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Coworker Passion in Toronto
By Anonymous (address withheld)

***

Two longtime male/female coworkers who are also best 
friends, on a business trip. She unloads her sexual 
history to him, getting aroused in the process. (MF, 
mast, oral, anal, rom)

***

She sat across from me, in the lounge area of her 
hotel suite in a suburb north of Toronto. We were both 
there on business from the US and had worked off and 
on together for many years. Both in our mid-forties 
and both in average shape. To many men, Kristin 
probably looked nothing special. I thought she was 
beautiful, but I was also somewhat biased, as she'd 
been my best friend for several years now and she knew 
just how to flirt with me to bring out her best 
features. Those would be her smile, her shoulders and 
her butt.

On a physical level, our relationship was purely 
platonic. I couldn't speak for her, but from my 
perspective, she was my ideal fantasy fodder and I 
spent goodness knows how many hours imagining what it 
would be like to undress her and explore her pussy and 
her butt. 

I honestly didn't harbor any great longing to have 
intercourse with her - all I wanted was to be 
permitted intimacies she granted to very few. I wanted 
to experience her orgasm, I wanted to press my face 
between her butt cheeks, I wanted to taste her juices 
and I wanted to introduce her to the pleasures of anal 
titillation. Not too much to aspire to, eh?

Of course, I'd raised some of those subjects with her 
over the years, always in a light-hearted environment 
so as not to make her feel so uncomfortable she 
couldn't just laugh them off. Sometimes she'd give me 
a quizzical look, as if unsure as to how serious I was 
with my request. Other times she'd just smile and give 
a quick "ha ha," "cute" or "in your dreams!"

We'd had dinner in a nearby pub, watching a hockey 
game. Then we'd walked back across the parking lot to 
our hotel and she'd suggested having a glass of wine 
in the hotel bar. I always enjoy spending intimate 
time with Kristin, so I had no reservations about that 
activity! She selected a quiet table for two and I 
ordered us both a glass of Cabernet from the waitress.

As soon as the drinks arrived, she took a substantial 
sip, leaned forward toward me and launched into 
stories of her early sexual history! This was 
completely unprompted and caught me a bit off-guard, 
but not unpleasantly so. She went through her teenage 
years (some of which I'd heard before) and into her 
college years and then early married life. By now, the 
bar was closing and we'd had three more drinks each. 
And she had more she wanted to share, so she invited 
me up to her room, which was really more of a suite.

I was torn between sitting beside her on the couch or 
across from her in one of the easy chairs. I chose the 
latter (I really have no idea why!). She hesitated a 
bit before continuing with her tales of sexscapades 
over the years, wishing out loud we had a bottle of 
wine with us. It's really not like her to drink very 
much and I'd never seen her consume so much before, 
but she wasn't showing any ill-effects. Finally, she 
got to the present day, recounting it had been "a few 
years" since she had sex with her husband. 

I asked her, "How about with anyone else? Have you 
ever cheated on him?" 

She kind of hesitated a bit and looked a little 
pensive, a slight chewing of her lower lip, before 
replying quietly, "No, not since we were married."

"And how about him?" I asked. "Do you think he's ever 
cheated on you?"

This caused an even longer and more thoughtful pause. 
"No, I don't believe he has," she finally replied, 
looking me straight in the eye.

Kristin had done most of the talking so far this 
evening. Now it was my turn to take over. "Do you wish 
you had sex more often these days?" I asked her, 
looking carefully at her face during her reply. "Oh 
yes," she replied wistfully. "I'm fine for a few 
weeks, then I have to... take care of myself," as she 
dropped her eyes from my gaze and crossed her thighs 
firmly.

"You masturbate?" I asked.

She nodded slowly, avoiding eye contact completely as 
she reddened a little. "That's nothing to be ashamed 
of, although you ARE terribly cute when you blush," I 
told her. That just made her blush and press her 
thighs together even more. "I play with myself even 
more frequently, sometimes daily," I told her. "How do 
you get yourself off?" I asked. "Do you use any toys, 
a vibrator or a dildo, or just your fingers?"

She hesitated and squirmed a bit before answering, 
still avoiding eye contact, "Just my fingers... and 
they're not nearly as satisfying as the real thing..."

"Oh yes? What's different?" I asked her, quietly.

"I like the sensation of, I like to, squeeze around 
something when I'm about to come," Kristin whispered. 
"It makes it so much more intense for me..."

"So you like something in your vagina when you come 
and fingers don't cut it?" (I know she hates the word 
'pussy').

"Um, yeah, yes, I guess that's one way of putting 
it..."

I stood up, walked the three paces across the room and 
got down on one knee. I put my right hand over both 
her clasped hands, which were on her left knee, and 
squeezed gently. "I understand. I really do. And I'd 
like to help you, I'd do almost anything to help you, 
but we're not going to have intercourse."

At that, she raised her eyes to meet mine and a slight 
smile broke across the corners of her delicious-
looking mouth. "Why did you feel the need to share all 
this with me? Do you have an ulterior motive?"

"I'm not really sure," Kristin replied. I did want to 
get it off my chest and you're the only person I felt 
I could share it with. I hoped you'd understand"

"Do you feel better for sharing it?" I asked, still 
holding her gaze as I looked up slightly at her, and 
still gently squeezing her hands.

"Or are you starting to feel a little aroused now, for 
telling me all this?" as I slid the fingers of my left 
hand along the inside of her left thigh. And she 
didn't move to stop me. Grabbing her left knee 
lightly, I encouraged her to uncross her legs and 
leant closer so our faces were almost touching. We 
both cocked our heads very slightly toward our 
respective rights and I leant in further until our 
lips met, just a very soft brushing at first, then a 
more powerful press as we gained confidence in our 
abilities to read each other. 

I moaned, she moaned, we moaned as one. And as kisses 
go, it probably gave the superficial appearance of 
chastity. But when you took the moaning and the slight 
interlocking of our lips into account, the exchange of 
breath with one another, the little tongue darts 
between each other's lips - it was far from chaste.

Kristin broke the kiss and leant her upper body back 
against the couch at almost the same moment my 
exploring left hand made its way to her groin. I 
curled my middle finger under and pushed into her a 
little, feeling a definite yield. Her dark grey (maybe 
they were actually black, I was never quite sure) 
pants felt soft beneath my touch, almost like cotton 
or linen. Her eyes were closed and her face had a 
mildly pained expression, her jaw now rigid as her 
chin jutted up, slightly. She was breathing through 
her nose, her nostrils somewhat flared.

Her right hand fell to her side, palm upward on the 
couch, while I held even more tightly onto her left 
hand, now atop her thigh. She grasped back and our 
fingers intertwined. I wiggled the extended middle 
finger of my left hand a little, feeling the give in 
the fabric around the front of her crotch. I was 
almost sure the cushioning I was feeling was a 
combination of thick pubic hair and maybe a little 
extra body fat lurking down there. I had no problem 
getting the whole width of my hand between the tops of 
her thighs - she had very slender legs.

"Please..." she muttered. Please what? I extended my 
forefinger to meet my middle finger and massaged a 
little more firmly, also sliding further back, under 
her. Deciding to see if "talking naughty," as Kristin 
called it, would lead somewhere, I whispered to her, 
"Remember that one time in the auditorium? We stood on 
the top step during CPR training and you let me try 
the Heimlich position on you?"

Her mouth opened with a slight smile "I didn't let you 
- we took turns and the instructor TOLD us to..."

And as I increased the movements of my fingers in her 
crotch I continued, "And I stood behind you and 
pressed against your butt with my cock, laced my hands 
around your waist and sought out your belly button, 
then pulled myself closer into your butt"

"And you felt me getting hard and we were in front of 
all these people and there was nothing you could do 
about it... and the instructor kept adjusting my hands 
while my cock got harder and longer and I had to 
shimmy a bit to keep it between your cheeks."

Her breathing was definitely quicker now.

"and what if we had no clothes on - I could have 
pressed the tip of my cock against your ass and you 
wouldn't have been able to do anything but revel in 
the anticipation...I could have slipped my hands down 
a bit and sought out your throbbing clit as I started 
to push my cock into your ass..."

She was quite distinct in her next, breathy words 
"No... Please... Help." But I had no idea what she 
actually meant by them! Her next actions clarified 
that a little, as she shook her left hand free from 
under my hand and used both hands to undo the clasp at 
the top of her pants, then moved my hand out of the 
way, pulled down her zipper, raised her butt and 
pushed her pants down to her knees in a somewhat 
staccato motion. When she raised her lower legs, I 
pulled the pants all the way off, tossing them on the 
floor behind me.

Her panties were purple and the rear of the crotch was 
most definitely wet. Little wisps of dark hair escaped 
from the edges, around her thighs. I bowed my head 
over her pubic area and breathed deeply. Oh yes, I 
could smell her and it was a good smell. Not earthy, 
but a clean smell with a hint of essence of woman. 
Well, maybe more than a hint. I raised my head to look 
at her face again. "I want to taste you." Her eyes 
were closed as she complied by hooking her thumbs over 
the waist of her panties and shimmied them down to 
mid-thigh. 

The aroma grew a hundredfold in intensity. My head 
reeled in disbelief this was really happening. I 
extended my left hand again and stroked my middle 
finger up the length of her slit, from the bottom 
until there was nothing but hair. She moaned a tiny 
bit as I traced over her lips, feeling the slight gape 
at the start, with a little moisture, then the lips 
closed as I neared her clit.

I repeated the motion, a little more firmly for better 
penetration. This time, I scooped quite a bit of 
moisture and distributed it either side of my finger 
as I drew it up the full length of her quim. This 
time, I made contact with her clit and she responded 
with a whispered, "Yes, that's it," of encouragement.

With my right hand, I drew her panties all the way 
off, allowing her to put her feet on the edge of the 
couch and open her legs a little more. This had the 
effect of making my stroking movements more awkward, 
so I re-angled my fingers, closing the middle finger 
and forefinger together and used them to ease into her 
vaginal hole.

Inside, she was dripping. And so hot. I had no bother 
gathering some of her oily wetness on my fingers in a 
kind of scooping motion, then withdrawing them and 
bringing them to my mouth. She had one of those 
undefinable tastes. A tiny bit sweet, but overall very 
hard to even start to describe. Not salty, not bitter, 
just - woman. Natural, lovely woman. Maybe a touch 
acidic.

I made a show of licking all around my fingers and 
noisily sucking them clean, all the time muttering how 
wonderful Kristin tasted. This made her squirm a 
little, much to my delight. And when I slipped my 
fingers back inside her, I could feel her tense and 
grab them with her vaginal muscles. However, she was 
so hot and slippery. I had no problem thrusting them 
very gently in and out a few times, curling my fore 
and middle fingers up to search for her G-spot at the 
deepest part of the stroke.

Her heels kept slipping off the edge of the couch as 
she moved a little, trying to return my thrusts with 
her whole pelvis. After the fifth or sixth time this 
happened, I placed the soles of her heels against the 
front of my shoulders, which had the pleasant effect 
of affording her more "push back" and me deeper 
penetration. I made another show of sucking and 
licking her juices from my fingers as she murmured "I 
want it, I want it".

I took my middle finger and rubbed gently on the area 
around her ass. I made a point of staying clear of the 
actual entrance. Kristin moaned in encouragement. "Do 
you like this? Does it feel nice? Are you a naughty 
girl who likes men to play with her ass?" In response, 
she cooed and wiggled her pelvis some more, causing my 
finger to briefly come to rest upon her rear entrance.

I moved my finger back to her vagina once more, 
getting it nice and slick for my next move. I traced a 
path down her perineum to her rear entrance. "How did 
you say your husband described your ass, Kristin?" No 
meaningful response, at least that I could make sense 
of. So I tried again, this time rubbing her own 
moisture over her asshole as I repeated "what does he 
tell you about your ass?"

"Mmmmm. Too big..." she replied. I wasn't sure if she 
was referring to my finger or if that was the answer 
to my question.

"What else? What does he say?" I asked again, starting 
to press my fingertip inside her most delicious-
looking rear hole.

"Mmmmm. Exit-only, exit-only..." was her response as I 
moved in up to the first knuckle.

"And does this feel like exit-only to you, Kristin? 
Can you feel my finger sliding into your sexy ass? And 
does it feel good?" as I pushed in further, up to the 
second knuckle.

She was sweating now, visibly sweating. "Oh God! Oh 
God! Oh God! I can't believe I'm letting you do this. 
I'm nearly there, nearly there... Oh God!"

I could feel her tensing and starting to shake at the 
same time. She pulled my head down to her clit and 
ground against my lips. I managed to get my tongue out 
and used that, almost in self-defense, permitting 
myself the space to breathe at the same time. It 
didn't take much more to put her over the top. I 
managed to maneuver my forefinger into her vagina as 
she started to come. With both holes now occupied, she 
clenched down hard, very hard. I forced my middle 
finger all the way into her ass, as deep as I could 
get it, until her perineum pressed down upon the 
webbing between my fingers.

I could feel her pulsing inside, gripping and pulsing 
and moaning and keening in all sorts of lovely 
combinations. Kristin squeezed and pinched her own 
breasts through the kind of shapeless, indigo shift-
style top she was wearing. She'd never bothered to 
remove that, or the bra underneath. I could see the 
right side strap where the neckline of her shift had 
moved to my left. I assumed it was her nipples she was 
pinching, but nothing really showed. But her face was 
such a picture, totally slack, in contrast to the rest 
of her body, eyes dancing around in their sockets and 
eyelids fluttering.

Her breaths seemed to be mostly exhalations - and 
quite audible ones at that, almost the kind of huffing 
noise a deer makes. Her calves and thigh muscles were 
taut as she really, really pushed back against my 
upper body with her feet. I had to press forward quite 
firmly to keep my fingers embedded in her two, tight 
holes. Seconds passed and she began to relax. At 
least, Kristin mostly relaxed. Her ass and vagina 
showed no indication of releasing their grip on me, 
until her arms flopped by her sides and her head 
rolled back.

Obviously, I was still extremely aroused as I hadn't 
had any attention paid to my cock, throbbing as it was 
in my pants. And in that state, I felt extremely 
naughty and figured on seeing how far we could take 
things, even though Kristin had just had an enormous 
orgasm.

Her feet slid down me and to the floor. I took the 
opportunity to move onto the couch next to her, my 
fingers still buried in her pelvis. I leant over and 
gently kissed her left (face) cheek. I kissed her a 
few more times, nibbling my way down to her neck, then 
along her jawline and up to the corner of her still-
parted lips. I felt a quick compression on my fingers, 
but no noise escaped Kristin's lips. Then she did it 
again, a very short squeeze of my fingers, primarily 
felt on my middle finger, which was still 90% in her 
ass. I wiggled the top two knuckles a little, 
eliciting a grunt from her. "Do you feel that?" I 
whispered in her ear. "Do you feel that? Do you know 
what that is?" I didn't wait for a response before 
continuing: "that's you letting me finger your 
ass...that's my finger up there... (wiggle, wiggle)... 
do you like that?"

Hearing a small whimper from her, I continued "why did 
you deny us this pleasure for all those years? You 
obviously like it..." (A small "uhhhh" from Kristin). 
I started to rotate the end of my middle finger inside 
her anal canal, feeling the differing amounts of 
"give" in various orientations. Kristin's whimpering 
resumed. I considered how I might be able to get my 
cock in there, but she really was new to this and even 
my one finger felt significantly constricted.

"So you like me fingering your ass, eh? Is one finger 
all you can take?" 

At that, her eyes, which had been closed, flew wide 
open and she muttered: "Oh, God, no - no more. I can't 
take any more fingers back there. You'll split me 
open, I'm too tight!"

I smiled and kissed the side of her mouth again, 
before breathing into her ear "I wasn't thinking of 
more fingers... do you know what else I might have 
been thinking about?" She squirmed and blushed again, 
an even deeper shade this time.

"No, no - I think I know what you mean and there is NO 
WAY you're putting that inside me, just NO WAY, not 
ever..."

In my heart of hearts, horny as I was, I mentally 
conceded she was right. My cock was going to be 
substantially thicker than my finger and I could 
already feel her trying to push my finger out by using 
her defecation muscles. "What if I don't want to 
remove my finger?" I asked her. Maybe we should keep 
this going a while longer?"

"No, please," she replied. "Getting uncomfortable, 
please take it out," Kristin pleaded.

I figured if I ever wanted another chance, I should 
comply. So I eased my middle finger from her now-very-
tight ass and, at the same time, popped my forefinger 
from her slick vagina. I took the opportunity to drag 
my forefinger up the length of her gash, deliberately 
applying pressure around her clit as I reached the 
top. She trembled a little. I made sure to keep my 
middle finger away from her cuntish juices as I 
brought my hand higher. "Close your eyes," I 
instructed her.

For the first time in a while, she looked me directly 
in the eye, puzzlement clearly showing. "Please close 
your eyes, do as I tell you," I repeated. Kristin 
resigned herself to compliance, settling her head back 
and closing both eyes. I brought my left hand up to 
her face, spreading my fingers to isolate them. I 
moved my forefinger beneath her nose "Now, tell me - 
cunt or ass?"

No response came forth. "Which is it? Cunt or ass? 
Where has this finger been? Has it been in Kristin's 
cunt, or has it been up Kristin's ass?" Catching onto 
my meaning, she reddened once again, blushing 
furiously.

"That smells like my front" she replied, softly.

"You're what? Is it your cunt or your ass?" I 
interrogated. I wanted to hear those words from her 
sweet mouth.

"My vagina. It smells like my vagina."

"That wasn't exactly what I asked. Is this Kristin's 
cunt or is this Kristin's ass?"

Resignedly, she finally responded "It's my c-cunt".

"That's right, Kristin - it's your cunt".

I switched fingers under her nose. "And this one?"

She hesitated and tried to recoil her head into the 
back of the couch "that smells like butt!"

I tut-tutted at her "You know that's not one of the 
options - is it Kristin's cunt or is it Kristin's 
ass?"

"Ass. It's ass".

"WHOSE ass is it, Kristin?"

"It's my ass, it's mine"

Having gotten her this far, I wondered if I could take 
her one more step.

"Which finger are you going to lick clean, first, 
Kristin?"

If it had been possible for her to recoil further, I'm 
sure she would have. Her eyes flew open and she leant 
a bit toward her right to get her mouth further from 
my waving fingers.

"It's OK, Kristin. I can see you're not quite there 
yet. But I want you to keep your eyes open now and 
watch what I do, OK?" I asked.

She pushed her thighs together (which had been lying 
apart this whole time) and nodded slightly, lips now 
firmly closed. She kept her eyes on the fingers of my 
left hand.

"Kristin, you know where these fingers have been - you 
let this one (I extended my forefinger) into your 
cunt. And now I'm going to fulfill one of my ambitions 
and lick your cuntish juices from it, while you watch 
me. Remember - this finger has been in your cunt and 
I'm about to savor your "special sauce" you share with 
so few."

She was beetroot red at this point, very visibly 
squirming, her left thigh still pressed against my 
right leg as I held her gaze and ran my forefinger 
beneath my own nose "Oh, Kristin, your special sauce 
smells delicious, especially when it's fresh from your 
neglected cunt" I put my fingertip onto my own tongue 
and swirled it around a bit. "Mmmmm - this is nice, 
really nice. Are you sure you don't want to taste your 
own juices, Kristin?" She continued to squirm, this 
time starting to press her thighs together, I noticed. 
I could see the lower part of her belly twitching a 
little as she tightened and relaxed her pubic muscles. 
She was starting to get off on this, too, just like 
I'd hoped!

I pushed my finger all the way into my mouth and 
sucked it totally clean. She really was quite 
delicious.

"Now, Kristin, I still have another finger which has 
been inside you. Do you remember where it was?"

Her breathing was most definitely indicative of 
arousal again. Her eyelids fluttered and then settled 
into a hooded position. I asked again "do you recall 
where this finger was?"

"In...My...ass" she haltingly replied.

"Very good, yes. This finger was up your ass. You 
haven't had a lot of fingers up your ass, have you, 
Kristin? When was the last time you had someone's 
finger up your ass?"

"Never... you're the only one" her breathing increased 
yet again, she was almost panting now. I hadn't even 
noticed her right hand move to her groin, fingers 
reaching down through her pubic hair to caress the top 
of her mound.

I sniffed my finger. "And do you know what we're going 
to call this finger from now on, Kristin? You and I 
are going to call it my ass-finger, because it's the 
only finger to have been up your beautiful ass."

"Ass finger, ok," her words were uneven and her eyes 
were almost closed. Her hand movements had become more 
frantic as she masturbated next to me. 

"Look at me, Kristin. Look at me," I commanded. I used 
my right hand to pull her chin in my general direction 
and her eyes opened wider. I put my "ass finger" into 
my mouth and rolled my tongue all around it, 
deliberately keeping my mouth open. She couldn't tear 
her eyes away. She watched that finger, which only a 
short time ago had been up her ass, get licked clean 
inside my mouth. 

Her eyes widened and her left hand flew up the inside 
of her shift to her left boob. I could see her fingers 
burrowing inside her bra, pushing it up while she 
pinched her nipple. She was jerking and starting to 
come, just pushed over the top by the naughty things 
she was hearing, being made to say and watching.

"You are such a naughty girl, Kristin. I can see 
you're enjoying all this naughty talk and I love the 
effect it's having on you. It's bringing out the real 
Kristin, the Kristin that's been locked up inside for 
too many years. You love this, you really do. It's 
what you want more than anything when you're with me, 
you can admit it to yourself now..."

I noticed the cries of, "God! Oh God!" had ceased. 
She'd not only come hard by her own hand, she'd 
actually passed out. I was now pretty sure we'd have 
other opportunities for lovely intimacies in the 
future, but there was no harm in gathering a memento 
or two. I took out my iPhone and snapped a few 
pictures of Kristin lying there, naked from the waist 
down, on the couch. 

I moved her thighs apart a little more and snapped two 
photos of her lovely, moist snatch. I couldn't figure 
out how to get one of her ass without moving her too 
much, so that would have to wait for another occasion. 
I took one last, loving lick all the way up her 
furrow, stood up and left her alone to recover.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 74