[Fiction] Becoming Her pretty sissy

[oddjobber]

*SMACK*!!! "100! Thank you Maam!", I shouted as the paddle landed on the mark. My ass throbbing with the heat and my eyes waterred from the pain as She patted me on the head with a comforting word. She let me linger in my restraints a while longer to think on my recent behavior. I needed to learn more self control I thought. She left me alone for a whilewith nothing but the heat of my ass to continually remind me of my place.

When she returned moments later she carried a small bundle that she set on the table. She sat down and told me her new plan for me. Since I failed to make a worthy male sub she had decided it was time for her to have a woman. The first step she said was preperation. She unfolded the bundle and I saw a shaving razor and cream. Her command was for me to shave my body completly from the shoulders down. I would see her again in a weeks time and by that point my hair must be cut short and my body shaved. This would be the first step in my transformation into her obedient sissy that she now craved. My denial was increased and an order of no touching was given..aside from cleaning and prep wrok.

She undid the restraints and asked if i understood my new assignment. "Yes Maam" I replied. She told me when I returned I would be inspected and any stray hairs would mean lashes from the belt so i had best be thorough.

I had never shaved that much of myself before so i was a bit apprehensive but I would not fail her. I took my bundle or shaving components and when she left I dressed and headed home.

That night I stood naked in the bathroom ready to start. I was hesitant...shaving that much would really be a strange look for me and if i wore shorrs, how would i explain that to people?? Somehow it felt like my masculinity was washing away at the thought of this task.

I grabbed the razor...grabbed the shaving cream..took a deep breath and began.

[work in progress]

[oddjobber]

Starring at the razor and then the mirror I never realized how truely hairy i was. I thought about where to start first. Even my nipples are hairy I noticed and thought them a descent place to start. I put a bit of lather in my hand and applied it to my nipples and the cautiously slid the blade across. i went around the part that stuck up, didnt want to slice it off...just clean it up. With that done i did the second and looked at the smoothness. Not bad. Next i decided for the chest. that would be pretty straight forward and still maintain some semblance of manhood. i guess i was still unsure about this path She had set for me.

But i continued and shaved, small patches as every movement clogged the blades with hair. This was going to take sometime i thought as I looked down to my legs. I finished the chest and moved down to my stomach, that went next. By this time it was starting to get late so taking one last look i decided to wait for the morning to continue. i dried off and went to bed, sleeping naked as I am supposed to do.

That morning I was awoken by the vibrating of my phone. A text from Her asking about my progress and demanding a picture to see that I was shaved. I jumped up and not wanting to make my Mistress wait I snapped a pic. carefully showing the bare chest and stomach.

An immediate message back...angry and dissappointed that i wasnt completly shaven. 100 whips of a belt to my useless balls she demanded. Ugh..this was going to hurt. But i had to obey so i found my belt, put a leg up on the bed and whipped myself in the balls. each strike painful and after a few i was on my knees, my stomach churtling with the pain. I took a deep breath and swung a few more. I tried to switch the area so i tucked my balls between my thighs while on my knees and swung the belt like spanking my ass. fuck that hirt even worse on the tight balls. i think i may have even cut them.

i checked..no blood but it aure did sting. kneeling i threw 10 more strikes before fallong to my side clutching myself. I was getting there...but after a few minutes i got up and threw another ten each increasing the pain and sickening feeling in my gut.

When i finally finished i was hirtong. I sent my Miss a note that i had finished and she said to now finish the shaving as i was supposed to habe done and not dissappoint her again.

i got up and decided to shower to be able to best do this shaving job. Taking the razor in hand i entered the shower and decided to just go for it. I felt an already amooth part of hairless skin on my hip and enjoyed it. This will be good i thought..so i started at my hip and moved down the thogh. this was slow going as i could only do small patches again before needing to clean the blades. The front of my thighs took time and moving round the back was awkward. how the heck do women do this i thought.

i continued on and got into a rythym with it. before long i had both my legs shaved and my goodness what a feeling!! i couldnt resist running my hands up and down my own thighs and haveing naughty thoughts.

i moved on then to shaving my ass..pulling my cheeks open and getting the razor in there...goodness my ass was hairy. but when i finished..it felt so smooth. i could get used to this. Slowly and carefully i shaved the balls and my cock and relished in the smoothness.

When i finished i sent Her a picture. An immediate response saying only "Armpits?" aw crap i thought...i just reakized i forgot the armpits....i reluctantly sent a pic....and then..nothing..aw crap..i know i'm in trouble now!

[oddjobber]

after what seemed an eterntity, she replied back "Finish the job then come see me, immediatly." Well, this was a change. usually we kept to weekly sessions with the rest of time spent virtual so i knew this was big. I jumped back in the shower and shaved the pits carefully. I did cut a little but nothing too bad.

I got dressed and headed to her place. I stripped at the door which was required, and knocked. and i waited....and waited...and waited. Finally i turned an saw a npte hanging on the post porch. There was a bag hanging there as well. The note had my name on ot so i opened it. The not said "Pit this on and drop the key in the slot. See you Friday."

I opened the bag...a chastoty cage?? omg..this was going to be a lomg five days. I did as instructed standimg there on the porch. One car drove by and embarresimgly beeped..but i got myself comfy in thos new device and locked myself in. Now i held the key. No turnimg back if i drop this in the slot. My belly was full of butterflies and my hand was shakomg but i trusted her and woth a deep breath i dropped in the key.

I tirned to grab my cloths when the door opened. "Good job my pet, you are on your way to becoming the woman I want ypu to be. " She invited me in and explained how i no longer would have a cpck for pleasure and how my now tight ass would be trained as my pleasure center. I gulped with each description and new rule she gave me...but i agreed to them all.

She told me fpr the remainder of the week i would not weae my normal under wear amd that i was to go now and buy eight pairs of panties. Those i would bring friday but was not to wear. no underwwar would be worn the rest of the week.

And with that she gave me one last reminder to shave everyday and to also get some moisturizing creams.

I agreed and left for the store. I was somewhat embarressed shoopimg in the womans section but had in my mind to say they were for a girlfriend if asked. but no one seemed to care. I bought several different colors that i thought would be pleasing, stopped for moisturizer and headed home.

It wasnt until i went to piss the first time that i was reminded of the cage dangling between my legs. I started to get nervous..what if i got hard? what would happen? why did i have this on? but i managed to calm myself down remeberimg my trust in my Miss.

Later that night sleep qas awkward. the cage was different and a constant reminder that it was there. I got up at one point and woth a bit of light on walked to the mirror. I looked at myself..shave and caged..i, almost instinctivly put my knees together and felt somewhat feminine. it was a comforting feeling and made me less nervous aboit the cage. I was resolved to see this thru and went back to bed to enjoy a comforting deep sleep.

[m55uk4younger]

Calm down, you are getting excited, check your spelling, sissy boy!

Sir.

[oddjobber]

thank you sir for your comments. i will try and be more careful with my spelling. tiny mobile keyboard doesn't keep up well

[oddjobber]

It didnt take me long to get used to the cage. The first morning was awkward and I felt like i was walking around with a huge bulge in my pants. But no one seemed to notice anything. It did keep me conscious of the fact that i could not get erect which in itself made me extremly aroused and seemed to keep my balls rolling around quite a bit.

Finally friday came and as soon as i was done i headed for Her house. Agian at the door i stripped, knocked and waited. She tended to make me wait and that I always found fair and a good thing. It helped to calm me and clear away all my thoughts of the world and any problems i may have. it helped to center me on what was to come and to focus on Her alone. She is always thinking of these things.

She opened the door and let me in. She told me to head upstairs and stand by the bed. Once there she had me lift up my arms and she inspected my arm pits and carefully inspected the rest of my body. She smacked me on the back of the head..a sign to bend over and put my hands on the bed. She pulled my ass cheeks open and inspected me for hair as well. She was pleased...i was quite hairless and i had cut my hair short as well. She stood me up and turned me around. Grapsing at the chain around her neck she slowly pulled the key from her bosom and reached down releasing my cock from its cage.

"You've been good and tonight we will take the next step. Go shower and prepare urself. Come back here when ur done."

I went and did as she bid. It felt strange now to be released and to feel my cock again. but i didnt touch it mucb except to wash. When i was thru i headed back into the bedroom. i stood by the bed. She sat on the edge of the bed. I looked at the outfit laid out on the bed in amazement. Heels, a pair of white stockings and what looked like a red dress. she told me to get dressed and as i started to fumble with the stockings she stopped and guided me in the technique helping me dress. i stood up and she helped me into the dress which all fit nicley. she knew my dimensions quite well. finally she came over with a wig of shiny, long straight black hair. she placed it gently on my head stepped back and said..my dont you look pretty.

she turned and brought over a pair of white gloves that went up to my elbows with tiny red bows over them. "Oh..now lets do your makeup!"

we sat and spent a long while doimg my makeup. she explaimed all the different types and thier uses. when she was finally done she told me that i was to now go stand in the corner and wait for her. i did so pondering my current state and how almost natural and comforting it felt. i wondered what was now instore for the evening as she was showering and getting ready to go out. omg..go out!?! i just realized what that meant.

She finally returned ready to go out. when she stepped close to me i couldnt help but inhale deeply her scent. it was intoxicating and arousing. she noticed my movement and pulled up my skirt. she smacked me hard in the balls saying "None of that!" and then reminded me it was time for my cage. she placed it backed on and tucked the key into her bra. "If you behave and do all that i tell you to do tonight, we might just let you out of there"

and with that we headed out the door. i carried her purse as was always the case but tonight, she drove.