SissyJune 21, 2026

Part 1 — The First Thong

Lucas, 24, crosses one night the threshold he had always avoided: the first lingerie, the first mirror, the first message to Madame A.

Part 1 — The First Thong

My name is Lucas. I'm 24 years old, I live alone in a small apartment in the suburbs, and until three weeks ago, I thought I was a completely normal guy.

Well… "normal". Let's just say I always had these kinds of thoughts. Thoughts that I pushed away as soon as they came. Images of myself in lingerie, on my knees, with something soft against my skin. I chased them away. I told myself it was just a phase, a passing fantasy.

One night in March, after a particularly shitty day at work, I found myself in front of my computer at 2 a.m., typing words I had never dared to search before.

"Sissy first time", "How to start feminization", "Buying first panties for sissy".

I spent almost three hours scrolling. Forums, Reddit, stories. I was shaking. Not just from excitement. From fear too. Because the more I read, the more I recognized myself.

The next day, I did something I never thought I would do. I ordered a black lace thong from a real lingerie website.

Three days later, the package arrived. I picked it up from my brother's place and drove home with my heart pounding.

Once the door was closed, I opened the package. The thong was small, thin, with lace on the sides. I took off my sweatpants and boxer briefs and put it on.

It was too small. The fabric got stuck between my ass cheeks and compressed everything in front. I got an immediate erection.

I looked at myself in the mirror. I looked… fragile. My hips seemed wider. The black thong stood out against my skin. And most of all, I was harder than I had ever been.

I spent almost an hour like that, walking around the apartment, getting on all fours, touching my ass to feel the fabric.

That night, I didn't cum. I jerked off several times but stopped right before. I wanted to keep that feeling.

The next day, I wore the thong under my jeans to work. I could feel it with every step. When I went to the bathroom, I pulled down my pants and saw the black thong. I took a picture. I looked at it for a long time before deleting it.

That same evening, I ordered something else: a small black pleated skirt and a pink thong.

When the order arrived, I tried everything immediately. The pink thong was even smaller. My cock had trouble fitting. I put the skirt on over it.

In front of the mirror, I had a shock. I didn't look like a guy wearing girls' clothes. I looked like a girl. My legs seemed thinner. And that pink thong pulling on my crotch was obscene. I got so hard it hurt.

I spent the rest of the evening dressed like that. Around midnight, I got on my knees in front of the mirror, lifted the skirt, and jerked off while looking at myself. I came violently, moaning like a girl.

Afterward, I felt very ashamed. I quickly took everything off and put my sweatpants back on.

The next day, I wore the pink thong under my jeans again. Every time I moved, I could feel it. I felt dirty. And I loved it.

That evening, I looked for more serious forums. That's where I found Madame A's profile. She talked about possession, transformation, and denial. Not just porn.

I hesitated for a long time, then sent her a message: "Hello. My name is Lucas. I'm 24. I just started wearing feminine clothes. I don't really know what I'm doing, but I know I need guidance."

She replied the next day: "If you're contacting me, it means you've already started something. Tell me exactly where you are."

I spent two hours telling her everything. The black thong, the pink thong, the skirt, the shame, the excitement.

Her reply came a few hours later: "You're not a sissy yet. You're a boy who is starting to understand that he wants to be one. That's good. If you want to continue, you're going to have to stop lying to yourself. Tomorrow, you will go buy feminine underwear in a store. Not online. You will choose at least one pink thong and a bra. You will pay for them at the checkout, without hiding. Then you will tell me how you felt."

I was very scared. But I already knew I was going to do it.

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