Category Archives: Email

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Discovery and due diligence

October 22, 2012 6:14 pm
From: The Lawyer
To: Sassy Girl 
I would love to be alone with you!!! I have a feeling that there’s a blazing fire awaiting us!!! My imagination is wandering all over the place, as the thoughts and images overwhelm!!!      MNNN… we need to think about logistics…. I don’t have any place available, and unless you have a love nest or a friend who’s in europe for the fall, we’ll have to make do….  are you put off by a hotel room?  I’m sure we could figure out a time and place that would give us some time and privacy…
the mere thought of this is turning me on!!! 
and, as a lawyer, i have a strong desire to engage in extensive discovery, and thorough due diligence– with you!! 😉
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October 24, 2012 7:24 pm

Hiya Tom, 
You make me smile!!!!
It has been so long… almost makes me cry, in a good way, to be wanted.  and it’s especially wonderful that it’s you.  And that it’s mutual!  Thank you, sweet man.  
Ah, logistics.  A hotel room works, though frugal me hates to think of you spending money on it but if you can… it would be lovely.  Anywhere you feel safe with me taking your clothes off, with a bed and you… sounds lovely.  If there are ways I can make it easier, let me know.  The other thing I require, to get right down to brass tacks – I assign you condom procurement.  
You being turned on was a fabulous thing to behold… even with nerves and people and sunshine.  Can’t quite imagine how much more fabulous it would be under better circumstances, but I am having fun trying!  Thinking sassy thoughts about my hands and my mouth and your body… hmmm…. I do wonder what would excite you most, so I can do it!  and then I think about your hands and your mouth and… more. Oh my… 
Har har… I’ve never been with a lawyer in such a proceeding… tempted to say something about your briefs but they might be boxers for all I know!   Hoping that occupations fade as we get closer… to the um…closing?  I should throw in some Latin phrase but I forget them all except pro bono which would be too much?!  
You are such fun!  Hugs with groping.  And a sensuous kiss.  or two or three. 

-S
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Mr Truck writes

October 22, 2012 3:34 pm 
From: Mr Truck 
To: Sassy Girl
Hello there sweet lady. Thanks so much for the nice detailed email. This is just a quick note to let you know I’ll be replying in kind soon, but let me also say that your enthusiasm for looking at and sharing erotic writing, photos, and video has greatly peaked my interest. This is a good starting point for us to begin cultivating your ‘inner slut.’ I love having frank discussion about sex, our bodies, our needs and desires & fantasies. Whispering hot dirty talk in each other’s ears while fondling and fingering is such a delight. I myself love those whispers followed by a warm probing tongue in my ear…..
I really am actually from the town I put in my profile so at least you’re familiar with the general area as you’ve been to places close by.
More soon but please don’t hesitate to write in the mean time.
Hugs and ass squeezes….

Stan
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Better than fabric

From: Sassy
Subject: Re: today
To: Rick
Hiya, Rick, 
Hope all is well with you.  
Thanks for not just focusing on the fabric… I was wondering if you’d notice that buxom gal in the background and you did!  I know the silky thing is the special thing.  But it is nice for me to be noticed, too. 
Thanks for explaining how your mind works… helps.  I am in odd territory but trying to be honest and let it play out, you know?  Our reactions are what they are, and if they can excite the other?  Very nice!
I’ve been thinking about touching you… listening to you moan, teasing you.
I can’t leave work to see you today but am trying to think of something else.  My arm definitely needs your fingers on it again. 
-S
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From: Rick
To: Sassy 
Subject: RE: today
Hi.  Home now, and able to look at that sexy picture more closely.
Of course I noticed that lovely, sexy woman!  She is more important than the fabrics.  Yes, I have a ‘thing’ for the lingerie, but can only share that information; and my kinks; when I respect and trust the person.  I’ve thought much more about you without any sort of fabric and the things we could do together than with the fabric. Reading that tumblr you sent me really has me fantasizing a lot about you having me on my back, playing with my cock, and fingering me.  Some fantasies have you telling me to lick my finger for you, saying how you want me to lube it up so you can play.  Other fantasies have you doing other things seen on the different tumblr pages.
Also, I’ve imagined a lot of hot-dogging with you, getting you sooo excited, begging for me to enter you.  And after enough teasing, I do oblige.  I also fantasize about you on your front, me rubbing your back as my cock rubs along your ass crack.  It is really exciting to me to think about that!  About playing with your backside, sliding in your crease, playing with it as well as your pussy.  I imagine how wet and wanting you would be when I finally enter you front behind, and in that position am able to go really, really deep.
So, yes, I noticed that sexy woman first. Having read what I wrote, I hope you believe it.  

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Sharing Lingerie

I’ve still talking with Panties Man.  I want to see if I can find a way to excite him and have some fun myself, if he can play outside of the humiliation model.

We’ve exchanged dozens of emails and had a lot of talks on Yahoo IM.  He was very impressed when I pointed out that it’s Halloween time… he could easily go to GoodWill or the Salvation Army and paw through their wigs, dresses, shoes or jewelry “looking for a costume” and no one would think anything of it other than he was going somewhere in drag.

He asked me about my lingerie.  Now… Sassy is not a lingerie girl.  I wracked my brain to think of anything he’d consider silky or sexy.  Suddenly it hit me – I do own one negligee.  It’s too small… haven’t worn it in years.  I’m not sure a man ever saw it on me.  But I figured Rick would get a kick out of it.  I told him about it as if I saw him wearing it in a dream:

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The negligee is a pale peach color, with lace in the bodice, an empire high waist, and long… swirling around your legs as you walk toward me with a very devilish smile.  (It hangs on the back on my bathroom door as a reminder of better days.  It’s about 5 sizes too small now, but still lovely to look at and feel sometimes.  I wonder if it would fit you? It probably qualifies as vintage!  Hee.) You dropped the spaghetti strap off one shoulder and winked at me.  I don’t know what I had on… you know how dreams are. 
Too bad you have no privacy… that’s almost like waving a red flag in front of a bull in terms of challenging me to tease you.  To talk about the wicked things… ah, well.  I’ll be good.  
 -S
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He begged for a photo of me wearing it.  It doesn’t fit, but I found a way to show it (and a bit of me) to him.

Date: Thursday, October 18, 2012
From: Sassy
To: Rick
Subject: Good morning

Happy Thursday to you! Sorry for the brevity…work being crazed. Maybe a photo is worth more than words? Hope you enjoy. 

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Date: October 18, 2012 11:59 am
To: Sassy
From: Rick

Oh..my..god.
 
This is beautiful.  What an absolutely wonderful present!!!  I love the pic!  both that you are in it, as well as the nightie!  And what an absolutely lovely nightie, it is.  damn, I want to see it…touch it….have you rub it on me….and I’ll definitely be fantasizing about wearing it for you, imagining such wonderful things we’d do.
 
I want to see it in person!!  And you!!
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From: Rick
To: Sassy

Another present, seeing you liked the other ones I’ve sent.  Maybe you’d like to see one of me hard in my panties from thinking of you, with my cockhead peeking out from the top?
 
So you know, I have rarely ever sent pics like this to anyone!!  Really; I don’t do this.  For whatever reason, I trust you and want to share, and you seem to like them.



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Wicked Wednesday

What is it about Wednesdays?!  I heard from all four of the Ashley Madison men I am talking to!  It’s amazing how much time this philandering takes!

I had shared with three of them (not Panties Man) that I was hearing from men with kinks (doms, subs, wearing women’s underwear – oh my!) that I could not deal with, probing to be sure they weren’t hiding such proclivities.  They reassured me they were not, each in their own way.  Phew.

Before I wrote this post, I had not looked at them side-by-side… as I do I realize how typical these emails are of each man, how similar and how different they are, and the range of choices I have!

Which one would you pick first?

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There was email from Ashley Madison, showing me six men in my area who signed up recently.  I like looking at them… it shows their nickname, age, town and a photo if they’ve posted one.  I am horrified by the face photos… seems like indiscretion of the highest order!  Dude!  Your wife can log on and see you!  Your boss can see you!  I clicked on a couple of profiles but as usual they hadn’t written much if anything yet.

Tip for men – don’t join AM until you have a full profile ready to go!  AM will show it to women right away and you’ll miss a big chance to get some attention!  And if you put a public photo, post one without your face!

I tried to think of writing to one, but that just didn’t seem possible.  It tells them I clicked and they can write or wink me if they are okay with BBWs.

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First up was The Professor:

12:32 am

Dear S.,

My fantasies are as unimaginative–and as electrifying–as can be: full-out, hours-long sex with a willing partner who has multiple orgasms.  That’s it.  No one has to play any “roles,” be “dom” or “sub” or whatever the lingo is.  I’ll settle for a woman who plays the role of “woman.”  That’s how plain-vanilla I am.

–Scot

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Next up – Panties Man:

6:52 am

ha!  You’re not sure what that mean???   aw, c’mon; that’s a simple dream to analyze! Was it pretty?  What were you wearing today?  

Thanks for that incredibly hot link!! 

Back to work today.  I’m having to share a cube due to space constraints.  Absolutely no privacy.

Date: Sun, 14 Oct 2012 19:04:16 -0700
From: Sassy
Subject: Sunday hot dogs
To: Rick

Hiya, 
Glad you hear your rolling along.  I had a dream of you in a silky nightgown… not sure what that meant!  Here’s a hot dogging gif for your pleasure.  Rock on, Rick!
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then along came Kevin, AM #1:

6:55 am

Sassy!  Here’s a little morning tingle as I stop you from doing whatever you are doing and pull you over to sit on my lap so you can feel some anticipatory throbbing as my hands work their away exploring your back and my lips lavish attention on the back of your neck.  Good morning!

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Finally I heard from The Lawyer, who had been silent for ten days.

3:54 pm

I hope the sassy girl hasn’t forgotten her lawyerly suitor!  He has returned….sounds like you’ve been busy whilst i travelled!! 😉   It’s absolutely amazing to me what (i) specific sexual eccentricities so many people have, and (ii) how willing, in the confines of cyberspace, they’re willing to reveal said eccentricities! Whilst I am generally amazed, often amused, and almost always tolerant of same, alas, I’m a little short-handed in matters of fetish! 


I hope you won’t find me boring, but I love touch, taste, intensity of feeling and the combined pulses of pure pleasure that come from fully pleasing one’s partner, and in return, being fully pleased. 

My fetish is the feeling of skin-on-skin, the delights of the heat of passion, the wet warmth of a beautiful woman in full throttled passion, her physical urgency and growing forcefulness as we mutually approach a climactic rush.  I hope that’s neither too forward, too explicit, or too “vanilla”… and I do have my own underwear– but wouldn’t mind removing yours…;-)… but I have no need to try them on!

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Teasing and tantalizing

I sent AM #1 a photo of my cleavage (you know the one, my icon with the black bra) to entice him to meet me.  He liked that.  We agreed to meet in ten days and here is a sample of how we spent the time… 
From: Sassy
To: Kevin
Sent: Friday, October 12, 2012 1:50 PM
Subject: Friday lunch fun

Happy Friday Kevin!
Well… that seems to have worked!  Your appreciation of my assets made me smile.  And giggle.  And swoon.  That means A LOT!  I’ve been missing that for way too long.  Please do explore… with your hands, your face… and another body part.  Since breasts are the topic, here’s another moving picture to um… titillate?  
I hope you had a lovely evening wondering what it will be like to touch me.  Since we didn’t meet up, I got into trouble on the internet, looking at images.  But I kept having to close my eyes and take my hands off the keyboard due to a vision (or was it a premonition?) of a tall man in a bar, hugging me… squeezing me, breathing me in and… it went several directions after that.  I try not to get too far ahead but it is so much fun!  My brain won’t shut up!  Even now in the midst of doing payroll!  

We are kissing right there in the bar, forgetting where we are, being alone together in the crowd.  Risky!  or kissing and groping, leaning against a car.  Cold steel on my back and you very warm pressed against me in front.  Hot!  Sometimes more… in a car.  Hands, mouths… button, zippers… whee!  Sometimes… even more.  Hmmmm.
I usually consider an offer to meet very carefully, but since you asked so nicely and wrote so beautifully that it made me wet, I’ll say a week from Monday sounds great, other than it is too long away!  But let’s make good use of the time in between…
My questions for today – do people ever say you look like a celebrity?  And which female celebrity makes you tingle?  
Have a great weekend!  
-Sassy
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From: Kevin
To: Sassy
Sent: Saturday, October 13, 2012 9:32 PM
Subject: Friday lunch fun

Good Morning Sassy:
That was easily my favorite of your short films. probably because that is exactly what we have been doing in my mind since you sent the picture of your delicious breasts.  Thanks for sharing – your visuals always get me nicely bothered! And I love what we have been doing in your mind – I am so looking forward to that moment where we first meet and hug, feeling our bodies against each other and especially when we manage to find a private spot later and share our first, heart-pounding kiss. I want your lips. I want your tongue. I want more…..
For our meeting, I will be downtown so pick whatever place you think will be the best. I can get to your area easily or we can meet anywhere convenient.
I do not get compared to any celebrities, but I can share some tingly female celebs with you. My first was Angie Dickinson. I remember her being on the cover of a magazine my mom had back in the 1970’s. I would sit and look at that picture and give myself massive erections when I was just starting to learn the joy of sexual excitement.  
In the 1980’s it was Phoebe Cates, who captured many a young man’s ….ummmm…heart?….with her topless emergence from the pool in Fast Times at Ridgemont High. My friends and I were so taken with her, we proclaimed that every day was “Phoebe Cates Day” and often wished each other “Happy Phoebe Cates Day” whenever one of us was in the dumps.  
Today’s most tingly females?  Salma Hayek? Yummy. Diane Lane? Makes me hard every time, which I don’t quite understand because I’ve never liked any movie she has been in. Elisabeth Shue? Adored her for years. Idina Menzel? I’d love to make her sing to me in bed. And my most recent one is Regina Spektor – on the younger side, but she has such a beautiful voice and fertile mind, that I’m willing to risk being considered a dirty old man for her:-) 
And if I could go back in time, Mae West wouldn’t have a chance at resisting my charm:-)
So feel free to analyze what my choices say about me:-)  And then share yours.

Speaking of sharing, wouldn’t it be nice right now if we were sharing lips…….

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On again again

It didn’t take long for AM #1 to get back to me.  So maybe the excuse about his daughter’s rehearsal had been true?  He said he was so sorry and we should plan another date.  I sent him a photo of my cleavage to entice him a bit more!  I know… bad bad Sassy!

Here’s part of his response, so typical of his charming self….

Hubba hubba! Wowza! Va-va-va voom! And any other sound of pleasure that isn’t quite an articulate word, because that’s how I feel after knowing you wore your lucky black bra just for me and after seeing those luscious breasts. I would love the chance to bury my face in them and explore!:-)  

The weekend and next week are tricky for me, but I can guarantee Monday night the week after if that works for you. I have a rare work event in downtown Boston until 7:00 that night. Can we get together afterward? (read that last question picturing me saying it in a seductively pleading tone with my baby blues locked right into your eyes so closely you can feel my breath flow into your mouth, my chest pressing up against your breasts and a throbbing in my pants up against your hips while we hold hands).
Kevin
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How could I say anything but yes?  It means another 10 days of teasing and tantalizing… yum!  Something about him makes my mind race in so many sexy directions!  I fantasize about hugging him… laughing with him… walking to my car and him kissing me.  Mmmm….

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Hugs with groping

[To read about my meet with this guy yesterday, click back to this post.]

He started the day off teasing me in email: 
Mmmm…I actually still don’t know what you mean by ‘hugs for groping’.  You might have to demonstrate it for me to really get it.
So I sassed him back at length
Good morning!  
You know how everyone online closes their emails with cutsey “Hugs!”  Well, Sassy can’t stop there.  She has to say, “Hugs with groping!”  Because she’s sassy!  And SEXY!  You won’t get that from any other girl.  It’s the moment when she cuts loose!  Because if you get that close to her, damn if she’s going to leave her hands around your waist!   A sassy hug includes at least one serious ass grab, some back massage, a little hip grinding and if you don’t let go, a hand is going to sneak into your front pocket to check on whether all that is having an effect!  If it’s an especially frisky day, your fly is in peril… unzip… slide a finger in… touch skin… ooooh.  
And you are encouraged to grab whatever you like… her amazing ass, a bounteous breast, and maybe even her face for a sensual kiss?  
It is best done in a public place like an elevator or an entryway to a big office building on a Saturday night, or in an alley where people are going to see you very soon, but not right this moment… it’s sexy, it’s dangerous and it’s incredible!!!  But it doesn’t go toooo far… it’s a promise of more.  When you’re alone with me… more… more… more… 
I want you to be totally dense about this concept.  I want to show you over and over!  Touch you again?  Hmmm… welll… YES PLEASE! 
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We shared porn back and forth, looking at various tumblrs.  They are great when you’re figuring out what someone is into.  
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What Makes You Beautiful

What Makes You Beautiful
sung by One Direction

[Verse 1] [Liam]
You’re insecure, Don’t know what for,
You’re turning heads when you walk through the door,
Don’t need make-up, To cover up,
Being the way that you are is enough,

[Bridge] [Harry]
Everyone else in the room can see it,
Everyone else but you,

[Chorus] [All]
Baby you light up my world like nobody else,
The way that you flip your hair gets me overwhelmed,
But when you smile at the ground it ain’t hard to tell,
You don’t know, Oh oh,
You don’t know you’re beautiful,
If only you saw what I can see,
You’ll understand why I want you so desperately,
Right now I’m looking at you and I can’t believe,
You don’t know, Oh oh,
You don’t know you’re beautiful, Oh oh,
That’s what makes you beautiful

[Verse 2] [Zayn]
So c-come on, You got it wrong,
To prove I’m right, I put it in a song,
I don’t know why, You’re being shy,
And turn away when I look into your eye eye eyes,

[Bridge] [Harry]
Everyone else in the room can see it,
Everyone else but you,

[Chorus] [All]
Baby you light up my world like nobody else,
The way that you flip your hair gets me overwhelmed,
But when you smile at the ground it ain’t hard to tell,
You don’t know, Oh oh,
You don’t know you’re beautiful,
If only you saw what I can see,
You’ll understand why I want you so desperately,
Right now I’m looking at you and I can’t believe,
You don’t know, Oh oh,
You don’t know you’re beautiful, Oh oh,
That’s what makes you beautiful

Na Na Na Na Na Na Na Na Na Na
Na Na Na Na Na Na [x2]

[Middle 8] [Harry]
Baby you light up my world like nobody else,
The way that you flip your hair gets me overwhelmed,
But when you smile at the ground it ain’t hard to tell,

[All]
You don’t know, Oh oh,
You don’t know you’re beautiful,

[Chorus] [All]
Baby you light up my world like nobody else,
The way that you flip your hair gets me overwhelmed,
But when you smile at the ground it ain’t hard to tell,
You don’t know, Oh oh,
You don’t know you’re beautiful ([Zayn:] Oh),
If only you saw what I can see,
You’ll understand why I want you so desperately ([Harry:] Desperately),
Right now I’m looking at you and I can’t believe,
You don’t know, Oh oh,
You don’t know you’re beautiful, Oh oh,
You don’t know you’re beautiful, Oh oh,

[Harry]
That’s what makes you beautiful

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Cowgirl

Year 2 – Week 43
Wednesday, June 6, 2012
 8:23 am
Good morning! Have a good Wednesday, kid.
9:21 am Phil
morning, you too!
11:40 am
Your words make me smile. Do I say it often enough – thank you! I woke up wanting to wake you by gently straddling your hips and pressing you inside me… mmmm, so the first thing you feel as you rise to consciousness is a wet, hot, tight place around a very sensitive part of your body. When you crack open your eyes you see a woman with large breasts, her back arched in pleasure, smiling her sexiest grin because you, yes you, make her feel so alive!
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From: Philip
Subject: At the beach
Date: June 6, 2012 3:30:18 PM EDT
To: Sassy 
Here’s a photo from my trip. 
[Philip in swim trunks on a gorgeous beach carrying a bucket of beer]
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11:45 pm
Here’s me on top… your reward for sending me the incredibly hot beach photo! 
Sleep well, sweet man.