Uncle Caught

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.

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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.

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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.

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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?