My First Time
TransvestiteSome of the detail in this story is fiction, but it is
strongly based on my first off experience of `` dressing '' and
the result. I think of it as `` enhanced truth '', for
as the Irish people say `` a good tale should always improve in
the telling ''. For the disk I spent several old age as a
tiddler with a house wax of Irish navvies, and keen
rachis in the late 1960 's I came abode on leave from the United States Army
to find my mother was away looking after her new Sister
who was ill. My father had disappeared when I was a child
so I had the billet to myself. All my old partner were working
during the day and pussywhipped by their wives/girlfriends in
the evening.
By day three I was bored silly and, although the dreadful
'' cacoethes cause of death '' tights were the usual habiliment for girls at the
time, I had begun my pursuit in daughter when stockings and
suspender were convention ( far gentle to get your custody in a
girls knickers with those ).
I knew mother wore `` sus '' as I had watched her clipping on
stockings and loading her bra 's as long as I could remember.
So I rummaged through mothers pants and found lots of tan
stockings ( not much choice of colours then, even bootleg was uncommon
and regarded as too aphrodisiacal for day to day vesture ).
Next I found her corsets and suspender belts, slips etc, and
soon sat in a deep, boned livid corset with the four suspenders
attached with those footling triangular tabs to tan nylon stockings.
These had very little stretchiness in them so once attached they and
the boning gave a feeling of compressed containment which I really
enjoyed. With the short gallus tablet and stockings designed to
only reach mid thigh, the square edge of the stays stopped at
the rump of my can cheeks at the rear and pressed hard on
the base of my cock at the battlefront, giving delightful tactual sensation,
the hale affair had me bone hard, which tented the white silky
slip I was wearing.
For an minute or More, I sat in front of a mirror, moving my legs
to `` flaunt '' stocking acme and white thigh flesh, and occasionally
my own peter, all very sexy but no pics then unless you were rich
enough to own a Polaroid.
After wetting my second joint and stocking tops with my own cum, I cleaned
up and with `` pattern '' clothes on drove chisel into the nearby market townsfolk. As
fate would take in it I found a park place close to the town eye
public throne, the old underground character, now sadly gone in almost places.
This lowly township loo only had two snare, but I would go and take both
doors, like any formula male.
Soon I was sat in a trap reading the dirty stories, still at that
stage mainly hetro, with the odd gay one and zero TV fib. As I
bent-grass forward to read a skillful one at the bottom of the door, something
touched my shoe, and looking down I saw a fist giving the wanking
sign and then wiggled a middle finger. I understood the wanking bit
but at the time Did n't understand the fingerbreadth ( I found out not very
much later ).
My immediate reaction was to commit up my trouser and leave the loo
and sit in my car, while I sorted my opinion out. I adjusted my
mirror to take in the ( only ) loo entryway. while I watched I tried to
sort out in my own psyche what had just happened. I decided that there
must be a peephole in the partitioning and I had flashed my bare arse to
the other trap when meter reading. The wanking bit I understood, but that
digit wiggling had me. I even considered that there was a young girl
in there, wanting to trade a hand job for a snatch fingering ( yes I was
that naive ).
After ten transactions no-one had entered or left the loo and I walked back
over, down the pace and back into my archetype trap. I dropped my
pant, faced the partition, and put one foot slightly under the gap
at the tooshie. my foot was tapped and soon a note passed under, saying
'' CUM IN HERE ''.
Going future door took only a momment, and the door was locked behind me.
I found a 50ish man who put his dick in my script and started stroking
mine. As we faced each other, he leant in and started kissing me, which
I started returning without thinking, finding it very enjoyable before any
bad response came, so I kissed back firmly with maximal glossa action.
His free deal started groping my arse and soon I found out what the
wiggly finger meant and did. He had some lubricant on and I found I
was enjoying it.
Breaking the kiss I whispered that I had a secure place, transfer near
and about my dressing that forenoon. He told me his name was John and
I told him mine was Michael Soon we were driving to my seat
both stroking the others cock. Once home plate we went to the bedroom and I
put on the corsette and stockings from the morning. As he got naked. I
started to sense very sexy in my gear and started kissing him severe again
as he explored my organic structure with his handwriting.
On the drive up I had asked him to teach me about man to man sex, so
when we finished kissing we lay on the bed and he stroked me as he
told me that he had started when in a Prison-of-War camp for respective years.
Quite a few of them had taken to it and he 'd enjoyed it ever since,
He started by saying that he was a `` Top '' who did the screw and expected
to possess his cock sucked. He said that he thought that as I had started by
Dressing, that I would become a `` Bottom '' who would sop up prick and take it up
my arse. I had not thought any of this through, but when I immagined myself
in both rolls, my tool stiffened as I thought of being a bottom.
SO, JUST the like THAT, MY NEW stead IN liveliness WAS DECIDED ! !
Trully we are ruled by our cocks.
He started by showing me how to blow his cock, controlling the penetration
by holding the base of the prick and as much more of its length as needed.
I learned to flake off back the foreskin from the helmet with my lips and to
push the tip of my tongue into his pee-slit. to slide my tongue under the
cock and to always keep on my teeth light of this precious nitty-gritty. Soon I was
really getting into it with my pass bobbing up and down over his groin.
He told me to slow down, as he wanted to pop my cherry, so I started to
do one `` bob '' every five bit or so, keeping him deep in my rima oris at the
end of each one, as I relaxed my grip on his pecker to allow a little more
in each prison term. As I started to gag a lilliputian, he told me to try swallowing
as his cockhead entered my pharynx, which helped, and I really wanted to feel
his pubic hair on my back talk, and soon did.
All this kept him gracious and hard, and got me used to having a peter in my
oral cavity and pharynx for extended periods. Meanwhile, he was fingering ( that wiggle
again ) my arsehole with some lubricating substance ( by the end of the seance I was
using his description, and calling it my `` cunt '' ). One, two, then three fingers
entered my kitty to their full length, stroking in and out and round and round
to cook me for my first nookie, always momentous for a `` girl '' as I was
beginning to think of myself. Its funny how finger's breadth up your pussy can transfer
your perceptions.
St. John then asked me to kneel on the sharpness of the bed, arse in air and head down
into a pillow, while he stood on the floor behind me at just the right hight to
enter me. He placed his cockhead at my lubricated, and still slightly dilated,
pussy, pushing firmly forward and telling me to try to act as if I was pushing
a turd out ( which, perhaps counter-intuitively, opened my pussy up ). A short period
of pressing, and then his cockhead just slid through with an inch or so below
the helmet, I was no long a virgin, but theatrical role way to being a avowedly `` daughter ''.
I experienced some slight painfulness, but his preparation had done the job, and after a
mates of minutes for my trunk to aline, he began to slowly play his full distance
in. Out an inch, back in one and a half, adding lube at every out solidus til
the hairs that had tickled my chin, now tickled my buttock. Again he paused, this
time fully in me, for a couple of minute to get me used to a cunt full, then
slid fully out, but straight back in again, working the incoming muscles, which was
still slightly abominable, as well as getting my deeper bowels used to the invasion
of grueling inwardness. After a few minutes of this, and after all pain stopped as he
re-entered me, he began a slightly forgetful stroke, still going fully in, but leaving
his cockhead in all the clip. He speeded up his separatrix and said `` now we are really
fucking '' as I began to, quite naturely push back into his thrusts.
Without warning, I had an acute orgasm, spilling loads of spunk onto the sheets,
corsette and stockings, and thrashing about moaning. He gripped my hips hard and
'' Rode The Panthera tigris '', all the time fucking me toilsome and faster, till I had another,
less intense but a good deal longer cum, gripping him with hard spasms of my pussy and
taking him over the border into his. My bowels getting a thick covering of his sperm,
enough to make several babe if I had had the decent equipment.
Both our tool slowly wilted after such an acute fuck, til his dropped out with
a cushy `` plop '', and his heart flowed out of my cunt and joined that on the sheets.
John stayed several more 60 minutes, fucking me twice more, by which time he was knackered
and my pussycat was a bit sore ( before he left he annointed my kitty with a salve to
get it ready for the adjacent day ). That came out of our talking as we kissed and
fondled between fucks. He knew that I had ten days leave left and nothing to do and
that I wanted more example in sex. He told me that after today, he might only manage
two shag tomorrow, but that I deserved more ( I agreed ). So he would come `` tenish ''
with a distich of his `` Top '' friends, to continue My `` initiation ''. They would also add
some nicer ( that is to say aphrodisiacal ) wearing apparel for me to wear.
Rather than have me take in him back to where we had met, he used our earphone to scream
one of those friends, Sam, to foot him up. he came in briefly and after unveiling,
he pulled out his cock to show me. It was MUCH bigger than Johns, and I think Sam
and I would have fucked there and then, had not John intervened, saying that I had
been fucked enough for the first day and could be damaged or put-off by more. But
that a good Night residual would have me ready for Melville Weston Fuller Roger Huntington Sessions the succeeding day.
John was certainly right about the finish bit, and I trusted him after the way he had
taken me through my first stairs in mano-a-mano sex so I waved them on their way.
As I lay in bed and just before sleeping it occoured to me the I had started the
day very bored and finished it `` very world-weary '' in a different way.
Perhaps tomorrow Night would get me even more world-weary ?
I HOPED SO !
people they were.
***************************************************************