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‘old woman’ stories

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30 DaysAll Time

Jori - A Fairy Tale of Sorts Ch. 04

Liberation.

by eidetic in Sci-Fi & Fantasy 10/31/2016
H
4.85
12.6k
14
9
16

Va-Cay

A new idea brings two people together forever.

by komrad1156 in Mature 04/07/2018
H
4.84
45.4k
78
14
99
0

Hell's Kitchen

Nepotism and a tragic loss bring two people together.

by komrad1156 in Mature 07/03/2018
H
4.83
29.3k
56
15
71
0

Jori - A Fairy Tale of Sorts Ch. 02

Iteration.

by eidetic in Sci-Fi & Fantasy 10/29/2016
H
4.81
15k
12
3
14

The Wheels on the Bus

Two hopeless romantics meet by chance and fall in love.

by komrad1156 in Mature 05/23/2018
H
4.8
28.6k
41
9
51
0

Love is in the Air

A sudden, near-death experience leads to love.

by komrad1156 in Mature 04/01/2018
H
4.8
35.6k
60
14
71
0

Stand Tall

A young jockey stands tall for the older woman he loves.

by komrad1156 in Mature 12/20/2017
H
4.8
35.3k
51
17
69
0

Jori - A Fairy Tale of Sorts Ch. 03

Transformation.

by eidetic in Sci-Fi & Fantasy 10/30/2016
H
4.79
13.9k
7
3
9

Jump Started

Retired schoolmarms last assignment, a 19 yr old virgin.

by R410a in Mature 09/02/2021
H
4.79
38k
44
18
85
0

Out of Gas

Running out of gas changes two lives forever.

by komrad1156 in Mature 03/01/2018
H
4.78
58.9k
62
16
78
0

The Storm Ch. 07

Sara finds purpose.

by Sara692 in Erotic Horror 12/25/2010
H
4.77
11.3k
4
2
8

Love Conquers All

An older woman proves to a younger man love conquers all.

by komrad1156 in Mature 05/18/2018
H
4.77
53.5k
62
13
88
0

Jori - A Fairy Tale of Sorts Ch. 01

Rejuvenation.

by eidetic in Sci-Fi & Fantasy 10/28/2016
H
4.76
23.4k
22
1
32

The Spinster and the Boy Ch. 09

Jocelyn always gets what she wants.

by peteh57 in Mature 07/24/2023
H
4.76
14.2k
28
17
38

Right in Front of You

Bad boys and bad decisions force an older woman to change.

by komrad1156 in Mature 05/29/2018
H
4.75
60k
60
17
86
0

Fame and Fortune

Fame and fortune are replaced by true love.

by komrad1156 in Mature 03/22/2018
H
4.75
37.2k
44
7
61
0

Vacation Park Out of Season Ch. 02

A Scandinavian vacation park where everyone is his slave.

by TrappistNun in NonConsent/Reluctance 01/29/2022
H
4.75
10.5k
0
1
12

Dark End of the Street

Tragedy and therapy bring two lonely people together.

by komrad1156 in Mature 01/03/2018
H
4.74
32k
45
12
55
0

Desperate Times, Desperate Measures

A woman's sense of desperation changes her life forever.

by komrad1156 in Mature 02/02/2018
H
4.71
44.8k
52
11
73

Old Betty

Old Betty brings out Adam’s taste for old women.

by st0rmbringer in Mature 10/04/2022
H
4.71
75.5k
64
33
110
0

Losing Faith in Faith

Death, divorce and doubt bring love to an unlikely couple.

by komrad1156 in Mature 03/03/2018
H
4.7
40.7k
56
21
74
0

Once Upon a Time in Florida Pt. 01

A handsome young man rocks Elise’s world to its foundations.

by st0rmbringer in Mature 12/07/2022
H
4.7
28.8k
36
14
64

The Spinster and the Boy Ch. 08

The slave MILF, her horny daughter, and the sinning priest.

by peteh57 in Mature 06/06/2023
H
4.7
18k
33
7
43

Once Upon a Time in Florida Pt. 02

They finally come together and satisfy their desires.

by st0rmbringer in Mature 12/11/2022
H
4.7
10.8k
14
5
20

GTO

Mature seductress adds 2 recruits to her stable.

by GTO_Racer in Mature 01/16/2018
H
4.7
39.9k
54
11
76
0

A Camping Weekend

Camping with my sister and her best friend.

by SEAWATER1 in Incest/Taboo 08/16/2022
H
4.7
154.5k
185
29
349
0

Beach House

Summer vacation leads a lonely, older woman to love.

by komrad1156 in Mature 06/19/2018
H
4.7
96.6k
135
26
175
0

The Widow Henderson

Young man discovers joys of his neighbor.

by blaster666 in Mature 01/31/2014
H
4.66
271.3k
209
38
280
0

No Frame of Reference (New Knees!)

Very old woman helped in knee-rehab by much younger man.

by XXscribbler in Mature 03/31/2018
H
4.64
29.5k
24
7
29
0

Rich Bitch Pt. 01

I become rich and start my journey to becoming a cougar.

by slimpic11 in Mature 07/09/2018
H
4.64
51.3k
39
1
60

Fleet Week

New York City, Fleet Week, old dowager... and surprises.

by atkins in Mature 12/12/2007
H
4.63
40.4k
9
7
13
0

Once Upon a Time in Florida Pt. 03

Elise goes shopping, gets a makeover and more.

by st0rmbringer in Mature 12/13/2022
H
4.63
8.5k
9
1
17

Nana Cotton's Secret

His long ago babysitter harbors a dark side . . .

by atkins in Mature 08/07/2015
H
4.61
62.9k
52
7
61
0

The Lady of Bathe Street

There's something really weird about her.

by MsCherylTerra in Mature 08/24/2020
H
4.61
43.4k
33
45
58
0

Rich Bitch Pt. 02

I find the right person to nurture my cougar side.

by slimpic11 in Mature 07/10/2018
H
4.61
24.5k
10
1
14

Doris Takes Over Ch. 02

Continuation of Doris Takes Over.

by tart_grapefruit in Mature 03/28/2024
H
4.6
7.3k
13
5
20

A Visit with My Mother-in-Law

Dylon stays with his mother-in-law for a few days.

by st0rmbringer in Incest/Taboo 10/18/2023
H
4.59
104.7k
131
18
226
0

Mrs. Tenholder Loses It

My 72-year-old neighbor finally loses it at the movies.

by atkins in Mature 06/27/2009
H
4.59
171.6k
81
8
103
0

You're The Boss

Young man starts a new job with a strict boss.

by chris4chat in Mature 01/26/2018
H
4.58
59.7k
39
8
45
0

Madonna Ch. 05

Consummation.

by TheGraduate88 in First Time 01/13/2022
H
4.58
4.7k
1
0
3

Personal Shower

Young man show old houseguest some new equipment.

by atkins in Mature 07/05/2006
H
4.57
194.8k
22
4
34
0

Nate and Jean

Young guy enjoys a much older mature woman.

by toynwithwords in Mature 12/19/2015
H
4.57
63.7k
33
5
39
0

A Married Woman's Mid-Life Crisis

An older married woman finds out what's missing in her life.

by Pussymad42 in Mature 06/22/2018
H
4.57
95.1k
65
15
93
0

The Girl Next Door

Pam discovers the truth about her neighbours.

by Sindy070 in Lesbian Sex 05/30/2014
H
4.55
175.6k
124
17
154
0

The Young Duke of Tupping

A loss of virginity in Victorian England.

by reminnes in Mature 10/02/2005
H
4.54
72.9k
16
2
26

Nick and the Librarian

Nick studies a new subject.

by Foxee Browne in Mature 02/27/2007
H
4.54
100.9k
10
7
13
0

Burgundy Lips Ch. 02

Elizabeth has her way with Kurt.

by qdata in Fetish 06/10/2014
H
4.54
23.3k
4
1
5

Older Than My Mum

College student meet an old lady.

by uksnowy in Erotic Couplings 12/30/2017
H
4.53
30.9k
16
4
20
0

Oh, I Love the Mature Woman

When a woman knows how to fuck, it's all the difference.

by savetheworld in Mature 02/10/2018
H
4.53
78.9k
62
7
86

Neighbors Ch. 01: Window to Paradise

Young man and older woman enjoy mutual voyeurism.

by sexagenerian66 in Mature 06/14/2016
H
4.53
42.3k
32
7
42

"Call Me Mommy"

A young man meets a woman with an interesting kink.

by calcul8ing in Mature 12/30/2017
H
4.52
141.6k
128
19
168
0

Denny Moves On to Gramma

Dennis consoles gramma after granpa's death.

by denny9 in Incest/Taboo 05/23/2001
H
4.51
393.1k
72
4
104
0

Sinful Degrees of Separation Pt. 06

Sexy mom fucks daughter's boyfriend's massive 13 inch cock.

by shoguy in Mature 12/12/2014
H
4.51
148.4k
86
5
114

A Slow Seduction of Jasmine Pilcher Ch. 04

She's breaking down in sweet slow-motion.

by atkins in Mature 07/05/2005
H
4.51
79.3k
10
2
12

Better Late Than Never

He met his petite old teacher and then her amazon niece.

by blackstroker in Mature 05/01/2020
H
4.51
33.2k
28
4
44
0

The Scent of a Rose

His experience with an old grandmotherly neighbor.

by atkins in Mature 01/19/2002
H
4.51
237.5k
51
8
64
0

A Slow Seduction of Jasmine Pilcher Ch. 06

The debauchery continues.

by atkins in Mature 09/24/2005
H
4.5
88.4k
11
6
13

College Guy meets MILF

College guy earns extra money.

by Brian6588 in Erotic Couplings 02/03/2018
H
4.5
54.3k
53
7
68
0

Better Late than Never

Ethan & Sally have an on and off again May-December romance.

by st0rmbringer in Mature 09/29/2022
H
4.5
14.1k
14
4
23
0

Edna

Sucking her tits makes an old woman cum wildly.

by kalodin in Mature 06/25/2014
4.49
99.4k
26
19
36

My Hot Teacher

Student gets private tutorial he didn't expect.

by Nikkiejanes in Erotic Couplings 05/29/2018
4.49
46.3k
40
7
49
0

Man-Child Pt. 01

Older woman shows younger man how to do it.

by HisLittleHotOne in Mature 05/31/2014
4.49
89.3k
58
9
64

A Tale of Two Grannies

Two old ladies find pleasure with a young man.

by goodyearman in Mature 05/22/2018
4.48
76.3k
45
6
66

A Fat BlackOldWomanLove Story

Seven steps is a short way for rewarding.

by BlackOldWomanLove in Mature 09/04/2005
4.48
201.5k
34
3
44

An Unlikely Hero - Alternate Version

A young blonde is rescued but things go a different route.

by st0rmbringer in Interracial Love 03/21/2023
4.47
11.2k
19
2
35

Once Upon a Time in Florida Pt. 04

Elise takes Javi to her family cookout. The final chapter.

by st0rmbringer in Mature 12/17/2022
4.46
5.2k
6
3
10

Before He Goes

Mother and son desire each other.

by standingstones in Incest/Taboo 01/29/2014
4.45
259.3k
222
3
277

Orthodontic Appointment

Mature orthodontist longs for young guy's dick.

by conradomoreno in Mature 10/12/2022
4.45
30.5k
23
2
38
0

Car Pooling Pt. 01

What will an older woman do for a ride to work.

by TonyMA70 in Mature 03/28/2018
4.45
97.5k
109
9
153

Grandma's Boy Toy

Grandmother and grandson enjoy a car wash.

by earlbrowder in Incest/Taboo 05/03/2005
4.45
486.2k
109
20
155
0

The Bull, the Cock, the Cuckold

Alpha male unleashes the animal longing in an old woman.

by atkins in Mature 03/04/2020
4.44
61.2k
50
6
68
0

Afterglow

Taking "love thy neighbor" literally...

by Dar_Jisbo in Mature 12/30/2020
4.43
41.8k
21
2
32
0

Life Goes On

College graduate is seduced by much older woman.

by Dar_Jisbo in Mature 12/08/2017
4.42
52.3k
28
0
37
0

Vera

A young man debauches an eager old woman.

by atkins in Mature 05/29/2006
4.4
276.7k
40
15
51
0

Watching Porn with Mature Friend Pt. 01

Young guy watches porn with mature family friend.

by ikemay in Mature 01/27/2018
4.4
133k
96
6
140

Wrinkly, Kinky and a Promise

Fuck-happy oldie raises her game.

by CuddlyAl in Mature 11/20/2011
0
132.1k
17
8
22
0

Eternal

Elderly woman hires young male nurse...

by Dar_Jisbo in Mature 09/04/2019
4.4
44.6k
32
4
45
0

Pornopolis: The Journey Ch. 01

Sacred sexual initiation ritual, and a disturbing prophecy.

by Christian Black in Sci-Fi & Fantasy 10/05/2007
4.4
29.5k
6
0
15
0

Every Man Should Have a Hobby

Mine? I like boning old ladies.

by atkins in Mature 12/10/2009
4.39
155k
30
11
37
0

Old Lady Plays with Crossdresser

An old lady gets fucked and then fucks a young cross-dresser.

by writinguy48 in Mature 12/03/2022
4.37
15.6k
7
4
19
0

Seducing My Son's Best Friend Ch. 02

The seduction is done and the play begins.

by jerrys1 in Mature 06/29/2018
4.37
28.3k
16
3
22

Helping Margaret Pt. 02

Margaret and David's friendship grows closer.

by LanceStone in Mature 02/17/2018
4.37
27k
15
0
18

From Ballroom to Bedroom

Philip finds dancing with divorcee very rewarding.

by goodyearman in Mature 01/22/2018
4.37
39.7k
11
3
13
0

Brenda's Misadventure

Mature woman gets discount on siding.

by TonyMA70 in Mature 02/14/2018
4.37
28.7k
15
0
16
0

Young Greg Ch. 03: Loretta's Story

Greg and the senior lady.

by StrattonChambers in Erotic Couplings 09/21/2020
4.37
8.6k
1
0
2

Cruising

Young man finds company on his first cruise.

by carolina67 in Mature 06/28/2018
4.36
47.1k
17
0
26
0

Surprising Old(er) Lady Ch. 06

Perverted but lonely old lady showing him more pleasures.

by Learningfast in Mature 10/23/2020
4.36
19.3k
10
1
21
0

Linda in the Darkroom

Email to a friend describes a man's first sexual teacher.

by pg2xxx in Erotic Couplings 10/05/2006
4.35
19.5k
1
1
5
0

A Fat BlackOldWomanLove Story Ch. 04

Elevator dreams.

by BlackOldWomanLove in Mature 10/25/2005
4.35
58.5k
6
3
8

Dominated by Mature HR

mature HR dominating and testing young intern for job.

by mistress_meeta in Mature 04/14/2022
4.35
26k
12
66
22
0

Lucky Collision

Old woman placates angry cyclist after collision.

by wigsworld in Mature 01/02/2022
4.35
30.1k
17
12
29
0

Scoutmaster's Wife

Wife of scoutmaster allows a violation.

by Magna12 in Mature 07/05/2018
4.34
97.2k
65
7
85

Growing Up Ch. 01

Young Man has Relationship with a Mature Woman.

by Jack1107 in Mature 05/27/2018
4.34
107.1k
81
6
120

The Mature Lady

What will the mature woman do for the younger man affection?

by TonyMA70 in Mature 03/22/2018
4.33
64.4k
30
5
38
0

The Nightcap

A visit to an old haunt brings pleasure for an older woman.

by carolina67 in Mature 05/15/2018
4.31
21.6k
12
0
14
0

Mum's Friends Ch. 01

Older woman attracted to young business man.

by Jack1107 in Mature 05/09/2018
4.31
107.7k
116
4
173

Mother and Her Bad Boys

A mother seduces her son's friend.

by cruiser_2015 in Mature 03/01/2018
4.31
62.6k
39
3
62
0

A Fat BlackOldWomanLove Story Ch. 03

I should have known better.

by BlackOldWomanLove in Mature 10/02/2005
4.31
65.8k
10
0
12
12
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