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By (user no longer on site) OP
over a year ago
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It constantly amazes me that I read so-called autobiographical stories about some guy who suddenly decides to crossdress or is forced to dress as a woman, and with no previous experience or preparation suddenly transforms from hairy man into a sexy stunning woman.
The story below as a tongue in cheek dig at these stories. I apologise to those guys out there who manage to just slip into a pair of stockings, high-heels, wig and makeup and suddenly look like Kim Bassinger; I'm sure all of your stories are real.
To read the story, just select any of the options a to d, to put together your very own autobiographical "Grab Bag" first time transvestite story
The Day I Decided to Become a Transvestite and Got Fucked
By
Mr Kinks
I had had the urge to wear women's clothing ever since:
a) I can remember,
b) I was a teenager,
c) I was forced to wear big navy blue pants to school instead of shorts,
d) I was a foetus.
By some fortunate coincidence, one day I found myself home alone; and
unable to repress the urge to dress as a woman any longer, I decided that
I would do so today. By some fortunate coincidence I had a disease with
the symptoms which meant that although I had a full head of hair,
eyebrows and eyelashes, the rest of my body remained hairless so I didn't
have to shave myself at all.
I stripped naked and made my way into my:
a) sister's,
b) mother's,
c) aunt's,
d) transvestite uncle's, bedroom
and sat at the dressing table. Despite the fact that I had never used
nailpolish before and even though my
a) sister,
b) mother,
c) aunt,
d) transvestite uncle,
could return home at any time without warning, I painted my finger and
toenails perfectly first time. Even though I had never used cosmetics
before in my life, it seems that just by reading my:
a) sister's,
b) mother's,
c) aunt's,
d) transvestite uncle's,
fashion magazines, I had learned enough to make myself up so that I
looked like a supermodel.
By some fortunate coincidence my:
a) sister,
b) mother,
c) aunt,
d) transvestite uncle,
kept a selection of good quality wigs so I selected a:
a) shoulder length blonde,
b) black bob,
c) waist length brunette,
d) green and red mohawk,
wig and set it neatly on my head. I looked stunning!
I rummaged around in my:
a) sister's,
b) mother's,
c) aunt's,
d) transvestite uncle's,
lingerie drawer and found exactly what I needed. I selected a pair of
a) silk cami-knickers,
b) satin thong panties,
c) nylon boy-leg panties,
d) cotton incontinence underpants,
and slipped them on. Next I selected a:
a) matching bra,
b) silk lined bustier,
c) black satin corset,
d) straightjacket,
and slipped into it. Unfortunately my
a) sister,
b) mother,
c) aunt,
d) transvestite uncle
had recently undergone a double mastectomy; but that meant there was an
assortment of breastforms available to me so I selected a set of 36 C's
and slipped them inside the bra cups.
Next I slipped into
a) a satin suspender belt and seamed stockings,
b) sheer-to-the-waist fashion tights,
c) fully-fashioned hold-up stockings,
d) stripey football socks.
I was now becoming aroused and my
a) eight-inch throbbing monster,
b) swollen brute,
c) purple headed kidney puncher,
d) three inches of snarling pork sword, was becoming uncomfortable in my
underwear.
I opened my:
a) sister's,
b) mother's,
c) aunt's,
d) transvestite uncle's,
wardrobe and was pleasantly surprised to find an incredible assortment of
sexy skirts, blouses, suits, and bizarre costumes. By some fortunate
coincidence all of the clothing was in my size. I selected:
a) sexy A-line miniskirt and silk blouse,
b) a smart but sexy business suit,
c) a satin fetish nurse's uniform,
d) a Jimmy Saville satin tracksuit,
and got myself dressed.
In the wardrobe there was also a selection of lovely high heels, fetish
boots and pumps, which by some fortunate coincidence also happened to be
in my size. I selected:
a) a pair of black high-heeled Stiletto's,
b) a pair of pink 'fuck-me' high-heels,
c) a pair of black patent-leather thigh-high boots,
d) a pair of Jimmy Saville training shoes,
and slipped them on.
By some fortunate coincidence, my:
a) sister,
b) mother,
c) aunt,
d) transvestite uncle,
kept a selection of clip on earrings and trashy jewellery, which I put on
and then I sprayed myself with perfume and as a finishing touch.
I looked at myself in the mirror and was amazed to see that although I
had never attempted to dress like a woman before, I had transformed
myself from a fat middle-aged man into a stunning sexy vixen! I decided
I would call myself:
a) Vanessa the Undresser,
b) Sally Swallows,
c) Bendy Wendy,
d) Jemima Saville.
By some unfortunate coincidence, even though I had decided to crossdress
in broad daylight with the blinds open and the lights on, I had failed to
lock or even close the door to the house and unbeknownst to me I was
being watched by:
a) my nosey pervert neighbour,
b) my nosey pervert paperboy,
c) my nosey pervert milkman,
d) Jimmy Saville (a well known pervert!).
He had slipped quietly into the house and was now standing at the bedroom
door. He sauntered into the room and held up:
a) a knife,
b) a gun,
c) a hatchet,
d) a Gary Glitter record.
"If you don't do exactly what I tell you, I'll use this on you," he
threatened, "I've been watching you through your window and by some
fortunate coincidence I was thinking about how much I have wanted to fuck
a transvestite. Ever since:
a) I can remember,
b) I was a teenager,
c) I was forced to wear big navy blue pants to school instead of shorts,
d) I was a foetus,
in fact," he finished and motioned me over to the bed.
"Ok sister open your mouth," he said, and opened his flies.
Out popped:
a) the largest penis I had ever seen,
b) the smallest penis I had ever seen,
c) the hardest penis I had ever seen,
d) the cutest penis I had ever seen.
This of course immediately turned me on because besides fantasising about
crossdressing; I had also fantasised about being forced to submit to a
strange man whilst I was dressed as a woman ever since:
a) I can remember,
b) I was a teenager,
c) I was forced to wear big navy blue pants to school instead of shorts,
d) I was a foetus.
I reached out and took hold of the man's throbbing, pulsing, quivering,
turgid, rock-hard penis and:
a) put it in my mouth,
b) licked it like a lolly,
c) deep throated it,
d) used it as a stylus for the Gary Glitter record.
By some fortunate coincidence, even though I had never touched a penis
before except my own, I was able to suck this man's cock like a world
class fellatrix.
The man began to:
a) moan with desire,
b) groan with ecstasy,
c) gasp with passion,
d) said "Now then, Now then Gals and Gals",
as he fucked my face. I was becoming more aroused as my own penis:
a) pushed against my panties,
b) tented my skirt,
c) poked a hole in my tights,
d) wriggled like a worm.
I spat out the man's cock and pleaded with him: "
a) please fuck me like a transvestite whore,
b) please take my transvestite cherry,
c) please fill up my transvestite ass-pussy with your cock,
d) please put your wee-wee in my poop chute,"
in my most sexiest voice.
The man threw me onto the bed causing my skirt to ruck up revealing my:
a) sexy nylon panties,
b) sexy stocking tops,
c) sexy sheer tights,
d) fat pimply white thighs.
"Now I'm going to:
a) fuck you senseless,
b) shag you until you scream,
c) bonk your brains out,
d) finish playing this Gary Glitter record,"
the man said and threw himself on top of me.
By some fortunate coincidence I had recently lubricated my back passage
so when the man:
a) tore off my panties and slammed himself deep inside me,
b) pushed his cock right through my tights and slammed himself deep
inside me,
c) pulled the crotch of my panties to one side and slammed himself deep
inside me,
d) finished playing his Gary Glitter record and slammed himself deep inside me,
I felt no pain and only pleasurable feelings.
The man shagged me like I was a transvestite whore begging to be fucked;
oh sorry I was a transvestite whore begging to be fucked, and I was
enjoying every minute of it.
The man groaned: "
a) take that you transvestite whore who's begging to be fucked,
b) I'm fucking your arse like a transvestite whore who is begging to be
fucked,
c) yeah baby, take my cock like a transvestite whore who's begging to be
fucked,
d) "Just imagine Gary Glitter is here as well"
as he fucked my virgin bottom.
I knew he was about to come because he really picked up the pace and
grabbed my thighs and slammed himself deep inside me; oh and he also
said, "I'm coming! I'm coming!" which was sort of a give away.
I was close to coming myself and could feel my orgasm approaching like:
a) an express train,
b) a runaway lorry,
c) a speeding bullet,
d) an orgasm.
"I'm coming too" I screamed and the man:
a) let his cock explode deep inside,
b) pulled out and creamed all over my face,
c) squirted his semen all over my legs and stocking tops,
d) decided to finish with himself with a wank because fucking my arse was
like sticking his cock in a bowl of cold porridge.
My own orgasm raged through me and I:
a) let go inside my panties,
b) sprayed my juice all over my tummy,
c) shot my load inside my tights,
d) farted and had to apologise.
The man got off me and pulled me to my feet. He kissed me and squeezed
my buttocks and said: "
a) I'm going to come over here and fuck you like this every day for the
rest of your life,
b) will you marry me?
c) next time lets both dress up,
d) next time can Gary join in?"
He then walked out of the room leaving me with ravaged makeup, a sore
arse and semen stained clothing. By some fortunate coincidence there was
a one-hour dry cleaner on the corner who specialised in removing semen
stains. But that was the least of my worries; what really concerned me
was that standing at the window, and who had been watching the whole
performance was my:
a) sister,
b) mother,
c) aunt,
d) transvestite uncle.
As it turns out my:
a) sister,
b) mother,
c) aunt,
d) transvestite uncle,
was not angry and in fact had been turned on. What happens next is best
told in my new, autobiographical, real life, true story. If this story
isn't true then:
a) may lightning strike me,
b) may I get run over by lorry,
c) may all of my stockings have ladders in them,
d) may I have to live with Jimmy Saville and wear shit nylon tracksuits for the rest of my life!
...........................Hopefully NOT to be continued. |
