To post pussy or not?

October 8, 2016 Saturday
8:03AM Sassy
Good morning kid!
9:45AM Phil
Goooood morning! 
Finished at the gym. Now for steak and eggs!
7:34AM Sassy
Good morning!  How was the mountain?

7:35AM Phil
She was good! Mountain was fun. Heading south

7:36AM Sassy
Yay!  Hope the trip is easy.
Great to see you dancing.

12:15PM Sassy
To post or not post the word pussy?  Interesting article about how media outlets are using or censoring the latest scandal’s key word.

The ‘p-word’ problem

Encouraging Randy

October 7, 2016 Friday

6:39 AM
Randy
Good morning,  
I am so sorry I fell asleep last night.  
It has been a very long week for me.
Sassy
Good morning hot stuff! 
No worries.. Happy Friday!
10:55 AM
Randy
Thx happy Friday to you too
Sassy
I’m going to the beach! Wish you could go and hold my hand.
Randy
That would be fantastic!!!
Sassy
Sit on a big rock and canoodle. 😉
Randy
Sounds very fun! 
Been a stressful week
Sassy
Going to the beach is always a double-edged sword… it’s so beautiful and it restores my soul. But it’s where I most miss having someone to hold my hand…*sigh.
Randy
I so know the feeling
8:56 PM
Randy
How was your day
Sassy
Fabulous!  You? 
Randy
Eh I’ve had better
Sassy
[photo of the ocean and the lighthouse]
Randy
This has been a long week
Nice 
were you there today? Looks great
Sassy
I was there 
Randy
Nice even looks warm
Sassy
It was!  Beautiful in the sun, sat on a big rock. 
Listened to the waves
Randy
Long walk?
Sassy
Nah… tide was in 
Had a great lunch at Lobsta Land
Randy
Sounds good. 
Miss having free time
I’m a bit envious
Sassy
I try to make good use of a beautiful fall day 
Randy
Nice 
sounds like fun
Sassy
It was so nice not to be at work, to get out of the city, eat good stuff, see pretty places… 
Randy
I don’t get out enough myself
Sassy
Maybe I can help? 
Encourage you… 
Randy
Perhaps I need to cut back working
Sassy
Is that possible? 
Randy
Not right now 
my boss is being very pushy
Sassy
Boo
Randy
???
 Sorry didn’t quite get that
Sassy
That stinks 
Randy
Yes started looking for a new job
Sassy
Maybe you can tell him your um… girlfriend needs you to work less.  😉 
Randy
That would be fun and interesting
Sassy
Are there recruiters who could help you? 
Former co-workers who are now someplace you want to be? 
I like to put you to work… sort of 
Randy
Sorry I fell asleep last night
Sassy
No worries… 
If you need sleep, that’s what you should do. 
Randy
Oh yes I get calls all of the time
Sassy
Nice! 
Randy
It’s been a long and stressful week
Sassy
Will being away be better or worse? 
Randy
Still have to do my work so will be 20 hour days
Sassy
Yuck!
Randy
Exactly 
I haven’t been tired like this in a while
Sassy
Anything you can delegate? 
Randy
Nope 
I tried to hire someone and she turned it down
Sassy
Yuck 
Randy
Yeppers
Sassy
Stressing yourself is rarely the right answer
Randy
Exactly but Wednesday was relaxing
Sassy
Oh good… I would like to help however I can 
Randy
It helped tremendously
Sassy
I may need an up-close photo of your cock
Randy
Hmmm I’ll see what I can do 
you liked him?
Sassy
Oh yeah… 
I close my eyes and see that beautiful mushroom top and go on in my mind licking, touching, sucking until you fill my mouth! 
Randy
I’ll have to take one when there’s fewer people around
Why do you like him 
he’s not very big
But he is good at finding g spots
Sassy
Classic beauty
I prefer average size 
Attached to you 
Randy
Ok thx and nice
He is thick and can fuck for hours
[photo of his erect cock peeking out from his shorts]
Ok?
Sassy
Mmmm… fantastic!  Great photo!  
Randy
Thx
Suckable?
Sassy
Oh yeah
Randy
Big enough I hope
Sassy
Causes quite a reaction over here 
We’ll see.  🙂
Randy
Nice
He is pretty sensitive so I can feel g spots pretty well
Sassy
I want to test that out! 
I’m having dozens of shoulda’s about Wednesday night… hope to be much better next time I see you 
Randy
Better it was great hearing and watching you cum
Sassy
I will be louder next time.. cars are tough 
But I thought we did pretty well under the circumstances! 
Randy
Yes but she climaxed
[Thumbs up]

 yep
She did pretty well
Sassy
You made it easier than usual! 
Randy
Oh it can take her a bit?
Sassy
Depends 
Have you ever done the traveling man feature on AM?  
Found women on your trips? 
Randy
No no time and no interest why?
Sassy
Just wondered
Randy
Seems like a weird thing to do
Sassy
Depends on your goals I guess
Randy
Yeah not my style 
I‘m guess probably not a prostitute too
Sassy
You leave tomorrow? 
Randy
Yes still haven’t packed or finished reservations
Sassy
Oh my
Randy
It will work out
Sassy
You have to dress up? 
Randy
I usually do
Sassy
You looked very handsome 
Randy
Thank you 
I liked your blouse that opened quickly
10:43PM 

Sassy
He he


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Beautiful Beach Day

October 7, 2016 Friday
8:40AM Sassy
Good morning kid!
11:53AM Sassy
Heading to the beach.  Wish you could go and hold my hand.
1:11PM Phil
Awwww, have fun!

1:13PM Sassy
Out and about in Gloucester on a beautiful fall day!  Started with a luscious lobster lunch at Lobsta Land!!

Lobster chowder
Hubby’s french onion soup
Coconut shrimp with salad
Hubby’s BLT
Paella with mussels, shrimp, clams, sausage and lobster!
1:15PM Phil
3:15PM Sassy

Marshall’s Farm stand, Gloucester decorated for Halloween!


4:15PM Sassy
Waves, doggies, sand, sun and a lighthouse! Oh my!

Wonderful walk on Wingaersheek Beach in Gloucester

Randy Thursday Thoughts

October 6, 2016 Thursday
1:05 PM
Sassy
Hiya!  It’s your Sassy lunch pal.  🙂 
Randy
Hey there how are you?
Randy
Last night was fun
Hello?
Sorry been sitting in meetings didn’t see you message
Sassy
No worries… 
just wanted you to know I was thinking of you.  I’m great! 
Mired in the payroll.  whee
Randy
Sounds like loads of fun over there
How is your day?
Sassy
I’m fine.  
Lots of good memories of last night to think about
You? 
Randy
Yes me too… it was fun
Sassy
Heading home.  
Should be around later if you feel like chatting.  
Have a great evening! 
5:15PM 
Randy
Sounds good 
I should be online later 
I have a number of things to do but should be on before 10. 
I hope you had a great day

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Ballgames

October 6, 2016 Thursday
7:49AM Sassy
Good morning kid!  Today is my Friday!

8:14AM Phil
Mine too! Heading to New York!

8:14AM Sassy
Another Ocktoberfest adventure?

8:17AM Phil
Yep!

8:18AM Sassy
Yay!
11:09PM Phil
Rooting for the Sox

11:11PM Sassy
Awww… thanks kid.
That Rangers game was brutal
How’s the family?

11:26PM Phil
Great game!
Having so much fun


Meet #1 Randy Time

October 5, 2016 Wednesday

5:02 AM

Sassy
Good morning! 
I fell asleep at 7:30…oops. probably the flu shot…
Only about 12 hours now until Randy time! Woot!
6:56AM

Randy
Hey good morning
Hope you feel okay after your shot
8:07AM 

Sassy
I’m feeling fine! 
Sleeping was great for me. 
How are you this fine morning?
Randy
Good 
a little crazy at work
Looking forward to meeting you
Miss Sassy
Sassy
I’m so excited! Hope this day goes by quickly
Randy
I am too. 
have meetings most of the day so it should
Sassy
So you’ll be at the bar area?
Randy
Yes or we could meet in the parking lot whichever works for you
Sassy
Inside is good
Sassy
All clean, heading to work
Randy
Ok see you later very excited

1:46 PM
Randy
A day buried in meetings and paperwork for me… sheer drudgery. How about you?
Sassy
Rolling along… pretty quiet. 
Getting more and more nervous. 
tell me it will be fine? 
Randy
Not too bad
It is a pretty nice day outside today
Sassy
What color do you have on today? 
Randy
[photo of his shirt front – blue dress shirt]
And a blue sweater if it’s cool

You?
Oh I won’t be wearing the headphones
Sassy
[photo of my “Sassy goes to a meet” outfit – blue top with silk scarf]
Randy
Nice!
Sassy
There are buttons under there… 
And a certain lucky black bra 
so you will know it’s really me. 
If you want to check
Randy
Well played miss sassy… get my mind wandering all day
Sassy
That’s one of my tasks, right?  
Lead your mind to um… greener pastures? 
Naughtier pastures? 
Randy
Indeed
I like it
Sassy
Let you escape from that desk into a fantasy 
Randy
Sounds lovely…. and warm
Looking forward to meeting you
Sassy
It is going to be fun!

Randy
Yes do you have a rough idea when you’ll get there?
Sassy
Planning to leave around 4:30 pm… 
depends on the traffic but I would guess in the 5:15 – 5:30 timeframe
Randy
Ok see you in a bit
Randy
Like the color we will match well
Sassy
I’m happiest in dark blue.
Your shirt looks touchable.
Randy
Thx it is
Dear miss sassy there appears to be a bulge in my pants but I’m not sure why
Sassy
I will need to verify tactilly
Tactfully
Tactically?
Mmmm
Randy
Nice!
Randy
I’m leaving in about 5 mins
Randy
I just got to summer shack
Sassy
I’m here. Let me know when you make it inside and I’ll dash inside too!
Randy
Where are you at 
sorry didn’t see you
I’m at a round table in front of the door

=====

REPORT ON MEETING RANDY

I left work early and traffic wasn’t too bad, so I made it to the Summer Shack near the Alewife T Station right on time.  They have a big parking lot.  I picked a spot toward the back near the fence, away from other cars, in case we wanted to sit out in my car later.  
We were chatting online right up until the moment I walked into the restaurant.  Heh.  This guy can really chat!  
He got there before me – I adore that!  He was sitting in the center of the bar area at a high table. There was no one else around.  He got down of the high chair and gave me a long hug.  Mmm… he is solid and cuddly!  We parted and I situated myself on the high chair.  
He took my hand and smiled at me, staring.  I smiled and waited for him to get his eyeful.  He is a big burly guy with lots of sandy blond hair and glasses.  He asked me about my community project and I regaled with some funny stories about it.  He got this odd look on his face and glanced nervously around.  I asked him what was up?  He said one of his co-workers had just walked in.  He suggested we move around to a table on the other side of the bar against wall where that person could not see us.  I agreed and we migrated to the new table.  
He asked me about my work and told me about his.  The waiter came around and I got an iced tea. He said that sounded good and got one too!  That doesn’t happen very often.  
He told me a story about an old flame getting in touch and he asked me questions about my adventures in that direction.  We agreed it is very exciting and fraught with peril.  He’s good at balancing listening and talking – an art.  
We talked for nearly two hours!  He mentioned that he probably should leave soon.  I was starting to think he wasn’t really interested in me when he suddenly said we should go to his car!  He asked me what kind of car I drive, decided mine was bigger than his, so we went to mine.  Thankfully no one had parked around me so we had some privacy.  We sat in the front seat. 
The moment I closed my door, he leaned over and grabbed my face and started nibbling on my lips!  Mmm… he is a good kisser.  I caressed his face and he moaned nicely.  He kep trying different angles, kissing faster and slower.  Yum. 
He unbuttoned my top and massaged my breast, groping my bra and trailing his fingers over my cleavage.  That got me tingling!   I alternated between giving him my “stare of fire” directly into his eyes and watching what his hands were doing.  
He wiggled his right hand down my tummy and inside my slacks.  He watched me, checking to be sure I was not going to stop him.  I shifted lower in my seat and spread my legs open to make it clear stopping was the furthest thing from my mind!  
His hand made it’s way inside my panties and found my clit on the first try.  Nice!  He rubbed back and forth across my clit.  My hips popped toward him and he smiled.  He pressed and flicked… wow… this guy knows what to do!  I was so wet.  
I tried to relax… I tried to focus… I even tried fantasizing, but there was no way I was going to be able to finish the first time with a new man in the front seat of my car.  *sigh  So I had as much fun as I could…  moaning and breathing funny and shaking until he thought I had cum.  He smiled and crowed about his prowess and sat back. 
He pulled his cock out of his slacks and I stared at it, making appreciative noises.  It was about average size in length but quite wide around.  Yummy.  I spread his pre-cum around the crown and did some work with my hand… a little hungry octopus squeeze and pull with all my fingers, then some barber pole twists.  I leaned over and tasted it, licking slowly up and down.  A car parked right next to us!  I froze.  Argh.  The guy got out and walked away without lingering… I hoped he had not seen me.   And that he had gone in for dinner and not picking up take-out!  

I took a couple of deep breathes, then kissed Randy’s hard cock and his hips shifted, while his hand pressed my head closer.  I sucked his cock deep into my throat for just a moment… then sat back up.  I really can’t do a full blow job at that angle in the front seat of my car with people parking around us.  I promised to do much more the next time!  He said he understood.  
He leaned over and sucked on my left nipple, doing some sexy little nips with his teeth that got me shivering.  He kissed me more.  He sighed and said he really had to be getting home to make sure his kids got to bed.  
He anguished that we had met when he was about to disappear for 2.5 weeks on business trips.  I assured him we could keep chatting and it would be worth waiting for!  He smiled and nodded.  
He gave me a fierce last kiss, stroked my cheek and was gone at about 8:15 pm.  
I went back inside to order take-out and mulled over his words and his actions, hoping I would continue to hear from him.  I didn’t have long to wait. 
=====

10:03 PM
Randy
Hello miss sassy 
it was meeting you tonight
Sassy
Hiya hot stuff 
It was what? 
Randy
Sorry premature message sending
It was terrific to meet you this evening!
Sassy
Yay!  You are very special.  
Get home okay? 
Thanks for the tea and company! 
Randy
Thx
There was construction on the freeway so a bit slow
Oh yes
Sassy
Got the kids to bed? 
Randy
Yes did you get dinner?
Sassy
Yes – it was very fast! 
Jerk off? 
Randy
Oh good hope it was good
Sassy
Tasty
Randy
Yes I did and thx
Sassy
Not as good as the pre-cum I ate earlier… 😉
Randy
Nice 
I taste ok?
Sassy
Yummy
Randy
Nice 
your mouth felt nice
I’m going to jerk off again later
Sassy
Really? 
Randy
Yes why 
I used to jerk off 3x per day
Sassy
At what times?  Morning, lunch and evening? 
Randy
2x morning 1x night
I cum more with fucking
Sassy
Wowzers…. 
Randy
I’m a hornet bastard
Sassy
🙂 
Randy
Or horny
Luv to kiss 
fuck and 
eat pussy
Sassy
Was I as advertised? 
Randy
Yes liked you
Sassy
You were sexier than I expected.  
When I look into your eyes… mmmm
Randy
Like the way you kiss and cum
Really?
I don’t think of myself as sexy
Sassy
There’s this.. impish grin that seems to say “Hubba hubba” 
Randy
Ic
I am very passionate
I’ll warn you that if you go down on me the first time I cum a lot
Sassy
Sounds good to me! 
I ain’t fraid a no cum 
Randy
Mmmmn yes
Sassy
(hum to the tune of Ghostbusters) 
Randy
I am sorry miss sassy but I am a bit tired and must retire
Sassy
Sleep well! 
Randy
Thx you too hope to chat tomorrow sexy
10:37PM 
Sassy
Yes please!  Mwah! 


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Jester jive

October 5, 2016 Wednesday

from: Jester
to: Sassy
date: Wed, Oct 5, 2016 at 9:37 AM
subject: Re: Dessert

Hi Sassy,

Hope your week is going well. Sorry about your weekend not being great. Holy Crap it took me forever to get out of the City after lunch. Brutal traffic leaving….

=====
Hmmmm… not sure what to make of this.  He waits four days and then… terse. Complains about traffic.  Nothing about our first meet or planning another.   What can I say to this?   I drafted a reply but didn’t send it.  I’m sorry about the traffic?  Zzzzz…. It’s tough to be enthusiastic when he’s not.  
Such a contrast between him and the other guy!  I’ll focus on Randy for now, see how our meet goes.  

Well enjoy

October 5, 2016 Wednesday
5:04AM Sassy
Good morning!  I fell asleep at 7:30…oops.  probably the flu shot…
Have a wonderful Wednesday!
I have a first meet tonight with a younger man.  Woot!

5:44AM Phil
Well enjoy!


Tuesday Randy Chat

October 4, 2016 Tuesday
7:00 AM
Randy
Good morning sexy
Was thinking about you and thought I should say hello
Sassy
Good morning hot stuff
Mwah!
Randy
Good morning 
how are you?
Sassy
I’m great! You?
Randy
Alright getting my windshield fixed
Heading into work?
Sassy
Yes
Randy
I will be in a bit
Sassy
I wish you were in me
Randy
So do I
Love morning sex
Sassy
; )
Randy
Hmmm love all morning long morning sex
Sassy
Might as well make it a day.
Randy
Yes please!!!!!!
That sounds wonderful
Randy
I am so looking forward to meeting you babe
Sassy
I’m thinking about you…hugging, smiling, listening to your voice
Randy
Likewise
Can’t wait to hear your voice
Feel your hands
Taste your lips
Hear your thoughts
See your smile
1:26 PM

Sassy
Heading to get my flu shot
You hanging in?
3:19 PM 
Randy
Yes drove to a meeting
Got my flu shot last week 
was ok
Sassy
Good.  
Randy
How was your day?
Sassy
Good! I got out of the office – got my flu shot and picked up ramen for lunch! 
I feel like Annie… 
TOMORROW!  TOMORROW!  I’ll see RANDY TOMORROW! 
Randy
I had soup trying to lose weight
And very nice
I am looking forward to seeing you too
Looking forward to knowing your name
Sassy
Why?
Randy
Learning more about you
Sassy
Ah.
Randy
Knowing that you trust me enough
Or do you prefer to remain anonymous?
Sassy
I will tell you. But mostly that name goes with my other side…reminds me of the responsibility and regular life I’m trying to escape for awhile. You want to be with my Sassy side.
Randy
Yes I do so
And I get it
How about a pseudonym
I like Marisa such as in Tomei?
Sassy
Hee hee
Sassy is the fun me!  
Or bodacious bombshell.  
Or Buxum Boston Bootylicious Babe. 
5:14 PM 

Sassy
Heading out.  
Hope your meeting goes well. 
 If it is safe, perhaps call me on your drive home? 
Tuesday, October 4, 2016 11:04 PM
Randy
Hey just got home… a productive evening. 
Chat tomorrow?


Serious chicken noodle

October 4, 2016 Tuesday
1:43PM Sassy
Got my flu shot!

1:54PM Sassy
Got ramen from Wagamama for lunch.  Figured some serious chicken noodle soup was in order after the shot!  I forgot to take a photo but it looked something like this:

1:58PM Sassy
Hiya kid!  Behaving yourself?
 4:04PM Phil
Hey there!  That’s not any fun

4:54PM Sassy
True!  Hope you are being naughty.  : ) 

5:08PM Phil
Ha!
5:09PM Sassy
If you need assistance, I am happy to assist.

5:31PM Phil
Ha ha, I know 
[devil icon]