Becoming a Sissy Wife - Ch. 01

At the age of 28, I made the most important decision of my life - to start a new life as a woman. I was so tired of hiding my sexy women's underwear beneath my rigid men's outer clothes when I was out every day, dressing up into full women's image immediately after back to my solitary apartment, and spending hours in admiring my female body in the mirror but not daring to step out of the room with it. I wanted to live a woman's life in the sun.

The first step I took was to quit my job as a software engineer department manager. This job had no appeal to me except for the decent salary. But wearing men's clothes every day, leading a group of uninteresting coworkers and dealing with boring code made me feel like I was living in a cage.

After putting on delicate makeup and beautiful women's clothes, I began to apply for new jobs - secretary, assistant, even shop girl, restaurant hostess, company front desk receptionist... In short, any job with a strong feminine label. I even fantasized about training to become a model or flight attendant.

Finally, I found a suitable job as a sales assistant at a large software company. I used to work for a such company, so I know that in such kind of male-dominated "barracks," the support work is mainly undertaken by girls with lower education and salary. But the work is easy, so they always have bunch of times to gather in twos and threes, competing each other with beautiful dress and make up, chattering about beauty, clothing, cooking or various gossip topics. They add a touch of beautiful color to the boring company and always make me envious.

When signing the employment contract, the HR staff also said regretfully: "With your experience and background, you can become a team leader in our R&D department and get at least five times more salary."

"Thank you, I don't want to go back to the 'barracks'. Maybe I will work hard to become a good salesperson." I quickly rejected her kind offer, fearing that the slightest hesitation would lead me back to my old life.

Just like that, I took a plunge into a whole new exiting water area...

On the joining day, I caused quite a stir in the company's sales team. My appearance and special identity aroused a lot of attention and curiosity. After a week or two, I got to know everyone and began to enjoy the benefits of being the only "female" in a whole-male team. The salespeople were more outgoing and enthusiastic than my former engineer colleagues. They helped me a lot with my work and often invited me to join them for meals and drinks. I began to become the "favorite" of the team.

At the same time, I was also feeling some of the lustful looks that fell on my face, my skirt-covered butt, and my stocking-covered legs. I began to receive some flirtatious requests for one-on-one dates. But among all my colleagues, the only one I had my eye on was Jim.

Jim was a senior salesman in the team. When we introduced ourselves to each other on the first day, our eyes locked on each other for more than 10 seconds, which was far longer than the eye contact I had with any other colleagues. Jim is a very charming man with an outstanding look and body shape. Every time I faced him, I couldn't help but blush and be shy, which I had never experienced before. As my mentor at work, Jim's help to my work far exceeded that of my other colleagues. Our friendly relationship soon developed beyond work, and we became close friends in life.

Jim often gave me good suggestions on my dress and makeup. Whenever I wore a piece of clothing that showed my femininity or put on beautiful makeup, he would always be the first to give me a heartfelt compliment. Gradually, I began to look forward to Jim's attention and compliments when I put on my makeup and picked out my clothes every morning. A wonderful chemical reaction slowly took place between the two of us...

However, I encountered a huge problem - Jim was already married. His wife was his girlfriend in college, and they had been married for ten years. Not long after, I met Jim's wife Jessica at a company party. She was obviously several years older than Jim, around 40 or so，a typical housewife. I have to say that Jessica must have been very beautiful when she was young, but she is now apparently neglecting her looks and figure, and dresses rather casually. She spent most of the party quietly by Jim's side, like an appendage of his.

I didn't get along well with her. She responded rather coldly to my warm greeting, with wary, jealousy, and even a hint of contempt in her eyes. Jessica's attitude deeply hurt my sensitive self-esteem and aroused my male's desire to win. I made up my mind to get Jim.

Soon after, I got a chance to get closer to Jim. One of his big deals in another city was about to be closed, and Jim convinced the sales director to take me along on the trip so I could get a better understanding of the project and learn some sales techniques on the spot. I was very happy to travel with Jim, and I had prepared my clothes and makeup, as well as a large bottle of lubricant.

The business went quite smoothly, and the client signed the contract with Jim at a nominal price reduction, and I was impressed with Jim's sophisticated sales skills. The night we returned, we decided to go to a bar to celebrate.

The bar was located on the top floor of a 26-floored building, and there were some stylishly dressed men and women lined up at the door as we arrived. Jim often visited this city on business, he was a VIP here, so we went right in. The building was located in a downtown area, and it fronted a river that ran through the city. The illuminated city was reflected in the water where some lighted ships passed by.

Under the catalysis of alcohol, night view and relaxed mood, the distance between us was quickly shortened. I told Jim about my growth process - how I came from a small inland village with only a hundred families to the big city to study and develop all by myself, and how I felt more and more lonely and depressed after I finally gained a foothold in the big city; how I wanted to be a woman since my teenage years, and how determined I was to get to where I am now. Jim also told me about his struggles in the workplace and his marriage...

After the third glass of wine, I finally plucked up the courage to tell Jim what was in my heart: "Jim, I like you. I fell in love with you at the first sight I saw you." After saying that, I stared at Jim's eyes nervously, observing his reaction.

Jim's also looked straight at me and replied: "Erica (my female name), I also fell in love with you since you showed up in the company."

Jim's grasped my trembling hand, and our lips touched...

We kissed for a while before I had to gently push Jim away and whispered to him, "Stop, my skirt is sticking up."

Jim quietly reached his hand between my legs and felt my swollen penis through the skirt and smiled softly. "Looks like you're a bad girl."

I reached my hand between his legs as well and felt a swollen outline that was much larger than mine. "Looks like you're worse than me." We both smiled knowingly and decided to go back to the hotel room, which was obviously more suitable for us to make further communication.

On the way back to the hotel, we happened to pass by a upscale women's clothing store. Jim took me by the hand and walked inside. I excitedly picked up a beautiful figure-hugging silk dress and compared it to myself in the mirror. But the moment I saw the price tag, I put it back. It was too expensive, more than my monthly salary as a sales assistant. Jim brought it over to me and said, "Erica, you helped me a lot with this big deal. I was just thinking of giving you a gift to thank you. I'll pay for this dress." I didn't expect Jim to be so generous to me, which touched me a lot.

Jim took me to the lingerie section and picked out two pairs of garter stockings with Cuban heels and a set of sexy and revealing corsets and panties for me. At the door of the fitting room, I pulled Jim into the room when no one was around. With my back to him, I wiggled my hips to remove the narrow skirt, as well as the blouse and shirt. Through the mirror, I found Jim reaching for his crotch. I asked him to help me unbutton my garter belt, took off my stockings and handed them to him, then smiled and said to him: "I recently found that someone always went through my stockings and high heels in the office locker. Could it be you?"

Jim's face went red, and he said embarrassingly: "I have to admit that I am one of them."

Jim's answer surprised me a little, "How many of you are there?" I asked.

"At least five from what has been made public so far. The five of us have each bet 100 euros in bonuses. Whoever gets you first will win the bonus. But, I'm afraid they may not have a chance." Jim smiled slyly.

"You bunch of pervert assholes." I pretended to be angry but smiled while my little penis became hard underneath my semi-sheer thong. I simply took off the thong and threw it at Jim's face.

Ignoring Jim who was burring his nose to my underwear and greedily sniffing the soles parts of my stockings and the string of my thong, I slid my body into that figure-hugging dress and surveyed myself in front of the mirror excitedly. The dress fits me perfectly and fully magnifies the feminine features of my body. I didn't even need to ask Jim's opinion, since his fiery eyes had already given me the answer.

"Poor boy." I sighed and squatted down to Jim's bulging crotch and unzipped his pants. I decided to repay his generosity on the spot...

The size of his cock overjoyed me. This is the biggest cock I had ever touched. I took the mushroom into my mouth without hesitation, teasing the urethra with the tip of my tongue, and sucking it hard with my mouth. Although Jim's cock was clean, after a busy day, it emitted a strong smell of sweat and male hormones, which intoxicated me.

Jim continued to savor the stockings and panties that were thoroughly "marinated" with my body fluids, while enjoying my oral service, his big cock was fully hard. Just as I was about to swallow this big cock deep into my throat, Jim pulled me up and turned me around and made me support myself on the wall.

Feeling the dress being lifted to my waist, I saw from the mirror that Jim had squatted behind my round ass.

I couldn't help but let out a squeal as Jim pulled apart my ass cheeks and pressed his hot, wet tongue against the opening of my boi pussy. A sharp, high-heeled footstep moved to the door, followed by the voice of the female clerk: "Ma'am, are you okay? Do you need help?"

"No, it's okay, I, I was careless and didn't stand still." I hastily covered up.

The female clerk, who was still worried, didn't leave the doorway until she had confirmed with me several times. During this time, Jim's tongue had traversed every wrinkle of my hole and began to invade my sissy pussy with the tip of his tongue. The tension and pleasure made my legs tremble so hard that I couldn't control them with my consciousness.

Jim turned my body, which was about to collapse, over so that I was leaning against the wall. Taking my sissy "clit" into his mouth, he began to suck it while bobbing his head back and forth.

The risk of being caught at any moment turned me on like never before, so I cum in Jim's mouth quickly. As my body slid down to the floor, I stuck out my tongue to catch Jim's approaching mouth and swallowed every drop of my cum from his mouth. At last, I gave his tongue a gently bit as the punishment for his rude action.

At that moment, the door of the fitting room was knocked by the previous female clerk. "Ma'am, are you okay? You have been in there for more than 20 minutes?"

I couldn't believe that time passed so quickly because it was like we had just come in for a few minutes. I stood up with Jim's help. Without time to put on my panties and stockings, I simply let Jim put them in his trouser pockets. Then we straightened up our clothes and made our way out of the fitting room.

The telltale white liquid remained on our face made the female clerk's face instantly harden. Jim paid the bill and left a nice tip, then we fled the store in a hurry. It wasn't until we were a block away that we both burst into laughter with relief. We hugged and kissed and licked off the white stains on each other's faces...

Kicking the door of my hotel room shut with my heel, I began to serve Jim to undress like a dutiful wife. After hanging his suit, shirt, tie and pants neatly in the closet, I removed my dress with Jim's help.

Jim's "awakening" cock caught my attention and I decided to take some measurements of its size. I knelt and swallowed it into my mouth. My lips didn't touch his pubic hair until I had struggled to get his glans into my throat. I pressed my lips on it and left a distinct circle of red marks on the base of his cock, then with the measurement of my fingers, I withdraw a length of two fingers wide, leaving the next red mark... until the sixth mark landed on the crown of his big cock. Finally, I brought my middle finger and thumb into a circle and clamped it to the thickest part of his cock to measure its thickness.

"Fuck, Jessica is so lucky. Your cock is at least 20 centimeters long and it's almost 5 centimeters in diameter and it's still growing." I said in surprise.

Jim laughed unknowingly and put his big, semi-erect, heavy cock on my face. His balls touched my chin, and the glans landed on my forehead, and the cock shaft with six neat lipstick marks almost covered half of my face. After Jim took some memorable pictures of my cock-covered face with his phone, I took his big cock back into my mouth and bobbed my head back and forth, all the while keeping my gaze looking adoringly into his eyes.

Jim enjoyed my oral service for a while and then called a stop. He lifted me to my feet and clasped his hand around my buttocks, and together we headed for the king-sized bed. My boi clit, which was only half the size of his cock, began to wake up as well, swaying in front of my crotch.

We got to the bed and Jim pulled out the stockings I had taken off at the store for me to put back on. Having just put on half of the stockings, I raised that leg in the air like a professional stripper, and teased Jim with my red nail-polished toes.

Grabbing my teasing foot in the first place, Jim began to lick the sole and suck the toes greedily.

I couldn't help but giggle and playfully asked, "Do you addicted to women in stockings so much? Doesn't your housewife wear stockings?"

"Jessica is fairly conservative，she hate stockings, especially these sexy ones, and thinks they are whores' wearing." Jim replied.

"Well I'm now your paid whore, you can do whatever you want to me." I slid on the other half of the stockings and buttoned up the garter belt. Hooking my feet together in the air, I made my legs into a big O shape, and then squeezed my arms, head and most of my torso through the center of the O. I ended up in the highly difficult "pretzel pose"，inviting the male to mate.

Stunned by the flexibility of my body, Jim gave me an incredible expression.

"I bet your housewife must not be as good at yoga as I am, huh?" My tone was filled with pride.

"No, Jessica thinks only sluts use the pose other than missionary pose."

"So am I slutty enough?" I asked mischievously.

"You're a nasty, bad girl. But I like you."

I took out the lubricant under my pillow and squeezed it into my boi pussy, then with two, then three fingers, I stretched my slutty bussy in front of Jim. Meanwhile, I stuck out my tongue and smiled, shamelessly giving Jim an inviting "come and fuck me" look.

Jim picked up my heels from the floor and put them back on my feet that were located behind my head. "I prefer to fuck the bitch I paid for in stockings and heels."

But instead of sticking his big cock into my watery pussy as I wanted, he once again bobbing my clit with his mouth while digging my waiting pussy with two, three, then finally four of his fingers.

Soon, I was so horny that I twisted and said in a charming voice, "My slut hole is completely relaxed and I want you to fuck it with your big cock."

This time, Jim stood up and stuck his iron-hard cock towards me. I grabbed his big cock and squeezed some lubricant onto it as well, then held the rod and ground my hole with the big glans. Jim lowered his body, and his huge glans slowly opened my anal ring. I wrapped my arms around Jim's torso and pulled him against me while moans of pain and pleasure escaped from my lips.

"Oh, it's so BIIIIIIG!" I closed my eyes and hugged Jim tightly, desperately sucking his tongue to ease the pain caused by his rod impaling my body inch by inch.

Finally, his two huge balls touched my ass announcing the end of impalement. Like a natural matching pair, my pussy wrapped tightly around Jim's erect cock. Both of us widened our eyes in surprise at the same time, marveling at this amazing perfect fit.

"Oh My God. My 'saber' finally found its long-lost 'sheath'." Jim exclaimed sincerely. As if to reconfirm the fit, Jim slowly pulled his cock out of my pussy and then plunged it all back in again.

Jim began to test his 'cock sheath' again and again. His big cock would kept staying outside my hole, waiting my hole to be closed, before it squeezed through my anal ring and entered me until his balls finally hit my ass again.

Being repeatedly opened from its initial closed state, my anal ring was forced to experience the penetrating pain and pleasure over and over again, causing a guttural moan to escape from my mouth. In order to please Jim, and also to satisfy my own desires, I used my special technique which I had been trained by an elder Sugar Daddy. Whenever his big cock was inserted, I deliberately relaxed my sphincter muscle to let the "invader" go straight in; whenever his balls hit my ass, I tightly contracted my muscles and squeezed the "intruder" so hard that it was difficult for him to pull out, until his mushroom popped out of my hole with a "boob".

This technique would multiply the pleasure for both of us, but it would also increase pain for both of us. Thanks to my long-term Kegel training and the daily grind on the dildo, my pussy is very tight while my sphincter is very strong. Usually, within three minutes, my opponent would either begs for mercy or "leaks" in my cunt.

Jim, as expected, was moaning in agony. A mischievous grin appeared on my face at the thought of this strong stud begging for mercy with his cock clamped by my cunt.

But three minutes passed, and although Jim's moans were uninterrupted, his big, hard cock was still plundering my "city" wantonly.

Another three minutes passed, Jim's rod was still as hard as iron, and it seemed to be even thicker and harder, and the happy tone in his moans began to become the main theme. My ever-so-proud sphincter, on the other hand, began to become sore and numb. Gradually, no matter how hard I pushed, my pussy couldn't clamp his big cock anymore. At this moment, my pussy was already "wide open," allowing the intruder to enter and exit freely.

It was Jim's turn to have a bad smile on his face. "You naughty, naughty girl. I love your technique, it makes your pussy so tight, just like a virgin's pussy. You have to use this technique every time we fuck from now on. Erica, will you call me Daddy during sex?"

"Yes, I promise, Daddy."

But Jim's frequent withdrawals caused a great deal of lubrication to be brought out of my cunt, and they dried up under the friction of our genitals, forming two circles of white foam mixed with red lipstick at the entrance of my hole and the root of Jim's big cock. The dry vagina made Jim's every thrust painful for me. I had to plead with Jim, "Daddy, please, don't deflower me over and over again, I can't take it anymore. My pussy is all fucked up by Daddy. Can you stop for a moment and give me some more lube."