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                 K R I S T E N' S    C O L L E C T I O N
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This work is copyrighted to the author © 2009.  Please
don't remove the author information or make any changes
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Penny, Todd and Me
by The Ratt in the Hat (address withheld)

***

An English boy living in America is sent to stay with 
his mothers' best friend whilst his parents jet off on 
a second honeymoon. However, his temporary guardian and 
her son have special ideas. (M/mf-teens, ped, reluc, 
1st, bi)

***

It all started when my parents decided to go on a 
second honeymoon. There had been a crisis in their 
marriage but thankfully it didn't last long and they 
soon managed to patch things up. They decided that the 
two of them needed to get away together so I was sent 
off to my mother's best friend Penny who lived a couple 
of miles away.

I was born in the south of England to an English mother 
and American father. Mum worked as a cleaner in the 
offices of the American vice-consulate in Southampton, 
a small diplomatic outpost of the United States dealing 
mainly with Americans passing through the cruise 
terminal and the small American naval base nearby. The 
two of them met when my dad was working late one 
evening processing a large backlog of paperwork, Mum 
worked mainly in the evening and didn't start work 
until 6pm. 

The term 'love at first sight' is an overused 
expression but very appropriate in the case of my 
parents. Very soon they started dating and before long 
they had moved in together.

Marriage followed and a couple of years later, I was 
born. Unfortunately, I was to be their only child as 
Dad had been struck down with cancer and despite making 
a full recovery, was rendered infertile by the 
treatment. He also lost his job at the vice-consulate. 

But it proved to be a blessing in disguise however, my 
parents took the decision when I was five years old to 
move to the US, and we ended up in a small town in New 
York State, an hour's drive away from New York City 
itself. Dad quickly found work as an office manager and 
Mum trained to become a real estate agent. By the time 
I was 13, my parents were both in well paid jobs but 
the stress of working long hours had taken its toll on 
their relationship.

So after patching things up they decided to fly to 
Hawaii for the dream honeymoon they had always wanted 
(a week in Cornwall was all they could afford when they 
first got married back in England). 

And so I found myself on a rainy Sunday afternoon being 
dropped off at Penny's house, a large detached property 
a mile or so out of town on the edge of a small patch 
of woodland. 

Penny was a teacher, 52 years old and had first met my 
Mum at a parents evening at my elementary school 
shortly after our arrival in the States. Upon hearing 
Mum's English accent, she decided to introduce herself 
and welcome us to the town and the US in general. The 
two of them hit it off instantly and were very soon 
firm friends.

By the time I was 13, Penny had been widowed, with a 
grown-up son at university and occupying a house far 
too big for a single woman on her own. Mum and Penny 
agreed that having me over to stay for the two weeks 
while they were away would be just the tonic she needed 
but little did Mum know at the time of Penny's ulterior 
motive.

With my bags taken upstairs to my room and all my 
things unpacked I waved off my parents with a kiss and 
a big hug. Penny already had dinner on the go and 
shortly after my parents left we sat down for our meal. 
The conversation that followed caught me totally off 
guard.

"So 13 years old eh? How does it feel to be a 
teenager?" Penny asked.

"Fine I guess" I replied, despite having lived in the 
states for over 8 years I had never lost my southern 
English accent.

"I remember when I was your age I already had my first 
boyfriend, are there any girls at school that you like? 
I bet that accent of yours has them all over you!" she 
chuckled.

"Yeah," I said, "there are a couple."

"Are they pretty?" she asked.

"Yeah, I guess," I replied.

"Tell me... do you ever... fantasise about them?"

"What do you mean?" 

"You know... imagine them without their clothes on."

"What!?! Why would I do that?"

"You know, when you masturbate silly! I take it you've 
started masturbating by now, most boys do at your age." 

I turned bright red, I knew exactly what she was 
referring to. Indeed, a few months earlier I had 
started masturbating and the girls at school were 
indeed often the subject of my fantasies.

"Its ok," she said, "I won't tell your Mom, you can 
talk to me about it."

"Well," I said, still bright red, "sometimes I do, when 
I'm in the bathroom."

"Does it feel good when you do it?"

"Yeah, I suppose," I said, beginning to loosen up a 
little, "it feels great, until the white stuff comes 
out of my willy, then it goes away." 

Penny giggled a little at my naivety.

"That white stuff is called semen and when it comes out 
of your... willy, it's called ejaculation" she 
explained, obviously not used to my idiosyncratic 
English expression for my male organ.

She went on to explain all about sex and masturbation 
and to be honest it was all a massive turn-on for me, 
my cock was massively erect and started to poke out of 
the top of my underpants.

I wanted to go upstairs and masturbate right away but 
Penny had other ideas and I would find out later for 
myself what she had in mind.

The job in hand though was to wash up and tidy up the 
kitchen, after that we went into the living room to 
watch some TV. A couple of hours later after I had 
thought that Penny had finished on the subject of sex 
she startled me with yet another revelation.

"How much do you enjoy masturbating?"

"Umm... well quite a lot."

"How often do you do it?"

"Most days I guess."

"Hmmm.... I was wondering.... Would you um.... Let me 
er... have some of your semen?"

"WHAT!?!? Why??"

"I read in a book that wealthy women in ancient Egypt 
often used the semen of boys as a moisturiser and it's 
supposed to be very good for the skin, I was wondering 
if I could have some of your semen to try it out and 
see if it's true."

Suddenly events had taken a turn which I didn't like at 
all, but what she said next floored me completely.

"I'll make it worth your while if you let me."

"How?" I asked in reply.

"Do you know what a handjob is?"

"No."

"It's when instead of masturbating yourself, someone 
else masturbates you."

"Oh no, no way."

"Please, it'll feel way better than just masturbating 
yourself."

This discussion went on for some time and I had to 
admire her persistence as I denied her what she wanted 
of me. But to be frank, I did start to warm to the 
idea, if it felt as good as she said it would. I was 
also enjoying the sense of power I had over her. 

It wasn't until 11 o'clock that night after several 
hours of her pleading that I finally caved in.

"Please, I'll be very gentle, you'll enjoy it."

"Oh..... alright, as long as you promise to be gentle 
with me," I sighed.

"Really?!? You'll do it!?!" her face lit up.

"Yes, just as long as no one finds out ok."

"Of course."

"Right, where do we start?" it was a logical enough 
question with, surprisingly, a logical enough answer.

"Umm... well, I suppose you had better take your 
clothes off."

Nervously and with a loud sigh I started to undress, I 
placed my sweater, t-shirt, socks and jeans on the 
coffee table in the large sitting room until I was down 
to nothing more than my white underpants, Penny stared 
at the masculine bulge in the front of my pants, I 
could tell what she wanted to do.

"Do you want to pull my pants down for me?"

"Ok, as long as you don't mind."

She came forward and got down on her knees before me, 
she placed her hands on my hips and hooked her thumbs 
into the waistband and then slowly pulled my underpants 
down to reveal me in all my naked glory before her 
eyes.

"Oh my, what a lovely penis you have! And I see you've 
not been circumcised either!"

"What's circumcised mean?" I asked.

She went on to explain what circumcision was and that 
most boys in America had it done to them, including her 
own son. Obviously, having been born in England I was 
left intact, as the vast majority of English boys are. 

This had always been a source of friction between my 
parents, Dad had been keen for me to be cut, as he had 
been, whereas Mum had always been against the idea. She 
had won out in the end but the resentment was always 
there simmering in the background. 

The argument had surfaced once again during their 
recent troubles and Dad had apparently demanded I be 
circumcised by a local doctor. Fortunately for me, Mum 
had once again persuaded Dad it was a bad idea and that 
at my age it should be my choice.

"Oh well, I suppose you want to masturbate me now," I 
said, eager now to get it over and done with, in the 
morning, I decided, I would go to the police and report 
her for child molesting, that'll teach her I thought.

"Just a moment, let me get something first," she said 
and disappeared into the kitchen leaving me standing 
there, nude, my flaccid penis awaiting its fate.

She came back a few moments later with, of all things, 
a wine glass in her hand. She instructed me to sit on 
the edge of the coffee table and she pulled up a chair, 
placing the wine glass beside me.

"What's that for?" I asked.

"I just need something to catch your semen in, but you 
must let me know when you are going to cum so that I 
can catch it ok."

"Ok," I sighed.

"Now then, let's see if we can get you nice and hard."

She sat me down on the coffee table, I looked on as her 
hand moved towards my private parts, it all seemed to 
be in slow motion. Closer and closer her hand came 
until I could stand to look no longer and I closed my 
eyes. 

A massive shock, like being struck by lightning flashed 
across my whole body as, for the first time, Penny's 
cold hand made contact with my soft, hairless genitals. 
But what I felt wasn't as unpleasant as I had feared, I 
was caught up in a rush of pure pleasure.

My god, it was fantastic! Her hand slowly caressing my 
penis and my testicles, it didn't take long for me to 
start to become hard and in under a minute I was fully 
erect. She motioned herself forward a little and spread 
my legs apart ready to masturbate me. But Penny had in 
store for me a painful obstacle to get across before 
the fun could really start.

In uncircumcised boys, the foreskin is partially 
attached to the glans of the penis and it is some time 
before it can be retracted fully, and it can be painful 
to retract it for the first time. At only 13 years old 
I had never had my foreskin retracted before, even 
though I had tried it, the pain becoming too much for 
me in the end. But Penny was unaware of this. 

She took hold of my stiff cock and started to retract 
me. It was unbelievably painful and I let out a silent 
scream as millimetre by agonising millimetre, my glans 
was exposed for the very first time. Finally after what 
seemed like an eternity, I was fully retracted, and 
Penny started to masturbate me for real.

She started to stroke up and down my dick in long, slow 
strokes. I opened my eyes to see her masturbating me. I 
was now both in a state of ecstasy and pure naked fear 
at the same time. Part of me wanted it to stop whilst 
the rest of me wanted it to never end.

My penis was still stinging a little after having been 
forcibly retracted but the pleasure of being 
masturbated more than made up for it.

I don't know how many males Penny had masturbated like 
this before but she sure seemed to know what she was 
doing. As I watched her masturbate me I could see a 
glint in her eye as if she was getting as much pleasure 
out of it as I was.

After a couple of minutes she picked up the pace and 
started to stroke me faster with shorter strokes. This 
sent another wave of pleasure washing over my body and 
I could feel an orgasm begin to build deep in the 
depths of my young scrotum.

An intense tingling took over my whole, naked body as 
Penny's stroking got faster and faster. I knew that I 
was about to cum but I didn't want it to end so soon.

Once again I closed my eyes and tried as hard as I 
could not to ejaculate too soon. I grabbed hold of the 
sides of the coffee table, my knuckles turning white as 
I gripped harder and harder.

The tingling built up until I started shaking, I was 
really holding on in desperation by then, determined to 
ride the wave of emotions and intense sensations but in 
the end it was no use and I had to utter the words 
which I knew Penny had been waiting for.

"I'm.... cummingggg!!!! I'm Cumming!!"

And with that signal, she sharply tugged my penis down 
and brought the wine glass to the tip just as I started 
to ejaculate my hot sticky greyish-white semen. It 
coated the inside of the glass as spurt after spurt 
erupted from my dick.

Never before had I cum so hard and ejaculated so much, 
Penny was right, it was way over a thousand times 
better than masturbating myself. I looked down to see 
the glass, its inside coated with my cum and breathed a 
huge sigh of relief. But what Penny did next left me 
utterly speechless.

She dipped her fingers into the pool of freshly 
ejaculated semen, MY freshly ejaculated semen, and 
smeared it onto her face.

"I'll need to keep as still as possible for the next 
half hour or so, would you be a sweetie and go into the 
kitchen and bring me a bowl of water and some cotton 
wool so that I can wash it off" she said as she 
continued to smear it all over her face.

I did as I was asked, still naked and still with the 
last remnants of cum dripping from my still fully hard 
penis. I used a paper towel from the kitchen to clean 
myself off and filled a bowl with water, found the 
cotton wool and brought them back into the other room. 
I found Penny reclined on the couch with my cum all 
over her face, I placed the bowl and the cotton wool on 
the coffee table.

"Thank you darling," she said trying to use her facial 
muscles as little as possible.

I just sighed and put my underwear back on.

That night, I sobbed myself into a fitful sleep, I felt 
used and dirty. Why had I let her do it? I asked 
myself. And why, more to the point, had I enjoyed it? 
She had committed an act of child abuse upon me and I 
had actually enjoyed it.

END

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The author does not condone child abuse, this story is
meant as an erotic fantasy not real life. Anyone acting
out such scenarios in "real life" can look forward to
many unproductive years getting it up the butt by a 
fellow convict in their local prison.
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Kristen's collection - Directory 63