Saturday Girl
It all began in one of those Saturday lulls when the shop was quiet and all the
work was done. Kerry and I were on the main pay desk when Dave, the manager,
came over. He told Kerry that she wasn't to wear jeans to work again and that
she should wear the uniform skirt as she usually did. This started an argument
of course, Kerry arguing that her jeans were black and smart (which they were),
that some of us guys wore them (which we did), and that it was too cold for
skirts (which it was).
I pointed out that insisting she wear a skirt was sex discrimination. Dave,
who's a good manager and not at all petty, tried to wriggle out of it but the
fact was he'd never objected to guys wearing jeans if they were smart so
stopping Kerry, or any of the girls, wearing them was a non starter.
My mistake was mentioning that the rules should apply equally to everyone as he
turned around and said, "alright, Bob, if you wear a skirt and blouse tomorrow,
Kerry can wear jeans."
Kerry laughed. "Yeah, go on Bob."
I grimaced at Dave and said, "okay, I'll call that bluff. Blouse and skirt
tomorrow."
Dave was a little taken aback but he couldn't back out now and it was agreed.
The girls could wear jeans in future if I showed up for work the next day in the
women's uniform.
The guys thought I was crazy and the girls thought I was their hero and spent
most of the day giving me tips about make up and how to walk in heels, it was
quite good fun.
And me? I was getting very nervous about the whole thing. You see I'd been
dressing in women's clothes for years but only in the privacy of my own home and
while part of me couldn't believe my luck the rest of me was panicking at the
thought of everyone seeing me dressed.
During my lunch hour I walked up the high street to the department store on the
corner and bought myself a lovely white blouse with some pretty embroidery on
the shoulders and cuff as well as a new lipstick in a more conservative burgundy
than the tarty scarlets I wore at home. My final purchase was a new pair of
barely black stockings that were not too sheer; after all, these were work
clothes.
Back at work we were mad busy for the next few hours but on my coffee break Dave
came into the staff room and gave me a skirt. "I think it'll fit." He said and
grinned. "Try it on if you like." I laughed at his joke but for a moment I
thought I saw a look in his eyes that wasn't laughing.
Of course that night I got home and tried my new outfit on and was quite pleased
with the results. I already had a pair of shoes that weren't too high and had
thick, chunky heels that could be used for a girl's work shoes and my hair was
long and usually tied back in a pony tail for work but I spent a good four hours
that night trying different make up combinations and hair styles before I
finally found the look I thought worked.
Once done I carefully undressed and laid out tomorrows outfit before getting
ready for bed and slipping into a satin night gown.
I woke up bright and early and spent an hour carefully shaving my face and under
arms and waxing my legs so that all was smooth and soft. I'm lucky in that my
hair is a natural blonde so doesn't leave much of a shadow and my make up could
be light and not look like it had been put on with a trowel. I brushed on just a
little pearl powder over my face then picked out my brown eyes with shadow only
on the lids and a touch of mascara. A little bronzing powder instead of blusher
to pick out my cheekbones in a subtle way then careful application of the new
crimson lippy.
I did my hair, combing it off to one side and holding it away from my face with
a grip and then put on my bra with two, gel filled balloons to give me a bust.
Very carefully so as not to disturb make up or hair I put on my new blouse and
fastened it up allowing it to gape open high enough to hide the fake breasts but
enough to show the sweep of my throat and upper chest. Once done I fastened my
garter belt and carefully rolled on my stockings making sure not to snag them as
I fastened the tops over my smooth thighs. I had difficulty pulling on my
knickers as they were very tight and designed to keep my crotch flat and once
they were on I shoved my hand in and pushed my balls up into my body and folded
my cock back between my legs, pulling my hand free and inspecting the flat
expanse that was now my crotch. I slipped on my skirt, which fit quiet well and
stepped into my shoes. Almost done, I fastened a gold necklace around my throat
and attached a pair of clip on earrings before finally sticking on a set of
nails with superglue and admiring the look of my hands with the new French
manicure nails.
I glanced up at my reflection in the mirror and even I was impressed. I turned
side on and admired the way my front swelled out over my new chest then
flattened all the way down, not a hint of a bulge. The skirt nipped a little at
the waist and it made my ass look full and round and my calves swelled out
gently and swept back in at my ankles, filling out the stockings in a very
attractive way. In fact I had to stop looking as I felt stirrings in my groin at
the sight of this pretty young thing in the mirror.
The drive to work was straightforward enough, I've snuck out at night, dressed
and gone for long drives so these low (for me) 3 inch heels were no problem
although it was surprising how many men turned to admire me at traffic lights.
I pulled up behind the shop and went in through the back door where Martin &
Julie the two warehouse staff were sat having a cigarette. Martin stood up "you
can't come in this way, love..." he began but Julie stopped him.
"Shut up, Martin, that's Bob." Martin did a double take that would have made any
comedian proud and I swear his mouth actually fell open. "You look lovely."
Julie said, "I wish I scrubbed up that pretty." I laughed, said thanks, and went
into the staff room aware of Martin's eyes following me.
My heart was beginning to pound as the moment of truth came and I stepped inside
to where all my colleagues were having a quick brew before the store opened.
"Holy shit!" Said Derek the supervisor and everyone turned to stare at me.
"Yey!" Kerry shouted and rushed over and hugged me. "Oh, Bob you look
FANTASTIC!" The three other girls came over and were crowded around me some
hugging and some kissing. I looked over at the three men who were sat with
coffee cups motionless between table and mouth and grinned. If they said
anything I could respond with how the girls loved it.
In fact the blokes didn't seem that bothered. The only time they seemed
flustered was when a customer wanted something and they had to call me Bob. That
didn't last long and they started calling me Bobby after which everyone seemed
okay with it all. The girls absolutely loved it, sharing make up tips and
stories of waxing and all sorts of girly talk. And the customers didn't bat an
eyelid either. Oh there were reactions from those who realised I was a man (the
majority I must admit) but apart from a little curiosity no one seemed to care.
It was a revelation for me that I could go out in public wearing make up and
heels and no one minded.
Dave called me into his office and I sat down in front of his desk keeping my
knees together and tucking my legs under the chair. "You didn't have to go to
all that trouble." He said, making us coffee. "I just thought you'd wear the
skirt over your trousers."
"In for a penny." I said taking the offered cup.
He squinted at my shins. "Did you shave your legs?"
"Of course. I'd look pretty stupid with hairy legs and all this," I gestured to
my clothes and face. "Beside, I'm expected to look smart while at work."
Dave shook his head. We chatted a bit longer while we drank, his allowing the
girls to wear jeans if they were appropriate, how much effort I'd put into my
garb and so on. As we talked I noticed that he kept looking at my legs and
breasts and I wondered if he fancied me. I tried not to think about it too much
as I felt stirrings in my groin and it wouldn't do to serve customers with a
hard on making my skirt tent.
By closing time I felt great. Many customers had complimented me on my attire
and how pretty I was (including a couple of men who obviously fancied me) and
the staff were all supportive and I decided that I would make some forays into
nearby Manchester and seek out other trannies who I could go on girly shopping
trips with.
We closed and Dave said he wanted to speak to me once we were done cashing up so
once he let everyone else out of the building and locked up, I dutifully
returned to his office.
I was a little concerned wondering if I was in trouble for coming to work as I
was, as Dave didn't seem his normal cheery self. He made us coffee again but
said little as he did so, handing me my mug and sitting on the corner of his
desk.
"You've done this before, haven't you? Dressed as a woman I mean."
I felt that terrible buzzing feeling inside as I realised he knew my secret. I
laughed nervously. "I just did it to show you up."
He nodded thoughtfully and took a sip of coffee. "Where'd you get the shoes?"
"I bought them. Yesterday in my lunch hour, you saw all the stuff I got from the
department store."
"No," he said, "those shoes are too worn down to be brand new."
I glanced down at my feet and saw he was right. Although they weren't scuffed
there was roundness to the edges that showed weeks of wear walking up and down
deserted country roads at midnight. I laughed, trying to give myself time to
think.
"I think you do this a lot." He said leaning over to put his mug on the shelf
next to the printer and as he did so I saw the bulge in his suit pants. I stayed
silent wondering what to do. I'd had fantasies of sex with a man while dressed
but reality was something else entirely.
Dave stood up and I could clearly see the fabric taught across his crotch where
his cock was pushing at it. He noticed my stare and stepped forwards so he was
standing next to me. "I've always liked you as a man, Bob, and as a woman you're
SO hot." As he said it he reached out and cupped the side of my face, his thumb
hot as it caressed my smooth skin and turned my head so he could gaze down at
me.
He knelt as my heart pounded and we stared at each other for a long moment then
he leaned towards me, mouth ready for a kiss. I didn't even try to resist, I'd
melted at his first touch and as his lips touched gently against mine I felt
myself go weak. I needed a man...I needed THIS man. His tongue slid into my
mouth as our kiss became more urgent and I raised my hand to hold the back of
his neck as his stroked my cheek. I felt his other hand on my knees, the warmth
of his flesh feeling sensuous through the thin material of my stockings. I've
always adored the feel of skin under hosiery but feeling it from the other side
was a magnitude of pleasure greater and I moaned deep in my throat as his hand
slid down my shin and back up again, our mouths pressing together harder with
our rising passion.
I could smell his after-shave, strong and manly, and the roughness of his cheek
as his five o'clock shadow grazed my own. His hand had begun to slide further up
and down my leg, fingertips touching the tops of my shoes and then gliding up
the silky smooth expanse of flesh toned black, over my knee and under my skirt.
His other hand had fallen from my face and was now caressing one of my breasts
and I was astonished at how arousing it was despite being merely a gel bag and
not part of me at all but it couldn't have made me any hotter if I'd had real
breasts under that firm hand.
Our tongues were exploring each other like two hungry snakes and our mouths
squeezed hard against one another as we kissed passionately. Dave's hand had
stopped exploring my lower leg and now stayed under cover of my skirt, stroking
my inner thigh and over the lacy top of my stocking to the cool, smooth flesh
above.
I was totally lost to him now and knew that whatever gender I was I wanted to
have sex with this strong, virile man who was doing such wonderful things to me
with only his hands. He undid my skirt and used both of them to pull it down,
never breaking the seal on our hungry mouths and then those hands were rubbing
against my crotch and my ass. The feel of a man's hand on my bottom was a much
greater turn on than I'd imagined and I enjoyed it to the full but I could sense
his confusion as his other hand searched for the expected cock and balls and
found none.
I broke the kiss momentarily. "Pull down my knickers." I gasped and thrust my
tongue back down his throat. I felt him take a firm hold of my girdle like
panties and tug at them. It was an awkward, fumbling moment as they were hard to
remove but our lust for each other kept us going and I stood up slightly as he
pulled them down over my legs whereupon I kicked hem off into a corner.
The scorching arousal I'd felt before at his touch was only the overture as his
fingers found my cock and began to play with it, his other hand behind me,
cupping my buttocks, the fingers exploring my most intimate of places. I raised
my leg to give him better access and the feel of his touch on my asshole sent
ripples of pleasure through me.
To my dismay he broke the kiss but his head dropped and he began to suck on my
balls as I sat, one leg raised, on his hands, it's fingers pushing against my
anus opening. I gasped intermittently as he played with me, the waves of
pleasure almost making me come but my leg was getting squashed between his arm
and his head that was toying with my sack. I pushed his head away momentarily
and raised my leg so he could get his head under it, my thigh almost vertical as
I slumped down, my knee bent and heel scraping his back.
I moaned in delight as his mouth began to work its way up my cock and as his hot
lips engulfed the end of it his finger pushed into my hole. I gasped and opened
my eyes wide at the shocking sensation but I quickly realised that startling
though it was it was making me really horny.
His mouth slid up and down my rigid tool, his finger slipping in and out of my
ass in time to it while his free hand fondled my stocking clad leg, the three
sensations driving me wild. "Oh, God, Dave." I gasped as I found myself pushing
my ass down onto his finger enjoying the sensation while his tongue and lips
serviced my cock expertly and his hand stroked my leg. "Ooooh." I moaned feeling
the pressure building within me and I sat down hard on his finger feeling him
slip another up me. "Uh." I grunted and my hips bucked as I erupted into his
mouth with a shattering climax the like of which I'd never experienced. Dave
kept going, swallowing every drop and still using his fingers in me and with his
other hand touching my shin and thigh. I emptied into him everything I had and
he took it all, softening his strokes as my cock waned and became more and more
sensitive, but all the while I found myself riding his fingers, still wanting
more.
His mouth left my cock and a moment later found my lips again. He tasted
different this time; a more metallic taste from my own juices which he'd
swallowed but still had traces of in his mouth.
We continued, mouths together and his fingers up my ass as I moved myself up and
down on them. It was a glorious sensation that I never wanted to end so when he
pulled his fingers free I moaned in frustration until I saw him tearing his
trousers open and pulling his cock free. It was long and hard, with pale skin
and a swept back head that was slick with his own pre-cum and when he hesitated
I lifted my legs high and moaned "give it to me."
He did, without any finesse he slid it right up into my ass and I was suddenly
full of hot cock. My legs were being pushed high as his shoulders pushed into
the backs of my calves and I looked down to see my own stocking clad legs in a
giant V sticking straight up as a sweating man gritted his teeth and fucked me.
One hand grabbed my left breast while the other returned to fondling my leg, all
the while that cock rammed in and out of my eager hole.
"Oh, Dave," I moaned, almost whimpering, "oh that's SO good."
Sweat was dripping from his face as he pounded into me and a small voice in my
head told me this is what I was born for as I took that cock and loved every
inch of it. I loved his hand on my leg, his other hand on my breast, the
lingering taste of my own come from his lips and of course most of all the
feeling of being fucked.
I swear I orgasmed as Dave thrust deep into me and unloaded his torrent of jism,
a great hot flood of juice filling up my insides with warmth like a good swig of
brandy. He grunted and gave a few more, weaker shoves as he emptied himself then
sagged to the floor.
I slid off my chair, enjoying the slimy feeling from my come-drenched asshole,
and lay next to him, my head on his heaving chest.
"I meant what I said before." He gasped and I turned over to look at him. "About
liking you as a man too." I said nothing just gazed adoringly at him. "We could
date if you like? Either as Bob or Bobby?"
I smiled at him and nodded, I liked him too and if the rest of the relationship
went as well as the sex I'd have to start looking for a nice wedding dress.
