Paul's Sissy Journey

I am a 32 year old married sissy, previously named Paul, who is continually at the beckon call of my wife. A relationship that developed slowly following our wedding 5 years ago. A surprising turn for a guy who always considered himself to be self-assured and in control. But I digress.

Losing My Virginity:

As far back as I can remember, I always tended to be more of a leader than a follower. In high school I was very involved in sports, being the captain of both the basketball and volleyball teams. I suppose I was considered to be very popular in my high school years, although I seemed to gravitate more to sports and music and not so much towards the opposite sex.

It wasn't until my freshman year in college that I lost my virginity. I got a job working in a retail music store as a salesperson right after starting college. My manager, Lynne, was a lady about 10 years older than me at the time. I did not consider her to be extremely attractive by any means. She was a bit overweight with long reddish hair and freckles. She did however have some large, luscious tits that were very prominently displayed in every outfit she wore.. She made it apparent right from the start that she was in charge of the store and I was to do as She said. Her strong personality and her mature attitude became quite alluring to me and I would find myself daydreaming about what it would be like to be intimate with her. I was soon to find out!

After working with Lynne for about a month, I found myself alone in the store with her one night doing the year-end inventory. We were towards the rear of the store. Lynne was sitting on a stool from a drum set holding the inventory sheets, jotting down the numbers from my counting of the different items on the shelves. Her beautiful breasts were literally poring out of a tank top that she was wearing. I was having a difficult time not staring.

"Paul, you seem to really like my tits. I noticed from the first day you started working here that you couldn't seem to take your eyes off of them."

Shocked and surprised, I stammered, " Yes, they are so sexy. I am sorry Lynne."

With a big smile Lynne looked up at me and with her take-charge attitude told me to come and stand before her.

" Are you a virgin Paul?" she asked.

Blushing immediately following the question, I stated what I suppose was the obvious answer to her, that I was indeed a virgin.

"Look at me Paul. It's nothing to be ashamed of. Actually, you are a very fortunate guy. Because you see Paul, you are going to learn all about sex from an experienced older woman who will lead you and guide you into becoming a very dynamic lover."

As she was telling me this, her immaculate manicured hands were unbuckling my belt and unzipping my 501 jeans. Pulling my shorts down, Lynne had my cock in her mouth before I could even understand what was going on. I was hard instantly, and her oral ministrations on my virgin manhood had me immediately panting and moaning. Her mouth swallowed my dick all the way to my balls, over and over again. Her deep- throating skills, I would learn later through other experiences, were second to none. She never gagged, she never wavered, she just was a marvelous cock sucker. Needless to say I came very quickly filling Her mouth with copious amounts of cum. I remember almost staggering over as I came, but she held my hips and sucked very bit of cum out of my cock. Lynne looked up at me and smiled as she swallowed all of my seed.

" I think we are done here for tonight Paul. Now when we leave you will follow me to my house. Let's get out of here."

Lynne lived very close to the music store and we arrived at her front door about 15 minutes later. As soon as she opened the front door and closed it behind us, she was unbuckling by belt again and pulling my pants off. She forcefully pushed me onto the carpeted floor in the foyer and began earnestly sucking my cock again. This was like a dream come true for me and I was once again in a wanton sexual state. As she was blowing me again, I heard the sound of keys rattling in the front door but it did not seem to slow down Lynne from her sucking my hard cock. Her roommate, a slender younger blonde, was smiling down at me with a mischievous grin on her face.

" Hi guys," she stated nonchalantly.

Removing her mouth from my cock, Lynne replied. " Hey roomie. Meet Paul. He has a gorgeous cock and will be hanging around here quite a bit in the future. Until tonight he was a virgin. But you know me, always a push over for young, untouched meat. Take a look at this beautiful dick."

"Hi Paul, I'm Barbara. And that is indeed a luscious cock.. Very nice."

I was, for lack of a better word, both smitten and speechless at the incredible scene that was transpiring before me. These two women were so comfortable discussing sex and my cock that, rather than being mortified and embarrassed, I was put at ease and I truly believe this attitude toward sex laid the foundation of how I would look at intimacy in the future.

My relationship with Lynne and Barbara continued for 2 years. Every night consisted of some sort of sexual encounter with one or both of the women. I was instructed in the finer art of pussy and ass eating as well as the many myriad ways to fuck. I was, as Lynne stated at the outset, a "very fortunate guy."

Meeting Crystal:

Following my wonderful two years of "apprenticeship", I headed off to college, and even though I continued with my involvement is sports, sex was now a big part of my persona. I had numerous relationships both during my college days and following. I was always the Alpha male in all of these encounters and I seemed to gravitate to rather submissive women, or at least now looking back I can say that. At the time I was blinded by their beauty and the eroticism of engaging in sex with them.

Once out of college, I got into Real Estate sales and never looked back. So except for the time working at the music store, I was always self-employed and my own boss as well the boss of the assistants that I eventually hired. I was the one who made all the decisions day in and day out.

When I was 26 years old, I was representing a buyer who was interested in a commercial building in Century City. It was a high end purchase and the negotiations seemed to be stalled because of the constant questions being sent to me by the seller's attorney.

Finally, when I realized these questions were delaying any chance of completing the purchase, I reached out to meet with the seller's attorney, Crystal Huntington. A meeting was set up and I was given directions to her office, which was perched atop a high rise, also in Century City.

I was taken to a conference room and asked to wait for Ms. Huntington. At this point I was a bit pissed and was anticipating letting my feelings be known to Ms. Huntington when she came in to meet me. Boy was I wrong!

Now I have heard of some women commanding a room, but the vision that entered the conference room that day could command a Universe. I literally swallowed my tongue when she came in and sat down. A raven haired Goddess sat across from me, dressed in a tailored business suit with a short black skirt, stiletto heels and seamed hose. A sleek white blouse was visible under a bluish jacket. Everything about this woman screamed class and authority. I was fucked!

But much to my chagrin and surprise what followed was a very intelligent, pleasant meeting that concluded in us both agreeing to the terms of the sale.

With a smile that literally melted me, Ms. Huntington ended the meeting by stating. "Well Paul, not that we have come to terms and solved any disagreements we might have had, it is imperative that you take me out for a celebratory drink. First off, you will call me Crystal, no more Ms. Huntington. And secondly, you will pick me up at this address promptly at 8pm."

She scribbled her address on a sheet of paper, slid it over to me and abruptly left the room, never giving me a chance to even acquiesce to meeting her later. I had never met or been treated in such a way, but I must say it was incredibly arousing.

At exactly 8pm I pulled up to Crystal's home, a magnificent structure built on the cliffs overlooking Malibu. When she answered the door, I once again was taken aback by her unbelievable beauty. Standing before me was a woman so out of my league that i had to pinch myself to stay in the moment. A tight black corset, looking as if it was painted on her body, was the first thing that captured my complete concentration. Her long dark brown hair flowed over her shoulders in such a way as to bring a man to his knees. A pair of spandex riding pants also clung to her and a powerful pair of leather riding boots completed the vision before me.

"I am guessing you like what you see Paul, since you are standing in my doorway gawking at me. Please come in."

I tried to apologize but she just smirked at my feeble attempts.

"I have a car coming around in a bit to pick us up. Now be a dear and sit down and relax. I promise I won't bite...yet."

She pointed to a chair in her living room and I staggered over and sat down. I can't really explain what had gotten into me, but I knew I was mesmerized beyond anything I could imagine. I felt like a child in her presence and I realized immediately that this was a woman who, like me was the decision maker and the Alpha dog.

Our first date was fantastic. Crystal sucked my cock on the way to have drinks, and on the way back she had me lick her pussy until she came violently, squirting all over my face. I spent the night and was virtually with her every night until our wedding day. I had gotten used to Crystal being the dominant partner in our relationship and actually was relieved to relinquish my lifelong Alpha role to someone such as her.

After we married, Crystal had me rent out my home near the beach and we lived in the cliff house overlooking Malibu. Both of our careers took off and within a few years time Crystal was made a partner in her law firm and I had a team working under me selling lots and lots of Real Estate. We amassed quite a healthy portfolio and approximately 3 years into our marriage Crystal had decided that I would start to extricate myself from my business and become more of an assistant to her, helping her from our home to manage our portfolio and help out with some of her scheduling.

SHE TAKES CHARGE:

As in any vanilla relationship as the months and years went by our sexual escapades with one another were not what they once were. Crystal was working all the time, and by the fourth year of our marriage I was basically relegated to running her affairs as an assistant and catering to her needs. I had given up my Real Estate career ( we certainly did not need the money) in order to be able to always be available for her. When we did have sex, I was always expected to orally pleasure her pussy and ass. Many, many times I did not cum during our sexual play. I was getting a bit frustrated and pissed off at being treated in such a way and started acting out in a somewhat rebellious way. I stopped working out all the time and soon was sporting a beer belly. I was certainly drinking too much and also neglecting many of my duties that Crystal expected me to do for her on a daily basis.

And then the sex stopped!

Every day that Crystal left for work she was just as beautiful and alluring as the first day I set eyes on her. And yet, our physical interactions were becoming a thing of the past. With all of the young, handsome bucks that Crystal employed at her law firm, I had my suspicions that my wife was seeking her gratification elsewhere.

I began really getting into a lot of different porn sites, and during the day, while she was at work, I would spend hours and hours on the computer. And when I discovered the world of feminization and sissification, well, my viewing became an addiction. I cannot explain it, but hot sissies all dressed up in heels and hose and garters and corsets, with their clitties caged in chastity just began to rock my world. Fetlife was a porn paradise for me and I began messaging CD doms, asking about certain aspects of being a submissive sissy and wondering if eventually I would go to the extent of dressing femme and sucking a real cock.

I decided to get a P.O. box and began the process of purchasing femme clothes and shoes for me to wear. The first time I pulled on some silky thigh highs and a pair of crotchless panties, I was hooked. And when my first pair of black stilettos arrived I was over the moon. I couldn't remember being this aroused in years. I was literally masturbating 3 to 4 times a day while dressed femme in our house, keeping my sissy stash hidden away in a box in the garage. I soon graduated to butt plugs and dildos, seeing that a real sissy was also expected to be an anal slut.

And then my friends, the shit hit the fan!

It was a Monday, near the end of the year and Crystal had left for work as per usual. I had finished up what I now considered to be some mundane work for her and decided to watch some sissy porn and get dressed up in my sexy, feminine clothing. As I was just getting my heels on, I received a text from Crystal.

"Paul, check your email. I will be home late."

I went to my email and opened the email from my wife. The subject bar of the email simply stated "watch the attachments."

I opened the first video attachment and was totally shocked. There I was, trying on hose and heels and masturbating on our bed with my sissy legs in the air. I began shaking and sweating, and as I opened each other video they literally had captured my metamorphosis into a sissy anal slut. Crystal had never told me about the cameras hidden throughout the house and it occurred to me that she had a good idea as to what I was up to for a very long time.

I tried texting and calling her, but there was no response. Her text has said she would be home late so I got back into my masculine attire and waited nervously for many hours. I was in a state of a shock and literally did not move from the chair in the kitchen, sitting and fidgeting for what seemed like an eternity.

Finally, I heard the driver pull up and my heart skipped a beat. I knew it was over and with the knowledge that I had signed a pre nuptial agreement prior to marriage and that I had essentially destroyed my Real Estate career, I realized I was totally screwed.

The door opened, and much to my surprise Crystal's male assistant Jeremy came into the kitchen. He opened his briefcase and handed me a letter.

"Read this, sign it, or leave immediately." Jeremy matter-of-factly stated.

The letter was on Crystal's legal letterhead. It read.

Paul,

To say I am disappointed in you would be an understatement. For the past few months I have watched what I thought to be my manly husband turn himself into something that is both effeminate and slutty.. All the reasons that have brought you to this point are really not important to me at this time. What is important is that you need to understand what will happen now.

But before that Paul, you need to understand something about my history with relationships before I met you. As you know, my dominant personality is who and what I am and it has always been a turn on for me to be in charge in and out of the bedroom. Before meeting you, I had a variety of boi toys at my beckon call. I had made sure to turn them into my submissive little slaves whose sole purpose was to pleasure me and make my life enjoyable. Some were Alphas and some Betas. Some were manly and others, and here is what will interest you, were turned into sissy sluts for my pleasure. These sissies were stripped of all of their masculine traits and were eventually molded into cute, pretty gurls for me.

When we met, I actually had two sissies who were my exclusive pets. But for some reason, I fell in love with you and your luscious, although somewhat small cock and decided to make you my husband. And just so you know, ever since we first went out together, I kicked my sissy sluts to the curb and have never looked back.

And then this.

So Paul, there really is nothing to discuss.

By signing below, you will agree to be completely feminized by me at my discretion. You will have no say in the matter.

That's it!

If you don't sign, a car is waiting outside to take you to where you wish to go. You will never see me again and we will divorce immediately.

If you do sign, and following your signature, you will immediately go upstairs and dress in heels, hose, garters, and corset.

When dressed, You will come back into the kitchen, get on your knees, and ask my cute gay assistant Jeremy if you may please suck his big black cock.

If you are a good sissy, and you are truly focused on cock sucking Jeremy, then you will go with him. You will be taken to a lovely hotel, where my process of making you my gurl slut will begin.

It's up to you Paul. You have 60 seconds to decide!

Sign and date here: ________________________________

Witnessed by : _________________________________

Holy shit! 60 seconds. I was so caught so off guard that I had no idea what to do or think. Jeremy stood looking at his watch.

And then I signed and dated the letter. Jeremy signed as the witness.

He smiled at me and pointed upstairs. I knew that I was to follow the letter's instructions so I headed up to the bedroom to change into my sissy attire.

I was still shaking as I began to take off my clothes. But what caught me by surprise was the erection that was beginning to form. I was actually getting aroused by the thought of following Crystal's instructions. But sucking cock? I wasn't sure I could go through with it.

As I slid my heels on, I heard Jeremy shout for me to hurry up. I carefully made my way down the hardwood stairs, listening to the click clack of my heels.

"Well you aren't much of a lady yet, but I am sure Ms. Crystal will get that taken care of. Now do you have something to ask me?" Jeremy leered at me as he spoke.

"May I please suck your big black cock Jeremy?" There it was, I actually asked it.

" On your knees bitch!"

I carefully kneeled in front of Jeremy and he approached me, soon inches from my face.

This was it I thought. My crossing of the river Rubicon. If I did this now, I instinctively knew there was no going back. My life would change forever.

Fuck it!

I reached up and undid his belt. I then unzipped his slacks and gently pushed his pants to the floor. And there it was, right in front of me, another man's cock. I reached up, and for the first time in my life I grabbed the penis of another man. It was warm and soft and getting harder as I held it. I had watched enough sissy videos to know what I should do to emulate the cock sucking sluts I had viewed so many times. I started with his smooth balls, licking them and sucking them into my mouth. As I did this, I continued to hold his black cock which was now hard, thick and pretty long. He was sighing softly and the idea that I was giving him pleasure began to really arouse me. I licked slowly from his balls up to his cock. I kissed and licked at that beautiful shaft, and then, I placed his cock in my mouth. As I placed the cock in my mouth, I looked up at him and made eye contact. He was smiling at me, quietly telling me that I was being a good slut for him. I was now quite happy that I had practiced on my different dildos and butt plugs and now I began to get more and more confident in my ability to take more of his large member into my sissy mouth. I went down more and more, sucking all the while, occasionally choking but sticking to the task at hand. As I would go really deep, I would then slide off of his cock, nibbling and sucking on the large head, and then would abruptly take him deep into my mouth again. I could tell this was driving him wild and his breathing was becoming very ragged. I could feel my own cock pushing hard against my panties as I continued to tease and suck him. The eroticism was heightened as my saliva covered his cock entirely and it dribbled down my chin. I was devouring him like a proper slut! And to my surprise it felt so good, so sexy and so natural.