Category Archives: AM

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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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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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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?

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Another personals site

I didn’t hear from any of the Ashley Madison men today, and a pal online mentioned another “married but looking” personals site called Private Affairs [sadly defunct now], another Canadian company similar to AM.  
  
It is set up to look very similar to AM, but even more kludgey, if you can imagine!  There are no graphics, no colors, just New Times Roman tiny font and an very strange email interface.  It is less focused on stats and more things I want to know like profession, eye color, hair color and so forth that take care of the early questions one might ask.  It asks for religion – an interesting variable I had not considered.  And it asks about “down there” with the choices “natural, trimmed or bare!”  Hee!  The pricing structure looked slightly cheaper than AM for men and free for women.
I could look for free so I searched within 50 miles of my zip code and found 4 pages of men near here!  So I signed up for another dating site!  I mostly copied my AM profile.  
I winked all the men over 6 feet tall – five of them, all of whom said they were interested in a long term affair!  One wrote back right away!  He says he is 59 (which likely means 60-something), 6’3″ tall, “athletic” weight.  When I asked if he looked like any celebrity, he said “Sean Connery.”  Yum.  Probably means he is bald but that’s okay. 
A second fellow emailed me about an hour later!  Cool!  I wrote back to both of them, describing my situation and asking them a few questions, trying to make them laugh.  The second man never responded.  The other three seem to have abandoned their accounts – they never logged in, even though the site emailed to tell them they’d gotten a wink.  
This guy seems better than the AM men in terms of not asking me to meet right away… we’ll see.  I was very blunt, told them I had a weird week with a man who wanted to wear my underwear!  The first guy wrote back a nice note, ending with “I enjoy good food, intelligent conversation and I don’t need to borrow your clothes!” YAY!   I offered to take our conversation to Yahoo but he said he felt safer just using the site.  Yuck.  
I’ve named the new guy “Coach.”  He played football in college and coaches his sons.  He is the first one I’ve run into who is a sports fanatic.  He is also very into politics.  He’s the first one who was born and raised in MA and never left.  He said he made dinner for his wife and another couple tonight, and I believe had wine, so after several very terse business-like emails in the afternoon, I finally got a frisky message!  Very nice and polite but wanting, as I am.  I want to say “Stop asking me my favorite music and come over here!” But I will wait until he thinks it’s his idea. 
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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!

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Panties Man

The truth came out today.  Guy #5 earned his nickname.  We spent another day on Yahoo IM while we worked at our desks miles apart.  I encouraged him to share his secrets with me, tell me what he really wants me to do.

He trusted me.  I have always been the one a man could talk to, tell his secrets to and feel safe.  He took me into uncharted territory.  He told me that he wears women’s underwear!  Every day… to work.  Under his khaki trousers!

So if I had been bold during our meet on Friday, unzipped his fly?  I would’ve found silk and lace and flowers!  No wonder he was so nervous!!

I poked around in his head, asked about how he got started.  He told me about playing in his mother’s underwear drawer as a small child, enjoying the feel of her slips and panties.  Trying them on.  Getting caught.  Being yelled at and called bad names.  She told his father and there was hell to pay.

He was very clear that he is not gay, doesn’t want to be a woman.  Though he is bi-curious.  He mostly just adores the silky fabric against his skin and the pretty colors.  Hey, fabric.  No big deal right?  I could deal with that.

He used a term I had not seen before – sissy.  He showed me web sites, filled with men in women’s clothing, being dominated, serving women and wearing various contraptions to deny them orgasms.
Check out some of these video clips if you dare.
http://mrslovings-sissy-feminization.com/What-s-New/whats-new.html

Hmmm… interesting.  It’s strange how I can think “Yikes!  I could never do that!” and “Damn, that’s hot” at the same time.

Then he said he wanted to be humiliated, dominated, called a sissy and forced to do degrading things.  He wanted me to be mean to him.  He said he was embarrassed.  And he likes that.

That’s where our train went off the tracks.  I told him I could not do that.  That I found it all fascinating but I was not going to be able to help him.  I made up my mind not to see him again.  I was very sad.  He asked if we could be friends, play in other ways.  I was hoping I would not have the time, that I would spend my time finding someone whose needs match mine.  But I agreed to keep talking.

I talked to my online pals.  All of them said to run screaming.  Except one.  A very kind man offered some suggestions, ways that both of us could have fun.  He said to give him little tasks to do for me.  Tell him photos I’d like to see or a story I’d like him to write for me.  Try domming him just a little.  If it didn’t work I could back away but it couldn’t hurt to try.  That appealed to me.  I felt bad that he trusted me and was so used to rejection… I would explore a little.  It seems worth a try – he is the nicest, most considerate friendly man!

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#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.  
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#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.  
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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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No iced chai latte

Michael J. Fox

It was a beautiful warm Fall day, more like high summer than an October Friday.  I took the day off, had lunch with a gal pal in the burbs so I wouldn’t get so nervous, then headed to meet him at 2 pm at the Starbucks about a mile from there, near his office.  
We had a back and forth in email – he was out running errands at lunch and kept trying to move up our meet,  “I’m at the store, can we meet here?”  
“No, sorry… I’m at lunch with a friend.”
“I’m at the bookstore now, can you come here?”  
“Where?”
“Never mind, stick with the plan.” 
He’s blond – looks like Michael J. Fox with glasses, only taller, in olive khakis and a pale plaid light blue dress shirt, another 6’2″ 200 pounder.  I wore blue slacks with a black button up jersey top with a silky blue scarf.  
When I walked up, he was sitting on the patio at Starbucks, reading his phone.  I gave him a quick hug and he smiled.  He said, “You’re not really thirsty, right?  Let’s go sit in your car. Ok?”  
For the record, I had been looking forward to a nice chai latte all day.  I hate it when a guy changes the plan!  First off, it made him look cheap.  He can’t even spring for a small chai?  Geesh.  Second, I had psyched myself up to sit opposite him in a public place and suddenly he wanted me to be completely alone with him?  ARRRGH!  Don’t do this, guys. 
We walked over to my car.  He asked me if I was nervous.  I told him a little, and he gave me another hug.  It was reassuring.  We got in and he suggested driving around to the back of the complex facing the woods.  This creeped me out even more, but I went along.  There were still people around but it was more private than the front lot.  
Our conversation was strange.  He asked me about my luck on AM.  This is different… it is an unwritten rule that guys don’t ask what else is going on with that.  I told him I had met two other guys, but gave no details.  He said he was talking to a couple other women, but they were grilling him in weird ways like a job applicant rather than a friend or lover, and he was much more comfortable with me.  He seemed very nervous… I asked when his last affair was.  He said four years ago.  It ended badly.  The woman paid for a hotel for his birthday.  Her husband found the receipt.  She gave her husband his name.  The husband called his wife.  Ugh.  I told him that was not a concern with me – I have Hubby’s blessing and I would never give up any real life info.  That I help friends online fly under the radar, know all the tricks to stay safe.
He asked me real world details… I gave vague answers about where I live and where I work.  He did the same.
He stroked my arm and stared at me.  He has piercing blue eyes.  I closed my eyes and took a deep breath.  I could not think when he did that.  I can’t wait until I am past that point!  I am so starved for touch… he watched me, marveled that so little contact could set me off.  I told him he knew why.  He asked if I would be upset if he stroked me elsewhere.  I smiled and he shifted to teasing a nipple through my clothes.  I had to cross my legs… all I could think about was kissing him.  But he stayed in his seat and every time I leaned slightly toward him, he looked away and said be careful, a guy was getting into a car two over etc.  He was scanning around constantly, seemed very nervous even when we were just sitting there talking.  
I put my hand on his leg midway between the knee and the top.  He covered my hand with his to keep mine from moving, and told me he wanted to go slow.  I put my hand on his cheek and we kissed once.  I pulled back but he followed and deepened it.  But very carefully… every time I tried to suck or lick, he backed off.  I began to think he didn’t enjoy it, so I went back to my seat and stared at him.  He played with my scarf, wrapping it around his hand.  
He talked about what he is looking for… said he is a switch. He likes to dom sometimes and be dominated others.  I had not run into that before.  It is not my thing, but I tried to stay open to his ideas.  It’s usually not as scary as I’m imagining.
He gave me another big kiss at the half hour mark and said he had to go back to work.  I assumed that meant he didn’t like me.  I smiled and he disappeared.  
I sat there replaying the meet in my mind, deciding that I was not bowled over by him. but he could be the kind of guy who takes awhile to get to know.  I do wish he had bought me an iced chai.
Before I could get home, there was a long email from him, saying how much he liked me, how he enjoyed listening to my breathing and watching his effect on me.  And he wants to see me again.  After the silence from The Dancing Man, it was a relief to hear from him.  
He emailed the rest of the day with different fantasies he wanted to be our next step.  I sent him to look at Freya’s tumblr… that really set him off – said he liked the dominatrix and her frilly panties.
If I had to decide right now, I would cut him loose.  But there is time to explore and understand more. So we’ll see…

I closed the day with one last email:

Hiya, Can’t go to bed without saying thanks again for making this a very special Friday.  Now when I say “Hugs with groping” you have a better idea of what I mean.  🙂