Shaved And Flipped To A Sissy

I've had a fetish for panties since wearing my sisters growing up, I would always search thru the dryer before mom sorted the clothes and pull out a fresh pair and hurry to my bedroom and slip them on and jack off. Once I left home, I accumulated a stash of stretch nylon panties and porn to jack off with. I found it exhilarating walking into a store and picking out panties then taking them to the counter to pay, often wondering what the sales lady thinking was. The embarrassment always got me aroused and led to me having many masturbation sessions wearing my new panties. After getting a job in construction I found womans nylon panties much more comfortable than the male cotton underwear that stuck to your ass in hot weather and I loved the way the stretchy material hugged my cock and balls, my jeans would glide over my ass. So, I began secretly wearing them under my jeans, wearing only white or black at work in case my coworkers would catch a glimpse. But after work I could indulge in all the other colors; pink, blue, yellow etc. that made my cock throb.

I began watching porn while jacking off, at first seeing beautiful women getting plowed by huge cocks then started watching double penetration videos. Somewhere in one of these videos the woman encouraged her (husband) to suck the cock that had just filled her shaved pussy with his seed, reluctantly he agreed tentatively licking the cum covered cock before she forced his head down engulfing his mouth with cock. Before long he was eagerly sucking the fuck juices off the glistening rod

As she exclaimed it looks like he enjoys a hard cock in his mouth, he picked up the pace as she watched her husband turn into a cocksucker. She began stroking the

man's cock as her husband's head bobbed up and down, causing the man to unload into his mouth which he tried to swallow but it was to much. Wiping the cum from around his mouth she then fed it to him as he licked her fingers clean.

I blew my load all over my chest and face, I closed my eyes and scooped it up and fed it to myself pretending it was the wife from the video, it was one of the strongest orgasms I've ever had. I knew then I needed a dominant woman to force me to take a hard cock in my mouth and swallow his load, the hot cum coating my throat and mouth with his seed.

From then on, I began watching tranny and gay porn wanting to suck cock and then began fantasizing having a huge cock pounding my tight ass. To fulfill this desire, I bought various size butt plugs and vibrators to plow my ass while watching men get ass fucked on screen, this always culminated with me blowing my load and feeding it to myself,

I had to keep all this a dark hidden secret from my coworkers so every so often I would take a few girls on a date and have uninspired sex and then drop them to satisfy my (manhood) around my coworkers. That changed when Lisa asked me out. We met when I cut my finger and needed stitches. She worked as a nurse at the local clinic and after wrapping my finger and giving me instructions on preventing infections asked if I would like to go out sometime. Lisa felt different from anyone I ever dated, and I quickly agreed to a date Saturday night.

I arrived at Lisa's place around 5:30 to pick her up for dinner, I was strangely nervous in a good way as I knocked on the door of a beautiful home situated in an upper-class neighborhood. The lawns were well manicured, and the homes well kept, I began to wonder how she could afford such a house when she answered the door interrupting my thought. I knew Lisa was an attractive woman but was shocked to see how beautiful she was out of her scrubs and in clothes that showed off her figure and blond hair with blue eyes. Looking at her approx. 5'10" body that could turn anyone's head, her low-cut blouse showed off her c cup breast and her long-toned legs that disappeared up her short skirt which couldn't disguise her tight ass.

I've been told I'm an attractive man standing 5"11 and 150 pounds with a well-toned and tan body due to my work and exercise routine, I also have a nice sized cock at around 7 inches which always seemed to pleasure my sex partners, but I felt out of my class standing before this beautiful lady. She didn't seem to notice as she greeted me, and I led her out to my car.

After a nice night out as I pulled up to her house she leaned over and gave me a passionate kiss and invited me in, my cock growing in my pants I instantly accepted. I was already infatuated about this girl and i felt there was something different about her and I was soon about to find out what it was. As we entered the house, she pushed me up against the wall and kissed me before working her way down my body removing my clothes as she went, as my pants hit the floor, I noticed a look of disappointment on her face before pulling down my shorts and taking my cock into her mouth. Her tongue swirled around my blood engorged mushroomed head before she worked her way down my shaft, soon I felt her mouth moving up and down milking my hard member as she suddenly started to probe my ass. Finding my hole, she wiggled her finger past my sphincter causing me to let out a load moan, only to add another finger opening my sphincter further. she began to work her fingers back and forth and I began to match her rhythm as she finger fucked my ass using them like a small cock before locating my prostate.

When her fingers reached my prostate my cock erupted, my knees began to buckle as I pumped out what felt like a bucket of cum. Never in my life had I experienced an orgasm like that, looking down I could see Lisa smiling as she slid her fingers past my sphincter and out of my ass. With my cum running down her chin she rose and kissed me, pushing my load deep into my mouth as I gladly swallowed fulfilling a fantasy long unfulfilled. After feeding me my load she pulled away and led me to her bedroom, peeling away her clothing allowed me to realize how intoxicating she truly was. I was under her spell as my eyes drifted from her firm breast to her shaved bare pussy and legs, I started at her calves and trailed my tongue to her moist sweet folds of her swollen cunt, I lapped at her creamy juices before finding the way to her clit. As I tongued her button, I slipped Two fingers up her slit and slowly sawed them back and forth while returning the favor slipping a finger up her ass. She began to buck like a horse as an orgasm rocked her body releasing a flood of juices soaking the bed. I pulled away to kiss her as she guided my rebounded cock into her soaked pussy, rolling over she rode me cowgirl having multiple orgasms until satisfied, she worked a finger into my ass causing me to flood her pussy. Sweaty and exhausted she walked on her knees until her cum soaked and well fucked pussy was above my mouth, she grabbed my hair pulling my mouth into her swollen cunt and demanded I clean up my mess. I ran my tongue through her slit capturing the cum was leaking and quickly swallowed it before running my tongue around her soft petal's before burying my tongue deep into her pussy scooping my cum and her sweet nectar.

After resting a while Lisa looked at me and asked why I wasn't wearing panties tonight, I gave her a puzzled look, but she explained why she had asked me out. At the clinic she noticed I was wearing panties and the thought of me wearing panties excited her. Maybe it was the sex but I soon I found myself spilling all of my secret desires to this beautiful creature. I even told her my fantasy about wanting to suck a cock while another was stuffed up my ass balls banging, worried I said too much I looked at her as her eyes lit up as the smile spread across her face when she confessed that when she saw my panties she masturbated with her vibrator hoping I would be the one to fulfill her fantasies Relieved of my secret desires and exhausted from sex I fell into a deep sleep waking to the smell of breakfast.

Over breakfast we had some small talk, she told me she inherited the house from her aunt who also left her enough money to live on, but she chose to work, I told her about my life which led back to my sexual fantasies. She smiled and told me we were going to start and work on those right after breakfast. Afterwards she told me of her fantasies, and it looked like we both were going to live them out together.

First, she led me to the bathroom where she explained I needed to get rid of my pubic hair to wear panties properly, I feigned resistance but my cock steadily growing gave me away, she took a small pair of battery clippers and sheared all my pubic hair to a short stubble. I secretly wanted her to remove all of my body hair and soon figured out that this was her plan all along, she lifted my balls and slowly clipped them bare. Lisa then began to remove the hair on my thighs working down my legs until they were nothing but stubble, she then had me turn around as she slipped the trimmer between my ass cheeks eliciting a loud moan from me. Laughing she exclaimed my legs were fantastic, for someone who didn't want a panty shave you sure seem to like this. My silent answer was my cock bobbing up and down. After moving to my chest and underarms she produced shaving cream and a razor, I asked should I shave in the shower.

She said no that it was always one of her fantasies to shave a man turning him into a cock loving faggot, the words shocked me but also excited me beyond what I thought possible. Lisa then produced a large plug telling me a cock whore like myself should get used to having my man pussy stretched, lubing it and after slipping a lubricated finger up my ass she slowly worked it past my tight sphincter. Ignoring my cries of pain, she pushed it until my sphincter relented and accepted her gift clamping down around the smaller shaft. I sighed in relief from the pain and pleasure of being stretched beyond what I thought possible. As I was lathered up, she dragged the razor across my balls stripping them of any stubble, telling me that this was just the first of my training, the freshly skin felt wonderful in her hands as I pondered what she meant. My brain swirled with anticipation as I clenched down on the plug filling my ass sending waves of pleasure through my body as Lisa continued working, shaving all of my remaining hair. Looking at my now hairless body she said I was going to make a beautiful faggot and how she couldn't wait to see her sissy suck her first cock.

Wasting no time, she brought out an enema bag filled with warm water with a hose and clamp, Lisa then told me to bend over, she then attached the hose to the butt plug in my ass, hands on the wall with legs spread she released the clamp sending warm water gushing into my bowels. The feeling was incredible like nothing I've ever experienced before, I was told I could not move until the bag was empty as she slowly rubbed my stomach. Pleasure slowly turned to pain as the last of the enema drained from the bag. Satisfied Lisa led me to the toilet and had me expel the plug and all the enema solution. This was followed by another to insure I was clean. Only then was I allowed a long shower with Lisa making sure I was scrubbed clean, afterwards she was waiting with a warm towel and gently patted my skin dry. She rubbed me down with witch hazel stinging as she applied liberal amounts to my freshly shaved skin to prevent infection, this was followed by dusting my dewy skin with baby powder to reduce any friction my new clothes may cause.

Showered, shaved and powdered she reached for a large glass butt plug to replace the old butt plug with a slightly larger one, smiling as she worked it deep into my ass. Telling me how much I was going to love having it replaced with a large cock burrowing into my shaved ass until his balls slapped my backside as she watched.

Next, she brought out a fresh pair of pink panties, pink stockings with a corset. I tried to protest what was happening when tone of Lisa's voice changed from a suggestion to ordering me to put them on. I was naked and shaved of all my body hair and having confessed all of my secret desires to this woman I knew I had no choice. First, she put the corset on me and tightened it as it sucked the breath out of me, satisfied it would go no tighter she pushed me down on the bed.

I started to tell her I didn't want to go any further when she slapped me, staring into my eyes, she told me there was no going back and that I was now her personal Cock sucking slave. Lisa who I must address as Mistress now showed me the audio video of me confessing wanting to be shaved and in panties sucking cock and having my virgin ass plowed and bred by a real cock instead of strap-ons and vibrators.

Beaten I slid the stretchy nylon pink hose up my smooth legs, the hose hugging my legs as they massaged them. The sensations of the huge butt plug stretching my virgin ass and the hosiery sending a million messages to my brain of pleasure caused blood to rush to my cock and leaking precum.

My engorged cock and balls pushing any reservations from my mind about who I am, Mistress Lisa commented that it appears someone likes her hosiery as she wiped the precum from the tip of my cock and spread it on my lips before helping me connect the corset straps to the hose. She laughs as I reach for the pink panties wanting to feel them around my hairless cock and balls, sliding them up effortlessly over the stockings while Mistress tells me how sexy I've become, pulling into place the tight panties they cradle my cock and balls, more precum leaking from my inflamed mushroom from the pleasure of thousands of little fingers arousing every inch of my nylon clad body. unable to ignore the truth, I now admit to myself that this is who I am, and I belong to Mistress Lisa

Mistress informs me that I need to finish getting dressed so we can go shopping for some new clothes, seeing the fear in my eyes she assures me I can wear the pants and shirt I came with over my panties and hose. Breathing a sigh of relief, I quickly dress making sure to hide any evidence of my secret. Mistress informs me in public I may call her Lisa but do not question me at any time for I am your Mistress, and you will receive punishment for any indiscretions, I reply yes Mistress.

I wasn't sure to be thankful for the long ride out of town to do the shopping because of the butt plug stretching my ass or the corset crushing my chest, we finally arrived at the shopping plaza to my relief. I soon would regret arriving as Mistress would announce in every store that we were there to buy girly clothes for a new sissy cocksucker, this always received a chuckle from the staff to my embarrassment. Mistress would only comment that I will learn to embrace my embarrassment. After a full day of shopping buying panties, garters, stockings, short skirts plus any number of feminine items and a selection of double sided dildoes, I was ready to leave when we passed a hair salon. After a quick look at my hair Mistress Smiled as she pushed me through the door.

The gal in the salon said she was closing but stopped midsentence upon seeing Lisa, her eyes lit up as she said she could squeeze us in but would lock the door to prevent any other customers. We stood as she locked the door, and she came over and hugged Mistress Her name tag said Jenny and she was gorgeous with a smoker's voice. I instantly knew that this was planned by Mistress, she immediately took charge explaining she was making my fantasy come true by turning me into a Cock sucking sissy and that I need a haircut to match. Jenny was delighted and asked me if it were true, I was too ashamed to answer so Mistress slapped me and ordered me to remove my man clothes. As I peeled off my clothes revealing my corset, stockings and panties Jenny couldn't resist running her hand down my ass tugging on my butt plug exclaiming I have the perfect cut to finish turning her into a beautiful sissy. Jenny led me to the chair and put the apron around my neck, but instead of cutting my hair she began to pluck my eyebrows, asking Mistress would she like the full treatment. I'm sure the sissy would be disappointed with anything less. With that Jenny went to work transforming me into a full-fledged sissy, as she did this Mistress told her about how she found me wearing panties and begged to be shaved and suck cock then be ass fucked and bred,

Mistress told me I was going to be the prettiest cocksucker she's ever created. I froze at this, was I just another conquest. with this thought in mind my hair began to fall in clumps as Jenny whispered in my ear, look in your lap sweetie your old life is gone, this is your new one. My head was pushed forward, and I heard the clippers as the cold steel touched the nape of my neck, as they moved upward.

Hair the color of mine began to fill my lap, after a few minutes the sound of the clippers stopped. I looked at Mistress who smiled and said I would like it a little tighter, as I will want to feel the hand on the back of my neck as cocks were forced down my throat, as I began my new life as a sissy. Jenny removed the clipper guard as the sound began again this time leaving a shorn head with a small crown of hair on top.

Jenny brushed away any stray hairs and shook out the apron, but before I could protest, she produced a gun piercing my ears. Mistress handed her earrings we had purchased earlier not knowing they were for me. As she pushed the pins thru my ears, she told me that I made a beautiful sissy. She slowly turned the chair towards the mirror as I caught a glimpse of myself. I could not believe in a day I've been transformed into this beautiful woman.

Mistress said it was time she saw those Ruby lips wrapped around a cock as she looked toward Jenny who was removing her smock to reveal bra and panties with a huge bulge. She pulled down her panties revealing a huge cock with precum leaking from its mushroom head. I wasn't the first-person Mistress had flipped but I no idea beautiful Jenny was one of her Gurls and didn't care as I dropped to me knees in my lust to suck her dripping cock, Jenny laughed as she told Mistress this one definitely is going to be an eager learner as I waited to taste my first cock, I crawled to her and opened my mouth taking in her mushroomed head. It felt so smooth and velvety with a slight musky taste, I swirled my tongue around the head before she gently pushed her cock deeper into my hungry mouth. I began bobbing up and down trying to take more of her massive cock only pausing for air. Every time I pushed a little further down her shaft, I could see my lipstick marks which made me want to take her deeper. I wanted desperately to taste her cum. Mistress encouraged me to enjoy living out my fantasy just as Jenny began stroking her cock sending a stream of her seed in my mouth and down my throat. Mistress scooped up what I couldn't swallow and spread it onto Jennys still rock-hard cock.

Coming up behind me Mistress worked the plug from my ass and spread my cheeks inviting Jenny to fill the gap left behind with her cock still hard she quickly slid her cock up the crack of my ass, finding the void she plunged her stiff shaft deep into my ass stretching my sphincter even further. Any pain quickly subsided as she began plow my ass with her shaved balls banging against my hairless ass. Mistress asked if this is what I wanted, to have my ass filled with hard cock and to be bred like a sissy faggot. I cried yes as I rocked back meeting her thrust wanting her to spill her seed deep within me. As she pounded my ass I felt a slow boiling deep within me, an orgasm building as my prostate was being awakened and all of my fantasies fulfilled, Streams of cum shot out of my aching cock splattering my chest and chin. My sphincter muscle grabbed hold of Jennys cock buried deep inside me and milked it causing her to drive it deeper smacking her balls against my ass before delivering her precious seed into my virgin ass.