Parking Lot Fender Bender

I was a 19 year old kid struggling to make it on my own, late for work I backed my old toyota out of the parking spot and bumped into a new Mercedes convertible setting off the alarm. I instantly pulled back into the parking spot and got out to appraise the damage with the thought that I could barely afford my car insurance as it is. Relieved that that damage was very minimal to the Mercedes I waited for the owner to return after calling work and telling my boss I would be late, he informed me not to bother since I no longer had a job since I couldn't make it to work on time.

The stress of losing my job, the accident and needing to make rent caused me to start crying as a attractive woman in her late 30's approached and asked if I was ok, I looked up and explained what had happened wiping the tears from my eyes. she put her arm around me and whispered everything would work out. She explained that she owned the car and could see no significant damage and that she was impressed by the fact that I stayed to take responsibility, she introduced herself as Jen Acme and that she was looking for a young man such as myself for work around her estate that was trustworthy. I finished wiping away the tears and introduced myself as Jim and told her that I only had limited skills. She smiled saying now she was sure I was the right young man for the job because of my honesty and she was sure she could make use of the skills I possessed. I was given her address and told that she would see me at 8 in the morning. I thanked her and she gave me a hug and told be careful driving home, this is when I first felt the physical attraction I had towards her as my cock grew in the pink panties I was wearing.

When I got home I couldn't resist the urge to jack off fantasizing of Jen, I pulled down my shorts and quickly pulled my blood engorged cock out of the silky leg band and almost immediately started to spray ropes of cum splashing my chin and chest. I scooped the cum of my chest and licked it of my hands pretending it was Jen forcing me to eat my mess. I was still hard and worked a vibrating anal plug up my ass and repeated the scene again emptying my balls sending more cum on my chest and pretending to be forced to eat it. After this I took a shower and sat down and looked up Jen on the internet and was suprised that her family had a controlling interest of a large drug company, then googled her address to find a sprawling estate secluded on the outskirts of the city.

I was amazed how someone like myself could get a opportunity like this, I was raised in foster care and at 5'7" with a slight build was never comfortable around girls. I suppose that was why I started stealing and wearing womans panties from my foster care mother and after leaving started to buy them on my own. I found that I preferred the hi-cut and nylon panties because of the way they stretched tightly around my cock and had aquired enough to throw out all of my male underwear. I picked out a fresh pair of white panties and slid them up my leg and tried to get some sleep.

After a restless night alternating between fantasies and fear of blowing it I left my apartment and drove to Jen's estate stopping at a entrance gate and pushing the speaker button, immediately the gate started to open and a voice said to come to the main house, I passed through the gate and down the driveway, Jen met me at the front door looking stunning wearing a short wraparound dress that stopped at her mid thighs accenting her tanned and toned legs and her perfectly proportioned breast. The light shone on her chestnut brown shoulder length hair pulled back into a ponytail showing her natural beauty as she smiled and welcomed me in.

She appeared to not notice my amazement of her home as she invited me to take a seat, Jen began by asking me about myself and I told her about my childhood and what I was hoping for. At this point she knocked me back with her forthright manner asking how long have I been wearing panties, embarrassed I started to deny that I ever wore panties when she put her hand on mine and said I had shown myself to be honest up till now and not to be ashamed. Explaining that she noticed my pink panties yesterday and was hoping to see if I was wearing panties today. I slowly stood up and dropped my shorts for the first time sharing my secret fetish, Jen smiled and told me she noticed yesterday that I was wearing panties as she cradled my cock trying to bust through the nylon fabric.

Jen proceeded to tell me the real reason I was invited to her home, her personal assistant was leaving to get married and she was looking for someone to replace her, standing with my shorts around my ankles and my cock straining against my panties I explained I had no experience in being an assistant. Jen told me that would be the easy part and if I was interested she would explain the most important requirement. Knowing I would never get another chance like this I would do anything. Even so I was suprised but not deterred when she told me what was required.

Jen told me when she saw me wearing panties she knew that I would be the perfect replacement as her assistant. I would dress and live as young woman full time, all my male possessions would be donated and be replaced with feminine clothing etc. She further explained that i would submit to all of her sexual proclivities and would be available for the pleasure of business associates and friends. She would be my Mistress and would be addressed as such at all times while on the estate. I would submit to estrogen therapy to transform my body to a more feminine shape, in return I would live on the estate with a generous salary and a car. I would have to agree to a written contract to be in her service for a year then would be renewed with a substantial raise if my performance meets her expectations.

I wasn't sure what would exactly be required of me but knowing I would always struggle in life, I jumped at the chance. Not having to worry about where I would sleep at night or if I would be able to eat, I said yes. Jen smiled and told me the contract was already written and we could get started as soon as I signed.

With the ink dry on the contract I was led to a large room with various restraints, a chair with stirrups, some sort of saddle, numerous tables, strap-on dildos, anal plugs and devices that I had no idea what they were used for. When I looked at Jen in bewilderment she laughed and told me not to worry that I would enjoy all of them in due time. A pretty girl dressed in a short skirt introduced herself as Susie and told me to remove all of my clothing. She smiled and commented to Jen that I was perfect. After stripping my clothes were removed and Susie took a small set of electric clippers and started removing my pubic hair, within a few minutes my cock and ball area was shorn to a short stubble. She then proceeded to remove all of my body hair, my cock bobbing and leaking pre-cum as the clippers sent a electric charge through my body. She then explained that Mistress wanted me shaved clean from the neck down until electroylis would permantely remove my body hair. Next I was told to sit and place my feet in the stirrups as she spread shaving cream on my legs, cock and balls, she wielded the razor and quickly denuded my body of any hair. I will never forget the feeling of being hairless for the first time as she raked the razor across my body. I wanted to grab my cock and get some relief but I knew on some level that my cock didn't belong to me anymore.

Mistress sat and nodded her approval as Susie sprayed me with witch hazel stinging my leaking cock and balls then moving to my ass and legs. Mistress told Susie to make sure I was clean inside and out before doing my make up and nails. Also to cage my little clit before being dressed. I was lead out of that room into a shower where I was flushed out repeatly with an enema, this was my first time having an enema and found it highly erotic as she worked a lubed finger up my ass working it in and out preparing it for the inflatable enema nozzle. As she did this she pumped my cock and concentrated on my prostate, I knew then that I made the right decision as she told me that I would make a fine sissy slut while commenting on my tight ass. My knees went weak as I pumped a load of cum emptying my balls into her waiting hand which she brought up to my lips, ordered to clean her hand I eagerly lapped up my cum and sucked on her fingers licking any remaining seed. Your Mistress will be pleased when she finds out how much you enjoy swallowing cum because you will always be required to clean up your mess and others with your tongue. Susie smiled as she pulled her finger from my ass and worked the enema tip into my ass and inflated it stretching my sphincter causing me to let out a soft moan as she released the clamp filling my insides with warm water. As the water flowed in, She took advantage of my orgasm and shoved my deflated cock into a cage and locked it. She explained that my cock would remained locked up and only released for Mistress Jens pleasure, I nodded my understandind and was given instructions on how to care for my encased cock. The cleansing continued and after expelling multiple enemas I was told to shower.

Satisfied I was clean, I was told to towel off and was led back to the room with the restraints. I sat down while still naked and I was given a manicure and pedicure then my nails were painted a bright pink, while my nails were drying my eyebrows were plucked, and make up applied. Next a apron was wrapped around my neck, the cool material resting on my hairless body causing my cock to fight the restraint of the cage, I heard the sound of electric clippers as my head was forced down. The cold steel was placed at the nape of my neck and worked its way up causing clumps of my blond hair to fall into my lap, this was repeated until my lap was filled with hair. Just when I thought the assault on my scalp was done Susie removed the guard on the clippers and I once more heard the sound of the clippers as they were pressed close to my scalp. This time short hairs floated into my lap as she explained Mistress requested a tight cut, she ran the clippers to the crown of my head leaving a patch of hair about a 1/4 high on top. She had left approx a swath of hair approx 1 inch wide towards the front which she then trimmed into bangs about an 1 1/2 inches long. She then used a soft brush sweeping any remaining hair off my head onto the apron. Unclipping the apron she shook my hair to the floor. Looking at her through the mirror I could see her smile as she told me now I truly looked like sissy cocksucker I was meant to be. Seeing the look on my face she laughed as she said I must not have read the contract I signed

An older lady then came into the room carrying clothes that I was to wear from now on in service of Mistress Jen. This was a pink garter belt, pink panties and bra with padding, flesh colered hose and open toed shoes. Susie helped with with the garterbelt, I rolled the stockings up my shaved legs causing my cock to strain against the cage it was imprisioned in. The feeling of the hose against my smooth skin was indescribable, in a short period of time I have experienced sexual tension and desire that I would never have believed possible. I trembled from excitement as managed to attach the stockings to the garter straps and began to slide my panties up my legs. My cock bobbing and rebelling against its imprisionment as the panties glided over the stockings to cradle my cock and balls nestled in its cool smooth fabric. I paused to appreciate the massaging effect on my skin before stepping into the shoes, Off to the side was a summer dress which I slipped into. Its hem falling mid-thigh brushing the stockings that sent sparks up my spine and into my balls and causing my sphincter muscle to spasm.

Satisfied Susie took me to another room where I was presented as Jaime to my Mistress who was waiting attired in a black corset which showed off her firm tits with light brown nipples, black stockings and high heeled boots. Her pussy was hairless and smooth, she looked every bit the dominatrix that she would prove to be. I instinctively knelt in front of her as she inspected her new slave, she ran her hand over the back of my head complimenting Susie on a job well done. Mistress explained my head would be shaved in this manner while I transformed and learned to love sucking cock, My first estrogen treatment was administrated in the enema that I received and only required the catalyst to activate it. Susie told how I greedily ate my cum and said I'm probably a natural born cocksucker. This seemed to please Mistress who was amazed how quickly I was adapting to my new life.

She pulled me to her cunt, I took in the aroma as I stuck out my tongue for my first taste of pussy, I slipped it in between the folds and was rewarded with a buttery sensation as I lapped up her juices. Though inexperienced I did what I've seen watching multiple porn videos finding her clit and concentrating on that button. I was soon rewarded with Mistress bucking and grabbing my head and pulling me further into her moist pussy. Satisfied she pushed me away and reached for a double sided strap-on dildo, burying one side of it into her wet pussy. Susie helped her adjusting the straps and told me to bend over after applying a generous amount of lubricant on her stiff cock. She lifted the hem of my dress and slid down my panties and worked the lube in and around my sphincter muscle elicting moans from me as I arched my back and rocked to meet her invading fingers. What an eager little slut you are Mistress commented as she positioned herself behind me. She rubbed her cock up and down the crack of my ass, telling me what a nice ass I have well aiming to take my virginity.

She found my asshole and probed my sphincter slowly working her cock into my ass, having worked a anal plug up my ass yesterday it easily swallowed her hard cock. Mistress was delighted as she slowly buried it deep into my ass, She was slowly working up a rythym as my chin was lifted up. Susie had pulled her panties down and a rigid 7 inch cock was being pressed to my lips, As Mistress picked up the pace she told me that Susie was her assistant leaving as her cock found its way past my lips and into my mouth. The musky taste flooded my senses and I was amazed at the smoothness of her cock, maybe I was a natural cocksucker because I loved the feel of a cock sliding in and out of my mouth. Mistress was soon pounding my ass working herself to a orgasm and I rocked back to meet her every thrust while pulling Susie's cock deeper into my mouth. Every nerve in my body was on edge with my cock straining in its cage as Mistress brought herself to orgasm burying her cock deep in my ass. I continued to suck on Susies cock while Mistress recovered and slipped her cock from my ass leaving it wanting for another invader, Susie slowly withdrew her cock from my mouth with me wanting more.

Mistress impressed with my performance instructed my cock be released from its confines which promptly responded by growing to its full length, She then instructed Susie to finish breaking in my virgin ass. She quickly grabbed me by the hips and plunged her cock balls deep into my ass as I pushed back meeting her thrust slapping my balls against hers, my sphincter stretched and prostate massaged by her cock we quickly devolped a rythym. We were like two animals, her wanting to bury her cock in my ass and me wanting it deeper as my body was on fire. Soon it became too much for me as I shot ropes of cum with an orgasm never touching my cock. My cock was bobbing back and forth and my sphincter was clamping down on her cock. She continued plowing my ass with her rigid cock then buried it deep in my ass. I could feel her cock as it spasmed releasing its load. Exhausted I collasped as her cock softened and fell from my ass leaving an empty feeling again as her cum began to trickle past my spincter. Mistress pleased, reached down and scooped up my cum and brought it to my lips. She told me the estrogen catalyst was the cum Susie just deposited deep in my ass and that I was going to make a wonderful assistant, eager to please on my first day on the job I licked them clean.