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Losing It On Holiday
by Paddy Toute (paddy22@aol.com)

***

A teenage boy on holiday with his parents has an 
unexpected encounter with a hotel made while jacking off 
in his room. (F/m-teen, 1st)

***

Author Note: Although parts of this are true, the most 
part is fantasy (worse luck). DO NOT READ THIS IF YOU: 
Are under the legal age for reading tasteful pornography 
where you are living. Are a prude. Are a prune, or other 
fruit or vegetable. Are likely to be offended by naughty 
stories. Are incapable of reading. Thank you. Enjoy. 
Paddy.

***

My heart was thumping as I left the hotel. I walked up 
the road, turned left into the high street, headed for 
the newsagent's at the far end of town.

I was seventeen, and on holiday with my parents. How un-
cool can you get?

It was as though my entire life had been leading up to 
this point. I was alone, and I was going to buy my first 
porno mag. I had feigned illness that morning to avoid 
going on the bus tour, and my parents had left the hotel 
for the day.

You see, I had had a very strict upbringing. Mother had 
made it plain that pornography was bad, and that sex was 
something married people did to each other in private, 
but what it actually entailed, you didn't find out until 
you were married yourself. Consequently I had developed 
into a very shy seventeen year old who had had next to 
no physical contact with the opposite sex.  

In fact, the nearest I had come to actual physical 
contact with a girl was having my backside felt during a 
"which sixth-former has the squeeziest ass" competition 
between the girls.

My misery was compounded by the fact that I was 
overweight. Mother said it was puppy fat, but my 
contemporaries teased and jibed mercilessly. 

My sex life (such as it was) was limited to my 
imagination and my black-and-white portable television 
in my bedroom. I would spend night after night surfing 
the various channels in the pursuit of female nudity. 
Each glimpse of breast or uncovered buttock was 
carefully stored away in my memory, and a fleeting 
glimpse of pubic hair was enough to send me into 
rapture.

I had never seen any live female flesh save for my 
mother (and I wasn't that kind of seventeen year old), 
and an actual porno film was like Halley's comet - you 
know it's out there, but you don't expect you'll ever 
see it.  I'd recently come across a few tattered 
remnants of an old porno magazine on the school playing 
field, and, having secreted them away in the lining of 
my coat, took them home and pored over them for many 
nights. 

I would never have dreamt of buying one for myself at 
home ( - my mother might find out, and the risk just 
simply wasn't worth it, believe me), and I had resolved 
that on holiday I would, by some means or other, get my 
hands on a porno magazine of my own.

So there I was in the newsagents, doing the four-eyed-
cross-eyed shuffle - trying to see the porno magazines 
out of the corner of one eye whilst pretending to look 
at the car magazines with another, and keeping one eye 
on the door and one on the counter. Judging the moment 
to perfection, I made a desperate grab and made for the 
counter with my purchase. 

My heart was definitely making an escape attempt. It was 
hammering so hard against my chest, that I was convinced 
it would break free with the next beat. It didn't, and 
the man behind the counter hardly took his eyes off the 
picture on the portable TV he was watching as he took my 
money. I hurriedly concealed the magazine in my coat, 
and hurried back to the hotel, convinced my mother must 
surely somehow on my tail.

Once back in the hotel, I started to relax somewhat, no 
longer convinced I was about to be arrested or grounded 
for eternity, though my excitement was building. I was 
shortly to experience pornography first hand (if you'll 
pardon the pun), and I practically floated up the narrow 
stairs to my small room at the rear of the hotel. 

Once inside my room, I divested myself of my coat and 
collapsed onto my small bed. My heart was now back up to 
jackhammer pace as I picked up the magazine and started 
to drink in the contents. So many breasts! I never 
imagined there could be such diversity. Large ones; 
small ones; ones with small nipples; ones with large 
nipples; upturned ones; saggy ones. And all these 
beautiful women were naked for me! And real life, actual 
cunts! Some had shaved their pubic hair off completely, 
and their labia were visible. I'd only just begun, but I 
was in heaven.

At this point, I undid my trousers and slid them down to 
my knees to give some relief to my stiff, aching prick, 
which was harder than I had ever felt it, and poking 
through the fly of my shorts with yearning, demanding to 
be caressed, to be teased, and to be jolly well wanked. 
I curled my clammy fist around my straining pipe, and 
began to joyously masturbate. I was lost in my own 
little world, and that's perhaps why I didn't hear the 
discreet knock on the door that preceded its opening.

Horror-struck, and convinced my mother was about to 
discover me in flagrante masturbatio, I frantically 
tried to make myself invisible, cover my embarrassment 
and die, all at the same time. None worked, and I was 
mentally preparing to meet my doom when I realised that 
the head poking round the door did not belong to my 
mother, but to the hotel manageress. There was a split 
second of silence as we looked into one another's eyes 
before we spoke.

"Oh! I... umm... err..." I began.

"Oh, excuse me!" she said. "I was coming to clean the 
room. I didn't realise you were..." She tailed off, 
realising what I'd been doing. She looked from my face 
down to my cock, to my jazz magazine and back to my 
face. "you were.... busy."

It's funny, but I had often imagined a similar scenario 
when wanking - that of being discovered whilst in the 
act of masturbation, and I had always found it a big 
turn on. The reality appeared to be somewhat different. 
My cock appeared to be succeeding where I had failed - 
making itself invisible. My fright and embarrassment had 
contrived to cool my ardour, you might say.

I was wishing she would go away so I could just kill 
myself, when she stepped into the room, shut the door 
behind her and spoke again.

"You know, it's such a shame to waste yourself like 
this. I could show you a much better way to pass the 
time." And without further ado, she turned to face me 
and with infinite slowness began to unbutton the front 
of her blouse.  I watched transfixed as her black lacy 
bra was revealed to me with its globes of delight.

I have to say I hadn't taken much notice of her during 
my stay at the hotel up to that point. I had been aware 
of her, but she would have been, I suppose, about 
thirty, which to me at that time was quite old. However, 
I was rapidly beginning to change my perception of her, 
and to look at her in a new light.

Her hair, which hung down to just below shoulder height 
was black. I mean jet black. Her skin, more of which was 
being revealed to my incredulous gaze each moment was 
pale, almost white. Her breasts, still in their lace 
confinement were full, and swayed very gently as she 
moved. 

Her waist was slender without being thin, and her hips, 
clad in blue denim were delightfully flared. She removed 
her blouse from the waistband of her jeans and began to 
unbutton the jeans, revealing to me a pair of matching 
briefs. She pushed the denim down her thighs, and stood 
before me, a vision in black lace.

"Well, are you going to stay down there, or shall we 
make you a little more comfortable?" she said. I sprang 
from the bed, proceeded by my re-tumescent organ, which 
now felt long enough to pole vault with, and hard enough 
to cut diamonds. I stood before her, still unsure how to 
proceed. Sensing my naivety, she began divesting me of 
my clothes. 

I stepped out of my jeans and shorts, and my shirt 
joined them on the floor. Taking my trembling left hand, 
she placed it on her right breast, and oh joy! . For the 
first time, I was feeling female flesh! I watched as if 
from outside my body as my right hand met and moulded to 
the shape of her left breast through the lacy bra. I 
slowly massaged her bosoms, enjoying their firmness, yet 
somehow feeling unreal, worrying that I might wake up at 
any moment.

She turned around without speaking, and presented me 
with the fastener to her bra. After a momentary fumble, 
I released it, and eased her bra straps down off her 
shoulders. The garment slid to the floor. She turned 
back to me, her breasts swaying gently from side to side 
with the motion. I stood staring at them, transfixed. In 
fact I would probably have remained like that for ever, 
had she not taken my trembling hands and placed them on 
her hips at the waistband of her panties.

Coming back to the present, I took her gentle hint and 
slowly rolled the panties off her hips until they joined 
the rest of our clothes on the carpet.

She stood before me naked. Naked for me! This couldn't 
be true. Surely I'd wake up at any moment. 

My eyes were now drawn to the thicket of her jet black 
pubic hair.  Incredulously I moved my hand towards it, 
convinced that she must be a mirage, that my hand would 
go right through her, but it didn't. She must have 
wanted things to speed up a little, as she encircled my 
wrist with her arm and placed my hand right between her 
legs, so that I could feel the warmth there. I could 
also smell what I now know was the fruits of her 
arousal.

Meanwhile, she took hold of my throbbing erection, 
rubbing my foreskin back and forth over its cherry tip. 
Her palm opened and then shut over the full girth, and 
she began to slowly pump me. She hadn't given above a 
dozen strokes when my orgasm was upon me, as if from 
nowhere. 

I had precious little warning, and as I started to say 
"hey! hang on!" my first globule of semen splashed onto 
her belly, followed by several more, making a pattern on 
her midriff and thighs. A cum-collage, you might say. I 
bucked at the knees as she milked the last few drops 
from my penis.

I expected her to be angry, or at the very least 
disappointed that I'd cum so quickly, and I didn't dare 
look her in the eye, for fear of seeing her disproval 
painted there. But she simply said "Never mind hon. 
It'll make it better next time."

And with that knelt before me, and with both hands 
cupped my genitals. One hand gently kneaded and massaged 
my balls, while the other took hold of my penis and 
delivered it into her mouth. Reason tottered on its 
throne, then fell off. My first hand job, immediately 
followed by my first blow job!

My penis fitted completely in her mouth at first, though 
under her tender ministrations it swiftly began to swell 
and enlarge once more, at which point she stopped what 
she was doing, lay down on the bed, looked me in the eye 
and said "now, fuck me please".

My earlier hesitancy was more or less a distant memory 
as I joined her on the cramped single bed. I began to 
suck greedily on her pink nipples, which responded by 
tightening and lengthening within my mouth. She once 
more was slowly wanking me, but with my recent 
ejaculation, the danger of a repeat performance of prem-
ejac was not so great. 

Presently she nudged me into a position so that I lay on 
top of her, my penis jammed between our bellies.  After 
a few fumbling attempts on my part to reach her cunt, 
she helped me out, taking my glans in her fingers and 
placing me at the head of her tunnel.

She was very well-lubricated, and I more or less slipped 
inside her. My rapture was almost complete. Here I was 
actually fucking someone other than my teddy bear! 

Instinct more or less took over, I suppose, because 
within seconds I was pumping in and out of her like a 
veteran (or so I supposed).  Soon I recognised the signs 
that I was about to cum again, and told her so.  "Go on, 
enjoy it" she said, so I did. I increased my pace to 
warp factor 9 and within seconds was at my peak again, 
jamming my spurting penis deep into her vagina.

Utterly spent, I now slumped against her, and tried to 
utter my thanks. All that came out was a stream of 
garbage about my mother and god knows what else. I think 
she sensed my jumbled up feelings, because she simply 
said "that was lovely. Thank you. We won't say a word of 
this to anyone, and it won't happen again." With this, 
she swiftly put on her bra, blouse and jeans and was 
gone.

I hardly saw her again, and three days later it was time 
to leave, the end of  our holiday. Nothing was said 
between us, nor did it really need to be. I do feel a 
little guilty that I never officially thanked her for 
what she did for me. She'll never know how much she 
actually did for me on that rainy afternoon in an 
English hotel room.

She left her knickers behind - did I tell you that? I 
don't know whether that was intentional on her part, but 
I chose to believe that. I still have them today, 10 
years on. Even now just looking at them turns me on a 
little, and all I have to do is close my eyes, and I can 
see her beautiful, mature body.  Naked. For me.

May 29th 1997

Email responses to: Paddy22@aol.com

*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*
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 67