Category Archives: Lawyer

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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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A Month on AM

Saturday, October 13, 2012
[from my private journal]
My month on AM 
I have gone off the deep end into online dating! 
I was in a terrible funk on Sunday night, September 16.  I was in chat with {a lady}, who patiently listened to a rare whine from me about how both my guy and my husband forgot my birthday.  And how it’s been a year since I saw my guy with no prospect to see him again… don’t know if he’d even make arrangements if he was going to be close by or not.  She suggested signing up for online dating.  I resisted.  Mostly because I think no man would want me if I was even close to honest about my height and weight.  The last thing I need is more rejection!  
But she said they would want me.  And to give it a try.  That it would cheer me up.  Even if I never met anyone, just put up a profile and enjoy the attention.  So before I could lose my nerve, I opened a new Yahoo mischief email account, slapped together a profile and put it up there.  I showed it to a couple of the chat denizens, made sure I didn’t say anything stupid.  
The first couple of days 73 guys looked at my profile!  13 winked me and 2 emailed.  I wrote back to the two who emailed, and three of the winks that interested me, so there were 5 guys in play.  Not a tsunami, but I only need one!  All these men are 6’2″ tall and around 200 pounds.  I’d like someone beefier but not finding him. 
1) AM #1
The first guy who emailed me was incredible!  I adored him and we messaged a lot.  Then he disappeared and I was crushed.  I know, I’m an idiot.  But I felt something.  I waited a couple of days, then contacted three guys who had winked me.  
He reappeared after awhile, said he had backed off because he really liked me.  WTF?!  He had not cheated yet, despite having met 7 women, and was afraid I’d be “the one who would make him cheat.”  People said this is a familiar brush off.  But I wrote him back anyway, offered to talk it out with him or only flirt online, whatever.  He wrote back with a photo!  Somewhere between Greg Kinnear and Tom Hanks.  He set up a meet.  Which he postponed.  But rescheduled.  Then postponed.  But I still feel such a connection!  So we’ll see!
2) The Lawyer
Think Sam Waterston – educated, charming urbane senior partner… we used to work at the same firm at different times!  We had a lovely lunch and he told me he wanted more! Wow!  I AM WANTED! We had a delicious kiss in the afternoon sunshine and he asked me to email him.  I did.  We’ve been emailing and waiting for him to find time.  But I fear he is too busy.  Or he doesn’t really want me.  
3) The Dancing Man
Think Anderson Cooper –  intense, edgy and blunt.  Said he was coming off a 3 yr relationship and looking for another long term lady.  He invited me to a hotel room.  I angled for the bar instead.  We had a hysterical run-in with a brand new bartender who wouldn’t leave us alone, but ended up in his room being very nice to each other.  WOW!  and then I never heard another word from him.  I wrote a thank you note.  Nothing.  That stung.  But at least I got to play!  *sigh
4) The Professor
Brilliant, deep, polite and nervous. Well-educated.  Slow.  Careful.  Uses his real name.  Wants mine.  Showed him my chest instead.  He disappeared, then reappeared a week later.  Still negotiating.  
5) Panties Man
Think taller Michael J. Fox – super nice, focusing on finding a friend.  Met him last Friday, felt comfortable, kissed a little in my car.  He left after 30 minutes, so I assumed he didn’t like me.  Less than an hour later he wrote a long email saying how nice I was and he wanted more. 
Chatted online all weekend.  Saturday he told me he’s a switch – wants to dom me sometimes and have me dom him other days. Hmm… Monday he told me he likes to wear ladies underwear.  and wants to be yelled at and called a sissy for doing it.  Like his mother did. So if I had tried to give him a blow job on Friday, I would have found lace and flowers!  I can deal with silky fabric but NO! I can NOT be mean… just… NO.  I feel bad that I can’t help him, but NO.  I told him that but he is still writing.  Ugh.   Need advice on how to make him stop wasting both our time.  Everyone said just run.  But one friend told me ways to play with him, to make his life fun and not be too tough for me.  Assign him tasks.  So I tried a little of that.  It was strange but wild and fun!  And he appreciated it so much!  
So I have three maybes – The Lawyer, The Professor and AM #1.  None of them are particularly chasing me, though they whine if I don’t write back. Even the best one doesn’t click with me the way bloggers or chatters do, but they are local! 
Tuesday night I was talking about AM in chat when someone mentioned another site online, Private Affairs [the site has disappeared since].  I signed up and found four pages of men in this area.  There is less focus on stats and more in info I want to know.  You can look without signing up, which is lovely.  I winked all the men over 6 feet – three of them. I’ve already heard back from one!  So maybe some fun in that direction.  But he’s awfully droll.  
This doesn’t feel like where I want to be but I am learning a lot about what I want and maybe this will get me somewhere better?

Stay tuned!

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The Front Pocket

Sam Waterston in “Law & Order” 

I DID IT!  I MET A MAN!  

It was wonderful!  I got the restaurant before him, sat in the entry watching men going by… he told me what he’d be wearing – I counted 16 men with that on before he appeared!  He finally showed up about 15 minutes late, just as I was about to give up.  
I gave him a hug as he entered and he squeezed me for 2 seconds and breathed mmmm… into my ear.  He led me to a table and we sat not facing each other, but on two sides of the table.  He apologized profusely for being late.  He explained that he’d walked right past the restaurant (it’s on an upper level) and gone quite a ways before he figured out he missed it and had to double back.
He is a charming, urbane, classy gentleman.  He wore the classic business casual lawyer outfit – blue blazer, blue & white striped shirt, and khaki pants.  He reminds me of Sam Waterston, the D.A. from “Law & Order.”  I had on black pants, black unconstructed silk blazer, purple/pink squares silky blouse, a pink and silver necklace nipple length, tiger underwear and my lucky black bra!  
He made lunch very easy and comfortable.  He told me to order whatever I wanted – that he was paying.  Wow!  He had the sole and I ate broiled scrod and steamed carrots.  We talked and talked… he seems like someone I know already, in the best possible way.  He knows a lot of people I used to work with.  He was interested in my project work.  
After about an hour he said that he likes me a lot and he’d like to see me again.  That it can be anything I want… he is not demanding, doesn’t require exclusivity, just wants to be with me, however I want that to work. Then he winked and said, “But you should know that I’d like to get my hands on you.”  Wow!  Someone wants me! What a feeling!  You know that affect where you feel sexier because someone else thinks so?  Yeah… that.  He stroked my wrist with his thumb and I thought I’d faint… so simple and sexy.  He asked me to think about it and email him.  
As we left the restaurant, he took my hand and asked if there was anything else I wanted to know.  I said yes, but… I needed somewhere more private to find out.  He nodded (understanding that I wanted to know how he kisses!) and led me down an alley by the big brick church.  We grabbed each other – kissing, groping.  He put his fingers in my hair to hold my head and plundered my mouth, my neck, my ear… Yowza!  There was magic in the autumn afternoon sun!  Yum.  He squeezed my left breast.  I was very bad and put my hand in his front pocket to see if I was causing a reaction.  YES!  ðŸ˜‰
I waited about two hours… could not figure out what to write.  I ended up with “MORE!  SOON!”  heh.  He liked that.  But then I haven’t heard from him today.  Note to all gentlemen – if a woman kisses you, make sure you wish her a good morning the next day!  
So… I met The Lawyer!  
I am off to drinks with Dancing Man this afternoon.  This is going to be completely different.  He is so blunt.  He does strike me as a player.  But you know what?  I want to play! 
The Professor wrote back last night after two days away.  He is a much slower worker, but that’s okay.

AM #1 (who had disappeared and then reappeared) wrote back all excited to meet, but then hasn’t written with details.  Ah, well.  I am very calm about it.  
I told Philip I met a guy and am meeting another today.  He said, “Wow! You go girl!”  I am left to wonder why there are two men I love (Hubby and Philip), neither of whom care if I fool around.  I should feel lucky I can do what I want but… *sigh  

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Meeting The Lawyer


Here’s my report back to the blogger who was kind enough to give me advice: 


* I DID IT!  I MET A MAN!  I MET THE LAWYER FOR LUNCH!

* I had fun!  And he said he did too!  It was very easy and comfortable.  He felt like someone I already know, in the best way.  

* I did not screw!  I did find out he is an excellent kisser.  In an alley by the big brick church! 

* Will write it up… dunno if it will be blogged.  But I am telling you FIRST!  

Having a Sally Field moment here… “He likes me.  He REALLY LIKES ME!” WOOT!

If there are other details you are curious about, don’t hesitate to ask.  I never know what you’d find interesting. 

And the first guy I really liked who disappeared has reappeared!  Whee!  

So… onward and upward.  Think of me Friday at 4:30 pm having drinks with Dancing Man.   He is going to buy me an iced tea.  

To be completely frank… these guys are very entertaining.  But they make me long to… um… visit you. 🙂  

-Sassy

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A Different Game

Just when I had started to forget my first contact, AM #1, of course he reappeared!  He wrote another charming message, saying he’d been run ragged at work unexpectedly, so sorry, he still thought I was the best gal in all of AM… so I swooned for a second time!  

So I have a lunch with The Lawyer tomorrow.  Drinks with Dancing Man Friday.  And AM #1 back in the mix.  And the Professor writing every day.  My head is spinning!   

I spent quite a while trying to figure out which man I would choose.  Imagine… me… talking to four men and being able to choose one!   I had never done that in my life!  How was I supposed to do it?  

  • The urbane cautious Ivy-educated lawyer like the men I’d worked, but better? 
  • The charming, flaky AM #1 – the first guy to recognize my potential?
  • The uber-sexy gray fox who sent me a naked photo and wants to fuck like a rabbit?  
  • The staid slow-but-sure turtle of a Professor?  

I like them all!  Arrrgh!  

Then I realized… this is NOT “The Dating Game.”  I don’t have to choose!  I can have lunch and drinks and whatever, and choose or not choose some other day!!! Wow!  There’s no guarantee that any or all of them will want to see me again, so it’s good to have a back-up plan.  Or two.  Or three!  Hee hee.  Wow.  This is not about marriage, children, being seen in public… just sex and fun!   This online dating game is a whole new world!  

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The next step

Wow!  Things are happening fast on the Ashley Madison front!  I’ve only been on there a week and I am learning a lot, in the midst of talking to three men!  It doesn’t feel like my kind of place.  But it did cheer me up. 
So I’ve tested the waters, found out men will write to me and write back to me.  Yay!  Now the much tougher test… meeting in person.  Gulp.  
I have a DATE!  with a MAN!  Gosh… I didn’t think I’d ever say that again!  
Tom, the lawyer who worked at my old firm, asked me to meet him for lunch on Thursday!  
Lunch invitations are considered a good sign.  If he was cheap or iffy, he’d ask to meet for coffee at Starbucks.  Heh.  I am telling Sis and Hubby about it, as a safety precaution.  
What am I going to wear?  What are we going to talk about?  What if he is a creep?  What if he doesn’t like me?  What if I don’t like him?  What if we like each other – then what?  Arrrrgh!!!!
Scot, the professor, sent me several messages today.  He told me enough to find his web site, seems fine with me knowing who he is.  That freaks me out a bit… but I’m rolling with it.  
Of course, I really wanted to hear from Kevin and he’s silent.  Figures.  
Wish me luck!  
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The Ivy League

So… AM #1 is gone.  I woke up the next morning filled with a new spirit.  I am not going to let him ruin this experiment!  Onward and upward! 
Friday I decided to write to two guys who “winked” me.  People told me to ignore winks – if the guy couldn’t be bothered to spend credits on me then forget him.  But there was something about each profile that caught my eye.  They both wrote right back, shared more about themselves.  
The Professor
“Scot” sent me a brief message and the “key” to unlock his photos on the site.  There were four photos!  He says he’s 6′ 2″ 195 pounds and in his late 40’s, a professor who went to Yale!  Wow!  He’s got a great smile, graying, fit… I wrote back and asked a few questions.  I didn’t hear back from him right away but it is common to not hear over a weekend.  
The Lawyer

“Tom” wrote to say he’s a lawyer in downtown Boston.  His profile lists him as tall 6″2, and thin 200 pounds, in his 50s.  Hmmm…. I had a hunch and told him in a cagey way that I worked for a large law firm but have been gone 10 years and not kept in touch and don’t work with lawyers now, but he might have known me as the demure lady down the hall if he worked there (and I added something that only a person who worked at my prior employer would know).  
He wrote back saying “sounds like you might have worked at the same place??  if so, no worries– I will admit to having worked there, but it was long, long ago (think late 70s!!) and I seriously doubt whether our paths have crossed.   even so, I can keep a secret….and if you were that demure lady, I probably fantasized about you anyway!!”  That probably means he went to Harvard (as they had not started their affirmative action plan – letting in Yalies and other Ivy League law schools) until about the time I arrived in the mid 80s.  
Two Ivy Leaguers right off the bat.  Wow!   Who knew smart men would find me?!  Woot!