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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