Three answers and cleavage

May 16, 2019 Thursday
From: Floridian
To: Sassy
Sent: Thu, May 16, 2019 at 10:58 AM
Re: Wednesday wondering

Hi, Sass,
Pester away but I don’t consider it pestering. 

In answer to your questions:

1) AM

I really don’t know. Fantasy, maybe? Hope? Time on my hands? About time? All of the above? I signed up years ago for a free account but never paid to connect with people. I retired and per my wife’s desire, we bought a house and moved to Florida so she could be near her family. Our relationship has been chaste for years because of some medical issues with her but working, friends, and grandchildren kept me too busy to realize the void. Now we’re here and while she has her relatives and some other activities, I’m pretty bereft of friends and things to do so the mind wanders and other parts tend to follow. I’ve actually never hooked up with anyone but think I’m open to the right person. You very much seem like the right person but I so wish it happened while I was still up there.

2) How was I when I first had sex? 

Inexperienced and drained. But I’m assuming you mean how old. I guess we’d also have to define “had sex.” I was 13 when a helpful blonde chesty 30-something neighbor named Bonnie took my needs into her hand, so to speak. I was 17 when I first had intercourse with an age-appropriate girl/woman, and about 20 when I really learned how to do it right so it actually worked for both of us. I learned in my mid-20s that my tongue had both verbal and oral skills and that’s been my best experience since.
3) Favorite 
Again, we need to define this question more narrowly. Favorite part to look at? Hair and eyes. No particular color, style, or length, though the longer, the more alluring to me. But soft and deep on both just melt me. As for favorite part to touch, wherever my tongue can linger and generate a response, lips, ears, neck, breasts, or between the loins. Or all of the above.

Now you.

From: Sassy
To: The Floridian 
Sent: Thu, May 16, 2019 at 11:15 PM

Re: Wednesday wondering

Hiya Josh!

So fun to see your name in my mischief email inbox, and to read your words!

Thank you for indulging my curiosity. I adore hearing your stories and poking around in your head. Here’s a window into my mind:

1) AM
These days I am mostly on AM to help friends fine-tune their profiles.

Hubby and I are good friends but nothing happens in the bedroom except sleep. I went without sex for 10 years, thought that part of my life was over. Then an old flame from high school found me after 37 years. We only dated for 3 weeks in h.s. and never did much except hold hands at lunch and kiss under the stairs but there was this chemistry, and he wanted to see if he could re-ignite it and finish what we started. Hubby encouraged me to fly off to meet him. I figured there was no way he would touch a curvy old married lady, but I was wrong. 🙂 He resurrected me sexually, taught me that I could enjoy sex! He helped me hone my ability to “entertain” a man long-distance. And how to keep him safe from discovery. But he was married, military and miles away, so he encouraged me to find a local option.

About that time, I was diagnosed with cancer. He talked me into getting the test that found it early, so I owe him my breast and maybe my life! I spent 9 months in 2010-11 “going to the doctor a lot” but I am whole and healthy now. I came out of that with a renewed sense of “life is short” and “you only live once” and “sex has to be part of it!”

Several of my friends were on AM and talked me into putting up a profile one rainy night of September 2012. I figured I would not hear from anyone. I was wrong. 🙂 

I have met good, bad and worse men. I’ve learned not the expect much, to have fun while it lasts and been pleasantly surprised several times! I am NOT looking for love or leaving Hubby or any serious stuff. Just smiles and fun and good food and sex and knowing another interesting person.

Wait… so you are from MA? That’s interesting. 

We do seem to have a spark… I adore these early stages when we’re both perfect. 🙂

2) The first time
Age 17. High school sweetheart. We starting dating in October when I was a senior and kept going further and further until February when we “went all the way!” It was… boring. We were clueless. We couldn’t believe that was what all the adults went on about! I have learned a lot since then.

3) Favorite
Eyes. That twinkle a man gets when I say something sassy or touch a certain spot. And shoulders. I’m a sucker for shoulders. If you talk about oral I may have to like you a lot.

Excellent answers! My hair is below my shoulders now… I had waist-length dark hair when I lost it all to cancer and it came back in gray and curly! So I never want to cut it again but I make myself do it once a year to keep it healthy!

Are there questions you want to ask? Please do – I am open to sharing. I find it enhances our interaction, and can give us more reasons to be nice to each other and discover the best ways to do it. Or keep us from wasting each other’s time if there are deal breakers we stumble on.

If you are enjoying it, I will ask three more questions:

1) Work

Want to say what you did or more about what you do now?

I am an office manager – you know the type – the demure efficient older lady who sits in the back office and takes care of the administrative stuff so the senior staff can do their work?

2) A restaurant 

If I were to take you out for a special meal, what would you like to eat?

I don’t cook but I make great reservations. 😉 I have an eclectic palate. I adore lobster dipped in butter. The gnocchi in a short rib sauce. Fried chicken. A beet and goat cheese salad. Chinese, Thai, Indian, Vietnamese and even Afghan food! The perfect warm chocolate chip cookie.

3) Music 

Favorite artists? Do you sing or play an instrument?

I listen to songs I can sing along with – folk music like David Wilcox, John Gorka, Christine Lavin or Cheryl Wheeler or James Taylor. Broadway show tunes. A cappella groups. I do like almost all music and gave hum along to rock, pop, country, classical etc.

I sing and play the piano, though I haven’t done much of either in a while.

I’d better quit before this becomes a cure for insomnia. I will send you two other things… a photo of my best assets and a snippet of erotica. Hope they entertain you.

Sweet sexy dreams J!


From: Sassy
To: Floridian 
Sent: Thu, May 16, 2019 at 11:16 PM
Subject: The black

Hi! I fought hard to keep them, so I get to flaunt them now, right?


From: Sassy
To: Floridian
Sent: Thu, May 16, 2019 at 11:17 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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