Category Archives: Randy

by

Randy remembering

January 18, 2017 Wednesday
6:00 AM
Randy
Good morning beautiful

7:53 AM
Sassy
Good morning hot stuff!

8:14 PM
Randy
How are you this fine Wednesday?
My week has been very busy. 
Getting very demanding at work

Sassy
Great! You?
Getting ready to go away?

Randy
Tired already a long week
Yes picked up dry cleaninng

Sassy
I know that feeling

Randy
Getting rest of clothes together
reservations made
A bit of a hassle
How are you?

Sassy
So happy to be home relaxing

Randy
Long day?

Sassy
Yeah
Helping run a conference all week
Asked a month ago – do we need more than 2 lunches ordered?

Randy
Oh what kind of conference?

Sassy
They said – Nope, all set
This week – can we have another lunch?
Can we order coffee?
We said 10 bags of oranges but we need 5 more
Orienting incoming people

Randy
Oh boy 

hungry uncaffienated and tired people not the best combination

Sassy
I don’t mind, just wish they could decide more than 24 hrs ahead
Last minute makes it tricky

Randy
Indeed
Were you able to pull it off?

Sassy
Oh yes
Did I send you the boob cum shot?

Randy
Yes very nice reminder baby

Sassy
I keep looking at it and smiling

Randy
It was a great morning

Sassy
I’ve been wanting a man to do that for ages. 

Thanks for letting me cross that off my bucket list!

Randy
It was wonderful
Felt totally drained afterwards
Thank you for such a wonderful morning

Sassy
In a good way?

Randy
Yes drained in a good way

Sassy
You’re most welcome!

Randy
A little (lot) sort of great though but in a good way
that should be short of breath

Sassy
Well we know how to do better next time

Randy
Yes absolutely!

Sassy
Gotta keep you breathing so you can eat me

Randy
Yes that did suck a bit couldn’t catch my breath for a while

Sassy
Something to look forward to!

8:27 PM
Randy
Yes please!
Hang off wife calling
er on

by

Randy morning

January 17, 2017 Tuesday
5:22 AM
Randy
Good morning
Sorry I fell asleep
Never made it to the movie☹️

7:15 AM
Sassy
Good morning hot stuff!

7:36 AM
Sassy
I’m getting out early to let the cleaners clean. 

Hope you’re Tuesday is off to a terrific start.

by

Randy writes

January 16, 2017 Monday

5:51 AM
Randy
Good morning sexy

7:58 AM
Sassy
Good morning hot stuff!

9:57 AM
Randy
Sorry been driving
How are you this sunny morning?

Sassy
I’m fine, musing under covers

Randy
Nice I’m out running errands

8:45 PM
Randy
Hey there, how was your day?

9:25 PM
Sassy
Quiet. 

Hubby came home sick. Did you get to the movies?

by

Meet #2 Randy in my bed

January 15, 2017 Sunday

5:57 AM
Randy
Good morning sexy

7:01 AM
Sassy
Good morning hot stuff

Randy
How are you this morning my beautiful lover?

Sassy
I’m super! You?

Randy
Great
Super horny
Thinking about you all night

Sassy
Oh my

Randy
Hope that’s ok
Leaving shortly
Ok on my way and very excited

Sassy
Yay! See you soon!

Randy
Just going over the Tobin bridge

Sassy
Wow!
I’m hopping into the shower!
Stay in your car until I get out!

Randy
Ok
Will be a little bit

Just parking now
Found a spot around the corner

Sassy
Hooray! I’m ready!

Randy
Yeah!!!!
I’ll grab my stuff and walk over

Sassy
Yay. So ready! 

Randy
Ok on my way

Sassy
Goody goody goody goody

Randy
Just walking up
Which #?
Or can you buzz me in?

Sassy
I’ll buzz you in, turn right to elevator, go to my floor and I’ll meet you

8:10 AM
Randy
Ok

========

Report #2 Randy
in my bed

Background

I met this guy for a drink in early October right before he took off on business trip and we had a sexy time in the car that night. We chatted every day after that, while he traveled on business, then back home.  November 1 he went silent.  It seemed to me that he was too busy to cheat – crazy busy job, kids, volunteer work… so I smiled and moved on. 
After two months, he reappeared!  Apologized for being busy at work, wanted to get a hotel.  Of course, scheduling was a nightmare over the holidays, and then I got the stomach flu and then a cold and I despaired of us ever meeting.  
Finally came MLK weekend.  Hubby was away at a convention for three nights!  I had my condo to myself and no one to come over to play!  Weekends are tough for most men, and holiday weekends even worse in terms of getting away from the family.  I mentioned it to Randy.  He said he had a long list of ‘honey-do” items and events with the family.  *sigh 
Then suddenly he offered to come by Sunday morning!  We had a fun chat, imagining what that would be like.  He said he’d know on Saturday afternoon.  I was on my way to meet a gal pal when he pinged to say he couldn’t make it.  He had to take his kid to a sporting event.  Ah well… 
I went on to afternoon tea, had a lovely time and finger sandwiches with my friend!  Then I went out for dinner and a movie with Sis.  We saw “Hidden Figures.”  So good!  
Randy pinged me as I was driving home.  He said he was really looking forward to tomorrow morning.  I was like… Wait.  What?  I thought you canceled?  He said I misunderstood!  WOW!  He is going to visit me!!!
It hit me that my condo was in no shape for visitors.  So at 10 pm at night I dug in to clean up, hide away, and rearrange!  Randy was chatting with me while I cleaned!  He took off to bed at 11 pm, and I spent another two hours working.  I even got out the broom and got the cobwebs off the ceiling over my bed!
I finally fell into bed at 1 am, faced with having to get up at 7 am to shower and be ready for him at 8 am.  Whee! 
===== 
Touching

My alarm went off at 7 am.  Ugh.  Too early!  But my excitement was enough to get me out of bed, through my morning routine and ready for him by 8:03 am!  He found a parking space and was waiting for my signal.  I buzzed him up and met him at the elevator in my nightgown (and nothing else!)  We had a lovely hug and kiss, then I led him into my unit. 
We had another long kiss just inside the door, then I led him to the bedroom to put down his bag and take off his coat.  I introduced him to my cats and he admitted he is allergic.  Crap!  He said he’d taken allergy meds (he does every day) so he’d probably be okay.  [I have to remember to ask men about their allergies!!!]
We hugged and kissed for a while more, then helped each other out of our clothes.  We sat on the bed touching, exploring, kissing… then rolled over into a lovely naked hug!  He played with my clit and explored that area until I was squirming and shrieking.  He has great big hands and knows what to do with them! 
He reclined and I put my head on his chest, ran my fingers around, then down.  There was a nice glob of pre-cum for me to spread around while I explored his cock.  It’s not long, but average with a wide girth!  

 Swallowing

I moved around to give him a Sassy blow job!  I licked him up and down, pulled on him, stroked his balls, then sucked him down my throat and bobbed back and forth.  He warned me that he might not last long because it has been so long since he’d had sex and he was all revved up! 
And sure enough, I pulled him deep into my throat and BOOM!  I swallowed a big load of cum! 
Oh, I do adore that! 
We relaxed and I put my head on his shoulder and we talked about high school crushes and whether the new president will mess with his industry.  I reveled in the luxury of being able to cuddle naked and touch him all over.  I asked if he wanted to taste me.. He had been so “I adore oral in both directions!” but he said his nose was stuffing up so he wouldn’t be able to breathe if he went down on me.  Ugh.  

Pounding

Eventually he said he needed to be inside me.  He said he was going to fuck me good.  So he got up to find the condoms he brought.  A Trojan wearer!  He brought a box of 20!  He pulled me to the edge of the bed, pulled my legs up and slid inside.  Mmm… such a wonderful feeling!  He pounded me for awhile.  He was having trouble finishing, so we rested awhile more, nestled together.  Then I offered him doggy style and he grabbed another condom and stood by the end and entered by the rear door!  He pounded me!  So so hot!  I was trembling and screeching! 

He still didn’t cum… hmmm… he had talked so much about being able to cum over and over.  Ah well.  Maybe we can try something else? 

Bucket List Item – CHECK

He asked if it would okay for him to jerk off and cum on me.  Yes!  I am finally going to get someone to do it on my breasts!  Wowzers!  He used his hand and I licked him a little and BOOM!  Five spurts onto my chest!  It is something to watch!!  
I had to take a photo!  Here’s proof.  A rather demure photo of my cleavage except for the globs of hot white cum!  Hee hee.  

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We had another nice cuddle but then his nose and lungs were getting painful so he said he had to go.  *sigh Another man who can’t visit me here.  

 Farewell

 We chatted as he dressed then I gave him a quick kiss on the lips and he was on his way about 10:30 am.  

========

12:07 PM
Randy
Hey there thank you very much for a magical morning.
It looks like I left just in time
got home wheezing and out of breath.

Son’s nebulizer worked
Feeling better now

[Bless him for writing so quickly!]

Sassy
Phew! Thanks for letting me know.. I was worrying about you!
It was a special morning!
I am writing about it in my journal… lots of yummy words like hot and sexy and mmmm

Randy
Very nice I like it

9:17 PM
Randy
Thank you again for a magical morning.
The steroids make me feel a bit wacky but feeling better now
Messed up afternoon for me
Daughter disappeared with friend when she was supposed to be studying
Had a lot of fun this morning. I hope you did too.
Next time should be at a hotel

9:28 PM
Sassy
Hiya! I am still beaming about your visit!!!

9:37 PM
Randy
You’re probably out huh
So am I.
My insides are all a buzz. 

But then again some of that is probably the steroids
Lol
Tired
by

Randy plans

January 14, 2017 Saturday

6:48 AM
Randy
Good morning my sexy lass

Sassy
Good morning hot stuff!

Randy
How are you this morning

Sassy
Fantastic! You?

Randy
Good not much sleep thinking about work
Moon was phenomonal

Sassy
Awww

Randy
Thinking about fucking you with my thick cock

Sassy
Mmmm

Randy
Yeah competing thoughts in my head
I’ll figure out this morning if I can get away tomorrow morning

Sassy
Okay.

Randy
I am very horny for you baby

Sassy
Yay!

Randy
Yeah I have masturbated but to no avail. Still pretty worked up

Sassy
😉

Randy
Still sleepy?

Sassy
Yes…going back to sleep soon. 

Just got up to pee and you pinged at exactly the right moment!
What’s on your agenda?

Randy
Taking in recycling 

de christmasing the house, a couple of home repair projects, a movie then dinner

Sassy
I’ll be thinking of you

Randy
The thought that keeps going through my head was you touching my cock with your thumb rubbing around the precum.
 It felt so unbelievably good
I keep imagining how experiencing you fully must be like

I’m even hard now just thinking of it.

Happy to see da pic to prove it

Sassy
So glad to hear we made great memories

Randy
Yes very great
Heres to more to come….

Sassy
Yes!!

Randy
DO you like to give BJs?

Ok good night baby

Sassy
I adore Bjs
I used to just like making the guy feel good but have learned to adore the way they make me feel too.

Randy
AWESOME
They really get me going
And I love love love to return the favor

Sassy
Mmmmm

Randy
And given how you made me feel in a few minutes I imagine that you are a tremendous lover
Damn rock hard again

Sassy
I don’t know if I can match your imagination but I’d like to try!

Randy
You already have baby
I did not get enough kissing time last time

Sassy
We can fix that

Randy
Yes please
I love kissing
And gentle touching
You feeling for my underwear was tremendous
Almost overwhelming
Can I ask with oral do you like your clit focused on or the whole area

Sassy
Whole area narrow down to the clit as I get close to exploding

Randy

[Photo of his underwear with a huge bulge]

Sassy
Oooh

Randy
More?

Sassy
Sure!

Randy
Okay will do

[photo of his cock sticking out of his underwear]

[photo of his cock next to the Christmas tree]

Not the best pic but merry christmas?

Sassy
Yummy
I’m imagining touching

Randy
Take me in down to my balls baby
Yes PLEASEEEEE!

Sassy
Licking from bottom to top

Randy
Nice

Sassy
Sucking

Randy
I want to explore your pussy with my tongue sucking your lips gently and tickling your pussy with my tongue as i go

Sassy
Hearing your moans
Oh my

Randy
gently working my way around until I encounter your hard clit

Yes baby yes

Then sucking in your clit and exploring round and around with my tongue until you climax hard

then hold you in my mouth until you can;t cum anymore

Can I see you pussy?

Worked up here

Sassy
I’m all bundled back under the covers

Randy
Smiling face?

Sassy

[photo of my smiling face]

From yesterday after I finished at MGH

Randy
Very nice 

love the smile!

Sassy
Kinda goofy in my relief

Randy
You look happy not goofy
You like the cock pics?
I just asking because some don’t

Sassy
Oh yes…great pics, great cock and I really appreciate you taking the time on a busy morning!

Randy
TY he has served me and a couple others well
I enjoy chatting with you it is a great part of my day

Sassy
Awww. Thank you!
You make my day!

Randy
You are a tremendous woman in many regards: intellect, creativity, emotionally, and sexually

Sassy
Wow! What a perceptive man….
Hee hee

Randy
Not really, you are great 

I enjoyed meeting you

Sassy
You are a fascinating mixture of business man, kind soul, and sexy dude!

Randy
TY
I am working on deepening my soul

Sassy
I feel like I have a lot to learn about you

Randy
I find sex really focusses and tenors my life
Yes I am a guarded person

Sassy
I don’t need to know most normal things, but I adore poking around in your mind and exploring your body

Randy
Yes that is what I like about you: you seem like the kind of person to say “I don’t want your home address, but I do want to address your hornyness”

I don’t want to know what day you were born but rather what you would like to do the rest of your life

i.e. you seem to be a deeper person

Sassy
I don’t think of myself as deep…just different in my focus, on what’s important,
Oh man I want you next to me

Randy
That would be very fun right now.
I am so hard and it won’t go away

Sassy
I want my head on your chest, listening to your heart beat

Randy
Phenomonal
I love that
Sorry baby I have to run I need to get started on my chores
I look forward to chatting soon. and I’ll let you know about tomorrow morning

Sassy
Hope you have a great day!
Mwah!

Randy
Thanks and you too. I hope you get some sleep

7:07 AM
Randy
I loved the sound you make as you climaxed

1:25 PM
Randy
I think I’m on for tomorrow
Will only have a few hours
I am sooooo looking forward to seeing you again

Sassy
Wow! When might you arrive?

Randy
What time is good?

Sassy
Whatever works for you. I’ll be home

Randy
Is 8 am too early?

Sassy
Nope

Randy
Where are you?

Sassy
[my street address]

Sundays are great because you can park anywhere

Randy
Looks easy to find
Oh that’s my next question

Sassy
Not in the parking lot – they tow

Randy
Should I bring some supplies?

Sassy
Either on my street or around the corner
Like what?

Randy
Oil, towels, live, condoms
Music?

Sassy
Oh my…
Whatever you like

Randy
Been thinking

Sassy
I have towels
I bet you have

Randy
Ok
Condoms yes?

Sassy
Yes please

Randy
Ok

Sassy
What’s live?

Randy
Sorry lube

Sassy
Ah…I have lube

Randy
Ok
Are we safe for unprotected oral, I was recently tested and am clean

Sassy
Yes

Randy
Yeah!!!
I love giving

Sassy
We’re going to have fun
And laugh
And feel good

Randy
I hope so
It has been a while

Sassy
I have to shower…type any other questions and I’ll answer when I get done.

Randy
Ok
Pics?

Sassy
If we don’t get it quite right, we’ll have to practice more.

Randy
Oh are you pretty tight? 

It can take me a while to cum with condoms
I like your thinking

Sassy
I’ve been told I am tight. 

And lack of use probably makes it even more so

Randy
Nice
Will be very fun
Can’t wait
I hope you can cum multiple times

Sassy
If I don’t cum, I still have fun

Randy
Oh I’ll make sure you cum
Why is it hard for you?
In the car was pretty easy

Sassy
I’m waiting for a Lyft

Randy
Ok ttyl?

Sassy
Going to the Taj Boston for afternoon tea

Randy
Nice!
Have fun

Sassy
Thanks!
Have fun at the movies!

Randy
I forgot my daughter has a swim meet so we’re going tomorrow

Sassy
Awww

9:41 PM
Randy
Hey baby sorry I have been booking flights
How was lunch?
I am looking forward to tomorrow

Sassy
I went to the movies, just getting home
Wait…are you visiting or no? I thought you cancelled?

Randy
No I’m sorry 

I’ll go to the movie after our date

Sassy
Yay!

Randy
I’m still planning on seeing you if that is okay

Sassy
Yes!
Glad I asked!
Oh my…I have seen some prep to do!

Randy
I’m sorry is it okay?
And you don’t have any hidden cameras in your house do you?

Sassy
It’s great!
What?

Randy
Just kidding
You don’t have to do anything special for me baby
I hope you’re clean and ready to get dirty

I packed a bag
You ok?
Scare you off?

Sassy
I’m great
Just dashing around doing stuff

Randy
Baby it’s all fine
I just want to see you

Sassy
I know. Just a few things to make it easier
You set?
Ping me when you arrive in the entry and I can buzz you up

Randy
Yep packed a bag
Do you prefer casual or dressed up?

Sassy
Naked
Definitely casual

Randy
OK Jeans then….
Naked underneath

Sassy
Oh my

Randy
What about you?

20 condoms enough?

Sassy
🙂
Maybe.

Randy
you have lube?

Sassy
Yes. What do you want it for?

Randy
fingering

Sassy
My plumbing still works

Randy
ok and great!
Want to tickle your clit

Sassy
I have two kinds if we need them

Randy
OK
BTW I was checked last month

I am clean no disease

Sassy
Very good to know

Randy
You ok?

Sassy
Yes

Randy
And sorry to confuse you
I don’t want to miss tomorrow

Sassy
We’re on the right track now

Randy
Should I let you clean up?

Sassy
I’m fine now

Randy
And honestly the only thing I’ll be looking at is you

Sassy
Awww

Randy
And true

Sassy
I’m going to blame all clutter and mess on Hubby. 🙂

Randy
OK works for me.

Sassy
Hee hee

Randy
We should have an orgasm for him
okay that doesn’t sound as funny as I thought it would
Lingerie?

Sassy
I don’t own any.

Randy
SO I guess you’ll just have to be naked

Sassy
I’ll have on something for you to take off

Randy
Nice
I like slow
BTW I’ll have to leave around 11 so I can make it home by 12
I hope you’re loud
Cleaning up?
You ok?

Sassy
Yes… doing a bit more.

Randy
OK

Sassy
If I am going to be awake to greet you, 

I’d better get to bed! 
Ping me when you leave home?

Randy
Yep will do.

Sassy
How long do you think it will take you?

Randy
Good night baby
40 mins?

Sassy
Okay.
Drive carefully!

Randy
I can txt you when I hit the bridge

Sassy
Sounds like a plan!
Sleep well!

10:54 PM
Randy
You too
I am soon looking forward to seeing you baby