Reading Cross Dressing

Cross dressing and Slut Training often go hand in hand and the two fetishes compliment each other beautifully! Here’s an account from a recent session!

I picked up the phone the other day to the sweetest girly voice! “Hello I’m Nathan” said the voice “But you can call me Nancy or Nancy Boy or anything of your choice Mistress.”

I chuckled and asked Nancy if he was a sissy. “Yes Mistress. I would love to come to Watford and have you feminise me and make me into your slut. I am very obedient, loyal and highly trainable.”

Nancy sounded just perfect so I arranged a two hour for session for her the next day. Nancy arrived in normal attire and as she wanted an intense session I explained the rules:

  1. Nancy would have to speak, walk and move like a girly slut for the entire session.
  2. Nancy would be trained to suck my strap on cock.
  3. Nancy would wear a butt plug the whole time, apart from when she was taking my strap-on.
  4. Nancy would moan like a girl whenever instructed.
  5. Nancy would be open to my suggestions and put her all into it.

Nancy likes pink so I picked out some saucy little baby pink fishnet stockings for her and a matching suspender belt which made her peachy bottom look delightfully cute! I felt compelled to take advantage of that creamy, curvy arse straight away so had my slut bend over the bed. Guess what I popped between those jiggling cheeks? A nice medium sized pink butt plug of course! She squeaked in enjoyment as the butt plug entered her, which pleased me immensely. The high pitch tone was just perfect and I was convinced that Nancy could be a really genuine girly slut with a little training. To hide the silly man parts I gave her a a soft and silky pair of pink panties to step into. Then she wriggled into a tight little spandex dress she had brought with her and a blonde shoulder length wig. I ordered Nancy to step into a pair of Sissy heels and she looked an absolute vision!

Cross Dressing Sissy in Reading

I took photo’s of Nancy from behind holding some sexy poses and instructed her to cover her face with her hair.  Then I told her that some of my other subs would be very turned on at the vision and would love to experience her cock sucking skills, but first I must see a demonstration to measure her value as a worthy sissy slut. I donned my StrapOn and Nancy sunk to her knees, her pink mouth opening wide like a little dolly waiting to suck some cock  – and with a good deal of desperation. The minute I allowed her to make contact between her lips and the strapon she moaned in absolute ecstasy. Her eyes blinked and slowly closed as she sucked it back deep in her mouth.

Then I told her to give me sex doll eyes. She looked up at me with big wide eyes under her lashes whilst she slowly sucked the 10 inch strapon into her naughty little mouth! She did a wonderful job of worshipping my cock and I praised her and said that if it was a real cock it would be throbbing all over! I had Nancy then suck another even bigger and wider dildo for me whilst I took her from behind on the bed. I pulled her knickers down to her knees, pushed her over the bed and pulled out the pink butt plug. I could tell she was desperate for my strapon as she was arching her back and shaking her naughty bottom. I teased her for a while first and used my magic wand against her man pussy which drove her crazy. I put on a video of a sissy sucking cock and told her to keep her eyes on the screen and learn how to be a good bitch and she agreed readily.

“Are you a slut worthy of my strapon?” I asked.

“Yes Mistress, I’ll do anything for you!” 

“You will wear panties all the time slut? And suck cocks for me?”

“Always Mistress. I will always do what you say!”

My slut was so horny and eager to please that I am sure she would have done anything I asked of her at that moment!

My naughty little sissy was squeaking like an excited puppy and when I finally slid the strap on in her whole body trembled with joy. I thrust slowly to start with, and made Nancy beg for a harder pounding. She was eager and desperate and I smiled knowing that I had her at my mercy. I began to pound Nancy harder with the strapon and told her that she would think of eating some lovely frothy jizz when I let her come.

“Mistress, I’ll even eat mine for you!” she exclaimed desperate to be allowed to come.

“It’s a deal, but no spilling any or wasting a single drop!” I warned.

“I promise” she squealed. I gave her a good hard pounding and eventually allowed her to sneak a hand down towards her panties. She had barely stroked her man pussy twice before she came all over her hand. I told her to quickly lick it all up like a good girl to avoid punishment. The slut was lightening fast and licked it as if she were a man starving in the dessert! She ate her jizz with relish and showed me that she was capable of being further slut trained. Perhaps next time I will have her shoot it into a shot glass so she can neck it!

Shot Glass

Nancy is going to try her first experience of sucking a real cock next time. I  have the perfect sub for her and she will love going to town on him! Of course, I will update you on her progress and share the naughty secrets with you. Nancy is very excited to have her sessions shared with my readers and subs and would love to hear your comments and thoughts!



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  1. Jazlyn - 5th October 2016 at 6:53 AM -

    This was very good for me to read. Master and i have a complete TPE, and that includes financial control. W/we only have difficulties when i don’t understand what is going on and where we are at in O/our journey. Thankfully, this part of O/our journey is drawing to a close and W/we will be rid of the hindrance in O/our life very soon. My Master is also very clever with money and I never have to suffer from a lack of trust in Him ever, in any aspect of O/our D/s reoisilnthap. He is truly a World Class Grand Master and my Hero!! i love Him.