Category Archives: #1

by

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
===========

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….

by

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!

by

Off again

AMguy #1 pinged me two nights ago and asked me to meet him at a big sports bar near Fenway Park in Boston tonight.  We spent all day yesterday working out the details.  I was soooo excited!  I fantasized about walking up to him in the upstairs bar and throwing caution to the winds and kissing him right there!  Feeling his arms around me… his lips, his tongue… a bulge…mmmm… Hussy! 
He emailed me at 2 pm today to say something had come up with his daughter – an extra rehearsal for the school play.  Hmmm… I was disappointed but stuff happens.  Hope it is true and not some game.  He said he will re-schedule soon.  *sigh

Will I ever meet this guy?  And if it’s like this at the start… what am I getting myself into?

by

On again

I told Kevin (AM #1) that I like his photo and he wrote back to schedule a meet!  Yay!  In two days!   Wow… that certainly was a fast change from zero to 100.   When he gets back in the game, he is ready to play!

He has a late afternoon meeting in Boston.  We agreed to meet at sports bar near Fenway after work.  Easy to find, lots of parking, lots of people to blend in with… I adore it when a guy makes a plan and invites me!

My mind began to race at the thought of seeing him, listening to him, touching him… whee!  Will he actually show up this time?  And will he like me?  Will I like him?  Please please please!

by

#1’s face

I was astonished to hear from #1 again this morning!  He wrote an apology for being out of touch, and told me he REALLY LIKES ME and that was causing a crisis of conscience, because he had not actually cheated yet, despite meeting 7 women but he could not stop thinking about me, thinks I was the one who he could not resist.  So he needed time.  
My online pals said not to respond.  GUILT KING!  Hard to tell if this was a gentle way of letting me down easy or some kind of truth.  I hear this excuse a lot – my friends on AM get it all the time, so I am skeptical.  
I responded encouraging him not to cheat if he can avoid it.  Then offering to talk it out with him – I can be objective, or just flirt and not meet if that would be fun for him.  He may be a chaser not closer, so I told him to go do that if that’s what turns him on, and let me know how it goes because I want him to be happy even if it’s not with me.  It was very flattering to have the guy say I am special!  He is the one I think about most… his series of initial questions was brilliant. So worth some extra effort. 
He wrote back with a photo!!  Hmmm… cute!  I told him he looks like a cross between Tom Hanks and Greg Kinnear!  Great smile, head of dark hair and very nice shoulders.  Yum!   He replied: “A cross between Kinear and Hanks? Now I want to date myself :-)”
Greg Kinnear
He told me it was okay not to send a face photo back.  So I sent him my cleavage instead!  I asked him why he didn’t sleep with all those women he met, wondering if it would give me a clue into whether he was picky, unlucky or what.  He told me: 
The woman I met that were nice all were looking for something slightly different. 

I had a hot make-out session with one and we were really attracted to each other, but her husband was deployed and she wanted me to be available for her several times a week. I just don’t have that kind of availability.  

Two were very nice, but the irresistible compulsion to take them in my arms and into bed wasn’t there. 

And two seemed like they were in it for revenge against their husbands and that was a train wreck in the making I wanted no part of. 

Two were kind of crazy. One claimed to be a non-smoker and was lighting up when I pulled into the parking lot where we met. That’s a deal breaker for me. And the other spent the entire time talking without any real need for me to participate in the conversation. 
That all seemed reasonable.  It told me he was not the “Yuck but ah, just fuck em once for the hell of it” types.  And made me want him all the more.  
by

#1's face

I was astonished to hear from #1 again this morning!  He wrote an apology for being out of touch, and told me he REALLY LIKES ME and that was causing a crisis of conscience, because he had not actually cheated yet, despite meeting 7 women but he could not stop thinking about me, thinks I was the one who he could not resist.  So he needed time.  
My online pals said not to respond.  GUILT KING!  Hard to tell if this was a gentle way of letting me down easy or some kind of truth.  I hear this excuse a lot – my friends on AM get it all the time, so I am skeptical.  
I responded encouraging him not to cheat if he can avoid it.  Then offering to talk it out with him – I can be objective, or just flirt and not meet if that would be fun for him.  He may be a chaser not closer, so I told him to go do that if that’s what turns him on, and let me know how it goes because I want him to be happy even if it’s not with me.  It was very flattering to have the guy say I am special!  He is the one I think about most… his series of initial questions was brilliant. So worth some extra effort. 
He wrote back with a photo!!  Hmmm… cute!  I told him he looks like a cross between Tom Hanks and Greg Kinnear!  Great smile, head of dark hair and very nice shoulders.  Yum!   He replied: “A cross between Kinear and Hanks? Now I want to date myself :-)”
Greg Kinnear
He told me it was okay not to send a face photo back.  So I sent him my cleavage instead!  I asked him why he didn’t sleep with all those women he met, wondering if it would give me a clue into whether he was picky, unlucky or what.  He told me: 
The woman I met that were nice all were looking for something slightly different. 

I had a hot make-out session with one and we were really attracted to each other, but her husband was deployed and she wanted me to be available for her several times a week. I just don’t have that kind of availability.  

Two were very nice, but the irresistible compulsion to take them in my arms and into bed wasn’t there. 

And two seemed like they were in it for revenge against their husbands and that was a train wreck in the making I wanted no part of. 

Two were kind of crazy. One claimed to be a non-smoker and was lighting up when I pulled into the parking lot where we met. That’s a deal breaker for me. And the other spent the entire time talking without any real need for me to participate in the conversation. 
That all seemed reasonable.  It told me he was not the “Yuck but ah, just fuck em once for the hell of it” types.  And made me want him all the more.  
by

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!  

by

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!  
by

More AM #1

If you missed the first part of my story about Kevin, click here. 
Q. Could it be so easy to find a nice guy?  Would the very first guy who contacted me be the one? 
A. No.  I was an idiot.  After I told him I couldn’t meet Friday, he stopped writing mid-day Wednesday.

On Thursday when he still had not written, I fell apart.  I know… it’s silly.  But he seemed so fun and interested and I need that so badly.  

Our boss took us out to a fancy hotel restaurant for a celebration lunch for a successful conference, and I sat there watching well-dressed couples… you know the thing… how can they be together and I am good person and I am so alone?  Ugh.  I had to go to the bathroom and cry.  I had heard that men write to a lot of women and just go silent when they find someone they like better.  *sigh
I wrote a thinly disguised “Good bye and good luck” message Thursday evening and didn’t get an answer and gave up.  I was very close to closing my account.  Who needs this new roller coaster?

by

AM #1 Kevin’s Questions


I started to hear from men!  If you missed that part, click to read that first.

Let’s call the third man “AM #1” because he was the first, and because he had the best approach I’ve ever seen!

I wrote back to him.  He stood out because his profile didn’t use the “check boxes” for what he was looking for or what he’s like.  He wrote nice paragraphs!  I had my chat buddies look at his profile to check for any danger signs and they approved.  I felt a real spark!  He had a great sense of humor, was open and smart!  And he made me laugh!  
He told me to call him “Kevin.”  Sometimes that is a real first name, sometimes a persona they’ve chosen.  It doesn’t matter to me.  I told him I wanted to stick with Sassy and he was fine with that.  
Kevin sent me six questions, explaining he’d had great success with it as a compatibility test.   They got me thinking.  It’s so hard to choose one answer, but I ran with it. 
Kevin’s Questions
1) What are you looking for from me as a potential lover? In other words, what fantasies can I help you fulfill?

2) If you were stranded on an island with a satellite radio that only got one genre of music, what would you pick?

3) What is your favorite feature on a man?

4) Pub or nightclub?

5) If you had two magic tickets to any event, concert or show in history, where would you take me?

6) What passions do you have?
=============
Sassy’s Answers
Your questions certainly got me thinking.  Nothing like starting off a Monday with sunshine and sexual fantasies!  

1) Sassy’s Six – Equality.  Passion.  Pleasure.  Variety.  Communication.  Fun!  

If I must name one thing – I’d like to see and feel you explode on me.  I’ve never seen it… it’s always inside me somewhere!  I will help get you to that point, of course.  
  
I want an equal partner who will try things with me, and let me try things, then share what felt good and what didn’t and how to make it better.  I want different things on different days – sometimes slow and gentle savoring, other days… wham!  It’s been quite awhile for me, so the basics are very alluring.  But I read a lot, and look at…ahem…a certain kind of photos and videos that have given me a long list of things I want to see if they feel good.  

2) Broadway show tunes – varied, evocative of their time, and I can sing along!  

3) Shoulders. 

4) Pub on a weeknight and nightclub on a special occasion.

5) The Ed Sullivan Show the night the Beatles debuted.  

6) The demure lady is into a fabulous community project in her “spare time.”  And finding that hidden gem – a cheap, fast and good new restaurant.  

Sassy adores poking around inside a man’s head, and scours the internet to find that hot sexy photo or .gif or video to give him something to… think about, and make him look forward to being alone with her.  Have you seen the photo of the woman looking stern?  The caption reads, “I found the porn on your computer.  We should try that!”  😉  Would it weird you out if I sent you some favorites?  

I’d like to know your answers to those questions.  And three other things: 

a. How old you were when you lost your virginity?

b. Is there something about you women find surprising?

c. Your perfect meal for a special occasion

=============
Kevin replied:
He started with, “Hooray!  Absolutely loved your message this morning. You’re a keeper – a inimitable combination of sexual excitement, energy and ability to articulate thoughts in real sentences.  I shouldn’t tell you this and keep you to myself, but that’s a one of a kind” then added his answers to the questions and answers to the questions I asked in return. 
Answers from Kevin

And if that wasn’t enough, you would take me to the first Beatles night on Ed Sullivan. If I could return the favor, I’d take you to a Beatles show at the Cavern Club in Hamburg, Germany in the early sixties before they hit the big time. Imagine the raw energy of the Beatles and the sexual charge of a night with wild Europeans in the early 1960’s!  But I’m getting ahead of myself. That was question 5. Here are my answers in our compatibility test:
1) You couldn’t have more eloquently stated what I am seeking sexually. My wife has lost all interest in sex. I haven’t. The basics are as alluring as an oasis in a desert, but so are the luxuries. Explode on you? How much fun would that be to get to the point and have you moaning for me to do it. Yum. I feel literally ready just imagining it as I type.  Photos and videos that you pick to seduce me? Please, please, please, please, please – send them:)
2) Broadway? Good choice. I love musicals – Avenue Q, Rent, Drowsy Chaperone (it’s super corny, but dang it, I love it!). But my remote island pick would have to be rock for its variety. If you were a stickler and limited me to one subgenre of rock, I’d adopt a ‘tude and pick blues instead:)
3) Smile. I melt for them. Sexy, sweet, sly. Yum. How would you describe yours?
4) Pub. Pubs are for talking. I like to chat and laugh.
5) See above.

6) Playing adult sports – volleyball, running, tennis, etc..  Also microbrews. And I’m a book nerd.
============
He answered my questions on another email: 
And now your final three questions:
a. How old you were when you lost your virginity?

18. First month of college after a long term high school girlfriend who thought dry humping was the bees knees.

b. Is there something about you women find surprising?


I don’t know if this counts as surprising, but I find women are way more interesting then men once you become a real adult. Women still enjoy talking about a variety of topics. Men want to talk about business and golf. At least that’s how it is in the dang suburbs. I should have stayed living in the city.

c. Your perfect meal for a special occasion

On Maui eating outside with a spectacular view of the Pacific Ocean, eating Ono, fresh pineapple and drinking a microbrew from Kona Brwing Company while staring at the beautifully tanned smile of the woman across from me.

Hope my answers hold your interest:)

xoxoxoxoxo

Your fantasy man,.

Kevin

===========
He is smart, funny and sexy… doesn’t go on about work or sports.  He is 49 and lives about an hour out of Boston.  I managed not to talk about Philip or my blog or whine about my weight!  You would’ve been proud of me!  
My head filled with images of smiling, touching, stealing kisses… groping!  And sometimes… MORE!
The fantasies roiled my brain and sometimes my body.

So the emails sailed back and forth Monday, Tuesday and Wednesday. He asked to meet Friday.  I told him not this weekend due to the project, but anytime after Saturday. I started to hope.  Could it be this easy?