The Waitress - Week 1 free porn video
It all seemed so innocent at first....
She was the one with the job, so I stayed at home and did the
housework. I was quite proficient at cooking and she asked me if I
would mind cooking for a few of her women friends - there would be four
of them including herself. I agreed and the meal was arranged for the
following weekend.
SUNDAY MORNING
As I returned to the bedroom after my shower, I wore my bath towel
around my waist as usual. She watched me from the bed and said, "You
know, that towel looks like a long skirt. It looks very elegant on you
as you are so slim. I might see if I can find a long skirt to fit you -
you could wear it on Friday evening and make my lady friends feel more
at home. Would you mind, dear?" She spoke sweetly, but I knew she could
be very determined. Sometimes it was better to go along with her ideas.
And anyway, I couldn't see any harm in looking elegant to please her
and her friends, so I said it would be OK. She was soon up and checking
my measurements - waist, hips, inside leg - before letting me put on
the rest of my clothes and go downstairs to do my chores.
MONDAY EVENING
She arrived back at the house with several shopping bags. "Well, I
think that's been a successful visit to the mall," she said. "How long
before the meal is ready?" I replied that I had just put the casserole
in the oven and it would take about an hour. "Right," she said, "I want
this skirt to look really elegant, so it will be best if you shave your
legs. The material needs to slide easily against your skin. So go and
have a quick shower and shave yourself. Then you can try the skirt on."
Although shaving my legs seemed to me to be an unnecessary precaution,
I knew better than to start an argument.
In the shower I shaved my legs, then my bottom, and then thinking I
might as well go all the way I shaved off my pubic hair too. I walked
to the bedroom with my towel on as usual. She was waiting for me and
nodded approvingly at my hairless lower body. "Very smooth," she
remarked. "Now to help your skirt slide easily against your body I
bought a waist slip to wear under it. Oh, and also some silky knickers.
Finish drying yourself and slip them on." The pink knickers felt
deliciously cool and soft on my hairless skin and she noticed my cock
stiffen slightly. "You like those, don't you dear?" she giggled. I
stepped into the black waist slip and pulled it up to my waist. The
carefully stepped into the long black skirt, taking care to avoid
catching my slip in the zipper of the skirt. "Breathe in," she said,
then fastened the skirt at the back and closed the zip.
Stepping back, she looked at the effect. "Hmm, I thought it might be a
little long," she said, "so I got something to make you a little
taller. Sit on the bed for a moment. She slipped pop socks on my feet
and then helped me on with some black shoes. She helped me stand up on
what seemed quite high heels. "They're only one and a half inches high,
but they make all the difference. Your skirt is now the perfect length!
Now slip this blouse on and let's have supper." She gave me a black
blouse, which I struggled with a little because the buttons were on the
opposite side from what I was used to. "Don't worry, you'll soon get
the hang of them," she said.
I walked downstairs very carefully. Not only was I wearing heels, but
also the long skirt restricted my movements. But I couldn't help
noticing the way the layers of underwear slid against each other and
against my skin. Wearing heels made my bottom feel larger and move more
as I walked, so that the cheeks of my bum were caressed by my silky
knickers. My knickers also gently supported my cock and balls. I
realised that I liked wearing them very much!
I found myself moving more elegantly as I served supper, and was
careful to use my napkin to protect my skirt from any splashes - I
hadn't usually bothered with a napkin before. After supper she watched
me clearing the table. "I think that outfit really suits you," she
said. "Does it feel good?" I nodded, not wanting to say just how
stimulating it really felt. "I think you should wear it all week. I can
see that you still need to get used to walking in those heels and
taking dainty steps when wearing a skirt. I got you a few changes of
underwear and blouses."
At bedtime, she showed me how to hang up the skirt to avoid creases.
Then as I was taking off my other things she said, "You can leave your
knickers on if you like. I can see you enjoy wearing them. Your little
dickie is already semi-hard." Once in bed she fondled my balls in my
silky knickers until my cock was harder than it had been for months.
Then she pulled my knickers down and straddled me, taking full control,
partly with the rhythm but also by the grip of her cunt muscles, until
finally I not just spurted, but positively gushed inside her. When she
had finished milking my cock, and it had started to shrink, she moved
up to straddle my face so that I could lick out her juices mingled with
my own cum. When she was satisfied, I could at last get my breath back,
pull my comforting knickers up round my aching cock, and relax like a
baby in her warm embrace.
TUESDAY
I was up first as usual and put my knickers in the washing basket. In
the shower I found that my shower gel had disappeared, so I had to use
the one with the more feminine fragrance. Returning to the bedroom I
reached out a clean pair of knickers from my drawer, noticing that not
only were there now a large number of pairs of silky feminine knickers,
but that none of my male underpants seemed to be there any more. I put
on pop socks before stepping into slip and skirt, then put on my blouse
and stepped into my shoes. Once again I was aware of the change to the
shape of my body made by these quite modest heels, and the resulting
increased awareness of the feel of my silky knickers on my bottom and
genitals.
During the day, I found that while the long skirt might be superb in
terms of elegance, it was rather restricting with regard to housework
activities. I mentioned this over supper. "Well, I did think this might
be the case, so I bought you a shorter skirt to wear round the house,"
was the reply. "Come upstairs and we'll see if it fits." At her
instruction I removed my long skirt and slip. She held up the new skirt
to my waist. It was made from quite a light fabric and was pleated to
allow plenty of movement. It came to just below the knee. "I think
you'll find this more practical for housework," she said, "but it will
look a bit silly with pop socks. So I got you some full length
stockings. But you'll need to wear a suspender-belt to hold them up."
She helped me fasten the suspender-belt around my waist and told me to
thread the suspenders down inside my knickers, which I did. I took off
the pop socks and she showed me how to gather the tan stockings in my
hands and carefully deploy them onto my legs, finally fastening the
shiny stocking-tops to the suspenders. This activity resulted in my
cock stiffening into semi-erectness, a fact which (to judge by her
expression) did not escape her notice. "Just slip off your blouse for
the moment. The suspender-belt was part of a set and I had to buy the
bra as well, so you might as well put it on. I got the smallest cup
size available."
As it was a minimum cup size, the bra was already slightly padded, but
not enough to give me a noticeable bust (at least that's how it seemed
to me). But the padding made it comfortable to wear without the need to
insert any other material in the cups. I put my blouse back on, put on
my pleated skirt, and stepped into my shoes. I became suddenly aware
that for the first time I was really dressed entirely in girly clothes.
Not just knickers and a skirt, but now bra and stockings too. And
instead of a long skirt that clung to my legs, I now had a floaty
pleated skirt that almost felt as if it wasn't there.
We ate supper and then watched television. I don't remember what
programmes were on, but I do remember her hand reaching up my skirt to
fondle my nylon-clad thighs. There followed another night where I was
surprised by the power of my erection, but again she was on top and
completely in control. Once again I had to lick the juices out of her
cunt before I could pull my comforting knickers up over my aching cock
and relax.
WEDNESDAY
Before she went out she showed me a pair of flat-heeled Mary Jane shoes
and also a pair of black trousers. "If you need to go shopping, you can
wear these," she said, "but you can wear all your underwear like you
had on yesterday". I understood it was more than just a suggestion. But
there again, it had been a long time since we'd had such great sex
(indeed any sort of sex on more than an occasional basis), so I knew
that I would be wearing what she said. After she'd gone to work I found
she had already started a shopping list:
1 x Maybelline Royal Red lipstick
1 pack x Tampax Pearl Regular
1 x Calvin Klein "Seductive Comfort" T-Shirt Bra size 36B
She had also specified at which stores I should purchase each item.
I didn't know whether all these items were meant for me to use, or
whether it was just a challenge for me to go out and buy them. But
anyway, I added the other items we needed to the list and went back
upstairs to change. The trousers were stretchy and tight-fitting above
the knee. The knickers she had chosen for me this morning had frills
around the leg-holes, so there was a definite Visible Panty Line. Even
without an erection, the trousers showed off the bulge of my genitals
and the outlines of my suspenders were also apparent. The legs were
slightly flared, so definitely rather girly, and I realised that unless
I stood absolutely still they would not conceal that I was wearing Mary
Janes over nylons. There were no pockets to put money in. Nevertheless,
I knew that my coat would cover the upper thigh area and decided that
the risk of people recognising my footwear for what it was would be
either unlikely or stimulating.
But when I got to the front porch, my coat was nowhere to be seen.
There was a pink, zip-front jacket hanging up, with a note on the hook
saying "Wear This!" Realising that I could not escape the inevitable, I
put it on and zipped it up. It only came down to my waist, where it
fitted closely. It was a looser fit around my chest, which somehow gave
the impression that I had a bust. And of course it did nothing to
conceal how my trousers fitted closely around what was underneath them!
There was a purse on the hook with it, and as there was no other option
I had to carry this with my money and credit cards in.
I did manage to purchase all the items on the shopping list, although I
did have to endure a few comments: "This colour makes a statement,
doesn't it?" (lipstick); "I haven't tried these, are they good?"
(Tampax Pearl); "Keep the receipt in case it doesn't fit you, sir"
(bra). I noticed that the girl at the supermarket where I bought the
regular items had a good look at the way my trousers fitted (and
presumably recognised that they were women's trousers), but as she
handed me my change she merely remarked, "That pink jacket suits you!"
I got back home, aware that a number of women had recognised that I was
out in public, dressed in clothes designed to reveal the fact that I
was a sissy. I reflected that they probably realised that I was under
the control of a strong woman (rather than being just a sad loner), and
this made them feel empowered to make their remarks. With a feeling of
satisfaction that I had empowered several women I changed back into my
skirt and heels. While hanging up my (women's) trousers, I discovered
that they were now the only trousers in the wardrobe. A tingle ran up
my spine.
That evening she trained me how to curtsey. I'm not sure that this was
the traditional way of doing it, but I had to lift the front of my
pleated skirt to about mid-thigh, then bend my knees while keeping my
hands a constant height from the floor. In other words, having
partially lifted my skirt I then had to bob down so that my stocking-
tops and the front of my knickers were revealed below the hem of my
skirt. She made me do this dozens of times before she was satisfied,
but eventually she was satisfied enough to snog me on the settee, with
her hand up my skirt, stroking the bare flesh above my stocking-tops,
then fondling my dick through my knickers. I realised that this was the
essence of girliness - a skirt offers no resistance to one's partner's
hand exploring one's underwear, and one can part one's knees to
demonstrate one's compliance. I also realised first hand how erotic it
is to feel fingers stroking the bare flesh between stocking-tops and
knickers. I knew I would never wear pantyhose.
After a day in which I had not only realised my true sissiness for
myself but had been made to reveal the same to several women, my cock
seemed more eager than ever to pleasure my wife/mistress. And after I
had sucked and licked our juices from her cunt she reached under the
pillow and presented me with a short silky nightie, just reaching down
to my waist so as not to conceal my knickers. She, of course, slept in
the nude.
THURSDAY
She showed no signs of going to work at the usual time. "I'm taking the
morning off and we have an appointment at the beauty salon. Make sure
you have a close shave. Wear your new bra - it will look more natural
to have a bust in a beauty salon, won't it? Probably you'll want to
wear trousers with stockings and Mary Janes." I took this last comment
as an instruction, but also didn't want to go there in a skirt, which
was the only other possibility.
As it was early there weren't many customers at the salon, so I'm not
sure how many realised I was male. My hair was styled into a sort of
page-boy look - somewhere between feminine and effeminate, but somehow
definitely subservient. My nails received a lot of attention and were
then painted red. My eyebrows were severely plucked and minimalist
make-up applied. As we returned home I felt quite feminine except that
I was very conscious that the tightness of my girly trousers would
reveal my maleness to any who looked. And with my new haircut I was
conscious of more male eyes looking in my direction. I wished now I'd
had the confidence to wear a skirt.
I spent the afternoon planning the meal for Friday evening, not just
the food, but how to decorate the table, etc. This was an aspect I'd
never really considered before. I made my shopping list for the next
day, and then prepared our supper. When she arrived home I remembered
to greet her with a curtsey, which I guess she appreciated, because
while I was getting the meal ready she kept lifting my skirt to stroke
my panty-clad bum. We went to bed early, me wearing my bra and nightie
at her prompting, and after my throbbing cock had relieved its copious
cum inside her and I'd licked it all out again (maybe this recycling
was why I had so much juice in my cock to pump into her every night?) I
pulled my knickers up round my tired manhood and slept like a baby - or
should that be like a babe?
FRIDAY
Despite the way my girlie trousers revealed the outline of my maleness
(as well as of my underwear), I did not have the courage to go shopping
wearing a skirt. At the supermarket checkout I was relieved to see that
it was the same girl who had served me before. She smiled. "Hello
again. Your hair looks nice. You have pretty nails, too." I smiled
back, but didn't know what to say.
I returned home, changed into my skirt, and prepared for the evening
meal. When my wife arrived back I greeted her with a curtsey. "How's it
going?" she asked, "All under control?" I smiled and said it would all
be ready. "And what about you," she went on. "Will you wear that skirt
or your long one?" I replied that I preferred the shorter one. "Good,"
she laughed, "so much more accessible. And anyway, you have nice legs.
Now you need to come upstairs and get pretty." I checked that it was OK
to leave the kitchen for half an hour and followed her upstairs.
"Take your skirt and top off and have a wash and close shave," she
instructed. It was strange but exhilarating to do this wearing bra,
knickers, stockings and heels! She came into the bathroom with the pack
of Tampax and showed me how the applicator worked. "As it's an all girl
evening, you need to wear a tampon," she explained. "Take your knickers
down, put a drop of handwash on your middle finger, squat down and
gently transfer the handwash from your finger to your bum hole - it
will act as a lubricant. Then let your bum muscles relax so that you
can insert the tampon. Then wash your hands again before you get
dressed. And if you need to have a poo during the course of the
evening, remove the tampon using the string, do your dump and then put
a fresh tampon in afterwards. Now I know you probably haven't done this
before, but be quick!" She left me to it and I managed to insert the
Tampax without too much delay. I was conscious of the plug in my bum,
and also of the string dangling down. I pulled up my knickers and
washed my hands thoroughly.
Back in the bedroom she applied my new lipstick and a bit of other
make-up, brushed my hair, spritzed me with a heady perfume and helped
me into blouse and skirt. "You look and smell lovely, darling. Do you
feel good?" I smiled and nodded. In fact I did feel very good. I felt
comfortable with and comforted by the feel of my bra - the cups were
warm around my nipples and I was almost constantly aware of the gentle
but insistent straps around my back and shoulders. My knickers were
cool and soft and silky against my skin. I had adjusted my suspenders
so that they were taut, pulling at my stocking-tops with every step. I
loved the way my stockings rubbed together and was also conscious of
the bare flesh above them. The modest heels on my shoes were enough to
give my legs and bum a more feminine shape. They made me walk more
daintily, and of course I was now also aware of the Tampax inside me -
I realised this also affected the way I walked. My skirt floated around
my knees and brushed my legs, but I had the feeling that any sort of
breeze could lift it up above my waist, revealing my underwear to the
world - scary but very erotic.
When the guests arrived I was shocked (but aroused!) to find that they
were the ladies who had served me with my purchases - they each asked
if I was wearing them and I was able to truthfully say yes to each.
The meal went very well and I was complimented on my cooking skills. I
was a little surprised how earthy the conversation became after a
little wine had been consumed, and was also not expecting the hands
that fondled my bottom and groped up my skirt as I was serving the
food. But I began to notice the women more and wondered what sort of
underwear they had on, and I was jealous of their breasts. I wished I
had tits of my own. Finally, my wife said, "Well dear, that was lovely.
Thank you very much. But I expect you have some clearing up to do in
the kitchen?" I took the hint and stood up. "Be a dear and give the
ladies a curtsey," she said. I complied and a few repeats were
requested. There was some applause and some comments. "Nice legs!",
"Pretty pink knickers!", "Sexy stockings!"...
As I cleared up in the kitchen I could hear them talking and laughing,
but couldn't make out what was being said. I heard them getting ready
to leave and went back out of the kitchen. "Thanks, dear. A lovely
evening," said one, "and see you next weekend." After they'd gone my
wife explained that we were invited over to the house of one of our
guests next Saturday. "You won't have to cook, but they would like you
to be a waitress!" She took my hand and led me upstairs. "You've been
so good you deserve a treat. But first you better remove your Tampax.
Your first period is now over."
Back in the bedroom she gave me a marvellous blow-job. I was surprised
how good she was because she'd never given me one before. After the
long build-up of the day my cock was ready to explode. I lay back on
the pillow. She put her lips against mine and my cum trickled back into
my mouth.
SATURDAY
When I woke up she had already gone out. There was a note to go and buy
food for the weekend. Bra, knickers, suspender-belt and stockings had
been laid out for me, along with a frilly white blouse. She had left
the option open concerning trousers or skirt. I shaved and showered and
brushed my hair into shape, put on my underwear and stockings, then
applied lipstick and a little spray of perfume. I put on the blouse,
noticing that when the buttons were fastened it fitted snugly and that
my bra showed through the material. I felt that I still did not have
the courage to go out on my own in a skirt, so put on the trousers
again. My Mary Janes were nowhere to be found, nor any of my male
shoes, so I had to put on the heels again.
When I checked my appearance in the mirror, I realised that my
hairstyle, eyebrows, lipstick and shoes looked fairly girly, but the
trousers were too revealing. Not only were the outlines of my underwear
clearly outlined, but there was also a bulge at the crotch, which gave
away my true gender. I changed into the skirt, feeling my pulse rate
increase. Although the hem of my pleated skirt was just long enough to
cover my knees, the material of the skirt was so light and floaty that
I almost felt as if it wasn't there.
I put on my pink jacket and picked up my purse. Checking that I had my
keys, I stepped outside. Immediately I felt the cool air reaching up my
skirt to accentuate my naked and hairless thighs. I was suddenly very
aware of my knickers and taut stockings and felt a tingle in the end of
my dick. Walking without trousers, I was only intermittently aware of
my skirt and felt as if my knickers and stocking-tops were on display.
I had to keep checking my reflection in shop windows to build up
confidence in my appearance. I realised that, despite my anxiety to get
back to the safety of home, I needed to walk not too quickly and with
dainty steps. Also to hope that it did not get windy!
I bought what was needed and started to go back home. Although I now
had more confidence wearing a skirt, I still needed to check my
reflection in shop windows. Suddenly I realised that I was looking at a
display of women's underwear. And that there were some knickers that I
really liked. Almost without thinking I entered the shop.
The sales lady, who I realised was probably the proprietor, was a few
years older than me. It occurred to me that she could have been my
mother, or my mother-in-law. "Hello dear. What can I help you with?" I
managed to explain that I liked the look of the red knickers in the
window, hoping that my voice did not sound too masculine. "Oh yes, I
know the ones you mean. What size do you need?" Suddenly I realised
that I did not know anything about the sizes of women's underwear. "Er,
I'm not sure," I stammered. She smiled and measured my waist.
Opening a drawer, she reached out a selection of red satin knickers.
"Any of these will fit you, dear, "she smiled. I picked out a pair with
generous frills around the waist and leg-holes, and a dainty bow at the
front of the waist. "An excellent choice, dear. This style allows
plenty of room for growth." As her smiling eyes met mine, I realised
that she knew exactly what sort of growth might occur. I paid, and as I
was leaving she said, " You know, we have an embroidery service. Some
of our clients like their name embroidered on their knickers. I hope
you will come here again." I smiled politely saying nothing, but I knew
that I probably would return.
When I got home, my wife had still not returned. But there was plenty
of housework to do. I put the washing machine on and got on with
hoovering the carpets. It was quite late in the afternoon by the time I
had finished the ironing. I was just putting the ironing-board away
when she returned home. I helped her unload several packages from the
car. She said she would have a shower and meanwhile I could prepare our
meal.
The meal was nearly ready when she came into the kitchen. She wore a
short wrap, and her stocking-tops were just visible; I felt a tingle in
my knickers to be reminded that I was wearing stockings and suspenders
too. She held up the bag containing my purchase from the ladies'
underwear shop. "I'm pleased to see that my husband is now buying his
own knickers," she giggled. "I know the lady who runs this shop. She is
probably used to men buying their underwear from her!"
After we had eaten we got a drink and sat in the lounge. Her hand
reached up my skirt to fondle the flesh above my stocking-tops. "You
know," she began, "at the meal last night, several of the ladies said
you were staring at their breasts. So we all agreed that you should
have some of your own. After all, if you are going to be allowed to
wear feminine clothes, you should at least appreciate what it is like
to have a couple of large tits." I realised it was pointless to quibble
about the phrase "be allowed to wear feminine clothes". Although I had
initially been "persuaded" into knickers and a skirt, the fact that she
knew that I had now bought some knickers of my own rather undermined
any possible objection on my part. "I've got you some breast forms and
a new bra. You can try them on tomorrow. Now why don't you show me what
your new knickers look like? Take your skirt off so I can see
properly."
I slipped out of my shoes and took off my skirt and then my knickers.
Stepping into my new red knickers, I pulled them up and stepped back
into my shoes. The new knickers felt so deliciously cool and soft on my
bottom that my cock started to stiffen immediately. "Ooh, I can see you
like those," she laughed. She stroked the front of my knickers until my
cock was ready to burst, then took it out and made me come into what
was left of my drink. She milked out the last drop and then gave me the
glass. "Drink up, dear. Swallow your sissy-juice."
A few minutes later we were in bed and I fell asleep, contentedly
sucking her breast.
India
- 14.09.2021
- 13
- 0
