[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.

[oddjobber]

We entered the crowded bar and instantly i could feel the eyes upon me, although i am sure the men were more interested in my Miss. I did here some giggles as we passed...coincidence, i dont know. But i follow Miss and she sat me at the bar and ordered us some drinks. We sat and chatted and she told me how pretty i looked and reminded me to be good and relax.

I did try to relax. As time went on Miss got up and walked to one end the the bar to chat with a group of men. I could not hear what was being said but did notice an occasional glance my way and my Miss pointing me out. At one point she did return and had a guy with her. "Lift your skirt" she said which i did, showing this guy my caged dick. He laughed andjust said "cute." Miss walked away with him as i heard her say how obedient i was. That praise made me smile.

I enjoyed another drink and before I knew it my Miss was back with two gentlemen and told me it was time to go. I thought that Miss was going to have an enjoyable night with two men as we left the bar. We headed to the car in the parking lot which took me sometime really just getting used to the heels. I followed along as Miss walked with the two men ahaed of me.

When we got to the car they stopped and stood there watching me as i strugggled to catch up. The three of them were leanong on the car starring at me. Miss turned to them and asked "Well, who wants to go first?" I whitened..what was going on? i thought. What did she mean? The guy in the middle stood up and grabbing his belt buckles said "I will, I hope she knows what shes doing". My miss replied that I would learn. And she approached me, leaned into my ear and whispered "Now you will become the sissy slut that I deserve to possess. You will do as I bid and your life as my slut starts now. Do you understand? " Yes maam was all i could whisper back. She smiled...grabbed me by the hand and brought me over to the first gentleman. "Knees" she commanded..and i dropped to my knees. i starred ar the bulge in his jeans not quite sure what i was doing or thinking. "well, take it out slut" my Miss commanded as the guys looked at each other and laughed. I hesitantly reached up and undid his button..unzipped the fly and running my hands inside the band of his underwwar i pulled down. His montorous cock sprang out at me and i gasped..oh my goodness.."They all laughed. Miss croutched down next to me and said "time for you to become that sissy..no turning back now" as she pushed the back of my head closer to his throbbing shaft. i could feel the heat off of it..the mix smell of sweat and my Misses perfume. She grabbed his dick in hand and guided it to my mouth.."Open wide" she said..and with that there was a dick in my mouth. I had to open my mouth so wide as hamds went to my head and this big piece of meat slid in and nearly chocked me. back out and then in again..i found myself making that gagging sound and all i could hear was the slurp slurp as my mouth was being drilled. Anoccassional good girl qas said but i lot track of from whom. all i could think about was not closing my mouth and how humiliating this was to be doing in a parking lot. I found my hands resisting, pushing against this mans hips bit it didnt help. That only made him thrust harder. After what seemed an eternity his friend pushed him aside and said "My turn" and before i knew it there was another cock in my mouth. This one with a much more bulbous head that seemed to hit my teeth with wvery thrist..forced me to open even wider. The other cock was still in my peripheral vision..he stood stroking it.

My Miss grabbed my hand and put it on his cock telling me not to forget that too. So i did...and then something in me snapped and i just felt at home. I went from resisting to enjoyimg to craving and wanting more. I grabbed both cocks in my hamds and strokeed them and looked up at the men who each smiled. I then devoured each cock one after the other sucking amd stroking.

This went on for sometime before Miss said it was time for a drive.

I got up and the men piled into the back seat. She said for me to get in there too. i sat in the middled and found myself naturally stroking their cocks in my hands. They were each groping me at this point, running their hands on my thighs. they had me kneel on the seat and each squeezed my ass. I felt a finger tip press against my hole. I was so horny at this point i knew what i needed to do. Thankfully Miss had prepared me for anal with a strapon in previous sessions. I straddled over the first man and sat back down..feeling his hard shaft against my hole.

"Time for the sissy to lwarn her place" he said..i smiled and pushed myself sown on his dick. the head spreading my ass open. it felt so good i could feel my dick squeeze in the cage and leak. i squated up and down taking in more and more of his dick with each thrust. the other man watched and stroked himself as i continued to slide down this shaft. it was all i could do not to scream in pleasure.

My. Miss looked back in the mirror and said "now thats my girl!!"

and that encouraged me more..i bunced faster and faster...long slow bounces as his dick filled my hole. my arms around his neck i could see in his face the pleasure. it made me bounce faster and faster..his head fell back and his hands squeezed my hips and he started thrusting into me..holding me in palce as he pounded me...a few more pumps and he let out this moan and i felt it. his cock swelled and spurted and it felt like someone stuck a hose up my ass and turned it on high. it felt so warm. i slowly pulled up and off as he shudder from the sensation. i turned on all fours as my ass lay open in front of him..he smacked it and told my Miss how such a good slut i was.

Now me said the other guy. I bent down and took his cock into my mouth to wet it..then got up facong him. "turn around" he said. I did showing him my ass and back. I squatted up and he guided his dick into my gaping hole. it was easier to take him in now and i was so horny i just wanted that full feeling again. i bounced on him as he spanked and squeezed my ass. he luved my aas i could tell. he fucked it hard and soon he filled me with his spunk as well.

when he was done Miss pulled the car over. The two gentlemen gout out and thanked her.

We headed home. I sat there feeling my throbbing asa slowly leaking more and more of their cum. Miss was impressed and proud of my transformation. When we got home i got up and there was a puddle of cum on the seat. She said i would clean ot in the morning but for now i was to go inside. inside she told me how proud she was and said for a reward i was to follow her.

she brought me to her room..to the closet. she opened it and onside the walkin closet on one side was a full wardrobe of clothing..pretty stuff and frilly things. she said these were all mine and the only clothes i woukd wear from now on as her live in sissy. She was letting me move in. Now that was a reward beyond compare!!

I am such a happy sissy now.

Fin