Sonoma erotica in play

October 10, 2017 Tuesday

7:55AM Sassy
Good morning Philip!
8:30 AM Phil
Good morning! Have a great day!
10:37 AM Phil
[photo of a computer screen with a shot of my nipple and his cock in the lower corner!]
[photo of a computer screen with the photo I sent him and his cock in the lower left]
Thinking about you ; )
I know I’m bad, sorry : )
10:59 AM Sassy
You are so bad!  And I adore you for it!!
11:05 AM Phil
Hee hee, hope I didn’t distract you
4:39PM Sassy
You are THE MOST distracting man I know!
I found that story I wrote from Santa Rosa… it’s long but lots of sex. 
5:23 PM Phil
Wow!  Hot stuff!
You write well but you had a good subject 😉 

I never saw that before but the story is familiar and very sexy
5:30 PM Sassy
Thank you!  
You are an incredible inspiration.  
Can’t believe all those places are burnt out.
5:30 PM Phil
That’s so sad
5:30 PM Sassy
It was part of the bunch of stories I wrote while I was in chemo.
Seems so possible, so real
5:33 PM Phil
For good reason 😉 
The pussy lubed finger caused body parts to jump!
5:37 PM Sassy
Oh!  Good!
5:38 PM Phil
Well actually all of it
Sitting on the porch, cigar in one hand, cock in the other
5:40 PM Sassy
Wow!  I’m at a little hole in the wall Thai place
5:41 PM Phil
[photo of him sitting out on his balcony with his erect cock sticking out of his gym shorts]
To show I enjoyed the story
5:41PM Sassy
Oh my!
Looks way tastier than my soup
5:42 PM Phil
Ha! Here’s to you sweet girl
[photo of his smiling face with a cigar in his hand]
Some random old fart
5:45 PM Sassy
[photo of my face, and a restaurant window]
[photo of the interior of the restaurant]
You are looking so sexy!
5:45 PM Phil
We have a Thai place just like that here minus the cute chick
I liked how you stroked my cock under the table 😛
5:47 PM Sassy
We had talked about that a lot online, had to make it happen
5:48 PM Phil
Very naughty but very hot
Not sure you noticed but I was staring at your tits today
5:50 PM Sassy
So glad they were useful

5:50 PM Phil

Had to clean off the screen
5:51 PM Sassy
Made me smile through a rather rough day
5:51 PM Phil
Well cool!
5:51 PM Sassy
Oh my!
5:52 PM Phil
Smiles are good for you as are damp panties
5:52 PM Sassy
You think about cumming on my tits?
5:52 PM Phil
Oh hell yeah
I sort of did
5:53 PM Sassy
5:55 PM Phil
I have a bit more work to do and I’m going to do the floors 
and then sit out here naked playing with myself
5:55 PM Sassy
Great plan!
I’m eating dinner, then home to play!
5:56 PM Phil
After that story I need to cum
Oooh! Tell me about it, I’ll cum with you
5:56 PM Sassy
I’m going to read it again, probably with the same result
5:58 PM Phil
I like the thought of those sweet juices running between your legs and over your ass.
You need a warm tongue lapping them up
6:01 PM Sassy
I do!
6:04 PM Phil
I’ll bet a tongue flicking over your ass would increase the flow. A toy on your clit a finger slipping into your pussy and a tongue slipping over and into your ass might help
Just saying
6:06 PM Sassy
I want to try it and see.  ; )
6:06 PM Phil
6:14 PM Phil
I tasted you at the airport you know.

I had your cheeks spread on your bed and was tempted but wasn’t sure how you’d react to suddenly having a tongue  in your ass.

Gotta do my floors, take a shower and get naked
May slip a finger in my ass thinking about you doing it
Sorry I interrupted your dinner with my lascivious thoughts
6:28 PM Phil
[photo up from under of his balls and cock]
I’ll behave myself now
8:21 PM Phil
Hope I didn’t upset you
8:42 PM Sassy
Not at all!
8:44 PM Phil
Oh good!
8:44 PM Sassy
I licked the screen again
8:44 PM Phil
Mmmm, prefer you licked the real thing
8:45 PM Sassy
Me too!
I’ve been playing.
8:45 PM Phil
Wish I got to watch
8:46 PM Sassy
I re-read that CA story

Better than I expected
8:46 PM Phil
Made me horny
8:46 PM Sassy
8:47 PM Phil
Well yeah 😉 
8:47 PM Sassy
I took photos while playing
8:47 PM Phil
Hope you are going to share
8:47 PM Sassy
So you can see bits of it
Where are you now?
8:55 PM Phil
On the porch
8:55 PM Sassy
Nice evening?
8:55 PM Phil
It is
8:55 PM Sassy
Beautiful here…
8:56 PM Phil
Same here. Gorgeous nite
Naked of course
8:57 PM Sassy
You got me going…shed my clothes and got in bed the moment I got home!

8:57 PM Phil
Damn, I like that
8:57 PM Sassy
[photo of my face and chest naked lying in bed]
8:58 PM Phil
8:58 PM Sassy
Thought about you…
What you like
8:59 PM Phil
[photo of his furry tummy and erect cock naked outside in the dark]
Me now

9:00 PM Sassy
Ooh….I know what to do with that beautiful body!

[photo of my left nipple and breast]
9:02 PM Phil
Mmm oh yeah!
Would love to wrap my lips around that
9:04 PM Sassy
I thought about that and tugged on it
9:04 PM Phil
Love how your nipple is aroused
9:04 PM Sassy

[photo of my tummy and legs lying in bed]
9:06 PM Phil
Mmm, like to lick my way to the v
Pre cum is sweet tonight tasty
9:09 PM Sassy
I got out my purple friend

[photo of my purple Lelo vibrator in my left hand]
It reminds me of you
9:11 PM Phil
Oh damn babe
9:12 PM Sassy
[photo of my face and shoulders with the Lelo vibrator in my mouth]
9:12 PM Phil
Oh yeah suck it Sass,
Thought about sucking you
Hot, wet, tight…in and out
My hand on you
9:13 PM Phil
9:14 PM Sassy
My mouth on you
9:14 PM Phil
Mmm yeah stroke my cock, suck me
9:15 PM Sassy
Your voice makes me tingle!

[photo of my naked shoulders, chest and tummy with the Lelo vibrator between my breasts]
9:15 PM Phil
Love that
9:16 PM Sassy
Put it where you might put that gorgeous cock
9:16 PM Phil
Would certainly put it there
9:17 PM Sassy

[photo of the furry spot between my legs]
Pushed my panties aside
9:17 PM Phil
Oh yes! Sweet pussy
9:18 PM Sassy
So empty…need to fill it
9:19 PM Phil
Want to rub my cock up and down it and then thrust in deep
9:19 PM Sassy

[photo of my tummy and legs with the Lelo vibrator on my clit]
I buzzed my clit…back and forth
Thought about you watching
9:20 PM Phil
9:21 PM Sassy
Thought about my cock in there…
You talk so well!  When you say fucking…my insides go crazy!!
9:22 PM Phil
Fingering my ass thinking about your finger there
9:22 PM Sassy

[photo of my tummy and legs with the Lelo vibrator on my clit]
9:23 PM Phil
Oh yeah, fill that pussy
9:23 PM Sassy
I thought of you balls deep, slapping against my ass…and BOOM
My inner muscles clenching
9:24 PM Phil
Like to slide cock in under that toy
9:24 PM Sassy
Oh yeah
9:25 PM Phil
Oh yeah cum on my cock as I shoot inside you over and over again
Filling you with cock and cum
Love feeling your pussy clench around my cock
9:29 PM Sassy
Mmm mmm mmm
9:30 PM Phil
9:34 PM Sassy
Wow!  It is mind blowing to watch you cum!
9:35 PM Phil
Glad you enjoyed it, I sure did!
9:36 PM Sassy
So so good
9:36 PM Phil
Hit me on the chest
9:37 PM Sassy
Oh my!
9:37 PM Phil
I am off to bed sweet girl! Thanks for a fun evening
9:38 PM Sassy
Sleep well!
9:38 PM Phil
You too  XXoo
9:38 PM Sassy
I’m going to cuddle beside you
9:53 PM Phil
Plenty of room

WrySmile opens up

September 16, 2017 Saturday

from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:31 AM
subject: Sassy Saturday

Good morning! Time for a Sassy Saturday! 

In lieu of my presence, I will send you some virtual treats!

Evenings are possible! I’m not doing much for this project except every other Saturday and then the final prep in a couple of months.

Thank you ever so much for the p0rn! I didn’t have a chance to get alone to watch but I will soon. Do you have a Tumblr account? Most of my current faves are on there, and they’ve recently clamped down so you can’t see them without an account. Here’s a little loop I think works in the clear:
(sorry it doesn’t work… it was a woman licking a man)

Thanks for telling me about the failed attempts at anal. My last try was in my 20s with a long-time boyfriend… he got carried away and ripped me into bloody shreds – lack of knowledge there are well. After all that p0rn you ought to be as knowledgeable as an anal virgin can be, right? Every one tells me the key is going slow and lots of lube.

Here’s a .gif with exhibition and anal – definitely need a Tumblr to see it. Ah, those French.

I have two cats! They are mostly Hubby’s – he got them while I was in chemo as an emergency rescue from a project peep who developed allergies. I look forward to hearing your story about kicking the allergy! I ask because there was an AM man I met and affectionately call “Sneezy.”

Glad to hear you’ve discovered the fun of toys! They are a recent addition to my life – still figuring out their best uses.

I write erotica too! I adore it as a window into a man’s mind and a way to tell a man things about my fantasies. Please share! I’ll send you a snippet. If that one appeals, let me know and I have another with some anal action.

I’ll send a couple of photos too. Start with the face below. This was the hottest day of last year, on a boat, on Lake Winnipesaukee!

[photo of my smiling face]

Have a lovely day and don’t think about my ass too much! Mwah!



from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:32 AM
subject: The Black


Here’s a photo of my assets.

I fought hard to keep them so I get to show them off, right? 😉


[Photo of my cleavage with the black bra]


from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 11:42 PM
subject: The Drink

Sassy, let me know what you think.


The Drink

[He sent me a snippet of erotica about a couple at a bar discussing what they might do if they could be alone]


from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:32 AM
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: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 9:01 PM
subject: Re: The view

Thanks that was fun. I’m polishing up some of my stories and I’ll send some to you soon.

Do you have time to talk Sunday?


from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 9:56 PM
subject: Re: The view

Hiya! Glad that was fun. It gets to me every time I read it.

Hope you had a lovely Saturday. I survived another project event!

Oooh…the thought of hearing your voice is revving me up! What a good idea! I am around tomorrow – should be home from brunch by 2 pm. Not sure about dinner plan. What time works for you?



from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 10:40 PM
subject: Re: The view

Great! I can be available after that until 5:00ish. You pick the time and place somewhere near the Red Line. Toscanini’s?


from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 11:29 PM
subject: Re: The view

I hope you enjoy this story; I expanded it and polished it tonight.


[he sent a story about a woman going to a party with a vibrator insider her and having anal sex with her]

Connection with WrySmile

September 15, 2017 Friday

from: Sassy
date: Fri, Sep 15, 2017 at 9:17 AM
subject: Connection

Hiya! Happy Friday! Tap…tap… is this thing working?

Is this the right email address for the guy from that website? I like to check before launching into anything more…



from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 11:01 AM
subject: Re: Connection

Hi Sassy,

Yes, it’s me! To prove it: I sent you two excessively long messages last night.

I wait for your response with breathless anticipation. ;+)


from: Sassy
to: WrySmile 
date: Fri, Sep 15, 2017 at 11:42 AM
subject: Re: Connection

Hiya Wry!

Hope your Friday is off to a grand start! Thanks for the long luscious messages! I read them in bed last night and went to sleep with a big smile on my face.

I’m at the office, just finished wrestling with the payroll. Whee! Mundane but important. Now it’s time to take a break and be with you for a few precious moments!

Your offer of ice cream was original! Much better than the usual coffee or bar meet ideas… I roll with them but I don’t drink coffee or booze so this is better. I will admit I like Christina’s Ice Cream in Inman better than Tosci’s but I rarely get to either. I’ve been to JP Licks recently. They are tasty but not in the same league!

I was actually asking how you heard about AM. Heh. But your answers to the different questions were entertaining!

Are you still in touch with Donna? My first time was at 17 with my high school sweetheart, after we dated for 4 months. We kept going a little further and further until… all the way. It was… dull. We had no clue what we were doing. We puzzled over why the adults thought this was so fun. I’ve learned a lot since then!

I gave up on my sex life ages ago when Hubby decided I was not attractive. I thought he was right and that part of my life was over, but an old flame from high school found me after 37 years, wanted to finish what we started when I was 14, see if the chemistry still burned. We spent a magical two days together 7 years ago. He resurrected me sexually, taught me that a woman can participate and enjoy! He was military, married and miles away, so he encouraged me to find a local option. My friends pushed me to AM. I thought no one would want a curvy, 50-something woman with long gray hair… I was wrong!

I was going to make some pithy comment about misspelling discreet in your profile, but the moment has passed! If you keep using that profile, please fix that!

Nuts? All double-entendre are completely intended. Sassy! Groping is a fine art and I’m happy to tutor. It is fun for both parties! You can help me with the finer points of hugging and caressing. I also volunteer to check out your kissing prowess and report my opinion. I’m having a lovely time imagining that…

Your career path is strangely aligned with mine – I’ve worked with many of those professionals! Though I am not my job… I help run a community project and that is more what fulfills me. Do you mostly work in an office or home or visiting clients? I was educated at a prestigious women’s college, mostly about how corrupt and insular such places can be!

Answers for you:

>Have you had affairs?
Yes. With Hubby’s consent. Old flame and some AM Men.

> When was the first time you had sex – see above

> When was the last time you had sex
Aug 25. There is a nice man who pings me a few times a year for a meet, no communication otherwise. He is sweet and vanilla and falls into the “much better than nothing” category but I definitely need more! More communicating, more sex! Once a month would be nice? Or more?

> When was the first time a lover gave you a powerful orgasm? How did it happen?
It was on the phone… mmm. Oof… that man could talk.

> What kind of porn do you enjoy?
I have a wide range of favorites, mostly fall into the “a man and a woman being nice to each other” category, but as it gets longer since I’ve had sex, my tastes get raunchier. I am currently having fun with Tumblr exhibitionists who post scandalous public displays of flesh. Not something I want to do but I enjoy their naughtiness! I like .gifs, those little loops that act as a springboard for my imagination. I can send samples if you’ll reciprocate. I tend to look for things I know a man will like, since most p0rn is made for them.

Tell me or show me what you like and I’ll watch out for it and share stuff I find?

> Please name some of your favorite movies
I don’t see many. I like movies with kissing. My all-time favorite is a period piece – the Merchant/Ivory romance called “A Room With A View” about Brits traveling in Italy. I adored “Spotlight!” I tag along with Hubby who has to see “Star Trek” or “Star Wars” the first night. The last movie I saw was “The Big Sick” which had its moments. Did you see “Lion” with Dev Patel and Nichole Kidman? It was intense and delightful.

Do you know about the 70mm festival at the Somerville Theatre? We saw “West Side Story” last year… spectacular! They’ve commissioned a new print of “2001: A Space Odyssey” for this year along with a lot of strange and wonderful films.

> Enjoys jazz
I don’t know much about it. Who are your favorites?

I like music I can sing along to. Do you sing?

I’m a folk music fan in the David Wilcox, Christine Lavin, James Taylor vein. Or Broadway show tunes. Or a cappella.

> Has eyes I can get lost in
If you like blue eyes with a twinkle.

> Loves long sessions (10 minutes +) receiving oral sex
[I think I know the answer to this]

20 minutes would be good. With a finger or two added at the right moment. ; )

> Makes me laugh
[We already know the answer]

Ha ha. You know it.

> Hates most current comedies; thinks action movies are mostly boring
Agreed. I did like “The Italian Job.” Seen that? The trick with the traffic light… I long for that on my daily commute!

> Has a nice butt
You betcha!

> Enjoys giving head
[We know the answer to this too]

Oh yeah… I’ve been told I have mad skillz. Heh. I had never done this until old flame requested it, had to watch videos to catch up on the best techniques but I think I’ve got it now. I used to think it was all about sucking but now I am more into licking and stroking…

Mmmf… where was I?

> Politically liberal or, if not, enjoys a good debate
So so liberal. Not a debater.  Politics these days makes me sick. *sigh

> Enjoys back door play or is willing to experiment
Would take a lot of trust and lube… I have had success with prostate massage… nothing like hearing a man say, “I’ve never cum so hard in my life!”

> 420 friendly
No experience with this. Brownies? Smoking?

I am fascinated with all this – I appreciate you asking questions! We can have wonderful conversations and laugh and smile. I can’t tell yet about more. Wish it could help me know how the skin on your wrist would feel under my thumb… how your beard would tickle my inner thigh… mmm.

I’d better go do more work before this turns into a novel! Hugs with groping… and an ear nibble.



from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 8:47 PM
subject: Re: Connection

Where to begin? First, I want to say that I’m having a lot of fun communicating with you and I’m looking forward to talking to you voice-to-voice or face-to-face. I think I’d like to get to know you, even if we never get into bed together.

Next: what are you up to during the day Saturday? (When I first typed it, it came out Satyrday; how appropriate.) My wife will be out of town until late afternoon. (Just to talk – and maybe stroke – not a tryst.) Let me know.

The ice cream invitation was just me being me. I figure it’s a more relaxing way to meet. And talking about interesting ice cream flavors can help when conversation flags. (Can you imagine the conversation over coffee: “I usually get the Extra Dark French, but sometimes I go for a lighter Colombian blend.” “Oh really! How did you get into Extra Dark French?”)

Ooh ahh! Which community project group??? I was in and around several a dozen years ago.

I do sing! I was in a chorus years ago. I’m terribly out of singing shape now. I used to play the guitar and sing obsessively. But in my 40s, I started doing it less and less; then a health problem forced me to stop playing guitar. Singing show tunes karaoke isn’t as much fun for me. (“Stars”, “Empty Chairs at Empty Tables”, “Luck be a Lady”, “Man of La Mancha”.) When in shape, my voice is pretty good and my sense of pitch is very good.

I like your taste in music and movies.

My taste in porn is almost always amateur porn, and a lot of it includes anal. To me woman’s orgasm is the sexiest thing in porn – and in person. The woman must be enjoying it a lot. Not acting – or at least acting really convincingly. I’m setting up a space on my Google drive to share videos with you.

Prostate massage? Wow! Never tried it; it sounds amazing. Similarly, I’ve given powerful results by triple stimulating – tonguing and fingering front and back. (My mouth is watering.) (On our second date, I ate my wife to orgasm – a first for her. I think that’s why she married me.) I’m intrigued by your 20-minute idea, but even the tongue gets tired after a while. And the payback would have to be pretty great.

I am still in touch with Donna; we had coffee together about 5 years ago (really nice) and we emailed each other a few weeks ago.

Where have you met your lovers? I presume you throw hubby out of the house for a few hours and bring them home. Do you use any sex toys?

I’d be happy to introduce you to smoking pot. (Speaking of powerful orgasms.) But, do not try eating it until you’re more experienced! It’s very hard to control the dosage and the high lasts for hours. (Remind me to tell you about an adventure with cookies.)

That’s enough for now. I hope this email makes bedtime more fun. Let me know about Saturday.


from: WrySmile 
(via Google Drive)
to: Sassy
date: Fri, Sep 15, 2017 at 9:05 PM

subject: sassy – Invitation to collaborate

WrySmile has invited you to contribute to the following shared folder:
SASSY folder

Sharing some downloaded videos


from: Sassy
to: WrySmile 
date: Fri, Sep 15, 2017 at 10:26 PM
subject: Re: Connection

Hiya! Thanks for perking up my Friday night! This is fun! You are a quite an interesting man.

Oh! It would be grand to see you tomorrow! But I can’t…argh. I am helping on the community project all afternoon. Let’s find another time soon?

I like you being you! You are so clever! Ice cream is definitely a fun, safe subject. Will we ever run out of topics?

Anal, eh? Fascinating. Have you done it or is it a bucket list item? I look forward to seeing the videos you like.

Awesome that you still see Donna! Speaks well of you!

> Meeting places?
Varies. Hotels mostly. I brought a few men home after I knew them better. Are you allergic to cats?

> Do you use any sex toys?
Oh yes. Do you? I own a bunch – friends recommend them when they’re on sale, and I had no idea what I’d like so I got them all. Heh. I find they enhance things with a man, and keep me calmer in between. Oof… I sound like such a hussy. Ah well!

I have two faves right now – These are made for internal use, but I use them outside to buzz my clit. Or help a man tingle.

1) Lelo Gigi 2

2) Nasstoys Ultra Elongated Vibrating Silver Bullet

> I’d be happy to introduce you to smoking pot.
This scares me… though I should try it once to see what happens?

I would have to trust you to take care of me.

(Speaking of powerful orgasms.) That is tempting!

Have you smoked for a long time or picked it up recently?

I’d better send this along. Sweet sexy dreams! Mwah!



from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 11:44 PM
subject: Re: Connection

This is fun. It’s great to have someone to talk with about intimate and “dirty” things. It’s a shame we can’t meet tomorrow; when are you free? Can you meet for ice cream on a Tuesday or Wednesday night? Next weekend?

Some quick responses go your message:

Unfortunately, anal is a bucket list item. I’ve tried it a couple of times: once a failure (the last woman I had sex with before 38 years of fidelity) and once an epic failure (wife refused all future tries). We had no idea what we were doing.

We also have cats (2). Mostly they’re my wife’s. I used to be allergic; I’ll tell you how I got over it.

Toys: my wife had no interest. I recently bought a fancy stroker for my “practice” sessions (Blewit); it feels great. (My wife has been curious about the device, but that’s it.) I’ve read about the Lelo Gigi 2; it sounds amazing.

There’s no reason to fear marijuana; if you want, I’ll make sure you start slow. I started smoking early in college. I smoked through my 40s — a friend grew great weed and kept us supplied. But when he stopped growing, I had to quit for lack of a source. Until recently.

A few months ago, I tried writing some porn. As literature, it was a dismal failure; but they might turn you on and they’ll tell you something about my fantasies. Shall I send you one? If I do, you’ll be obliged to reciprocate by telling me some of your fantasies. Or maybe your failed attempts at writing fiction. (Another Freudian typo — it originally came out as “fuction”.)

Have fun tomorrow. Let me know when you’d like to meet. And please consider sending me a picture of your face.


Nice to be wanted

June 17, 2017 Saturday

4:13 PM Phil
[photo of his cock with pre-cum on the tip, sitting at his desk]

I was just thinking of you

4:15 PM Sassy
Oh my. What about me?

4:25 PM Phil
Well all of you but you were naked

4:25 PM Sassy
What was I doing?

4:28 PM Phil
You were on your hands and knees being fucked hard

4:32 PM Sassy
Mmmm. Sounds fantastic

4:32 PM Phil
There were toys involved

4:35 PM Sassy
Very good

I used my Gigi on Hubby this morning
he has a pinched nerve in his shoulder!

He didn’t see what it was

4:36 PM Phil
You were using it lower on me in my fantasy

4:37 PM Sassy
Oh… between your legs?

4:38 PM Phil
Oh my!
Yes indeed

4:41 PM Sassy
I have been wishing I could explore your lower regions with a toy… learn what makes you moan.

You relaxed on my bed… the vibe buzzing… mmmm

4:49 PM Sassy
Tall ships are in Boston Harbor! A friend posted 20 photos of the US Coast Guard Eagle.

4:52 PM Phil
Wouldn’t take much.

4:57 PM Sassy
I so need some of that… been 6 weeks!

I was fantasizing about you disappearing for an afternoon when you’re in the old hometown…. meeting me at the mall… FUCKING

5:09 PM Phil
Well damn!

Six weeks, you need some cock

5:11 PM Sassy
Gonna go play right now!

Look at some nasty tumblrs and rock

5:12 PM Phil
Mmmm, I like nasty tumblrs

5:13 PM Sassy
If I see something hot, I’ll be sure to send it along

Been rather paltry lately…

5:13 PM Phil
Feel free to send a pic of you too

5:14 PM Sassy
[photo of me in bed on my side with my kitty cat in my arms, rubbing his tummy]

5:20 PM Phil
Ahh rubbing the pussy

5:20 PM Sassy
[photo of my legs spread in bed with my hand between them]

5:21 PM Phil
Mm, like that pussy better

5:21 PM Sassy
Thought you would

[photo of my naked breast, tummy and legs with a toy between my legs]

5:25 PM Phil

5:25 PM Sassy
[photo of my legs with a toy between them]

5:25 PM Phil
[photos of him lying in bed stroking his cock]

5:26 PM Sassy
Oooh yum

5:26 PM Phil
Take good care of that sweet pussy

Fits right where that toy is

5:27 PM Sassy
[photo of my legs spread with a toy on my clit]

5:28 PM Phil
There we go, spread those legs, mmm

[photo of his cock in his hand lying on his bed]

5:29 PM Sassy
My hands could be there

5:29 PM Phil

Oh yes

5:29 PM Sassy
Pump it.

5:30 PM Phil
Like to pump it in you
Hope that’s helping moisten things up
Feels good

5:33 PM Sassy

5:34 PM Phil
Mmm, nice!

5:43 PM Phil
You need a tongue to go with that toy, lapping up those sweet juices

5:43 PM Sassy

5:44 PM Phil
Oooh there we go!

5:44 PM Sassy
Target for your tongue

5:46 PM Phil

Or for that

5:47 PM Sassy
One then the other.

5:47 PM Phil
Or both! One will spray your burning hot pussy with cream

I remember being the first to cum in your sweet pussy is some time. Felt so good cumming inside you and you seemed to enjoy it as much as I did

5:51 PM Sassy
10 years without

5:52 PM Phil
Still very fresh in my memory

5:52 PM Sassy
Hottest night of my life

5:54 PM Phil
Oh just cause I tore your pants off and stuck my tongue inside you followed very soon by my cock, I’m sure it happens all the time

😛 it was spectacular

5:57 PM Sassy
You were so good to me

5:59 PM Phil
It was hot and sexy and fun and you were pretty good to me too
And we found some good food too

6:00 PM Sassy
Perfect night
And I played the old a cappella tunes

6:02 PM Phil
Wonderful. Those were good times.

I can’t see a girl in overalls without thinking about having a handful of your ass and tits


I smile every time I go by that Thai place

6:03 PM Sassy
I know so much more now…tough to believe but it could be even better

6:04 PM Phil
You are a bit more experienced and adventurous.
I’m intrigued by the toys too

6:07 PM Sassy
I want you

6:09 PM Phil
Nice to be wanted XXoo

6:09 PM Sassy
Oh yes

Fingers exploring

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March 10, 2017 Friday
From: TimmyTim
To: Sassy
Date: Fri Mar 10, 2017 at 6:08 AM
Subject: FRIDAY!

It’s finally Friday! No more waking up early! Not snowing yet at 6:00, but the air smelled like weather and glorious! So get your caffeinated beverage and attack your day!
Look at your schedule and see what works for you next week! I’ll check to see what our plans are around the potential snow storm. I just so want to put my arms around you and make you squirm with pleasure! 

Do you think we could talk on the phone Sunday night?! We could catch up on our lives and have a real sassy time. Oh I just want to intertwine my body with your beautiful body! I want to give you the pleasure you give me every time we meet! You are such an erotic, sexy soul! We can talk about our next phase of the syllabus! John Henry misses you!
Hugs with fingers exploring our most intimate, sensitive parts!
Take care,
From: Sassy
To: TimmyTim
Date: Fri Mar 10, 2017 at 8:09 AM
Happy Friday T!  
It’s snowing!  I’m rolling to work!  I’m thinking of you!  
I’ll look at my work calendar and let you know.  Boss is out today so it should be a calm day.  
Talking to you Sunday sounds awesome!  What time Sunday?  I have a meeting at 5 pm but nothing else planned.
I got Gigi going big time last night, thinking of you and all the fun we’ll have!  Mmm mmm mmm.  
Be careful in the snow.  Imagine us clandestinly kissing in a doorway with the snow swirling!
Sent from Yahoo Mail on Android

Always amazing

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March 9, 2017 Thursday

From: TimmyTim
To: Sassy
Date: Thu Mar 9, 2017 at 6:01 AM
Subject: Thursday already!
It’s Thursday, or the day of the Germanic god Thor! In Latin it was Mars day! So this is a day to do battle! But on the peaceful side, only one more day to wake up early!
Now, for a “triste”, would Thursday, weather pending be an option? I just have to see you, hold you, feel you, taste you!
Let me know!
Hugs with deep penetration!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTim
Date: Thu Mar 9, 2017 at 8:29 AM
Re: Thursday already!
Hiya T,
Hope you’re having a terrific Thursday!  I am off work, going to see the tax accountant first thing.  Whee!  It will be so good to take anothet step to finish tasks for Mom and my annual chore.  I hope I have all the right papers.  For the past few years, I’d go to H&R Block, sit there for over an hour, then be told to go find a bunch of other papers!  Ugh.  
Do you follow the Iditarod?  I had fun looking at doggies and beautiful Alaskan scenery last night as the leaders crossed on to the Yukon River.  
Not sure what we’ll do the rest of the day…hope for a nice lunch and a nap.  I got Gigi out last night and can report she’s back in fine form!  Maybe I can use her again today!  And think of you.  Mmmm
Next Thursday sounds fantastic!  But let me get back to my calendar at the office tomorrow to be sure.  Do you want to come here or have another idea?  I’m so excited to be with you again!  I want you to feel so amazing!
Gotta roll.  More later!
Sent from Yahoo Mail on Android
From: TimmyTim
To: Sassy
Date: Thu Mar 9, 2017 at 2:29 PM
Re: Thursday already!
for me with you, it is always amazing!
Hugs witha huge erection!
Take care,

wet, wet, wet

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March 8, 2017 Wednesday
From: TimmyTim
To: Sassy
Date: Wed Mar 8, 2017 at 6:01 AM
Subject: Humping day
It’s hump day again! How is my hump partner?! We got to celebrate hump day soon! But once up the weekend is practically here. You’ll be happy that it is warm outside, but it is wet, wet, wet! We need the rain though. Talking about wet, how is Gigi?
I have my thoughts about our next meeting which should be next week! But what are you thinking? After watching tumblr videos, I would love to lick you while using your long toy! Then the thought of us bent over in front of the mirror just turns me so on. I love how deep I can go in you from behind and it’s like John Henry was just made for you. Maybe we can try the “headboard” position again!
I have a million questions for you but I will write later when my brain is more focused. Right now John Henry is in charge!
Hugs while making passionate love!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTim
Date: Wed Mar 8, 2017 at 7:37 AM
Re: Humping day
Good morning T!  Hope you have a wonderful Wednesday!  Even if it’s wet…
I’m under the covers indulging in the fantasy of rolling over and waking you up in a sexy way.  Mmm…
Your fantasies have me nodding…yes, yes, oh yes!!
I fell asleep at 7 pm last night so no Gigi.  But she’s charged up and ready when I get time!  
Put your hand on your knee and rub…imagine my hand there and where it will go next.  😉

Sent from Yahoo Mail on Android

Straight not narrow

March 5. 2017 Sunday

From: Sassy 

To: TimmyTim

Date: Sun Mar 5, 2017 at 12:47 PM
Subject: But it’s cold outside…
Hope you are relaxing and keeping warm this cold Sunday morning! I can think of a few ways to warm you up! Just thinking about them is already making me warm (and John Henry stand at attention)!
Hope you had fun celebrating hubby’s B-day yesterday. I like going to the beach on my B-day. How about you? What do you like for your B-day? Anything special?
I am going to a fitness club because the doctor said my blood pressure is boarder line and if I don’t work out, eat better and watch it, he would put me on a beta blocker. Did my research and found they can cause erectile dysfunction, so I started this health thing! Yes, I’m going to use you as a cardiac exercise when we meet! Today will be my third time and I am feeling better. Didn’t realize I was so out of shape!
Now I should be prepping for work, but you make it so easy to procrastinate!
So you have your first trans-gender worker. I had my first transgendered student about 16 years ago when the world was not yet enlightened. Lost a few co-worker friends while advocating for him. Learned so much. Figured I didn’t need those narrow minded “friends.”  I have always maintained I am straight but not narrow. At least our company is rejecting that Trump garbage about not hiring transgendered people. I have one now who is confused. The present Idiot In Chief is not helping!  
Hope to hear how you are keeping warm and I hope (work promises but has not said anything) to have our training schedule early this week so we can have some heart healthy fun!
Hugs with a good romp in bed!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTim
Date: Sun Mar 5, 2017 at 4:45 PM
Re: But it’s cold outside…
Hiya T!  
How’s your Sunday going?  Hope you are warm and happy.  
I am tackling triple tax prep for my mom, her estate and myself, getting things ready for the new accountant.  It is one of my least favorite chores!  Luckily I make up a series of folders and toss things in all year, so I only have to organize them and total up the medical expenses etc.  I finished Mom’s stuff and am taking a break before doing mine.  I puzzled over whether expenses incurred before death but paid after count as mom or her estate… noted the details so the accountant can do what’s right.   
When you were writing, I was playing!  Hubby was out getting breakfast, so I had fun with the silver bullet and tumblr and thoughts of John Henry and BOOM!  Hee hee… I wish you were here to warm me up… make me burn.  Mmm… I’d do the same for you!  
It is lovely when Hubby has a birthday and I get to tag along on his food adventures.  And he is unusually nice to me, noticing me in ways he does not most of the year. I get that treatment on Valentine’s, my birthday, his birthday and our anniversary.  Of course it’s a double-edged sword because it makes me aware he is capable of doing it, just…doesn’t the rest of the year.  *sigh
The beach is great for my birthday!  I try to get up to Gloucester to Lobsta Land for lobster, and find a beautiful ocean view at Good Harbor.  Or go down to Rhode Island to my favorite restaurant, The Boat House on Mount Hope Bay in Tiverton RI.   
Glad that you can do the gym thing if that’s what they say will help.  I went to a gym while I was unemployed for 4 months in 2003.  I lost 30 pounds but hated every moment of it.  Hope it isn’t like that for you! 
I have a button that says “Straight but not narrow!”  I am so glad you help people who need advocates and understanding and support.  That can make such a difference.  You would have smiled at the Oscars when several of the winners thanked their teachers!  No one ever thanks the office administrator.  Heh.
We’re headed out for sushi with another of Hubby’s lady friends and her beau.  She is a lot of fun – won big bucks on “Jeopardy!” a year ago and puts some of her winnings to good use doing social stuff with friends. 
Hugs with John Henry deep down my throat. 

Hugs with toys

March 3, 2017 Friday

From: TimmyTim
To: Sassy
Date: Fri Mar 3, 2017 at 6:02 AM
Subject: Friday!

It’s Friday! You made it, once you are up, it’s just a downhill slide to the weekend!
Worked out yesterday for the first time in the 21 century, and I am in pain and over slept! So I will write more after workl! So much to talk about!
Can I pull a rabbit out of your hat! Is John Henry’s friend Gigi going yet?!
Hugs with toys!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTim
Date: Fri Mar 3, 2017 at 10:35 PM
Re: Friday!
Hiya T!  Hope you had a Happy Friday!  And stayed warm… I was not prepared for the sudden shift in temperature!  Brrr…. 
What possessed you to go to the gym and overdo it?  Hope the pain goes away!  
No Gigi – still waiting on the cord.  Silver bullet fills in nicely.  
Today was wacky…  had a new worker show up at 9:15 am.  First trans person that I know of that we’ve hired.  Nifty!  Then an hour with the boss, who as usual, loaded me down with four more projects on top of the 15 I told her about.  *sigh 
It’s been a lovely evening… quiet… Chinese food… thinking of you and smiling! 
Take care! 

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Rabbit trick

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March 2, 2017 Thursday
From: TimmyTim
To: Sassy
Date: Thur Mar 2, 2017 at 6:07 AM
Subject: Thursday Already!
Once you are up, it practically Friday already! So start planning that weekend!
The problem with the dentist was she couldn’t deaden the tooth she was working on! I had like 5 novicain shots, so my face was dead but the tooth was raw and painful! Worst of both worlds! I went to sleep when I got home which threw my whole evening off! Feel much better today, but I’m behind in my work!
I saw a great video of a woman having oral while using a toy! We should try that next time! Once the new training schedule comes out, we can make some plans for some magic moments together! That’s what I’m calling them because our time together is truly magic!
Giving some quizzes today but otherwise today is pretty easy in the training realm today!
How does your day shape up?
Hugs with a little toy!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTim
Date: Thur Mar 2, 2017 at 7:15 PM
Re: Thursday Already!
Hiya T!  Hope you’re having a lovely Thursday evening.  How’d the quizzes go?  
I had a wacky day!  I took a huge file of data and sorted and chopped it up to make email lists to send out hundreds of invitations to two receptions, and made four more lists to post on the web.  My eyeballs are about to fall out!  I always think it can get it done in one day but something always interrupts me so it takes part of two days.  At least I know that so I don’t wait until the day before the deadline!  I have to do this painful project twice a year and it feels like hitting myself over and over with a 2 x 4…. it will feel great when I stop!  
Dental stuff is so gross!  I was at the dentist years ago and he couldn’t numb a back tooth enough to pull it, so he put me into a cab (full of Demorall and 10 shots of Novocaine) and sent me across Boston to an oral surgeon!  I stumbled in and there were four 6 foot plus tall thin black women assistants and a tiny 8 months pregnant dentist!  I couldn’t think enough to fill out any paperwork or answer any questions, so they just popped me into the chair and I prepared for some new torture.  The dentist reached into my mouth with these tiny tweezers and pulled out the tooth in 3 seconds.  I was stunned!  She was a miracle worker!  
You have a great idea there… I am so glad you’re not intimidated by the toys and can see how to use them and your skills to make me swoon!  We are magic… mmmm…. just don’t pull rabbits out of my vagina, okay?  
Hubby is out, so I can play!  I’m off to do that now!! 
Mwah!  Squeeze JH for me!