Setting up meet #3

Guy #5 found me online on Yahoo IM early this morning.  We chatted all day on and off.

He was very interested in what I was wearing and I asked about his clothes too – the “boxers or briefs” discussion.  He is a briefs man!  He sent me a photo of his shirt front and neck.  Heh.  He asked my bra size.  I asked if he was comparing me to his other AM women… he said there are no others, he is focusing on me.  Whatever.

He asked for another photo.  I sent him my belly button.  He didn’t comment on my navel but liked my panties.

He told me he couldn’t meet tomorrow as we’d tentatively planned – new meetings had come up.  Whatever.

He said he’d like to send me another photo – what did I want to see?  I decided to goof around – I asked for his toes!  A little while later he sent a photo of all ten!  He’d gone to the men’s room, taken off his shoes and snapped a photo!  Wow!  It was such a hoot to ask for something and get it!

I told him I had to sign out – was going out for drinks with my co-workers.  He signed off with some very sexy talk.

I went out and he sent me a very hot message hoping I would read it at the bar.  He described what he would do the first time we were alone.  Oh my!  Luckily I didn’t look at my email until I got home.

I sent him another photo of my cleavage, in a simple white bra this time.

He had asked for a naked breast but I just couldn’t do it.  The demure lady part of me ruled.  He commented a lot about the bra.  He said he has a thing for lingerie.  I felt a little sad, as I don’t.

He told me two of his meetings were moved so he had time in his schedule tomorrow.  He asked if I could I drive out to a Starbucks in the suburbs near where he works?  I decided to break the “the guy should come to you” rule and said yes!  My first “coffee meet!”  My third meet!  Whee!

Connection #5

He wrote back!  I made a connection with the 5th guy!

Hi, Sassy!

Thanks for the honest email.  I do enjoy keeping in shape, but here, what I really seek first and foremost is a mental connection.  With that, everything else should work out.  People do come in all sizes, and I’m ok with that with the assumption that the person is a nice, and not lazy.  How does that sound?

Also, I do love breasts, so reading what you wrote was tantalizing. ðŸ™‚ 

I look forward to hearing more from you and learning more about you.

R
 =========

It’s okay that I am not a gym rat!  Hallelujah!

I replied outlining my situation, and attached a photo of my famous cleavage!  He wrote right back, very impressed, and gave me his Yahoo IM.  We chatted for about two hours into the evening.  He asked if I would meet him for coffee.  I asked for more time to get to know him.  He was very friendly, nice, interesting, interested in me.  He asked good questions and answered mine.  It was easy to relax and just chat along!  Yay!

There’s more!

I have tossed The Dancing Man into the “one and done” pile.  *sigh

Just as I was realizing that I would never hear from him again, I got email from Ashley Madison announcing “Today 1 Member has contacted you!”

It may seem like simple concept, but it didn’t occur to me that new men would write to me after the first wave.  Duh.  He sent a message (which costs money) unlike most of the others who viewed my profile hoping I write to them or winked me.

He started out very simply:

Hi!

I liked all that you wrote in your profile. I’d enjoy learning more about you, if you are also interested. Yes?

==========
The message was too short.  Not specific to me.  But he spent money, I’m a polite person, so I viewed his profile.  Hmmm… a little younger than me.  If he is telling the truth.  No one I have contacted told the truth about their age.  Whatever.  6’0″ tall.  Yes!  180 pounds.  Oh dear… even skinnier than the first batch.  Even if he is fibbing by 20 pounds, still skinny!  Where are the beefy men?!  I want someone about… 235?  250? who will make me feel smaller.  His limits: Undecided.  Ugh.  Any of the other choices are better.  But I shouldn’t focus on stats.  I should read the content.  That’s what I want men to do for me.

His profile was another wonderful “no check boxes” work of art filled with well-written paragraphs!  I picked over each word. It was very different from the list of sexual qualities most men specify under “What really turns me on:”

  • Intelligence  
  • Kindness  
  • A mental connection
  • I truly appreciate mature women 
  • Good communicator
  • Sense of humor
  • Sass.  

YES!  That’s me!  With that last word, you know I had to answer, right?

The only hang-up was under “What I am looking for” the only thing he listed was “Physical fitness.” Hmmm…. of course he wants that.  But no one would describe curvy me that way.  So I decided to reply with more tantalizing words about me, and ask if that was a deal-breaker, an item he could not live without.

If you’re counting, this is the 5th man I’ve replied to (#1, The Lawyer, The Professor, The Dancing Man).  Several people told me I should do my own searches, contact men I like, that was how they met the best guys, but I did not have the courage to do that.  I wanted someone who looked at my stats and my words and wanted to explore further.

There's more!

I have tossed The Dancing Man into the “one and done” pile.  *sigh

Just as I was realizing that I would never hear from him again, I got email from Ashley Madison announcing “Today 1 Member has contacted you!”

It may seem like simple concept, but it didn’t occur to me that new men would write to me after the first wave.  Duh.  He sent a message (which costs money) unlike most of the others who viewed my profile hoping I write to them or winked me.

He started out very simply:

Hi!

I liked all that you wrote in your profile. I’d enjoy learning more about you, if you are also interested. Yes?

==========
The message was too short.  Not specific to me.  But he spent money, I’m a polite person, so I viewed his profile.  Hmmm… a little younger than me.  If he is telling the truth.  No one I have contacted told the truth about their age.  Whatever.  6’0″ tall.  Yes!  180 pounds.  Oh dear… even skinnier than the first batch.  Even if he is fibbing by 20 pounds, still skinny!  Where are the beefy men?!  I want someone about… 235?  250? who will make me feel smaller.  His limits: Undecided.  Ugh.  Any of the other choices are better.  But I shouldn’t focus on stats.  I should read the content.  That’s what I want men to do for me.

His profile was another wonderful “no check boxes” work of art filled with well-written paragraphs!  I picked over each word. It was very different from the list of sexual qualities most men specify under “What really turns me on:”

  • Intelligence  
  • Kindness  
  • A mental connection
  • I truly appreciate mature women 
  • Good communicator
  • Sense of humor
  • Sass.  

YES!  That’s me!  With that last word, you know I had to answer, right?

The only hang-up was under “What I am looking for” the only thing he listed was “Physical fitness.” Hmmm…. of course he wants that.  But no one would describe curvy me that way.  So I decided to reply with more tantalizing words about me, and ask if that was a deal-breaker, an item he could not live without.

If you’re counting, this is the 5th man I’ve replied to (#1, The Lawyer, The Professor, The Dancing Man).  Several people told me I should do my own searches, contact men I like, that was how they met the best guys, but I did not have the courage to do that.  I wanted someone who looked at my stats and my words and wanted to explore further.

Dancing Man postscript

If you missed the posts about my meeting the Dancing Man, start here. 
Post-coital thoughts 
It is so stunning to be wanted!!!!
And for men to do nice things for me and pay for lunch or a hotel room to get me!  And they are nice, smart, sexy, beautiful men!  I can get online and find a man, get to know him and be in bed with him less than two weeks later!  Why didn’t I do this YEARS AGO? 
Sex with a stranger.  A new milestone.  Of a dubious nature.  I certainly feel a long way from the mundane old married woman I’d rather be.  But it is so lovely to have physical release, to meet a new man, to feel that calm and confidence.  I can please a man even if I don’t have romantic feelings for him.  He can please me!  
I am learning that the rules are different in the EMR world (extra-marital relations).  It’s not about forever or going places together or children or whatever other long term things we think of on the marriage track.  It’s about searching for what you want, enjoying each other for as long as it works.  Reaffirming your sexuality and desirability, physical satisfaction, experimentation, passion.  This week feels like a big fork in the road.  This is not where I want to stay, but I hope it is moving me to where I want to be and giving me the tools to get there.

Postscript

I waited 90 minutes after we parted to see if he’d write, but no.  I sent him a short email – two sentences of thanks for the drink and all that followed.  No response.  Nothing today.  It is the weekend but… hmmm.  It is not going to surprise me if this was a one night stand.  and I am amazingly calm about that. I suppose it is the lack of emotional connection between us, and the possibility of other men.
So… I  never heard another word from him.  Not one word.  That was tough. I HATE SILENCE!
I spent a long time wondering if there was something wrong with me.  I was puzzled that I thought it went so well and he didn’t think it was even worth one email more.  I wondered if that had been his plan all along, or if something I did or said changed him from a “seeking something long-term” into a one-and-done man?  
Note to gentlemen – even if you have made up your mind that you don’t want to see me again – write one email.  Thank me, say it was fun, but I’m not the one, best of luck.  Don’t make silence the capstone of our encounter.  

The New Bartender Part 2



You can find Part 1 here


The question

He asked how long since I had some dick.  I answered six months, smiling at the thought of my idyll with Simon Templar.  He rolled his eyes and said, “Let’s fix that, right now.”  He leaned toward me, and whispered, “Yes?”

The answer
The bartender came back to check on us.  “Another drink?  Some snacks?  Can I recommend a nice place for dinner?”  He shook his head and I thought he was going to strangle her.  He dug his fingers into my arm to keep from smacking her.  I turned my back to her and leaned toward him, whispering, “Patience” in his ear.  She got the hint and walked away.  He stared and raised an eyebrow, imploring me to answer his question.  I whispered back. “Yes!”

His smile was very wide and he winked at me.  He asked for the check, paid in cash and we went upstairs.  He mentioned that we should be careful in the open spaces as he knows people around here.  I asked if he wanted to go up first but he said just no touching.  He had a room on the seventh floor.  I set my bag and raincoat down on the sofa.  He had already checked in, turned down the bed, his blue blazer over the desk chair, his laptop on the desk.  

Being very nice to each other
He came up behind me, started kissing my neck and turned me around for lots of kissing while he twisted my nipples.  I was moaning into his mouth, touching his head and neck.  He took off everything above my waist in record time, while I unbuttoned his shirt.  There was that fabulous first skin-to-skin hug.  [Note to self: look for heavier guys.  These 6′ 2″ 200 pounders are too skinny!]  He moaned and rubbed all over… arms, back, ass, holding my head and kissing more.  He had white fuzz on his upper chest… I’ve never seen that before!
He sucked on my nipples and squeezed my ass, told me how gorgeous I am, how he loves big tits.  He has a very bold, experienced touch.  I was extremely turned on and started to cum.  He held me and bit my neck, marveling as I trembled.  I told him he was good at what he was doing but he scoffed and said it was just my long time without any.  I told him not to underestimate his talent.  I was having trouble standing up, so I asked if we could lie down.  
We moved to the bed.  I sat on the edge.  He took off the rest of his clothes.  He had on Hilfiger black bikini briefs with a very sexy bulge.  He helped me take off my slacks and underwear.  He had talked online about taking off my clothes slowly and kissing as he went, but that didn’t happen.  He was standing in front of me, so I reached out and touched his cock.  He is cut, and trimmed.  I kissed the tip and blew on it, he moaned and I gave him a sassy blow job!  I was channeling the videos I’ve watched, trying to mimic them – licking from bottom to top, circling the top, sucking him in and out, making smacking, sucking sounds then seeing how deep I could go.  He said he is 7 inches, less wide than some I’ve tasted, and I can deep throat that with some concentration.  I can’t hold it for long because the gag reflex sets in, which disappoints me but he liked that sound.  He talked through it, telling me how great I was doing, how wonderful it felt, moaning… I looked up into his eyes like a good girl.   I told him I felt rusty, that I would get better with practice and he moaned saying much better and he would be in big trouble.  He still had trouble staying hard, but I would work him with my hand and he’d perk back up, then I’d gobble him down again.  He let me control it, even at the most intense moments, which is unusual in my experience, and gave me confidence that I was doing it right.  
He stopped me at a certain point… and flattened me out on the bed asking me what I wanted next.  I asked him to reciprocate.  He put a pillow under my hips and crawled between my legs.  He has a very talented tongue but was rather rough and fast, going straight for the clit.  I slowed him down a bit, and lay there squirming and moaning. Just as I was going to ask for his fingers, he read my mind and put them inside me… one, then two, then three… commenting on how tight I was and that he was going to stretch me a bit.  He didn’t curl them and I was about to request that but I came hard and couldn’t talk.

He went off to the bathroom briefly… I wasn’t really paying attention but I think he wiped his face and rinsed his mouth.  I sucked on him a little more when he returned.  Again, trouble staying hard.  I haven’t run into that before… not a big problem, just need tactics to work it and not make a big deal out of it.  

Woof 
He grabbed the lube and a condom and we had a doggie style extravaganza.  My first lube!  Not sure why he wanted the lube… I was soaked.  Maybe he is used to that with someone else?  He slapped my ass and my lower lips as he applied the lube.  When I made a nice sound at the latter, he did it again harder.  Hard enough to get my attention and get the nerves tingling but not too hard.  Very nice.  
The lube made for interesting sliding up and down my ass crack and inside me.  He rimmed my ass but didn’t try to go in.  He stretched out full on top of me, biting my neck – so wonderful to feel his weight on me!  He couldn’t stay in, so I inched back onto my knees to raise my ass.  He kneeled behind me and that worked much better.  He told me I have a tight, hot pussy… so good for him.  I liked this position for how it feels down below but hate that I can’t see or touch him with my hands.  I grabbed the sheets and tried to reach back to touch him but he told me to just enjoy this time.  
He did a few rounds of “push in, pull all the way out, tease the opening until I whimpered and then slam back inside” – so good.  I felt wonderfully full!  I asked him to describe what he was seeing so I would know what he was focusing on, and he did a good job.  He said watching his cock go in and out was very erotic.  He said he loves a nice ass and mine is!  He talked about my beautiful alabaster skin and my curly hair.  I slammed back against him and came again when he had hold of my ass and was slamming… the full feeling, sound of balls slapping my ass and a man moaning gets to me!  
Finishing Fantasy Fail
I had told him early on about my fantasy of wanting to see a man cum on me.  He remembered.  He flattened me on my back, crawled up with his knees around my chest, took off the condom, lubed up my tits and slid in and out between them.  He said it was almost as good as pussy but not quite.  I put two fingers on him to press down and provide some more action – he liked that a lot.  He said watching it slide and reappear near my chin was very hot.  He got very worked up and then asked if I was ready… did I want it on my chest or face or both?  I said both and to make sure some of it got into my mouth.  
At the last moment, he changed his mind!  WHAT?  He grabbed another condom and shoved himself back inside me.  He gasped and moaned, seemed very impressed, whispered… “So hot… hot…”  Wow.  I was cumming and shaking so hard, making a lot of noise.  The look on his face was so hot!  
There are so many variables that go into a first encounter, and so many ways to goof it up as two people try to figure out how to make each other cum.  This was definitely the easiest match I’ve had – almost business-like in it’s straightforward focus on pleasure and fun.  I wasn’t sure I could do without any romance… but the online chats helped and it was a great way to get back into play after so long.  
Recovery
He collapsed next to me, whispering, “so hot… so… damn…. hot.”  I grinned my evil grin at him.  He rolled onto his side with his hand over my waist and closed his eyes.  I was full of energy, still roiling inside.  I explored his arms and chest and legs… learning his body.  He said something about “nothing like finding a hot woman under a shy lady’s exterior.”  He started to perk up and did this pinching thing to my nipples… made me moan and writhe.  I stared into his eyes.  He watched what he doing did to me, wiggling his eyebrows, goading me.  I bit my lip.  I really wanted him to mark me, but I held back as I don’t know who I will see next week!  I was disappointed that he is not able to go again.  It made me miss Philip – he can go and go and is never soft, but I know that is a rare gift.  
Cleaning up
He said he needed a shower.  I asked if he wanted help but he said he was running out of time and the stall was a bit small.  I sat on the toilet and he chatted while he washed the evidence down the drain, asking me questions about my projects and what I was doing this weekend.  I handed him a towel and we kissed more.  He was surprised I could go home without a shower, but I’d rather use my own bathroom and Hubby won’t notice or care.   
We chatted while we dressed.  I looked him over to make sure there was no sign.  I told him he was too far away and he hugged me again, more kissing.  We gathered our stuff and headed out.  He kissed me in the elevator.  We strolled out through the lobby three feet apart.  It was pouring rain. I put up my umbrella and he did the same.  He turned as we got outside to ask where my car was.   I pointed left and he nodded right and said take care! and was gone. 6 pm.
THE DROUGHT IS OVER! 
TWO FOR TWO!

The New Bartender Part 1

Anderson Cooper

Here is my report on Dancing Man – my second AM meet!  

We were IMing all day while I slogged through payroll processing – revving each other up, re-checking the plan.  I sent him sexy tumblr links to get him going.  ðŸ™‚  He actually sent me links back, which no other man has. 
We were scheduled to meet at 4:30 pm.  At 3:15 pm he pinged me to report that his last meeting of the day had been cancelled.  Could I get there earlier?  I checked to see if Hubby could bring me the car earlier.  He said sure, so he picked me up, I dropped him off at home and headed to the hotel.  I had seen a face shot and a full nude from the neck down, so I knew who I was looking for.  He also told me what he’d be wearing.
The meet
It was a dreary, rainy afternoon and people forget how to drive, so the traffic was awful and I was 15 minutes late, right at 4 pm.  I emailed him from a stoplight to tell him I was on my way.  He told me to meet him in the bar.  There was a man in the lobby leaning against a column reading his phone who looked like it might be him but I walked right past him, and didn’t figure it out for a few seconds.  Just as I turned to backtrack, he was there in the doorway.  I gave him a quick hug and he led me to the bar.  He had on a light blue dress shirt and grey dress pants.  I wore dark blue pants, a lighter blue top and scarf that match my eyes, white underwear with black dots all over and… my lucky black bra!  
He looks like a very trim Anderson Cooper, a “silver fox” with a buzz cut.  His face shot online is at least 10 years old. Not sure about his real job… sales something.  Sleeps with wife, but rarely.  Needs more.  Had been with a woman for 3 years, but they recently moved on and he says he is looking for another long term lady. 
The new bartender

There was no one else around.  We sat at the end of the bar.  There was a brand new bartender – first day – who wouldn’t leave us alone!  He asked what chardonnays they had by the glass, and she was looking at the red wines.  Ugh.  He told her it’s a white and she pulled out a bottle for him to look at.  I asked for iced tea.  She poured his wine and went in search of the tea.  She came back to say they didn’t have it.  So I ordered a diet coke with lime. She brought that and started asking us questions – where are you from?  What brings you to Boston?  How long will you be here?  I let him answer.  He put his hand on my arm and rolled his eyes at me.  
Not subtle
He is the opposite of the lawyer – very intense, edgy.  Not subtle, this one. When she finally left, he turned to me and said, “Wow.  I thought she would never leave!  What am I doing here?  I came here to fuck you!”

I was stunned that he wanted me.  He put my hand between his legs.  I put my hand on his upper leg and he chided me, “Higher!”  I sassed him back, “Patience.  I’ll get there…”  Very nice bulge there.   He said he was very turned on that I watch porn and had expressed interest in trying things.  He stared at me.  I stared back.  He asked how long since I had some dick.  I answered six months.  He rolled his eyes and said, “Let’s fix that, right now.”  He leaned toward me, and whispered, “Yes?” 

Tune in tomorrow for Part 2

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  

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

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!