Cross Dressing scene: 21/6/11

On Tuesday, 21 June 2011, I met with my crossdresser submissive.  I have named him Tammy, and now refer to him as “her”.

I first met Tammy in February 2011 referred to me via a submissive friend in Melbourne.  Tammy travels often, and gets down to Hobart 3-4 times year and is exploring her kink more and more.

She has been private about her fetish to wear women’s clothing for many years.  She has a passion for panties and is quite willing to steal panties because she loves the look and feel of them.  She is quite submissive but still uncertain of her path.

We have decided to explore her kink together.  She will serve only me until I believe it is time for her to find a mistress in her state.

This was the first time Tammy had ever met with a real Mistress.  She had played with a submissive friend but that was more just little ‘plays’. 

The Scene

I met Tammy at her apartment at 8.10pm. 

Awaiting for me was a dozen oysters and a bottle of Marlborough Sauvignon Blanc, with a glass poured.  I could tell Tammy was extremely nervous being in my presence.  I looked around the apartment, remove my coat and gloves.  She babbled for a little while.  I let her, while I ate my oysters and drank the white wine.

Once I’d finished my sustenance, I went to view all the lingerie that was laid out for my perusal.  I selected the stockings, suspender belt and panties Tammy was to wear with her red dress along with a cincher.  Refinement is required but I will address that in time.

Tammy kneeled at my feet, hands behind her back and awaited my instructions.

At 8.35pm, I requested Tammy to remove her work clothing and dress in her feminine clothing.  I watched.  Her clothes were thrown on the floor so I directed her to hang up the business shirt and fold the trousers.  This was done promptly. 

When she removed her underwear, her cock clit was dripping precum.  Oh, excitement plus do I detect? *grins*

First her ball stretcher was attached.  Followed by her pink panties with the bow in the front… the obvious excitement of Tammy was evident.  Next was the suspender belt, along with the silk black stockings.  Alas there was a hole in the toe end of the right stocking.  Tammy was reminded to inspect stockings before she dressed for me again.  Next, the red dress was put on.  It was very pretty, fitting and feminine.  It was a nice snug fit.  Next the black cincher was donned.  Tammy’s face was deadpanned but I could see the flush in her face indicating exhilaration.

I directed her to come forward so I could inspect her, adjust her clothing.  I then applied clover clamps.  Wincing in pain was a pleasure for me to see.  I turned her around and restrained her wrists.  She was told to lay on the bed, face down.  The clover clamps pinched viciously.

I asked Tammy what was it like to be in the presence of a Mistress.  She said it was a dream come true and she was in awe that it was me, and she has not felt this happy in a long time.  To be with another person who accepted her kink so easily.

I then donned my Strap On cock.  It was peeking out under my PVC skirt… very hot.  A condom was put over the cock. 

I lay on the bed beside Tammy on my side while she was face down.  I told her to move to her side so my cock was near her mouth.  I said kiss it.  She did.  I said that was pathetic, kiss it again.  She did with more enthusiasm.  Then, I directed her to suck it.  I allowed her to do this for a period of time.  She had a rest, then I had her continue sucking the cock.  Just sucking, sucking, dribbling and sucking.  Pity I couldn’t have video taped her, she sucks very well for a virgin.

I removed her restraints for a short time as she was getting sore shoulders and not used to being in this type of position.  I told her to get used to it when she is in my presence.  I removed the clover clamps and she was rather tender, so I squeezed her nipples… she winced.  I smiled gleefully, wickedly.

Tammy was then requested to come over and kneel between my legs.  I saw her eyes riveted on the cock, and they were shining.  The emerging of a real slut - methinks.  I directed Tammy to kiss the cock.  She did.  I told her to suck the cock.  She did with passion.  She was almost taking the cock all the way down… almost. 

Tammy and I talked about general matters as I lay back on the chair, arms behind my head, cock protruding and Tammy trying her best not to look at the cock… she couldn’t resist of course.

I extended my stiletto shoe for Tammy to kiss. 

We discussed her being my cross dresser submissive, and she was delighted that I was interested in being part of Ms Neta’s kinky family.  She considers me a Dominant with immense power.  I smiled.

It was 10.00pm, and I said “Is there anything you wish to say to me, Tammy” and she looked me straight in the eyes and says “I should kiss your cock goodnight”… I was taken aback at that, and realised she loves sucking my cock, albeit, my dildo cock but whose to say what will happen in the future… with some encouragement she may move on to sucking flesh cock with Ms Neta’s assistance of course.

She sucks well.  A budding slut she is.

I donned my coat and gloves, bid farewell to Tammy, and left.  It was such an enjoyable evening to help someone explore their crossdressing kink.

It was 10.07pm.