Ladyboys Moving to Thailand and my first Ladyboy
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Young 'Lady' Gina's Homeschooling free porn video
Young 'Lady' Gina's homeschooling
I was still called George when I moved in with my slightly excentric
aunt Celia almost two yeas ago, after my mother had a serious nervous
breakdown due to my lecherous oger of a father leaving us. For some
reason aunty, after walking in on me wearing her prettiest undies and
high heels, had taken up encouraging (and accomodating) my little
transvestite affectation to the full. Aunty sorta found it a
delightfull and classy foible and decided that she was from now on
going to refer to me as Georgina and that I was going to be her
'special project.' I was a stroke of luck, an exotic delicacy she
could proudly present to her exclusive circle of 'strange' friends.
Aunty was a beautiful and well preserved woman in her early fifties.
She was definitely slightly depraved and had a seriously mischievous
nature but she always hid these assets behind her delightfull and
totally irresistable charm.
I was provided with the prettiest lingerie, stockings and dresses.
There were beautiful wigs and the most exquisite of highheeled shoes.
Everything a glamorous young society miss could possibly desire and
more. On top of that, aunty spent hours and hours instructing me how
to walk, talk and in all aspects behave like the ultra feminine
debutante she wanted me to portray. I would elegantly mince around her
apartment in the highest of heels untill it became second nature. In
the end, when my calve muscles had adjusted to them it actually became
a chore 'not' to wear them. Aunty had by now completely taken over my
life but for someome like me, who had already been attracted to the
delights on offer, the rewards were just too big and there was no way
I could possibly fight the temptation, even if I had wanted to. And
although her tone of voice always sounded almost sugary sweet, there
was often a slight undertone of wickedness in it and when I didn't
react to her demands fast enough she didn't hesitate to use her
elegant little riding crop on my stockinged legs or my silk encased
girly bum.
For my further education I was made to read excerpts from romantic
novels, girly- and fashion magazines and was made to watch romantic
moviescenes. Of course I was to do so from the vieuwpoint of a
romantic young miss, and one afternoon a week a ladyfriend of aunty
gave me speech therapy where I was to read out loud from said
publications in my sweetest feminine voice. My dressing was not just
restricted to girls clothes, it was only the most feminine apparel
that would do, only silks, satins and taffetta were allowed and I
would never be seen without full make-up and glamorous false lashes. I
always wore fully fashioned nylons, the prettiest of silk undies,
beautifully decorated corsets, lacy bra's and when apropriate for the
dress or skirt, ellaborate petticoats or slips. Having my smooth body
caressed and at the same time permanently restricted by these sensual
materials made my head spin and made me feel like I was living in a
strange but beautifull dream.
And then there were the romance and dating lessons for which I was
dressed particularly sexy and glamorous, just as if I was a real lady
going on a romantic date with a gentleman.
For my tutoring in the romantic arts aunty had an expensive replica of
a classic Pierre Imans mannequin of an older gentleman, dressed in an
expensive conservative suit and tie, sitting on the sofa beside me.
She told me he was called Herbert and was now my 'boyfriend.' She told
me she had a few little improvements made to it so he'd be more
lifelike and 'anatomically correct' as aunty explained with a slightly
mischievous look on her face. I had actually already noticed that
Herbert appeared to have a quite substantial manly bulge in his
trousers and I didn't think that's standard for mannequins like these.
For my tutoring in the romantic arts aunty had an expensive replica of
a classic Pierre Imans mannequin of an older gentleman, dressed in an
expensive conservative suit and tie
Under aunty's supervision I was taught how to flirt with my handsome
masculine boyfriend, resulting in being made to act out a serious
making out scene which involved me sitting on his lap arms around his
neck and passionately kissing him. That's when I found out that aunty
had some more improvements added to Herberts functionality as the more
passionate my embraces seemed, his manly bulge started to softly
vibrate and my fantasy suitor actually produced a heavy breathing
sound and gave of soft manly throath sounds.
I very soon started to enjoy the pretend kissing sessions whilst
sitting on his lap, feeling his manlyness come to live under me. In my
little warped wanton mind he'd put his manly hand on my silky smooth
stockinged legs, and I would eventually accidentally touch him 'there'
and have an innocent little feel. I would wriggle my little girly bum
about and teased him mercilessly, all of it resulting in a gradually
intensifying of the vibrating in my boyfriend's manly regions.
At first I thougt I would hate having to master flirting techniques
like batting my eye lashes, pouting just so and even to how I should
lick my lips or feign feebleness or fragillity to attract male
attention but I was really getting into the role now and getting very
exciting by it. Aunty would be making loads of pictures to show me how
to act and to be as convincing as I possibly could in my role. She'd
instructed me how to coquettishly adjust a strand of hair, to cross my
stockinged legs in a certain way or to timidly adjust his tie, she was
very thorough when it came to these details. And to keep the fantasy
alive she kept telling me how Herbert fancied me and how I was falling
desperately in love with him in her sweetest voice.
When I finally got to see aunty's pictures, the scene was that of a
beautiful young miss in a pretty partydress, passionately making out
with a distinguished older man. Through the lighting and the camera
angles, my brilliant aunt made it so that there was almost no telling
that 'my' Herbert wasn't real and seeing myself like this was both
confusing and so very very exciting...... A few of the best pictures
were neatly framed and now decorated my ultra feminine bedroom as a
reminder of my desired romantic orientation. It worked of course, when
I lay in my bed, dressed in one of my ultra sexy satin nighties, I
kept imagining myself as the girl in the pictures with the difference
that in my fantasy the gentleman in the picture wasn't Herbert but a
real man. That mere thought at first scared me but in the end it had
little hormonally challenged me relieve myself multiple times into one
of my pretty silk hankies like aunty had taught me.......
Aunty had obviously forseen the effect her machinations were having on
me and decided to take it a step further so one evening I was told
that I should learn to dress up a bit special for the more intimate
romantic moments a young lady may encounter. Aunty had obviously done
some shopping for the occasion as there were a number of bags from the
chiquest lingerie shop in town on the bed in her room. First, after my
bath, I was fully made up and a beautifully styled blonde wig was
added. Of course I was already wearing a set of glamorous salon
nails.The cutest black satin and lace french knickers matched the
'Kiss Me Deadly' waistcincher/suspenderbelt perfectly and a pair of
black fully fashioned nylons were now encasing my smooth legs.
Next was the frilliest and flounciest transparent babydoll nighty i've
ever seen. It had a matching floorlength robe and fluffy bedroom mules
to go with it. Looking in the mirror almost made me buckle at the
knees, for looking back at me was an absolute dream of overtly
sexualized femininity. I could easily have featured in a Frederick's
of Hollywood lingerie catalogue. When aunty hugged me she whispered,
"I bet you'd love to show yourself off to some handsome man
now,darling."
"Yes aunty," I meekly replied. "Let's make some pretty pictures then,"
she then said whilst ushering me to my own bedroom. She had obviously
planned everything as she had the whole photography thing
professsionally set up with lighting and everything and to my
surprise, there in my bed was Herbert dressed in classic striped
gentlemans pijamas in burgundy satin. I now he isn't real of course
but he looked soooooo handsome and the promiss of the undoubtedly sexy
pictures to come from this little scenario made aunty's game rather
exciting. When aunty had taken her place behind the camera, I was
instructed to seductively slip out of my robe and sit down on the edge
of the bed before slipping between the lush satin sheets with my
boyfriend. Meanwhile the camera was clicking away. For the next shots
I was to position myself in his arms for a first kiss and a closer
body contact when I again felt his manhood softly starting to vibrate
againsy my own girlish little penis. Aunty had also added a few new
sounds to Herberts repertoire as a low manly voice softly moaned
things things like "Oh, yes baby," "Darling" and "I love you" at my
touches. She took pictures from several angles and moved us around
where needed to achieve the most erotic and realistic images. Meanwile
I was having the time of my life, rubbing my boyclit against Herberts
large vibrating manhood and virtually squirming in my imaginary
boyfriends arms whilst once again pretending he was a real man.
My hand had almost accidentally moved to his crotch, and I threw my
other arm around his neck and kissed his lips I didn't care that his
eyes stayed open or he didn't respond, I was totally lost in the
fantasy of being close to a mature manly man and now both my arms were
around his neck drawing myself even closer to him.
My right hand was moving over his crotch again, touching his hard
manhood, stroking it lightly through the material of his pijamabottoms
which resulted in a moan and another husky, "Yes darling." For the
next shot, my 'lover' was to lie on top of me and the realistic weight
of the doll really made me feel as if this 'man' was physically in
controll of the delicate little lady I was becoming. I was once again
in extacy but it got even better as aunty explained that Herbert was
actually so anatomically correct that I would be able to let my lover
enter my boipussy.
So, after lowerin' his pj bottom, a cushion under my girly bum and
some lubrication aunty helped us get in the right position to let his
very realistic vibrating 8 inch enter me. Of course my darling was
moaning again and telling me that he loved me. I had of coursed
practiced with the dildo my aunt had provided so initially he went in
without much problems but the full 8 inch was still a new challenge.
There was however another feature aunty had not informed me about for
after a while of quiet gentle vibrations I actually felt a kind of
thumping action going on as if my fantasy lover was actually starting
to actively fuck me....It drove me crazy and by now I was so randy
that I was now loudly responding to my boyfriends programmed moans and
utterings of affection with similar statements of my own. My legs
encircled his and my hands were holding on to his hard bum
enthousiastically welcoming the whole 8 inch of his manhood into my
now so wanton pussy.
With me now totally in rapture, aunty's camera was clicking away shot
after shot of her totally adorable 'niece' and her suitor. At a
certain point my body was actually shaking with anticipation as I
almost passed out in a prolonged almost female orgasm like I had never
experieced before. I must still have laid there for almost 20 minutes
basking in the afterglow of the experience after aunty had shut down
Herberts active functions and gently relieved him of his manly duties
by getting him off and out of me. I don't think it really counts as
being deflowered but it kinda felt that way to me. I haven't really
given myself to a man but i've surrendered myself to the concept of
giving myself to a man if you see what I mean. I really couldn't wait
for the photos..........
Aunty knew how to play a game as next day, fifty yellow roses were
delivered with a card from Herbert thanking me for the night........
The following days passed in a virtual daze and I was especially
enthousiast and motivated to become the perfect glamorous little lady
that aunty had coerced me to become. Even more so when after a few
days aunty showed me the final printed pictures of my night of
passion. They were even better than the earlier ones and a permanent
reminder of my obvious talents as an extremely sexy young seductress.
So when later that week I once again found myself dressed up to the
hilt in an expensive taffetta evening gown and in the highest
stilletto's I had ever worn, I knew something special was coming. So
when aunty had led me into the lounge where I had expected Herbert, I
noticed something was different. My delightfully immoral Aunty had a
mischievous smile on her face and whispered in her most amenable tone
of voice, "Now little lady, I want you to meet my good friend Harold
who volunteered to stand in for Herbert today. I had shown him some of
your romantic pictures as he had helped me out with Herberts wardrobe
and as a result he insisted on helping us out today. I think you two
are going to become very good friends so go sit with him and give him
a sweet little kiss."
As soon as I did Harold immediately posessively slipped his arm around
my corsetted waist and whispered, "Pleased to meet you, darling."
Harold looked quite a bit like Herbert, maybe slightly older and
wearing the same type of suit and tie. He was definitely a real man of
flesh and blood though. When he spoke I got convinced he had also been
the source of Herberts voice recordings. It was very familiar and
after my earlier experiences with that voice slightly unnerving. I was
already starting to get very excited at today's lesson. As this was
supposedly my exam I already knew what was expected of me and of
course i'd enthousiastically participate in said scenario. Seducing
this masculine older gentleman and making him fall in love with me
would, for the time being, be my only goal in life...........
The poor man never had a chance, I'm a very very good student....so
when aunty had left us alone to get 'acquainted' and Harold's arm was
still around my waist, I took the initiative and I daringly put my
hand on his thigh and whilst fluttering my eyelashes I timidly looked
up at him. He obviously got my cue and a tender kiss was the result,
followed by a much more ardent one where his muscular tongue slipped
into my mouth, which totally overwhelmed me. The feeling of surrender
when I let this older man's tongue invade me was immense. I virtually
threw my arms around his neck to make this sensual mouthcontact
continue whilst pressing my slender silk-encased body tantalizingly
against my suitor's strong masculine frame. So when aunty returned
half an hour later she found us lovebirds still enthousiastically
making out while I was seated on his lap rubbing my silky bum against
his hard throbbing manhood and his hand was under my taffetta skirt
and petticoats, lovingly caressing my nylon encased thighs.....
Mikhaela
- 15.11.2022
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