The characters from the Gilmore Girls are the property of Amy Sherman/Warner
Bros. I'm just borrowing them.
Gilmore Girls: Gilmore Girlfriends Part 2 (Ff,inc,anal,mast,voy)
After dinner Mom suggested we settle down and watch a couple of DVDs. After
seeing Mom's collection of sex-toys I had high hopes that she had a stash
of porno films as well and that we'd be watching them. If she has, she's
keeping them to herself for the moment and instead we watched `Pretty
Woman', followed by `When Harry met Sally'.
I was still as horny as hell. Mom was sitting next to me in a silk nightrobe
and as the night wore on, both it and my skirt rode up our thighs. I kept
feeling Mom's flesh brush against mine, each movement sending a tingle of
lust coursing through me. It was hard to concentrate on the films - luckily
I'd seen them before.
The credits started to roll and Mom gave an exaggerated stretch and yawn.
She looked at me with a grin, "Fancy an early night."
It wasn't ten, early for a weekend. However, from the glint in Mom's eye I
didn't think it was sleep she had in mind.
"Well, it's been a long day," I agreed and followed Mom upstairs.
Once in her room she dropped out of her gown. I admired her body and hoped
I looked as good when I was in my mid-thirties. Both her tits and ass were
firm, and there was hardly a trace of fat on her thighs. Her skin was
smooth, even around her slit, which she has freshly shaved.
Mom gave a polite cough, "Rory," she said, "when I say an early night its
code for `let's go upstairs and fuck like bunnies'. And you're still
I blushed and began to strip off. As I did so Mom went to a drawer and
pulled out the strap-on with which she'd been fucking me with earlier. Once
it was in position Mom gave it a little waggle and its movement sent lustful
thoughts into my mind.
"I thought we'd try something else tonight," Mom said, "And for that we'll
need this cock well lubricated. Time for your first deep-throating, Rory."
I knelt in front of her. There was still a light aroma of pussy juice from
the dong. I moved forward and took the cock in my mouth. I started to move
my tongue round the tip of it and then bit lightly down.
"Lucky that wasn't a real cock," said Mom dryly, "don't chew, just suck."
She began to push the cock deeper into my mouth, so it started to fill me.
My mouth strained to take its girth as it went in. It pinned my tongue to
the bottom of my mouth and I began to fear I was choking. Mom ignored the
looks I tried to signal with my eyes and continued to slowly thrust the
cock in. I felt it hit my tonsils and I gagged against the cock.
"Don't worry," said Mom, noticing my discomfort, "just breathe through your
Easy for her to say - her mouth doesn't feel like someone is pouring a
bucket load of cement into it. I gagged again as I saw that the cock still
had a way to go and Mom wasn't finished. She continued to push and I could
feel the rubber ease past my tonsils and down into my throat. Tears pricked
at my eyes as I fought the urge to throw-up.
It was made worth it by the look on Mom's face. She was moaning and
grappling with her tits, her eyes were closed and her expression was off
utter bliss. I tried to relax as Mom began to thrust in and out of my
mouth, each blow rippling down my gullet. Mom gave an extra hard heave and
her leather strap rubbed against my lips as the dong went so deep down my
throat I'm sure it ended up in my stomach. Then she pulled the cock out. It
was well lubricated with my saliva dripping off it.
I wiped the tears from my eyes and gave Mom a smile to show that I was all
right. She patted my shoulder, "That was great Rory, but next time try not
to waggle your head so much. It puts me off my stroke."
She helped me to my feet, "Now it's nice and damp, we're going to do
something special," she said.
"What?" I asked.
"I'm going to pop your anal cherry."
A shiver of excitement went through me, at the same time as I looked at the
large ten-inch toy and wondered if, even with my spit, it would fit.
I let Mom guide me onto the bed and onto my hands and knees. Once I was in
position I could feel her lips against my cheeks, then her tongue came out
and she gently licked at my back hole. Grabbing my cheeks she pulled them
apart so her tongue could get in deeper. I could feel her tongue pushing in
as deep as it could go. Then she withdrew it.
I could hear her swirling saliva around in her mouth and then feel her spit
land on my ass crack, before it slid down to the hole. Mom's started to
push her finger in and I tensed as I could feel her knuckle graze within my
tunnel. She wiggled it for a few seconds, before withdrawing it. When it
returned it had been join by the finger beside it. I gave a gasp of pain as
they pushed my ass-hole walls apart. Then as Mom started sliding them back
and forth I felt a jolt of pleasure run through me.
Mom must have felt my shudder, as she pulled out her fingers, "It'll be a
squeeze, but it should go in now."
She was right, even with the preparations and her hands pulling apart my
cheeks it was a struggle. I groaned and cried out in pain, as Mom forced
the cock in. I could hear her grunts of exertion, interspersed with moans
of pleasure as the end of the cock rubbed her pussy. But eventually it was
in, I could feel Mom's smooth thighs against my butt. Mom let go off my
cheeks and gripped my waist hard as she started to rock in and out of my
"Oh Rory, fuck, fuck, fuck," cried Mom in excitement as she banged me. Her
hands gripped my waist so tightly that nipping of her nails almost drowned
out the pain in my butt. However, slowly I became aware of a new feeling -
a sensation of almost indescribable pleasure. Within each thrust of Mom the
cavalcade of excitement grew within me, until my cries of incoherent
pleasure were drowning out Mom's muttered oaths.
I thought nothing could out-orgasm this morning's fucking. I was wrong. A
shrill scream of pleasure escaped my lips and I could feel my arms give
way, such was the intensity of the rush of enjoyment flooding through me. I
fell face down on the bed, and the only Mom's strong grip on my waist
stopped my legs buckling.
And through all this Mom continued to pound into me, with such vigour I'd
have bruises on my buttocks tomorrow.
"Who's Mommy's butt-fuck bunny?" Mom called out.
I was still gasping for breath and didn't answer - though I guessed the
answer would have been `me'.
* * *
Several things struck me when I awoke the next morning. Firstly, I was
lying naked beside my Mom, secondly, my ass might have more bruises than
apple used as a baseball, but the orgasms had been worth it and thirdly, I
hadn't woken naturally, but because Mom was diddling my pussy with her
"Morning sleepyhead," said Mom and nibbled tenderly at my ear.
I muttered a weak morning and then let out a gasp as Mom's finger rubbed at
my clit. It was much better than an alarm clock and I lay against Mom as
she continued to frig me off until I came.
She offered me her finger and I sucked it clean.
"I thought we might go and buy some new clothes after breakfast," Mom said,
* * *
Ever since I've been little Mom has been pretty good about letting me wear
what I want. She's not one of those Mom's who want to either want to
recapture their youth or make their daughter into a fairytale princess. In
the last couple of years she's given me a pretty generous clothing
allowance and given me a free reign in how I spend it.
However, she had been much more controlling this time. Which is why I
returned laden with bags containing naughty lingerie, nightwear with easy
access, short skirts that barely covered my ass and T-shirts which didn't
conceal my midriff. All the apparel to look like a blue-movie star - I'd
even been bought one T-shirt with `Porn Star' emblazoned in bright letters
across the front.
We had only just put the bags down on the table when Mom was rooting
through them, pulling out a very short mini-skirt and what can best be
described as a cropped vest.
"Why don't you got to your room and try these on?" she said, almost
"Okay," I picked them up and started upstairs.
"Oh and Rory," Mom called after me, "I think they'd look best without
I did as Mom suggested. Standing in front of the mirror in the room I
admired my reflection. I'd had to hand it to Mom; her choices made me
looking daringly sexy. Even if, going out in public, I had to make sure I
stood up straight for fear of the slightest bending might result in me
flashing the neighbourhood.
I walked downstairs, Mom whistled appreciatively.
"Give me a whirl," she said.
I did so, feeling my skirt fly up as I twisted round.
"Very sexy," Mom purred. Then she gave me a smile, "I've an idea. Why don't
I get the DVD camera out and we can film you."
"Er, if you want Mom," I said, she obviously wanted some masturbation
material for when I was out.
Mom got out the camera and gave me my instructions, "I'll film you from the
top of the stairs. You come down and pretend to look round to see if anyone
is in. Once you're sure the coast is clear, pick the dildo up from the
table, sit on the sofa and frig yourself. Try and make it sensual -
remember this is for viewing."
The instructions seemed easy enough to follow. I went upstairs and waited
for Mom to shout `Action'. When she did I crept downstairs quietly, looking
around for anyone. I peeked in the kitchen and hall, Mom following me
closely with the camera. I had a feeling she was focussed on my butt.
`Satisfied' no one was in, I picked up the eight-inch purple toy Mom had
helpfully put on the table and went over to the sofa. Mom stood in front of
me with the camera as I hoisted up my skirt. I could see her go in for a
close-up of my naked cunt. I started to stroke it with my left hand, whilst
with my right I slid the dildo sensually in and out of my mouth. I didn't
put it in as deep as Mom this morning, but it still went in pretty far and
by the time I'd finished sucking it the rubber dong was soaking. As was my
pussy from the tender ministrations of my hand.
If I hadn't been on film I'd have stuffed the toy straight in, but I
remembered Mom's instructions and I used the dildo to trace patterns round
my pussy lips, rubbing the outside of my labia. Only when I was sure that
Mom had enough of an eyeful did I slide it into my twat.
As I pulled the dildo in and out, I reached up with my other hand and
pulled up my vest. I began to tweak at my naked nipple, rubbing the teat
between my middle-finger and thumb. It felt good, if not as much as the
rubber bouncing against my clit. Juice began to dribble out of my hole and
between my thighs, leaving a damp spot on the sofa.
I could feel self cumming and I let out a cry of pleasure.
"Mmmm," I moaned, "that was nice."
And then to give Mom a treat when she's rewatching I pulled the sodden
dildo out of my twat and slowly licked it clean.
"That was great," Mom complimented me. She took out the DVD and replaced it
with a new one, "What about another scene? Upstairs?"
I nodded. Since Mom introduced me to sex, self pleasure isn't as much fun
as it used to be. But it still fun and there is something liberating about
doing it in front of someone.
"Do you want to choose some lingerie?" Mom asked.
I went into the shopping bags and pulled out a slinky night-dress. It only
went down to just below my belly-button and was designed so that the straps
on the shoulder, didn't come anywhere near covering my titties. I followed
Mom upstairs to my room.
"For this shoot," said Mom as she placed a six-inch dildo in my beside
drawer, "I was thinking you could pretend to be asleep. Then you wake up,
throw of your bedding, get the dildo and then get on your hands and knees
and shove it up your ass."
"Sounds like a plan," I said as I got into bed. For a few seconds I lay
there pretending to be asleep. Then I gave a yawn and a stretch and sat up,
showing the audience my tits as they peeked over my quilt. I rubbed my eyes
and then pushed the bedding onto the floor.
I deviated from Mom's plan, by getting onto my hands and knees first. I
wiggled my ass at the camera as I pretended to root around in my drawer for
the dildo, though in reality it was on top of the various magazines sitting
in there. Finally I pulled it out. Mom moved round to film me as I suckled
it like a lolly for a few minutes, just to make sure it was lubricated.
Then with one hand I pulled at my ass-cheek, with the other I pushed it in.
Even with the butt-banging I'd had last night my hole was still small and I
couldn't stifle a small cry of pain as I entered.
"Don't worry," called out Mom, "we can edit that out."
I didn't reply, as I was too busy trying to concentrate on pushing the toy
down my back passage. It was a tight fit and I had to push hard to fit the
smooth plastic down. Then I gave a gasp as it hit my anal g-spot. I felt a
new batch of jizz starting to form in my pussy, it started to increase as I
moved the dildo in and out. I groaned and moaned as it banged against my
I thrust faster, falling down on my face as I moved the arm I was leaning
on so that I could use it to tickle my pussy at the same time. The bed
bounced as Mom got onto it and from the corner of my eye I could see her
feet as she stood over-me getting a close up of my anal self-play.
I gave one final scream as I came and then my legs buckled and I lay on the
bed, gasping for breath. Mom continued to film, focussing on the toy still
stuffed in my ass. Then she said, like she was a Hollywood Film Director,
"That's a wrap."
I gingerly pulled the dildo out, feeling my asshole contract back to a more
normal size with nothing to hold it open.
"Let's do one more shoot, before dinner," said Mom.
I nodded weakly, "Give me ten minutes to recover my senses."
"Sure," replied Mom, "I was thinking for this one you could be pretending
to make a salad and see an alternative use for a cucumber. Whilst your
resting I'll just go and pick a costume."
By the time I came downstairs Mom had cleared all the clothes from the
table with the exception of a pair of itty-bitty shorts and the porn star
T-shirt. She'd also set up some props including a massive cucumber, which
I'd been planning to have as part of tomorrow's salad.
I cut a few tomatoes and tossed them into the bowl, and then took the
cucumber. I raised the knife and was about to chop, when I (or rather my
character) decided not to. Instead I pretend to look out into the garden
and lounge, to check if anybody was around.
Then I undid my shorts and let them fall to the floor. Then my T-shirt
followed it. I gave a quick waggle of my tits to the camera before picking
up the cucumber and lying back on the kitchen table. Grasping the vegetable
I slid it between my cleavage. Mom got on the table and stood above me. I
could see her crack, through her panties and it was turning me on. But it
was too soon to use the cucumber in my own slot, so instead I grasped one
of my tits hard with my spare hand and fondled it.
Eventually I couldn't wait any longer, "Mom - I'm going frig the cucumber
now. Are you at the right angle."
Mom climbed off the table and knelt down in front of me so that the camera
was directly pointing at my twat. I pushed the cucumber in. It was cool,
but not so much that it deaden the feeling in my clit as the nub of the
vegetable banged against it.
"Oohhh, uurrggghhh," I grunted I frigged myself to completion. Juice
started to soak against the cucumber, trickling down its green skin to sop
against my hand. I continued pushing.
"Aaaarrrggghhh" I screamed as the orgasm rushed through me.
I slid the cucumber out. Then I gave a smile to camera and bit into it. The
skin tasted awful.
_ _ _
If you have any comments on this or any other of my stories, e-mail me at
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