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
June 15, 2018 Friday
From: Sassy
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.
Gotta go do the payroll! Maybe you can think about hiding under my desk and distracting me with your tongue. Hee!
-S
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From: Reggie
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.
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
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From: Sassy
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
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From: Reggie
Mmmmm…Are you shaved or natural? Or in between?
From: Sassy
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
Trimmed
Mmm… nice. Gonna play there!
Sent from Yahoo Mail on Android
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
Toraya is wonderful. Eat some unagi for me.
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
American. Why?
From: Sassy
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!
From: Reggie
Landed. Flight was fine. I have my kid with me.
June 14, 2018 Thursday
From: Reggie
To: Sassy
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.
Question for you – are you multi-orgasmic? Do you orgasm easily? Are you loud? 🙂
From: Sassy
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
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
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
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
June 13, 2018 Wednesday
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
HI Sassy
Delighted with your hump day e-mail with the little dose of fantasy and planning.
*kiss*
R
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
June 12, 2018 Tuesday
From: Sassy
Good morning! Hope your Tuesday is rolling along well! Such amazing weather… makes it tough to stay in the office.
A week… does it feel like a week we’ve been talking? Wow.
Three more questions? I’m thinking about drinking! and you!
1) Day drinks – Are you a coffee drinker? Tea? Diet coke? Mostly water?
I’m an iced chai latte gal first thing, but mostly stick to cold water. I either make it at home from a Tazo box or at work from the stash of free Keurig cups. I never took to hot drinks except when I’m sick.
When I got to college, the second year students told me I would learn to stay up all night to finish a paper, drink coffee and stop listening to John Denver. None of that happened!
2) Night drinks – Are you a wine man? I think you mentioned something about that. Beer? Cocktails?
Sadly, I can not drink alcohol. Not even cough syrup. My stomach rebels. I miss being able to sample Sis’ wine cellar or a good rum cake or a festive frou frou frozen daiquiri!
I order iced tea or Thai iced tea with dinner out, or a ginger ale or Shirley Temple if I’m feeling festive. I adore places that have festive non-alcoholic drinks on their menu.
3) May I drink with you? Do you know enough about me to feel like it’s worth a look? A hug? I’d like to hear you laugh.
-S
Re: Tuesday times
It is so hard to be in office. I should be out cycling, walking, running or just sitting on a park bench and contemplating life. As should you and everyone else. “We have no time to stand and stare”
1. Day drinks – I have a cup of coffee in the morning and then a nice large pot of tea in the afternoon. Unlike you, I don’t like cold drinks. I drink my water at room temperature and the only really cold thing I will drink is beer.
2. Night drinks – I like alcohol in many forms and worry about how much I drink but my GP assures me that I am not an alky. Yet. It is not as bad as you are thinking – I end up drinking about 12-13 drinks in a week which is well below acceptable limits. I like beers (IPAs, APAs, Stouts). I like red wine – full-bodied and dry – Bordeaux, Chianti, Cabs. I love Islay Single Malt Scotch.
3. Would love to drink with you. This week is getting so full with the end of the school year and some event or the other in the evenings. I am flying Friday – away for the weekend. But next week? I want to see you…
Re: How to stay under the radar
This is such a well curated list! It is interesting to see your commitment to this 🙂 Lot of useful info here. I should delete and I never do!
From: Sassy
Hiya!
So fun to hear your drinking preferences. They sound quite civilized!
I forgot I do enjoy afternoon tea in the English way. A gal pal and I went on a hunt over the past year for the best fancy afternoon tea served in Boston and made our way through the big hotels – the Taj, the Langham and Rowes Wharf. The final one is the answer! We sat overlooking the harbor, at a table strewn with rose petals, noshing on tiny sandwiches and sweets, sipping one of their house blend teas freshly steeped at the table! So civilized! I tend toward vanilla rooibus or hibiscus teas at those occasions but am totally open to sampling your favorites! Am I allowed to add milk and sugar or is that sacrilege?
So next week… pardon me as I put my admin/scheduler hat on – I’ll toss stuff out there but feel free to propose other ideas as I don’t know your parameters.
Here’s what my calendars say:
Midday – Monday, Thursday or Friday
Late afternoon or evening – any day except Tuesday
Decisions:
1) What day?
Goals – see you, hug you like an old friend, talk, see if there’s chemistry, touch, perhaps kiss?
I usually find first meets a little strange… second meets are tricky as we figure out which…dance and steps, but if we can get past that, third meets are spectacular!
Hope this is sounding appealing… we’ll get past logistics and on to FUN soon!!
-S
Re: Next week’s drink
I love it that you are so organized and think of everything. I really do. I am stumbling and bumbling my way through this and feeling so awkward but you are sure footed and that is lovely. You have thought of everything including goals for the meeting. Love it.
So, at this point, possibilities are:
1. Drinks late afternoon on Monday or Wednesday – say around 4:30 pm?
2. Lunch on Thursday.
Place: I like John Harvard’s. MBTA friendly is good and you know Cambridge far better than I do.
Yes, first meetings are strange but you are making it easier.
Related to the general do’s-don’ts of cheating that you sent out earlier, do you have a view on STIs, especially in the AM world? I worry about it constantly although, I have been (I think) safe and limited so far. Do you have a HOWTO on it?
I am thrilled to be meeting you..touching you.
From: Sassy
Hiya!
Thank you for responding so quickly. It is reassuring in lots of ways.
Oh this is so exciting!
Let’s aim for Wednesday at 4:30 pm at John Harvard’s – sit at the end of the bar nearest the stairs if that works. Perhaps save lunch Thursday as a Plan B if something messes up Wednesday?
Ah… we’re down to brass tacks now! May not need to think about STDs for the drink, but I understand how important it is. I lost numerous friends and colleagues to AIDS in the late 80s, and my best friend in 1996, None of them were my sexual partners, but I know the risks. I waffle between wondering if I am risking my life with someone who is likely to lie, and not worrying about it much other than asking for condoms. If you need me to buy them and store them to keep safe, let me know which brand.
So glad we are taking the chance to touch!
-S
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Re: Next week’s drink
Sounds good to me. My schedule changes quite a bit and so, we will have to reconfirm this on Monday / Tuesday. Hopefully, you will not be too disappointed if there are any changes.
The STI question has been bothering me, not so much because I have unprotected sex which I don’t but mostly because I am very orally inclined and I don’t particularly like the idea of licking with a saran wrap on something beautiful. Also, I have only been with my wife and one other person recently – so, the anxiety is directed to the future and not the present 🙂
-R
From: Sassy
Good evening!
Don’t fret if your schedule changes. We’ll roll with it. I know stuff happens.
Ah… I get it now. IRC folks on the West coast often talked about genital herpes and chatted up dental dams and female condoms. No one on the East Coast knew what they were talking about. I’ve never dealt with any of that. You may lick whatever you like. Since I’m seeing lots of doctors this month, catching up on annual check-ups, I may go ahead and request a full screening. Always better to be sure.
I will state for the record that I am post-menopausal, can not get pregnant. One of the great advantages of older women!
Wow… need to do something sexy to offset all the logistics above…hmmm…. I’ll send you a photo. Mwah!
-S
From: Sassy
Subject: A sassy hand
Hiya! Here’s my hand. It can do things to parts of your body. Use your imagination. 😉
Good night. Sweet sexy dreams!
-S
Re: A sassy hand
That hit the spot. I have a thing for women’s hands and feet. I want one of your foot too, when you get a chance. Your hands are lovely and yes, it did set my imagination off.