Randy Monday

October 3, 2016 Monday

9:19 AM
Sassy
Good morning! Have a marvelous Monday!
Randy
Good morning to you.
I hope you have a great day too.
In my 3rd meeting of the day so off to a busy start

Monday, October 3, 2016 4:12 PM
Randy
Hey there finally got a few minutes to myself.
I’ve been thinking about you hope your day hasn’t been too hectic
Sassy
Not too bad. Mwah!
Long hug
Randy
Kiss on your neck back to you
Sassy
Trying to plan October…get the info I need to cater 9 events
And plan days off
Randy
Wow that’s a bunch!
Can’t wait to meet you
Sassy
Is it fun or nervous to anticipate?
Randy
Fun very fun
Anxious and wonderful anticipation
Sassy
Good
I’m excited
Randy
Me to
Sassy
Makes me tingle to think of hugging. 
Laughing. Touching
Randy
Me too and love it
Miss the contact
Sassy
When did you last have a new meet?
Randy
Months
You?
Last one was odd. No chemistry
Sassy
Aww…sad
Busy summer for me…met 3 guys. First one disappeared in silence which was okay because he told me he likes to smoke weed every day
Second turned out to work where I do, decided fishing in his own pond was too risky
Third went silent after what I thought was a great meet…no clue on that one.
Randy
Oh boy
Sassy
Hope that doesn’t scare you
No sex with any of them
Sigh
Randy
I didn’t even kiss
Sassy
Did you talk awhile first and think might work?
Randy
Yes she showed up with her daughter 
teeth clearly not brushed
Arrrgh it was aweful
Or awful
Been a while
Sassy
Strange
Randy
Yes very
Sassy
I will definitely not appear with any offspring
Randy
Thx
Scared me
Kind of ruins that discrete thing
And your history doesn’t scare me
Everyone has a past and is searching online for a reason
Sassy
I go through cycles…no one for months, then a bunch, then nothing again
Randy
So you’re in the it’s raining phase
Not a bad place to be
I’d like to think I’m different at least 
I know what I’m looking for and try to take the time to think about who I’m meeting
Sassy
AM makes that happen. 
If I write to one guy, they somehow show me to 10 other similar men
Yes, i try hard not to waste men’s time
Randy
Oh I get a lot of PYTs emailing me with hey let’s hook up…. no thank you not for me
Oh put=pretty young thing
Or PYT stupid spell check
Sassy
Hee
Gotta drive now. More later?
Randy
Funny you got connected with someone you work with that must have been awkward
Ok I’m driving soon too and yes please Susan
Sassy
Well, there are a lot people where I work, so I thought we’d be okay
Randy
Oh yeah that should be fine

Monday, October 3, 2016 9:21 PM
Randy
Hey how are you?
Sassy
Great! You?
Randy
Alright
Long day trying to get my windshield fixed
Will go in the morning
Sassy
What happened to it
Randy
Rock hit it but the cracks keep growing
Sassy
Ugh
Randy
Yeah but the insurance covers it it will just be a little lost time
Sassy
Oh good
Randy
Yeah
Maybe I could take you on a really nice date?
Sassy
I’m game
Randy
It sounds like you’ve had some sucky dates?
Sassy
Dates usually okay but nothing after
Randy
Oh 
Sassy
Wish I could sense it
Randy
That’s tough
This whole thing is tough
Sassy
Eh.. win some lose some
Randy
Yeah – look I had a date where a lady stuck her finger in me. 
Scared the hell out of me at first
Sassy
And then?
I’ll tell you my plans, get consent
Randy
So we went to dinner, she picked a restaurant where her family was going to be.  Met her family that was weird played off of her story.  We went for a drive to a make out spot.  We started kissing next thing I know she is sucking me off with her finger in my ass.  A little too much all at once.  Took me forever to cum.  I went down on her and got her off and then fingered her off.  Then she started sending me crazy emails and stuff.  My work got really busy and coincided with her crazy emails so we broke it off because I was too busy
Ok would love to hear your plans
Sassy
Can be fun, increase anticipation
Randy
What’s that?
Clarise?
Sassy
If you or I say what is going to happen
Ha
Randy
OH yes
Im with you
I like happy people
Sassy
Do you share s bed with your wife?
Randy
yes
How about you and your husband?
Sassy
Yes
Randy
Sex every 6 months
Sassy
Random or some occasion
Randy
Random
She says sex is painful 
have tried all kinds of stuff.  
I think the pain is emotional
Sassy
Bjs?
Randy
Never
Sassy
Huh
Randy
I mean never 
she’ll suck him a bit but doesn’t want me to cum
Sassy
We have not done anything in years
Randy
She says hey it’s always good for the guy.  
I’ve tried tot tell her it isn’t always good 
even though there is a result
That is sad
It is funny with other women I can hold back often can wait forf them to cum
 with the wife I can’t … I’ve tried
Sassy
Interesting
Randy
Did your husband ever pleasure you?
Sassy
Not really
Randy
Same here
I thought that was what a relationship was and the sex would grow but it didn’t
Sassy
I didn’t know any better
Randy
I had better I just though I needed to get better at doing it
We would have sex once every 2 weeks to a month yet I would jerk off at least 1 if not 3x per day
Sassy
I really hope we click
Randy
I do too
Our relationships are sad
I guess it is what we do if we don’t know better
Sassy
But if not, it has been so fun
Randy
Do you think I’m running away?
Sassy
No
Randy
Know something I don’t know
Sassy
Nope
Randy
But yes it has been fun
You’re alright and I love your sense of humor
Catherine
Sassy
Giggle
Randy
I am still finding out who I am sexually
I know I like normal
Sassy
That’s great
There’s a word
Randy
I like a little bit of not normal
And am game for exploring
I love gals with big tits
I love gals who are happy and know how to kiss
I like real women with bigger than barbie asses
Sassy
Dirty talking?
Randy
Yes love it, you?
Sassy
Yes
Randy
Oh and I love loud
Sassy
Yes
Randy
I like long sex sessions and cuddling and fondeling
I am weird because I like holding hands and talking 
I like the tease either visually like a way too low cut blouse
Or a gentle finger placed to your lips just to let me know
Sassy
Any exhibitionists tendencies?
Randy
Maybe, you
Sassy
I like to fantasize but am quite shy
Randy
It has to be safe public
It isn’t really a fantasy for me
Do want to be caught doing something stupid
do not want
Sassy
Of course
Randy
You’re sexy to me.
Have high hopes for wednesday
Sassy
Oh yes
Randy
Sorry got sucked into show
This is us
Can I ask, dear Penelope, what do you need out of a relationship
Sassy
Talk, touch, laughter, to be needed and wanted
You?
Randy
Pretty much the same, funny for you and me sex is low on the list
But it is a strong need
I guess it comes from everything else
Sassy
The more I get, the higher it gets on the list
Randy
Same here
It is important but I’m looking for a relationship.
Need passion 
It stems from all the basics in a relationship
Too deep?
Sassy
Not at all…makes way too much sense
Randy
Yeah I guess were in the same boat
Life’s not supposed to be this complicated eh?
Afraid to fall in love?
Sorry I get a little sappy when Im tired
Sassy
Try not to but can’t control it exactly
You’re cute when you’re sappy
Randy
I am a bit
Thx
Afraid that I’ll find out that I wasted a lotto my life
lot of
Sassy
Maybe but good you’re searching for better now
Randy
Yes I guess
Okay sorry I’m a happier person than this
Sassy
I know
Hope to make you even better
Randy
Thx
You’re alright Abigail
Sassy
Solve the problems of the world together
Or fuck really well
Randy
Oh yes but that would be on the first date 
what do we do for a second one?
Like that too
Need some intimate connection
… without a finger in my ass at first
Sassy
Practice until we get it right
Randy
Yes
Sassy
Duly noted
Randy
Just give me a heads up
And I’ll do anything you want
Sassy
Oh your head will be up
And dripping
And warm
Randy
Yes nice
Love to fuck
Sassy
Mmmm
Randy
Love to give oral
Sassy
I want to undress you
Randy
Slowly please
Sassy
Look at you
Randy
With lots of kisses
Sassy
And caresses
Randy
Yes very much
I want to explore you
Sassy
Be easily naked
Randy
Bring to orgasm sweetly
I love your body
Very sexy
Especially for someone named Prudence
Sassy
Ha
Randy
I try
Sassy
Can you sit around naked?
Talk, snack naked?
Randy
Yes
As long as were cuddling
Would love to have my cock in you while we discuss the day
Straddling me face to face
Sassy
Imagine a woman who wants you, welcome your touch
Randy
That would be phenomenal
Sassy
You can touch me
I will touch you and smile
Randy
Nice
Very nice
That would be lovely
very sexy
Deep kisses
Sassy
Look for ways to be naughty
Randy
Yes please….
Sassy
Tempt you
Set you on fire
Randy
Yes I like taunting too
69 with tits rubbing against by stomach
pussy dripping on me
I can just picture it now Fiona
Sassy
Might need to tour your skin with tits
Hee
Randy
I would love that
Cover them with cum
Sassy
You need to sleep?
Randy
Yes I need to head off now early morning
It has been great as always
Sassy
Sweet sexy dreams
Randy
Same to you my dear sweet Angelica
Sassy
Snort
Randy
I’ll get it right sometime
Now its a sport
Sassy
Good night
10:43 PM Randy
Good night hope to chat tomorrow
I have a dinner meeting until late tomorrow

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So I might not be on until late


Tempting Brett

October 3, 2016 Monday

From: Sassy
To: Brett
Sent: Monday, Oct 3, 2016 11:54PM
Re: The week that was
Hiya Brett! 
Happy October!  Hope this month is off to a good start.  It was so good to see the sun today after so many gray days.  
We buried Mom’s ashes on Saturday, standing under umbrella’s in the rain reciting poetry and singing a hymn.  Good to have that done.  My cousin came from NC – I took her up to Essex for lobster on Sunday. 
Work has finally calmed down after the crunch.  My new boss is getting worse.  I am thinking of taking off on Friday, if you happen to have time to play.  
Hope your dreams are sweet and sexy! Mwah! 
-S


Sunday Randy chats

October 2, 2016 Sunday

7:06 AM
Randy
Good morning
Randy
Hope you had a great night.
Been thinking about you this morning
Sassy
Good morning!
Randy
Hey sorry was cleaning the kitchen
Sassy
Now that’s sexy!
Randy
Yea kids made a disaster while we were out
I try and help
How are you today?
Sassy
Great! Have only made it from bed to bathroom so far…
You?
Randy
Good.  been up for a few hours doing a little cleaning
Going to do some siding in a bit
Have to start packing of army trip
or for my trip
Not a morning person?
Sassy
I can be but not today!
Randy
It is cold wet and dreary
Perfect day for staying in bed
Sassy
Made it to my desk
Randy
Nice
Im sitting in a comfy chair watching Gold RUsh
Trying to worm up before heading outside
SO any plans today?
Sassy
I’d like to warm you up
Randy
That would be very nice
Spend all day in bed
And make love all day
Sassy
mmm
Do you drink coffee in the morning? 
Randy
Are you insatiable?
Diet Pepsi
Sassy
oh my
Randy
Tried coffee can;t drink it
You?
Sassy
I’m satitable… but then it wears off
When I went to college, the older women told me I would learn to drink coffee, stay up all night and stop listening to John Denver.  
Randy
funnt
or funny
Sassy
Never did! 
Randy
Still like John Denver?
Sassy
Yeah… he’s fun and sweet 
Have to figure out where to take my cousin for a lobster roll 
Randy
Yeah I play some of his stuff 
I think my favorite to play is Grandmas Feather rBed
Sassy
Poems and Prayers and Promises 
Or Thank God I’m A Country Boy! 
Randy
Aren’t there pretty good places near you?
Both strong as well as This Old Guitar
Sassy
It’s good traveling music 
I sing along.  
Randy
Apparently my typing still sucks
FUn
Sassy
Don’t worry… I know what you mean
I was thinking to take her to CK Pearl in Essex but it hardly seems worth it with this mist
Randy
That is a bit of a drive but not far from me
Sassy
I like the food at Lobsta Land better but the view is better in Essex
May just go out to Belle Isle Seafood in Winthrop
Randy
Purple Cow in Newburyport
Sassy
Never been there!  
I’ve been to Micheal’s on the waterfront… 
Randy
Sorry I meant black cow.  And Michaels is good
Sassy
And that other place… um… Starboard Galley
Randy
Never been there
Sassy
With this weather, the 99 might be the answer 
Randy
Funny
Sassy
She’s a down home kinda gal, more impressed with cheap and good 
Randy
My family hates the 99 not sure why
Sassy
My mom adored it. I took her out for lunch every Saturday and about half the time she wanted to go there 
Randy
Nice memories
Sassy
That or the Chinese buffet 
Randy
Wow nice
Chinese buffet scares me a bit
But then Im a bit food phobic
Sassy
It was so odd because my dad was a steak and potatoes guy so that’s all they did, and when he died, she was like “How about Mexican or Indian today?”  and we were weirded out 
Randy
Funny 
sounds like she wanted to see him happy
Sassy
Oh yes.  It was great to see her become her own person 
They always had white sheets.
When he died she bought PINK FLORAL! 
Randy
Wow
Sassy
Lots of little things like that 
Randy
Funny
My wife has a list too
Sassy
Oh? 
What she’ll do when you die? 
Randy
Flower sheets is one of them
Sassy
I did that when I got my own place. 
Randy
She wants a roommate
You have you own place now?
Sassy
My room mates were plain, plain, plain… white paper towels, white shower curtain, white dishes 
I got patterns and as much dark blue as I could find! 
I bought a condo when I turned 30 
Randy
Oh IC
My wife is pastels 
I am more bolds
Sassy
Decided I was probably never getting married, might as well get on with being a grown-up alone 
I’m the navy blue gal
Randy
Oh ok
I like blues.
Sassy
I am not girly in many ways 
Randy
I want a robins egg blue Austin Healey
Sassy
Do they make that? 
Randy
Yes It is a 60’s car
Sassy
NO florals, no make-up, no perfume, no shopping, no collectibles! 
No cooking, no crafting, so sewing, no cleaning.  
I need a wife.  Heh 
Randy
[messed up URL]
Sorry let me try that again
Sassy
Purdy! 
Randy
Yes fun
Sassy
http://www.kruseclassics.com/index.cfm?id=209&auc_code=A14&lot=228
Randy
I like your list
Sassy
Seems like too small a car for you
Randy
The Bigeye is but the “Big Healeys” are a better fit
Sassy
It can be good for you… I won’t get lipsitck on your collar or perfume on you sleeve 
Randy
Marry me?
Sassy
Maybe in a week or so.  🙂 
Randy
You seem like you’re well grounded
I love the list
I have crafting hoards around the house
LOL
Old GF left lipstick on the little man once.  
I didn’t catch it until I got home. That could have been bad
So It sounds like you’re the pragmatic one
Sassy
It’s just how I am… 
Randy
Me too
Sassy
I despise pink… 
When I was sick everyone gave me pink this and pink that… bleh 
Randy
Oh that should have been BugEye
Sassy
I had to smile and pass it on to others! 
Randy
I am more of a woodworking handcar guy
Sassy
That’s handy
Randy
I meant to ask… hopefully this isn;t too personal why not get divorced?
Sassy
I made a promise 
And he can’t really function on his own
Randy
Oh
Sassy
He’s very talented, creative
Randy
And yes I am very handy
Sassy
but can’t balance a checkbook or remember to pick up his meds 
Randy
Oh jeez
Sassy
He’s on disability 
Randy
It is pretty good of you to keep your promises
I plan on getting divorced at some point
Sassy
We’re a good team, just not in the bedroom 
Randy
Just found out wife has been hitting daughter so may be sooner than later
Oh OK
Sassy
WTF?
Randy
Yeah  my daughter talked to me Friday
Sassy
That is not right. 
I’m so sorry you have to deal with that! 
Is that a new thing?
Randy
Yeah I’ll figure it out. 
My daughter was really mad at her mom so I want to make sure she isn’t exaggerating before next steps
She told me it has been happening for years
I was unaware
I saw her hit her once and I told her if I saw it again that would be it
My father was brutal and I have no tolerance for that
I’ll figure it out
Going to talk to daughter this morning
Sassy
oh dear… 
Randy
Yeah life is tough sometimes.  I have worked out a backup plan
Sorry to bring down the mood
I will alway protect my kids
Sassy
It’s fine to talk about whatever
I want into your head 
Randy
Ok and thank you
I’m a decent guy
Pretty down to earth.
Love science things
With a very high libido
and love to please
Sassy
I’m going to check that out. 🙂 
Randy
Please do
You can give me a grade sheet
Oral:
Making love:
Kissing:
Sucking nipples :
Sassy
Hee hee
Randy
Attention to needs:
etc
let me know
Sassy
It can make things much better if we can talk about things… ask for more or slower or whatnot… 
Randy
Yes I take instruction well
Sassy
Me too 
Randy
Ok a little more about me. I try to be discrete not only because of the family but also I have a fairly high level position and also hold elected office
Sassy
Eep
Randy
I love BJs but then who doesn’t
I love to give in return
Hang on need to pee
Sassy
I’ve actually been with two men who didn’t like BJs… kinda drives me crazy not to be able to use my talents in that way! 
I thought it was just that they had been with women who weren’t good at it but no… 
Very relieved to hear you do! 
Helps a lot if you can cum more than once
Randy
Yes I can cum about 5x
I do like at least 1 kinky thing and not sure why
Sassy
What’s that? 
Randy
If you give me a BJ hold it in your mouth and french me
Too weird?
ut oh did I scare you off?
Sassy
Not at all 
Randy
How about you and kinky desires
Sassy
we can snowball… pass it back and forth.  Heh 
Randy
You like that?
Sassy
I don’t even know what anyone considers kinky anymore 
Randy
True
Sassy
I used to think anything other than missionary in the dark was wild 
Randy
Funny
Sassy
I did! 
I’ve read a lot about different things, tried things… 
mostly come back to… not vanilla but… butter pecan?  
I like nuts. 🙂 
Randy
I like your style
3 comes are a bit much to me
that should be threesomes
Like to focus on 1 person
Have you dated much?
Sassy
What counts as much? 
Randy
Not sure
Sassy
I don’t dream of 3’s 
but might go along in the right circumstances 
Randy
>1 suitor a month?
Sassy
I am mostly a one man woman 
Randy
Agreed 
Sassy
I was in a 4some once in Mexico a long time ago 
Randy
what configuration?
Sassy
MFMF
Randy
how was it?
Sassy
It was glorious
Randy
really ?
Sassy
DIdn’t track who was doing what, just enjoyed 
Randy
were you with the girl ever?
Sassy
I tried once but I am 100% het
Randy
me too
Sassy
A friend from work got really drunk 
and I had to take her home and put her to bed 
Randy
That might be okay more 1:1 ish
Oh
Sassy
She came on to me and I thought i could but.. eh 
Randy
Oh awkward?
Sassy
She didn’t remember any of it 
Randy
Good
Sassy
She fell asleep right about the time it was getting bad 
You tried with a guy? 
Randy
I won’t fall asleep on you primise
promise
Kissed and that was it mostly.
Sassy
I think it’s good to explore 
Randy
my two best friends went at it when I was in the bed next to them though
they thought I was passed out
Sassy
I would think a guy could give a really great BJ, he’d know what works 
Randy
I am definitely het though
That’s what a gay friend says 
who knows more about what a guy wants more than another guy
I think that is a bit false
Sassy
I see a lot of girl on girl porn and I watch a little to see what they do 
but it doesn’t get me going 
Randy
Me either funny
What about anal?
Sassy
It looks really sexy in theory but in practice I don’t see how it works… 
Randy
some like some don’t some only at the right time
Sassy
I got torn up by a guy a long time ago
Randy
Need lots of lube
Sassy
But with lots of lube might try again 
heh
If the guy really wanted it, I’d try 
Randy
Know its only worth trying if you like it
Sassy
I know younger guys like it 
because they can go bareback 
and avoid pregnancy 
but that is not an issue for me anymore 
Randy
I’ll finger your ass while going down on you then you’ll know
Sassy
I did do a prostate massage on a guy once 
while sucking him
Randy
Did he like it
Sassy
Nothing like hearing a man say, “That was the hardest I’ve ever cum in my life!” 
Heh 
He said he felt like he was cumming for the whole time…. 
Randy
I went on a first date and it got hot and heavy 
next thing I know she is sucking me off with her finger in my ass it was a little weird
Sassy
He was used to being with Pros and I was a little intimidated but he said I was better! 
Oh my… not first date material! 
Randy
I’ll try it again though if you want to… I’ll just have to prepare first
Sassy
First dates are often really weird… please try not to judge 
Randy
Never been with pros and don;t have any interest
I am not judgemental
Cast not the first stone…
Sassy
I’ve had first dates that were disasters but after that it was fine. 
Randy
Do you date more than one suitor at once?
Sassy
Not very often 
I may be talking to a couple of guys, waiting to see what pans out 
Randy
Okies I know the feeling
Sassy
but never long term 
Randy
really?
Sassy

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If I get past the first date I usually focus on that guy 

Randy
I am looking for something on many levels
Sassy
I’ve never left someone… 
Randy
that usually leads to long term
Sassy
I expect it to last forever 
Randy
Guys are turds sometimes
Sassy
I get it
I don’t get lying or slience
but I get the new pussy appeal 
Randy
Yes
And fun but I find the second and third can be phenomenal
etc
Sassy
I like getting the learning about someone new but then using it over and over to make it great 
Randy
Me too
Sassy
And building trust 
Randy
Pay attention
Yes
That should be I pay attention
Sassy
I got attacked once so I changed how I start a
nd am way more careful, but it makes first dates a bit terrifying 
Randy
Oh shit that is terrifying
Sassy
It was… and the fact that I had no warning… 
no way to tell if the next guy would be like that 
Randy
Very scary
Im not that guy 
I respect women
I’m a pretty normal guy and I have a fairly public life
Sassy
Here’s a fun site 
http://www.sexinfo101.com/sp_deckchair.shtml
I learned a lot about different positions 
and the animation is oddly hypnotic 
Some of the desciptions and comments are hysterical 
Randy
My cock isn’t huge which limits some things
Sassy
Some of them look like something out of Cirque de Soleil 
Randy
But women really hate it when you bottom out
Sassy
I’ve had fun with all sizes 
Randy
Does’t want to open for me right now
Sassy
I find smaller men learn to do more than pound 
I like doggy a lot 
Randy
Ok
Sassy
or the up from under type side thing 
Randy
I’ve never been with a woman who I didn’t make cum by fucking
except my wife
Sassy
oh that is sad
Did you do it before you were married to her? 
Randy
yes but I was young and naive
Sassy
A finger and tongue can often be better for me 
because I’m a clit girl more than a g-spot girl… but it varies a lot 
Man…. you have me revved up
Pulsing over here! 
Randy
When I started dating my wife she said most women can’t cum with fucking
She used to take an hour to cum and I would tongue her that long
Sassy
Wow
This may qualify you for sainthood some day
Randy
Yes I then cheated 
I met with a woman she came in like 30 seconds (and I can tell)
She came almost 5x in about 1.2 an hour
My wife used to complain that my cock was too big and I was going too deep
I then learned that might be desirable
Sassy
Fascinating 
Randy
My old high school GF found me 
and we hooked up because she said I was the only guy ever that made her cum
I thought that was very sad that guys would treat her that way
Sassy
I definitely want to check this out! 
Randy
I made her cum 4x on the first date
Sassy
There was one guy that made me cum 7x in 2 hrs… I lost count after that 
Randy
2x which making love 1x fingering and 1x oral
Then she was tired out or I would have kept going
Sassy
And a guy I met for nearly 9 months who never made me cum
Randy
Hmmm
I am told that I am a good kisser and great with oral and my hands
I think it is more that I pay attention
Sassy
I am “the best kisser ever.”  😉 
Yes.. that is key 
Should I let you go do stuff? 
Randy
Awesome I love kissing
Yes in a minute
Sassy
I lost track of time… I adore that 
Randy
I’ll have to check that out
Me too
Sassy
Yes please! 
Randy
Maybe Wednesday?
Sassy
Yes
It’s an important piece of info to discover 
Randy
Yes I love to kiss
Love to do much more
I like the exploration
Sassy
I want to hug you right away, like an old friend 
Randy
To me the sound of a woman climaxing is very very sensual
Me too could use it this week
and kiss you like a new lover
Sassy
Do you need to be careful in public? 
Randy
A bit
But I am very add and can quickly spot in a room people I know
Sassy
Should have a story ready so we don’t fumble if you see someone you know
Randy
But we should be okay
I always do
dear old friend
Sassy
If I see someone, you are talking to me about donating to my community group.  🙂 
But I’ve never run into anyone 
Randy
Ok
Sassy
It’s really tough not to be bad in public 
Randy
I did get caught one time
 and the guy was being nosy 
I said she is an old friend that is having a hard time so back off so that we can go and fuck for a few hours
…. he thought I was joking
Sassy
Ha! 
I went to a guy’s house one time (won’t ever do that again!) and his wife came home unexpectedly
Randy
I  would never do that
Sassy
Luckily, he had shown me the closet where I could hide 
Randy
How did that work out?
Oh boy
Sassy
He’d put a chair in there 
Randy
Not my style
Sassy
So I sat there listening to her scream at him 
Worst part was later when I asked why she screamed at him over little things and he said, “Was she?  I didn’t notice” 
Randy
Sounds like my life
Sassy
It made me realize why he would brace himself sometimes when he told me something 
He was waiting for me to scream
And I never yell 
Randy
That sucks
Sassy
He was really into me being in his bed 
I did it that once to please him 
Randy
Weird he needed to spite his wife
Sassy
Yes. 
Randy
No my focus is on a relationship
Not vindictiveness or any other odd emotion
Or to satisfy ego
Ok I should go and get some stuff done
I really want to masterbate with you
Sassy
Hope it goes well! 
Randy
but family is around
Sassy
I think we can have a lot of fun! 
Randy
would’ve to hear you cum
I think so too
that should be would love to hear you cum
Sharon?
Sassy
Ha ha
Randy
Maybe could kiss you in public
Sassy
I’m going to go play
Randy
could I listen?
Sassy
You can think of me lying on my bed, legs spread 
I have to be pretty quiet here 
Randy
Oh well
Sassy
BUt you can imagine 
Randy
Yes I have a good imagination
Sassy
Phone in one hand, big silver bullet in the other 
Randy
Nice
Wish my tongue were there
Sassy
You sitting in the corner jerking off 
Whee! 
Mwah! 
Randy
I’ll cum on your tits
and then rub it into your nipples
Sassy
mmmm
No one has ever done that 
I want that! 
Randy
I cum a lot just to warn you
Okay I should run I could talk to you all day
Sassy
That bodes well!  
Randy
I hunger for you babe
My balls ache
Chat later?
Sassy
Yup
Randy
Catch ya later.
Have fun pleasuring yourself
Think of my face between your legs
Sassy
Mmmm… 
Randy
Bye babe chat later

Sunday, October 2, 2016 6:18 PM
Randy
Hey I had a few minutes so I thought I’d say hi
Hope you had a good day
Sassy
Hiya! 
Done with dinner. We did go to Essex. Thought of you…
Randy
Very sweet of you 
how was dinner?
Sassy
Delightful
Spicy lobster carbonara
How was your day?
Randy
Good a bit tired lots of work.
Doing smeo electronic stuff for work now
The spicy lobster sounds wonderful
Sassy
What did you eat tonight? 
Randy
Um nothing exciting Firehouse subs.. turkey sub
small
going for the next 50 pounds
Sassy
Sounds yummy 
I was super bad… 
There’s a fresh pie stand at a farm on the way in to Essex… 
I hadn’t had pie in forever, so I stopped and bought two! 
Of course, I had to try them both when I got home 
Randy
What types of pie?
Sassy
Cherry and Burgandy 
Randy
I love cherry… my favorite
How were they?
Sassy
I think I may take them to work so I don’t eat any more
Perfect 
I’m not usually a dessert person… but sometimes… mmmm
Randy
I’m the same way
But I love cherry pie.
My brother and I tried for a while to retreat the recurring scene from Twin Peaks, cherry pie and coffee
We found a place in Oregon that was perfect
Sassy
You said 4 siblings? 
Randy
Yes 2 brothers and 2 sisters, 3 steps sisters
Sassy
Wowzers
Randy
yeah catholic family
Sassy
I have one sister 9 years older and 1 9 years younger 
Randy
wow that is a pretty big spread
Sassy
My older sister is… a challenge 
She tries to mother us 
So I tend to avoid her 
My younger sister is my best friend 
So most of the time when I talk about “my sister” I mean the younger one 
My older sister was a “honerymoon baby” born 9 mos and 5 days after my parents got married 
Randy
Better than 7 months for a cousin of mine
Sassy
I took a long while to come along 
“premature”  🙂 
Randy
took 9 years to perfect you?
Sassy
My little sister was a complete surprise when my mom was 43 
Are you the youngest? 
Randy
Oldest
Sassy
Aha
Randy
And I guess that is where I get the leadership qualities from
Sassy
I am the middle child, the peacemaker 
Do you get along with them all? 
Randy
Yes… I avoid one of my sisters when her husband is around he is a bit much for me
My one brother just started remembering his childhood so he is struggling a bit to deal with it.
I have been helping him some.
I have or really had a nearly eidetic memory SO remember almost everything
Sassy
Is he getting help? 
Randy
Yes professional
Both brothers 
I dealt with the issues a long time ago.
always thought they were more mentally healthy than me because I confronted issues 
They seemed to make their peace with them
I didn’t think it would stew within them for 30-40years and then erupt
ever had anything like that in your family?
Sassy
No but I have good friends who dealt with it, or didn’t 
Do they live near you? 
Randy
No they were in the Midwest.
They both almost died in the past 2 years
Sassy
Yikes 
Randy
Funny I had the troubles in High School and was done with it
The brain is a complicated organ
Sassy
 Indeed
Randy
It seems like they are both in a much better place now
SO I am happy of rthem
Sassy
 When are you going away? 
Randy
Saturday
Meetings all week.  Back for the weekend then off again Monday- Wed
Very long trip
Sassy
So out the 8th, back the 14th, then out 17 and back when? 
Randy
Gone 8-14
back 15-16, then gone 17-18 and maybe longer
Tough couple of weeks
Also budget time
Sassy
So if we decide we get along… it will be weeks before we can act on it? 
Randy
yes sadly
Sassy
Ah well
Randy
Too long for you?
Sassy
Hope we can keep talking, teasing, anticipating 
Not at all 
Randy
Yes I need to set up my wifi but I should be good
Sassy
I got this new phone in May, people says it makes international travel a breeze because it just works… 
Have you heard of Google Fi? 
Randy
Yes never tried it.
Im not sure if my iPhone will work
Sassy
It halved my phone bill
Randy
I know people like the Google phone
Sassy
It won’t… that’s the one big con 
Randy
Yes prefers wifi.
Sassy
You have AT&T? 
Randy
Yes I do
Sassy
I am smiling… thinking of meeting you are the airport… getting way ahead of myself! 
Randy
I thought it would work
Sounds fun!
Sassy
You’ll probably be a fuzzy jet-lagged mess 
I envision you are a big cuddly teddy bear… is that right at all? 
Randy
Yes I am 6’3″
Sassy
Wow!  
Randy
OK?
[Sent me a nude photo]
Just took that
Sassy
That’s quite a photo! 
Yum… 
You have shoulders… 
I have a sucker for shoulders! 
Randy
Yes lots of muscle too
Sassy
So you’ll win at arm wrestling? 
Randy
yes
Sassy
Hee hee
That is such a HOT photo!  Thanks! 
Randy
he is at about 1/4 hard so decently thick I don;t normally look
Need to lose the belly
Thx
Yea big shoulders great for hugs
Just so you know what you’d be getting
Well I hope you like
Maybe I should have warned you before sending
Sassy
[photo of me just out of the shower casually wrapped in a towel]
Randy
Now?
Nice tits! 
I like it
You’re cute!
like the careful towel placement
Now I’ll be busy later tonight
Sassy
🙂
Thanks
Randy
Sexy!!!
Sassy
I try to be a little creative… a peek is sometimes better than the whole shebang
Randy
Yes
I like it
Was that just now?
Sassy
Nope
I am rarely a real time photo sender
I usually take like… 12 and delete them all… then try again… then… 
Randy
Oh IC.  I felt spontaneous
SO I’m okay for you then?
Sassy
That was very special 
You are fantastic! 
Randy
TY
another 30 pounds and my belly will be gone
Sassy
My fingers itch to touch you there… and there and…. there 
Randy
My arms are always huge
and very nice
love foreplay
Sassy
You do have tree trunk legs! 
Randy
Yes I used to cycle 45 miles a day
and no fat there
Last time I took a pic like that I was much thinner
In the old days my cock could touch my belly button
Those were good pics
like your arms and soft shoulders
You are a very sexy woman
Sassy
Thanks… my skin is so white.. 
Randy
I like the middle nipples but just enough to show that you have some very nice tits
that should read hidden nipples
and a pretty crotch
your probably hiding a lovely pussy
and there I have made a grammatically error that I hate… you’re
Sassy
It’s funny what that random photo shows and doesn’t 
Randy
I like it
love demure 
Like the scene from total recall
Be honest it will make the whole experience more pleasurable
BRB
Okay back
Sassy
🙂 
Mirrors are good… can stand or lie in front of them and get new sights 
Randy
I can never seem to take a good mirror photo
Sassy
I saw a video where the woman was on the bed and the guy was standing and he could see in the mirror while she sucked on him… looked like a great idea! 
Randy
Oh sounds interesting 
although whenever it has happened to me I am too lost in the moment
Sassy
Mmm… nice 
Randy
Then cum all over your tits
Sassy
I never get to see that… I want to!  
It’s always somewhere inside me so I can’t see 
Randy
Nice sounds like fun then
Sassy
I’ve only seen a man cum once… when I had a bad cold and had to do a hand job instead of sucking 
Randy
Oh well then that is something to try then
Sassy
Could be fun? 
I may have to send you my favorite hand job video
Randy
Yes If you suck me to almost coming and then I jerk off sometimes I can cum for a while
like multiple ejaculation.  But that usually wears me out 
but I cum a lot when I do that
Sassy
I want you to feel so good 
Randy
the best is sucking hard when I cum it empties me and feels out of this world
Sassy
I can usually do that 
Swallow all around you 
Randy
very nice
Cant wait to kiss you
and hug you
Sadly my sweetness I need to head off to bed.
I need to get up in a few hours
Sassy
Here’s a 1 minute video to take with you
Sleep well Randy
Randy
TY and I hope you sleep well to.
Chat tomorrow?
10:58PM Sassy
Yes please!


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Brett checks in

October 2, 2016 Sunday
From: Brett
To: Sassy
Sent: Sunday, Oct 2, 2016 11:11PM
RE: The week that was
Sassy,
Sorry for your losses.  It reminds me how lucky I’ve been and that I  should not take life for granted.
I’ve been busy as well, cleaning up around the house…as task that after years of accumulation seems to have no end.  Also at work my project is just starting to come up with deadline after deadline.  I got a new computer at work and need to get all situated with that.  
Other than that, life has matched the weather lately, dreary.  Leaves me mostly with my dreams….

brett


DInner on the river

October 2, 2016 Sunday

9:59AM Phil

Heading home! 

7:38PM Sassy
A gray afternoon at CK Pearl in Essex with fantastic food and fabulous company!  Took my cousin out for dinner along the river.  
Oysters! 
Island Creek, Spearpoint, and two others I can’t recall.
Spicy lobster carbonara

Jester thanks

October 1, 2016 Saturday

from: Jester
to: Sassy
date: Sat, Oct 1, 2016 at 4:57 PM
subject: Dessert

Sorry for the delay-haven’t been able to get on line. Enjoyed lunch very much yesterday, and the taste of dessert! Will write more when I have a chance.

=====

from: Sassy
to: Jester
date: Sat, Oct 1, 2016 at 5:14 PM
subject: Re: Dessert

Hiya D! I had a strange day, standing out in the rain to bury Mom’s ashes, big lunch with family… but all that is over. When it got bad, I thought of us being naughty and I could smile again. Ha! Hope you’re having fun!

=====

WOW! He wrote back.  I am surprised.  But he didn’t write much.  Hmm… once again, it won’t surprise me if he doesn’t write more.  Just does not seem enthused.