The Adventures of Jessica Ch. 01

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Nis 28, 2021 // By:analsex // No Comment

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I walked briskly down the street, school had just gotten out and I knew that the sooner I got home, the more time I would have to spend in my own secret fantasy world. Mom would be home just a few hours after me, as she should have left just recently to go to the airport to pick up my older sister Cate who was returning home from spending the past year in Paris studying fashion. Although from her emails that she sent back to us from time to time, it seemed more like a vacation to me. All this would give me a few hours alone to spend indulging my own personal kink, dressing up in women’s clothing. I had been doing this for a few years now, successfully keeping the small collection of items that I have a secret from anyone else, tucked away in a locked box that I kept hidden buried in my sock drawer where nobody would find it, since I’d been doing my own laundry for the past few years now.

Arriving home, I quickly slipped the key into the lock and opened the door and let myself in, being sure to lock the door behind me. I turned and disarmed the security system which also confirmed that I did in fact have the house to myself. Dropping my backpack on the floor next to the door, I made my way upstairs to my room. Once inside I shed all of my clothing, grabbed a towel, and made my way to my Mom’s personal shower in her room. Normally I would have used the other shower that was for my use, and when my sister was home, her use as well. This time however I used Mom’s shower because all of her feminine hygiene products would be there.

Turning on the shower, I held my hand underneath and adjusted the water until the temperature was to my liking, normally I would have liked to of taken a nice bubble bath as I’ve done in the past, but that was time consuming, and today I didn’t have that sort of time. Hoping into the shower I took my Mom’s shampoo and squirted some in my hand and began scrubbing it into my hair, as the scent of fresh apples from the shampoo wafted in the air. After scrubbing my hair clean and rinsing out the suds, I reached for the bottle of conditioner and, after reading the instructions on the bottle, squirted some into my hand and scrubbed it into my hair.

While waiting the recommended 15 minutes for the conditioner to do its thing, I reached over and picked up my Mom’s razor and shaving foam, and proceeded to work up a lather of foam on my legs. I had done this plenty of times before, so shaving my legs came natural to me even if I was a guy. A lot of people had questioned me as to why I did this when they first discovered my hairless legs. Lying to them I told them that the hairs caused my legs to itch immensely, so I had shaved it all off, but in truth I had done it to enhance the smooth look of my legs when encased in a pair of stockings or pantyhose, which would come later.

Once I finished with my legs, I proceeded to rinse them off as well as rinsing out the conditioner from my hair. Once that was finished I reached over for the body wash and proceeded to give my body a good scrub down, once again, the smell of fresh apples could be smelled in the air, obviously my Mom liked the smell of fresh apples. Once I was satisfied that my body could not be any cleaner, I rinsed off under the water and turned it off, stepping out of the shower I grabbed my towel and began to dry myself off.

Once I was dry, I made my way back to my Mom’s room and over to her dresser, opening up the first drawer, I was greeted with the site of a vast selection of different colours and styles of panties and matching bras. Reaching in selected a black lace bra and the matching panties, which I laid out on my Mom’s bed. Walking back to her dresser, I opened up the next drawer and pulled out a black lace garter belt, and a pair of black stockings, and laid them on the bed with the bra and panties I had already picked out.

Having finished with the dresser, I walked over and into Mom’s walk in closet, and browsing through the racks, I selected a short black mini-skirt, a white blouse, and a pair of 2 inch heels that I hoped would fit. As I walked out of the closet I noticed a small box similar to the one I owned pushed back into the corner almost as if Mom was trying to hide it. With my hands full I submitted to the fact that I would have to return at a later time to investigate the box and perhaps its contents. Walking back over to the bed I picked up the rest of my choices and went back into my own room and laid the items of clothing I had selected out on the bed.

Kneeling down on the floor, I pulled out my own box from beneath my bed and, after fishing my keys out from the pocket of my jeans that I had left on the floor; I unlocked the box and removed the contents. A blonde wig which I had purchased online a few months ago, and a set of fake breasts which had been my most expensive purchase, and also the one I was most afraid of being discovered with when it arrived, I had had to order it under a fake name, and when it arrived, I was fortunate enough to be izmir escort bayan the one to receive the package since it surely would have been sent back if anyone else had been there instead of me.

Once I had everything I needed in front of me, I proceeded to start to put it all together. I started by hooking the garter belt around my waist, lining up the garters properly, then sat down on my bed and carefully rolled a stocking up each smoothly shaven leg, then hooking them up to the garter belt and insuring everything was still straight. Once that was done I spent a moment to admire the smoothness of my legs, before reaching over to the bed and picking up the pair of panties and stepping into them one leg at a time and pulling them up to my waist. I then picked up the bra, and proceeded to hook it together around my body so that the hooks were in front at first, I never really understood how women could put these things on with the hooks at the back, and then spun it around on my body until the cups were properly positioned on my body. I then picked up the fake breasts one at a time and slipped them into the cups of the bra before slipping my arms through the shoulder straps.

Turning to look in the mirror, I examined my reflection to insure that everything was properly aligned, and then just for the heck of it, gave my false breasts a quick squeeze which looked rather funny to me. Turning back to my bed, I picked up the skirt and held it so that I could step into it and pull it up around my waist, I noticed that it hung a lot shorter then I had first realized as it was about half way between my knees and my waist.. Once that was done I picked up the blouse and slipped my arms through the short sleeves, and buttoned up all but the top two buttons, leaving some cleavage exposed.

Turning back to the mirror I again examined my reflection, it wasn’t bad but I still needed some work, first I picked up the wig, put it on over my hair, and pinned it down so that it wouldn’t come loose. The reflection in the mirror looked good, but it was still missing something. So after slipping on the two inch heals, I hobbled my way back to my Mom’s room, I had practice on heels, this wasn’t the first time I had worn them, but I still didn’t have it down perfect just yet.

Once back in my Mom’s room, I sat down at her make-up table and started to work on my face. I had nearly perfected this from watching my Mom and sister doing this, and from trial and error. So a little while later, after some lipstick, blush, eye shadow and mascara, I was almost done, and after a coat of nail polish, the job was complete. One day I’ll get a set of fake nails to put on as well I thought. Looking up from my hands, I examined the reflection in the mirror which barely resembled my former self. Instead there was an attractive young blonde staring back at me. I smiled, and she smiled back at me.

Looking at the clock on my Mom’s bedside table, I noticed that I still had about an hour until Mom and my sister were expected home. So I decided to go downstairs to get myself a drink and maybe something to eat. Once in the kitchen, I opened up the fridge and pulled myself out a cold coke. Standing at the back window, staring out into the clouds, I daydreamed about my future, of what would happen to me if I was ever discovered. It wasn’t until it was to late though that I realized I wasn’t alone anymore. As I heard my Mom comes walking in the door, and into the kitchen, where she found me

“Oh hello there, I’m sorry I didn’t realize that Jason had a friend over” My mom said, for a moment not realizing who it was, and reaching her arm out to shake the hand of what she thought was a friend of her son’s, before pulling it back to her chest with a gasp.

“OH MY GOD!” she screamed “JASON?”

I went to speak but was interrupted by my sister coming into the kitchen to see what was wrong.

“Mom are you al…oh my god, Jason is that you?”

I could only nod my head in embarrassment. For my life as I knew it was over.

“What are you doing in Mom’s clothes” my sister asked, I wanted to answer, but I was still unable to find my voice.

“Go upstairs to your room Jason, and wait for me there, I need to talk to your sister” My Mom stated. I could barely walk on the heels that I was still wearing because my legs were still shaking from being caught.

“Don’t bother to change” I heard my Sister add as I made it to the top of the stairs.

When I made it to my bedroom, I threw myself down on the bed and started to cry, my Mom and sister probably thought that I was some sort of pervert for doing this. They were probably discussing right now what sort of help I needed. I wanted to run but I didn’t know where I’d go. So I just lay face down on my bed crying into my pillow. I don’t know how long it was, but I must have fallen asleep, because when I came around my Mom was sitting on the side of my bed gently stroking my shoulder, and my sister sitting in the chair next to my escort izmir computer desk. It took me a minute, but when I remembered what I was wearing, I broke out into tears again.

I guess now would be as good a time as ever to tell you about my family. My name, as you’ve probably already figured out, is Jason, I’m 21, I’m only 5’7″ tall, I have sandy blonde hair, brown eyes, I weigh in at a measly 122lbs, not much muscle on my body, but I’m not fat either. My sister Cate is 22, a brunette, with baby blue eyes. She’s taller then I as well at 5’10” and I know from having borrowed her stuff as well in the past that her measurements are 32b-24-30. She could almost be Mom’s twin, who even at the age of 41 still had the looks that turned men’s and women’s heads in college. The only difference between my Mom and my Sister was the fact that Mom is a voluptuous 44dd. Mom had always told my sister that her bust size would increase once she found the right man and had a few kids, to which my sister would always respond by saying that there could never be a man that could keep up with her busy lifestyle, which led me to believe that my sister is a lesbian.

I never knew my father, but Mom had told me that I wouldn’t want to, she said that he was a drunken louse and not the romantic gentleman that she fell in love with in college. My parents met in their first year of college, both wanting to become Phys Ed teachers, and fell in love, and after a brief courtship, got married, and had Cate, it wasn’t an easy time for my Mom, she said she would constantly be spending time with her parents away from our father because he just refused to do any sort of work around the house unless he knew that she wasn’t going to do it for him, which was when she left for her parents, taking Cate with her after she had been born. He did shape up, for about a year, which is when they had me. It was after I had been born that everything fell apart at the seems, Dad started drinking again, worse then ever, and when he lost his job as a teacher at the local elementary school because he had shown up drunk one day and passed out in the hallway, that Mom divorced him. But that was 18 years ago and doesn’t have anything to do with the situation I find myself in now.

Finally when I had calmed down enough, Mom was the first one to speak to me.

“Jason honey we need to have a talk” she said.

“Can you sit up and look at me baby?”

I wanted to say no, but I knew that I was already beyond the point of no return; I had gone past that point when I decided to get dressed this way. I sat up anyways though, but was greeted with the one sound that I didn’t want to hear, a giggle from both my Mom and Cate. I knew that they thought I looked stupid dressed up like this, and I knew it as well. Surely they we’re just waiting to lecture me on not doing this anymore, and even without the lecture, I knew this would be the last time anyways.

“I’m sorry baby, it’s just that, you look rather silly with your mascara running down your face from the crying, come with me, why don’t you come with me and I’ll get you fixed up.” She said, taking my hand in hers and standing up next to my bed. Looking into her eyes, I could see that she wasn’t mad at me, or disgusted with what I had been caught doing. I stood up on wobbly knees, and remembering the shoes I had on, sat back down and removed them, before following my Mom off to her room. She sat me down at the make-up table which I had been sitting at alone a while earlier, and picking up a small container, proceeded to wipe down my face. I noticed in the mirror, that it was removing all the make-up that I had applied.

“You did a good job on your face surprisingly, but you still need some improvement, so I’ll show you where you could improve okay hun?” All I could do was nod.

“We’ll use what we have here for now, but soon I want to take you to a consultant and have them help pick out some things that would be better suited to your skin type, but there’s one condition you have to agree to.” Mom stated, her voice getting a bit more firm then the soothing voice she had been using since my room. Finally I was able to find my voice again and spoke up for the first time since she had found me like this.

“What condition Mom?” I asked, afraid of what the answer might be.

“I’ll explain, after sending you off to your room, your sister and I sat down at the table and discussed what we had just discovered, at first I was intent on coming up here and forcing you to undress in front of me, hopefully embarrassing you and causing you to never want to do this again, but you owe a great deal of thanks to your sister, because she talked me out of it saying that if I did, I would most likely warp your perception of sex, either causing you to be more private about your sex life, or causing you to think that sex in general was something wrong, this is a sexual thing for you right hun?”

“Uhuh” I answered

“Okay then, there’s nothing wrong with that, izmir escort so instead of scolding you for this, your sister suggested that we should support you in this, whether it be just a phase in your life, or if its something more permanent.” She explained

“Thank you Mom” I blurted out

“Oh you’re welcome dear, but don’t forget to thank your sister as well later on, now let me continue telling you what happened before I forget where I was. After your sister and I agreed on the fact that we would support you and help you with this part of your life, we began discussing how we would help you with this. As you already know, you’re going to see someone who will help you to pick out some make-up products that will better suit your skin type, also, since borrowing our clothes all the time just wont due, since your obviously of a different stature then us, we’re going to take you shopping for some women’s clothing of your own”

A look of fear came across my face, one that Mom obviously picked up on.

“Don’t worry, I wouldn’t send my little girl out into the world without making sure she looked good. You’ll borrow an outfit from either your sister or I, and wear that while we are out shopping, and yes you heard right, from now on when you are dressed like this, you will be referred to as my daughter, now have you chosen a feminine name for yourself?”

“No Mom, I haven’t” I said, the small details of picking a girls name for myself never having crossed my mind.

“Well then, I guess we’ll just have to decide on one now won’t we?” she said, as more of a statement then a question.

“How about the name Jessica, at least then your initials will still be the same”

“Yeah, I like it” I responded with excitement in my voice.

“Okay then, from now on, whenever you are dressed up like this, you will be my youngest daughter Jessica. Now why don’t you look at yourself in the mirror dear and tell me what you think” Mom said, placing the brush she had been using on me down on the table.

Looking over at the mirror, my breath caught in my throat, Mom was right, I did need some work on my make-up application skills, for the blonde haired girl who I saw in the mirror, looked nothing like the one I saw when I had done this myself.

“Well I don’t know what you two think, but I’ve always wanted a little sister to play with, and I think she looks absolutely gorgeous” My sister said, she had been standing in the doorway to my Mom’s room watching us silently until now.

Walking over to me, my sister reached out her arms and pulled me against her, hugging me up to her body. I could feel her breasts mashed in against the false ones I had inside the bra that I was wearing.

“You look absolutely wonderful Jessica, and I’m glad to have you as a little sister, and here I thought that I was the one who would be giving the gifts upon my return home” she continued, placing a kiss on each side of my face, and playfully giving the false nipple a tweak.

“Oh, I think our little girl is getting aroused, feel this Mom, her nipples are hard” my sister joked, taking Mom’s hand and placing it on my left breast, while her hand remained on my right. I felt a smile creep across my face and my Mom and sister openly fondled my breasts.

“God I never thought I’d be saying this to a daughter of mine, but let us see your tits Jessica, I want to see how you make them look so real” my Mom said, trying to hold back a laugh at the same time.

“Um, they only stay on because of the bra, if I take that off, they go with it” I stated, informing them of how it all worked.

“Well okay then, just open your blouse and let us see, you can leave the bra on for now, but we’ll have to look into a way of keeping them on your body even without a bra, right Mom” my sister suggested

“Right, now let’s see how Jessica’s tits compare to her older sister’s and Mom’s” My Mom said, reaching up and beginning to unbutton the blouse of hers that I was wearing.

I couldn’t believe what was happening, here I am standing in my Mom’s bedroom with her and my sister, dressed in my Mom’s clothes, and she’s unbuttoning the my blouse, slowly revealing the lacy black bra of her’s which encased my breasts.

“My what beautiful breasts you have dear, in fact, I think there almost as big as your sisters, Cate dear take off your top so I can compare them”

“Mom are you serious, I can’t let Jason see me without my top on” My sister retorted

“Nonsense, all I see here are three women and not to mention that we’re all family!” My Mom stated it was obvious to me that she was taking this whole Jessica thing serious.

“Oh all right Mom” My sister said, submitting to Mom’s request. It was then that it hit me, I was about to see my sister in her bra, as she undid the buttons on her blouse, I noticed that there were no straps over her shoulders where her bra straps would be, I barely held back a gasp as I began to realize that my sister wasn’t wearing a bra, but was greatly surprised when I saw a lacy white bra that wrapped around her breasts. I could barely take my eyes off of my sisters beautiful cleavage, her breasts were firm and without a hint of sag, even if she was wearing a bra.

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