Jester to gmail

September 28, 2016 Wednesday
Date:Sep 28th – 8:23am
Hey Sexy Lady, Absolutely let’s chat-you’re getting me all fired up! lol 

I’m usually available during the day to chat-and I’m up for “adventure” too. I have a light day today-one appointment this afternoon. What are you up to?
Date:Sep 28th – 8:58am
So I wrote this nice long message and when I sent it I was “timed out”…. So now I will try to reconstruct it but I know it won’t be as good….. 
Thanks for the last email but don’t worry about wasting my time, I’ve always felt good conversation and some laughs are never a waste of time. 
Curiosity is good, killed the cat-who likes cats anyway…..just kidding. 
I like the idea of the “boobs thing” going on….not sure what that means but I like the sound of it. 
How do I respond to “hugs with groping” …hmmmm, How about kisses with a light touch of the tongue on the neck???  J
Date:Sep 28th – 12:08pm
Hiya J, Hope you’re having a wonderful Wednesday! 
Thanks for your messages. Sorry about the time-out thing… AM’s interface is rather bizarre. If you want to switch to email or something else, let me know. 
What do you wonder about that might help us figure out if we’ll click? Chemistry is so tricky… Here’s three questions for you: 
Have you been in MA all your life? 
How old were you when you first had sex? 
If you could take me to any concert in history, what would it be? 
I wish you were around the corner right now and could go to lunch and eat and laugh and then find a quiet place and rock each other’s worlds! Mwah! 

Date:Sep 28th – 2:29pm
So did you know the Urban Dictionary defines Sassy as: 
1. A bitch who sasses everyone. 
2. A dog who refuses to eat her food. 
3. A tiny penis with big balls 
I’m hoping you’re not the last two….lol 
Kind of a drab Wednesday…although rain makes me horny…. 
My secure email is: [redacted] 
With regard to your questions: 
Have you been in MA all your life? 
Yes with the exception of a year of college. 
How old were you when you first had sex? 
I’m still waiting….but really 16. 
If you could take me to any concert in history, what would it be? 
Jimmy Buffet in Key West 
I’m up for lunch, I’m around tomorrow-not too far away….
switched to his gmail
From: Sassy
To: Jester
date: Wed, Sep 28, 2016 at 2:52 PM
subject: Connection
Hiya Jester! 
How’s it going hot stuff? 
I usually adore the Urban Dictionary… it has taught me a lot.  In this case they are way off!  In my case, the term means a Scottish Lady who will tell it like it is!  
Rain makes me want to stay home under the covers with a man who wouldn’t mind a long conversation punctuated by sex here and there, and a naked nap cuddled around each other. and cocktail shrimp and chocolate-covered potato chips! 
I was raised in upstate NY, came to MA for college then went to visit my older sister in Somerville “for three weeks.”  Stayed with her until I bought my own place years later.  Ha.  Been here ever since.  
When I was 17, my high school sweetheart and I kissed and cuddled for 4 months, going a little further and then a little further and then one day… all the way.  It was… dull.  We had no clue.  We puzzled over why the adults liked it so much!  I’ve learned quite a bit since then.
Aha!  A parrot head!  Have you seen Jimmy?  I’ve never been but I have friends who go all the time.  Key West is beautiful… I was there in March after Hurricane Andrew, marveled at how Miami was a mess and the Keys were mostly fine. 
My my… you are eager!  I can’t do lunch tomorrow.   Work meeting midday.  Would Friday work?


Bon voyage

September 28, 2016 Wednesday

8:10AM Sassy
Good morning kid!  Have a wonderful Wednesday!

8:49AM Phil
Good morning!  
On the boat at 1:00 and underway at four. Be nice to be on the water again
11:52AM Sassy
Bon voyage!
12:07PM Phil
Thank you!
2:52PM Phil
[photo of his hand holding a drink and a hot tub on the deck of a ship]
4:13PM Sassy
Roughing it already?
Wish I was there to put my hands under the water in a very naughty way!

10:46PM Sassy
The Red Sox are officially American League East Champions!  Woohoo!

Heavy petting hopes

September 27, 2017 Tuesday
From: Randy
To: Sassy
Sent: Tue, Sept 27, 2016 at 7:05 AM
Re: Connection
Hey great to hear from you,
Of course loved the pic.
I should apologize for my last email I shouldn’t write during political debates.  
As far why I work where I work, it is more that the city chose me.  The industry I work in has lots of offices there.  I love the field I am in as I love the idea that I could potentially help many people at once.  Yes I have been success and am one of the executive types,.  At my last job I had an administrative assistant who took care of tons of things for me.  I appreciated her very much because without her, I wouldn’t have the time or frankly ability to do many of the things I was able to do.  I hope you do get some appreciation where you’re at.
Where would I take you for a concert in all of all time?  That is a tough one, I would have to say Woodstock.  Perhaps that is obvious but it was a transitional time in American history that I would love to experience.  I really enjoy some of the music but that would be more about the experience.  I would have loved to have seen Johnny Cash, Ray Charles, the Sex Pistols, and the Grateful Dead.  It would also be tremendously interesting to seen original Shakespeare at the Globe (I know, not so much a concert, but more of a spectacle?). 
As far as geeky things, I like museums, I like all things mechanical.  I love trying to understand how someone identified a problem and figured out a solution.  Or took something seemingly mundane, such as how a wheat field is harvested, and turned it into something transformative, like the TV (Philo Farnsworth).  
So might I ask what kind of relationship are you looking for?  As for me I am looking for a LTR, a discreet one.  I basically have a roommate and I want much more.  (I will spare you the details)  I am a very passionate person who loves life and wants to explore much.  
Looking forward to your response with heavy petting hopes,
From: Sassy
To: Randy
Sent: Tue, Sep 27, 2016 at 8:05 AM
Re: Connection
Good morning!  
Hope your day is going well despite the dreary weather.  
You’re email was fine, especially if you had that farce going on in the background. Tell me you are not a Trump fan.  
Aha…so you are in the city during the day.  How convenient!  Thanks for noticing admin folks.  It can mean more to hear “thank you” than most people realize.
That photo is me in so many ways…demure but sexy.  I had breast cancer five years ago, so I get to show them off now, right?  I am whole and healthy and want to live life to the fullest!
I have to drive now, will answer more soon but I wanted to give you a nice morning message with a big wet kiss with my hand stroking your cheek and my other hand woven into your hair!
Sent from Yahoo Mail on Android
From: Randy
To: Sassy
Sent: Tue, Sep 27, 2016 at 10:59 AM
Re: Connection
Yes the city is convenient in many regards and may prove to be wonderfully convenient someday if things work out with you.
Music wise I do like folk music but I would be hard pressed to name any artists.  I like most music although I can’t really take rap. How about you – what would be your concert of choice?
I will admit that politically I lean to the right but I certainly am not a Trump fan by any stretch.
As far as admin folks I constantly thank them.  They make a world of difference.
Regarding your picture:  I love demure, I love the tease.  Getting through breast cancer is a huge deal and I am glad it is a life affirming experience for you.  I have seen many people go a different direction with those challenges.
From: Sassy
To: Randy
Sent: Tue, Sep 27, 2016 at 1:30 PM
Re: Connection
It’s lunch time at my office and I want to spend it with you.  Well… as best I can right now.  
The big question is can you touch an older woman with long gray hair and curves?  And let her touch you?  I know… there’s no way to tell online.  Chemistry is such a tricky thing!
When I mention folk, most people mention James Taylor. He’s probably the most successful one.  I like music I can sing along to – Broadway show tunes, a cappella, rock anthems.  But I also like classical and jazz… depends on my mood.  For my concert, let’s go to the Beatles in the mid-60s when the fans adored them and they were so pop and fun.  
I lean pretty far to the left, so perhaps politics is not a good topic to discuss!  
I was very lucky on the cancer front – I kept my sense of humor through being cut, poisoned and irradiated!  They found it early, I got in to the Yawkey Women’s Health Center at Mass General, was able to work straight through except for treatment days.  I don’t think about it much now – it’s just a time in my life I went to the doctor a lot, except when someone new is diagnosed and comes to me for help.  It did help me realize how much I want to enjoy life! 
You ask what I want?  Please don’t feel any pressure to help me with any or all this, but ideally I want a long-term thing so I can get off AM and find 
1) a confidante I can write to every day to share what’s going on, hear about their day, be involved and caring and flirty and send whatever great p0rn I find!  
2) someone to touch me and let me touch him.  I get nothing at home, so I am starved for the basics – someone to hold my hand and rub my wrist with his thumb, a back rub, a long hug.  
3) SEX!  PASSION!  I want a variety of positions… different things on different days… hard and fast sometimes, a slow conversation with sex here and there on other days. I like to be an equal – you do things, I do things, we do things.  My desires will probably broaden as I have time to get beyond longing for basics.  I know it tough to find time, but at least once a month would be grand and more if possible.  Is there ever enough? 
4) FUN!  I want to take a break from work and home and all that to laugh and relax and enjoy life! 
Any of that match up with what you want? 
I try very hard to stay anonymous.  I hope that won’t be a big deal for you.  It’s not about you so much as who might see your phone or your email.  I may tell you a lot in person but keep things electronic more narrow.  I am an expert on discretion.  My first fling was with an old flame from high school found me after 37 years.  He was military, married and miles away, so I learned how to entertain a man far away, and how to protect a man who would not only face a furious wife but the military code of justice if discovered.  He encouraged me to find a local option, which eventually led to AM.  I have also read a lot online – blogs from men and women using AM, and I was online in an IRC chat room for cheaters for years.  They are wonderful people just trying to make the best of it.  So I know how to keep men safe, and I’ve heard all manner of screw-ups and know the consequences which incentivize me to avoid them and help any guy I see avoid them!  Ask me about the bank robber someday when you are lying naked on my chest in a post-coital haze.  
Wow… I better stop before this turns into a novella.  What else would help you know if we might click?  Ask away! 
I’ll go eat leftovers and wonder how your skin will feel on mine… and how you taste!
From: Randy
To: Sassy
Sent: Tue, Sep 27, 2016 at 8:39 PM
Re: Connection
Hello Sassy,
I don’t really think you’re older than me.  I love long hair and curvy women.
As far as politics go I like to think that people have the same goals just different ways of going about achieving that end.  I know this is a bit naive but for me I have to hope for the best in people otherwise I would become completely cynical.  I am very comfortable in what I believe and why, so I don’t tend to get emotional about political arguments. Also I respect that others may have completely different opinions.
Yeah I must admit seeing the Beatles and the fan reactions would be fun, also the famous “Elvis has left the building” concert, early Chuck Berry, Ritchey Valens love it – truly a changing time in music and would love to have seen or been a part of it.  I play a lot of instruments – albeit not very well but respectably.  I very much love music and would love to play in a band again someday.
Okay the tricky part.
1) I also would like a confidant, someone to connect with to tell my secrets to and hear theirs.  To share their joys and sorrows.
2)  I totally agree with you – I miss the touching caressing, flirting, stealing a casual feel.  Gazing into someones eyes and feeling a connection.  I want that again!
3) I agree about sex.  I am a very passionate person.  I very much enjoy pleasing and it stirs up huge passion within me.  I can cum about 5x so I like to enjoy sex for several hours.  I also like to give almost more than receive.  I have been told that I am a particularly good kisser and have a very talented tongue for oral. 
4) Yes I want someone I can date – yes I mean really date.  I want to have fun too and am willing to discreetly travel on vacation.
As far as discretion, I would like to know your name.  I am very good at keeping my secrets well secret.  My phone is locked, I have separate credit card accounts and secret email accounts.  I also try very hard to be discrete.
A little about me: I too was in the military a very long time ago.  When I got out I went back to college and grad school.  I do tons of volunteer work and like to give back because I have been very blessed. 

I had a girlfriend a while ago and we dated for several years.  She moved away and so we broke up.  I tried some of the dating sites but the people I met frankly scared me…. I simply wasn’t ready for that.  
You seem very down to earth.  I like your sense of humor and clearly you can write.  So I think we are a very good match and would very much like to get to know you better.
What do you say?

The Jester appears

September 27, 2016 Tuesday 
I heard from a new man today!  Wow.  Busy week for new contacts!  

Ashley Madison Message
Date:Sep 27th – 3:56pm
Ok so the line “won’t save you money on your insurance” is an absolute grabber. How long did that take you to come up with? it’s great. Are you in advertising? lol With that sense of humor we definitely can chat I hope. I’m also rather humorous, dark humor, often in a self deprecating way. 
Check out my profile. Let’s chat! And even if you don’t I’m coming back to that profile when I need a laugh…
Jester huh?  That’s original.  

He likes my tag line!  Ha!  I went to look at his profile. 
He knows how to spell discreet!  Yay! 
• Age: 48 
Hmmm… he’s probably 50 or so but.. I don’t do that well with younger men.  
• Location: [redacted]
About half an hour away in the burbs.  That could work. 
• Height: 6’0″ (183cm)
Oh!  Yes please! 
• Weight: 180 lbs (82kg) – Fit
Hmm… kinda skinny.  I like burly better, but it could work.  Kris weighed about that. 
• My Limits: Undecided
Really?  I don’t like this one.  Eh.  Pick something!  
• Status: Attached Male seeking Females
• Gender: Male
: ) 
• Smoking Habits: Never

He checked a few boxes about his preferences – good stuff, nothing scary.  He wrote some good paragraphs.  Says he likes a good conversation.  Oh please, let that be true!

Seems worth an answer. 
He’s online right now!  I’ll write something quick so he gets a reply soon.  I sent out “don’t log off yet!” vibes.  
Date:Sep 27th – 4:12pm
Hiya J! Thanks for your great message! I like to make you laugh. I can’t take credit… a nice guy saw my boring old greeting and told me I needed something more peppy and came up with it! It felt like “me” immediately! Though I did look a little like Flo from the Progressive commercials in my younger days! 
I like your greeting… there is nothing like a man who knows how to spell discreet! I am happy to talk. Though I should say that unless you have a thing for older women, I’m probably not your gal. I have my best luck with older guys who don’t mind my long gray hair and curvy body. But I didn’t want your message to go unanswered. 
Best of luck to you! Hugs with groping! -Sassy

Date:Sep 27th – 4:19pm
That was a good laugh. 
And hopefully it’s not too perverse but I do like slightly older woman on the larger side. Is that freakish? So to be honest I love big boobs….that should at least give you a laugh!
Date:Sep 27th – 4:26pm
Here’s to more laughs! 
So you want to talk? Explore? See if we click? It’s not perverse… just like to be honest so I don’t waste your time. I certainly have the boobs thing going on! I can make a “boob man” very happy! Mmmm…. 
I should also warn you that I am almost as curious as I am Sassy… hope you like answering questions! You are welcome to ask a lot too! 
Hugs with groping… and an ear nibble… just because. -Sassy

Dance in the mirror

September 27, 2016 Tuesday

6:07AM Phil

Good morning! 
Off to the Big Apple! 
Have a great day!
[photo of a street scene]
A friend is starting school up there.
6:41AM Sassy
Good morning!
What’s in NYC?
Oh my…that bar is right down the street from my office.  Heh.
6:58AM Phil
Going on a cruise tomorrow
6:59AM Sassy
7:30AM Sassy
I’m heading in early to let the cleaners clean. 
Hope you have a grand time!
2:20PM Sassy
Are you afloat already?
Beautiful pix!  Much nicer day down there than here.
2:24PM Phil
System Island Ferry
2:24PM Sassy
Nice! Statton? Staten? 
2:29PM Phil
Yeah, damn spell checker
2:30PM Sassy
Ha ha
I’ve never done that…should try it.
4:12PM Phil
View is spectacular
4:13PM Sassy
Wow!  You are doing it up!  I adore how you do that…
Let me know how the show is… I’ve been thinking of going to NY sometime soon.

10:10PM Sassy
Amazing duet… gave me so many feels.
[90 sec video]
Dance in the mirror


11:47PM Phil
It was fabulous! 
Great music, lot of humor, wonderful color and a terrific theater. Loved it!

Witty Randy retorts

September 26, 2016 Monday

I wrote directly to his gmail account.  A first for me… going over straight to email with a new guy.  Hope he isn’t a creep!


From: Sassy
To: Randy
Sent: Mon, Sep 26, 2016 at 9:41 PM
Subject: Connection 
Tap… tap.. is thing working?  Are you that guy from that web site?  This is that gal from that web site. You cleverly embedded your email in your sweet message to me.  And let me see your handsome face.  So here I am.  Tell me what you’d like to know.   Hugs with groping! 
From: Randy
To: Sassy
Sent: Mon, Sep 26, 2016 at 10:26 PM
Re: Connection 
Hey there,
Like your witty retorts.   
It looks like you are from Boston.
My profile has me there but I live elsewhere.
Do you have any pictures you would like share?
Also do you chat? Email can take a while for a response.
Would be nice to get to know you better.
As for me I enjoy theatre, running, playing music and geeky things
For work I am in an office.  Too much.  
Hugs with deep kissing?
From: Sassy
To: Randy
Sent: Mon, Sep 26, 2016 at 11:35 PM
Re: Connection
How are you this fine evening? 
Great to hear from you.  I am in Boston. I like to go to elsewhere too.  Have you always been in MA?  I was raised in upstate NY but came to MA for college and stayed.  
I do have photos… I’ll attach my favorite below.  
Let’s email a little and I can switch to a gmail account to chat if we hit it off. 
For work I am an office manager, that efficient woman in the back cubicle no one notices, who takes care of the mundane administrative tasks so the senior staff can focus on their work.  I also help run a community project in my spare time.  
What sort of music do you like to see live?  I mostly get into folk types – recently saw Christine Lavin and David Wilcox.  They are both great story tellers, song writers, guitarists and singers!  If you could take me to any concert in history, where would we go? 
What are geeky things?  
Mmmm… deep kisses… yes please!  More hugs with groping… and an ear nibble… just because. 
[Attached “the famous photo of my cleavage in the black bra]

New Randy Man writes

September 25, 2017 Sunday
I got a message from a new Ashley Madison guy today!  

I still get excited seeing the notification email, even with all the crap I went through earlier in the month – getting to know a man and then having it not work out – TWICE.  Argh!  I keep thinking I can’t put myself out there again… why am I doing this?  Oh yeah… talking to a nice men…being touched… sex… *sigh.  Okay.  I’ll go read it.  Can’t hurt to read it, right? 
Ashley Madison message

Date: Sep 25th – 5:49pm
From: Randy
To: Sassy
Hey there, Loved your profile. 
I am a full size, happy guy, I’m 6’4″ and love real women (BBW). 
I am well educated and can hold a conversation. 
I would like to exchange emails and get to know each other better? 
I am [email address redacted] at gmail dot com. 
Looking forward to your response, 
Hmmm… brief.  Kinda sweet. Always fascinated and sort of repelled by men who say they like BBW (Big Beautiful Women) but better than him saying he doesn’t!  I went to look at his profile.
He says he’s 50.  Probably means he’s at least 52.  Whatever.  I don’t usually do well with younger men, but it’s worth trying? 
He’s tall!  I like that.  Makes me feel a little smaller.  
And he’s burly.  That’s good.   
Want’s something long term.  Hunh.  Nice of him to say that, even if it rarely works.  Better than “undecided!”  
And he’s attached.  That’s a must.  No single men. 
He checked a bunch of boxes for his preferences.  Eh.  Some I don’t want to deal with… but mostly fine.  
Refers to his wife as a roommate.  I know that feeling!  
He wants the basics… kissing, holding hands.  I know that feeling so well!  
Ooh!  He sent me access to his photo!  Awww… such a nice smile.  Though it’s a cropped family photo with the top of a little girl’s head beside him.  Don’t do that guys!  Use that mobile phone, smile and snap a photo.  Geez… 
He put in his email… maybe I’ll use it instead waiting a day or two and dithering on AM. 
Okay.  He deserves a reply.  I’m writing back.  But not until tomorrow.  I want to see if his words and his smile stick with me.  
 Time to get back out there!

National Punctuation Day

September 25, 2016 Sunday

6:00PM Sassy
Happy National Punctuation Day! Here are some lesser-known punctuation marks for your consideration.  I’ve never heard of some of these!  

9:53PM Sassy

One of the oddest plays ever in baseball tonight – winning run comes in from first on a ground ball in the top of the 10th when he should have been out 3 different ways… for the 11th win in a row for the Red Sox, that ties them for the best record in the league. Pitchers broke two records – 11 strike-outs in a row to break a 46 year old record, and 21 strike-outs in the game. This team is beyond the “unbelievable” stage into some unprecedented spooky twilight zone of a season-ending streak!

Sausage with sausage

September 24, 2016 Saturday

8:04AM Sassy
Hope the boat is being fun! Wave as you go by Boston?

3:16PM Sassy
Lovely lunch at Olive Garden with my gal pal!  I so adore their sausage soup and spaghetti with sausage!  Forgot to take photos, but you’ve seen them a dozen times already!

11:59PM Sassy
The Cambridges are in Canada!