freak out? If you start yelling or demanding we stop, the gag goes right back in, understand?”
I nodded again. Fuck, yes, Audrey’s gonna take out the gag.
She reached behind my head, undid the gag straps, and worked it out of my mouth. Once out, she dropped it on the towel.
“Thank you, Mistress. May I have more poppers?”
“Mistress? Oh fuck, I like that. Hear that, Jerry? I’m Mistress Audrey. You better not fuck with me now!” And she laughed.
She brought the popper bottle to my nose, and I inhaled deeply. Three deep long draws for each nostril – holding it for about ten seconds. Woah, maybe too much – the room was almost spinning, and my eyes lost focus momentarily. I shook my head, trying to clear it.
Audrey’s pussy came back into view, and I smiled. Jerry’s reaming of my ass seemed less intense but oh so fucking pleasurable. But I needed him to pick up the pace. I needed him to really start pounding me.
“Please, sir, fuck me harder. Rape my sissy cunt. Pound that big fucking meat stick into my pussy until I scream. Make me your bitch. I’m your cum addicted little fuck slut. Breed me. Rape me. Use me. Beat my ass. Fill me with your man batter, then make me lick your cock clean when you’re done. Please, Daddy, fuck me.”
“Oh, you lecherous little cunt. How fucking delightful. Daddy is it. So you really do want to be a girl. Well, you heard her, Jerry. Rape her cunt. Beat her ass red while you fuck her. Start long dicking her and pick up the pace lover boy. And start degrading her while you’re at it.”
“Come on, Aud, I don’t like dirty talk, you know that. It just seems so fake to me.” Jerry whined.
“God! Why are you so confident in everything else but such a whining pussy when it comes to dirty talk.” Audrey blew out an exasperated breath.
Jerry didn’t respond, but he did start fucking me faster and started to slap my ass. Nice hard slaps. Sometimes with his whole palm, causing a delicious sting. Other times with just the heel of his palm, resulting in a solid meat tenderizing thump to my glute muscles.
He put one foot up on the table, causing his dick to change angles, and it really started rubbing my prostrate. His hands were planted on my hip bones, and he ramped up the speed. I began to yip each time he thrust forward and punished my prostrate. Short, high-pitched, girlie, inarticulate cries of pleasure.
“Oh, ah, unh, eh, aw….” Over and over.
“You love this, don’t you, sissy? You love Jerry’s big meat missile raping your sissy cunt. I bet you wish I had a big cock to fuck your pretty mouth, too, don’t you? Wouldn’t that be great? A cock in each hole. Spit-roasted like the sissy cum slut you are. Pounded till you blow your load all over the floor. Maybe I should put an ad up on Tinder, no wait, Grindr. Sissy cum slut in need of big cocks. No cock is too big. No holes barred. Guaranteed to clean your cock and swallow.”
“Oh, god, yes! That sounds incredible! Could that really work, Mistress? If it makes you happy, I’d love to service cocks for you.”
I was lost in a popper and cock-lust haze. I’d agree to anything. No thought of possible repercussions. If she could get me more cocks, I’d suck and fuck them all.
I pulled my eyes from her pussy and looked up into her eyes. She stared at me.
“You really would do it, wouldn’t you?”
“For you, Mistress, anything. Anything!” I raved. “I…” my train of thought shattered, “Oh god, yes! Just like that! Fuck me harder, Daddy!”
Jerry had changed up his rhythm again and was pulling out slowly and then ramming his cock back in like a battering ram. My eyes dropped back to Audrey’s cunt. Her fingers were covered in juice, exploring her folds and dipping in and out of her hole. She used them to gather some juice, and my eyes followed her hand up to her mouth. Our eyes locked as she sucked her fingers and moaned around them.
Jerry changed it up again. Now pistoning in and out like a jackhammer. As fast as any of my fucking machines, but with more force. The strokes were shorter now but deep in my bowels. His fingers dug into my hips and pulled me back with each thrust, slamming his hips into my ass.
Over and over. Even faster, if that was possible. My overloaded mind registered a guttural groan building in Jerry’s throat. He was gonna cum soon. The thought of him filling me, blowing his load in my pussy, sent me over the edge.
My brain and guts exploded. The orgasm was like nothing I’d ever experienced, maybe because I wasn’t in control and couldn’t stop the assault on my sissy cunt. A continual, low, strangled groan escaped my wide-open mouth. Audrey’s pussy drenched fingers invaded my mouth, adding fuel to the fire. My body went rigid as steel. Every muscle pulled at my bonds, trying to lift my torso off the bench and change the position of Jerry’s cock, which was now abusing my hyper-sensitive prostrate.
I wanted him to stop. I needed him to stop. But I couldn’t articulate words. I just kept groaning around Audrey’s fingers. Jerry continued to ream my overworked hole. In and out. In and out. I thought I’d lose my mind. I was having anal orgasms, one after another. Over and over.
It’d hit like a punch to the gut, causing me to clench and shake. Then subside for a few seconds, giving me a short reprieve. Then hit again.
Suddenly, my guts and sphincter clenched, and my pelvic floor muscles contracted and started spasming. My cock exploded and shot jizz all over the towels and the bondage frame. A sissygasm! Stream after stream of cum shot out of my cock. My ass tried to twerk against the bench as I shook and shuddered.
Jerry drove deep and stopped, slamming his hips into mine. Warm cum filled my over-stuffed cunt. He’d buck, squirt, and pause. Buck, squirt, pause. Over and over. It seemed to go on forever. I could actually feel my bowels filling. It was glorious.
Now that he had stopped abusing my prostrate, my mind began functioning. My mouth closed around Audrey’s fingers, and I greedily sucked her glorious pussy juice from them. Running my tongue around each digit. Not wanting to miss a single drop. I moaned my appreciation and pleasure and looked up into her eyes. God, I loved this woman!
Audrey smiled at me. It was a warm, almost loving smile and warmed my heart. She’d watched me fucked like a sissy cum slut and hadn’t rejected me. Heaven on earth.
I opened my mouth, and Audrey extracted her fingers. “Thank you, Mistress. Thank you, Daddy. That was the most amazing thing I’ve ever experienced. Thank you both so much!” I gushed, gasping for breath as I tried to articulate how much I loved them both.
Jerry had finished and was still buried deep in my cunt. “Whoa! That was pretty fucking epic. I’m about to pull out Aud. Wanna watch and see if he gapes?” He was clearly winded, sucking large gulps of air as he spoke.
Audrey patted the side of my face and stood up. I watched her tread back to Jerry, pick up the camera, and point it at my ass.
“Is your cunt in focus, Dawn honey?”
“Yes, Mistress.”
“Jerry, when I tell you, pull out real quick. Don’t give her pussy time to react. Dawn, try to relax. Don’t push, and don’t contract. Just let it happen.” Audrey directed.
I watched the cam feed. Audrey held her hand up in front of Jerry and used the same silent countdown you see on live TV shows, obviously trying to be sneaky. I smiled to myself but tried to remain relaxed.
When her hand made a fist, Jerry pushed off my hips, yanking his cock from my worn-out and abused cunt. I felt air invade my pussy, then my sphincter flexed several times and slammed shut. The feeling was electric. I grunted and groaned as another mini-orgasm rocked my world. It felt like someone had their hand inside my anal canal and was twisting and massaging. My guts and anal cavity clenched and flexed repeatedly. But it had worked. I’d watched on the cam feed and seen my ass gape momentarily, and it had been huge and epic in my mind.
“Wow!” Audrey and Jerry chimed in unison.
I watched as they high-fived one another.
“Should we let him up now?” Jerry asked.
I looked in the cam feed – they were standing beside the fucking machine, staring at my ass, Jerry behind Audrey, stroking her tits and pussy.
“I don’t know. I like the idea of being a Mistress. I’m not sure I want to let her up just yet.” Audrey purred.
I smiled. Perhaps my life was about to get exciting…
———–
If you enjoyed this, let me know if you’d like to know what happens next, I have some delicious ideas, and Don/Dawn has a pretty stellar dungeon.