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Tght Jeans
by Lauran Travis
I managed to wriggle into the jeans by lying down and pulling a lot. The
zip came up easily when I breathed in, but they were on, there was the belt
to fasten with its big buckle felling like a shield between my hips. I
pulled at the waistband a little to try and get it over my hips but the
crotch was already tight into the tops my legs. So a belt on my hips I could
cope with. But standing up the hem was under my heels, I thought to turn
them up and put on my trainers, but with the flair they would never stay up,
and the trainers were soaked as well as everything else. It was bad enough
borrowing the clothes, to return them dirty because I had been dragging them
on the floor would seem ungrateful.
'Are you decent' Julie asked, 'depends how you mean,' I replied.
She came into her room and saw me in her jeans. 'Very nice, tight looks
good' to which my response was 'do you have anything looser?' 'You being
that little bit bigger than me means everything will be tight, these are
loose on me, remember' I did remember and they kept on slipping down her, so
anything else would cut me in two.
'OK can I turn them up? I don't think I have anything that will keep them
up, but you might' she looked at the legs then at me, another surprise was
coming 'what size feet?' I furrowed my brow ' why' 'well you are right they
wont stay up, so slip these on and the heels will keep the hem of the floor'
she passed me her black ankle boots 'they should just about fit' I slipped
my feet in and pulled the zips up, they were not toe curling tight,, just
snug. 'Stand up' she took my hand and helped me to my feet, after a few
seconds I got my balance and looked down I could not see my feet the flairs
covering them and just touched the floor. 'That is perfect, just right' she
explained. I had a careful look and felt that they could pass as mine; the
block heel under the flair would not look too bad.
'Now do you want a jumper or a shirt?' 'Jumper I think, but I will borrow
what you give me, I don't want to stretch your good stuff' 'this has grown a
bit for me, but try it on' if the boots and flairs had me worried about
walking out of her place unnoticed the deep pink angora jumper would make it
no easier, it had ¾ sleeves and did not really meet the jeans in a male tuck
in way at all, just resting about belt height was the best I could manage.
Good job I had washed my belly button was not my first thought. But it did
fit. I commented on the bright colour which she dismissed because she liked
the colour and it had been one of her favourites, but gave me a denim jacket
to help me hide my pink, I thanked her too quickly, the jacket was not made
to fasten and was an inch shorter than the jumper.
Unfortunately I caught sight of myself in a mirror and blushed; I looked
very female, heels, tight hipsters, bare belly, pink fluffy jumper. I tried
to say this was not a good idea, I should just put my wet clothes on and go
home. She insisted I would get a chill doing that and after making sure I
could walk in her heels, told me I would be fine, but there were a few extra
things she wanted to do, that was unless I wanted to go home looking like a
male with no dress sense.
She pulled the ponytail out, then dried and brushed my hair out so it
swept across my face, and with plenty of gel it was going nowhere. Next was
sunglasses even though it was still cloudy, and lipstick nothing to bright
thankfully.
I was declared ready, I felt far from ready. We put my clothes into a
bag, and emptied my pockets into a shoulder bag, nice pink to match the
jumper she said. 'Do you want me to hold hands, so we stay close just in
case?' 'Until I get used to walking please' she smiled, gave me a very
affectionate kiss and led me out of the door.
Checking no one was around I followed, soon we were out into the town and
heading for the buses and the way home.
On the bus she started talking to me, I had avoided talking thinking my
voice would be too deep, but when she got a text asking who the new
girlfriend was, she showed it me and I just involuntarily said 'me?' 'Yes
sweetie do you fancy being a lessi?' More quietly I replied 'never thought
about it, thought you liked men' she was sliding a hand down my thigh, 'but
not all men are the same, and this one is very feminine' then she
reconsidered 'Perhaps you are female, but just have an extra bit here' her
hand now sliding up my leg, with a peck on the cheek she finished her
teasing.
Once of the bus, and I realised the next half mile would be the hardest,
people knew me around here, or so I thought. We walked as quickly as I could
in her heels, and fortunately only saw 2 people I knew, but I looked past
them and they said nothing. We had linked arms in a girlie sort of way, so
when I got nervous she squeezed my arm and told me to relax and reassured me
they had not even looked at me.
Half a mile seemed like 2 miles, at last I was routing through the pink
bag for my keys, just wanting to get in as quick as possible. Once inside I
threw my clothes at the washer, and slumped onto a chair declaring that to
be the hardest thing I had ever done. She came and cuddled me, telling me
how thrilling it had been to walk with me dressed as a 'sexy woman' (her
words) and how it had turned her on. Then got me to agree it was not
frightening, but there was a buzz about it, and that in some way I had
enjoyed the thrill.
It was as I was relaxing and about to say it was time to change when my
mum came in. 'hello Sara, no Dan with you?' and was about to introduce
herself to me, when she took a second and a third look at me, 'would you
like to explain?'
I started but Sara did most of the story telling, there was an occasional
'and you agreed?' to which I had to explain why I had taken certain actions,
like wearing high heels. At the end she asked how we felt, told me I looked
good, and somehow Sara told her what a buzz it had been.
She sat drinking a coffee we had made during the talk, then looked
straight at me, 'how's about I take you both out, and maybe I could feel
this buzz also' I was about to say 'mum this was really just a one off' when
Sara said 'that would be nice' and did that thing squeezing my hand to let
me know she wanted to do this. Mum looked at me 'Dan?' I just said 'oh call
me Danielle then'
Mum wanted to change out of her work clothes, then she and Sara said I
could not wear the shades at night so make up was required, then they looked
through the jewellery, a couple of rings, a watch, bracelet and a necklace.
Finished off with her best perfume.
She drove us to a pizza restaurant we had never been too before, and to
be honest had a really nice meal, we chatted about allsorts, not just the
gender issues. Even college, work, and her past experiences came up for
discussion which was very eye opening to a son who thought mum's were just
parents. The comment that stuck with me but at the time I tried to duck was
'how far would I go in bending the gender image'
Things went back to 'normal' until the weekend. Sara suggested I try on
some clothes she thought I would like, nothing too girly just androgynous. I
was fine with the idea remembering how soft the jumper had felt. And so
started a transition in my clothes. First I was wearing the soft jumpers,
then Sara came in with a pair of trousers that were fitted at the hips but
loose down the leg, and very soft. The next move was mine; I bought some
knickers, and would wear them under my usual jeans for college. Sara found
out and thought it wonderful, buying me some more. I also stopped tying my
hair back and took more care of it, so it became fuller and in my face,
which made me sweep it back, very girly I was told more than once, but I
continued.
Mum had gone quiet for a few weeks, then about the middle of term,
whatever was on mum's mind lifted, something about work she said, and she
once more took an interest in what I was doing, commenting on the panties
and nice tops I was wearing, then coming back to question I had forgotten
about, 'how far would I go?' meaning a dress. Then she noticed a film she
wanted to see and asked Sara and me if we would like to go with her, when I
said it was a chick flick, their reply was immediate 'well you know what
that means then, no boys' I agreed to wear my trousers and heels, if I could
borrow the satin top Sara had not worn for ages but was beautifully silky
and pastel pink, they both smiled at me in a knowing way and that night we
went out as three women again. The film was actually enjoyable, maybe I had
never bothered before, or it was the company or maybe the clothes had
changed me, but I joined in with mum and Sara as they discussed the merits
of the plot and the characters, particularly how nice the male lead had
been.
A week later was the anniversary of dad dying and we always went out, at
first to remember and be sad, later to have fun thinking how he would like
to have been with us, and dad liked the theatre, he enjoyed the whole thing.
He would like it most when it was a good play, and he and mum had got all
dressed up, eat out and make a full day of it. Mum this year wanted to go to
see a play, and said it would be a dress up occasion, Sara knew straight
away what she meant, 'how dressy?' 'How dressy can we get him?' 'Well he
does not do male dressy, his suit is tight and I am sure ties are lost in
his room' 'have to be 3 girls then' they announced. Next question was would
I wear a skirt, what is wrong with the soft trousers and a smart blouse this
time and maybe a dress next time if it feels right. Somewhere I was hanging
onto the idea that trousers were masculine no matter how they were cut. Mum
wore a smashing outfit, she looked really glamorous, Sara wore a dress for
the first time in ages and looked stunning, which made my trousers look very
common beside them, but I knew I had said I would wear a dress, and feeling
quite dull by them I knew one day I would. The play, that was fine, not the
best, but I was distracted weighing up the smartly dressed women, thinking
what a dress would feel like.
After we all agreed it had been a good night out, not sure how dad would
have accepted my clothes, but thought he would have been fine after the
shock. Sara accused me of looking at the smart men, and declared that if I
was eyeing up men then she would need to make sure I was eyeing her up, and
no amount of protest would stop her teasing me, I insisted I was looking at
the women. Then mum joined in and teased me about which style I liked the
most. I gave up in the end, saying they won and to just tell me what I
should be doing and when, which brought a laugh and a smile to their faces.
It is hard to say why I did what I did next. I had a study week, that
usually means I caught up with college work, had a rest, and would have
something prepared for a meal in the evening to save mum doing it after
work, which she usually does. Anyway why I do not know but after mum went to
work on the Monday I got up, usually I would slob around, but instead I
showered and dressed in tight jeans and a mohair top, blow dried my hair
then studied. Come the evening I had a meal ready and when mum came in she
thanked me for the meal, and opened a bottle of wine. Then over the meal
asked about my day, particularly why I was dressed girly and my hair loose,
which she said I had done really well. But then continued with an offer to
show me how to style it rather than just dry it.
So Tuesday I tried what I had she had taught me, styled my then lacquered
it. But mum when came home that evening with styling gel to try, we played
with that.
Wednesday, I invited Sara over; she came in a skirt, she said to please
me, and loved my gelled hair, and then suggested colouring it, which is just
what mum, had in mind as well. So after we had eaten I was given a temporary
dye, which meant instead of mid brown I had a mahogany coloured head of hair
with a great shine.
I still am not sure why but playing with my hair got us all into a really
good mood, chatting and discussing how each of us might restyle, mum fancied
a 2 layer light and dark colouring, the dark being hidden when still, Sara
had never had short hair, and for me I liked mine long and maybe blonde.
Thursday mum left out a Cosmo mag, which I saved till I had finished my
studies, then had a read, which lead to playing with make up I had in my
room from weeks ago. I thought I had done it very muted, just enhancing my
features, but mum's first reaction on coming home, was to stroke my cheek
and lift my fringe, taking in what I had done, then smile, 'nice' she said
'what is for tea'
Friday, I had to get plenty of studying done so I could work the weekend,
but did shower and pull on a bra etc, then while the meal was cooking
slipped to put on some lip-gloss and mascara. Not sure who I was doing it
for, mum or me, but she said I looked nice again, I was enjoyed taking care
in my appearance and being flattered.
As far as dressing, that weekend saw me scruffy as I worked both days,
but relaxing with Sara and mum on Sunday evening before we went out, mum
suggested that once the exams were over she would treat us all to a special
time, then winked, how special? Very special, but let me think about it some
more and I shall have it all sorted for the day after you finish.
So the exams came, I concentrated on them and the part time job, trying
not to think about what treat mum might have in mind, but expecting it to be
something we all would enjoy. Sara's exams finished a week before mine and
would be round at our house cooking for us when we got home, then when I
went to revise would chat with mum and giggle excitedly, all adding to the
anticipation, part excitement, part dread.
My last exam was on a Thursday, and I went out with my classmates for the
evening and had a farewell drink with them, plenty of what are you going to
do now chat, and mucking about as well. I did not know what I wanted to do,
or even what I was doing next; except for mum's special treat which I could
hardly talk about with straight friends.
Friday, I woke up late to find Sara in the house making herself some
lunch, and looking very pleased with herself. By mid afternoon I was
recovered and dressed in a bra and full girls outfit at her request. I had
styled my hair, done a quick make up and then was surprised to see mum come
home early. It was then I noticed she had a small suitcase and a hold all in
her room packed, all she wanted to do was change and freshen up and told me
to pack, which Sara was already doing.
We loaded our bags into the car and left for I knew not where. I drove
which kept my mind elsewhere, arriving at our London hotel about 7. Booked
in, then out for something to eat, when I felt we had stopped moving I asked
what we would be doing. This created a 'should we tell him, or leave him
guessing' conversation. In the end they looked at me and said it was best I
just follow them, go with the flow, but what was booked was a weekend
theatre break. And not to worry I would be asked to do nothing they were not
prepared to do themselves, and it was going to be fun.
The fun started in the morning, I had noticed parcels arriving over the
past weeks, now I found out what they were. But first Sara helped me shave
all over; telling me waxing and creams need time to heal. So with my downy
hair all gone mum produced a pair of false tits, which she said would look
real by the finish. And when she had glued and made up the edges I could not
see the join, next she said only mum's could do this not girlfriends. She
slide a tight tube over my penis then put the hair dryer on it which made
the tube shrink onto the penis, then she took the tails hanging from it and
pulled it behind me till my penis was up between my legs and looking
backwards, and stuck them down. We then all had an admiring session, was
told how good I looked in the nude, to which I had to agree.
The black trousers fitted better now and mum had bought a new bra to take
my new chest size. By now it was mid morning and we were off out for a
coffee, then we had an appointment. Which turned out to be a ladies salon.
All three of us booked in already for the work we each needed. This was
largely new to me and tried to see what the others were having done, but
would see them with their heads covered like mine so had no idea what was
happening, just that I was being treated the same as them.
My hair was washed, but from then everything was new but for reading
bottles I had no idea what the salon girls were doing. Mum and I ended up in
the hood dryers together, I tried to talk but she just took my hand and
smiled at me. Then nail technicians set about us, massaging my fingers first
which was very relaxing, then when I opened my eyes they were making the
nails longer. Several hours after going in we were stood in the reception
area staring at each other, mum had basically booked us in for the styles we
had discussed all those weeks ago, her bob was dark on top with blonde
underneath, Sara was really short, and I was blonde, centre parting with
everything flicked backwards. The other thing to realise was our nails,
mum's talons were burgundy which I knew would match the dress she had
brought with her, mine I was told were French tips and seemed ridiculously
long until I later compared them to mum's, who smiled at me, and said I
could have the same next time if I wanted.
We now had to shop I was told. They also told me it was to be my
introduction to fabrics and styles, I thought reading a few of their
magazines would help here, but we had 4 hours to get me sorted they said, so
first a dress for the theatre. I tried to protest that trousers can look
really classy and what is wrong with culottes, but they just told me to go
with the flow and enjoy. After what seemed like endless trips to changing
rooms, which thankfully were not communal, I was getting used to being in a
woman's environment and attracting no attention other than comments on how
nice the dress looked, not, there's a man in here call security. It was
decided a white dress, virginal they suggested, with a very full skirt,
loose cross over top and flared sleeves was chosen. Then we had to get the
underwear and shoes. Sara insisted I get stockings and a white fine lace
undies set. Then all we needed was white sandals, which had the highest
heels I had ever seen, but they both told me they looked great. Last we got
what I called a wide scarf but was told was a wrap, and assured would look
very elegant.
After a rest for a drink it was back to change for the evening and I was
really getting very excited by all the attention. Mum was sweet as she asked
how I had liked the day, I had to admit to loving it, Sara asked how I liked
the new look, getting used to it I smiled in response. Well mum said the
best is to come, the getting glammed up, then going out and strutting about
feeling great and being noticed is something I hope you enjoy. 'Like I am
not feeling noticed already, try being a boy dressed like this and you will
feel noticed'
Anyway mum assured me I would enjoy the next part. Sara went to her room
to change leaving me with mum. She said we should get ready together, so we
stripped and put on our clean underwear, which felt very strange seeing mum
naked, and quite strange to see she does have a good figure, not something
sons usually think. She showed me how to put on stockings, and then make up.
I had been thinning my brows already but she pulled more out to get a
thinner line, they grow back she assured me, how long I asked she shrugged.
Now for the dress it was hung up waiting and after the sensations of the
day, following the stockings and delicate pants, the feel of the dress
floating down my body made goose bumps appear everywhere along with a
tightening in my groin, which hurt a bit as the restriction was felt, not
for the first time I must add. As I fastened my shoes mum slipped on her
burgundy dress, I had seen it hanging but on it was stunning, strapless and
fitted at the bust then flowing around her legs. When I told she looked
great, she thanked me and said that was the point, and I looked brilliant
also. I just blushed.
Sara had been out all the time and I had not thought to ask what she was
going to wear. Mum rang her room to tell her we were ready, she was round in
a flash. I do not know who was the most shocked me or her, she just stared
at me then mum, 'Two stunning ladies, absolutely' I stared back she was in a
black suit shiny lapels, bow tie, flat hair and trying to speak with a deep
voice. I must have had a gormless look on my face, she came to me and kissed
my cheek, 'we decided that it would be fun to have a man around and I
fancied short hair, and why should you get all the fun of being a different
gender' mum just said the suit fitted well, picked up our clutch bags and
were ushered out by Sara.
I was in a sensory overload on reflection, I had never worn such high
heels, or stockings, or a dress, or been made up so well, every part of me
wanted to say this is different, some parts telling me this feels very nice.
The skirt swished around my legs as we walked to the foyer, then the cool
air hit my near bare skin as we stepped outside, and people were looking at
us as we walked out. This was a real adrenalin buzz, what if we are caught,
how embarrassing. We got into a cab, I relaxed slightly, then we were in the
west end, Sara lead us to a bar for a strong drink, mum checked she had the
tickets, and we realised we had no idea what she had brought us to see.
Ballet she told us, then explained the audience dress up more for ballet,
and the story she felt appropriate, the ugly duckling theme. I just blushed
and looked at my empty G & T.
Mum is very good at the strutting, so I tried to copy her confidence,
Sara just tried to be manly but probably only doing as well as my girly
impression. But I knew I was having more fun than both of them.
Ballet is surprisingly entertaining, and the women in the audience were
mostly well dressed which made me feel as if I nearly fitted in, except for
the minor difference of what I keep in my knickers.
Having hardly eaten all day, we made our way to a nice looking restaurant
full of people like us who had been to a show. Mum was in her element, and
encouraging me to enjoy the atmosphere, and the whole female experience. I
did try but doubted I was anywhere near as confident as my mother. Sara just
kept up the man role for all she was worth, and not doing to badly, possibly
better than me.
It was early morning by the time the cab had dropped us back at the
hotel, and we had been to the bar for one last drink. Somewhere in the
evening we had talked about our rooms, mum booked 3 singles, but hers and
Sara's were twins, mine was a double. So after we watched mum close her
door, we just looked at each other, 'yours or mine' we said together. The
double was unanimous, but Sara said she had one last treat, slipped into her
room, and then came to mine with a bag.
I hardly had the door shut before she was kissing me, we broke for air,
'undress, then look in bag'. This took time, but as I undressed Sara was
getting out of her suit. I came out of the en suite wearing her gift, a red
silk nightie, to see her wearing just boxers and a t-shirt. We had never
done anything like this before, and climbed into bed to find out how things
were when you get really intimate.
Next morning we woke feeling unsure of what we had done the night before.
My penis was still sore from it's straining against the sheath, but as I
moved the nightie rode over my skin and reminded me of all the nice
sensations.
'So what are we supposed to be doing today?' I asked my horizontal
partner, who happened to be looking at me. 'Well a coffee to start if you
are offering' and without thinking I got up switched the kettle on. She
watched me 'you still look great you know, even first thing with messed up
hair and make up you should have cleaned off, you are still a very
attractive woman' 'Give over' I told her 'you know what I am really' then
with a grin told me 'Even knowing that, you are still hotter than I ever can
be' I was about to protest when mum rang on the hotel phone. She wanted some
breakfast and were we joining her to discuss what she had planned.
After our breakfast discussion, we heard more of mum's plan that we would
agree too, it was decided that Sara was going to be Sam until we went home,
and if I wanted I could be Danielle too, as if I had any choice without my
Dan clothes.
The choice we did have was this, we could stay in London. Go to the
coast. Or go home. Whichever we choose we would stay as Danielle and Sam
until we got back to our house. Mum then looked at us both, 'if you shared a
room it would make the money go further', we acted all innocent, but she
smiled and winked, ' I know you can't get up to much at present, what with
Danielle looking so neat in the panty area, and I would be fool to think you
went straight to bed when you left me last night'. I blushed and dared not
make eye contact, 'thought so' she said, 'wasn't sure, but I am now' she
paused, 'So where?' Sara made the decision, she wanted to have a few days in
London, and later told me most hotels have twin rooms and we had a double
which was unlikely to happen at another hotel.
We went our separate ways in the daytime, but in the evenings mum
insisted we dressed smart for dinner. This meant we wore pretty androgynous
clothes for sight seeing, but come the night I had to wear a skirt,
surprisingly I never complained, even spending time buying a new one that
mum would approve of, but with Sara's encouragement I bought a short kilt
that felt like I was showing the world everything including my knickers, but
Sara insisted I wore daytime, which had the effect of sending her into full
time male mode, as I teetered about on the heels trying not to show my
pants, after three days I had to admit it was great fun being Danielle. The
daytime with Sara was fun, the evenings with mum were great, and especially
all the effort that went into getting ready. And the nights were full of
surprises and discovery, we even managed to make each other come, though I
did not fancy a second time as I was so sore with my penis so securely tied
up, but at the time it was brilliant.
The Wednesday morning I went to breakfast in the kilt, mum quietly asked
if I intended going out in it, 'already have' I answered, 'fulltime skirts
then?' 'For today, yes' She changed the subject 'I was thinking of heading
for home today, I had a call from a friend late last night, and I think we
have done enough here, what do you say?' we looked at each other, mum wanted
to go home for her friend, so told her what a great time we had had, but we
should head back to normality. To which she asked 'and what is that now?' We
looked at each other for a few moments, then I raised the subject of what to
wear, and maybe the kilt was not quite right for going home in. Sara had to
ask if the skirt was out, did that mean the hair, nails and make up were out
as well. I gave mum the choice, if she wanted I would go and clean up, wash
my hair and do something with the nails. I was trying to say I like this,
but it is up to you from now on, what about the neighbours?
Somehow she made it sound like a compromise when she suggested trousers
would be better for travelling rather than a short skirt. Sara squeezed my
thigh, 'better pack and get ready then'
For the next few days I went back to a fairly androgynous style, except
my hair at the front was to short to go in a ponytail, so I had a big fringe
and long wispy bits at the sides. Also the nails were too nice to remove, I
also had a chest that was inappropriate for a man, but a baggy top possibly
hid them. Mum was helping her friend with a crisis, so I spent my time with
Sara or keeping house for mum, and cooking for her when she came home.
The next week was a turning point, I had two months off till the results
came out and mum had wanted me to get some work, but now I was rather hard
to employ given the way I looked, but she suggested there would be openings
in the gay bars, and she had done her research. So armed with a list of
bars, and dressed in heels, tight trousers, ¾ top, not much make up and a
baggy jacket, I set off in search of a job.
Neither of us knew there were different sorts of gay bar, but I quickly
learnt. Most wanted butch men or camp boys, I did not fit, but one was
interested. The Nine Bob Note had a restaurant and needed staff, but there
was a uniform of sorts. I agreed to a week's trial starting the next day,
and had to arrive early to change, and was to bring some black heels. I
thought nothing of it except mum would be pleased, and she was.
Next morning I found some money with a note saying 'for the shoes, get a
nice neat pair' PS 'you can pay me back' I had never really shopped alone
before but thought I could just walk past a few windows, see what I like
then go in and ask for my size. I did see what I liked, but when I went in
and asked, the sale girl somehow had me sitting and trying on a pair, then
another, and another. In the end she was right, I would have bought the
wrong size, and after finding out where I was going knew what they would
want. Black, patent, stilettos, it was less than an hour before I realised
she was right.
When I arrived at the Nine Bob Note I was taken to a locker room by a
nice person that I thought was a girl, who explained the uniform and what
the entailed. First the clothes, she showed me a dress asked if I would be
happy in one, I said I had worn dresses before, when she said how short, I
described the kilt, so I should be OK with this. She pulled a blue dress off
a rail, and told me it should fit. Well to shorten the tale I was soon
wearing it, the bodice was tight when the laces were pulled in, with puffy
little sleeves of the shoulder, and the skirt was short but with the net
underskirt it seemed shorter, the stockings I was given were hardly covered
when I moved, then with my heels on I knew why they had been suggested.
The work was easy, two other girls? Dressed the same just different
colours worked with me, I was a waitress dressed as a fantasy maid and the
men loved it. Dee and Jen, the other two girls gave me tips on wandering
hands and getting tips, best summed up as let them see but no touching. By
close that night my feet were worn out when I flopped in the locker room, I
sat as Dee quickly cleaned herself up and changed into a smart boy, I was
shocked, are we all the same, I asked, they smiled at me 'of course we are,
why do you think you got a job, the kitchen staff are all men, the boss,
Sheila is a woman, and all the bar staff and us are the same, don't knows'
it took a bit to take in, I was sure there were at least some women here.
Sheila then walked in with the tips, I had money in my hand, a bit shell
shocked, but would be back the next evening.
I got home late and found mum still up wanting to know how things had
gone. I described it as a waiting on job, not going into detail about the
'uniform' and told her how much I should be making, and offered to help with
my contribution to the housekeeping. She seemed pleased and pointed out we
would see little of each other as our jobs were different hours.
I know she wanted me to enjoy the job, and I know she enjoys me dressing
as I do, otherwise why would she have taken me out so many times. But I was
not sure she would like the outfit I was wearing at work. I did not realise
it but would find out soon.
Sara rang and wanted to know everything as well, so gave her the edited
version I had given mum, and said I would see her for lunch.
The week passed quickly, mid afternoon I was out in my androgynous look,
change at work, and get to know the others better, wait on tables, change
back, and go home.
This was my first real job and I enjoyed the money, as well as the work,
and in a way the clothes with the attention they brought. Men and some women
were definitely not there for the food, we were floorshow, a bit like an
offbeat hooters in the states.
As predicted I did not see much of mum, and Sara only for lunch twice,
but I was off on Sunday and we could catch up then, but things would need
some explaining by then. On Friday evening I was doing my usual thing
serving the customers, learning to flirt and get more tips, when mum and
Sara came in unnoticed by me. They got a table in a corner and did not make
themselves known until it went quiet. How considerate! They had seen me
flirting with loads of people, had seen the outfit I had forgotten to tell
them about, there was so much I wish they had not seen. It was Sara who came
up to me, approaching from behind she said 'nice legs' and I froze. Her
voice brought me down very quickly, and my mind went into shock thinking how
she would take this, why was she there, did I have nice legs?
I joined them later at their table with my drink; they did indeed have
some questions, and some comments. They liked the dress, I did have nice
legs, who are the others, I seem to get on well with the men, and did I like
the attention they made of me. I wanted to know why they had come, what they
thought of the place, should I be doing this, was I gay, did I really have
nice legs?
I had arranged to go out that night with the staff, so I promised not to
be late and would see them later. The 'girls' changed out of their costumes
and into their street clothes, I had jeans and a jumper, they had hot little
dresses. 4 of us apparently were on the pull, I was not asked it was assumed
I was apart of it. So we went too a couple of late bars, they said to get in
the mood, then to a club. I was trying to just watch what was happening, and
keep in the group, but the group one by one disappeared, till there was me
stood next to Dee who was engrossed in a man. I was surprised when a voice
asked if I would like drink, he looked at my empty glass, I must have nodded
agreement as he returned with strong vodka. Next thing I am dancing with
him, and then when he touches I do not recoil. Another drink, another dance
– closer – and I feel his hard on, then his lips, again I do not recoil.
Thoughts are going through my vodkaed mind about whether I should be doing
this, should I enjoy it, what would Sara say. Then his lips touched mine and
I responded. I have no idea how long we kissed, but soon enough Dee was
touching me asking if I would go to the ladies with her. There she told me
to touch up the lipstick, and gave me a condom. 'Be sure and safe' was all
she said on the subject, was it so obvious it was my first time. It was also
getting late and we were doing lunches, as it was Saturday next day, her
advice was to get his number and save it for another day, as she was going
to do.
I crept into the dark house, and fell asleep with all sorts of things
whizzing round my head. It seemed like I had only just gone off, when the
alarm woke me. I was not sure what to say to mum, so just dressed then
quickly left the house, with time short it was not a good time for the talk
we would end up having. Sunday I would have to face her.
Work was fine, Dee was really friendly, wanting to know how my head was,
did I get his number, which way do I swing. To which I answered, not too
bad, yes, not sure. She then kissed me and told me I was definitely going to
be fun, not sure what she meant and with so many options unexplored I knew
Dee might show me some new things, and then with a stroke of my stocking
top, she said 'time for work'
The Sunday talk was unpredictable, by me anyway. Sara had apparently been
around the evening before, she was still there in the morning, and I guess
discussing me. So I had to tell them how I felt about the job, they called
me a sex object, a tart, then told me I looked great, that I should show my
legs more often, which had me confused. Then we got to sexuality, I realised
mum and Sara were sitting together, and that they were smiling and giving
each other looks that I later recognised as virtual hand holding, but I was
into trying to describe how it felt to be attractive to men and possibly
attracted by men, when Sara reminded me how I liked her as a man. None of
this was helping, and said I was going out for a while to think.
I rang Dee to ask if we could meet, of course come round, was the simple
reply. I put on my kilt, and silkiest blouse leaving lots of buttons undone,
I felt wanton and wanted to see were I would go. Leaving the house with a
coat covering my outfit, I took it off at Dee's who just welcomed me with a
hug and a kiss. 'So what do you want to know?' she asked, I had a lot of
whys, and a few how's. Dee assured me the why is never answered, the how can
be easier. Then as we talked she/he got closer, there had been plenty of
touching already, but then Dee undid the last few buttons and asked ' would
you like to see how I can make you smile?' 'Meaning' I asked. She just slid
a hand round my neck and pulled me to her. She was soon out of her trousers,
and unlike me had nothing holding her male parts back, I am not sure how we
did it but I sucked her, she licked me. And I left with a smile.
I got in still smiling, to find mum in a good mood and dressed in her
wrap, and when Sara appeared to help making the meal, she mum kept touching
her in an affectionate way. I only said 'mum' but the tone was odd and mum
just turned round to Sara then told me to sit down. While I have been doing
some exploring, the outfit I wore had not gone unnoticed earlier, they too
had been doing some exploring, and seeing as how I was off seeing what men
were like they had had a look at what women were like, and initial findings
were good, they liked it. I was shocked, but I was put in my place as they
had guessed most of what I had done over the last days, then they told me
how the visit to the restaurant had been the start, but they chatted about
me and other things latter on the Friday night with a drink at home, and
then ended up kissing. 'Oh' was about all I could think to say, but thought
I really must get that phone number out, and go shopping, I need a new
dress, my nails are needing help, my hair needs a wash, must pick up some
condoms from the bar, KY jelly. So much to think about now I was being
allowed try with the quiet help of my mum. I came back to earth as mum read
my thoughts, ' We could go shopping when you are free, get you something to
go out with Dee in, if you like'
The next few days were a turmoil, I was confused about who I was, why I
was dressing so feminine, was I gay, where did Sara fit in my life after she
had lead me into this whole new world. It was time for a heart to heart with
Sara, she thought we should clear up a few things as well, and said she
would see me when I got up next day.
She was always persuasive, just look at how I was first persuaded to wear
her clothes, and I agreed somehow that we should stop seeing each other as a
couple, and consider ourselves as sisters. It had been over a week since we
had been intimate, what with one thing and another I was just too busy, so
maybe we should be friends. We sat back and reflected on the new situation,
I could see myself as free to go out with Dee and not feel unfaithful, Sara
I hoped would be the sort of friend/sister I could confide in but that
needed time I guessed. In the meantime I told her she was welcome to come
around any time, apparently mum had already told her that, and they were in
fact off out that evening to the pictures, just the two of them. As friends
I asked, very good friends she replied, after the weekend revelations I took
that to mean more.
So come my next day off, mum insisted on taking me shopping after she
finished work. We meet, had a quick meal then hit the shops. 'Still want
trousers?' she asked, 'not sure, what do you think' as I tried to duck the
question, and find out how far she was prepared to let me go before she
called me a tart or bimbo. 'Well we know you have great legs, shame to hide
them!' oh I thought how short could I go. I soon found out as mum pulled out
a party dress, which barely covered the panties, with gloss tights, and
matching shoes 'A stunner', she remarked. I tried looking at trousers for
old times sake, but we did not have much time and had to make a choice. I
went home with a mini dress that really was a big pink satin vest that had a
large belt sitting on the hips, glossy tan tights and 4" pink sandals. 'Now
all you need is to arrange a night out and show it off' I was relieved but
at the same time shocked that my mum actually wanted me to go out dressed
like this.
I saw Dee the next day and told her about the dress, she immediately told
me we were going out after work the next day. So next day I turn up for
work, with an extra bag of clothes. Work dragged, but soon enough we were
changing. Dee put on plenty of wows, and plenty of touching, 'I would love
to have you all for myself, but I think you should experience the effect you
will have.' She added some bangles and declared us ready, even if I did not
feel it, I felt naked, nude knickers and a skimpy dress did not seem
suitable protection against the elements, but Dee was in a similar state and
she did have hold of my hand and was dragging me through the door.
I never bought a drink, even refused them, I enjoyed the attention, I
could allow hands to wander unlike work, and enjoy the buzz. One man was
really nice, we danced and chatted and drank, Dee was off with his friend
enjoying himself, so I some how found myself once again kissing a man and
not running away shrieking. It was nice. When his hand got under the hem of
the dress I stopped him and told him I might have a surprise hidden there,
he just reassured me by telling they knew Dee and about her, so he hoped I
was just like her, when I said yes, his hand just slid to the top of my
legs, touched my straining penis, I felt a buzz through my body, and he just
smiled, ' that sort of surprise I like'.
Ralph lived not far away, so invited us all round for 'coffee' the thrill
of a strong arm holding my waist as I teetered by his side, he gave me his
jacket as he thought I would be cold, my mind was not registering such
things until later. This was brilliant.
Once inside Dee got me to one side as the men made some drinks, 'you can
say no' she insisted, 'well make sure you are safe then', I smiled and
showed her a packet. 'Right in that case, you take Ralphy to his bedroom,
and leave me and my man here, OK' I hugged her, and the drinks arrived,
pretty strong gin with less tonic, I did as I was told and whispered in his
ear that I would like to see his bedroom. And he did. Then showed me a few
things that had not been on display. Soon the panties were off along with
his trousers, and we were enjoying making him hard. Then I heard Dee making
orgasm noises, and I rolled on my back and told him he had to do that to me.
So covered and KYed he set about me, I came draped over the footboard of the
bed with him stood behind me, and me biting his duvet.
Once spent he went to pour another drink, Dee sneaked in and found my
still as he left me, to exhausted to move. She pulled my face to hers,
'happy?' I nodded. 'Time to go then, slip this in' handing me a tampon 'and
pull your pants on, I have rung for a taxi'
We left them sitting on the couch looking as knackered as we felt, and
promised to do it again soon. The drive home was quiet, but holding hands
seemed so right, we kissed as we parted. What a top night I thought as I
crept in, I nearly did not notice Sara's coat and the two of everything,
Sara had not gone home, how odd I thought.
Next morning I was woken by the shower, I had not washed before bed and
knew I looked a mess, and then my arse reminded me it had been stretched. I
needed to pee so had to get up. Sara caught me on the landing, 'that must
have been a good night looking at the state of you sister, hope he was worth
it?' 'I just need the toilet, please' but the way I walked must have given
good clues as to what happened the night before.
Eventually I was ready to face my mum, she was sat drinking a coffee and
offered to make me one, which I accepted. Then facing one another over the
kitchen table she asked 'was the dress a success?' 'Oh yes it went down
well' 'thought it would,. You were back late, was it good?' where was she
leading with this, and what was Sara doing here. Hoping to avoid the
question I asked about Sara. This got me confused as she told me how they
were growing closer, and if I was going to experiment then why shouldn't
they, but my mind vaguely reminded me this is your mum and ex girlfriend how
can that be right, mum finished with a direct question 'so is it as sore as
it looks?' 'What do you think?' 'What I was thinking was, you never had sex
as a man, but now a man has had you. How does that feel?' I was trying to
organise my thoughts when she filled the silence. 'I am fine with whatever
you do, just be careful, and enjoy it. If you don't then stop. Understood?'
'I think so, and you do not mind me pretending to be a girl?' 'How can I, I
encouraged you, and I like you this way' 'and Sara?' I asked 'that is
something we are enjoying, and if that stops, then we move on.'
Over the next month, Sara moved in fulltime and did not use the spare
room that often from what I could make out. She had rarely worn skirts, but
she was always in trousers, and bloke style tops, then she got a job at a
builder's merchant, and would come home filthy. I guessed she was doing the
male thing to balance me, but then maybe she just liked it. I meantime had
got more girly. Mum had suggested when I had my nails first done I could
have longer ones later and now was later. I also got my ears pierced and
promised to have my navel done. And while getting my roots done had my hair
streaked.
Dee became a firm friend and helped me explore all sorts of new things.
She taught me the art of caressing, and could make me cum several times.
Other times insisting I give her all the attention. We dated some men we
meet at the bars, with varying success, but when I bumped into Ralph on
evening I felt myself getting hard just thinking about him, so much so that
I made sure he took me to his flat to see if he was as good as my memory
insisted he was, he was, but this time instead of a taxi, he wrapped me in a
duvet and made me coffee in the morning. He wanted to run me home, but
instead I persuaded him to make love again, and then run me to work. He just
smiled cleared the cups off then laid me over the kitchen table.
And so my future was sealed, I became sex mad, Ralph never refused, and
Dee was always there if I needed a change. Sara and mum seemed happy in each
other, becoming a public couple, which raised a few eyebrows, which was
nothing compared to the gossip I must have caused. Goodness knows what
people must have thought when we were all out, and we meet someone we knew.
It gave them something to talk about anyway.
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