Category Archives: Jester

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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….

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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.  
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Meet #1 Jester groping

September 30, 2016 Friday

from: Sassy
to: Jester
date: Fri, Sep 30, 2016 at 7:44 AM
subject: Meeting day

Good morning! Hope you had a great evening. I fell asleep at 7 pm. Oops.

Still looking like lunch can happen? I’ll see you there. 

Hope it’s okay if I greet you with a hug like an old friend?

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from: Jester
to: Sassy
date: Fri, Sep 30, 2016 at 9:08 AM
subject: Re: Meeting day

Can I grope you like an old friend with benefits?

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from: Sassy
to: Jester
date: Fri, Sep 30, 2016 at 9:47 AM
subject: Meeting day
Absolutely!  Looking forward to it!  

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Meet #1 

This morning went so slowly!  I was so excited to get out for lunch and meet this funny man.

I left work just in time to make it to the restaurant.  I turned the corner and there was construction everywhere!  The sidewalk was closed, so I had to cross the street, walk up past the place then cross over and walk back.  Ugh… would not have picked this place if I knew it was going to be construction central! I had told Hubby I was having lunch out today but forgot to tell him where, I stopped to text him.  Always good to have him know where to start the search if I disappear.  Heh.  
I went down the stairs and there he was!  He was sitting at the bar and turned and smiled up at me!  I adore it when the man is there first!! 
I hugged him and he let go quickly.  We found a table in a back corner and started right in talking.  I took his hands and smiled and he smiled back.  He had on a dark red dress shirt and khakis.  He is quite nice looking and has dark hair!  He looks sort of like Dean Martin.  Yum.  I wonder if he dyes his hair?  So black – that’s unusual in older men these days!  

Dean Martin

He said, “It is so nice to see you.  I realized we don’t even know each other’s names!  My name is Dan.”  I hate this part… I told him my first name but then explained I don’t want to be called that.  It is too tied to my responsibilities and work and… I’d rather be Sassy!  He smiled and seemed to get it. 
I asked him if he had any trouble finding the place.  He admitted he had never been to this area before!  He got there early and wandered around taking in the sights.  I am surprised he didn’t ask me for any help – great that he can find his way in the heart of the city. 
I asked him about his work – he is retired!  He still works part time on projects he chooses, but is very flexible.  He asked me about my work.  I admitted the name of my employer but kept the specifics vague. 
I ordered an iced tea and he got a lemonade.  He got the chicken BLTA and I got the bratwurst with fries. 
I asked him what brings him to AM now – does he get nothing and want something?  Or get something and want something else?  He said the former.  I told him I am the same.  He said he is not interested in changing his situation but needs some sex somehow.  He said he had some luck once on AM, but the woman moved away and they couldn’t keep up.  He has also met some crazies and elected not to meet others.  He told me about women picking fights over odd things, like getting hassled by a woman who wanted him to post his photo on AM and refused to open a mischief email.  He even offered to open a special Facebook for her… she was mad at him.  Weird.  I assured him I am not a fighter and completely sane! 
I told him about my old flame finding me and how he resurrected me.  And about chat and how much I learned there.  He told me he has no one to talk to about it, but read stuff online and knows to use gift cards and another email and meet in public the first time.  

He got the check and insisted on paying.  I thanked him but explained that I am not looking for a sugar daddy, how my life has changed since my mom died, and I don’t expect him to pay for everything.  He nodded but said he is flush and can do it.  I told him I don’t want him to take me shopping or whatnot…he has seen those profiles and ignored them! 
I asked him about places he’s traveled.  He said his wife teaches, so they are limited in when they can go and then everyone else with kids is traveling then, so they don’t go as much as he’d like.  They do get the summers free and spend most of it down on the Cape.  I told him about Hubby not wanting to travel so we do day trips, and about going to Mexico with my sister. 
We talked about the Red Sox winning the division.  He said he’s not much of a sports person.  I talked about figure skating for a bit. 
He excused himself to use the men’s room and was gone longer than I’d expect.  I checked my phone.  He returned and said sorry he was delayed – it’s tough to pee when you’re hard!  Ha!  I held his hand and played with his thumb and he said I wasn’t helping.  I said sorry… not sorry!  And he winked!  He is fun! 
He said he would like to be alone.  I said I’d like to know how he kisses.  I suggested we try out the handicap bathroom.  He looked shocked!  He asked me where it was.  I pointed and told him to follow me.  I grabbed my stuff and went there.  Eventually he joined me. I forgot my purse in the rush… he went back to grab it for me.  Awww… 
I leaned against the wall and he flattened me to it, kissing gently and groping my breasts. I squeezed his ass with one hand and caressed his face with the other.  I reached around and rubbed his hard cock.  Mmmm… he thrust against me… wow.. Push, push push… so sexy! 
He broke off way too quickly, saying he had to get back to his car at a parking meter.  He left and told me he’d wait for me outside.  The construction people were gone, thank goodness!  I thanked him for lunch and “dessert.”  He said that was not really “dessert” that he would show me a real one later!  He promised.  I asked him to write to me.  He walked off in one direction and I went the other.  
I went around the corner and texted Hubby to let him know I was done and heading back to my office.  
Not sure why, but I had the distinct feeling I will not hear from this guy.  It went well, he was fun but… ah well… time will tell! 

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Jester photo swap

September 29, 2016 Thursday

From: Jester
To: Sassy
date: Thu, Sep 29, 2016 at 8:28 AM
subject: Re: Connection
Hey Sexy Lady,
Sorry for the delay in replying, I could not log on. 
I love Jimmy Buffet but have never been to a concert. In fact I’ve never been to a concert-period. Shocking I know. I like a wide variety of music and never one particular artist enough to go to their concert. 
I’ve been to Key West about 15 times-love it there.  
Soooo-I was not trying to rush things, I always find meeting someone in person gives you a much better feel for the person, looking into someone’s eyes when speaking with them, their dress and mannerisms, their voice inflections-all of these cannot be felt on a computer screen. I’ve been pleasantly surprised and sometimes disappointed but I’ve found its never exactly what you expect. I enjoy the thrill of meeting new people.
Would you like to exchange photos first? Or do you find the excitement of walking in blind to be stimulating….     
I was going out of town Friday afternoon but with the weather forecast, that doesn’t look like its going to happen. So I could probably do lunch on Friday-I’ll know for sure later today. What are your thoughts??
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From: Sassy
To: Jester
date: Thu, Sep 29, 2016 at 10:27 AM
subject: Re: Connection
Good morning!  
Hope your Thursday is off to a grand start. 
No worries.. I learned long ago not to look for replies, just enjoy them when they appear!  
No concerts?  Wow.  I haven’t been to many but I’ve been trying to do better lately.  I saw my absolute favorite folk singer, David Wilcox, in the back room of a bar with about 100 people.  It was stunning!  He is a great storyteller, incredible guitarist, fine singer… so fun!  Last time I saw him was back when WBOS was having concerts in Copley Square for 5,000!  
I’m up for lunch tomorrow if the pieces fall into place, or next week if it’s easier.  
Hmm… mixed feelings about photos.  I like to see if a guy looks just like my husband (which I can’t deal with) but other than that I don’t pay much attention.  Can’t tell much from photos.  Whatever you like.  I will send one, pertaining to our earlier discussion and because I am Sassy.  
[attached the photo of my famous cleavage in the black bra that adorns this blog]
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From: Jester
To: Sassy
date: Thu, Sep 29, 2016 at 11:00 AM
subject: Re: Connection
So I opened up my email and quickly had to shut my office door as these fantastically awesome breasts appeared to the side of the message. And of course I opened the photo to full screen because that’s just who I am… I’d send you a picture of my chest but it just wouldn’t have the same effect…. This was taken two years ago, its still accurate. 
To show you what a good sense of humor I have, the second photo I texted to my sister (who hates to fly) as she boarded a plane…about the horrible weather expected down there.  I found it terribly amusing…If you can’t torture your siblings…
The problem I now have is I can’t get up for a while….. Looking forward to lunch tomorrow although I’ll probably have the same difficulty in getting up….
[attached photo of him on the back of a boat sitting in a river or lake – lovely dark hair, sunglasses, big smile, nice shoulders, skinny arms and legs, nice feet in sandals!]
[attached a graphic from a weather map with heavy thunderstorm warnings]
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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 11:27 AM
subject: Re: Connection
I probably should have said I’ll have a problem standing up….no problem getting up….lol
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From: Sassy
To: Jester
date: Thu, Sep 29, 2016 at 12:42 PM
subject: Re: Connection
Well gosh, if you’re gonna show me your face on a boat, I can do the same.  And you can run now.
That’s me on the Lake Winnipesaukee mailboat on the hottest day in August.
[attached a photo of my face]
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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 12:49 PM
subject: Re: Connection
Nice, you should be in a bathing suit on the hottest day in August…any other pictures to share? 
Looking forward to lunch!
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From: Sassy
To: Jester
date: Thu, Sep 29, 2016 at 3:53 PM
subject: Re: Connection
Greedy fellow!  Here’s another pic

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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 3:58 PM
subject: Re: Connection
OK so now I’m rock hard….It seems the blood has all left my brain and traveled south….
FYI I have something that would like so good between there….
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From: Sassy
To: Jester
date: Thu, Sep 29, 2016 at 4:04 PM
subject: Re: Connection
My my… bats eyelashes… whatever could you be referring to?  😉 
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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 4:17 PM
subject: Re: Connection
I’m heading out shortly to meet an old work friend for dinner, he wants to go to Hooters! Isn’t that a hoot-I crack myself up…  Still up for lunch tomorrow, where and when should we meet?
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From: Sassy
To: Jester
date: Thu, Sep 29, 2016 at 4:22 PM
subject: Re: Connection
That sounds… interesting.  This will be quite the booby day for you!  Have you been before?  I’d like to hear your impressions of it.  
Can you make it to Harvard Square?  I am flexible for a time.  Do you like oysters?  There’s a 50 cent oyster place with the best lobster chowder. Or an Indian buffet?  Or American food like John Harvard’s?  
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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 4:27 PM
subject: Re: Connection
I’ll let you know about Hooters…lol
I think I can find Harvard Square, John Harvard’s sounds good, noon?
Gotta run but I’ll check my email tonight if I can but tomorrow morning definitely. 
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from:Sassy
to:Jester
date: Thu, Sep 29, 2016 at 5:19 PM
subject: The view
Just as I was finishing my last meeting of the day yesterday, 
gathering my papers off the marble table in the conference 
room on the 36th floor, the sound of sirens wafted up from 
the expressway below.  Everyone else had left the room, so 
I took a minute to lean over the marble counter and stare 
down at the roadway.  There was a horrible wreck of mangled 
metal and shattered glass, several cars and a tractor trailer 
twisted together.  The traffic was stopped behind the mess, 
and the cars on the other side barely moved, rubbernecking.
Suddenly, I heard the door close. I straightened up, but before I
could turn, I felt your arm around my waist, and felt the heat of you
on my back through my dress.  You were already hard, pressed
tightly against my ass.  I started to speak, but you put a finger
on my lips and teased a corner.  I licked your thumb, and you moved
your hand down to unbutton my dress.  Just enough to slip
your hand inside and tease a hard nipple.  I moaned and let my head
fall back against your shoulder.  You bit my neck and ran your
tongue across my skin.
You slipped your hand under my skirt and inside my underwear,
teasing my most sensitive spot.  You pressed a finger inside,
unsurprised at the moisture gathered there.  I was startled
as you lowered my underwear.  I felt like my knees would
buckle, but you tightened your grip and spread my legs to
balance me against the counter.  I panicked when I heard
the rasping sound of your zipper, but before I could form the
words in my mind to stop you, I felt you hot and hard against
my skin, and a low moan was all that escaped my lips.  You
shoved it inside me, and your breathing grew ragged as you
watched yourself slide in and out.  You kneaded the flesh of
my hips as you moved, then reached around me to rub the top
of my slit in time with your strokes.  I was trying to be
quiet, but could not hold in all the gasps of pleasure as
you thrust deeper and deeper inside me, your balls slapping
against me.  You felt the trembling start inside me, and
the clenching around you.  You felt the pulsing, the searing
heat and suddenly lost control, pounding me into the wood
and stone, spurting up inside me over and over.
The only sound was our uneven breathing and the whirring
air conditioning.  You pressed your cheek to my back and
whispered, “What a view…”
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From: Jester
To: Sassy
Thu, Sep 29, 2016 at 7:23 PM
subject: re: The view
Wow……no words can describe…..
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from:Sassy
to:Jester
date: Thu, Sep 29, 2016 at 7:44 PM
subject: The view
Never had sex at the office but this gets to me every time.

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Jester to gmail

September 28, 2016 Wednesday
Date:Sep 28th – 8:23am
From:Jester1968
Message
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?
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Date:Sep 28th – 8:58am
From:Jester1968
Message
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
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Date:Sep 28th – 12:08pm
From:Sassy
Message
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! 

-Sassy
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Date:Sep 28th – 2:29pm
From:Jester1968
Message
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]@gmail.com 
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….
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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?

-S


by

The Jester appears

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

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Ashley Madison Message
Date:Sep 27th – 3:56pm
From:Jester1968
Message
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…
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Jester huh?  That’s original.  

He likes my tag line!  Ha!  I went to look at his profile. 
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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
Good. 
• Gender: Male
: ) 
• Smoking Habits: Never
Good. 

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!

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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.  
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Date:Sep 27th – 4:12pm
From:Sassy
Message
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
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Date:Sep 27th – 4:19pm
From:Jester1968
Message
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!
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Date:Sep 27th – 4:26pm
From:Sassy
Message
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