A Step Off the Path

By Aqualityofmercy

3.2K 46 19

This is a varied collection of short and very short stories that involve male-to-female crossdressing or tran... More

Hope
The Velvet Touch
A Sweet Cadence
Best Year
Helen's new family
Missed Chances
Alicia, the schoolgirl
A Soldier's Fate
Amanda
Could be Nasty
Josh and Irma
Backfire
Two Bags
A Conversation with Patsy
A Joke Too Far
I'm Lainey
Witch
My face and . . .
As we dream . . .
Lady Ryanna
Blackmail
How things can work out
Flower Girl

Bailey's Secret

84 2 0
By Aqualityofmercy


Chapter 1: new pyjamas

"Bailey, I think those PJ's have had it."

I looked down at myself and conceded with a smile, "You're right, Mum."

"I'll get you some new ones today after work. Do you want to come with me?"

"Yeah, sure, Mum."

Mum picked me up from school - I was nine years old at this time - and we drove to the nearby shopping centre.

We went into one of the big department stores and started looking through the boys pyjamas. I pulled a face, "They're all pretty daggy, Mum."

"Well, we could look elsewhere, but I suspect that they will be much the same."

"Yeah, they're either little kids styles - spiderman and so forth - or horrible striped grandpa types."

I was standing there frowning, picking up items and putting them back.

"Shall we try somewhere else, then," Mum said with a rather tired grimace.

"I suppose," I replied as I gazed around.

Then I spotted a sign that read 'Girls sleepwear'.

"I bet girls don't have to put up with daggy PJ's," I declared as I headed towards the sign.

"No, look at these, Mum. Girls have much better stuff." I held up a pair.

My mother walked across reluctantly and stood there as I poked around among the various items.

"Bailey, what are you doing?"

I didn't answer her directly, instead I held up a pair of PJ's and said, "Oh, these are really nice."

I turned towards her and asked, "What do you think, Mum? Do you reckon they'd fit me?" I held them up against myself.

Mum gave me a slightly exasperated smile, "Bailey, they're girls . . ."

"Yeah, I know, but what does it matter? I like them and only you and Dad will see me."

We stood there for a few moments, then rolling her eyes, Mum walked over and held the pyjamas up against me. "You'll need the next size up."

I got them off the rack and handed them to Mum with a coy smile.

"This seems pretty silly to me, Bailey," but with head-shaking and me trailing along behind, she made her way to the checkouts.

It took my father three days to notice.

"Those pyjamas are a bit fancy, Bailey."

"Yeah, do you like 'em, Dad?"

He pulled a face and I just laughed.


Chapter 2: more stuff

A couple of months later, and the weather had started to cool down.

"Bailey, go and put your dressing gown on; you'll get cold."

"It's no good, Mum. It doesn't fit properly anymore."

"Oh, show me."

"Well, I don't think it's that bad, Bailey. It would probably see you through for this winter."

"It's not very comfortable, Mum."

"I suppose it is a little tight."

Then, "Oh, of course, you don't think it goes with your girly PJ's, do you?"

I gave her a twisted smile.

"So let me guess, you now want to get a girly dressing gown."

"Just so it matches, Mum."

We got it the next day. It was really good.

A week passed. "Bailey, you need a few more pairs of undies. I'll . . ."

"Er, Mum. I've been thinking that I should try a different style."

"A different style, ay? Hmmm, Bailey, I know what you're on about."

"It's good to try different things, isn't it?"

"Oh, Bailey."

"Please, Mum."

"I'll see," (exasperated grimace).

She got me a four-pack of plain white girls panties. Loved 'em.

Not long after. "Mum, I keep running out of undies."

"Bailey, I'm not going to do the washing more than once a week. The only reason you think you're running out is because you won't wear your proper boys undies when you're at home."

"I don't like to wear them at home, Mum. They don't feel good."

"Bailey, your father thinks that this stuff is weird, and I'm beginning to think he's right."

Mum got me another four-pack of girls undies.


Chapter 3: freedom on the home front

My father was looking at me seriously, "Bails, just what are you up to?"

I was standing there showing him the t-shirt I'd talked Mum into buying me for my tenth birthday. It was a girls t-shirt. Not over the top, but unmistakably female.

I suddenly felt close to tears.

"I don't know, Dad. I just like wearing pretty things and cute things."

"Bailey, you know what it makes you look like?" His voice was serious, but kind.

"I guess I look a bit of a sissy," I replied with a weak smile.

"You do, mate, and you most likely would cop it if people saw you," he said with concern.

"Oh, Dad."

He sighed and then there were a few moments of silence.

"Dad, it makes me feel happy to wear these sort of clothes, they feel good on me."

He sighed again, and then with a wry smile, he nodded, "I'd rather see you happy than miserable, but keep it a secret, son. Only do it at home, okay?"

"Yes, Dad. I will. Thank you, Dad, thank you."

With my father 'onside', so to speak, I pestered my mother to buy me more girls clothes. She did, but with a show of reluctance for every single purchase. Nevertheless, I did slowly built up my 'wardrobe', and I began to dress-up more and more at home.

I'd say by the time I was eleven, I was almost always dressed in girls clothes at home. There were now only a few occasions when Mum and Dad saw me in boys clothes, like on the mornings of school days - I was already 'girl-attired' by the time they got home from work - or when we had visitors, or went visiting ourselves.

The folks had gotten used to me, but I could hardly say that they were approving.

Then, after a year or so, I began to do it less for some reason. I still always wore girls pyjamas to bed, but I was now only dressing up in my other girls clothes a couple of times a week. Maybe I was getting over my fascination, I don't know. I'd say that my parents were hoping that I was 'growing out of it'.


Chapter 3: what's it all about?

When I look back, I think I can honestly say that I didn't understand what was going on; I didn't know where I was heading.

I do know that I had this seemingly primal urge to wear girls clothes at times, particularly when I went to bed. It was a compulsion that had emerged and grown to the point where I could no longer resist it.

Even at the time, I was aware that I wasn't acting like a girl, and my parents weren't treating me like a girl; I was literally a 'boy in a dress'. Just basically a normal boy who had this strange proclivity to wear girls clothes.

I don't recall having at any stage, a desire to put on lipstick, or nail polish, and I had no wish for earrings or bracelets. The clothes were solely what it was about.

I have to concede that what I was doing was decidedly odd.

Just after I turned thirteen, Mum and Dad sat me down for a serious talk.

"Darling, we have to work out this dressing up business that you're doing. You will soon be starting to mature into a man, it's time to . . ."

"Bailey," Dad interrupted, " we don't really know what's going on with this girls clothes stuff. Do you?"

"I don't think I do, Dad."

"Love, look ahead. Do you think that you will still be wanting to do it in, say, two, three, four's years time?"

"I don't know, Mum."

Silence for a while.

"Bails, you don't behave like a girl and you've never said that you want to be a girl. You don't say things like you want to go out dressed as a girl, or go to school as a girl. Mum and I don't understand."

"I don't either, Dad. I'm sorry."

"Sweetheart, we think that you are going to have to see a counsellor or psychologist, someone properly qualified and experienced with this sort of thing."

"Do you think I need to be cured somehow?"

Dad jumped in quickly, "Bails, that's not what we're looking for. What we want is understanding. You need to understand what it's all about, and so do we. That's what we're looking for, understanding."

I was nodding, it made sense. "Okay, how do we go about this?"


Chapter 4: the psych

We didn't seem to get very far during the first few sessions with the psychologist. I think she was just as puzzled as we were as to the nature of my compulsion. Then she got us all together and proposed an experiment.

"Bailey, I would like your Mum and Dad to take you out, say to a restaurant, fully dressed as a girl. I mean the whole bit, shoes, clothes, hair, lipstick, etc. I want you to try to pretend that you are a girl, to act like a girl, to feel like a girl. Do you understand me?"

"I think so, but I don't know . . . it sounds a bit scary," I replied doubtfully.

"What I'm getting at here, folks," the psych went on, "is that I think Bailey is currently straddling the fence; unsure which way he wants to go. If we can give him a bit of a shove, maybe it will help him decide which way he wants to fall."

Mum and Dad were nodding, but I was beginning to feel frightened. The psych could see it.

"You should take Bailey somewhere that nobody will know him; a neutral place where he will not be afraid of being recognised."

"Dear," Mum turned to Dad, "why don't we go away for a weekend?"

"Yeah, sounds good," he responded.

"That would be even better. Bailey could present as a girl for a couple of days in a place where you are not known."

There was an exchange of smiles, mine a very weak one.

"Bailey, some boys try dressing in girls clothes for various reasons, fun, curiosity, sexual stimulation, etc. Some males continue (or start later) to crossdress also for various reasons like: they want to look pretty, for sexual arousal, they feel good dressed up, or even just for friendship. Such men may or may not be gay. Some do it secretly, some get together with like-minded men.

Then there are the males who genuinely believe that their essence is female, that their body is the wrong one, and they are driven by a need to become and live as a female.

We're trying to help you find out where you fit into this spectrum."


Chapter 5: no, no

The weekend away at a holiday park:

I hated it. I felt scared and awkward the whole time, but I had to stick it out because I hadn't brought any boys clothes with me.

I couldn't avoid having to go outside a few times, but really I just wanted to stay inside our cabin. Mum and Dad didn't try to force me to go out, so as a holiday it was all a bit of a fizzer (failure).

Back home, sitting down with the psychologist and reporting. I think she was pleased that her suggested experiment had helped to clarify matters, and it certainly had.

I didn't want to be a girl, I didn't want to live full time as a girl or transition from a boy to a girl, I just wanted to dress in girls' clothes for my own private pleasure. I guess that's a bit strange but it's also a rather harmless obsession; you could call it a fetish if you like. Anyway, there it is.

Time has passed and I'm now twenty-three and work in the office of a large building company. I'm going out with this lovely girl and the signs are there that we're becoming serious.

So, I look at myself in the mirror, take a big breath and say, "Well, Bailey, my boy, if you and Jenny are thinking of moving in together, you are just going to have to tell her about your secret passion. I hope she will be understanding."

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