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