Category Archives: Randy

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Such a hussy

Monday, December 26, 2016
7:26 AM Randy

Good morning sexy

12:11 PM Sassy
Good afternoon hot stuff!

4:04 PM Randy
Hey sexy sorry I just saw your message it doesn’t seem to be alerting me
How are you

10:26 PM Randy
Hey sexy how was your day

10:50 PM Sassy
Hiya! I napped a lot. You?

Randy
Took my daughter clothes shopping
oh and shoes

Sassy
Oh my
I despise shopping. But that sounds fun.

Randy
Wasn’t too bad
She found nice stuff
Do anything fun today?

Sassy
Just helped a nice man in Atlanta cum but pretty quiet otherwise. Never got dressed

Randy
Nice 

by Skype or something?

I like your nonchalant approach

Sassy
Phone. He was in his mother’s guest room

Randy
Nice, fun?

Sassy
I like to be helpful

Randy
And did he take care of you?

Sassy
Nope. Fell asleep

Randy
Bad guy
Hmm I’ve been working on my stamina 

trying to go back to when I was good for 5x

Sassy
I probably should not tell you these things.

Randy
can only manage 3x lately with my hand
why?

11:00 PM Sassy
Makes me sound like such a hussy

Randy
It’s only over the phone and i like it
I like that you’re very sexual

Sassy
It’s odd this year… Holidays are usually quiet, men busy with family stuff

Randy
Do you do that a lot?

Sassy
But they’re popping up from every direction today

Randy
I like the metaphor
Are you getting what you need?

Sassy
Ha ha
It’s something…

Randy
Ok-
I did like seeing you and loved getting you to climax
Can’t imagine what you would do with your clit in my mouth

Sassy
Fun to imagine

Randy
Have you been dating a bunch?

Sassy
No
You?

Randy
No I took down my profile because I wanted to see where this was going and was very busy with work

Work has been a drag was very busy with travel 

was away for 3 weeks in Nov

I finally hired 1 person and will be hiring another person shortly

Let me ask this 

is it too late for us or should I keep trying?

Sassy
Do you have a plan? What you’d like to do?

Randy
You mean for us or for work and freeing up time?

Sassy
For us…next step…

11:15 pm Randy
Not sure figured I would see what you want
And go from there
I did like you teasing my cock and would like more

Sassy
Mmm

Randy
Wonder if you have a g spot and if my cock can find it
am wondering if you squirt and can cum multiple times
What would you like for a next step?

Sassy
See you. 

Alone. 
With a bed.  🙂

Randy
Nice…. can you cum multiple times?

Sassy
Depends

Randy
I need to be drained baby 

I need to cum at least 3x 
I would need you to drain me

Sassy
I can do that.

Randy
Would you suck me off 

make me cum hard
Let me cum on you tits

Sassy
Sure

Randy
What do you like
Do you like anal?
Too much?
And I would be up for meeting
Would like it very much
Did I scare you off baby?

11:30 PM Sassy
No no…

Randy
So in your fantasy world what is the ultimate sexual experience

Sassy
Tough to say. 

I miss the basics so I tend to focus on them and not get to fancy acts

A back rub…a long hug…kisses, exploring slowly

Randy
I like it
Love exploring and teasing
Love slowly removing clothes
I am very very oral

Sassy
Doggy style pounding.
Learning what helps you feel good
Figuring out how you are at helping me

Randy
Do you need a big cock to get off?

Like doggy style

Sassy
No… Prefer average… Easier to deep throat

Randy
Nice

Sassy
Most large men have been lazy…

Randy
I usually shower beforehand 

I am very smell sensitive

Yes that’s what I hear

I can keep it up for hours

And as you’ve seen I try to be a pleaser

Sassy
We could have fun

Randy
Yep
Do you like 69?
I do like kissing… a lot

Sassy
Oddly no…

Randy
Not odd too much going on for some

Sassy
I have trouble on where to focus

Randy
Are your nipples sensitive?

Sassy
Also not so keen on the whole cumming together thing

Want to be able to focus, savor

Oh yes

Randy
So sucking nipples = good/great?

I love nipples
Love exploring with my tongue

Love how you sound when you cum

Sassy
Just remember there’s an entire breast there

11:45 PM Randy
Oh yes two hands 1 mouth
while fucking

What about cumming together while fucking?
and are you loud ?

Sassy
Not so much… But it depends

Yes.. squeaky

Randy
Ok.
My cock is pretty sensitive so I am pretty good at finding a g spot

Sassy
First time can be odd.

Randy
You already came with me baby in a car no less

When do you typically have free time to get together

Sassy
Try not to judge too much by it… Usually gets much better

Randy
OK

Sassy
Pretty flexible

Randy
Alright would you want to meet at a hotel?

Sassy
Sure

Randy
Perhaps outside of the city (less expensive)

Sassy
You have ones you like?

Randy
Baby I’m sorry 

I fading fast and need to get up early so will need to head off to bed soon

And no I haven’t done this in a long while

I can look

Sassy
No worries. Ping tomorrow?

Randy
Yes please

Sassy
Sleep well

Randy
You too baby and am glad we could reconnect

Sassy
Mwah!

Randy
You’re awesome

11:53 PM Sassy
You betcha!

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Randy resurfaces

December 25, 2016 Sunday

9:41 PM Randy
Hey miss sassy. I hope you had a terrific Christmas and a tremendous new year!
Sorry I have been MIA, I have been engrossed in work
I hope all is well with you

Sassy
Merry Christmas to you!

Randy
Thx how are you?

Sassy
I’m great. Santa was kind to me, I’m in the midst of 11 days off and finished a big chunk of settling my mom’s estate last week.

Randy
Nice to have the time off especially with the emotional challenge you must have with closing out her estate

Sassy
It’s glorious!
You still with the same company?

Randy
Yes my boss is being an ass
Been very busy
We are shut done this week

Been thinking about you

Sassy
Hope that’s fun

Randy
It is … wondering what a longer date would be like

Had a few naughty dreams about you

Sassy
Ah…glad I could inspire you

10:00 PM Randy
Well I liked our date

Sassy
It was fun?

Randy
Yes I liked spending time with you both talking and otherwise
Did you like our date?

Sassy
I did.

Randy
Sorry work has taken over my life the last few weeks 

very long days

Sassy
I figured that might be the case

Randy
Been traveling a bunch too

I figure if I could get you to climax in a car what things might be like in private

Sassy
Fun to ponder

Randy
Yes
Indeed
Well as long as you can handle multiple orgasms
Sorry too much?

10:14PM Sassy
No, just dealing with family all around

Randy
Oh in sorry baby I know it can be hard

Sassy
Tricky

Randy
Yes money and emotion can be a tough combo, add in family then very rough
And if you would be up for a second date I’d love it

Sassy
Wow… Interesting idea.

Randy
Maybe more intimate?

Sassy
I dunno…if work eats your life it doesn’t seem wise

Randy
I hired 2 people to help at work so things are slowing down
But I understand you’re hesitation

Sassy
Sorry, hubby keeps popping in.

Can you ping me tomorrow?

Randy
No worries
Yes
Great reconnecting with you

Sassy
Yes! A nice surprise!

Randy
I look forward to chatting tomorrow

Sassy
Sweet sexy dreams Randy

10:30 PM Randy
Ty you too
I’ll dream of you
Kissing you was wonderful

by

Invite to my place

January 13, 2017 Friday

5:30 AM
Randy
Good morning

8:13 AM
Sassy
Happy Friday hot stuff!

11:22 AM
Randy
Same to you
I hope you have a great day
Mine is off to a rocky start

Sassy
Oh no! Why?
I’m in the waiting room at MGH

Randy
Just too much work not enough time
Good luck today

Sassy
Thank you!
Exam was normal, just waiting for the squish
I took 4 ibuprofen, shouldn’t feel much
Hubby is away this weekend. 

You should stop by!

Randy
Hmm sounds wonderful
Wife has long honey do list for me
Glad things went well

12:54 PM 

Randy
Very sexy baby

Sassy
All done! Out for Chinese lunch!

Randy
Very nice I hope you have a good time

8:47 PM
Randy
How was lunch?

Sassy
Fantastic!

Randy
What’d you have?

Sassy
Lion’s head meatball, wonton soup and yushiang pork with Chinese bread

Randy
Sounds great!!!
Worth the drive?

Sassy
Oh yeah… cheap, fast and good!

Randy
Who could ask for more?
I’m a fan of mushu chicken

Sassy
Yum!
Pancakes…

Randy
Yes I like the sauce too

Sassy
Usually a nice mix of veggies and meat

Randy
Yeah a good balance
Not too greasy

Sassy
Busy weekend?

Randy
Yeah have some work to do
Clean up the house
A few projects
Then see Rouge One
You?

Sassy
I’m having afternoon tea at the Taj Hotel tomorrow with a gal pal
Have a meeting Sunday
Get some stuff done around my place
It’s so odd having the place to myself
Do you ever get to be home alone?

Randy
Yes Sunday morning the only quiet time during the week

Sassy
But overnight?

Randy
Rarely overnight
Why?

Sassy
Hubby rarely goes anywhere, and especially not without me. 

 Just so strange to have him gone for 3 nights…

Can’t recall him ever doing that except when he had surgery

Randy
Oh I go away on business for several days 

wife hates it
I hate it too 
often very tired and takes a while to recover
Where’d he go?

Sassy
He’s at the big sci fi convention in Boston
I know you go away… but do they ever go away and leave you home alone?

Randy
Yes they have gone on vacation without me.
My wife gets upset when I can’t take too much time off
Sometime it is nice to have the alone time
Sometimes very nice

Sassy
I bet
I wish I had thought more about it, planned more…
found someone who could spend the night!

Randy
Had a sexy weekend?
IC
DO you get that a lot?

Sassy
But it’s rare…
weekends are tough… and holiday weekends even worse

Randy
You get to have suitor every so often?

Sassy
It’s been a very long time
But I can if I like

Randy
Oh yes the internet is wonderful isn;t it?

Sassy
I don’t usually let me visit here until I’ve known them awhile

Randy
I don;t know if I would ever feel comfortable with something like that

Sassy
I won’t go to a guy’s place if his wife is not aware. 

I did it once…. big mistake
But here is different, where Hubby knows and approves

Randy
Oh what happened at the other place

Sassy
I think I told you about that day… 11 things went wrong one after the other…

Randy
I don;t remember are you sure

Sassy
The worst was me hiding in a closet when his wife returned home unexpectedly.

Randy
Oh yes I remember now
That must have sucked

Sassy
The worst part was listening to her scream at him

Randy
Because she knew what was going on

Sassy
No
totally random
And then it got worse…
when I asked him about it
he said, “was she screaming?”
I never raise my voice…

Randy
Oh boy

Sassy
so shocking to hear it is so regular for him he doesn’t even notice

Randy
Kind of like my house

Sassy
Oh gosh… I hope not
I sat there, texting old flame, who of course laughed his ass off at me

Randy
Ok that sounds sad

Sassy
At least I learned from it!

Randy
Yes
Just one thing I could never do
Risks are too high

Sassy
Well, he’s divorced now. 

She only yells at him in capital letters in texts about their kids now.
I had a great play time this afternoon. 🙂

Randy
Oh do you still see him?

Sassy
I saw him once after he left, 18 months later, last June

Randy
Oh
What time do you usually get up in the morning?

Sassy
7:30 am

Randy
Maybe I could head into Cambridge Sunday morning?

Sassy
Oh my…
That could work

Randy
I’ll have to see if I can get out for a bit

Sassy
Of course… don’t take any big risks.

Randy
No never
Just so you know what your getting in to
[naked photo of him standing in the mirror]

Hope that’s ok

Sassy
Yum
No. It’s uber sexy!

Randy
Cock’s not too long right now but he’s thick and I can keep it up for a while
Thx
And he can cum 3x+

Sassy
I’ll be here. 

If you can make it, great! 
If not, no worries. 
It’s fun to think about!

Randy
Yes
Just got to check if I need to take daughter to volleyball
Any more pics?

Sassy
Just Chinese food pics today. 🙂

Randy
Oh

Sassy
And MGH… heh

Randy
Oh boy not so fun

Sassy
It’s a nice place
With nice people
Kinda of like driving to a beautiful spot, looking over a cliff
Just hope they don’t shove you off!

Randy
How’s that?

Sassy
If they were to tell me I have cancer again… adds a big scary element

Randy
Oh IC
Was trying to think positive thoughts

Sassy
I can feel them… there’s this energy that surrounds me on days like today
I got 49 responses on Facebook when I posted about being okay

Randy
Cancer is tough
The second worst C word

Sassy
I have a mixed reaction… 

half “oh, just shoot me” and 
half “well… I got around it before, I can get around it again!”

What’s the first worst?

Randy
The one that is universally hated by women

Sassy
Have you ever seen The Vagina Monologues?

Randy
No it was recommended by several people

Sassy
I should give you the script to read

Randy
Sounds good

Sassy
I was in it a few years ago
Only time I’ve been on stage

Randy
yeah you mentioned on our date

Sassy
There is one vignette about that word, helps to reclaim it a bit, give it a different power

Randy
Yes still hated
I don’t know Ive had several friend that could care less… only a word
Hope my total package is good enough baby

Sassy
Please don’t worry!

Randy
I’m not worried just up front

Sassy
I appreciate it
Not sure why I trust you to visit me, but I do

Randy
I’m not a psycho
The voices in my head told me I’m not

Sassy
Ha ha

Randy
I am hoping to get my cock back to where he used to be in size
Hoping if I start using him he’ll return a bit more
He used to be 8″ now he’s more like 5

Sassy
I’m sending you the script.

It’s little stories, easy to read in bits

Randy
Ok

Sassy
I learned so much from it..
Some are funny, some are awful

Randy
Ok I’ll give it a read

Sassy
Thank you. 

 I think you’ll find it coming to mind in lots of different areas of your life

Randy
Hmmmm okay

Sassy
Thank you.

Randy
Should be interesting I hope

Sassy
It is meant to entertain

Randy
Need some quality skin on skin time

Sassy
only 35 script pages…

Randy
Short

Sassy
Yup

Randy
Sorry baby I’m falling asleep. 

Its been a very very long week
super tough
Oh when does hubby come back

Sassy
I thought it was about time for you to sleep…
He’s back late Monday

Randy
OK

Sassy
Sleep well Randy

Randy
Thank you and you too.

10:18 PM
Sassy
Mwah!

by

Halloween hello

October 31, 2016 Monday

5:59 PM
Randy
Hey there Miss Sassy,  
I am sorry that I haven;t been around much.  
Work has been kicking my butt!  
I hope you’re having a very Happy Halloween!
Sassy
Hiya! 
Hope you’re getting more treats than tricks!
Randy
Thanks 
work has been full of tricks…  
I will get some treats tonight with the Daddy Tax.  
Sassy
Do you get kids at the door?
Randy
Yes  
a lot of new families moved in this year.  
What about you?
Sassy
Nada
Randy
No kids in the building?
Sassy
Not really…. 
A few babies but most folks move by the time the kids grow
Randy
Oh IC.  That’s too bad.  
My dog is going crazy she wants to chase the kids!
Sassy
Your kids dressing up?
Randy
Yes they still do it 

Sassy
Cool!
Randy
I’ve got to run and take them out.  
I’ll try and be on later
Sassy
Have fun! Mwah!
6:08PM
Randy
Thx you too

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Sassy secret

October 26, 2016 Wednesday

10:49 AM
Sassy
Good morning!  
Guess what the Word of the Day from wordsmith.org iis? 
http://wordsmith.org/words/sassy.html
Hee! 
Hope you’re having a great one! 
Randy
Hey it’s great to hear from you. 
Funny about the word of the day, how are you?
Work has been insane 
so a bunch of stuff going on
Sassy
I’m great!  
Off work for the rest of the week.  
It’s my 20th wedding anniversary.  🙂 
Randy
Congratulations ?
Sassy
Indeed.  
To the outside world, I have a long and happy marriage! 
You know the secret. 
Randy
Oh well done then miss sassy
Sassy
We’re going to Helmand.  Ever been? 
Randy
No I haven’t is it nice
Sassy
Fantastic… Afghan place, sort of a cross between Greek and Indian
Randy
Sounds nice 
good view?
Sassy
Pretty place, painted yellow with fireplaces
12:06 PM 

Randy
Sounds lovely


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Get close

October 23, 2016 Sunday

9:27 PM

Randy
Hey I think I finally recovered from my trip
I have been very tired and lots going on at work.
How have you been?
Sassy
Great!  I had an adventure to RI today
German lunch in Bristol, beach in Little Compton, had a divine dinner on the bay in Tiverton. 
Randy
Oh sounds tremendous.  
I had a burger for dinner.
Sassy
Yum
Randy
Spent most of the weekend sleeping
Sassy
Good! 
Randy
Almost feel normal again
Sassy
Hooray! 
Randy
Yeah work has gone crazy though
Sassy
OH? 
Randy
Yeah you know how people are. 
Love to power grab
Sassy
Ewww
Randy
Exactly
Sassy
Can you escape?  
Or grab something yourself? 
Randy
No I am in charge in a way.  
I am looking for a new gig… way too strange of a place
Sassy
Hard to tell when you interviewed there? 
Randy
I am looking at startups where there is a very small group
That way there is less politics
Sassy
Have a little beach moment
[photo of the beach in RI]

Randy
Looks lovely
Sassy
It’s glorious 
It was so clear… 
I swear I could see Martha’s Vineyard 
Randy
Nice 
is that today?
Sassy
Yes, about 4 pm 
My dinner
[photo of baked stuffed lobster]
Randy
Nice 
mine was;t so well presented
How was your weekend
Sassy
Busy. Took snacks to a project work day yesterday, then went to a surprise birthday party
Randy
Sounds fun
Sassy
It had its moments
Randy
I mowed the lawn and worked around outside… I
 would argue a bit less fun
Sassy
Maybe so… 
but productive!  
Randy
Yes true… not so fun
Sassy
Get close to me… I will help you have some fun! 
Randy
I like your thinking
Sassy
Depends on what you think is fun, I suppose 
Randy
Many things are fun.
Sorry I guess I’m still tired
Sassy
No worries… good to hear from you no matter how you’re doing. 
Get some more sleep? 
I’m headed that way 
Randy
Yea I’m off to bed myself.  
Sorry  
I’m not much fun tonight …still tired
Sassy
Take care of yourself.  
Hope tomorrow is better! 
Randy
Thx 
chat tomorrow?
Sassy
Yes please! 
Randy
Ok tty soon
10:04 PM 
Sassy
Mwah! 


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Randy heading home

October 21, 2016 Friday 

1:46 PM

Randy
Hey sexy 
wow what a crazy week. 
Sorry I haven’t been around much 
i have been very busy with meetings
Sassy
No worries. 
I smile when I see you and try not to worry otherwise. 
You hanging in?
Randy
On my way back to Boston
Sassy
Hooray! 
Gonna stay awhile this time?
Randy
Gosh I hope so 
I am very tired


9:17 PM
Sassy
You back in MA?


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Yes it is!

October 20, 2016 Thursday

12:32 AM

Randy
Yes it is!
5:09 AM
Sassy
Good morning hot stuff! 
Hope you have a wonderful Thursday!


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Funny good?

October 19, 2016 Wednesday 

2:45 PM
Sassy
Is funny good?  Hope so! 


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Tit cum plan

October 18, 2016 Tuesday

5:56 AM
Randy
Good morning miss sassy, sorry to be absent yesterday it was a very busy day and I am a bit under the weather. This morning I am off to Chicago for the next couple of days and then on to Colorado
Sassy
Good morning hot stuff! Hope you have easy travels!
Don’t think of my boobs….too much. 😉
Randy
Hey sexy lass, thx . 
Is there really such a thing as too much?
Sassy
Hee hee
4:25 PM
Sassy
Hope you made it easily and are having a productive day!
Randy
Yes flight was pretty good 
Meetings are delayed
so lots of standing around. 
How was your day?
Sassy
Rolled along. 
Prepping for a big event tomorrow
Randy
Nice I hope. 
Sorry for the delay 
people were talking to me here. 
I need to head into next meeting

9:19 PM
Sassy
Hiya 
Randy
Hey how are you?
Sassy
Great!  
I had a Chicago hot dog for dinner.  Thought of you… 
Randy
Funny 
I like it … 
I am in burbs. 

Sassy
Do they wine and dine you or are you on your own at night? 
Randy
On my own 
I had work to do
Sassy
You hanging in?  
Randy
Tired
Sassy
Sleep soon? 
Randy
3 hours of work still
Sassy
Oh no! 
Randy
Yes… how are you
Sassy
Well I won’t slow you down, just wanted to pop in and kiss you silly.  😉 
Randy
Ty 
it is always great to chat with you. How was your day?
Sassy
Busy but manageable.  
Trying not to worry about tomorrow’s big party.  
Randy
Oh for a bunch of people?
Sassy
150
Randy
So that’s a bunch 
I hope it goes well
Sassy
Should be fine… 
lots of good helpers, perfect weather. 
Randy
Yes
Sassy
You get your coworkers in good shape? 
Randy
Oh I like these guys 
The next stop is trickier
Sassy
Do your visits scare them? 
Randy
No I hope not 
I try and be collaborative
Sassy
🙂 
What do you have on? 
Randy
[photo from his hotel bathroom of him in gym shorts and a t-shirt]
[photo of him with the shorts pulled down showing off his cock]
Ok?
Sassy
Oh my… mmmm
Delightful! 
Thank you!  Mwah mwah! 
Randy
You like
Sassy
I want! 
Randy
[photo of the curtains]

Oops
Sassy
[photo of my cleavage
Randy
Ooooh very nice and suckable
[photo of the curtains with his erect cock]
Pretty good effect on me
Sassy
Was thinking about something from that second photo in between those
Wowzers!
You have such a gorgeous cock Randy!
Randy
Ty
Love your tits
Sassy
Thanks!  
Very happy to share them with you
Randy
God I could cum all over those
Sassy
I hope so! 
No one ever had
has
You could blaze a trail all over
and take a photo! 
Randy
Oh yes
Sassy
Maybe a short video, if there’s brain enough to swing it 
spurt spurt whee 
Randy
When I cum it is too intense to focus on anything else like that
Sassy
Yeah… I’d probably be too busy too 
Randy
I would want to make you cub again and again
Sassy
Okay. 🙂 
Randy
Or cum
Sassy
Yuppers 
You are so fun! 
Okay… you go back to work.  
And off to play and sleep for me! 
Randy
Ok good night 
I’m going to masterbate before I can work
Sassy
Ha! 
Remember my hand
and my lips 
Randy
Nite babe
Yes all of them
Sassy
MWah! 
10:02 PM
Randy
You’re funny


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