Exposed by My Own Hubris Pt. 01

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Young man is blackmailed into being a full-time sissy.
1.6k words
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On this early Friday evening, I was eager to start my week-long vacation.

After filling up a 2-quart enema bag with warm soapy water, I hung it on a hook next to the shower head.

Kneeling in the bathtub, I lightly lubed the long nozzle tip, then slowly inserted it into my rectum. Confident that it was secure, I bowed my head down, then reached over and released the clamp.

The sound of water rushing down the tube excited me as it filled my abdomen.

With my right hand, I held the nozzle in place.

A few times, I felt the urge to release, but I tightened my rectum each time.

Once the bag emptied the warm soapy liquid inside me, I sat on the toilet as my bowels emptied soapy water into the toilet.

Before taking a shower, I stood in front of a tall mirror and examined my body. I never liked having body hair and being on my own; no one would question why I had it removed.

"No body hair. Damn, that hair removal foam is great."

Four weeks ago, I tried a new hair removal foam recommended on a Reddit group. The company claimed that its product would slow or even prevent hair growth.

When I tried other hair removal products, my body hair would regrow within twelve days.

I took a long hot shower, padded myself dry; applied skin moisturizer to my body; then headed to my bedroom.

Over at my dresser, I had laid out my toys and clothing the night before.

The first thing I put on was The Holy Trainer, a pink chastity cage. Then I put on a black shoulder-length wig. Next, I put on a pair of white stockings and a white garter belt to hold them in place. My next outfit was a pink satin baby doll. After adjusting my stockings and garters, I put on five-inch heels with lockable straps.

After locking the high heels, collar, wrist cuffs, and ankle cuffs, I placed the key to the side.

Satisfied that the locks were secure, I lubed a large metal butt plug. Closing my eyes, I slowly insert into my rectum. I took a few deep breaths to relax. When it passed the wide base, the butt-plug easily slipped inside me.

The last two items were a ball gag and VR goggles.

I grabbed the last two items along with the keys, then walked back to my bed and climbed on top.

I loved how the satin baby doll brushes against my soft skin as I walked.

I placed the keys to my chastity cage, collar, wrist cuffs, ankle cuffs, and heels into the bin. After closing the lid, I turned the dial until the timer read 8 hours.

In the past, I gave in to my urges too quickly and would always unlock myself after 40 minutes.

The time lock bin will put an end to any temptation.

I took a deep breath and pressed Start on the timer.

A leg spreader bar was at the foot of the bed; I then attached the ankle cuffs. Then I placed and secured the ball gag in my mouth.

Grabbing my cellphone, I unlocked the Secure Folder, which had a hidden app. The butt plug that was inserted inside me operated on Bluetooth technology. And the app that I installed had various settings, from sensual vibrating to mild electric shock.

From the options, I selected sensual, then selected a five-minute delay, and set the duration timer to eight hours.

After pressing Start, I put on the VR goggles and turned it on.

The hooks were extra large, making it easier for me to hook and unhook the wrist cuffs while still giving me the feeling of being restrained to the bed.

The butt plug vibrated, as my pre-selected porn captions and videos played on the VR goggles.

To set the mood, sissy and chastity captions would play for about three and a half hours, then it will transition to short videos of Mistresses talking to you about being locked in chastity cages, and finally videos of sissies being fucked.

The feeling of the butt plug vibrating against my prostate was getting intense, especially when the butt plug changed from low sensual intensity to high sensual intensity. I wanted to jerk off, but fortunately, the keys were in the time-locked bin.

My first ruined orgasm was intense. I felt my cum oozing against my leg.

When the feeling subsided, I wanted to get out of my restraints. But kept telling myself to endure being restrained. To know what it felt like to have no control, to surrender all control. Besides, I couldn't use the keys since they were in the time-locked bin.

I nodded several times as the short videos of Mistresses talking about locking me in a chastity cage. Can you imagine if they saw me in my current situation?

Then the playlist transitioned to videos of sissies being fucked. The first video was a sissy dressed in a pink puffy sissy outfit, wearing a pink chastity cage like mine. She was lying on her back, her wrists handcuffed together. While lying on her back, a muscular man with what looked like a ten-inch cock was brutally fucking her in her ass as she kept yelling.

"Yes Daddy, fuck me, Daddy. Fuck me hard, Daddy. Be rough with me, Daddy."

This video turned me on more than the previous videos and captions. Was it the model? Was it the outfit she wore? Or was it the male model who was fucking her?

I felt my cock stiffening against the chastity cage, as the vibrating butt plug changed to high intensity.

As the video showed the muscular man being rough with the sissy; I tried to yell fuck me, fuck me, but the ball gag muffled my words.

Frantically, I kept arching my back up and down, while trying to yell, fuck me, fuck me.

At some point, I must have passed out.

When I came to, a different video was playing. It was a sissy dressed as a schoolgirl, on her knees with six men standing over her, stroking their cocks.

The video didn't show who, but you heard;

"Don't you fucking swallow until I tell you?"

She nodded as the other men filled her mouth with their cum.

The camera did a close-up of her face; her mouth was wide open full of cum. As she gargled the cum, a voice told her to swallow.

She swallowed with a big smile on her face.

I squinted and noticed that there was an hour left.

Part of me wanted this to end, while another part of me wanted to continue.

I must have had one or two more ruined orgasms. The VR goggles turned off and the butt plug stopped vibrating.

I unhook the wrist cuffs from the headboard, then removed the VR goggles and the ball gag.

As I caught my breath, I unhooked the ankle cuffs from the leg spreader. Turning to my side, I removed the butt plug.

Slowly, I stood up and took small steps as I walked around my bedroom. I noticed some cum stain on my stockings and satin baby doll outfit. I'm sure it will come out.

Taking my time, I made my way to where the time lock bin was. The timer flashed at 00:00. I was about to open the lid, but briefly paused.

Maybe I should try to do another six, twelve hours, or even twenty-four hours?

"Baby Steps, Baby Steps."

After washing the butt plug and placing it on the charger. I opened the lid, took out the keys, then unlocked the collar, wrist cuffs, ankle cuffs, and strap for the heels.

As I slipped off the 5-inch heels and stood on my feet, I felt a sigh of relief. I enjoy wearing heels.

The last thing to unlock was the chastity cage, and as I removed it, my cock was half erect.

I felt the urge to jerk off. I logged into my computer, opened my folder containing my porn collection, and jerk off to the first photo; it was a caption of a Mistress saying to lick cum off her boots.

"Yes! Yes! I...I'm cumming, I'm cumming"

Four months have passed.

About two months ago, HG8 Company laid me off as one of their project managers. The severance package I received was decent.

During this time, I balanced job searching and exploring my feminine side. On some days, I would search online for work while dressed as a sissy maid or dressed in just some sexy lingerie.

Last week, I received a call for an interview with a small company. While the salary was nowhere near what I was making with HG8; they offered a hybrid schedule and a lighter workload.

I stood in front of a tall mirror; satisfied that my suit looked perfect, I grabbed my attaché case and was about to head out when I got a text message.

"Hi. Is this Candy?"

After a brief pause, I texted they had the wrong number.

"Are you sure? Candy Lace born on 10/7/2004?"

That text message gave me an unsettling feeling, but I tried to play it off.

"Look, I really think you have the wrong number."

"Oh! I don't think so."

Just then, a text attachment came in. When I tapped to open it, my eyes widen my heart felt like it skipped a beat; it was a photo of me dressed in a pink sissy outfit.

My hand trembled as I tried to reply.

"Hw..hw di u ge photo?"

"LOL... I found your flash drive."

Flash drive??.... Flash drive!!

About two months ago, I took a risk and copied a few photos of me in different sissy outfits with contact information onto a flash drive. Then left it under a bench in a public park. I would never imagine someone would insert a flash drive that they found in public; into their computer.

I texted back.

"What...what do you want from me?"

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  • COMMENTS
6 Comments
4Leather4Leather8 months ago

Knowing that he’s fucked now. Waiting for the controlling / blackmailing text to arrive. Please the next chapter. Need to see witch rabbit hole you lead him down.

Tinytim123Tinytim1238 months ago

Great start to the story. Very well written and the "cliffhanger" ending is perfect. I agree with Failedscout; I also hope the blackmailer is female. PLEASE keep writing this one!

KatiwantsKatiwants8 months ago

Mmmmmmmmm mmmmmmmmm such a wonderful story!!!

jleetechiejleetechie8 months ago

He's got the toys and now the blackmail takes over. Hmmm...female domme might be entertaining.

SamanthaSatineSamanthaSatine8 months ago

Hot sexy start and left in limbo and anticipation of what comes next or even cums nest darling xxx write more soon?

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