Camboy's New Mistress

Story Info
Boy reveals his secret life as a crossdressing camwhore.
1.4k words
4
24.2k
18
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

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate.

He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs.

His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver hoop earrings were swinging back and forth underneath his wig with each thrust.

Daniel was a college dropout. Camwhoring is how he earned a living. At 5'6'' tall, skinnyfat and completely hairless, save for his crotch and armpits, Daniel was never popular with girls.

So he became the girl he always wanted to fuck with his laughable tiny dick. All those years of pent up sexual frustration eventually made him want to be the girl.. so that he could be the one GETTING fucked.

"You're not getting any pussy with that pathetic little baby carrot of yours. Hahaha. That's right, babe. Your little clitty should be locked up. In fact, I bought you a present. It's a chastity cage. I want you to put it on.

You are my bitch now. I want you to wear it 24/7. Yes, it looks so cute! You're finally right where you belong. I'll put the key around my ankle to remind you that you belong at my feet.

You will give me full access to all your credit cards, and you will do all the housework while I have fun with real men. If you're a good little slave, I'll even have one of my big black bulls fuck you.

That's right. From now on you will learn how to cum like a girl. This is how it's going to be.. for the rest of your life.. if you don't want me to divorce you and tell the police that you raped me. You do know what happens to weak little sissy rapists like you in prison, right?"

Daniel had been watching sissy hypno porn videos for years now.

He had nearly completely dedicated himself to the sissy lifestyle. No one knew of his ever-growing camwhore career. In fact, it had grown so well over the last year that he wanted to take it to a whole new level.

Daniel was looking for a mistress, and he might have just found her in the neighbor next door. And the best part was that he didn't even have to chat her up. She was coming to HIM. For the third time this week.

There were several loud bangs on his door. "YOU BETTER OPEN UP THIS DOOR RIGHT NOW OR I'LL CALL THE POLICE". She was dead serious. Daniel had been making way too much noise setting up all the lighting, moving his fuck chair around (the one he stuck the dildo on), as well as lustfully pounding the hell out of that dildo.

When he heard Antoinette's voice again, he became so hard that his dick protruded painfully from the small chastity cage pee slit. He wasn't even scared of her anymore. He was making so much money from camming that he could easily just shrug her off. In fact, that was Daniel's newest thrill. He WANTED her to see him as a girl, with his sexy leather corset, high heels, wig and hoop earrings.

He lusted after her so much that he dreamed of giving her full control over his earnings and the key to his chastity cage. He wanted her to dominate him on camera. He wanted to give her compromising videos of himself.

He wanted her to pound his cute boy butt with a huge strap-on for all his viewers to see. He dreamed of the day she would bring a big black hung guy and force Daniel to please him.

"I KNOW YOU'RE IN THERE. YOU AREN'T GONNA HIDE FROM ME ANYMORE. OPEN UP!"

He slowly approached the door, brushed his hair back to reveal his hoop earrings and smiled. He put his hand on the handle and took one last glance at his camwhore setup.

Two ginantic lamps were illuminating the fuck chair with the huge black dildo sticking out, all lubed up and ready to be consumed by his thirsty, well-worked butthole.

Daniel opened the door and just stood silent, ready to shock Antoinette into losing her words. Much to his surprise, she proceeded to carry on with her rant as if nothing ever happened.

"Do you know what time it is? How many times do I have to keep coming here at 2 AM and telling you to stop moving furniture or whatever it is that you're doing in there? I'm calling the landlord right now."

Daniel was mesmerized by her dominant nature and her well preserved middle-age body. Antoinette was as tall as him, had short ashy blond hair and brown eyes, wore glasses, had perfectly round, medium-sized breasts and a cute perky butt, in addition to a bit of fluff in all the right places. Daniel just stood there absorbing her cuteness with a smile on his face. The angrier she got, the more he liked her.

"Annie, I am sorry. This will not happen again. Will you please forgive me?"

Antoinette was already dialing the landlord when her eyes suddenly popped and she put down the phone. "How do you know my name?" Annie asked as she put her hands on her child bearing hips.

"I heard your boyfriend call you that yesterday." said Daniel in a calm, soothing voice.

"He's not my boyfriend. He's my brother, you little creep. And why are you dressed up like that? Are you with a customer? Is this what's been making all the noise? What are you hiding in there? Well, you're nosy so I might as well be nosy myself, huh?"

Annie pushed Daniel aside and entered his room.

"Oh my god, what the fuck?"

Now was his chance to tell her.. To tell SOMEONE about his secret.

"Please don't call the landlord. Let me explain, please? I can show you what I'm doing, just don't tell anyone."

Daniel's confidence suddenly turned to panic as he finally realized that the woman of his dreams was frozen with shock, staring at his camwhore setup with her mouth open. He closed the door, hands shaking. He wanted to make his career choice sound somehow prestigious to her, but the simplest truth came out of his mouth.

"I'm a cam model. People pay me to dress up as a girl and fuck myself."

Antoinette exhaled a chuckle that perfectly conveyed her mixed emotions of shock, pity and careful curiosity.

"S-so all this time you've been doing THAT.. a few feet away from me?" said Annie while making a circling motion with her finger aimed at his setup.

"Yes, I am sorry. I'm a huge weirdo and I should probably kill myself."

"You should." said Annie with a worried look.

"I make a sh*tton of money though." What was he thinking saying that? Tryhard. What a turnoff. He instantly regretted it.

"Yeaaah, I bet you do." Daniel could read the skepticism on her face. "I'm gonna leave now."

The thought of offering her hush money ran through his head, but he knew that would just creep her out even more and that she would really call the police this time.

Antoinette reached for the handle.

"Look, I know you don't like me and that you're probably really creeped out right now, but I think that underneath all that coldness lies a really sweet girl.

She paused for a moment.

"I thought that you'd be at a loss for words when I opened the door and you saw me in my full glory, but you proceeded to school me as if none of that mattered. You didn't even stop or go easy on me because of who I am or how I look."

She stood at the door, thinking for a few seconds.

"You're semi-decent at passing as a girl, I'll give you that. But you REALLY need to work on your makeup skills. And black nail polish? Please, you aren't fooling anyone."

Annie opened the door.

"Will you help me with that? I'll owe you dinner."

She was already outside, her hand still on the door frame. Daniel thought he'd blown it, but she put her head back in through the opening and smiled.

"Yeaaah suuure, and I'll bring my makeup kit."

Was she being ironic? What the hell just happened? Daniel was unable to process reality, then the door shut and pushed a wave of air on his face. It hit him. This really did just happen.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
mrwidehorizonsmrwidehorizonsalmost 6 years ago
Great start!

Lot's of potential here!

cdCindy1cdCindy1almost 6 years ago
Please continue

Great start. I can't wait to read the next few chapters

SamanthaSatineSamanthaSatinealmost 6 years ago
good read...

good read and hope there is more to come darhling xxx

Share this Story

Similar Stories

Social Media Star Boy becomes an unwilling lingerie model for online viewers.in Transgender & Crossdressers
Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
Hung like a Grape A small dicked Sissy is outed and humiliated.in Transgender & Crossdressers
A College Sissy Ch. 01 Freshman is feminized, used by male roommate and girl.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
More Stories