Disclaimer: This story was adapted from one written by Pocketpack. It does
not intend to infringe on the WB's TV series in any way. It is a "parody" of
the show only - and has not been produced for profit.
Keywords: Ff, inc, voy
Summary: A voyeur sees something very interesting when he peeps through the
windows at the Gilmore's house.
Gilmore Girls: Peeping At Lorelai
I'm a peeping tom, and have been for more than 3 years. I guess I'm not real
proud of it, but I'm addicted to looking into other people's private worlds
without their knowledge.
I live in Stars Hollow Connecticut and at 16 my main interest is sex -- and
I've seen a fair amount of that in my neighborhood. If you're brave enough to
sneak up to someone's windows at the right time of night, you're bound to see
something you were not supposed to.
Following my passion, I was going strong with my almost daily trips through
the neighborhood, seeking out the naked bodies of my neighbor's wives. It was
funny, but I sometimes got a chance to peek into the window of girls my own
age or a little older, but I much preferred their mothers.
I had a regular list of women who I would visit, but I was always on the
prowl for new worlds to conquer, and Mrs. Gilmore was one of those new
She was a pretty brunette, with perky breasts. She was a real knockout. When
I met her sometimes around town she always had this way of flirting with me
and I'd always end up that night using her as my masturbatory fantasy.
Lorelai, (her Christian name) had never married, but the story went that
she'd got herself pregnant when she was about my age. She had a daughter
who had been in my class at school until her mother got her into a big
time preppy school in Hartford.
I had never peeped into her window before because her bedroom was on a second
floor, but after one of our impromptu flirting sessions I decided that it was
time to take a shot.
Her house was set back and easily accessible for a peeping tom. There was a
lot of cover and big trees. The lights were on and as happened more often
than not, there was a view through the shades right into her bedroom.
I crept up the tree quietly to the window and took my first look in. What a
shock I got!
Let me preface what I'm about to tell you by saying that the word around the
neighborhood was that she was a little strange. Strange in what way, I wasn't
quite sure, but strange nonetheless. Her daughter, Rory, was pretty and she
seemed to have reached maturity a lot earlier than most of the girls in my
I peeked in and there was Mrs. Gilmore, walking around the room, putting some
clothes away. But she was naked as a Jaybird! I excitedly caught a glimpse of
her pussy. She had very sexy moves, her body was nicely proportioned, and she
moved with an unconscious grace that was pleasant to watch. I was really
getting into her when I saw her turn towards the door. The window was open
somewhat and I could hear her say, "Come on in, Rory."
It seemed kind of weird that she'd be totally naked and tell her daughter to
just come in. But Rory walked in, wearing an oversized tee shirt and no
pants. She had pretty nice legs, too. Rory and her mom hugged each other, her
mom running her hands through her daughter's long dark hair.
I heard them both laugh and Mrs. Gilmore pointed to the bed, and Rory walked
over and hopped up on it sitting back on her elbows watching her mother
walking around the room naked completing her tasks.
I was enthralled. I watched and waited, not knowing what was going to happen.
I just figured that she liked to walk around naked and didn't care that her
daughter could see her.
Finally Mrs. Gilmore finished her work and walked over to her daughter,
still lying there on the bed. She had her knees up and I could see that she
had on a pair of panties beneath her T-shirt. They were talking to each other
quietly and I could only make out a few words of their conversation.
Then Rory pulled her shirt off over her head, and laid back again using her
elbows to prop herself up in a reclining position. She had no bra on and her
firm tits were out in the open for me to see. They were really great looking
and made me wish I was in there sucking on them. I think my mouth was hanging
open as I intently starred through the window.
I couldn't believe what happened next. Rory slid down to the edge of the bed
while Mrs. Gilmore lay back, spreading her dark hair clad cunt apart. Then as
I watched in total shock Rory pulled her hair back behind her head with one
hand and in a businesslike manner began to eat out her mother!
Man, was I going crazy! Not only was I watching two good-looking chicks going
at it (which I had never seen before) but it was a mother and daughter to
boot! I had never really given any particular thought to Rory before, but now
watching her supple body astride her mother's, and eating her pussy -- well
all I can say is I was seeing Rory for the first time, and it was making me
horny as hell.
Mrs. Gilmore was flailing around on the bed as Rory ate her pussy. She was
moaning and yelping and I knew she was cumming hard when she started to
scream. It was glorious.
Then after she'd come down from her orgasm a little, Mrs. Gilmore pulled her
daughter up her body and Rory lay right on top of her totally naked except
for a small pair of panties. They started to kiss each other. They had
obviously had lots of experience with each other before this night as they
comfortably lay in each other's arms.
Watching two women kissing was more than I could bear and I came in my pants.
I was amazed as I felt my dick jerk and hot wetness fill my confined crotch.
But I stayed at the window my cum cooling in the night air. I didn't want to
miss a thing.
And sure enough, the next thing you know, Mrs. Gilmore rolled her sexy
daughter off and on to her back and quickly pulled her panties to one side
and began to do the same thing to her daughter that she had just received.
She sucked away at her daughter's pussy for a minute or two, then braking
away she reached into the draw of the night table and pulled out this pink
thing. It took me a minute to realize what it was. OH MY GOD! It was a
She sat back down on the bed, next to her daughter and spread her legs and
that pink penis stood up like the Washington Monument between her hands.
Rory's mom straddled her and, with her fingers between her legs, slipped
that thing right up her wet cunt. Man, was that hot looking!
Then Mrs. Gilmore started pushing that dildo in and out of her daughter, her
tits flailing from side to side and up and down until Rory grabbed them and
squeezed them tight. "I love you, Mommy! I love you Mommy!!" She cried over
and over as Mrs. Gilmore kept pumping away. Finally, she started to yelp and
moan as she came.
And boy, did she ever cum! I watched as her body jerked in ecstasy, over and
over again as her mom relentlessly thrust that dildo in and out of her slick
pussy. God, what a sight. At that moment all I wanted to do was climb in that
window and join them in their sex play. It was really hard to hold myself
Finally Rory took her mother's pumping hand and she slipped the dildo from
her cunt and then climbed on top of her mother again. Mrs. Gilmore wrapped
her arms around her daughter and they kissed passionately. I felt as if I
had just won the lottery!
The two of them lay there for a while and I thought they were finished, but
they were far from done. After a while Rory took the same dildo and straight
away plunged it into her mom and pumped away.
It didn't take long before Mrs. Gilmore was screaming and coming again only
a few minutes later. Rory sucked on her mom's tits as she came and then they
repeated the same kissing and hugging scene again as they lay in each other's
By this time I already had my sticky dick out and had cum right along with
Lorelai as her perfect body shivered in its second orgasm of the night.
I planned to make the Gilmore residence a regular stop on my rounds. I
figured that the Gilmore girls just might be the best entertainment I'd ever
get. And besides maybe, just maybe I could figure away out to become part of
their little love nest.
I can tell you that I awaited my next "flirting session" with Lorelai with a
mixture of nervous inpatients and longing...