Friday, April 10, 2009

Each Way Bet

"I'll bet you $500 that I can get Lisa to eat my sister's pussy, and you can

I was in the pub with Pete who had started working with my company a few
weeks ago and his offer was so ridiculous that I was already thinking about
how I was going to spend his $500. Lisa was my new boss and I really didn't
like her at all. It was nothing to do with her being a woman, or at 30,
being 15 years younger than me. In fact she was a very attractive woman with
shoulder length brown hair and a nice figure that was always well hidden
under her smart business suits. No, it was just that I thought she was bad
at the job and I think she resented me because I was part of the old team.
She took every opportunity to give me a hard time.

Pete was 24 and had recently joined the marketing team. He seemed like an
easy going guy who had a rugby players build with short fair hair. I
appreciated that he bothered to spend time with an older member of staff
like myself. I had also met his sister, Jenny, who lived next door to him.
Now she was a stunner, an 18 year old blond student with full firm breasts
which she liked to display by wearing tight tee-shirts with no bra. Just
thinking of her shapely legs and cute ass was enough to get any red blooded
males blood flowing. A fleeting vision of Lisa with her tongue buried in
Jennys hot twat was enough to seal the bet, although I had no fear of having
to pay up.

It was 2 weeks later on a friday morning and absolutely nothing had happened
so I was about to pop into Petes office to ask for my payment. I had made
discreet enquiries and found out that Lisa had a long term boyfriend so I
was pretty sure she wasn't a lesbian.

Pete looked up as I walked in.

"Hi Chris, fancy coming over to my place this evening for a few beers?. Oh,
and bring plenty of money, if you know what I mean" and he winked at me.

"Sure thing Pete, but i'm sure the beers won't cost me $500" I replied,

I didn't think for a minute that anything was going to happen but I was
quite happy to spend an evening in Petes company sharing a few drinks.
Five o clock arrived and Lisa said goodnight as normal. She was wearing a
smart well fitting grey business suit, jacket and just above knee length
skirt. I wasn't sure but I reckoned she probably wore stockings covering her
legs and just for a moment I allowed that fantasy thought to flash through
my head which gave me a pleasant twinge in the groin area. I quickly
shrugged it off and went home for a shower and to change into jeans and a
tee-shirt. I picked up some beers and was round at Petes house by 8 o clock.

Three hours later we had consumed several cans each and we were both slumped
comfortably on Petes large leather sofa. Suddenly Pete reached for the
remote control and with the press of a switch an impressive large screen TV
came to life in front of us. Except it wasn't a TV, rather it was a picture
of his sister Jennys empty sitting room. I was just about to ask what was
going on when the sound of a street door being opened could be heard,
followed by two female voices, Jenny and Lisa! They soon both came into view
each clutching bottles of something and clearly both were somewhat tipsy as
they flopped onto the settee. Jenny seemed quite distressed about something
and as we listened it became clear that she had just been dumped by her

Lisa was trying to comfort her but Jenny then burst into tears and threw
herself against Lisa, her head resting against the older womans chest as
sobbs wracked her body. The smartly dressed manager hesitated at first but
then she put her arm round the younger girls shoulders and began to gently
stroke her hair to try to calm her. Jennys head was now resting directly on
Lisas jacket covered breasts with her right hand touching Lisas stomach. The
girls sobbing had now changed to soft mewling sounds as the older woman
continued to stroke her hair. The top of Lisas cleavage was just visable
above her buttoned jacket and it seemed to me that Jennys head was gradually
turning into that part of Lisas chest.

I suddenly realised that Jenny was gently kissing that small exposed area of
Lisas breasts and her hand was fiddling with the lower buttons of the
jacket. I felt my cock lurch with excitement in my jeans and glancing next
to me I saw Petes hand stroking over an already prominant bulge in his
It was only when the last button came undone that Lisa even realised what
was happening.

"Wwwwhat are you doing Jenny?" she murmered.
"It's alright Lisa, just relax and let me take care of everything" Jenny
replied, as she parted the older womans jacket.

I heard myself and Pete gasp as we saw the sexy white satin bra which held
Lisas full firm globes. Glancing again at Pete I gasped again as he pulled
his fully erect 8" cock from his trousers and began running his hand up and
down the thick shaft. My own penis stiffened and throbbed uncontrollably as
my eyes went back and forth from the screen to Pete. I told myself that it
was only the two women which excited me-I'd never had any interest in
men-but I couldn't ignore the big naked cock which was starting to leak
precum just inches away from me.

Back on the screen Jennys hand had slowly moved up and now covered Lisas
left breast. She gently squeezed it and an involuntary low moan escaped from
my managers lips.

"Please Jenny, stop. This is so wrong. I have a boyfriend. I've never even
thought about being with a woman. You must stop, aaaaargh".

This last exclaimation came as the younger girl fondled the breast more
firmly and pinched at where the nipple would be. Or to be more precise,
where Lisas nipple was, because despite herself her body was starting to
betray her and we could clearly now see the outline of her stiffening
nipple. Jennys mouth now closed over the right satin covered breast as her
skillfull fingers worked on the other.

Suddenly a hand was at my groin and before I could speak or move Pete was
tugging my zip down over my straining dick.

"No Pete" I mumbled weakly.

Too late I tried to move as he grasped my stiff cock and released it from
the confines of my jeans. I grunted as he gently squeezed my aching 7"
organ. I fell back on the settee as he started to stroke me, my mind
whirling in confusion and shame but also undeniable arousal.

Movement on the screen showed Jenny quickly peeling off her teeshirt to
reveal her small firm breasts, the nipples were half an inch long and
throbbing in her excitement. Lisa just lay there looking discheveled and
confused but she did not resist as Jenny reached around her to unclip her
bra. Her full swollen titties swung free. She had big puffy nipples, the
tips erect with her unwanted arousal. I was hardly aware of Pete between my
legs tugging off my shoes, socks, jeans and briefs as Jennys head lowered
and her lips closed around the older womans stiff teat.

"Aaaaaaaagh, god, noooooooo. Please stop"

I wasn't sure if it was me or Lisa speaking as the younger girl slowly
pulled Lisas skirt up to expose her stocking tops and then her panty clad
pussy. I looked down just as Petes lips touched my hard smooth cockhead, his
tongue flicking out to taste my first oozing drop of sticky precum. I barely
registered that Pete was somehow naked, his big cock waving like a baton
between his legs, as he went to work on my rigid member. He peeled off my
teeshirt leaving us both nude as he gently fondled my tight aching balls. I
was now completely helpless to resist and my groan of surrender and pleasure
was matched by one from Lisa on screen.

Her skirt was off and she was now clad only in her stockings with the garter
and suspenders as a naked Jenny slid her sheer black panties down her smooth
shapely legs. As Jenny was on all fours between the older womans thighs I
could clearly see her shaved pussy and tight little rosebud, both slightly
parted and glistening with the secretions of her arousal. She pushed Lisas
legs apart and raised her knees to totally expose her dark haired pussy. Her
fingers pried the moist cunt lips apart, the abundant juices already leaking
from her opened yearning hole. She slid two fingers into the slick passage
as her tongue made contact with the tiny aroused nub of Lisas clit.

"Aaaaaargh, yeeeeeeeeeeeeesssssssssss. Lick me baby. Pleeese make me cum"

Pete took my straining cock deep into his mouth and I thrust upwards seeking
a quick release but he pulled off me and pushed my thighs apart and raised
my knees, just like Lisa had been positioned, as his tongue bathed my
quivering balls. Then he was rimming me, lapping deliciously at my virgin
pucker, opening my asshole to his probing tongue.

"Fuck yes, eat my ass" I groaned.

Then first one, now two fingers were pushing into me. I squirmed with
momentary pain but then it soon started to feel good as his fingers sawed in
and out of my moistened back passage.

Lisa seemed she was approaching her much needed orgasm when Jenny suddenly
withdrew her raping fingers and tongue from the thrashing, gasping womans

"Please Lisa, I need it too. My cunt is dripping. Eat my fucking pussy Lisa
darling, make me cum"

Lisa looked momentarily stunned as Jenny climbed over her into the 69
position, but she was too desperate in her own sexual need to resist as
Jenny lowered her juicy bare snatch onto her waiting mouth. Her tongue
snaked out as she lapped at another womans essence for the first time. The
taste was wonderful and she quickly went to work on the younger girls
pulsing slit, running her tongue from the erected clit through the lovely
juicy pink folds of her vagina, even down to her crinkled little asshole.
Jenny quickly dove back down to complete her job of bringing Lisa to a
crashing orgasm.

I had a vague thought of something to do with $500 when Pete stood up and
shoved his leaking throbbing prick towards my mouth. I hesitated for only a
second before parting my lips and allowing the first ever cock to enter my
mouth. I swallowed the copious precum and sucked and licked deeply on the
pulsing organ. Oh, it was so good to feel that jerking cock filling me. Then
it was gone. He grabbed my legs, lifting them and spreading me wide. I felt
his spit slickened cockhead probe at my tight virgin ass and gasped as he
thrust in passed my sphincter. Again the initial pain quickly faded to a
wonderful feeling as he slipped deeper into my bowels finally touching my
prostate as he was fully embedded in me. I felt his balls on my upturned ass
as he began a slow fucking motion. My own cock was massively erect and my
bollocks were aching to pump out a massive load of hot spunk. I was vaguely
aware of the screen being empty and I thought I heard a door opening but was
too far gone to pay any attention.

"Yes, fuck meeeeeeeee, I'm gonnna cuuuuummmmmm" I shrieked.

Suddenly Pete pulled out of my clenching asshole and aimed his jerking cock
at my face. His hot seed jetted out into my hair, eyes and mouth as my own
prick gave a final spasm and I shot my own jism over my chest.


It was Lisas voice.

"Jenny said it would cost me $500 to see Pete fuck your ass and cum on your
face. Never in a million years thought I'd have to pay up"

Jenny and Pete were smiling happily at the two of us.

"It's ok, we both accept checks or credit cards"

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