“You either get a pink slip (and walk out the door) or you get a pink slip, put it on, and wear it to work tomorrow.”  That’s what your new boss tells you and you have no choice. You go to a department store, and find a pink slip that fits, and wear it to work….


Fashionista, Dear Madam, Missing Panties


Your rich society aunt leaves you her fortune. . .with one catch. You must take her place as the Dress Critic for the Oscars. Once a year, on Oscar Night, you must present yourself as a fashionista-critic and comment on the dresses worn by the celebrities. In preparing for this yearly role, something happens…


One day, as you are writing a letter to the local utility to complain about their terrible service, you realize how  you would write a very different letter to  a Sir, than to a Madam. You realize that your letter to a “Madam” is much more polite, considerate and forgiving…. You get an idea.


The thing you resent most about your new condo is the fact that there is no washing machine or dryer in the condo. Instead there are little “laundrettes” at the end of the hallway where all the condo owners do their laundry. One day, as you take your clothes out of the dryer, you discover a beautiful pair of pink satin panties….  You hide them underneath your towels and bring them home. From that day onward, you wonder who the panties belong to. Every time you see one of your female neighbors coming or going you ask yourself whether the panties belong to them?


Little Sissy Humiliation & Punishment

“Ryan what are you doing out there? Get out of the pool this minute! Don’t make me come in there and get you. oh my god……….. look at you. are you naked? I am furious with you! how dare you go skinny dipping little boy. Don’t bother to cover that little thing up! You wanted to be naked so hands off your little pee pee. awww look how shriveled you are from the cold water sweetie.”

Little Penis

You would think having a bald little baby penis would prevent you from doing these silly things. what am i going to do with you? ill tell you what, the problem must be your bathing suit. yes you need a new one. one that is more appropriate for my little sissy. I’ve got just the thing for you.

You stay here. i don’t care if the neighbors can see you. here we go! yes dear your sisters little little pink and purple polka-dot bikini!!! Im sorry baby i cant help but laugh at you! You are going to spend the rest of the summer in this tiny little bikini. Yes honey the top and bottom.

Bad Little Boy

And by the end of the summer you are going to have the cutest sissy tan lines ever. Awww don’t cry baby ryan. This is your punishment for being a bad little boy. Just think how funny you will look on the beach getting your bikini bottoms pulled down for a spanking by your mommy in front of everyone . Your little weener is going to be on display quite often this summer, honey. I’ll be walking you up and down the beach and you will be crying like a little sissy school girl won’t you.

Now when our day at the beach is over and its time to go home, we will take off your bikini while we are in the cold water to rinse it out. Then you can hold mommy’s hand and walk up the beach naked, everyone will see your little ass jiggling up the beach, and know that your mommy is humiliating you. Most of the time your naked ass will be bright red from all the public spanking you’ll be getting. You know what that cold water will do to your tiny little balls.

No one will even be able to see them they are so small. When we get to the outside shower area mommy will wash you while you stand there bare ass naked. Don’t you dare try to cover your hairless penis or you will be punished right there with an anal fingering in front of everyone. We are going to go to the beach every day this summer so get used to it.

Making Mommy Mad

Any time you make mommy mad I’m going to take your little bottoms away from you for the rest of the day! Then I will measure your tiny pin-dick, and post it on line for everyone to see!  understood?

And sweetie, every Saturday you will go to the beach with your big butt plug in. and everyone will be able to see the outline of your plug through your tiny bikini bottoms! If anyone asks tell them that your mommy makes you wear it as part of your potty training.


On to tonight’s punishment. tonight your aunts and your sister will be joining us for a special punishment for you. Honey i know your sister has never seen you naked or punished but its time that she did. I know you’re worried she will tease you about your little baby pee pee! I’m sure she will laugh at you just like the rest of us do. Once she sees you have a hairless baby dicky she will want to babysit for you. And wouldn’t she  just love to give you a bath, dress you up in your little girly clothes, change your diaper? Then take you to the beach to show you off to all her friends!

As you can see this cup has a little warm soapy water in it.  Mommy is going to mix this all together and pump it all in your bottom with this turkey baster. Once your bottom-hole is all full you will pull your panties up and start your house work wearing your french maids outfit.

The feeling of that warm cum oozing out of your asshole and staining your panties is going to degrade you very much. when our family members arrive they will all start to notice that you are leaking cum from your butthole and have a big cum stain in your butt-crack — and they will know that mommy has punished you hard.


Once your chores are done, you will be hoisted high over my knees for a spanking so all the young women can see the results of your dildo-ing: a raw and reddened bottom-hole with cum slowly oozing out. Not to mention your tiny raw shriveled penis. Baby, for the rest of the night you will be laying over the arm of the couch, ass in the air, panties around your ankles with the big black dildo stuck up your ass.

If that rubber cock slips out, we will start this entire punishment all over again. Every time it starts to slide out we expect you to reach around, spread your cheeks and push it all the way back in your exposed backside. Ryan you have a long night of fucking yourself in the ass ahead of you. Your poor bottom-hole is going to be so sore! Your sister will bring her camera, we need more pictures for your display on the fridge

Fated for Femininity

As a lawyer, it is not unusual for you to speak out and defend women. One day, a female client decides that you are not really a man, and that is why you are so good at your job!

One day after your father remarries, you are removed from your all boys school and enrolled in a school of your stepmother’s choice. She wants you to learn how to be dainty and feminine. And so you do!

Your wife has gained lots and lots of weight and so began to wear your clothes. At first just at home, and then to work, too. To get even, and also because you were running out of your own, you borrowed hers. Every passing day you found yourself becoming more feminine in actions, dress, and conversation.

Sissy Phone Fantasy Sessions (Mothers, Wives & more….)

Two mothers teach their sons about being girls.

Chrissy’s mother tries to stop her daughter
from marrying a cross-dresser.

After your wife has an accident, you are forced to fill in for her at the Bed & Breakfast you run together — as Hostess and Housekeeper!

As part of your psychotherapy, you are asked to live out the “ideal marriage,” — by
putting yourself in your wife’s shoes…also her panties, nighties & evening gowns

Your marriage is falling apart until your marriage counselor tells you to switch roles.

Destined for Dresses!

The story of what happens to you and your next door neighbor when both your wives
sign you up for a Charity Fashion Show.

Now that you’ve retired, your wife volunteers you out to her Nail Salon — as an after hours maid! Will you find happiness?

After a problem with a girlfriend, you are sentenced to 9
months of dressing like a girl. Your mother decides she doesn’t mind having a daughter! Your girlfriends hands you back to your mother, thoroughly trained.

Your landlady rents a room to a cross dresser and
finds him to be the perfect boarder. . .She decides that all her boarders can either leave, or stay and live as girls.