Saturday, January 20, 2018

Chat #3 Trainer

January 21, 2017 Saturday

Tim 9:52 AM
HI, GOOD MORNING!!

Sassy 9:52 AM
Good morning hot stuff!

Tim 9:53 AM
Thank you!
So glad we have the time for a nice relaxed morning chat

Sassy 9:55 AM
I'm smiling.
Are you dressed?
Had your tea?

Tim 9:55 AM
I liked the pictures you sent, one was like your last story. Sassy story brought that picture to life
I am dressed and I have my tea.
what are you wearing?

Sassy 9:55 AM
I saw it and thought... He will get this.

Tim 9:55 AM
Oh yes

Sassy 9:55 AM
What kind of tea?

Tim 9:56 AM
Will we be able to wait? I wonder aloud
I am having Irish breakfast tea straight up

Sassy 9:58 AM
Did I tell you I went to afternoon tea at the Taj last Saturday? So civilized... rooibus was my tea that day.
I haven't gotten around to any food or drinks this morning...

Tim 9:59 AM
That sounds like it must have been fun. I do have tea with my trainees sometimes. Trying to civilize them

Sassy 9:59 AM
Get your wife off to the march?

Tim 9:59 AM
But What are you wearing

Sassy 9:59 AM
The usual... big old t-shirt and cotton panties. You?

Tim 10:00 AM
yes she is off with my "bonus" daughter, I hate the term "step"

Sassy 10:00 AM
nice

Tim 10:00 AM
is it a thong? I am in my undies

Sassy 10:01 AM
My sister is going with their UU church group
What color undies today?

Tim 10:02 AM
boring white!
This whole Trump thing has me depressed and worried

Sassy 10:03 AM
Sad
Hope I can perk you up!

Tim 10:04 AM
Is there anything on your mind you would like to talk about?
Are you demure Sassy, or Brassy Sassy?
I just want to talk

Sassy 10:04 AM
Hmmm... about 1100 things.

Tim 10:04 AM
pick one and lets have a heart to heart

Sassy 10:05 AM
Hang on one sec... giving Hubby my breakfast order

Tim 10:06 AM
That’s OK, you are worth the wait

Sassy 10:08 AM
Awww... you are such a charmer!
What time did you wake up today?

Tim 10:09 AM
With anyone else, but with you it’s what I want to do!
I got up at 8. I normally get up at 5, so sleeping in a bit

Sassy 10:09 AM
Nice!

Tim 10:09 AM
how about you

Sassy 10:09 AM
I usually get up about 8:45 on weekends but I woke up at 5:30 am today... not sure why

Tim 10:10 AM
you were waiting to chat!

Sassy 10:10 AM
Exactly

Tim 10:10 AM
What are you having for breakfast

Sassy 10:10 AM
Chicken bacon ranch sandwich and a coffee roll from Dunkin

Tim 10:11 AM
That sound good!

Sassy 10:11 AM
Not my faves but Hubby has to have his hazelnut iced coffee so I let him grab me something

Tim 10:12 AM
maybe someday we could have each other for breakfast!

Sassy 10:12 AM
I'm more of a McDonald's breakfast person... like their burritos, egg McMuffin... hashed browns!

Tim 10:12 AM
so what is on your mind this morning?

Sassy 10:12 AM
I would adore having you for breakfast!

Tim 10:12 AM
I hogged our last chat and today it’s about you

Sassy 10:12 AM
Nothing like an extra shot of protein first thing.... ;)

Tim 10:13 AM
and a special breakfast sandwich

Sassy 10:14 AM
I wish you were here

Tim 10:14 AM
me too

Sassy10:14 AM
This is when I usually play...
Hubby takes about 30 minutes to go and come back...
So I grab a toy and tumblr and indulge

Tim 10:15 AM
When I had a partner who wanted me intimately, this was our time
but I am glad I have you to talk to know

Sassy 10:15 AM
Saturday mornings?

Tim 10:16 AM
yup
so I now take a longer shower

Sassy 10:16 AM
I was thinking of you in the shower
with me
Being silly
and sexy

Tim 10:17 AM
I was thinking of you too.
then John Henry might let me have some talking time
but it’s not working

Sassy 10:17 AM
Oh?

Tim 10:17 AM
which tumblr

Sassy 10:19 AM
I usually start with skincast.tumblr.com
exhibitionists
little videos
so naughty

Tim 10:19 AM
do you like exhibitionists

Sassy 10:19 AM
In videos

Tim 10:19 AM
have you ever been one?

Sassy 10:19 AM
Not exactly

Tim 10:20 AM
I have never either

Sassy 10:20 AM
There have been a couple of times I got frisky in public places
But I tried to keep it under wraps

Tim 10:20 AM
but what does exactly mean, and what type of places

Sassy 10:20 AM
A busy parking garage at a mall
leaning against a car

Tim 10:20 AM
I would be so nervous, but that must be the thrill

Sassy 10:21 AM
that was totally Sassy

Tim 10:21 AM
yes it was
how about the back of a red mini van

Sassy 10:21 AM
and... um... in a cemetery

Tim 10:21 AM
that is so funny, I did that in college

Sassy 10:21 AM
on a rainy day
on a bench in a copse of tree

Tim 10:22 AM
it was a full moonlight
over a bench

Sassy 10:22 AM
I may have given someone a bj amongst the dead
Bad bad Sassy

Tim 10:23 AM
guess there were more "stiffies"

Sassy 10:23 AM
Har har

Tim 10:24 AM
depends on how you define bad
i do like that tumblr, just opened it
you are wicked

Sassy 10:25 AM
You betcha!
So I am not the "hey, let me show off my tits in public!" type...
more of the "they couldn't wait" type

Tim 10:26 AM
I get it, but having some fun with the spectre of getting caught
You said you have taken pictures in the past, have you ever recorded yourself

Sassy 10:28 AM
I have taken exactly one video and it was awful
Someone wanted to see me playing...
He said it was like watching paint dry
and then the wall explodes.

Tim 10:28 AM
someone once said the worst way to change a good self body image was to video your self

Sassy 10:28 AM
Heh

Tim 10:29 AM
that is an interesting metaphor
you were brave to send it to someone

Sassy 10:29 AM
I have done sexy things on the web cam a couple of times, but usually technical difficulties and the performance pressure make it very odd

Tim 10:30 AM
I could imagine they would

Sassy 10:30 AM
Have you?

Tim 10:30 AM
I have never, but
with the right person, it is on my bucket list

Sassy 10:31 AM
With someone I know really well, it's not 100% bad

Tim 10:31 AM
Well, lets get to know each other 100%

Sassy 10:32 AM
Sorry... I only go to about 96%
Gal has got to have some secrets!

Tim 10:32 AM
Yes, not having some mystery will make us boring

Sassy 10:33 AM
I have a feeling you are going to go all the way there though
and it will be a good thing

Tim 10:33 AM
I am trying, because you are very special and unique

Sassy 10:33 AM
Really?

Tim 10:34 AM
I went back to your profile on AM the other day, and you are who you said in that short bit
The only one ever

Sassy 10:35 AM
Wow
I wrote that in about 15 minutes on a rainy night when both Hubby and old flame forgot my birthday
I was whining in the chat room and my pals there egged me on

Tim 10:35 AM
When is your birthday, so I never forget

Sassy 10:35 AM
Oh you are too good!
September

Tim 10:36 AM
I am not good, but respectful and try to think of others
my sister’s was in september, can I ask the date

Sassy 10:37 AM
That will take you a long way!
8th

Tim 10:37 AM
why

Sassy 10:37 AM
When is yours?

Tim 10:38 AM
Mine is [redacted],
my gift to myself when I made a wish was to find a good person! My wish seems to be coming true

Sassy 10:39 AM
A lot of men's New Year's resolution was to get laid
Glad you have slightly higher goals!

Tim 10:40 AM
Mine was not a get laid, but if I found that person, then let it happen
but I really needed to find a person who wants more

Sassy 10:42 AM
When you write about what you want... I could have written it. Freaks me out a little…
We can do it!

Tim 10:43 AM
me too! but when you look and are honest, great things can happen.
BE honest
you get me so hot that I can’t type

Sassy 10:43 AM
I do?
Are your hands busy elsewhere? Or your mind addled?

Tim 10:44 AM
mind addled at this point, how about you

Sassy 10:45 AM
My mind keeps wandering off to the possibilities

Tim 10:45 AM
mine too

Sassy 10:46 AM

You know in Star Wars when Luke is flying down the trench and the other pilot says, "STAY ON TARGET! STAY ON TARGET!"

Repeating that to myself. Heh.

Tim 10:46 AM
me too!

Sassy 10:47 AM
How can I wait until Thursday?!
I want to get in my car

Tim 10:47 AM
I don’t want to get too far ahead in my mind, but you have definitely made those possibilities cum to life
could you with you party

Sassy
  10:49 AM
I am used to demanding my brain have no expectations of any man... so I can be pleasantly surprised if anything happens... but it is straying
It's better to wait... *sigh... know more...
Doesn't keep me from daydreaming about seeing you today!

Tim 10:52 AM
me too! The wait will make all the more better
but I do day dream about seeing you too
That first hug will be magical
God, sometimes I curse that calendar

Sassy 10:53 AM
why?

Tim 10:55 AM
When I am being romantic me, it gets in the way of seeing you
but level head me knows its better
"but"
it is the battle of the minds

Sassy 10:56 AM
I can't believe it's only been just over a week since you wrote to me

Tim 10:57 AM
On the one hand it seems such a little time, on the other I feel I've know you for a long time

Sassy 10:57 AM
Yes... very true.

Tim 10:58 AM
That is how I know we clicked
I am I going to fast?

Sassy 10:58 AM
Interesting
No... I marvel at how you suggest each step just as I feel ready for it

Tim 10:59 AM
don't want to freak you out, but I have this third sense that it is right

Sassy 10:59 AM
What is right?

Tim 11:00 AM
You! you are a different person from the rest I have talked to. You are indeed a special soul. One I want to know, be with

Sassy 11:00 AM
Gives me hope that you will good in bed…
 pay attention to my reactions. :)

Tim 11:02 AM
Yes, and you also. As I said, I am a giver, I want you to feel as special as I do
I want to learn those reactions, anticipate them, feel with you

Sassy 11:02 AM
Mmmm

Tim 11:03 AM
That’s why John Henry has been talking :) but I also want something out of bed too

Sassy 11:04 AM
I aim to make you smile every day... whether we can see each or I am miles away.

Tim 11:05 AM
i want to peer into your eyes when we just talk, woo you when I know it might not happen that time
Make you smile when you open an email

Sassy 11:05 AM
As you have seen, I like to send stuff... to help you smile, make you think... get you hard!

Tim 11:10 AM
Yes I am smiling and hard
But on a higher level
more of me than just John Henry is writing to you
I want to capture your mind, know your soul
I don't think I ever could have written that to anybody I have "met" on
"AM"
should type with my penis
he might do a better job than my fingers
I hope I haven't written too much here?

Sassy 11:11 AM
It's beautiful...
hope I can be worthy of all that!

Tim 11:11 AM
thank you
you are
that was heavy, want to change gears

Sassy 11:13 AM
Shift at will!
Are there litmus test questions you ask to gauge women?
deal breakers?

Tim 11:14 AM
While waiting for you to respond, I was looking at that tumblr. There is a lot of female masturbation movies. Have you ever done that for your partner?
sorry, missed that question of yours, lets explore that first

Sassy 11:14 AM
Let him watch me?

Tim 11:14 AM
yes

Sassy 11:16 AM
Men talk about it a lot but rarely want to do it
Kind of like jam in Alice in Wonderland
or is it tarts? Hmmmm
anyway.... there's jam every other day... but there's never jam...

Tim 11:17 AM
I've always wanted to watch, bucket list thing I guess.
My wife is very funny about that
I make a "special" jam :)
Would you

Sassy 11:17 AM
Let you watch me?

Tim 11:18 AM
When we are at that stage of comfort

Sassy 11:18 AM
Of course
I'm up for almost anything

Tim 11:18 AM
I always told my wife it was a way I could learn about what you really want

Sassy 11:19 AM
Hmmmm

Tim 11:19 AM
You asked about a "litmus" test?

Sassy 11:19 AM
I dunno... seems like a different thing to me. But worth a try

Tim 11:20 AM
you asked before I went down that avenue

Sassy 11:20 AM
Yes

Tim 11:20 AM
but you had passed my test in the first few emails

Sassy 11:20 AM
Like what?

Tim 11:22 AM
I want someone who needs more, not just out to cheat
someone who wants to share their life, fill a void, not use people and discard saying they notched another
have i passed yours

Sassy 11:22 AM
Yes
Though it is always tough to tell

Tim 11:22 AM
and what was yours

Sassy 11:23 AM
Men with a big kink won't admit it up front
I saw a very nice man twice and the third time he told me he was sub
I wanted to help him... but I can't

Tim 11:24 AM
Yes, I can see that.
That is a dynamic that both must be into.

Sassy 11:24 AM
There are a lot of things...
don't push to meet right away.
Don't ask for photos right away
Being curious about me beyond what sex positions I like

Tim 11:25 AM
I am also turned off by that photo right away thing, there is so much more you will miss that is so much more beautiful

Sassy 11:26 AM
I had to laugh (in horror) when one man said to me he broke up with his AM lady because she wanted to hear from him EVERY DAY!
*sigh
I know it takes times but gosh... I adore hearing from someone, even if it's just "Good morning!"

Tim 11:28 AM
Yes, the conversation has to be deeper than, "what’s your next free date" my heart jumps when I see your email, and yes, I love to email, even to say just "hi"

Sassy 11:31 AM
Thank goodness!

Tim 11:31 AM
what else is on your mind?

Sassy 11:32 AM
Do you know how to keep yourself safe from detection?

Tim 11:33 AM
yes
It will be something we discuss when we get to that point
I take each step as it goes
I will take any advice as it comes

Sassy 11:34 AM
Do you like your balls stroked? Squeezed

Tim 11:35 AM
YES, both
and suckled too
are you into balls

Sassy 11:36 AM
Oh yes
Paying attention there adds a lot, I find

Tim 11:37 AM
right now, even taling about it adds a lot!
"TALKING" wow I'm bad typing this morning

Sassy 11:37 AM
Excellent!

Tim 11:38 AM
how about you, do you like finger, tongue or both

Sassy 11:40 AM
Tease me…
make me wonder when you will ever touch my clit...
Long, slow licks...
some munching...
a finger or two may send me right over the edge

Tim 11:42 AM
Do you lick it when a man sucks on your inner and outer lips in the teasing phase

Sassy 11:43 AM
Yes please
nibbling...
pulling, pressing
Okay... breathing funny now!

Tim 11:43 AM
Do you like your clit sucked on or licked?

Sassy 11:44 AM
yes
both
you are making me tingle
and drip!

Tim 11:44 AM
After a man goes down, and kisses you, do you mind that he still has your taste on his lips
and I am glad I can make you drip from the computer! ;)

Sassy 11:45 AM
I do not mind
I like it
I know it's a thing

Tim 11:45 AM
good, that can be an awkward moment

Sassy 11:46 AM
Many women won't so I do!
Don't know if it's true right now, but there are a whole class of questions where I want to say "I am NOT your wife"

Tim 11:46 AM
there are some men who don't, and I can't figure that one out

Sassy 11:47 AM
I want the lights on,
I want to give you a bj,
I want to swallow, I
 want you to take your time...

Tim 11:47 AM
God. I am sooo sorry, but these last few were not that.

Sassy 11:47 AM
Usually the more things I find out their wife won't do, the more I want to do them!
It's okay either way

Tim 11:47 AM
oh, that is interesting

Sassy 11:48 AM
If they've been dealing with lights-off only for years, I want to fix that right away!

Tim 11:48 AM
me too

Sassy 11:48 AM
If they've been dealing with "I never get to see her naked" I want to lie naked in the middle of the bed with my legs open and let him STARE!

Tim 11:48 AM
But I wanted to know what you want, I want to please you and avoid that awkward moment

Sassy 11:49 AM
I got that too... and I so appreciate it!

Tim 11:49 AM
now you got me over the edge

Sassy 11:49 AM
I hope we won't be awkward...
I hope you can say Oh, wow.. not like that!

Tim 11:49 AM
And I want to do the same for you

Sassy 11:50 AM
Or "slower..."
"move to right a little"
It's not criticism... just... fine-tuning... being totally allowed to ask for what you want
And I will do the same

Tim 11:51 AM
that exploring each other should never go away

Sassy 11:51 AM
I also like different things on different days...
will try to say, "Can you pound me into next week today?"
or "take it slow... I need to chill out"

Tim 11:51 AM
And I am glad you can ask, so many women can’t

Sassy 11:52 AM
I had way too many years of lying there taking it... not going back there!

Tim 11:53 AM
I too have days where I want slow languid love and other I can't wait
I am so glad you got to that point so lets get to the next level, in our own time, step by step

Sassy 11:55 AM
First times can be weird... I try not to judge, just plan a second time soon
One of my best guys was a disaster the first time... couldn't stay hard...
the second time I helped him cum twice for the first time in 20 years

Tim 11:55 AM
that is a great attitude.
But the more we honestly talk, the more likely we will come into it with the right frame of mind

Sassy 11:55 AM
Absolutely!

Tim 11:55 AM
And that is the beauty of it all, the mind

Sassy 11:57 AM
I hope it's not too weird that I share my experiences
the demure lady is bashing me about the head for mentioning the cemetery!

Tim 11:57 AM
not at all, I seem to be asking to learn about you, and the past is relevant.
hey, don’t get mad at the demure lady
I hope I am giving you the opportunity at ask enough about me

Sassy 11:58 AM
I want to lock her in a closet

Tim 11:58 AM
does the demure lady want to branch out into other topics?

Sassy 11:58 AM
I feel like I am asking way too much!
Funny that you think I'm not

Tim 11:59 AM
Funny, I feel that I am asking too much too.
That shows that we do have a mutual respect going on

Sassy 12:00 PM
That part of me is so... eh. I want to escape the dull, responsible, good girl
But I am a whole person... just like the Trainer and John Henry!

Tim 12:01 PM
I know!
I just got up to let the dog out to chase some birds

Sassy 12:01 PM
What was the hottest night in your life?
So you're the one who let the dogs out!
Woof woof woof woof woof

Tim 12:03 PM
Wow, let me think about that one
that was a good joke
The first woman after my first wife passed away!
I think I came in every orifice that night

Sassy 12:04 PM
Oh my!
A little pent up were you?

Tim 12:04 PM
I went around the world so to speak
yes, and she was too

Sassy 12:04 PM
Lovely

Tim 12:04 PM
but it never got past that carnal animal stage

Sassy 12:04 PM
Who was she?

Tim 12:05 PM
but had fun while there
she was an old friend from college that I had lusted after

Sassy 12:05 PM
Oh... I adore reconnections

Tim 12:06 PM
I know. learned a lot from her

Sassy 12:07 PM
Do you pull out nights like that to enjoy again from the memories?

Tim 12:09 PM
yes
and i learn from them for future
also to help sleep on lonely nights  ;)

Sassy 12:10 PM
Sounds very healthy

Tim 12:13 PM
how is that demure lady
knock, knock.... still there

Sassy 12:13 PM
We are pondering
whether you can possibly be as fantastic as you seem!

Tim 12:14 PM
good, I think the awkward silence hit me

Sassy 12:14 PM
Sorry!

Tim 12:15 PM
I am what I have said, and I have pondered much on what you have said
you are so unique and special

Sassy 12:15 PM
I want you

Tim 12:15 PM
I pinch myself now and then
and I want you

Sassy 12:16 PM
that is incredibly alluring

Tim 12:16 PM
Thursday cannot cum quick enough for me

Sassy 12:17 PM
Do you have time to cheat?

Tim 12:17 PM
yes

Sassy 12:17 PM
I run into so many men who work too much and have younger children and really have not thought out when they could get away and the truth is they can't

Tim 12:19 PM
Yes, my youngest kids are in college, I have done it before and if there is a will there is a way
This might sound very corny, but I feel this is meant to be
But this is a partnership and we must always promise to be open and honest at all times

Sassy 12:20 PM
Yes. I feel like I can deal with almost anything if I know what's going on

Tim 12:20 PM
me too

Sassy 12:21 PM
I am used to being very open

Tim 12:21 PM
so are you ready for the next level?
if I am going 100 mph and you want 99mph, tell me

Sassy 12:21 PM
It was so tough for me to learn to keep my adventures to myself
Sure!

Tim 12:22 PM
now we can share our new adventures with each other

Sassy 12:24 PM
People used to ask me questions and I would answer
Now it's like "How was your weekend?"
Um...niece's birthday
DO NOT ADMIT HOT CHAT WITH NICE MAN!
Having you to talk with will help a lot

Tim 12:24 PM
well, if you are in open relationship, can’t you share a little
hey, who is that hot man

Sassy 12:24 PM
You are making me burn...

Tim 12:25 PM
yes, that fuse is burning in me too.
I am trying my hardest not to jump in my car

Sassy 12:26 PM
Oh we are so sensible
it sucks. :)

Tim 12:27 PM
So glad you have demure and I have the corporate trainer
But John Henry keeps grabbing the keys
I thank god he can’t drive without me

Sassy 12:28 PM
Hee hee
Do you collect anything?

Tim 12:32 PM
yes
I started collecting stamps with my grandpa and my son and i now share that hobby
It’s fun, don’t think it has anything more than bounding value, which make it priceless
do you

Sassy 12:33 PM
When you attend a figure skating event, they sell these little pins specific to the event... I have those to remind me of trips

Tim 12:33 PM
That is cool
do you miss the doing that with your sis

Sassy 12:35 PM
Most of the merchandise at events is stupid expensive but the pins are usually $5 or $7 so an economical way to get a souvenir
And when you wear them to competitions, other serious fans know you're not a random
In some ways... but we went to Worlds in Boston recently so I got a big slug of it
It's a brutal way to vacation though... sitting in a cold arena from 7 am to 11 pm

Tim 12:35 PM
if the pin brings back great memories, then it is worth a million

Sassy 12:35 PM
watching people fall down and smash their dreams

Tim 12:36 PM
how about the ones that had the magical win?

Sassy 12:36 PM
Those are priceless

Tim 12:37 PM
I had a dream smashing event in my life
would not trade it for anything in the world

Sassy 12:37 PM
You got back up
dreamed new dreams

Tim 12:38 PM
made me realize that doing it was something not many could have done, not many will ever experience

Sassy 12:38 PM
The first Nationals I went to there was a young woman who came in last in the figures competition. She sat in the stands bawling... because that was the last figures competition ever. She kept whispering... I will never get a chance to do better.
I hope she found other ways.
It made you special

Tim 12:39 PM
but the chance to dream is magic, and you must be able to say, "being there was the dream”
i ran cross country as a kid and I just wanted to make senior nationals

Sassy 12:39 PM
It reminds me of the broken Japanese pots that are mended with gold and even stronger and more beautiful

Tim 12:40 PM
I qualified my jr year in high school and was 4 seconds off the world record

Sassy 12:40 PM
Wow!

Tim 12:41 PM
but when I got there, 50 other people were just 4 seconds away

Sassy 12:42 PM
That is quite something though, to be part of the top eschelon
and get to go
What was your race?

Tim 12:43 PM
I ran my heart out, was winning for 2/3rds of the way, then it was like a piano hit me. The winner set the world record and I ended up 50th
but for one brief second, I was the man

Sassy 12:44 PM
Are there photos of runner you?

Tim 12:45 PM
Dad just sat there with me for a long time silent, and finally said, “no one will ever have that story.”
he was right and I will never trade that.
Yes, I have a sexy one of me bald in tiny shorts, I’ll bring it Thursday

Sassy 12:45 PM
Wow!

Tim 12:45 PM
wish I still fit into those shorts

Sassy 12:45 PM
Nah

Tim 12:46 PM
maybe we can try together
it would be a sexy failure

Sassy 12:46 PM
try both fitting in the shorts?

Tim 12:46 PM
no, you put it on me

Sassy 12:47 PM
Aha
I can put it on your head?

Tim 12:47 PM
I'll settle for both of us fitting under the blankets

Sassy 12:47 PM
I won't settle until you fit inside me. :)

Tim 12:47 PM
you can put yourself on my head

Sassy 12:48 PM
Which one?

Tim 12:49 PM
BOTH
talking about shorts, do you like to wear lingerie

Sassy 12:49 PM
I don't own any

Tim 12:50 PM
may I ask why
not that I expect, but you seem so Sassy

Sassy 12:51 PM
Some combination of lack of money, tough to find any my size, and not much occasion for it
But that could all change

Tim 12:51 PM
yeah, they come off so quickly

Sassy 12:52 PM
My friends are always trying to get me into a corset

Tim 12:52 PM
my angle here, was what makes you feel sexy
a corset sounds good

Sassy 12:53 PM
I have a great photo I'll show you sometime four of my friends, all in corsets.  BOOBAGE!

Tim 12:53 PM
Love boobage

Sassy 12:53 PM
Have you ever worn a kilt?

Tim 12:54 PM
no, but I would only with no underwear

Sassy 12:54 PM
They make these great utili-kilts
very sexy

Tim 12:54 PM
never saw one

Sassy 12:54 PM
Most of our guys where biker shorts too

Tim 12:55 PM
otherwise I would wear it Thursday
but with you I'd rather be commando

Sassy 12:56 PM

Mmmm... makes my fingers twitch

Tim 12:57 PM
in reality, i want you to feel sexy, unjudged

Sassy 12:57 PM
unbutton a button...slide down a zipper...slip a finger in there and press...

Tim 12:59 PM
still looking at the link
couldn't you just reach up from under
buttons seem like they wouldn’t be needed
but i won’t complain

Sassy 1:00 PM
You will make it tough for me to behave

Tim 1:01 PM
hey, it takes two to tango
and I have to hide the keys from John Henry

Sassy 1:02 PM
Have you sat on a woman's face?

Tim 1:02 PM
yes,
have you sat on a man's face?

Sassy 1:02 PM
suddenly had this vision of you above me, holding on to a headboard, buried deep in my throat

Tim 1:04 PM
that is an image I crave
sometime a blow job is what i want, sometime when the beast is unleached i love that

Sassy 1:05 PM
mmmm

Tim 1:06 PM
i have a vision of you standing next to the bed, me on my back, head hanging over and...
that position is on that crazy animated positions site

Sassy 1:06 PM


Tim 1:07 PM
that is such a turn on
i could play with your breasts

Sassy 1:08 PM
Yeah... so many of those have both the man and woman's hands idle
I'm like NO!
touch her! touch him!

This one is mis-named
It's mostly blow jobs. But that's okay.

Tim 1:10 PM
idle hands are the puritans boredom,
or is that the devils workshop
: )

Sassy 1:10 PM
Have you heard of the porn star Camille Crimson?

Tim 1:11 PM
no
But I'm sure I will now

Sassy 1:11 PM
Here's my favorite blow job video from her. It's under 5 minutes.  She is such an artist! 

https://www.redtube.com/41790

Tim 1:12 PM
ok
god we have so long until thursday

Sassy 1:15 PM




A lick you might like.

Tim 1:15 PM
is that liki[

Sassy 1:15 PM
Are you typing one-handed?

Tim 1:15 PM
is that link the same as the one u emailed

Sassy 1:15 PM
no

Tim 1:15 PM
yup

Sassy 1:16 PM
ha ha ha
I'm so glad

Tim 1:17 PM
I will watch the video later.
I rather talk to you while I have you

Sassy 1:17 PM
Yes... good to watch when you are alone
and have both hands. :)

Tim 1:17 PM
you are so evil

Sassy 1:18 PM
You betcha
Sassy is full thrall today!

Tim 1:18 PM
you never said if you like to sit on a man’s face
glad to have sassy

Sassy 1:18 PM
Oh... I tried to think if I've ever done it
Not for a long time, if I did

Tim 1:19 PM
put it on the list

Sassy 1:19 PM
I have been on my hands and knees with the guy under me licking upwards

Tim 1:19 PM
but when a woman orgasms that way, it is such an erotic moment
like that too.

Sassy 1:20 PM
all of my orgasms are erotic moments!

Tim 1:20 PM
have you been on your hands and knees and he approaches from behind

Sassy 1:20 PM
Oh yeah...

Tim 1:21 PM
i can get my tongue so deep

Sassy 1:21 PM
adore hands on my ass
squeezing, pulling, pushing

Tim 1:21 PM
yes all orgasms are erotic, but when you are on top, it envelops my face

Sassy 1:22 PM
Mmmm
that caused a big twinge!

Tim 1:22 PM
good

Sassy 1:22 PM
Dear John Henry, cum here please!

Tim 1:22 PM
are you typing one handed yet

Sassy 1:22 PM
Ha ha... no.
Hubby is sitting 4 feet from me

Tim 1:23 PM
He’s trying to get the keys
john henry, not hubby

Sassy 1:23 PM
*giggle

Tim 1:23 PM
wish we got in our cars

Sassy 1:24 PM
Too cold at the cemetery today

Tim 1:25 PM
but there was that one woman on skincast masturbating in the snow

Sassy 1:25 PM
Wacky

Tim 1:26 PM
The Trainer agrees

Sassy 1:26 PM
Should I let you go? eat? do things?

Tim 1:27 PM
unless you to i have an hour
but don’t make me keep you on

Sassy 1:28 PM


Tim 1:28 PM
i am just addicted to talking to you
that was a picture

Sassy 1:28 PM
I just looked at the clock for the first time... couldn't believe we've kept going so long!

Tim 1:31 PM
me too. I thought it would be noon
Only big thing for me is to finish some work and working out details for thursday
Is there anything I can do to make sure you feel safe
I recognize that this is more dangerous for you

Sassy 1:32 PM
The current plan is good

Tim 1:33 PM
do you need to go. no guilt
do you know where you would like to meet

Sassy 1:33 PM
I can list off restaurants if you like

Tim 1:34 PM
send them in an email

Sassy 1:34 PM
Okay

Tim 1:34 PM
then i can find them at my leisure
you still good to chat

Sassy 1:34 PM
Yes

Tim 1:35 PM
I will understand
what else is on that beautiful mind of yours

Sassy 1:35 PM
Do you go to the movies?

Tim 1:38 PM
yes. tonight we are going to manchester on the sea
we alternate movie picks
I choose hacksaw ridge last time
you still there?

Sassy 1:39 PM
Yes
What did she pick?

Tim 1:39 PM
manchester one for tonight

Sassy 1:39 PM
Have you seen Rogue One?

Tim 1:41 PM
not yet, but i teach nerds and they kind of told me everything
i think that’s next
how about you

Sassy 1:41 PM
We had to go the first weekend...
Hubby would've preferred first day but I couldn't find seats
He also picked Doctor Strange

Tim 1:42 PM
It’s great when you share movie likes
we have a mutual likes in theater

Sassy 1:42 PM
I couldn't follow it but drooled over Benedict Cumberbatch

Tim 1:42 PM
That’s what the secretaries at work said

Sassy 1:43 PM
I saw Hidden Figures with Sis last weekend
I seem to be the only person who had problems with it

Tim 1:43 PM
how was it. i want that to be my next

Sassy 1:44 PM
It definitely has its moments and it's important to know about those women
Have you seen the movie A Room With A View?

Tim 1:45 PM
i know, especially with our new Groper in Chief
no did not see that

Sassy 1:45 PM
It's my all-time favorite

Tim 1:45 PM
You said you like to travel

Sassy 1:45 PM
Yes!

Tim 1:46 PM
can I unfold, or peal back a layer of mystery

Sassy 1:46 PM
Sure!

Tim 1:47 PM
I live to travel, used to go to many countries

Sassy 1:47 PM
Where?
Awesome!

Tim 1:49 PM
I have been to all western European countries, Scandinavia, Egypt -
but terrorism is killing me and I had to mostly stop

Sassy 1:50 PM
Wow

Tim 1:50 PM
I don't think I told you why I left teaching first time, did I

Sassy 1:50 PM
no

Tim 1:54 PM
It is a sad story and you could google it, but since we are meeting, I feel comfortable sharing
it comes from that life event question I asked earlier
but it is something that has made me the person I now want to be

[story redacted.  Sorry – it’s too specific to risk]

Tim 1:58 PM
so I have made an effort in my life to always just remember to realize what I have, realize that just one smile, nice thing can be the difference each day
I had my first affair in the wake of that

Sassy 1:59 PM
Best way to affirm life

Tim 1:59 PM
sorry if I became too heavy, but it is part of me

Sassy 1:59 PM
Thank you very much for sharing that...
I like to understand those moments ...
can make other things you do make more sense

Tim 2:01 PM
i never dealt with PTSD at first, and found I just forgot how to live.  A lot of stuff triggered me

Sassy 2:01 PM
I'm amazed you could go on

Tim 2:02 PM
I had to! I can't let that win. That's why I have such trouble with Trump

Sassy 2:02 PM
I hear that!

Tim 2:04 PM
what a jerk
sorry, but it is what it is
I would like to lie in your arms and tell you what it is like, safe and hugged
and be there for you

Sassy 2:04 PM
We will...

Tim 2:04 PM
that is why I find you so special

Sassy 2:05 PM
I can so easily see us...
my head on your shoulder... sharing all those stories
Sassy will be drawing circles around your nipples while the demure lady listens. :)

Tim 2:06 PM
I don’t know why, but as we talked, I knew you are a person who would understand
that is that special thing I feel
you asked me once, and I didn't want to tell, but I did.

Sassy 2:07 PM
I asked you what?

Tim 2:07 PM
never had this on AM
why I thought you were extra special

Sassy 2:08 PM
ah
I am honored to be let in to the inner circle

Tim 2:08 PM
that is half the reason I so want to meet you and talk, the other....
y'all have to ask John Henry

Sassy 2:08 PM
He wants to get wet

Tim 2:08 PM
Can we both be inner circle members?

Sassy 2:09 PM
yes. we make our own circle

Tim 2:09 PM
yes, he wants to get very wet

Sassy 2:09 PM
and warm

Tim 2:09 PM
yup

Sassy 2:09 PM
and be squeezed
and pulled

Tim 2:09 PM
how did you know?
Does he email when I am sleeping?

Sassy 2:10 PM
Now that would be something....
Hee hee

Tim 2:11 PM
Can we try to always keep that communication piece?

Sassy 2:11 PM
It's essential

Tim 2:11 PM
Corporate trainer with demure working girl and John Henry with the brassy broad

Sassy 2:12 PM
It's how you will get the best of me

Tim 2:12 PM
Let’s go to a happier topic

Sassy 2:12 PM
that and Sassy bjs
CHEESECAKE!

Tim 2:13 PM
only if I get to go down on you

Sassy 2:13 PM
Plain? With strawberries? Turtle?

Tim 2:13 PM
put strawberries, since I get my cherry later

Sassy 2:14 PM
I lost my cherry awhile back
but you can have the box it came in. : P

Tim 2:14 PM
That’s a deal!

Sassy 2:15 PM
Heard that before?
I like it.

Tim 2:20 PM
:b
so want to talk brassy or demure
or do you have to get ready for tonight
you still around

Sassy 2:20 PM
Hmmm
Pondering

Tim 2:20 PM
pondering is good

Sassy 2:21 PM
I think of stories but then decide to tell that one in person

Tim 2:21 PM
that is fine

Sassy 2:21 PM
Who is your favorite classical writer?

Tim 2:23 PM
oh, you asked that because I studied Classics?
That perve Catullus
his poems are about his intellectual love and his intimate love of her body
He is so torn, tortured

Sassy 2:24 PM
I told my friend the Classics major I was talking to a guy who had studied Classics.
She told me to ask, that she can tell a lot by who you pick. :)

Tim 2:24 PM
Then tell her Vergil

Sassy 2:24 PM
She read a Greek poem at my wedding
Ha ha

Tim 2:26 PM
that is so cool. I’ve read at weddings… such an honor
you can throw in St Augustan and throw her into confusion
I'd love to hear you read to me some time, your voice is so beautiful

Sassy 2:27 PM
Glad to.
She read Sappho
Our wedding was a great showcase of our friends

Tim 2:27 PM
that is so cool
Sassy 2:31 PM
I didn't marry until I was 37

Tim 2:32 PM
I married young but did not start kids for awhile
HOW did no one catch you earlier!

Sassy 2:33 PM
I worked 70 hrs a week at a law firm, had no life

Tim 2:33 PM
neither did those lawyers

Sassy 2:34 PM
and many men don't look twice at the big tall gal,
especially when they find out how smart she is
The internet had to come along to get me a man!

Tim 2:34 PM
yes, men are threatened by smart women, but why i can’t fathom

Sassy 2:34 PM
I am not militant about it

Tim 2:35 PM
Did I say I am turned on by big tall gals

Sassy 2:35 PM
My sisters are the deep, intellectual, philopshy debater types

Tim 2:35 PM
and you are too

Sassy 2:35 PM
Not really... I am the practical, administrative one

Tim 2:36 PM
but you wax so poetic on these chats

Sassy 2:36 PM
I'm so glad you can deal with a big tall gal!

Tim 2:37 PM
deal is not the word I would use.
It would be cherish

Sassy 2:37 PM
Mmmm
Worship? :)

Tim 2:39 PM
but it’s the inside I look to first, the rest is pure fantasy
yes, I think the word worship will come out of my lips at some point
I can’t wait to explore your curves
do you like a sensual massage?

Sassy 2:40 PM
Oh yes
I am so starved for touch
I will luxuriate in everything from a pat on the arm to the deepest sex

Tim 2:40 PM
I will give you one under one condition

Sassy 2:41 PM
I am not wearing a bunny tale ass plug

Tim 2:42 PM
no - that it comes with a very happy ending!
but now that you raised the stakes

Sassy 2:42 PM
ha ha
Did you giggle?

Tim 2:43 PM
I would never have you humiliate yourself

Sassy 2:43 PM
Oh they look great on some women!
Just not my thing!

Tim 2:43 PM
but yes it made me giggle

Sassy 2:43 PM
Good

Tim 2:43 PM
have you ever tried a butt plug?

Sassy 2:44 PM
I used to have a little one, about the size of half my pinkie
it was fun

Tim 2:44 PM
what happened to it

Sassy 2:44 PM
Of course, it broke pretty quickly

Tim 2:44 PM
over use!

Sassy 2:44 PM
So I bought another one
and I didn't pay attention

Tim 2:44 PM
have you tried anal sex

Sassy 2:45 PM
So I have this plug the size of my fist sitting at the back of my desk drawer
I did it long ago
Got ripped to shreds

Tim 2:45 PM
try with a man

Sassy 2:45 PM
I am looking for someone I trust
who wants to ... with lots of lube

Tim 2:46 PM
there is a lot that goes into the whole process
doesn’t always happen first time

Sassy 2:46 PM
The day after my first colonoscopy I was dying to have someone do it
You do it?

Tim 2:46 PM
that would be the time

Sassy 2:47 PM
:)

Tim 2:47 PM
yes I have, but she must enjoy to make it work

Sassy 2:48 PM
I've had men press fingers or tongues in there

Tim 2:48 PM
usually spooning is the best way to start after all the forepay

Sassy 2:48 PM
mmmm

Tim 2:48 PM
I love to tongue too

Sassy 2:49 PM
We are going to have so much fun!

Tim 2:49 PM
also there’s that area
between the pussy and ass that is fun to include

Sassy 2:49 PM
taint!

Tim 2:50 PM
include in oral
you got it, rimming

Sassy 2:50 PM
Give JH the keys. :)

Tim 2:51 PM
now there is not enough time for John Henry to drive out!

Sassy 2:51 PM
I am tempted to write a syllabus

Tim 2:51 PM
boy is he hot and bothered

Sassy 2:51 PM
Month 1... kissing, touching, massage, oral, doggy style
Month 2 - toys!

Tim 2:51 PM
where would you start

Sassy 2:52 PM
Month 3 - anal
Month 4 - outside

Tim 2:52 PM
yes warm weather

Sassy 2:53 PM
I should probably go soon
:(

Tim 2:53 PM
It is now pushing three!
do you want to take a breather
and get ready for your night
and I can finish my work
so I am free for thursday

I had the best time
three words
WOW

Sassy 2:54 PM
5 hours! This may be a record
Wow... mmmm
I concur on that

Tim 2:54 PM
I'M HOOKED
I WANT MORE

Sassy 2:55 PM
Hooray!
Prosaic but... I DO TOO!

Tim 2:55 PM
not sure how time will play out for chat,
but I do want to write you an email at the least

Sassy 2:55 PM
Okay. I will stay tuned.

Tim 2:55 PM
and let’s get our plans tuned

Sassy 2:56 PM
okay. I will try to send a list of ideas when I get home

Tim 2:56 PM
I just don't want to meet you, I need to!
you are not home?

Sassy 2:56 PM
I mean after dinner tonight

Tim 2:56 PM
are your cotton panties a little damp

Sassy 2:57 PM
Is there pre-cum?

Tim 2:57 PM
YUP

Sassy 2:57 PM
a bulge?

Tim 2:57 PM
big

Sassy 2:57 PM
I feel quite flushed and drippy

Tim 2:58 PM
till we chat again

Sassy 2:58 PM
Mwah!

Tim 2:58 PM
hugs and blown kisses with tongue

Sassy 2:58 PM
mmmm
going now!

Tim 2:58 PM
and share with your vjayja


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