All posts by Allyson Medway

Transgender Romance Bundle: Three LGBT Novellas with Strong Women in leading roles

I thought I’d bundle together three stories where Transgender women play dominant characters and show some men exactly whose in charge. A good one for all those interested in transgender erotica.

The Amazon description is as follows:

Bundled together are three erotica stories with strong Transgender characters. If you like strong women showing little sissy boys just how they should act then look no further and read these three books bundled together for cheaper than 3 for the price of 2.

Inside you’ll find over 45,000 words of steamy action which includes an alpha male having the tables turned, a man who ends up marrying a transgender bride and loving life, along with a story about someone whose actions deserve severe punishment and boy is a harsh lesson given out.

This bundle isn’t for the faint-hearted. If you like your stories hot and heavy with plenty of action but also some actual plot then this is the book for you!

You can read it for free using Kindle Unlimited or buy it for $5.89 (and currency equivalents thereof) via any of the following Amazon Locales.

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

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

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.

Dixie Becomes the Sissy Maid

My latest short story actually developed from a flippant comment my partner made. Soon we are buying our first house together and she thought we should have a big housewarming party where I served all the guests wearing one of my maid’s outfits. Well I ran with that idea and wrote Dixie Becomes the Sissy Maid.

The Amazon description is as follows:

After years of searching for a partner who understood his desire to crossdress, Dexter finds Poppy who doesn’t just understand but is willing to play an active role in helping him find his female side.

Quickly they establish a hierarchy in the bedroom where Poppy blossoms in a dominant role. It doesn’t take long for her to ascertain that Dexter is extremely submissive.

Having enjoyed the delights of both Dexter and his femme persona Dixie, Poppy thinks it is time for Dixie to come out from the shadows.

Once out in the open, all bets are off about just how far Poppy can push Dixie down the road of ultimate submission…

Coming in at just over 10,500 words, this story explores sissy maid, humiliation and submissive themes.

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.

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

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

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.

My First Real World Sissy Experience

Considering I write about sissy erotica, I thought I’d share with you some thoughts on my first sissy experience many years ago. It will probably be the basis for a story in time. Even though I write about this type of thing, I just wanted to show that I’m also living it at least part-time. It gives me a lot of inspiration.

I had been flirting with a local pre-op TS over twitter and I had informed her that I was submissive. She said that we should have some fun. I was interested to experience it all so readily agreed. She wanted me to prove that I would be a good sissy, so she made me get into my chastity device, lock it up and stay locked up until we met. I still had the key but she text me asking for pics and messages/time stamps to prove I stayed locked up. I did and after the first couple of days I got used to it. Chastity had been something I’d played with on and off but it really does heighten your sexual feelings, it is well worth doing if that is what you are into.

Over the course of the next few days she would order me about in the evenings. Usually making me watch lots of gay porn as she told me I had to get used to lots of cocks. About ten days after we started, she text me and ordered me to report to her house immediately. I was freelancing at the time but luckily I could slip away for a few hours without any big drama.

She had been partying and her place was a mess. Her orders were to pleasure her and clean up her house. So I went there and dressed up in an outfit that she picked out and gave her a blowjob. It wasn’t an unpleasant experience although sadly she didn’t finish in my mouth. She pulled out and tried to fuck me but as it was my first time and she was huge, it wasn’t getting all the way in. This led to her giving up and getting me blow her again. Sadly she didn’t spurt into my mouth (which really disappointed me as I had done the work and wanted my cum reward) and didn’t even cum on my face, she just came over herself and cleaned herself up with a towel.

After this, I was ordered to clean her house and go. She didn’t speak to me again after that and stopped following me on twitter. I don’t know if it was because I was crap or because she found me unattractive or what. So a very curious and a tad unsettling experience for a first time.

I really didn’t mind giving head but I wanted to get my reward. Giving head was such a new experience that I really wanted to get the feeling of cum flooding my mouth, to feel properly submissive. Alas that wasn’t how it went down. I also didn’t mind her cock up my butt (what she could get up there) but felt this overwhelming sense that I needed to pee.

Actually experiencing this with someone was far better than getting excited watching porn alone. When you do that, often its an orgasm and then a sense of remorse. When you don’t get that post-orgasm come down, your remorse levels are a lot lower. Walking back home, my biggest regret was that she hadn’t cum on or in me. I try to use these feelings when I write because I know first-hand what it feels like, the first time you submit to a cock.

So yes, I wanted to share with you my first real-world sissy experience. thinking about it, I’m positive I’ll make it into a story but with a more exciting ending!

Candy’s First Craigslist Encounter

What sissy hasn’t fantasied about meeting a strange man in a hotel room and losing their anal virginity? Well this book is all about that scenario as we follow Terry’s journey to becoming Candy and submitting to Ian in more ways than one…

The Amazon description is as follows:

Terry had been leading a double life for most of his time on this Earth. To most people he was a regular guy with a doting wife. One person knew that he was different and as she continued to push the boundaries, a cover was blown. Life would never be the same again.

In an attempt to make something of his two world’s colliding, Terry decided to fully embrace his female persona he’d named Candy. At the time it wasn’t clear just how far things would go but buoyed by the support of another in a similar position, the wheels were set in motion.

Momentum is tough to stop as he would find out. In a seedy hotel room one Friday evening, it was clear where everything was heading and that Candy was very much part of his personality.

This 7,500 word story tackles the journey from a sissy’s fantasy and seeing it all the way to a very steamy reality.

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.

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

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

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.

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Biker Gang Alpha turned Biker Girl Bimbo

Out today is a tale which I’ve certainly enjoyed writing. I do like putting together a story where an alpha male gets their comeuppance but this I feel is doing it is a rather different manner. I hope you all enjoy 🙂

The Amazon description is as follows:

Getting out and having a good time with the ladies was all Darren lived for. Every summer he’d join his dad’s biker gang and hit up all the hot spots along the British coast line.

Worried that his son was going to end up lonely like he had, Darren’s father took it upon himself to intervene and try to mend his offspring’s wayward ways.

At the end of his tether, he turns to witchcraft to teach his son a lesson. It leaves Darren’s mind in tact but his body was not his any more and he’d find out first hand just what life was like for women.

Instead of fixing the problem, it creates many more as things don’t go exactly as planned…

This is a 11,500 word short story.

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.

Caught Crossdressing by the Neighbour

Going back to one of my favourite fetishes, my latest book is all about a young man who gets caught in the act of crossdressing. He’s in luck that the person who discovers his little game doesn’t use it to blackmail him, instead she decides to help him along with his journey…

The Amazon description is as follows:

Julian had dabbled in crossdressing but only in private. He was too scared that any public exposure would lead to ridicule amongst his university friends. His fantasies though were starting to become ever deeper and darker.

With his parents away for a week, it was the perfect chance to really go to town and explore his crossdressing habit. What he didn’t bank on was that someone would discover his little secret.

Instead of being shamed, his neighbour took him under her wing and allowed Julian to fully experience what it was to be a young girl. The only question is did she understand where his limits were…?

This 15,000 word short story explores crossdressing, feminization, humiliation and first time gay themes.

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.

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

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

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.

Locked up by Lust: A first time Lesbian Romance Prison Fiction Story

My first attempt at lesbian erotica follows the path of a young woman finding herself sexually not only in who she wants but what she wants and that is to be extremely submissive. We see her go to jail not only to see what its like but also to get turned on.

The Amazon description is as follows:

Being beautiful and popular was the dream of any young woman going through high school. Instead of enjoying the attention from all her classmates however, Donna struggled finding happiness and always wondered if there was something wrong with her.

After getting a full ride to study at UCLA, Donna was determined to take up the opportunity to meet people from all different walks of life. She left her small town in the deep south looking for adventure and to find herself.

What Donna could never have imagined is what was out there that truly made her happy and that was being told what to do by other women.

This is a 13,000 word short story that includes lesbian themes and steamy hot prison scenes.

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.

Transgender Fantasy Turned Reality

This is a darker story than most I’ve written so far. Eli is fighting the demons in his mind about what he wants from a partner and burns a few people along the way. When he’s given the chance to find out what he wants once and for all, it leads him to quite the revelation about who he is…

The Amazon book description is as follows:

Eli was a very confused young man. Unable to be honest with himself, he continued to live a lie and pretended he was straight despite his love of transgendered women.

One of those he’d had a relationship with offered him the chance to finally find out exactly what he was looking for from a partner. It would involve being her live in sissy as she expanded her dominatrix business, The opportunity was one that wouldn’t come around again and Eli felt like he needed to fully immerse himself in a world where he wouldn’t feel judged to find himself.

Packing up his bags and moving north away from his friends and family, Eli looked forward to being under the ownership of Mistress Leah. The one thing he didn’t know was what was in it for her, something he’d only find out in time…

This 16,000 novella explores transgender, crossdressing and sissifiction themes.

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 pride of getting a positive review

In the week I was overjoyed to get a thoughtful positive review from one of my readers. I’ve had a few reviews in the past or comments via e-mail saying they enjoyed a story but to get my first in depth review, it gave me a sense of pride along with an urge to work even harder to get more stories written.

My next book is currently going through a first edit, it will either go live in the next 24 hours or it may have to wait until next weekend. The darned real world gets in the way of so much doesn’t it?

Whilst I do that, I thought I’d share with you the review for A very public day locked in a Sissy Maid’s Uniform.

For my first taste of Allyson Medway, A Very Public Day Locked in a Sissy Maid’s Uniform was absolutely lovely. It puts a creative, realistic, yet deliciously kinky spin on the genre, exploring the willing humiliation of a young man who has discovered his sissy nature through submission to the right Mistress.

I love that the story addresses how Noah came to belong to Mistress Jasmine, acknowledging that other Mistresses failed him by trying to force him into the role of pain slut, when what he really craved – what he really excels at – is humiliation. It is Mistress Jasmine who first introduced him to feminine clothing, triggering something a revelation that opened them both to a deeper, more fulfilling relationship.

Personally, as much as I love sissy attire and female domination, humiliation has never been something that appeals to me, but Allyson struck a chord with me. There is a definite appeal in the anonymous sort of humiliation that Noah craves, and I loved how his transformation into Lola allows him to use that humiliation to drive him towards his ultimate goal of exploring his bisexual curiosity.

The details here are lovely, the dialogue simple but effective, and the personalities really make the story come alive. When it does finally come time for Lola to taste her first sample of manhood, the scene is a realistic as it is erotic, mixing sensations of lust with disgust. At the risk of spoiling the story, I was delighted by the way Lola explores her fantasy, without undergoing an instantaneous conversion in her orientation.

If that sounds like the type of book you’d like to read then please buy or read for free on Kindle Unlimited 🙂