Grease the skids

September 19, 2017 Tuesday

from: Sassy
to: WrySmile 
date: Tue, Sep 19, 2017 at 7:18 PM
subject: Re: A Feast.

Well well well… this email was full of treats!

I had a wonderful time talking and walking with you on Sunday! You are a wonderful storyteller. Thank you for getting me back to Tosci’s after far too long, showing me a new park, and your old neighborhood!

And this feast story? Yummy! I am pulsing inside. Whee!

I’ll send you another of mine. This is fun!



from: Sassy
to: WrySmile 
date: Tue, Sep 19, 2017 at 7:23 PM
subject: The Storm

The Storm

He made it inside just as the first thunder clap sounded. BANG! It started to pour as he walked past the living room windows. Wow. That was close. He loved thunderstorms! He was very tempted to stand outside to watch the storm. Maybe even dance in the downpour. But there was something more important he had to do.

He knew where to find her. He shed his clothes as he made his way to the bedroom and sure enough, there was this lump the size of a person under the blanket. He rubbed where he thought a leg might be, and a slight whimper filtered out through the covers. There was a crash of lightning and another big boom, and she shrieked.

“It’s okay. You’re okay. I’m here,” he said calmly, trying to be soothing. He crawled into the bed next to her. She clung to him and wrapped herself around him, burying her head in his chest, trembling. He couldn’t believe she was still such a wuss about thunderstorms. She was so brave about almost everything else.

But he knew how to distract her. He put his hands on her back and rubbed gently. He explored up and then down, surprised that she was naked. He pressed her ass so that she fit tightly against him. She moaned sweetly when she felt him hard against the top of her leg. She shifted her head up and grabbed his head with her hands, kissing him frantically. He slowed her down a bit, pressing his tongue into her mouth at a leisurely pace and making more soothing noises.

“We have plenty of time…” he pointed out, squeezing her breast and teasingthe nipple.

“Fuck me,” she whispered fiercely. It sent a shock wave through him. He loved it when she talked dirty to him. Everyone else saw her as an ultra-polite, demure lady. Only he knew about the wild girl inside. She was turning the intense fear into another emotion, putting it to good use. Smart girl.

“Yes, ma’am…” he chuckled. He hugged her, pondering which position would be best.

“Fuck me now,” she urged him. She wasn’t going to let him go slow today. She flattened him onto the bed, straddled him and pressed him close, shifting her hips to rub him against her. He could feel her dripping already. It made him a little crazy. He shifted slightly and she took him inside her and began to move. Up and down she went. He put a hand on her hip and one on her breast, twisting, teasing…

He knew her inside and out, as much as any person can know another. But it never stopped surprising him how tight and hot she was, how he fit inside her like a sculptor had made him to be there and made her to make him feel so incredible every single time. When he first touched her as a green boy, he realized that she was different. He had felt an emotional connection for ages, but when they finally kissed, he felt a physical connection to her that he never felt again in his life. Special, comfortable, exciting… and at times, inflammatory. Chemistry. That had never changed. He thought he would get tired of her, stop thinking about her, stop wanting her… but it never happened. Sometimes it drove him crazy, when he couldn’t get to her. When he could and he couldn’t get inside her fast enough. But it was the best kind of crazy… it made him feel alive. Kept him young. Made them both happier than anything or anyone else. And the most amazing thing was that she felt the same way. He marveled over that every day.

She stopped moving… sensing that his mind had drifted. He snapped back to her body and what she was doing, putting a finger at the top of her slit and flicking her most sensitive spot. She sighed in pleasure and started moving again, rising up, arching her back and driving down on him again, shoving him so deep inside…. and then out again. Her tits looked amazing when she did that! It was the sweetest form of torture… so hot, so wet, so…. hmmmm.. he could not think when she was like this. He could feel… oh, man could he feel! Every nerve in his body was on fire. And he craved the heat. She kept turning up the temperature… taking him closer and closer… and then stopping. She was panting. She leaned over and kissed him again, sucking his tongue, twisting her hips… damn. He felt the magic start. He wasn’t going to last long if she kept this up… it was as if every muscle inside her was trying to squeeze him, milk him… whoa, baby. What a woman…he thought she was going to make him peak. But when he thought he couldn’t take it another moment, she stopped, flipping over onto her back on the bed.

She lay there breathing loudly. He tried to figure out what she was up to. She turned to him and kissed him, wrapping herself around him on her side. She stroked him, then put her hand lower, caressing his balls, pressing the spots she knew would send him soaring. His breath grew ragged.. what would she do next?

She pressed a finger inside his ass. Oh, wow… she was really trying to push all his buttons this time! His hips rocketed off the bed. She pumped in and out, whispering in his ear. “You like it when I fuck you, don’t you, fella? Like it when I give your ass the love, eh?” she said, making a little sucking sound. He moaned. She knew just what to do. She moved down his body, putting her mouth where her hand had been, licking his cock and sucking it deep into her mouth, then kissing his balls and sucking them and finally sticking her tongue in his ass! He moaned and trembled. She could be such a vixen!

That was it. He rolled over, pulled her legs up to his shoulders, and dove back inside her, pumping, deep, long strokes while she moaned and then screamed, her head thrashing from side to side. He watched her shake, felt her hips crashing up against him. She opened her eyes and the look… the look nearly made him explode. So many words popped into his head… lust, passion, fire… love. No one loved him like she did. Her mind, her body… it all went together to make him know… mmmm….

There was another big thunderclap and she jumped. He went wild on her, his hips thrusting in and out, hearing the slap of his balls on her skin and her moans… he let go, let his body take over, let the pulsing inside her trigger the flow…. he filled her, shooting over and over inside her, grunting and moaning and… exploding. He collapsed beside her, feeling his heart beat, listening to her breathing… smiling. He did love thunderstorms! And her…


from: WrySmile 
to: Sassy
date: Tue, Sep 19, 2017 at 7:58 PM
subject: Re: The Storm

Very nice. And told from the man’s point of view! Nicely done.

I’ve got a few more stories started, but they’re not ready for sharing — well, maybe one is close. Let’s keep trying.

When do you want to meet again?

I’m working on my reluctance, but it’s been two steps forward, one back. And sometimes two back. Maybe you could find some ways to encourage me, grease the skids, so to speak

I hope you’re having a good week.

When will you have time to talk more?


The Feast

September 18, 2017 Monday
from: WrySmile 
to: Same Sassygirl 
date: Mon, Sep 18, 2017 at 9:51 PM
subject: A Feast.


I truly enjoyed our time together. You’re interesting, fun and clever. I hope we get a chance to continue our conversation soon.

I finished cleaning up another story for you. I hope you enjoy it and that you send some of yours to me.



A Feast

We talk on your couch, accompanied by the quiet moans and gasps of a porn video. We sit close to each other, drinking wine and making snide comments about the activity on the screen. Her makeup is wrong. I’ve never seen one so big. Those are definitely not natural. Now and then you stroke my arm or my knee; I stroke the back of your hands, your thigh, your side.

We share a joint and start to make out, kissing, rubbing and nibbling each other. We remove each other’s shirts and pants. I push you back on the couch and kiss your mouth and nuzzle your neck. You pull my right hand to your left breast; I gently squeeze and massage your breast and play with your nipple. My mouth moves slowly from your mouth and neck to your chest, the space between your breasts. I inhale deeply, enjoying your earthy scent.

My mouth moves to your right breast; I kiss and suck the nipple through the bra while squeezing your left breast firmly. You hold my head, occasionally pulling me closer to your breast, sometimes running you fingers through my hair.

I look you in the eye and we again kiss passionately, my right hand firmly massaging your left breast, your right hand holding onto my hard cock. I again kiss and taste your neck; moving up your neck I approach your ear. I squeeze your breast firmly and gently pinch your nipple as I give you a light lick in your ear and exhale lightly. You giggle and shiver.

I straddle you, sitting on your belly and lower ribs, kiss your kips passionately, then nuzzle your neck. As I lean forward my cock rubs against you. Then I hold both of your hands back over your head. I kiss, lick and nibble your throat and rub my cock between your breasts. I lie down on top of you and slowly taste you from collarbone to earlobe. Letting go of one hand, I squeeze your left breast hard while I flatten my wet tongue against your ear and lick your ear from earlobe to top.

You cry out, wiggle and squirm, but I pin you down, squeezing your breast, pinching your erect nipple, flutter-licking and blowing into your ear. Your body bucks, “Oh god. No! Stop!” but you’re clearly loving it. I stop and kiss your neck and mouth; you look both relieved and disappointed. So I pull down my briefs to let my erection loose and bring it to your lips.

Have you ever had a puppy? You’re both in the kitchen; she’s hungry and excited, knowing she’s about to be fed. She jumps against your leg excitedly, whimpering and giving little barks of anticipation. Then you feed her hamburger and her excitement redoubles, wiggling with excitement, she can barely contain her joy. Occasionally she glances up at you with gratitude.

That was your reaction to my cock at your lips. You sucked my hard penis into your mouth and out and in, occasionally making sounds of joy and looking up at me to see how much I’m enjoying it. (Immensely!) Squeezing the base while your lips move up and down and up and down then down your throat!! (I almost scream with pleasure.) You suck a few more times and back down your throat while you cup and stroke the underside of my balls. And again and again and again. It couldn’t have been more than 10 minutes, bit it felt like lifetimes – I had lost my sense of time, of anything, really, other than the overwhelming pleasure of your hand lips, mouth, tongue and throat.

After a little while, you ease off and push me onto my back, panting. You remove your bra and your wet panties. You rub, kiss and lick my face and body, sometimes holding or stroking my cock. Then you straddle my head and say, “My turn.” I don’t need convincing.

There’s nothing subtle about your approach: facing away from my cock, you drop your vulva on my lips almost before I can open my mouth and start to pump. I lick slowly and probe your labia and vagina with my tongue. My licking gets a little faster as I grab your buttcheeks in both hands and pull you onto my mouth with a rhythm that matches my tongue. Sometimes I grab your cheeks harder and my licking speeds up, up and down, side to side; then back to a slower rhythm again.

You moan and start rocking back and forth in your own rhythm. I slide my hands gently over your sides and up to your tits. I lick faster as I squeeze your right breast while I roll your left nipple between my fingertips. I ease off, then get more intense, three or four times; during the next ease off I slide first one, then two fingers in your vagina. I nibble your labia while my fingers slowly fuck your pussy, then I lick your clitoris gently. You moan and gasp repeatedly.

You’re really getting hot, grunting, pumping your pussy onto my mouth… so I slow down my fingers and my tongue. I roll you on your back, my two fingers deep and still in your very tight vagina. I lick my way from your pubic hair across your belly up to your breasts. I lick my way around your right breast spiraling in from the perimeter towards the nipple. I give your nipple a few slow licks, with my tongue flat and wide; my fingers gently start moving inside your pussy. Your breathing speeds up, I move my fingers firmly in and out and in and out while I suck your nipple hard and gently rub slide it in and out between my teeth. Your back starts to arch; you cry out.

But I slow to a stop and let you catch your breath. I gently remove my fingers from you wet cunt and slowly start to lick and stroke my way back to your erogenous center. My hand is holding your mound as I spend a long time licking, stroking and running my beard over your belly, hips, knees, the inside of your thighs. You smell and taste like deep pleasure, matching you gentle gasps and sighs. You reach for my hard cock, but I don’t let you.

Then without warning, my mouth is on your vulva again. My left hand is squeezing a butt cheek rhythmically as I start licking – slowly, but not gently. My fingers slide into your cunt again, slowly, but not gently. Your gasps, moans and movements tell me that the time is coming. My licking and pumping grow faster (and less predictable). Your moans are almost constant. My fingers pump deep and fast, my tongue flutters wildly.

And I slide a finger into your butthole and start to pump slowly.

That pushes you over the edge. Far over the edge! You thrash, pump your hips, cry out unintelligibly and loud as I pumping fingers into your cunt and your asshole, rapidly flutter-licking your clit. Until your back arches hard, your body spasms three or four times as you yell, “FUCK. FUCK! FUCK FUCK!FUCKFUCKFUCK FUCKFUCK!!!!” You fall back to the bed, panting and quivering.

This time, when you reach for my cock, I let you.

Sneezy checks in

September 18, 2017 Monday

From: Sneezy
To: Sassy
Date: Mon, Sep 18, 2017 at 1:43 PM
Subject: checking in

Hello Sassy-

Finding any fun out there? I’ve been thinking about you:)
Hope you’re well.
Any interest in getting together??

Another man who is interesting enough but never leads to anything… I just don’t want to deal with that right now.  *sigh 

Philip’s back

September 18, 2017 Monday

11:32 AM Phil
Hey there lady! Hope you have a marvelous day!

11:49 AM Sassy
Hiya kid!
Looks like you had a beautiful vacation!
Hope re-entry isn’t too tough.

3:28 PM Phil
It was terrific!
Re-entering slowly and already ugly

5:56 PM Sassy
Regina Pizzeria at Station Landing in Everett

Italian wedding soup we shared
Free bread and oil
Large sausage Lasagna is large
Hubby’s Giambotta pizza with lots of meats and veggies

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

Tupelo brunch

September 17, 2017 Sunday

12:48 PM Sassy
Delightful birthday brunch at Tupelo in Inman Square Cambridge with my older sister and her beau! Just can’t seem to stop celebrating.  One of the best brunches of the year!

Iced tea
“The Dude” fried chicken breast, buttermilk biscuit, 
sausage gravy and scrambled eggs
Tupelo sandwich with scrambled eggs, chorizo, roasted red 
peppers and cheddar on a Portuguese sweet roll with home fries
Oyster po’boy with lettuce, tomato, Tabasco aioli, 
house-pickled vegetables and apple fennel coleslaw
A side of Applewood smoked bacon
Brown butter pecan pie
Mississippi mud pie with bourbon ice cream
The colorful exterior

WrySmile opens up

September 16, 2017 Saturday

from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:31 AM
subject: Sassy Saturday

Good morning! Time for a Sassy Saturday! 

In lieu of my presence, I will send you some virtual treats!

Evenings are possible! I’m not doing much for this project except every other Saturday and then the final prep in a couple of months.

Thank you ever so much for the p0rn! I didn’t have a chance to get alone to watch but I will soon. Do you have a Tumblr account? Most of my current faves are on there, and they’ve recently clamped down so you can’t see them without an account. Here’s a little loop I think works in the clear:
(sorry it doesn’t work… it was a woman licking a man)

Thanks for telling me about the failed attempts at anal. My last try was in my 20s with a long-time boyfriend… he got carried away and ripped me into bloody shreds – lack of knowledge there are well. After all that p0rn you ought to be as knowledgeable as an anal virgin can be, right? Every one tells me the key is going slow and lots of lube.

Here’s a .gif with exhibition and anal – definitely need a Tumblr to see it. Ah, those French.

I have two cats! They are mostly Hubby’s – he got them while I was in chemo as an emergency rescue from a project peep who developed allergies. I look forward to hearing your story about kicking the allergy! I ask because there was an AM man I met and affectionately call “Sneezy.”

Glad to hear you’ve discovered the fun of toys! They are a recent addition to my life – still figuring out their best uses.

I write erotica too! I adore it as a window into a man’s mind and a way to tell a man things about my fantasies. Please share! I’ll send you a snippet. If that one appeals, let me know and I have another with some anal action.

I’ll send a couple of photos too. Start with the face below. This was the hottest day of last year, on a boat, on Lake Winnipesaukee!

[photo of my smiling face]

Have a lovely day and don’t think about my ass too much! Mwah!



from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:32 AM
subject: The Black


Here’s a photo of my assets.

I fought hard to keep them so I get to show them off, right? 😉


[Photo of my cleavage with the black bra]


from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 11:42 PM
subject: The Drink

Sassy, let me know what you think.


The Drink

[He sent me a snippet of erotica about a couple at a bar discussing what they might do if they could be alone]


from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 7:32 AM
subject: The view

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.

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…”


from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 9:01 PM
subject: Re: The view

Thanks that was fun. I’m polishing up some of my stories and I’ll send some to you soon.

Do you have time to talk Sunday?


from: Sassy
to: WrySmile 
date: Sat, Sep 16, 2017 at 9:56 PM
subject: Re: The view

Hiya! Glad that was fun. It gets to me every time I read it.

Hope you had a lovely Saturday. I survived another project event!

Oooh…the thought of hearing your voice is revving me up! What a good idea! I am around tomorrow – should be home from brunch by 2 pm. Not sure about dinner plan. What time works for you?



from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 10:40 PM
subject: Re: The view

Great! I can be available after that until 5:00ish. You pick the time and place somewhere near the Red Line. Toscanini’s?


from: WrySmile 
to: Sassy
date: Sat, Sep 16, 2017 at 11:29 PM
subject: Re: The view

I hope you enjoy this story; I expanded it and polished it tonight.


[he sent a story about a woman going to a party with a vibrator insider her and having anal sex with her]

Sushi to Big Fish

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September 16, 2017 Sunday
From: Sassy
To: Thad 
Date: Sun Sept 16, 2017 at 10:29 AM

Hiya Thad!  

Saw this article and couldn’t resist sending it… wondering if you’d agree with their choices.

16 Outstanding Boston Sushi Restaurants 

From simple perfection to mountains of gold flakes and truffles 

Cafe Sushi 
 Rachel Leah Blumenthal/Eater

Sent from Yahoo Mail on Android