Across My Pussy Lips

January 9, 2008 – 10:00 am

What, you are wondering was my Magical Moment. Well, it
was that moment when I discovered that pain was the key
to the gateway of pleasure. My first multiple orgasms
came as a direct result of my being caned. How can a
19-year-old girl enjoy being hurt? But that is the
point, it doesn’t hurt in the accepted sense.

Surely as a child you must have fallen and grazed your
knees, got up and carried on playing without giving it
a thought but if your mother lightly smacked the back
of your hand, you no doubt broke down crying. There in
lies the key. Psychological, if it’s done with love or
within a game, it is pleasure.

Perhaps before I start my tale of my sexual exploits, I
should give you some background.

I discovered masturbation in my early teens and had the
usual wrangling in the back row of the cinema with boys
struggling to ‘cop a feel’.

I lost my virginity two days after my eighteenth
birthday. It was to Jack who, almost to the day one
year later, made me his bride. And now I am going to
tell you all about losing my virginity and my
introduction to SM.

My word, what a time I have had. I have discovered
things about myself that I could never have imagined
anyone doing. Certainly not me. I am only 5 feet tall
and I just love to be dominated by tall older men. They
can use me for sex or beat me, either way I have
wonderful orgasm so I don’t much care, which they do.

I met Jack in the public library. He was kind and
courteous. I think I was attracted to him mostly
because he treated me like a Lady. As a grown up. When
you are seventeen and trying to act sophisticated and
adult, it is a tremendous boost to your moral if an
adult sees you as an equal and Jack was twenty years
my senior. He invited me to lunch at a local Bistro. We
chatted about authors and movies and such like. It was
just everyday chat. Nothing was mentioned that would in
anyway give me a clue to the darker side of Jack’s

We began to see each other two or three times a week.
He took me to concerts and movies and generally, to my
sheer delight, just made a fuss of me. He never made
any sexual advances to me. Oh! We did kiss now and then
but he never tried to grope me the way boys my own age
had. We had been seeing each other for about two months
when Jack announced that he had to go away on business
for two weeks.

‘But you’ll miss my Birthday party,’ I complained.

‘But I will be back two days after that and we will
make it a very special day,’ he replied with a very
broad grin.

I was sad that he wouldn’t be there for my eighteenth
Birthday party. My mother had expected me to bring him
along, as she had been wanting to meet him. I had told
her very little about him, other than that he was a bit
older than myself but she could tell that I was very
fond of him.

I did manage to enjoy myself at my party. All my old
friends that I had been neglecting because I was seeing
Jack were there and I was able to catch up on all the

Two days later Jack phoned to say he had returned and
would I meet him that evening at his house for dinner.
I of course was delighted. After dinner, he gave me my
Birthday present. A rather expensive bottle of perfume.
Now I really did feel grown up.

We sat on the couch and he kissed me long and hard. Not
at all like any kisses we had shared in the past. I
caught my breath and said,

‘Wow! That was some kiss!’

‘Well you are a woman now, aren’t you? And I expect
that you would prefer it if I treated you as such,’ I
could sense the meaning of his words. Tonight he
intended to make me a woman. To take my virginity. My
breath was becoming laboured at the prospect of what
the evening had in store for me. I was excited beyond
anything I had ever felt before. None of my
masturbation fantasies had ever made me feel so hot.

He kissed me once again and I could feel his strong
hand stroking my cheek. His hand caressed down along my
neck. I felt his finger wrap around the back of my neck
and his hand gripped me tightly. It gave me a warm
comforting feeling as though I were being possessed,
being held in his strong grasp.

He pulled away from me and sat me up straight. ‘Fold
your arms behind your back,’ he instructed. I did as he
said, he then pushed me back so that my own weight had
my arms pinioned behind me. Then, very slowly, using
both hands, he opened each button of my blouse.
Tantalisingly slowly, one, then two, then three. My
chest rose and fell.

He was deliberately tantalising me. He certainly knew
what he was doing. He was getting the response from me
that he had anticipated. Eventually all the buttons
were undone but my blouse was still closed. Then, with
great show, he very slowly opened both sides of my
blouse. It was like an unveiling ceremony. He pulled it
off my shoulder and I sat there with my small cotton
bra on display.

For the first time since I had known him, he placed his
hands on my breasts. Gently and lovingly massaging
then. I closed my eyes and luxuriated in the feeling. I
then felt him reaching behind me and undo the clasp. My
bra hung loosely. He pulled it up and gazed at my
breasts for the first time. ‘Mmmm! So delicious. I do
love little pink nipples, and small firm tits’ His
words thrilled me. To know that my body was pleasing to
him meant so much.

He pulled me forward once more and removed my blouse
and bra completely then pushed me back with my arms
folded behind me once more. He bent down and sucked on
each nipple in turn. Such delightful feeling ran
through me at his touch. He sat up and took each nipple
between forefinger and thumb and suddenly squeezed as
hard as he could.

‘Aaaaaauugghh!’ I screamed as fingers of flame shot
through my breasts. Tears fell down my cheeks. I didn’t
know what to say or how to react. The man I was falling
in love with had just inflicted the cruelest pain on me
that I had ever felt in my life.

‘Wha- why?’ I managed between sobs.

‘It’s okay!’ he said. ‘Trust me,’ and with that he
squeezed once again.

‘Aaaauuuugghh!’ I screamed once again.

‘Can you feel your pussy juices flowing?’ he asked.

‘What?’ He was right, my pussy was wet. It was tinkling
and felt on fire. ‘Yes! Yes it is.’ I was suddenly
forgetting the pain and feeling the wonderful sexual
feeling that were starting to flow through my body.

‘Stand up!’ He ordered. I struggled to my feet and then
without another word, he set about stripping me naked.
To my amazement, he then fastened a dog leash around my
neck and led me up stairs to the bedroom. There was a
large four poster bed at the foot of which, was a large
quilted Ottoman. I was lain face down on the Ottoman
with my legs together and my arms folded under my head.
The dog leash was fastened to a ring on the side of the

I lay there for a few moments whilst I heard Jack
doing something on the other side of the room. He
returned and stood beside my head. I turned to look at
him and was surprised to see that he was naked and his
cock was hard and sticking straight out.

‘You enjoyed the pain to your nipples, didn’t you?’ he
asked. I nodded my head in agreement. He repeated the
question. ‘You enjoyed the pain to your nipples, didn’t
you?’ This time I answered ‘Yes!’

‘In that case, you are going to simply love this.’ I
heard a swishing noise over my head but couldn’t see
what it was. He moved out of my line of sight and
almost at once I heard the swish again.
‘Aaaaauuuugghh!’ I screamed out once again as a
stinging pain tore across my bottom.

Swish, and yet another pain only this time my body
started to shake and shudder. I could feel an orgasm
building in my pussy. ‘Oh yes! Oh yes!’ Swish, this one
sent me over the top. ‘Oohhhh! Ooooohh! Oooooh!’ My
whole being became one long orgasm. A much stronger
orgasm than I had ever experienced whilst fingering
myself in my bed at night.

I lay there trembling and shaking as a result of the
nerve wracking explosion that my body had just
experienced. Jack knelt by my head and kissed me
tenderly on the cheek.

‘How are you feeling now, my lovely little Birthday
girl?’ he asked.

‘Exhausted!’ was my only reply. He undid the dog leash
from the Ottoman and told me to lie on my back. He then
pressed a remote control and a trapeze like thing
descended from the ceiling. It had only one centre wire
connected to a cross bar. The bar had two leather
straps dangling from either end. Jack lifted each of
my legs in turn and fastened the straps around each

This left me in a most un lady like position with my
legs pulled open about as far as was possible. He then
pressed the remote and the trapeze rose slightly taking
up the slack. When my legs were in an upright position,
he then pulled the Ottoman forward so that my feet were
directly above my head. He then fastened leather straps
to my wrists and secured them to the sides of the

‘I am now going to hurt you!’ He said ‘but you will
love it.’ What did he mean? He had already been hurting
me- swish. My thoughts were interrupted by the cane
once again striking my bottom. ‘Aaaauuuugghh!’ I once
again screamed as I felt it tear into my left cheek.
Swish. ‘Aaaaauuugghh!’ It tore into my right cheek.
What had gone before, in no way prepared me for what
was to follow. Swish. A pain so severe that I never
made any audible sound.

The scream stuck in my throat. Jack had stood directly
in front of me and had brought the cane down as hard as
he could directly onto my pussy lips. I bucked and
bounced against my bonds as a mixture of pain and
pleasure vied with each other for control of my very

Swish. ‘Aaauuugghh!’ This time I managed to let a cry
escape from my throat. The first blow to my pussy had
caught me across from the top of my right lip to the
bottom of my left lip. This second one had gone the
other way, from top left to bottom right.

Now, this brings us to the moment that I told you
about. The moment that changed my life forever. Jack
brought the cane down- Swish – right down the centre.
The centre of my pussy. The centre of my body. The
centre of my very being. Straight between my pussy lips
and just smashed against my clit. For one split second,
the whole world came to a standstill.

A bright light exploded inside my head, it filled my
brain as the searing pain enveloped my very soul. And
then – then I drifted down and down as wave after
beautiful wave of multiple orgasms washed over me,
through me. To touch me in places I never new existed.

From that moment on, I belong to Jack to do with as he
wished. Any time, any where, what ever…

When I came to my senses, I was untied and kneeling on
the floor but draped over the Ottoman. Jack was behind
me and I could feel his cock touching my pussy lips. He
was waiting for me to come back out of my orgasmic
shock before he entered me. He wanted me to be aware of
my virginity being taken. Wanted me to know the pain of
becoming a woman and to know that it was him who took

‘Are you ready to become a woman?’ he asked in a rather
horse voice. It seems that I was not the only one who
was turned on.

‘Yes! Oh yes, please. I am ready.’

‘Ready for what?’ he enquired.

‘Ready for you to make love to me,’

‘But are you ready for me to fuck you?’ He asked.

‘Yes!’ I said in a shaky voice.

‘Say the words!’ His voice sounding impatient.

‘Yes, I’m ready for you to … fuck me’ I found it
difficult to say the words he wanted to hear but I knew
it meant a lot to him, so I continued. ‘Fuck me! Fuck
me nowwwww aaauuuugghh!’

I felt as though a red hot iron had been plunged into
my body. Jack had thrust his cock, mercilessly into my
virgin pussy, tearing me open. I felt him pull out then
thrust in again but the second time I only felt
discomfort. By the fourth stroke, it was beginning to
feel nice. We settled down to a nice rhythm. I was
beginning to feel a glow spread over me with Jack’s
love making, I mean fucking.

I felt his hand reach around me and find its way to my
pussy. His fingers explored between my legs and found
my pussy. With his fingers stroking my clit, I was soon
reaching higher and higher building up to an orgasm.
When just then I felt Jack’s cock explode inside me,
filling me with his love juice. This in turn triggered
of my own orgasm.

It felt wonderful to be brought to such delights by
being made love to. The orgasm was no where near as
strong as the one I had experienced with the cane but
this one had more meaning. It was a sign of love, of
pleasure shared with the man you love. I was truly

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