Jessie was in her twilight years, as she referred to her
age, she had turned 70 and was alone. Her husband had
died 20 years ago and her children were living overseas.
She was thrilled that her two sons had done well in
their chosen professions but missed the company provided
by their families. Her days were spent pottering about
her garden and the occasional visit to friends from long
ago. It was on one such visit that a sparkle of her
youth returned.
Tim and Vera were her friends almost from childhood and
she looked forward to their irregular meetings. The main
problem was the distance she had to travel by public
transport to their home. It was on a cold Sunday that
Jessie set off to have dinner with them.
It had been nearly two tears since she last made the
journey and on the final leg she realized that she had
come too far. She made her way to a gas station to seek
directions and a helpful young guy behind the counter
assisted her. She had come about two miles too far and
was faced with a long wait to get back to her
destination. A gentleman in his forties was queued up
waiting to pay for his fuel and overheard the
predicament. He took an instant liking to this slim grey
haired lady and offered to drive her. Jessie looked
outside at the wind and rain and happily accepted his
offer.
He introduced himself to Jessie as Charles and assisted
her into his vehicle. Jessie chuckled to him as they
drove. “I can hardly remember the last time that a young
man drove me home, back when I was a teen I suppose.”
She stopped as if reflecting on her younger days, then
said without much thought. “I wonder how I can repay you
for your generosity?” Charles seemed almost offended at
the suggestion and insisted that what he was doing was
an act of kindness and “Your pretty smile is it’s own
reward.” Jessie blushed then said “Regardless, I will
think of something.” Charles then inquired as to how
she would get home that night and on hearing that she
would rely on public transport was horrified. “Jessie,
here is my business card. You will give me a phone call
from your friend’s place when you are ready to depart
and I insist that you be driven home.” Despite her
protestations she agreed. Secretly she was delighted
with the care and attention from such a nice young man.
Jessie tingled with expectation throughout the visit and
kept her new gentleman a secret, telling them only that
a friend had arranged for her to be taken home that
night. At around nine that night she rang Charles who
informed her that he would be there in ten minutes. On
the way across town she learned that Charles was now
single, having been divorced some 10 years ago and lived
by himself. He devoted his time to building up a small
importing business. “Don’t you miss female company
Charles.” Jessie inquired, wondering if he was gay. “Oh
at my age I have given up hope of finding a life
partner, although as you say, there are certainly times
that I really miss the company of a lady.”
“Now Charles.” Jessie said as they pulled up in front
of her apartment, “I insist that you come inside for a
cup of coffee and I have a little gift for you.”
Charles was now intrigued and followed the dainty little
granny inside and watched as she prepared some coffee
and cake. Soon they were sitting together on the couch
chatting and enjoying each other’s company. Charles
could not help thinking what a pretty girl Jessie would
have been long ago. Jessie then shocked him by
announcing. “Charles, I promised you a gift for the kind
way you treated me today and I know of only one way to
reward a man. When I was much younger, I’m not sure how
to put this but, I errr used to end up with my head in
the young mans lap. Besides it’s been so long since I
have had the company of a gentleman, there are certain
things that I miss also.”
This was about the last thing that Charles thought would
happen and it took him by surprise. He said immediately
that such a suggestion was beyond belief and that,
“Surely you are joking.” Jessie leaned towards him and
placed her hand over his manhood and gently tickled him.
Charles knew that she was serious and suddenly a rush of
excitement swept through him. He held her head in his
hands and gently kissed this sweet woman.
“Now Charles, while I get rid of this silly dress, I
expect to find you in all your glory relaxed on the
couch.” With that, she quickly disappeared from the
lounge room. Charles stood in disbelief and with a shrug
of his shoulders began to undress. He carefully placed
his clothing on a vacant chair and was amazed at the
state of his cock. The way he had to stretch his
underpants around it reminded him of those lustful teen
years so long ago. He felt rather silly sitting there
naked with his dick pointing skyward and briefly
wondered if he was being set up, but this was
immediately dismissed when Jessie returned.
She had let her hair down and was wearing only a see
through nightgown over lacy black underwear. She dimmed
the light, came over to him and sat on the floor at his
feet. “Hello Charles, I think that you are just a little
bit excited to see me.” As she spoke, her small hands
wrapped around Charles’s cock and slowly stroked it.
“Charlie, you have no idea how it feels to me to be able
to play with a man again. “Jess,” he replied, “I think
we share the same problem but I think that you have
found the answer.”
“I have certainly found something Charles and I think it
likes me.” Charles found it difficult to contain
himself; it had been a long time since he had been in
such a situation. To Charles’s amazement Jessie grinned
up at him, opened her mouth and removed her false teeth.
This was to be Jessie’s gift to him.
Charles could only sit there dumbfounded as Jessie
proceeded to mouth his eager cock. Apparently she had
forgotten very little over the years and it embarrassed
him to think what a damn fine cocksucker this granny
was. Jessie pulled his cock to the back of her mouth
then clamped her gums tightly around his cock and chewed
back toward the head. She only did this twice before
Charles lost it as his cum emptied into her mouth, she
kept the biting motion going which gave Charles orgasmic
feelings like never before. Jessie kept his cock in her
mouth while he calmed down, continually licking and
cleaning with her gifted mouth.
“Thank you for the lift home Charles,” Jessie said with
a grin.
Charles sat there speechless for a minute and then said
“Jessie, I have not felt like that in my life and to
think that I drive within one mile of you each day.”
Jessie responded instantly, “Well Charles I must go to
bed now but if you are passing through in the morning, I
would enjoy being served a cup of coffee by a naked man
before the sun comes up.”
Charles drove home convinced that he was in a dream such
were the events of the day. He drifted off to sleep
eventually holding his firm cock. At five in the morning
he put his work clothes on a hanger and threw on an old
tracksuit. Jessie’s door was not locked and he quietly
made his way to the kitchen. Jessie had left everything
ready for him. He slipped out of his tracksuit and, as
requested, took her coffee into her bedroom. There was
only a small nightlight on and he could make out Jessie
sitting up in bed. “Thank you Charles,” she said “Now
please put the cup down beside me on the table and stand
close to the bed.”
Charles stood there while Jessie moved to the side of
the bed and tickled the shaft of his rigid pole. “I am
so glad that you came Charles, I miss this so much.” Her
mouth quickly covered his cock and her gums started
working on him.
Charles was able to try and fondle Jessie from this
position and he followed the curve of her shoulder to
her chest. He felt the lacy bra and just enough flesh to
excite him and Jessie as it turned out. He leaned
carefully forward and raised her gown up her back
exposing the catch of her bra. Undoing it, he reached
around her and held her two breasts. They were not teen
tits by any stretch of the imagination, but in a dark
room Charles did not care. He fondled them as Jessie’s
gums extracted another shattering orgasm into the back
of her mouth . Jessie swallowed rapidly and left his wet
tool swinging in the air as she reached for her coffee.
“That is a nice way to start the day, don’t you think
Charles?” Charles sat down beside her and held her head
as he kissed her. “Jessie,” he whispered there is
another way to finish the day and I am afraid that you
have got me body and soul and I must return your
kindness.”
“Why Charlie!” she giggled, “I believe you want to fuck
me and I am nearly old enough to be your granny.”
Charles nodded and agreed that was exactly what he had
in mind.
“Ok Charles, on your way home tonight be sure to buy a
big bottle of baby oil so that I can slide all over you.
I can’t wriggle around like I used too. Now Charles, get
dressed and get to work, I need my rest because I have a
long night ahead of me.”