Weekend wishes

June 22, 2018 Friday
From: Sassy
To: Reggie
Sent: Fri Jun 22, 2018 at 2:48 PM

Subject: Friday finds

Hiya Reggie! Hope you’re having a fantastic Friday!

Work is rolling along – hiring people, interviewing people, paying people – crucial but tedious!

I had the blood tests this morning for the STD tests. Hope to hear the results next week.

Hubby is having dinner out, so I am on my own tonight. Hope to find something fun to send you with naked people doing sexy activities – maybe some oral or exhibitionists?

Still thinking of a kiss on the stairs… mouths, hands… mmm mmm mmm. Need to make more memories in private!

Have a wonderful weekend! Mwah!

-S

Adulting

June 21, 2018 Thursday

From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 8:15 AM
Subject: Adulting

Happy Summer! Hope your day is starting well.

Most days when I am heading to work, I have a mild case of “I’d rather be doing something else.” I’d rather sleep a bit more, go to the ocean and eat lobster, read fun stories on the internet, or have lunch with a friend. But I go to work. That’s what adults do most of the time. Go to work, eat dinner, talk with the family, do chores, read a little. Get ready to do it again. Adulting.

But today? I have one of the worst cases of what I have to do conflicting with what I want to do that I can remember. My mind screams to run and find you! The memories of our first meet are playing over and over, mixed with the myriad of possibilities for our next one. I don’t want to go to the office. I want to see you! Touch you… listen to you, taste you!! I long to invite you to lunch but I know you have other things to do.

This may have been the best first meet I’ve ever had. The first hug was a fantastic mix of comfort and excitement. There was that “rightness” of your arms around me, of the fit of our bodies close together. Then your smile… oh my. I relaxed enough to enjoy our conversation immensely. You are easy to talk with – an excellent foundation for whatever else we build. Thank you for talking about the past, the present and considering a future with adventure!

We went to a buffet last night, even though we didn’t eat anything. We sat and talked about many dishes – the appetizers, the meats, the vegetables, the rices and the sweets! We allowed ourselves one taste. I hope that wasn’t too scary. I couldn’t resist finding out a few more facts in that certain way. It was incredible! It set off all my senses! I want MORE! SOON!

Finally, thank you for quickly reassuring me that it went well… that there will be more. I want it…I want you. I want to rush, and yet take our time. I want to skip work and have FUN. Help me figure out the best way to do that? I will be in touch soon with some ideas. Have a terrific Thursday!

-S

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From: Reggie

To: Sassy
Sent: Thu Jun 21, 2018 at 9:55 AM
Re: Adulting

Sassy

Yes, I have been adulting since dawn and I know about this feeling only too well. Not a day goes by when I don’t think of my corporate enslavement and how I would rather be doing something else.

I loved chatting with you and learning a little about what makes you tick. Your sex-positive, vivaciousness is infectious. I like the self-assurance that you have about seeking sex – I must say I don’t. It is too wrapped up in subterfuge and some amount of guilt and your attitude is very reassuring.

I am eager for you to tell me about your ideas.

-R

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From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 11:33 AM

Subject: Meet planning

Hiya Reggie!

I am trying to work but… ugh. I’m supposed to be reading resumes and planning incisive interview questions to choose a new colleague, but I have to write to you!

Two logistical questions:

1) When?

As I thought about the logistics for our next meet, it suddenly occurred to me that lunches work for you and me but don’t work hotel-wise. They’re locked down from 12 noon – 3 pm. Argh. I have two theories:

– Afternoons
Can you leave work early, meet from say 3:30 – 5:30 pm?
I can do Monday, Wednesday or Friday next week at those times. Fridays are cheaper at a hotel.

– Mornings
Meet before work 8 – 10 am?
I can do that any morning next week.

If the answer is yes but it will take time to set up, I can wait. Somehow. If this is not possible, let me know and I will try to figure out something else.

2) Where?

Are you comfortable with hotels near work? Or would you rather be further away?

Close: Friday 6/29, I’m looking at the Marriott @ 50 Broadway $151. 

Further: Or there’s the Holiday Inn Express near McDonald’s/Twin City Plaza on McGrath Hwy for $146

Or I can look further around T stops heading up the Red Line for safer and/or cheaper spots.

Cash cab option: Green Cab 617-625-5000. I’d say pick an address up the block or around the corner for pick-up, so you’re less likely to be seen by colleagues and your office address is not in their records.

NOTE: These questions may only apply once, as after that I hope to have gained enough trust to invite you to my condo, which is walkable from your office. Hubby can work at a cafe and we can enjoy on our own schedule!

Very soon we’ll get through these questions and on to FUN!

More hugs… more groping… more!

-S

=====

From: Reggie

To: Sassy
Sent: Thu Jun 21, 2018 at 11:59 AM
Re: Meet planning

Your planning is impeccable. I am totally comfortable with hotels near work and Marriott sounds very doable. I just pretend to go to a work meeting which can be anywhere in the “sprawling” complex of buildings and go to the hotel. Maybe Friday next week but I will have to confirm that.

Damn..I am excited to see you in private. I want to see you naked. I want to touch you.

Did I tell you that I have a friend coming to visit tonight. He is in town for work and is visiting us for the weekend. My emails will be a little sparse over the next couple of days but I do want to hear from you about all the things you have been fantasizing about us.

=====

From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 12:30 PM

Re: Meet planning

Hiya Reggie!

Wow… don’t think anyone has used the word impeccable on me before… I am beaming! I worry that it is too much trouble, but I try to make it as easy as possible. Good that we have a theory rolling. I usually put a doctor’s appointment or something on my work calendar so no one schedules over whatever time I have planned to be with you. I use Dr AMY. AMy… heh. It makes me smile every time I look at it.

Let’s try to keep in the forefront what this is all about. SEX! Ha! That includes hugging, kissing, exploring, laughing, moaning, and penetration! And afterglow with cuddling and conversation.

We didn’t talk about frequency – I want to see you A LOT but I know there are many other pulls on your time and all plans are subject to change to keep you employed and safe. If we have fun and want to continue, I would hope for at least once a month. But whatever we can manage, more or less, I have that tingle that tells me each time will be a marvelous interlude.

I do have to warn about first times… they can be weird. But you have given me confidence that we can communicate and get beyond that. We can test things and check in and try other things and… have fun doing it! Please don’t be shy about saying or showing me what works best. Slower, faster, harder… I can adapt. And don’t take those words coming from me as criticism – just suggestions on how to make it even better.

Wonderful you get to see people! I do appreciate the heads-up, especially in these early stages. I try not to expect emails, just enjoy them when they appear, but so appreciate you removing any doubt that you’ve given up on me. I will try not to pester you too much, but my brain is full of possibilities and they may leak out in your direction.

Hugging, groping, kissing… like yesterday only in private and for much longer!

-S

=====

From: Reggie

To: Sassy
Sent: Thu Jun 21, 2018 at 12:40 PM
Re: Meet planning

lol@ Dr. AMY.

Yes, it is about sex and I would love for it to get to a place where it is uninhibited and immensely pleasurable for both of us. And I realize that the first time will be awkward. I know you can be open about things (while being kind, gentle, compassionate) and that means a lot in being able to open up and get to that place of sexual satisfaction for us both. I will try to be as well but I am (and I will say this without any shame) much more inexperienced than you are.

As for frequency – twice a month would be nice as long as we don’t have to spend on hotels. I like it that you think we can get to place where you can invite me over. I truly appreciate it.

=====

From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 2:35 PM

Re: Meet planning

Hee hee… told ya I have fun names for everyone.

We’ll see if we can up your experience level. I have a feeling you’ll catch on pretty quickly when you notice that I don’t react badly to what you say. Even if we don’t manage sexual perfection, I hope we can be “way better than nothing!” And have fun practicing. 😉

Are you used to running things in the bedroom? I will mostly let you do that, at least to start, but don’t want to shock you if I try to have a turn at deciding what’s next. Most men seem to be stuck in the “she lets me…” and I want you to know I am not just letting you, I am into it too!

Twice a month? Oh sweet man… that sounds amazing! I will not expect that but it sure is fun to think about!

My instincts say I could have you over right away but my experience tells me to wait. Giving away where I live is a huge Full disclosure – My place is a cluttered wreck due to Hubby’s current reorganization effort and his general lack of interest in un-cluttering, and the cats best efforts to create chaos. But I do have a cleaner in regularly, and I keep the path to the bedroom and my uncluttered bathroom clear! I hope if there is a king-sized bed, a bathroom, and me, you’ll be okay. It is an excellent place for a tryst, as someone might see you go in, but they’d have no idea which of condos you go to. We can even take you in through the garage which is hidden from the street, if that extra step helps your peace of mind.

One other thought – I do not own you or demand exclusive sexual rights. What you do on your own time is your business, as long as you stick with safe sex, and treat me well when you see me and write me now and then. 🙂 If you get other chances, take them. Tell me about them or not, as you see fit. Let me know if you want to hear about mine or not. I recommend talking about things, but I know that may seem radical to you. Right now the only man I see is The Northerner on the rare occasions he can get away. I will say, the thought of being with you will keep me from prowling. I hope that makes sense.

Off to interview. Keep smiling. And daydreaming. Mwah!

-S

=====

From: Reggie

To: Sassy
Sent: Thu Jun 21, 2018 at 3:40 PM
Re: Meet planning

I am a little naive when it comes to risks that I put myself through unlike your other friend who “forgets” his wallet in his car. Nor do I mind clutter as long as it is not on your bed 😉 I don’t know about taking charge in the bedroom but I will not come to you after the first couple of times and say that I am sub and wanted to be domme’d – that will not happen 🙂 As for other encounters – there is one other and I will tell you about her when we lie in the afterglow and touch and talk.

I have been feeling very aroused and I think I need relief. Right now, in the restroom at work!

=====

From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 5:20 PM 

Re: Meet planning

Hiya Reggie!

You are so cute. I wouldn’t call you naive – you’ve had no reason to know all the crappy things that can go on. I happen to have listened to people in IRC and men from AM for awhile. With some luck I can warn you of ones you need to know, and you don’t need to worry about most of the awful things. I don’t want to be a downer, but I do want you safe. Remind me to tell you about the bank robber. You’re not a bank robber right?

If you have any kinks – things that you need to get off – be sure to say. I can’t tell what is kinky anymore. One guy was shocked I want to leave the light on, and several who thought blow jobs were wild. And then the guy who wanted to listen to me poop! Called him Mr. Scat and never went there!

Did I say something arousing? Feels like all I did was logistics today. Or are you remembering or planning for the future? Did you really go get relief? Mmm…. may have to get you to film bits of that sometime and send it to me! I adore watching and listening in.

-S

=====

From: Reggie

To: Sassy
Sent: Thu Jun 21, 2018 at 10:11 PM
Re: Meet planning

Hi Sass

I like listening to your experiences. You come across as genuinely curious and caring about your lovers while not being judgmental at all. Not even about Mr. Scat. 

We will have time to talk about kinks. I definitely do like lights on. I told you that I like lingerie and heels but you are not too much into them. I love oral sex. More later – right now, entertaining our visitor.   🙂
=====

From: Sassy

To: Reggie
Sent: Thu Jun 21, 2018 at 11:05 PM

Subject: Summer evening

Hiya Reggie!

Hope you’ve had a fun evening and your visitor made it into town easily. How old a person is he?

I managed to get work done and go out to Border Cafe for dinner. Their gumbo and crawfish etouffe are delicious! All I wanted to do was write to you but I kept on with “real life” placated by the thoughts of seeing you again.

Sleep well! Dream sexy dreams of a bodacious buxom beauty who is thinking of you!

-S

Meet #1 Grabbing Reggie

June 20, 2018 Wednesday

From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 6:28 AM
Re: Until tomorrow

Wow! Wow. I…um…wow. what a way to start my day! Thank you.

10 hours!


Sent from Yahoo Mail on Android

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From: Reggie

To: Sassy
Sent: Wed Jun 20, 2018 at 7:42 AM
Subject: Today is the day

And now 9

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From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 7:44 AM
Re: Today is the day

Hee hee. Yes!

Today’s gonna be a good day!

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 9:18 AM
Re:Today is the day

Lower your expectations hot woman 😉

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From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 9:37 AM
Re: Today is the day

Ha! I have no expectations. Can’t lower them!

Do hope to be pleasantly surprised.

7 hours…tick tock tick


Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 9:39 AM
Re: Today is the day

🙂 I have meetings all day and my mind is so fuzzy.

=====

From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 12:53 PM
Subject: Sassy time

Hiya! It’s afternoon…less than 4 hours until I see you, hear you, smell you and hug you!

I have meetings too. Luckily the last one of the day is with you! So excited!!

See you soon. Almost Sassy time!

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 12:54 PM

Re: Sassy time

Hi. See you very soon, Sassy.

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 2:56 PM

Re: Sassy time

One last meeting and I am done for the day.

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 3:57 PM

Re: Sassy time

See you soon, Sassy!

=====

From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 4:18 PM

Re: Sassy time

Are you inside already?
=====

From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 4:25 PM
Re: Sassy time

Yes! Come on down! And get sassed.

Sent from Yahoo Mail on Android

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First meet with Reggie

I left the office a little early and made my way to John Harvard’s in Harvard Square so I would get there before he arrived. I usually want to get there after the guy but I had a feeling this would be okay. He emailed while I was on my way. I prepped an email to send when I got inside.

I sat at the end of bar under the stairs where there’s a wall behind the stools and a wall to the right and the bar blocks any front on views. A great spot for touching without anyone seeing.  I sent him email to let him know I was there.

The cute young lady bartender came over and I ordered an iced tea. Another woman brought it to me. Just as I was about to take a sip, Reggie appeared! He spoke standing behind me. I whipped around, jumped down from the stool and hugged him. Oh yes… he is taller than I am and we fit together nicely. He squeezed just a bit and I stepped back. We grinned at each other and stood staring for a few moments. He had on a dark blue knitted golf shirt with a collar and pleasantly worn blue jeans.

Sendhil Ramamurthy 
I was overwhelmed with how handsome he is! And how young.  And immediately hit with the big question, “Why would such a man be interested in me?!” I pushed that into the back of my mind for now.

He pulled out a stool on my left and commented on the privacy of the corner. I said I felt like a hussy for knowing such things but the knowledge comes in handy! We stared some more, and grinned more. I imagined him visibly relaxing. The bartender asked what he’d like to drink and he ordered a dark beer. She asked if we wanted food – I deferred to him – he said he didn’t need anything so I went with that. 

He asked me questions. I adore that, when a man is interested enough to ask and listens to my answers. We talked about how we came to live in the area, our travels, how we met our spouses, my community project, his hobbies. He is such an interesting mix of sophisticated businessman, world traveler and a shy, sweet relatively inexperienced sexual man.

I told stories and he told stories and it was so easy to talk with him! We laughed and I touched his arm. He gave me a side eye and touched my knee. I touched his knee. He waved a hand to emphasize a point, and brushed my breast “by accident.” Ha! This is such fun.

I asked when he needed to go – he checked his watch – an hour had gone by so fast! He sighed, said he should leave. Then kept on talking and ordered another beer! I asked if the beer helped his nerves – he said it made it a big easier but I was helping him feel at ease too. Phew.

He asked if I knew of places for a second meet. I said I do. He asked for details. I said, “a hotel” and watched to see if that made me a total hussy. He nodded and looked like that would be okay. I told him I could arrange it, charge it and he could pay me cash. He said that would be fantastic! I said, “If you decide you want to,” and he grinned and said he had already decided. I asked if he has a theory of when – he asked if weekdays during the day can happen. I assured him I can have a “doctor’s appointment” or take time off because I get lots. He asked if lunch time would work for a couple of hours. I said I could. I was amazed we were already into logistics for a second meet! Wow!

I told him we might be able to meet at my place in the future but I needed to see him at least once somewhere else to build up trust, that it was not him but that I had had a bad experience. He asked about that. I told him I was attacked. He looked shocked. I told him I wasn’t careful, that the law of averages caught up me, but I used it to learn lessons and be more careful. He nodded and touched my arm. He is so sweet!

He said he really had to leave. He signaled the bartender for the check. I offered to help pay but he waved me off. I told him doesn’t always have to pay. He said he’s old-fashioned that way but we can talk more about that. He said he’d have to check his schedule, but he’d email me tonight. Please let that be true!

He asked to be excused to use the bathroom. I asked if he wanted me to follow him and he declined, but quickly asked if he could have another hug up on the darker part of the stairs on the way out? I nodded. Probably for the best, though it worried me that he didn’t want to be alone with me.

He returned quickly and we went up the stairs. We got to the landing where no one could see us from above or below. He turned to me and smiled and we grabbed each other. I put my hand on his cheek and he put his arm around my waist to pull me in close and we kissed, tentatively at first but then fiercely! He moaned into my mouth… oh my. He grabbed my breast. I angled a bit so I could rub the sexy bulge between his legs. He is so sexy! I would have gone on and on but he wisely pulled back. The door above opened and a man started down the stairs.  We jumped apart and continued up the stairs and out to the sidewalk.

He pointed to the left, said he was off to the train. I told him I wanted to walk with him but it was a bad idea. He nodded and repeated his promise to write me soon to make a plan to be alone. I smiled.  He grinned. 

He took off to the left and I went off to the right. I glanced back once to watch him walk. I felt really calm in a way I rarely do. My instincts said I will him again. I marveled that he wants me. But I want to believe it!

I sat down at a cafe table across the street and called Hubby to talk him into coming to get me and go out to dinner. He agreed after I named one of his favorite restaurants, so I sat and re-lived the meet and fantasized about the next one until he appeared. We certainly got through the toughest parts with aplomb. This may have been the best first meet ever!

Reassurance came quickly – bless him.

=====
From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 6:22 PM

Re: Sassy time

Mmm mmm mmm

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From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 6:47 PM
Re: Sassy time

Oh yes.

Sent from Yahoo Mail on Android

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From: Sassy

To: Reggie
Sent: Wed Jun 20, 2018 at 9:07 PM
Re: Sassy time

Thank you for the drink and so much more! I had such a good time.

You are so charming. And tasty. ; )


Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Wed Jun 20, 2018 at 7:48 AM

Re: Sassy time

It was lovely meeting you and easy to talk to you. I had a lovely time as well. Let us plan to meet again soon.

So aroused now

June 19, 2018 Tuesday

From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:13 PM
Subject: Tuesday Titillation
Hi Sass

Haven’t heard from you. All well? 

I kept thinking of how you imagined me with my knees on either side of you feeding you my cock, my hands on your headboard bookshelf. I am getting hard again thinking about it at work now.

-Reggie

=====

From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:13 PM
Re: Monday Musings

Oh yes…I know about your gorgeous cock – stared at the photo you sent for a long time!

I’m with Hubby at the doctor for his routine checkup. Whee. 

Thinking of tomorrow while we wait. Of getting to find out so many things – your smile, your laugh, your voice!

Sent from Yahoo Mail on Android


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From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:18 PM

Re: Tuesday Titillation

So happy to hear that was a…useful image to plant in your brain. When did you cum last?

All is good. Wacky morning at work, ran catering for an all staff lunch, then raced out to take Hubby to Kenmore.

Now I’m picturing sitting with you at the bar, hearing your stories and trying not to grab you!

-S

=====


From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:22 PM
Subject: Gif for you

Nsfw!

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:24 PM

Re: Tuesday Titillation

I last came yesterday morning reading one of your earlier e-mails. Woke up with thoughts of you and jacked off in the bathroom.

John Harvard bar if I remember right is so open and exposed that even the casual touch of our legs as we sit close to each other is going to be visible and get me all worried 🙁

=====

From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:26 PM

Re: Gif for you

Mmmm…I want to watch my cock disappear into you!

=====

From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:28 PM

Re: Tuesday Titillation

I’m so happy to inspire you to do sexy stuff.

I will behave. I will be tempted not to and I may say sexy things but anyone watching will get a definite business meeting vibe. I want to keep you safe.

25 hours…

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:31 PM

Re: Tuesday Titillation

I will be tempted to as well – that is my bigger worry 🙂

Is the disabled bathroom really an option? Will the waiting staff not know?!

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:31 PM

Re: Tuesday Titillation

Damn, I am so aroused now!

=====

From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:36 PM

Re: Tuesday Titillation

Is that okay? Does it feel good? Hope so!

-S

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:39 PM

Re: Tuesday Titillation

The record you said is 7 times in 2 hours? 😉

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From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 3:34 PM

Re: Tuesday Titillation

Ah…I see. Gosh I hope that’s true tomorrow! We can deal.

Accessible bathroom? Yes. For a short time. They’ve never paid much attention. And we’ll make sure they only see one of us at a time. It’s rather hidden. It is fun to consider? Don’t feel pressured at all. We can make other plans.

Tomorrow is more about filling in lots of puzzle pieces…asking questions better not done in email, checking the chemistry, may be a little more? Do you have other goals?

=====
From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 3:49 PM

Re: Tuesday Titillation

I agree that tomorrow is more about seeing if there is a spark and there is chemistry. I don’t have a “goal” at all.

Can’t wait to see you. Will I just walk into JH and see you there? Or will you come in after I do?

=====

From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 4:07 PM

Re: Tuesday Titillation

Sounds like we’re on the same page.

Which do you prefer?

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 4:08 PM

Re: Tuesday Titillation

I’d love to walk in and see you there 🙂 If you don’t mind, that is…

=====

From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 4:56 PM

Re: Tuesday Titillation

I should be able to do that. 🙂 23.5 hrs!

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 4:58 PM

Re: Tuesday Titillation

Mmmm. I am at a point where even a simple e-mail like that from you sends a pulse through my loins 😉 Is that crazy?

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From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 6:31 PM

Re: Tuesday Titillation

Totally wacky. And wonderful!

Sent from Yahoo Mail on Android

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From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 7:11 PM

Re: Tuesday Titillation

I’m home after a yummy dinner at the Yard House in the Fenway.

Sitting on my bed, changing clothes, thinking of you. There’s a mirror, so I could touch you and you could watch two ways. Mmmm. A simple concept that can enhance your pleasure a lot!

=====

From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 8:25 PM

Re: Tuesday Titillation

I love mirrors in the bedroom. I’d love to watch you and me in the mirror. Mmmm

Sent from Yahoo Mail on Android

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From: Sassy

To: Reggie
Sent: Tue Jun 19, 2018 at 8:54 PM

Re: Tuesday Titillation

Is it kinky that I like the light on?

Sent from Yahoo Mail on Android

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 10:36 PM

Re: Tuesday Titillation

It is kinky and it is good that you do. I would not have it any other way. I want to see as much as touch, smell, taste!

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From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 11:10 PM

Subject: Until tomorrow

Something for you…

[photo of him naked from chest to knees in a bathroom mirror standing sideways so his erect cock sticks out]

Super-naughty

June 18, 2018 Monday

From: Reggie
To: Sassy
Sent: Mon Jun 18, 2018 at 10:52 AM
Subject: Monday Musings

Hello Sassy

Got back in town late last night and had a rather intense weekend – so haven’t been able to respond to past e-mails. Landed into a brouhaha at work. C’est la vie.

I too have been thinking about our meeting. I may be a little awkward and shy in our first encounter as well. Especially with thoughts of all that you have hinted at. I like your adventurous, sensual but always compassionate style. I am thinking of your hand on my growing tumescence as we kiss passionately.

What did you wear to work today?

-Reggie

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From: Sassy

To: Reggie
Sent: Mon Jun 18, 2018 at 3:00 PM

Re: Monday Musings

Hiya Reggie! Hope your Monday has calmed down. It’s strange how Monday has such a bad rep and often ends up deserving it! I had to hit the ground running – we have a new temp and the boss assigned me a list of a dozen things to get her up to speed on.

We’re going to be fine on Wednesday. I keep telling myself we’re grown-ups, used to meeting new people. We can deal with whatever. If you sense any possibilities, give me a sign and we’ll roll in that direction. We can go as fast or slow as we like. If not, let me know – no harm, no foul, it’s been fun, best of luck. I do appreciate your giving us time to get to know each other before meeting! Makes me so much calmer.

I have on blue slacks, a blue shell short sleeve top with a wiggly pattern in white, a black bra, white panties, black socks and shoes. Very demure business lady. My hair is tied back so I don’t melt! What’re you wearing? It’s fun to think about helping you out of it so I can explore your sexy body!

Definitely thinking about hugging and groping but I try to behave until I know which way things are going!

-S

=====

From: Reggie
To: Sassy
Sent: Mon Jun 18, 2018 at 3:25 PM

Re: Monday Musings

I have on a tan T-shirt and dark blue jeans. My underwear – black boxer briefs.

Looking forward to Wednesday!

=====

From: Sassy

To: Reggie
Sent: Mon Jun 18, 2018 at 3:30 PM

Re: Monday Musings

Oooh. Thanks for saying! I am musing about sliding my hand under that shirt to find a nipple to tweak. and down inside those jeans and… watching your face. And squirming in my desk chair. So good… mmm.

-S

=====
From: Reggie
To: Sassy
Sent: Mon Jun 18, 2018 at 3:32 PM

Re: Monday Musings

Mmm..that got me instantly hard. I am imagining you unzipping me and your soft hands fondling my balls, veiny uncut hardness. I want to touch your wetness when you do that.

=====

From: Sassy

To: Reggie
Sent: Mon Jun 18, 2018 at 5:30 PM

Re: Monday Musings

Sounds like a wonderful idea to me!

I’m home. Sitting on my bed…fantasizing

-S

=====
From: Reggie
To: Sassy
Sent: Mon Jun 18, 2018 at 8:39 PM

Re: Monday Musings

Did you fantasize? What did you do? What did you think of?

=====

From: Sassy

To: Reggie
Sent: Mon Jun 18, 2018 at 8:47 PM

Re: Monday Musings

Oh yes. I was super-naughty! I imagined you there with me… helping each other get naked then enjoying your talents at giving oral, then you putting your knees on either side of my face, your hands on my bed’s bookcase, your cock down my throat! Could happen, right?

Then I ordered dinner delivered. And dealt with an Instacart delivery. *sigh

Hope your place has a/c! The weatherman used the technical term, “Beastly hot” today. Ha.

We had a fierce thunderstorm about 7:15 pm. I thought of “The Storm” and you. It’s 20 degrees cooler!

What have you been doing? Hope you are smiling and hard as a rock. 😉

-S

=====
From: Reggie
To: Sassy
Sent: Tue Jun 19, 2018 at 12:03 AM

Re: Monday Musings

Do you know what that cock looks like Sassy? 8.5″ when fully turgid. Veiny. And a dark dark brown. Oh, and did I mention, uncut?

If I was close

June 17, 2018 Sunday

From: Sassy
To: Reggie
Sent: Sun Jun 17, 2018 at 8:44 AM
Subject: Sunday surprises

Happy Father’s Day! Hope you have a fantastic day with your friends!

I’m thinking of you and how I’d make this day special if I was close to you. Mmm…

I’m off to brunch!

-S

Sent from Yahoo Mail on Android



Sweet kiss

June 16, 2018 Saturday
From: Sassy
To: Reggie
Sent: Sat Jun 16, 2018 at 10:45 PM

Subject: Saturday sundries

Good evening Reggie! Hope you had a delightful day. It was mostly quiet here other that a short foray out for a meeting.

I had lots of time to think about you… meeting you. Got kinda shy about it but am fighting that! It feels like starting over in a parallel universe. Hope we can merge it with this one easily.

Hugs with groping and a sweet kiss good night!

-S

Shaved or natural?

June 15, 2018 Friday

From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 10:12 AM
Subject: Friday fun

Good morning Reggie! Happy Friday! Hope your day is off to a grand start.

I got to fast this morning and have blood test done for routine check-ups. Whee!

Do you usually eat breakfast? I am snarfing a lovely bowl of greek yogurt with fresh blueberries and granola from Flour Bakery. Do you ever go there? It’s mostly evil bliss in terms of sugary baked goods, but they do have some innovative healthy items!

Anything fun for your weekend? We’re going to see theater tonight – Shakespeare’s “Midsummer Night’s Dream” in the park. 

Saturday I have a quarterly community non-profit meeting in the afternoon. Running a 501(C)3 is a bit tedious. Sunday is another brunch with my older sister and her beau.

Gotta go do the payroll! Maybe you can think about hiding under my desk and distracting me with your tongue. Hee!

-S

=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 12:39 PM
Re: Friday fun

Good afternoon, Sassy.

Suddenly, I have a tranche of work that has landed on me and I am scrambling to finish up before I head to go away for the weekend to meet a friend. 

I love Flour Bakery and used to go to the one in the Seaport area all the time when I worked there.

Thanks for telling me about Midsummer Night’s Dream – we might go for it next week perhaps.

Enjoy your weekend and do write if you have a moment.

*kiss* *hug* *lick*

-R

=====


From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 4:29 PM
Re: Friday fun

Hiya Reggie! Hope you rolled through your work and are off to an excellent weekend! Safe travels! Please look both ways crossing the street and come back healthy. Nothing bad can happen to you before I get to see you! Take selfies and email them to me?

I actually took a few minutes in envision us talking, then kissing, hugging and licking! Oh my… I can’t quite fill in all the pertinent details but I hope to soon. Along with details about other activities soon after that? mmm… maybe you will find that spot on my back that makes me squirm in the best possible way? Mwah!

-S

=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 4:38 PM
Re: Friday fun

Mmmmm…Are you shaved or natural? Or in between?

=====

From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 4:42 PM
Re: Friday fun

Oh you… Natural but sparse. I lost it all during chemo and it came back soft and thin. You?

Sent from Yahoo Mail on Android


=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 4:47 PM
Re: Friday fun

Trimmed

=====
From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 5:07 PM
Re: Friday fun

Mmm… nice. Gonna play there!

Sent from Yahoo Mail on Android

=====
From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 6:08 PM
Re: Friday fun

Eating sushi in Somerville. Yoshi, across the street from the show. Remember you said you like it…

Ever been to Toraya in Arlington? So tasty!

Hugs with groping and another ear nibble!

-S

Sent from Yahoo Mail on Android


=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 6:18 PM
Re: Friday fun

Toraya is wonderful. Eat some unagi for me. 

Enjoy the performance. 
On my way to the airport
=====

From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 6:22 PM
Re: Friday fun

Ah, you like Toraya? I see that as an excellent harbinger of good things to come. AND I just had unagi. 😉

Are you on JetBlue?

Sent from Yahoo Mail on Android


=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 6:32 PM
Re: Friday fun

American. Why?

=====

From: Sassy

To: Reggie
Sent: Fri Jun 15, 2018 at 10:30 PM
Re: Friday fun

Just wondered. Last time I flew I was on JetBlue.  And if there is a crash, I don’t want to be wondering if it was your plane!  

Hope the flight was uneventful and you’re having fun. I’m off to tumblr to look at naughty photos and imagine it’s us. Ha!

Sent from Yahoo Mail on Android
=====

From: Reggie

To: Sassy
Sent: Fri Jun 15, 2018 at 10:32 PM
Re: Friday fun

Landed. Flight was fine. I have my kid with me. 

Enjoy the rest of the night and weekend
=====

Titillating emails

June 14, 2018 Thursday

From: Reggie
To: Sassy

Sent: Thu Jun 14, 2018 at 3:43 PM
Re: Wednesday waiting

I never replied to your e-mail because I had to leave early yesterday for a meeting at school year-end. And then, this morning, our entire team had a meeting!  I was thinking of you. 

I don’t know whether I would be so bold as to sneak into a handicapped bathroom for a kiss. I must confess that it has been part of many fantasies to do that and more in such places but I haven’t actually done it. 
As for your “random” question – no, I am not allergic to cats.

Question for you – are you multi-orgasmic? Do you orgasm easily? Are you loud? 🙂

=====

From: Sassy

To: Reggie
Sent: Thu Jun 14, 2018 at 4:59 PM
Re: Wednesday waiting

Hiya Reggie!

Busy man! No worries. I know you have things to do. Fun to hear about them!

Hmmm… maybe we can fulfill a fantasy or two or more… the bathroom thing is quite easy. You can think about which makes you more comfortable… you go in and I join you 20 seconds later? Or I go in and you join me?

The key is not to stay long, so not get too crazy, but for a lovely test of the “is she THE BEST KISSER EVER?” and “Oh… I see what hugging and groping can mean!” and perhaps even some cleavage flashes… it’s excellent. Just lean against the sink or press against the wall and mmm mmm mmm. But we do not have to. We can wait. Stretch out this tasty torment.

Ah… orgasms. You are so cute when you ask direct questions. Can you cum twice? I only ask so know whether to hold back or help you over the edge with a blow job and know you can also be inside later if you like. There was a man who told me he was a “once-and-done” – I used my “mad skillz” and he was able to. It’s awesome when someone says they haven’t cum twice in 20 years and they’re exploding the second time! Oof… I am sounding like such a hussy again! Whee! If these tidbits bother you, just say and I’ll stop.

For me… it depends. One man helped me cum 7 times in two hours. Some men I had a grand time but didn’t quite make it to a physical completion. If it’s tricky, I may suggest different positions or bring in a toy to help. I aim to not fret about it much and keep practicing until we get it right. I am loud if circumstances allow. 🙂

I’m off to a community project meeting – may not reappear until later tonight.

Hope that helped rev you up! Mwah!

-S

=====

From: Reggie
To: Sassy

Sent: Thu Jun 14, 2018 at 5:15 PM
Re: Wednesday waiting

Oh, I would love to kiss and grope in the bathroom except what happens on the way out is what I wonder. Oh, I am so eager to discover your kisses.

Seven times in two hours is indeed very intense.I love the female orgasm and love being part of inducing them 🙂 It is my biggest turn on.

What project are you working on? 

=====


From: Reggie
To: Sassy

Sent: Thu Jun 14, 2018 at 5:44 PM
Subject:  Thursday thoughts…

I wish I had your turn of phrase when it comes to being so tantalizing in your e-mails. Thanks for putting in the effort to write such titillating e-mails. I look forward to them.

Enjoy your evening, sexy lassie!

=====

From: Sassy

To: Reggie
Sent: Thu Jun 14, 2018 at 7:12 PM
Re: Thursday thoughts…

Awww… come on. You write beautifully… charming, sexy, fun! Your words certainly get me going. You’ve taken me from zero to 100 mph!

If you like, as an exercise, turn off your filters. Write what you are thinking. Be completely real. Ask what you want. You are used to screening what you write, being polite, being careful, not “going there.” Go. I’ve seen flashes of it – turn it up. In my brain, it means shutting the door on the demure lady and letting my Sassy side write.

Imagine a woman who will do what you want, answer honestly, and not just to please you but enjoy it herself. Who wants to hear it. Who wants to know. Who will gladly talk about it… and smile while you look and touch and suck and… mmmf. I give you permission to “misbehave.”

If you want to wait until after you’ve seen me, I understand. or if you don’t have time.

If your wishes are not my thing, I will tell you, without judgement. I’ve rarely had to do that – the results have been quite fascinating.

-S

Fantasy and planning

June 13, 2018 Wednesday

From: Sassy
To: Reggie
Sent: Wed Jun 13, 2018 at 2:09 PM
Subject: Wednesday waiting

Good afternoon Reggie! Hope your Wednesday is going well.

Welcome to the Wednesday edition of my real life mixed with sexy fantasies and what-ifs!

My boss is off the next two days, so she’s on a mission to do EVERYTHING RIGHT NOW before she goes! Heh. Just 3 more hours and I will have a quieter time for the rest of the week.

I had a delightful Thai bento box lunch at 9 Tastes with a temp who is leaving. She’s headed to London for two weeks to visit a brother diagnosed with stage 4 cancer. *sigh

I’m thinking about next Wednesday… maybe see you if the scheduling fates allow…stare and smile and laugh at this strange and wonderful situation that can add a bright space in our lives. I’m having visions of simple things…must be careful in public but perhaps a short hug to see if we can fit vertically that might transfer to horizontally? Perhaps a hand on your arm to emphasize a point? Or my thumb on the inside of your wrist rubbing little circles… hmmm. Probably should not put my fingers on your fly, slide down the zipper and sneak inside to touch skin, eh? Bad Sassy…

I hope you’ve done this before with good results so there are positive associations. Is there anything more I can do to make it easy for you? Anything else you wonder? I want to up the excitement quotient and decrease the terror as much as possible!

Mwah!

-S


=====

From: Reggie

To: Sassy
Sent: Wed Jun 13, 2018 at 2:17 PM
Re: Wednesday waiting

HI Sassy

Delighted with your hump day e-mail with the little dose of fantasy and planning. 

I am awkward at first meetings but having done this a few times now, it won’t be that bad, I promise. 
As for the little touches..my hand on your knee or the accidental (not quite) brush against your breasts. We have to be really careful and discreet in public 
(btw, have you noticed how many people on AM want to have “discrete” experiences. I wonder…versus “continuous” experiences?). 
Eventually though I want to feel your touch all over me. Do you know where we can go from a public meeting? I mean, the logistics. But it can all be worked out in time.

*kiss*

R

=====

From: Sassy
To: Reggie
Sent: Wed Jun 13, 2018 at 4:55 PM

Re: Wednesday waiting

Hiya Reggie!

Is it time to leave yet? 🙂 I’ve done all I can at work today, so I will write to you!

Discreet. Oh yes. That was a constant refrain in the philandering chats I used to frequent. Women say over and over, “…and he can’t even spell discreet!” Heh. However, it does not indicate much about a man, i.e. good men don’t know how to spell it, so I try to ignore it except for a little giggle, and appreciate the thought.

How high should I up my hussy quotient? Hmm… should I admit knowing that John Harvard’s has a large handicapped bathroom where two people can pop in for a brief kiss? Mull over that. 😉

As for a second meet, I know several options. More on that when it becomes important.

Random question – are you allergic to cats? It’s tough to give a man a blow job when he’s sneezing. Don’t ask me how I know!

-S