Welcome to my blog, titled 'Owning My First Sissy', which is a real account of how I came to have a little sissy-boy willingly give himself over to me, to be dominated and humiliated. Allow me first to tell you the story of how this little sissy came to be my property.
One evening, the little sissy-boy had an idea. An idea to create a scenario where he could find a mistress who would help him to become the dirty little slut he so desperately wanted to be. Using a fake name, and posing as his sister, he logged into a chat room I happened to be using. He messaged me asking if I was dominant, and tells me that he is a girl who is furious at her brother for catching him jerking off onto her panties, that her brother treats girls like crap, and that he needs to learn a lesson.
"What kind of lesson?" I inquired.
"He needs to learn to treat women better. He should be humiliated and turned into a slutty girl to know what it's like" was the reply. Still posing as his sister, he told me that several items hat been left in a shopping bag in his apartment to get things started. Makeup, clothes, bras and panties, and a reasonably sized cucumber. I was asked to approach him on skype, pretending to be someone who knows his sister, asking about advice on football jerseys as a gift for a friend.
Continuing to pose as his sister, he tells me to say that I have pictures of him wanking into his sister's panties, and that if he doesn't learn some respect, I'll send them to his friends and family, unless he does whatever I tell him to, and asks me to please humiliate her brother as much as possible with the things she'd left, and the fact that I'm transgendered would be even more humiliating for him.
Suspecting that this is just a joke or a bit of role play, I decide to play along. I added the girl's alleged brother to skype, and he reacts exactly as I was told that he would. I tell him that I know what he's been up to, and that I have the pictures to prove it. At first he acts coy, but then finally admits to ruining his sisters undies, and then says (suppressing a smile) that he'll do whatever I want him to do, as long as I don't share the pictures (of which there are none).
I followed the script, and instructed him to grab the bag, show me the contents, and get pretty.
He tried to act embarrassed, and said he would only do it if he had to, but the excitement on the little slut's face was undeniable as the scenario played out exactly as his "sister" had told me, with him being "forced" to dress in girls clothes, underwear, and makeup, and fuck himself with a cucumber, as punishment for cumming into his sisters panties.
I'll save the rest of the details for another post, and skip ahead a little bit here.
A few evenings later, he messages me on skype, trying to act all macho and studly, and I decide that this would be a good time to tell him that the "girl" he's trying to hit on has a cock under her skirt.
He pretends not to believe me.
I tell him it's true, but he asks me to prove it. So I send a picture of myself fully dressed, but showing an obvious bulge.
He says that he still doesn't believe it, and that he bets that I've just stuffed something into my undies to look like a cock, to fool him. He goes on to say that if I prove that I'm not lying, he'll give himself to me as a slave to do whatever I want.
This is where I would like to remind everyone that he already knows that I'm transgendered, and is merely acting out his little sissy fantasy.
So I send him another picture, proving it undeniably, and he says "Well a bet's a bet, I guess you own me now...and I have to call you Mistress"
And thus the little sissy had managed to fulfill his fantasy, and give himself over to a mistress, to become the dirty little slut that he always dreamed of being.
