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23 Little Penises From 23 Little Virgins For Your Birthday (Emasculation Fetish)

23 Little Penises From 23 Little Virgins For Your Birthday (Emasculation Fetish)

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, Helpless, Weak. I Know You're Out There.

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, ...

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, Helpless, Weak. I Know You're Out There.

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, ...

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, Helpless, Weak. I Know You're Out There.

I Make Captions For Those Of Us Who Like To Feel Castrated, Emasculated, Humiliated, ...

The Husband Had Been Emasculated And Cuckolded When His Defiant Uppity Wife Had The Nerve To Run For Vice President, Without Asking His Permission First. Under The New Patriarchy He Ensures That Madame Vp Receives A Daily Beating As She Is Cleansed Of Her

The Husband Had Been Emasculated And Cuckolded When His Defiant Uppity Wife Had The ...

He Was So Turned On, It Didn't Even Occur To Him That The Woman Was Emasculating Him

He Was So Turned On, It Didn't Even Occur To Him That The Woman Was Emasculating ...

The Epitome Of Emasculation

The Epitome Of Emasculation

Gosh I Think I Just Found Out Im Into This Fetish. Theres Something About Being Called A Fag Or Gay That Turns Me On As Fuck

Gosh I Think I Just Found Out Im Into This Fetish. Theres Something About Being Called ...

Are You One Of Them?

Are You One Of Them?

Following Up To The Strip Club Story

Following Up To The Strip Club Story

Dress Up (X-Post: R/Sissycap)

Dress Up (X-Post: R/Sissycap)

But In Your Deepest Heart, You Knew Someone Was Gonna Do This To You Eventually

But In Your Deepest Heart, You Knew Someone Was Gonna Do This To You Eventually

All In

All In

Pussified Beta Faggot

Pussified Beta Faggot

The Video Title Sums Up My Goal As A Mef

The Video Title Sums Up My Goal As A Mef

Bullied By My &Amp;Quot;Girlfriend&Amp;Quot; And Her Friends, Just A Story I Wrote Around One Of My Pics :)

Bullied By My &Amp;Quot;Girlfriend&Amp;Quot; And Her Friends, Just A Story I Wrote ...

Are You Ready For Your Closeup?

Are You Ready For Your Closeup?

When They Recognize You For What You Are

When They Recognize You For What You Are

Pretty Much

Pretty Much

Hindsight Is 20/20

Hindsight Is 20/20

You Always Knew You'd Step On That Slippery Slope

You Always Knew You'd Step On That Slippery Slope

Sissies Bounce (X-Post: /R/Sissycap)

Sissies Bounce (X-Post: /R/Sissycap)

Mike Adriano Is The Alpha A Lot Of Us Probably Fantasize About

Mike Adriano Is The Alpha A Lot Of Us Probably Fantasize About

I Have A Massive Male Emasculation Fetish. This Is Me, Would You Say Im Doing A Good Job ? :)

I Have A Massive Male Emasculation Fetish. This Is Me, Would You Say Im Doing A Good ...

You Were Destined To Go Down That Road. Just Not So Fast.

You Were Destined To Go Down That Road. Just Not So Fast.

Wondering If Anyone Else Resonates With This

Wondering If Anyone Else Resonates With This

This Is What You What You Really Wanted To Happen, Wasn't It?

This Is What You What You Really Wanted To Happen, Wasn't It?

He Laughed, She Came, You Cried

He Laughed, She Came, You Cried

My Wife Gave Me A Pedi, She's Starting To Realize What All My Ex-Gfs Did And Its Fun But Scary

My Wife Gave Me A Pedi, She's Starting To Realize What All My Ex-Gfs Did And Its ...

Sissy Caption - Pushed

Sissy Caption - Pushed

Assume The Position, Loser.

Assume The Position, Loser.

How Could You Resist His Power?

How Could You Resist His Power?

Sissy Masturbation: Position One

Sissy Masturbation: Position One

Not Much Of A Life, Is It?

Not Much Of A Life, Is It?

There's No Going Back Now

There's No Going Back Now

Next Time, He's Gonna Make You Wear A Blonde Wig

Next Time, He's Gonna Make You Wear A Blonde Wig

Feminization Caption - A Single Mistake

Feminization Caption - A Single Mistake

Whatever You Try To Achieve As A Man, Two Things Are Certain: You'll Fail Utterly, And You'll End Up Here

Whatever You Try To Achieve As A Man, Two Things Are Certain: You'll Fail Utterly, ...

I Love The Idea Of Something Like This Happening To Me

I Love The Idea Of Something Like This Happening To Me

Sissy Caption - First Deposit

Sissy Caption - First Deposit

Meme I Was Referring To

Meme I Was Referring To

No Matter How Hard You Pretend, You'll Never Measure Up

No Matter How Hard You Pretend, You'll Never Measure Up

Deep Down, You Know Your &Amp;Quot;Masculinity&Amp;Quot; Is A Fraud

Deep Down, You Know Your &Amp;Quot;Masculinity&Amp;Quot; Is A Fraud

Spoiler Alert: Because It's What You Deserve

Spoiler Alert: Because It's What You Deserve

Tg Caption - Coming Home

Tg Caption - Coming Home

Crossdressing Caption - Women's Studies

Crossdressing Caption - Women's Studies

This Absolutely Is How You Will End Up

This Absolutely Is How You Will End Up

What's Going To Happen To You And The Reason Why

What's Going To Happen To You And The Reason Why

Dick Shrinking: How To

Dick Shrinking: How To

Sissy Anxiteties...

Sissy Anxiteties...

Tg Caption - An Easy Choice

Tg Caption - An Easy Choice

Forced Sissy Caption - A Long Night

Forced Sissy Caption - A Long Night

You Can't Hide From Her

You Can't Hide From Her

It's Better To Be A Sexy Woman Than A Weak Man

It's Better To Be A Sexy Woman Than A Weak Man

A Common Story (Xpost From R/Sissyperfection)

A Common Story (Xpost From R/Sissyperfection)

After Weeks On End Of Being Hounded By The Single Moms In The Gym Locker Room, Elise Reluctantly Switched To The Men's Section. At Least Over There They Would Feel Too Emasculated To Harass Her. Well... Most Of Them Anyway.

After Weeks On End Of Being Hounded By The Single Moms In The Gym Locker Room, Elise ...

Tea Parties Are Inherently Pretty Emasculating, But Your Little Sister's Friend Made Sure Of It When She Suggested Making It... &Amp;Quot;More Fun.&Amp;Quot;

Tea Parties Are Inherently Pretty Emasculating, But Your Little Sister's Friend Made ...

Emasculated For Your Pleasure

Emasculated For Your Pleasure

First Time Upload &Amp;Amp;Amp; Sissygasm After Being Locked In Chastity For 3Days, Teased With Hypno, Please Call Me A Sissy And Emasculate To Keep Me Motivated!

First Time Upload &Amp;Amp;Amp; Sissygasm After Being Locked In Chastity For 3Days, ...

Not Your Typical Emasculated Gay Sissy

Not Your Typical Emasculated Gay Sissy