Tuesday, January 16, 2018

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


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