Jess and Jessica

IRL Foreword: Just seeing if people enjoy my writing. While this is loosely based on actual events, I have personal real life experiences I'd love to write about. So if you enjoy this I'll happily get started on a "biography journal" of some sort.

This is dedicated to my wife and her boyfriend, who used the jealousy emotion to twist my mind into what it is today, and make me fall in love with the cuckold/genderplay lifestyle. So let's begin...

Jess and Jessica

Jessica... I met her in high school. She was beautiful and she didn't know it. Kind of a geeky girl who would hang out with the with the geeky crew.

I was part of that crew.

I wasn't really the sports type, nor did I stand out academically. I was just about average. We would always joke that if we didn't meet anybody by the time we graduated college we would get married.

I remember graduation day like it was yesterday. After the ceremony, we all hung out at a friends house and partied. She mentioned that she was going away plenty of times before. However, she was so excited, that was all she could talk about. It drove me crazy that the only chance I had of getting some action was about to leave for four years. See, I was a virgin, not really because of my looks, but more because of me being such an introvert. The only exciting thing I took part in was me dressing in my sister's clothes and walking around the house. Yeah, I was a bit of a girly boy for lack of a better word.

I was working part-time at the pizza shop down the block, so I had some extra cash to buy my own things finally. It was embarrassing the first time I walked into the clothing store and purchased my initial set of bra and panties. A pink matching set of bra and panties that were made of a silky nylon material. They were snug and stretched to fit my body in a way to push my four-inch cock back to make it look tiny. I would wear them to bed almost every night for the first week or two. Soon, I became comfortable enough to go lingerie shopping every payday. I loved to play video games so my mom figured I spent my money on them. I soon had such a collection that I would go to bed every night for a month and wear a different set. I was in heaven.

So college travel was starting for everyone. Except me, who chose to go to the local community college for nursing. Ask me why, I couldn't tell you, but at the time it seemed like the right choice. I didn't have many friends, so my weekends were spent indoors playing video games, dressing up, and sometimes both. Dressing alone started to get a little boring, and I found myself seeking something more.

One night I looked at myself in the mirror and gazed at my girly attire, the idea dawned upon me that I should step it up a bit. Hell why not, it's not like anybody sees me naked anyway. My sister always kept her razor in the shower, why not just use hers. As I spray the cream over my legs and glide the razor over my skin, I felt a tingle of excitement. It took me thirty minutes to shave my whole body, however, it was well worth it. That kept my desire happy, through most of college.

Three years pass.

I managed to find a decent part-time job and apartment, and there wasn't a day that went by without me being completely shaved. I forgot what men's underwear felt like, as I was wearing women's underwear under my clothes wherever I went, and wearing full lingerie or girly pajamas to bed every night. And it also didn't hurt that I started to grow my hair out. It was about shoulder length, and I wore it an a tail when out, so nobody questioned me. I even bought myself a curling iron and some makeup to femme myself up during my stay at home weekends, which in fact, was just about every weekend. Everything I learned about hair and makeup was via the internet.

The woman in me was in most control, being feminine was my ultimate desire. So the only name I could come up with for myself was the one name that had meaning to me... Jessica.

About three months since I graduated nursing school, and I found a well-paying job at the local hospital. I remember that day like it was yesterday. My hair - well past my shoulders - was up in its usual ponytail, wearing my typical light blue scrubs, underneath my baby blue boy-shorts, matching bra, garter, and white thigh highs - I tried to wear some sort of nylons at work to keep up with the "traditional" nurse look - and my purple glitter toe nail polish. I was working the ER, and it was a pretty slow day, when out of the corner of my eye, I see her. Jessica, looking amazing as I can remember, except she has matured and grew out if her shell. She saw me and did a double take. She yelled my name loud enough for the whole ER to hear it. She was sitting on a hospital bed with a cast on her leg. I ran over, and we hugged like I've never been hugged before, while trying to be careful she doesn't feel the lining of my bra. We talked for a while after she told me about her nasty sprain while jogging. You could tell she was active. She was wearing tight jogging pants, with a form fitting running top that showed the amazing shape of her body. We made plans for dinner that night.

She didn't forget to remind me about the deal we made in high school.

A few weeks went by, Jessica and I went out on a few casual dates, and she seemed to show an interest in me, which I found hard to believe with my petite build. She looked like more of the "alpha-male" type of girl. It made me a little nervous every time I would go out with her, beings that I no longer owned any men's underwear, I had to be careful not to let my secret out. It drove me crazy that if our relationship progressed, I would probably have to get rid of my female underwear, which at the time, became my everyday wear.

Six months go past, we were pretty serious about what our intentions are with each other. I ended up putting my clothes in storage, I couldn't get rid of them so easily. My hair was growing back on my body some, it's not like I was very hairy to begin with, so I coped well with this. I was back to being a normal boy, well except for my hair, which Jessica seemed to like anyway. We were even talking about moving in with each other, which was still crazy to me because her looks rivaled most women I've seen.

Jessica was about five-foot-eight, one hundred and ten pounds, a full perky C cup bra, and straight dirty blonde hair that went down to the middle of her back. Like I said, she was perfect. People would stare at us like we were a mismatched couple when out on dates, or they would think she was just a fag hag, and I'm her gay friend. Which served embarrassing when men would hit on her in front of me. But she played it cool, she always did, it's was her job, being a lawyer and all.

With in two years of us dating we were moving in with each other and had a wedding date set, I loved her more than anything and found her more attractive than ever. I tried my best to pleasure her sexually, but always seemed to come up short. Most of our sessions would end with me finishing too quickly and apologizing, in which she insisted that sex isn't important, and she loved me for how I treat her. I had my doubts sometimes, like when she would come home late from the office, smelling like she's been drinking a bit, or her weekend business trips. I tried to ignore that stuff, I was happy to have her. We eventually got married and life continued in the same fashion.

It was almost obvious that Jessica was cheating on me. Her weekend business trips were far more often, and there were times I came home from work, and her business partner, John, was leaving. John was the typical alpha male. Football scholarship, works out everyday, he's a successful lawyer, the whole nine yards. John always treated me like I was one of his typical nobodies. He was very condescending and arrogant, but only when talking to me. I guess he couldn't grasp the fact on why Jessica was still with me. I would look at her when he treated me like that, hoping she would intervene and set him straight. But she would just shrug me off. This was my life for the next year or so.

Jessica and I were no longer intimate, except for the occasional drunk nights, she would come home and have me perform oral sex on her without returning the favor. She would taste different on the nights she was out longer, almost a salty taste. I guess it was just her working up a sweat from being out all night. One day she told me that she was planning a week-long business trip, which bothered me because it fell during valentine's day. She left that morning on a Sunday. Little did she know, I've been going back and forth for the past few months to my storage locker I've been keeping secret, to bring some of my girl clothes home to keep busy during her long weekends. I've been shaving as well, it's not like she noticed, my hair was faint anyway, and we never saw each other naked, due to out lack of intimacy. I called in work and told them I wanted to use a week of my vacation time. Jessica was back into my life. This Jessica understood me, and was honest and excepting of who I was. I stayed dressed constantly for the next few days, and even painted my nails. Wednesday night came around, I was sitting in the living room of our house, watching TV in my black teddy, matching panties, thigh highs, and a pair of cute black slippers that I purchased earlier that day. I ended up falling asleep.

"Wake up Jessica!" I heard the voice faintly. "Wake up sweetie!" I wake up, but keep my eyes closed hoping that what was happening was a dream. But it wasn't.

There I am sitting in the living room. Jessica, my wife, sitting opposite, and John in the kitchen preparing drinks. I am mortified as she stares at me. I start to explain.

"Shut up" she says, "I already know about this."

I look at her in disbelief.

"I set up a camera to keep an eye on you, I was hoping to catch you cheating, so I can divorce you and take you for all you were worth. But this is even better."

I couldn't think of any words to help the situation.

"Maybe I'll keep you around, I could use another woman around the house," she said.

I got up and walked into our room. She followed.

As I started to take off my sexy attire, she intervened, "Keep it on, this house is a mess. Tomorrow morning I want you to write a letter of resignation to your job. I like the thought of having a live-in house maid."

My face turned white.

"But what about the expenses?" I asked.

"Johns staying with us, if you're stupid enough not to realize that he's been filling you're place romantically, you're more of a fool than I thought. Plus, I think I have some ideas on how you can earn some extra cash to contribute. You can stay in the guest bedroom, don't worry, I bought you some pink bed sheets to make yourself at home."

John walks in the to the room with a hard drink in his hand. Lays back on my side of the bed, and kicks his shoes off.

"Okay" she says, "Get your new bedroom set out of the car, and fix up your room. And wherever you're keeping your clothes, feel free to grab all of them. And find something appropriate to wear, I'm getting rid of your male clothes. We're in this for the long haul."

"But all I have is skirts to wear. It's freezing out," I pleaded.

"Then you better wear nylons to help keep warm, I don't need you sick, we have a lot to get done," she says, unconcerned about my problems.

I drive to the storage locker where my previously secret life had been kept. It was outdoor thankfully, so I could pull the car right up the the door. I was wearing my short denim stonewashed skirt, my black heels, black sweater, and black pantyhose. The pantyhose really helped fight off the cold, so maybe my wife did have my best interest at heart, and that's why I adore her so much. I had a lot of things to load into that car, so tried to hurry and make sure no neighboring lots showed up. As I was finishing with the last of the fifteen or so bags, I had to spend extra time making them fit. I was bent over into the car adjusting everything when I heard a whistle in the distance. I peeked my head up in freight to see who it was, and plan a speedy getaway. A construction worker was unloading his equipment into his rented garage, well actually, he was more focused on me.

"Do you need help with all those bags hun?" He yelled.

I panicked.

"Hello?" he said. "Do you need help?"

I spent plenty of time practicing my female voice in front of a mirror, or into a tape recorder. I was always semi-please with the results. Like I said before, the Internet is a great source for learning new things. I always fantasized about passing as a woman vocally.

"So you're just going to ignore me?" said the man.

I reached down deep, and gathered my courage, and looked directly at him.

"Uhm... No thank you" My heart was racing.

"Okay sweetie, let me know if you need a hand" he said.

I nodded.

As I continued to arrange and push bags to make them fit, I slipped, and some bags fell out. I pick one up and place it back.

"Hey hun, let me get that for you," I hear behind me.

I froze, still halfway inside the car.

"A petite lady like yourself shouldn't be struggling with this."

I slowly get out of the car and turn and look at him.

He looks me up and down. I'm done for.

He smiles and says "Wow! And beautiful as well."

"He doesn't know? Wow!" I thought while still trying to maintain a womanly composure. I just smiled. My skin was crawling with excitement. This was the first time I was being passed as a woman.

He proceeds to rearrange my bags to make them fit snugly into the car.

At the time I never really considered the sex appeal of a mans muscular body. But if I did, his body would be the ideal starting place. He was about six feet tall, two hundred and twenty pounds, built with raw muscle, and a very handsome chiseled face.

"Now you should be good," he says as he closes my car door.

I thank him in my most feminine voice.

There was an awkward pause.

"Hey, I don't normally hit on women in storage lots, so I'm not very good at this, but, could I call you sometime?

I just stared, not knowing what to say.

"Okay, how about this, I'll just give you my number. And if you feel comfortable, call me whenever. Here's my business card."

I took the card, and he walked away backwards, still looking at me as if he was assuring his interest before turning around to get into his truck. He pulled away and gave me a honk.

The name on the card was Bruce.

I barely remember the drive home because my mind was racing so fast. From getting caught by my wife, her inviting John to live with us, and me being forced to resign my career, he night couldn't get any worse. As I pull up to the house I noticed that the TV in our room was on. That usually means bedtime. I walk into the living room, nobody. The kitchen, same... The only room occupied was our room... Well, her and Johns room now apparently. As I walk past their room I can hear faint talking and chuckling, same goes for my room which is right next to them. The walls are thin so I can hear muffled sounds just clear enough to determine whether they were awake or not. They were busy while I was gone obviously, because all of my belongings were put in there. My TV, laptop, my remaining girl clothes were also neatly put away into my dresser. It dawned upon me that this was for real when I noticed that all of my male clothes were nowhere to be found. So, still dressed in my outfit I started to unload the car, and hurried so none of the neighbors would see me. As I walked back into the room with the last of my things, my wife was in there unpacking. She was floored by the amount of things I had been hiding.

"Well, let's get this stuff put away," she said, "Because tomorrow is the first day of your new life."

She helped me put my things away without saying a word, ignoring my plea to just sit and talk about it. She wanted no parts. I laid in bed in the bra and panties I wore that evening.

I could hear in the next room Jessica, my wife, making love to her new housemate John. It couldn't have been the first time they've done this, because she was doing things to him that I couldn't even fathom her doing to me. I couldn't help not to pleasure myself to the sounds they were making.

Maybe I should have enjoyed my self satisfaction a little more, little did I know it would be my last.

The alarm clock goes off at 5am. Jessica must have set it while I was out last night. My smooth body clad in women's underwear partially covered by the pink silk sheet rolled out of bed and walked over to the dresser. There was a note...

"Shower, get dressed, make breakfast.

No you can't use the main shower, use the guest room shower."

Confused, I walk to the guest bathroom in my new assigned living quarters. We never really kept anything in the guest bathroom, so I wondered what I would use for hygiene. To my astonishment, it was fully loaded with feminine care, such as lotions, shampoo and conditioner, razors, and hair dryer... There were even douche kits under the sink, why I needed them was beyond me at the time. No expense was spared. Jessica wanted a woman, so she made sure she had one. I cleaned myself up and shaved my body to be fresh for the day, as Jessica would have wanted me to. I went into my panty drawer and picked out the silver matching bikini and bra set, put them on, and walked in front of the mirror. It was amazing how feminine I was. I step into the walk-in closet and look for a good outfit to wear for the day. I picked a pair of slim fit jeans that were so tight I had to squirm on my back to get them on, but I loved the way they felt. For my shirt I kept it simple with a super tight black tank top that showed the silver straps of my bra. The only shoes I owned were heels, and if I was going to be wearing them all day, I wanted to be comfortable. So picked out my shiny, black, round toe high heels. I walked back over to the mirror to check myself out and do my hair and makeup.

I'm standing in the kitchen reading the order list for my wife an her boyfriends breakfast. Just toast, and smoothies. They took care of their bodies, which meant they ate well also, which made this a little easier for me. The sound of the blender must of woke her up because she walked out as I was finishing her and Johns drinks. I noticed that she took extra precaution to keep her robe closed, as if I was a stranger. John followed a few minutes later, wearing a black robe, fully open, only wearing boxer briefs. He had an amazing body, so I don't blame Jessica for being attracted to him. They were sitting at the breakfast bar while I cleaned up my mess.

"I took the liberty of typing up and faxing your resignation letter," she said, "I mentioned in the letter that you are having a difficult time dealing with your gender identity and you're moving across the county to spend time with supporting friends."

I stopped and processed what she had just said.

"Thank you," was all I was able to say.

John lets out a quiet laugh.

"Also, when you are done, meet me in your room, I have a surprise for you," she says, as she goes into conversation with John about work.

I finish my cleaning and walk back to my room as Jessica requested, "Click clacking" the whole way. It's hard to be quiet walking in heels on hardwood floors.

I enter my room, and spend the next few minutes looking at the setup Jessica has supplied me. A vanity mirror with all sorts of lotions and perfumes nicely organized along the top. There was a trunk we bought for the foot of the bed when we furnished the house, but it was locked, which was strange because we had no reason to. My hands were a little dry from cleaning. So I sat in front of the mirror and applied lotion to my dry skin. All while admiring how feminine I looked in my new vanity.