A Sissy Slave's Autobiography Ch. 01

Story Info
A divorced man’s first step to becoming owned.
1.6k words
4.4
22.1k
12

Part 1 of the 4 part series

Updated 06/12/2023
Created 12/01/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

With a sigh, I sank down into my couch and cracked open a beer. I closed my eyes and listened, silence and the distance hum of a highway was the only thing I heard. I opened my eyes and looked around and saw no one. It began to sink in, I was finally on my own.

I recently got a divorce and just moved into my 'new' apartment, honesty it was anything but new. It was nothing compared to the beautiful house my now ex-wife and I used to share. But, it was mine, and a wave of possibility and excitement flooded over me.

I had pushed back my sexuality for 10 years, getting by on the horribly unsatisfying sex my ex and I had throughout our marriage. I couldn't please her, and she didn't want to be pleased. She couldn't please me, and didn't want to either.

Now, here on my own, possibility beckoned, my submissive desires began to fill my mind and body. My bisexual desires that I have denied myself for a decade were now possible.

I got up and closed all the blinds in my small apartment. I went into my bathroom and took off all my clothes. Looking in the mirror at my naturally feminine, skinny, hairless, shaved body and tiny cock. I smiled and whispered, 'you were made for this.' I dug through an unpacked box and found my favorite panties, a lacy black thong with "Victoria's Secret" written in bedazzled jewels on the waistband.

Striding back to my living room I laid down on the couch and took a long drink of my beer. I grabbed my phone and went to work.

Opening various apps and websites I began to put myself out there. I spent the most time on Reddit, uploading faceless pics of myself in my panties to various sissy, femboy, gay, and faggot pages. All with the same message...

"Recently divorced slave looking for someone to serve in real life."

I posted and posted and posted, then I waited....

Before long, I was met with various "hey sissy," "hey boy," and simply "hey," messages.

All the conversations were dead ends, not producing the real deep conversation I was looking for.

All night I texted potential masters without any luck, I video chatted some, send out what felt like hundreds of photos and videos of my smooth hairless body, endured quite a bit of humiliation and degradation (which I loved,) but didn't find the fit I was looking for.

After awhile I fell asleep, on my couch wearing nothing but my adorable black panties.

The next morning was Saturday, and I woke up to a message that would be the beginning of discovering my true self, looking back, it was the first day of my new life.

Here's what it said....

"Hi Adam, I saw your post and photos looking to be a slave for a real master or mistress. I think you have great potential, please respond with your details, are you available for a video chat interview today?"

This message was obviously entirely different, it was so formal, so 'nonsexy' it was like I was applying for a job at target and got an interview with the store manager. Something about this was... incredibly hot and intriguing, I quickly responded...

"Mistress, thank you for your response, I am 5'10" 175 lbs. I have short brown hair and brown eyes, I am recently divorced and in the greater Las Vegas area, I am looking to serve and submit to a master or mistress and do anything I can to please them, I am free anytime today, thank you."

I hit send and got up off the couch and wandered into my shower, I dropped my panties to the floor and turned on the water. When it was hot I stepped in. I touch up shaved my armpits, stomach and around my cock and balls. I couldn't help think how much better they'd look locked up in a tiny chastity cage. I'd definitely need a small one, I used to say I was a 'grower not a shower' but I really was neither. My cock was about 1 inch long soft and about 4 rock hard. It was, as the many men told me online "pathetic". I admitted it to myself years ago, but now I wanted to please someone not with my cock but with my mouth, asshole and devoted servanthood.

After my shower I checked my phone. The response was cold and made my heart sink. It simply said...

"Okay then, 2:00... video chat at this number..."

It was 10:00 now and the next 4 hours were agonizingly long. I was so nervous my stomach was in knots, I thought about backing out.

Finally, after an eternity and a mental whirlwind of emotion the clock said 2:00.

I didn't know what to wear or do, so I just wore gray sweats and a t-shirt. I sat down on my bed and called the number. I didn't want to show my face so the camera just faced down looking at my legs, bare feet and the floor.

I was shocked when a man answered. "Adam, thank you for calling," a stern yet friendly voice began.

My heart was pounding, I wasn't expecting a man to answer.

"Uh no problem," I said weakly.

The only way to describe the man in the video was... intimidating. He had to be older than me, I just turned 30, he was probably in his late 40's. He had wavy black hair and seemed strong and confident. He had icy blue eyes and a stubbly beard, he looked either like an important business man or an ice hockey coach. Whatever he was, he made me weak in the knees at the thought of worshipping his cock.

"My name is Greg, but you will call me sir, you spoke with my wife Amanda, you will call her ma'am."

"Uhh yes sir," I stammered.

"Now, turn the camera around and let me see your face," he said.

With my heart racing and my cock growing already in my pants I obeyed.

"Good boy," he said, "we can work with you, some makeup and you'll be a pretty sissy in no time."

"Thank you sir," I said, I was super embarrassed and not proud of my receding hairline, beard and frankly unremarkable features.

"Now, time for your interview," he continued, "prop your phone up so I can see your entire body and strip naked."

"Yes sir," I said and did what he commanded. Already feeling humiliated I put my hands over my cock as it was already getting hard.

"Hands at your sides!" He snapped with clear dominance. With those words it was clear who was in charge.

I obeyed and proceeded through the next 45 minutes of the most humiliating, invasive 'interview' imaginable.

Greg inspected every inch of my body up close, asking questions about scars and birth marks. He demanded to look at my cock, balls, feet, hands, my tongue, and of course, my ass. He spend by far the most time inspecting my ass. Making me spread my cheeks, inserting my fingers into my ass, spreading and opening my hole, he was clearly doing it so in depth to see how little self esteem and pride I had.

Lucky for him I had none. This in addition to my growing horniness which always brought the desire for humiliation, I showed him every part of me without hesitation. I just had a messy divorce that took most of my possessions and money. On top of it all, my ex wife ran off to Florida with some fancy real estate agent right after the divorce was finalized which of course left me with 0 pride and a nothing to lose attitude.

I was going to impress him no matter how degrading it would be.

He continued to ask in depth questions about my sexual history, desires, and limits. He asked about my job, my finances, my relationship with my family and much more.

At the end of it all I stood in front of him completely naked hands at my side staring at the floor and he said, "Amanda will be very pleased to hear all of this, I have been screen recording this entire conversation and will send it to her since she is away for business."

My heart dropped "uh please don't keep this sir! I don't want it to get out!"

I started to panic and began frantically putting clothes on.

"Stop slave!" He said the word slave and it hit me like a slap across the face. I dropped my pants and stared at him through the screen.

"The only way anyone besides Amanda or I will see this is if you ghost us or try to back out, if we agree this relationship is not a good fit, you can trust I'll delete the video but not until then."

So there it was. All my secrets, every inch of my body, everything about my mind and soul were there for this guy I just met to do whatever he wanted with. I had no choice but do whatever he commanded me to do and hope for the best.

Defeated and scared I said, "yes sir, whatever you want sir," and as those words escaped my mouth I noticed a little bit of precum leaking out of my hard cock. I didn't just want this, I needed this.

And with that he said he'd send me his room number at the Cosmopolitan on the strip and I was to meet him there tomorrow at 7:00pm with more instructions to follow.

I was about to discover how 'made for this' I truly was.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousover 1 year ago

need more to follow, b his slave

affinajosephaffinajosephover 1 year ago

Would have loved if Amanda had been a main domme and more cerntral role rather than a guy.

Adam_s5111Adam_s5111over 1 year agoAuthor

Thank you! Chapter 2 posts tomorrow and chapter 3 is pending, Thanks for the kind words!

AnonymousAnonymousover 1 year ago

Good start. Let’s see where it leads

Jaydean409Jaydean409over 1 year ago

Eagerly awaiting next chapter!!!

Show More
Share this Story

Similar Stories

Pretty boy to Sissy girl Married pretty boy enjoys being cuckolded.in Transgender & Crossdressers
White Dom Turned Sissy for BBC Alpha white man learns his inferiority to BBC.in Transgender & Crossdressers
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Not Careful Enough Ch. 01 A boy isn't careful enough and gets propositioned.in Transgender & Crossdressers
Caught by My Boss A closeted sissy gets careless and ends up exposed.in Transgender & Crossdressers
More Stories