Making Sissy Dreams Come True!

One of the great pleasures of My profession is taking a boy’s fantasy, and helping him realize it as a reality. This is not always possible, due to some of the more freakish imaginations I’ve encountered. However, every once in a while, I come upon a boy that simply needs My controling helping hand. ~laughs~

SissyMaid is just such a boy. Indulge Me for a moment while I give you a bit of history to lay the groundwork of this story. Trust Me, it will entertain even the most ‘kink ingnorant’ readers.

After over a week of tryin to contact Me for a domination session via Instant Messenger, I finally got to talk to SissyMaid. He told Me about his fantasy. You see, he’s a sissy boy that longs to be controlled by a dominant woman, who is willing to use him in the capacity of a cuckold. He knows better than to expect this woman to use him in any sexual manner (other than, perhaps to “clean up” after her dates with real men). He simply longs to serve her as any good sissy maid should.

He begged Me to make it impossible for him to back out of exposing himself to the “older, sexy single woman” that lives in an apartment downstairs from him. After discussing the possiblities, we agreed that the best course of action would be for him to prance his little ass (fully locked in chastity and dressed up as a girl) down to her apartment, and drop the keys to his chastity belt and locked on spike heels into her mail slot.

I had him attach a note to the keys that said “These keys belong to lavinia@ladyevilsdungeon.com if found please email Me, a man’s health weighs in the balance”.

Needless to say, not long after our session ended, I received an email from a woman in Germany, stating that although she didn’t understand why, she wound up with My keys mixed in with her mail. I wrote her back, giving her My boys phone number and apartment number, and asked that she please excuse his silly, clumsy nature, and have him come collect the keys from her. Of course I thanked her for her time, and asked that she please make sure that he comes to collect the keys, as she had been bothered by him quite enough already.

Soon after, I received another mail from her, stating that she had called, and she was confused as to why the bashful boy showed up wearing a sweatsuit and high heels of all things, trying to avoid her seeing his shoes. She couldn’t help but laugh at him of course, and asked who I was, and if this in fact was the boy from upstairs. ~laughs~

When I told the boy that I wouldn’t respond to her unless he paid for my additional services, he quickly thought better of complaining that he couldn’t afford it, and bought an additional session.

This page, dear reader, is the result of that session. This boy begged Me to post more pictures of his sissy ass on My website, because the humiliation it affords him excites him to no end. He also begged Me to reveal his fantasy of serving the sexy woman downstairs to her. This page, was in fact set up as a way of explaining this entire adventure to her.

Below are the pictures I agreed to post, as you will see, they are nothing to be ashamed of. Ever sissy should look this good when dressing to please their Mistress! Remember boys, be careful what you wish for! Lady Lavinia WILL make your most deviant dreams come true. This is better than DisneyLand!! ~laughs wildly~