Crazy Sex Stories: Sissy Boy Humiliating My Little Brother*

Crazy sex stories are so much better when they’re close to home

I love crazy sex stories, and they’re so easy to have when you can find inspiration from home.  There is truly nothing that really pleases me more than crazy sex stories of sissy boys, and treating them like the little faggot fairies that they are.  The first time this ever happened I found my brother in my best pair of satin panties, walking around in my heels like a naughty slut when I had come home from school early.  This behavior did not go unnoticed — or unpunished.

See, if you want to dress up like a dirty whore, you’ll be treated like one, too.  Panties and stockings and heels?  That’s for the tame, and you want to go all out, don’t you?  Be like my brother, the good sissy boy.  He was so red in the face, so I quietly shut my door and spoke softly: “It’s okay babe, we can make you a real girl.”  Now, this is where all the fun is when playing with sissy boys.

Lucky for him, I had the matching bra for those panties.  A good first layer to pretend you have a real pretty pussy and beautiful, natural tits like I do.  Next, I thought a nice button-up shirt, tied right up under his wannabe tits, and a short denim skirt with his tiny little cock peeking out from the bottom.  We could tuck it to make a man pussy, sure, but his cock was so pathetically little it was almost as if he had a real girl’s clit.

We could tuck it to make a man pussy, sure, but his cock was so pathetically little it was almost as if he had a real girl’s clit.

Kept some thigh-high stockings, traded out the heels he had chosen for something a little more outfit appro pro, and painted his face like a real whore.  Blue shadow and bright red lipstick, now aren’t you a pretty girl?  I was so proud of my creation, and I saw tears in his eyes as he realized how pathetic he looked, and how badly he wanted it.  Last step of feminizing you?  Penetrating what you wish was a pussy.

While he was ogling himself in the mirror, I wasted no time slipping my little buttplug into him, stretching his asshole the way he always imagined.God, that’s fucking hilarious.  Why keep the fun to myself?  I heard my sister and her friends laughing in the living room, so I gently pushed him towards my bedroom door, opened it quickly and gave him a shove out — in the direction of the laughing, which was now a mixture of shock and literal uproar.  What a pathetic wannabe cunt, am I right?

And yourself?  I’m sure we can find you a really pretty outfit to match that little sissy boy attitude you have been hiding.  Humiliation phone sex can be a new form of sex therapy for the simple of mind like you.  Do you listen to Shania Twain?  I can have you saying, “Man, I feel like a woman.

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