Some of the detail in this story is fiction, but it is
strongly based on my first experience of "dressing" and
the consequences. I think of it as "enhanced truth", for
as the Irish say "a good tale should always improve in
the telling". For the record I spent several years as a
child with a house full of Irish navvies, and great
Back in the late 1960's I came home on leave from the Army
to find my mother was away looking after her younger sister
who was ill. My father had disappeared when I was a baby
so I had the place to myself. All my old mates were working
during the day and pussywhipped by their wives/girlfriends in
By day three I was bored silly and, although the dreadful
"passion killer" tights were the usual wear for girls at the
time, I had begun my interest in girls when stockings and
suspenders were normal (far easier to get your hands 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 drawers and found lots of tan
stockings (not much choice of colours then, even black was rare
and regarded as too sexy for day to day wear).
Next I found her corsets and suspender belts, slips etc, and
soon sat in a deep, boned white corset with the four suspenders
attached with those little triangular tabs to tan nylon stockings.
These had very little stretch 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, giving delightful feelings,
the whole thing had me bone hard, which tented the white silky
slip I was wearing.
For an hour or more, I sat in front of a mirror, moving my legs
to "flash" stocking tops and white thigh flesh, and occasionally
my own cock, all very sexy but no pics then unless you were rich
enough to own a Polaroid.
After wetting my thighs and stocking tops with my own cum, I cleaned
up and with "normal" clothes on drove into the nearby market town. As
fate would have it I found a parking place close to the town centre
public toilets, the old underground type, now sadly gone in most places.
This small town loo only had two traps, but I would go and read both
doors, like any normal 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 tales. As I
bent 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 middle finger. I understood the wanking bit
but at the time Didn't understand the finger (I found out not very
My immediate reaction was to pull up my trousers and leave the loo
and sit in my car, while I sorted my thoughts out. I adjusted my
mirror to watch the (only) loo entrance. 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 partition and I had flashed my bare arse to
the other trap when reading. The wanking bit I understood, but that
finger wiggling had me. I even considered that there was a young girl
in there, wanting to swap a wank for a pussy fingering (yes I was
After ten minutes no-one had entered or left the loo and I walked back
over, down the steps and back into my original trap. I dropped my
trousers, faced the partition, 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".
Going next door took only a momment, and the door was locked behind me.
I found a 50ish man who put his cock in my hand 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 reaction came, so I kissed back hard with maximum tongue 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 kiss I whispered that I had a safe place, transport near
and about my dressing that morning. He told me his name was John and
I told him mine was Michael Soon we were driving to my place
both stroking the others cock. Once home we went to the bedroom and I
put on the corsette and stockings from the morning. As he got naked. I
started to feel very sexy in my gear and started kissing him hard again
as he explored my body 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 camp for several 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 fucking and expected
to have his cock sucked. He said that he thought that as I had started by
Dressing, that I would become a "Bottom" who would suck cock and take it up
my arse. I had not thought any of this through, but when I immagined myself
in both rolls, my cock stiffened as I thought of being a bottom.
SO, JUST LIKE THAT, MY NEW PLACE IN LIFE 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 peel 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 my teeth clear of this precious meat. Soon I was
really getting into it with my head 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 seconds or so, keeping him deep in my mouth at the
end of each one, as I relaxed my grip on his cock to allow a little more
in each time. As I started to gag a little, he told me to try swallowing
as his cockhead entered my throat, which helped, and I really wanted to feel
his pubic hairs on my lips, and soon did.
All this kept him nice and hard, and got me used to having a cock in my
mouth and throat for extended periods. 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 "pussy"). One, two, then three fingers
entered my pussy to their full length, stroking in and out and round and round
to prepare me for my first fucking, always momentous for a "girl" as I was
beginning to think of myself. Its funny how fingers up your pussy can change
John then asked me to kneel on the edge 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 longer a virgin, but part way to being a true "girl".
I experienced some slight pain, but his preparation had done the job, and after a
couple of minutes for my body to adjust, he began to slowly work his full length
in. Out an inch, back in one and a half, adding lube at every out stroke til
the hairs that had tickled my chin, now tickled my cheeks. Again he paused, this
time 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 painful, as well as getting my deeper bowels used to the invasion
of hard meat. After a few minutes of this, and after all pain stopped as he
re-entered me, he began a slightly shorter stroke, still going fully in, but leaving
his cockhead in all the time. He speeded up his strokes 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 loads of spunk onto the sheets,
corsette and stockings, and thrashing about moaning. He gripped my hips hard and
"Rode The Tiger", all the time fucking me harder and faster, till I had another,
less intense but much longer cum, gripping him with hard spasms of my pussy and
taking him over the edge into his. My bowels getting a thick coating of his sperm,
enough to make several babies if I had had the right equipment.
Both our cocks slowly wilted after such an intense fuck, til his dropped out with
a soft "plop", and his spunk flowed out of my pussy and joined that on the sheets.
John stayed several more hours, fucking me twice more, by which time he was knackered
and my pussy was a bit sore (before he left he annointed my pussy with a salve to
get it ready for the next 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 lessons 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 couple of his "Top" friends, to continue My "initiation". They would also bring
some nicer (that is to say sexier) clothes for me to wear.
Rather than have me take him back to where we had met, he used our phone to call
one of those friends, Sam, to pick him up. he came in briefly and after introductions,
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 nights rest would have me ready for fuller sessions the next day.
John was certainly right about the last bit, and I trusted him after the way he had
taken me through my first steps 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 night would find me even more bored?
I HOPED SO!
people they were.
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