u/SometimesJudith

Part 1: Prologue for slow build up lovers and context: https://www.reddit.com/r/cdstoriesgonewild/s/2oWUGlfGsV

At a certain point, my persistent questions clearly began to make him uncomfortable. He shifted in his seat, suddenly realizing how much he had just opened up. But the alcohol coursing through my veins gave me a sudden surge of reckless courage. I couldn't hold it back any longer.

"You know... hmmm... how should I put this?" I stammered, my heart hammering against my ribs. "I kind of... like dressing up, too."

Adam looked as if he’d been hit on the head with a sledgehammer. His eyes widened, completely sobered by the revelation. "What? How do you mean?"

Hesitantly, my face burning in the dim light, I began to tell him everything. I expected shock, disgust, or at least an awkward silence, but I was stunned to see him react... completely normally. He was obviously surprised, but as the initial shock wore off, he started asking genuine follow-up questions. He wanted to know what it felt like, if anyone else knew about it, and even ventured into more direct territory—asking if I considered myself trans, gay, or bisexual.

I answered as honestly as I could, though I carefully held back a few spicy details about the small collection of personal toys I’d gathered over time, and how profoundly they helped me unlock an even deeper, more intimate sense of my own femininity.

The conversation stretched on deep into the night, lasting until we finally finished the beer and began packing up. Adam turned out to be a true friend—he offered his unconditional support and reassured me that my secret was entirely safe with him, stressing that this wouldn't change a single thing about our friendship. By the time we started walking back toward our houses, the first pale light of dawn was already creeping into the sky.

As we reached my front gate, Adam turned around to head home, casually throwing out one last question. "So... rain is forecast for tomorrow. Repeat party at your place?" With a playful grin, he added, "Maybe you can show me your collection then," before waving goodbye and walking down the street.

I hadn't planned for any of this. My parents had just left for a long vacation, and tomorrow I was scheduled to drive my sister to the airport so she could catch a flight to Italy with her girlfriends. That meant the official kickoff of a two-week festival of lace lingerie, sheer fabrics, bold red lips, long press-on nails, and every other delicious attribute of femininity. Judy would have free rein over the entire house—I kinda hoped Adam wakes up with a brutal hangover and decides to bail on his offer.

Stepping inside the quiet house, I went straight to the bathroom and stood beneath a steaming hot shower, letting the water wash away the smoke and alcohol. I resited the urge to touch myself as I soaped my smooth body. Once I finally climbed into bed, sleep felt completely out of reach.

My mind was racing - I've been scrolling some nsfw subreddits and one of entries gave me some inspiration...and got me really turned on.

Too excited to sleep, and still a bit tipsy, I've decided to try something I haven't done in ages. I quietly went to the bathroom that I share with my older sister Natalie and started going through dirty laundry. Her clothes from today were on just laying top, and after a quick search I found her panties - a tiny pink G-string with a sheer front and flowery lace trim.

My sister might've developed a more adult taste in clothes, but these panties were a proof that she still had the inner slut in her. I slipped them on and realised she must've taken them off quite recently because they still felt a bit moist.

Like the old days, it felt sexy instead of creepy or disgusting. All the memories of going through her dirtly laundry came back. I tucked myself so I could feel like I have a clitty instead of a cock. Her panties were tight enough to prevent the unwanted bulge. I realized that I can feel my sister's scent mixed with my unisex shower gel and that got me even more excited. Even though she was my sister, I have to admit she wasn't only hot - she was the perfect, beautiful woman and at that point I'd do everything to trade bodies and maybe even lives with her.

I just went through her clothes to feel the fabrics to smell her delicate parfume, so I could Imagine I'm her - Natalie who has just came back home after discussing vacation plans with her girlfriends. Judging be the condition of her panties, they must've discussed hooking up with some handsome Italian fellas. 

On the bed, I played one of my favourite girl-on-girl pov videos. I wanted to get into mood so I started by gently running my hands against my silky smooth legs - my natural hair was mid-lenght boyish cut, long enough to feel the tips on my neck and higher back. As soon as the nipple play started in the vid, I licked my fingers and gently started playing with my nipples. After some gentle squeezing, pinching and massaging, I could feel the first drops of precum mixing with my sister's juices.

While one hand remained to stimulate my boobies, they other one explored my flat belly, inner thighs and ass cheeks. When the action moved to taking the panties down and some soft cunninlingus, I've decided to leave mine on. The first touch gave me shivers - the soaked delicate fabric felt amazing both under my fingers and on my throbbing clitty that was unable to escape the tight grip of the sheer material.

I rubbed my clitty like any girl would, gentle using just two fingers and still playing with my nipple. My body demanded an orgasm at this point but I challenged it. Knowing what's gonna happen in the last few minutes of the video, I reached out to my nightstand and got my tube of lube - I used it on my fingers, and got to my knees, sticked out my bum and put my G-string to the side.

I'm slowly started fingering myself, gently at first I explored my inside. At a certain point, just after I took whole finger in, second one followed to meet my needs. I have been on edge for some time, but fingering and nipple play were not enough. Actresses climax was just around the corner, so I changed position so I could both ride my finges and massage my clit - knowing that climax is close, I allowed myself a few quiet moans matching my tempo with the video.

I matched my orgasm with the video perfectly - it was so intense that I felt contractions all over my body like I'm possessed. A wave of warmth and moisture flooded the pink panties.

Knowing that my excitement is leaving me, I've decided to try one last thing - I thought about it in the past but never got the courage to do it. I took off my panties and had a taste of my own juices - I think I would not have liked if not for what was left by my sis. Her leftover cream was like a spice that makes a meal perfect. Surprisingly, I have licked the panties clean and put them on again knowing how future me is gonna thank me tomorrow for such a wake up.

When I was falling asleep, I had no idea that this was just a beginning of Judy's adventures this summer...

TBC...of you like it

Hi before we start, I just wanted to say I've always enjoyed CD fantasy stories and erotica. I've developed my own taste, and decided to start creating something that I'd love to read myself. This first entry should be considered as an intro to a collection of stories about Judy. Appreciate your feedback!

Having just turned eighteen, my name is Sebastian, but the story of who I truly am began long before reaching this milestone. For as long as I can remember, I have been deeply fascinated by femininity and the intricate elegance of women’s fashion—especially lingerie and pantyhose. It all started during my early teenage years with quiet, inquisitive steps into my older sister’s room. Over the years, as I watched her wardrobe evolve from playful teen styles into something distinctly more feminine and bold, my fascination only grew.

​Under the pretense of helping her clean and organize her room, I regularly sifted through the clothes she intended to discard. Instead of carrying them down to the local charity bin, I secretly set aside the pieces that captivated me most. In doing so, I slowly built a hidden collection of my own. The age gap between us and our complementary tastes meant that the garments she outgrew or left behind were almost tailored for my journey. As her cute tops and skirts were gradually replaced by a more mature wardrobe, my private sanctuary expanded.

​Because our parents often left us home alone for an evening or an entire weekend, and because my sister loved to party—trusting my responsible nature to keep the house in order—I was granted precious time alone. In those quiet hours, I didn't just manage my growing collection; I began celebrating the gradual emergence of my alter ego, Judy. Beyond the delicate lace and silky fabrics I salvaged, my collection soon expanded to include a synthetic wig left over from an old Halloween costume. The transformations became far more intentional and refined as I quietly borrowed makeup from my sister and mother, spending hours practicing techniques alongside online video tutorials.

​What began as quiet curiosity in the shadows of my childhood home gradually transformed into a structured, deeply personal art form. Every hidden pair of stockings, every carefully applied layer of lipstick, and every moment spent perfecting Judy brought me closer to understanding a part of myself that had been waiting years to fully step into the light.

Fortunately, I was always quite short and relatively slim. Swimming and running shaped my body beautifully—giving it a lean, toned contour without any bulky musculature—while also serving as the perfect excuse for keeping my legs completely smooth and hairless. As I grew older and started earning my own money, a dedicated portion of my income always went directly into investing in Judy. I bought my first pair of silicone breast forms in a full B-cup, crafted from soft, flesh-toned gel that settled with a realistic weight and teardrop contour inside a supportive lace balcony bra. Shortly after, I upgraded to a far superior, heat-resistant synthetic wig with a natural lace front that blended seamlessly into my hairline.

​Eventually, I began discreetly ordering my own wardrobe, delicate lingerie, cosmetics, and red almond-shaped press-on nails. The physical routine of assembling Judy became deeply satisfying. Pressing each acrylic nail onto my fingertips instantly softened the way I held my hands, causing my fingers to extend with a newfound grace. Fastening the slender ankle straps of a pair of four-inch patent leather pumps shifted my entire center of gravity, forcing a posture that felt entirely natural yet utterly transformed. When I stood before the full-length mirror, enveloped in smooth nylon, soft knits, and a refined face of makeup, there was no trace of Sebastian left—I saw only Judy.

​The next natural step was mastering the art of movement and communication. I spent endless hours practicing my posture and stride, learning to place one foot directly in front of the other to achieve a subtle, fluid hip sway while keeping my shoulders relaxed. I also dove into online voice-training tutorials focused on pitch control and resonance modification. By shifting my vocal resonance away from my chest and higher into the throat and palate, I practiced speaking in a softer, more melodic register until the cadence of my voice matched the woman looking back at me in the glass.

Judy had never truly revealed herself to the outside world—her transformations took place strictly behind the closed doors of my bedroom. My sister had nearly caught me a few times over the years, which provided more than enough adrenaline and stress to keep my secret contained. Occasionally, under the dense cover of night, I would muster the courage to step outside onto the quiet pavement for a brief walk in my favorite heels, listening to the muffled, satisfying click of my steps in the dark. More often, though, I contented myself with a subtle compromise: wearing silky lace underwear, sheer pantyhose, or a soft camisole tucked securely beneath my oversized, unisex hoodies and loose jeans.

​When it came to romance, I had never been in a serious, long-term relationship with a girl, though I had my share of brief flings and enough casual experience to know my way around. What I did have, fortunately, was a vibrant circle of female friends. I was endlessly grateful for them; without even knowing it, their effortless grace, personal styles, and everyday beauty served as constant inspiration for my own transformations into Judy.

​Among those friendships, three stood out above the rest: Kate, Anna, and Adam. Together, the four of us formed an inseparable tight-knit crew. We had just graduated from high school, every one of us officially an adult, standing at the precipice of a completely new chapter in life. With the stress of final exams behind us and a wide-open summer stretching ahead before we scattered to different universities and cities, we knew this was our moment. It was our final chance to cut loose, throw caution to the wind, and create unforgettable memories together before everything changed.

One night, however, planted the seed for everything that was to come. Naturally, I was much closer with Kate and Anna than with Adam, but during one particular night out, we ended up drinking a little more than usual. The girls eventually grew tired and called it a night, so Adam and I walked them safely home. Once they were inside, Adam convinced me to stay out for one quick beer in the park—which quickly turned into a second, and then a third.

​Settled under the open night sky, we talked about everything: girls, future plans, and complete nonsense. At some point, the conversation took a turn toward strange, crazy experiences we'd had over the years. That was when a slightly tipsy Adam let slip a story that caught me completely off guard. He admitted that a while back, just for fun, his ex-girlfriend had done his makeup and dressed him up in her clothes. Hearing him casually describe living out my ultimate, secret dream made my heart race. I fought hard not to let on just how envious and fascinated I truly was, so I subtly kept the conversation going, asking casual follow-up questions to keep him talking.

​Then came the real shocker—the confession that left me speechless. Dropping his voice, Adam shared a secret he had never told anyone else: he admitted that he hadn't just found it funny, but that he had actually really enjoyed it, and even found it surprisingly exciting.

You know what's funny? He had no idea, that at this exact moment, I was wearing a sheer and lacy black thong that became tighter with every detail he shared about his first dress up.

I realized that I might've had someone who can really understand me right under my nose and now he's going to leave to another city miles away.

But this was still just the first weekend of a long summer...

TBC if you like it😊