Category Archives: Email

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WrySmile thanks

November 23, 2017 Thursday

from: WrySmile
to: Sassy
date: Thu, Nov 23, 2017 at 1:33 PM
subject: Re: Turkey times

Happy Thanksgiving, my friend. I hope yours is scrumptious, relaxing and fun.

I really enjoyed the event! And the opportunity to talk to you.

So you enjoyed the story, eh? Your comments made me think about what it revealed about me. In the future, I’ll be more mindful about that.

The story is based on a real relationship I had with a woman in college (let’s call her Sarah), and the basic story is true — about our long friendship ultimately ending up in bed. Of course the story about our first time is invented (except for the line “WHAT ARE YOU DOING?!?!?”). And obviously, I don’t know what was going on in her head, but I’m very sure that she was in love with me.

Writing from her point of view was a challenge, but not that hard, but I have no idea if I did it well. What did you think about my portrayal of her thoughts? Was I in the realm of real or was I way off base (remember, she was a virgin)? Was it just what a man hopes that a woman was thinking? I’m pretty sure the deep throat ending was quite unrealistic, but it was the best ending that I tried.

If you give me some insights or edits, I may revise the story.

BTW, I’ve kept in touch with Sarah on and off for the last 40 years.

My sex life is unchanged — still just me and Rosie Palms. I’m off AM for now, but I’ve made a few contacts using a Facebook app, but none have gone anywhere. (I’d appreciate hearing your point of view about a couple of cases where I hurt women’s feelings.) I’m meeting someone promising this weekend.

How about you? Any luck?

Let’s meet soon. Let me know if you have time Friday or Sunday.

Darrin

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Thanks to WrySmile

November 22, 2017 Wednesday

from: Sassy
to: WrySmile 
date: Wed, Nov 22, 2017 at 10:21 PM
subject: Turkey times

Hiya D!

How are you doing this wet Wednesday? Hope you are having a good week.

Thank you so much for seeing the event with me! It was lovely to share that with you!

This week has been a bit nutty, trying to squeeze five days of work into 2.5 and my boss was leaving on vacation and pushing up deadlines and so forth. But I finished everything up in style and can relax and appreciate 4 days away from the office!

I read your story tonight. I’m so glad I could inspire you to create it. Did you find it a tough challenge or easy as it rolled along? It is a fascinating window into your perspective on how women think, and sex. I got caught up in it and got quite a few tingles!

Are you still active on AM? Meeting anyone fun?

Have a wonderful Thanksgiving! I hope it is a good combination of social and relaxing time!

-S

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WrySmile meet #2 – My event

November 18, 2017 Saturday

from: WrySmile 
to: Sassy
date: Sat, Nov 18, 2017 at 12:47 PM
subject: You asked me to write this, and I did…

Sassy,

It’s clear that you don’t want to keep in touch, and that’s OK. But a few weeks ago you asked me if I could write an erotic story from the woman’s point of view. I’ve been working on it ever since and wanted to share the results with you and get your comments. (And to thank you for giving me the challenge.)

It’s based on a real relationship from senior year in college. Of course the details of the scene are imagined except one that I’ll never forget: her saying “WHAT ARE YOU DOING?!???” (She and I occasionally email each other 40 years later.)

Let me know what you think of the story and please suggest any changes.

I hope you’re doing very well and that Hubby is holding up OK. Let me know if you’d like to keep in touch. But either way, I wish you joy.

Darrin

Attachment: Erotic Story

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from: Sassy
to: WrySmile 
date: Sat, Nov 18, 2017 at 1:44 PM
subject: Join me at an event?

Wanna see an event at 3 pm? I can get you in for free. Email back for details if you can dash out to join me.  🙂

Thank you for writing! Email and story. I promise to read it and comment soon.

Mwah!

-S

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from: WrySmile 
to: Sassy
date: Sat, Nov 18, 2017 at 2:01 PM
subject: Re: Join me at an event?

what’s event? 3;00 might be tight

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from: Sassy
to: WrySmile 
date: Sat, Nov 18, 2017 at 2:08 PM
subject: Re: Join me at an event?

Hop a Lyft?

[more on the event]
[address]

I will meet you at the entrance to get you in.  And save you a seat.

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from: WrySmile 
to: Sassy
date: Sat, Nov 18, 2017 at 2:11 PM
subject: Re: Join me at an event?

I’ll be late, but I’ll be there

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from: Sassy
to: WrySmile 
date: Sat, Nov 18, 2017 at 2:23 PM
subject: Re: Join me at an event?

Ok, see you soon! Hooray!

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What is the matter with me?!  I am such an idiot. 

It wasn’t until he had confirmed and I replied that it occurred to me – what did I do?  Why did I invite him to a public event with most of my community project people?  Argh!  

I have talked for years with various men about them attending these community events I work on, sitting with me in the dark, seeing the results of my efforts. I didn’t occur to me how risky that could be until after I did it.  Duh.  

He doesn’t know my real name or my role in these events.  How am I going to stay anonymous in the midst of my friends?  Is it still a priority?  Am I going to introduce him to people?  “This is Darrin.”  What will they think?  

Why am I continuing to communicate with someone who doesn’t want me as a lover?  Who would be a high-maintenance friend.  *sigh  I suppose because I was so proud of this event and wanted to share it, wanted his feedback, wanted him to have a nice afternoon out.  

I told Hubby that Darrin was going to appear.  He raised his eyebrows but didn’t say anything.  I went about my usual routine and waited, trying to put it out of my mind.  The event started and I concentrated on it.  

He showed up about half way through.  I happened to look over at the entrance as he came wandering in.  I dashed over to greet him, gave him a big hug and he hugged me back, holding on extra long.  I had saved him a seat and pointed in that direction.  He went along with me.  I wondered if he could gather enough about what was happening to make sense of it, having missed the first part, but he quickly got engrossed in the goings-on.  It was marvelous to see him paying attention, nodding, smiling over at me.  I worried that he’d get overly familiar and people would notice, but he didn’t. 

Then it was over.  He leaned in close and told me how much he had enjoyed it and how impressed he was and that he was so glad he’d made the effort to get there.  We stood up and I talked to several people as they departed, accepting their positive feedback.  Several of my friends asked questions about cleaning up and he listened as I answered.  I could feel him trying to figure out what my role was, but he couldn’t ask as people kept coming by.  

Finally, the crowd thinned and I turned to him.  He said more wonderful things, seemed astonished at the quality of the event and the comments from others, so happy to have seen it.  I was very nervous as another friend stopped by to chat, and started chatting with him, but the conversation stayed on the topic of the event and then he said he really should be going, it was obvious I had things to do, that we’d talk more next week!  He thanked me.  

I walked him out to the curb and we chatted while he waited for a Lyft.  When it pulled up, he hugged me, grinned, slid into the back seat and was gone.  

Wow… I can’t believe I got away with that!  I will think a lot more about it before I do it again, if I ever do!  

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Pinging Brett

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November 15, 2017 Wednesday

From: Sassy
To: Brett 
Date: Wed, Nov 15, 2017 at 7:19 PM
Subject: November notions
Hiya Brett!  Hope you are staying warm these wintery days!  
I’ve been home sick since Saturday with a bad cold, mostly sniffling.  Bleh.  I am finally starting to feel better, even did a bunch of work at home today.  Now it’s time to rest some more and relax, so I am thinking of you!  
The latest event for my community project got off to a wonderful start last Friday.  I wish you could see it.  It is amazing to watch all the pieces come together and the people there appreciate it.  
Hugs with lots of groping to you!  Mwah! 
-S
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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!

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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!  
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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!

-S

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Brett dreaming

October 26, 2017 Thursday
From: Sassy
To: Brett
Sent: Thu, Oct 26, 2017 at 7:39 AM
Re: Wonderful fall

Hi Brett! 

Yay! I am so excited to see you! Tomorrow! Mmmm…. I’ve already started thinking about your arms around me. And your hands on my chest. Tingling!

I made a reservation. Let me if I should meet you for lunch or at the hotel. Thanks!

See you soon!!

-S

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From: Brett
To: Sassy
Sent: Thursday, October 26, 2017 6:12 PM
Subject: RE: Wonderful fall

I don’t think I can make it for lunch this time. I’ll try to get there as early as possible. Let me know what time you think you will be there.

dreaming….

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From: Sassy
To: Brett
Sent: Thu, Oct 26, 2017 at 6:27 PM
Re: Wonderful fall

Hi Brett. Let’s aim for 2:30 pm? Don’t worry if you are later than that… I will check in as soon as they let me and wait in the bar. Can’t wait to hug you! And kiss you!!

-S

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Brett plans

October 25, 2017 Wednesday
From: Brett
To: Sassy
Sent: Wednesday, October 25, 2017 7:42 PM
Subject: Wonderful fall

Sassy,
I haven’t heard from you in a while!
What wonderful fall weather we are having. I’ve been able to spend a little time outside.
Are you keeping yourself satisfied? Maybe you’ve found a new lover.
Are you busy with community projects and other extracurricular activities?

brett

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From: Sassy
To: Brett
Sent: Wed, Oct 25, 2017 at 7:55 PM
Re: Wonderful fall

Hiya Brett! So wonderful to hear from you! The weather has been amazing – glad you got out into it.

I’ve been so busy at work and with community projects, but I finished my last big work event for awhile so I am hoping for quieter days!

I’ve been playing with my toys and behaving otherwise, waiting to hear from you. 🙂

-S

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From: Sassy
To: Brett
Sent: Wed, Oct 25, 2017 at 8:44 PM
Re: Wonderful fall

Hi again. I should add that I am off work tomorrow and Friday. If you can get away from the office either day, let me know. It would be fantastic to see you!

-S 

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From: Brett
To: Sassy
Sent: Wednesday, October 25, 2017 10:57 PM
Subject: RE: Wonderful fall

Pretty sure I could leave early on Friday!

mmmmm

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WrySmile wishes

October 23, 2017 Monday

from: Sassy
to: WrySmile
date: Mon, Oct 23, 2017 at 11:24 AM
subject: Re: Not goodbye

Hiya D! Hope your week is off to a grand start! Is there anything new going on with you?

You are the sweetest man… I so appreciate the offer to listen and be a friend. That is special. I don’t know if I can keep up my end of that, but let’s try. You are so smart and interesting and fun!

Thanks for asking about Hubby, and reminding me to check at the effects on me. He is back off the ledge, but still precarious. I am having to focus on him even more than usual. And it is getting to me more than usual.

I also appreciate your making the situation clear about us being in the friend zone. It may be useful to have a friend who understands a bit of the Ashley Madison dynamics etc. among his many experiences.

I hope things will calm down soon for me and I can get back to some fun conversations with you in my regular cheerful way!

-S

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from: WrySmile
to: Sassy
date: Mon, Oct 23, 2017 at 9:28 PM
subject: Re: Not goodbye

Sassy,

As I think you know, I’m just that kind of guy. I wish I had more friends I could share with, be mutually supportive with… and share secrets with without being judged. Married dating, dating websites, even sex fantasies and practices; my wife is terrific, but I certainly could never talk to her about these.

Here’s one that I can’t tell anyone else: I made a great dating connection with a woman in Quincy; everything seemed to click. Based on emails we would have been great together and we both wanted it to happen. We were about to meet, and…

I felt that I had to tell her that I love my wife. Boom! She called it off and cut me off. She said I had made her very sad.

Do you have a suggestion? Should I have waited until we met to tell her? Waited until I’d had a chance to grow on her? If it were me, I would have been furious to have this popped on me after we’d made a connection. I’m horny, but I’m not horny enough to do that. Especially not to someone I liked.

Was there anything else I could have done that would have been honest yet might have given us a chance?

Well, we’d both had gotten our hopes too high and now we’re both unhappy about it.

You asked about my Monday; it was annoying. It’s annoying to be ignored, but it’s infuriating to be ignored when you’re the only person in the room who truly understands the problem. I squirmed through a 45-minute discussion of something that should have taken 5-10 minutes.

Let’s stay in touch and keep trying to meet. Good luck in restoring (something like) normalcy to your life.

Darrin

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Wry Not Goodbye

October 21, 2017 Saturday

from: Sassy
to: WrySmile 
date: Sat, Oct 21, 2017 at 5:51 PM
subject: Re: goodbye

Hiya! Hope you got out to enjoy this beautiful day!

Please don’t take it personally that I have not been back in touch! I honestly meant to, but the past month has been a nightmare in three directions! My boss tortured me even more than usual, my project group was oddly busy, and my husband had a major nearly-suicidal episode! So, it was me and not you, dear man. I did not want to impose any of that crap on you, and barely had the energy to deal with that mess much less getting to know someone new.

I think often of our afternoon stroll and smile. You were so much fun to talk and walk with! 

However, I got the impression that I am not what you are looking for… I don’t look the way you want a woman in your arms to look, and the anal sex videos or having your cock in my ass is not a turn on, so I don’t want to waste your time. You deserve to have your sexy dreams come true with someone who is into your idea of fun and has a body that rocks your world! I wish you every success in finding her!

-S

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from: WrySmile 
to: Sassy
date: Sat, Oct 21, 2017 at 11:17 PM
subject: Not goodbye

Sassy,

I’m glad you responded.

What a horrible time. How is your husband now? And how well are you handling the aftermath? (I’m sorry for the pop psychology, but…) Please remember that the events were traumatic for you too and remember to take care of yourself. If it would help to talk to me – to vent, to get things off your chest, to cry to, for whatever reason, please let me know. I’m a good listener.

No, I do not want to have sex with you, anal or otherwise. But you’re a good person and I think you are fun and interesting to talk with. I’d really like to have more conversations and become friends. Not friends with benefits, but the friendship between two people who enjoy and respect each other. Everything I’ve written to you since our meeting I’ve written purely as a friend. Even the erotic stories were sent to you out of friendship, and not as a prologue to sex.

Does your crazy, busy life have room for a male friend you’re not having sex with? If so, let’s have lunch or tea or ice cream or a phone call and continue our conversation. If not, please say so and I’ll stop trying to keep in touch.

I hope your life is improving and will continue to improve. I’d like to play a small part in that.

Darrin