tagTransgender & CrossdressersBecoming Jacqueline Pt. 01

Becoming Jacqueline Pt. 01


Summers were always so boring. All the other kids I went to school with loved playing baseball, riding bikes, chasing girls, or going to the beach during summer break, but not me. I usually spent my time in my room playing online games or watching movies or helping with chores around the house.

I did not like most sports -- I never did. It was so much effort, and team sports were so rough and scary, and the past few years, as all my friends grew so much bigger and stronger than me I feared that I might get hurt. I was scared to death to stand with a bat and have someone throw a baseball at me. I could never hit it, and it might hit me, and everyone always laughed when I swung and missed. Sports were humiliating.

Being the absolute smallest boy in school did not help. I was still not even five-feet tall yet and, having just turned 18, I was literally the proverbial "ninety-eight-pound weakling" and I hated that, along with the fact was that I probably was not going to grow any more in height than I had already attained. All my friends grew into much taller, more masculine and muscular men. Not me. I didn't even grow any facial or body hair, at least not yet. Heck, I was tinier that 98% of the girls in my high school!

Oh yeah, where was I? -- ahh, yes... sports. Yuck! During the school year, playing flag-football scared me to death. I could not catch the ball, and then guys would run and try to push you, or worse, knock you over. It seemed like such a rough and stupid sport. Full-contact football seemed like the dumbest idea ever. But there was one sport I loved - distance running.

In fact, that was one of the things I truly loved about summer -- no team or school sports!! Distance running was the only thing I did at school, and I liked that. No one but me, and I could get in my head and run forever.

This particular summer was starting off like every other one -- I was bored, in my room goofing off, and the days of early summer began to meld into an unending pattern of similarity. But one morning my Nonna (that is what I called my Grandmother) came to my room and said "Mrs. Russo is downstairs, and she has a question she wants to ask you. Get dressed and come to the kitchen, Jackie."

My brain exploded.

Mrs. Russo lived in the adjoining house directly behind our house - we shared a common backyard fence. She was this amazingly beautiful lady -- married to a fireman by the name of Mike Russo, she was the hottest lady in our entire neighborhood. She had long blonde hair, a tanned and tone body, and huge curves -- boobs and an ass that looked as if she were a headliner stripper. She was, however, a nurse.

One of my other summertime hobbies, besides playing video games and watching movies, was to peek out my second-floor bedroom window as Mrs. Russo lay in her yard in a tiny bikini sunning her lithe, smooth brown body. I would jerk-off as long as she stayed outside, cumming sometimes two or three times in an hour.

Already wearing baggy shorts, I threw on my t-shirt, pushed my shoulder-length, stringy, dirty-blonde hair behind my ears, and went down to the kitchen, nervous as to why she came to our house. Maybe she was complaining about my jerking off to her one too many times? Could I have been caught? I was freaking out. I had only ever said "Good morning" or "Hi" to her in all my years living here.

"Hi, Jack," she said with a smile. Her face was stunning, her lips were full and pink -- she was so sensual and lush. Wearing a tiny and very short one-piece pink jumper that covered very little of her amazing body, her nipples stood erect, and her long blonde hair was pulled up into a tight pony-tail that cascaded down her bare back almost to her waist. She reminded me of a hot MTV pop-singer disco babe.

"Hi, Mrs. Russo," I said, and then fidgeted trying to not look at her face (failed), or her incredibly round and exposed breasts (failed), or those wonderfully sexy legs (failed), or those sexy feet in such arousingly sensual heeled sandals (you guessed it - failed!).

My Nonna liked Mrs. Russo generally, but occasionally let it slip that she dressed so "trashy" or "slutty" all the time. She complained that her dresses were way too short (true), her breasts were always showing (very true), and "that woman never wears anything but the highest heels (absolutely true)!" Nonetheless, she kept these opinions mostly to herself and occasionally shared them to the wind, with me overhearing her mumblings.

"So, Victoria, how is your summer progressing?" my Nonna inquired.

"It has been so very busy," said Mrs. Russo. "Mike has been working so much overtime at the fire-station, and there is currently a shortage of nurses at Memorial Hospital so that I am right now working 50 hour weeks, or more."

"Oh my," said Nonna, "I am sorry to hear that; how are you keeping up with things with all your time taken up like that?"

"Well, that is what brings me here to visit with you, and to ask Jack a favor," she glanced my way but only briefly at my face. She took a decided glance at my little bulge in my shorts and smiled. I gulped, but Nonna took no notice.

"Jack, how would you like to earn a bit of extra money this summer painting some of the rooms in our house? Maybe doing a few other chores as well? Mike and I so need help, and we thought maybe you'd like to earn a bit of cash for some things."

She went on to explain how Mr. Russo had redecorated and redesigned their master bedroom and bathroom, and made a few other changes to the house before his job became so busy prior to summer.

"So, just as the house interior was ready to paint, we both got so busy that nothing got done at all; we are mid-project on the painting and it needs finishing," she said. "I was hoping you might help us out, Jack. Would you like to do that?"

I explained I never painted anything, and I might mess it up, to which her response was "Mike and I will teach you! You will be brilliant at it." Her enthusiasm was hard to argue with. Finishing up, she said I could come over tonight after dinner and she and Mr. Russo would show me what to do and where to start.

I admit I thought it would be good to earn some extra cash for things I wanted to do but Nonna had said no to -- like maybe get a tattoo or a piercing or something like that.

After Mrs. Russo left, Nonna said it would be good for me to learn a skill, and to earn some money as well. She told me to be respectful and just learn as much as I could from the Russo's. "Especially pay attention to Mr. Russo. He is a real good man and a very respected person. He can probably teach you a great deal of things, and he is a good role model. You can learn a lot from him, Jackie."

Nonna occasionally seemed worried that she alone was doing little to help me grow up. I came to live with her when I was six years old. It was just the two of us in this big, old house.


After dinner, I went upstairs and put on some jeans and a clean t-shirt, threw on my Chucks, and walked around to the Russo's front door. Walking up the porch I went over and rang the doorbell.

"Well, hello Jack!" said Mr. Russo, extending his huge baseball-mitt sized hand to greet my little fingers in a one-sided handshake. "Come on in," and with that put his huge, long, muscular arm around me and brought me into his home.

The house was beautiful. Mrs. Russo had clearly decorated the remodeled home in a very chic and elegant modern style. I had never been in their house before, but it was so very different to our home. This house looked like a movie set -- white rugs with marble floors and stylish furniture. There was artwork on the walls, and the place was just so overwhelmingly different and -- I don't know how else to describe it -- but it was pretty and somehow sexy at the same time. I felt cool, but so very out of place.

Mr. Russo got right down to business.

He showed me the paint cans, mixing sticks, drop cloths, and rollers and trays and big and medium and little brushes in the utility room. Mr. Russo was a big, muscular man. He worked out and had a barrel chest and muscular thighs. His arms always looked like they were going to rip his shirts. Every one of my friends Mom's talked about him. To me he seemed like three or four times bigger than me. I literally felt like a tiny elf next to him. His voice boomed with enthusiasm, just like his wife, and it seemed like he was a very happy and extremely confident man. I could understand why Nonna thought he would be a good role model.

"So, Jack, let me show you where you need to start painting. Come on, follow me," and we left the utility room, crossed through the kitchen and entered another wing of the house.

"This is our bedroom. I need that wall, there," he motioned, "where I redid the plaster...I need that painted. And in here," we walked into the master bath and beyond in a massive closet, "is Vickie's closet, and the whole thing needs painting in that pastel color I showed you. But for now, you should start in the master with the eggshell white paint, and when finished we can start you in here."

The place was amazing. It was bright and fresh and hip and cool. It was befitting this young and vibrant couple -- she the Goddess and he the Hunk.

"Jack? Sound good, are you good? Think you can handle this?" he said.

"Yes, Mr. Russo, I think I got it, sir," I said.

"Perfecto, bro'. I am off to the station, then, as I have a night shift coming up. You can start now if you want," he said.

"Now, but..." I stammered.

"Oh yeah, also, no more calling me 'Mr. Russo', Jack. Just call me Mike, ok?" he said.

Now that was dope. "OK, Mike," I said and smiled. Damn. He is so very cool.

"Vicky is also working night shift at the hospital, Jack, so make yourself at home. Finish whenever. If you get too tired, just head home, ok?" he said.

"OK, Mike," that sounded so cool calling him by his first name, "I will." And with that, he was out through the garage door and gone.


I called Nonna and told her I was going to start painting. It was only 730PM and I could get in about 4 to 5 hours of time. She agreed.

I went into the utility room and grabbed the drop cloths and the eggshell white can of paint and brought it to the master bedroom. I returned and grabbed the rollers and tray and brushes. I laid out everything at the base of a simple flat wall in need of paint. I figured I wanted to do a really good job, and I should go slow enough not to screw it up. As I prepared to start, I kept wondering what a house like this had in it. I wanted to see what Mrs. Russo had in her closets and drawers and such. I told myself "No, it is none of your business," but my curiosity got the best of me. I had to just take a tour!

I first went to the dresser and opened the drawers. There were "his" and "hers" drawers, although he seemed to only have two of them. Mike had underwear and t-shirts and socks in his drawers. Mrs. Russo had tops and shorts and panties and bras in hers, and I began to get turned on and immediately erect. The colors were pastels -- pinks, blues, yellows, reds, prints -- and were, for the most part, "everyday wear" for her. Another drawer, smaller, had some jewelry and sunglasses and hair bands and such -- accessories and things. I went through every drawer of hers and noticed and fondled all of it. I was fascinated.

I went to the bed, and on either side looked into the bed-stand drawers. Already aroused, Mikes side had condoms (Extra-Extra-Large Magnum's) and lube in his side, plus some other things I did not understand the need or use for (silk belts, rope). I went to her side, and she also had lube (but cherry-flavored) and a few pink jelly dildos, as well as some other sprays and gels I did not understand the use of -- yet. I now began to get very, very hard and erect. I had seen enough porn videos to understand. Wow. I had never seen any of this stuff before.

By now I was totally turned on. I went to the master bathroom and rummaged around, but then I proceeded to where all the treasure was to be found... in what, for me, would become absolute heaven -- my sanctuary, my place of comfort and place of worship -- I found my way into Mrs. Russo's amazingly large, girly, sexy, spacious closet --totally stuffed and brimming with fashion and accessories!!

Her wonderfully scented closet was at least twice the size of my bedroom -- it was huge! Upon entry, there was a center pedestal drawer with a layout table. On either side were floor-to-ceiling hanging closets, and along the back wall, floor-to-ceiling cubicles containing the most amazing collection of high heels I had ever, and frankly, would have never seen until now. I had no idea one person could own, much less wear, so many shoes and dresses and outfits.

A wonderful, happy, self-absorbed feeling of contentment came across me -- I was overwhelmed with the entirety of the experience. I made my way to the central set of drawers in the island pedestal. The first drawer was her collection of bikinis. I almost fainted. I moved to the next drawer, and upon opening it I felt as though the heavens came down and cherub angels were singing songs!! It was the sexiest. silkiest lingerie!! A drawer full of it. I pulled out a lavender teddy and ...right then and there, without having ever touched myself - I suddenly felt light-headed, almost as if I were fainting, but instead of fainting I began to orgasm and came with such a pulsing and throbbing intensity into my little-boy cotton "tight-whiteys" that I literally lost my balance and fell to the floor, still cumming like crazy. I totally soaked myself with my own jizz, and then lay there for like five minutes with the silky teddy draped across my face.

I lay there reliving the experience. I had just had the best orgasm of my life, and I didn't even touch myself. That was a first. "Wow. Holy shit. Double wow!" I whispered to no one.

Getting up, I made sure I put everything back in place and then began to paint the master bedroom wall -- for about 20 minutes!

I just could not resist the pull of the unknown. I returned again to Mrs. Russo's closet, and began to look at all the high heels she had. They were amazing -- so pretty, so feminine, so sexy, and so many of them. Why I was drawn to them I do not know, but in a moment of impulse I took off my Chucks and socks and tried on the black, pointy-toed high heels with red soles (I would soon come to know this brand, Christian Louboutin, and the style, 'So Kate', intimately). Amazingly, they fit me perfectly. I tried to walk but fell onto the white carpet. I could care, I lay there looking at my legs in these sexy heels and was speechless.

Impulsively, again, I rapidly stripped entirely naked - throwing my clothes off- and went and grabbed that same lavender teddy, slipping it on over my once-again erect yet tiny cock. I put the heels back on and looked at my smooth body, and without a touch of my little penis, I once again orgasmed and came with spurts of explosive intensity-- everywhere!! I shot cum across the room!! Holy shit! This was amazing. Like, literally, I thought "WTF!?"

And, just like before, after laying there for a few minutes, I got up and put everything back, cleaned up, turned off the lights, and returned to painting the master bedroom wall. I had no guilt or shame, because the overwhelming intensity of the experience blew me away. "Why do I react like that?" I thought.

I picked up a roller and decided to get after the painting, but my curiosity got the best of me. Twenty minutes of painting and I, again, found myself drawn back in to her sexy closet, and in to my emerging sensual fantasies.

I was so obsessively turned on by my newfound interest in all of Mrs. Russo's things. My tiny body was all of a sudden something that was an asset -- I never thought if being tiny and petite as a boy was a good thing, because it wasn't -- until I tried wearing women's clothes! I realized that, as I stood naked in front of her mirror, my anorexic-thin skinny upper body went well with my thicker thighs and bubble-butt that came from all my distance running. As I looked at myself I realized I had a feminine shape. I actually had hips and an ass!! Frankly, my legs and thighs and butt were very shapely -- and my 22-inch waist accentuated my hips and ass.

Instinctively, and, as I would soon find out that every decision after this was of the same kind, I once-again impulsively did something I never did in my life -- I ran a bubble bath. I found a razor and shaving cream and proceeded to shave my entire body -- legs, chest, armpits, and pubic hair. Not that there was much to shave, but all the peach-fuzz was removed and in 15 minutes, I stood drying off my very-smooth self in front of her mirror. Once again, I was solidly erect from seeing myself in this way. I allowed my shoulder length blonde-locks to drape across one eye and saw how very feminine and alluring I looked.

"Holy fuck," I said quietly to myself in the mirror, "I am fucking hot." I stood back and took in the view. "Baby girl, you are smoking hot. You are the bomb. Fuck yeah. You could get anything you wanted, ha!" I stood there for another ten minutes, checking out my legs and ass and overall look. I took Mrs. Russo's brush and teased out my hair and put it into a more feminine, billowing style. My cock was straining seeing myself like this.

I went to the wall of heels and picked out a pair of pink caged-heel sandals -- another brand I would come to love, Giuseppe Zanotti -- and put them on. They fit perfectly. I stepped delicately back to the mirror, took one look at my full-body feminine self - my perfect bubble-butt ass standing proud in those sexy heels -- and shot another load of cum across the room, an orgasm that hit like ever-building waves crashing on the beach. I collapsed, stunned. It happened again.

I had now cum three times in slightly over one hour, and not once did I ever touch my cock. In each instance, I never even felt the orgasm coming. This third time, I did not immediately clean up after myself and go back to painting. Instead, I looked hard at myself in the mirror, and I began to see the feminine features I was blessed with but, frankly, ignored until right now.

Looking at her make-up table, I grabbed some pastel pink lipstick and, slowly and with effort, applied it to my full, lush lips. I had no idea they were so girly!! Back to the mirror I went, and then to the closet racks and I found a cute pink mini-dress. Putting it on I was once again erect, but I proceeded to the lingerie drawer, but found no cute panties.

I had not tried the drawer beneath, and on opening found what must have been at least 100 panties of all colors. I found a pink tanga pair that I put on. It covers my erect 3" penis, and really accentuated my bubble-butt cheeks amazingly well.

There I was, all pretty in pink, in front of the mirror. I felt like I should be feeling that "this is wrong," or "Jack, you pervert, stop!" but none of those feelings were present. I was simply fascinated and overwhelmed by my feminine look, and also by my response of three hands-free spontaneous orgasms upon seeing myself.

An hour and a half had passed, and I had done more crossdressing than painting. I felt like I still had many hours before I needed to worry if I was to be discovered. Dressed as I was, I began to explore Mrs. Russo's closet and drawers more thoroughly. I was also starting to figure out how to stand, and walk slowly, in such high heels.

I think I was in there for about half an hour when I stumbled upon this amazing party-gown. It was low cut in back and front, with a dangerous slit up one side. I put it on, along with another pair of those red-soled platform heels. It hugged my ass, made even rounder and more lifted with the heels, and my little narrow shoulders and skinny little no-muscle arms elegantly fell to the side as I walked to the mirror -- and, upon first glance of myself, I came, orgasming now for the fourth time, initially on the inside of the gown but pulling the slit to the side for my little pee-pee to shoot its love juice across the floor.

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byJacqueline_Love© 25 comments/ 35089 views/ 68 favorites

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