Category Archives: Trainer

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Chat #2 Trainer: Pussy words

January 19, 2017 Thursday
Tim   8:27 PM
Hi! I’m on for a while. Hope to hear from you!
Sassy  8:30 PM
Hiya!
I was watching the first episode of “Victoria” on PBS. 
Sorry to be slow joining the party!
Tim  8:34 PM
that’s OK, glad you are here
so… what are you wearing?
Sassy  8:35 PM
I am still dressed from work
Tim  8:35 PM
And what would that be?
Sassy  8:36 PM
Blue top that buttons all the way up the front (or unbuttons) with a silk scarf, blue slacks, You? 
Tim  8:45 PM
my home clothes, blue jeans and a sweatshirt
I like the unbuttons thing!
Is this not a good time for you?
Sassy  8:54 PM
Sorry.. Hubby distracted me. I am back!
What would you like to know tonight?
Tim  8:55 PM
My favorite subject…Sassy
Sassy  8:55 PM
Awww
If you mean to be charming, you are succeeding
Tim  8:56 PM
Is there a problem, I dont want to be a pest
I am serious that I want to know you
Sassy  8:57 PM
You are the furthest thing from a pest!
Tim  8:57 PM
While waiting, I was looking at your tumbler site
Sassy  8:58 PM
The courtesan?
Tim  8:58 PM
yes
Sassy  8:58 PM
nice distraction?
Tim  8:59 PM
Yes it is. One of the first pictures was a man who came on a woman’s breasts  and I thought of your fantasy
Sassy  9:00 PM
I better go find that photo!
Tim  9:00 PM
Can I be truthful and honest about that sight?
Sassy  9:00 PM
Sure
Tim  9:01 PM
I do like larger woman than they had
Sassy  9:01 PM
Interesting…
Tim  9:02 PM
any picture that got you interested
Sassy  9:04 PM
There was a set a long time ago of kissing that got me started
Tim  9:05 PM
interesting! 
but now my mind jumped to your car metaphor on your last email
i have a mini van
Sassy  9:05 PM
Hee!
I used to…
Tim  9:06 PM
but I hope you understood what I meant about being built for comfort
Sassy  9:08 PM
Yes! That was a great phrase!

Here’s the kissing gifs set
http://companyofthecourtesan.tumblr.com/post/155985422365
Tim 9:09 PM
I love a good restaurant. Italian would be my favorite
that is a great picture set
Sassy  9:09 PM
Have you been to the one on the lake in Marlboro? Allora?
Tim   9:10 PM
Did I tell you I love to kiss
Yes, it’s a lovely place
Sassy  9:10 PM
It has the lip nibbling I was talking about
I went once… yummy
Tim  9:10 PM
Several fine restaurants near there
Sassy  9:11 PM
Wow!
Allora is a favorite of the Boston Hidden Restaurants  guy
Tim  9:11 PM
I like lip nibbles and a good tongue. 
passionate kisses are divine
Sassy  9:12 PM
I tend to suck on the tongue that makes its way into my mouth…
Tim  9:12 PM
There is a great small family owned one in Marlborough called Linguinies
Sassy  9:12 PM
What do you order?
Tim  9:12 PM
Wow I should wait before I write, 
It’s like two conversations at once
Sassy  9:12 PM
I probably shouldn’t admit it, but I like Olive Garden.
Tim  9:13 PM
I like it all.
Sassy  9:13 PM
We go to the one in Shoppers World sometimes
Tim  9:13 PM
It’s not bad, there is one out here too
Sassy  9:13 PM
Are you really in the town you listed? 
Tim  9:14 PM
Yes, and you?
Dont answer if you dont want
Sassy  9:14 PM
Definitely!
I live and work here
Tim  9:14 PM
Cool
Sassy  9:15 PM
Yup
I own a condo
Been here since 1990!
Tim  9:15 PM
Do you like it? do you live in a house or apartment
Sassy  9:15 PM
I adore it
Condo life is pretty good for me, especially in the winter
Tim  9:15 PM
I moved here about 15 years ago
Sassy  9:16 PM
Why?
Tim  9:16 PM
I have the driveway from hell
Sassy  9:16 PM
Snowblower?
Tim  9:18 PM
We found an old house on 5 acres. 
coming from PA, I loved the concept of space. 
Yes, I got one but it did not start this winter!
But it’s not the snow I need blown 🙂
Sassy  9:18 PM
Do you have a name for your male member?
Tim  9:19 PM
Sorry, the wild me is out right now
Yes, I hate to admit
Sassy  9:20 PM
Hi Wild Tim!
You don’t have too. 🙂
Tim  9:20 PM
Just wanted to make you ask
Sassy  9:20 PM
What term do you like for sexy banter – dick? Cock?
TELL MEEEEE!
PLULEEZE?
Tim  9:21 PM
He is so special, I gave him two names: John Henry!
Sassy  9:21 PM
Does that pre-date the Red Sox owner?
Tim  9:21 PM
I named him in middle school when he developed his own mind
Sassy  9:21 PM
That’s a perfectly fine name!
I like it better than many others I’ve heard….
Tim  9:22 PM
Do you have a name for your sweet spot, or is that a guy thing
Sassy  9:22 PM
I wish I could find a word for my lady parts
It’s kind of a joke…
someone sent me a list of 217 synonyms for pussy
Tim  9:22 PM
I will suggest names when I meet her
Sassy  9:23 PM
I carefully read each one… tried it on, so to speak
Nada
nothing sounded right
Tim  9:23 PM
Wow, that man needs a hobby!
Does the term pussy offend you at all
Sassy  9:24 PM
I think it was a compilation of responses from women
No… just doesn’t seem right
vagina is too clinical
Tim  9:24 PM
an example
Sassy  9:24 PM
tunnel of love 
makes me giggle
Tim  9:25 PM
of one of the names
and you are right, vagina is a health class word
heard that one, but vagina is latin for a sheath for a sword
Sassy  9:27 PM
that makes sense
vulva… bleh
cunt… um… no
hooha is okay 
but still makes me giggle
Tim  9:28 PM
The c-word has a very interesting history, 
I adore the history of words
What about an alter ego woman’s name
like Betty
Sassy  9:28 PM
Nah
 it works sometimes
Tim  9:28 PM
Not Betty, but one like us men do
Sassy  9:29 PM
Have you read or seen the Vagina Monologues?
Tim  9:29 PM
no.  heard of it but never read or seen

Sassy  9:29 PM
I should send you the script from the one I saw
Tim  9:29 PM
I would like to read it, maybe with you
Sassy  9:29 PM
It’s only 35 pages and I think you’d find it funny, sad, interesting, angering, and glorious
Tim  9:30 PM
I dont really know about the play, but I would really like to know
Sassy  9:31 PM
It’s little vignettes, so easy to read in spurts
Tim  9:32 PM
Did I tell you I love pussy, vagina, tunnel of love, or what ever you call it, a rose by anyother name is….
Spurts … like the sound
I think she is so beautiful
Sassy  9:33 PM
I am amazed at how they vary so much
A pal of mine collected photos… fascinating the variety
Tim  9:35 PM
from the internet or from people he/she met
I think god or the creator etc. got that body part so prfect
Sassy  9:35 PM
A mix
Tim  9:35 PM
Is it on line or private collection
Sassy  9:36 PM
I sent the script.
I think it was a tumblr… let me look
Tim  9:36 PM
thank you, I will read it in case we have some silent, awkward pauses when we meet
Sassy  9:40 PM
The thing that brought it to mind is the skit about CUNT
trying to reclaim that word
Tim  9:43 PM
Do you have a positive self image of your pussy?
Sassy  9:45 PM
I don’t think about my parts much…
I do like that my plumbing still works
And men say I am tight
Tim  9:45 PM
I will have to read the script, but your insights will help
Sassy  9:46 PM
Most of the skits are on youtube 
if you get the urge to see them performed
I will be interested in your comments
either in writing or in person if that’s easier
I looked up “vagina photos tumblr”… there are a bunch!
Tim  9:47 PM
why don’t you think about it much? I am glad the plumbimg works, more than you will know. comments  on the play or your parts?
you can send the link if you wish
Sassy  9:47 PM
which link?
Tim  9:48 PM
the vjays tumbler links
Sassy  9:49 PM
http://beautyofvaginas.tumblr.com/
Tim  9:50 PM
I hope I did not make you feel uncomfortable when I asked about you self body image
I just want to get to know how you think, and that was insensitive
Sassy  9:51 PM
That was fine!
http://mikeyd198709.tumblr.com/
Tim  9:52 PM
thank you for the pictures
Sassy  9:52 PM
I can’t find the one I want… hate that
It’s just close ups of vajayjays
Something very… artsy about it
Tim  9:53 PM
I unfortunately have to go now! I so love talking to you
Sassy  9:53 PM
Good night! Mwah!
I keep meaning to give you virtual bj and getting distracted… sorry!
Thanks for letting me noodle about terms
Tim  9:54 PM
I can’t wait to meet you and have a wonderful face to face talk! I hope we can become confidants
Sassy  9:54 PM
Pet John Henry for me!
Tim  9:54 PM
Oh I will
Sassy  9:54 PM
Yes please!
Tim  9:54 PM
do you pet yours
Sassy  9:54 PM
🙂
Tim  9:55 PM
that is a big smile, pet her for me!
someday. maybe I can help
Sassy  9:55 PM
Soon
Tim  9:57 PM
 sleep tight and be safe
we will chat in the future! 
bye and kisses. 
kissing with some tongue, 
can you blow tongue kisses
got to go, but I so want to stay
Tim 11:23 PM
you still on?!
I just finished watching a show with my wife, have a few


by

Talking to the Trainer

January 18, 2017 Wednesday
From: TimmyTim
To: Sassy
Date: Wed, Jan 18, 2017 at 7:43 AM
Subject: Enjoy Your Lunch!
Sassy,
Thank you for that wonderful chat last night!  I enjoyed learning so much about you, both the playful and the serious! I do not want you to think that you were a hussy! We talked about the fun, the serious and the sexy! In your profile you said that you enjoy sex talk, so don’t feel guilty! It’s an important part of our lives and I thank you for sharing!
I am so glad we are meeting! You have lit the fuse of desire, and I do want to explore the next level. It amazes me how quickly we connected and passed the superficial. I so want to see your smile and blue eyes. You have mentioned your sultry voice and I would like to hear that also! Would you like to talk on the phone sometime, …. Tonight? We can discuss the details of a meeting!
I never had a chance to ask you about your love of theater. I love the theater. We have season tickets to two places. Please tell me more about what you’ve seen where?  I’d love to sit in the back in the dark with you and… Wow how quickly I digress! (Cut me some slack, it’s been like a year!)
Well it is Wednesday and I have to go train a roomful of eager and not so eager folks! Consider a phone call tonight!
Hugs with some serious French kissing!
Take care,
Tim
Sent from Yahoo Mail for iPhone
=====
From: Sassy
To: TimmyTim
Date: Wednesday, January 18, 2017 1:08 PM
Subject: re: Enjoy Your Lunch!
Hiya Tim!  Hope you’re having a wonderful Wednesday!  
I am smiling, remembering the words you typed.  I can’t believe how fast the time went – that is a sign of a fun time!  Thank you for sharing and making it easy for me to share.  
I don’t feel any guilt… I probably should but I don’t.  It’s more like the two sides of my brain arguing… the brassy Sassy acting out and the demure lady piping up about risk and propriety.  Heh.  Our job is to keep Sassy in the forefront!  
Phone is fine!  Tell me a time or email me when you’re ready with your number.  Are you set up to be safe in terms of no one seeing your calls?  I lost a guy with a family phone plan and an inquisitive son.  And he lost his family.  
Wonderful that you get out to support the arts on stage!  What is the best show you’ve seen lately?  I usually talk a lot about  up theater everywhere I go, but I will keep the details vague for now.  We could definitely find ways you could attend with me…and hold my hand in the back.  In the dark. 
I have another sexy story I’ll send so you have something fun to help pass the hours until I can wrap my voice around you.  
Now I’m going to go think about your tongue.  Mmm… 
-S
=====
From: Sassy
To: TimmyTim
Date: Wed Jan 18, 2017 at 1:07 PM
Subject: The Storm
The Storm
He made it inside just as the first thunder clap sounded.  BANG!  It started to pour as he walked past the living room windows.  Wow. That was close.  He loved thunderstorms!  He was very tempted to stand outside to watch the storm.  Maybe even dance in the downpour.  But there was something more important he had to do. 
He knew where to find her.  He shed his clothes as he made his way to the bedroom and sure enough, there was this lump the size of a person under the blanket. He rubbed where he thought a leg might be, and a slight whimper filtered out through the covers.  There was a crash of lightning and another big boom, and she shrieked. 
“It’s okay.  You’re okay.  I’m here,” he said calmly, trying to be soothing.  He crawled into the bed next to her.  She clung to him and wrapped herself around him, burying her head in his chest, trembling.  He couldn’t believe she was still such a wuss about thunderstorms.  She was so brave about almost everything else. 
But he knew how to distract her.  He put his hands on her back and rubbed gently.  He explored up and then down, surprised that she was naked.  He pressed her ass so that she fit tightly against him.  She moaned sweetly when she felt him hard against the top of her leg.  She shifted her head up and grabbed his head with her hands, kissing him frantically.  He slowed her down a bit, pressing his tongue into her mouth at a leisurely pace and making more soothing noises. 
“We have plenty of time…” he pointed out, squeezing her breast and teasing the nipple.
“Fuck me,” she whispered fiercely.  It sent a shock wave through him.  He loved it when she talked dirty to him.  Everyone else saw her as an ultra-polite, demure lady.  Only he knew about the wild girl inside.  She was turning the intense fear into another emotion, putting it to good use.  Smart girl.  
“Yes, ma’am…” he chuckled.  He hugged her, pondering which position would be best. 
“Fuck me now,” she urged him. She wasn’t going to let him go slow today.  She flattened him onto the bed, straddled him and pressed him close, shifting her hips to rub him against her.  He could feel her dripping already.  It made him a little crazy.  He shifted slightly and she took him inside her and began to move.  Up and down she went.  He put a hand on her hip and one on her breast, twisting, teasing…
He knew her inside and out, as much as any person can know another.  But it never stopped surprising him how tight and hot she was, how he fit inside her like a sculptor had made him to be there and made her to make him feel so incredible every single time.  When he first touched her as a green boy, he realized that she was different.  He had felt an emotional connection for ages, but when they finally kissed, he felt a physical connection to her that he never felt again in his life.  Special, comfortable, exciting… and at times, inflammatory.  Chemistry.  That had never changed.  He thought he would get tired of her, stop thinking about her, stop wanting her… but it never happened.  Sometimes it drove him crazy, when he couldn’t get to her.  When he could and he couldn’t get inside her fast enough.  But it was the best kind of crazy… it made him feel alive.  Kept him young.  Made them both happier than anything or anyone else.  And the most amazing thing was that she felt the same way.  He marveled over that every day. 
She stopped moving… sensing that his mind had drifted.  He snapped back to her body and what she was doing, putting a finger at the top of her slit and flicking her most sensitive spot.  She sighed in pleasure and started moving again, rising up, arching her back and driving down on him again, shoving him so deep inside…. and then out again.  Her tits looked amazing when she did that!  It was the sweetest form of torture… so hot, so wet, so…. hmmmm.. he could not think when she was like this.  He could feel… oh, man could he feel!  Every nerve in his body was on fire.  And he craved the heat.  She kept turning up the temperature… taking him closer and closer… and then stopping.  She was panting.  She leaned over and kissed him again, sucking his tongue, twisting her hips… damn.  He felt the magic start.  He wasn’t going to last long if she kept this up… it was as if every muscle inside her was trying to squeeze him, milk him… whoa, baby.  What a woman…he thought she was going to make him peak.  But when he thought he couldn’t take it another moment, she stopped, flipping over onto her back on the bed.
She lay there breathing loudly.  He tried to figure out what she was up to.  She turned to him and kissed him, wrapping herself around him on her side.  She stroked him, then put her hand lower, caressing his balls, pressing the spots she knew would send him soaring.  His breath grew ragged.. what would she do next? 
She pressed a finger inside his ass.  Oh, wow… she was really trying to push all his buttons this time!  His hips rocketed off the bed.  She pumped in and out, whispering in his ear.  “You like it when I fuck you, don’t you, fella?  Like it when I give your ass the love, eh?”  she said, making a little sucking sound.  He moaned.  She knew just what to do.  She moved down his body, putting her mouth where her hand had been, licking his cock and sucking it deep into her mouth, then kissing his balls and sucking them and finally sticking her tongue in his ass!  He moaned and trembled.  She could be such a vixen! 
That was it.  He rolled over, pulled her legs up to his shoulders, and dove back inside her, pumping, deep, long strokes while she moaned and then screamed, her head thrashing from side to side.  He watched her shake, felt her hips crashing up against him.  She opened her eyes and the look… the look nearly made him explode.  So many words popped into his head… lust, passion, fire… love.  No one loved him like she did.  Her mind, her body… it all went together to make him know… mmmm….
There was another big thunderclap and she jumped.  He went wild on her, his hips thrusting in and out, hearing the slap of his balls on her skin and her moans… he let go, let his body take over, let the pulsing inside her trigger the flow…. he filled her, shooting over and over inside her, grunting and moaning and… exploding.  He collapsed beside her, feeling his heart beat, listening to her breathing… smiling. He did love thunderstorms!  And her…
=====
From: TimmyTim
To: Sassy
Date: Wed, Jan 18, 2017 at 2:40 PM
Re: Enjoy Your Lunch!
Sassy,
This will be a quick reply (I promise since I have a scheduling meeting in like 10 minutes).  Thank you for the story!  It is a gift I shall cherish. You are a very good writer and the stories are erotic and sublime.  Have you ever written stories for Littorica (sp)?  We can talk about it tonight?
Do not worry about the demure lady and the brassy Sassy lady.  I cherish and respect both.  I have a very playful side and that prim and proper corporate trainer side also. Together we can let each side have their time in turn.  I want to get to know all facets of your mind, soul and personality.  You are a very complex, beautiful person.
Can I quickly email you at 9:00 tonight with my number? I would love to have you wrap your voice around me.   I do not feel i have a great phone voice, I am better in person.
Well I hope I can keep myself from thinking of where and what my tongue can do for you until this meeting is over! Oh no, they just announced the meeting, I must go…. will text my number to you around 9, but if that is not a good time, please let me know.
Hugs and light butterfly kisses on your neck!
Take care,
Tim
=====
From: TimmyTim
To: Sassy
Date: Wed Jan 18, 2017 at 8:55 PM
Subject: Good time to call?
Sassy, 
Good time to call, but remember to only call when coast is clear! 
# [redacted]
Tim
Sent from Yahoo Mail for iPhone
=====
I sat down on my bed and called him.  Wow.  He has a very sexy voice.  He jumped right into talking about what he would like to do with me in bed!  Oh my, oh my.  A lot of times that doesn’t really work for me but tonight it got me going!  So hot.  So well-spoken.  All things I would like to do!  Mmm… I ended up lying down, squirming… I really want to meet this guy!  I keep wondering what the catch is… 

We started planning to meet.  The tentative plan is for NEXT THURSDAY!  Whee!  
=====
From: Sassy
To: TimmyTim
Date: Thurs Jan 19, 2017 at 12:48 AM
Re: Good time to call?
Hiya! Can’t go to sleep without writing three thoughts: 
Wow!!  That was fun!
MORE!  🙂
And thank you. 
-S
Sent from Yahoo Mail on Android

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by

Chat #1 with the Trainer

January 17, 2017 Tuesday 
Tim  8:09 PM
hey, I’m on early if you are around!
Sassy  9:59 PM
Hi
Tim  10:02 PM
how are you tonight
Sassy  10:03 PM
I’m fantastic now!
Tim  10:03 PM
so glad we could connect!
What do you want to chat about first?
Sassy  10:04 PM
What do you have on? 🙂
Tim  10:05 PM
fully clothed with a sweater, it’s cold outside
and inside too
What about you?
Sassy  10:05 PM
Boxers or briefs?
Tim  10:05 PM
briefs
Sassy  10:05 PM
I have on a big old t-shirt and cotton panties.
What color?
Tim 10:05 PM
not a thong
Sassy  10:06 PM
You can think that if you like!
Did it snow out there?
Tim  10:06 PM
My briefs are “bad boy” black
Sassy  10:06 PM
Oooh….
Tim  10:07 PM
Yes it is snowing, but still have to work anyway
are you wearing a bra?
Sassy  10:07 PM
Nope
Tim  10:07 PM
Oh!
Sassy  10:07 PM
Where are you? I’m sitting at my desk
which is in the living room
Tim  10:08 PM
me too, at my computer, I was working but wanting to write to you
Sassy shared a photo  10:08 PM
[my cleavage in a black bra]
Tim  10:09 PM
Wow! that is very nice!
Just thinking what I could do with those
Sassy  10:09 PM
Mmm hmmm
Tim  10:10 PM
but I thought you were not wearing a bra
Sassy  10:10 PM
That’s an old favorite photo
Tim  10:10 PM
Oh, now the picture is not in my window
Well I like it
Sassy  10:10 PM
Can you scroll back?
Tim  10:11 PM
So you are feeling frisky tonight
I am every time I send a response
Sassy  10:11 PM
There is something about chat that brings out my Sassy side!
Tim  10:12 PM
Me too!
Are you going to treat me to any other pictures tonight?
Sassy  10:12 PM
Maybe.
Tim  10:12 PM
Sorry, I was just scrolling back
Sassy  10:13 PM
Hee hee
If you click it, it should go full screen.
Tim  10:13 PM
Now, about your toys,
I am not intimidated, just challenged
Sassy  10:14 PM
Ah… good!
Tim  10:15 PM
I just clicked out of the chat while perving your picture
Do you own any others?
Sassy  10:15 PM
Other what?
Tim  10:15 PM
Toys
Sassy  10:15 PM
Yes.
Tim  10:16 PM
like what?
Sassy  10:16 PM
There’s one I call the “three ring circus”
Tim  10:16 PM
What is that?
Sassy  10:17 PM
It’s a combination dildo, rabbit and vibrator/undulator
Wacky
Tim  10:17 PM
Do you use it, sounds complicated
Sassy  10:17 PM
Nope
Tried it once
Tim  10:17 PM
didn’t live up to expectations
Sassy  10:18 PM
No
On the other end of the spectrum, there’s the tiny silver bullet. It looks simple and small but…. oh my
Tim  10:18 PM
So ask me a question
Sassy  10:18 PM
What color are your eyes?
Tim  10:18 PM
what Oh my
blue
Sassy  10:19 PM
When you press that little bullet on a sensitive spot? Mmm mmm mmm
Tim  10:19 PM
I do love brown eyes
Sassy  10:19 PM
Mine are bright blue.
One of my best five features. 🙂
Tim  10:20 PM
I meant to say blue eyes
Sassy  10:20 PM
Right
Tim  10:20 PM
What are the other 4
Sassy  10:20 PM
My boobs
My smile
My sultry voice
Tim  10:21 PM
that was 3
Sassy  10:21 PM
My eyes
Tim  10:22 PM
I love a smile!
I have been told I have a nice smile
Sassy  10:22 PM
Do you smile a lot?
Tim  10:24 PM
Yes! One has a choice to embrace life and smile or be a downer
We have such limited time, I don’t want to spend it on negatives
Sassy  10:24 PM
Well said!
Do you have a favorite joke?
Tim  10:25 PM
I love Helen Keller jokes… simple, awful
Sassy  10:26 PM
Like what?
Tim  10:26 PM
how about you, what jokes do you like
Sassy  10:26 PM
My favorite is… Which is better? A TV or a newspaper?
Tim  10:26 PM
OK, why did helen wear tight pants
Sassy  10:27 PM
Why?
Tim  10:27 PM
So her mom could read her lips:)
Sassy  10:27 PM
Whoa! Hee hee hee
Tim  10:27 PM
I like the newspaper
Sassy  10:28 PM
It is better because you can’t swat flies with a TV!
Tim  10:28 PM
That was bad
Sassy  10:28 PM
Thanks!
Tim  10:29 PM
I like the bad ones
I hear so many a day
just as long as they are not mean spirited
Sassy  10:30 PM
Yes.
I get mired in elephant jokes some days
Tim  10:30 PM
How do you know elephant had sex in your house
Sassy  10:30 PM
How?
Tim  10:31 PM
Your Glad trash bags are missing
Wow, we degenerated quickly here
Sassy  10:31 PM
Oh! That’s so bad!
Tim  10:32 PM
But I hope it put a smile on your face
Sassy  10:32 PM
Oh yes…
How old were you when you first had sex?
Tim  10:33 PM
I would like to meet you and see that smile and blue eyes
I was 15
Sassy  10:33 PM
Who was she?
Tim  10:33 PM
I was a little slut
Sassy  10:33 PM
Oooh….
Tim  10:34 PM
We were at the lake and I drove my brother to a party, since I would be sober (due to my age) and when they paired off, the leftover college girl said that the little brother was better than nothing
Sassy  10:35 PM
Was it fun?
Tim  10:35 PM
Oh God, it so beat masturbating
Sassy  10:36 PM
Phew
Did she know you were her first?
Wait… she was your first?
Tim  10:37 PM
Yes, she knew and she was my first.
She gave me a few pointers
and I was hooked on oral sex from then on
I think she took advantage of me a bit:)
Sassy  10:37 PM
Did you ever see her again?
Tim  10:38 PM
Yes, at his wedding.
We were paired up as groomsman and bridesmaid
Sassy  10:38 PM
Did he know?
Tim  10:38 PM
Awkward!
yes, but his wife did the pairing
Sassy  10:39 PM
How old were you then?
Tim  10:39 PM
In my 20s, I think a sophomore in college
How about you
Sassy  10:39 PM
I was 17
Tim  10:40 PM
what were the circumstances
Sassy  10:40 PM
He was my boyfriend.
We’d been dating for 4 months
Tim  10:40 PM
Was it a positive experience?
Sassy  10:41 PM
Just kept going a little further…
a little further… then one night… ALL THE WAY!
Hmm… we had no idea what we were doing. It was… underwhelming.
We were both like…
“THAT is the what the grown-ups go on about? Huh…”
Tim  10:41 PM
unfortunately, first time can be weird
Sassy  10:42 PM
It got better. 🙂
I dated him for another year
Tim  10:42 PM
What college did you go to?
Sassy  10:42 PM
[redated]
Tim  10:44 PM
Really, that’s where my grandmother and great grandmother went
My family was all went to the same place but I rebelled
Sassy  10:44 PM
Wow!
Tim  10:44 PM
Such a small world! what was your major
Sassy  10:44 PM
Econ and Psych double major
Tim  10:45 PM
I love a smart woman
Sassy  10:45 PM
I took courses in 11 departments.
Tim  10:45 PM
Wow
Sassy  10:45 PM
Were you an English major?
Tim  10:46 PM
Why did you not become a psychologist?
FYI – that picture has me all tied up!
I was a classics major! Ancient Greek and Latin
Sassy  10:47 PM
Ooh! I took a couple of classics courses.
Tim  10:47 PM
I knew you were special
Sassy  10:47 PM
My best gal pal was a Classics major
She went on to Yale
Tim  10:48 PM
She teach?
wow
Sassy  10:48 PM
She’s a museum curator
Did a fine arts masters program
Tim  10:48 PM
I wanted to do that after my masters at [redacted], but I was starting a family
Sassy  10:49 PM
When were you in grad school?
Tim  10:50 PM
Late 80s early 90s. as I said. it was the best 10 years of my life
Sassy 10:50 PM
I lived in near there then!
Tim  10:51 PM
Wow!
Life kind of overwhelmed me at that point
Sassy  10:51 PM
I bet
Do you still have kids at home?
Tim  10:53 PM
No. My two youngest are in college
Both on semester abroad now
do you have kids?
sorry I am kinda going crazy here
Sassy  10:53 PM
No kids
What can I do to help?
Tim  10:54 PM
Not that way, I just have this stream of questions going
Don’t want to scare you off
Sassy  10:54 PM
Not at all!
It’s so fun to have someone curious about me, interested…
Tim  10:55 PM
I just find you fascinating!!
Sassy 10:55 PM
Aww… you are enthralling!
Tim  10:55 PM
I think in a different life, we could have been friends
Sassy  10:55 PM
Can we now?
Tim  10:56 PM
I would like to be friends!
Sassy  10:56 PM
I feel this heady combo of comfort and excitement
Tim  10:56 PM
me too!
Sassy  10:56 PM
But I try not to get too far ahead of myself
Tim  10:57 PM
Are we moving too fast?
Sassy  10:57 PM
No… seems fine to me
Thank you ever so much for not pressing to meet right away
Tim  10:58 PM

I really like chatting with you, I want to get to know you

Sassy  10:58 PM
I find it so much better when I have a chance to know someone, poke around in their head…
Build the anticipation…
Tim  10:58 PM
So we are not doing lunch Tomorrow
Sassy  10:59 PM
🙂
I had a lovely lunch with you today.  Virtually.
Tim  11:00 PM
I like to poke around in the head too, but you are a very dynamic, complex woman
Yes you did, I enjoyed our breakfast
Sassy  11:00 PM
I got that impression
Tim  11:01 PM
Don’t tell IT, I had tea and a muffin over the computer
Sassy  11:01 PM
Do you drink coffee?
Tim  11:01 PM
No, mom was English and tea has always been my choice for hot caffeine
Sassy  11:03 PM
When I went to college, the older students said I would learn to drink coffee, pull all-nighters and STOP listening to John Denver
None of that happened!
Tim  11:03 PM
you still wearing that shirt and panties
Sassy  11:04 PM
Yes
Tim  11:04 PM
you could have lied!
Sassy  11:05 PM
Ah… not my thing.
Tim  11:06 PM
mine either
ask me a salacious question
something juicy
Sassy  11:06 PM
Do you shave “down there?”
Tim  11:06 PM
No
Sassy  11:06 PM
Good!
Tim  11:06 PM
I’m afraid I might nick myself
Sassy  11:06 PM
I like it natural. Something to play with
Tim  11:06 PM
how about you
Sassy  11:07 PM
Nope
After losing all my hair during chemo, I don’t want to cut any hair ever  again!
Tim  11:09 PM
Great! I like a woman and don’t know why guys have a fascination with that little girl thing
And you earned that right!
I love the feel of pubic hair when I run my hands through it, on my cheeks
Sassy  11:09 PM
The prepubescent hairless look is creepy to me
Tim  11:10 PM
Do you trim at all?
Sassy  11:10 PM
I get a trim of my head hair once a year…
Do you have head hair?
Tim  11:11 PM
Yes! I still have all my head hair
Sassy  11:11 PM
Wowzers!
Tim  11:11 PM
are you bushy down there?
Sassy  11:13 PM
No. I used to have quite the bush but it came back in sparse and soft
I had ass-length dark straight hair when they shaved it… and came back in silver and curly!
I wondered whose hair I had…
It’s just below my shoulders now
Tim  11:13 PM
My sister had curls when her hair grew back, that is so weird
Sassy  11:13 PM
Enough to grab when you’re… um..
Tim  11:13 PM
Did you have chemo and/or radiation
Sassy
 11:14 PM
All of it… surgery, chemo, radiation…
Didn’t end up with any super powers…
Spent 10 months in treatment
Tim  11:15 PM
You have more power than you give yourself credit for!
I love to run my hands through a woman’s hair
Sassy  11:15 PM
My hair looks like steel wool somedays but it is very soft
Tim  11:16 PM
did the radiation leave a scar
Sassy  11:16 PM
A kind of dappled pattern underneath
Tim  11:16 PM
and how invasive was the surgery
Sassy  11:17 PM
Not much
Tim  11:17 PM
maybe someday I can kiss the scar
Sassy  11:18 PM
2 inch scar upper right, and where they took the sentential node
I also have 5 tattoos.  Whee
The tattoo tech said they look like the earth from very far away!
Little blue dots you can find. 🙂
Tim  11:18 PM
Wow, I love tattoos on a woman
Sassy  11:18 PM
They used them for radiation
Tim  11:19 PM
I will kiss them too
Sassy  11:19 PM
Mmmm
Have you broken any bones?
Tim  11:21 PM
well, I put my left pointer finger in a table saw once
They did some awesome reconstruction surgery
I call it my special finger
Sassy  11:21 PM
Don’t do that again please!
That is a very manly injury.
Tim  11:22 PM
NO, I stick to only training now!
but the finger still can do its most important job
Sassy  11:22 PM
What’s that?
Tim  11:22 PM
your pleasure
Sassy  11:22 PM
Ah…
are you left-handed?
Tim  11:23 PM
right handed
Can I ask one more breast question?
Sassy  11:24 PM
Sure
Tim  11:26 PM
did the treatment for cancer affect the sensitivity of your nipples or breasts?
I might have to sign off temporarily, but I will be right back
Sassy  11:26 PM
Not really
Tim  11:26 PM
Do you have sensitive nipples to begin with?
Sassy  11:26 PM
Medium
You?
Tim  11:27 PM
mine are sensitive but not sexually
Sassy  11:28 PM
Do you like blow jobs?
Tim  11:29 PM
Yes
but I really enjoy giving oral
do you like giving blow jobs?
Sassy  11:29 PM
Yes
Tim  11:30 PM
do you swallow
Sassy  11:30 PM
Yes
Tim  11:30 PM
do you like receiving oral?
Sassy  11:32 PM
Yes
Sometimes a tongue and a finger can be more explosive than sex
Tim  11:33 PM
I think oral can be the most intimate, closest two people can come
Sassy  11:33 PM
I certainly hope they cum!
Can you cum more than once?
Tim  11:34 PM
I am very tactile and my tongue is very sensitive to touching. so it is just an unreal experience for me
Sassy  11:34 PM
Just wondering if there can be a bj and sex
Tim  11:35 PM
Yes I can with proper motivation and attention
Do you like to 69
Sassy  11:35 PM
Not so much…
Tim  11:35 PM
Why?
Sassy  11:35 PM
I have the “chew gum and walk” problem of where to focus
You?
Tim  11:36 PM
i do like to have my face down there when I cum
I like the feel of the two pressing bodies
Sassy  11:38 PM
skin to skin is marvelous
Are you furry all over?
Tim  11:38 PM
yes, but not bear like
Sassy  11:39 PM
dark hair?
Tim  11:39 PM
light, but not blond
Sassy  11:39 PM
any facial hair?
Tim  11:39 PM
no, but I can grow a beard fast
Sassy  11:41 PM
Heh
Tim  11:41 PM
what is your favorite position?
Sassy  11:42 PM
Depends…
I like doggy a lot
or the lying next to each other, my leg over your hip, up from under thing
deck chair is nice
Tim  11:42 PM
Depends with me too
Sassy  11:43 PM
http://www.sexinfo101.com/sp_deckchair.shtml
Tim  11:43 PM
I like doggy, but I will add woman on top
since it let’s me look you in the eyes
and run my hands all over your body
Sassy  11:44 PM
Strange site but very educational. 😉
Tim  11:44 PM
I will have to check it out
I’ve been to that site you naughty girl
Sassy  11:45 PM
oh really?
Tim  11:45 PM
Yes, we will have to try all the positions and rate them
Sassy  11:46 PM
Heh
Tim  11:46 PM
maybe start our own blog
Sassy  11:46 PM
A google spreadsheet. 🙂
Tim  11:46 PM
I can spread many things on a sheet
Sassy  11:46 PM
Though some look like one needs Cirque du Soleil training
Tim  11:47 PM
Yes, but if we can’t quite figure it out, it will still be a magnificent failure
Sassy  11:48 PM
Yup. Failed experiments are important…
there’s some quote from Edison…
Tim  11:48 PM
I have totally enjoyed chatting with you tonight
Sassy  11:48 PM
No awkward silences you were worrying about?
Hope I wasn’t too much of a hussy
Tim  11:50 PM
true
i don’t want to be pushy, so don’t take it that way, 
but would you be interested in the concept of meeting
Sassy  11:50 PM
Absolutely
Tim  11:50 PM
you were not a hussy, just a liberated woman
Sassy  11:50 PM
I am not an email queen. 🙂
Tim  11:51 PM
any time frame on your part
there is just so much I want to talk to you about
Sassy  11:51 PM
Next week?
Tim  11:52 PM
sounds good, it is our quiet time at work so I could get away for a lunch time meeting
Sassy  11:52 PM
Hooray!
Tim  11:52 PM
Wednesday or Thursday
Sassy  11:53 PM
I can usually take off pretty easily but this week I am helping run a big conference
Sounds good
Tim  11:53 PM
can you do a lunch?
Sassy  11:53 PM
Yes
Tim  11:53 PM
I am so excited to meet you
Sassy  11:54 PM
I want to touch you
Rub the inside of your wrist with my thumb
Tim  11:54 PM
and I want to hug you with groping
Sassy  11:54 PM
Ha!
Isn’t that a great concept?
Tim  11:54 PM
That’s your phrase
Sassy  11:55 PM
Yup
A lot of folks close out with Hugs!
so I looked for a way to make it… better
Tim  11:55 PM
I have to go to bed now, I’m up at 5:00 AM
Sassy  11:56 PM
Oh my! Thank you ever so much.
Can we chat again?
Tim  11:56 PM
I still have some prep for work to do
Sassy  11:56 PM
I promise not to keep you up so late next time
Wow!
Tim  11:56 PM
It’s my usual bed time
Sassy  11:57 PM
Sweet sexy dreams T
Tim  11:57 PM
But if I had you next to me in bed, it would be 7:30 pm
I do feel chemistry here
Sassy  11:57 PM
Mmm… that sounds wonderful
Indeed!
Tim  11:58 PM
Good night, and beware of my silent blown kisses
Sassy  11:58 PM
Good night.
First chat. A+
Tim  11:59 PM
I’ll write tomorrow for your lunch
sweet dreams
Sassy  11:59 PM
mwah!
Tim  11:59 PM
caught it