Meeting LOLBob

November 9, 2017 Thursday
9:06am
From: Sassy
Message
Good morning hot stuff! 
I’m dressed in dark blue with a light floral silk scarf and so excited to see you!
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9:58am
From: ogs1967
Message
Very excited to see you too! I have blue shirt, tan pants, brown jacket. 
2:30 still good for you?
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12:42pm
From: Sassy
Message
Yes indeed! See you at John Harvard’s! Mwah!
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1:15pm
From: ogs1967
Message
Awesome! See you there
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2:13pm
From: ogs1967
Message
I’m here at the bar whenever you get here!
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Report #1 Bob 11/9/17
November 9, 2017 Thursday 
Put in AM messages from Nov 6 on
I made it to the bar at John Harvard’s at exactly at 2:30 pm.  I walked slowly down the stairs, looking around.  A man seated about halfway down the bar looked up and smiled.  I checked his clothing and it was him!  He stood up to greet me and opened his arms for a lovely hug!  He’s cute!  He is tall and skinny and has a shock of reddish hair!  
He asked if I wanted to join him at the bar or get a table- he had a beer half-drunk and a glass of water, and a glass of water for me!  Very thoughtful! I said it was fine to sit at the bar and thought “that way I can touch you more easily” but I didn’t say it.  I hopped up on the bar stool and pulled closer to him.  He stared at me and smiled.  There was no one close to us so we could talk freely.  
The bartender came by and I ordered a diet coke with lime.  Bob asked me if I didn’t want something stronger?  I told him I can’t drink.  He seemed a little startled, but I assured him it was fine that he was.  
He said he’d gotten there early and nervously looked up every three seconds hoping I’d arrive.  I told him I was so glad he was there first so I didn’t have to do that!  He said every time his phone pinged he thought it would be me flaking out.  I told I don’t do that.  He said he didn’t mean me, just him being nervous.  I patted him on the arm and told him I understand.  
He asked me where I live and when I moved there, so I got to talk about my condo a little. 
He told me about his history on AM – he’s been on and off twice in the past two years, met four women, none of which seemed worth following up with.  He said it’s a big step and he didn’t feel ready to take the risk for any of them.  I said it’s true, and you have to be careful, but it should be fun!  It’s not a huge deal… it’s… scratching an itch.  It doesn’t “go anywhere” except a few hours of amazing physical contact and someone to listen and appreciate him.  He smiled and said he was way overdue for that!  
I told him that my husband and I are open, so I don’t need to worry about stealth, but that I know how to help men keep themselves safe, and I try to stay anonymous.  He nodded.  He said he wanted to keep using the AM interface – no texts or emails – to keep himself safer.  Probably a good idea but… yuck. 
He asked how my meets usually go – where, when.  I said mostly hotels or after awhile, maybe at my place.  And that I can pay and he can give me cash.  He nodded but seemed daunted at the idea of paying for hotels.  He said he has kids in college. *sigh
I got him talking about his work.  He had some great stories.  He talked about the sports he likes to participate in – hockey, basketball, skiing.  I told him I am only athletic in bed.  He grinned.  He said he is really out a practice in bed but hopes to get up to speed quickly.  I told him about how I’ve learned so much in the last few years.  Like what?  He asked.  So I got to tell him about how I used to think blow jobs were just sucking but I’ve learned they are more.  “Oh?”  he asked.  I said they are about licking and touching, and he trembled.  Heh.  I am so sassy! 
I mentioned I might retire in a couple of years.  He said he could never retire – he has kids in college and other expenses that will keep him working and he likes it, so he’ll keep at it.  
We talked about tumblr and my toys.  He said the internet is very helpful for “inspiration.”  
It got to be an hour and I decided this was enough for a first meet.  He seemed surprised but said he hoped we could see each other again soon for “more adult activities.” I offered to take him into the handicapped-accessible bathroom right now for some kissing and groping.  His eyes went wide but he declined.  He said there would be time and a bed soon.  He said he wanted me to know right away that he was interested.  That was sweet.  
I stood to leave and he got up and hugged me again.  I felt good in his arms.  He pulled back a little and kissed me quickly on the lips.  So chaste.  This guy has not been with a woman in a long time.  And maybe never with one who likes sex.  
He smiled and asked if he could do it again.  I grinned and nodded, and he pecked my lips again and looked very pleased, like he had crossed some line and not gotten hit by lightning and was emboldened.  Heh.

I smiled and took off up the stairs, wondering if I’d hear from him but not really caring either way.  Which is probably good so I don’t get my hopes up but am pleasantly surprised if he writes.  He does not seem to have thought this out, the cheating thing.  Wonder if he will? 

Planning with LOLBob

November 8, 2017 Wednesday
8:55am
From: ogs1967
Message
Hi Sassie, what’s up today?
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10:09am
From: Sassy
Message
Hiya Hot Stuff! Hope you’re having a wicked good Wednesday! 
I’m puzzling over when, where to see your smiling face. 
Do you have any time tomorrow? Could hug you for real!!
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10:31am
From: ogs1967
Message
Yes, that would be wonderful to meet you! 
Free in the morning till 11 and then after 2 pm…. 
love to meet so let me know if that works.. Bob
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3:35pm
From: Sassy
Message
Hiya Bob! How’s your day going? 

Could you do 3:30 or 4 pm in Harvard Square? I’m thinking to get out of work early and meet somewhere public like the Starbucks on the corner of Dunster & Mt Auburn Street (in the Garage) if you want coffee, or John Harvard’s on Dunster Street if you’d rather sit underground at their bar or a table. If you have some other favorite around there, chime in. 
Mwah! 
-Sassy
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3:47pm 
From: ogs1967
Let’s say 2:30 pm?  John Harvard’s sounds perfect.  
Can’t wait! 
=====
3:48pm
From: Sassy
Message
Here’s a 2 part snippet of erotica for you 
The View 
Part 1
Just as I was finishing my last meeting of the day yesterday, gathering my papers off the marble table in the conference room on the 36th floor, the sound of sirens wafted up from the expressway below. Everyone else had left the room, so I took a minute to lean over the marble counter and stare down at the roadway. There was a horrible wreck of mangled metal and shattered glass, several cars and a tractor trailer twisted together. The traffic was stopped behind the mess, and the cars on the other side barely moved, rubbernecking. Suddenly, I heard the door close. I straightened up, but before I could turn, I felt your arm around my waist, and felt the heat of you on my back through my dress. You were already hard, pressed tightly against my ass. I started to speak, but you put a finger on my lips and teased a corner. I licked your thumb, and you moved your hand down to unbutton my dress. Just enough to slip your hand inside and tease a hard nipple. I moaned and let my head fall back against your shoulder. You bit my neck and ran your tongue across my skin.
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3:49pm
From: Sassy
Message
The view
part 2 
You slipped your hand under my skirt and inside my underwear, teasing my most sensitive spot. You pressed a finger inside, unsurprised at the moisture gathered there. I was startled as you lowered my underwear. I felt like my knees would buckle, but you tightened your grip and spread my legs to balance me against the counter. I panicked when I heard the rasping sound of your zipper, but before I could form the words in my mind to stop you, I felt you hot and hard against my skin, and a low moan was all that escaped my lips. You shoved it inside me, and your breathing grew ragged as you watched yourself slide in and out. You kneaded the flesh of my hips as you moved, then reached around me to rub the top of my slit in time with your strokes. I was trying to be quiet, but could not hold in all the gasps of pleasure as you thrust deeper and deeper inside me, your balls slapping against me. You felt the trembling start inside me, and the clenching around you. You felt the pulsing, the searing heat and suddenly lost control, pounding me into the wood and stone, spurting up inside me over and over. The only sound was our uneven breathing and the whirring air conditioning. You pressed your cheek to my back and whispered, “What a view…”


Carmina Burana on ice

November 8, 2017 Wednesday

7:33 AM Sassy
Good morning! It’s COLD…38!  Wish you could cuddle.
8:08 AM Phil
Awwww : ) 
it’s that time of year finally! I like the cool air. My buddy is staying over tonight and tomorrow so fun evenings.

6:57 PM Sassy
Plushy skating to Carmina Burana in NYC last week. Wowzers
I adore it when Youtube recommends a video I might like to watch and yes…yes I do!

Evgeny Plushenko: Carmina Burana 

2017 Ice Theatre of New York

[youtube=https://www.youtube.com/watch?v=HQzVrk0Fsjc&w=320&h=266]

Excellent answerer

November 7, 2017 Tuesday
8:09am
From: Sassy
Message
Good morning Bob! Hope you’re having a terrific Tuesday so far! I’m off to vote. Whee. 
Tell me about your favorite meal? 
Favorite part of a woman’s body? 
Your favorite movie? 
Mwah!
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8:20am
From: ogs1967
Message
Catching up on answers – AM is safer for me than email: 
I’m mostly out and about for my job.
Let’s go for some rock – Bruce Springsteen!  
Not allergic to cats. 
love Frutti di Mare 
love all parts of a Woman’s body but love nice big breasts…and curves, waist, thighs…necks too…
mmm I’m a softy so movies with happy endings…officer and a gentleman…the Natural…Rudy…but I do love sci-fi and action…Bourne movies are great…xmen, iron man… 
Voting is a good thing!
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10:15am
From: Sassy
Message
Hiya Bob! Busy day for you? 
I’ve done my civic duty and made it to my office so I have a moment to escape into writing to you! 
You are an excellent answerer! Are there any questions you want to ask? Any deal breakers you should check on? Any kink you should ask if I can help with? 
For a special meal, I adore lobster pie… just meat and Ritz cracker crumbs and butter. Though I do like all sorts of food – Thai, Chinese, Vietnamese, Afghan, Italian and a steak or a pizza now and then! 
If I am looking at a man, I check out his shoulders. Not necessarily into big or broad, I just adore the different shapes and sizes. If I am touching, the list is much longer! 
So sweet to hear the movies you like! I usually go for movies with kissing, or Star Trek or Star Wars, or ones like “Hunt for Red October.” I just saw “Victoria & Abdul” at the Kendall… Judi Dench is spectacular! 
I’m more of a folk music type – just saw David Wilcox in the back room at The Burren… a man, a guitar and amazing songs! 
So glad you are not allergic to cats! Do you have pets? 
Thank you for giving us time… I feel much safer and can have a lot more fun if I know who you are and what you like. Gotta do some work. 
Think about a sexy French kiss today! 
-Sassy
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12:34pm
From: ogs1967
Message
Hi Sassy, I think it would be nice to meet for coffee sometime if you’re up for it. I work in your area so easy for me. Let me know if you can sneak out at your work or if you can fit me in your schedule. If you still feel you need to chat more before you get comfortable, no worries, I just think it would be nice to meet. Let me know, Thanks 
I love Star Wars and Star Trek movies too! the new Star Trek are surprisingly good, they really got the new actors right on them.


Voted

November 7, 2017 Tuesday

7:53 AM Sassy
Good morning Philip!  I’m off to vote!
8:16 AM Phil
Good morning! Enjoy!

9:03 AM Sassy
45 degrees. Brrrr…I caved and turned on the heat.
10:19 AM Sassy
Civic duty done!

[photo of me with my “I Voted” sticker on my shirt.]

LOLBob writes

November 6, 2018 Monday
7:01am
From: ogs1967
Message
Your profile greeting made me laugh.  I didn’t expect that on here! Haven’t seen that commercial in awhile…lol…can you help me save myself and others the pain of a sexless marriage…lol.
I’m Bob, Say Hi, I won’t bite…lol…
=====
A new guy wrote to me this morning!  
Hmmm… He got the joke in my profile!  Means he looked at my profile.  Good.  

He used lol three times 5 sentences.  He’s nervous? 
I took a look at his info.  
Okay tag line… describes him succinctly.  (Much better than the men who write, “Hello”)  
Age? 50.  A bit young but might be okay, especially if he’s really 52 or so (which is common). 
Location – north of me a ways.  Good.  I somehow do better with guys from the north! 
Height: 6”0”  – good 
Weight: 170 Slim – hmmm… I like men burly and he sounds skinny but might be okay. 
Limits:  Whatever excites me – good.  Much better than “undecided.” 
Status: attached – good 
Preferences – looks good, nothing scary 
Didn’t write much.  Tough to tell if he’d like me, or I’d like him.  I’ll think about it. 
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8:49am
From: ogs1967
Message
Any interest after seeing my profile? I love voluptuous women!
=====
Whoa… a second message already?  
He’s got that feature turned on where he can see that I looked at his profile.  Eager fellow.  
And he l likes big women?  
Okay.  Haven’t met anyone in awhile… Worth a try I suppose.  
=====
8:56am
From: Sassy
Message
Hiya Bob! Thanks for making me smile on this dreary Monday morning. 
So glad you read my profile and got the joke. 
Three quick questions for you – 
what brings you to Ashley Madison right now? How did hear about it?
Have you always lived in MA? 
How old were you when you first had sex? 
I am curious as well as Sassy! 
Hugs with groping! -S
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9:13am
From: ogs1967
Message
Ok, on here because I am in a sexless marriage, it’s pretty well known website,
 I’ve always lived in MA and I 1st had sex at 20. 
You seem fun so maybe meet? Coffee, tea or me… lol 
no really sincere here so if you’d like to get a coffee and meet that would be fun
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9:36am
From: ogs1967
Message
I work in and around Boston during the day
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10:09am
From: ogs1967
Message
Did I lose you already with my responses? ….lol
=====
5:08pm
From: Sassy
Message
Hiya Bob! Hope you had a marvelous Monday!
Sorry for the delay… one of “those days.” You certainly made it better! 
Hubby broke his phone for the second time in 3 weeks, so we got to dash to T-Mobile first thing, and then it was a wacky day at work. Hope tomorrow will be better. 
So… where were we? Ah yes… thank you for the answers! Here are my answers – I am also in a “nothing at home” situation. Never thought I’d venture out, but I fought off cancer 7 years ago and decided I want to live a full life and that includes sex! Glad you found AM and wrote to me. I first had sex at 17 with my high school sweetheart. We didn’t know what we were doing and it was… boring. I’ve learned a lot since then! 
I’m not into coffee or tea but maybe you? And some iced chai. 🙂 Give me a day or two to be sure you aren’t an axe murderer and we’ll see. 
Three more questions – 
1) Want to say something about your work? Are you in an office mostly or out and about? I’m an office manager – you know, that quiet, efficient older woman who takes care of all the administrative stuff so the higher-ups can do their work. 
2) If you could take me to any concert in history, what would it be? 
3) Are you allergic to cats? 
If you want to switch to email to answer, send me your address and I’ll reply there. 
Hugs with groping and an ear nibble for your patience. 

-S


Lobster Macmuffin

November 5, 2017 Sunday

9:20 AM Sassy
Good morning Philip!  
Have a wonderful time today!  Mwah!

12:53 PM Sassy
First time for brunch at Article 24 in Allston
Bloody Mary without alcohol
Deviled eggs with bacon
Pork lollichops with hoison sauce
Veggie omelette
Reuben sandwich and fries
Lobster Macmuffin

1:00 PM Phil

8:47 PM Sassy
Apple streussel pie and vanilla bean ice cream from Skowegan ME, at The Ninety Nine restaurant in Somerville



Mouthful

November 4, 2017 Saturday

7:36 AM Phil

[photo of his legs and bare feet on the couch with a cup of coffee and a dog in his lap]
Good morning! Enjoy the day!
7:37 AM Sassy
Good morning kid!
I wanna rub those feet.
7:38 AM Phil
: ) 
7:41 AM Sassy
And other body parts.
And those doggos!
I’m taking lunch to a project gal whose mom died Thursday night.   Triple sad – mom, best friend, roommate.  And died 3 weeks after they discovered a brain tumor!
I’ve discovered $100 of bbq is a great comfort at these times.
7:44 AM Phil
That’s sweet and it sure does help!
[photo of his legs and bare feet sitting on the couch with his cock sticking out of his shorts]
 hee hee
7:45 AM Sassy
So your hanging out this fine morning?
Yummy
7:45 AM Phil
Yep, just hanging out. Off to a wedding this afternoon
7:52 AM Sassy
That should be fun!
I’m thinking of sitting at your feet
And licking
7:55 AM Phil
That would generate a reaction!
7:56 AM Sassy
Definitely some squeezing
And sucking!
7:57 AM Phil
That will get you a mouthful of cream
7:58 AM Sassy
Mmmm
I adore that

8:00 AM Sassy
Foliage!  
[photo of the beautiful tree outside my living room window]
8:02 AM Phil
There is no more intense orgasm and so many ways to vary it. And then tasting my cum on your tongue, mmmm
4:45 PM Sassy
Fun wedding reception blow job.  Hee!
[15-second video]
https://ritual-sex-and-magic.tumblr.com/post/175688241666/hopelessslave-beagryzzly-malessupremacy

“That should be mandatory at every wedding. The bride showing publicly her obedience and submission to her new husband and owner. This is the perfect…”

9:05 PM Phil
Well damn
9:05 PM Sassy
Hee hee.  “Obedience and submission” is not my thing, but it’s wicked sexy!
The wedding you saw didn’t have that?
9:33 AM Phil
Nope!
10:03 AM Phil
Liked the link though
10:03 PM Sassy
10:03 PM Sassy
So naughty even if you can’t really see
10:19 PM Phil
Loved it