Now I'm a crossdressing Domme?

by BillyBoy

20 Nov 2021 1458 readers Score 9.0 (10 votes) PDF Mobi ePub Txt


I surf the gay and sissy porn chat rooms. I've dressed secretly for years. I've even had a few experiences with men wanting to date me. I've sucked a few of them off while in my favorite bra and panties. 

Timmy wants to be dominated by his wife. But she is a prude and doesn't fuck him much anyway. And she has never sucked him off. Ever. Asking her to peg him or lick his ass or do anything kinky has always been out of the question. 

He wants a gay guy or a sissy or a trans to pretend to be her and do all the nasties with him. It's been a slow time sense Covid, and he lives pretty close, so I agree to meet him. 

We meet for a beer in Spokane. Yep, he is s wimpy little fucker. Tall, but skinny and kind of a jerk. He is trying to take charge, telling me what will be what. He said he has some of his wife's clothes in his car. He expects me to dress just like her. I go along and we agree to split a hotel room for the next night, He warns me I better look cute in his wife's clothes. I'm beginning to really not like this guy. Which is  just perfect, isn't it?

When I arrive he is already there. He is sitting in a chair, fully dressed and nervous. On the bed are several leather bondage cuffs, leather straps, some bottles of anal lube, a couple of dildos and a ball gag. He musters up some courage and asked in a stern tone "Why aren't you already dressed?{"

"Because I'm going to dress here, ass bite. Now shut up and get your fucking clothes off."

When i came out of the bathroom he was naked and sitting on the bed. He was wearing the leather cuffs on his wrists and ankles. He was trying the ball gag on for size. 

"Here, I'll help you with that you little bitch."

He was looking me up and down out of the corner of his eye. I was in his wife's favorite white and blue flowered sun dress. I'd stuffed her pretty white lace bra with bath tissue so the top of the dress was full and perky. I'd put on her bone white wedding corset with garters and white lace toped thigh high stockings. My hair was pulled back and I'd used a little make up just the way she does. I could tell he was excited to see me looking like her. His little cock sprang up every time I touched his warm, baby smooth skin. But he groaned and tried to ask me to be more gentle when I pulled the straps and stuffed the ball deeper into his mouth. 

"You're the one who wanted to be topped, you little fuck. So hold on for a wild ride."

I locked his wrists together behind his back and shoved his face into the pillows. I pushed one of the dildos up his ass and told him to take it like a man.

"Mummph! Mummph!"

I was enjoying my role as a Dom Master. I guess I'd never really had a chance to explore it. It felt good holding the back of his head by his hair, pushing it down. I loved shoving the dildo in his ass just to hear him trying to scream and cry for help. It was great! I was hard. And now, I decided not to waste any more time, I was going to fuck him.

I climbed on, pushing my cock between his wet, slippery butt cheeks. He let out a loud yelp for mercy. I reached up under his chest and grabbed his nipples. While I pinched as hard as I could, I whispered to the little fuck. 

"You worthless little prick. I never should have married you. You wonder why I never let you fuck me? Your little dick is pathetic! No woman would ever suck that thing. And you certainly will never satisfy any woman with it either. You worthless piece of shit!" 

The dildo had opened his virgin hole some, and there was lube everywhere, so I slipped right in. I felt him shake and struggle while I pushed harder and harder. it felt really good with my cock in his tight little hole. I loved it! He loved it too.

"You fucking cock whore! You worthless faggot bitch. You deserve to be a slut for real men, you cunt! You deserve to be fucked like the pathetic sissy bitch you really are."

While I was pumping his tight little hole, he was bounding and rubbing his crotch against the bedsheets. His skinny little 5 inch dick was hard. It was purple and red. He was working it on the sheets really hard. Moaning and choking on the big rubber ball. I pulled his hair and tried looking him in the eyes. I hit him harder and harder. My cock entering his never touched, deep tight little places. His face was red and flushed. He was blubbering, drooling and crying. Tears were running all over down his face. Crying like a little bitch!

I grabbed his ass and pulled his hair extra hard when I came. I pushed deeper and squirted for a long, long time. He was screaming, crying for mercy like a rape victim. The noises that came from his gagged mouth were precious. I loved that. 

I stood in front of him like a bitchy wife. Hands on my hips and distain in my voice. He was on his side, still crying. Looking up at me with his red, crying, exhausted face. He had cum, leaving a little pool of jizz under his belly. "There you are, you whore. You finally did something you are good at. You took a load up your ass like a real bitch."

I changed leaving his wife's clothes in a messy, cum stained pile on the floor. I slapped his sore butt. I put the keys to the handcuffs in his hand. 

"That was fun, you little bitch. Call me when you're ready for another round. You may not want to right away, not after this. But I know you will. Because you loved it."

After writing this story I realized the reader could put himself in the the place of either guy. Who would you want to be? 

by BillyBoy

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