Tag: stories

Part 10.

Sitting in the garden, just by where Ali had completed a rather unusual example of topiary depicting Cleopatra’s Needle and two of the Elgin Marbles, not to scale, I poured my wife a glass of wine.

“Darling,” I said. “have you ever had a boyfriend who liked to crossdress?”

“Well, I really don’t know,” she replied nonchalantly. “What they get up to in their spare time is a mystery to me.”

“Yes, but surely,” I persisted, “there must have been one who showed interest. I mean, so many men talk about it these days. I can only think there must be some women who find it, I don’t know, exciting?”

“Well, I’ve always thought men look rather odd in dresses. Not to mention heels.”

“I’m sure,” I replied.

“On the other hand,” she went on, her voice dropping a little, “it does give me a feeling of power.” At that point she paused and corrected herself. “That’s to say I’m sure it would. If someone were to, you know.”

I looked at her sideways.

“Are you quite sure you’ve never…”

“Well, there was this one young man in college. A very unusual chap, but certainly very liberated. Exciting even,” she murmured.

I could see she was leaving a great deal unsaid, her mind wandering through what seemed to be some happy memories.  I decided it might be best to let it hang for a moment.

“I think it wonderful how much energy women put into their look, and it’s always seemed a little unfair. A man shows up to a date with a clean shirt and he’s considered well dressed. A woman spends two hours putting on corset and suspender belt and god knows what, and she’s not even remotely satisfied how she looks.”

“And ten minutes after you’ve left the restaurant they’re trying to get the damned stuff off! You have no idea.”

I kept my desire to say ‘I know exactly what you mean’ in check.

“Well, I must say I can’t help thinking that now and then a man should have to try doing that. Just to remind themselves how much trouble you girls go to.”

I topped up my wife’s wine.

“I think you may have something there. I think it would be a great idea to help men understand.”

I sipped my wine quietly.

“Well,” I murmured. “If you really insist. I suppose I could try.”

Part 8.

I’d had it in mind to tell my wife that I was a crossdresser for several months before I actually said the words.  By the time I did I’d shown a more gentle side of myself on numerous occasions and in many ways.

I was already taking her for regular shared nail appointments and had a wardrobe of increasingly androgynous clothing. It can hardly have been a surprise when one day I said I was going to start wearing a kilt to the office now and then. There was a drama series showing at the time that she enjoyed. When a brightly colored kilt arrived from Amazon one day I put it on, and her first words were, “Oh god, you look like that guy in that show.”

“I do?”

“Hey, big boy, where’s your sword?”

I looked a little nonplussed.

“I don’t think I have a …. Oh, I see where you’re going with this.”

I didn’t expect the kilt to have quite that effect. The first day I wore it to the office I got a combination of admiring glances, and one or two interesting comments. By day three it was accepted and normal. Admittedly I wanted to wear heels and panties with it, but that wasn’t on the cards yet.

Before long my dress sense was being complimented, and my kilt was both ‘so very masculine’ and also considered daring. I loved it. As for my wife, she was in highland heaven every time I wandered in with it on.

It suppose it had been three months since I’d made the decision to start adopting these changes, before I eventually spoke a word to my wife about it. I’d been wearing the kilt every now and then for at least a month before I broached the subject. I decided that when I did so it would have to be somewhat obliquely. I like being married. I have children. I’ve been divorced before and it’s no fun.

This would have to be done carefully.

Part 7

Get all parts of this series here.

I gradually moved from a very masculine and Alpha style of clothes, to really looking at the feminine clothing I enjoyed and looking for first ways to move more toward the centre of the gender spectrum, and then becoming more overt about the clothes I was choosing.

It started with the colors. Then the cut. A more fitted pair of jeans. A slightly more tailored cut to my shirts, and then the complete exclusion of shirts. I would choose soft lambswool sweaters that could easily be mistaken for women’s clothing. Gradually some of my sweaters were being bought from women’s clothes stores and became more overtly feminine.

Up until this time I’d not mentioned the shifts to my wife.  There was simply no need.

Then one day we had a conversation that moved into how we felt about something or other.

“I don’t really feel very strongly about it, darling,” I said. “I don’t know, I feel a little more sensitive these days. I feel more inclined to accept a softer approach.  What do you think?”

At first she looked at me a little strangely. After all, I was usually the forthright one of us.

“Well, I think you’re probably right.”

In that moment I was aware she’d seen a shift, not in my clothes but in my nature. And there had indeed been one. I was accepting so many things ina less aggressive and Alpha manner. I was allowing the softer sides of myself to emerge. It seems a small thing, but really it’s not.

Gradually I started allowing myself to think differently and be more gentle in my approach to life. It so happened that I replaced my vehicle around this time. Instead of looking for the fast muscle car that perhaps was more expected from a middle aged advertising executive, I opted for a powerful – but understated vehicle. That raised more eyebrows than my gradual shift to less gender binary clothing.  

One day my wife said to me, “I like that you’re being more thoughtful these days. It’s like you’re maturing.”

I smiled and let it go.  It was lovely comment.

Then one day I suggested, “Hey, when was the last time you had a pedicure?”

“I don’t know. Months I guess.”

“Well, why don’t you have one this week. I’d like to go with you.”

“You?”

“Sure,” I said. “There’s a couple of guys in my office do, and I wondered what it might be like. Besides, we have a new client who want’s us to start promoting their chain of nail salons. I might as well know what I’m talking about.”

“Well, I guess,” she said.

Of course, I paid. And made a follow up appointment. And got spectacular nails as well.

Over the coming months we went several times and before long my wife was booking appoints for us both, aware I enjoyed it. If she didn’t travel so much I’ve no doubt we’d go even more often.

Part 6.

Get all parts of this series here.

Ali, my gardener, is a Syrian refugee. He arrived in Canada a few years ago after fleeing Syria with his wife and two little girls.

After being in the country a week, he found himself on a bus travelling to northern Alberta, with over a hundred other Syrians who went up to Fort McMurray to help fight the forest fires that had encroach on the town and were burning it to the ground.  A group of Syrian refugees had seen that the forest fires were devasting the area and volunteered to go and help the country that had offered them a home.

Like all refugees he had a story. In his case he was a professor at Damascus University and taught Botany. It would be hard to find a more educated gardener. He also speaks excellent English when he chooses to, but doesn’t allow this to stand in the way of his random comments about my neighbours garden.

“Marjory’s chlamydia is out early this year,” he might quip. “The vulvodynia is coming along nicely!”

Currently he is on his hands and knees head to the flower bed pointing east. He’s either praying or carrying out the jihad he’s declared on the weeds in the garden.

I like Ali very much. He is wise beyond his years, and I often listen to his advice. He is something of a fundamentalist, in a botanical sense rather than an Islamic one.

“Ali,” I said when he’d finished what he was doing, “how would you go about telling your wife you were into crossdressing?”

Continue reading “The Crossdresser’s Guide To Marital Bliss – Part 6.”

Part 5.

Get all parts of this series here.

Just as the yin yoga helps my body find that impossible position after a gentle and gradual approach to the objective, so I can see my members finding a solution to how they approach their partners.

Amanda is my wife’s best friend, and a woman of particular personality. She has an association with tweed that few crossdressers will understand. I certainly don’t. I suspect even her underwear is made of the coarse material, she seems to wear it with such frequency.

For all Amanda’s faults, and they are many, she also has some interesting views on things. The fact that she has known my wife for so many years is a point in her favour.  She’s been a good friend to her.  And then there’s her journalism. She is editor of Pig and Pig Farmer, a publication that shot to prominence under her editorial guidance when it came out and endorsed Donald Trump for president in 2016. There’s just too much there to go into, so I shan’t be drawn.

“How would you feel,” I asked her, “if you learned that your partner was interested in dressing as another gender.”

“What,” she said in panic. “Has Marjory told you something?”

Continue reading “The Crossdresser’s Guide To Marital Bliss – Part 5.”

Part 4.

Get all episodes here.

I am wearing some lovely patterned leggings. I do yoga in them with my personal trainer, Sebastian. He’s a very good sport and I know he likes the way my body moves. He looks at me at times with a sort of lustful hunger, and I have to say I enjoy it.

But before I go too far telling you about Sebastian, let’s go back to Rose – so much older than myself and a woman who knew very decisively what she wanted. She would dress me up, make me up and then use me like I was some sort of toy for her amusement. In every respect I was bought and paid for. The degradation and the humiliation came right along with the discomfort of allowing her to do things to my body that certainly weren’t covered in my biology studies in high school. It was disgustingly wonderful.

Continue reading “The Crossdresser’s Guide To Marital Bliss – Part 4.”

I said nothing, instead staring at my feet. She sat quietly on the bed, and motioned me to sit beside her. I did so, doubtful of her good intentions, but aware that this was surely better than the beating she could so easily have resorted to.

“Now, tell me the truth. Did you do it because it feels nice?”

I continued to look at my feet, but nodded silently. I couldn’t face her.

“Well, at least we have the truth, now.”

She put her arm around my shoulders. Her body was warm and soft, and she said softly, “Michael, you’re not the first young man to put on panties. It’s ok, you know.”

Continue reading “The Long Game. Part 2.”

A young boy is caught crossdressing.

The long game.

I was twelve years old when my step sister caught me.  I was in her room, returning her panties. She was older than me, a beautiful 19 and fully a woman. I stood in her room, guiltily holding her red silky panties.

Inside I could feel the tears welling up. I was confused, and had been taking her panties now and then, unsure why, but enjoying pulling them on and posing in front of the big mirror in my mother’s room, when the house was empty.

“I should tell your mommy, you know. It would break her heart, of course,” she said condescendingly. “You wouldn’t care about that though. Why would you care for other people’s feelings, if you think it’s ok to creep around taking their clothes.”

Continue reading “The Long Game. Part 1.”

Our mothers had secrets too, long before you were old enough to even think of what they might get up to when you were safely occupied at kindergarten or pre-school. Learn what happens when an old notebook reveals the sordid truths of the past.

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Enjoy this ongoing series from Mistress Meg.