MILF seduced a teen lesbian girl

She tells me her name is Gail. It’s a leather bash at
Chicky’s and I’m standing at the bar with my second beer and a
taco chip. She tells me her name is Gail, and then she says: “You
have such lovely hair.”
She’s very thin, tall, wasted looking, too much dark hair.
She says she runs a clothes boutique on Oak Street, but I don’t
know if I should believe her. Oak Street is swank, chi-chi, one
long block of phoniness, and maybe I should not believe her. But
why would anyone come to Chicky’s and tell a lie like that? No,
it must be the truth. I think I’ve seen her other places too, but
I’m not certain. I ask her if she owns the shop and she says yes,
she owns it and she runs it. “It’s all mine,” she says. “Believe
me, it gets boring.”
What she does for excitement is cruise the bars looking for
cunt. Yes, that’s how it is. I can see it clearly. She’s looking
for it. She’s looking at me. The only leather I’m wearing is my
watchband. I look at her boots. I look at her vest. Well, it’s
enough, isn’t it? That’s enough black leather to make the point
without equivocation. As if to be certain I understand things,
she pulls back one side of the vest to uncover a silver chain
dangling from one pocket. I get a rush as I stare at it. It looks
like real silver, a dangling silver chain. Why am I hesitating? I
have no job and almost no money. My life since Teresa threw me
out has been completely stupid. And now Gail is here. She has
money, she wears leather, she has that poisoned look in her eyes.
Outside Chicky’s, she waves down a taxi, and once we’re
inside it she puts her hand on my knee and she squeezes it. It’s
a possession; she already possesses my knee.
She takes me to a hi-rise on the Gold Coast, a building with
a uniformed doorman and vases filled with roses in the lobby. “I
walk to work,” Gail says. “I adore living here.”
The apartment is filled with streamlined Italian furniture,
leather and chrome and furs on the chairs. It’s more luxury than
I’ve seen in a long time. Teresa doesn’t have as much as this.
Gail tells me to make myself a drink and she leaves me. I don’t
want to drink anything. My hands are shaking too much. Instead I
stand at the window and I look down at the water and the beach.
When Gail comes back, she’s wearing the vest and the boots
and nothing else. The silver chain is gone, but in one hand she’s
carrying a riding crop.
Her cunt hair is dark, trimmed to a perfect black triangle.
Ignoring me, she walks to the bar and she pours something
from one of the bottles into a glass. “I always use a word,” she
says. “When it gets to be too much for you, say Claudia.”
Why Claudia? Who is Claudia?
She says: “Aren’t you drinking anything?”
I tell her no. I watch her as she adds two cubes of ice to
the drink. She sips the drink, then she turns to look at me.
“Come on, get naked,” she says.
There’s not a hint of warmth in her voice. Maybe the warmth
will come later. Sometimes I get it and sometimes I don’t.
Usually I don’t care, not at the beginning. Right now I’m not
here for the warmth, I’m here for something else. My legs are
trembling because I know she intends to use that riding crop. I
avoid her eyes as I peel my clothes off. I take everything off,
get myself completely naked, my bare toes curling into the thick
rug.
She looks at me. She can’t hide the interest in her eyes.
She puts her drink down, and then she walks toward me with her
eyes on my belly. When she’s close enough, she surprises me by
sliding her free arm around my waist and kissing my mouth hard. I
feel the leather vest pressing against my breasts, her hand
sliding down from my waist to my ass. Then she finishes the kiss
and she pulls away from me and says: “First, let’s find out what
you can take. Why don’t you bend over the back of that chair?”
I look at the easy chair. It has a low roll back and no
arms. I walk over to it, stand behind it and then lean forward to
double my body over the roll. My head is hanging down, my legs
apart, my feet on the rug, my hands trembling as I grip the
upholstery to steady myself.
She comes to the front first, and then she taps the riding
crop against my face, against my mouth.
I kiss it. I kiss the source of imminent pain.
She pulls the riding crop away and she moves behind me. I
keep my eyes closed, waiting, feeling the blood in my head,
feeling my heart pound.
I hear the stroke before I feel it, a hissing sound, then a
burning slash across my buttocks.
She does it again. And again.
And the fire begins in my cunt as I wait for the next
stroke.

* * *

I don’t like the pain that much. If I have a choice between
pain and other forms of punishment, I usually choose the other
forms. But pain is often necessary because many of the tops like
inflicting it. They like watching you get it. I’ve never met a
top who seemed bored while inflicting real pain. They get bored
only if they have a need to inflict real pain but the opportunity
isn’t there. Sometimes the opportunity isn’t there because they
can’t admit to themselves how much they want it. That’s the best
kind of top. She’s always irritated by you, and she finds ways to
make your life a constant torment. She never ignores you, because
whenever you’re there you remind her of the inner conflict she
feels.
My goal in life is to find the perfect top, someone who will
never ignore me, never mark me permanently, inflict only minimum
pain and have enough money to pamper me.
I do need to be pampered.

* * *

But now I’m not being pampered, I’m being whipped.
And I’m moaning.
Gail hears me moaning, but the whipping continues.
I lose count of the strokes, but finally Gail stops whipping
me. I can’t move. My ass is on fire and my body is covered with a
film of sweat.
I moan again.
And Gail says: “Shut up, will you? I’ve stopped.”
Then I feel her hands on my ass, her fingertips running over
the welts. Her touch makes me wince, but I do my best not to
moan; if I moan now, she might whip me again and make the hurt
even worse.
She starts probing. I knew it would happen and I’m ready for
it. When I feel her fingers in my cunt, I whimper to show my
pleasure. I’m wet, of course; the whipping has brought the juices
out and her fingers have no difficulty penetrating me deeply.
Then I feel another finger pushing at my anus. Maybe it’s her
thumb. Yes, it must be; I can feel the thickness of the second
knuckle. She pushes her thumb deep inside my ass while she holds
the other fingers in my cunt. She starts fucking me. She takes me
completely, hard, fast, no dalliance at all. I start coming
almost immediately, and now I’m squealing with happiness as she
makes me her complete slave.
Then suddenly the fingers are gone, my two holes empty.
“Don’t move,” she says. She backs away and she leaves me. I
hear her go to the bar. I hear the ice dropping into the glass.
My cunt is tingling, the aftereffects of the strong orgasm not
yet dissipated. When I close my thighs, I can feel the wetness.
Gail returns. She knows I want her fingers again, but
instead I get the riding crop. I cry out at the first blow. She
does it harder this time and the pain quickly becomes
excruciating. I’m afraid to use the code word for fear she’ll
find me unworthy, find me too quick to end the physical
punishment, too unsuitable to keep at her beck and call. I don’t
want to be unsuitable. I sob. I beg her to stop. But of course
she pays no attention and she goes on with it.
Finally it’s too much. My soul at the edge of destruction, I
gasp the word she gave me: “Claudia!”

* * *

She has me on her bed on my belly as she soothes me with
tenderness and dabs of anesthetic ointment on the welts. “Poor
little girl,” she says. She kisses my shoulder. She tells me the
skin isn’t broken anywhere. “Is it still bad?”
“No, it’s better.”
“I’ll get you some aspirin if you like.”
“No, I’m fine. Really I am.”
She strokes my head and she kisses my shoulder again. Then
she leaves me and she walks around to the other side of the bed
to lie down beside me. I turn my head to look at her. She’s naked
now, her nipples like tiny dark turrets at the tips of her small
breasts. As she lies on her side, she sees me looking at her
breasts and she smiles and maneuvers her body to get one of her
nipples between my lips.
She toys with my hair as I suck her breast. Then she murmurs
something, her hand pushing at my head, the meaning clear. I turn
my body and move over her, slide my face over her belly and down
to the perfect dark triangle. With a sigh, she raises her knees,
then lifts her legs over my shoulders as I burrow into the wet
trough.
At first it’s the wetness; the flowing stream is all I
experience. The whipping caused her faucet to flow, and the cunt
syrup is everywhere. I lick slowly, gathering the nectar,
avoiding her clitoris except for an occasional rub with the tip
of my nose. My mouth and chin quickly become inundated with her
warm juices. Now my tongue probes more deeply, my mouth pressing
against the opening as I hold the long lips to each side with my
fingers. She starts rocking her knees as my tongue dances in her
vagina. Using her hands, she pulls her knees all the way back to
her breasts and she lifts her legs to point her toes at the
ceiling.
No sound penetrates the room from outside. The only sounds
in the room are an occasional moan made by Gail’s throat and the
liquid sounds made by my tongue and lips as I suck at her cunt.
I adore the wetness. The wetness is an affirmation of her
interest in me, this wetness caused by her excitement when she
hurt me. I scour the hole, cleaning it, sucking at it, still
avoiding her clitoris that now protrudes like a tiny animal
seeking to be stroked. With a groan, she pushes my head further
down, and immediately I attack the smaller opening, licking it,
applying my lips to it, pushing my tongue inside her ass as once
again she rocks her knees in her pleasure.
“Oh, you little bitch,” she says. She hooks one leg around
my neck to hold my face in place, to keep my mouth sucking at her
dark little hole. I lose myself in it, unaware of anything now
except her anus, her thighs, the wetness of her cunt against my
face. Then I feel one of her hands touching my forehead, and the
next moment she begins rubbing her clitoris while I continue
sucking her anus. That’s how she comes. She rubs herself off as I
work my tongue in a frenzy. Her legs rock, she groans, and still
my lips remain fastened to the twitching ring of her anus.
Later she says: “Have dinner with me tonight. I know a place
on Clark where the Spanish chicken is marvelous.” Then she
questions me about my life in the city. “Where are you living?”
I give her the name of a women’s residence near Lincoln
Park. “It’s ugly.”
“Do you have a job?”
“No.”
“But what do you use for money?”
“I scrounge.”
“Oh dear.” She goes to her purse and she pulls out some
money. “Here, take this. Do you have anything to wear this
evening? Take taxis, will you?”
She hands me five twenties. The bills are brand new.
Everything is so easy when you have money.

* * *

I go home to shower and get dressed for dinner. A girl I
know sees me walk into the lobby after leaving the taxi.
“Hey, what happened to you? You get rich?”
“I’ll write you a letter.”
“All right, I won’t ask.”
She won’t ask where I got the money or she won’t ask to
borrow some? When I get to my room, I lock the door and I strip
my clothes off. I feel good. I feel like something will happen
with Gail. A shiver passes up my spine as I remember the
whipping. I climb up on the bed and I look at my ass in the
dresser mirror. The stripes are red and purple, five or six
across both cheeks. There’s no pain now, nothing at all, and when
I run the flat of my hand gently over the stripes I don’t feel
any hurt from it.
After a while I put a robe on, grab a towel and some soap
and leave my room to hurry down the hall to shower. I hate this
place. The halls are dingy and the bathroom stinks. Sometimes the
pipes in the bathroom are broken and it’s a filthy mess. I heard
someone talk about a girl on one of the upper floors who killed
herself a month ago.
When I’m finished in the shower, I hurry back to my room to
dress. What should I wear? Now I’m sorry I didn’t ask Gail if she
wanted me to wear something special. What does she like? I try to
imagine what she likes as I pull the clothes out of the closet.
There isn’t much anyway, but I do my best to throw together an
outfit that doesn’t look too freaky. I don’t think Gail wants me
to look too freaky. I think what she wants is an all-American
girl type who just happens to be a sick masochist willing to have
everything done to her, even the worst of it. I’ve had the worst
of it, and let me tell you while I’m having it I love it. It’s
only afterward that I feel horrible. Afterward I feel like
crawling into a dark hole.

* * *

“You look lovely,” Gail says.
The restaurant is cozy, chic, the lighting dim enough to be
like candlelight. Classical guitar music can be heard in the
background. Is it Segovia? We both order a chicken dish. Gail
has a bottle of red wine brought to the table, and after the wine
is poured, she lifts her glass. “To Marcy and Gail,” she says.
When our eyes meet, I remember how I was bent over that
chair in her living room with my ass under the riding crop. I
remember the taste of her flooded cunt, the warm juices sliding
over my teeth. I listen now as she talks about her business
affairs, the fashion shows in New York, her travels in Europe.
What I want to know is who was her last slave, but I’m afraid to
ask. Instead I sip the red wine, think about her, hope that she’s
thinking about me and what she’d like us to do later on.
Then she wants to know when I came out. “In college?”
“Yes.”
“College is always a great transition for people.”
“Yes.”
“You’re lovely.”
Does she mean I’m lovely as a slave or lovely period? Is she
remembering things? Her eyes tell me nothing; I want so much to
know everything, but her eyes tell me nothing.
When we leave the restaurant and stand on the sidewalk
waiting for a taxi, she takes my hand in hers and she holds it. I
suppose anyone looking at us would think I’m her niece. It’s
amusing, isn’t it?

* * *

“Can you stay?”
She says this the moment we enter her apartment. It’s now
nearly eleven o’clock and I’ve already planned to stay the night,
packed the necessities in my purse because I’m desperate to stay
here. The idea of going back to that dreary hole I’ve been living
in puts a knot in my chest.
When I tell her I can stay, she smiles and she takes me in
her arms. She says: “I wouldn’t let you go anyway. I was just
asking.”
Then she kisses me, and as she presses her mouth against
mine, I’m feeling the red wine and my legs are unsteady. She
pushes her tongue between my lips and she gives it to me in and
out, in and out, her wet tongue sliding like a living thing while
she puts her hands on my ass.
When she pulls her mouth away, she says: “Does it still
hurt?”
“No, I’m fine.”
She takes me to the living room and she makes me stand in
the center of it while she undresses me. When she has my breasts
uncovered, she takes my nipples with both hands and she says:
“Let’s try this.” She starts pinching. She pinches hard, and the
sudden pain is too much and I cry out like a wounded animal. She
laughs and releases me. “All right, finish undressing yourself.”
She leaves me. She goes to the bar to pour some brandy into
two glasses. By the time she returns to me, I’m naked, and when
she hands me one of the brandy glasses I want it in order to
fortify myself. Tonight it will be bad with her. I sense that. I
can see in her eyes that everything will be bad. We sip the
brandy awhile without saying anything, and then she takes my
glass and she puts it down on one of the small tables and she
puts her glass down beside it. Then she turns to me and she takes
my breasts in her hands again, but this time she’s gentle,
fondling them, lifting them, then bending her head to take a
nipple in her mouth and bite it gently with her teeth. Then she
wants to look at my ass and I have to turn my back to her so she
can see the marks on my buttocks.
“Much better,” she says. She makes me turn around again to
face her. She laughs and says: “The marks turn me on.”
She sits down and she has me stand in front of her. Then she
wants one of my legs raised to make it easier to see my cunt. So
I do that; I put my left foot on the edge of the sofa beside her
and swing my knee to the side to expose myself.
She touches me. She separates my labia with her fingers to
look at my clitoris. She looks at me a long time, tugging here
and there, touching me in various places, the examination more
clinical than casual, and of course before long my syrup is
flowing in abundance and that amuses her. She toys with me,
stroking me with her fingers, a light feathery stroking designed
to make me want more. I moan and move my hips as her fingertips
graze around my clitoris. Then she pushes two fingers inside me.
She curls the fingers and she lifts her hand, the fingers acting
as a hook to pull me forward.
She looks up at me. “Hello, darling.”
My knees tremble. “Hello.”
“Move your ass some more. Yes, that’s better.” Then suddenly
she pulls her fingers out and she says: “Turn around.”
I do that, and in a moment I feel her hand gliding over my
thighs and then between them to find my cunt. Without her asking
for it, I move my legs apart and bend forward a bit. She slides
her fingers inside me again and she tells me to move my hips as
she begins fucking me. “That’s it. Go on, come if you want.”
It’s like a damn breaking open. I hear the grunting in my
throat, feel her fingers thrusting in and out of my wet hole as
my body shakes from head to toe.
After that she takes me to her bedroom. She undresses while
I lie on the bed and watch her. Is she wet? I imagine her cunt is
dripping on the insides of her thighs and I want to sniff it and
lick each drop with my tongue.
Before long she’s on the bed. Naked, she straddles me with
her knees under my shoulders, her hands gripping the headboard,
her cunt grinding against my face.
“Yes, like that,” she says.
She pushes down, the hairy mouth possessing me, swallowing
me, her syrup gushing. She rocks back and forth. She moans. I
hold her buttocks in my hands as I drink from the fountain.
Afterward she says: “There’s a spare bedroom down the hall.
You don’t mind, do you? I never like sleeping with anyone.”
I don’t care one way or the other. After all the wine and
brandy, and then her juices flowing in my mouth, I’m drunk with
happiness. The spare bedroom is really a maid’s room, but it’s
better than the hole I live in at that women’s residence. In the
morning Gail has breakfast with me, but then it’s clear she’s had
enough of me and she wants me out. The hundred is sufficient,
isn’t it? I tell myself the hundred she gave me is fine, so why
complain? When I walk out on Lake Shore Drive, it’s a new morning
and I can pretend I actually live here. What I decide at this
moment is that I’m not taking any more punishment. Am I lying to
myself? I’m not sure one way or the other.