The Crossdresser’s Guide To Marital Bliss – Part 1.


The Crossdresser’s Guide To Marital Bliss is a series of episodes taking a hilarious look at how one crossdresser brought his wife to a place of understanding and acceptance. It’s also instructive and full of good advice to those of us who wish to introduce our dressing to the principal relationship in our life. I hope you enjoy it. Get all episodes here.


Part 1.

I sat in the garden enjoying the cool spring breeze. Sylvester crossed the lawn carrying a tray of tea and ginger biscuits.

“I’ve just had yet another experience with one of my members that leaves me feeling quite sad,” I said as Sylvester’s ham like fist gripped my delicate tea pot and poured.

“What was that, then?” he asked.

“Well, I had this chat with another member who just felt he couldn’t talk to his wife about crossdressing. I mean, really, it’s awful. So many of my lovely gurls are out there and barely even able to talk to anyone.”

“But that’s what you’re here for,” said Sylvester.

“Well, yes,” I replied. “But there are certain things that a wife can do that even I may struggle to!”

Sylvester looked at me with that heavy eyebrowed look of his.  He really is quite an extraordinary creature. He is and has been a mechanic for many years.  He’s also an inventor and has managed to create a number of quite interesting devices over the years, some of which can be operated relatively free of danger to life and limb.

“The problem seems to be that people don’t really know how to raise the subject – how to introduce it – without frightening their wives half to death.”

“Well, you can hardly blame them,” sympathised Sylvester.

I thought back to one of the early forays I made into the world of crossdressing. I’d been dating a young woman named Caroline who came home to find me wandering about the home in her panties and a blouse. It was a serious lapse of judgement on my part.

“Some women seem more receptive to it than others,” I mused, remembering the way Caroline had doused my male clothes in gasoline and set fire to them on the front lawn. Her words of good bye still echoed in my ears from all those years ago. The term ‘steaming poof shirtlifter,’ seemed to feature prominently, if inexplicably, considering we’d enjoyed what could only be described as a prodigious and intense sex life. Caroline was a debutante, and apparently felt my exploration of gender fluidity was something that wasn’t what young affluent girls in Chelsea should expect from their partners.

 Happy memories. About three weeks after we’d had such a firey break up her mother, Rose, had called and promptly installed me in a nearby apartment, along with a wardrobe allowance and a new 750 cc motorcycle to help convince me that despite the age difference there were indeed compatibility areas that might be worth investigating. Her generosity of spirit was matched by her voracious appetite, and let’s just say the mother had it over the daughter when it came to experience and her desire to expand the limits of a young twenty year old’s boundaries.

Much to Caroline’s horror I remained a close companion of her mother for some three years before being unceremoniously replaced by a younger more effeminate model – Danny. Rose and I remained close friends until her death, and even at the her mother’s funeral young Caroline still fumed, much like the burning pile of clothes had on her front lawn. I think it was me that she was still angry at, from across the graveside. Danny, myself and a number of other younger consorts attended the dear woman’s funeral and drank to her memory fondly. Perhaps not the way her daughter would have imagined a funeral, but a lovely way to exit an exciting life.

But then, that was the eighties, and in the time of the new romantics one could get away with a lot. Heels, gothic black ruffled shirts and eye makeup.

It was a pretty cool bike, too.

Be sure to join and enjoy further episodes of The Crossdresser’s Guide To Marital Bliss. Fiona

Get all episodes here.

6 Replies to “The Crossdresser’s Guide To Marital Bliss – Part 1.”

  1. I’ve been lucky to have had girlfriends who didn’t get attached, although some of their mothers wanted them to, but I really didn’t either. So when I lost one I didn’t feel bad. I felt lonely but somehow relieved. But it was hard to find a girl who didn’t mind if you dressed in prettier clothes than she did. But sharing this part of your life with a woman who you lived with for 35 yeas and has never seen this side you is difficult. I know if I continue to peruse becoming feminine she will eventually become suspicious. I don’t know what I’ll do. But just like Andrea I’m finding out this is a part of me and I can’t escape it.

    1. I find that a gentle approach is definitely wise. Telling her outright is often a bit more of a shock than a person needs, and it is a hell of an adjustment. Better to use softer langauge and gently to emerge over a period. It’s often wiser to move to a more androgynous clothing choice, and let people get used to seeing you in that image for a while. (You may enjoy my Pinterest page about this – Then gradually ease the more feminine aspects of yourself out over a period.

      Most of all though, remember it’s not all about clothes. It’s as much about how you think and act, and even how you talk and connect with people.

      1. Thank you. You make an excellent point. I want my feminization to focus on how I think, act and react, and connect with people the clothes I am use to. I pay attention to how the women in my life interact with others, and I try to emulate them, however I feel that I need more work in this area. I think dressed as a man my intentions are perceived more as a predator than as a caring nurturing human and it hurts me so much to be seen that way. It may take me several days to weeks to recover if someone does this to me. I think if I was “En Fem” the reaction would be different. You just expect to get a hug or kiss from a woman. And I think hugs are just great! Am I wrong or is my approach not appropriate?

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