The Feast

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

Sassy,

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.

Darrin

————

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.

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!

-S

=====

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

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:

http://advizortoall.tumblr.com/post/37135662621/this-kills-me-and-i-love-it
(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.

http://enmoi-fr.tumblr.com/post/165009908309/wow-girls

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!

-S

=====

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

Hiya!

Here’s a photo of my assets.

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

-S

[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?

-S

=====

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]

Connection with WrySmile

September 15, 2017 Friday

from: Sassy
to: wrysmile688@gmail.com
date: Fri, Sep 15, 2017 at 9:17 AM
subject: Connection

Hiya! Happy Friday! Tap…tap… is this thing working?

Is this the right email address for the guy from that website? I like to check before launching into anything more…

-S

=====

from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 11:01 AM
subject: Re: Connection

Hi Sassy,

Yes, it’s me! To prove it: I sent you two excessively long messages last night.

I wait for your response with breathless anticipation. ;+)

=====

from: Sassy
to: WrySmile 
date: Fri, Sep 15, 2017 at 11:42 AM
subject: Re: Connection

Hiya Wry!

Hope your Friday is off to a grand start! Thanks for the long luscious messages! I read them in bed last night and went to sleep with a big smile on my face.

I’m at the office, just finished wrestling with the payroll. Whee! Mundane but important. Now it’s time to take a break and be with you for a few precious moments!

Your offer of ice cream was original! Much better than the usual coffee or bar meet ideas… I roll with them but I don’t drink coffee or booze so this is better. I will admit I like Christina’s Ice Cream in Inman better than Tosci’s but I rarely get to either. I’ve been to JP Licks recently. They are tasty but not in the same league!

I was actually asking how you heard about AM. Heh. But your answers to the different questions were entertaining!

Are you still in touch with Donna? My first time was at 17 with my high school sweetheart, after we dated for 4 months. We kept going a little further and further until… all the way. It was… dull. We had no clue what we were doing. We puzzled over why the adults thought this was so fun. I’ve learned a lot since then!

I gave up on my sex life ages ago when Hubby decided I was not attractive. I thought he was right and that part of my life was over, but an old flame from high school found me after 37 years, wanted to finish what we started when I was 14, see if the chemistry still burned. We spent a magical two days together 7 years ago. He resurrected me sexually, taught me that a woman can participate and enjoy! He was military, married and miles away, so he encouraged me to find a local option. My friends pushed me to AM. I thought no one would want a curvy, 50-something woman with long gray hair… I was wrong!

I was going to make some pithy comment about misspelling discreet in your profile, but the moment has passed! If you keep using that profile, please fix that!

Nuts? All double-entendre are completely intended. Sassy! Groping is a fine art and I’m happy to tutor. It is fun for both parties! You can help me with the finer points of hugging and caressing. I also volunteer to check out your kissing prowess and report my opinion. I’m having a lovely time imagining that…

Your career path is strangely aligned with mine – I’ve worked with many of those professionals! Though I am not my job… I help run a community project and that is more what fulfills me. Do you mostly work in an office or home or visiting clients? I was educated at a prestigious women’s college, mostly about how corrupt and insular such places can be!

Answers for you:

>Have you had affairs?
Yes. With Hubby’s consent. Old flame and some AM Men.

> When was the first time you had sex – see above

> When was the last time you had sex
Aug 25. There is a nice man who pings me a few times a year for a meet, no communication otherwise. He is sweet and vanilla and falls into the “much better than nothing” category but I definitely need more! More communicating, more sex! Once a month would be nice? Or more?

> When was the first time a lover gave you a powerful orgasm? How did it happen?
It was on the phone… mmm. Oof… that man could talk.

> What kind of porn do you enjoy?
I have a wide range of favorites, mostly fall into the “a man and a woman being nice to each other” category, but as it gets longer since I’ve had sex, my tastes get raunchier. I am currently having fun with Tumblr exhibitionists who post scandalous public displays of flesh. Not something I want to do but I enjoy their naughtiness! I like .gifs, those little loops that act as a springboard for my imagination. I can send samples if you’ll reciprocate. I tend to look for things I know a man will like, since most p0rn is made for them.

Tell me or show me what you like and I’ll watch out for it and share stuff I find?

> Please name some of your favorite movies
I don’t see many. I like movies with kissing. My all-time favorite is a period piece – the Merchant/Ivory romance called “A Room With A View” about Brits traveling in Italy. I adored “Spotlight!” I tag along with Hubby who has to see “Star Trek” or “Star Wars” the first night. The last movie I saw was “The Big Sick” which had its moments. Did you see “Lion” with Dev Patel and Nichole Kidman? It was intense and delightful.

Do you know about the 70mm festival at the Somerville Theatre? We saw “West Side Story” last year… spectacular! They’ve commissioned a new print of “2001: A Space Odyssey” for this year along with a lot of strange and wonderful films.

> Enjoys jazz
I don’t know much about it. Who are your favorites?

I like music I can sing along to. Do you sing?

I’m a folk music fan in the David Wilcox, Christine Lavin, James Taylor vein. Or Broadway show tunes. Or a cappella.

> Has eyes I can get lost in
If you like blue eyes with a twinkle.

> Loves long sessions (10 minutes +) receiving oral sex
[I think I know the answer to this]

20 minutes would be good. With a finger or two added at the right moment. ; )

> Makes me laugh
[We already know the answer]

Ha ha. You know it.

> Hates most current comedies; thinks action movies are mostly boring
Agreed. I did like “The Italian Job.” Seen that? The trick with the traffic light… I long for that on my daily commute!

> Has a nice butt
You betcha!

> Enjoys giving head
[We know the answer to this too]

Oh yeah… I’ve been told I have mad skillz. Heh. I had never done this until old flame requested it, had to watch videos to catch up on the best techniques but I think I’ve got it now. I used to think it was all about sucking but now I am more into licking and stroking…

Mmmf… where was I?

> Politically liberal or, if not, enjoys a good debate
So so liberal. Not a debater.  Politics these days makes me sick. *sigh

> Enjoys back door play or is willing to experiment
Would take a lot of trust and lube… I have had success with prostate massage… nothing like hearing a man say, “I’ve never cum so hard in my life!”

> 420 friendly
No experience with this. Brownies? Smoking?

I am fascinated with all this – I appreciate you asking questions! We can have wonderful conversations and laugh and smile. I can’t tell yet about more. Wish it could help me know how the skin on your wrist would feel under my thumb… how your beard would tickle my inner thigh… mmm.

I’d better go do more work before this turns into a novel! Hugs with groping… and an ear nibble.

-Sassy

=====

from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 8:47 PM
subject: Re: Connection

Where to begin? First, I want to say that I’m having a lot of fun communicating with you and I’m looking forward to talking to you voice-to-voice or face-to-face. I think I’d like to get to know you, even if we never get into bed together.

Next: what are you up to during the day Saturday? (When I first typed it, it came out Satyrday; how appropriate.) My wife will be out of town until late afternoon. (Just to talk – and maybe stroke – not a tryst.) Let me know.

The ice cream invitation was just me being me. I figure it’s a more relaxing way to meet. And talking about interesting ice cream flavors can help when conversation flags. (Can you imagine the conversation over coffee: “I usually get the Extra Dark French, but sometimes I go for a lighter Colombian blend.” “Oh really! How did you get into Extra Dark French?”)

Ooh ahh! Which community project group??? I was in and around several a dozen years ago.

I do sing! I was in a chorus years ago. I’m terribly out of singing shape now. I used to play the guitar and sing obsessively. But in my 40s, I started doing it less and less; then a health problem forced me to stop playing guitar. Singing show tunes karaoke isn’t as much fun for me. (“Stars”, “Empty Chairs at Empty Tables”, “Luck be a Lady”, “Man of La Mancha”.) When in shape, my voice is pretty good and my sense of pitch is very good.

I like your taste in music and movies.

My taste in porn is almost always amateur porn, and a lot of it includes anal. To me woman’s orgasm is the sexiest thing in porn – and in person. The woman must be enjoying it a lot. Not acting – or at least acting really convincingly. I’m setting up a space on my Google drive to share videos with you.

Prostate massage? Wow! Never tried it; it sounds amazing. Similarly, I’ve given powerful results by triple stimulating – tonguing and fingering front and back. (My mouth is watering.) (On our second date, I ate my wife to orgasm – a first for her. I think that’s why she married me.) I’m intrigued by your 20-minute idea, but even the tongue gets tired after a while. And the payback would have to be pretty great.

I am still in touch with Donna; we had coffee together about 5 years ago (really nice) and we emailed each other a few weeks ago.

Where have you met your lovers? I presume you throw hubby out of the house for a few hours and bring them home. Do you use any sex toys?

I’d be happy to introduce you to smoking pot. (Speaking of powerful orgasms.) But, do not try eating it until you’re more experienced! It’s very hard to control the dosage and the high lasts for hours. (Remind me to tell you about an adventure with cookies.)

That’s enough for now. I hope this email makes bedtime more fun. Let me know about Saturday.

=====

from: WrySmile 
(via Google Drive)
to: Sassy
date: Fri, Sep 15, 2017 at 9:05 PM

subject: sassy – Invitation to collaborate

WrySmile has invited you to contribute to the following shared folder:
SASSY folder

Sharing some downloaded videos

=====

from: Sassy
to: WrySmile 
date: Fri, Sep 15, 2017 at 10:26 PM
subject: Re: Connection

Hiya! Thanks for perking up my Friday night! This is fun! You are a quite an interesting man.

Oh! It would be grand to see you tomorrow! But I can’t…argh. I am helping on the community project all afternoon. Let’s find another time soon?

I like you being you! You are so clever! Ice cream is definitely a fun, safe subject. Will we ever run out of topics?

Anal, eh? Fascinating. Have you done it or is it a bucket list item? I look forward to seeing the videos you like.

Awesome that you still see Donna! Speaks well of you!

> Meeting places?
Varies. Hotels mostly. I brought a few men home after I knew them better. Are you allergic to cats?

> Do you use any sex toys?
Oh yes. Do you? I own a bunch – friends recommend them when they’re on sale, and I had no idea what I’d like so I got them all. Heh. I find they enhance things with a man, and keep me calmer in between. Oof… I sound like such a hussy. Ah well!

I have two faves right now – These are made for internal use, but I use them outside to buzz my clit. Or help a man tingle.

1) Lelo Gigi 2
https://www.lelo.com/gigi-2

2) Nasstoys Ultra Elongated Vibrating Silver Bullet
https://www.amazon.com/dp/B001BNNWUK

> I’d be happy to introduce you to smoking pot.
This scares me… though I should try it once to see what happens?

I would have to trust you to take care of me.

(Speaking of powerful orgasms.) That is tempting!

Have you smoked for a long time or picked it up recently?

I’d better send this along. Sweet sexy dreams! Mwah!

-S

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from: WrySmile 
to: Sassy
date: Fri, Sep 15, 2017 at 11:44 PM
subject: Re: Connection

This is fun. It’s great to have someone to talk with about intimate and “dirty” things. It’s a shame we can’t meet tomorrow; when are you free? Can you meet for ice cream on a Tuesday or Wednesday night? Next weekend?

Some quick responses go your message:

Unfortunately, anal is a bucket list item. I’ve tried it a couple of times: once a failure (the last woman I had sex with before 38 years of fidelity) and once an epic failure (wife refused all future tries). We had no idea what we were doing.

We also have cats (2). Mostly they’re my wife’s. I used to be allergic; I’ll tell you how I got over it.

Toys: my wife had no interest. I recently bought a fancy stroker for my “practice” sessions (Blewit); it feels great. (My wife has been curious about the device, but that’s it.) I’ve read about the Lelo Gigi 2; it sounds amazing.

There’s no reason to fear marijuana; if you want, I’ll make sure you start slow. I started smoking early in college. I smoked through my 40s — a friend grew great weed and kept us supplied. But when he stopped growing, I had to quit for lack of a source. Until recently.

A few months ago, I tried writing some porn. As literature, it was a dismal failure; but they might turn you on and they’ll tell you something about my fantasies. Shall I send you one? If I do, you’ll be obliged to reciprocate by telling me some of your fantasies. Or maybe your failed attempts at writing fiction. (Another Freudian typo — it originally came out as “fuction”.)

Have fun tomorrow. Let me know when you’d like to meet. And please consider sending me a picture of your face.

G’night

WrySmile Answers

September 14, 2017 Thursday

Ashley Madison Message

Date: Sep 14th – 2:24pm
From: Sassy
To: WrySmile

Message
Hiya Wry! How’re you this warm day?

I am having a wacky day at the office but decided to take a break and write to you! Thank you for your message! And the photo. Adore a man who still has hair on his head and a beard!

Give me a little time to get to know you before I jump to email and share a photo?

Three quick questions –

What’s your favorite ice cream flavor.

How did you hear about it? (I’m curious as well as Sassy!)

When did you first have sex?

Here’s more about me – I am not into vanilla… I like butter pecan! Nuts are so yummy. 😉 I’m on AM because Hubby and I are great friends, but we haven’t had sex in a long time. He does his thing and I do mine. He’s fine with that. I heard about AM while reading a blog by a guy who shared his adventures pleasing married women and himself. And I’m here because I beat cancer six years ago. I’m whole and healthy, and want to live life to the fullest! I am an office manager by day. You know – that shy, demure, efficient lady who takes care of the administrative tasks so the senior staff can focus on the business. Men say I am an awesome kisser, a great communicator, discreet, no drama, super-nice… looking for fun and passion and a confidante. Is that you?

Finally… please feel free to ask me whatever you like to see if we click, and tell me more about you.

Hugs with groping! -Sassy

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Date: Sep 14th – 10:36pm
From: WrySmile
To: Sassy

Message
Responses #1. (I enjoy writing.)
Favorite Ice Cream: I would normally say Toscanini’s burnt caramel, but I had some basil ice cream at a fancy (“artisanal”) restaurant that sent me to the place where poets get their inspiration. Unfortunately, I probably can’t afford to go back there for a long time, so I’ll stick with burnt caramel.

How did I hear about it? I used to live near Toscanini’s, and went there frequently (clearly I was much younger). I tried burnt caramel and was sold instantly.

(I have to tell you: when I skimmed your message I thought you were asking me how I heard about sex! That was probably from Marc Schalater in junior high school. Of course he really didn’t know anything.) I first had sex second semester freshman year in college on a mattress on the floor of my room. Donna was one of my best friends in high school, but we didn’t start dating until I was in college (she was still in high school). She came up to visit and we finally got our chance. It wasn’t good – worse for her.

“Nuts are so yummy.” Did you intend the double-entendre?

I’m not much of a groper – I’m more of a hugger/caresser. You might have to demonstrate. Am I an awesome kisser? I have no idea. But I’m a respectful lover, always reading and responding to my woman’s reactions and level of arousal. Am I a great communicator? I guess so: I’ve been called a great listener and a great conversationalist.

Discreet, no drama? Definitely!

Super-nice: I’m confident that you’ll find that I am.

Looking for fun and passion and a confidante. Definitely. My wife and I do less together, don’t share passion together and talk to each other a lot less than we used to. And there are things we don’t talk about – like sex and what I do on the web. I want to fill in all of those gaps.

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Date: Sep 14th – 11:04pm
From: WrySmile
To: Sassy

Message
BTW: I never said thank you for your great reply. Thank you.

More about me: I’m generally quite modest, respectful, open and friendly. I’m very analytical and VERY verbal. I love to meet people and I love to make them laugh. I’m not a man’s man or a ladies’ man. Throughout my life, many of my closest friends have been women who were not also lovers. My work history is all over the place – [redacted impressive list of professional office positions] and [current job]. It sounds much more impressive than the reality. I’m one of the least impressive graduates of two very impressive universities.

My wife and I love each other: we hug, kiss and hold hands. But she lost interest in sex years ago and gave it up completely soon after that. The last time I had sex with a woman other than my wife was 1979. So I’m badly out of practice. But I think I’m still pretty good; as Woody Allen wrote: “Countess Alexandrovna: You are the greatest lover I’ve ever had.

Boris: Well, I practice a lot when I’m alone.”

My wife knows about my “practicing” and has no problem with it, but also no interest.

——– Questions for you: > Have you had affairs? > When was the first time you had sex > When was the last time you had sex > When was the first time a lover gave you a powerful orgasm? How did it happen? > What kind of porn do you enjoy? > Please name some of your favorite movies

Please respond to items in my wish list: > Enjoys jazz and “serious” movies (e.g. “Spotlight”) > Has eyes I can get lost in > Loves long sessions (10 minutes +) receiving oral sex [I think I know the answer to this] > Makes me laugh [We already know the answer] > Hates most current comedies; thinks action movies are mostly boring > Has a nice butt > Enjoys giving head [We know the answer to this too] > Politically liberal or, if not, enjoys a good debate > Enjoys back door play or is willing to experiment > 420 friendly

New guy – Wry Smile

September 12, 2017 Tuesday

Ashley Madison Message

Date: Sep 12th – 9:06pm
From: WrySmile
To: Sassy

Message
Hi Sassy
Let me buy you a Toscanini’s sundae or cappuccino so we can talk. I really enjoy your profile, your tagline and the fact that you live nearby. I have to admit that I’m a bit put off by your dimensions, but you seem like fun. So let’s meet.

About me: I’m friendly, open, warm, honest, well-educated and occasionally quirky. I’ve been called a great conversationalist. I love to make people laugh. I’m occasionally called handsome, but I doubt I’ve ever been called sexy. I’m told I have kind eyes, but I have no idea what that means. My wife described me this way: “You’re interested in everyone and you respect everyone.”

To echo what you want in your profile: I’m smart (at least that’s what my degrees say), I believe I have a good sense of humor, and I’m often upbeat. I like a wide variety of restaurants. I love to make people laugh and smile – especially women.

The relationship I’m looking for will be based on good conversation and sex. I think my profile describe me quite well. Take a look and see if you feel like a trip to Toscanini’s with me.

PS1: You can use wrysmile688@gmail.com to contact me.

PS2: Got a photo?

=====

Hmmm… he jumps straight to wanting to meet. And gives me an email right away. That usually does not bode well. But an offer of ice cream is different… how creative! and one of the best places across the river! I usually get invited “for coffee” or “for drinks” neither of which appeal. Ice cream? YUM!

But the line about my “dimensions?” Ugh. Normal I guess, and honest but… yuck. It reminds me of the line about what people fear when meeting a person online. Men worry the woman will be fat. Women worry the man will kill them. *sigh

Otherwise, he sounds possible. I’d better go look at his profile to see if it makes him look better or worse.

Let’s see….

Good tagline around humor!  That’s a great start! 

Photo is not great…his face cropped from some random group photo with the added goofy Ashley Madison eye mask. Not smiling. He has hair on his head! Nice beard.

A little older than I am. Good.

Lives nearby… okay.

A little taller. Okay.

Weight… skinny. Eh.

Wants something long term. Good.

Didn’t answer the smoking question?

Wants someone smart! Yay!

Nice guy. Yes, please.

Wants to charm me, make me smile, make me laugh. Great!

Says no sex with his wife and she’s okay for him to look elsewhere. Wow.  Never seen that before.

Spelled discreet wrong. Twice. Heh. What it is with that word guys?!

He put requirements, which I can easily meet. Then he put a wish list – good way to express that! He mentioned one of my favorite rather obscure movies!

He mentions anal sex. Eh. But then a lot of guys do, sort of a litmus test to see if you’re flexible and non-vanilla, but then they never try to do it.

He would like 420 friendly. Bleh.

An interesting mix… maybe worth responding to and eating an ice cream to see if the positives outweigh the negatives?  Do I really want to jump back into this again?  I need to think it over.