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Chapter 8
by
caitlynmasked
What's next?
Chapter 07 - Body shaping
Changing into ‘Paris’ started first thing the next morning. Grace insisted that I start getting up as early as she did since for at least a few weeks I’d have to be reporting to the office before the sun broke the horizon. While she called into work, getting the next few days off so we could focus on me, I jumped into the shower with a pack of razers and two cans of Skintimate Coconut Delight Foaming Shaving Gel for women. Even after watching those YouTube videos I found on how to shave your whole body, it took forever to get every part of my body baby smooth. From my cheeks and chin to my neck and chest. My arms and back, my belly and groin. My ass and hips, my cock and balls. My legs and ankles and even my feet and toes. By the time it was all said and done I not only felt every single drop of water on my body, I also smelled distinctly like coconut. Which because of my experiences in the strip club will always remind me of strippers.
I thought that this was enough skin prep, especially as I wouldn’t be fully dressing up today, but Grace insisted that I start every routine and then maintain it until we’re done. That included full skin care. So, after I got out of the shower and pat dried everywhere and after letting Grace inspect my body for missed hairs, of which she found man, I got to apply a moisturizer, some shay butter lotion, and then something called body butter that was also strongly coconut scented. After all that my skin practically glowed and was incredibly soft to the touch. Even so, Grace promised that the more I did this over the next few weeks, the smoother my skin would feel. Both to others and to my own sense of touch. I couldn’t imagine it feeling smoother as just touching my new bare thighs was enough to start me growing hard.
After going through a similarly thorough process on my face, Grace helped me with my hair. On a day like today where we’d be shopping and moving from train to train all day, I’d normally just pull my hair up into a man bun to keep it out of my face. But Grace insisted that not only do I gently dry and comb out my hair, she wanted me to add some volumizing mousse. While this didn’t change the cut or style of my hair, it gave it so much more body that along with my smooth face, it had a more androgynous look. My hair wasn’t outright feminizing but it wasn’t exactly masculizing either.
Even my clothes were specially selected for today’s shopping. While I was working on my hair Grace went snooping through my drawers and found an old pair of underwear briefs that I hadn’t worn in years. I’d stopped wearing them because they were too small. The only reason I didn’t throw them out is that they were practically new and it just seemed wrong to throw away underwear that didn’t have holes or stains in it. As little as I wanted to walk around in these tighty whities, Grace again made perfect sense. Not only would this help me get accustomed to being tucked and wearing something tight down there, it would allow me to try on panties, shorts, and skirts without bulky underwear showing and ruining the look.
After I pushed my balls up into my body and tucked my penis back between my legs, I pulled the briefs up and yanked them tight. It didn’t even approach the idea of comfortable, but it wasn’t painful and was entirely bearable. Once on I added my thinnest pair of dress socks to mimic stockings when trying on shoes and then put on some loose sweatpants and a loose t-shirt, both picked out specifically because they’d be easy to get in and out of. I didn’t even balk at tossing my wallet keys and other everyday carry items into an old fanny pack to carry around. It helped me with the idea that I’d be carrying around a purse soon enough.
Thinking to myself on the train, I realized that the idea of being seen as ‘Paris’ was pretty easy. I know I’d have to work with Grace on the bimbo secretary attitude in order to properly entice Mr. Orpheus, but I’ve had audiences see me as a woman before. Hell, at the costume party guys were flirting with me. So, I knew that being seen as a woman wouldn’t be too difficult. Becoming a woman though, that’s an entirely different story. People weren’t looking at me as a woman right now. But they also weren’t seeing me as a normal man that I’m used to. I’m somewhere else on the spectrum. And I had a full day ahead to look forward to, picking out and trying on skirts, blouses, heels, and other accessories.
Our first stop was oddly the least stressful. We got to a little transgender specialty shop up in the medical district just as they opened at eight AM. It was a little stressful as I had to get my entire body measured, from my feet to my hips, from my waist to my ‘bust’, my shoulders, my arms, my thighs, my calves, even my neck, but at least everyone here knew that I was a man and was going to present myself as a woman. Unlike later when I’d simply stand out as a guy looking closely at bra and panty sets.
With all the measurements in hand we worked on something called a fajas Columbianas. I’d figured we’d start with a normal corset to pull my waist in, but once I saw the fajas I realized the advantages. One single garment would help shape my thighs, my hips, my ass, my waist, and my breasts. When properly put on, it would have seams only at mid-thigh and at bra level, leaving the rest of my body between smooth. While there were plenty of off-the-shelf options, Grace and I worked with the sales associate on ordering a custom fajas Columbianas. That way it would be as tightly shaping as we needed and fit exactly for my size. No extra material to bunch up and no areas that were too tight and might cause damage if worn for too long.
Since they were designing and custom making the fajas, we looked at breast forms that would be able to work perfectly with it. They would be separate pieces as they’re from medical companies, but the fajas would be designed specifically for the ones I picked, making them sized perfectly. Grace, the sales associate, and I went back and forth for about an hour on size. Surprisingly, I was the one arguing for a double D cup. I figured since we wouldn’t be able to show off the cleavage, we should at least show a massive chest. Grace was concerned about my ability to carry around the heavy forms in a bra all day and the sales associate was concerned that the size would be too big for my body shape.
After modeling six or seven different sets of breast forms in the mirror with various bras to give me an idea of the type of support I could expect, we finally settled on an set of incredibly realistic D cups. I still thought we could go larger, but this brand didn’t have DD’s available outside of special ordering them, where the D’s were in stock, in the perfect color for my skin tone, and we could leave with them today. And compared to the other sets, they really were the most realistic. Both in the way they moved on my chest and the way they felt. Again, it was strange how we tested that sensation. I thought I’d have to test them and was trying to find someone roughly my size to put them on when Grace walked up to me, turned me to face her, and then reached up and grabbed both of ‘my’ breasts. Looking down I saw her hands moving in a familiar and comfortable manner, realizing that she liked women with large breasts as much as me. And she’s felt them up as much as I have. She assured me that these ones felt like the real deal. Even though I could barely feel the breast forms moving against my skin, just standing there and having Grace ‘fondle’ me was incredibly arousing. It really put my briefs to the test as I felt I was hard enough to rip them in half. In fact, I wasn’t comfortable spreading my thighs apart and testing the durability for a good twenty minutes after Grace pulled her hands away.
Finally, just before lunch, we put all of it together. I slipped into an off the shelf faja that was close to what my custom fit faja would feel like. And ‘slip’ is completely the wrong word as I needed help three separate times to get the tight form changing garment on. But once we added the breast forms, a bra, a gaffe to hold me back, and a thong like pair of panties, the effect was bewildering. I must have stood silently in front of the triple mirror for a good five minutes, slowly turning side to side, and occasionally turning around and looking at my backside. If I only looked at my face, it was clearly me. It did look a little strange to see me without my chin fuzz, and my face was a little off because of the more poofy hair floating around my head, but it was still me. The body though. My body shape was just astoundingly, stupefyingly changed. My thighs were curvier without there being any obvious new bulges. They curved up into what I would call a damned fine ass if I saw it on anyone else. It was hard to look at it as a body shaping piece of clothing as the shape was perfect. It looked like a woman’s ass with a thong pulled up between the cheeks. And it jiggled as I turned and even clenched my own thin ass under it. My hips were rounded out so that the new ass looked natural on the body, especially from the rear, but when I turned and looked at the front it was clear that my hips were much larger.
As enticing as my new ass and hips were, I couldn’t keep my eyes from exploring my new thin hemmed in waist. I would have bet big money that only a heavily boned, and therefore obvious, corset could pull this much off my body but there was no seam, no hard looking points, no boning showing whatsoever. I could feel all of that on the inside as I could barely take a full breath, let alone a deep breath, but on the outside, it looked devastatingly female. And when combined with my large proud breasts I had exactly what you’d call an hourglass figure.
I had no clothes on outside of the panties and bra. I had no heels on and no jewelry. My hair was just hanging down with no real style and I had no makeup on. But looking at myself in the mirror, there wasn’t any mistaking what I was looking at as masculine. This one piece of clothing, along with the breast forms, was more effective at feminizing my body than the entire play had been or the entire French maid’s costume was. And it would only be more effective once all those accessories were added.
With as difficult as it was to get into the faja, and with as unusual as it felt, Grace and I decided that it would be helpful for me to remain in it. I knew I’d need the practice of having the weight on my chest, the jiggle and movement of my lower half, and the new breathing required form this tight pulling in of my waist.
The faja I was wearing out cost a hundred and fifty dollars. The gaffe, panties, and bra, added another fifty. The two custom fit fajas were seven hundred dollars apiece. And the breast forms were an eye watering three thousand dollars. I didn’t understand half of the features that the sales associate explained made the breast forms worth that kind of money, but Grace said these were the ones that Rhea had suggested. And since breasts would be such a defining part of my disguise, it felt logical to get ‘the best’. They even threw in all the care products we’d need including adhesive for the breast forms, solvent to get the breast form adhesive off, and cleaning supplies for the fajas.
Our next stop was a nearby secondhand shop. We weren’t buying anything here that I’d use in the office, but as my sweats now barely fit, too loose at the waist and far too tight around my hips and ass, obscenely tight around my chest, we picked up something that would work for shopping the rest of the day.
That little secondhand shop was where I got the crash course on women’s clothing and sizes. I’d just always assumed they sized pants like men’s but it made sense that these new measurements needed to be taken into consideration. After all, how many women had I seen with big asses on otherwise normal frames? It’s obvious now that I’m living in that world that the pants for that woman wouldn’t be the same as the ones Grace would wear, even if their waist and inseam were the same. Unfortunately for me, that meant the huge selection of women’s wear was quickly cut down to one or two items that would fit. We decided against the jeans as they’d be almost as tight and difficult to get on as the faja itself. There were three or four skirts, but I balked at jumping into skirts so early, especially in casual dress and the cold. That left the two pair of gym sweats.
Initially I opted for the white sweats with the word ‘Princess’ written down the leg and matching hoody, also with ‘Princess’ on the back in rhinestones. It’s not exactly the sentiment I wanted, but it was better than the alternative in my opinion.
Before I could even take them to the fitting room though, we found out that the pants were ripped. Right at the crotch. Even though it would only be for the rest of the day, that was still a big no. So instead, as we walked out and got back on the train heading downtown, I find myself wearing a pair of tight black track pants with the word ‘Juicy’ emblazoned on my ass and a matching black and pink oversized t-shirt with ‘Slut’ written across my new breasts. I’d only agreed with the t-shirt since it was loose and didn’t fit tight across my bust, thinking that I could cover up the offending word with my jacket. Should I have given that more than a moment’s thought and I would have realized there was no way my jacket could close around these new punching bags on my chest.
As much as I wanted to elbow Grace right in the ribs, I eventually had to join in with her giggling and laughter. After all, this really was a ‘laugh or cry’ moment and I would be put in much more embarrassing situations before we got Mr. Orpheus to quit.
What's next?
You're Not The Boss Of Me
Going undercover as a secretary backfires for poor Paris
Paris agrees to help his apartment mate Grace help
Updated on May 10, 2026
by caitlynmasked
Created on Aug 26, 2025
by caitlynmasked
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