The Sitter
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The House Sitter free porn video
My name is Donald and I'm a house sitter. It started off when I was in
my teens and I baby sat for a few of my parent's friends and as I'm very
conscientious and my Dad's senior partner needed someone to look after
his house while he was on holiday, the whole thing grew from there. I'm
27 now and I house sit full time, supplementing my earnings with a spot
of book reviewing. I'm not rich, but I have a comfortable living as I
have virtually no overheads.
Of all the grand houses I look after through the year my favourite is a
place near Dumfries called Glen Moraldi, a small place that was formerly
the gate house to a large mansion (which has since collapsed). It's
quiet, lonely, and I have to drive almost fifteen miles to the shops but
I love it. Why? Because as well as a house sitter and book reviewer I'm
also a transvestite.
For those of you who are unfamiliar with the term it means I like to
dress as a woman, though it doesn't mean I'm gay. Okay, I am gay but
most transvestites aren't. I sometimes dress at my other charges but
here in the wilds of Scotland I can wave goodbye to Mr & Mrs Hodder as
Donald then change into my alter ego "Deborah" until it's time for them
to return. I have been caught once or twice by the postman or utility
people but I am fortunate in having a face and body that are
convincingly feminine. In fact, now I've told the Hodders that my
"girlfriend" sometimes stays with me I can spend the whole fortnight as
Deborah without fear as long as I change back to greet them as Donald.
They're happy to have my girlfriend here as they trust me (and I
wouldn't do anything to abuse that trust). They're a wonderful couple,
Charles is a consultant cardiologist and Maria is a surgeon (I think
they were a bit miffed when their son Thomas left medical school and
went backpacking to Australia) and despite being very high powered they
are very friendly. They probably wouldn't mind if they found out I
dressed but I don't have the nerve. It's so much fun to dress completely
as a woman, and I usually shop in Dumfries as Deborah and I have yet to
have any problems.
But I digress. My story starts when I was asked to look after the place
over the Millennium. Of course everyone wanted my services and I was
offered some substantial cash bonuses for doing so, but the thought of
spending the New Year away from it all as Deborah was too much of a
temptation and I drove up on Boxing Day after spending Christmas with my
folks.
It was New Year's Eve and I was curled up on the sofa, sipping some wine
and munching a little cheese as I read Terry Pratchett's latest when I
heard a car pull up in the drive. I got up, slipped on my heels and
walked quickly into the hall. My one fear has been that the Hodders
would come home unexpectedly and although for all intents and purposes I
was a woman, they might recognise my features so I played it safe. I
walked to the bottom of the stairs trying to decide whether or not to
answer the door if it was a casual caller when the sound of a key in the
lock scared the life out of me. I turned to sprint up the stairs but it
was too late; the door swung open and a young man walked in.
I froze, halfway up the stairs. I had to get rid of him. Convincing was
a term that only applied to brief meetings, anything longer and I'd give
myself away somehow.
"Hi," a vaguely Australian accent said. I swallowed nervously and turned
around. "I'm Tom. Who are you?"
Oh shit. Their son Thomas! I managed a nervous smile. For a moment I
almost told him who I was but I modified the "Donald" to Deborah just in
time.
"Pleased to meet you, Deborah," he said with a friendly smile and my
heart just melted.
He was a tall man, hair sun bleached to blond and with a deep tanned and
wrinkled face though he couldn't have been more than 30. His blue eyes
held my heart completely and I suddenly knew what it felt like to be
smitten by a handsome man. He shrugged out of his heavy jacket,
revealing a thick sweater beneath and his worn out jeans and scuffed
walking boots completed the picture of a rugged man who had spent the
last five years wandering the world.
"You look exhausted," I said, partly because he did and partly so I
could hurry him up to bed before he got too close a look at me.
"Y'could say that, love." He dumped his backpack at the foot of the coat
stand and threw his jacket over it. "How about I make us a nice cup of
coffee each?"
He strode towards the kitchen and I scuttled down the stairs after him.
"Actually I've just opened a bottle of wine. Would you like some?" Maybe
he'd tire more easily with some alcohol in him.
"Sure," he replied, changing direction and sweeping past me, his eyes
taking in my body. I felt both afraid and exhilarated at this unexpected
attention, then I came down to earth with a bump. He thought I was a
woman, and even worse there was a possibility he fancied me. I had to
get him into bed as soon as possible. I stopped abruptly and pursed my
lips to stop the shocked laugh. What I meant was I had to get him to
sleep as soon as possible. In the morning I would be Donald again and I
could pretend Deborah had left.
I strode into the lounge to find Tom emerging from the kitchen with a
glass and a chicken leg. He picked up my bottle and poured himself a
glassful then topped up mine before sitting in one of the chairs.
He smiled as I moved to the armchair and sat down carefully, crossing my
legs and thanking my lucky stars I'd got a knee length skirt on.
"So where are my folks? Gone off to some dry old party?"
"Yes," I replied with a smile, "some guy from the hospital."
He frowned. "Not Coburn?" He rolled his eyes when I nodded. "That guy is
such a prick. One of the reasons I left medical school." I must have
looked shocked as he held out his hand and apologised. "I'm sorry, I've
spent too much time on rusty old ships talking to rusty old sailors." He
grinned in a very charming way. "I guess my language has got a bit
salty."
"How long have you been back from Australia?" I asked taking a sip of
wine. I was enjoying his company but I knew I had to get him out of here
before I did something to give myself away.
"Well I left Perth in '98 and went to Japan for a while. Then I headed
for Malaysia, then I stayed in Thailand for about six months then just
sort of wandered back on what ever ships were available. I spent a week
in Bangalore, two in Aden, a month in Naples," he laughed, "about half
an hour in Gibraltar and I arrived in Portsmouth this morning."
"Wow! That sounds marvellous."
"Yeah," he said, taking a sip of wine and, I noticed, a quick glance at
my legs, "it was good fun."
I took a drink of my wine too, partly enjoying his interest but getting
more and more worried about what would happen when he found out.
"Tell me," he said, putting down his glass and leaning against the arm
of his chair, "why someone as pretty as you is all alone in a big house
over the Millennium?"
I blushed and looked away. This was getting out of hand. He was
obviously interested in me and although I was interested in him I could
see a very short, one sided fist fight occurring if I wasn't careful.
"I like being on my own," I said.
"Me too." He picked up his wine and drained it, reaching for the bottle.
"I've spent the last five years on my own, for the main at least. But it
is nice to have someone to talk to."
I managed a smile as he leaned over towards me and picked up the bottle,
his eyes wandering all the way up from my feet to my face. He refilled
his glass and moved to top up mine. "No," I said, my hand moving over
the top of my glass, "I'll pass."
"Ah, c'mon, Debs," he grinned, waggling the bottle so it sloshed,
"there's only a little left."
I met his gaze and for a moment we stared at each other and I swear my
heart began to pound. I broke away. What was I doing! Tom took the
opportunity I'd left him and emptied the bottle almost filling my glass.
"It's the Millennium, push the boat out."
Oh God! I'd actually forgotten about the Millennium. He'd want to stay
up until well past midnight. I glanced at the clock. Half past ten! I
could feel my fingers shaking, I was in serious trouble. If I went to
bed early he'd expect Deborah in the morning and I was sure he'd be
staying until his parents returned. But what was the alternative? Could
I convince him until after midnight? He'd only been here half an hour
and already he was coming on to me. I looked over at him, his broad
shoulders, tanned face, wavy blonde hair, the way his eyes crinkled when
he smiled.
Oh no, I was really falling for him. How could I discourage this man
from taking an interest in me when I couldn't keep my eyes off him? His
eyes flicked up and caught me staring. I blushed and reached for my
drink.
"Where are you from, Deborah?"
I thought for a moment. There was no point lying. "Halifax. In
Yorkshire."
"That's a lovely part of the country."
I shrugged. "If you like hills, I suppose."
He laughed and I found myself gazing longingly at him. I tore myself
away and buried my gaze in the wineglass.
I put the glass down and saw he was staring at me with a slightly
worried frown. My heart missed a beat. What had I done to give myself
away?
"Are you alright?" he asked.
"Me?" I was puzzled. "Yes. Yes I'm fine." I put the glass back on the
table almost knocking it over.
Tom lowered his head. "I'm sorry. I should go."
"Go?" Now I was totally confused.
He stood up and drained his glass. "I didn't think. You're alone in a
big house miles from anywhere with some bloke you don't know from Adam."
Good God! He was concerned for me.
"I'll go into town and stay in a hotel."
"Um," was all I could manage. "Stay," was what I wanted to say. "Stay
here and take me to bed," was what I really wanted to say, but I
couldn't. It didn't matter how long he'd spent alone on ships I was sure
he would remember that what was between my legs wasn't the usual woman's
arrangement.
I followed him out into the hall, wondering if I should just tell him.
After all I'd fallen for him big time.
"I'll phone tomorrow and give you my number." He picked up the backpack
and started to shrug into it. "If you could call me when my folks get
back." I nodded, a little disappointed that his reasons were so mundane.
He looked me over, quite obviously this time, and smiled. "You are very
pretty."
I blushed again, looking away, then forced myself to look back at him,
after all he was going, I was safe. So why was I so devastated?
"And you are very handsome, Tom."
He started to smile then stopped, his eyes searching my face. I stood
there enjoying his stare as I stared back at his worn and handsome
features. We drew closer and I made no effort to resist as his eyes
closed and his lips touched mine.
It was all I could do to stay standing. His mouth was hot and soft, his
lips gently pressing mine in a light, delicate kiss that burned right
down to my stomach. For just a moment he let it get passionate, our lips
pressing harder, our mouths opening, and then he broke away, almost
sending me falling forward into his arms. I'd forgotten about who I
really was, for just that moment I was his girl and I'd forgotten about
everything else, including gravity. He reached out and grabbed my elbows
to steady me.
I was totally flustered. I couldn't even look at him.
"I'll speak to you tomorrow, Deborah."
"U-huh," I managed, but looked up at him and smiled warmly.
"And don't worry, I won't tell my folks."
My smile slipped. Tell his folks what? "I don't understand," I said. So
he'd kissed me, would his folks object?
"About you dressing while you're here." He opened the door as I reeled
from the realisation.
"Hold on!" I said, and slammed the door closed again. "You knew?"
There was a slightly bemused look about him. "Not at first, no."
"Then how did I give myself away?" I thought I'd done so well and now I
found out he was on to me I was almost angry.
"You didn't really. There were just a few points I noticed."
"Like?" I demanded.
"Your neck is a little thick for a woman..."
"I've seen plenty of women with thick necks," I countered.
"True," he conceded, "but you have large feet for your height and your
upper body is a little broad. And your hips are narrow."
"Lots of women..."
He held up his hand. "I'm not saying you're not convincing. I'm saying
I've had medical training so I notice theses things, and I knew a lot of
transsexuals in the east so I know what to look for."
"Oh," I said, a little deflated, not to mention a tad upset I'd been
seen through when I thought I was convincing.
He reached out and took my hand. "I'm sorry Deborah, I didn't mean to
make you feel bad. I've seen a lot of transgendered people and not many
of them are as good looking as you."
I smiled at him as he rubbed the back of my hand with his thumb. I felt
much better about myself now, and after all, I did shop in town dressed
and no one had commented so far.
"Hang on," I said as another thought occurred to me. "If you knew, why
did you kiss me?"
It was his turn to look puzzled. "Because you are very attractive. And
I'm sure you're as lovely as a man as you are as Deborah." My mouth fell
open, no really, it did just that. The man of my dreams had just told me
he fancied me. As I stared at him I felt his hand move up to my upper
arm. "I hope I wasn't out of line kissing you."
"No," I breathed and felt his other hand grasp my other shoulder. I
tilted my head back and he drew me to him, our mouths meeting in a kiss
every bit as dreamy as the first.
I opened my eyes and looked out of the bedroom window across the Loch.
For a moment it took me a while to remember where I was then I sighed
sadly to myself. The dream was so vivid in my mind. The romantic chat,
the revelation, the kiss, him leading me upstairs and our passionate
lovemaking. I sighed again even deeper.
My head was fuzzy and my mouth felt sore. The fuzziness was undoubtedly
due to the drink we'd consumed... I'd consumed but my lips felt raw.
Other sensations started to make themselves felt, rather intimate
sensations and I rolled over and sat up. I was still wearing my
stockings but the rest of my things were scattered all over the place
and mixed among them were jeans, a sweater, and other clothes from my
dream. The bed was empty but I could smell the aroma of sex, and in the
bedside bin were some condoms. Rather a lot of them.
I remembered it all suddenly. He was like a machine, we must have made
love for hours, I don't know how we sustained ourselves. My body was
sore all over but I hugged myself in delight as I recalled the hours of
exploration of one another. It had happened, it had all actually
happened!
I lay back and spread my arms across the covers, revelling in that
morning glow.
I heard the sound of someone outside the door. For a moment I panicked
thinking it might be Mr & Mrs Hodder but then I relaxed. It couldn't be.
It was Tom, my man.
The door opened and in walked Tom with only a breakfast tray to cover
his manhood.
"Morning Debs," he said, putting the tray down on the bedside table.
"Did you sleep well?"
"Yes, Tom. I slept wonderfully."
He leaned over and kissed me and all my exhaustion melted away. I
reached out and touched him and we forgot about breakfast.
So that was how I spent my Millennium. Tom and I are now a couple and we
spend our time house sitting mainly. I still review books, he's writing
one about his travels. There are a few new homes on our list now and
some of them know us only as Tom and his fianc?e Deborah. We decided to
pretend to be engaged as it sounds more committed than "girlfriend" and
some of these people are very select about whom they let into their
homes.
I've casually mentioned the subject in conversation and Tom sees no
reason why two men shouldn't marry especially when I would look terrific
in a wedding dress. I'll give him until our first anniversary over New
Year and if he hasn't asked me by then I'll ask him. After all, if I
have to be a man underneath I may as well take advantage of it.
Miracle
- 30.10.2020
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