Becomming A Sissy To A Bdsm Mistress

Over the years, I have had BDSM sessions with several Pro mistresses as my wife does not wish to participate. She knows that I need this outlet and reluctantly consents to me visiting professional Dommes from time to time. As long as its a professional encounter, without emotional involvement, its fine with her.

My favorite Domme is in a city that's about a 3 hour drive from home. I have sessioned with her many times and enjoy her particular form of torment. She has stretched my horizons on many ocassions with all of her various toys and particularly with her seductive and evil domination of my mind!

On a recent ocassion, when I called to make an appointment, She inquired about my tendencies to wear a bra and panties under my male clothes. Going down that path, she commanded me to dress fully en femme and to travel to our upcoming session dressed as a woman, something I had never done before. The day before our session, she texted me to instruct me to buy a butt plug and insert it just before getting dressed for my journey.

I must confess that I was very excited and fearful of making the trip dressed in a skirt & top with my wig, makeup, nails, jewelry and all in place. (I have a rather large frame and obviously do not pass very well!) Just driving the car in heels was a new experience, as was keeping my nylon clad knees together in my pencil skirt as I drove.

While I was enroute, she called and had me stop at a convenience store along the way to get some mints as "a lady should never have bad breath". That encounter with the clerk in the C store is a whole other story. All the time, the full feeling of the butt plug reminded me of my submission to her authority.

Once I arrived at my Mistress home and rang the bell, she opened the door dressed in male trousers, shirt & tie and she was playing a masculine role with me. She commented on my pretty outfit, placed a collar around my neck, attached a leash, and led me into her dungeon (with which I have become quite familiar!). She had me remove my dress and panties (leaving my bra, nylons and garter belt in place) and then had me sit in her Gynocological chair, place my feet in the stirrups and get ready for my "exam". She applied wrist and ankle cuffs and secured me to the chair. After checking out and manipulating my genitalia a bit, she applied electro pads to the underside of my balls and a wired ring around the base of my penis.

She hooked up all of the leads to a control box and started a rhythmic but low level shocking pattern that alternated between the sensors. Being quite exposed, she removed my butt plug and replaced it with a wired ***** vibrator. She knew that I was an anal virgin and she announced that today, her little sissy would lose her virginity. With all of these sensors vibrating at varying strength and rhythms, she leaned in close to me barely touching her lips to my lips ever so gently. She had me open my mouth as she allowed her saliva to drip onto my tongue. This was most sensual to me.

She then prepared an enema, removed the vibrating *****, inserted the enema probe and began the fluid flowing. Turning the vibrating sensors on a little higher, whe left the room and allowed me to savor the misery as my intestines spasmed and contorted. It was agony.

After what seemed like an hour, but was really only 10-15 minutes, she returned, now dressed in a black vinyl outfit that accentuated her fantastic body. She removed the enema, unhooked me from the chair and directed me to the ladies room. When leaving the restroom feeling rather empty, she grabbed my leash and lef me over to her bondage bench where I was told to kneel down and lie forward onto my chest. She secured my wrists and ankles to the bench and gently massaged my back and butt, snapping my bra straps and garter belt while reminding of my femininity and pending loss of my virginity.

She came around to my head to show me the huge ******* ***** she was wearing, had me suck on it to get it lubricated and then she went back and spread a gel lubricant on my anus. Then she lovingly and gently took me from behind, easing in at first and then ramping up to a frenzy! WOW! That was quite an experience! I soon found myself bucking back in rhythm to her thrusts! I was no longer a virgin and I was truly her "sissy ****"!

Afterward, she offered me her ladies room for a shower, but I declined for fear of further messing up my makeup. So, I repaired my makeup, reinserted my butt plug, put on my dress and began my journey home, still en femme! What a wild day that turned out to be. It is one that I will not soon forget!



DonnaSue10 DonnaSue10
66-70, M
Jan 16, 2013