This is a story about a date I had about 6 months ago with a 36-year-old woman called Karen.
I had worked with Karen previously before she had left our place of employment for another job.
We always gotten on well in the workplace - she was a married woman at the time with 2 children and displayed quite a shy and reserved demeanour for the most part but not in a boring way. She simply wasn't possessed of an outgoing personality but more than made up for it with a good sense of humour and a very earthy attitude to things, which had always impressed me. And of course she was very cute – not overly tall but a nice body with curves in just the right places.
I would stop short of saying we flirted with each other but I think we both sensed that if the situation were any different, it might have been nice to see each other outside of work at some stage.
My feelings towards her were enhanced when I happened to catch a glimpse of her undies one day when she bent over at a certain angle.
Her shirt lifted and her jeans pulled down just enough in the other direction to catch a brief peek of her white cotton undies at the top of her jeans and this was a moving enough experience to encourage me to masturbate over Karen quite regularly for some time to come.
I got particularly excited at work whenever I knew she was going to visit the ladies room, as I imagined, (often in graphic detail) what might have been going on in there.
At the time of her departure, I was naturally disappointed but accepting of the situation and was equally happy just to let things be.
That was until about 6 months ago when I ran into Karen for the first time in probably 5 years purely by chance.
We ended up talking for about 10 minutes and exchanged phone numbers willingly but most significantly, she let it be known that she had separated from her husband.
The signals I got that from that encounter that she was indeed quite keen to catch up, so after a few days of deliberation, I decided to take the plunge and send her a text.
It was fairly basically along the lines of "let's catch up soon if you're available." I'm often not overly confident when I engage these types of encounters and am just as happy to let them go and expect little if any response once I've put it out there.
To my surprise on this occasion, Karen returned my text within 30 minutes with a positive response to the effect that her husband had the kids which meant that she was free over the upcoming weekend, so let's make a date.
Now totally encouraged, I fashioned a time and place and locked in a rendezvous for Saturday evening.
Needless to say, I had been masturbating quite enthusiastically leading up to the big night.
Images of Karen and her pretty undies were at the forefront of my fantasies along with plenty of imaginings of her in the ladies room taking care of what she needed to.
Putting these lewd thoughts aside as Saturday evening arrived, I met Karen initially at a local bar and we then continued to a local Mexican restaurant for dinner.
The evening was a great success and quite frankly I would have been happy to leave it at that, certainly keeping it open to meet again sometime soon.
But as the evening progressed, the topic of conversation, perhaps inevitably moved onto Karen's separation from her husband.
Rather than developing into an emotive counselling session, Karen instead expressed how relieved she was to be out of a generally unhappy situation and moreover that even though she had been estranged from her husband now for over 2 years, she had not been in another relationship since.
It so happened that I hadn't had a girlfriend either for an extended period and I also made this known to Karen.
There now seemed to be something of a common cause at hand and shortly thereafter, I found myself offering Karen a lift back to her apartment.
Happily for me, Karen accepted and even more happily, ended up inviting me in for a coffee.
Karen had removed her shoes from the time we arrived back at the apartment and looked particularly sexy slinking around in bare feet as she poured me another cup a coffee.
The conversation continued healthily as the clock ticked steadily beyond midnight.
"One thing I really miss about not being in a relationship for so long is the massages." Karen admitted. "I used to get them all the time when we were first together but funny how they just faded away with everything else...."
"Well I'm sure I could oblige if you wanted," I responded.
"That would be nice!" Karen confessed.
Karen's sexy bare feet seemed as good a place to start as any, so this is what I offered.
She quickly accepted and for the next 10 minutes sat there massaging her feet and ankles, making a point to massage some distance up her legs inside her jeans.
Not wanting to force this issue to quickly, I then offered to plunge into her shoulders, which she also keenly agreed to.
I then checked myself as Karen now sat herself on the floor between my knees with not only her shoulders but pretty much any part of her body that I may have wanted to touch, available.
Using her shoulders as the obvious pretext, I applied as firm a massage as I thought she would enjoy - Karen was not a big boned girl and although she had ample flesh in the right places, I was careful not to fracture any part of her as I dug in firmly but sensually.
I gained permission within a few minutes to slide Karen's cardigan off her shoulders to give me "better access" which is exactly what her tightly fitting cotton top gave me, along with the better part of a throbbing hard-on.
Still resisting the urge to advance too rapidly, I continued to work her shoulders at the back but ever so gradually moved my hands towards her collarbones and chest.
My fingers inched downwards towards her cleavage – Karen was not big-breasted but certainly had appropriately shaped boobs for a woman of her size.
Karen slowly opened her eyes, directing something of an obvious look up at me.
"Would you like to touch me there?" she queried.
"If you'd like me to," I replied.
"I'd really like you to!!" she urged.
At this, my hands found their way fully around Karen's breasts, gently squeezing and kneading them through her thin cotton shirt and bra.
"NICE!!!!" I cooed in Karen's left ear.
Karen paused after a few minutes and removed both her top layers, giving me a lovely first look at her small and well-shaped breasts. My hands were able to move directly to her nipples which became quite erect immediately with the flesh-to-flesh contact.