Heyyy, my name's Ollie, and this story begins when I had just finished university and was in my early twenties. All my life, I had done whatever my parents had told me. Growing up, I had always concentrated on my studies and never had time for parties. Being only 5 foot 8 tall and scrawny, I never had much luck with girls anyway. At university, I managed to sleep with a few women, but that was few and far between, and onl...

After my adventure as a slutty sissy schoolgirl, a switch in my brain had flicked. Perhaps it was all the dick I had been made to suck that night, but the day afterwards, I went online and bought myself a small pink chastity cage, a dildo, and a new douche. I had also bought a trio of metal butt plugs of different sizes. On the base of the largest plug, it had the word 'SLUT' enamelled in big bold letters. In the same sho...

At the end of the first Covid lockdown in 2020, I was able to start meeting up with friends again. I had a group of mates who all lived in a flat in a swanky development in central London. The development was right next to the River Thames, with 24-hour security and a concierge. Best of all, my mate’s flat was great for having parties. I was having a BBQ with them one day when they mentioned someone was moving out, and th...

When COVID-19 took hold of the world in 2020, my parents sheltered in their countryside house. I continued to go to the office until the night the UK entered its first lockdown, and I was stranded, living alone in my parents' London house until the country opened up again. Whilst on the face of it, this wasn't ideal, the major benefit was that I got to be Sissy Ami full-time. There was no risk of anyone finding out about...

I was now twenty-three, had left university, and had found a job in the city. My retired parents had bought a second home in the countryside, where they spent most of their time. This meant I would often have weeks alone back home in London, giving me the freedom to dress as Sissy Ami for almost all my private time. Every evening, I would get home from work, strip down to the panties I had been wearing underneath my men's...

In the three years since the barber had used my mouth, university had gone well for the most part. I had made some straight guy friends through playing sports, and I ended up living in a house with them for the remainder of my time at uni. The sports, in turn, caused me to put on a bit of muscle. I was by no means bulky, more just athletic now, as opposed to having the frame of a skinny girl like I used to have. I met ano...

After the immediate elation from losing my sissy virginity to the bricklayer Steve. Strong feelings of shame had set in. I didn’t want my family to find out about my girly side. So, in September, when I started university, I chose to bury Sissy Ami. University started well, and soon, I had struck up a romance with a girl I had met through a society called Em. Em was the first girl I had caught feelings for. Unfortunately,...

When I had just turned 18 whenever I was home alone, I would get dressed in whatever I could find in my older sister's room that I thought looked pretty, run into the bathroom to admire myself, and then wank to my reflection in the mirror. Sometimes if I was feeling extra naughty, I would lick up my cum afterward, but most of the time I washed it away. I remember once finding a dildo hidden under my sister’s bed. The next...