Category Archives: Traveler

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Hey darlin’

From: Sassy
To: Mr Truck
Sent: Wednesday, April 24, 2013 12:06 PM
Subject: Re: Sunday
Good morning sweet Stan, 
All the mess down here makes me appreciate life a lot… simple things like being able to go out of my home!  But it also makes me realize my life is not how I wanted… I needed a man soooo badly.   Not just the sex… the hugs, the listening.  *sigh. 
Ah restaurants.  You know I can go on and on about those!  Have you been to Rudy’s Tequilaria in Teele Square?  They are smaller scale and low key compared to Painted Burro but better food and you can hear!  Red Bones is fun – I adore barbecue.  We’re often there with about 40 project people and whoop it up down under.  
I’ll have to check out your suggestions.  Thanks!  We used to go to Allston a lot to eat at a tiny Vietnamese place called VMajestic.  But it closed suddenly 3 years ago.  We adore the authentic Chinese at Shanghai Gate over at the corner of Comm and Harvard Ave.  
Are you really not getting anything?  When was your last roll in the hay?  How can you stand it?  Why don’t you let me help?!  I do wonder if you are an email king… which is fine with the wonderful emails you send!  Being together still feels like a great idea if the stars ever align.  You seem so much better than anyone else I am talking with, so I hold out hope it will be true in person.  Touching.  Tasting.  Fucking.  YES!
No fun sex lately.  I used to be juggling several guys but I have grown weary of that.  I am mostly on AM these days only to help friends edit their profiles.  I get hot messages from my old flame, but I am completely starved for male company.  I have been alone with a man doing sexy things exactly 5 hours this year.  NOT ENOUGH! 
1) An interesting Friday afternoon in February with a much-older local AM man at the Hyatt – he craves big women and despite me being large he wants someone bigger!  He wants to see me again but it’s tough after someone says you are not what they want.  He did send interesting videos that you have benefitted from, so he has his moments.
2) A delightful expensive dinner and “dessert” at a fancy hotel with an even older traveling AM man from Florida the first week of April – he is a complete sub and I am not a domme!  I tried but… it’s not as easy as you might think.  He only wants to email to set up a meet, so no fun day-to-day. Can’t decide if the perks of seeing him outweigh his quirks.  
You are so cute – it’s wonderful that bodies of all kinds can get you going!  Enjoy the view.  
I’m off to run a big reception with sweets and champagne.  I will eat an eclair and when the sweet cream slides down my throat, I’ll think of you and smile!  
-S
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From: Mr Truck
To: Sassy
Sent: Apr 28, 2013 9:23 AM
Subject: re: Sunday
Hey darlin’ loved your email. Your words made me want to love you affectionately, talking and kissing into the wee hours of the morning.
I’ll have to look for the Rudy’s and the Shanghai Gate.
Yes I’ll show myself to you to be real, the email king comes alive!
Interesting encounters even if not totally fulfilling. Any fun heavy petting?
How was the reception and especially, how was that cream doing down your throat? 😉 I sure won’t let my cum go down your throat (well not all the time!) but rather let us play with it on your lips….
What’s up today? Nice weather huh? What clothes does this weather have you wearing? Me, shorts and t-shirt.
Let’s talk soon xoxo
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From: Mr Truck
To: Sassy
Sent: Apr 28, 2013 9:24 AM
Subject: Vid clip
Thought you might like this. Love how she’s on top fucking him hard to get herself off:
http://xhamster.com/movies/1799712/teen_alyssa_branch_screaming_orgasm_fucking_on_kitchen_table.html
[Sadly, this video has disappeared. Here’s another of Alyssa Branch to entertain you.  Enjoy!  
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You would think

Monday, April 15, 2013

So there was a thing in Boston today.   A VERY BAD thing.  And it was all over the news.  All over the world.  Late afternoon, I started hearing from friends and family and project people and co-workers and bloggers and blog fans and chatters and Philip and…

You would think I would hear from the AM men I am corresponding with regularly.  Mr Truck?  Panties Man?  Mr Hyatt?  Maybe the Traveler who had just been here?  Maybe they’d inquire as to how I am?  Was I there?  Am I close to the area?  Tell me how they got along today with so many roads and services disrupted?  I thought they’d check in.

Wrong!

The only man I heard from was Schenectady Sam, the guy over 100 miles away who had helped me try to unravel and AM Mystery in late March, that I hadn’t talked with much at all.

Not a word from any of the others.  Zip.  Nada.  Zero.  They were the only subset of my social circles that were silent.  Why do you think that is?

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IM Apr 15 4:27 PM
• Apr 15 4:27 PM Sam: are you OK?????
IM Apr 15 9:38 PM
• Apr 15 9:38 PM Sassy: Yes. I am fine. Thanks for checking on me!
• Apr 15 9:38 PM Sassy: Scary shit Sam. 
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From: Sassy
To: Sam
Sent: Monday, Apr 15, 2013 9:46 PM 
Subject: Checking in 
Hiya!  Since IM is being so freaky, I am switching to email.  
Thank you very much for checking on me!  It’s been a long strange afternoon, but I am fine, and as far as I can tell, all my pals are safe too.  Several of them were right there, but got lucky. 
Here’s a fun video of a man hard at work, to keep us smiling.  This is NSFW!  
http://www.redtube.com/28931
-S
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To: Sassy
From: Sam
Sent: Tues, Apr 16, 2013 9:10 AM
Subject: Re: Checking in
What a thing.  I watched it all unfold on the camera feed from WBZ.  I’m glad to hear that you and yours are safe, but man … it just makes you shake, doesn’t it?
Thanks for the video.  🙂  I watched it this morning BEFORE I drove in to work.  And now that I’m here, I’m …
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From: Sassy
To: Sam
Sent: Tues, Apr 16, 2013 11:42 AM
Subject: Re: Checking in
Good morning!  
I flipped back and forth between the Boston Globe tweeter feed and CBS live feed… so bizarre.  How can this happen in my city?  On this day?  Then my phone, email, IMs and Facebook went wild with people checking on me.  It is lovely to be cared for!  
We are trying to focus on the good done by hundreds of people rather then the evil done by a few.  I do feel the need to reconfirm that I am alive, say things to people I care about.  Never forget that you are a special man and there is a sassy woman in Boston who thinks so!  and wishes she could kneel at your feet and have a blissful look on her face while she pleasures you slowly and carefully with her hands and mouth for 5 minutes!  Have a great Tuesday! 
-S
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From: Sam
To: Sassy
Sent: Tues, Apr 16, 2013 2:18 PM 
Subject: Re: Checking in
well that idea just made me totally melt …
xxx
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Traveler Twinges

From: Sassy
To: FredRRoberts
Sent: Fri, Apr 5, 2013 10:47 AM
Subject: Re: Let’s get together Wednesday!
Good morning!  Happy Friday!  
I am having twinges in certain places… fun remembering why.  🙂  
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I never heard from him again.  And that was okay.  I hope he found a great domme! 
After a couple of months, I did more research online, plugged his photos into Google Images to see if I could get a name so I could check for news of his retirement or an obituary.  Wow… this guy is a BIGWIG!  I felt a small thrill that I can attract such a high-powered, successful man.  I should have ordered dessert! 
NOTE:  If you want to stay anonymous – Do NOT give a woman your business head shot.  It will lead her to your business, your bio and all your contact info in one click.  

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The shawl mystery

From: FredRRoberts
To: Sassy
Sent: Apr 4, 2013 12:22 pm 
Subject: Re: Let’s get together Wednesday!
Hi Sassy:
Great night with you. 
You lost a shawl in the room–it’s at the front desk–they are holding it for you.
F.
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From: Sassy
To: FredRRoberts
Sent: Apr 4, 2013 1:42 PM
Subject: Let’s get together Wednesday
Hiya Fred!  You really have me smiling today!  Dinner and dessert were delightful!  You are such a special man.  
Hunh… I’m not missing anything that I know of.  But I will check my coat/scarf etc.  Thank you!  
Hope you had an easy trip home and will come back soon.  

-S
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Yay!  Email from Fred! So he is a gentleman with manners.  Phew. 
The shawl thing is a mystery.  I know I didn’t leave anything behind.  Shawl?  I wasn’t wearing one.  Maybe it was a terminology problem.  I double-checked my coat – my scarf was there.  So… what did he leave at the front desk?  Maybe he had a bought a beautiful shawl that he wanted me to have and this was his way of giving it to me?  Maybe there’s be a box with a gift?  Hmm… I was so curious!  I talked to the folks in chat.  No one had a theory that made any sense.  
The traffic down there is crazy, and the parking worse, so I made up my mind to drive down there about 10 pm, ask the doorman to watch my car for 3 minutes while I ran in to the front desk.  That worked and I strolled up to the desk clerks and realized… I don’t know the guy’s name! and he didn’t know mine.  Would he have left it for “Sassy?”  Hmm… I can finesse this.  Vague.  
“Good evening.  A guest left a shawl for me this morning?”  
“Oh!  Yes.  I was here when he came by.  Just a moment,” the older male clerk said as he rummaged under the counter.  Phew.  That was easy!  He pulled out a carefully folded… white fleece blanket that was at the bottom of the bed from the room.  We stared at it.  
“That’s definitely not mine.  It’s the throw from the room, right?”  The clerk nodded.  I open it and shook it, to be sure he had not hidden something in its folds.  I could not fathom why he would have thought that was mine, or left it for me.   Or why he would have wanted me to go back to the hotel?  It was a little embarrassing, but the staff were very good about not going there.   
“Do you want to keep it anyway?” he asked.  I shook my head, shrugged, thanked him and went back to my car very puzzled.  
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Meeting The Traveler – Perks & Quirks

Wednesday, April 3, 2013


The 10th man I met from AM – he called himself FredRRoberts, a journeyman basketball player who spent a little time with the Celtics in the 80’s.  I call him The Traveler.  
Fred Roberts
I got email through Ashley Madison from Fred, a traveling businessman coming to town from FL.  He was looking for a domme.  I told him that was not my thing, but I’d be glad to have dinner with him if no one else stepped up.

This is what I thought all AM dates should be like – free dinner, pleasant conversation, touching, then a hot time in a hotel room on a man’s expense account!

I got dressed up in black silky pants and an unconstructed blazer, with a pink silk top with black abstract squares, my lucky black bra and panties, black knee-his and clogs. I wore my hair down. I dug out my classic dark blue wool coat with the colorful silk scarf. My husband gave me a ride downtown.

I met him at the bar of The Oceanaire, an elegant seafood restaurant downtown.  It used to be a bank, with high vaulted ceilings and marble all around.

I found him sitting at the bar, sipping wine. We hugged and he groped my ass and smiled such a big smile!  We had dinner, sitting at the only booth in the restaurant, the most sheltered space in the passage between the bar and the dining room, at the head of the elegant stairwell.  It has a very “elegant, old Boston business” feel to it.

He was charming – tall, handsome and debonair in that “older tennis player” way, told great stories. His AM profile says he is 61 but I am betting 70. He seemed much older than I am. He reminds me of Ken Howard, the actor.


Ken Howard
We talked and touched, held hands.  I craved lobster but the only option they offered required dealing with the shelled version, so I settled for the had Seared Flounder Louie (a rather modest portion of a bland mix of seared local flounder with lump crab meat sprinkled on top, and a caper beurre blanc sauce presented rather haphazardly) and shared sides a la carte- steamed asparagus with Hollandaise and Caesar salad.  He had salmon which he requested plain broiled. He sipped more wine while I had my usual iced tea. The waiter was fantastic – just the right mix of attentive but not intrusive – a professional. The bill was $125… so not worth that! Thank goodness for expense accounts!
He told me he’s is a sub, as in “wants the woman in charge and telling him what to do.”  He said he has to run everything in his business and his family and wants to relax in the bedroom and let someone control him. Which sounds easy but is not for me. He said we could still have fun even if I was not up for that, invited me to his hotel down the street.  As it’s been six weeks since I’ve had a hug, I decided to give him a chance.
He put an arm around me as we walked across the restaurant to reclaim our coats, pecked me on lips in front of the hostess – he was definitely getting off on being seen with me and letting people know I was his lady this evening. It was an interesting change from the usual clandestine meets!

The Ames Hotel

We strolled down the block and I went up to his first class hotel and we played.  He hugged me and I stepped him backwards until we were facing the mirror.  He was very pleased with that, watching as we kissed and groped and undressed each other. It felt so good to hug and kiss! He had a very fit body with smooth, tanned skin. He wore a toupee – I was afraid to touch it. I had not realized how much I play with a man’s hair!
He pulled me over to the bed and we stretched out next to each other. Nothing like skin on skin! He lavished attention on my clit and my chest.  He knows what he’s doing! But he made the same noise over and over… sort of like a boat motor! It got old fast!  
I played with his nipples, then his cock which he reacted to in the “wow… no one has done that for awhile” way.  I tried telling him what I wanted, which seemed to satisfy his sub needs a little.  He asked me to order him in a harsher tone but I just couldn’t. I tried to pretend, to act it out but I ended up giggling, apologized and gave up.

The condoms he had were ancient and broke when we tried to open them… so he asked if I could finish him with my mouth. We stuck to kissing and groping and oral.  I swallowed.  He is very sweet and skilled, but I was very nervous and could not cum… need to learn a way around that! First times are weird.
We cuddled for awhile but I could see he was tired. So I gave him a big kiss, got dressed, and gave him another big kiss. He got up to hug me and pressed a $20 bill into my hand, asking if that would cover a cab home. I nodded, thanked him and checked around to be sure I had everything. I headed out and down to the curb. The doorman hailed me a cab. I tipped him and took my ride home, puzzling over whether I want to see The Traveler again. 
It wasn’t clear at that moment. The perks may outweigh the quirks, and it could be a nice evening once a month or so.  He only wants to communicate to set up meets, which may not give me enough info to please him, but I might try if he contacts me again. And I’d like to know what sex with him is like! But I certainly wasn’t able to do what he said he wants, so I won’t be surprised if he disappears.


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The Traveler Plans a Meet

Apr 1 – 7:03 pm via AM
From: FredRRoberts
To: Sassy
Message:
Sassy:
Just making sure you got my note–we are ON for Wednesday night–will make dinner reservations for us. I am staying in town at the Ames.
Can’t wait to see you.
Fred
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Apr 1 – 7:08 pm via AM
From: FredRRoberts
To: Sassy
Message:
What kind of food do you like–any dietary restrictions?
=======
via Yahoo 
From: FredRRoberts
To: Sassy
Sent: Apr 2, 2013 9:45 PM
Subject: Re: Let’s get together Wednesday!
Hi Sassy:
We have reservations tomorrow at Oceanaire Restaurant 40 court St. I am staying at the Ames right down the street.
Excited about seeing you and the possibilities!!!
Fred
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From: Sassy
To: FredRRoberts
Sent: Tue, Apr 2, 2013 at 10:04 PM
Good evening Fred!  That looks delightful.  What time?  Will I find you in the bar? 
 -Sassy
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via Yahoo 
From: FredRRoberts
To: Sassy
Sent: Apr 2, 2013 10:45 PM
Subject: Re: Let’s get together Wednesday!
yes you will–see you at 7
really looking forward to it!
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Apr 2 – 11:23 pm via AM
From: FredRRoberts
To: Sassy
Message:
Sounds wonderful! The secret of 31 will be revealed to you and you alone tomorrow!!
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Apr 3 – 3:01 pm via AM
From: FredRRoberts
To: Sassy
Message:
See you in 4 hours–will keep you smiling!

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Traveler plans

Date: Mar 31 – 5:30 pm via AM
From: The Traveler 
To: Sassy 
Message:
Hi Sassy:
I don’t have to be submissive to be happy–you definitely meet my specs otherwise.  If full domination to you is groping, that’s fine. Let’s give things a chance.
Can you please give me access to your pic and let’s see what happens!
F
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Date:  Mar 31st – 8:38pm via AM
From:  Sassy
To: The Traveler 
Message:
Hiya Fred, Great to hear from you. Thanks for clarifying your situation, and for taking a chance. Sounds great! Please email me at the same ID on Yahoo, and I’ll share a photo or two. I am wary of trusting AM that far. I am open Wednesday night if you decide you want to meet. Hope we can have some fun!
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Via Yahoo
From: FredRRoberts
To: Sassy
Sent: Mar 31, 2013 9:25 PM
Subject: Let’s get together Wednesday!
Hi Sassy–here I am–please send me pics and we’ll go from there–really look forward to meeting you.
[attached his business head shot photo]
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Date: Mar 31 – 9:30 pm via AM
From: The Traveler 
To: Sassy 
Message:
Sassy:
Just sent you an email. Wednesday looks great–can’t wait to see your pics!
Fred
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Date: Mar 31 – 9:39 pm via AM 
From: The Traveler 
To: Sassy 
Message:
Please send pics to [his gmail address.]
Thanks!
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Via Yahoo 
To: FredRRoberts
From: Sassy
Sent: Sun, Mar 31, 2013 9:43 PM
Subject: re: Let’s get together Wednesday!
Hiya Handsome, 
Thank for another photo!  Your photos are making me smile.  Here’s one of me from a year ago when I was going to a party and dressed up.  My hair is longer now, but otherwise about the same.  
-Sassy
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Via Yahoo 
From: FredRRoberts
To: Sassy
Sent: Mar 31, 2013 10:45 PM
Subject: re: Let’s get together Wednesday!
Terrific. We are on for Wednesday night. Details to follow–wow!
Fred
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Traveler tries again

Remember The Traveler from earlier this month?  The one who sent a blast email to a bunch of ladies in Boston hoping to meet while he visited?  The one I decided not to answer?  Well, here he is again.  With a personal message this time, with some personality!  It’s been such a quiet month.  I figure it can’t hurt to email him, see what he really wants. 
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Date:  Mar 30 – 6:16 pm via AM
From: Traveler
To: Sassy
Message: 
Hi there Sassy:
I could be the man for you! 6’4″, 215, well-built, athletic, handsome (see pic). Professional–smart, funny, caring.
Absolutely LOVE BBWs! Only attracted to larger, fun women. Wife has no interest in sex.
I travel to Boston a lot and will be coming to town next week. Would like to see you on Wednesday if it works out–we could do dinner in Boston.
Let me know if that works–happy to email/talk beforehand.
You won’t be disappointed.
Fred
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Date:  Mar 30th – 6:58pm via AM
From:  Sassy
To: Traveler 
Message:
Hiya Fred! Thank you for your lovely invitation! And access to your photo. You are a handsome fellow! Unfortunately, I am not into most of the things you are looking for, so I won’t waste your time. I do hope you find a lovely lady to be your companion. 
If you end up facing dinner alone and would prefer company, I’d be glad to meet somewhere low key, talk and give you a nice hug with groping, but that’s about the limit of my domme tendencies! Safe travels and happy hunting! 
-Sassy
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The Traveler

You have new email from FredRRoberts!


     View   Profile    Lists    Search   Mailbox   Viewed Me

With QuickieMail, just reply to this email to respond directly to FredRRoberts! No need to log in to your Ashley Madison account!
FredRRoberts sent you a message
Age: 63
Location: Key Biscayne, Florida, United States
Height: 6’4″ (193cm)
Weight: 220 lbs (100kg) – Fit
My Limits Are: Anything Goes
Status: Attached Male seeking Females
Gender: Male
Ethnicity: Caucasian (white)
Mar 3 – 3:03 pm
Hi there. You are my type, and I’m exactly what you’re looking for–I meet your profile.

Come to Boston regularly and will be there on March 14-15–can we meet?

Fred

============
It was a quiet week on the Ashley Madison front.  On Sunday, I heard from a new man. 
The above is what an email from Ashley Madison used to look like.  Rather odd.  The magenta row across the top has links that take you directly to the site.  
On this day, it was from a “Traveling Man,” AM’s name for a man looking for a woman somewhere far from their home.  AM gives them a special deal so they can blanket their destination with messages to a lot of women.  So message is not specific and often the guy is not someone I am interested in at all.  However, the basics on this man were tempting – tall, in the age range I’ve had success with, not too skinny, and a simple message with no typos! 
I find the idea of a traveling man very attractive, if he visits regularly.  Free dinner and the hotel on his expense account, likely well-off and well-traveled with interesting stories, and on a regular schedule with advanced warning.  Far from almost anyone who would recognize him.  Right? 
I googled his user name – a Celtics basketball player!  Hmmm… someone with Boston-area roots I’m guessing.  I looked at the rest of his profile.  There wasn’t much more there, but it was very forthright and different from any other I’ve seen in that it stated his kink right up front. It looked something like this – I think all of thees are checkboxes he checked.  Or maybe he wrote the second section? 
===========

Preferences and encounters I am open to:
Conventional Sex, Light Kinky Fun, Being Submissive/Slave, Bondage, Fetishes, Spanking, Role Playing, Erotic Tickling, Experimenting with Sex Toys, Threesome, Open to Experimentation, Erotic Movies, Aggressiveness, Sensual Massage, Extended Foreplay/Teasing, Likes to Give Oral Sex, Likes to Receive Oral Sex, Kissing, Cuddling & Hugging, Sharing Fantasies, Sex Talk
What really turns me on:
BBW, Naughty Girl, Sense of Humor, Imagination, Creative and Adventurous, Aggressive/Take Charge Nature, High Sex Drive
============
What an interesting mixture, eh?  He likes BBWs!  Many things I find very attractive, yet one big kink – a submissive.  
I thought hard about this… do I have an “Aggressiv/Take Charge Nature?”  Um… not so much.  I’m not submissive but I am certainly not a domme.  Could I role play, act it for a night?  I’ve never done it… how can I know if I’d like it or not?  What if I really didn’t like it?   If I was going to try it, I’d want to talk for quite awhile first, set expectations and…. I can’t do this.  I decided not to answer him.