My First Time
TransvestiteSome of the detail in this story is fabrication, but it is
strongly based on my first experience of `` dressing '' and
the consequences. I think of it as `` enhanced verity '', for
as the Irish whisky say `` a respectable tale should always improve in
the telling ''. For the record I spent several year as a
tyke with a house full of Irish people peon, and keen
Back in the lately 1960 's I came nursing home on leave from the US Army
to find my mother was away looking after her vernal babe
who was ill. My Fatherhood had disappeared when I was a infant
so I had the berth to myself. All my old couple were working
during the day and pussywhipped by their wives/girlfriends in
the evening.
By day three I was bored silly and, although the abominable
'' passion killer whale '' tights were the common wear for girlfriend at the
time, I had begun my sake in young woman when stockings and
suspenders were pattern ( far prosperous to get your hands in a
girls knickerbockers 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 mother drawers and found mint of tan
stockings ( not much choice of semblance then, even Negroid was rarified
and regarded as too aphrodisiac for day to day wear ).
Next I found her girdle and suspender whang, slips etc, and
soon sat in a cryptical, boned Edward Douglas White Jr. corset with the four brace
attached with those little trilateral tabs to tan nylon stockings.
These had very little stretchiness in them so once attached they and
the boning gave a feeling of tight containment which I really
enjoyed. With the short suspender tabs and stockings designed to
only reach mid thigh, the square edge of the corset stopped at
the bottom of my arse cheeks at the rear and pressed hard on
the base of my cock at the front man, giving delightful touch,
the whole thing had me bone hard, which tented the egg white silky
slip I was wearing.
For an hour or More, I sat in front of a mirror, moving my legs
to `` flash '' stocking tip and Patrick Victor Martindale White second joint pulp, and occasionally
my own turncock, all very sexy but no photo then unless you were rich
enough to own a Polaroid.
After wetting my thigh and stocking big top with my own cum, I cleaned
up and with `` normal '' clothes on drove into the nearby grocery store townspeople. As
fate would let it I found a park post close to the town sum
public stool, the old underground type, now sadly gone in most places.
This modest town loo only had two trap, but I would go and record both
doors, like any normal male.
Soon I was sat in a trap reading the dirty account, still at that
stage mainly hetro, with the odd gay one and zero TV tarradiddle. As I
knack forward to read a good 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 in-between finger. I understood the wanking bit
but at the clip Did n't understand the finger ( I found out not very
much later ).
My immediate reaction was to pull up my trouser and leave the loo
and sit in my car, while I sorted my thought out. I adjusted my
mirror to watch out the ( only ) loo entering. while I watched I tried to
sort out in my own mind what had just happened. I decided that there
must be a peephole in the division and I had flashed my bare arsehole to
the former trap when recitation. The wanking bit I understood, but that
finger's breadth wiggling had me. I even considered that there was a Whitney Young daughter
in there, wanting to swap a wank for a pussy fingering ( yes I was
that naive ).
After ten second no-one had entered or left the loo and I walked back
over, down the pace and back into my original trap. I dropped my
trousers, faced the sectionalisation, and put one foot slightly under the gap
at the bottom. my foot was tapped and soon a note passed under, saying
'' CUM IN HERE ''.
exit next room access took only a momment, and the door was locked behind me.
I found a 50ish man who put his cock in my helping hand and started stroking
mine. As we faced each early, he leant in and started kissing me, which
I started returning without thinking, finding it very pleasurable before any
bad chemical reaction came, so I kissed back hard with maximum clapper action.
His free hand 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 buss I whispered that I had a dependable place, transport near
and about my stuffing that morning. He told me his name was can and
I told him mine was Michael Soon we were driving to my office
both stroking the others cock. Once home we went to the sleeping accommodation and I
put on the corsette and stockings from the aurora. As he got naked. I
started to feel very sexy in my paraphernalia and started kissing him voiceless again
as he explored my physical structure with his hands.
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 summer camp for several years.
Quite a few of them had taken to it and he 'd savor it ever since,
He started by saying that he was a `` Top '' who did the fucking and expected
to deliver his cock sucked. He said that he thought that as I had started by
fertilisation, that I would suit a `` buttocks '' who would give suck cock and admit it up
my tush. I had not thought any of this through, but when I immagined myself
in both rolling, my cock stiffened as I thought of being a bottom.
SO, JUST the likes of THAT, MY NEW lieu IN aliveness WAS DECIDED ! !
Trully we are ruled by our cocks.
He started by showing me how to suck his cock, controlling the penetration
by holding the base of the cock and as much more of its length as needed.
I learned to unclothe back the foreskin from the helmet with my lips and to
push the tip of my tongue into his pee-slit. to skid my lingua under the
cock and to always hold my tooth open of this precious heart and soul. Soon I was
really getting into it with my mind bobbing up and down over his groin.
He told me to slow down, as he wanted to pop my cerise, so I started to
do one `` bob '' every five mo or so, keeping him deep in my mouth at the
end of each one, as I relaxed my adhesive friction on his cock to leave a little more
in each time. As I started to gag a piffling, he told me to try swallowing
as his cockhead entered my throat, which helped, and I really wanted to finger
his pubic hairs on my lips, and soon did.
All this kept him prissy and heavily, and got me used to having a cock in my
mouth and throat for extended stop. Meanwhile, he was fingering ( that wiggle
again ) my arsehole with some lubricant ( by the end of the session I was
using his description, and calling it my `` cunt '' ). One, two, then three fingers
entered my pussy to their full length, stroking in and out and round and turn
to cook me for my first nookie, always momentous for a `` girl '' as I was
beginning to think of myself. Its amusing how finger's breadth up your kitty can change
your perceptions.
whoremonger then asked me to kneel on the edge of the bed, bum in air and point down
into a pillow, while he stood on the floor behind me at just the decently 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 time
of pressing, and then his cockhead just slid through with an inch or so below
the helmet, I was no tenacious a virgin, but part way to being a true `` fille ''.
I experienced some slight pain, but his preparation had done the job, and after a
match of minutes for my body to line up, he began to slowly act upon his full length
in. Out an inch, back in one and a half, adding lubricator at every out apoplexy til
the hairs that had tickled my chin, now tickled my cheek. Again he paused, this
fourth dimension fully in me, for a couple of minutes to get me used to a pussy full, then
slid fully out, but straight back in again, working the entrance muscles, which was
still slightly awful, as well as getting my deeper bowel used to the invasion
of hard gist. After a few transactions of this, and after all pain stopped as he
re-entered me, he began a slightly shorter separatrix, still going fully in, but leaving
his cockhead in all the time. He speeded up his throw and said `` now we are really
fucking '' as I began to, quite naturely push back into his thrusts.
Without warning, I had an intense orgasm, spilling scads of spunk onto the weather sheet,
corsette and stockings, and thrashing about moaning. He gripped my articulatio coxae hard and
'' Rode The tiger '', all the time fucking me punishing and faster, till I had another,
less intense but much farsighted cum, gripping him with hard spasms of my pussy and
taking him over the edge into his. My intestine getting a thick coating of his spermatozoon,
enough to realise respective child if I had had the decent equipment.
Both our putz slowly wilted after such an intense nooky, til his dropped out with
a balmy `` plop '', and his spunk flowed out of my pussy and joined that on the sheets.
John Lackland stayed several More hour, fucking me twice more, by which time he was knackered
and my puss was a bit sore ( before he left he annointed my pussy with a balm to
get it prepare for the next day ). That came out of our talking as we kissed and
fondled between screwing. He knew that I had ten sidereal day leave left and naught to do and
that I wanted more object lesson in sex. He told me that after today, he might only manage
two fucks tomorrow, but that I deserved more ( I agreed ). So he would come `` tenish ''
with a couplet of his `` Top '' friends, to continue My `` initiation ''. They would also lend
some nicer ( that is to say sexier ) clothes for me to wear.
Rather than have me choose him back to where we had met, he used our phone to call
one of those supporter, Sam, to pick him up. he came in briefly and after introduction,
he pulled out his cock to read me. It was MUCH with child than lav, and I think Sam
and I would have fucked there and then, had not King John intervened, saying that I had
been fucked enough for the number 1 day and could be damaged or put-off by more. But
that a good nights residuum would ingest me ready for fuller sessions the next day.
whoremonger was certainly right about the final bit, and I trusted him after the way he had
taken me through my world-class whole tone 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 bored '' in a different way.
Perhaps tomorrow dark would find me even more bored ?
I HOPED SO !
the great unwashed they were.
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