Doing it properly.
Part One; Friday. Caught.
I don't know who was more shocked. Me, at finding my Mum coming in the
through the back door of our home. Or her. At finding me, her sixteen
year old son, sitting in the kitchen, doing his homework and wearing a
school girls uniform. For the longest time, we simply stood there
looking at each other. And then she spoke.
"Okay Gavin, We obviously need to speak about this, but I'm in a bit of
a rush, so just stay as you are. I'll be as quick as I can and then we
can discuss this."
She walked into the hallway and picked up her cleaning bag, which was
full multi-surface sprays and aerosols and all manner of cloths and
dusters and other cleaning equipment. Obviously she had forgotten to
take it with her that morning.
I couldn't speak, I was on the verge of tears, I had gone from being
calm and confident to feeling overwhelmed with guilt, fear and shame in
about a quarter of a second. Guilt at wanting to wear girls clothes in
the first place, fear at what would happen now that I had been
discovered and shame at being caught. Mum paused at the door taking a
last look at me, and then she was gone. I was just glad that my Dad
wasn't here to see this. He had passed away from cancer when I was eight
years old. My memories of him are vague, but I remember him as a kind
loving man who cared deeply for his family and made sure that they were
financially cared for after he was gone.
Then I began to wonder how I had been found out. What had caused the
discovery of what I thought was my private guilty secret?
My Mum Angela was a domiciliary care worker. She had gone out that
morning to see her client, Mr Carter, who lived a few streets away. He
was in his nineties, with onset alzheimers and a pair of dodgy hips. But
he was fiercely independent, insisting on living in his own house, the
home he had lived in and raised a family in for over sixty years. She
had left ninety minutes earlier and was not due back for another two
hours, at least. Though it was a Friday, I was off school as it was a
teacher training day, so with a few hours to myself, I had decide to
indulge in my guilty hobby for a little while. And do some home work of
course. I had the following Monday off as it was a bank holiday so there
was an opportunity there as well.
Since I had been young, I had been crippled with a fascination for
women's clothes. It had started when I was ten, with a swim suit. I
don't know how or why, but I had found a girls swim suit at school. It
had just been laying there on the floor. I had picked it up, stuffed it
into my bag and had taken it home. It had been a further two weeks
before I found the courage to actually put it on. That first time had
been a revelation. It had been soft and comfortable, the clinging fabric
encasing my slender frame and it had felt incredible.
I had not had access to any other clothes until I was thirteen and was
able to go out and shop for myself, with the generous allowance I was
given and cash from the odd jobs for the other families in the
neighbourhood. I had bought underwear and hosiery from Primark and tops
and skirts and dresses from charity shops. Some fit me, and others
didn't, but I learnt my sizes as I had gone on and over the last couple
of years, I had amassed a bag full of girls clothes which I hid in a
large rucksack in the back of my wardrobe. I tried to present a feminine
image, but with puberty came problems. I grew hair on my arms and legs
and my chest, and muscles filled out the lean short frame that I had. I
had not gotten the growth spurt I hoped for, but I had risen from five
foot five inches, to five foot seven. I was no muscle bound body
builder, but at least I had grown up, a bit. Though I was popular in
school, my nickname was The Runt. Which tells you all you need to know
about me I suppose.
Also with puberty came the sexual urges, the fantasies, the masturbation
sessions in my bra and panties, but these had passed and yet I continued
dressing. I simply felt calmer, more confident and more caring when I
was dressed. I didn't really understand the issue and though I could
have looked it up on the internet, I dare not use the computer for such
a search. We only had the one machine in the small family room and Mum
also had access to it. If I had left that particular search history on
the PC, then my Mum would have undoubtedly found it, leading to
questions I had no answers for.
For the next hour, I sat in the living room with my thoughts raging
uncontrollably through my head. The upcoming 'discussion' with my mother
went through various scenarios in the movie theatre in my brain. She
would make me throw the clothes away and promise to never wear girls
clothes again, which was a promise I knew I couldn't keep. She would
call all my friends and tell them about my secret to expose me,
humiliate me, shame me. She would get angry, scream and shout at me, and
then throw me out. Into the street. Dressed as a hairy schoolgirl. For
all the neighbours to see. The one thing I desperately wanted to do, was
to go up to my room, change out of these things, get dressed in my
proper clothes and pretend that this had never happened. But it was also
the one thing that I didn't do. Something that Mum had said had stopped
me. Stay as you are, we can discuss this situation. Also, she had not
looked angry, or disappointed, or shocked. Just... resigned? Yes, that
was it. Resigned. After an hour and a quarter, I heard the back door
open and heard Mum call out from the kitchen.
"Gavin? Could you come here please?"
I rose, my body trembling and I shuffled into the kitchen. Mum was
preparing coffee for us. I sat the table. Mum put the two cups of coffee
down and then she pulled out a chair opposite me and sat down. She did
not fold her arms across her chest, or cross her legs, or any of the
things that she normally did when she was upset with me. She simply sat
there with one hand in her lap and the other wrapped around her coffee
cup.
"Okay Gavin. Here's the obvious question. Why are you wearing a girls
school uniform.? No, answer me this first, where did you even get a
school girls uniform?"
"I got the uniform from a charity shop. The underwear came from
Primark," I mumbled.
"Stop mumbling and speak clearly please," mum said with a soft smile on
her lips, "And don't slump in your chair, sit up straight."
I settled back in the chair and sat up. I sniffed and then answered her
again.
"The uniform came from a charity shop and I bought the underwear from
Primark."
"A boy buying girls girls clothes? That must have been a little
embarrassing?"
"It was at first," I said. I remember the first item I had ever bought.
It had been a leotard from a charity shop. I had been blushing so much
that I was certain I was glowing.
"It got easier though, when I realised that they didn't care what they
were selling and just wanted my money. "
"I see," said Mum, her expression growing both thoughtful and pensive,
"And have you gone outside while dressed up?"
I shook my head emphatically.
"No! Never."
Mum nodded and seemed to relax a little. As for me, I was not lying.
With my hairy arms and legs, I would never have passed and would have
easily been spotted as a boy in drag, even at night. And that would have
led to humiliation and name calling at best. I didn't want to even
imagine the worst.
"So, my original question, why are you dressed as girl?"
I glanced down at my clothes, my girl clothes I suppose. At the moment,
I was wearing a short sleeved blouse, that was tailored for a bust that
I didn't really have, but a bra and a couple of pairs of rolled up socks
sorted that out. I was wearing a classic gym skirt, that hung just above
the knee and a pair of black tights. I was wearing my own trainers with
the outfit, and they sort of worked. I sighed as I tried to compose my
thoughts. The usual go to answer of 'I don't know' seemed totally
inadequate, and while it was the truth, I did have sort of an answer.
"I guess I'm just fascinated by the feel of the clothes and the cut of
them. I like wearing them because, I feel... different."
"In what way?" Mum asked.
"I feel calmer. I feel more confident and I feel... nice."
"Right then." Mum took a sip of her coffee, then she smiled broadly. "Is
this why you've been growing you hair out?"
For over three years now, I had resisted her repeated demands to get my
short brown hair cut. I wanted a hairstyle that I could tie back in a
ponytail so it wouldn't look out of place and yet could be styled in a
feminine cut when I wanted it. It was now down to my shoulder and when
loose, it hung in a very feminine style. As for facial hair, there was a
little peach fuzz. I had to shave once a week, if that. Unlike my good
friend Max, who shaved two, maybe three times a week. I reached up to
stroke my hair.
"Yes. It beats wearing a wig."
My mum actually laughed.
"I'll bet it does. Okay. Now for the uncomfortable question. Are you
gay?" I glanced up at her. I opened my mouth to tell her no, I wasn't
gay, but some of my masturbatory fantasies... eventually I shrugged.
"I don't know, I don't think so. I do like girls, but..."
"That's okay. I think you're a little too young to know which way you
swing if I'm honest. So, do you have any other female clothes?"
"Yeah, I've got a bag full upstairs."
"And have you ever worn any of my clothes?"
I almost laughed at that. Mum was tall and slender, but she clearly
bigger in stature than I was. I shook my head with a slight grin.
"No, you're bigger than I am, no offence. I don't think your clothes
would fit me properly."
Mum nodded.
"None taken, and I'm glad you haven't been in my wardrobe."
She took another sip of her coffee and took a deep breath, in through
her nose and out through her mouth. It was a sign that she was thinking.
"Okay. So, let me get this straight. You dress up at home while I'm out
or at work and you do it because you like the clothes and because they
make you feel calm and confident. Is that right?"
I nodded. Mum smiled.
"Okay Gavin. I know a little bit about this. It's known as transvestism.
I'm going to be honest with you, I'm a little... shocked, to find you
dressed up. But I'm not angry."
I glanced up, hope beginning to blossom in my chest.
"You're not?"
"No. Not even disappointed."
I relaxed for the first time since the discussion had started. Mum
continued.
"First off all, do you think you're the only boy who dresses up as a
girl?"
I nodded.
"I thought I was weird or something."
"Well you're not weird. About half the male population of the world has
crossdressed at some some point in their lives. Either for a dare, or
fancy dress, or they've lost a bet. Or won one... and about half of that
fifty percent goes on to do it full time. Well, it's a little lower than
that. But I would guesstimate, that one in five men dress up as women,
for varying reasons. And while it's known as Transvestism, I prefer the
term crossdressing. Transvestism makes it sound cold and clinical, like
a mental illness or something." She looked disgusted for a moment and
then brightened up. "When in fact, it's a harmless hobby that has long
been removed from any list of mental of psychological disorders.
Unless... you don't want to be become a girl, do you?"
She actually looked worried at this. But I was adamant about it.
"No. I don't want to be a girl. I just like the clothes."
"Okay. That would raise serious concerns that I don't particularly want
to address right now. But that's another matter. If you don't want to be
a girl, but just want to dress as a girl, then it's fine."
That surprised me.
"It's... fine? That I'm dressed as a girl? Really?"
She nodded in an encouraging fashion.
"Really. I'm surprised, shocked even. But I'm not angry. And if you want
to dress like a girl, then that's fine with me." She then gazed at me
shrewdly.
"Stand up. Walk to the doorway, turn around, walk back and sit down." My
puzzlement must have shown in my face, because she smiled. "Trust me."
I stood up, walked to the doorway. Then I turned around, walked back to
the table and sat back in the seat. Mum laughed out loud.
"You dress like a girl but you walk like a boy. Watch me."
With that, she rose. She walked to the doorway gracefully. She turned
and walked back to the table, where she sat down and crossed her legs,
right over left. She smiled at me.
"That's the way a girl walks. Now, you try it."
I stood up and walked to the doorway like Mum had. One foot in front of
the other, in a line. It added a wiggle to my hips that I hadn't had
before. I turned, spinning on one heel and walked back to the table.
Where I sat down again, reaching back to sweep the hem of my skirt
beneath me. Then like Mum, I crossed my legs, right over left, and
placed my hands in my lap. I looked at Mum expectantly. Her expression
did not bode well.
"Hmm. That's better, but it's not perfect yet. You just need a bit more
practice. Anyway, show me your clothes."
I took her upstairs to my room and dug out the rucksack, emptying it on
the bed. Mum sorted through it, praising me for my taste and style. I
obviously had good fashion sense. We then spent the next few minutes
placing my mismatched underwear in my dresser and hanging the meagre
collection of dresses, skirts and tops in my wardrobe. She asked me to
change, out of the uniform and into a pale blue dress that had caught
her eye, and then meet her back in the kitchen. I changed, hanging the
skirt and blouse in my wardrobe and climbing into the dress. It was
short, above the knee with a high neckline and lace full length sleeves.
I was later to learn that it was a called a peplum dress. I didn't know
that at the time, I just liked the colour, and the lace.
My mum and I spent the evening watching television and rather than cook,
she ordered a takeaway pizza. She also spent the evening giving me tips
and advice on ow to walk and talk like a girl. I seemed to doing
something right, because the tips, which I followed, came less often.
She smiled at me, as we sat on the sofa, watching a movie.
"Gavin... I can't keep calling Gavin if you're dressing as a girl. If
you'd been born a girl, your father and I were going to call you Gabby.
So that's your... girl name. If that's okay?"
Gabby? I liked it. It suited me better than Gavin, well, in my current
clothes at least.
"Yes please, Thank you."
Mum merely smiled at me.
"You're welcome, Gabby."
At bedtime, she leant me a nightgown to sleep in. It was a bit big, but
it was silk, and it hung well. I slept well. But I had some strange
dreams that evening. I barely remembered what the dreams were about, but
I remembered a state of contentment.
Part Two; Saturday. Proper planning.
I woke late on Saturday morning, unable to remember when I had had such
a decent night's sleep. Grabbing my phone from the beside cabinet, I
noted the time was just half past ten. I got up, had a shower to wash
the sleep from my head and body and scrubbed myself clean of dirt, both
real and imagined. Then I dried myself, I dressed in male underwear, a
pair of clean jeans, a baggy old t-shirt and my trainers. I went
downstairs to find the house empty. There was a note on the table from
Mum.
'Gone shopping, will be back at midday. Breakfast in the cupboard.'
I made myself a plate of scrambled eggs on toast, and a cup of coffee.
Then, with no jobs to do or errands to run, I went on the Playstation.
That gobbled up an hour. I heard the front door open and heard my Mum
come upstairs and head into her bedroom. She stayed in there for about
ten to sixteen minutes before she knocked on my door. She poked her head
around the door,
"Ah, Gavin. Come downstairs will you?"
She left my room and I heard her footsteps retreat down the stairs and
into the living room. I turned my Playstation off and followed. I paused
at the door, wondering if I should get changed, but then with a sigh, I
headed down the stairs. Mum was sat in the kitchen. She was smiling
broadly.
"Sit down Gavin."
I pulled a chair out from the table and sat down.
"Right then. After I discovered your secret yesterday and after asking
you about it, and giving you your femme name, I have decided that if
you're going to do this, you're going to do it properly. And that means
you do exactly as I say, and you don't question me. Do you understand?"
"Yes," I said. I was not sure I understood what I was signing up for,
but I was sure that Mum knew what she was doing.
"Good." She stood up. "Follow me."
She led me back to my room. She reached into the wardrobe and pulled out
a short black skirt and a white top.
"Get undressed and meet me in the bathroom."
I undressed to my underwear and followed her to the bathroom Mum was
sitting on the toilet, with two bottled in her reading one of the labels
when I entered. She looked up and smiled.
"Take you underwear off. Get naked." I blushed a little at this. "And
don't be shy. I used to change your nappies. I've seen it before."
I stripped off my boxer shorts and my socks. Standing there in just my
birthday suit was a little embarrassing, especially as my... my thing
had changed substantially since puberty. My Mum looked up fixed her gase
on mine, for which I was grateful.
"Right then. This is depilatory cream. The instructions say to smear it
all over your body, apart from your head and wait for fifteen minutes.
Use the whole bottle." She handed it to me. "When you're finished with
that shower thoroughly and then dry yourself. Oh and pat yourself dry,
don't rub, or you'll irritate your skin. And when you're dry, use this."
She handed me a second bottle. "It's a moisturiser. It'll keep your skin
soft and supple. Then meet me in your bedroom okay?"
I looked up from the instructions on the first bottle.
"Okay."
What on earth was I getting myself into? I was a little scared, but I
was also curious. Mum left me alone and I started with the depilatory
cream. It had a noxious chemical smell that irritated my nose a lot and
my eyes a little. It felt cold and goopy in my hands. I spread it over
my legs, my arms and armpits and then over my chest. I even smeared it
on my the peach fuzz that was covering my bum. With the bottle empty, I
stood in the shower, shivering. It began to itch, and there was a mild
burning sensation on my limbs.
When the fifteen minutes passed, I turned the shower on and stood under
the stream of water. I began washing myself for the second time that
day. It felt weird having a second shower in one day, but the surprising
thing was that the hair on my body began falling away, leaving bare
patches on my skin. After several minutes I was hairless from the neck
down, apart from the sparse patch of pubic hair around my penis and
testicles. I dried myself thoroughly, remember to pat myself dry,
instead of rubbing. When I was dry, I spread the moisturiser over my
body. It had a floral scent, lavender. And it felt good on my hairless
limbs. When I had finished, I tidied up. The empty bottles went in the
bin, the moisturiser was placed on the shelf, the towel was folded and
placed on the rail. At a loss for what to wear, I put my underwear back
on. It was still clean and I wanted to cover up. Back in my bedroom, I
found my Mum waiting in the chair at my desk which had three large
shopping bags on it. She smiled at me.
"So, you're hairless now? What's it like?"
"Erm..." I rubbed my hands over my arms and then my legs, noting how
smooth and silky they felt. "It's a little weird, but It feels nice."
"Good. Now, I've thrown some of your underwear in the bin." She held up
her hand to forestall my complaints. "It was a bit worn out and you
really need matching pairs. So I brought you some new pairs." she
reached for one of the shopping bags that was sat on the desk and tipped
it out on the bed. Out spilled a collection of fresh new underwear.
"Go on," Mum said, "pick something."
I sorted through the bra's and panties, selected a matching set in a
pale yellow. Mum nodded approvingly.
"Good choice. Now, before you put it on, I need you to put this on."
She held out a flash coloured object that looked like a cross between a
thong and a torture device. "It's a gaff," she explained. "The tube at
the front holds your penis back between you legs and pushes your
testicles back up into you body. Now it's nice and tight and will
present a smooth front, instead of an unsightly bulge."
She left the room to give some privacy. I took off my boxers and
threaded my legs through the leg holes. Then I pulled the garment up to
my thighs. I forced my penis into the tube and felt it being pulled
back. As I raised the gaff up around my hips I felt my balls being being
squished upwards and my penis straightening out between my legs. I
pulled the hem of the gaff up to my waist and felt it settle everything
into place. It was a peculiar sensation. It was not the torture device I
had thought it was but it wasn't comfortable either. It left my groin
smooth, flat and feminine. Mum returned after I called out and informed
that I had struggled into the garment.
"How does it feel?"
I flexed my legs and the gaff pulled on my genitals in an uncomfortable
way, but it wasn't too bad
"Not bad. I could get used to this."
"Good. Put the underwear on."
I donned the panties, surprised at how comfortable they felt. Then I
hooked the bra in front of me, spun it around my waist and pulled it up
around my chest, drawing the straps up over my shoulders. I reached for
the tights, but Mum held up a hand.
"Wait a minute." She picked the second bag off my desk and and pulled
out a large box, which she opened. Inside were two very realistic
looking breast forms.
"These are C cup silicone breast forms. They sit inside the cups of your
bra and there's even a special adhesive so we can glue them into place
if we want." She took one of the forms from the box, holding it in her
palm. "These will do better than socks don't you think?"
"Wow. These are great. They must have been expensive," I said.
"They were. Very expensive. So take good care of them." She reached into
the book and pulled out a sheet. "These instructions tell you how to
look after them."
Standing up, she slipped one form into the left cup and the second into
the right cup. They were a little cold and clammy at first, but they
warmed up quickly. As I stood marvelling at the weight and feel of them,
Mum adjusted the bra to accommodate and hold my breasts, firmly and
properly.
"Right put your tights on now," she said, sitting back down.
I had several pair of tights, before, but there was only the one thick
pair left. The others must have gone in the bin. There were several new
pairs however, some patterned and some plain, I decided on a new pair
that had a diamond pattern to them. I pulled the package open and
removed the tights. Sitting on my bed, I bunched up the left leg. placed
my left foot in the fabric and pulled it to my knee. I repeated this
procedure with the right leg. Then I stood and eased the remainder up my
legs. I could not get over how nice it felt. My legs, which were smooth
and soft now, reacted to the feel and touch in fabric in a way that I
had never felt before. It was exquisite. I pulled the tights up and
settled the waist band around my slender waist to rest against my tummy.
Which was fluttering by now. With the underwear in place, I reached for
the skirt. Mum stopped me again.
"Wait a moment." She stood and reached into another shopping bag,
pulling out a short pink robe. "Put this on and follow me."
She strode to the door and I pulled the pink robe on, pulling it around
my body and tying the belt. It was like my regular dressing gown in a
way, but it was a world apart in others. My male gown was dark blue and
was a thick course material and hung down to my knees, this was robe was
thin and silky. It felt wonderful against my hairless body. My senses
reeled from the new sensations I was experiencing. It was also short.
Barely covering my thighs. Mum was in her bedroom when I followed her
out and she was stood at her dressing table. All of her stuff which was
usually arranged over the table, had been moved and was now set out on
the left hand side. Several new items were arranged on the right hand
side of the table and the mirror that stood on the table was covered
with a long cloth.
"Right. Hair and make up. Sit down."
Hair? Make up? I didn't want to wear make up. Did I? I remembered my
promise. To do whatever she asked and ask no questions. We were doing it
properly, after all. I sat at her dressing table and Mum plugged in a
hair dryer. Then, using a a brush, she dried my long hair. Before she
became a domiciliary care worker she had been a hair dresser which came
in handy for some of her clients. Men who wanted a short back and sides
and women who wanted their hair bleached and styled. Using the brush and
the dryer in a swift practised motion, she dried my hair, but also
styled it in a feminine style.
"Ooh, there's a lot of split ends here," she remarked. "Do you use
conditioner when you wash it?"
I shrugged. I had never considered hair care to be a priority until now.
"No, not really."
"Well you should. However you want it, you should take care of it. Not
only that, it gives it body and volume. I will need to trim it at some
point..."
"No!" I said, a little too loudly. Mum stepped back.
"Oh relax Gabby. I'm not going to cut it all off, or give you a crew
cut. I'll just trim the split ends off and tidy it up a little. Besides,
It encourages growth." She stepped forward again and continued drying my
hair. When it was dry, she continued brushing it, letting it hang in a
soft style, that bounced around my face and shoulders in soft waves.
"With care and conditioning, it's going to look absolutely beautiful. Do
you promise me to keep it clean washed and conditioned?"
"I promise," I said.
"And will you let me trim it?"
I hesitated for a moment.
"Yeah."
Mum beamed with delight.
"Excellent!" She frowned through a thoughtful expression. "I wonder what
you'd look like as blonde."
"Or maybe a red head?"I turned and smiled at her. She chuckled.
"Ooh, adventurous. But let's learn to walk before we start running.
Right then. Make up. As you can see, I've arranged the dresser so we can
both use it. All my stuff is on the left, so don't use it until you ask
and all your stuff is on the right. I won't use it unless you give me
permission. Agreed?"
"Agreed."
That threw me a bit. Had I just agreed to sharing make up with my Mum?
"Right. First step, foundation."
She then explained what she was doing as she applied a layer of
foundation to my face and then, still explaining what she was doing, she
applied a layer of powder. She then worked on my eyes with eyeliner,
mascara and eye shadow. She added a little blush to my cheeks, just to
give me a glow she said. She then outlined my lips with a lip pencil and
filled the outline with lipstick. She then stood and left the room,
returning with the top and the skirt.
"Right then. You can finish dressing." I took the skirt, it was short
and tight and, being Lycra, clung to the body like a second skin. It
had red piping down the sides and I thought I looked good in it. The top
was a white cold shoulder top. This too was tight, but it was stretchy.
I pulled it over my head, careful not mess up my hairstyle, or my make
up, and thinking how strange that was, and stretched it down around my
torso. My new breasts tented the fabric in a prominent but not
outrageous way. Mum had left the room has I had dressed and come back
with a shoe box. She opened it up to reveal of ankle boots.
"Try these on," she said. I took the boots marvelling at them. They were
a light grey with zips on the outside and a small two inch heel. I sat
on the bed, placed them on my feet and zipped them up. I stood up. I was
dizzy by the additional two inches added to my height and shook on them.
Mum grinned at me.
"How do they feel?"
"They're a perfect fit," I said. "How did you know my size?".
"I'm your mother Gabby. I've been buying your clothes since you were
born. I know your sizes off by heart."
"Oh, right." I was steady on the heels now. As long as I didn't move, I
would be fine.
"Take a few steps," Mum said. I stepped forward and the movement felt
awkward, forced somehow.
"You're still walking like a boy, take smaller steps and put one foot in
front of the other. Walk in a straight line now. And don't swing your
shoulders, swing your hips."
I did as instructed. It was like having to learn to walk all over again.
But after a few steps I felt I was getting the hang of it. And judging
by the smile on Mum's face, she too was impressed.
"You're getting there girl. Want to see what you look like?"
"Okay."
"Come over here." I walked over to her wardrobe which had mirrored
doors. Both doors were open so I had been unable to to see my reflection
while I had been dressing. She closed the doors and I saw my image for
the first time.
"Oh my god!"
The young girl in the reflection put her hands up to her cheeks, a look
of amazed surprise on her face. She had a long mane of dark brown hair
that that flowed in waves around her face. She was wearing a white cold
shoulder top, a short black skirt that and diamond patterned tights that
clung to her feminine curves. She had a light layer of make up, with
smoky full colours around the eyes, a light blush highlighting her cheek
bones and a layer of pink lipstick on her lips.
And the girl in the reflection was me. I couldn't believe that I looked
so...
"I look like a girl," I said. I stood in a feminine gesture. I cocked my
left leg and placed my hands on my hips. Mum chuckled.
"You're looking good girl."
"I'm feeling good Mum."
It was early in the evening that Mum dropped what I would later call the
'bombshell'. We had spent the afternoon with me practising my feminine
movements. How to sit, how to stand, how to walk, how to talk...
everything I had learned in my sixteen years in the world, I had to
learn again, but from a girl's perspective. And I was a quick learner
apparently. We had just finished a light meal of salad; I had to look
after my figure now, when Mum told me forgo the washing up and we
retired to the living room.
"Right then Gabby. You need more clothes and a few more pairs of shoes,
more than I could get for you this morning. So, how do you feel about
going shopping tomorrow?"
Now normally, I hated going shopping and avoided shops and supermarkets
as much as I could, preferring to order stuff on line when I could. I
even had an arrangement with Mum. As long as I asked her, and as long I
paid her first, she would provide her credit card details for these
purchases. She never let me see them so I didn't know them, or needed
to. However, this time, there was a new eagerness.
"Yeah. I'd like to. I can finally afford that new Playstation game I've
been wanting. And if I check the used good stores, I can probably find
it cheaper."
"That's good, because you'll be going dressed as you are now. As Gabby."
Emotions rushed through my head so quickly that I couldn't keep track of
them all, but one emotion registered above the rest. Fear, for a variety
of reason. Fear at being recognised as a boy in girls clothing. Fear at
being ridiculed for what I was. Fear at bringing shame to my Mum. I
shook my head.
"I can't. I just can't. I'll be spotted as a boy and get laughed at.
You'll get laughed at. I can't do that to you Mum, I can't."
It was Mum's turn to shake her head.
"Gabby, you look extremely passable now. You look like a young girl, you
walk and talk like a young girl. And we both know that sooner or later
you're going to want to go out dressed like that. And if it's going to
be sooner, then so be it and I'd prefer to be with you."
"But... but I'm a boy dressed as a girl. And I wouldn't want to
embarrass you like that."
"Gabby," my Mum was actually laughing now, something that annoyed me,
"If I thought for one minute that you were going to embarrass me, I
wouldn't let you dress in the house. Let alone take you out. So what do
you say?"
I didn't say anything for a few moments, I didn't know what to say.
Eventually I sorted out my confused thoughts into coherent words.
"I hadn't really thought about going out dressed as a girl, or passing
for a girl. I just liked dressing like one. But if you think I can do
it." Mum was nodding eagerly. "Okay. I'll do it."
"Good." Though the smile remained on her face, she seemed to sag a
little, as if she was deflating. "Well, it's been a busy day today and
you've come a long way. I'm proud you."
"Really?"
"You've learned a lot today. So let's have a relaxing night in front of
the telly shell we?"
"Sounds like a good idea. What shall we watch?"
Mum sighed deeply as she considered the evenings entertainment.
"Oh, choose a DVD. Only no Marvel Comics Universe films please."
That raised my hackles and the argument that followed was heated, but
only slightly and light hearted. I eventually persuaded her to watch
Guardians Of The Galaxy vol 2. because I knew my Mum had sort of a crush
on Kurt Russell. She watched it without complaint. I think she might
even have enjoyed it.
Part Three; Sunday. Shopping.
I was roused from a deep sleep and a comfortable dream by a hefty
knocking at my door. I raised myself up and glared at my alarm clock. It
was just turned nine o'clock in the morning, which, as far as I was
concerned, equated to silly o'clock in the morning. It was a Sunday
after all. I pulled the covers up over my head.
"Go away," I grunted. I heard the door open. Then the covers were ripped
off the bed. I glared up to see my Mum, already dressed, frowning down
at me. It broke into an easy smile.
"Get up sleepy head. It's time to get up. Have a shower then put your
underwear and robe on. Come downstairs for breakfast. We have a lot to
do today."
She left the room. I looked about my room in the mid morning light and
tried to remember what was happening. Oh yeah, I was pretending to be a
girl called Gabby, and my Mum was helping me do it. I would have thought
it was a bad dream, only I hadn't had any bad dreams lately. I was
dressed in a pale blue nightgown that my Mum had brought the previous
morning. I rose and for a moment, I thought I was still dreaming, only I
knew I wasn't. Mum had already selected my outfit for the day. A knee
length black skirt, dark blue blouse and the pale yellow matching bra
and panties from yesterday. I got undressed and in just my panties, I
made way onto the bathroom. Mum's voice floated up from the bottom of
the stairs.
"And don't forget to condition your hair."
I stood under the shower for a moment, still waking up. Then I washed my
body, washed my hair and used Mum's conditioner on my long mane of hair.
When I got out, I patted myself dry and went back into my bedroom, one
towel wrapped around my waist and my long hair in another towel. I
stopped by the mirror in the hall for a moment. My refection didn't look
right. I undid the towel, wrapped it higher, covering my chest and tied
it off. That looked better,
In my bedroom I blew dry my hair and used some hair spray to set it, it
was soft and fell in soft waves around my face and shoulders. I was
pleased with the effect. I donned my gaff, and yes, it was as
uncomfortable as I remembered, and then I put my panties on. I donned
the bra, but before I pulled it up around my shoulders, I settled my
false breasts into the cups. I was tempted to read the instructions, to
see how they felt when they were attached to my chest, and hanging like
they should have hung there. I had the solvent, I could have done it,
but I felt like that was a step too far. As if I hadn't taken too many
steps already After donning my tights, I pulled my robe around me. And
headed down to the kitchen.
"Good morning Gabby. How are you feeling?"
"Okay I guess. I'm still getting used to..." I gestured towards my
breasts, Mum chuckled.
"Well get used to them girl. I've had to," she said, placing a boiled
eggs and a plate of soldiers in front of me to go with the coffee I had
already poured for myself.
"You've had more practice than me," I said. That clever remark earned me
a smack on the back of my head. I was tempted to tell her not to mess
up my hair. But I knew how far to push my luck. After breakfast I loaded
up the dishwasher and set it going. Then I followed my Mum to to her
bedroom where she sat me at her dresser.
"Now, a memory test. Where is my stuff?"
"On the right?"
"Correct. So where is your stuff?"
"On the left."
"Correct again. Now, where is your foundation?"
"Erm..." I reached for a tube which, since it was labelled foundation,
was really easy. I held it up.
"Is this it?"
I knew I was right due to her wide smile. What followed was myself
applying my own make up under instruction from my Mum, who explained at
each step what I was doing and generally correcting my mistakes as I
made them, but mostly before I made them. By the time the lip gloss went
on I was looking good.
A soft natural look around my eyes with light blue blending into dark
blue over my eyes which popped out due to dark eyeliner that I had
applied so carefully I had a champagne blush to highlight my cheekbones
and a light red shade on my lips. I looked good. I looked sophisticated
and elegant. It was amazing that I could present such a feminine image.
It had taken us an hour, and Mum said that, with practice I could apply
it in about half that time, maybe less. But it would take time and
practice. And with the wide variety of colours on offer, I could create
a look for all occasions.
"Okay. Go and dressed now." My mum said. I rose from the dresser and
returned to my bedroom. I pulled the blouse on first, it was a dark blue
and felt smooth and silky. I later learned it was satin. The skirt had
appeared to be knee length when it was on the hanger, but when I stepped
into it and pulled it up around my waist, I realised that it was above
the knee. It wasn't short by any stretch of the imagination, but it felt
nice and had a flair to it that I liked. I examined my image in the
mirror in my bedroom and couldn't resist doing a twirl. I heard someone
laughing and turned to see my Mum stood in the doorway.
"How do I look?"
"Like my daughter."
A little while later, we were driving to a shopping centre on the edge
of town. Well away from the local town centre and where there was less
chance of bumping into anyone we knew. Leaving the house for first time
had been the most nerve racking thing I had ever done. I stood in the
hallway wearing a jacket that Mum had bought me. It was black leather,
but it was a feminine style. She had given me one of her handbags, she
had at least five of them. In it she had placed my smartphone, my cash
in a purse which my Mum also gave me. She also added a hair brush, a
compact mirror and mascara, my eye shadow and my lipstick, just in case
I needed to make repairs to my look over the day. I had waited in the
doorway as Mum walked out to the car and started it up. Then I had put
on a pair of dark sunglasses and scuttled out, pulling the door shut
behind me. I had scurried to the open passenger door. I dropped my
bottom into the seat and then, with my knees together, I had swung my
legs into the car, pulled the door shut, placed my handbag on my lap,
and had tried to sink into the seat.
"Seatbelt please. And no hiding," Mum had said as she snatched the
glasses from my face. "Now sit up straight and stop slouching."
I tried to sit up and relax but I was still very nervous. I was after
all a boy, in a skirt and blouse and a layer of make up, pretending to
be a girl. And I was outside, in public, in the outside world. Well, I
was in a car, but you know what I mean. However, as we left the streets
where we lived, I found myself nervousness dissipating. Of course, there
was still the possibility that someone who knew my Mum would see us and
would wonder what she was doing driving around with a young girl. As we
left the area, I grew more confident and sat up in the seat, looking out
of the window and watching the other cars. Wondering who they were,
where they were going and why they were going there. As we drew nearer
the shopping centre Mum pulled into the car park and drove close up to
the edge of the centre. She parked a hundred feet away from the
entrance. As she parked the car and applied the handbrake, she turned to
me.
"Are you ready?"
No, I wasn't ready, I was scared to death, I wanted time to roll back to
Friday lunchtime and change this, change it to a time when I was doing
this in secret, in private. For a moment I wished that I had never found
that damned swim suit, never tried it on. I glanced at the entrance, and
then back Mum.
"Yes."
Mum beamed.
"Let's go then." We stepped from her car and Mum locked it. As we strode
towards the entrance, I saw people coming and going. They were too
wrapped up in their own actions and thoughts, to take much notice of us.
I walked side by side with my Mum as we entered the shopping centre. I
hesitated for a moment, There were too many people. Too many... I felt
my Mum take my hand. It instilled a sense of confidence in me. I could
do this. I let go of her hand.
"Right. Where too first?" I asked. Mum smiled at me, a warm benevolent
smile that flowed into me, increasing my confidence.
"Essentials first, than window shopping. Business before pleasure."
We spent that first hour getting essentials. More underwear, more make
up and three pairs of new shoes. Two pairs of flats and a pair of three
inch stocky heels. They were white, and Mum said I needed a new dress to
go with them. Loaded down with shopping bags, and we had not finished
shopping yet, we returned to the car and placed our bags in the boot of
the car before returning to the shopping centre.
We spent the next hour window shopping and admiring the dresses in the
windows, occasionally going into the shops to try dresses on and see how
they fit. The first time that Mum suggested I try a dress on, I nearly
had a fit of hysterics. But Mum calmed me down, and I actually went into
a changing room and tried it on. It was white, a hemline that settled
just above my knees with lace sleeves and was absolutely adorable. I
took off my blouse and skirt and I wriggled into the dress, managing to
zip it up. The look of delight on my Mother's face showed her approval.
She commented on how well it hung on me and after checking the price,
agreed to buy it for me. We saw the same dress in black and put it on a
wish list.
I paid for the dress myself, with cash that Mum pressed into my hand. I
was really nervous approaching the young saleswoman. Thinking that she
knew, she would treat me with disdain and disgust, and announce to the
store that I was a boy in drag. She smiled at me as she took the dress,
scanned it and then folding it and placing it in the bag. She took my
money and gave me my change with swift efficiency and a cheerful smile.
What she said at the end of the transaction gave me a swell of approval.
"There you go miss. I hope your boyfriend likes it."
I walked away with a buzz. Mum had a final store to visit. She steered
me towards a Victoria's secret store and we entered. I was immediately
embarrassed and flushed red. It was weird being surrounded by all this
lacy feminine underwear.
"You need some pretty matching underwear. So, look for something you
like. I think you should go far something with a garter belt and
stockings. Ultimate femininity." She grinned and then guided me to a
rack of matching underwear. One set did indeed catch my eye. It was
black. The bra had a gold and silver pattern on it. The panties had a
similar design and the garter belt was plain, but the suspenders straps
were in silver, and three gold bows adorned the front of the belt. It
was ludicrously expensive, but Mum agreed. We then chose three pairs of
stockings. Two were plain 15 denier and one pair had a diamond pattern
and all three pairs were seamed. My Mum saved my embarrassment by
purchasing them herself while I waited outside. But once we were
outside, she pressed the bag into my hands. We decided to get a coffee
and then head home. I had relaxed enough now to be more expressive in my
movements and gestures and was relaxing into the role. This was great,
it was too good to be true. And of course, it all came crashing down on
us.
"Angela? Angela!"
We had reached the fountain by the entrance when the voice interrupted
our conversation. Mum turned and found herself suddenly engulfed in an
embrace. Mum reacted with surprise and embarrassment for a moment,
struggling free of the embrace, until she recognised the woman, her face
breaking into a wide smile. She then returned the embrace, warmly and
lovingly.
"Linda! Hi. Long time no see. How are you?"
Her name was Linda Whitely. A tallish woman dressed in skin tight pale
blue jeans a white top and black leather jacket. She had been our next
door neighbour until eighteen months ago, when she and her son, a lad a
year older then me called Alan, had left to move in with Linda's
boyfriend, and Mum had lost contact with her. Odd, since they had been
inseparable when they were neighbours. Linda was a few years younger
than my Mum but they had so much in common that they could have been
sisters.
Alan and I had also gotten on fairly well, We cycled, played video games
and walked in the park. I looked around for him, he wasn't there, but
someone else was. It was a tallish young woman, who had stood back and
was stood with her head down, a long mane of golden hair hiding her
features. She was dressed in a pale blue skirt, a white blouse with
black tights and black high heeled shoes. Like Linda, she was wearing a
leather jacket, but this was white and biker style. She appeared to be
embarrassed for some reason.
"My god Angela, you haven't changed a bit," Linda said.
"Except around the waist maybe," Mum replied. Linda laughed.
"Nonsense, you've lost some weight actually."
"And you're just the same too. How are things with... erm..."
"Daniel?" Linda offered.
"Yes, that's right. Daniel." Mum sounded embarrassed.
"We're fine. He's just proposed actually."
She held out her left hand and Mum gasped at the sight of the ring. It
had a huge diamond held between two pearls.
"That must have cost a fortune!" Mum said. Linda shrugged.
"He's been saving for ages. We're planning the wedding actually. Oh, we
must catch up with each other, here let me give you my number." Linda
dug into her purse for her phone as Mum glanced at me nervously. Linda
followed her gaze and caught me looking up at her, giving her a good
look at my face. I almost immediately turned away, looking at the nearby
store. I felt Linda peering at me.
"Angela, is this who I think it is?" she asked quietly
"Oh," My Mum suddenly sounded embarrassed, "Err, this is my... my
daughter. Gabby."
"Your daughter?" Linda said, I turned back to Linda, she was peering at
me in a curious fashion, then she shrugged her shoulders, with a what-
the-heck expression and smiled at me.
"Hello Gabby. My how you've grown. You're very pretty."
I blushed.
"Thank you Aunty Linda."
Linda smiled and then turned to the woman at her side, who was trying,
crablike, to walk away.
"Let me introduce you to my daughter." The girl looked to be on the
verge of making a run for it. Linda grabbed the shoulder of the leather
jacket and pulled the girl forward. "This is Helen. Say hello Helen."
The woman looked up. I was confused. Linda had son, called Alan, who the
hell was... wait a minute I thought. Helen's eyes grew wide as we
recognised each other. Helen looked from me to my Mum and grew a little
more confident in her appearance.
"Hi Aunty Angela." She glanced awkwardly at me. "Hi Gabby."
I merely glared at Helen until, common sense intervened and I managed to
slap my mouth shut. I opened it again, after careful thought as to what
I should say.
"Hello Helen. It's nice to meet you," I finally managed.
Helen looked up at me, a little embarrassed, then she straightened up
and drew her hair back over her right ear.
"It's nice to see you again," she said. There was an embarrassed silence
for a while. I don't know the others were thinking, but one word was
ringing loudly in my head. Awkward. Then Aunty Linda brightened up.
"Hey, I've just had a great idea. Why don't we split up?
"Meaning?" Mum asked.
"Well, there's a coffee shop just down the way there. And there's a
McDonald's on the upper tier. Let's say you and I, Angela, catch up over
a coffee and the girls can have a cheeseburger and a milkshake and get
reacquainted. And we meet back here in an hour. How's that sound?"
My Mum considered it, she actually considered it. And then she smiled.
"I think that sounds great. What do you think girls?"
I thought it sounded totally bonkers, and the look on Helen's face told
me that she thought the same. She glanced at me and then smiled, the
change in expression mirroring the change in her thinking.
"I think that's a great idea. What do you think Gabby?" I gritted my
teeth and was about to answer, when Mum answered for me.
"That's agreed then. We'll see you in an hour."
I was about to argue that I hadn't agreed to it, but Helen stepped
forward and took me by the arm.
"Come on Gabby, I think we have lots to talk about."
In a daze, and I honestly don't remember the next few minutes, Helen led
me through the shopping centre by hooking her arm in mine and leading me
to the upper tier. My mind was in an absolute mess. So much had happened
in the least few minutes and it had raised dozens... no, hundreds of
questions. Questions that I did not really want the answers to. Whoever
said that ignorance was bliss, hit the proverbial nail right on the
head.
We garnered little attention as we entered the McDonald's where Helen
ordered, then picked up and paid for two Big Macs, two medium packs of
fries, a sprinkled doughnut for me and a hot apple pie for her. We had
two large Pepsi's instead of the milkshakes that Aunty Linda had
suggested. We made our way out onto a balcony that overlooked the nearby
park and the small river that ran through it. We found a table right on
the edge of the balcony, away from sensitive ears and sat down. Helen
placed my meal before me and set hers in front of her before setting the
tray aside on the next empty table.
"Right then," Helen said, unwrapping her Big Mac, "let's swap stories,
who goes first?" She then took a big bite of her burger and began
chewing.
"Er... I will," I said, placing my arms on the table. "I've been
dressing up since I was thirteen, I've always been fascinated by women's
clothes and I started buying clothes then. My Mum, found me on Friday
afternoon and since then, she's been teaching me how to act like a girl
and, basically... pretend to be a girl. When I'm Gabby, I feel calmer,
more confident and... just nicer."
Helen chuckled as she took a sip of her Pepsi.
"So is this you first time out?"
I nodded as I opened up my Big Mac and began munching on it, piking up
the scraps of lettuce from the box and eating it. Helen nodded in
appreciation.
"Well, You look great. And your mannerisms are perfect. I think your
mum's done a good job. Anyway, I've been dressing up for years. It
started with my Mum's clothes and she caught me when I was about nine,"
Helen paused to take a big chunk of her hamburger and chewed it, washing
it down with a gulp of Pepsi, I was in a bit of a daze. That was two
years before I had found the swimsuit and a further five years before I
started dressing up properly. Helen finished off her burger and wiped
her mouth with a napkin
"My Mum was angry at first but when she had calmed down, she asked me a
load of questions. By then she had read up on it and found that it was a
perfectly ordinary thing for a young boy to do, no stranger than stamp
collecting or train spotting. And then she started buying me my own
clothes and taught me make up skills and how to act like a girl."
I had finished my burger off by now and was starting on the fries,
between sips of my drink. To know that Alan had been dressing up as
Helen while I had known him was a little puzzling.
"You've been doing it that long?" I asked. Helen nodded. Then with a
frown, she dig into her handbag for her phone, which was ringing. I
turned away to give her some privacy.
"Hello? Oh Hi. No, it's Helen. I'm out shopping with my Mum." She
glanced sideways at me. "I ran into a friend actually, an old friend I
used to know, she's called Gabby."
Helen listened to her end of the conversation for a few moment and then
she smiled.
"No, she's... a girl like me." Then her expression turned to one of mock
shock. "No of course not, You know I'm not like that. I don't think she
is either."
There was a garbled noise on the smartphone and Helen was suddenly
smiling broadly.
"Hey, that's a great idea. I don't know, I'll ask her." She dropped the
phone to her shoulder for a moment. "Are you free tomorrow afternoon?"
she asked.
"Er... I've got nothing planned...?" I was puzzled now. Helen raised the
phone to her ear. "She's free, but listen, we only met up again today,
so we need to talk properly to get to know each other again. Also, we've
only just fond out about each other."
Helen listened for a few more moments and then with a big smile, she
nodded.
"Okay, okay. I'll call you later. Yeah, see you soon." She chuckled a
little. "I love you too." She ended the call and put her phone back into
her handbag.
"That was Frankie." She placed her hand up the side of her face. "She's
my girlfriend," Helen whispered.
"And she knows?" I asked gesturing to her clothes. Helen nodded
earnestly.
"Oh. Yeah. She's cool about it. Anyway, tell me more about yourself."
I shrugged.
"I've told you everything."
Helen rolled her eyes.
"No, you idiot. Tell me about you and what's been going on with you.
I've missed you."
I suddenly cottoned on to what she meant.
"Oh, you mean, since you and your Mum left?"
"Yes doofus. Honestly."
We spent the next half hour filling each other in on what had happened
in our lives since Linda and Alan had moved in with Daniel. Alan's real
Dad had run off when he had been two so he did not know his Dad, but
Daniel had been good, both for his Mum and Him. He had stepped up to
become a father figure to Alan and even knew about Helen who he treated
with equal courtesy. He had met Frankie at college and they hit it off
pretty quickly. She had been nervous telling Frankie, real name
Francesca, but she preferred Frankie, about herself, but Frankie had
been fine with it and she had embraced Helen eagerly.
I also told him about my time. I had a few friends, Max had taken his
place as best friend and how I spent my days doing homework, revising
for my upcoming exams and how well I was doing. I was heading for sixth
form and A levels the way I was going. Helen congratulated me and then
called me a swat. But then she admitted that I had always been smarter
then her.
"So you're heading to university?" she asked.
"I don't know yet. I don't know if we can afford it," I replied.
"Can't you get a grant or a loan, anything?"
I shrugged.
"I'd rather not leave University with a heavy loan still hanging around
my neck. And since I don't know what I want to do yet I wouldn't know
what to focus on."
"I didn't know what I wanted to do either. But forget the future for
now, let's focus on the present. What are you doing tomorrow?" I sat
back. I hadn't planned on doing anything really. I was hoping I could
relax after the last couple of days and come down from the high. Maybe
spend the day dressed as... god forbid... a boy. I shrugged after a few
moments thought.
"I don't know. I wasn't planning on doing anything. Although I do have
some homework that needs doing, it's not due till the end of the week so
I can possibly..."
"Good. Can you come round to my house tomorrow?"
"I don't know where it is."
"I can give you the address but can you come?"
The more I thought about it, the more I remembered Alan and the
friendship we had. I nodded.
"Yeah. I'd like that."
"Okay. Now, I'd like you come as Gabby."
A mixture of different emotions raced through my head. Surprise,
anxiety, fear... why was guilt in there? I did not know why, but I did
want to know one thing.
"Why?"
Helen smiled.
"Well, you're not the only boy who dresses like a girl in this town and
neither am I. When Mum was doing her research she found a local
crossdressers group, called, get this, The Sequins."
"What? Here?" I asked in an incredulous tone. The town we lived in was
northern and provincial. It didn't even have a soccer team. To know that
there was a group who helped people like me was a revelation. Helen was
nodding vigorously.
"I know, it's crazy right? Anyway, it's a group dedicated to promoting
understanding and tolerance and also to provide a safe environment for
crossdressers to get together, Anyway, every Bank Holiday one members
family provides a space and since it's the beginning of summer, my Mum
decided to hold a barbecue at our house. Because Daniel has this big
arse house with a massive back lawn, and it's set back from the road a
little so there's plenty of privacy."
Having finished her burger, Helen put her rubbish into one pile and
reached for her apple pie. I had long since finished my doughnut, so I
put my rubbish with hers. I suspect that she was letting the information
seep in before she continued.
"Anyway, there's about twenty five people coming, most of them are
crossdressers like us, of various ages, who have promised to attend.
Now, the party is due to start at two o'clock, but if you could come
round for about one o'clock, that gives me a chance to introduce you to
Frankie and Daniel. What do you say?"
Helen, having let the apple pie to cool sufficiently to eat without
burning her mouth, as well as placing the conversational ball in my
court, looked up. I didn't know what to say. In the space of seventy two
hours I had gone from a boy with a guilty secret to a confident young
woman. Of course, I was still a boy, but I looked like a young woman.
I'll admit it, my thoughts were a little fuddled, but I had the rest of
my life to sort it all out.
"I'll need to settle it with my Mum, but I'll let you know. Okay?"
Helen smiled so brightly, she was glowing.
"Okay. Oh, speaking of Mum's we'd better get going. We're supposed to
meet them five minutes ago."
We cleared our rubbish away and put the remnants of our meal in the bin,
the tray on top. We then left the restaurant and made our way back down
to the fountain. Neither my Mum or Aunty Linda were there, so we sat on
a bench. I saw a branch of a popular technology store that sold pre
owned goods. Thinking of the game I wanted, I suggested to Helen that we
go in for a look around, and she readily agreed. No one paid us any
attention as we walked over and went into the store. I scanned the
shelves for the title I wanted and saw that I could still afford it,
despite spending some of my money earlier in the day.
Helen and I stood in line while we waited to be served. As we waited I
glanced around and saw that though a few people were checking us out,
the looks we attracted were mostly non-descript and non-committal and
though we were examined, and under scrutiny there was no indication that
those who looked had any suspicions about us, accepting us as what we
appeared to be. Or if they did suspect us to be something different to
what we appeared to be, they said nothing. I began to suspect that if
they did realise we were two boys dressed up as girls, they didn't care.
As we waited for the sales assistant, a young woman with a heap of
tattoos and several piercings, to retrieve the disc and manuals for the
case, we chatted about nonsense and when she came back, I gave her the
cash. She put the game in a bag and handed it over.
"There you go miss," she said with a smile. It may have been false, it
may have been my imagination, but I walked out of that store with a big
boost of confidence. We made out way back to the fountain where Our
parents had finally arrived. We spent a further few minutes chatting,
exchanging phones numbers and addresses and then we parted. Helen and
Aunty Linda heading to the local bus exchange and Mum and I headed back
to the car park and made our way home. All the way, I felt as if I was
floating on air.
We arrived home at about four that afternoon and spent the remainder of
the early evening putting my new purchases away and then after a light
meal of salad, with a juicy pork pie each, we retired to the living
room. Mum opened a bottle of wine and handed me a glass. I accepted it
gratefully.
"Ooh, thank you," I said.
"Don't get used to it," Mum said. "You're still under age you know. But
you've earned yourself a glass." She sat down on the sofa opposite me
and took a sip.
"So, you first time dressed as a girl out in public, how did it feel?"
I sat back and tried to sort my feeling into some sort of order.
Different words flowed through my mind as I ran the experience through
my head. I finally came up with to words to describe my day.
"Scary and exhilarating."
My Mum frowned.
"How so?"
"Well it was scary because I was dressed as a girl, but it was
exhilarating for exactly the same reason..." I frowned. "Does that make
sense?"
Mum thought for a moment, then she nodded.
"In a way. I can only imagine what a rush it must have been. But you
handled it extremely well. I'm proud of you."
"So, can I do this again?"
"Of course you can, but only when I'm with you." She suddenly brightened
and sat upright in her chair. "Which reminds me, Linda told me that
Alan, as Helen, is a member of a transvestite support group that meets
up regularly and tomorrow, they are holding a summer barbecue. She's
invited us."
Oh, I had forgotten about that in the rush. And to be honest, I still
did not know what to make of the offer. I had spent one day out, dressed
as a girl... oh hell, I'd spent the best part of the weekend dressed as
a girl. I was sort of hoping I could go back to being dressed as a boy
again. But a small part wondered what it might be like... Mum sensed my
hesitation.
"If you want go go, I'd be happy to take you. It will give me and Linda
a chance to catch up," Mum said. "But I don't want to push you of the
front door in a dress again. Not if you don't want to go. But let's face
facts. If I left you alone in the house on a Bank Holiday for a few
hours, how long would it take before you were dressed up again?"
I considered her answer. And I had to admit I'd be in a bra and panties
before she was out of the door. So as anxious as I was to appear in
public again as a girl...
"Okay. I would like to go out again and I want to see Helen again. And
if it means being in the company of other men who crossdress, then so be
it."
Mum rolled her eyes.
"Oh don't be so melodramatic. It means being in the company of like
minded individuals. They won't judge you at all. They might even help
you. Now pick another movie and we'll wind down after an exciting day."
We argued again over the movie we wanted to watch. We eventually settled
on Mamma Mia. I didn't want to watch it, but I settled down to watch it
anyway. And if I'm honest, I actually enjoyed. A little. Mum had
promised me one glass of wine. But she actually poured me a second.
Part Four; Monday. Accepted.
Bank Holiday dawned. It was a bright hot morning and I lay in bed for a
moment. Staring out through the window, at the golden sunlight that
streamed in through the window. Eventually I realised that I was wide
awake and that it would be pointless to stay in bed any longer. I
reached for a my phone and saw that the time just just turned nine
o'clock. Was My Mum awake? I doubted it for some reason. Unable to
sleep, I dragged myself out of bed and found myself in a -shirt and
shorts, my regular night outfit. I debated with myself for a moment and
then dressed in a pair of boxer shorts and clean socks. Then I shrugged
into a pair of jeans and a t-shirt.
I looked at my reflection. I was surprised by the image that presented
itself, An androgynous looking figure. Clearly a boy, but with soft
feminine features. Only the lack of hips and a bust showed a male. I
headed down to the kitchen and made myself some toast and a cup of tea.
I wondered then what I could do. I was often at a loss as to what to do
on a bank holiday. I was roused from my thoughts, which had turned to my
bike and a short ride through the park, when Mum, still in a nightgown
and her dressing gown came into the kitchen.
"Morning Gavin. Sleep well?"
"Yeah, really well. Yourself?" I jumped up to make her a cup of coffee.
"Oh, I slept like a baby," she said. "Anyway, Linda wants us at her
house for one o'clock which means we have to leave by half past twelve
at the latest. Which means you have start getting ready by eleven at the
earliest."
"Okay." I glanced up at the clock and saw that it was only just turned
half past nine. "I might go out on the bike for bit if that's okay?"
"Sure. Just don't be gone too long."
I headed into the garage and pulled my road bike down from the hooks on
the wall. It was an old bike, at least five years older than I was, but
it was well maintained and well loved. Still in the garage, I strapped
on my helmet and mounted the machine. I free wheeled down the drive,
before turning onto the road, aware of the traffic and other vehicles.
After fifteen minutes, I reached the park, surprised to find it rather
empty on a bank holiday, but it was still early. As I powered along the
footpaths and up the hills and down the banks, I found myself wondering.
A pair of feminine sports leggings and a sports bra. Could I actually
pull that look off?
By quarter past one we were pulling onto the drive of a big house with a
double garage. The drive was easily big enough to accommodate several
cars so there was plenty of space to park. Linda was waiting for us
outside and with a tall man at her side. We were a little late, but
judging by the smiles on their faces, they were forgiving. We were late
not because I had been too long in the park, but I decided to wear the
fancy underwear with the garter belt and the stocking. I would have gone
with tights, but I wanted to feel the sensations of wearing stockings,
to feel pulling on the garters tabs as I walked. It felt way better than
I expected. Anyway, that took a little longer to put on and of course, I
wore my white dress with the lace sleeves so of course, I also had to
wear the three inch stocky heels. They were taller than the ankle boots
so I had to get used to them, before we set off. and of course, the
traffic slowed us down a lot.
Linda stepped over as Mum and I climbed out of the car. Her arms
outstretched, a big warm smile on her face. The tall man hung back.
"Angela so good to see you again," she said, embracing my Mum.
`"Thank you for having us over. What a lovely house you have."
"Wait till you see the inside, it's huge." Linda then turned to me,
"Hello Gabby, you look fabulous."
I blushed, a reaction that I was becoming accustomed to.
"Thank you."
"Helen is getting stuff ready in the back garden. Oh, by the way," she
gabbed the hand of the tall man, who was standing back a little, his
hands in his jeans pockets, a bright smile on his face, and pulled him
forward, "This is Daniel. Dan, this is my friend Angela and her daughter
Gabby." Daniel held out his hand.
"Angela, it's a pleasure to meet you. Linda hasn't stopped talking about
you since yesterday. I feel as if I knew you already."
Mum took the offered hand and pulled him into her embrace.
"Daniel, it's great meeting you at last. But I know next to nothing
about you, apart from the fact that you have a lovely house."
Daniel chuckled.
"Perks of being a self employed electrician," he confessed. My ears
pricked up.
"You're an electrician?"
Daniel smiled at me.
"You must be Gabby," he said, he extended his hand I shook it, surprised
at how gentle his grip was. "And yes I am an electrician. And believe
me, it's a lucrative little job. Is that something you want to do?"
I thought about it. One of the many job ideas that had drifted through
my head over the last couple of years was the possibility of something
in construction, so maybe... electrician?
"Er... I don't know yet, but, probably?"
"It's hard work getting a foot in the door but once you're in there,
you're made."
"Anyway," Linda said. "Let's continue this inside before it gets
awkward."
We entered the house and into the hallway which could have contained our
whole living room. Linda showed us into the living room and we sat down
with Linda as Dan fussed about in the kitchen making drinks. As Mum and
Linda chatted I gawked at their TV, It was fixed to the wall, and was
absolutely bloody huge. I saw Helen enter the room. She was dressed in
light grey jeggings and a white t-shirt. Seeing her dressed so casually,
I felt a little over dressed.
"Hey Gabby, great to see you again."
"Hi Helen."
I would have said more but Linda cut me off.
"You're not wearing that this afternoon are you"
Helen looked aghast.
"Of course not. I'm going to get changed in a bit. Come on Gabby, I'll
show you round."
I was shown the kitchen which looked something out of a cookery show.
All that was missing were the cameras. I was shown the back garden,
though it looked more like a local park than a garden, it was that big.
It even had a pond, though no fish. I was shown the dining room, laid
out with sandwiches, pastries and confectioneries, ready for upcoming
barbecue.
Helen then led me upstairs where I was shown the bathroom which was huge
with a large tub, a walk in shower and even a bidet. Helen showed my her
male bedroom which was tastefully decorated and obviously male. I was
envious of the guitar and amplifier that stood in one corner. It was a
Gibson style , and it looked like a genuine Gibson. Helen then showed me
her room. It was clearly a female's room. Pastel colours, a soft carpet
and a large bed with a canopy. A large dressing table with a vast array
of make up was set against one well and against the other were two large
wardrobes which she threw open and were crammed full of clothes. She
reached for a pale blue dress with lace sleeves and bodice.
"I'll be wearing this for the barbecue." She held it up to her body.
"What do you think?"
"It's gorgeous," I said.
"Oh, thank you," she said, "I'm thinking of wearing stockings with it.
What do you think?"
"You should. I'm wearing stockings after all."
"Really?"
I pulled up the hem of my dress, revealing the lacy stocking top and a
flash opf bare thigh before I dropped it down again. Helen nodded
appreciatively.
"Frankie loves it when I wear stockings."
Just then the doorbell rang.
"Oh, speak of the devil, that must be her now."
Helen headed for the door and I followed her, but held back. Helen
opened the door to show the newcomer. It was a tall slender girl. She
was dressed in a pair of black shiny leggings and a lace blouse, which
clearly showed her bra. She was also wearing a pair of four inch heel
boots. Her blonde was short, but it was in a feminine style and her make
up was soft and understated. They embraced after greeting each other and
then Helen showed the young girl in.
"Frankie, I'd like to introduce to an old friend of mine, this is
Gabby."
Frankie's eyes widened in surprise.
"Oh yes. I've heard a lot about you since yesterday." She took my hands
in a gentle hold and looked at me closely. "You look fantastic, very
natural. I love the dress by the way."
"Thank you. You look great as well."
"Oh, thank you." I found myself being embraced briefly before Frankie
pulled back. Her smile was warm and genuine. It turned into a frown when
she looked at Helen's outfit.
"You're wearing that this afternoon?"
Helen's expression grew angry as she looked down at her jeggings and t-
shirt.
"What's wrong with this top?"
An hour later, the barbecue was in full swing. Daniel was stood at the
Barbecue with an apron on, cooking burgers, sausages and jacket
potatoes. Music flowed out through from the living room through the open
patio doors, almost drowned out by the lively chatter of the guests that
were assembled either in the living room or in the garden on chairs and
stools. Some were sat on blankets. And the only person dressed in male
clothes was Daniel. All the rest were actual women and and men dressed
as women. Their ages ranged from teenage like Helen and Myself through
to the oldest member of the group, a sixty seven year old gentleman who
called herself Vanessa and was the founder of the group. Vanessa was
accompanied by her wife, a sixty year old lady called Fiona. I was
introduced to them first as they were the first to arrive. Despite her
age, Vanessa looked a good sixteen years younger and was dressed
conservatively in a two piece business suit in peach with an off white
blouse. Fiona was wearing a similar suit, though hers was a light grey
matched with a red top. I complimented them on their appearance and
Vanessa had smiled graciously.
"I moisturise. And I exercise rigorously," she explained. Fiona leant
in.
"Not to mention all the padding."
Vanessa went on to explain that she had founded the group in 2010 when
she had taken early retirement from her position as CEO of a major
company and had finally been given the freedom to dress as often as she
had wanted. Fiona explained that she knew about Vanessa as soon as they
had started dating in the late seventies. Back then there had been a
massive amount of prejudice against crossdressers so he had done it in
secret, but this had been a lonely life. With the millennium, attitudes
had shifted and Vanessa had come out more often.
She had started the group after finding several other crossdressers in
the area. From a small group of five people, it had grown into an
organisation with about forty members. Admission was free, provided that
members paid their own way on any social outings that the group
arranged. By then others had started arriving. I was introduced to so
many different people that it was difficult to remember them all. But
the overwhelming response was that I looked very good and looked
passable.
Sadly, not everyone was passable. There was one crossdresser that did
not look passable at all. For a kick off, she was well over six foot and
largely overweight. She was dressed in a yellow summer dress and because
she didn't shave, she had a fine covering of dark hair on her arms and
legs. She just liked the clothes she said, she didn't want to pass. She
was however, very sociable and was accepted by the others.
There was also one girl there who called herself Penny. Dressed in a
knee length black skirt with a white blouse, grey tights and black high
heeled shoes, she looked extremely natural, but she was on her own.
Apparently, she was married with a young child. Her partner did not like
this aspect of Penny's personality and refused to let her dress at home,
especially with a young toddler running around. She was a member of the
group because she needed to dress up and could only do so within the
group. I felt sad for her in that her partner did not accept her
dressing. Hearing her story made me realise how lucky I was to have my
Mum, who not only accepted this but was helping me.
There were several couples present who were men dressed in female
clothes with their girlfriends who accepted their men dressing as women.
Two of the couple were dressed in identical outfits and one couple
looked more like twins than boyfriend and girlfriend. One couple, in
their early twenties I got to know very well, as our stories were very
similar.
Hannah, her real name was Andrew, and her girlfriend Kelly had sort
monopolised my presence. She too was a new member and we were sat on the
couch on the living. Hannah and Kelly were sat with bottles of beer
while I nursed a large glass of coke.
"I started dressing when I was very young," Hannah told me. "I had two
older sisters and one of them was really into gymnastics. And I was
fascinated by her leotards. So I tried one one and that led to other
clothes. And when she found out, she helped me out. And Hannah's been a
part of my life ever since."
"I've known about Hannah for ages," Kelly said. "I was a little freaked
out at first, but then I realised that Hannah was just an extension of
Andrew. And a nice one too."
"So, what about you?" Hannah asked me. "A swimsuit you said?"
"Yeah. When I was ten. I didn't start dressing up until I was thirteen
but my Mum's been helping me since she found me on Friday."
"Well, I think you look fantastic," said Kelly, "And It's so unfair that
men get teased for dressing up."
"I know," Hannah said. "Tell me about it. I mean, If Kelly got up in the
morning, put on my underwear, a pair of my jeans and a t-shirt, or a
suit and tie and stepped out through the door, no one would bat an
eyelid. But if I get up and put on her bra and panties, put on a skirt
and blouse, or a nice dress, and a layer of make up, and I step out
through the door? People start thinking what's wrong with this picture?
They start calling out names and making all sorts of false assumptions,
like I'm gay or weak or something. It's not fair that we can't be who we
want to be. And all we want to be is our selves."
As we talked about other things, such as movies, hobbies what television
programmes we liked and so on, I can honestly say that I forgot Hannah
was a twenty four year old man called Andrew. Weird. And I don't think
that they even considered the fact that I was a sixteen year old boy
called Gavin.
The party went on till the early evening. And despite it being early
Summer, it grew chilly in the garden so the party moved into the house.
It was a good thing that it was such a big house. As I talked to the
other members, I learned more about this hobby of mine. How it was not a
perversion, that it was not a fetish, that it did not mean that I was
gay or even that I wanted to become a girl. I also learned from a
doctor, who had come dressed as a nurse even though it wasn't a fancy
dress as such, that medical research had shown that men who dealt with
stress by inventing a female persona for themselves and dressed as women
were healthier and more compassionate and in general led less stressful
lives because they chose to wore dresses. I had not even considered
this. My Mum, after catching up with Linda, had spoken to the others and
also learned more, through hearing their personal stories. I think my
Mum learned as much, if not more than I did.
Another couple who were present at the party were a brother and sister
called Jilly and Tammy respectively. aged sixteen and nineteen, also
respectively, and were wearing matching black dresses. Jilly was a
slender girl with a long mane of auburn hair that she wore in a tight
bun on the top of her head. A style that suited her. I was also trying
ignore how attractive she actually was. She had almond shaped eyes that
were a clear blue. And if that was not enough, she had a smile that
could melt an iceberg
Tammy's real name was Thomas, which in her youth had been shortened to
Tommy and led to her being called Tammy She was pretty as well. A crop
of short brown hair was cut in a feminine style. Her eyes were also
blue, but they were a pale blue with a hint of green.
"I've been dressing up since I was nine," Tammy explained. "I'd been
wanting to dress up for ages. I don't know why and I still don't know.
Anyway, I asked my mother if I could try some girls clothes."
"I've told him since that he could have asked me, but he didn't want to
embarrass me," Jilly said. "Not that I would have been embarrassed."
"Anyway, Mum agreed, grudgingly admittedly. But she borrowed some of
Jill's clothes and let me try them on. She later said that if she let
me, dress up, it would be a phase that would pass," she threw her hands
up to indicate her dress, "It clearly hasn't." she said with a large
smile.
"She's fine with it now," said Jilly. "She's given up trying to stop
him."
Tammy rolled her eyes.
"No one can stop me, or make me stop." She thought for a moment. "I'm
not sure why I dress up. All I know is that I like dressing up. It makes
me... a better person?"
Jilly was nodding emphatically.
"Tom is a great big brother, but she's also a really great big sister."
Tammy looked happy. Tearful, but happy. She embraced her little sister.
"Aww, thanks Jilly."
Helen, who been mingling throughout the party, entered the room.
"Hey guys, Hope you enjoyed the party."
Tammy leapt to her feet and embraced her.
"Hey! Helen. You should really sit with us. We're having a great time
with Gabby. She's great." She smiled at me. "We should go out together
some time."
Frankie entered the room, an idea forming in her mind, judging by the
look on her face.
"Well, we're all working tomorrow, as it's back to normal. So, how about
going shopping at the weekend?"
"All five of us?" Jilly asked. Frankie nodded. "That's a great idea."
She turned to me.
"That is of course you want to come."
"I'd like to, I'll need to check with my Mum," I said. "But I'm sure
she'll be fine with it."
Jilly beamed with delight.
It turned out that Tammy was a friend of Helen's from their work at a
local call centre and had discovered that they shared the same hobby
when they arrived at work, in drag, for a fancy dress charity day. Helen
had come as french maid and Tammy had worn a second hand wedding dress.
Tammy had joined the group about six months later. We fell into
discussing our various and varied lives Soon, all five of us were sat
around the dining table still holding the remains of the buffet and
chatting like old friends. We discussed, movies, hobbies, our plans for
the future, all manner of things. And of course, we were discussing
fashion.
By eight thirty, the party was all but over and people were leaving.
Angela and Linda were in the kitchen discussing their lives and how they
would stay connected this time around. After admiring each other
dresses, Helen, Frankie and Tammy had taken themselves up to Helen's
room to show Tammy her range of clothes and I was left in the dining
room with Jilly discussing my favourite topic, Marvel Comic Universe
Films.
It seemed that Jilly had the same interests in me. We both science
fiction movies, especially the MCU movies, we both had a Playstation, we
both liked reading. We even rode bicycles. I had my old street racer and
she had a twenty one gear mountain bike, though only nineteen of those
gears were actually working. I found myself offering to take a look at
it for her. I was comfortable in her company and got the impression that
she felt the same way. I'll admit it. She was an attractive young woman
and I was attracted to her. But was it mutual?
At quarter to nine, Mum appeared and said that it was time to go home. I
said goodbye to Helen and Frankie at the door. As we walked to our car,
Tammy and Jilly were walking to their Mum's car, who had arrived to pick
them up. As Tammy was getting into the car, Jilly rushed over to me.
"I'll see you soon Gabby, and I hope I get see Gavin sooner."
She paused for a moment, and then kissed me on the cheek. I was stunned
for a moment, unable to speak. Then my brain rebooted and I was able to
respond.
"I look forward to it. I'll see you soon."
Jilly turned and was walking back to her waiting car.
"You got my number right?"
"Yeah, yes," I said. "I'll call you later."
"You'd better." Jilly. Then she gone, the car pulling away. My mum was
gazing at me in a shrewd manner, her smile wide and pleasant.
"I think you've pulled Gabby."
I rolled my eyes and sighed in an exasperated fashion.
"Oh please Mum. I hardly know her."
Still, I was thinking that possibly, Jilly might have been interested in
me. I was so wrapped up trying to think things through that when Mum
offered to buy pizza for tea I agreed. It took me a while before it sank
in that I was in the takeaway with the money, alone. Mum had stayed in
the car. I think I managed the task without arousing suspicion.
Back at home, I got changed out of the white dress, the lingerie and
wiped the make up from my face. I dressed in a fresh pair of boxers and
socks with a pair of dark blue jeans and a t-shirt. I was about to leave
my room when the phone rang. I felt a swell of joy when I saw the caller
ID.
"Hey, Jilly, you okay?"
"I'm fine. Just checking that you got home okay."
"Oh yeah, we made it. We're just about to sit down and watch a movie."
"Good, that's good. And speaking of movies, I was thinking about two for
one cinema tickets on Wednesday. We could go to the cinema in town on
Wednesday evening, They're still showing that science fiction film we
talked about. Do you want to go?"
"Hell yeah. Do you want me to come as Gabby or Gavin?"
"As Gavin of course. I think Gabby is cute and all, but I want to get to
know Gavin. I sort off..."
She paused, and I waited. Fearful of what she might say next. You know
what? Forget it. I don't even like you and I prefer it if we were just
friends. I'm sorry I bothered you. Goodbye.
"Okay, I'm going to say it," she eventually continued. "I fancy you. And
I'd like to meet you as a boy. We're already good friends, I'm hoping we
can get closer."
"Okay," I said, my confidence rising, and making me add. "I fancy you
too. And if you like me as Gabby, you'll love me as Gavin."
Her laughter was heart warming.
"I hope so."
We made arrangements to meet up at the cinema. I decided to get my one
and only suit cleaned and pressed. I Had already made a good impression
and I wanted to continue making good impressions. I turned my phone off
and headed downstairs. Mum was already in the kitchen, setting out the
pizza's on plates and sorting out the accompanying fries and drinks.
"Hey, you're Gavin again."
"Yeah. I don't want to be a girl all the time. And as I've spent the
weekend dressed as girl, I'd like to be for a boy for a while."
Mum nodded, in understanding fashion.
"Okay. No problem. Who were you talking to?"
"Jilly. She invited me out to the cinema on Wednesday."
Mum, smiled brightly.
"Ooh. Has my boy got himself a date?"
"Possibly."
"So are you going as Gabby or..."
"No, she wants to meet me as Gavin."
"That's great. That's wonderful. My little boy is growing up into a
confident young woman."
I almost choked on my drink, I had just taken a sip of coke and it went
down the wrong way as I tried to laugh and swallow at the same time. Mum
watched with a smile on her face as I composed. myself
"There's just one thing."
I looked up from the pizza that was cooling on my lap.
"Oh?"
"If you're going out on your first date young man, you're going to do it
properly."