Becoming my best friend’s crossdressing sissy girlfriend CH 05 – Passion

I practiced everyday what my sister taught me. Each night when everyone else went to sleep, I went to work. I always started with a shower and shaving myself all over. I used female body lotion to keep my skin smooth and soft.

I then sat in front of the mirror and worked my makeup routine until it was muscle memory. I tried on all the outfits and I practiced walking, sitting, and even speaking in my girl voice. I brushed out my hair and even experimented with a flat iron. I was more confident than I had ever been and felt more feminine than I ever have in the past.

When Jax told me what time he could come over that weekend, I was excited. I planned it perfectly. When he range the door bell to come in, I left the door unlocked so he would eventually just walk in. I stood a few away in the entry way hallway, my arms draped along the walls, my hips bent, and my chest lifted. I wore black stockings, black panties, a black satin bra and a black garter belt attached to the tops of my stockings. I wore a black secretary pencil skirt and a loose white off the shoulder blouse. I relaxed my eyes and pouted my red lips when Jax walked in.

Becoming my best friend’s crossdressing sissy girlfriend. CH 03 – Emotions

Recovering from our first time together was slow and painful. In the days after, my ass was sore and I had to walk slowly. I hadn’t anticipated how tight I would be nor the burning sensation that accompanied him fucking me like that. Still, I caught myself daydreaming about the feeling of his hot stiff cock in my ass and longed for it again.

This weekend, both of our families were at home. The opportunity to spend our time together seemed hopeless. Jax text me on Saturday and asked if I wanted to go for a ride. “To where?” I asked. “Just around.” He said. I knew what that meant. In our younger years, Jax and I used to smoke a lot of weed. To avoid stinking up the house or garage, we would go for these long drives around some rural roads, away from people and the town. Some of these roads would go for dozens of miles in all directions and never more than an house or two on each.

Becoming my best friend’s crossdressing sissy girlfriend. CH 02 – Exploring

Jax did text me later. He told me about what his family had for dinner and we swapped a few memes. Neither of us said anything about our encounter or what happened. Was he avoiding talking about it? Was he even thinking about it? I went to bed that night with a million thoughts running through my head.

A few days later my sister was out of the house again. I used the opportunity to go through the box in the back of her closet again. I desperately wanted to wear that old pair of skinny jeans she had in there, but couldn’t get them past my squishy thighs. I could fit in the skirt she had though. It was khaki with heavy pleates at the bottom that stopped above the knee. The silk black blouse fit as well.

That weekend she had another tournament that my parents took her to. Jax text to see if he could come over. I told him to come around lunch, that gave me a little time to get ready.

Me (18M) becoming my best friend’s (20M) crossdressing sissy girlfriend. CH 01 – First Encounter

Jackson and I grew up just down the road from each other. I always called him Jax for short. Even though he was 2 years older than me, he never acted too cool to hang out with me and during our teenage years we spent a lot of time together.

As we got older I began to notice him a little more. Maybe I looked a little too long when he took his shirt off at the pool and caught a look at his butt when we had to change clothes or something. I never thought I was gay, but Jax just seemed stronger and more masculine then me. I never developed the strong chin and jawline he did and I could never grow any facial hair. I was just thinner and smaller than him and never gained any muscle. I was just “softer.”

I remember how it started… I was going through a goth emo phase. I grew my hair out and let it fall over one side of my face. My dad hated it, but my mom encouraged it. I even wore a little eyeliner from time to time. I guess I was just trying to find myself.