Sissy boy needs a little upgrade on his style.

He’s been visiting quite often and it’s not hard to tell how much of a pathetic sissy boy he is. I know exactly how to get this boy off. Soon I’m going to make him my cross-dressing whore! Of course, we are going to have so much fun and he has no idea!

He rang the doorbell and as a result, he handed me a plate of homemade cookies like he usually does. I grab him by the wrists and told him to follow me, I had a fun surprise waiting for him in the bedroom. We went all the way upstairs and into my room. On the bed was a set of blue lingerie. Blue lacey bra and some garters to go with it. I love Adult Chat!

Next, I tell him to put the skanky outfit on for me and with confusion in his eyes, he did what he was told. He was eager to find out what I had in store for him. Then, he tried running to the bathroom to change but that’s not what I wanted. I want this pathetic boy to strip in front of me. In short, I told him to do so and embarrassment filled his eyes as he did what he was told. Soon his tight pants fell to the floor around his ankles, followed by his tight white underwear.

Later, I watch him as he tightened and adjusted his slutty outfit. This wasn’t his first time being a little cross-dressing whore. After he got his outfit on comfortably, I tighten each strap just a little bit more, then put a ball gag into his mouth.

“You’re going to be my dirty little cross-dressing whore tonight,” I whisper into his ear.

Next, I order him to get onto his knees on the floor as I put his collar and leash on around his neck. My cross-dressing whore did what he was told and didn’t argue one bit. Then, I grabbed my ten-inch strap-on, lubed it up, then dripped a couple of drops onto his asshole. Soon, I’ll use my thumb to rub the lube all over his dirty asshole and push my thumb inside him without warning. He let out a little gasp and lightly moaned. Next, I pulled my thumb out and grabbed the shaft of my strap-on and pressed the tip slowly into his ass.

As I’m slowly pushing the whole thing into his ass, I start to slowly pull on his leash. Making it just a little harder for him to breath,  I watch his cock grow from the pleasure I’m giving him. So then, once I have the whole thing inside of him, I start to pump it in and out of his ass nice and hard. He moans and yells with pleasure. He loves being my cross-dressing whore!

Finally, I watched his cock twitch and he came all over himself. I told him to clean up the slutty mess he made. He licked up all his cum and he enjoyed being my cum eating whore! That boy had the time of his life!

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