TITLE    : Becoming Jacqueline Pt. 01
STORYID  : becoming-jacqueline-pt-01
SUMMARY  : Jack arouses his emerging feminine self, and likes it...
AUTHOR   : Jacqueline_Love@lit
DATE     : 2018-09-11
CATEGORY : transgender-crossdressers
FLAGS    : h
TAGS     : |sissy|transvestite|transsexual|sissification|


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.

<hr pg="2" />I immediately licked my warm, salty jizz off my fingers and cleaned it up, and put everything back, and went into the master bedroom and painted like a madman until midnight. I kept thinking I should feel guilty or weird as I painted, but none of those feelings arose. Rather, a new-found curiosity emerged inside of me. For my entire life I always felt like this tiny, punk-ass, skinny Goth-Emo kid that everyone bullied. I was too tiny, too lightweight, and of no use to anyone for a team sport or even to hang with. I was an oddity. 



"So, I am used to being an oddity, right?" 



"Fuck it. You are hot as fuck, dude. Bring it on. Own it."



----



I went home at midnight. My Grandmother was sound asleep. I washed myself off and slipped on a pair of tiny baby-blue panties with cute little yellow flowers on them, and crawled between the sheets. My smooth body felt wonderful, and I couldn't keep my hands off my ass. I began to feel my round, firm butt cheeks, and squeeze them. One hand went to the front of my panties, the other went to the back. Pushing the g-string aside, my fingers began to play with my asshole. I tasted my fingers, wet them, and put them back there again. It felt nice. I pushed a little deeper. A new feeling, yes, but nice. My other hand felt my tiny little penis behind the lace. I always hated that it was so very tiny. But tonight, as I fell off into a nice sleep, my last thoughts were "Maybe it was never meant to be a penis, not a real one. Maybe it is just a clit after all?"



And to that thought, I fell asleep feeling my smooth feminine body, and what I came to think of as my pussy-hole, and my little itty-bitty clitty. I didn't know it at the time, but my life was about to change in a whole different direction, and as the coming days merged into weeks, I just could not care less.



-----



I slowly woke the next morning to the awareness that my skin was totally smooth; I loved how it felt as my hands felt my bare silky thighs and arms. I recalled now that I had shaved my entire body last night. Last night. I smiled. 



My hands went to my bottom, and I felt and pressed against my hole, and the pressing felt really nice. That hand stayed and fingered my bottom. As I reached for my little cock with my other hand I felt the silky smoothness of the panties I had swiped from Mrs. Russo's closet. I had developed a raging hard-on in the few minutes I was awake, and as I went to stroke myself, I immediately orgasmed all over my smooth tummy. It was intense, the pumping building harder force with each squirt. Memories of last night flashed through my mind. Then it stopped, and I was spent; I went limp everywhere.



I spread the warm jizz around on my belly, and then brought my hand to my mouth and tasted and licked all the sticky goodness off until it was gone. It was an odd, salty taste -- not good, not bad...just new to my taste buds.



As the remaining cum cooled on my belly, I lay in bed thinking about all that happened in the past day -- Mrs. Russo asking me to help paint her interior of the house, Mr. Russo coaching me on how to do it, the beauty of their home, and my curiosity and explorations inside their bedroom and her closet. What was so vivid was how much I enjoyed seeing and wearing her things -- lingerie, panties, dresses, and heels.



I said to myself that it was just a passing thing, it was really no big deal. I didn't exactly feel guilty, but I also knew I probably needed to cut back on this newfound attraction I was showing to feminine clothing. I liked girls, I told myself, but I didn't want to be one. Even though I saw myself yesterday in Mrs. Russo's mirror as a very attractive girl, I didn't want to live the life of a girl -- I frankly never thought about it before.



Well, it was fun, but it is probably over. That was probably a good thing - I mean, this shit could get addictive pretty quick. I thought maybe I'd watch some reruns of my favorite movies or log on and play some games for the rest of the morning.



I got up, went to the shower and washed off the cum, and washed out my hair for the first time in days, using conditioner (which I never used) twice. My mind could not totally get away from what I did last night at the Russo's. I had to admit I was turned on - I mean, like, I came 4 times without ever even touching my dick, so it must have been a turn-on! Same thing just happened this morning - I came after just touching my cock for a few seconds and BAMM! I shot all over the sheets and my belly. "Man, this attraction to Mrs. Russo's stuff is powerful mojo," I thought.



I was toweling off in the bathroom, and as I glanced in the mirror, I saw my shoulder length hair and thought "I wonder if I can style it like a girl's hairstyle?" 



Next thought: "Don't be stupid, you're a guy. Stop it, dude." But then I thought, "What the hell, what does it hurt, just try it."



So, impulsively (as was now becoming the norm) I grabbed the hair dryer and a brush, and began to blow it out from underneath to give it fullness. It was shoulder length, not trimmed very well at all, but it was long enough, for sure. 



I blew it out, from the underside, and then just experimented, brushing this way and that way and directly back, so that it was really blown and dried full-out. Normally I never ever blow-dried my hair, chicks do that but not me. Hence, it always just lay on the side of my head kind of straight and stringy, and often I had it pulled back into a pony tail anyway. 



The color of it was nice, for a girl, I thought -- it was a light blonde but with light brown streaks running through it. The more I looked at it I thought, "You have really pretty-color hair, man." For a fleeting moment I wondered how long I might grow it.



When I finished I was shocked -- my hair was full of body and it actually had a nice wave curl running through it. It was definitely a very feminine look. I began to think about how full my lips looked with Mrs. Russo's pink lipstick on them last night.  



Once again, I began to get a hard-on, but I ignored it and tried to suppress the thought of how feminine I could be. Looking in the mirror one more time, I really was taken aback at the full-bodied texture of my very pretty hair.



Hit by a tinge of guilt and feeling odd, I worked hard trying to push that thought out of my mind; I pulled all the hair back into its normal pony tail and went back to my room. "Time to be a man again, dude," I said to myself. 



I put on my baggy Nike shorts and a t-shirt and went downstairs to make myself some breakfast. The house was empty, as Nonna had gone off to work hours ago.



Eating some cereal, flipping through my iPhone, checking out my Facebook and Twitter feeds, a text message popped up with a number I did not recognize. It said "Good morning Jack. If you have time could you come by to help me with a few things around the house? Vicky."



Wow. I just got a text from Mrs. Russo? I guess Nonna gave it to her. I texted her back, "I can be there in half an hour, is that ok?"



Her reply was immediate: "Perfect!"



I went around the block and rang the front doorbell. The door opened and there stood Mrs. Russo in another tiny, revealing jumpsuit of the same lavender color of the lingerie I wore the night before. He sexy shape was hardly hidden - her breasts were round and full, her nipples erect, her tiny waist just accentuated the wonderful curves of her hips and ass. 



But something, also, was different, and then I noticed it. She was exactly the same height as me! I always thought she was taller. Then it hit me - "Doh, she has always worn high fuck-me heels, dumb-shit," I thought to myself.



"Jack, don't just stand there gawking, come on in!" she said. As I walked into the house she touched my shoulder - which sent a thrill through me -- and directed me towards the kitchen.



"Have you eaten breakfast yet, Jackie?" she asked, using the name my Nonna uses for me.



"Yes, ma'am, I had some cereal just before you texted me."



She proceeded to load a bowl with some fresh fruit and put it in front of me, saying "Cereal is just empty calories and sugars, baby. You need good food, and fruit is the best. Here, eat this bowl and drink some fresh, clean water. This helps with digestion and keeping a clear complexion -- your skin will be very healthy."



"Thank you, Mrs. Russo," I said. I thought, "Wow, she called me Baby". I liked that, it implied a comfort and intimacy and, in some way, some ownership of me and my well-being.



"Jackie, stop the 'Ma'am' and 'Mrs. Russo' stuff -- it makes me feel old -- call me Vicky," she said with a teasing smile.



"Yes, ma'a...yes, Vicky," I said with a blush. She came over and grabbed my cheek in a pinch between her thumb and forefinger and said, "You are adorable, Jackie!" I just blushed again and proceeded to wolf down the sweet fruits she gave me.



"OK, so here is todays plan. I need to get some sleep because I worked night shift last night and I will tonight, again. Mike ... wait, you are not calling him Mr. Russo, are you?" I shook my head 'no'.



"OK, good. Anyway, Mike is already asleep, and I have a few things I want you to do for me today, before I turn in, ok?"



I nodded.



She motioned me to the living room, where there were two boxes on the coffee table. "Jackie, this needs to go to Goodwill donations center in town, if you could; would you be able to take it there; can you?"



I nodded again.



"It's just a few things from the kitchen - pots we do not need, and a few things of Mikes and some of my old things I do not need anymore."



"OK, I can take it later today," I said. She smiled.



"Alright, good. So, Mike and I both leave this evening around 6 o'clock for our shifts at the firehouse and hospital. You can come by then, or afterwards," she said.



"I will be here then, but I can take these things now if you'd like," as I nodded towards the boxes.



"Oh, wait a minute," Vicky said, smiling, "I have another small bunch of things that needs to go to Goodwill. Wait here," and she disappeared towards her room. As she walked away I couldn't help admiring her smoking hot body -- her blonde hair, her tiny arms and shoulders, her even-tinier waist, and the most amazing round bubble-butt ass as she walked away. God she was hot.



She came out of her bedroom about a minute later, and I was shocked to see what she had folded into her hands. There was a towel, folded, and a dress, folded, and on top of that was the lavender teddy I had worn the night before, and... on top of that... a pair of sexy black pumps. Not the Louboutin's, but a wildly sexy pair nonetheless.



I choked, literally, and began to cough. I almost died right there. But Vicky acted totally normal. "Jackie, let me get you another glass of water," as she rushed to get it to me. I drank it and looked at her, but she indicated nothing out of the ordinary.



"Baby, let me add these to the boxes. These are just some things I meant to give away a while ago. Thank you so much for doing this, helping us out and all."



"You're welcome, Ma'am," I said.



She pinched my arm and said "Vicky! Call me Vicky! Don't make me into an old lady just yet!" she said with a devilish twinkle.



"I'm sorry, Vicky," I nervously laughed.



"OK, so see you at 6?" Vicky asked. 



"Yes, Vicky, I will be back at 6, and thank you for these," I said, motioning to the boxes. "I mean this, uh, the boxes, uh, the chance to help out you and Mike." I blushed. Why did I have to say "these," why did I thank her, for what? Does she know? Fuck. I am an idiot, I thought. 



She came straight up to me, and holding her hand against my face, she held my gaze, then smiled, and then -- as we looked eye-to-eye-- I dropped my eyes down to avoid her gaze, only to look at her huge breasts in that lavender jumpsuit. I was lost, I wanted to cry and run, but then she said "Jackie, you are welcome, baby, but it is you who I should be thanking. You are helping us here. You are a lifesaver, baby."



I didn't know what to say. I was speechless. She continued, "Look, you take these things to Goodwill. If you or your Grandmother want anything -- you know, a pot or pan or something - just keep it and take the rest to Goodwill, ok baby?"



"Uhhh...ok, Ma'am," I said.



She gave me a pouty glance, and then leveled her eyes at mine and spoke seriously, saying "Jackie, are you ok? You look lost."



"I'm ok, I just, uh, I'm a..." and I trailed off unable to finish my sentence. I was sure she knew I was in her things last night. She approached me, and once again face to face, she brushed my hair back and grabbed me by the chin and made me look up into her eyes.



"Baby. Look at me," and our eyes met. She continued "You need to just cheer up, nothing is happening for you to be upset. You are helping me, and Mike, and we are very grateful. I have watched you grow up into a very nice young person, and you are sweet and adorable and unique. You just need to relax."



I just stood there, totally unable to speak or move. I was freaked out but was frozen in place. I realized I was now helpless.



"Jackie, what is wrong? Why are you nervous? Do I make you nervous? Is that it, do I make you nervous?"



Silence. She just stood there. I fidgeted. I tried to talk, but I couldn't. I started to sniffle, and then slowly sob.



"Baby, now, c'mon, it's not that bad," and she came to me and hugged me, she embraced me, and I felt her breasts press against me, her hair as my face was pulled in, her perfume smelled amazing. She held me and rocked me as I cried, and then pulled back and looked me in the eyes and said "Jackie, calm down, baby, calm down," and she kissed a tear off my cheek. She grabbed me by the hand and led me to the couch and motioned for me to sit, and she sat next to me.



She sat with me, and as I was calming down she stroked my hair and wiped my tears. I was calming a bit, and she said "Jackie, you have such pretty hair. It is so soft. Do you use any products or is this softness natural? I must know, I need to steal your beauty secrets."



I looked at her, puzzled, but answered "No, it is just my hair, no products or nothing but I used conditioner this morning."



She held my gaze, then grabbed my chin and turned my face from side-to-side, sizing me up. She said "Jackie, you are handsome... almost too handsome for your own good." I blushed and then smiled. "You are so handsome you are downright pretty, do you know that?"



"Thank you, Vicky", I said, sniffling through my tears.



She smiled, and added "OK, well, it is true. But don't get taken all up in the compliments -- I mean, so you have a pretty face, pretty skin, perfect symmetry and perfect hair -- I may get jealous of you!! And don't like Mike notice!! Anyway, you go, and I need to go to get some sleep. I have night shift. You go home now, baby." And she led me to the door.



As I went to pick up the boxes for Goodwill, she said "Come here," and opened her arms and gave me a big squeeze of a hug. I giggled and smiled and blushed. She kissed me on the cheek and said "Off you go, baby. Enjoy."



As I carried the boxes out of the front door, she said, smiling, and with an odd look in her eye, "See you later, Jackie."



----



The boxes were heavy, I could barely manage them, but I so wanted to get out of that house that carrying the two of them at once was my only rapid escape. I didn't know what to think -- I was totally flustered.



My brain was firing in a hundred directions all at once. How could she know? There was no way, no way. I am pretty, really? She likes my hair? Why did she say "Enjoy" as I left her house? Enjoy what? Why did she say that about Mike noticing if I am pretty? Should I keep the heels or what? I kept replaying these things in my head, and decided it was all just a coincidence.



Back at the house, in the garage, I went through the boxes. There were, as she said, some kitchen pots and pans, a cupcake tin, some of Mike's old shirts, and then quite a few things of hers. The latest additions -- the lavender teddy, the heels, a really silky red mini-dress -- I laid those to the side. Inside the towel, folded up in it, were three pairs of panties -- a pink g-string, a purple tanga, and a leopard-print bikini. In the other box, I found some a ton of make-up -- lipstick, eye shadow, mascara, blush, unused eyelashes and nails - some that had been clearly used but still with much life left in the products, some were unused and usable. 



My first thoughts were "Don't. Just don't. Do not keep this stuff, it is not right, it is hers, it is supposed to go to Goodwill."



My next thoughts were paranoid: "This can't be coincidence! Shit, she knows. She is teasing me. Is she tempting me? What the fuck, how? Nah, she can't know."



For the next 20 minutes I had this debate in my confused little head -- "Do not do it," versus "I am found out," and it kept raging in my head non-stop. But then, I realized I had a hard-on just being near these things, and Nonna not being home for many more hours, I decided that I would just go upstairs and try these things on. So, I grabbed them, ran up to my room and tried on everything.



Stripping my clothes rapidly, I slipped on the leopard panties, the red dress, the black heels. Fuck, this felt SO GOOD, oh my God, my body wanted this feeling. I went to my mirror with the makeup and put on the lipstick -- it was fire-engine red--and it made my already-full lips pop in the sexiest way.



I had no idea what to do with all the make-up products, so I went to YouTube. I sat at my computer and Googled "wearing make-up lipstick eyeshadow mascara" and a number of YouTube tutorials popped up. The first two were useless, but the third hit it just the way I needed it. I applied the eye shadow, a mascara, and a few of the blushes and other products. Like most beginners I overused it, but it made a huge change to my look.



I went to the full-length mirror in the bathroom, and what I saw astounded me.



There was this chick, in sexy heels, a tight-fitting red mini-dress, with a very pretty face -- she had tiny arms and thin, tiny shoulders, a narrow waist, and the beginnings of an hourglass figure because of her bubble-butt from all the distance running. I was so, so very hard. I was about to come, but I held back. I looked away. One last thing was missing.



Closing my eyes to not see myself in the mirror, I reached behind my head and pulled my hair out of the ponytail I was wearing. With my eyes still closed, I shook my head to make my hair fill out and get that full look I had from this morning.



I opened my eyes. In front of me was a really hot, pretty woman with an amazing ass and gorgeous hair. I looked, and said to myself out loud, "Oh yeah. Fuck yeah, I'd fuck her."



I came, right there, another no-hands spontaneous orgasm, without any warning. My little pee-pee had, with her (yes, I began to think of it as a "her" this morning), with her cute little clitty enthusiasm for sexy women's clothing, wriggled her tiny little self out of her bikini panties, and was aimed into the room with her girlish enthusiasm. I shot a massive load of sissy-juice right out from under my dress onto the mirror. I loved the feeling. I was overwhelmed with the pulsating pumps as I came for what seemed like an eternity. All the while, I kept staring at this smoking hot chick in my mirror -- tiny waist, plump ass, pretty hair and face. Holy fuck, THAT was really me? Un-fucking-believable.



This time, there was no cleaning up or putting anything away. I remained dressed. I walked in those heels, loving the sound they made on the wood floor of the kitchen. I put mirrors in areas where I could watch myself walk, and practiced and practiced walking in heels.



I went onto YouTube and found instructional videos for "walking in heels," and "feminizing," and "feminization." I found even better tutorials for make-up and hair styles. Lunchtime came and went, I did not eat. I absorbed myself in the internet searching for all things feminine.

<hr pg="3" />The afternoon went on with me sitting, cross-legged of course, at my bedroom desk on the internet checking out make-up and hair tutorials. I went onto websites looking at women's clothing and heels. Every 10 or 15 minutes I was up and walking about the house, practicing my feminine techniques. I was becoming comfortable with the heels, so much so that I put in my earphones and cranked some music through and began to dance. I found my normal music - metal, heavy rock, and such -- to not fit my mood. So, I went onto Apple Music and streamed the hottest and sexiest pop-dance and club music from all my favorite female artists, and really got into it. I listened to the lyrics and beat, and I got where they were coming from. I stood before the mirror and danced to all the dance hits I usually avoided listening to. I loved it. I was so hooked!! 



I switched out my panties, as they were getting soaked from my little thingie hiding inside of them. Having a sub-three-inch cock was not fun, it always bothered me. I gave up thinking, at age 18, that it would grow any more -- I had to face it, I had a micro-penis. That sucked. It was probably the biggest obstacle for me having the nerve to ask out a girl. I feared she would laugh and tell everyone, so I never even tried.



My favorite panties were the g-string, I loved how the back thong massaged my asshole all day. It was barely there, and my little cock stayed nicely tucked behind the tiny fabric. In fact, all three panties felt much more comfortable than my regular white cotton underwear. Nonna kept buying me underpants with a pouch, but all that did was remind me I had nothing to even come close to even begin half-filling the little pouch. I had no junk at all, none. It was humiliating.



By four in the afternoon I decided to stash my new and exciting girly wardrobe deep in my closet, under some old boxes with some games and toys I never used anymore. Just before 5PM Nonna got home from work, and we caught up on the day. I lied and told her I had been to Goodwill and had done some chores for Mrs. Russo, and that I needed to be back there by 6PM before the Russo's left for work. I said I wasn't hungry, so I left for the Russo's early.



----



At 530PM I rang the doorbell. Mr. Russo answered the door wearing just gym shorts and running shoes. Bare-chested, his body glistened with sweat as he motioned me inside, saying "Jack, my man. How are you today?"



"Fine, sir. I am good."



"Follow me into my workout room, Jack, lets catch up," and I did just that. Mike was really built, he was very muscular. He seemed like a perfect fit for his hot wife. His arms were bigger than my thighs, and his chest and pecs were really well-developed. I thought I could never, ever measure up to a stud like him. As I followed him, I thought "How do I compete for a girl if I am always up against a guy like that?"



His workout room was really impressive -- a main work-out station with racks and towers and pulleys was in the center of the room. Dumbells and barbells of different weight classes were around the perimeter. Another frame held some huge weights on a single barbell, and as I stared at that Mike said "Squats. That's for squats."



"Huh?...what?" I said. Mike looked at me, then shifted the conversation.



"Jack, what sports are you into?"



"I only like distance running," I said. "I like just running hard and long. I can run for hours without getting tired."



"OK, then that squat machine is what you want. It will build up your thighs and butt muscles for distance running. Want to try it?" and with that he began to remove the big weights and put on weights for my size. He then showed me how to do it, then motioned for me to try it.



I stood inside and lifted the weights off the rack. I slowly mimicked his effort of a slow deep squat, then returning upright. I replaced the barbell.



"Whoa, no, no. Not that easy. Give me 25 reps," so I pulled it off and by my fifth rep, I said "No more." He replied, "Bullshit, bro', you got 20 more to go." His look was serious. I obeyed.



At 10 I was barely making it. At 15 I was pleading to stop. He refused, "You got 10 more to do. Do it. You don't want me to call you 'Jacqueline', do you, Jack?"



I was slowing. My muscles were screaming. At 20 I was pleading, "Mike, please?" but he said "Five more, Cupcake." He seemed pissed I could not lift the weight.



At 25 reps I placed it on the rack, and I was just too exhausted to even be proud. I said, "There, did it", and he replied, "Take a 5-minute break, then repeat. Yes, I am serious, Sunshine." At that point, Mrs. Russo, I mean Vicky, walked in.



"Mike, what is going on here?" she asked sweetly.



"Babe, I am teaching Jack here how to do squats -- build up his runner's muscles and all. He has a long way to go from where he is starting, but I will get him in shape."



"Jackie, are you ok with that? Mike can be a real ball buster," she said with a twinkle in her eye. Mike just smiled.



I nodded affirmatively but couldn't speak. 



"Well, if you boys are starting Jackie on a workout, I am going to make sure he gets all the help he can get with the proper vitamin supplements to make his goals," and with that she disappeared for a few moments.



"OK, Jacqueline, off your sweet little ass now. Time for set number two", Mike said. He meant business, fine, but did he have to humiliate me? I started and could barely lift the bar, but slowly and then slower even still, I pressed out the first five. Mike just stared at me, so I kept going.



Mrs. Russo popped into the room and began to whisper to Mike, who, after listening to her nodded, looked at me up and down, then smiled and nodded again. I squealed out when I made 15, but Mike said "Look, Jackie, life doesn't start for you until you give me 10 more squats." After what seemed like a painful eternity, I placed the bar back on the rack, saying "25," and then collapsed.



----



While Mike took off to his room to throw on his fireman's uniform, Vicky, in her sexy tight nurse's uniform, took me to the kitchen and said "Don't worry about Mike, baby, he is just a hard-ass sometimes, especially when it comes to a guy being a man's man. Now, these vitamins I am going to be administering to you will help you grow in the right places, Jackie. There are three types here, and they all work in conjunction. You use them every day from now on, understood?" 



I just nodded. I felt humiliated by Mike. Why did he have to call me Cupcake, and Jacqueline? Why? It hurt.



Vicky continued, "First, the transdermal patch we apply directly to the skin. It allows the vitamins to be absorbed all day and night. We replace it daily, OK? First, we wash the area we want to put the patch, so in your case on your tummy or just above your butt," and she washed me and patted me dry, applying the patch. "Every day, understand?" I nodded yes.



"OK, next, we have a two little vitamin pills -- one taken daily, the other taken twice-daily, ok?" she asked. I nodded yes. "I will write all this down and make sure you have enough and do not forget, ok, Jackie?" 



"Yes, Vicky. This is so nice of you to do this for me," I said. She smiled and said "Jackie, you are going to become so healthy from all this effort. I have a summers worth of projects, and you can work out and become the best version of you. Mike and I will be here to guide you, if you want."



My heart jumped at the thought. A full summer hanging out with Vicky seemed like a dream come true. Mike I was not so sure about, but I would do anything to spend my days being around Vicky.



"Yes, I would love that, really! I can do whatever you need, Vicky. Thank you!" I said with true enthusiasm.



"Well, you may not want to thank me so much after this next step, baby. Roll up your sleeve," and with that she drew out a needle and a vial and filled it with a clear liquid. "Baby, this is a booster shot, to kick-start the effects of all these fantastic vitamins." With that, she rubbed my arm with an alcohol wipe, then injected me with the shot. "There, all done. Now Mike and I must go," and she kissed me on the forehead. 



I smiled. She is so nice. Mike is a hard-ass, but maybe he means well. I liked them both. Before they departed Mike ran through all the same things he told me the night before about the painting job. Then they left.



----



Alone in the house, I sat for a few minutes to just reflect on the whirlwind past 24 hours, my good fortune to come into my own little wardrobe this morning, as well as all I had learned online this afternoon. I decided to run myself another bubble bath and soak.



I went into Vicky's bathroom, and put in some really pretty smelling scents and the bubbles. As the tub was running I continued my exploration of her vast playground of a closet. I found a pretty black, sexy teddy and set it aside. I then went and found some pretty black heels to go with it. I laid them both out to see from the tub, and then proceeded to strip naked and hop in.



I shaved my legs and face and chest but felt nothing come off -- I was as smooth as could be - but it felt nice. I washed my hair and used her products to make my hair soft and pretty. I emerged and toweled off, then proceeded to style my hair with her brushes and hairdryer, trying my best to do what I had learned on YouTube. It actually wasn't bad, I was impressed. I then proceeded to apply makeup and was pretty fast at making a very passable face. In time I would take longer and do a much better job, but for me at this time I was very satisfied. Hair and face, done!



I felt a little dizzy. Maybe it was the vitamins and the shot. Maybe it was the squats. Maybe it was both, but I felt a little light-headed, so I slowed a bit. I had all night. I had not eaten much all day, and it showed. I was so fucking skinny in my midsection that if I didn't eat, my hip bones protruded even more than usual. Whatever. My ass and thigh muscles screamed out in pain.



I slipped on the black teddy, it fit perfectly. My shoulders, my skinny arms, my thin neck and tiny upper body allowed the front to drape sensually over my upper body. The lower part tucked right into my ass cheeks, and hugged me well, and really accentuated my bubble butt -- sore as it was from all of those squats. I took the heels and slipped them on, and then went to the mirror. 



My God, I was fucking stunning! I was downright pretty. I looked like a little goddess. I walked back and forth, admiring myself, and feeling so comfortable and so content. I decided to explore the house, and off I went with my heels clicking across the marble floor of the kitchen. I put in my headphones and hit the "dance/club" playlist. It was perfect for the mood. I danced and strutted through the house. What I also noticed was that this was the very first time I didn't just cum spontaneously. My little pee-pee was, finally, being more behaved! Good girl, I thought, and smiled.



After 20 minutes or so of exploring, I found myself in the kitchen finishing my second glass of red wine. I loved it. Never having tried it before, I had no idea it's effect. Finishing it off, I went into the bedroom and decided to paint in the outfit I had on. I was very careful to not splatter anything on the teddy or the heels. After an hour I was to dizzy to continue, so I slowly stepped away from the paint and laid down on Vicky's side of the bed. As a precaution I set my iPhone alarm for 10PM and every 10 minutes after until 11PM, in case I fell asleep.



----



I barely remember the decision, but I do recall reaching into Vicky's nightstand and pulling out this very large, very pink, very soft long double-ended dildo. I recall adding the strawberry flavored lube and sucking it, but I remember well the feeling of deeply fucking myself with it. I fucked myself frantically and it felt better than anything that went before it ever. I recall screaming and panting, the whole time along the music track continued as I fucked myself silly. I think I did this twice, maybe three times, but then I collapsed, passing out from the combo of vitamins, wine, no food, and too much self-pleasure. I am not sure if I ever came, but it felt amazing.



I woke at midnight. No alarm woke me. I was groggy, and yet just reached for the dildo, lubed it up, and began to fuck myself slowly. My hips bucked, and I moaned, and just humped myself to ecstasy. This was wonderful. All of a sudden, a feeling inside welled up, and I began to have an orgasm, but from somewhere deeper within my body -- it was not from my penis. I began to pump harder and the intensity of the feeling increased. All my muscles pulsed in unison, and then, from my soft -- soft? -- yes, my soft little pee-pee, a clear stream of thin liquid just poured out. No white, creamy jizz, rather a clear flow of slippery juice. I caught it my hand and slurped as much of it up as I could get to my mouth. The deep intense contractions increased to a point where I screamed out in pleasure.



I collapsed. I lay still, the pink dildo deeply impaled into my bottom. I was in heaven. Whatever I just did, it was the best, ever, and I must do it again. Yet...



...it was time to clean up, and get some painting done. By 1AM all was back in place, and I was frantically painting with a splitting headache - a combo of hungover, no food, and sheer exhaustion. By 310PM I called it quits, and as I got back into my bedroom I saw the lights of the Russo's car pull into their house.



Slipping quietly into my house, I tip-toed into my room and stripped naked. I put on my lavender teddy and collapsed in bed, totally and utterly exhausted. Yesterday was an amazing day, and today, somehow, someway, topped even that. These two wonderful days, so full of new discoveries and excitement, were to repeat themselves in both a similar pattern and yet more wildly interesting ways for the next few weeks to come. My life would never be the same.



...to be continued...

