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‘younger man older woman’ stories

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Military Mom's Morning Ritual Ch. 01

She discovers son's unusual routine - and helps him with it.

by milfleglover in Incest/Taboo 10/31/2015
4.42
182.4k
206
17
277

Trading in For an Older Model

A young man in a bad marriage finds true love in older woman.

by MayDecemberRomance in Mature 08/16/2014
H
4.7
178.6k
280
49
371
0

A Nip in the Christmas Air

How had he not noticed his grandmother's tits before?

by milfleglover in Incest/Taboo 12/07/2015
H
4.56
169.2k
225
18
302

Steve and the Widow Laura

20-something guy gets it on with a sixty something widow.

by bucksilver in Mature 07/22/2009
H
4.51
142.5k
38
5
56

My Big Milking Tits

A woman in her mid 50s with baby has large lactating breasts.

by jon.hayworth in Mature 06/05/2017
4.32
133.6k
111
7
151

Pictures of Lily

Young tenant finds old photos of his mature landlady.

by Swampcooler in Mature 11/15/2017
H
4.74
126k
172
26
232
0

Jaycee and the Nerd H.S. Teacher

Jaycee seduces and takes another woman

by bucksilver in Mind Control 07/08/2009
4.4
120.1k
37
2
49
0

Granny Nurse Sonia to the Rescue

His grandmother knew what ailed him – and how to fix it.

by milfleglover in Incest/Taboo 11/03/2015
4.45
118.4k
115
13
156

3 Families Vol. 02 Ch. 02

Alex Loses His Virginity To His Aunt Vicky.

by RicoLouis in Incest/Taboo 10/10/2014
0
93.4k
97
9
118

Things Her Husband Won't Do

Older woman, younger man, tired feet, and too much wine.

by KentPreble in Mature 12/19/2018
4.39
91.3k
56
6
93
0

James and His Best Friend's Mom

James fantasy comes true with his best friend's mom.

by Lrt83 in Mature 04/04/2018
3.96
89.4k
42
7
67
0

Family First Ch. 01

Nathan moves in with his aunt before college, hijinx ensue.

by thestepfordgirl in Incest/Taboo 05/31/2020
4.36
86.2k
179
5
345

Carol's Christmas

A Loving Husband recruits a virgin boy as a Christmas Gift.

by Belongs2Beth in Group Sex 11/15/2012
4.1
83k
36
15
50
0

My Sweet Sandy Ch. 01

Young man at a crossroads meets MILF who changes his life.

by Eosphorus in Mature 04/21/2022
H
4.75
77.4k
124
24
233

Making A Deal With My Son’s Bully

A mother visits her son’s bully to confront him.

by ck119 in NonConsent/Reluctance 12/25/2022
4.35
75.5k
111
17
206
0

The Very Young Man Ch. 03

Married couple brings a young man into their sex.

by metacarpal in Group Sex 06/25/2006
H
4.58
69.2k
15
0
22

The Very Young Man Ch. 04

Married couple brings a very young man into their bed.

by metacarpal in Loving Wives 06/26/2006
4.43
67.7k
10
2
15

Understanding Mother-In-Law

Cheryl is an empathetic mother-in-law to Brian.

by imhapless in Loving Wives 04/09/2022
4.43
65.1k
91
24
176
0

Watching Porn with Mature Friend Pt. 02

Sex with mature Jane continues as porn plays on TV.

by ikemay in Mature 02/02/2018
H
4.5
64k
50
4
64

A Trip to Remember

While hitch hiking I caught a ride and got taught about sex.

by Comshaw in Mature 08/23/2020
H
4.65
62.6k
45
11
68
0

Reconnecting with Rene

A fantasy with my former boss becomes a reality.

by dpingjessie in Mature 09/02/2016
4.49
58.5k
40
3
58

The Spinster and the Boy Ch. 05

The old woman decides she can't live without the stupid boy!

by peteh57 in Mature 05/16/2020
H
4.75
55.4k
83
48
108

Francine and Her New Neighbors

Francine plays with her new neighbors.

by Lrt83 in Mature 04/03/2018
4.25
51.7k
33
7
50

Her Silent Hand Ch. 02

Sexy and silent domination continues.

by milfleglover in Mature 10/28/2015
H
4.57
50.5k
36
9
48

A Better Anniversary

Disastrous anniversary date is saved at home.

by Sutty93 in Incest/Taboo 09/07/2023
H
4.58
50.5k
140
20
253
0

Hooking Up Mrs. Curry Ch. 03

Their affair turns romantic on the road.

by milfleglover in Mature 11/06/2015
H
4.69
50.2k
30
5
42

Bartering Sex, Bride as Payment, Ch. 04

Husband has sex with wife's mother, his mother-in-law, Anne.

by SusanJillParker in Incest/Taboo 12/24/2017
0
46.2k
46
6
57

Transforming Genevieve Ch. 04

Her transformation complete, she explores her new sexuality.

by R_U_Romantic in Erotic Couplings 02/05/2007
H
4.66
42.1k
8
7
15

The Trojan Lasagna Ch. 02 - Second Helping

Josh's prom date dumps him; her mom heals his broken heart.

by NewOldGuy77 in Mature 09/12/2021
H
4.73
42.1k
60
30
91

Elaine's Dirty Knickers Ch. 06

Elaine's teenage babysitter indulges her dirtiest secrets!

by Paradiggler in Fetish 08/25/2016
H
4.52
41.9k
23
4
32

Black Book Diary Entry: Gertrude

We were just friends and co-workers.

by PositiveThinker in Mature 12/19/2009
4.16
38.4k
8
2
11

Cathleen the Cougar

35M meets irresistible 55 year old redhead.

by devoutmalesub in Mature 09/20/2019
4.29
34.9k
16
3
30
0

Sequestered Jury

Being sequestered changes some jurors lives.

by imhapless in Loving Wives 02/06/2024
4.48
34.9k
80
65
141
0

My Sweet Sandy Ch. 02

MILF Sandy continues introducing James to new experiences.

by Eosphorus in Mature 04/23/2022
H
4.78
34.4k
40
11
59

Mrs. O'Malley's Golden Juices Ch. 14

Naughty young repairman gets more than he bargained for.

by milfleglover in Fetish 11/23/2015
4.45
33.5k
19
3
23

Pam's Houseguest Ch. 02

David joins Pam and her good friend, Toni, for dinner.

by cnp_dudley in Group Sex 04/01/2018
H
4.67
31.6k
26
4
39

Linda Gets Lucky at College

Single woman finds love with a college student.

by Lrt83 in Mature 04/07/2018
3.97
29.7k
17
3
30

She Let Herself Go Free: Final Time

Sex-free conclusion to their fantasies.

by RedHairedandFriendly in BDSM 09/03/2006
4.43
27.9k
2
6
3

Root and the Léger Sisters

The Root meets the Léger sisters and their grands tétons.

by RootRadio in Incest/Taboo 03/26/2020
H
4.66
25.3k
41
3
65
0

My Sweet Sandy Ch. 04

A day out with MILF Sandy followed by new sexual adventures.

by Eosphorus in Mature 04/26/2022
H
4.82
25.1k
31
8
49

The Douche Valve Kit

Haley wants a douche valve kit for her birthday.

by imhapless in Loving Wives 10/15/2023
4.35
24.5k
38
46
82
0

Spy Games Ch. 01

A young man's first time.

by Aaroneous in First Time 03/22/2022
H
4.62
24.4k
22
3
67

Audacious CEO

Strip Aerobics classes change the life of a CEO.

by amyyum in Loving Wives 06/11/2023
4.4
23.4k
43
26
84
0

Bobby 03

Will Bobby get his huge cock back inside Mrs. Carter?

by LuckyNumber in Audio 10/16/2020
H
4.61
22.5k
2
2
8

Albino and Redbone

Opposites attract at a local restaurant.

by Swampcooler in Interracial Love 03/09/2018
H
4.74
22.3k
41
10
63
0

Bobby 01

Make a good impression in your neighborhood.

by LuckyNumber in Audio 10/01/2020
4.13
20.4k
8
1
17

Marianne... A Short Story

A mature woman introduced me to the joys of anal sex.

by micjammusic in Mature 04/03/2022
4.4
19.6k
15
2
21
0

Dan Loses Control for a Toe Ring

Young man finds mature women sexy, and loves their toes.

by Lrt83 in Mature 04/08/2018
4.37
17.4k
13
4
18
0

MILF Club: Naughty Moms At The Bar

The MILF Club is on the prowl, and no dick is off limits!

by Colt45Fan in Erotic Couplings 09/18/2023
4.43
16.5k
18
3
35
0

T&D: Get Your Date to Dominate

Younger sub craves to please prospective Domme.

by Tigger_Lilly in Fetish 01/04/2019
H
4.6
16.3k
31
16
36
0

Maria and the College Boy Pt. 02

Maria finds a spot to let it all out.

by samreed in Mature 01/28/2022
H
4.66
15.1k
16
3
29

Bobby 02

Bobby returns to Mrs. Carter's house.

by LuckyNumber in Audio 10/09/2020
4.45
14.5k
3
3
6

Adriana Lima: MILF's Night Out

Victoria's Secret MILF Adriana Lima fucks a teen heartthrob.

by dirk_gently69 in Celebrities & Fan Fiction 11/19/2020
4.27
11.3k
15
3
26
0

Oh My! Ch. 01

MILF Maris and lifeguard Eric flirt. Coitus interruptus?

by VictorCabana in Erotic Couplings 04/15/2021
H
4.71
6.9k
12
0
17

Missing Miss Ellisondra's Mouth

Wealthy man fondly remembers a long-term prostitute.

by Limnophile in Fetish 07/11/2021
4.34
5.6k
3
0
7
0

A New King for Peggy Hill

Peggy's feet finally get the worship they deserve.

by Mericalovess in Celebrities & Fan Fiction 08/21/2022
H
4.68
5.4k
7
1
13

Oz Beach Boy Recalls a Female Hero

Matt reminisces about a quietly heroic older woman...

by MyBareTorso in Erotic Couplings 07/14/2023
4.36
4.9k
4
3
9
0

Sister Cities Ch. 05

Time moves along. A talk show with interesting information.

by PinkIris in Novels and Novellas 05/28/2020
4.4
2.1k
1
1
3
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