Sissy life

Sissy life

Jake likes to crossdress

Chapter 1 by Kaori_chan Kaori_chan

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane.

Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish developed over the years growing up together.

Now we are both 18, just finished highschool. Our parents expectations for both of us very different. I was to be expected to move out and get a job while my sister had her whole college paid for by our parents.

I needed to get the most out of my fetish while I still could. I wouldn't be able to wear my sisters clothes anymore when I move out and get a job. My sister of course had a bf, a life, constantly sneaking out and partying. It's really hard to tell what's she up to every night.

As soon as she snuck out, I knew immediately I had all night to crossdress and play in her room. First I found the cutest panties I could find. I dug through a pit of thongs and panties. They were all sorts of sizes and colors. The bottom of the pit was the most exciting, rarely used and very spicy. I found some blue Victoria's secret cheeky panties that read "I <3 boys". I was so excited I pulled them on immediately and wanted something cute over top of them. I wanted some spandex or cute leggings to go over these cute panties so I dove into the closet. I was unconsciously wiggling my butt, loving the feel of these panties between my cheeks and with a naughty message to top it off. It's like the panties were made for me.

Instead of leggings and spandex, I found wigs. My sis would wear these all the time interchangeably like it was a part of her personality. It always made her extra cute and cool at the same time. I always wanted to try them on for myself but never got the chance. Now was the time. I put on a pink medium length wig and looked in the mirror. As I looked up, I SAW MY SIS IN THE MIRROR. My heart dropped instantly as soon as I knew I was caught.

I turned around fast but no one was there. It was me in the mirror. I scared the shit out of myself. My sis Jane being my twin always looked like me but as a girl, she even had a tiny chest like mine. With that wig all I saw was a cute naked girl in panties that said "I heart boys". I was so turned on how cute I was, my tiny dick started to rise and I knew I wanted to cum as a girl. I hopped in her bed and dug into the nightstand. I needed lube or a vibrator or something to make me extra girly. I wanted to fulfill my sissy desires. Bam! I found what I needed. There was lube that made everything tingly and a buttplug vibrator that was oversized, for me, and had cool electric features to help you cum.

I lubed up the top of the butt plug and popped it inside while laying face down. It was way bigger than I was used to and I let out a moan when it slipped in. I pulled the underwear up and between my cheeks pushing the buttplug deep. I was so girly in my panties and this huge buttplug in my ass. My tiny penis was being squished and the plug had me already on edge from being so big. I pressed the ON button on the wireless remote. AND SOMEONE LEFT IT ON FULL BLAST. The electric shocks had my ass contracting around this huge buttplug that I could barely fit. I started spurting cum non-stop. It was so big I couldn't get it out especially with all those electric shocks. I was clinching down while cumming all over my sister's bed. I was stuck orgasming with the vibrations until in my horny haze I realized I could turn it down or off with the remote. The batteries in the remote on the other hand, were not as forgiving. The batteries were so dead in the remote I was stuck cumming over and over like a sissy. The batteries in the buttplug finally died but I was long passed out. There I was, in my sisters room, Crossdressed and laying face down in her bed, soaking in cum.

Who catches the sissy?

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