A Story of a Sissy Ch. 03


After I’d exposed myself to Joan she ramped it up. She wanted easier ways to keep in contact and we started WhatsApping and FB messaging throughout the days. She told me to start wearing panties under my clothes at all times. I didn’t need to wear hose or chemise, but she told me I needed to be constantly reminded of my sissy. She told me to go buy enough pairs of panties to ensure I had a clean pair for every day of the month. I didn’t tell her I’d already had enough panties, because it gave me an excuse to buy more. I wasn’t wearing panties under my man clothes on work days, I’d reserved that for weekends, but because she asked me, I followed her instructions. It was tough at first. Every time I’d go to the bathroom or had a quite moment alone, I’d realize I was wearing panties and I’d have to focus on something to get back on track.

She wanted to know how my crossdressing began, how it advanced, and what I still wanted to accomplish.

I remember so vividly how she started to take control of me. Remember, I still didn’t know she’d read all my stories on Literotica. I’d told her a lot about my sissy, but I painted a picture of a man who fetishisized women’s lingerie and had some shared experiences with two women with whom I’d had serious relationships, but that those experiences were limited. I’d told her I’d had some closet homosexual sex with men, with me performing oral sex exclusively. And I’d told her that I shave my legs, crotch, and ass, and that I’ve experimented with makeup and nails. I’d also shared some pics with her wherein I was dressed up as my sissy.

She didn’t know that I’d begun a kind of relationship with my sissy. That my sissy had become my metaphorical lover. That I’d begun enjoying my time with her more than I enjoyed being with real people. I didn’t tell her about my profile I’d created and built up over the years with clips and pics of my sissy. But, because she’d read my stories on Literotica, she knew, at the very least, that I’d fantasized about all of the above.

Soon after I’d sent her responses to all of her questions she sent me a WhatsApp message: Sissy, after work on Friday, go to your favorite department store and buy a new sexy linerie outfit. Go home and bathe, shave, have a drink or two, smoke a joint, and then go to your favorite hangout. When you’re there, send me a message and wait for my instructions.

That was the first time she called me sissy. I will never forget that. I was falling for her hook line and sinker.

I went to Karstadt near my flat, a risky move because I had friends in the neighborhood who I could run into, but I threw caution to the wind. I walked into the store and browsed the panties and bra section. I couldn’t decide and moved to the hosiery. I found a pair of Wolford wide-net fishnet stockings. The kind I’d only ever seen in porn magazines. They were over a hundred Euro but I didn’t bat an eye about putting them in my basket. Then I found a nylon/polyester blended, tight-fitting black with purple lace trim chemse that was form fitting and came down just below the bottom curve of my round ass. Having the wide-net hose and black tight-fitting chemise, limited my options for the panties that would coordinate the outfit. I returned to the panties and found a tandoğan escort microfibre polyester/nylon purple thong. It was perfect.

I made my purchase in the lingerie department before going and picking up a nice candy-apple red nail polish in the makeup department. Then I stopped by a drug store that was located in the same mall as the Karstadt and picked up depilatory cream (3 tubes), and a bottle of baby powder. I always used baby powder after performing my ablutions. I picked up some scented candles and some bath oils.

I rushed home. My flat was literally down the street and I almost broke into a sprint to get home. I poured a whiskey/ginger ale, lit candles, and spread out my purchases on my bed. I took a picture and sent it via WhatsApp to Joan.

Joan: Very nice. Document your evening for me sissy. I want pics of every stage of your process. I might be able to help you.

In the bathroom I began my ablutions. I opened two tubes of depilatory, I’m very tall and from practice I knew that a good thick layer of cream works much more effectively than just a thin coat. I smeared white cream all over my legs, tops of my feet, and over my curvy ass and in every nook and cranny of my crotch, balls and base. Standing in front of my full-length mirror, [snap] and [send].

Then I smoked a cigarette and sipped my whiskey/ginger ale. I’d learned through trial and error, if I smoked a liesurely cigarette, by the time I’d finished, it would give the cream the time it needed to activate and work its magic.

I stood in the middle of my claw-foot bath tub and used the plastic paddle to scrape away wide swaths of hair, working from my feet, up my calves, thighs and finishing in my ass. The curves and crevasses of my crotch always proved challenging but I’d learned how to contort and twist my parts to reach every hair. Then in ceremonial fashion, used my extendable showerhead to wash away my disgusting man down the drain watching as the last of my male swirled down the drain. [snap] and [send]. The first pic of me standing totally nude with my sissy clit standing straight out from my sissy smooth body.

Evening was setting in Berlin. I lit candles around my flat, walking from room to room nude, my clit bouncing and flopping around I’d catch glimpses of myself in any reflective surface. I left all my curtains open, but being on the third floor, only those windows facing my flat would be able to see. I started my bath, poured in some oils and bath beads, and poured a drink and smoked a cigarette and waited for my bath to fill.

I put on some Coltrane. I set my camera up so the bath would be in full frame and then slid into my hot bath and the familiar burn from the cream seeped into my soft skin and I lay back in my tub. [snap] and [send].

I smoked several cigarettes and sipped my drink. I felt my sissy, so nearby. I felt Joan, imagined her looking at my photos, imagined her, “I have you sissy! You are mine now!” I imagined her thinking. “You will do whatever I ask now. You are my slave now. I control you from now on, you are no longer in control.”

The warm slick water worked on my body. Soon the burning sensation dissipated and was replaced with smooth, oily sensations that made me feel so tunalı escort sissy. I played with my pussy and clit. Teasing myself, fingering myself with the slick water making my pussy wet and slippery.

With my drink drained, I stepped out of the tub and stood on the plush bathroom throw rug and padded the dripping water off my slick body [snap] and [send]. I walked around my flat nude and wet. I did some minor cleaning and tidying up while letting my body air-dry. I liked letting myself air-dry while doing little domestic tasks, not only did it feel good, but it ensured a clean and tidy flat.

Once completely air-dried, I powdered myself all over. [snap] and [send].

I go into my living room and put on some Netflix and watch Game of Thrones while I paint my toes. I usually would paint my nails too, but because I was going out, and the paint was candy-apple red and easily recognizable, I only did my toes. I wanted to see how they’d look through my hose. I was very good at painting my toes. It was a labor of love. I love painting my toes. My body smelled like baby powder, my skin felt fantastic and smooth and slippery. Mixed with the paint I was intoxicated. [snap] and [send].

Joan: Very sexy sissy. I love your documentation. Your process is so interesting 🙂

My clit twitched uncontrollably.

I lay back on my couch with my feet up on the arm of the couch and watched the rest of an episode letting my toes dry. I was checking out my new wide-net fishnet Wolford’s. I’d never seen such a sexy and slutty pair of hose, and that Wolford made them was surprising, I’d always thought you could only get these kinds of hose in a porn shop and those hose are always so cheap. Wolford hose are top of the line. And I noticed the toes and heels on these had tight-nit netting for reinforcement. I couldn’t wait to put them on.

They were tricky. I pointed my toes and snuggled them tightly into the reinforcements and pulled them over my heels making sure the reinforcements lined up and then pulled them up my legs. The wide-net was tricky but because I’d done this so many times I was pretty good the first time. I only made a few littel adjustments and then I stood in front of my full-length mirror and marvelled at the woman in front of me. My legs, hips and ass filled out the hose so right, I looked like a real woman.

I realized, in my haste, I’d forgotten my panties. [snap] and [send].

It wasn’t a problem, it was the putting on of my lingerie that was the most thrilling aspect of being a sissy. I slipped off my hose and slipped up my new purple microfibre thong that slipped deliciously between my ass crack and against my smooth asshole. The soft and silky pouch barely contained my hard clit. My clit stretched the band that would normally nestle against my pubis, was pulled just enough forward that I could see my smooth clit if I looked down at myself. Then I reapplied the same process as before and pulled on my Wolford’s. [snap] and [send].

I fondled my new chemise, I don’t know if it called a chemise, because it’s not like any other chemise that I own. It had spaghetti straps and a nice breast support with purple lace trim and if I had breasts the outfit would reveal my cleavage nicely. Designed ankara türbanlı escort for a small C or a B cup, my chest filled it out less than adequately. It was smooth, silky, stretchy and tight. I pulled it on and had to pull it down, it didn’t cascade down my body the way a chemise does. It was tight. I pulled it over my chest and stomach and left it stretched around my waist with my ass poking out lasciviously. [snap] and [send].

I had to pull it over my ass and stretch it into place. It felt like a second skin. It clung to my ass and stopped just under my ass and barely covered my panties. I looked so sexy. [snap] and [send].

I took several pics and sent Joan the best ones.

Joan: I love your outfit sissy. How much did it cost?

Me: total, Wolford hose: 125 euro; Thong: 20 euro; top: 35 euro; polish: 5 euro LOL, I love them. The hose are my absolute favorite 🙂

I started getting dressed. I put on my favorite man outfit, black slacks, black sport coat, black t-shirt and black leather shoes, no socks. I wanted the risk of exposing myself. If I was walking down the street you couldn’t see under the hem of my slacks because they fell on the tops of my shoes. But, if I sat and lifted my leg to cross it over my other leg, you could see my stockings. If I sat on a barstool you could easily see my stockings. If I walked up steps you could easily see my stockings.

Once I was completely dressed I admired my normal man look in front of the mirror. I was thrilled. [snap] and [send].

Joan: you are a sexy man!

I knew from her original story, she was into my look. I’m a rugged looking man. If you knew nothing of me and saw me walking down the street you’d never suspect. You would see a normal man. I knew she liked that rugged man type and yet she was so convincing in her encouragement of my sissy that I let that part dominate my psyche. I started in that direction and nurtured that side to an extreme. Knowing what I know now, I would have catered to her needs more. Like giving her more “normal man” elements. But, because she was so inviting to my sissy and this was something I’d dreamt of happening for so long, I became narrow-minded in my pursuits.

I rolled a joint for the road, put out the candles and locked the door on my way out.

Me: Heading out.

I walked around my neighborhood. It was a nice spring evening and didn’t need a jacket over my sport coat. I felt the cool warm air slipping up every crevasse of my clothes tingling my body and mind. There’s an irish pub in my neighborhood where the bartenders know me so I went there.

It was pretty busy. I sat at the bar, making sure to rest my feet on the bar in front of me. There were enough people in the place that my feet were concealed by people standing around casually. If you wanted to get a look at someone’s feet sitting at the bar you’d have to crane and tork your gaze in a very deliberate and awkward way, so I felt pretty comfortable and at ease.

Me: I’m here. [snap] and [send]

Joan: tell me how you feel?

Me: I feel good. This is so exciting. Thank you for doing this, it’s thrilling. I’m sitting at the bar, and because I’m not wearing socks, anyone could see my hose. But I’m pretty confident, because there’s so many people here, no one is looking at anyone’s feet.

Joan: I want you to find a table, if you have to wait for one to open up, fine, but find a table and write me a story about a time you were with Jacqueline or Maria that excited you. It should include panty play of some kind.

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