Self bondage gone...wrong? Pt. 03

This is part 3 of this series. It involves predicament, non-consent/reluctance, BDSM, cross dressing, etc. I hope you enjoy it! Apologies for not editing - I simply don't have time at the moment.

Over the past few weeks I had sent pics of me wearing every last stitch of naughty clothing that I and my wife owned to my blackmailing mistress. I'd also had to send images or video of me playing with every toy from my toy box.

"Finally! Last one," I texted her, a pic of my face, mouth pushed a bit wide by a large ball gag. Hey reply was quick - "ooh! I like that! Bring it to our playdate as well! ... Does it lock? If not, get a locking one!"

I gulped. I had recently acquired several new toys, including a posture collar (locking, of course), a still bigger butt plug, and now this. I was also not allowed to wear unsexy underwear. During our last playtime (again, it was me handcuffed to a pole in a park) I had been required to deliver all my unsexy undies and been measured for a custom cock cage because I had confessed that I could get off in mine.

I still got excited remembering - her quietly talking next to my hooded head, me now cuffed laying on a picnic table spread eagle. "Good job getting this in your ass," she said, pressing gently on the giant plug that filled my ass. I felt her unlock the cage, pull it off, then gently wash my member with a wet wipe. I swelled quickly - fully erect before she finished washing. She gave me a slow blow job - torturously slow, up and down while her hands twisted at my nipples and piercings, pressed on the huge plug in my ass, teased my desperate body...

As I was building slowly to a glorious orgasm, she opened my hood to expose my mouth and removed my gag . As I neared a tiny bit of heaven, she stopped, asked "is this your first since I caged you?" ... I said nothing as she continued teasing. "Be honest and you'll cum..."

"No mistress! I can cum in the cage... It's not great, but..."

"Mmm. Good slut," she said, returning to my stiff member. She slowly carried me to the edge, then pushed me over into bliss. I felt spurt after spurt fly into her mouth, until I finally lay spent. My mouth was slightly open, breathing labored after cumming. She climbed up my body, pressed her lips to mine in a passionate kiss - I returned it, her mouth opening mine, her tongue forced it's way into my mouth, along with every drop of my cum! I coughed as it hit the back of my throat, started seeping down. She sat up, forced the ball gag back in, buckled it.

"No more cumming without permission, slut. I'd better measure you for a cage you can't cheat... Swallow or don't - either way you get to taste it for a while." So now I knew that the next time we "played" I'd be completely locked away...

Buzz! A new text pulled me from the memory. "Are you excited for next week?" Despite my status as blackmailed slut, I was! My wife had business and grandparents would have the toddler for 2 nights! I replied "Yes...?!". I loved and hated being exploited like this.

"Gooood. Start imagining how it will feel to walk the park trail in your sluttiest outfit, slutty makeup, high heels... At 7 p.m. ]:)"

I froze. People would see me!

"What's wrong, honey?" My wife asked, noticing my expression. "Na-nothing," I said. "Just remembered work I forgot to do..."

"Oh. Can you give the toddler a bath?"

"Sure." I felt my phone buzz in my pocket, and was aware I couldn't check for a while...

The toddler kept me busy until her bedtime, so the message sat unread, teasing and terrifying. Finally my wife and I sat in the living room, playing on our phones, and I read: "the best part is you standing at the crossroads trailhead, holding a big sign that says 'honk 4 sluts' ... With your hood locked on, hands cuffed, waiting for your ride ]:)"

I chew on my lip subtly, trying to be sure that my wife won't notice. Reply to the text with "mmmmmm...", simultaneously terrified and aroused.

"You know," my wife says, interrupting my thoughts, "you've been wearing a lot of sexy underwear lately," my phone buzzes as she talks, "I can tell you're really horny - I could throw you a bone... A boner?" She said smiling. Oh shit! What to do? ... I decided to play it cool.

"I'm in such a naughty mood - I'd sure like to please you, but not get an orgasm out of it," I said smoothly, biting my lip in a sexy way.

"Are you sure?" She asked hesitantly. "Ohhh yes," I growled.

I slipped her shoes off, lifted her legs up on the couch, and started massaging them. When she was good and relaxed I started running my hands up and down her legs slowly, sensually, until she purred. Then I slipped her pants off, kissed up her legs, finally removed her panties gently with my teeth. Kissed back up her legs, settling my head between them I began to lick-long strokes up her intimate lips, then back down, each lick a bit closer to the middle, until my tongue found her creamy center. I licked and sucked gently on her clit, then slipped two fingers inside her, started pumping as I licked. After a long, slow build-up she finally screamed in pleasure, squeezing my head between her thighs. "Ohhhh!"

Afterwards I covered her in a blanket and sat holding her. She was relaxed and content, but I was hornier then ever! At least I'd prevented her from finding I was caged ...

After our nightly routine, my wife and I climbed into bed. I waited for her to sleep - finally, I was able to sneak out of bed, grab my phone. I coated the next huge butt plug in a generous glob of lube and sat it on the tub edge, positioned myself over it and slowly began to impale myself. I moaned quietly as my ass stretched further then ever before. After a good session I still hadn't got the toy in, but it was important to not push too hard - ease it in further and further over several days was the best way.

I cleaned off, pulled my thong on and went to the living room. With my ass still sending pleasure signals, I checked my text message. "Well slut, I'm making so much bank selling your slutty pics to gay porn sites that I'm buying some fancy new toys. I'm excited to try them on you..."

I gulped. Had she really sold some pics of me?! Were they out there for all to see?!

"Really, Mistress?" I replied.

"Yes really, slut. Remember, you do what I want. Or do you want me to post pics w/ ur name and place of work?"

"No Mistress! Please! I'm sorry ..."

"Good, slut. It might interest you to know I'll be recording parts of our next play date ]:) ... Now tell me something naughty."

"My wife suspects something! I had to woo her and convince her I wanted to please her orally with no return favor! :( "

"Goooood. And you know you liked it. Has she seen the naughty background pic of you yet?"

"No Mistress! I try to hide it..."

"A Well, I'm going to send you a pic to make your lock screen... Maybe you'll have worse luck w/ it ]:) "

The pic came through - a picture of my upper body spread eagle and bound, a woman's pussy smothering my mouth, my hood covering the rest. I bit my lip but didn't put it on my lock screen.

"Is it on?" She texted.

"Yes Mistress!" I lied.

"Are you suuure?"

"Yes Mistress"

Another pic came thru - the blackmail one of my face, me on my knees from the day this all started. The text said "liar".

Suddenly my phone acted on its own, downloading the image and setting it as my lock screen and background!

A new text came in.

"Don't lie to your mistress - she always knows. You are in some trouble for disobeying - if you want to make it a lot of trouble, go ahead and change the image..."

I gulped. How the hell did she do that?! I replied, "Yes Mistress".

"One other thing slut. Start a list of things you like and hate - I can see I'll need to start handing out rewards and punishments. Bring it with you next week."

With lots of deviant kink to worry about, the time dragged. Would she really record me as she degraded and abused me? I bit my lip, my cock betraying betraying me and trying to harden in the cage. Finally the day came. I waved bye to my wife as she pulled away (we still weren't kissing b/c our marital problems), then drove the kid to our meeting with grandma. I kissed the kiddo and handed her off to grandma before hurrying to work. That day did fly by, until 5.

I ate some dinner, then prepped. Another full body shave to be sure it was all smooth. Then make-up and fiddling with my hair, trying to get it arranged like a woman - I usually just put my long hair in a pony tail. Working the huge new butt plug into my ever stretching ass. Finally pulling on all my clothes. I looked in the mirror. That girl was dressed like she wanted attention!

I had pre timed the route, and I didn't want to arrive early! Standing on the side of a road like this felt really risky, but doing it cuffed, gagged, and hooded was nuts! I meant to be there at precisely the appointed time, even if I couldn't control when Mistress would arrive...

I grabbed my little purse and headed out the door. Of course my neighbor was out! I waved back quietly, afraid to talk, and climbed into the car. Still light out... So people would definitely be judging me for my slutty look... I worried about every stray glance that came my way.

Driving wasn't half as bad as the park! There were moms everywhere, and I could feel their eyes on me as I clicked to the trail, carying a cute little purse and a big (folded in half!) sign.

Walking the trail to the road took longer in heels, and I hurried as best I could. When I finally stood in the cover of the last few trees before the road, I didn't really feel any relief - I was about to stand next to a road, cuffed and helpless while holding a sign that drew more attention then the outfit!

I quickly gagged myself, cuffed my hands, plugged my ears, then lowered the hood ... With great trepidation I locked the hood on. Now, I was locked up and only Mistress had the keys! I could feel my hands shake as I opened the sign! They continued to shake the whole time I stood there.

Honk!

Honk honk honk!

At least 3 cars had honked at me before I felt hands touch me. I jumped! I hadn't heard the person approach. Was it Mistress?! Someone else?! I had no way of knowing, but it didn't matter much b/c I had no way to fight - they grabbed the chain of my cuffs and dragged me several steps, then pushed me into a car. I was covered with a blanket, the door was closed, and after a long second the driver's door opened and shut and the car moved. I lay frozen with fear the entire ride - was this my Mistress?!

The car stopped several times - stop signs? Lights? After 7 such stops, including more turns then I could keep count, the car slowed to a stop, then rolled forward slowly, stopping before the engine was turned off.

I was roughly pulled out of the back seat by one person, pulled by my cuffs through a door, then slowly down steps ... Finally sat in a seat. My cuffs were removed, but then My hands were just cuffed behind me with the chain threaded through the chairs spokes.

"Mmmm, mmmm!" I tried to talk through my gag. My captor pressed my face against their pants - I felt a firm cock! I struggled like mad but only scuffed up my wrists on the cuffs. This person couldn't be Mistress - they just happened to have cuff keys! ... At least they couldn't unlock my hood ... But they would soon discover I was not a female! What would they do!

My panic was so high that I didn't notice my hood being unlocked. It was unzipped partly, my gag was unlocked, then a massive dildo was shoved in my mouth. I was face fucked hard and deep for several eternities, until finally the big dildo was pulled out of my gagging throat. My ear plugs were removed.

"Mmmm, I love seeing you panic. Mind fucking you gets me so wet."

She pressed her sopping wet pussy against my face, coating my mouth and nose in her juices. She ran her hands down my shirt, grabbing my nipple piercings, twisting until I screamed, then she lowered the chair, laying it on its back so that I was also laying on my back, still cuffed to the chair. She lowered her pussy over my face, saying one simple word - "lick."

She didn't climb off my face until her third orgasm, when I was gasping for air and nearly crying from the pain of how I was cuffed.

"Good girl," she said. "Now. I want you dressed in only your heels and thong, cuffed and sitting upright in the chair when I get back - understood?"

"Yes Mistress!"

She unlocked my cuffs, then I heard her leave the room. The door closed, and I heard a lock click. I slowly stood, removed the rest of my hood and the blindfold, and studied my surroundings. It was a room without any windows - a simple double bed (with metal headboard) was there, along with a bureau - locked - and a metal frame with anchor points strategically placed for tying a person in various poses. The door had a deadbolt which locked from the other side.

I gulped. No options here except obedience, so I quickly stripped as Mistress had said to. I sat the chair up on all 4 legs and used the cuffs to again secure myself to the chair.

I sat helpless, staring intently at the door. Mistress hadn't said to put the hood on, so I did exactly what I was told ... I desperately hoped it was right! The lock clicked and the door slowly swung open - my jaw dropped as she prowled into the room. She wore a cat mask, bright red lipstick highlighting her full lips and contrasting w/ the black mask. Her fuck-me heels accentuated her curves, fishnets wrapping around her legs, disappearing into the folds of her short, leather skirt. A tight leather corset pushed her ample breasts out - covering them, but zippers showed it was easy for her to free them. Her first order of business was to take my clothes and leave the room. She came back after a minute without them.

She stopped 10 feet away, letting me get a good look at her. My mouth was agape as she struck a sexy pose with her hips cocked, then did a slow, sexy turn - bent over so I got a good view of the back - her black lace thong just peaked out as her skirt rode up just enough for a reveal. She locked the deadbolt with a key from a chain around her neck, then deliberately looked into my eyes as she slid the key back between her breasts.

Her heels clicked on the floor as she walked purposefully to the bureau. She unlocked it, pulled it open and pulled out some equipment. I gulped as I watched her wordlessly set out a camera and mics. She was efficient in setting up.

"Now, slut," she said in a sultry tone, "let us see ... What is in this box," she pulled a large package from the bureau, carried it to a folding table she had set up at the same time as the camera. She looked at me like the cat that ate the canary as she pulled a dagger from a garter sheath I had not noticed, slowly slit the box open, the knife obviously very sharp.

Mistress pulled metal bars and boxes wrapped in styrafoam out as I watched with an excited uncertainty. She slowly unwrapped each piece, laid it on the table, and as she went I started to get a bad feeling - metal rod, a motor, a circular cog ... The final box came out - it was labeled, unlike the other boxes - it said "anal destroyer". I gulped audibly as she pulled the huge dildo out of the box

"Too much noise, slut" Mistress said, striding over and shoving the huge dildo in my mouth. She fucked my mouth enough to get some saliva, then inexorably pushed it down my throat - the - entire - 18 - inches. My gag reflex was not even able to work properly by the time she was done. From a little purse on her hip she produced a spool of bondage tape, which she used to hold the dildo in place.

"Sluts are best seen and not heard," she said, aiming the camera at my distressed face. "Now, I need to put this fuck machine together ..." I watched helplessly as she did, drool trickling down onto my chest, ass feeling uncomfortably full after hours of being stretched to what felt like the biggest possible gape.

Mistress had the machine together in no time - she had obvious experience with mechanical things, raising a new question - was she one of my co-workers? I knew several ladies about her size with that mechanical aptitude. Just one more thing to worry over!

After setting up, she approached me quietly, producing a posture collar from somewhere. She smiled at me as she unlocked one hand, then the other, an "I dare you" glint in her eye. I obeyed her unspoken commands, getting on my hands and knees in front of the machine. I stared at the hardwood floor as my arms were brought behind me and taped together from the elbow down. My feet were spread apart and shackled to the frame of the fuck machine.

"Push, slut," Mistress spoke as she tapped the big plug in my ass - the first words in several tense minutes. I pushed as she pulled and the massive plug popped out of my ass. "Ohhh - look how slutty" Mistress said, getting the camera and going close up on my gaping ass. Before it had a chance to really relax she had the destroyer lubed with boy butter and stuffed in deep. She turned it on and let it slowly fuck me while she flew the camera all around at various angles - focusing on my ass as the toy pumped relentlessly in and out, then on my face as I moaned in pleasure, then on my arms, now pulled up over my back by a rope, then on my face, now gagged with a massive ball and copious spit running down my chin ... The cum dribbling out of my caged cock, falling into a little bowl for later...

Just when I felt I could take no more, she set the camera down ... And began setting up a cushion at my face. She sat down with her hips right in my face, now sporting a well endowed dildo, and promptly gave me a good face fucking for the camera, followed by an eternity of culingulus.

"Ohhhhh yes!" She screamed around her fourth orgasm, her body visibly relaxing. The intensity of her pleasure triggered the strongest assgasm I'd yet experienced - it felt like a real orgasm! - which made me moan/scream into her pussy, revving her engine back up! She took the posture collar off and looked mischeviously into my eyes before turning her back end to me and spreading her nether cheeks.

"Come on bitch - more licking! If you do a good job I might play with your cock..." Despite my exhaustion I did my best to please her ass - an activity I was starting to like ... after her 3rd orgasm with me providing anal stimulation, she finally pulled away.

"Mmmm. Mistress is pretty satisfied for tonight. I'm feeling hungry, aren't you?"

"Yes Mistress!"

"Great ..." She said. I missed the evil glint in her eye as she blindfolded me. I heard her move around, the door open ... Eventually the door closed and I could smell glorious food! My stomach rumbled despite my ass's continued pounding.

"Open wide!" I did and recieced a spoon of salty cum. I obediently swallowed, knowing I would be punished if I didn't. I swallowed every drop of what she fed me. "Good girl. Wouldn't you like to know how many men helped make that cum?" She teased. I have a small moan of worry. "Bad slut. Now you get to entertain me while I eat."

I felt my poor arms finally lowered, but before I could get comfey, they were raised a bit, and I felt a chain being attached to my nipple rings. A little experimentation confirmed my fear - a rope and pulleys now connected my poor, exhausted arms to my nipples so lowering my arms would punish them! I let our a breathe of pain, and even that was too much.

"Tsk tsk," I heard. The huge ball gag went back in my mouth, and then mistress's feet went right under my nose. The mix of her carryout Chinese food with pungent feet was maddening - I couldn't even enjoy the smell of her food.

At long last my arms were lowered, the fuck machine turned off (my ass was so numb that I was feeling only the pressure of the fucking). I sagged into the floor, too exhausted to move.