Slut Training With CrossDresser Jessica Dee

I have many sissy followers on Twitter and I keep on eye on those who strike me as particularly slutty. I had been talking to Jessica Dee on webcam for a while and it seemed we have many common interests, so a kinky day of filming seemed very appealing.

I am extremely selective about whom I shoot with, but I do love a cross dresser who makes a huge effort to feminise themselves and act in a girly way. Jessica seemed to tick all the boxes so we arranged a shoot at my venue.

Jessica told me that she would arrive locked into her chastity cage which I was pleased to hear. I insisted on having a peek when she arrived. It was baby pink and squeezed her balls nicely and tightly. This should make for a very interesting day I thought!

Jessica Dee Wear's A Pink Chastity Cage

With her man pussy under lock and key, I felt that her naughty little bottom should be used as much as possible! We embarked upon some slut training and I fed various dildo’s and Strap On cock’s of increasing size into Jessica’s willing holes. I have to give Jess her due – she took them all with nothing but pure enthusiasm and really seemed to get off on the largest – a big black 18 inch beast of a strap on! Oh my, I started to gently slide in the biggest cock a centimetre at a time but the greedy girl just slid herself back on that whopper and took it deep. I certainly didn’t wait around then, I took a hold of her hips and began to thrust, slow, deep and hard! You should have heard her moans as sounds of absolute ecstasy came from her bright pink lips.

Jess admitted that it made her naughty cock twitch when I pounded her arse and frustrated her further as she was unable to get an erection whilst in chastity. This pleased me all the more and I enjoyed the thought of her suffering – unable to get a proper stiffy but dying for release! I felt my magic wand would exacerbate her frustration so I teased it all over her balls and then her cock cage  – making it rattle! Of course she began to writhe and seem as if she might orgasm I pulled the toy away and left her to suffer. This was a delicious game of tease and denial and she would not be enjoying an orgasm today!

After a while I decided that even this was far too much pleasure for her so I would have to discipline her and ensure her obedience at all times.  The idea of Jess as a college girl slut really appealed to me so I gave her a school uniform to put on and show off her long nylon clad legs. I dressed as a strict and stern Head Mistress in a knee length grey skirt and contrasted with a slutty blouse to tease my little cross dressing Slutifer.

Mistress Kaz Spanks Cross Dresser Jessica Dee

The theme was that I was privately educating Jess and caught her watching porn, smoking and drinking. I reprimanded her on her delinquent behaviour and ordered her to lie across my lap for an over the knee spanking. The slut obliged and I began with a slow teasing spank to lull her into a false sense of security. After a while though I just could not resist some hard, stinging slaps that made her moan and yelp like a bitch! I stroked her arse, trailed my long finger nails over her cheeks and administered stinging hard slaps that made her cheeks quiver and turn bright red.

I followed this punishment with a good paddling. Each blow made her omit a sweet sound of pain and the resounding thwack of the paddle was music to my ears.

Occasionally I do have a little mercy for my sweet little man sluts, so now and again I was kind another to let her rub her stinging cheeks in between. Not for long though and I increased the punishment each time to ensure that she learnt her lesson!

Finally as a humiliating punishment for drinking in my lesson, I forced her to lick champagne from my feet. She willingly lapped in all up and thank me for punishing her and helping her to see the error of her ways!

This was such a superbly kinky shoot and you will be able to see the videos very soon on my adult work profile here: Kinky Fetish Videos

 

 

 


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