Tommy
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Tommy
© Titania Midsummer
People
Jeff and Linda Scott
Their only child, daughter Lily
Lily's friends - Sophie, Catherine, Brigitte
Phillip and Emily Sorenson
Their son Tommy and daughter Katie
Mrs Krieger - next door neighbour of the Scotts.
*******************
"I once had a boyfriend who was a transvestite, you know, a cross-
dresser." Lily had used a brief pause in the conversation to change the
topic from the usual bitching about the males where they worked. 'They'
were a group of four young women, mid to late twenties, all very good-
looking and expensively dressed. Some would call it power dressing but
that could be almost anything these days. All four were rising stars in
their professions. Perhaps it was the effect of the second cocktail that
prompted the outburst. Certainly it got the attention of her three
companions ensconsed in a trendy bar.
She paused not only for effect but was wondering if such a confession was
sensible.
"Come on, come on. Don't keep us in suspense." This from Sophie. She was
in marketing and was the most pushy of the four-some. Not that the others
were shy violets. The other two were Brigitte, a stock broker and like
Sophie a bottle blonde; and Catherine, a lawyer and hair that some called
'fair', between brown and blonde.
"Well..." Lily looked around but her companions were all ears, and there
didn't seem to be any eavesdroppers on nearby tables. "I was sixteen
turning seventeen at the time, no longer jail-bait but still na?ve, and a
real handfull to my parents. Anyway, one Friday morning I said 'Mummy,
can Tommy come over and sleep with me tonight?'. Now my mum's pretty laid
back and not someone to fly off the deep end, and she was used to my
weird urges. She said 'I think I need more information. What exactly did
you have in mind?' Now I hadn't quite realised what I was saying, but I
certainly wasn't thinking of full on sex. I explained 'Oh I wasn't
thinking of having sex or anything like that. It's just that we get on
well together, he makes me laugh, and he smells nice. I was reading how
in Sweden courting couples are allowed to sleep in the same bed, but
seperated by a big bolster down the middle. We could do something like
that.'
Her audience had to laugh. "This sounds fascinating. Go on," from
Brigitte.
Lily continued. "Well my mum said 'Lily dear, I don't think that's a good
idea. I doubt if any bolster could keep two young teenagers apart, and I
know your father will back me up.' So I said, 'Oh Mummy, I hate it when
you don't trust me. We would be as good as gold. I don't want to have sex
for years and years, if ever, and I know Tommy feels the same.' Which was
probably true at the time.
"Now my mum didn't want to provoke a hissy fit by calling me a liar, or
by laughing at my protestations which would be the same thing. 'There
could be a compromise,' she suggested. 'We could fit you with a chastity
belt.
"Have you ever seen pictures of those things? They look awful and so ugly
and uncomfortable. I already knew that then and I said so.
"My mum changed tack 'Then what about that old wedding telegram
Take a tip from one who knows
Tie your nightie round your toes.
Maybe you could wear a modified nightie?
"I giggled, then I thought about that. 'If I had to pee dining the night,
how would I do it?' 'We could leave a funnel with a long tube in the
bathroom. You would have to work it up from the bottom between your
legs.'
"Again yuk. 'Mummy,' I said, 'that wouldn't work sitting down; and
standing up I think I would spray everywhere.' Then I had an idea 'But
much easier for a boy. Tommy could easily point his thing into the funnel
whilst standing up in the shower cubicle. That's a great idea!'
"It wasn't premediated, but I had trapped my mother into agreeing to the
sleep-over. All she could say was, 'Well, I need to see if your father
will agree, and he probably won't.'
"But I knew he would as my mum could get my dad to agree to anything.
I've seen her do it often. Usually to get me out of trouble.
"Anyway, my mum telephoned Tommy's mother and explained what was
happening. Amazingly they both agreed that it was good for young people
to get to know each other, provided it didn't go too far. Tommy's mum,
Emily Sorenson she was, thought the nightie idea was very clever. 'I just
hope he doesn't get too upset wearing a female garment.'
"So my mother and I went shopping. From the local hardware we bought
cable ties and thin rope. From a nightware shop she bought a suitable
nightie. Pale blue because we figured pink might turn Tommy right off. It
was the longest we could find, in a fairly heavy shiny satin. It had
rather pretty white lace trim round the hem and the collar.
"The nightie had wide shoulder straps but no sleeves. Should she sew them
up to keep his hands inside? She discussed it with me. 'Do you want his
arms outside? They could wander where they shouldn't.' By this time I was
a bit concerned as to what I had let myself in for. But I certainly
wasn't going to show any of those doubts. As it was we decided to keep
his arms confined inside, so mum sewed up the arm holes.
"The nightie had a few buttons down the front so to be safe she sewed
them up so that it was wide enough to slip over his head but not his
shoulders, nor was there room to poke his arms through. Then she sewed
some rope into the hem so that it was quite restrictive, but still easily
wide enough to slide a funnel on a tube up from the bottom. That last
item she made up from a length of garden hose, a plastic kitchen funnel,
and some spacker tape.
"Being Friday evening, when my dad came home from work he really just
wanted a drink and to relax after five days of challenging work. When mum
explained about Tommy sleeping over he felt he should raise strong
objections. However what with the precautions she was taking and the
whole thing being a fait accompli he just made a few token noises and
dived for the drinks cupboard.
"Tommy came over to join us for supper. He had walked as his house was
less than two blocks away. During the meal very little was said about the
arrangements for the night, however dad did say 'If you want a lift home
in the morning, you need to be up early. I'm leaving at seven for golf.'
Mum added some emphasis. 'Next door old Mrs Krieger is a real nosebody.
She is a dreadfull gossip and goes to a different club or meeting every
evening. If she sees a boy walking out of here in the morning the news,
misinterpreted, will be all over the village. So when Jeff drives out
make sure your head is down out of sight till he's round the corner.'
"After supper and leaving Jeff to watch TV the three of us went to my
bedroom. Mum took charge. 'Now Tommy, I know Lily has briefed you.'
Actually I hadn't, but that didn't mattter. 'Take off all your clothes
except for your underpants. Hands by your side.' So she pulled the
nightie over his head and used the cable ties to link each ankle to the
hem. 'There. Done!' she said. 'Now if these or anything else is cut,
torn, or broken in the morning you two will never see each other again.
You understand?' We both nodded agreement. 'If you need to pee during the
night there is a funnel and hose there in the bathroom. Stand in the
shower recess to do it, then flush it with the shower. Any emergencies
then come and wake Jeff and me up.'
"Tommy went to walk down the corridor to the bathroom intending to
inspect the arrangement. He nearly fell over, hobbled as he was by the
tight hem. We both laughed and he blushed. 'Lily,' my mum said, 'he looks
really pretty when he blushes. Especially in that nightie. If I just
pretend that it's one of your girl-friends sleeping over I'll feel much
happier.' I had to say, 'Oh Mummy, don't be cruel. You're making him so
embarassed.' And she agreed, 'Yes you're right. Sorry Tommy, no offense
meant. I'll leave you two together. Sleep well.' As she left the room I
called out, 'Night-night Mummy.'
"I remember feeling a bit shy, so I chose a fairly demure brushed cotton
nightie and turned out the light before getting undressed and putting it
on. I already had Tommy lying in the bed by then. When I got in beside
him it really was a thrill. I was also pleased that his arms were trapped
inside that satin nightie. It meant that I could kiss him without having
his hands where I didn't want them. I could tell he was excited as once I
brushed his tummy to find he had a raging erection. Anyway, eventually we
both managed to get to sleep.
"Of course we both overslept so my father refused to wait for Tommy but
shot off for his golf just as Tommy was shuffling into the breakfast
room, actually the kitchen.
"My mum took charge. Having used a proper electrician's tool to clip the
cable ties she said to him 'Now go and take that nightie off, drop it in
the laundry, and put this on'. She handed him a rather feminine dressing
gown. He was hoping to put his own clothes on, but not knowing where they
were he did as he was told. In fact I think he rather enjoyed the soft
clinging material of the gown.
"Breakfast was almost over when mum broke the news. "Children, we have a
small problem. The old lady next door is a terrible sticky-beak and
gossip, and is always peering out of her window. If she sees a boy
leaving here in the morning she will draw the wrong conclusion and we
will all be embarrassed by the ensuring gossip. Originally I had planned
for Jeff to drive Tommy home - he could have ducked down till we were out
of sight - but Jeff has taken the car. So what I propose is that we dress
Tommy as a girl and he can walk home. His house is only two blocks away,
that's five minutes max."
"Of course Tommy was very anti this idea. 'But why can't I stay here
until Mr Scott gets home?' My mum didn't really want him hanging round
all morning, so made up a white lie. 'That doesn't really work. Lily and
I were planning on taking the bus into town to do some shopping. Look,
you won't be seen as we will walk either side of you, and you can wear a
big sun bonnet. Just flouncing a skirt will be enough to fool old Mrs
Krieger. And I'll ring your mum so she knows what to expect.'
"So mum and I fitted him with a skirt and blouse, and a bra with big
falsies underneath. Then we looked at him and decided that to anybody
walking past them in the street he still looked too much like a boy. So
we had fun making him up with some blush and lipstick, and clipped on
some dangly earrings as well.
"He was allowed to wear his own underpants, but with the skirt wafting
across his legs, the pressure of the bra straps on his back, the pull of
the falsies, the taste of lipstick, the tingle of the clip-on earrings he
felt quite stimulated. As he explained to me later, he got such an
erection that it pushed through the fly of his underpants. The result was
a skirt draped over a very unladylike bulge.
"Mum noticed immediately. 'We can't have that big swelling there. It
totally ruins the cut of the dress.' So she marched him upstairs to her
bedroom. She told me to stay where I was, but of course I pussy-footed
upstairs as soon as they were out of sight. I heard mum say, 'Now lie
down on the bed on your back,' and peeking I saw her grab some stuff from
the en suite cubboard. She returned and pulled his skirt up and
underpants down. I'm sure he did not know what was going to happen and
the apprehension had deflated his cock somewhat, but when she started to
fondle it it soon sprang up again.
"I was enthralled and no longer hiding as mum had her back to me. Then
she turned and caught me looking. I might have said 'Mummy! What are you
doing?' 'I'm just getting rid of this unsightly bulge under his skirt.
And I wish you hadn't crept in on me like this. However, now that you are
here a short lesson on male anatomy wouldn't hurt. You have probably done
some feeling around, but I doubt if you have had a good look in daylight.
I was not fazed, in fact I was fascinated. After observing for a few
seconds I asked 'Mummy, can I have a turn now please?'
"As mum later explained, she thought, 'Well he is her boy-friend so I
guess that's a fair request.' So she replied, 'Yes dear. Now let's see if
you can start from the beginning. To make these things go down you do
this,' and she gave his erect cock several hard fillips. Tommy yelped
'Hey, that really hurt!' But it had had the required result as he quickly
deflated. I took mum's place on the edge of the bed and under her
direction used the soothing cold-cream on his hurt member, massaged his
balls gently, and kissed him sweetly. I found it odd and rather thrilling
to taste the lipstick he was wearing. Once he started to grow again, mum
handed me a small packet. 'Every young lady should know how to roll on a
condom. So here you are.' So with a bit of fiddling I opened the packet
and after one false start (it was upside down) I rolled it on.
"It was not long before Tommy, to his great relief, did indeed come. Mum
was quick to point out how with a condom the cleaning up was much
simpler. 'See! No sticky sheets or embarrassing stains on clothes.'
"He looked around for his underpants and was about to retrieve them when
mum winked at me and said 'Now just a minute. If you're going to pretend
to be a girl you don't want to be wearing those. Here, I think Lily can
find you something more suitable. So I went to my room and picked out a
pair of dark blue schoolgirlish cotton briefs with white frills. They
were fairly tight, which was just as well as they compressed his boy bits
to be less noticable. Later he admitted that putting them on felt nicer
than his rough underpants."
"Once we got him dressed again he really did look sweet. His legs weren't
especially hairy so from a distance you couldn't tell, but I did make a
mental note to get him to shave them one day. He was still reluctant to
go walking down the street in drag so I suggested we run. 'You just have
to run like a girl,' I told him. 'Kick your heels out to the sides and
wave your hands in small circles as if you were polishing a car.'
"And that's how we arrived at his home. Both red-faced, me from the
running, he from that and the embarrassment of greeting his mother and
sister looking like a girl."
Lily paused briefly. Her companions were absorbed in the story and all
wanted to find out how the affair played out. So Lily had to continue.
"Well Katie, that's his older sister, and his mum were both very
sympathetic. They didn't laugh or tease him, though they did laugh when
they heard how old Mrs Krieger had been fooled. Then we all sat down for
a cup of tea.
"Now I recalled how he got that bulge when my mum and I first got him
into a dress. So I told Katie and her mum, Mrs Sorenson, that I thought
that Tommy was really enjoying dressing up as a girl. Of course Tommy
blushed again, (he did look pretty when he blushed), and was very
unconvincing in his denials. Mrs Sorenson said, 'I've got things to do so
I'll leave you kids to play dressing up games. Call me if you need me.'
Which was really carte blanche to do what we liked with Tommy.
"First we shaved his legs and under his arms. Katie was for taping his
thing down with surgical sticking plaster but I pointed out that pulling
it off later would very painfully rip out his hairs. Instead we shaved
his pubic hair as well, and then taped his thing down. We left just the
tip peeping out low down between his legs.
"Katie produced a pair of false boobs. She admitted that she had only
worn them once as her mum ticked her off saying they looked gross and her
own boobs were quite nice as they were. Anyway, we stuck them onto Tommy
and then proceeded to dress him. That took some time as each item of
clothing provoked some debate and then had to be rummaged for. Eventually
we got him dressed in stockings, suspender belt, silk french knickers,
bra, a really tight half slip (Katie narrowed it on their sewing
machine), and a little black cocktail dress. After we had touched up his
makeup and added a wig he looked gorgeous.
"Once we had him in high heels taking tiny steps, all he could do in that
slip, we called in Katie's mum. 'Well,' she said, 'looking like that we
can't call him Tommy any more. He needs a girls name.' That's when I had
a brain-wave. 'If he's no longer a tom he must be a cat.' So that is how,
as a girl, he became Kat with a K. It also let him pass himself off as
his sister to those who did not know her well, or as a cousin to those
who did.
"So that weekend Tommy was Kat all day Saturday and Sunday. He even slept
in one of his sister's nighties. It also became the routine every weekend
till we finished school. Friday afternoon he got out of his school
uniform, dressed as Kat, and walked to my place. There we slept chastly
together and in the morning he would continue as Kat for the rest of the
weekend. We were not completely chaste; I would usually give him a hand
job with my arm up his tied-on nightie. Then one day I went to the
hardware and bought some identical cable ties and the right tool,
'sidecutters' they call them. That night I cut him free and we made out.
That's when I lost my cherry. We still used condoms, but as we were too
shy to buy them from a chemist he or I would get them from a dispenser in
a public loo.
"Life went on like that for several more weeks. Then one Friday evening
when I went to my stash of duplicate cable ties I found they were
missing. Instead was a packet of condoms. Oops! My mum knew, but she
never let on. I suspect she never told Dad but he probably guessed.
"Weekends became an exercise in dressing up Tommy. Once we ran out of
interesting clothes of our own we would hire outfits from the local fancy
dress hire shop. I remember once he was Alice in Wonderland, another time
an 18th century courtesan - all huge skirt and tight thin bodice. Tommy
was great. He would play along talk in falsetto and ham up the parts.
Caroline butted in here. "But what were you two thinking? What was
motivating you?
Lily hesitated a moment. "Partly it was a hangover from when we were
little girls playing with dolls. Now Katie and I had a life-sized doll we
could dress up. For me it was also the thrill of being a tease. Once he
was taped up, or rather taped down, of a Saturday morning the more sexy
clothes would get him really aroused without him being able to get
release. At least not till the next Friday night. I guess I just liked
being in control."
"Anyway, let me finish. Once our final exams were over and we were both
out of school for good, Tommy declared that he wanted to really look a
girl, permanently. That would mean a lot of expensive operations.
Amazingly his parents agreed - I guess they realised that his weekend
cross dressing was more than a passing fad - and being pretty well off
they paid for it all. So over the next twelve months Kat missed an awful
lot of lectures. How she passed at end-of-year I don't know. (By this
time I was thinking of Kat as 'her' now, Tommy and 'he' seemed so long
ago). Her operations included bone surgery to thin down her face and
forehead: Adam's apple shaving and vocal cord shortening; skin
transplants for no more beard, a boob job and stomach binding for a
narrow waist. The biggest change was the bone surgery to widen her
pelvis. That had the intended co-product of giving her a 'pocket' into
which she could hide her boy bits. So now, even stark naked, you could
not tell by looking that she had once been a boy. But if you got into bed
with her you could tell!
Lily drew breath. It had been a long story, nevertheless it had held her
audience. Eventually Sophie broke the silence. "Well, what now? Do you
still see... her, see Kat?"
Lily replied, "Of course. We are still the very best of friends." She
looked directly at Catherine. "Aren't we, Kat?"
Marisol
- 03.01.2023
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