Wartime Comfort House Diary Day 8 Shemale
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The Diary Of A Shemale Whore On Tour free porn video
This one comes by popular request and is dedicated to all you naughty people
who fe-mailed me and complained that whilst you enjoyed my stories you felt
that I could perhaps be a little more filthy instead of being suggestive!
Well, I've always said that I'll give you what you want, well, you got it and
I hope you like it!
Disclaimer; (seriously!) The following story does not reflect the writers
personal tastes and depicts entirely fictitious characters and fantasy scenes
of an adult and transgendered nature. If you're under twenty-one years of age
I suggest you go and find something more suitable to read, if you're under
twenty-one and of a nervous disposition I suggest you do likewise! If however
you're over twenty-one and in need of some highly explicit shemale erotica
read on, but, be advised, you have been warned and the writer accepts no
responsibility for soiled garments, furniture or you being caught by someone
who never believed that you play with yourself.
The Diary of a Shemale Whore on Tour
By Jennifer Richardson
Hi, my name is Lisa, a shemale whore, slut, prostitute, escort, working girl,
whatever you want to call me. Please yourself, I've been called a lot worse
than anything you could come up with I promise you. So, anyway, I started off
cross dressing when I was a kid, went full time when I was twenty-two and
started my hormones as soon as I found a regular supplier.
I'm 36c, 32 waist, 36 leg, tall, slim long bottle blonde hair with a
permanent show of brunette roots. It pays not to look to polished. Why did I
become a whore? Because I wanted to, I love cock, love pussy and love ass. I
lust for cum, in me on me and down my throat, I'm addicted to it, so the best
way of getting my fix is to whore myself. Plus I get paid and get to see
different places, mostly the ceilings of hotel rooms.
You want to know what I get up to? Well, here's some highlights from January.
Don't worry about the missing dates, they're mostly travel time, then again,
there are the blow jobs for ten quid in train station toilets or my ass
getting well and truly fucked in the back seat of an overnight bus. We'll
start with that one shall we?
Friday 2nd January. National Bus Service 353,
London to Newcastle, about 0230.
I hate travelling on buses but it's cheaper than the train though it takes
ages longer. The worst is the boredom but on this trip things were looking up
when this really cute guy got on in Luton. Quite short, blonde hair, blue
eyes. Pink floral shirt and white strides gave him away though!
Waited until the bus moved away the wandered up to the toilet, gave him a
blasting smile when I went passed. Felt his eyes on me and he was still
looking when I came out of the tiny cubicle. Gave him a wink then slid into
the back seat. The bus was busy but most seemed to be asleep so I beckoned
him up with a finger and stared into his eyes as he got closer.
He sat down next to me and looked confused, taking in my tits that were
stretching my black sweater and the tightness of my faded jeans over my
thighs. I saw him stare at my groin so I took his hand and rubbed it over my
growing cock. I rubbed him through the strides and felt a very respectable
cock getting interested.
Smothered his mouth with mine and sucked his tongue into my mouth. Sucked on
it like I would a cock at the same time as opening his pants and taking him
out into my hand. Very slim dick but lovely length. Kept stroking him as I
stood and leaned on the back of he chair in front. Little old lady sitting in
the seat asleep. Peeled my jeans down, hitched my thong aside and wiggled my
ass at him.
Felt his tongue trailing between my cheeks, then he shifted and held my hips,
guiding me back until I felt his cock nudging my ass. Settled on to him and
pushed his hands under my sweater and onto my tits. Started bouncing up and
down on him, biting my tongue to stop myself from squealing with pleasure. It
didn't stop him though, when he came it was with a high pitched yelp which
woke half the bus.
Shame I didn't get to cum but the hostess put us both off in Doncaster after
threatening us with the Police!
Tuesday 6th January, Swanlodge Motel Bristol.
Booked for a post Christmas and New Year stag party who want something a
little exotic. The booking confirmation came in plenty of time so there was
no problem at the reception desk.
The room was small and had twin beds in it, stripped the bed, pushed the beds
together and turned the top mattresses round so there's plenty of room for
later. Had an hour to get ready so showered and got ready. Short red and
black pleated tartan skirt, mesh teddy with no bra beneath. Tits on show with
nipples poking through. Black hold up stockings with black lace frills,
easily visible under skirts hem. Tight tanga thong barely covers my cock and
balls. Very slutty red patent stiletto's and painted up like the whore my
clients are expecting.
Lee, the guy who booked me arrives with his four friends. They're aged
between 19 and 55 and all look a little nervous. Begin to play with my
nipples through the lace to get them going and soon enough there are five
nice hardening cocks facing me. They formed an orderly queue, typically
English, and I moved along them wanking and sucking them until they were all
nice and hard, pricks glistening with my spit.
Two of the guys stood me on the bed, down came my panties, to amazed gasps
and some choking from those who had almost come with a shemale whore sucking
hard on their cocks! Felt a tongue snake between my ass cheeks and probe
deep, shuddered when I feel the bed move and the youngest guy sticks his head
under my skirt, licks and sucks me hard the darling boy!
Dropped to all fours, two cocks in my mouth, one guys nudging his cock at my
ass and someone else is wanking my cock. The cocks I'm sucking explode into
my throat at the same tome as the prick invading my ass plunges deep until
his balls slap against mine. Single cock replaces the two in my mouth, cum
dribbles down my chin, gulping hard and gasping, the queue forms again, three
plough my ass until it aches, two spurting their juice over my back, one
spills his in me.
Drenched in cum I collapse on my back, lace teddy ripped away. Looking up
through pasted eyes I see them kneeling all round me, all wanking furiously
while the darling boy finishes me off too. Gallons of flooding spunk cover me
from the forehead down. My hands and fingers spreading it and smearing it all
over my skin. Lee shakes up a huge bottle of sparkling wine, pops the cork
and sprays it all over me.
They thank me for my time, get dressed and head for the bar for a celebration
drink. I shower again, change of clothes, leave ruined panties, stockings and
teddy on the bed with the rest of the mess.
Thursday 15th January. Stay-a-while Hotel Carlisle.
Nice comfortable room, double bed, nice furniture. Client, Robert, very well
to do, wants to experience everything and that apparently includes having a
sexy shemale secretary! Found a slutty scarlet suit skirt in a charity shop.
Fits too tight all over, no blouse jacket closed by a single button below
tits. Scarlet lace lingerie beneath, black seamed stockings and "sensible"
shoes.
Collected me from railway station and took me for a meal which was a nice
touch. Told me to flirt outrageously with one of the waiters, Robert playing
the offended Boss. Back to hotel by taxi, booked in as man and wife!
Once up in the room he ordered me to undress him, found he was wearing
stockings, suspenders and panties. Panties did nothing to hide his huge thick
prick. He pushed the jacket off my shoulders without unbuttoning it so
effectively he had me trussed. Pushed me to my knees and told me to suck him.
Really a hug mouthful, felt his hands in my hair, pushing more and more of
his cock into my mouth and down my throat until I was gagging.
"Suck it you bitch! This'll teach you to flirt on my time."
I don't think I've ever swallowed as much cum, couldn't manage all of it and
had quite an amount smeared round my mouth by the time he had finished. Made
me lick him clean and got as hard again under my tongue.
Put me on the bed, still in skirt and jacket, raised the skirt onto my back
and started kissing my ass, parted my cheeks and pushed his tongue deep.
Waggled it round which made me squirm, he stroked me hard and then backed me
up to the end of the bed. His cock just about split me in two, inched it in
bit by bit until he was balls deep. reached under me and started playing with
my tits and nipples then told me to wank off while he was still in me.
Just as I was about to cum he told me to stop and started spanking my ass,
then started shafting me until a second flood filled me. When he'd finished
he stepped back and pointed to a waste paper bin in the corner of the room.
"Squat over it and dribble my juice into it while you jack off."
Dirty old bastard! Still, it was nice and kinky and he had e sucking him off
while my ass emptied his cum, mixed it with mine in the bottom of the bin. He
pulled out of my mouth and shot down my tits so his juice dribbled down my
front. Managed to catch most of it before it stained my skirt but not all.
Monday 19th January, Oxford Lodge Motel, Oxford.
Collected from motorway as arranged by Patricia, mid forties, grey suit,
plump running to fat. She wanted a hitch hiking hooker and that's what I gave
her. Long black PVC mackintosh, knee high black boots on spike heels, low cut
leopard skin blouse open at the front down to belly button and red micro
mini.
Drove to Motel with her left hand stroking my cock, skirt hitched up to my
waist. Told not to speak unless spoken to.
Motel made up of separate lodges, small, sparse but comfortable.
She led me straight into the lodge, took off her skirt and sat on the end of
the bed. Opened her legs to show her very hairy cunny.
"Lick and kiss me 'til I come."
Between her legs without even taking my coat off. Closed her thighs on my
head, muscles like iron trapped me there. Lapped at her very hot, very wet
cunt while she read letters aloud from a porn mag! When she came she was
squealing and screaming, once she'd calmed down she told me to take my
clothes off so she could see what a shemale slut really looked like, the
cheek of some people!
Gave me a lovely long blow job though and slipped her fingers up my ass,
holding me there until she'd milked me dry.
Friday 23rd January, Swallow Inn, Newcastle.
Met in the cocktail bar by a very sexy looking girl called Anita, long dark
hair, tits trying to escape a very tight fitting sheath dress. From what
she'd said on the phone she was sick of her hubby going on and on about
watching her go girl on girl so she'd checked out my website and decided to
give her hubby something of a treat. Namely me fucking his ass after we'd got
him all turned on!
Went up to the room with her and found that hubby was naked but for a rubber
hood, he had a ball gag tightly fitted and his wrists were tied behind his
back. There was a spreader bar at his heels keeping his legs wide apart. He
was chained to one of the beds and me and Anita got down to it on the other.
She was so stunning that I almost forgot I was working, what a lover! She's
wasted on men I promise you that. Anyway, I kept my frenchies on all the
while, Anita stripped completely and let me loose on her tits and cunt until
she was cumming, tasted so sweet and sexy, shaven too, very smooth and soft.
She got my nipples nice and hard to a chorus of moans from her hooded hubby,
his short stubby cock grew as hard as it was going to get and he began trying
to hump the bed.
Anita slid away from me and slapped his ass a few times until he got the
message. After unchaining him she bent him over the back of the chair in
front of the dresser so he was staring into the mirror.
"You wanted to see me fucking with a girl? Well you've got your wish, now I'm
going to have mine. I want to see you being fucked by a girl."
Taking my cue I stood up and moved to stand behind him, stroked my fingers
across his spine and slipped a finger between his cheeks and probed his ass.
He grunted through the gaga when I fingered him, then his eyes went real wide
when Anita pulled my frenchies down and my cock reared up from between my
legs.
If he hadn't been gagged I'm sure he'd have been begging no, no, no! I slid
my cock into him bit by bit, real slow so that he knew it was a real length
of hot flesh he was getting. Very tight muscles trying to push me out so I
slammed passed the resistance until my balls slapped his.
His groans and moans were music to my ears, I glanced to the side and saw
Anita capturing the moment on video for posterity.
When I shot my load I just had the head of my cock in him so plenty of it
filled his ass while I shot the last dribbles over his cheeks. We left him
there sobbing while Anita and I went back to the bed for some fun. I loved it
so much I didn't even charge her other than her sending me a copy of the
video of me fucking her man and then the two of us fucking each other
senseless.
Wednesday 28th January, Metro Hotel Manchester.
I met him in the foyer, he was sitting just where he said he'd be, reading a
newspaper at a table next to a large potted palm. He'd actually sent me a
script which, he had instructed, I was to learn by heart. When we'd first
made contact he had asked me what I was and what I wasn't willing to wear,
obviously I have no worries whatsoever but when he actually sent me a box
with the body harness in even I was taken aback!
It had a high broad collar from which there were long stainless steel chains.
One ran from the collar to each of two wrist cuffs. From the collar downwards
were leather straps which shaped round my tits, when buckled correctly they
pushed into the flesh making them stick out even more. A cross belt ran
beneath my tits from which there were three straps, two went either side of
my cock and balls while the third, the broader of the three, went over my
bits and pulled them back between my legs where the strap buckled at the
bottom of the strap covering my spine.
There was a large stainless steel ring just over my belly button and another
at the bottom of the collar front and back. Other than black hold up
stockings and spike heeled black patent I wore nothing else bar the my long
raincoat with the rubberised lining. That had been another specific, I had to
arrive wearing a rubberised riding mac or the whole thing was off. The money
offered was too much of a good thing to miss so I'd gone to a specialised
equestrian shop and bought one.
"Good morning Sir, I'm a very naughty slut." I said, the script demanded it!
"Are you indeed? And are you properly dressed?" He didn't even look up from
his newspaper.
"Yes Sir."
"Good, will walking up a lot of stairs in your high heels hurt your feet?" He
asked, this wasn't in the script so I improvised, it helped knowing that the
very high, very slim heels were already making my legs ache.
"Yes Sir, they'll begin to weaken and then they'll start to tremble until I
find it difficult to stand up."
"Good, follow me, there are only a dozen flights of stairs." He unfolded
himself from the chair and barely looked at me when he walked passed. Very
sharp, very expensive black suit, white shirt and thin red and gold banded
tie. He didn't say that the flights of stairs doubled back on themselves!
He was leaning on the door post by the time I made it along the long corridor
of the twelfth floor. I could barely put one foot in front of the other. He
pulled me into the room and opened my coat without a word, checking to make
sure I was wearing it correctly. The first thing he did was to gag me with a
latex ball gag, then he began to add more cuffs and straps which he took from
a metal briefcase. Ankles, calves, knees and thighs, then a criss-cross
spiders web of chains which tightened and tightened until the chains
themselves were biting into my flesh. Two spring loaded clamps were fitted to
my nipples which had heavy steel balls attached.
Because of the gag I couldn't express how much the clamps and weights made my
nipples ache, once the blindfold was fitted and foam plugs were placed in my
ears my senses were
seriously deprived. I felt him open the coat again then realised that he was
attaching the various straps of the coat to the cuffs and chains.
A long metal rod slipped through the sleeves behind my back which meant the
coat was held open displaying my bondage openly. I heard a curtain being
opened and then sliding door, I thought he was going to put me on display at
the window but it was worse than that. He took me out onto the balcony and
locked my wrists to something, I guess the frame of the door. Reaching round
my back to the buckle of the strap which trapped my cock and balls he
released it. I felt a long cold length slip easily up my ass, then suddenly
it began to vibrate. My cock tried to harden but the re-buckled strap held it
painfully trapped.
"You have been a naughty girl haven't you? So you can stop there for a while
so that my friends across the way can watch you through their binoculars.
There are a dozen naked guys over there and all of them are naked, wanking
over you. When each of them has come five times I will receive a phone call,
then I will release your clittie and they will see they have been wanking
over a shemale. I'll enjoy thinking of them squirming in self loathing."
I have no idea how long I was out there on the balcony, the wind chilled my
tits but the aching nipples at least kept them warm whenever the breeze
dropped. The vibrator had me writhing in torment and though throbbing of my
trapped cock was a torture verging on painful pleasure.
When I finally felt hands about me they squeezed and caressed until the
sensations were overwhelming, how many hand there were I couldn't count, who
they belonged to I didn't know but the delicious softly caressing torture
finally ended when my cock was released and provoked into a bone jarring
orgasm that must have arced my cum right over the balcony twelve floors up. I
pity whoever may have been passing.
I was freed from the door frame, taken back into the warmth of the room and
felt the chains being removed from my hands.
"Keep the harness on, keep the chains to your wrists, remove the rest of the
chains but leave the straps and cuffs on your thighs, knees and ankles. Pick
up the envelope and then leave." He ordered.
Once I was free of the gag I gasped for breath took the blindfold off and
found I was alone. As ordered I took the chains off, kept the straps, picked
up the envelope and left. When I opened the envelope later I found my fee and
note.
"Next time I'm going to bend you over and chain you to the balcony then fuck
your ass for hours. In that time you will suck every cock put in front of
your mouth until it spills it's seed. You will not swallow, you will allow
the cum to dribble into a bucket. After the last prick has creamed and the
bucket is filled with a cum cocktail I'm going to piss in it. Then I'm going
to pour the bucket all over you. As you will be dressed in a very expensive
dress at the time I hope you will appreciate the efforts I've gone to in
order that you are subjected to the ultimate shemale humiliation."
I await the phone call, though I think I might contract the job out!
Saturday 31st January, Olympia Hotel, London.
Gave a latex uniform naughty nurse massage to a visiting French shemale by
the name of Sasha. We have an arrangement where she pays no fees when she
visits London and I pay nothing when I visit Lyon.
Wonderful time for both of us, though when she invited a friend up to the
room I was a little put out until I saw the huge black cock that he owned.
With Abdele deep in my ass and Sasha sliding her sweet little clittie deep
into my throat I felt utterly complete. Abdele actually lifted me off the bed
once Sasha had sent her lava flow of cum jetting down my throat. He held me
tight against him, cock embedded in my ass while Sasha knelt between my legs
and sucked my cock until I exploded. She and Abdele kissed over my shoulder
and I just knew they were exchanging my cum mouth to mouth.
It was my turn later, I was giving Abdele a lovely long blow job while Sasha
shafted my ass. She shot load after load into my ass then pulled me off
Abdele's cock as soon as his juice filled my mouth. While Sasha and I kissed
Abdele ate Sasha's cum from my ass while wanking me off into his hand which
he then presented for Sasha and I to lick clean. All in all a very satisfying
end to the month and a very kinky time was had by all.
Enjoy that insight into my world? Like to enjoy something else? Well you just
read on darling but please, have your lovely cock in your hand or a nice long
vibe in your cunt while you do so.
You see, I'm ever so lonely and I'm lying back in this huge empty bath in
nothing but a crotch-less fish net all in one body stocking. My nipples are
poking through and I have vibrating nipple clamps locked on them. A long real
feel butt plug is shivering delightfully deep in my ass and I'm stroking my
cock with one hand, sucking my thumb deep into my mouth wishing it were a
thick prick or a wet cunny pressing into my face.
I'm going to keep stroking and caressing myself for you darling, cum with me,
closer, closer, yes baby, let me see you spurt, let me taste you flooding.
Now darlings, form a queue and let Lisa make you cum and cum again until
you've covered me in your hot juices.
Then you can go to the back of the queue and wait for your next turn. By the
time the bath is filled with cum it will be time to make the cocktail that
bit more fruity, when you come to the front of the queue again I want you to
straddle the bath, then piss all over me and wash all the lovely sticky cum
off. Then when you're all done you can watch me bathing in the cum and piss
filled bath until you're ready to fuck my ass while I kneel in it, you can
even push my head down into the cocktail if you like darling.
And the first one to track me down gets a tour poster which has a wonderfully
filthy photo of me in action.
Maddy
- 19.10.2022
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