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I've always been very curious, ever since I was a little boy. I'd always
ask my parents and older sisters annoying questions, always want to know
why people were doing what they were doing, never satisfied with a
throw-away answer. Nothing escaped my curious mind, which I suppose is
what led to me, at the age of 10, trying on a pair of my sister's
panties.
I'm not really sure what my question was when I picked a pair of silky
red panties out of her drawer and slid them up my legs, but I liked the
answer. Over the next few months whenever I managed to get some time
alone at home, often when Mum and Dad went out shopping on a Saturday
night and my sisters were out with their friends, I would explore their
wardrobes further. It wasn't long before I was regularly spending all my
time home alone dressed up in full make-up, lingerie and clothing
enjoying my femininity. There were more than a few close calls and one
evening I had spent terrified someone would spot through my socks the
nail varnish I hadn't had time to remove, but I always managed to get
away with it. I was always careful about putting everything back exactly
as I had found it and my methods never failed me.
Did I want to be a girl? I had thought to myself on more than one
occasion. I didn't think so, but I certainly enjoyed dressing and
looking like one. I had grown my blonde hair long and staunchly fought
off any attempts from my Mum or Dad to get it trimmed. I had a perfect
set-up at home to indulge my crossdressing lifestyle, though this all
fell apart when my sisters left for university. I endured three long
years of being unable to dress up as I had done before. Oh sure, I tried
with my Mum's stuff but she never wore that much make-up and her range
of skimpy and sexy clothing wasn't half as wide as my sisters. Most of
her stuff didn't even fit me, as she was quite overweight and I was
rather petite.
Both my parents were quite short and I felt this was quite the blessing
for me. By 18 I had only grown as tall as 5' 5'' and was towered over by
the rest of the boys in my year group at school, but this was the height
I was happiest at. I enjoyed being short, it made me feel more feminine
and as I could no longer dress as frequently as I had during my youth I
clung to anything that could give me the same thrill of sliding on a
lacy thong. Throughout school I was never bothered about getting a
girlfriend - I don't think many of them would have wanted to date a boy
that looked girlier than them anyway. The only reason I saw in my mind
to date a girl would to be to get access to her wardrobe.
Don't get me wrong though, I did find girls attractive, but I always
viewed them more as role models than objects of sexual attraction. When
I watched porn I always imagined myself as the girl, but that didn't
mean I was attracted to boys either. All that appealed to me was
dressing up. I couldn't wait to get a job, leave home and get my own
place so I could spend all my free time en femme. So when I was 18 I
took a job working at the Starshine Hotel, and it was there I discovered
my future.
*
"Rich, got an order through from Room 315 especially for you!" My
supervisor Charlie barked at me, snapping me out of my daydream of the
pair of high heels I wanted to buy online. They were crimson stilettoes
with a 5in'' heel and I had been saving up for them over the past few
weeks so I had something lovely to start my new collection of clothes
off with. It had been a toss-up between the shoes or some new lingerie
but the shoes had won out. I had managed to smuggle away a couple of
pairs of my sisters which would do for the time being. "Rich!" Charlie
shouted again, and I shook myself from my trance, properly this time.
"Sorry, Charlie! Room 315?" I asked.
"Yeah, that's right! You are covering the east half of floor 3 today
aren't you?" Charlie replied, cocking her head and placing her hand on
her hip.
"Yes, yes, of course!" I stuttered, eager not to annoy Charlie any
further. I was aware I'd been daydreaming a lot at work recently and
didn't want to give her any excuse to fire me. I liked working at the
hotel, it was relatively fun work that served to satisfy my curiosity.
There was no shortage of stories and gossip that went round the hotel,
from the copious amounts of sex toys poor Lisa had stumbled across in
room 442 last month, to the seemingly respectable vicar in room 607 who
had been meeting with a rather muscular man every weekend, to the couple
in room 103 who had to be moved rooms as you could hear the bed thumping
from down in reception.
I took the order slip from Charlie and glanced through it. It was a
request for a bottle of some of our most expensive red wine, which was
simple enough to prepare. I grabbed my trolley and wheeled it down to
the wine chillers, where I located the bottle easily enough, swung by
the glass cabinet to pick up a couple of wine glasses, arranged them
lovingly on the trolley and headed to the service lift. The lift doors
slid shut behind me and I pressed the faded number '3' on the panel,
which lit up green. Before long I was trundling along the hallway
towards room 315, trying my best to keep quite as it was fairly late at
night and most of our regular guests would be sleeping. I arrived at
room 315 and rapped on the door.
"Room service!" I called out pleasantly. No reply. I knocked again, a
little louder and called out once more. I tried one last time but no-one
answered. Oh well, I sighed, reaching into my pocket and pulling out a
master key card that would let me into all the rooms on this floor. I'll
just drop the wine off and head back down, and hope I don't see anything
too mentally scarring left lying around in this room. Lisa had taken two
days off after discovering that cache of sex toys littered around the
room, and I prayed I wasn't about to walk into a similar situation.
The door swung open to an empty room with the lights left on. I left the
trolley outside and carried the wine and glasses in, peeking around
corners gingerly and calling out for anyone who might be listening. The
door shut behind me with a soft click and the room was silent. If the
room's empty, who ordered the wine? I thought, putting it down on the
bedside table and scratching my head. Perhaps someone had got the wrong
room? This room looked immaculately clean, as if no-one had slept in
here so perhaps Charlie had got the number wrong. I decided to have one
last search around the room and then head back to check. I slid open the
door to the en-suite bathroom and that's when I saw it.
On a hanger on the shower rail was the most gorgeous red dress, which
shimmered in the bright light of the bathroom. It looked exquisite and I
was drawn to it from the doorway, running my hands down its fabric that
made the fine hairs on the backs of my hands tingle. As I examined
further I saw there was also a matching bra and thong set made from
black velvet with red lacy trim, and what looked like a small black
make-up bag. I looked over into the bath and saw a pair of strappy black
high heels that my feet yearned to wear. I hastily glanced at my watch.
It was 9:47 - I'd already been away from the staff room for five
minutes, but Charlie wouldn't really start looking for me any time soon.
As I'd already mentioned, most guests would be asleep by now so unless
there was a major incident I could probably hide away from more work for
about... half an hour? That would be more than enough time to try on the
clothes and still get back in time. I poked my head back out into the
room again to check no-one had magically appeared, and began to strip
off.
*
My uniform lay in a neat pile on the chair in the corner of the room as
I admired myself in the full-length mirror. I'd let my long blonde hair
out of its ponytail and it cascaded down over my shoulders, where I ran
my hands through it, puffing it up and out, pouting at the mirror as I
went. Inside the make-up bag had been all manner of essentials which I'd
used to doll myself up so I looked gorgeous. My eyes popped out thanks
to my slightly rusty yet skilled application of mascara and eyeshadow,
and my scarlet lips looked plump and kissable. I ran my hands down my
chest to my hips, admiring the silky feel of the red dress that clung
tightly to my feminine body. There was a mesh window cut down from the
neckline of the dress that plunged towards my waist, and if I had any
boobs to speak of it would have been very revealing. The hemline of the
dress was similarly revealing, cutting off halfway down my slender
thighs. I was so glad I had decided to keep my legs waxed out of habit,
it had all paid off in this moment as I marvelled at my calves in the
mirror. My feet looked beautiful and delicate too, slipped into the high
heels and buckled in by the numerous straps that wrapped around my
ankles.
I was so narcissistically transfixed by my own appearance that I didn't
even hear the door open and close. The first sound I heard was the bolt
sliding into place and a deep, chocolatey voice say:
"Well, well. Hello there, darling." I yelped and twisted towards the
sound, losing my balance in the heels and falling back so I landed
sharply on my bum on the bed. A tall, athletic looking black man strode
into the room, stood where I had been a second ago and smiled broadly at
me. I got the feeling he was undressing me with his eyes and I felt very
exposed.
"I'm sorry, I - I think I must be in the wrong room-" I began, trying to
stand up before being effortlessly pushed back down onto the bed by one
hand.
"Oh no, you're in the perfect room little lady," the man grinned, "I've
been waiting for you."
"For me?" I asked nervously, my heart pounding in my chest.
"Yes, indeed. Ever since I saw you mincing up and down the hallway the
other day I knew you were a little sissy girl, and here you are, proving
me right." He purposefully moved over to the bedside table and picked up
the wine I had brought there earlier, though that felt like an eternity
ago now. He uncorked it deftly and poured two large glasses. "Wasn't
even a particularly difficult trap I laid for you, but then I guess some
sissies are dumber than others." Joe chuckled in synchrony with the wine
glugging into the glasses. He took a couple of tablets out of his
trouser pocket and dropped them in one of the glasses, where they fizzed
and disintegrated.
"I - I'm not a sissy." I flustered, but I was cut off again.
"Of course you are, sissy. What kind of man sneaks into hotel rooms,
dresses up in clothes like that, does make-up as well as that and looks
as damn sexy as you do? Damn girl, look at those legs of yours!" I tried
to cross them out of sight but it was impossible to avoid his hungry
stare. He passed me the wine glass he'd put the tablets in, which I took
with shaking hands. "Drink." He stated, and I hesitated. "Drink, it'll
make the next bit easier for you." He grinned devilishly and took a deep
swig from his own glass.
"What's in it?" I quivered.
"Grapes, mostly." Joes grinned and laughed at his own joke. I pouted,
then realised how girly this must have looked and attempted a scowl,
though this made him laugh more. "God, you look so damn cute when you're
mad!" I blushed, despite myself. "Just a couple of relaxants, so you're
not so nervous sweetie. Loosen you up a little faster than the wine
alone will." He smiled, though it was a threatening smile that made me
realise that what was going to happen this evening was happening whether
I was relaxed or not. Deciding the easy way was the best way, I took a
large sip from my glass which made my head tingle. Blinking, I realised
I'd left a lipstick mark around the rim. I'd never felt so girly and
submissive before, which both aroused me massively but terrified me as
well. Who was this man? What did he plan on doing to me?
"Uh-" I stuttered.
"Oh, where are my manners?" the man asked, sitting next to me on the bed
and swinging a heavy muscular arm around my waist. "The name's Joseph,
but you can call me Joe. What might I have the pleasure of calling you,
my little cutie?" I blushed under the man's powerful charisma and stream
of compliments and attention. I had never been looked at so intensely
and with such sexual lust in all my life and it was making my heart skip
and my body flush.
"I'm, um, Richard." I responded meekly. Joe smiled.
"No, what's your girl name?" he asked politely. I stuttered once more.
"I, um, don't have one." I said, trying to look away from his eyes that
were lapping me up.
"Well then, how about Rachel?" Joe chuckled. "Do you like that name,
Rachel?" I was lost in a sea of mixed emotion, panic and pleasure
dancing wildly in my mind. Despite myself, I nodded. Rachel sounded so
nice, so girly, so me - much more so than Richard ever had. "That's
good," Joe smiled, "I'll call you Rachel then, hot stuff." I blushed
again. "Now I do believe you're wearing clothes that belong to me,
Rachel. Don't worry, I don't need them back just yet. But if you're
going to keep wearing them then I'm going to need something in return."
I gulped, awaiting the next words out of his mouth.
"I'm going to need a kiss." He said, smiling and pointing towards his
lips. My stomach twisted slightly. I wasn't interested in guys, I never
had been. Why then did this invitation turn me on so much? I could feel
my penis stirring in the velvet panties, which as it brushed against the
material turned me on even more and I began to feel even more hot and
sweaty. "Come on then, gorgeous. Why don't you give me a kiss?" I found
myself leaning forward into his embrace before I could think about what
I was doing, and in a heady instant our lips met.
I don't know quite how I had imagined my first kiss to have gone, but
suffice it to say that dressed up as a girl, sat on a hotel bed as a
black man ravished me would not have been my first guess. I wouldn't
have had it any other way, though. All those conflicting thoughts about
sexuality seemed to have faded away in the instant our lips had touched
and I'd inhaled the scent of Joe's cologne. I'd melted into his arms as
he kissed me deeply, his tongue parting my lips softly but firmly and
meeting my timid tongue which hesitantly touched his in return. As we
kissed I felt Joe wrap his arms around me and I felt my head forced back
as he deepened the kiss and lifted me up onto his lap. I squealed as he
effortlessly placed me down and my hands wrapped around his broad,
muscular shoulders. We kissed passionately for the next few minutes,
sparks of electricity running through my body until I felt a large
swelling beneath me. I broke the kiss, gasping heavily and looked down
at the massive bulge in Joe's trousers which was still growing. I looked
into Joe's eyes and he winked suggestively, licking his lips at me.
I slid down off his lap and rested my knees into the plush carpet of the
hotel room as Joe shuffled to position himself on the edge of the bed,
one leg either side of me. His large, strong hands undid his belt and
zip and shuffled his trousers down to his ankles. A massive black cock
sprung out at my head height and I marvelled at the glorious dick in
front of me, reaching out my hands to touch it as my jaw dropped. I had
never thought much about my cock but now mine felt like a finger
painting compared to the masterpiece before me. Joe's cock was long,
hard and thick whereas mine was short, limp and thin. If he had told me
his was three times the size of mine I wouldn't have called him a liar.
Almost instinctively, with Joe's hand on the back of my head as
encouragement, I began to suck his big black cock. I struggled to fit my
small mouth around the bulbous head but persevered, licking it furiously
until it glistened in the light from saliva. My head bobbed up and down
the length of the shaft, my slender hands pumping from further down so I
could see my ruby red fingernails flash in front of my eyes. Joe moaned
and groaned as I sucked as if my life depended on it, having discovered
a new-found pleasure in the act I was performing. To hear Joe moaning in
pleasure from the blowjob I was giving him made me feel wanted, desired,
more than I ever had before in my life. My place was here, on my knees
sucking his big black cock. All my life had been leading up to this
revelation, I thought, and it was all worth it to get here.
I could feel Joe tense and his body shook as I plunged his cock deeper
and deeper into my mouth, almost managing to get halfway before I felt
the head of his dick brush against the back of my throat. I gagged and I
choked hard, but Joe just moaned louder and I knew I couldn't stop. My
vision started to fade as I forced myself to take more of his cock into
my mouth but I took a deep, intoxicating breath in through my nose and
persevered once more. Not long afterwards I felt Joe tense and shake
again, and without warning I felt my mouth fill with his warm, salty
cum. His cock was so far into my mouth it felt like it was being shot
directly down my throat and I gagged once more as he squirted load after
load of cum into my mouth. I gulped it all down greedily and presented
my clean tongue to Joe, who chuckled happily and stroked my hair
playfully.
"Such a good girl," he panted, "a natural at sucking cock. Room for
improvement, of course, but I'm sure you'll be more than eager to
practice again?" I nodded, lost in lust. I was so horny, desperate to
orgasm myself, and began to rub my cock through the soft fabric of the
dress. "Ah, no touching your little clitty!" Joe warned, wagging a
finger at me. I quickly removed my hand, fearful of upsetting him. "Good
girls never touch their clitty, they only get to cum from being fucked
in the arse, understand me?" he asked. Without need for words I quickly
stood up and with a practiced shimmy of my hips the black velvet thong
slipped down my legs and I stepped out of it, expertly hooking it over
my high heel and tossing the thong into the corner of the room. It was
moments like these that I knew no man would have practiced such a thing.
I was a sissy girl, and more than that - a slutty sissy girl.
Joe chuckled heartily at the sight and took hold of his cock, shaking it
in his hand and stroking it until it quickly sprung up hard as a rock
again. I gaped, my lipstick-smeared lips forming a perfect O. Normally
when I came it would take a good half hour to be able to get erect
again, but Joe had shrugged off the orgasm like nothing and was ready
and waiting for round two. He pulled his shirt off over his head and
swept me up in his arms again, my legs dangling hopelessly in the air as
he lowered my ass towards his cock. I had never taken anything in there
before and my heart began to whirr into overdrive.
"I've never had anything in my arse before!" I squealed helplessly as I
was lowered closer and closer to his cock. Joe held me in one hand and
pulled my heels off with the other so my feet could be placed on his
thick thighs to balance myself.
"Then brace yourself." Joe grinned evilly and pushed me down onto his
cock. It was slightly lubed by my spit and saliva but even so when the
head of his cock popped into my virgin asshole I think everyone in the
entire hotel must have heard my squealing. I panted and gasped and
screamed as I tried to push myself off his dick but every inch I got up
Joe would pull me down two. I writhed in pain as his monster cock felt
like it was ripping me apart, my asshole burning as it was relentlessly
stretched wide open. My eyes teared up and I felt tears running down my
face as Joe began to thrust up into my arse slowly, so I bounced like a
pathetic puppet on his cock. I whimpered and moaned as Joe continued to
slowly and steadily fuck me, until the pain in my arse started to fade
and be replaced my pleasure.
My tiny limp cock - clitty - flopped pathetically as Joe's powerful
black rod pumped in and out of my arse like a piston, filling me up and
stretching me out. I gasped and squealed as he fucked me deeper and
harder, speeding up with every minute. Pleasure unknown to me seeped
into my entire body, sparking from every thrust deep into my arse that
leapt around my whole body. This cascade was met by a steadily rising
heat that enveloped me, making my legs weak and my hips numb and tingly.
Just as it was reaching a crescendo Joe stopped and I felt his dick pull
out of me with a soft squelch. He flipped me onto my front and I laid on
all fours as he pulled the dress I was wearing up, exposing my raw
arsehole to the air.
Joe mounted me from behind, his legs placed both sides of me and his
cock dangling down directly above my arse. This time it didn't hurt so
much when he entered me, and felt more like a familiar pressure
returning. Joe launched into a relentless rhythm, furiously fucking my
arse until it was numb with pleasure. My body was on fire as this
powerful, dominant black man made me into his naughty little girl, using
my body for his pleasure. My little clitty flopped back and forth as he
humped me, his weighty balls slapping against my arse cheeks with each
thrust. I could feel my clitty tingling and ready to burst, teetering on
the edge of orgasm. Joe sped up one last time and I felt myself leaking
all over the bed as his thrusts came thick and fast, pounding powerfully
against my prostate.
"I'm cumming, Rachel!" He grunted and forced his big black cock as far
into my raw white arse as he could, spurting more copious streams of cum
deep inside me. This pushed me over the edge and I came furiously, my
hips bucking and shivering, my mouth agape, squeals and moans escaping
my drooling lips and my eyes rolling back into my head. My legs
collapsed underneath me and I fell into a warm pool of my own cum, Joe
falling on top of me, his monster dick still buried deep in my arse,
still pulsing and filling me up with his warm, thick seed. I felt his
ragged hot breath against my right ear as I lay there gasping for
breath, trying to focus as my head spun and my body reeled from such an
intense assault of pleasure.
"I - I..." I moaned.
"You're such a good girl, Rachel. Such a good girl for your daddy."
"I - I love you, daddy." I sighed, moaning with pleasure as I felt Joe's
cum start to dribble out of my arse and run down towards where my itty-
bitty clitty was leaking cum itself. Joe kissed and nibbled my ear as we
laid there, panting and euphoric. Reality began to seep in through the
haze and I caught sight of the clock on the bedside table. It was 1:30
in the morning. We'd been fucking for what must have been about three
and a half hours. "I've definitely lost my job for this..." I groaned,
imagining Charlie's furious scowl when I hadn't returned at the end of
my shift. I didn't seem to really care, though. Joe brushed my
dishevelled, messy hair out of the way and kissed the nape of my neck,
holding me tight in his thick, muscular arms.
"As long as you're my girl Rachel, I'll take care of you. I'll give you
a roof to live under, food to eat and water to drink, all the clothes
and make-up you could dream of. All I ask is every night you suck my
dick and take my cock in your arse as you have tonight. Is that what you
want, darling?"
"More than anything!" I squealed, and I found I really, truly meant it.
"Oh daddy, I love you so much!"
Ofelia
- 06.10.2021
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