Girlfriend’s Mother Part 1

I received an email one day that both confused and excited me.
There was no subject line in the header but I could see that if had come
from my then girlfriend’s mother. I didn’t really understand why she would
be emailing me, we were no on the best of terms, but I opened it anyway. It
contained only a single attachment, no message, and no signature. Knowing
that she isn’t really very computer literate I figured it wasn’t a virus or
anything so I popped it open and was amazed at what it was. She had sent me
a digital picture of herself wearing only her bra, panties and 4″ stiletto
heels, all a beautiful satiny black.

To help my readers understand my confusion I need to cover a
little back-story. It had been in our fourth year of dating, I was not into
commitment at 25. I had always found my girlfriend’s mother attractive in a
skanky sort of way. She had just turned 40 and had been living with a guy
she had known in high school before her first husband knocked her up at 18
with my girlfriend; so as you can see her initial track record wasn’t really
very good. We were used to watching her bounce from courtier to
ex-husband(s) (yes plural) to old friends-The really interesting part is
that we knew that she wasn’t having sex because she always bitched about it.
In fact she came home one day having been to the Ob/Gyn and felt the need to
share. Apparently her doctor had commented on her tightness and suggested
she needed a dildo that she could put inside herself once a week so as no to
have such a difficult checkup next year. I always wondered if that was why
she switched me so often. Anyway at 5’8″ her 110-pound frame held the
perkiest little B-cup breasts that always seemed to be pointing straight
out. Her hips were shaped such that they were basically nonexistent, just a
little shape but definitely not wide, complimented perfectly by here really
tight little ass and very long lean legs, which she tended to hide under
khaki pants and t-shirts.

For whatever reason she had started to grow her over-dyed
dishwater blond hair back out and it was reaching the perfect length,
hanging just below her shoulders in a sort of layered look. She had also
started to wear shorts again since it was the beginning of summer. The best
part about this was that she had always felt the need to ship in the Juniors
section of department stores, so the shorts were really short-less than a 1″
inseam, and they cupped her ass perfectly. In fact when she sat down I
often found myself stealing glimpses of her panties riding up with her
shorts and just revealing the sharp angle of her butt where torso meets leg.
She was still wearing baggy t-shirts but that seemed to excite me even more.

I decided to do something about my desires so I set up an
anonymous email account (I’m a bit of a computer geek) and blocked my ISP’s
information. It was almost perfectly anonymous. And decided to send her a
couple of erotic poems. Receiving no response I stupidly followed those
emails up with a message suggesting that she had a secret admirer (yes, I
know its corny) and then later on that may be we should meet and do all
kinds of nasty stuff. I did do one smart thing in al of this mess; I never
came right out and suggested anything specific, instead I alluded to acts of
intimacy, sharing of erotic emails, and even a sharing of a partner or two.
Unfortunately she had decided to react to something for the first time in
her life and turned the whole mess over to a detective friend. He managed
to track down who was sending the stuff and she confronted her daughter with
the information. Big drama!!! I managed to talk my way out of the mess,
although I did dump my hard-drive just in case, and we had not spoken to her
mother in 5 months when I received the mystery email, so you can see how I
was a little thrown off.

I sat on the email for about two weeks pondering what to do
(obviously I spent a great deal of that time admiring the picture and
fantasizing). Eventually I guess I just decided “what the hell.” I grabbed
my phone one morning and before I knew it I had dialed her work number.
Listening to the phone ring I almost hung up and am really glad that I didn’

Awoken from my daze by her voice answering in a polite “County Prosecutor’s
office this is Michelle.” I only managed to squeeze out “did you send me an
email about two weeks ago?” To which she responded in a hushed, suddenly
husky voice “yes.” My mind reeled, what was I going to do. I definitely
needed time to think so I made some excuse and told her that I’d have to
call her back later. To which she responded enthusiastically expressing her
gladness that I’d called. When I hung up the phone I just had to kick back
in my chair and breather for couple of minutes, to let my raging hardon
slowly go down, and to think about what to do next.

After a few minutes I realized exactly what I needed to do; her; in every
way imaginable. Ana a plan started to take shape. I quickly drafted a
nondisclosure agreement covering past present and future conversations and
actions; not technically legally binding but she wouldn’t know the
difference. I attached a handwritten note suggesting that we would move
forward as soon as I got the signed document back, and immediately sent it
out FedEx. Two days later I had it sitting on my desk with her signature
and a note saying that she couldn’t wait. In the meantime I had been
drafting a kind of sexual contract; I had specified things like amount of
time, and her utmost cooperation and willingness and my absolute control
over the whole situation (again it would never stand up in court but worked
for my purposes). I’ve placed a copy of both the nondisclosure agreement
and sexual contract at the end of the story for my readers’ perusal. A
couple of days later I got the call, from her. This time I was expecting
it. She wanted to know, was a little timid about signing the contract after
all it did give me total control of her life for a minimum of 72 hours.
Luckily being an attorney makes med a great salesman and I convinced her
that everything would be all right and that she shouldn’t worry. She signed
it and now all I had to do was set up the whole encounter.