Escape to Ecstasy
By Pippa HighHeels (
[email protected])
[Driven by irresistible desire, yet consumed by immoveable guilt, our
hero(ine) forms a plan to become the slut of his dreams. Meeting a TV
with similar tastes confirms his actions and takes his pleasure to new
heights.]
1. The escape.
All the twists, turns and decision points in the course of my life
sometimes astonish me; all have conspired to result in me standing on
this particular piece of the Earth at this particular time.
These were my thoughts as I looked out from the sandy cliff on to a
grey and threatening sea. It was late October and the weather, though
not yet cold, was rainy and blustery. The clouds were multiple layers
of interleaving greys, throwing thin dashes of rain in the gusts of
wind. I had taken a walk from my little flat, which had been my prison
for most of the summer. But the physical prison was one from which I
could easily escape; the previous prison had taken months of planning.
Those months had been some of the most changeable at any time during my
life; the highs had been the exhilaration I had first sought, yet at
the expense of dangerous, black lows in the realisation of the pain I
may have left behind.
Driven by my frustrations and my innermost desires, I had, in the early
spring, loaded all my most prized possessions into my car and simply
driven off to a new life. Could it be that simple? After all, there is
always something left behind. In my case, it was a wife of 18 years and
two children and their dependence upon me as loving husband and father;
but I had to face the simple truth - I was not happy now, had not been
happy for several years, and had no prospect of happiness in the
foreseeable future. I left a note:
Dear V...,
I know this will come as a shock, but you are well aware of how unhappy
I've been. The daily grind has taken up so much time I've never had
opportunity to do the really creative things I've wanted to do.
Selfish, maybe, but I've suppressed my true feelings for so long and
can't do it any longer. You have no idea how boring 'family life' is to
me; I always feel like a powerful car forced to trundle along in first
gear. Maybe I'm arrogant too, but I refuse to be conformist. I don't
think we have much in common now; you have the children you always
wanted, but they've stolen you from me and now we are so diverse in our
ideas of how to enjoy life; we are so apart in mind we may as well be
apart in body too.
You can have the house, its contents and the remains of the money; I've
just taken a few thousand to tide me over until I get settled. My
recent inheritance is intact and should see you all in comfort for at
least 8 years. I shall send money if and when I make enough. I have
taken my clothes, laptop, some books and some music.
Other than that, I can only wish you all well.
Those sentences will now have been read many times over and they remain
clear in my head even after all these months. I remember the morning I
leaned the crisp envelope containing their fateful contents up against
the kettle in the kitchen; my wife had taken the children to see her
parents for the day. I simply packed up my stuff and bundled it into my
car; I went through my checklist multiple times. I had to make sure I
had all the documents I may need for a new life. Then I drove to a
nearby town with a good camping shop where I selected a good-sized tent
and all the kit I should need for a few weeks under canvas, away from
telephones, email and dependents.
I knew exactly where to go too - a campsite where we had enjoyed a
holiday whilst still single, where we had first made love and where
life was good and carefree.
The drive took most of the day; I kept thinking about the letter
propped up against the kettle. Would there be tears of sorrow or anger
at my deceit; how would she handle the questions from the children? And
why do I care? Why should I care? I was not happy; now I am happy. I AM
happy, aren't I? What time is it? Will they be home now? Will she have
read it? What will her first reaction be?
It was around 5:30 in the afternoon when I drove up to reception at the
selected site on the North Wales coast. It was too early in the season
to be busy, so I booked in for a week and paid in cash.
The weather was chilly now and a blustery wind was blowing. I was going
to have a tricky job in erecting the tent but eventually, in fading
light, I was done. I ate a sandwich I'd bought in a garage on the way
and drank a bottle of water. Then I went to the toilet block and took a
shower and prepared for bed, even though it was still early. By 9
o'clock I was zipped up and snug in my new sleeping bag, listening to
the gusts of wind and the light rain on the tent. I thought of my wife
and the children, wondering of their feelings and emotions, what they
were doing. I started to sob gently; almost immediately, I sat up and
grabbed my mobile telephone from my trouser pocket. Thank goodness
there was no signal where I was. I resolved to throw the telephone away
the following day, but then thought better of it.
I was angry with myself; I had told myself over and over that I could
only go through with this by being mentally tough. I was NOT going to
feel guilty. I WAS going to grab back my freedom. Tomorrow was the
first full day of my new life and I was going to have to discipline
myself hard in order to have the mental resilience. I did not want to
return weepy and pathetic, I did want to escape triumphantly.
The following day was bright but chilly in the spring sunshine. I felt
refreshed from my night's sleep considering I had so much on my mind;
but, I said to myself, I must cut off from the past and plan for the
future I want, not one I was obliged to have.
So, even though it was early, I strolled across to the deserted toilet
block and had a shave and a shower. On my return, I boiled up some
water on my new stove. The tent had an extension 'porch' area where I
could keep thing dry and prepare food in some shelter. With a bowl of
hot water, I went back into the tent with my washing equipment. I was
going to do something I had always wanted to do; I was going to do
something to symbolize the new me; I was going to do something which
would stop me going back to my wife, something that would require a lot
of explanation if discovered. I was going to shave my legs and as much
of my body as I possibly could.
I was almost trembling with anticipation as I sat, hunched up, but not
caring about the discomfort, and brushed the lather onto the lower end
of my right leg. I took the razor and swished it in the bowl of hot
water; in an almost ritualistic way, I started to shave the long wiry
hairs from my legs. I had to be careful not to spill my water; several
times I had to dress to be able to go and pour away the dirty water and
wash out the bowl; then I would boil up some more water to return to my
shaving. I took me nearly 3 hours to shave my legs, arms, chest,
armpits and as much of my pubic area as I could and dared to under the
circumstances. I dressed again and took a small case from my car. I
went back into the tent and undressed again. From the case, I fished
out two items that had driven me onto these excesses, two items that
had spent the vast majority of their time hidden deep in the loft away
from prying, non-understanding, wifely eyes - a black satin waspie with
six suspenders and a pair of black seamed stockings. The 'true
feelings' I had mentioned in my letter were never explained there, nor
could they be explained there. Quite simply, I was a transvestite; I
had always been a transvestite. But now there was a difference; for
now, I was always going to be a transvestite. There would be no going
back, no throwing it all away in an attack of guilt, just the ecstasy
of the feeling, that wonderful erotic thrill that I yearned for. Now it
would be much, much better. Freedom would give just that, freedom to be
me, to dress as I wanted when I wanted; to be excited again, to have
one's breath taken away by the sheer erotic power of feminine lingerie,
high heeled shoes, make-up and all the other trappings of the sensual,
alluring sex goddess.
As best I could in the cramped conditions I laced the waspie about my
midriff; sliding the stockings over my freshly shaved legs and
fastening the suspenders tight gave me such an electric thrill. The
feeling, for me, was better than any narcotic and amplified to an
ecstatic bursting point by my smooth legs. Instantly I was erect; I lay
back in the semi-darkness of the tent to submerge myself in the luxury
of the feeling and all too soon great plumes of my cum pumped out of my
turgid cock and up on to my naked chest.
2. Two months later.
I had spent the spring and early summer at several camping sites up to
coast. I was not entirely idle, for I was very aware of the need to
earn reasonable money if I were to find somewhere permanent to live and
to be able to live out my dream of freedom to dress and enjoy myself. I
worked as a programmer but I was going to have to learn new skills in
order to work entirely from 'home', wherever that may be. I was
convinced that all I needed was a fast communications link to the
internet and the world could be my customer. So, I studied long and
hard, driven by the temptation of 'that feeling', the one that I loved
so much, the one that I wanted to enhance, to be whole, to be female,
to be sexy, to be a tart, a whore, a slut, a goddess of sex.
As it turned out, one June day the Gods were on my side. I was walking
down a rather dingy, dusty street in a small market down near where I
was camping when I passed a rather sorry-looking cheap furniture and
carpet shop. In the corner of the window, amongst the dead flies, a
faded card advertised a 'Flat to let, apply within'.
At the back on the shop, a rather stout man put down his newspaper and
observed me over the top of his half-glasses. I almost felt I was
intruding on a private space, for there were no customers in the shop.
'I saw the advert' I said, enquiringly. He looked at me, puzzled.
'About the flat..." I reminded. 'Oh, oh, yes, the flat'. Eventually, he
rose, folded his paper and threw it down. 'It's not exactly luxury.
What were you after?' 'Somewhere to live, simple as that' I replied.
'You're not just out of prison are you?' He looked worried and stern,
as though he were about to give me a lecture on morals. 'No, no,
nothing like that. I'm just trying to start again after my marriage
broke down; it's tragic really, but I'm determined to get on with my
life and re-build it. So I arrive at your shop this fine Tuesday
afternoon. Could I see the flat please?' I was determined I was not
going to say too much.
He went back into the store room and returned with keys, then grumbled
'I'll have to shut the shop for 10 minutes' as though he were about to
lose a crucial sale. He led me around the corner to the narrow road
behind the shop. Set back from the street was a plain door with peeling
dark-green paint. 'I haven't been in here in months' he said, kicking a
yellowing pile of papers, mostly junk mail from behind the door. He led
me up a dingy flight of stairs to another door. This led to a small
hallway with 3 doors off. The first door led into the main living room,
which, as it turned out, was also the bedroom. There were windows on
one side of the room; these were above the shop, looking out onto the
original road, hung with brown, rotting net curtains. The room was
indescribably filthy and hung with cobwebs. The other two doors led to
tiny kitchen and bathrooms respectively; these two were in a truly
appalling state; the bath, washbasin and toilet did not, at least,
appear to be broken, and the kitchen showed no signs of vermin. So,
although filthy, the place appeared to be sound and self-contained. I
enquired about the hot-water system and heating and was satisfied. Ron,
for that was my new landlord's name, was at a loss to name a price on
the rent. We agreed that I would clean, decorate, carpet and furnish
the flat (the latter two from his shop) in return for a low rent pegged
for one year. I had to check I could get a fast internet access and all
should be well.
I felt such joy cleaning up the place; this was to be my base, my
haven, my sanctuary, where I could do as I pleased. I swept and cleaned
and polished; I painted all the ceilings, walls and woodwork. Within 2
weeks I was able to call the place my own, had it furnished and
comfortable. And finally, I had a desk, a computer and a link to the
outside world.
I sold my car, moved my money into a local bank and made a list of
resolutions aimed at keeping myself fit, healthy and motivated. I
exercised early every morning by running down by the sea; I ate very
healthily and started to lose some weight. I kept a detailed diary of
every day's activities. I was using the net to try to get paid work -
anything I could do on the computer to give me an income. I had said to
myself that I would not buy more clothes until I had earned my first
money. The temptation to buy some shoes across the internet was
overwhelming, but I resisted.
However, the freedom and security of my own place did allow me to
indulge in my other great passion - using my sex toys. At home, these
were secreted away with my small collection of clothes and it was
certainly difficult to use them and clean up properly in a tent. But
once I had hot running water and a lockable door, I could be clean,
tidy and safe. Most nights I would play a hardcore DVD on my computer -
again from my home secret stash - put on my waspie and stockings and
relax with my toys. I had a selection of plugs and two large realistic
dildos, the largest of which was immense and literally took my breath
away each and every time I used it. Each night I fitted my monsters
deeper and for longer. I was in my true heaven here; every night I
produced a great gush of cum into a bowl. I raised the bowl to my lips,
called myself a filthy whore, and savoured the smell and finally the
taste of my own love cream, licking the bowl clean and then laying back
with deep, lasting, satisfaction.
3. A Tuesday in August
I did, after much persistence, finally get some programming work for
which I was paid. I had also created web sites and done some
consultancy work. I bought a server upon which to host some web sites
and was charging a monthly fee. In 2 months - working 16 hours each day
- I had a reasonable income, growing each month. I started a company,
engaged an accountant and paid tax again. I thought about paying some
money to my ex-wife (as I now thought of her) but decided to buy
clothes - sexy female clothes.
I decided on a strict budget for my first purchases. My first priority
had to be some high stiletto heeled shoes. These had always been a deep
fetish for me; a girl in high heels would leave me transfixed. I had
had several pairs before in my life but I'd always regretted I could
not wear them for longer periods. So, I ordered a pair of 5 inch
stiletto court shoes with half-metal heel; I also ordered some new
lingerie and stockings, some make-up, my first-ever wig and a micro-
mini skirt. Then, I ordered a new, even larger dildo, plus a long
double ender. All I had to do now was wait, in great anticipation, for
my purchases.
One morning, a morning just like every other morning, I had been for my
run and had shaved, showered, breakfasted and started work by 7:30. By
11:00 I needed a break and some fresh air, so through open the windows
that looked over the road. I was stopped by the tip-tap-tip-tap sound
of high heels on the pavement. I looked out and saw a tallish, elegant
woman who was, indeed, wearing high spike heels. She was striding down
the road at quite a pace; I watched as she stopped at the fish and chip
shop further down the road. The shop was closed but she knocked at the
door and was let in by a man in white cooks clothing; so, she must work
there... I had been so careful in my diet, so wanting to lose weight,
trim my waist and flatten my stomach, that I had banished any thought
of fast food, even though the smell was sometimes tempting. But now
there was another reason to be tempted.
I kept an eye on the shop to see when it opened and at 11:30 promptly
the man in white turned the sign on the door to 'Open'.
I finished my current task and just before noon strode into 'Atlantis
Fisheries'. I was not the first customer; a young woman and two pre-
school children were sat at the side of the shop; the children were
arguing and not eating their lunch, despite the entreaties of the
mother. Instantly I thought of the life I had left behind and one huge
reason I had done it.
I sat down, held the menu for a moment and within a minute she was
standing by my table; she had a striking face that almost looked
startled. She had obviously spent a long time at her make-up, which
seemed incongruous with a job at a fish shop. Her foundation had made
her skin look flawless and her eye make-up was heavy and dark. Her lips
were full, well-defined deep blood red and her hair was a shoulder
length red-brown with bronze highlights. She wore a black roll-neck
sweater, which covered her modest tits. She took up a pencil to write
and said 'Are you ready to order, Sir?' Her voice started out deep, and
after the first syllable she coughed and lightened her voice. Instantly
I knew and a huge surge of adrenalin hit me - perhaps she was not what
she seemed to be... Completely flustered, I tried to say 'Small Fish
and Chips, please', but nothing came out. I blushed deeply, smiled,
coughed politely and repeated my request whilst avoiding her gaze. She
wrote down my order and moved off to the counter; of course, I could
not help but look at her legs, which were shapely and encased in smooth
barely-black nylon; her heels were around 4 inches high and a classic
stiletto. She knew I had looked and quickly looked back at me, catching
me a little embarrassed again; she smiled at me in a knowing, cheeky
way. She was good in her heels and seemed comfortable in them, even
though she was probably not going to be able to sit down for the next
few hours and knew it before her choice of footwear. So, I concluded,
she must be wearing them because she feels good in them; I knew that
feeling all too well.
I was just coming to the end of my meal, when the door swung open and 3
large workman blustered in and took a table; they had parked their van
outside the shop although parking was forbidden there. One of them
continued to smoke although there was a large sign asking patrons not
to smoke in the shop. "Come on, Graham, yer great puff, get yer arse in
gear, we're 'ungry" barked one of the men loudly. The waitress came
over, looking worried, holding her pad. She looked down at the man
smoking and politely asked him to stop. He looked up at her
aggressively and shouted 'Don't you fuckin' tell me what to do, you
fuckin' fairy, keep yer fuckin' gob shut and get us our dinner!'
Inside, I was raging. I stood up, looked directly at the man, and found
myself saying: 'That's no way to talk to anyone, and certainly not in
front of ladies and children! You should apologize now!'
I heard the children behind me say to their Mother 'Why is that man
angry, Mummy?' 'What does "fuck" mean, Mummy?'
'Do you want a smack, pal?' said the man to me, getting up. 'Leave it,
Gerry', said the eldest of the three, 'We'll go down to the Feathers'.
'I'm not letting 'im get away with that!' postured the man again,
stabbing the air towards me with a grubby finger. He was like a dog on
a leash. 'I said leave it, Gerry!' said the elder man again, grabbing
the younger man by the arm and leading him out of the door.
The owner of the shop, who, I later found out was known as Greek Tony,
came out from behind the counter to see what all the shouting was
about. 'Oh, ees ze Allen brothers again. They really bad news, mister.
But they won't do anything here 'cos o' ze cameras, see'. He pointed to
the security camera. 'They think they owna theees town 'cos their
father, he a chief in the police'.
I sat down, breathing hard. 'I think I should like a cup of tea,
please' I said to the waitress. I didn't particularly want one, but I
didn't want to leave her. 'Thank you for what you did there' she said
sweetly. 'Do you have to put up with a lot of ignorance in a town like
this?' I empathized. 'I'll get you that tea' and she walked off behind
the counter to make my tea. The shop started to get busy, mainly with
take-away customers. I sipped my tea very slowly, but I couldn't take
my eyes off her as she served the customers and glided between the
tables. She stopped to collect my cup; as she put her hand down to take
the cup I slipped my hand over hers and said 'What do I call you?'
'Gloria' she said in a distinctly male voice. Was this an attempt to
put me off. I watched her collect other plates; she bent over the table
in front of me and I had a glimpse of black stocking top. Had she done
that deliberately? As she passed me again I said 'I'd better pay my
bill and go'. She walked off and got me the bill. She sat down opposite
me whilst I fiddled with my money. 'And what about you? You've never
been in this shop before. Are you just passing through?' she said,
reverting to her 'Gloria' voice. 'No', I said 'I've moved into the
flat above the carpet shop up the road. I, errrr, work for myself - and
live by myself, I'm errr, separated. I've had a bad time, so I've
started afresh'.
She looked at me closely. 'You haven't been able to take your eyes off
me, have you?' I did not know what to say; my mouth was dry despite the
tea. I was going to say something bold, but then decided against it,
smiled and shrugged ' I don't know what to say, but it's a fair cop...I
think you are very, very brave. I guess you've had to put up with a lot
in a small town like this...' There was a heavy pause. 'Your boss seems
nice' She smiled at me again 'Greek Tony? He puts up with my little
ways. Some days he gets Graham, some days he gets Gloria. He doesn't
mind if I do 'it' on our quieter days. Most of the locals know me. The
tourists sometimes read me, but many don't. I'm past caring really. He
gets me cheap because I need the job'. She picked up the money and
gestured towards the counter, as there was a customer to serve. 'Keep
the change. Goodbye'. 'Bye now, thank you', she said cheerily, 'do come
again'. 'Oh, I will, I will'.
I walked out feeling like schoolboy who has fallen in love for the
first time; not that I could call it 'love'. I just could not get
Gloria out of my mind.
4. Tuesday afternoon
After my introduction to Gloria and the events of the lunchtime I found
it very difficult to concentrate on any work. After an hour, the outer
doorbell sounded. I wondered if it could be Gloria, or maybe it would
be Gerry Allen, come to beat me up. It was neither; it was a delivery
of two large parcels. I got the parcels inside and locked the doors
behind me. Now I was certain no work would be done that afternoon.
The fist parcel contained the two toys and several tubs of lubrication
I'd ordered at the same time. Since I had found myself this place to
live my existing toys had seen a lot of use. I guess I was making up
for all the time of deprivation when I lived with my wife. Most
evenings, I would wash myself out to prepare for the pleasure to come;
sometimes I would just wear a plug, other times I would fuck myself
vigorously with my dildos. They were super-realistics with large
suckers on the base such that I could attach them to my hard wood chair
and ride them. One was 10 inches long and around 2.5 inches thick -
this I had now fully mastered and could insert it such that I could sit
on the balls at the base; the other was nearly 3 inches thick with a
big bulbous head. This too was gradually being tamed as I regularly
took 7 to 8 inches of this with no problem.
So, I was well reamed out and had a good 'gape' when I observed myself
in the mirror. The new toy was a real beauty, black and slick and much
thicker than I'd ever tried before, being nearly 3.25 inches thick. I
felt its weight and felt nervous and excited at the prospect of playing
with such a monster.
[Author's note: see model 'Erik' at www.dildos.co.uk My thoughts are
based on this beauty.]
The other toy was a long, flexible double-ender, some 18 inches long
and 2 inches thick. I had bought this for depth training. I was
wondering who I should like to go on the other end with me. I didn't
have to think long to come up with a suggestion...
The other package was going to be as exciting and I was trembling as I
opened it. The first thing I saw was a shoe box! High Heels at last! I
ripped open the box and they were in my hand; a pair of the most
beautiful shoes I had ever seen. They were classic black 'court' shoes
with 5 inch half-metal heel. They had low vamp and sides and the tip
came to a classic point. The heels were narrow and elegantly curved. I
kissed them, smelled the leather, held them to my face.
Immediately I pulled the curtains to my room and quickly stripped. From
the trunk kept under my bed/settee I took out my waspie and stockings.
I could hardly get them on, my hands and body were trembling with such
expectation. I had to stop and take several deep breaths to calm myself
down; eventually I managed to lace up my waspie and pull it adequately
tight. I slid my fingers into the toes of a stocking and, with utter
joy, slid my leg into the sheer nylon. I clipped the stocking tight and
repeated with the other leg; with newly shaven legs the feeling of
being caressed by the nylon was truly gorgeous. I sat down; now I was
praying I had chosen the correct size of shoe. Sure enough, I slid my
first stockinged foot into the cool leather of the shoe. Perfect,
neither too big or too tight. I slid the second foot in, lay back and
kicked the air in excitement. Carefully then, I placed my shod feet on
the floor and tried to stand up, feeling the crush of the muscle at the
back of my legs. Slowly I stood up then took my first step. Then I
walked into the kitchen to make a cup of tea - in short corset, black
stockings and high spike heels. I was truly in heaven.
I could not but help but walk around my tiny flat as much as possible,
wondering if there was a telltale sound to Ron in the shop below. I
opened the other items in my parcel - my first wig, blonde and long
with lots of curls, and a large bag of assorted make-up. I was going to
have to learn some new skills, but could not wait to learn them. I also
had a bra and some fillers, some new black stockings with seams and a
tiny flared mini-skirt that I hoped would fit such that the hem would
float around about my stocking tops. I put on my bra and inserted the
fillers. Then I pulled my tightest T-shirt over my head and wondered at
the swell of my chest; this was a new feeling for me. I could not help
but fondle my tits, feeling their gorgeous weight and bounce.
Carefully, I stepped into my new black skirt and fastened it. It was
tight around my waist and flared out; standing still, it just covered
my stocking tops but the slightest movement showed stocking top and the
white thigh above it. I posed in front of my long mirror; my cock was
rock hard.
Although I wanted to have a go at making up I did need to do some
research first, so I deferred this until later.
Instead I took the huge new dildo, placed its base squarely on the
floor and applied lots of lubrication. I removed my new skirt and
walked around the new beauty, anticipating what it could do to me,
half-afraid, half-longing. Eventually, I squatted in my new shoes over
the toy. I teased my willing hole with the beautiful knob end, opening
more and more with each squat. Eventually, after maybe 20 minutes of
this, I felt penetration. Immediately I withdrew, applied some more
lubrication and slowly, very slowly took the beauty within me again. As
I did, with about 4 or 5 inches of this monster in me, I screamed 'For
you, Gloria, Gloria!!!' and my cock, without any stimulation from my
hand, pumped globs of hot, creamy spunk.
5. Discipline
I always felt my happiness could only come from mental discipline. I
ensured, absolutely ensured, that I exercised, ate proper freshly
cooked food, kept the flat and myself clean and tidy. I adhered to
strict working times and worked hard to ensure I had an income; I kept
records of all that I spent and did; I kept a detailed diary to re-live
my new experiences. Above all, I had to be free of guilt and
sentiment.
In many ways I had surpassed myself; for my small outgoings I now had a
reasonable income, though not enough should I have to suddenly pay
maintenance. But I had been lucky and had been able to give them a very
substantial lump sum. With some care this could last for several years.
In the days after, that long, hot August became a haven of total self-
indulgence. But, above all I was enjoying myself. I thought of the dark
days of squabbling and shouting; I had never wanted to live in such
circumstances. I had concluded that the only way I could be truly happy
was to be alone and live to my own standards. But, surely, this was
selfishness in the extreme; how could I not be happy except by helping
my dependents? Yet in doing so I had made myself so unhappy, to an
extent where I had seriously considered 'ending it all'. Who would I
help then? I had to rationalize my feelings; my inner desires, to dress
and enjoy my sexual self was infinitely strong. I knew that I could
never dismiss them or sublime them with other activity; I had to accept
these feeling for what they were. Any post-orgasmic self-disgust must
be eliminated by understanding and absolutely accepting, that, like it
or not, this is the way I am.
Each night I would dress and make my attempts at make-up. I had looked
at several web sites giving advice, and whilst I tried, carefully and
slowly, I could never get the effect I wanted. I enjoyed the process
but was always disappointed by the result. I needed help and I knew
where I'd like to ask for it.
I had, of course, watched for the re-appearance of Gloria. I had seen,
who I assumed to be the male persona of 'Graham', report for work at
the shop several times, but I had not seen 'Gloria' appear again since
that first day. I was disappointed, as I thought that by only using the
shop when she was 'Gloria' that I should send the obvious signals.
I called in the fish and chip shop for lunch the next time I saw
'Graham' report for work. I was early, for I was dying to ask him about
'Gloria'. I sat down and he came across to take my order. I had thought
long and hard about the first words I was going to say to him. I wanted
to avoid any cheesy joke about how different he looked. In fact, it was
he who spoke first: 'Don't say it...you don't recognise me without a
skirt on...' I smiled and replied 'I was determined not to come out
with some corny line like that'. 'Maybe, you'll find it easier to keep
your eyes off me today?' he suggested. Again I smiled. 'Well, I can't
deny it, Gloria has some distinct attractions'.
He seemed to want to get on with taking my order. My heart was beating
so fast because I was nervous. Then I said, with somewhat trembling
voice "I'd like a small fish and chips please" and then I added "...and
some advice."
"Well, I think the fish and chips will be OK. How else can I advise
you?"
Now, I was sweating profusely, although it was not the hottest day. I
mopped my brow and whispered, "Could you possible give me some..." I
hesitated again, for I was about to divulge my secret to a stranger.
Above the booming of my heart I heard myself whisper "makeup lessons".
"I'm sorry", he said, "I couldn't quite hear you". "You know..." I
flustered, "to help me look like a, you know..."
"Are you alright?" he asked, "You do look very hot"
"I'm just fine." I said, taking some deep breaths.
Then he turned. "I'm sorry, I have to go and serve. I'll put your
order in, won't be long". With that, Graham walked behind the counter
to serve. I was in agony. I was so ashamed at my cowardly behaviour.
How was Graham possibly going to be offended by my request? Still, I
was terrified; I nearly left before my lunch. After a few minutes, the
queue had been served and he came over to me with my lunch. "Are you
alright now?" He didn't wait for my reply. "There you are, I selected
that fish for you, I'm sure you'll like it. Now is there anything else
I can get you? Sauce? Vinegar?" My chance was now or never.
How I did it I'll never, ever know. Without the slightest waver in my
voice, I looked Graham in the eye and said: "As I tried to say before,
I was wondering if you could give me some private make-up lessons? Of
course, I'll pay for your time."
"Are you also theatrical?" he asked. "No", I said, "I'm simply a closet
TV..." I smiled. He turned again to go and serve. Smiling he said,
"I'll be back in a minute".
I started, slowly, to eat, though found it difficult in my nervous
state. I could not let Graham down now after he'd personally selected
the fish I was about to eat. He kept glancing over to me whilst serving
the customers and once, when I smiled back, he winked at me. My heart
thundered again.
Ten minutes later, Graham was back. "Sure. I can do that for you. Maybe
you'd prefer Gloria to help you, I'm sure she would if I ask her nicely
for you. When were you thinking of? I'll have to make arrangements with
Dad..." He started to think of the logistics. This may turn out far
better than I'd hoped. I said 'Why don't you pop over to see me when
you finish here". I told him how to get to the back door leading up to
the flat. "Oh, the fish was delicious, thank you. I'll see you in a
while".
It was only 1 o'clock when I got back to the flat. I tidied up,
although there was little to do. I paced the floor nervously, keeping
an eye on the front door of the shop further up the road. Sometime
after half past two, Graham emerged from the shop and walked up the
road in my direction; he saw me in the window and gave me the thumbs-up
sign. I went into the kitchen and switched on the kettle before going
down to the door to let him in. "Please, go on up" I said, shutting the
door behind us. I followed him up the stairs. Looking up I thought how
better the view would have been had he been Gloria; I thought to make a
joke about it, but then thought better of it.
"Please, take a seat. I'll make us some tea. How do you like it?"
He looked around at the Spartan room. Over by the window was my large
desk with computers humming quietly and my work chair.
Other than that, the only other piece of furniture was my sofa-bed -
sofa by day, bed by night. Under the sofa-bed and largely unseen, was a
large trunk closed with a sturdy padlock and also padlocked by a thick
chain to the bed frame. This contained my current bedding, clothes and
my secret collection.
I returned from the kitchen with two large mugs of hot tea. We placed
them on the floor and faced each other across the sofa.
"So this is your living room, bedroom, office, everything?" he
enquired.
"Yes, I rent it from Ron in the shop below. It was in a filthy state
when I first moved in. But within a couple of weeks I knocked it into
shape. I have a small kitchen with all I need and my own bathroom. It
beats living in a tent".
He looked at me quizzically. "I've just realised you're my first
visitor, so welcome, Graham" I raised my mug and he did likewise. "A
toast!" "To privacy!" and we echoed the sentiments with a large pull on
our mugs of tea.
"You said you'd been living in a tent?"
I told him my story. He was sympathetic and listened attentively
without interruption. I must have gushed, but I tried to be cogent. I
told him of my mental battle and my fear of being judged selfish and
weak.
"You seem to be relieved to get that lot off your chest" he smiled. "I
must really go - I have my Dad to collect from the Day Centre in a
while and can't be late. He leant over and put his hand on my arm. "I'm
so glad you've been brave and recognised your true self. Really, we can
only live for tomorrow; there is no point in regretting the past. You
have to be true to yourself to have any chance of happiness. I'll see
if I can come round on Sunday afternoon. Can I call you?"
I gave him my mobile number.
He was at pains to be reassuring: "I'll not let you down; you're on the
right road now. You can relax with me, I'm not going to tell everyone
in the town I'm not the only cross-dresser, so don't worry. Thanks for
the tea"
That night I lay in bed, worrying that I'd said far too much, far too
soon.
Then I heard my phone bleep. I'd had a text message: 'Sunday at 2 4 a
new u. Gloria". I tried to sleep, but the image of Gloria and thoughts
of Sunday flooded my feverish mind.
6. Sunday at 2
I tried to analyse whether I was excited or nervous; whatever it was, I
woke early and felt apprehensive. It was as though, when preparing for
a big event, the thought is worse than the event itself. Yet, surely, I
was going to enjoy myself, wasn't I?
I went for my morning run down by the sea. Upon my return, I had a
long, fragrant bath and shaved myself as completely and closely as I
could. I cleaned myself inside too; even if not needed for Gloria's
visit, it was likely I'd be so turned on by the time she left that I
would be desperate to fuck myself with a large dildo. During the
morning I could not settle to anything particularly constructive, so I
tidied up and cleaned the flat again. I got out my trunk containing my
secret collection. The feel of the clothes and shoes was starting to
turn me on, so I put them away. I assumed I would dress once Graham
had arrived, but maybe he would expect...'Oh, stop it' I said to
myself. 'It just doesn't matter'.
Two o'clock came and went. I began to think he would not come.
Eventually, my phone beeped: 'On my way. G'.
It was not long before the outer doorbell rang and I was ushering
Graham up to my tiny flat. He was full of apologies. He entered with a
large holdall. 'I assume Gloria is in there?' I asked. 'Some of Gloria
is in here, yes. Now how do you want to play this?' I did not
understand and my look at him said so. 'Would you prefer it if I
dressed in your bathroom, whilst you dress here, or shall we dress
together, or shall we dress each other, or ... It's entirely up to you.
I want you to be comfortable and relaxed.' I'd not thought about the
logistics.
"Well, if you don't mind I think I'd prefer it if we dress separately,
then meet each other again as two girls." This was my first thought,
though in retrospect one of the other suggestions may have been even
more exciting.
"I'll use the bathroom then, see you in a bit" and Graham took his bag
into my tiny bathroom to begin his transformation into Gloria. I pulled
the curtains most of the way and undressed completely; then I opened
the trunk and dressed in the order I always did: short corset, laced-up
as tight as I dare; black stockings with seams; tiny panties in black
satin; bra and breast-forms; tight sleeveless polo neck top, cut high
at the arms; short skirt with ruffled hem floating over my stocking
tops; 5 inch heeled stiletto shoes; wig. I was trembling as I dressed
from nerves and excitement. What was going to happen to me? Was I going
to enjoy myself? What was Gloria thinking about me? What were her
intentions?
I looked at myself in the long mirror; below the neck looked fabulous,
above the neck looked ridiculous.
Shortly, a soft voice called from the bathroom 'Are you decent? Can I
come out?'
'Please, please, come in.'
'Wow! You look a million dollars!' I gushed, speechless at how utterly
sexy she looked. Her hair was now bleach blonde in long cascading curls
which covered much of her face. Her eyes were heavily made-up with
black liner, blue-black shading, and thick, black mascara. Her lips
were bright red and shiny. Her skin was flawless and a haze of the most
seductive, sensual perfume surrounded her. She wore a white frilly
blouse over a lacy bra with a neckline, which plunged intriguingly. At
her waist was a wide black patent belt atop a short skirt in black
leather, which had a slit up one side. Her slim legs were encased in
the sheerest black stockings. On her feet was a pair of dainty high-
heeled sandals with ankle straps and chain details.
'And you look pretty good yourself! Come on, let's get some slap on
you! Have you got some of your own or shall we use mine?' She
approached me, sensing my nervousness.
'Take a few deep breaths and relax. You've done a lot and been very
brave by doing your own thing' I noticed she avoided saying 'Leaving
your home, wife and children.'
She held my hands and looked at me, forcing me to look her in the eyes.
'Don't you feel good?' 'Oh, God, Yes, I do feel very good' I stammered.
She approached me closer and embraced me. Every touch from her sent
signals of excitement to my brain; her breasts touched against mine;
everything screamed sex.
'I don't even know what to call you; what's your femme name?'
'I've never really thought about it' I said truthfully. 'I'm Philip, so
call me Philippa, or even Pippa.'
'Well, Pippa' she started, 'I can see you're a real sexy girl, just
like I try to be...' She was oozing sex, being as suggestive with her
lips and tongue as possible. 'You can't deny it, wearing such a short
skirt and those fuck-me shoes.' She smiled seductively again. 'Please,
no need to worry, move the chair in front of the mirror and I'll show
you what to do'.
We rigged up my desk light to shine on my face. She removed my wig for
a while and showed me how she applied multiple foundations to get a
good base.
As she worked I felt her sweet breath on my face. She explained how her
Mother had died leaving Graham and his two elder brothers to be brought
up by their Father. Both brothers had become engineers and now worked
abroad in Australia and South Africa. Graham had gained a place at
Drama College in London, but had had to return home to look after his
Father who had some form of dementia. Graham had his job to supplement
their meagre income and had some respite when he took his Father to a
Day Centre. It was at Drama College that he had his first taste of
freedom away from much of the prejudice of small-town Wales. It was
here he began to dress more fully and where he learnt his obvious make-
up skills.
Gloria came to make-up my eyes and showed me her sequence and how to
get a good line around the eye and shade the lid. She applied lots of
mascara, lipstick and lip pencil, a little blusher, a squirt of
perfume, popped my wig back on and Pippa was truly born.
'Wow, what a difference! Thank you so much!' I was amazed by the change
she had brought about in my appearance. No longer was I a man in
women's clothes, but a potentially passable woman, even though I did
dress like a cheap hooker.
'Oh, this feels truly wonderful, so erotic, so sexy!' I couldn't stop
admiring my appearance in the long mirror, posing and pouting.
Gloria said: "Why don't I take some pictures?" She took a digital
camera from her bag. "Shall we have some tea first? Sit down and relax
for a moment."
I tottered into the kitchen to make our drinks. Soon we were facing
each other across the sofa again.
"Do you want to go back to Drama College and finish off the course? Did
you enjoy it there? I bet you did".
Gloria explained that she had had her first taste of freedom in London.
With little money she had dressed as best she could when she could; at
home she couldn't dress at all. She had, like me, gone through the
cycle of guilt, throwing it all away and then re-buying to enjoy
herself again.
"So, why, do you think you're a TV? What makes you do it?"
Gloria smiled her knowing smile. "I am the way I am because I am the
way I am. Having tried to give up and failed so many times, I know I
can't, so I might as well enjoy it. It's not like smoking or drinking;
the addiction there is physical. With dressing, the addiction is mental
and thus much more powerful. Why I started I don't know, but it felt
good and exciting when I first dressed in my Mum's clothes as a boy. I
had to do it, I was compelled by some inner desire. Now, I regard it
as an innocent hobby; I'm harming no one and maybe attracting some. I'm
not forcing anybody else to do the same if they don't wish to. How
about you?" She crossed her legs slowly, exposing her suspender.
"Dressing for me has always been full of erotic power. I just love the
decadence of it all. Even now, it's a powerful prelude to getting off.
I just adore wearing these things; high heels have always been the
deepest fetish for me. If I could change places with someone, I'd
choose an attractive big-boobed porn star who really enjoys what she
does. I have such admiration for them."
"So is it to attract men?" she enquired.
"No. As a married man I was always straight, but in my dreams I was
much more, how shall we say, adventurous..."
She pressed home the implication of her question. "Has Philip or Pippa
ever had sex with another man or a TV? Do tell all to Gloria". She had
a gleam in her eye, half inquisitorial, half predatory. She came nearer
to me on the sofa and started to softly stroke my black-nyloned leg.
"No, no, I've never done that, except a bit of playing around at school
- you know. How about you?" I'd gone coy and nervous again.
"You first, what was this 'playing around'?"
"I used to get together with another boy and wank together." There was
a pause and then I said, "We used to suck each other too. I sucked him
to completion a few times."
Gloria pretended to be shocked. She'd moved closer, her arm on the back
of the sofa behind me, her left hand was stroking up and down my leg
very seductively. "Gosh. You are wicked. You're not going to tell me
you didn't enjoy it are you? I bet you swallowed too..."
I was hard by now, enjoying thinking back to those days of first sexual
experiences and the feeling of David's big, hard, brutal cock in my
mouth, the feeling of the lovely clothes I was wearing and Gloria's
hand sending little shivers of delight up and down my legs. "At first I
hated the taste, more I think through guilt than anything, but, yes, I
swallowed his load. I'm so glad I did now. I'm not ashamed of it; we
both enjoyed it and were willing - more than willing. It's not
something I want to forget. It's a memory I'll treasure always."
"Good girl. It's the only way. Yes, I've had a few guys - and girls as
well, but only one regular boy friend as such. He used to like me to
dress in lingerie for him; he was a real stallion, but he would take as
well as give. That's the advantage of a relationship like that - it
doubles the fun."
I was getting apprehensive with her talking like this. I thought about
the obvious implications and my toys in the trunk.
She moved forwards as though to kiss me. "Shall we take that photo?" I
said, feeling unsure. "Sure. I've brought my little digital."
She started with me standing and took shots from several angles,
including a saucy up-skirt shot. She took some head and shoulder
portrait shots, with me smiling, smouldering and pouting for all I was
worth.
Sitting back on the sofa, my skirt naturally rode up to show my
stocking tops and suspenders; she was keen to take these shots,
encouraging me all the time.
"Time for some pantie shots." she said and in a trice she had me open-
legged, showing my bulging black silky panties. Then she got me to
kneel and show my panties from behind, skirt now around my waist. Then
I felt her fingers caress the panties on my arse and try to wriggle
them down. "Let's show that lovely bum." She had my panties down to
expose the full cheeks of arse. "Lovely. Very cheeky."
I turned over and sat down again on the sofa; she joined me again, as
close as ever. She looked at me closely. "You enjoyed that. Can I
possibly persuade you to..."
The sentence was never completed as our lips crushed together in the
most passionate kiss; I felt her tongue probe my mouth and I let her
in, enjoying her snaking exploration of my mouth. I did the same for
her and felt her left hand start to stoke my leg above my stocking top
and on to my bulging panties.
This urged our kissing on to even greater passion as our hands started
to explore each other's bodies; I felt her breasts, her legs and
finally my right hand was over her panties too. We kissed and embraced
and explored, our tongues intertwined and our hands explored further.
Gloria now had hold of my cock, which was absolutely rigid. She too was
fully erect in my hand, caressing her lovingly.
I pulled away. 'Not yet. Not yet. I can't come yet'. "Lets take some
more photos of you. Would you like to try my bigger breast forms? We'd
better fix your make-up too".
Gloria went over to the mirror and put some repairing touches to her
make-up; she dropped her panties to the floor. "They'll only get in the
way." she laughed.
I could not believe what I had done. I'd kissed my first person since I
had left my wife and it had been a man. But not an ordinary man but a
TV like me, someone with very similar tastes who was kind and gentle; I
had enjoyed our intimacy and wanted to do it again very soon.
She came and stood in front of me and slowly lifted her skirt to show
her cock swinging in front of her. My head went forwards, but then she
backed away "Not yet you naughty girl, you slut".
What a wonderful experience - to be called a slut and to have deserved
it. There was no higher compliment as far as I was concerned.
"Come on, try these" she called, fishing in her bag. Gloria dug out
some large bulbous jelly-like breast forms and bra to accommodate them.
"Try this too". She proffered a tight red top with a keyhole neckline.
She got me to carefully remove my wig, top, bra and fillers and replace
them hers. They felt more bulbous and heavy and the top exposed the
cleavage nicely. Gloria re-applied my lipstick and checked the rest of
my make-up before helping me back into the wig.
"These feel great" I said, unable to stop myself fondling them and
feeling their weight. "Try walking round and feel the wonderful bounce
and swell. Look at your cleavage when you bend forwards". I did as she
suggested, trying to imagine how it would be to live every day of your
life with such beautiful breasts this size or even bigger.
I started to pose for more pictures; sitting on the sofa I leaned
forwards to show my new cleavage. I held beneath my breasts and lifted
them, then went onto my knees to dangle them.
"Let's have some more bum shots. Come on, slowly drop the panties" I
was really getting into the swing of this, rolling over onto my side,
panties exposing my cheeks. Then I gathered the fabric to form a thong.
With the panties by my knees, I rolled over to expose a partially erect
cock. Then, losing all inhibitions, the panties were lost and I started
to pose sitting, standing and lying. Eventually, I leaned back in my
seat with my cock fully rigid, whilst Gloria took extreme close-ups of
my cock. I lay back, and for the first time, exposed my bum-hole to
Gloria.
"Christ! What a beautiful, gaping hole. Fuckin' Hell, Pippa, that looks
as though it's seen some action. Wow. If its one thing that turns me
on it's a hole like yours".
There are many different things that arouse sexual interest in man; for
Graham / Gloria it was the sight of a distended arsehole which really
turned him / her on. My hole, from its long practise in accepting very
sizeable toys was now a pronounced muscular ring. Instantly, she was
one her knees for a closer look. "Oh, oh", she whimpered, "Please, may
I touch your beautiful, beautiful, ring."
"Of course" I pouted, "I'm so glad you like it...what else would you
like to do? You can kiss it if you like."
Gloria did not need asking twice. I knelt with my back to her to expose
my hole as much as possible. I felt her hot breath as she approached
me; she was moaning, obviously in raptures at my stretched hole. She
licked her fingers and slowly circled my hole, delicately and slowly.
Her fingers were soon replaced by her tongue, circling at first, but
spiralling nearer and nearer the hole all the time. I felt her tongue
flick into me for the first time, causing me to moan too. My cock was
rock hard and I knew Gloria's would be too. "Oh, that's so good, so, so
good". She pushed her tongue deeper into me, circling all the time.
Then she darted her tongue in and out, in and out, moaning and groaning
with sheer pleasure. She must have spent 20 minutes licking around and
within my hole. She was so turned on; eventually she said breathlessly
"Pippa, turn around and take me". I turned around and there was
Gloria's priapic cock, pointing up, absolutely rock hard, right in
front of my face.
During her licking of me she had not touched her cock once, yet she was
fully erect, bulbous and beautiful. I wanted to satisfy Gloria, yet
also wanted to savour the moment. "Please, please, suck me, suck me."
she cried.
Now it was my turn to enthuse. "That's so, so beautiful. It's 30 years
since I've done this, such an erotic and beautiful practise." I was sat
on the edge of the sofa and put my hands on her naked buttocks and
brought her forwards to meet my lips. I nibbled up the shaft before,
not being able to resist either my desire or Gloria's imploring, taking
the full knob-head into my mouth. I pulled her onto me and she pulled
my head onto her such that her knob was right down the back of my
throat. I resisted the urge to gag. I could tell Gloria was so turned
on from her deep tonguing of my hole she wasn't going to last much
longer. I eased her out and tried to go slowly to make the moment last.
Without removing my mouth from her cock, I gently moved my hot mouth up
and down her, slowly, sensually, using my tongue very, very gently, to
try to delay her moment. Eventually, amongst all her whimpering and
moaning she said "Oh, God, Pippa, I'm gonna cum, babe. Will you take
my load?" I looked up into her eyes. I smiled in full agreement with
what was to come.
I held her full knob in my mouth, continuing to suck gently in pulses.
The first spurt hit the back of my throat. "Oh my Goooood." she
screamed, after pulse after pulse of cream unloaded into my eager
mouth. I closed my throat, for I wanted to hold my mouth in place until
she had fully finished. She was panting when she eased out of my mouth.
I opened up to show her I had a mouthful; I savoured the wonderful
musky, salty taste, like good Brie cheese and pears. Looking deep into
Gloria's eye's I swallowed to lot. I pulled her back to my and licked
the big bead of cum from the end of her knob and massaged as much as I
could from her now-slack cock.
We lay back on the sofa and kissed again. I probed her mouth to ensure
she got a taste of her love cream.
"Oh, God, that was so good", she gasped. "Oh, it was. You tasted
gorgeous. I loved it, loved it", I replied.
"You did seem to enjoy my hole?" I enquired, knowing full well how
turned on she was.
"Your hole is the most exquisite I've ever seen".
I got up and opened my trunk. Without saying a word I handed my toys,
one by one, to Gloria, each getting bigger and bigger as I did so.
"So this is your secret. Well if it does that to your bum, please carry
on".
"I certainly don't intend to stop using them. Would like to see me use
them? "
She didn't need a second invitation. I laid a towel on the sofa and
handed her the tube of lube. "Would you mind?" I smiled. "My pleasure"
she replied with glee, "Just relax back and let me do the rest."
I did not know which dildo she was going to use for I closed my eyes to
concentrate on the wonderful feeling of being taken, being fucked,
being filled and invaded by a monster cock which was never satisfied.
She talked to me as she lubricated a toy and my hole, about how she
wanted to see me really gape. I lay back on the sofa with my legs apart
and bum held open. She probed me with the big knob end of the dildo; it
was big, but not my biggest and the knob-end was soon in my hole. I
gasped and Gloria withdrew it. "You OK?" she enquired, worried that she
had hurt me. "That's just fine, more please! It's better if, when you
go a bit further in, you withdraw first, then do it again; then
gradually, more and more goes in. The more that goes in, the more I
like it!"
Gradually, she probed me. It was really good as she massaged it I and
out, slowly and deliberately. I was partially erect all the time and
she teased me with her lips as she dildo-fucked my arse. Eventually,
after 5 minutes, all the toy was within me and I knew which one she had
used.
"My God, that's amazing to be able to take that. How on earth do you
manage to do that?"
"It's easy" I replied. "It's come with long hours of dedication and
practise, and frankly, I've enjoyed every minute of it."
"Have you only done it since you've been here?" she enquired, taking a
mouthful of my cock.
"No, I've done it for years but since I've been free I've done it much
more often. Frankly, I do it most days now."
Having someone else use a toy like that added another huge dimension;
whereas I would have normally withdrawn fully and inserted again, she
had held the toy within me and it took me to another level of
experience. She continued to massage me with it very gently, sucking
slowly on my rock-hard cock as she did so. My moaning and gutter
language told her how turned on I was.
"Would you like a bigger one? I'm sure you would enjoy something just a
bit bigger." She wasn't expecting a reply and I wasn't going to object.
The current toy was left fully embedded whilst she prepared the
replacement. Gently she removed the first toy; before going any further
she could not resist a good look at my gaping hole. She gasped in
approval then teased the knob of the second toy against my hole,
nudging it slowly. I felt myself slowly open up, but she was thankfully
gentle with me, teasing to open me up just a little bit more with every
push. "Come on, you beautiful filthy whore, you slut, you cocksucker,
you cum-drinker, open your beautiful fuck-hole for me." she whispered.
She massaged my hole some more, added more lube, and continued.
Eventually, my ring must have been fully extended and I felt it
collapse down on over the knob of the dildo. "Oh, oh, my God, my God,
that's huge. Don't stop. Oh I love it. I'm a filthy whore, a filthy
whore. I'm a Queen of sex and Goddess to fucking and sucking and cum.
Fuck, oh, fuck, fuck, fuck".
She slipped out the toy, which I now guessed must be my new, super huge
dildo. Immediately, she eased the heavy monster back in again, this
time a little further. She repeated the process, each time getting
further in. Eventually, having enough in, she started to massage it in
and out. It had got more comfortable with each push, and now I was in a
state of supreme enjoyment, my arsehole now distended and huge.
Gloria leaned over to suck me again; I was flaccid, but I was so turned
on I was soon very hard again.
"Snowball with me?" she asked, wondering if I knew what she meant.
"Oh, fuck, yes, now that would be beautiful" I moaned.
She continued to suck me whilst massaging the huge dildo in and out of
my hole. I was in true ecstasy, unable to think of anything except the
stimulus to my hole, my cock and the hyper-erotic feeling of my clothes
and shoes. My head was awhirl with feeling so intense I almost thought
I should faint. Then, teased by her mouth, I knew I could hold out no
longer.
I screamed. "Fuck me, oh, take my cum in your fucking mouth. Take it
all. Don't stop. Don't stop. Oh, oh, oh, here it coooommmmeeeeessss."
I felt my gland contract to pump love-cream coating Gloria's willing
mouth. She moaned in appreciation of my gift to her, casting glances in
my direction. She held me in her mouth, anxious not to allow any of the
precious fluid to escape. She moved up to my face, smiled without
opening her mouth; very slowly she dribbled cum into my open mouth; I
rolled over onto my side and did the same to her. Her head rose to meet
mine and she pushed me over onto my back again, her lips compressed
against mine, her tongue deep inside my mouth, desperate for more cum
to swallow.
When our lips parted we both knew we had shared something very special.
"My God, you are SO sexy!" she panted, "That was unbelievably
beautiful. Thank you darling, sexy, Pippa."
"If that wasn't the best cum I've ever had..." I gasped, easing the
monster dildo from my hole. I turned around on the sofa, leaned back
and opened my hole for Gloria. I must have been really gaping now,
spasming between a relaxed gape and a relatively tight hole.
Again Gloria approached, quite in awe with what she was seeing. "I can
see I'm going to need lessons from you now" she said.
"How's that?" I was confused.
"I want you to help me achieve the same level of beauty as you. But
that must be another time. I must go now." We kissed again before she
changed back to Graham. I made her promise to come and see me another
time and she said she would call or send me a message.
When she had gone, I lay back on the sofa and relaxed, still dressed as
Pippa, adamant I did not want to change. I had enjoyed walking around
in my new stilettos and feeling the erotic sensuousness of sheer nylon
against my legs. I realized I was still sporting Gloria's boobs and
that she had photos of me on her camera. I was not worried, though I
should have liked to see the pictures myself as a testament to the
fantastic time we had enjoyed that afternoon.
Amazingly, so I reflected afterwards, I had no guilt feelings
whatsoever. At no time did I feel what I was doing was sordid, dirty,
or for us, unnatural. It was just the way we were.
My phone buzzed. Her message said: "That was best ever. Want more? Luv
G."
I replied. "Still enjoying your tits. Want more! Luv P."
I wrote up all the day's experience at some length in my diary,
reliving the excitement and sheer joy of the wonderfully erotic things
we had done together. Before, I may have wanted to throw all away;
tonight I wanted to savour the experience - and do it again as soon as
possible.
That night I went to bed slightly sore and tired. Yet I felt truly
satisfied and invigorated, as though enlivened and inspired. Maybe I
could now work without consuming feelings of frustration and anger. And
my final thought was simply, after many years and months of unmitigated
unhappiness, I now, at long last, had something to look forward to.
7. Sublime transcendence.
The week went well. I worked like never before, able to concentrate on
every task in hand. I was productive, stimulated, and happy. I felt
alive and free, not crushed by duty and guilt.
Gloria had obviously been turned on by my distended, gaping hole. I was
not going to disappoint her the next time we met. I dressed each and
every night, applying the make-up techniques Gloria had taught me. I
also used my toys every night, dreaming of Gloria and our sex together.
I wore a plug whenever I could and wore my very biggest plug for most
of the day on Saturday.
By 10 o'clock the next Sunday, Gloria and I were dressed, made-up and
had enjoyed our first passionate kiss of the day. In place of the long
blonde wig she'd worn the previous Sunday she was now wearing a shorter
dark wig in a simple style. As her habit, her eye make-up was very
sultry and attractive using