All posts by Allyson Medway

The Sissy Bride and her Transgender Groom: A Sissy Wedding Story

This story has twists and turns the whole way and personally speaking, I think it is one of my best. It is about a man, Jerry who was a crossdresser in a very conservative town. He had to keep his fetish under wraps but once he met a Mistress who found out that his biggest fantasy was to be a Bride, well se found a way to make it happen. The only problem was, who would be the groom and what would they want on their wedding night…?

The book description is as follows:

‘Keeping his crossdressing private was important to Jerry as he had no idea how it would play out in his community. Seeing his employee Gemma walking down the aisle though led him to be full of jealousy. He wanted all eyes upon him for once.

‘Luckily for him someone would walk into his life that would help him discover that he could have such a special day. It had everything he ever wanted, a chance to dress as a woman and to have a proper wedding day how he dreamt of it.

‘The only problem was if he was to be a sissy bride, someone had to be the groom. Would they would want all the perks of a wedding day…and a wedding night?

‘Jerry would discover all that and more as his adventures turn from fantasy to a very real reality in this 11,000 word short story.’

This book is just over of 11,000 words and you can read it for free using Kindle Unlimited or buy it for $2.99 (and currency equivalents thereof) via any of the following Amazon Locales.

USA
UK
Germany
France
Spain
Italy
Netherlands
Japan
Brazil
Canada
Mexico
Australia
India

If you live in any other country then you can buy it via the USA link.

I’m always delighted to hear from my readers, whether the feedback is positive or even negative. Tell me what you liked and what you didn’t. Tell me what you want to read more about. Tell me what you’d like to read less about.

You can contact me at and I’ll endeavour to get back to you as soon as possible. If you like the book then please do leave me a positive review on Kindle so that other readers can find the story.

The photo on the front cover of this book is copyright © paulasatjin on Flickr – https://www.flickr.com/photos/paulasatijn published under a CreativeCommons license – https://creativecommons.org/licenses/by/2.0/

Feminized into a Sissy by his crush

The next story I’ve written is all about a lonely man who has a bit of a crush. It seems sweet and innocent enough but he’s also a crossdresser who yearns to be exposed. Little did he know that the person who he was crushing on was all too willing to accept him for who he was, not only that, she had a plan to push his limits even further than our protagonist could ever have imagined…

The book description is as follows:

‘Simon has a crush on the woman who delivers his post. Instead of plucking up the courage to just ask her out, he develops an elaborate plot to show her his true crossdressing self in the hopes that she’ll reciprocate his strange advance.

‘Instead of it working and asking her out on a date, Simon finds himself at the mercy of a woman who knows exactly what she wants and it isn’t being wined and dined in any convention manner.

‘A 12,500 word short story about feminization and how with just a little bit of encouragement, someone’s eyes can be opened to a world that they had never even contemplated before.’

USA
UK
Germany
France
Spain
Italy
Netherlands
Japan
Brazil
Canada
Mexico
Australia
India

If you live in any other country then you can buy it via the USA link.

I’m always delighted to hear from my readers, whether the feedback is positive or even negative. Tell me what you liked and what you didn’t. Tell me what you want to read more about. Tell me what you’d like to read less about.

You can contact me at and I’ll endeavour to get back to you as soon as possible. If you like the book then please do leave me a positive review on Kindle so that other readers can find the story.

From Crossdresser to the Cosplay Café: A Crossdressing Journey

One of my sweetest stories is a short story about a crossdresser who grows in comfort and eventually has a chance to work in a Cosplay Café whilst wearing women’s clothing.

I have to admit I love this story. It is so heartwarming and goes to show all transvestites that they can find happiness along with acceptance when they open up and allow themselves to be who they are.

The description on Amazon is as follows:

‘When one of David’s university housemates comes home early from class only to find him cleaning the kitchen wearing a French Maid’s uniform, he is confronted with the realisation his crossdressing secret is no longer just that.

‘With trepidation he allows himself to be helped along in his journey down the road of wearing women’s clothing. With support and love, he finds a happiness that he’s been longing for along with way.

‘An uplifting first person short story about how David finds acceptance amongst his friends but also how he manages to keep both his male and female personas flourishing. We follow his growth from shy crossdresser into confident maid and into the big wide world as a happy adult, just one with two very distinct lives…

‘This book is suitable for everyone who is interested in understanding how having interest in wearing women’s clothing is perfectly normal and acceptable in the world today. It is also one for those who enjoy the idea of wearing a French Maid’s uniform in public.’

This book is just shy of 8,000 words and you can read it for free using Kindle Unlimited or buy it for $2.99 (and currency equivalents thereof) via any of the following Amazon Locales.

USA
UK
Germany
France
Spain
Italy
Netherlands
Japan
Brazil
Canada
Mexico
Australia
India

If you live in any other country then you can buy it via the USA link.

I’m always delighted to hear from my readers, whether the feedback is positive or even negative. Tell me what you liked and what you didn’t. Tell me what you want to read more about. Tell me what you’d like to read less about.

You can contact me at and I’ll endeavour to get back to you as soon as possible. If you like the book then please do leave me a positive review on Kindle so that other readers can find the story.

The photo on the front cover of this book is copyright © Nayuki on Flickr – https://www.flickr.com/photos/nayukim under CreativeCommons – https://creativecommons.org/licenses/by/2.0/

Carl’s Arrest Fantasy Gets All Too Real

The next book focuses on one of my very favourite fantasies, getting arrested. I have no desire to ever see the inside of a jail cell but the thought about being a sexy hooker and being arrested, handcuffed, bundled into the back of a police van and locked up is terribly exciting. This story is about a man and wife who have been upping the ante recently with regards to sexual thrills. Once he lets slip he would like to be locked up dressed in women’s clothing, well all bets are off and his wife makes sure it happens…

The book description on Amazon is as follows:

‘Carl and Karen have an extremely spicy private life and are always trying to explore new ways to give them their next thrill.

‘One day Carl tells his wife about how he’s always liked the idea of being arrested as a woman and spending a couple of days locked up. Karen’s eyes light up and before he can stop her, Carl finds himself on the streets waiting for a police van to come around the corner and take him to jail.

‘Crossdressing adventure as Carl faces up to the reality of his situation but Karen has one or two surprises in store…’

This book is just shy of 8,000 words and you can read it for free using Kindle Unlimited or buy it for $2.99 (and currency equivalents thereof) via any of the following Amazon Locales.

USA
UK
Germany
France
Spain
Italy
Netherlands
Japan
Brazil
Canada
Mexico
Australia
India

If you live in any other country then you can buy it via the USA link.

I’m always delighted to hear from my readers, whether the feedback is positive or even negative. Tell me what you liked and what you didn’t. Tell me what you want to read more about. Tell me what you’d like to read less about.

You can contact me at and I’ll endeavour to get back to you as soon as possible. If you like the book then please do leave me a positive review on Kindle so that other readers can find the story.

The photo on the front cover of this book is copyright © Melle_oh on Flickr – https://www.flickr.com/photos/melle_oh/ under CreativeCommons – https://creativecommons.org/licenses/by/2.0/

Sissy Maid at a sleazy motel

This Sissy Maid story is all about how a young man is strong-armed into becoming a maid at a sleazy motel but it isn’t all about cleaning, well unless you count giving head as cleaning cocks that is…

The working description of the book is as follows:

Johnny is offered the chance to fully fulfil his sissy crossdressing fantasies by his good friend Gloria. Little does Johnny know that she has big plans for him that involve far more than he could ever have bargained for.

‘After spending a day working as a real life chambermaid in a very low budget motel, he finds out what working at a place like this really entails.

‘A first person sissy maid short story about how a throw away confession can lead someone to a world that they could only dream about…or maybe it is a nightmare…’

This book is just shy of 8,000 words and you can read it for free using Kindle Unlimited or buy it for $2.99 (and currency equivalents thereof) via any of the following Amazon Locales.

USA
UK
Germany
France
Spain
Italy
Netherlands
Japan
Brazil
Canada
Mexico
Australia
India

If you live in any other country then you can buy it via the USA link.

I’m always delighted to hear from my readers, whether the feedback is positive or even negative. Tell me what you liked and what you didn’t. Tell me what you want to read more about. Tell me what you’d like to read less about.

You can contact me at and I’ll endeavour to get back to you as soon as possible. If you like the book then please do leave me a positive review on Kindle so that other readers can find the story.

The photo on the front cover of this book is copyright © Tanya Munroe from Flickr – https://www.flickr.com/photos/sissyfifi/ – published under a CreativeCommons license – https://creativecommons.org/licenses/by/2.0/