Journey into Feminization Ch. 01

***Chapter 01 - The Beginning

Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.).

During my childhood I always battled my weight up and down. Some years I felt confident with myself, others not so much. Looking back on it, my eating habits were pretty horrific which contributed a lot to it I came to realize. But as I grew into my teenage years, instead of diving into young blissful relationships I turned to fantasies in order to orgasm.

It first started when I understood what masturbation was and someone I knew described it as healthy. So with that knowledge at hand and growing into my body, I dove into pornography. It started with browsing websites, leading to downloading stills thanks to relatively slow internet and finally led to downloading whole movies when the internet cooperated.

I was savvy enough to keep it away from my family growing up, although there were a few close calls that I was able to talk myself out of. However as time went on my porn watching turned from vanilla fantasies (MILF neighbor, friends mom, etc.) to female domination ("FemDom"). Similar to other experiences I have read about it started with spanking, being tied up and the female controlling the traditional sex to things such as golden showers and strap-on play.

When the time came for high school I began to build confidence and become better looking finally controlling my weight. So I was able to lose my grip on porn and begin to have opportunities to date and orgasm without looking at porn. During this time my mind never really gravitated towards FemDom however I had subtle experiences looking back such as preferring the woman on top and getting pleasure out of assisting woman with homework/cheating, even if there was no sex or other reward I would get out of it, the most notable.

When the time came to graduate high school I was able to get into a college on the east coast and this meant really finding my own path. Throughout my college career the idea of FemDom slowly drifted back into my mind. This included searching notable FemDom websites for local gatherings or individuals who were in the scene. As I went to school in a large city, there were plenty of opportunities to begin to explore the lifestyle. However I always made an excuse as to why it wasn't the right time or what if someone from school saw me. So a successful college stint came and went however there was still no true FemDom experience outside of things percolating in my head.

I was fortunate enough during my college career to have a great internship within mathematics which I took an entry-level job with. During this time I began to study for the actuarial exams, which left little time for pursuing FemDom experiences. It was a long few years but the devotion to studying soon paid off as I had passed all parts of the incredibly challenging ten plus exams. At this time I was certified and a huge weight was lifted off of my shoulders.

With the exam passed, I switched jobs and moved to another large city on the east coast to begin my career as a certified actuary. As I settled into my career, the hours were long which led to flings as opposed to many serious relationships. However the idea of FemDom didn't just begin to percolate within my head however take more of a hold within my mind.

I started to look at porn again, not necessarily to experience sexual pleasure, but rather get an idea of things I was into within the lifestyle. During this research if you will by far the most excitement I got was from men being forced to wear women's clothing. The images and videos I saw were relatively tame, with typically just panties being worn and maybe a little make-up with the addition of strap-on play.

With this in mind, and a few years into my career, my searches moved from porn and into real life if you will. Given I lived in a large city I was able to search for professional Dominatrices relatively easily and the fantasies began to burn inside my head always looking for those Dominatrices specializing in 'Forced Feminization'. Still however I had trepidation in seeing one in person. Whether traveling to another city for work or in my home city I was always fearful for some particular reason. I always kept getting caught up on what if someone from work would see me or what would happen if it was truly an undercover sting and my career ambitions were ruined.

So a few years came and went and still no true sessions with a Professional Dominatrix. Instead when my roommates were away I would go down the route of phone sex and things of that nature. That would last until I orgasmed, at which point the burning desire faded for a brief period of time.

*** Chapter 02 - Introduction to Ms. L

After a couple of more years I had found myself changing jobs following a lucrative opportunity to move the Midwest. I was still continuing to use phone sex as an avenue to explore my fetishes. However I found myself having a week off of work and was staying up later delving deeper into my research. The city I was living in didn't really have much in the way of Professional Dominatrices. However after a few nights of research I had stumbled upon a magnificent Dominatrix, Ms. L, from an east coast city that I was looking to visiting more often and possibly moving once my contract in the Midwest was up.

I had remembered Ms. L from one of my previous travels along the east coast where she was residing at the time. I vividly remembered how closely I was to reaching out and contacting regarding setting up a session. However much like all the other close calls to this point in my life I chickened out and never went through with it. But for some reason she always stood out to me in the back of my mind, and when I came across her that night I thought it was fate, given I was exploring her social media profiles within the last month.

Going so far to implement one of her suggestions recently of significantly improving my skincare. It should have been done regardless, but she had indicated how it made such an impact on those wishing to be sissies.

It was late and my roommates were asleep, so I didn't want to risk waking them with me talking. Instead I noticed she had a text line, and was available, which after walking around the house to regroup I found myself back at my computer. I immediately dove in, deposited credits and said, "Hi Mistress L., i have admired You from afar and have an interest in getting into sissy play."

After a few minutes worth of waiting she responded, "Hello! It's -Ms.- L (I'm a Mistress, but I only allow my personal slaves to call me that, thank you for understanding). Thank you for the well wishes! Where are you from?"

I told her where I was from and continued conversing with her. This included discussion around my interests, which I told her varied from chastity, full transformation, and being used as someone's slut.

After diving into a little FemDom discussion, I was more enthralled than anything in the sophisticated manner in which we conversed. While I was interested in divulging the deep down fires that lay in my mind, it seemed so natural. I wasn't a fool to think this was going to become a relationship or anything like that it just seemed like we could converse so easily.

Topics included a bit about her background, where she lived, how often she came to the Midwest. Additionally she seemed keen to get into my background. She asked what about sissification was intriguing. I told her about how I had always had a desire from an early stage of life and even led to improving my skincare recently.

Upon telling her that she quickly responded, "You have no idea how much I am beaming right now that you are taking care of your skin!! So many cities and cross dressers have no idea that if they want to look like a girl they have to take care of their skin like a girl! Make up can only do so much unfortunately."

Our conversation continued for a few hours that night and it ranged from just discussing each others lives, to diving a bit more into my fantasies.

That night after we had ended our conversation, I rested my eyes. Given our conversation was the last thought on my mind before I went to bed, my head raced like no other that night. I imagined having the opportunity to kneel before her at her studio upon one of my travels for work. It was so vivid I could recall the play-by-play of the entire dream like I lived it.

It started the day before I got to the city. After having a few cancellations of travel recently, I wanted to make sure the trip was a go. I had reached out to Ms. L if she had availability tomorrow, in which she responded she did. Fortunately I had an off day and immediately booked a four-hour session following her deposit protocols.

After receiving the deposit she reached out through the phone number I had provided on my submission form and said, "Hi is this N?"

I responded, "Yes, who is this?"

"Hi this is Ms. Lydia. I just wanted to let you know I received your deposit and we are all set to go for tomorrow from 6-10. The address is N. Delaware St. If you arrive early please wait near the corner and only approach at 6 sharp. Once it is 6 please ring the buzzer at the door and you will be let in. Upon entering, kneel and place the remainder of the tribute on the floor. You will not get up until you are commanded. Do you understand?"

"Yes Ms. Lydia."

She responded, "Great we are all set then! Do you have any questions?"

"Yes should I prepare in anyway for our session?"

"Good question and I almost forgot. Given you are going to be my little sissy whore, please make sure your groin region and asshole are shaved completely. Anything more would be a plus but may be difficult in such a short period of time."

"Understood Ms. L, look forward to serving you!"

After our conversation ended, I immediately began researching places in which I could get an appointment getting hair removal. After a few calls, one of the more respected establishments had a morning cancellation and had availability before my flight. My ass and groin area was already well kept, but I wanted to make an impression.

I quickly showered and went to the salon. A friendly woman who had a smirk on her face when she confirmed a full body wax greeted me. I nodded and her smile brightened.

She ushered me into a salon booth and walked me through all the steps that would take place. She had me get undressed and so it began. Fortunately I wasn't an overly hairy male, however I got an indescribable feeling as they applied the wax throughout my body. Little by little they stripped the wax off and I felt immediate pain but kept it to myself trying to be strong and understanding this was for Ms. L.

After they were finished I felt incredibly bare and incredibly hot all over. Fortunately they had me robe and applied the post care soothing lotion and a cool towel. I left the salon with the post care instructions and spent a few more hours applying lotion and taking it easy before my travels.

As I traveled I felt an indescribable sensation. While I had not kneeled before Ms. L yet I knew I belonged to her. My skin felt so smooth against my clothing and I could hardly contain my groin rising throughout my travels and went immediately to bed to avoid edging myself, or worse, releasing myself.

After a restless nights sleep, I worked out in the hotel to avoid the sun or heat and then the rest of the morning and afternoon spent time using the lotion provided to make sure my skin was well cared for 24 hours after the procedure.

Finally, after what seemed like an eternity, it was 5 o'clock. I knew I needed approximately 30 minutes depending on traffic and got dressed and went to the nearest ATM to withdraw the rest of the tribute required. After securing it in the envelope I brought, I hailed a taxicab and was on my way.

I arrived at the corner Ms. L had described and was 5 minutes early. Following the instructions provided, I waited until 5:58 when I walked to the address provided. I waited until my watch hit 6 o'clock exactly when I hit the buzzer. After a moment there was a click and I was allowed in.

Trying to remember all the instruction I closed the door behind me, immediately knelt and placed the tribute on the floor beside me. I sat there trembling and my pulse increased as I heard her heels hitting the wood floor. After a minute she arrived from downstairs and greeted me.

I didn't look up until instructed and I could barely contain myself when I raised my head. She towered over me in her high heels, stood intimidating in her latex clad outfit and looked magnificent with perfect make-up along with her long dark hair.

After circling me for a minute, she stopped and said, "You follow instructions like a good little whore. Why don't you follow me, and crawl, do not get up."

I did as I was told following her up the stairs, instead of down. It was a little tricky crawling up stairs since the first time since infancy but managed to do it without looking too foolish I imagined. After I had successfully crawled up the first flight of stairs I followed her into the hallway and into the third door on the left.

What I found was sheer brilliance. I knew through reading her website she had a sissy salon, however I never expected this level of detail and amount of attire could be possible to be contained within one room.

Once I entered she closed the door behind me and motioned me to a sofa she had on the far back wall. This time she motioned it was okay to sit down and for the next 15 minutes we got better acquainted. I provided her more about my background and how I got to this place, which after I had concluded she began the discussion deeper into FemDom. She obviously knew sissification was the top interest of mine, which was confirmed through the excitement elsewhere in my body, however wanted to know more about my interests and limits. I rattled through the ones I knew I had which included interests of hair pulling, spitting, golden showers, strap-on play and light exhibitionism. Meanwhile the limits were severe and permanent marks (I never really liked pain and was far from a masochist), medical play, needles, fire play, along with several others.

One notable one she caught was Forced Bi and piqued her interest as to why that was a limit. I indicated never really thought of it before however would consider it soft as I said if I got far enough into sub space as a sissy slut that I would be eager.

She nodded in approval.

After I concluded she instructed me to strip off my clothes and present myself on my knees. I did as I was told and she went on to inspect me. As she was circling me she beamed with excitement, "My you weren't lying when you said you took care of your skin. I am very impressed and should make for a brilliant make over. Also I love you found time to properly present yourself and are fully shaven. This will make for a more thrilling adventure."

I didn't have any other words other than to say, "Thank you Ms. L."

Afterwards she led me to her wardrobe closet, which featured attire out of this world. The next while she spent laying out various outfits and after she was concluded pulled out a chair and commanded me to put on a show. I did as I was told trying on each outfit combination. As I was doing so she muttered her amusement and I could only help but get further aroused. After I was concluded she decided on the winner, which was a pair of pink double strapped open back panties and black nylon catsuit with my ass exposed.

Before she had me put on the attire she went to her refreshment area and grabbed an incredibly cold water bottle. She held it to my groin and I shriveled without having to be told too. After placing it on my groin she said, "Hold this here."

Doing as I was told she returned from a nearby drawer with a hot pink chastity device and said, "I don't think you will be needing any more distractions from this thing." After she concluded her sentence she locked me in the device and secured the keys around her neck.

After the lock was secured I could only muster to say, "Thank you Ms. L. it is an honor."

She proceeded to instruct me to put on the outfit she had laid out and didn't yet progress to shoes. Instead she motioned me to her salon chair where I took a seat. The following hour went by so quick. I sat relaxed as she tested and applied various make-up combinations until she found the perfect combination with a mixture of dark colors, bright red lipstick and extended lashes. Before I could see the end product, she rotated the chair away and said, "Not yet my little sissy slut."

Afterwards she went back to a cabinet and started going through her various wig collection. After five minutes she pulled away with one and returned. She kept me faced against the mirror and situated the wig which I could only tell was long in length. She spent more time and I could only imagine she was styling it. After about 15 minutes she stopped and proclaimed, "What a perfect little whore! You can certainly look the part."

Afterwards she rotated my chair and I saw the new me. If I didn't know what I was looking at it I would have thought I was a social media bimbo. I had long blonde hair, which was double braided into pigtails, and the rest of my face was utter perfection.

She continued, "Now that you look the part, why don't you show Ms. L how good you can suck a cock? Get on your knees whore."

I did as she instructed while she went to collect her toys she was going to use. Once she returned she pushed me down to the floor and applied lube to my exposed asshole.

She gasped in excitement, "So tight it is going to be a pleasure stretching out your hole little whore. However I can only call you whore so many times. I think a true sissy name will suite you. How about Kneeling Nancy?"

I responded in delight, "It would be an honor Ms. L."

She continued pressing her finger against my asshole until she could fit two fingers in. Once she was able to achieve that she quickly inserted a plug that my asshole swallowed with little effort. Afterwards her high heels clicked against the floors until she was in front of me. She applied a blindfold without warning, and continued, "Open your fuck hole Nancy."

I proceeded to open my mouth and as soon as I opened, I experienced my first thrill of being commanded to suck cock. It continued for what seemed like an hour. I licked the lifelike balls, head, and shaft and sucked in and out not minding my jaws as they began to hurt. Ms. L rewarded good sucking skills with a push of her remote, which sent vibrations into my asshole. Any bad sucking skills were addressed through a smack against my exposed cheeks with her riding crop.

After she was pleased with my skills she stated, "Nancy you are a natural born blonde bimbo. Sucking cock like a natural, if you didn't have suck a rocky start, I would have thought maybe you were lying about this being your first time. However we can't have that mouth not continuing to stretch."

After she finished she put a ball gag in my mouth while she moved to the back of me. After pulling the plug from my asshole, she inserted her strap-on. While she started slow to get started, she soon started to thrust with more fury. While every now and then I felt a bit of pain it couldn't have felt so good being stuffed like a Twinkie by Ms. L. My asshole swallowed each thrust with more ease as the time went by.

After a while the thrusting slowed and she withdrew her cock. Afterwards she took off the blindfold and removed the ball gag. After which, she continued, "Well I hope that was a lovely treat for you my Nancy. You certainly are such a slut."