I started dressing in various forms at a very young age, from wearing long t-shirts as dresses, to handfuls of bobbie pins in my butt as a stretcher. Each chance I got to be alone which wasn't often because of 3 brothers. When I was alone, I got dressed and often have them torn off. I have been a natural pain slut from day one.
Anything that could be slippery became a lube. Of course that meant that ever increasing sizes of broom handles, shovel handles, the most painful at first was the cone shaped kitchen sieve handle. Dressed or naked walks outside to the "Boys Clubhouse". In a box stored in a hidden place were rags for gags, Vaseline, rope, candles for wax melting. Of course my brothers had dad's old issues of Playboy and Penthouse magazines. The women of course became impossible idols for me, I loved the odd bondage cartoon, or True detective magazines.
As Kellianne I am never allowed even today to have an orgasm with a hard on. If I was limp or tucked back then if cum came out of my clittie it was smeared all over my crotch, face, and hair. I was required to leave it until it dried.
Years later I have my own wardrobe including several shoes and dresses. As hard as I try I could not be called "passable" So I Dress up when I take drives out of town daylight or dark wearing club length dresses, thigh high stockings, a modified bra, and my 4 inch heels.
When its not safe I pull on a tee shirt to cover top of dress and pull on sweat pants without elastic at the legs so I can cover my heels.
After my divorce my girl friend at the time aged me to go to a costume party on Halloween, I said sure and knew this was my shot to go full out in public as a woman. When she picked me up I was made dressed in my best, Sandy came to the door and was a little shocked. She said "lets fix your makeup so it looks more the the slut you look like". After a look at my toys she grabbed a set of clover clamps and we were off. I discovered that my dancing looks more like a woman in my high heels. We had a ball at the bar the party was at. After about an hour while sitting side by side, Sandy rubbed up my nylon covered leg until she felt the top of my gartered thigh high stockings. she didn't stop until she felt my lace panties.
Sandy looked me in the eye and said Kellianne who do you belong to tonight? "I am the property of Mistress Sandy tonight","what is your wish Mistress Sandy?" With a little thought she said in a very nice way. " Remove your panties here at the table!" I slowly slid my thighs apart and pulled my lace panties off. Mistress looked to see that my crotch was hairless. Mistress grabbed my hand, told me to leave the panties on the table. She also grabbed our waitress and the three of us went into the ladies room. Mistress asked our waitress, "Annie honey do have a sharpie marker for writing on beer cups?" Annie just nodded her head, Mistress said to both Annie and I, " Kellianne lift your dress and Annie grab your marker." We both obeyed her, Annie had never seen this version of Sandy before.
" Now Annie write in large letters "SLAVE" above her silly clit" Annie rewrote it 3 times so it was very dark. Before I could lower my dress Mistress pushed up my bra and had Annie attach the clover clamps then pull the bra back down.
Before we fixed our makeup Mistress kissed Annie hard on her lips while she fingered her cunt through her daisy dukes pant leg. Mistress got a stern look and said "Annie before you leave this bathroom you will remove your thong and bring it to my table and place it with Kellianne's" As we were leaving I french kissed Annie then almost ran from the bathroom. A little while later Annie came out of the bathroom with her thong in her hand and a wet spot in her panties. She walked by our table and dropped her thong on top of my panties. She whispered to Mistress Sandy " I need his cock in my ass while you fist my cunt." Mistress smiled and nodded her head. "Later."
We stayed til close so Annie could leave with us. Before the end of the night during a break for the band one of the female singers came by and reached under and grabbed my cock. She told Mistress Sandy either I eat her cunt now or everyone will she her cock. Mistress told me to go with her and obey but I was to bring her undies back with me. Needless to say I went and eat her skanky hairy cunt. When she came she tried to pull her jeans and thong up. I think she forgot I am a strong guy and I ripped for thong off and left the bathroom, adding them to the pile.
We began dancing to some good rock music so my dress moved around a lot. Besides no panties and being marked as a Slave, my dress was thin enough because its was fall that my "brand" was plainly visible through the fabric. About 8 people insisted on dancing with me with Mistresses permission All of them wanted to dance close to me, Their legs would drift between mine and each one gropped my clitty. I couldn't help myself of course I got a hardon, it pushed my dress out so everyone could see. I was feeling so female I never noticed people looking.
I am so very sorry, I didn't mean to write such a larger chunk of my life. I guess since I have you, I might as well tell what happened when I got dropped off at home.
The three of us parked in the street and walked to my front door. I took off my dress on the porch and Annie that submissives were to be naked inside when a Mistress is there. Mistress and I walked in and I closed the front drapes a minute of so later a very naked Annie walked in, Her blush was head to toe. Sandy looked me in the eye and said "Thank you for the role reversal tonight!" Sandy helped me remove my bra and stockings as I began to remove her clothes as well. We walked into my bedroom to find Annie self gagged, huge black office paper clamps on her titties, and handcuffs and leg irons. I used a marker and marked Sandy's pussy as "SLUT" and Annie's cunt " CUM SLUT". I grabbed her by the hair and dragged her to the edge of the bed. I lubed her butt and Sandy'd hand, once Sandy had her hand into her slut hole sand started hard fisting her. While I pushed my 8" long cock into her butt with one push. When Sandy and I finished with her request we all crashed. Waking a bout an hour latter I told both ladies. When I am dressed as a male you both serve me. Annie you know we come to dance on the weekend so you will begin not wearing bras or panties to work. The same goes for you Sandy on dance nights. On the weekend you will both mark your pussies just as they are right now. I will check each of you. If you are violating these 3 rules. I will make sure the violations are corrected very publicly. Next time that band plays I will make sure miss not so high and mighty is wearing a mid thigh skirt, no panties and no bra or I will humiliate her.
Good night all. Again I am so sorry.
KelliAnne, Pain Slut