‘older woman’ stories

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older woman 

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One Night in Cougar Town

Chance meeting with a younger stranger...

3.6
32.6k
1
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Neal and Tara Ch. 02

Neal and Tara have sex.

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4.57
32.6k
14
2
22

Sarah's New Life Ch. 03

Sarah first time with Matt and her dream lover.

4.48
32.6k
26
6
35

May to December Earth Day Romance

The young volunteer likes his director.

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4.56
32.6k
9
3
10
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Alternative Grad School

Grad student rooms in a widow's home.

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4.71
32.6k
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16
79
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03: Sheryl and the Caravan Part 2

A return visit and a first anal for both of us.

4.26
32.6k
8
0
8
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Too Much Sun

His wife is laid up so he meets new friends.

4.21
32.6k
11
1
15
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A Bit of Spice

Meg has to work late, so Justin has a different Date Night.

4.43
32.6k
39
2
68
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Massage Experiences

A compilation of massage experiences.

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4.58
32.6k
17
6
40
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Somewhere in the Urango Ocean

A BBW and her son meet a SSBBW and son couple on holidays.

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4.51
32.6k
62
5
90
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Smoke

A one night stand.

3.89
32.6k
3
7
3
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Manchild

Sexy MILF entertains young stud - with husband's blessing.

4.4
32.6k
105
53
162
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Marvelous Miss Claudia

That time you fucked your teacher.

4.28
32.5k
20
4
37
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By Design Ch. 02

Nerdy introvert meets shy, but horny, older woman.

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4.69
32.5k
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36

Personal Growth

Anna wants to be better. Her sister's man has other ideas.

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4.57
32.5k
22
5
55
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Annie Holder's House Pt. 05

An old man punishes an older woman and a young man.

4.43
32.5k
7
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18

Almost Heaven Ch. 09

From high school to hotwife: the conclusion.

3.9
32.4k
8
2
10

It’s Only Being Photographed Pt. 04

Sophie and I find out it's more than that.

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4.82
32.4k
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51

Desire

She couldn't help it.

4.1
32.4k
6
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8
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Obsessed with Youth

The remarkable rebirth of Eliza Doolittle.

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4.71
32.4k
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Mom's Biggest Fan Ch. 06

Mom shows daughter a few new surprises.

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4.68
32.4k
43
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Shareware

Continuing the education of a geek.

4.34
32.4k
3
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5
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Working at an swinger resort Pt. 02

My experiences, working at an exclusive swinger resort.

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4.77
32.4k
41
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69

Fate

A chance meeting at a lesbian bar leads to love.

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4.61
32.3k
45
15
65
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Colette, Laurel...and Me Ch. 01

Mature woman picks a sexual protege. Or two.

4.4
32.3k
13
1
16
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Thickness Galore Next-door

The thick Portuguese neighbor wanted a son and some cock.

4.46
32.3k
30
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44
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Teddy Bare, Maid to Serve

Good servants are so hard to find these days.

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4.5
32.3k
6
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15
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Shut In

A tragic loss and fear nearly cause a woman to lose hope.

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4.81
32.3k
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69
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Maria and Her Boys Ch. 02

Once jilted, now finding more pleasure.

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4.6
32.3k
29
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DMV

A visit to the DMV changes four people's lives forever.

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4.86
32.3k
115
24
147
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Vivid Dreams

Quitting smoking may lead to something special.

4.3
32.3k
51
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Tell MILF What You Want Pt. 01

She is not sure of a threesome with brother-in-law.

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4.58
32.3k
33
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Good Job/Bad Job

A lazy good-for-nothing tries a number of different jobs.

4.45
32.3k
45
17
65
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Sylvia's Mom Pt. 08

Life after Delilah - Beautiful Leann comes to visit.

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4.66
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Mom Named Barbie Ch. 17

Son discusses mom's slut activities at the party with her.

4.27
32.2k
30
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40

Running Through Shepherd Park

A 44 yo woman runs into 21 yo black man and his friends.

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4.52
32.2k
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Nice and Naughty

I hardly see him for half the year.

3.51
32.2k
1
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May to December Ch. 03

Younger man, older woman, lust, and love.

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4.7
32.2k
14
11
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After School Stud Ch. 02

Good intentions push a teacher to make another mistake.

4.38
32.1k
26
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Duplex Ch. 09

Mary and Jason watch the hidden video.

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4.52
32.1k
10
4
15

Claire Learns a Lesson

Claire's employee turns the tables on his boss.

4.44
32.1k
2
4
3
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In Loving Memory Pt. 08

Punishments must be finished.

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4.54
32k
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Lafayette Hills

A young writer falls under the sway of an older woman.

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4.71
32k
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103
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Unexpected Bar Encounter with a Cub

Cougar gets a surprise encounter with a younger man.

4.1
32k
22
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41
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Blessed

Chivalry isn't dead, she is a butch.

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4.7
32k
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55
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Black Bitches Of Ottawa

Black college man meets horny older Black slut.

3.43
32k
7
3
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Midlife

Peter thought he knew what he wanted.

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4.5
32k
10
6
19

The Devil Comes Out at Night Pt. 02

The devil comes out in the daytime, too.

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4.71
32k
19
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34

Kelsey's World Ch. 20

Everybody's a fuck buddy.

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4.76
32k
13
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The Lonely Receptionist

Lonely night shift worker enjoys some company.

4.17
32k
16
9
23
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The Touch Ch. 34

Brothers and their Sisters – Sisters and their Brothers.

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4.76
32k
49
16
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Fall From Grace BWWM

2 middle age female detectives, one well hung white lad.

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4.69
32k
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The Lonely Lady Ch. 02

The daughter returns scheming to reclaim her boyfriend.

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4.75
32k
49
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My Arrival

Young man meets his new land lord for the first time.

4.05
32k
10
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12
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Milf in the Mirror

Mirror, mirror on the wall.

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4.63
31.9k
35
2
55
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Amy

Finding love again.

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4.63
31.9k
15
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19
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Relaxing Ride Ch. 02

Classy older woman befriend a younger woman while on a road.

4.18
31.9k
8
3
10

The Warped & Wicked Gym Coach Ch. 02

Ms. Bandy needs to teach Jake a lesson in manners.

4.34
31.9k
17
8
22

My Summer Cougar Pt. 10

John collects his wages and gets a bonus...

4.43
31.9k
18
1
22

HOA

HOA rules bring a veterinarian and a contractor together.

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4.73
31.9k
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18
68
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BKP: Interview

A very unconventional job interview.

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4.51
31.9k
27
5
55
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Spring Break Teacher

Mature woman finds a virgin at the beach.

4.21
31.9k
23
2
29
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Anna

She was like a snapshot from long ago.

4.43
31.9k
5
4
7
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First Time and Many More Ch. 03

More Erotic Education with Barbara.

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4.54
31.9k
9
3
11

Diana's Tales - Tennis Pt. 01

Aunt and nephew combine forehands and foreplay.

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4.66
31.8k
62
7
112

The Blackmail and Retribution Ch. 02

Shanti Rangaswamy is fucked after lure and promise of Tape.

4.07
31.8k
10
0
13

Heather Finds the Cougar within Her

A woman seduces her son's friend while on a cruise.

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4.71
31.8k
59
10
125
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Ms. Laura Ch. 09

Hot Coffee.

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4.54
31.8k
18
7
22

Roberta Gives to the Bottle Drive

The Eagle Scout collecting was scared but returned.

4.48
31.8k
20
6
27
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Call Her Mommy

An older woman Doms and pegs a younger submissive dude.

4.45
31.8k
29
7
75
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Aunt Lotus

Lily discovers her aunt's secret -- sex ensues.

H
4.59
31.8k
50
3
114

As He Was Going to St Ives Ch. 02

The strangers draw the youth into their depraved world.

4.42
31.8k
6
0
8

Magnanimous

Follow-up to "Sometimes, Things Just Happen".

4.18
31.8k
20
6
36
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Titty Touch Therapy Ch. 02

A vulnerable young woman trusts her therapist.

4.4
31.8k
14
2
29

Fiftieth High School Reunion Ch. 01

College students discover the value of experience.

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4.64
31.8k
19
1
24

The Tutor has Needs

A married tutor finds sex with her student.

3.73
31.7k
23
0
46
0

The Absence Ch. 04

In which Seema loses her virginity.

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4.68
31.7k
7
1
12

Sheila Pt. 01

Sheila starts down a dangerous path.

0
31.7k
6
0
10
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New and Different

First face-to-face encounter between May/December lovers.

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4.55
31.7k
6
0
11
0

Joseph’s Birthday Present

Father knows best, and Peggy knows Father!

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4.58
31.7k
12
2
16
0

Small Town Sex Workers Ch. 01

MILF Gardening. Trimming, edging, and fertilizing.

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4.72
31.7k
78
15
194
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Stinky Sow-Mommy

Pervert with a stink kink dates a sweaty hairy milf.

H
4.68
31.6k
83
8
126
0

The Zoomatic 4k Ch. 07

Jamie, Andy and their moms make videos.

H
4.7
31.6k
53
4
73

Sleepwalking Mom Ch. 15

Silly and Tima get closer. Sylvia's younger sister visits.

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4.75
31.6k
69
11
87

Aunt Aprils Revenge Ch. 02 - James Education

Aunt April continues to educate her nephew James.

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4.66
31.6k
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38
104

Sexy Mandy Wanks The Bag Boy

Mandy Beats A Grocery Bag Boy's Meat.

4.05
31.6k
10
2
22
0

Mother And Son, In Bondage, In Love

Jenni and Peter, Mother and Son, fall in love AND lust!

4.29
31.6k
45
6
76
0

The "It" Factor

What do you do when you come across the "it" factor?

4.31
31.6k
46
28
85
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The New Handyman

I lust for a younger man who finally satisfies my desires.

4.29
31.6k
11
7
12
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Neighborhood MILF Hunter Pt. 03

My first encounter with a mature woman.

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4.74
31.6k
27
5
38

Loving Lusty Latinas: Vera

Black man seduces and fucks older, fit Latina.

4.45
31.6k
31
3
43
0

My Last Summer Before College Ch. 02

Christine's car breaks down.

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4.59
31.5k
16
3
19

A Mutual Learning Experience Ch. 12

Ruth and Martha tell their story; Mother and Martha connect

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4.69
31.5k
21
0
30

Mrs. Sherbitz Ch. 04

Younger man claiming the older woman he loves.

4.4
31.5k
21
1
26

The Touch Ch. 28

Love in the Afternoon.

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4.78
31.5k
59
24
60

Thea

My mature girlfriend of 1996-97.

3.98
31.5k
2
1
4
0
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