Meet #1 – Didactic Daniel

May 10, 2017 Wednesday

from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 8:39 AM
subject: 4 hours

Good Morning Mysterious Lady,

I woke to the excitement of meeting you.

I am surprised that I have not been to the Red House before. It looks gorgeous in the online photos. I will be dressed casually.

See you at 12:30.

Attachments:
[photo of his smiling face]

=====

from: Sassy
to: Daniel
date: Wed, May 10, 2017 at 9:47 AM
subject: re: 4 hours

Good morning! I woke up smiling because of you. Less than 3 hours!!

I have on my business clothes… with a fun silk scarf!

-S

=====

Meet #1 Didactic Daniel 

Danny DeVito

I went in to the Red House restaurant and saw Daniel standing at the bar.  He looked like a very serious Danny DeVito!  He smiled briefly and walked toward me.  He looked short standing there and seemed even shorter when he got to me.  He is definitely NOT my height.  I’d guess he is 5’6″ max and perhaps shorter.  We hugged awkwardly – his head landed firmly in my breasts!  Oh my… not sure how I am going to handle being with a man who is so height-challenged.  I kept telling myself it won’t matter – I will get used to it.  Right? I pondered why it is so engrained to be with a taller man… hmmm.

They put us at a table in the middle of the back dining room.  It was crowded, so we could talk without worrying about being overheard.  We settled in and stared at each other.  He smiled and I smiled back.  He looked over the menu and told me he was impressed and surprised he’d never been there – it was his kind of place!  I relaxed a bit.  He talked about his work and asked for more details about mine.  I was pretty vague.  He talked about an upcoming school reunion.  I mentioned that I had one on the horizon as well.   He ordered a salad and I got the lobster chowder.  I sipped along and he regaled me tales from his work.  He seems quite didactic in an irritating way, like he knows what is best for everyone and does not hesitate to say.  It was odd because I didn’t see much of that in his emails but it came out in spades here.  He whined about having to have dinner with his wife and two of her friends, about how the wife of that couple is so tacky and clueless.  I told him about my fun dinner plans out in Sturbridge.  He asked me if I would go to his “country home” for our first time alone.  I said that sounded a little scary, both to be so far from home and to be in such an isolated place.  He glossed right over my concerns, extolling the virtues of the remote place. 

He was eager to end the meal and have me walk him back to his car for “dessert.” I agreed – maybe he has talents in that area that will make up for his personality and lack of stature?

We strolled through the grounds of the Charles Hotel then down into the bowels of their garage.  He had picked an excellent parking space in between two columns in a corner that afforded us lots of privacy.  He leaned against the car and pulled me toward him.  I angled my knees a bit to get my face down to his level.  He grabbed my hair and kissed me in a quick, fierce way that was rather hot.  Then he started grabbing at my crotch!  I turned a bit and hugged him to my chest, pulling his hands up there and slowing things down a bit.  He squeezed my right breast rather roughly and made a growling sound.  There was no finesse, no gentleness… it was a compliment that he wanted to devour me but way too much too soon.  He did not sense my discomfort, and said we were going to be great together! 

I decided in that moment that the triple whammy of combo of his personality, his height and his roughness meant I was done.  I need someone who is sweet and gentle.  And I hate to say it, but I need a taller man, someone who can envelop me and make me feel smaller, not someone who makes me feel like the Jolly Green Giant! 

He wanted me to get into the car with him, but I suddenly “had to get back to the office.”  I hope I was subtle about it.. it was almost 90 minutes since I’d arrived and I had told him that was my limit.  He was very disappointed and whined at length.  I thanked him for a lovely lunch and hugged him once more, then made my escape. 

I strolled slowly across the hotel courtyard, took photos of the beautiful plantings.  They were on a purple kick!  I sat on a bench and gathered my wits.  I very rarely hope not to hear from a man after a meet, but I did today!  I found myself wondering how to discourage him if he did.  Not something I am good at!  I went back to the office and tried to put it all out of mind. 

Of course, he wrote back as soon as he got home! 

=====

from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 5:01 PM
subject: W Ma to Boston

Hello Sassy,

I thought we would be compatible. I thoroughly enjoyed our lunch and time together.

When do we get together again?

=====

from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 5:07 PM
subject: 4U

A suggestion for next time.

=====

from: Sassy
to: Daniel
date: Wed, May 10, 2017 at 10:14 PM
subject: Re: W Ma to Boston

Good evening! Thanks again for a lovely lunch and for sharing yourself. I’m just getting in from dinner and am worn out from all the driving.

Hope your dinner was better than you feared.  More tomorrow!

-S

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Sturbridge adventure

May 10, 2017 Wednesday
1:55 PM Sassy
The Charles Hotel courtyard is a festival of purple flowers today!

10:01 PM Sassy
Dinner at Kaizen Sushi & Grill in Sturbridge

 Soft-shell crab appetizer 
 Miso soup with crab slivers 
 Beef bulgoki

Daniel details

May 9, 2017 Tuesday

from: Daniel
to: Sassy
date: Tue, May 9, 2017 at 10:44 AM
subject: re: The View

Sassy,

I slept very well. Woke up with an erection…. but otherwise fine.

As you know, the mind is the primary erogenous zone. Where would you like me to meet tomorrow? Best time for you?

===== 

from: Sassy
to; Daniel
date: Tue, May 9, 2017 at 2:27 PM
subject: Wednesday wonders

Good afternoon Daniel!

How’s your Tuesday going? I’m mired in coding purchasing card transactions at work. Whee! And fantasizing about meeting a lovely man for lunch tomorrow!

Thank you for letting me inside your head so I can help make fun things happen! I enjoy finding sexy things to send to inspire you – stories, photos, videos. They can fill the gaps between meets. If you have favorites, feel free to share them. Here’s a sample – just a little 5-second snippet. You’ll need a tumblr account to see it.

Let’s meet at 12:30 pm Wednesday. I would love to show you The Red House if you see food you’ll enjoy. It’s tucked down Winthrop Street, a couple of blocks from The Harvest. They have a lovely bar with a fireplace where you can wait if you get there early.

Menu http://www.theredhouse.com/

Map https://goo.gl/maps/NfUKiwqYmx52

If you have a hankering for somewhere else and it’s a safe spot for you, that would be a special treat! Let me know.

If we run into anyone I know, I will mostly try not to explain anything but if I need to, you are a fan of my community group and I am talking to you about donating. I can explain more about that in person.

What else do you need to know before tomorrow? Any deal breakers you should ask about?

I feel like Annie… tomorrow! Tomorrow! I’ll see you tomorrow! Hee hee…

-S

=====

from: Daniel
to: Sassy
date: Tue, May 9, 2017 at 6:04 PM
subject: re: Wednesday wonders

Hello,

Here I am meeting you not knowing your name or what you look like other than your height and weight. LOL.

Thank-you for the “entertainment”. You even have a plan for when someone meets us. If it is my daughter, who works in that area…. lets say we are High School friends. OK?

See you at 12:30.

Daniel

P.S. That was quite a GIF

=====

from: Sassy
to: Daniel
date: Tue, May 9, 2017 at 6:14 PM
subject: re: Wednesday wonders

Hiya Daniel,

I sent two photos yesterday – did you not see them? Let me know and I can try again.

=====

from: Daniel
to: Sassy
date: Tue, May 9, 2017 at 7:15 PM
subject: re: Wednesday wonders

Never received them. Attachments?

=====

from: Sassy
to: Daniel
date: Tue, May 9, 2017 at 7:35 PM
subject: Fwd: Connection

Try #2

Attachments:

[the one of my black bra and cleavage, and me dressed up for a night out that shows my face]

=====

from: Sassy
to: Daniel
date: Tue, May 9, 2017 at 7:37 PM

subject: subject: re: Wednesday wonders

How strange! I just tried again. Did you get them this time?

The subject line is Connection.

=====

from: Daniel
to: Sassy
date: Tue, May 9, 2017 at 11:52 PM
subject: Re: Connection

And your first name is?

=====

from: Sassy
to: Daniel
date: Wed, May 10, 2017 at 12:12 AM
subject: Re: Connection

Ha! I’ll save the name thing for when I see you. Don’t like to put it in email where prying eyes might find it.

Glad you got to see the photos!

See you in 12 hours! Mwah!

-S

Raging boner

May 9, 2017 Tuesday

9:38 PM Phil
Hey cutie, hope your week is good!
9:38 PM Sassy
HIya! Looks like you’re having fun!
9:38 PM Phil
Having a great time.  Good to be away!

9:39 PM Sassy
The weather looks awesome!

9:40 PM Phil
Cigar and a drink on the board walk. 
Even had lobster last night
Spectacular

9:40 PM Sassy
Wow!  You been hearing the news?

9:41 PM Phil
Which news? Trying to ignore it
9:41 PM Sassy
Trump fired Comey.
9:41 PM Phil
Saw that. He should have been fired. FBI is a mess

9:42 PM Sassy
Not so sure of that.  Feels like obstruction. 
What kind of lobster?
9:43 PM Phil
Just a roll but delicious

9:43 PM Sassy
Oooh… yum

9:44 PM Phil
All the food is so good here.
Spent an hour and a half in the gym and then walked 30k steps

9:46 PM Sassy
Didn’t look too crowded.

9:47 PM Phil
No, was terrific

9:48 PM Sassy
Meeting a new guy tomorrow.  Think good thoughts.

9:49 PM Phil
Always. Good luck!

9:49 PM Sassy
Thanks!  
I have low expectations, so maybe I’ll be pleasantly surprised.  
Is it warm there? It’s freakin 47 degrees here!

9:51 PM Phil
80 now, in the 90s during the day

9:51 PM Sassy
Geesh…

9:53 PM Phil
[2 photos of the view from his seat – pretty lake front with lights]
Looking at this

9:53 PM Sassy
That is spectacular!

9:59 PM Phil
It’s so pretty

10:00 PM Sassy
So glad you can get a break.
10:01 PM Phil
It’s nice, truly is
10:11 PM Sassy


[photo of a woman’s lips on a man’s cock]
10:12 PM Phil
Damn baby!
Standing on the boardwalk with a raging boner

10:14 PM Sassy


[gif of a woman sucking on a man’s cock]

10:14 PM Phil
I know from experience you know how to lick and suck my cock like that
Oh fuck girl 
Mmmmmmm
You make me think such delightful thoughts

10:16 PM Sassy
Good

10:18 PM Phil
Yup
You are such a delightfully bad girl

10:19 PM Sassy
You betcha!

10:21 PM Phil
You would get a creamy reward for that

10:23 PM Sassy
Mmmm… sounds fantastic
I’d swallow it too.

10:25 PM Phil
I know!  Tastes marvelous on your tongue
Love filling your hot mouth
Got me rock hard and dripping

10:27 PM Sassy
Oh man… wish I was there to take care of that!

10:28 PM Phil
I would let you have your way with me, use me as your toy

10:32 PM Sassy
I’d treat you right.

10:32 PM Phil
Oh I know

10:32 PM Sassy
Lie back, relax… let me do my best.

10:33 PM Phil
That would leave you with a mouthful and pussy full of cum to start with

10:34 PM Sassy


I’m Glad You Came…
gladdyoucame.tumblr.com

10:36 PM Phil
Oh yeah
Walking through the lobby with an obvious tent and big wet spot on the front of my shorts. Thank you

10:38 PM Sassy
Always glad to help.  ;  )

10:39 PM Phil
: )
10:42 PM Sassy
Sleep well dear man.

10:42 PM Phil
[photo of his cock very close up]

10:43 PM Sassy
Oh my
I’m licking my screen again!

10:44 PM Phil
Thanks babe
[VIDEO of him jerking off]
10:48 PM Sassy
Mmmm
Yum

10:50 PM Phil
Have fun tomorrow. Hope it goes well!
Just getting you in the mood
10:51 PM Sassy
You are made of awesome
10:51 PM Phil
XXoo


Planning to meet Daniel

May 8, 2017 Monday

Date: May 8th – 3:33am
From: HC

Message
Hello Sassy, I taught English but please do not worry, my red pen is safely stored away! You write well. I would enjoy seeing some of your writing, please. Erotica… sounds lovely.

As you know, it is all about timing. She works long hours during the day. I spend time at the “country house” and she often stays home during the week to work. We do not have an open marriage, so I need to be very careful.

Yes, avoiding traffic and peace and quiet are important to me.

How does Wednesday look? I have to come up to Boston in the morning and need to get back for dinner at 6. Perhaps meet for coffee or lunch? Hugs with groping. Hmmm Perhaps hugs with touching? A kiss on the ear would be very nice. Where would you like to meet? Daniel

=====

Date: May 8th – 3:04pm
From: Sassy

Message
Hiya Daniel, 

Hope your Monday is off to a grand start. I greatly admire teachers for their creativity, patience, and the ability to cope with a wide range of students, parents and administrators! 
Wednesday looks wonderful! I am so excited! Want to try 12:30 or 1 pm? I can pop out of work work.  What are you up for? We can do a quick look at Starbucks or lunch with the 50 cent oysters and lobster chowder, or Border Cafe, Vietnamese, Thai, Indian buffet. It doesn’t look like picnic weather, sadly. 
I want to hug you like an old friend, talk a bit, then if you like, see how you kiss! I can probably take about 90 minutes if we need it. See you soon! Mwah! -Sassy

=====

Date:May 8th – 3:13pm
From:Sassy

Message
Hi again! Sadly even my shortest erotica won’t fit in under the 2000 character limit here. If you have an email you want to share, I’ll can do that. Or we can wait until after we meet if you’d rather check me out before taking that step. -S

=====

Date: May 8th – 7:17pm
From: HC

Message
Hello Sassy, I am excited about meeting you! May I suggest lunch? I like fancy places, but there are probably more intimate places, where we can have some privacy and not feel rushed.

I’ve attached a photo.  Could you send me a photo too, please? Your writing also fascinates me. 
Here’s my email [redacted] You have my undivided attention
=====

SWITCHED TO EMAIL 

from: Sassy

to: Daniel 
date: Mon, May 8, 2017 at 9:07 PM
subject: Connection

Hiya Daniel,

Hope you’re having a lovely evening.

Yay – we’re off AM! Their interface is yucky.

Gosh… a fancy place would be lovely if you’re serious. Also take a look at The Red House, or John Harvard’s Brewhouse?

You have a friendly smile! I’m attaching two photos – me dressed up on Opening Night and my best feature. I’ll send a short erotica next.

Your attention and interest is very alluring!

-S

attachments: two photos 

[the one of my black bra and cleavage, and me dressed up for a night out that shows my face]

=====

from: Sassy
to: Daniel 
date: Mon, May 8, 2017 at 9:34 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…”
=====
from: Daniel 
to: Sassy
date: Mon, May 8, 2017 at 10:26 PM
subject: re: The View
You are one hot lady!  
I enjoy oral sex and would have pleasured you that way first.  
=====
from: Sassy
to: Daniel 
date: Mon, May 8, 2017 at 10:54 PM
subject: re: The View
You betcha!  
Oooh… I adore it when a reader takes the story and adds their idea.  
I’ve never crossed the line at work… never been tempted.  But this story sprang out of my brain almost whole one day and it gets to me every time I read it! 
Sleep well Daniel. 

Daniel wants to meet

May 6, 2017 Saturday

Date: May 6th – 10:50am
From: Sassy

Message
Hiya Daniel! How’s your Saturday going? Thanks for answering! Hope you can answer a few more? You write so well. You can imagine the “interesting” missives I receive, from the “Yo, u wanna?” to amazing epistles like yours! You make me want to know more, to figure out if we can make each other smile. And tingle? I also want to explore enough so I don’t waste your time if our expectations don’t match.

Ah… lobster. When it gets warmer, I crave simple boiled fresh meat dipped in hot butter, but by the time my birthday comes around in the fall, I’m ready for baked stuffed! Do you cook? I don’t much… just no brain for it. But I do make great reservations! 🙂 
So sorry you are not getting what you need at home. So common. *sigh I never thought I’d be the person to step out, but so glad there is a way to have fun! Have you been getting out for awhile or are you just starting? An old flame from h.s. found me a few years back after 37 years and made it clear I was still someone a man could want, gave me the confidence to explore! 
I didn’t feel brave or strong during my cancer treatment… just went to the doctor a lot for 9 months. I try not to make it what I am about anymore. I was very lucky – they caught it early, I had access to the best doctors in the world, and worked straight through treatment except a day here or there. Cancer definitely sucks. Every time I hear about it killing someone, I wonder why I am alive. Still looking for the logic in that… 
I am the demure, efficient office manager that no one notices, taking care of the administrative details so the senior staff can focus on their work. In theory I work M-F 9-5 but I get a lot of time off, and Hubby doesn’t pay attention to where I go so I am quite flexible. 
How old were you when you first had sex? I was 17… found it quite boring and could’t figure out why guys liked it. I’ve learned a lot since then! Hugs with groping! -Sassy

=====

Date: May 6th – 1:26pm
From: HC

Message
Hello Sassy, I enjoy your messages very much. You write very well, which is saying a lot from this former English teacher. I guess once a teacher always a teacher. I’ve enjoyed teaching at all levels from kindergarten to college.

Yes, I cook and enjoy it. Nothing too fancy, but enjoy sharing time that way
=====

Date:May 6th – 6:28pm
From: HC

Message
Part II
Sorry for the premature send… here are my comments on your message.

“I am the demure, efficient office manager that no one notices, taking care of the administrative details so the senior staff can focus on their work.” That sounds very sexy to me….

“In theory I work M-F 9-5 but I get a lot of time off, and Hubby doesn’t pay attention to where I go so I am quite flexible.” My schedule is wide open during the day. I can go on fishing trips too.

My wife keeps an attentive eye on me. Weekends are spoken for with the exception of Saturday mornings. Are you a “morning girl?”

“How old were you when you first had sex? I was 17… found it quite boring and could’t figure out why guys liked it.” The first time I had intercourse, I was 17. My first true sexual relationship was not until I was 19. Two affectionate kids who enjoyed each other as often as possible.

Your story about reconnecting with your first lover has been a fantasy of mine.

I am here in the country for the weekend. I will be returning to the Cape on Monday. What does your schedule look like for next week? Daniel

=====

Date: May 6th – 10:52pm
From: Sassy
To: HC

Message

Hiya Daniel! This is so fun! Thank you for satisfying my curiosity. Wow… former writing teacher? That’s a little daunting. I have to write… started a daily diary at age 12 and depend on regular writing to avoid mental constipation and make sense of my days. I even dabble in fiction now and then. Maybe I’ll share some erotica if you’re interested.

Your flexible schedule sounds lovely. I can be a morning person. Or an afternoon delight. I can even “fish.” Though I try to stay out of my own pond. Heh.

Please tell me you know how to keep your activities under the radar. I don’t worry about it much for myself, but my old flame was military so I learned a lot to keep him safe, as he would’ve faced not only a furious wife but the military code of justice. Hubby and I are mostly what is called “open” where he does his thing and I do mine, so I don’t have to hide. It also allows me to invite men to my place at certain times, after I’ve known them awhile.

Fascinating that you have two places in a reverse commute sort of way. Hope that helps you avoid the terrible Cape traffic.

Are you thinking coffee? Lunch? Dinner? My work calendar is pretty clear M/Tu/Wed. If you want an early evening, I am free Monday, Tuesday, Thursday. Hugs with groping… and an ear nibble. Just because. -Sassy

Aung San Suu Kyi in London

May 6, 2017 Saturday

9:05 AM Sassy
Good morning kid!

9:28 AM Sassy
Majesty Magazine is focused on the Brits transferring duties, but I am overjoyed to see Aung San Suu Kyi at Buckingham Palace! I prayed for her for years while she was under house arrest and now, Nelson Mandela style, she has been freed to do bigger things for her country and the world!
10:08 AM Phil
Good morning! Beach bound!
10:19 AM Sassy
Yay!  It’s cold and rainy here, so I’m getting stuff done around my condo.

Having lunch with my older sister and her beau.  He has prostate cancer, surgery soon maybe.  Going to listen, see what I can do for them.
11:26 AM Phil
Aww, thinking positive thoughts

3:05 PM Sassy
Lunch at Court House Seafood!  Such fresh fish… mmm…