A Midlife Makeover

By Sally Bend

As much as I had dreaded its coming, I actually got through my midlife crisis reasonably intact, and without doing anything foolish. Considering I was a closeted bisexual and a slightly less closeted crossdresser, that was really saying something.

It was my wife’s midlife crisis that drove a wedge between us, and the ensuing divorce that freed me to be the gurl I'd always felt inside. Free for the first time in my life, I reconnected with Sharon, the woman I had once thought destined to be my transsexual goddess of transformation, and finally put myself in her hands.

Having made arrangements for a very expensive weekend of feminization and fantasy, Sharon set about tearing down my walls, deconstructing my identity, and transforming me into the perfect bimbo submissive.

This 16,000 word story contains detailed descriptions of feminization, sissification, transsexual domination, first times, piercings, and more. It is intended for adult readers only.

• Language: English
• Publisher: Sally Bend
• Release date: Nov 15, 2017
• ISBN: 9781370274116

Sally Bend

Sally Bend is a nonbinary author, editor, and reviewer. Although shy and polite (she is, after all, Canadian), she loves to boldly and boisterously express herself through stories that bend the binaries of gender while exploring submissive sexuality.A lover of fetish, futa, feminization, femdom, and fantasy, she is most content when confined in a collar and corset. Oh, and she tends to have an affection for alliteration, in case you haven't noticed!When she's not curled up somewhere with a book and a bottle of Coke Zero, Sally can be found online at http://sallybend.com.

Book preview

A Midlife Makeover

Sally Bend

Published by Sally Bend at Smashwords

Copyright 2016 Sally Bend

Smashwords Edition License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your enjoyment only, then please return to Smashwords.com or your favorite retailer and purchase your own copy. Thank you for respecting the hard work of this author.

All rights reserved. Without limiting the rights under copyright reserved above, no part of this publication may be reproduced, stored in or introduced into a retrieval system, or transmitted, in any form, or by any means (electronic, mechanical, photocopying, recording, or otherwise) without the prior written permission of both the copyright owner and the above publisher of this book.

Check out other Sally Bend titles here

Table of Contents

A Midlife Makeover

About the Author

Connect with Sally Bend

A Midlife Makeover

As much as I had dreaded its coming, I actually got through my midlife crisis reasonably intact, and without doing anything foolish. Considering I was a closeted bisexual and a slightly less closeted crossdresser, that was really saying something. I’d already come out to my wife several years before, and she’d taken it in stride. Basically, so long as she never had to see it, hear about it, or be a part of it, she was completely fine with it.

Yeah. So, basically, I got to slip into a bra and panties on the odd night that she worked late, so long as I took it easy on the wine and stayed awake so I could change before she got home. Not exactly the out-and-proud life I’d always dreamed of, but there was some relief in knowing that at least one other person shared my secret, even if she didn’t share in its expression.

It was my wife’s midlife crisis that drove a wedge between us.

I don’t know whether it was physical, emotional, psychological, hormonal, or a combination of them all, but she became an extreme thrill seeker pretty much overnight. Everything, and I do mean everything, was fair game. She wrote off both of our cars speeding recklessly down the highway – the second time with her license already suspended. Then, to top it all off, she stole a car and wrote it off as well. It was while she was awaiting trial that she started sleeping around, first with some tattooed thug she met at the courthouse, and then with some homeless guy she met outside the courthouse – on the same day.

At that point, I was still willing to forgive and forget, so long as she got herself some help. Unfortunately, she wasn’t interested, and she continued to spiral. Pretty soon she was dabbling in hard drugs, gambling for the biggest stakes she could find, and robbing drug stores to support both habits. By the time her case for car theft went to trial, she was already in custody on a slew of other charges.

She actually served me with divorce papers the same day the verdict came down.

She was guilty and looking at a few years in prison.

I only felt guilty. Otherwise, I felt like I’d just been granted my parole.

Faced with a wide open future, I decided to tear the doors off that closet and embrace the crossdressing sissy inside me.

What made me reach out to Sharon, I couldn’t tell you. I hadn’t thought of her for years. I didn’t even know if she was still working, much less still alive. As much as I was enjoying my femininity, treasuring and celebrating the freedom of expression in a way that only someone who has truly missed it can appreciate, I had made a conscious decision not to reach out to old friends. It’s not that I didn’t miss them – I did miss them, and terribly – but I was afraid that they wouldn’t welcome the contact. Having been away so long, and having left the community so abruptly, I was afraid they would be angry with me for abandoning them.

I know I was angry with myself for all the wasted years and wasted opportunities, so I naively assumed they would be angry with me as well. Of course, I knew deep down that many of them had likely purged their closets and slammed the door behind them as well, but I didn’t see it that way. As much as I loved being a sissy again, I still carried a lot of guilt, and was still feeling pretty down over the