Mistress Kira's Delights of a Crossdresser

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Steven is taken hard by Kira and loves every inch.
1.4k words
4.38
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Intro

Steven moaned again as he shifted forwards to steady himself on his hands and knees. Sweat stuck strands of his dark almost jet black hair to his face. His startling green eyes where closed in pleasure.

Behind him Kira thrust into him. Her double d cup breasts pressed against his back each time she thrust the 8 inch strap on into his puckered opening.

She, with her cocoa colored skin, large breasts and healthy sexual appetite, kept him coming back for more. Kira stroked his dick with a slick hand working him like a pro as she continued to both give him and use him for pleasure.

She sat up dragging Steven with her, never removing the strap on from him as she pulled him to sit on her lap. One hand went back to working his straining and leaking dick, the other to his lip gloss painted lips. The fingers pressed and he knew what that meant.

Get them wet.

Kira moved the wet fingers to grasp Steven's nipple, already slightly puffy from her earlier sucking and nipping. She started to roll and tug the slightly abused nub to the rhythm of her strokes both in him and on his dick.

Fuck but he wanted to cum. Steven knew better than to cum without permission. He knew he place and that was under Kira. He threw his head back when she bit at his neck hard enough to bruise.

"Do you want to cum Pet?" her sweet voice questioned.

He nodded but that wouldn't do. "You may speak Pet answer me." she commanded gently.

"Oh yes please!" he practically shouted.

Kira smiled into the side of Steven's neck as she started to thrust harder into him.

In the moments of his sexual haze Steven couldn't help but think of how it all started. How lucky he had gotten and of how far he had come.

Steven sat alone and living room of his two-bedroom apartment. He was alone, he was usually alone these days. Ever since he and his girlfriend of 4 years had split up, he spent most of his time working or at home.

It was very rare that he had one of his few friends over. Mike usually only contacted him if there was money involved.

Since he was alone he thought today might be the day. Today was the day that he was going to look further into something that he only thought about.

Pretty things.

Steven love wearing pretty things. Or rather, he loved the IDEA of being able to wear pretty things. He wasn't yet ready for the reality. He had often thought of wearing a lovely pair of panties, a camisole, some lip gloss, maybe even working his way up to a pair of high heels.

Steven pulled up a site on his laptop . It wasn't a site that he usually spent time on. He would have loved to be on a site where he could purchase something to wear, something lacey, but he wasn't that bold yet. The site he pulled up featured erotic stories in different categories.

He scrolled down trying to find something new and exciting to read. Steven figured if he couldn't experience the life he wanted, he could at least read about it.

He scrolled down trying to see if anything jumped out at him. He didn't see a store on the new additions list that stuck out to him. So he scrolled down further to where the categories started. There was a chat room?

He never really noticed it before, always finding something interesting to read and clicking on that. He clicked on the link for the chat room. It was something you had to sign up for.

It seemed simple enough though, very anonymous. He didn't even have to put any of his own information on the site.

Just his email but no one would be able to see that, only the site administrator. He took a chance and signed up for the site chat room. He didn't want to be too descriptive, just his sex and his username.

Steven clicked the box for male and filled in his user name as BluPanties. Whoever saw he was male would know or guess his secret passion.

There was a listing of chat rooms within minutes he noticed there were people conversing in the main chat room and it looked like there was also the option to converse privately.

Steven didn't know if he was ready to try to talk to someone privately so he posted in the main chat field.

BluPanties: "Hello everyone. "

He watched as his comment scrolled up the screen as people in the chatroom spoke to each other. He clicked around in the room getting a feel for it. He also found out how to access profiles.

MistressK: "Hi BluPanties."

Someone was responding to him!!?

He wasn't sure what to do. Well he should probably start by responding.

BluPanties: "Hi MistressK. How are you?"

He wondered how long it would take to get a response. While he waited, he clicked on the profile for MistressK.

Profile

Female (GG born female)

Name: Kira

Age: 33

"I love a man who will let me dress him up. Let me take charge and

show him how to be my pretty pet."

Steven licked his lips. Wow. Not only was MistressK a woman. She wanted to dress a man up, take control. What the hell was she doing talking to him!?

BluPanties: Nothing much. Just checking out the chat room.

Steven wondered how long it would take before MistressK responded. He stood up from the computer and went into the kitchen to grab myself something to drink.

It was still a bit early in the day to start drinking but what the hell, he was alone. He grabbed himself a glass pouring himself a generous portion of wine and brought the bottle back with him to the computer. Talking to someone on the site had him feeling a tiny bit sexy.

When they got closer to the computer he saw there was already a response. He couldn't believe his eyes.

MistressK: I see. You sound like you're a virgin. To the site that is.

BluPanties: I'm new to the chat room not to the site. I like to go on the site and read the erotic stories once in awhile.

Steven hit send. Then he stood staring at the words on the screen and horror. Why in the hell did he put that he liked to read erotic stories?

This woman was going to think that he was some sort of sick pervert. Then again she was in a chat room talking to a guy with the username BluPanties. Wasn't SHE some sort of sick pervert?

MistressK: What sort of stories do you like to read on the site?

Steven didn't respond. He didn't know if he wanted to put that his favorite type of story was first stories of forced feminization. The type when a woman took charge of the man and forced him in the pretty things. Made him wear it so he revealed his secret passion for loving the feel a soft silky things against his skin.

He knew that would lead to a question of if that was something that he wanted...and yes it was something he desperately wanted. He would love to have someone forced him into those things. He would love to have someone to wear pretty things for.

MistressK: I love forced fem stories myself. It's just in my nature to be dominant and I love dressing up beautiful man. Describe yourself to me BluPanties.

Steven was once again staring in horror at the screen. Not because he didn't like the response, but because this was like his dream coming true. A woman that was into what he was into. Someone that might want to dress him up. Then he got excited. She wanted him to describe himself.

He didn't believe himself to be anything special. Pretty normal. He never thought he was someone women would just drop their panties for. Let alone ask him to drop HIS for THEM. But he was very interested and he wanted to be as honest as he possibly could be.

BluPanties: 38. Black hair, green eyes. Average.

MistressK: 23, 5'3", DD, curvy. Hazel eyes, black hair. So tell me more about these...blue panties...

To be continued...

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2 Comments
cdCindy1cdCindy1over 6 years ago
great start

I can't wait to read the next chapters. I too am a sissy CD who has just recently started seeing a Mistress. She dresses me in sexy clothes, helps me with my make-up, and then feeds me her strap-on dildo both in my mouth and in my man-pussy. I love going to her and I'd love to read about what happens in your story.

AnonymousAnonymousover 6 years ago
Nice beginning

Can't wait for this story to develope.

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