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...

I stood, looking down at the small, bright pink chastity cage that had just been locked around my dick and balls, in complete shock. Moments earlier, Bella, the smoking hot ex-swimwear model, had been on her knees sucking my dick whilst wearing a leopard print bikini that barely covered her perfect breasts. With a wicked smile on her face, she was now slowly standing up. "What the fuck, Bella! What have you done?" I stamm...

I was still lying on the bed, savouring the taste of Don's seed in my mouth, wearing the leopard print bikini, contemplating what I had just done. I never would have thought it, but being forced to clean up Don's big black cock and eating all his cum out of Mistress Bella's pussy had really turned me on. My hard little clitty was pressing against the little pink chastity cage. At that moment, I wanted nothing more than to...

I had been living on the superyacht for two weeks now, as Olivia and I had settled into my new life with ease. I had an almost daily routine of going to the gym in the mornings with my sissy friend and roommate, Lexi, where she taught me exercises to grow my booty and tone the rest of my body. I still didn't have much in the way of girl clothes, so at the suggestion of Mistress Bella, I performed my morning workouts naked...

It had been a couple of weeks since my excursion to the gloryhole and outfit shopping in Positano, which resulted in my first breeding by Don, the older black Adonis who owned the superyacht. I had settled into my new sissy life well and finally felt like I had found my place in life. I hadn't worn boys' clothes in over two months and loved all the sexy, skimpy outfits I got to wear daily as I sunbathed and worked on my n...