Connection with WrySmile

September 15, 2017 Friday

from: Sassy
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…



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.



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

2) Nasstoys Ultra Elongated Vibrating Silver Bullet

> 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!



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.


Published by

Sassy Girl

It's the gal you knew in high school that you've wondered about. And she's got something to say! Time to heat up old flames!

Leave a Reply

Your email address will not be published. Required fields are marked *