Edge of the bed

March 30, 2017 Thursday

10:41PM Phil
[photo of his chest and smiling face right out of the shower]
10:42 PM Sassy
Hiya hot stuff!
10:42 PM Phil
Nite kiddo
10:42 PM Sassy
Mwah!
10:42 PM Phil
XXoo
1:09AM Sassy
Oh yes

[tumblr black and white photo of a woman’s head over the edge of the bed with a man’s hand feeding her his cock and his other hand gently massaging on her throat]

Sexy Link Fest

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March 12, 2017 Sunday
From: TimmyTim
To: Sassy
Date: Sun Mar 12, 2017 at 7:18 PM
Subject: Tonight
Sassy,
With the time change, I am behind a bit, can we shoot for 9:00?
Hugs with anticipation of things to cum!
Take care,
T
Sent from Yahoo Mail for iPhone
=====
From: Sassy 
To: TimmyTim
Date: Sun Mar 12, 2017 7:25 PM 
Re: Tonight 
Hiya T!  I was just writing to say I’m running late!  Not sure when I’ll get back – I will email.  Just starting dinner out, so guessing 9 pm or a little later.  Can’t wait to talk!
-S

Sent from Yahoo Mail on Android
=====
From: TimmyTim

To: Sassy
Date: Sun Mar 12, 2017 at 9:07 PM
Re: Tonight
Sassy,
Call at will until 9:30, then text just to be safe. The time change just made things a little crazy today! Can’t wait to talk!!
T
Sent from Yahoo Mail for iPhone
=====
From: TimmyTim

To: Sassy
Date: Sun Mar 12, 2017 at 9:11 PM
Re: Tonight
Sassy,
I meant email me, not text!

Sent from Yahoo Mail for iPhone
=====
From: Sassy 
To: TimmyTim
Date: Sun Mar 12, 2017 at 9:11 PM
Re: Tonight 
I’m home, getting ready to call!
Sent from Yahoo Mail on Android
=====
We talked for nearly an hour!  He is so easy to talk with, so knowledgeable, so sexy!  When we finished, I sent him several links we had discussed. 
=====
From: Sassy 
To: TimmyTim
Date: Sun Mar 12, 2017 at 10:31 PM
Subject: A day in Pompeii
Here’s an 9-minute computer animation of the last day in Pompeii. I always thought it was lava, but it was ash!!
A Day in Pompeii
Watch the Destruction of Pompeii by Mount Vesuvius, Re-Created with Computer Animation (79 AD) 
www.zerooneanimation.com

[youtube=https://www.youtube.com/watch?v=dY_3ggKg0Bc&w=320&h=266]

=====
From: Sassy 
To: TimmyTim
Date: Sun Mar 12, 2017 at 10:43 PM
Subject: Kitchen adventures

kitchen fucking gifs
=====
From: Sassy 
To: TimmyTim
Date: Sun Mar 12, 2017 at 11:00 PM
Subject: Office dreams
Office Dreams


Tits and cum

March 2, 2017 Thursday

7:47 PM Phil
Hope your week has been good. Been so busy. Watching what I eat and drink, back in the gym. 14lbs down and enjoying the feeling of sore muscles.
7:48 PM Sassy
Hiya!  Been wacky busy at work too!  Yay for your new weight!  Sore muscles are no good… moderation!  

Wanna see a sexy pic?
7:50 PM Phil
No, sore muscles are very good. I’m going slow but running upstairs again, knocking out sit-ups. I remember my age but feel good. 

Hell yes! Always!
7:52 PM Sassy


[photo of my left breast]
7:52 PM Phil
Well damn! I love it! <3
Beautiful 
Sassy


[tumblr photo of kneeling woman licking a man’s cock while others dance around them]
7:55 PM Phil
Mmmm
I like!
7:56 PM Sassy
Just a little snippet to get you thinking in a certain direction. ; ) 
7:57 PM Phil
Made my muscle leap to attention!
Hope you are giving your sweet pussy a little attention
8:02 PM Sassy
Hubby is out so I am!
8:03 PM Phil
So someone else is giving you attention? Good for you : ) 
Enjoy!
Appreciate the pic always
8:05 PM Sassy
No… just me and my imagination.
I do have a meet tomorrow the Northerner!
8:05 PM Phil
That’s pretty good too!
Ah, excellent
8:06 PM Sassy
Not sure what’s going on… heard from him and 3 other guys in the past two days that I have not heard from in ages!  One reappeared after 2.5 years!
8:06 PM Phil
Wow!
8:06 PM Sassy
No one beats your record of 35 years though.  : ) 
8:06 PM Phil
Ha! It was worth the wait
8:07 PM Sassy
Awww… you are such a sweet man.
8:08 PM Phil
Well it’s true.
It’s amazing when there’s a connection of the heart <3
Our dinner at Legal was full of romance as were our evenings in DC
8:12 PM Sassy
It stuns me sometimes how much fun we’ve had, and how we’ve gotten each other through some awful times.
8:13 PM Phil
Pretty cool
8:15 PM Sassy
And you inspired me to learn all sorts of sexy stuff!
And eat oysters!
8:16 PM Phil
Ah oysters
Yay for sexy stuff!
Makes life much more fun
Had amazing sweet steamed clams for supper
8:24 PM Sassy
I breezed through McDonald’s
Wish you were here… I’d eat you!
8:28 PM Phil
Mmmm, that would be fun, love that hot mouth
8:29 PM Phil


[tumblr photo of a kneeling woman with a man’s cock between her breasts]
8:30 PM Sassy
Your meat is my favorite!
8:30 PM Phil
My meat cums with special sauce
8:30 PM Sassy
Oh my… Tits and cum!  Great combo!
8:30 PM Phil
Absolutely
That’s a fun way to cum
Got excited looking at your tits
I’ve had those in my mouth
8:35 PM Sassy
I am rather wet thanks to you
8:36 PM Phil
Lovely, much easier for my throbbing cock to slide in that way
Nothing better than hot wet pussy
Even better with a hot load of cum
8:38 PM Sassy
Mmm hmmm
8:39 PM Phil
I loved watching you quiver as I shot deep inside you
I assume it was as good for you as it was me
8:42 PM Sassy
Probably better for me since it had been 10 years!
8:42 PM Phil
Oh wow! Happy it was me
So you didn’t have guys dropping to their knees yanking your pants down and shoving their tongue inside you on a regular basis?
I know you weren’t expecting that
8:46 PM Sassy
I was expecting nothing
Thought we’d have dinner and you’d go away
8:46 PM Phil
Yeah well, no. I had you for dinner  ; P
Thought we had a great time
8:48 PM Sassy
Fantastic!
8:49 PM Phil
I smile every time I walk past any of those places
Off to the shower for me. Early morning. 
Play and think of me and send me a sexy pic
8:51 PM Sassy
And get a little hard?
Night dear man!
8:52 PM Phil
Oh yeah, that always happens xxoo
Nite babe
Sassy
; )

Lady and the Tramp

February 11, 2017 Saturday

6:35 AM Sassy
It’s snowing again. And forecast to snow tomorrow. And Monday. Hmmm… It’s really winter. My decision to live in a condo with underground parking seems like the best one I ever made!

[photo from my balcony window of the snow coming down before sunrise]
7:30 AM Sassy
Good morning kid. Mwah!

7:32 AM Sassy

GIPHY.com Disney Gif
8:05 AM Phil

Ah Lady and the Tramp. Good one!
Good morning, starting the day with a work out

11:18 AM Sassy
I’d like to give you a work out!

6:21 PM Sassy
Chicken noodle soup I made for supper with the bones from a rotisserie chicken!  Perfect supper for a winter night. 

Winnie and Eeyore

January 30, 2017 Monday

From: TimmyTim
To: Sassy
Date: Mon Jan 30, 2017 at 6:10 AM
Subject: It’s Monday
Sassy,
It’s Monday! I know you hate Mondays, but think how much better this Monday is from last because we have met! and without Monday, we would never have Friday! So pick your head up, go to work and this could even be a better week!
John Henry and I did not need tumblr, just memories of our Friday! What tumblr sites did you visit? Can’t wait til we meet again!
Hugs, naked with kisses!

Sent from Yahoo Mail for iPhone
=====
From: Sassy
To: TimmyTim
Date: Mon Jan 30, 2017 at 8:17 AM
Re: It’s Monday
Good morning hot stuff!
You are so cheerful! Thanks for sending it my way! 
I found an anecdote – put in a couple of hours work last night so I’m ahead of the curve.  We’ll see if it matters.  
My tumblr journey started with skincast then moved over to sheersgreat for inspiration.  It mostly came from you, though.   

http://sheersgreat.tumblr.com/
Into the fray!  Onward and upward!  Have a marvelous Monday sweet one.
-S
Sent from Yahoo Mail on Android
=====
From: Sassy
To: TimmyTim
Date: Mon Jan 30, 2017 at 6:53 PM 
Re: It’s Monday
Hiya T!  
How was your Monday?  Hope it was better than mine.  Boss pounced on me at 9:05 am wanting three more things, when I already had no idea how I’d get done what I needed to do.  No lunch today!  But I got through it, smiling whenever I had a break, thinking of the twinkle in your eye and your hands and your mouth and John Henry!  So so good! I want to do all that again, and also do other things.  How will we choose?!  I don’t expect to have that long every time.  
I’ve ordered Thai food delivered for dinner.  I adore their shrimp tempura!   
I may have to sign you up for the “A.Word.Day” emails.  They’re doing Yiddish words this week, and one of my favorites – verklempt – showed up today!  
Hugs without hitting a ticklish spot! 
-S
=====
From: TimmyTim
To: Sassy
Date: Monday, January 30, 2017 7:45 PM
Subject: Re: It’s Monday
Sassy,
Had a tough day too! My department head is a tool (can women be tools? Don’t know about the nature of women since Trump’s election), and she stormed out of a meeting so they want me to patch that up with the client. Talk about a rock and a hard place (no, not that type of hard!). I think I smoothed that over, but now I have a pile of other work.  So I may be a little quieter until  Thursday when I’ll be back to my wordy, poetry filled emails! I just feel swamped now! We need a night to chat!
Had Chinese food tonight! That stuff is the best. But I’m now hungry again!
I have been thinking of Friday a lot, with smiles and an erection! You said session two will be even better, don’t know how that could be since you are awesome!😜
So tomorrow should be that much easier if today was that sucky! (Is sucky even a real word?) did you tell your classics friend say anything about me? Don’t know why I care except that she knows Latin! Silly I guess! 
Can’t wait to go down on you again! You are more tasty than a large helping of General Gao! I got some good ideas for the second meeting. What plans would you have? (And don’t leave out any details)
Hope you can write one more time before you go to bed! Especially if you have a racy story! Or pictures!
Hugs with a lot of breast play!
Take care,
“Tim”

Sent from Yahoo Mail for iPhone
=====
From: Sassy
To: TimmyTim
Date: Mon Jan 30, 2017 at 9:20 PM
Re: It’s Monday
Hiya Tim! 
So sorry to hear your day had its strange woman boss thing too!  How bizarre… hope tomorrow is better for both of us! 
I told my friend that I try not to expect much so I don’t get disappointed, but you seem like a keeper!  I haven’t said that before.  
I have very little brain this evening… feel like Winnie the Pooh for sure.  I am not up to spinning a big sexy story.  Maybe tomorrow!  I definitely want there to be one.  I definitely want to explore your back side next time… from your shoulders to the back of your knees!  
I scrolled through my photos looking for something to send.  Here’s the face photo I would’ve sent if you’d asked for one.  Hope it would not have sent you running screaming!  It was taken in 2012. My hair was still growing out but otherwise I think I look the same. 
Sweet sexy dreams!  
-S
=====
From: TimmyTim
To: Sassy
Date: Mon Jan 30, 2017 at 9:36 PM
Re: It’s Monday
Sassy,
You might be Winnie, but I got some Eeyore goin’ on here! That picture would not have me running away, only to!
Have a good night sleep, think we could both use a good night. Remember that today was only one day, but tomorrows are limitless. So we will have a great day tomorrow!
Keep smiling and the sun will come up and out for us! It’s going to be a great day, otherwise the win!
Sleep sound,
Tim
Sent from Yahoo Mail for iPhone


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


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
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!
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


Munch on me

January 12, 2017 Thursday

7:48 AM Sassy
Good morning kid!  Happy Mom Visit day!

1:49 PM Sassy
Lunch with Sis at a new restaurant – The Hourly Oyster House in Harvard Square Cambridge

Raw bar sampler with oysters and lobster tail
lam chowder with sourdough croutons
Sis had a Banker’s lunch – clam chowder 
and grilled cheese with bacon and tomato on rye
Lobster spaghetti
Berry crumble for dessert


7:04 PM Sassy
It’s oven night! Scalloped potatoes with ham and green bean casserole!

8:58 PM Phil
Hey there! Mom is here!

8:59 PM Sassy
Yay!  You doing fun stuff with her?

9:00 PM Phil
I worked this afternoon but maybe tomorrow

9:01 PM Sassy
I’m playing  : )
9:20 PM Phil
Mmmm nice.
That’s a wonderful image. Lick your fingers for me

9:26 PM Sassy
Oh!  You are so hot.  Makes me wet!

9:30 PM Phil
Well, I’d lick them myself but I’m not there. 

Of course if I was there I could have my tongue buried in your pussy while you buzzed your clit with your favorite toy

9:30 PM Sassy
Mmm…you are in fine form.  I like the way you think!

9:34 PM Phil
Mmmm, I’m glad.  I like your sweet pussy. Wasn’t that long ago, I was licking your sweet juices from my fingers at the airport

I like being naked in your bed better, watching you suck my cock

9:35 PM Sassy
Let’s do that again.

9:35 PM Phil
That was fun
And very hot, took you to dinner still flushed, very sexy

9:37 PM Sassy
Thought of you at lunch today… Oysters and lobster

9:38 PM Phil
Oh yum!

9:38 PM Sassy
So fresh and tasty!  Like you!  : )

9:39 PM Phil
You are pretty tasty yourself  : P

9:40 PM Sassy
Munch on me.

9:43 PM Phil
Mmmm, be happy to eat you from your clit to deep inside, get your juices flowing and work my tongue lower to catch what runs down over your ass and then back up. Back and forth probing both places

9:45 PM Sassy
Mmmm…
Would squirm and shriek!

9:45 PM Phil
Hopefully in pleasure

9:45 PM Sassy
The best!

9:46 PM Phil
Makes my cock hard thinking about it

9:46 PM Sassy
I need chocolate
I like your cock.

9:46 PM Phil
You could drizzle a little chocolate on my cock

9:47 PM Sassy
Ooh!
Might put some on my breast
Need help getting it off
9:48 PM Phil
Mmmmm, be happy to lick and suck it off of your nipples
As my fingers occupy themselves on your clit

9:49 PM Sassy
Mmm mmmm mmm
I need to lick you…for a long time

9:51 PM Phil
Lick, suck, poke, probe, take me

9:52 PM Sassy
You betcha
You know I can

9:53 PM Phil
Replace my hand on my cock with…..

9:54 PM Sassy
Whatever you want

9:55 PM Phil
Hand first, then mouth, breast, pussy

9:57 PM Sassy
Perfect

9:58 PM Phil
You could end up with a mouth or pussy full of cum that way

9:59 PM Sassy
You could get squirted on!

10:00 PM Phil
Ooooh, damn baby, squirt on me, shoot that delightful juice in my mouth, I love it!
Let’s get slippery and sticky

10:01 PM Sassy
Yes please
Slip, slide, mess

10:02 PM Phil
That’s the best, entire room filled with the smell of cum.
Maybe slide a couple of those slippery fingers up my ass.  Mmmm, damn

10:05 PM Sassy
Loan you my big black butt plug?
10:06 PM Phil
You have a black butt plug?  I love it! 
Slide that baby into my ass, mmm that’s fucking hot

10:07 PM Sassy
Never opened it…sits in the draw waiting for the right moment
Or right man

10:07 PM Phil
Mmmm, I’ll give it a try

10:08 PM Sassy
You are made of awesome!
And fun too

Sassy
[photo of woman in a cafe crawling across the table to kiss the guy]

10:10 PM Phil
I can imagine you lubing my ass, getting me ready, fingers sliding the lube in, my cock jerking as you do, so hard

10:10 PM Sassy
Talking dirty

10:11 PM Phil
Fuck me Sass, slide that fat plug up my ass

10:12 PMSassy
Let it buzz

10:13 PM Phil
Oh hell yeah, grab my cock baby, stroke it, feel it throb

10:14 PM Sassy
I definitely want to

10:14 PM Phil
Throbbing now

10:15 PM Sassy
Watching your face

Can you play?

10:16 PM Phil
Eyes Rolled back, breathing hard

[photo looking down at his hard cock and balls sticking out of his shorts]

Like that?

10:17 PM Sassy
Oh yeah…

10:17 PM Phil
My cock has been in my hand the entire time

[photo of his cock in his hand]

10:18 PM Sassy
So happy to know that

10:17 PM Phil
Licking pre cum off my fingers

10:20 PM Sassy
Damn…so so hot!

10:21 PM Phil
Hope it aids your play

Let me shove that inside you and fuck you hard and deep, balls slapping against your ass

Oh yeah, hot tight pussy, um babe, feels so good

10:23 PM Sassy

[photo of my right breast with my hand holding it]

10:23 PM Phil
Ohhh there we go, like to rub that drop over that nipple and lick it off

10:24 PM Sassy
Yum

10:25 PM Phil
Wanna slide my cock in your hot mouth, suck me, oh yeah, suck that cock Sass

10:26 PM Sassy
Suck it deep
Milk it
Hot, wet, tight around you

10:26 PM Phil
Damn baby, feels so good

10:28 PM Sassy
Swallow around you

10:29 PM Phil
Take it back in your throat. Feels so good, fucking your hot mouth

10:32 PM Sassy

[photo of my new toy in my hand – the Lelo Gigi 2]

10:34 PM Phil
Play

[15 second video of him pumping his cock]

10:34 PM Sassy
Mmm
Want
You
Inside

10:36 PMPhil
Yeah babe pounding your pussy, hard deep strokes followed by slow easy ones

Like that toy. Would love to watch and just slowly stroke watching you squirt and using your juices as lube

10:38 PMSassy
Mmmm

10:34 PM Phil
Would love to lick that toy clean

10:40 PM Sassy
It does get juicy

10:41 PM Phil
Mmmmmmm, love that
Coated in your sweet juices

10:47 PM Sassy
Remember the old Ronco commercial – it slices, it dices?

This thing buzzes and pulses…8 different speeds! Ha ha

10:48 PM Phil
[photo of… something. It’s completely dark]

Damn

10:50 PM Sassy
I just turn it up and press!

You ready to sleep?

10:53 PM Phil
I like that! That dark thing was the cum shot  : P

8 speeds. I remember when they were made of hard plastic and had one speed

Times have changed for the better

10:54 PM Sassy
Nice! We’re living in the future.
Sweet sexy dreams Philip

Sassy
[gif of a minion kissing the screen]

GIPHY

10:55 PM Phil
Ha! Gotta get up and make breakfast tomorrow. Nite sweet girl

10:55 PM Sassy
Mwah!

10:59 PM Phil
<3 XXoo

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Breakfast Pizza

December 5, 2016 Monday
7:58AM Sassy
It’s beginning to look a lot like Christmas!  First real snow.
[photo of my balcony with a little Christmas tree and snow on the ground below]
9:31AM Phil
Awesome! Good morning!

8:19PM Sassy
Breakfast pizza… it’s what’s for dinner! Egg, cheese and BACON!!  


10:06PM Sassy
The movement…

10:08PM Phil
There you go, deep and hard
10:09PM Sassy
From sadece-hayal.tumblr.com