Meet #19 Brett bliss

October 27, 2017 Friday
From: Brett
To: Sassy
Sent: Friday, October 27, 2017 6:49 AM
Subject: RE: Wonderful fall

sounds yummy!


Report #19 The Canadian All Kinds of Bliss
October 27, 2017 Friday
I was off work today but still managed to have a crazy day!  I had scheduled two items:
11:30 am Do a good deed by giving an old phone to a friend whose phone bricked earlier this week
2:30 pm Meet Brett 
I was also supposed to do a little work on the payroll.  
Then one of my gal pals got laid off at 10:15 am.  I read her texts about that. She’d had warning from her boss, who also got laid off, so she had a chance to take all her stuff home from the office and start to think about her options before the official word came, but it is never easy! 

I offered to take her to lunch and give her a ride home to the suburbs, so she wouldn’t have to stick around the office or somewhere until the commuter trains ran later in the day.  
So I showered and dressed in a hurry, throwing on my black floral top and yoga leggings that make me feel so trendy!  I drove and found an easy parking space and handed off my phone, then dashed to pick up my pal. I took her to lunch, took her home, then scurried off to meet Brett.  Whee! I was about 15 minutes late, but managed to text him before he left the office so he wouldn’t be stuck waiting around at the hotel. 
I waltzed into the hotel at 2:45 pm.  There was no one waiting to check in, so I made quick work of that. Just as I turned away from the front desk, Brett came walking down the hall toward me!  He got the biggest smile when he saw me. It makes me melt! 
He took the map to the room from me and gave me a quick kiss and a squeeze as he navigated to room 2031 on the first floor, down one hallway and around the corner and down to the end!  I used the keycard to open the door and we are alone! 
There were lawn service workers just outside the window, so I closed the curtains tightly.  He was behind me and put his arms around me, massaging my breasts and nibbling on my neck. I relished that for a long time, then sat on the ottoman to take off my shoes.  He pulled off my socks and my top, sitting behind me on the chair. He played with my breasts and my bra, then discarded it as well. He cupped my naked breasts and sighed, nibbling on my ear and moaning a bit.  Mmmm…. He turned me a bit so we could kiss. There was a fierceness to it today, likely born of it being more than two months since our last meet. So delicious! 
He finally pulled off my leggings and panties, then went to the bathroom to grab a “cum towel” and led me to the bed.  
He pulled me to him for a glorious horizontal hug and cuddle.  I said this was bliss and he murmured that it was a first kind of bliss but we were going to have many more!  
We kissed some more, for a longer time than usual.  He played with his tongue, and nibbled on my lips. Yummy. 
He moved down to suck on my right breast and rolled my left nipple between his fingers.  That got me squirming! He fingered my clit until I was shaking. Oh my! 
He rolled over to grab a condom from the nightstand and rolled it on.  He got on top and was inside me in no time.  He pounded in and out… I enjoyed being filled by his rock hard cock and watching the blissful look on his face.  He rolled me over onto my hands and knees and entered me again. I adore how deep he can get in that position! He pounded me… in and out… pulling my ass on and off his cock.  So so good! I told him he made me feel fantastic! He agreed that he was feeling fantastic too! He sped up a bit, then warned me that he was going to over the edge and did. He kept moving even after he came… prolonging the bliss, he said.  Yes indeed! 
He finally rolled off to my right and cuddled me onto his chest again.  He started talking after a short rest, asking how my work was going, how my community project work was, how my husband was, whether I had gone to my high school reunion.  I told him a pithy story about each item. I am so impressed with his memory and taking the time to listen. I asked him about his work and his family. He told me about a wonderful golf outing he’d had with a pal from work a couple of weekends back.  
I had to go to the bathroom.  I tried not to… I hate being away from him and wasting time.  But sometimes nature calls and I have to heed it! I apologized, said I might asphyxiate him.  He said I could do a “courtesy flush.” I asked what that was, and he said, “You know, like on Seinfeld.”  I told him I had never watched it. He was aghast! I said it was too NYC and they were too mean to each other for me to find it funny.  He said it was so classic and he enjoyed the irony. 
I rushed to the bathroom and back into his arms.  He got talking about another comedy TV series, “The Big Bang Theory.”  He said it makes him laugh a lot and I really should try watching it. He gave me examples of fun plot twists and guest stars.  
He started squeezing my breast again, then kissed me for awhile more, and sucked on my left breast.  I backed up against him and threw my leg over his hip. He reached to the nightstand for another condom and rolled it on in a hurry, then was able to slide inside me and finger my clit at the same time.  Oof… that position got me going! He came again and we cuddled until I noticed it was time for him to shower and go. 
I threw on my clothes.  He gave me money to cover the room.  I left money for the maid. He thanked me for GRRRREAT time, a la Tony the Tiger, the Frosted Flakes cereal mascot.  We walked out together. I groped his butt on the way down the hallway. He had on these silky black slacks that felt amazing under my hands.
He had parked at the other end of the hotel, said he wanted to explore the areas we never walk through.  So we parted in the lobby with a smile.  

I went on to my car alone and drove home in heavy traffic, reliving the blissful moments in my mind!  

From: Sassy
To: Brett
Sent: Fri, Oct 27, 2017 at 9:49 PM
Re: Wonderful fall

Hiya Brett! Thank you for a lovely afternoon! It was so many kinds of bliss!

Hope you had an easy trip home. It took my nearly an hour but I kept moving and thinking of you and smiling.

Have a wonderful weekend!


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Meeting WrySmile

September 17, 2017 Sunday

from: Sassy
to: WrySmile 
date: Sun, Sep 17, 2017 at 9:13 AM
subject: Meet

Good morning hot stuff!

2 pm at Tosci’s works! If I get out of brunch earlier should I ping you or should we plan on 2 pm?

Are you nervous? Excited?

Mmm… your stories are sexy and sensual! I can see myself in most of the moments. Tingling. Do you really drink bourbon? I’m so happy for another way to know you. Thank you for sharing!

Much more later!



from: WrySmile 
to: Sassy
date: Sun, Sep 17, 2017 at 10:25 AM
subject: Re: Meet

2:00 it is!

Bourbon? Sometimes


Report #1

Meeting WrySmile @ Toscanini’s

I had a lovely leisurely Sunday morning – got up late and had time to shower and dress and catch up on my Facebook reading!  
My older sister and her beau took me out for a belated birthday brunch. I was home for about an hour, then headed out to meet a new guy! 
He had chosen to meet at Toscanini’s Ice Cream in Central Square in Cambridge.  Such an original idea! Much better than coffee or a bar, where I can’t partake of the central beverages offered.  Hubby dropped me off a block away, and I walked in right at 2 pm. 
The new guy was sitting at a high table on a stool facing the door.  He smiled beautifully when I arrived. My first thought was “what a lovely smile!”  My second thought was, “Wow… his online photo must be at least 10 years old!” In the photo he is robust-looking with reddish-brown hair and beard.  This man is frail, with completely gray hair and beard.  I can’t find a photo that looks much like him but David Bradley of Harry Potter’s Mr. Filch fame can give you some idea. 

David Bradley, actor

I noticed a cane folded on the table, and he was rather unsteady when he rose to give me a hug.  He had on a typical blue polo shirt with an open collar and worn blue jeans with expensive running shoes. I had on blue gauze pants and a blue t-shirt with red, white and blue designs at the top – casual and comfortable for a warm, late summer day.  

I waited for the line to wane, and got up to get an iced chai. I was still full from brunch so I passed up the ice cream.  He requested a decaf cappuccino and said he should pay but I waved him off. 
We talked for two hours.  He told me one story after another – he is a wonderful storyteller!  He made me laugh. He said it was such a treat to have someone he could talk with about Ashley Madison and sex and whatever came into his mind.  I told him a little about the (sadly extinct) IRC chat room and how I saw that reaction over and over when new people found it. He told me how he met his wife at a party in grad school and I told him how I met Hubby online.
He was very upfront about his health.  It’s a mess. He has ALS, depression, ADHD, and ED.  Oh my. His legs are weak but he can still walk with the cane.  The depression is controlled with medication. He has success with viagra when he masturbates.  He is able to work.  He said he has a marvelous boss. I told him mine is not and I am envious!  
A woman went by with an odd phrase on her t-shirt and I wondered aloud as to what it might mean.  He got up, tapped her on the shoulder and asked! That is bold! He said he talks to strangers a lot.  He asked me why I don’t. It made me feel like such a New Englander! And it made me know how lonely he is.  Or how outgoing? Or some combination. 
The shop got quite crowded, so he suggested a change of venue.  We went for a walk to a gorgeous park a few blocks away, and sat in the shade on a wooden bench. I sat on one end and he sat next to me at arms-length.  I asked about any traveling he’s done, and he told me of several “failed trips” because he travels alone and can’t walk far and gets sad. It occurred to me that his wife has given up on him. 
When it got to his announced time to leave, I mentioned it.  He talked a little more and then rose. I got up and he offered me his arms.  We had a nice hug and a single kiss. He felt small and fragile in my arms. I fear I’d squish him!  Not a pleasant moment. Made me sad. 
I asked if I could walk him to the T.  He took me on a stroll through an area where he used to live and we ran into a couple of his old neighbors.  It was awkward but they were so pleasant to him, made me know he’s a good guy. He showed me lots of interesting buildings and told me stories.  It was marvelous!  We finally walked back to the T stop.  He gave me another quick hug at the entrance and we parted ways. 
I took a Lyft home and pondered this meet and what I want.  I could easily keep talking with him. I could probably cuddle and have vanilla sex with him.  I don’t see myself being able to satisfy his urge for regular anal sex. And I don’t think we are compatible physically.  I mostly feel sorry for him and have to fight my urge to help him. I am interested in how his life goes, but sadly, the last thing I need is another disabled, depressed man to support emotionally without sex!  I am sad… for him and for me. I wonder what he will want to do next.  *sigh

Meet #17 Spontaneous Brett

June 30, 2017 Friday

I had the day off from work to go in for my annual breast exam. I try not to be nervous but there’s always the specter of cancer and craziness… so I think about something else. I was remembering last year and seeing The Canadian and wishing I could see him today. But I haven’t heard from him in almost two months. *sigh

The breast exam went well and I had a celebratory ham & cheese croissant at Au Bon Pain. I had hoped to go off on an adventure with Hubby but he wasn’t feeling like going anywhere, so we headed home. I sat at my desk, deciding whether to nap or read Facebook. Yahoo Mail announced a new message. I only use that for men from Ashley Madison so I got a tingle and clicked over to see who had written.


From: Brett
To: Sassy
Sent: Friday, June 30, 2017 1:19 PM
Subject: Re: June jewel

I replied once to this email but it looks like it didn’t go through. If this is the second time, sorry bout that!

I been real busy lately, project at work is in crunch time, boss left and the new boss and I have history. Home is nuts too with contractors doing fixups. I haven’t even looked at this email account in quite some time. Sorry, and I’m happy for your patience.

I sure wish we had set up a date today. Somehow, it seems like the right kind of Friday for meeting.

Talk to you soon,



From: Sassy
To: Brett
Sent: Jun 30, 2017 at 1:25 PM
Re: June jewel

Hiya Brett! 

So happy to hear from you. This is the first time.

I could still pop out to see you if you like? Or we could plan for next week? Would be so good to feel your arms around me.



From: Brett
To: Sassy
Sent: Friday, June 30, 2017 1:27 PM
Subject: Re: June jewel

I could do today. Let me know when you could make it.


I popped on to the Hilton site, made a room reservation at our favorite place and wrote right back to Brett! 

From: Sassy
To: Brett
Sent: Jun 30, 2017 at 1:32 PM
Re: June jewel

Hi Brett! 

Hooray! I am so excited!

I am leaving now. Google Maps says 40 minutes, but it will likely be a little longer. Let’s say 2:30 pm or whenever you can make it after that?



From: Brett
To: Sassy
Sent: Fri, Jun 30, 2017 at 1:44 PM
Re: June jewel

See you soon. I’ve just got to finish up some things quickly.



I brushed my hair and put it up so I’d be cooler in the humid, hot afternoon air. I brushed my teeth. I put on lip balm. I wished I had shaved recently but there was no time now! I dashed to my car and drove out into the burbs! The traffic was beastly but I made it less than an hour.

I checked in… they didn’t have a reservation for me! The desk clerk asked how I made it… I said I made it online about an hour ago. She asked to see the confirm – I dug it up on my phone. She said it was for another hotel 5 miles down the road! Oh no! It was too late to cancel! Argh! I asked if she had a room – she did! She checked me in and then said she could cancel the other reservation! Phew. She gave me the key card. I checked the bar – no sign of Brett. I sat in the lobby. Three minutes later he appeared!

He offered me his arm and cuddled up to me as we walked down and around and over to our room – 2087 this time. It was so wonderful to see him and touch him!

The minute the door was closed, he took me in his arms in front of the window and hugged me! He nibbled on my neck. I sat down on the ottoman to take off my shoes and he did the same. He sat behind me in the chair and hugged and nibbled some more. He pulled me up, saying he needed a hug and a kiss! I was eager to do that! He makes me feel so wanted!!

We smooched and groped and hugged… mmm. He helped me take off my top and bra and pants. He got out of his clothes before I could get to them. I ogled his lovely body. He had on white underwear today. Interesting to see that he usually wears black to see me but white when he didn’t know he would. He has lost weight!

We kissed and hugged some more… ah… skin-on-skin. Yum. I pulled him onto the bed and we hugged horizontally. Mmmm…

He worshipped my right breast for a long while and put his finger on my clit. I savored both sensations then went a little crazy. I told him he makes me smile. He said he really wanted to make me quake! Ha! He did a pretty good job with that.

He rolled over to grab a condom from the nightstand, rolled it on in record time and was on top of me! He shimmied down until he could slip inside me. Mmmm… I usually can’t do missionary because of my sexy tummy but he makes it work! I talked to him, a little naughty… about how it felt to have him inside me… so hot, so hard, so full, so deep. He smiled and closed his eyes… the look of bliss. So hot! He moved faster and then slower… then faster again and warned me he was not going to last long because he had been wanting me for such a long time. He came hard and collapsed next to me. Wow!

He fell asleep cuddled around me. I listened to him breathe and snore softly. I rubbed his arm and waited. After about 10 minutes he started talking. We caught up on work and home and family and politics. He said he’d lost 25 pounds! He could definitely feel it, and his shirts and pants were getting loose. I told him I noticed it right off.

He kissed me some more. I pressed back against him, thought he might go up and under and in, but he rolled me over to go in doggy style! Oh my… he can get so deep that way. He slid in and out… his stamina is something! I finally started to get sore and rolled away, apologizing but he said it was fine, he was wearing out too and it was time to go.

He showered. I tossed on my clothes and looked around to be sure we had everything. We walked out together, groping and kissing just a little more! I thanked him for a lovely afternoon, told him it would make me calm for another month. But if he wanted to see me again next week, I’d be around! He smiled and chuckled.  I told him I mean it! 

We went out into the heat and he thanked me as he branched off to his car. I threw him a kiss and got into my car. I ate the free chocolate chip cookie the hotel gave me when I checked in, drank a lot of water, texted Hubby and was on my way.


Hubby wanted Chinese food, so we went right on out to eat and I didn’t get home until after 8 pm. I wrote to Brett first thing.


From: Sassy
To: Brett
Sent: Jun 30, 2017 at 8:33 PM
Re: June jewel

Hiya Brett,

Thanks again for a special afternoon! Hope your trip home wasn’t too slow. There was heavy traffic but it rolled along and I made it in 40 minutes.

Have a lovely evening! Mwah!


Sent from Yahoo Mail on Android

Meet #1 – Didactic Daniel

May 10, 2017 Wednesday

from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 8:39 AM
subject: 4 hours

Good Morning Mysterious Lady,

I woke to the excitement of meeting you.

I am surprised that I have not been to the Red House before. It looks gorgeous in the online photos. I will be dressed casually.

See you at 12:30.

[photo of his smiling face]


from: Sassy
to: Daniel
date: Wed, May 10, 2017 at 9:47 AM
subject: re: 4 hours

Good morning! I woke up smiling because of you. Less than 3 hours!!

I have on my business clothes… with a fun silk scarf!



Meet #1 Didactic Daniel 

Danny DeVito

I went in to the Red House restaurant and saw Daniel standing at the bar.  He looked like a very serious Danny DeVito!  He smiled briefly and walked toward me.  He looked short standing there and seemed even shorter when he got to me.  He is definitely NOT my height.  I’d guess he is 5’6″ max and perhaps shorter.  We hugged awkwardly – his head landed firmly in my breasts!  Oh my… not sure how I am going to handle being with a man who is so height-challenged.  I kept telling myself it won’t matter – I will get used to it.  Right? I pondered why it is so engrained to be with a taller man… hmmm.

They put us at a table in the middle of the back dining room.  It was crowded, so we could talk without worrying about being overheard.  We settled in and stared at each other.  He smiled and I smiled back.  He looked over the menu and told me he was impressed and surprised he’d never been there – it was his kind of place!  I relaxed a bit.  He talked about his work and asked for more details about mine.  I was pretty vague.  He talked about an upcoming school reunion.  I mentioned that I had one on the horizon as well.   He ordered a salad and I got the lobster chowder.  I sipped along and he regaled me tales from his work.  He seems quite didactic in an irritating way, like he knows what is best for everyone and does not hesitate to say.  It was odd because I didn’t see much of that in his emails but it came out in spades here.  He whined about having to have dinner with his wife and two of her friends, about how the wife of that couple is so tacky and clueless.  I told him about my fun dinner plans out in Sturbridge.  He asked me if I would go to his “country home” for our first time alone.  I said that sounded a little scary, both to be so far from home and to be in such an isolated place.  He glossed right over my concerns, extolling the virtues of the remote place. 

He was eager to end the meal and have me walk him back to his car for “dessert.” I agreed – maybe he has talents in that area that will make up for his personality and lack of stature?

We strolled through the grounds of the Charles Hotel then down into the bowels of their garage.  He had picked an excellent parking space in between two columns in a corner that afforded us lots of privacy.  He leaned against the car and pulled me toward him.  I angled my knees a bit to get my face down to his level.  He grabbed my hair and kissed me in a quick, fierce way that was rather hot.  Then he started grabbing at my crotch!  I turned a bit and hugged him to my chest, pulling his hands up there and slowing things down a bit.  He squeezed my right breast rather roughly and made a growling sound.  There was no finesse, no gentleness… it was a compliment that he wanted to devour me but way too much too soon.  He did not sense my discomfort, and said we were going to be great together! 

I decided in that moment that the triple whammy of combo of his personality, his height and his roughness meant I was done.  I need someone who is sweet and gentle.  And I hate to say it, but I need a taller man, someone who can envelop me and make me feel smaller, not someone who makes me feel like the Jolly Green Giant! 

He wanted me to get into the car with him, but I suddenly “had to get back to the office.”  I hope I was subtle about it.. it was almost 90 minutes since I’d arrived and I had told him that was my limit.  He was very disappointed and whined at length.  I thanked him for a lovely lunch and hugged him once more, then made my escape. 

I strolled slowly across the hotel courtyard, took photos of the beautiful plantings.  They were on a purple kick!  I sat on a bench and gathered my wits.  I very rarely hope not to hear from a man after a meet, but I did today!  I found myself wondering how to discourage him if he did.  Not something I am good at!  I went back to the office and tried to put it all out of mind. 

Of course, he wrote back as soon as he got home! 


from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 5:01 PM
subject: W Ma to Boston

Hello Sassy,

I thought we would be compatible. I thoroughly enjoyed our lunch and time together.

When do we get together again?


from: Daniel
to: Sassy
date: Wed, May 10, 2017 at 5:07 PM
subject: 4U

A suggestion for next time.


from: Sassy
to: Daniel
date: Wed, May 10, 2017 at 10:14 PM
subject: Re: W Ma to Boston

Good evening! Thanks again for a lovely lunch and for sharing yourself. I’m just getting in from dinner and am worn out from all the driving.

Hope your dinner was better than you feared.  More tomorrow!


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Meet #16 Brett day

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May 5, 2017 Friday
From: Brett
To: Sassy
Sent: Fri, May 5, 2017 at 8:09 AM
Re: Catching up
tic toc, these Friday mornings seem to go so slow.


From: Sassy
To: Brett
Sent: Fri, May 5, 2017 at 8:16 AM
Re: Catching up

I know! But soon…soon you can put your arms around me and have fun!

Sent from Yahoo Mail on Android


From: Sassy

To: Brett
Sent: Fri, May 5, 2017 at 12:36 PM
Re: Catching up

Hiya! I am heading out! See you soon! Mwah mwah mwah mwah mwah.

Here’s a little preview to get you going. 🙂


Report #16 The Northerner Tries New Things

It was pouring rain and cold – only in the 50s – the kind of day that can be really depressing.  But I had the most wonderful antidote!  Chinese food and alone time with Brett!  
I wore my usual business outfit – dark blue slacks, dark blue sweater with a silk scarf.  I tucked a fun floral bra underneath!  I could not resist showing it to him.  
I went to work and got done what I had to do, then took off at 12:30 pm heading west!  I rolled into the lot a little early, had time to check my email and Facebook.  I got out of the car right at 1:30 pm and he was walking up the sidewalk from the other direction!  He had the most beautiful grin!  We dashed inside.  
A. Lunch at Bamboo

We got a great table right near the buffet.  

I ate my way through two plates – one full, one half-full as it was late and the food was running out and I didn’t want to be too stuffed. I do adore their shumai! I talked about upcoming project events and a big meeting at work, a person getting laid off, another promoted.  He ran into a former co-worker who stopped by the table and chatted but didn’t even look my way.  Strange but good so he didn’t have to introduce me.  He said he enjoys the risk.  Hmmm… 

He told me about the diet competition at work, said he’s lost 6 pounds!  He talked about a recent trip north and sneaking off to visit relatives who have been shunned by the rest of the family.  He fantasized about finding a way to come home early while he wife stayed so he could spend time with me.  Nice to know he thinks of me.  We talked about concerts we’d attended.  I told him about movies I wanted to see and new restaurants I tried. He made a rare comment about his wife, said all she wants to is garden – no movies, no dinners out and no sex!  
B. Dessert at Bedford Glen Doubletree Hilton 
We split up and drove to meet at the hotel nearby.  The tulips were blooming!  They were my favorite – Lucky Stripe – so I had to stop and take a photo. 

I checked in.  They gave me Room 3059.  I turned and he was around the corner smiling at me! He took the key and the map and we walked to the elevator, had a very sexy smooch in there, then walked some more and he opened the door with the keycard.  I set down my stuff on the desk and he grabbed me from behind for a long hug!  It’s so fun to get that “he can’t wait a second” feeling that helps me feel so wanted! 
He rubbed his front back and forth against my back so I felt the big bulge in the middle!  I leaned my head back and his kissed my neck.  He massaged my breasts as he nibbled my neck.  Mmm…. He stepped back to take off his shirt then helped me out of my sweater and bra.  He hugged me again, skin on skin. 
I sat on the ottoman and took off my shoes and socks.  He took off all his clothes, shoes and socks!  I stopped to watch.  He stood me up for a long kiss, grabbing my ass to rub me back and forth against his body.  We moved over to the bed and he pulled down the comforter and sheets, then took off my slacks and panties and pressed me back against the sheet.  
He tried the position i sent him a photo of, sitting behind me, nibbling my neck, hand on my breast, other hand between my legs.  I got so wet!  Oh my!  He’s not usually that creative.  It was lovely to send him a suggestion and have him run with it!  Wow!  
I turned to face him and put a leg on either side of his hips, tried to sit on top, but we just couldn’t make it work.  I need to look at more photos online!  We had fun sliding around skin-to-skin and giggled a bit.

He rolled me over and grabbed a condom from the nightstand to roll on for some doggy style action.  I went up on my hands and knees – he slid inside and pounded me!  He had quite some stamina!  (I wondered if he had taken a little blue pill somewhere along the way).  He held my hips and went inside and out, over and over.  I felt so full, so hot.  He told me he was going to lose control and I encouraged him!  He held me tight and shuddered and moaned.  

He collapsed to me left and I rolled to my right.  He fell asleep!  He doesn’t usually do that.  I stayed still, listening to him breathe and admiring his body while I rested.  After about 10 minutes he startled awake and apologized.  I assured him it was fine.  
I turned at a right angle to him and cuddled up so he could go back inside me.  He grabbed another condom, rolled it on and slid inside me.  We talked while he casually moved in and out and played with my right breast!  
He asked me how I am dealing with Trump.  I whined. 

I asked him what his favoite porn is?  He said his top 3 are regular sex, two women, massage with a happy ending!  

He told me more about how the dieting competition at work is structured. 

He asked me to bring my toys next time so he can see them and what I do with them, maybe add them to our activities.  I was surprised at that, as he rarely wants to do anything different, but today marked a change! 
He went silent and breathed a bit heavier, then pressed a finger against my clit and pumped faster and faster.  I squirmed and squeaked!  I felt him tremble then stop.  He had cum a second time!  
He pulled out and rolled closer to me for a long kiss, then bolted out of bed and went off to shower.  I went in to heed nature’s call and got dressed.  He joined me and we chatted as we threw on clothes.  He gave me $120 to cover the hotel room, and I left the $20 for the maid. He looked around to be sure we had everything and gave me one more kiss!  
We walked back to the elevator, had another quick kiss in there, then made our way out through the lobby, saying good bye at the door and running to our cars in the rain! 
I smiled all the way home, which took quite awhile as everyone seems to forget how to drive when it’s raining. storing away all the memories I could use to tide me over until he contacts me again! 

From: Sassy

To: Brett
Sent: Fri, May 5, 2017 at 8:33 PM
Subject: Thanks and info

Hiya Brett!

Thanks again for lunch and dessert! Such a lovely afternoon!!

I made it home in about an hour… beastly traffic everywhere so I took the back roads through Lexington and Arlington and Somerville to the city but it was still slow going. Hope you made it easily.

Here’s the sites we talked about today that might entertain you:

Source for bargain tickets to concerts, attractions etc.

Softer videos

Massage video – MMF

Couple in bed





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Meet #15 Brett’s Back

March 3, 2017 Friday

From: Brett
To: Sassy
Date: Mar 3, 2017 at 8:00 AM
Re: Feeling better
Your theatre proclivities are showing.  Soon….
Report #15 
The Northerner

I drove to work, tossed the car in the expensive outdoor parking lot, then had a frantic morning at work pushing to get done the minimum I needed to do before taking off around lunch time. I helped a new person fill out their forms, met with my boss for an hour, then finished the payroll and a few more little chores and I was out of there at 12:45 pm!

The parking lot was busy with people arriving and departing. I watched the attendant move my car, then block it in with another car! I decided to intervene at that moment. He handed me my keys and moved the car behind me. I inched out between a bunch of cars then paid and took off!

It always seems like I am headed way out of town, and in a way I am, but I pulled in to my favorite Chinese restaurant near the hotel at 1:35 pm. Whee! I got a table for one near the sushi bar – Brett was not able to make it but I had the time and couldn’t pass up a great lunch if I was out there.

I went up to the buffet, filled one plate with Chinese appetizers and tastes of entrees, then a second plate with sauces and a few pieces of sushi. There was no one at the other tables near me, so I could relax and eat and text on Kik with The Pup! He is so curious, asked me lots of questions about what I’ve done and planned to do and made suggestions about things to try with Brett. It made the time fly! I went back to the buffet to grab a few more of my favorites, and a little scoop of ginger ice cream. I paid the bill and took off to the hotel. I arrived just before 2:30 pm.

There was no one in the lobby! They let me check in early and it didn’t take long. They gave me a chocolate chip cookie and two bottles of water! I then turned to the bar area and Brett was walking toward me! He makes it so easy!

He put his hand on my back and we smiled at each other. I handed him the map and keys to the room. I groped his backside… amazingly sexy dress pants! He winked at me. We strolled down one hallway and up another until we found Room #2030. He opened the door and I went in to see the usual king size bed. I took a big drink of water while he took of his leather bomber jacket. I smiled at him. He smiled back. It was so good to be alone with him!

He wrapped his arms around me from behind and nuzzled my neck. It felt so wonderful to be in his arms, and feel his breath on my skin and his body pressed against my back. He was hard, pressed against my ass. Mmm…

He kissed my neck then raised his hands to my chest. He sighed when he got his hands full of my boobs and whispered about how he dreams of them! He turned to kiss me. We merged together, tongues swirling, but I was too tall… had to take off my shoes! I pulled away and sat on the ottoman to get my shoes and socks off. He took off his shoes, shirt and pants, then sat behind me on the chair and kissed my neck and played with my boobs some more. I grabbed the water bottle for another drink… it was quite dry in that room. When I turned back, he helped me take off my shirt, then played with my chest and bra, finally dispensing with it. He pressed his body against my naked back… he had taken off his underwear! There was skin! Mmmm…

He finally let me stand and helped me take off my jeans and panties. He led me over to the bed and tossed back the comforter and sheet. I sprawled across the middle of the bed. I turned on my side and he joined me, facing me, stretching out so we could have a naked full-length hug.


There was a little more kissing, then he moved down to suck on my left nipple. He squeezed the breast and twisted a little… that feels amazing! I played with my right nipple and messed up his hair with my other hand. I let the feelings flow over me as he sucked and massaged my chest. He ran his fingers down my torso, then buried them in my slit and found my most sensitive spot to tease. Oh yes.

I squirmed and shook as he did his magic on my clit. He is quite good at that! He reached over to the nightstand to grab a condom, slid it on and pulled up my legs and was inside me so quickly! He had done a good job getting me wet! He slid in and out, going deeper each time. We looked into each other’s eyes, then he closed his eyes and concentrated. He leaned against me and I wasn’t sure my lunch would stay down, but right when I considered saying something, he asked if we could switch to doggy!

I rolled over and went up on all fours, and he was inside me again! He went very deep and moaned, then started to move faster and faster. He said he couldn’t wait and came hard inside me! Wow! He held my ass and stroked it as he faded, then collapsed next to me.

He offered me a pillow but I put my cheek on his shoulder and cuddled up next to him. I looked at the alarm clock – it was 3:34 pm. He relaxed and rested. He took a tissue from the nightstand, rolled off the condom and set it back on the nightstand.

He stroked my arm, my hip, my tummy. He is so good at making physical contact, remembering how deprived I am. I returned the favor…stroking, patting gently. He dozed for awhile. I listened to him breathe and stared at the ceiling.

After awhile, I put my hand down to play with his cock, see if I could get round 2 going. But he was completely flaccid and didn’t stir so I went back to staring at the ceiling. I turned so we could spoon and I could get even closer. I pulled to covers over us and he made a nice sound.

Finally he whispered in my ear, “So… how are you liking the Trump presidency so far?” Ugh. I chuckled and told him we’d better not talk about it. He said he was not happy but figured the other candidate would not have been doing what he wanted either. I knew better than to reply to that.

I asked how his family was and he told me stories about what had happened since Christmas. I told him about Hubby breaking his leg, which had curtailed our doing much. We talked about the Super Bowl and the Oscars. I told him about the one movie I had seen that was nominated for Best Picture – Hidden Figures. We talked about our work, ranted about my boss a little and he told me a new coworker who was making work harder. I told him about the seemingly never-ending process of taking care of paperwork for my mother’s estate.

I looked at the clock – it was 5 pm. I asked him what time he had to go, and he sighed and replied, “Not yet!” He kissed my shoulder and pulled my leg over his hip. He put a finger on my clit… very politely checking my wetness, then put on another condom and was inside me! I was lying flat on him at the waist and he moved in and out from underneath. He could play with my clit, squeeze my breast and kiss me now and then. Such a great position! He took a leisurely pace, then I began to tremble and he sped up and was coming again. He moaned so sweetly!

He hugged me and told me I am so good for him… get him so excited and then let him relax and he enjoys our time together!

He said he had to go and hopped up to head to the shower. I followed up, groping his cute ass then using the toilet as he showered. I adore sharing a bathroom with a man!

I hurried to get dressed and be ready to leave with him. He gave me $100 to cover the room. I left $20 for the maid. The room was only $85 today so I came out pretty close to even!

I kissed him one last time, then we made our way back to lobby and out to the parking lot. He split off toward his car and I said a serious, “Thank you very much!” He replied, “And thank YOU!” and was gone.

I checked my phone, texted Hubby to tell him I was on my way. I looked at the traffic on the highways and decided to take the backroads home. It was an easy drive. I noticed that it was still light at 6 pm! The worst of the long dark days are over! I listened to the radio news and rolled along home with ease, smiling and satisfied.


From: Sassy
To: Brett
Date: Fri Mar 3, 2017 at 9:29 PM
Subject: Feeling fine
Hiya Brett!
I made it home easily, stuck to the back roads.  Hope the same for you. 
Today was magical… again.  Thank you ever so much for each moment!  I will treasure them.  And pull them out when I get out a toy to get me over the edge!  Mwah! 

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Meet #2 Trainer in my bed

February 17, 2017 Friday

From: TimmyTim
To: Sassy
Date: Fri Feb 17, 2017 at 6:08 AM
Subject: Can’t Believe It’s Friday Already!
It’s FRIDAY! Once we are up, we can get up, if ya know what I mean! 😉
I will send a quick email as I get on your street at about 10 so you can meet me at the garage. If you want me to call at that point, just send me your number, but I understand if you don’t want me to call!
I am so excited to see you! And John Henry can’t wait to meet Gigi!
Until then, hugs with subtle erotic undertones!
Take care,
Sent from Yahoo Mail for iPhone
From: Sassy 
To: TimmyTim
Date: Fri Feb 17, 2017 at 6:10 AM
Re: Can’t Believe It’s Friday Already!
Happy Friday T!  
Can’t wait to see you!  And touch you.  And taste you…

Here’s my sassy number [redacted]
Sent from Yahoo Mail on Android

Meet #2

I got up and showered and picked up things around my place, hiding anything that had my name or Hubby’s name on them! I tried on my new black leggings and patterned top, to see if they fit. They looked so good I decided to wear them! This is my first-ever set of leggings! It feels like going out in my pajamas or gym clothes, but everyone does it these days so I will enjoy being comfortable too!

I was ready early so I logged in to my work email and paid one more person on payroll.

Tim called as he turned the corner onto my street, about 10:15 am! I was in the elevator heading to the garage when he called again to ask how to get the garage door open. I scurried to meet him and open it.

He had trouble fitting his big mini-van into my little parking spot. I tried to explain the trick but he couldn’t do it, so I offered to do it for him and he let me! I was wicked nervous but managed to thread the needle as it were and drive straight in on the first try! Phew!

I handed him his keys and phone, then locked it up and got out. He gave me a big hug and a quick kiss. He looked so business-y in his tweed jacket, Oxford button-down shirt with a monogram pocket and khakis slacks!

We strolled to the elevator and I gave him a big hug and kiss there. He seemed surprised and pleased.

He asked to use the bathroom, so I guided him through the condo, into my bedroom and to the master bath. He shut the door. I smiled and thought of Kris and our discussions of whether to leave the door open, closed or locked. Heh.

He rushed out of the bathroom and gathered me up in his arms! He has the best way of making me feel wanted. We had a long hug with lots of groping and playful kisses. He encouraged me to open my eyes so he could see my “beautiful blue.” I put my hands on his face, then ran my fingers in his long, straight soft hair.

He asked if he could see my toys, so I pulled the big bag out from under my desk, got my favorites out of the bedside table drawer and yanked the battery charger out of my bathroom with extra batteries. We explored and giggled our way through the little bullets and big bullets, the magic wand and the three ring circus that undulates, vibrates and lights up! The nine-inch stunt cock came out of its box – that’s good for giving men insecurity and does nothing for me – and the tiny pink keychain rabbit that is incredibly powerful. I even showed him the butt plug still in its package! We ended with my current favorite, the Lelo Gigi 2. I explained the controls and he played with that a bit while I stored the rest of them. He said he had played with a few toys in between marriages but the second wife has no interest in them.

He asked if we could lie on the bed. I eagerly flattened out and we cuddled side-by-side. He rubbed on my new leggings. Another advantage – he could play between my legs and I could really feel it! Much better than jeans! Ha! He noticed and smiled, said he liked these new fangled pants!

He asked if he could take my leggings off. They disappeared along with my panties! He kissed his way down my belly then went right on down to my lower lips and sucked on my clit. Oh my… my hips popped up to greet his tongue and I started trembling. He is so talented! I held his head while he teased and tasted me. I started to shake and he moved back up to kiss me and hug me, but kept playing using his finger, and I held tight to him and squeaked as I soared in pleasure!

He pulled a condom from his pants pocket and I helped him roll it on, leaving that cute tip at the end to be filled later. I tried to back up against him and get him inside me but we weren’t having any luck today. Not sure why. He said he has been studying the website with various positions and wanted me to try the reverse cowgirl! I crawled over him and faced away and shimmied around, but we couldn’t make that work either.

So he turned me over and pulled my legs up for a deck chair position and slid inside. Oh yes… that worked! He pounded me and I watched his face. He asked me to feed him a breast so I gave him the left one to suck on. That combo is fantastic!

He burst out with various cheers, “This feels SO GOOD!” “I adore being inside you!” “You are so beautiful!” It is lovely when a man in the heat of passion can muster the brain power to say lovely things, especially with all the blood having rushed lower. I have an interesting reaction of pleasure and disbelief. Need to get over the second part…

I talked to him, encouraging him to give it all to me, to feel my muscles pulse around him, to fill me up… do it do it do it. He kept going, lying on me until I could barely breathe, but then finally relaxed and filled the condom. He got the most amazing smile on his face!

He collapsed next to me and patted his shoulder. “Head here…” he whispered. I cuddled up beside him and put my head on his shoulder and reveled in the afterglow. Ahhh….

I listened as he talked about his sister’s death from cancer. So unfair. He asked me about how I ended up buying a condo so I told him that story. I told him about my sister who smoked and how a hypnotist helped her stop cold turkey!

I rolled over on my tummy to rest a moment, but he followed, pressing his entire body over mine. He put his cock between my legs and slid between my thighs, adoring my smooth skin and how it cupped him. I wondered if he thought he was inside me, but let him do his thing for awhile.

He rolled off and asked if he could watch me play with the Gigi 2. I told him I don’t do much and it would be boring but he said he wanted to learn from what I do, maybe do some things to enhance my playing, so I went along. He watched as I pressed the vibrator against my clit and moved it back and forth. After a little while, he took it from me and repeated my motions, with some added up and down motion that made me even hotter! That was a first!

He set Gigi aside and straddled my chest, pressing his gorgeous cock between my breasts. He slid back and forth, while I held them around him. His smile was so sweet! He went faster and then asked if he could come on my tummy. I said Absolutely! And he did! That was another first! It is so fun to watch his cock jerk and spurt! And feel the hot white cum flow on my skin.

We went into the bathroom together. He took a quick shower while I cleaned up my tummy with some wipes.

He gave me a long hug and a kiss, then it was time to throw our clothes back on.

I walked him out to his car and opened the garage door to let him drive out.

Hubby rolled in as he rolled out and they waved at each other. Heh. That’s always a little strange but harmless. Thank goodness we have our understanding so it’s no big deal.

I watched Tim’s car disappear into the distance, then went upstairs with Hubby.

What an amazing date! I adore this man!

From: Sassy
To: TimmyTim
Date: Fri Feb 17, 2017 at 10:58 PM
Subject: Mellow me
Hiya hot stuff! 
Hope you got home easily!  
Thank you for everything.  
Made me so mellow and smiley!  🙂 

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Meet #1 The Trainer Terrific

January 26, 2017 Friday
Report #1 The Trainer 
12 noon Heading out
I left my office and drove to Framingham.  It was quick and easy, so I was wicked early.  I parked near the TGI Friday’s at Shoppers World, sent the “meet info” email I’d forgotten to send to Hubby and Sis, scrolled through Facebook and re-read his profile until I got his email saying he was here!   
I checked my look in the mirror, then walked across the parking lot.  The temperature was not too bad, but the wind was bad.  I hurried to get out of the cold! 

1 pm  Meeting at Starbucks
I strolled into the Starbucks inside the Barnes & Noble bookstore, looked to the right and saw him immediately.  He stood up to greet me and we had a lovely long hug!  He’s cute!  He reminds me of the comedian Jim Gaffigan – tall, cute, fun, great hair for an older guy, and in good shape, with a sly smile.  
Jim Gaffigan
He had picked a great corner table in the back corner near the bookcases and next to the window with no one next to it.  I sat opposite him and he took my hand.  There was something both comfortable and exciting about that.  He looked me up and down and then stared into my eyes.  I stared back and smiled.  

We chatted a bit, talked about how easy it was to get there, how he knew me immediately even though he had not seen a photo.  We kept staring into each other’s eyes. 
He had assigned me homework to do and bring with me to our first meet – a list of my five likes and five dislikes.  I had written them out on a little piece of paper.  I gave it to him and he read it.  
1) The taste of warm lobster with a little butter
2) Hearing David Wilcox singing “Rusty Old American Dream”  
3) Feeling a man’s hands on my face as he kisses me
4) The view of the beach at Trunk Cove, St John, VI 
5) Watching figure skating competitions live in person 
1) Dealing with mean people
2) The taste of green peppers
3) Pain 
4) Not being able to fix what is making someone sad
5) Cancer 
2 pm Lunch at Olive Garden
We discussed our options and decided to go to lunch.  He had already eaten but humored me.  So we strolled over the Olive Garden.  He stopped me on their front steps as we were going in and pulled me in for our first kiss!  Wow… he is so romantic, and talented with his lips!  He pulled away pretty quickly.  Later he admitted he couldn’t go on or he’d never stop!  Awww… 
We got a corner table for two and I pulled the aisle chair around so he’d be close to me. He peeked at the menu and rubbed my knee.  Mmm… 
We had a tall, dark and handsome waiter who set off my gaydar in a good way.  I ordered my usual – sausage soup with spaghetti with meat sauce and two sausage.  He got the shrimp scampi appetizer.  I ordered a peach bellini iced tea and he had a diet coke.  We had a wonderful conversation as I munched on my food and teased him under the table!  
He apologized, said he has not planned beyond Starbucks and didn’t have cash to pay for lunch and didn’t dare charge it.  I told him I was fine with paying this time and he could cover next time. He seemed quite relieved.  
3 pm Canoodling in the Car
We walked out to his car and sat in the front seat canoodling! He is a very good kisser – slow and sensual!  He had parked in a bad spot, right in the middle of a lot of other cars.  He suggested we move to the back seat. I suggested he move the car to a more protected remote location, over by my car.  He drove over there then put down the middle seats and we crawled into the back seat and cuddled and kissed.  It became clear pretty quickly that we were ready for much more.  
4 pm Taking the next step
We decided to go to a hotel!  He seemed surprised and happy that I had scoped out the best options around.  He was quite embarrassed that he had not dared hoped for that, and that we didn’t talk ahead of time about money.  I told him not to worry about it.  I got on my phone, found a great low rate and made a reservation, got directions and he drove us over to the Crowne Plaza in Natick.  I checked in while he parked.  He met me in the lobby and we went up to the 7th floor.  
4:30 pm Hot in the Hotel 
We had a gorgeous view of the Natick Mall as the sun set.  I stood in the window, glancing out and watching his reflection as he took off his jacket and came up behind me.  He put his arms around me and nibbled my neck.  Mmm… I melted back into him, felt him hard against my ass.  He unbuttoned my top and put a hand on my breast, squeezing it with his hand outside my bra.  He glanced over my shoulder and whispered, “It’s really Sassy!” because that view matches the photo I sent him! 
I giggled and nodded.  
He turned me and hugged me close and he kissed me deeply.  It went on and on!  I put my hands on his face and rolled with his masterful use of his lips and tongue – nibbling, sucking, probing, twisting my head this way and that.  Oh my!  
He said, “You know that long, romantic email I wrote about our first slow, sensuous time?”  I nodded.  “And how it ended?”  
“Yes… with us throwing off our clothes and shagging like rabbits,”  I answered.  “That seemed like a much more likely scenario.”  
“Will it be okay if we do that?” He asked, being ever so nice. 
“YES!  PLEASE!” I consented.  He started unbuttoned his shirt and I did the same.  There was a pile of clothes and two naked people standing beside the bed in short order!   I have never seen such a gorgeous cock!  It was bigger than I had expected based on the rest of his body, but there it was… longish, thick and perfectly formed with a sexy mushroom crown.  He was very hard.  Oh my.  I am probably not going to be able to deep throat this guy but we’ll have fun trying!  
He pressed me back against the bed with my legs over the edge.  He stared for a few moments, touching my nipple, my belly button, and smiling.  My first impulse was to be shy, but I fought it, smiling back and winking!  He chuckled… “You sassy gal!” 
He put his face between my legs… mmm… he licked and pulled my lower lips with his teeth, ever so gently.  Then he slowly slurped inside, up and down around my clit.  Wow… this guy knows what he is going!  My hips bucked up to meet his mouth.  Oh!  He paid attention to my reactions, repeating things that made me squirm.  He pressed a finger inside and moaned….”so wet… mmmm.”  
He stood up and started teasing my clit with his cock.  “You ready?”  He asked. 
“Oh yes please….” I replied enthusiastically.  He grabbed a condom from his pants pocket on the floor, and I heard that magic sound of foil tearing.  He rolled it on and returned to teasing my slit with his cock until it was very wet with my juices.  
“I may not last long this first time,” he apologized.  “I am so keyed up and it’s been so long and I want you so so much!”  Wow… way to give a gal confidence.  It made me feel so sexy!  
“I understand completely,” I assured him.  “I want you!”  And he pressed slowly into me.  Oh, there is nothing like that first thrust deep inside!  Being filled after being empty for so long!  He held my hips and moved in and out… in and out.  I lost rational thought very quickly… thrashed back and forth, pressed forward to meet each thrust.  I was making a lot of noise… moaning, sighing, squeaking!  So so good.  I felt like I was floating… then soaring!  
He started to shudder.  He said, “I’m going to lose control.  Cum very soon.”  
“Do it.  Fill me,” I told him.  He pressed very deep inside me and my inner muscles pulsed around him and his face contorted and he was still.  He took four deep breaths, then opened his eyes and smiled the most beautiful smile!  
He turned me around on the bed, went to the bathroom to dispose of the condom, then joined me.  We rested for a few minutes, then he started making little circles with his finger on my right breast.  I stared into his eyes and he smiled, tweaked my nipple and squeezed my breast. 
 “Is this the rogue one?” he asked.  
“Yes… see the scar?”  He stroked the two inches of it.  “Can barely tell,” he told me.  He leaned over and kissed the scar.  So sweet.  Then he sucked on my nipple and I felt a big twinge lower down!  
I reached down to check on his cock.  It was already hard again!  Nice!  I leaned over and kissed his left nipple, then his belly button.  
“May I taste you now?”  I asked.  He nodded, then realized I might not see that and stated a firm, “Oh yes please!”  I got between his legs and looked up at him, then took his cock in my hand.  He moved up on his elbows so he could watch me.  I blew on it.  He shuddered.  I kissed the tip and smiled up at him.  He moaned.  I licked from bottom to top and around the crown.  He moaned again and closed his eyes.  I took him all the way down my throat as far as I could.  There was still about a third of it… no getting my nose on his stomach with this guy!  
I reached down to stroke his balls with one hand while I made a circle around his cock with my other hand, pressing him in and out of my mouth and making fun sucking sounds.  His hips rose to meet me and it pushed him deeper.  I gagged and he backed off.  I assured him it was fine and dove back down on him.  He moaned and his eyes rolled back in his head!  Ha!  I looked up at him while I sucked him in and out and he stared into my eyes with the hottest look!  Perfect.  
“I don’t know if I can cum again,” he signed.  
“Still feel good, yes?” I asked. 
“Absolutely!” he exclaimed.  I smiled and went back to licking him and stroking down below.  I twisted him and pressed him back into my mouth and sucked.  He moaned and I went faster, in and out… he put a hand in my hair and helped me set the tempo.  
“I am going to cum again…” he marveled, warning me like a good man should.  I hummed around him and went extra deep and started swallowing and BOOM!  I tasted several shots of cum!  Ah… I adore helping a man do what he doesn’t think he can do and making us both feel so good! 
I went back up to cuddle with him.  He kissed me deeply… nice he can taste our juices mingled together without being squeamish.  I put my head on his chest and played with his chest hair.  We were quiet for a while.  A comfortable silence. 
He turned on his side so we were facing each other, and stared into my eyes.  
“I thought you were going to be good,” he said.  “But I was wrong.  You are terrific!”  he crowed.  I smiled at him.  
“This is my best first meet EVER!” I assured him.  I meant it.  Each hour had been a treat from the original comfort to the easy conversation over lunch to the incredible sex!  I hoped I was not tempting fate and dooming myself never to see him again by thinking and saying that! 
As if he could read my mind, he said, “Awww… you know so many ways to make me feel special,” he told me.  “Please tell me I can see you again, and soon!” 
“I’d like that,” I answered, marveling on how we were on the same page.
“I’m driving to Pennsylvania tomorrow, family get-together, so I may not be in touch much.  But I will check in on Sunday and we’ll talk more next week and make a new plan, right?”  He asked.
“Yes.  That sounds perfect,” I told him.  He sighed and kissed me.  And then kissed me more.  
We talked about his upcoming trip, his job and my job, how we met our spouses, his kids and my cats and… I adore those afterglow conversations when we’re so mellow and open and comfortable!  
About 7:45 he looked at the clock on the nightstand and sighed.  
“I should go.  Don’t want to but it would be smart if I do,” he said.  “Come talk to me while I shower?” 
We rolled out of the bed, and he dashed to the shower.  I relieved myself and chatted with him, then pulled back the curtain a bit to kiss him while he rinsed.  So comfortable being with him!

8 pm Heading home
We dressed.  I left a tip for the maid and we headed out.  I got a bottle of water from the shop.  We went to his car and he drove me back to his car.  It was easy!  He walked me to my car, gave me one last hug and a quick kiss and walked away.
He tapped on my passenger side window – “Do you know how to get home from here?”  
“Okay.  Text me when you get there?”
“Of course.”  
“Good night!” 
I texted Hubby.  No answer.  So I called him.  No answer.  So I called again!  He finally picked up.  We conferred about a dinner order.  I went in to Olive Garden, placed a take-out order and sat at the bar shipping a kiwi melon limonada while they made my dinner.  I replayed the afternoon, smiling like a loon.  

9:30 pm Home
I made it home easily.  I sat in my car in the garage and read his email to me.  Good man, to email right away!  I emailed him right back.  
What a day!  Best first meet ever! 
From: TimmyTim
To: Sassy
Date: Fri Jan 27, 2017 at 8:54 PM
Subject: WOW
Brain no work! But I got home safe!
All I can say: “you are awesome!”
Will write more, maybe quote Latin, ask dirty questions, see how your Saturday went on Sunday! Till then let me know you drove home safe!
Real hugs with real groping!
Take care,
Tim, John Henry and even The Trainer

Sent from Yahoo Mail for iPhone
From: Sassy
To: TimmyTIm
Date: Fri Jan 27, 2017 at 9:30 PM
Subject: Re: WOW
Hiya T, 
Wow indeed! With an extra crispy bucket of woohoo! 
I got take-out from Olive Garden for Hubby and am home now. My mind is whizzing with so many marvelous memories! Thank you. 
Safe travels. I’ll be thinking of you. And John Henry!
Sent from Yahoo Mail on Android

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Meet #1 Mark at the Mall

January 16, 2017 Monday


I got an email from Ashley Madison on Saturday telling me a man from Australia had written to me. What use is that? Why would someone so far away write? Maybe he’s interested in cyber only? I was busy setting up a meet with Randy, and seeing a friend for afternoon tea and my sister for movie, so I didn’t go to Ashley Madison’s website to look until the next day.

By Sunday I was curious enough to look at what he had to say. Aha! He’s in Boston! A Traveling Man.

I have sworn off meeting the traveling men. I did it once but I really want to focus on someone I can see more than once! But he’s here for longer… hmmm… and an Aussie! I could just listen to him talk. I adore their accent!

Something about him intrigued me. But I am about to see Randy. I decided to wait before agreeing to meet… see if I think better of it and if Randy could be the one to enthrall me.

I couldn’t stop thinking about him. It could be really fun! It could be really dangerous. *sigh

Randy and I had fun on Sunday morning (he’s a sweet, cuddly guy) – but not enough to make me stop thinking the Aussie. So I wrote back.  And set up a meet.  Whee!

Meet at the Mall

I drove over to the mall, parked on the street a couple of blocks away and dashed to meet him at Starbucks. I found him right at 4:30 pm. He was sitting on a bench on the concourse. I walked over, stood right in front of him and he looked up and smiled! There was a marvelous sparkle in his eye!

He looks a bit like an older Russell Crowe – quite handsome and a little rough, with broad shoulders  and face. 

Russell Crowe

He offered his hand for me to shake and I gave him a big hug! Mmm…. he put his hand on my back and led me into Starbucks, asking what I’d like to drink. I asked him to get me a small iced chai. He said he’d stand in line, that I should find a seat. There was nothing open, so I stayed with him and kept an eye out. Just as we got to order, two seats in the window opened up! They are the perfect seats, in a little alcove where we can sit close together on high stools and no one can listen to us talk.

I checked my email as I waited, and he eventually appeared with two cups and a straw! He said he guessed I’d need the straw. Perfect!

Talking at Starbucks

We settled in and he asked questions. We had a wonderful discussion for TWO HOURS! He told me about coming to town on business, his traveling adventures in the snow (missed a connecting flight, luggage got delayed), having to buy clothes at this mall to tide him over, not having a warm enough coat… He talked about his city and traveling adventures and medical travails. I told him about my cancer treatment and my old flame getting me started on stepping out. We talked about places we’ve traveled and favorite foods and beaches he could get to close by. I asked if he still has sex with his wife and he said he does. I explained a little about Hubby, no sex, poly etc. We talked sports – he told me about learning to watch American football and going see baseball in Chicago. And how he is not interested in cricket at all!

Talking at dinner

He finally decided he was hungry and it was time to walk next door to the Cheesecake Factory. There were people waiting but I walked right up to the host and asked for a quiet table for two and they seated us in a great booth at the back! It took a couple of minutes to get it set up, so I made good use of the time by standing close to him and rubbing his back. He gave me a very hot look and winked. Ha!

We settled into the booth. He marveled at the huge menu. I checked to see if they still had my favorites and then concentrated on him. I ordered an iced tea. He asked what I drink when I want something harder. I admitted I can’t drink liquor. He said he only drinks beer and rarely. He ordered a Coke Zero. He was super polite to the waitress! She was charmed. So was I!

I ordered the French Country Salad with greens, beets, goat cheese and walnuts, then the pasta carbonara with chicken.

 He ordered the Cajun chicken littles with corn and mashed potatoes.

We went on talking for another two hours! He is so interesting! We even managed to talk about politics here and there without any problems. I didn’t have any trouble understanding him, either the accent or the vocabulary.

I offered to drive him back to his lodgings. He was very surprised and pleased that I’d do that.

We perused the dessert menu but admitted we were too full to try anything. He said he still had to try a Boston Creme Pie, though he already knows it’s not a pie. I told him about Dunkin Donuts Boston Creme donut and couldn’t help mentioning it’s sexual connotation for me. Maybe have ruined that treat for him!

He insisted on paying the bill. I told him he didn’t have to always pay for me… that I have money.  He said he could expense it through work.  We got into talking about my mom’s last days and he told me about his mom breaking her hip and how it signaled the beginning of the end.

Kissing in the car

I took a quick trip to the bathroom, then we strolled through the brisk night air to my car. We climbed in and I cranked the heat and he grabbed me for a long kiss! Yummy! I caressed his cheeks, played with his ear, grabbed his upper arm. He played with my left breast, then asked me to slip my jeans down a bit. He rubbed his way down my tummy then pressed his fingers down to my slit. Oh my… He found my clit and had a wonderful way of slowly sliding up and down it. I stopped being able to think! I enjoyed his touch and let the heat flow through me until I was shaking and shrieking!

He unbuttoned my sweater and grabbed my left breast out from my bra. He pulled on my nipple and cupped my breast. Very nice!

I wanted to touch him… I pressed my hand between his legs. He said it was too public, even though we were parked on a quiet street next to a big empty field, but whatever. We kissed some more, then he said he should be getting back to his place.


He said he’d like to be where he could flatten me out on a bed… maybe I could help him find a place? I said that sounded like a great idea! He said he would email me and we’d figure it out.

I pulled myself together and drove him back. He asked about various buildings we passed and rubbed my leg. Mmm…

He had me stop in the middle of a block, obviously didn’t want me to know exactly where he was staying.  Good risk management, I suppose. 

He kissed me once more, got out of the car, said, “Thank you ma’am!” ever so politely, and was gone. 
 I suddenly had this feeling that I would never see him again. I replayed our conversations, his reactions… trying to figure out when he had decided, and why I thought that. Nothing specific popped out. Ugh.

I drove home replaying his stories, his touches. It was a fun evening! I so hope I am wrong! But if I am right, he showed me a lovely time, I got a free iced chai and dinner and some amazing kisses. And I got to listen to that amazing Aussie accent! I would do it again!

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Meet #2 Randy in my bed

January 15, 2017 Sunday

5:57 AM
Good morning sexy

7:01 AM
Good morning hot stuff

How are you this morning my beautiful lover?

I’m super! You?

Super horny
Thinking about you all night

Oh my

Hope that’s ok
Leaving shortly
Ok on my way and very excited

Yay! See you soon!

Just going over the Tobin bridge

I’m hopping into the shower!
Stay in your car until I get out!

Will be a little bit

Just parking now
Found a spot around the corner

Hooray! I’m ready!

I’ll grab my stuff and walk over

Yay. So ready! 

Ok on my way

Goody goody goody goody

Just walking up
Which #?
Or can you buzz me in?

I’ll buzz you in, turn right to elevator, go to my floor and I’ll meet you

8:10 AM


Report #2 Randy
in my bed


I met this guy for a drink in early October right before he took off on business trip and we had a sexy time in the car that night. We chatted every day after that, while he traveled on business, then back home.  November 1 he went silent.  It seemed to me that he was too busy to cheat – crazy busy job, kids, volunteer work… so I smiled and moved on. 
After two months, he reappeared!  Apologized for being busy at work, wanted to get a hotel.  Of course, scheduling was a nightmare over the holidays, and then I got the stomach flu and then a cold and I despaired of us ever meeting.  
Finally came MLK weekend.  Hubby was away at a convention for three nights!  I had my condo to myself and no one to come over to play!  Weekends are tough for most men, and holiday weekends even worse in terms of getting away from the family.  I mentioned it to Randy.  He said he had a long list of ‘honey-do” items and events with the family.  *sigh 
Then suddenly he offered to come by Sunday morning!  We had a fun chat, imagining what that would be like.  He said he’d know on Saturday afternoon.  I was on my way to meet a gal pal when he pinged to say he couldn’t make it.  He had to take his kid to a sporting event.  Ah well… 
I went on to afternoon tea, had a lovely time and finger sandwiches with my friend!  Then I went out for dinner and a movie with Sis.  We saw “Hidden Figures.”  So good!  
Randy pinged me as I was driving home.  He said he was really looking forward to tomorrow morning.  I was like… Wait.  What?  I thought you canceled?  He said I misunderstood!  WOW!  He is going to visit me!!!
It hit me that my condo was in no shape for visitors.  So at 10 pm at night I dug in to clean up, hide away, and rearrange!  Randy was chatting with me while I cleaned!  He took off to bed at 11 pm, and I spent another two hours working.  I even got out the broom and got the cobwebs off the ceiling over my bed!
I finally fell into bed at 1 am, faced with having to get up at 7 am to shower and be ready for him at 8 am.  Whee! 

My alarm went off at 7 am.  Ugh.  Too early!  But my excitement was enough to get me out of bed, through my morning routine and ready for him by 8:03 am!  He found a parking space and was waiting for my signal.  I buzzed him up and met him at the elevator in my nightgown (and nothing else!)  We had a lovely hug and kiss, then I led him into my unit. 
We had another long kiss just inside the door, then I led him to the bedroom to put down his bag and take off his coat.  I introduced him to my cats and he admitted he is allergic.  Crap!  He said he’d taken allergy meds (he does every day) so he’d probably be okay.  [I have to remember to ask men about their allergies!!!]
We hugged and kissed for a while more, then helped each other out of our clothes.  We sat on the bed touching, exploring, kissing… then rolled over into a lovely naked hug!  He played with my clit and explored that area until I was squirming and shrieking.  He has great big hands and knows what to do with them! 
He reclined and I put my head on his chest, ran my fingers around, then down.  There was a nice glob of pre-cum for me to spread around while I explored his cock.  It’s not long, but average with a wide girth!  


I moved around to give him a Sassy blow job!  I licked him up and down, pulled on him, stroked his balls, then sucked him down my throat and bobbed back and forth.  He warned me that he might not last long because it has been so long since he’d had sex and he was all revved up! 
And sure enough, I pulled him deep into my throat and BOOM!  I swallowed a big load of cum! 
Oh, I do adore that! 
We relaxed and I put my head on his shoulder and we talked about high school crushes and whether the new president will mess with his industry.  I reveled in the luxury of being able to cuddle naked and touch him all over.  I asked if he wanted to taste me.. He had been so “I adore oral in both directions!” but he said his nose was stuffing up so he wouldn’t be able to breathe if he went down on me.  Ugh.  


Eventually he said he needed to be inside me.  He said he was going to fuck me good.  So he got up to find the condoms he brought.  A Trojan wearer!  He brought a box of 20!  He pulled me to the edge of the bed, pulled my legs up and slid inside.  Mmm… such a wonderful feeling!  He pounded me for awhile.  He was having trouble finishing, so we rested awhile more, nestled together.  Then I offered him doggy style and he grabbed another condom and stood by the end and entered by the rear door!  He pounded me!  So so hot!  I was trembling and screeching! 

He still didn’t cum… hmmm… he had talked so much about being able to cum over and over.  Ah well.  Maybe we can try something else? 

Bucket List Item – CHECK

He asked if it would okay for him to jerk off and cum on me.  Yes!  I am finally going to get someone to do it on my breasts!  Wowzers!  He used his hand and I licked him a little and BOOM!  Five spurts onto my chest!  It is something to watch!!  
I had to take a photo!  Here’s proof.  A rather demure photo of my cleavage except for the globs of hot white cum!  Hee hee.  

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We had another nice cuddle but then his nose and lungs were getting painful so he said he had to go.  *sigh Another man who can’t visit me here.  


We chatted as he dressed then I gave him a quick kiss on the lips and he was on his way about 10:30 am.  


12:07 PM
Hey there thank you very much for a magical morning.
It looks like I left just in time
got home wheezing and out of breath.

Son’s nebulizer worked
Feeling better now

[Bless him for writing so quickly!]

Phew! Thanks for letting me know.. I was worrying about you!
It was a special morning!
I am writing about it in my journal… lots of yummy words like hot and sexy and mmmm

Very nice I like it

9:17 PM
Thank you again for a magical morning.
The steroids make me feel a bit wacky but feeling better now
Messed up afternoon for me
Daughter disappeared with friend when she was supposed to be studying
Had a lot of fun this morning. I hope you did too.
Next time should be at a hotel

9:28 PM
Hiya! I am still beaming about your visit!!!

9:37 PM
You’re probably out huh
So am I.
My insides are all a buzz. 

But then again some of that is probably the steroids