The Liberation Of Father Mortimer
- 4 years ago
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My First Time free porn video
The first time
The part about the luggage is made up but everything else is completely
real and it gives you a fly on the wall description of a cross dresser's
first time with a man as it really happened including her feelings and
sensations. For those of you who have never had this experience I can
assure you this is as real a description as you will find without any
embellishment or misguided fantasy. You may not have the same experience
or sensations but this is exactly what happened to me. I hope you find
it sensual and helpful.
.......................................................................
Never give up - sometimes an impossible situation turns out to be
completely different in a way that you could never have imagined. That
was the case with my lost luggage bag at the airport a couple of weeks
ago.
Lost luggage is always a nuisance but in my case it was a disaster. I
was travelling for work and took the opportunity to pack a whole pile of
my girly clothes for some quiet dressing up time in the evenings when
alone in my hotel. It contained my sexiest lingerie including my
favourite pink burlesque corset and fishnet stockings. I had several
skirts and dresses most of which were in a dominatrix flavour with
leather and shiny tight pvc. But for a change I decided to take along my
very pretty little girl dress with red polka dots and a 6 layer fluffy
petticoat. Every now and then I just want to be cute and gorgeous. I
guess there are 2 Cindys - the cute little girl and the tough domme
depending on what mood I am in. I also managed to squeeze in a range of
boots and super high stiletto heels and finished off with my boobs and
makeup. Luckily business was mostly informal so I could get away with
just a few boy clothes!
I packed all of this in my very manly looking holdall with a unique and
distinctive racing car logo on the side. Anyone looking at me would
think I was a manly boy racer type. Little would they know that inside I
was all girl - well at least in my mind.
I had a wonderful week playing dressups all alone and had arrived back
at my home airport. Unfortunately I was late picking up my bag from the
carousel because I met a friend but luckily when I arrived my
distinctive bag was making its way round again. I dragged it from the
carousel, lugged it to my car and drove home.
When it was time to unpack I unzipped the bag and.... Shit! shit shit
shit! It wasn't my bag! It was jam packed with men's clothes. Smelly and
huge. I checked the label and indeed it was somebody called B Markinson.
Well Mr Markinson you are in for a shock when you open up the bag you
think is yours! Oh no. What the hell will I do because it will have my
name on the label - C Madison for Chris Madison. I panicked a bit but
told myself to sit down and work out some excuses just in case Mr
Markinson looked in the bag, which of course he will do.
I pondered and worried about this for an hour or so when suddenly my
mobile work phone rang. Who was ringing me at this time of night! I
answered with a rather abrupt, "Yes?" A rather cultured male voice
answered.
"Oh hello. I was after Ms Madison."
My mind raced. He said Ms Madison.. Ms not Mister. That could mean only
one thing. This was Mr B Markinson.
"Um yes. This is Ms Madison," I blurted out.
"Ms Madison," said the voice, "you are Mzz Madison," and he emphasised
the 'Ms'.
I realised I had just answered in a normal boy voice. Drat. I stammered
and answered again that I was Ms Madison in a slightly higher voice
trying to be as girly as possible.
It was a quite stilted conversation that followed but Mr Markinson, who
I found out was named Brad, explained how he had picked up my bag by
mistake and had the same shock I did. He thought it was great that a
girl had the same bag as him and was interested to know what she was
like. He apologised for rummaging round to find out something that
identified the owner and found a hidden label inside with my phone
number - and it did not have my full name on it thank God. He did laugh
about the nature of the clothing he found and was intrigued about the
girl owning this rather sexy array of gorgeous clothes (he actually had
said the word "gorgeous").
I told him my name was Cindy and followed up by a lame story that I was
a rep for a lingerie club and had been on a sales visit to some lingerie
parties, and luckily he bought the story. We chatted on for a while and
I must say I started to like him quite a bit. He was easy going, had a
great sense of humour and had such an amazing voice.
Then he really surprised me. "I know a little about life," he whispered,
"and from the clothes I see in your bag, and your voice, I want you to
know that I like cross dressers."
I was stunned. Do I continue my pretence or do I come clean. My mouth
inexplicably went dry and my tummy started to turn over full of
butterflies.
"Um... Do you really?" I stammered. What a stupid thing to say.
"Yes I do Cindy. And I would love to hand you back your clothes in
person. Would you like to meet in a quiet but public place this evening.
We can swap bags. Don't worry yourself at all - I will be a perfect
gentleman."
I was taken aback. I had never been out dressed before, let alone to
meet a man. But I realised this was too good an opportunity to miss.
After all, I can be sure it is a quiet place and can always get away if
I need to. We agreed to meet near the airport at a path near a park at
8pm. It would be very quiet and dark but there are houses nearby so I
could always get help if he turned out to be a creep.
You know it is really weird. As a boy I would have no problems and fears
going to meet a person alone there, but as a girl I was full of
hesitation. The thought of being dressed as a girl changes your whole
outlook.
I had 2 hours to get ready so set about my transformation.
Since I had been playing girlies all week I was already smooth all over
and even had my toes painted bright red. So all I had to do was to slip
on an outfit suitable for a first date. I squeezed into my purple satin
corset and tightened the laces completely as far as they would go.
Although I was going to be out for a few hours I wanted to make my waist
as small as possible so I was going to put up with the discomfort. I
could hardly breath as I pulled and pulled, giving me the tiniest waist
possible. I was quite thin for a boy and always managed to get such a
small waist such that I had a slim but very pronounced hour glass shape.
I pulled on my sheer black stockings, swearing yet again that I need to
do this before I put on my corset, and clipped them to the suspenders.
The corset had an attached bra and I slipped in my false breasts. I
loved the feel of these breasts - they felt so real to touch and made me
feel so feminine. I paused for a minute to enjoy my lingerie and caress
my breasts. Hmmm.
I pulled on my gaff to hide my little thingy and made sure it was over
my suspenders and not trapped. This was an interesting thing to do
because I was giving myself a signal. I could have pulled my gaff on and
clipped my suspenders over the top, making it difficult to get off. But
instead I made sure I could fling them off, or someone could take them
off, easily. In the back of my mind I wondered what it would be like to
be caressed by a man. It was exciting and nerve wracking at the same
time.
I sat down and applied my makeup. After putting on some foundation to
make my skin look smooth and to create some light and shade to create a
feminine oval face, I went for a real tarty look with dark smokey eyes,
long false lashes and bright shiny red lipstick with lashings of gloss.
I wanted him to see a very sexy girl, especially with my bright shiny
lips. I know my lips can be very pouty when made up and irresistibly
kissable. As I layered on my lipstick and gloss I imagined being kissed.
What would it be like to be the receiver of a manly kiss? Would he want
to kiss me. Would I want to kiss him when really faced with the
opportunity.
I found the perfect dress. I had just bought it from ebay and it was
just right for a cross dressers. It was black but with lots of gold
sparkles in the material. The material was very classy but the
shimmering in the light made it very sexy too. It had batwing sleeves
that gathered in at the elbow for long tight sleeves to the wrist. The
loose fitting top then made way for a tight fitting mini. The whole
dress was stretchy and hugged my bum closely. It was so perfect since it
allowed my larger torso to be hidden while it showed off my tight sexy
bum. Although loose at the top, the material perfectly draped over my
corset so you could get an idea of my small constricted waist
underneath. It was very sexy. I finished it off with lots of bracelets
and bangles on my wrists to help disguise male looking hands, followed
by a sparkly chunky necklace and clip on earrings.
I found my favourite wig. It was long, curly and a lovely strawberry
blond colour. A perfect counter for my black and gold dress. Finally I
squeezed into my high stiletto heels - I loved all 6 inches of them!
They were a leopard print, with colours nicely matching my dress. They
would be hard to walk in but I hoped he would hold me and help. We would
not be going far.
I finished off by painting my nails. I took my time and applied 3 coats
of shiny red nail varnish that matched my lipstick. I was ready for my
date.
I looked in the mirror. I was stunning and could not believe I was about
to share Cindy with another person - and a handsome man. I packed a
handbag with some lipstick, money and tissues. Tissues? What was I
thinking!
I hesitantly stepped outside to get into my car. It was a very ungirly
large 4 wheel drive. I felt nervous stepping outside, hoping no
neighbours saw me. But also I was exhilarated feeling the cool air
against my legs and the tug of my stockings being pulled against my skin
by my suspenders. That feeling is wonderful and so special. Men never
get to feel that sensuous caress against your legs. I Love it.
I drove across town to the appointed spot and as usual was early. I had
not been there before and I saw the small park with a walkway going down
by the river. It was closer to houses than I thought, which meant I had
to park across the road from them. I sat in my car nervously waiting. I
could not imagine how much activity was in the houses - people
constantly coming and going. I was afraid they may wonder why a girl was
sitting in a car by herself. I snuck into the back of my car where I was
shielded by darker windows and waited for what seemed like an eternity.
What was Brad going to be like. Have I made a mistake. How could I have
put myself in this position. What if he was a gay basher with friends.
All of these things ran though my mind. But every time I looked down and
saw my smooth stocking clad legs and stilettos the excitement took over.
What if he was gorgeous and handsome. What if he wanted to kiss me.
Would he hug me tight and would I feel him growing against me, excited
by my femininity.
Suddenly a car appeared and pulled in just in front of me. It was Brad.
He waited for a minute - maybe it wasn't him. Then he got out and looked
into my car, standing by his boot. He was indeed tall. Maybe mid 40's
with a well built but slim frame and a very handsome face. He was a
dish. Why did he want to be here with me? Was I good enough? My stomach
churned like a schoolgirl on her first date and I slowly opened my door,
stepped out gingerly on my heels and moved to the front of my car. I was
about to walk up to him and give him a hug when he held up his hand and
said, "Stop Cindy, let me look at you."
I knew I looked good. I knew I did. I felt confident and sexy. So I put
my hand on my hip, leaned back on one leg and put my other leg forward
turning it slightly to show off my stiletto. I could not smile because I
was too nervous. He looked me up and down, smiling. "Gorgeous. Stunning.
I love that dress. Turn round."
I turned round and showed him my back and the tight skirt of the dress.
I wriggled my bum a little and could not help but giggle a little. Brad
did not say much more. He just looked at me as I turned round to face
him again. I smiled nervously. Girls, I cannot tell you how weird it is
to be stared at like that. I guessed I turned him on - he had a longing
in his eyes as he looked me up and down. At my legs, my stilettos, my
tight skirt, my blond hair, my shiny red lips and my stunning gold dress
that I noticed was sparkling gorgeously in the street light as I moved.
I took the initiative. I walk up to him, swaying my bum from side to
side, looking him in the eyes and wrapped my arms round his neck. He had
piercing blue eyes that looked straight through me. He was so handsome
and I was a lucky girl. If anyone saw us it would be like boyfriend and
girlfriend meeting. I pushed myself against his front and looked into
his eyes.
"Hello," I said. Softly but just in my normal boy voice.
Brad smiled nervously back. "Hello," he said softly.
We stayed like that for a few minutes until I said, "Shall we go for a
walk."
"Sure" he smiled. And we parted. He held my hand as we headed for the
path by the river. I was a little unsteady so I wrapped my arm round his
as we walked silently side by side. I started to realise that men don't
say much. It is quite different when you are in the company of girls. He
pulled my arm away and changed it so we were holding hands. I would have
thought he would say why he did that but he just did it. Little things
like that start to mean more. In that simple motion he showed he was in
charge. He was going to decide how we were going to walk and as a girl I
was expected to go along with my man. It made me feel secure. It was a
lovely feeling strolling slowly with him by the river. I was a little
unsteady so he held my hand tight and was attentive when I slipped a
little. I realised he was looking after me and I started to fall in love
with him right there.
We walked for a short while and then he stopped and rested his back
against a low wall, low enough to sit on but he remained standing and
pulled me to him. No words were spoken.
I knew he wanted to kiss me, and I felt so feminine that I wanted him
to. He held out his arms and I walked between them closing my body
against his. It just felt so right. I lifted my arms up and held his
face in my hands, seeing my red nails brightly shining against his light
skin. He liked that I could tell. And I liked caressing my man's face. I
leant up and he bent down and we kissed. I was kissing a man for the
first time. I made sure I kept my lips soft so that I felt feminine to
him. I whispered to him that we could not have sex - I am not ready for
that. He nodded.
I expected him to push his tongue into my mouth and kiss me hard but it
did not feel like that. It did not feel too much different to kissing a
girl actually, which surprised me. I thought a man would be harder or
rougher. But it wasn't. We kissed for about a minute.
I pulled back and asked him to grab my bum. I felt his hands move from
my waist to my bum and he rubbed them softly over my skirt, pulling me
in to him. We kissed again as he held me close to him. I was mesmerised.
It is a lovely feeling having a man caress your bottom through the soft
material of your skirt. His hands wandered over my cheeks and along my
join but never too far. My hands moved to behind his head as we held
each other close. I moved my body slowly from side to side against him,
knowing it would excite him. I felt so much like a girl and he was
lovely. A lovely handsome man caressing me gently.
I knew I wanted to feel him. To tease him like I had imagined in
countless fantasies. So I took one hand from his head and slid it slowly
between us so I could feel him. I wanted to touch him on his....
I got quite a shock. His jeans were undone! I had no idea when he had
done that. Again he has control. He did things and I just had to go
along with it. So instead of feeling him through his rough denim I
suddenly felt some smooth undies. I was surprised again. They weren't
rough thick material, although they were male undies. But the material
was quite smooth and soft. Not a silk or satin but quite close. That
meant I could feel him almost as if I had him in my hand. He continued
to kiss me and did not say a word or make a sound. Again I thought he
would grunt or get rough. I guess my stereotypes of what a man does are
quite wrong!
I rubbed him softly with my fingers either side. Oh my. He was hard and
big. He was turned on enormously. I think he was maybe an inch bigger
than me. I loved feeling him and moving my small hand against it,
rubbing up and down. We kissed and I rubbed for a minute or so in
silence apart from the jangle of my bracelets. I could not believe I was
touching a man's cock, being held closely and being kissed.
Then he started to take charge. He pulled away from the kiss and moved
aside. Walking round to behind me. He had been leaning against the wall
so now I was facing it with him behind me. Instinctively I bent forwards
and leant over the wall with my front on the raised grass beyond the
fall at 90 degrees. I pushed my bum out towards him and he pushed
against me. My knickers were still on so I knew I was safe and he was
making no attempt to remove them.
I started to wiggle my bum from side to side. I wanted to please him and
could not believe how tarty I was acting. I felt him push against me as
I rubbed, and his hands held my hips as he ground against me. Again he
was not rough - I really expected men to be rough but when you think of
it most of us are gentle in our lovemaking. I pushed my bum out and
wriggled. I moaned slowly. I was very excited and loved the feeling of
him against me. If he was going to be silent I was going to let myself
go. "Oh yes... Push darling... Mmem yessss... Hold my breasts." I wanted
him to reach down and feel how wonderful my breasts were.
Brad reached forward and started to caress my breasts through my dress.
It was thin material so he would feel my silicone breasts easily.
Although I could not feel his touch directly, I felt him squeeze me and
pull by breasts up to my skin. So I could feel him move his fingers. It
felt gorgeous. A man was caressing my breasts. He spoke. "Mm they feel
so real."
He was still silent but then actually spoke again as his movements
increased in speed yet still not rough. He gasped that he might not be
able to keep his promise of being a gentleman. He was really horny. I
loved this position and looked back to see my outfit and a man pushing
against me. I started to moan more as I wriggled myself against him. I
moved my bum faster and faster, pushing back against him as he moved
against me.
Then he stopped and made me stand up. It was so interesting not to be
calling the shots - he knew what he wanted and had complete control. I
was in no doubt that he was the man and I was the girl. I did what he
wanted.
Still he did not speak. Why did he stop. What did he want. He led me
back along the path. Suddenly a boat appeared and the driver moved it
closer to us looking at us. Did he 'make' me. Was he worried about me.
Was he going to tell us to move along or shout abuse. I felt insecure
then. I moved to the side of the path away from him and snuggled up to
Brad who held me tightly. He was protecting me. I looked down like
Princess Diane and the man chugged past slowly. I wondered what the man
thought.
Brad took me back to my car and I opened the door. What did he want.
Still without speaking he climbed in and I climbed in after him on the
backseat It seemed right that I lay down as he sat on the other end of
the seat. I lay on my back and he knelt between my legs, moving them
open slightly. He pulled on my undies and slipped them off. Luckily I
had the stockings underneath instead of on top! He pushed my legs out to
the side and positioned himself so he could suck me. Oh my God. A man
was going to suck me. I thought this was interesting that he wanted to
suck my cock, suggesting to me he had a gay or girlie side. Perhaps this
was why he liked crossdressers.
I felt his lips on my girlhood. Oh it felt good. He dribbled on it and
then placed his open mouth over me pulling me Into his mouth. It felt so
much better than the feeling of entering a girl. It was softer and he
ran his tongue all over my most tingly and erogenous parts. I felt like
a girl, seeing my legs in the air either side of his head and my long
stilettos pointing in the air. I moaned loudly and long as he caressed
me with his lips and tongue. Oh my god the feeling was the most intense
ever and I moaned louder and longer. He sucked me softly, sometimes
sucking me into his mouth completely and sometimes just working round
the tip with his tongue. He was an expert cock sucker! Very quickly I
felt like I would cum in his expert mouth so I put my hands on his head
to stop him. I did not want to do that yet because I wanted to please my
man.
He stopped instantly and then moved on top of me. I wrapped my legs
round his body. That feeling in that position was so totally awesome.
You cannot believe what it feels like to have a man's weight on you and
your legs wrapped round him. My legs seemed to feel so easy and right
wrapped round him. It was heaven. Being s girl came so amazingly easy.
He started rubbing himself against me and I wrapped my legs higher so
his manhood was rubbing against my bum on the outside. I started to buck
and wriggle against him and moaned again. I knew my moaning turned him
on. He kissed me and grabbed my arms which he held in front of me
against my breasts. We writhed and wriggled as if we were making pretend
love. So close yet not quite.
Suddenly he held me extremely tightly. My arms could not move. Oh my god
- how strong he was and I could not move. Not even a bit. I had never
felt the strength of a man before like this and I was the feminine
helpless girl. I realised he could do anything he wanted and I would be
powerless to stop him. Moments before I felt I was in control and could
stop him if I wanted to but now I could not believe how much stronger he
was than me. I was helpless and it made me a little scared.
But after a short while he released his grip. Later I realised that he
was trying not to cum on my dress. He had great control!
We lay there for a while and I pushed him up. It was my turn to feel
what it was like with a cock in my mouth. The first cock ever. He sat up
and I repositioned my self so I could suck him. I wanted him to cum. My
hair cascaded over his body as I pushed it aside and lowered my mouth
into him. It was softer than I thought it would be and did not really
have a taste. I did not really feel the warmth as I expected but neither
was it cold. I licked round the outside and wrapped my hand round it,
moving it up and down slowly. Then I opened my mouth and slid my red
lips over his cock. My head went lower taking him all the way Into my
mouth so that I felt his tip push against the back of my tongue. It felt
lovely. I moved my mouth up and down as he pushed his hands back on the
car seat leaving me free to do whatever I wanted. Licking and bobbing up
and down, up and down, up and down. Feeling him inside my mouth.
Tantalising him with my tongue around his tip and trying to touch that
dimple of sensitivity where the skin meets. He laid back in the seat, in
a sitting position while I worked on him. I expected him to grab my head
but he left me alone as I worked on his cock.
He was silent and still as I moved on him. He never bucked or grabbed
me. He just left me to caress him with my mouth. I expected him to start
to writhe or push against me but he just laid there. Up and down.
Faster. Faster. Up and down. Licking and rubbing his balls. Up and down.
Faster. I expected him to moan and groan and tell me he was cumming.
From the male end, I knew what he was feeling. He would be almost out of
control and just before that moment of ecstasy he would feel his cock
get harder and grow. He would feel himself tense up and suddenly
everything would stop in that massive moment of tension where no muscles
move and you are about to explode. Then you explode, feeling the tension
and juices run out of you in one massive burst with your cock pulsating
and shooting.
But as a girl working hard on him and waiting for that glorious moment
of tension where I feel his cock grow massively and then pulsate in my
mouth, I heard nothing and did not feel anything until suddenly my mouth
was filled with wetness. He was cumming in my mouth and I had no idea it
was about to happen. I slightly gagged but kept my mouth there, and
started to suck on it, swallowing it all as it came.
It did not explode or run down my mouth as I had read about. It was a
silent and gentle affair. I sucked him dry and then popped up and kissed
him, letting him taste some of his own juices, which surprised him a
little.
I smiled at him and asked if he was ok. He smiled back and pulled me to
him. I said that a girl's job is to clean up her man so I leant over to
the front seat and grabbed a tissue from my bag. My bum was in the air
and he would see my knickers and stockings as my mini skirt was riding
up my waist. He spoke (at last). "Wow that looks so sexy with you like
that. You have a lovely bum and sexy legs."
I smiled to myself and giggled. "Yes I know, I thought you would like
that view." I wriggled my bum a little and then stretched back to wipe
my man's cock clean like a dutiful girlfriend.
As he leant back in the seat I snuggled up against him, laying my head
on his chest. My man. My darling. I was his girl.
"I was very nervous you might not like me" I whispered. And at last he
started speaking.
"You needn't have been nervous. In this light you look like a girl. Your
dress is stunning and I really like all the bangles which is a nice
touch. That guy in the boat would have thought you were a sexy girl in a
mini dress with heels and he came over to check you out. He was thinking
I am a lucky bastard and he probably went off and had a wank thinking
about you. You act like a girl and look like a girl. And you kiss like a
girl."
That really surprised me. "I don't think I kissed like a girl because I
was so turned on. This is how a girl kisses." I leant up to him and
kissed him gently on his lips. I made sure I did not tense my lips at
all but left them soft and squashy. I pushed myself slowly against him
with my breasts and my face so that my lips slightly squashed against
his. He opened his mouth and our lips touched more. I was very soft and
gentle. I pulled away and smiled at him.
"Gosh," he said, "that was amazing. So soft and sensual."
"That's a girly kiss." I smiled.
We stayed in that position for ages and chatted. Then it was time to go
so he stepped out and kissed me goodbye, caressing my hair with his
hand.
"You really are gorgeous you know." And with that he drove away.
It was only minutes later that I realised we had not swapped bags! That
meant we had to meet up again. When we meet he would have the chance to
go through my clothes with me. One of us would try on my little girl
frilly dress. But which one of us it was and what happened next is
another story.
Clover
- 08.02.2023
- 22
- 0
