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‘older male’ stories

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Cucked My Homecoming Date

Went with him, but getting fucked by another guy.

by SamanthaEros in NonConsent/Reluctance 01/24/2024
4.04
16.4k
21
1
58

Teaching, Off To College

Older male student has sexual adventures with a young woman.

by Onrecess in Mature 11/06/2022
H
4.8
27.6k
21
18
53
0

The New Neighborhood Ch. 01

Max moves into a new neighborhood and meets an older gent.

by EliasxM in Gay Male 11/15/2022
4.42
19.5k
21
5
35

Sharing Bed at Bachelor Party Pt. 02

Sharing bed with older male, second part.

by Just4Fun19999 in Gay Male 09/13/2022
H
4.59
25.1k
20
9
38

Serving Frank and Stacy

Early morning blow job for our bull.

by DuzzErotica in Gay Male 07/08/2020
4.46
17.6k
20
4
33
0

That Nice Friend of your Father's #02

Another young women is introduced to sex by father's friend.

by Tantricteacher2 in Mature 02/02/2021
4.24
29.2k
20
0
27

My Story, My Confessions... Pt. 02

I couldn't stop thinking about that night, so I went back...

by SamanthaEros in NonConsent/Reluctance 08/14/2023
H
4.67
8.9k
20
4
28

This Can’t Be Happening Ch. 02

Punished but I was loving my humiliation.

by Str4ng3rth4nf1ct1on in Gay Male 07/06/2022
H
4.62
18.9k
20
5
28

Grace Ch. 02

Grace thanks me for tutoring her.

by outdoorhorny in Erotic Couplings 12/22/2021
H
4.74
21.6k
20
6
30

My Favorite Student's Little Sister

Jesse's little sister gets to act on a long time crush.

by Notorious_PhD in Erotic Couplings 03/02/2023
H
4.82
14.6k
20
2
50
0

This Can’t Be Happening Ch. 03

Humiliation turns to desire.

by Str4ng3rth4nf1ct1on in Gay Male 07/07/2022
H
4.72
14.6k
19
5
25

Leslie Takes Over

Younger girl puts him in his place, but gives him everything.

by greaterimp in Erotic Couplings 07/14/2010
H
4.7
45.1k
19
3
24
0

Anchors Away!! Pt. 16

An old mans dream of sailing takes a few unexpected turns..

by buckneckid2000 in Mature 02/14/2022
H
4.86
30.7k
19
62
20

Amanda

Young Amanda gets the older man of her dreams.

by wyo66 in Mature 10/17/2010
H
4.65
63.8k
19
6
39
0

Anchors Away!! Pt. 17

Bonus chapter... The adventures of Rick and Bob Continue...

by buckneckid2000 in Mature 02/25/2022
H
4.72
11.4k
19
25
22

Perchance To Dream Pt. 01

A mystery woman appears as if from a dream.

by mojavejoe420 in Romance 12/18/2016
H
4.68
16.6k
19
7
40

Amy Ch. 01

A favorite student is not as innocent as she seems.

by Notorious_PhD in Erotic Couplings 02/04/2023
H
4.73
11.1k
18
4
39

Man Disciplines Sissy Ch. 06

Sissy ends purge, buys outfits, makeup, caught half dressed.

by LanaBehave in Transgender & Crossdressers 08/31/2020
H
4.61
14.7k
18
7
26

Caged in Chastity

I experience chastity for the first time...

by azink in Gay Male 12/13/2023
H
4.6
14.4k
17
8
37
0

Of Lords and Ladies Ch. 03

After dinner cums the dessert....

by peachesmelba in BDSM 02/21/2013
H
4.58
63.7k
17
5
19

Peter Ch. 02

Deb gets some details.

by cckready in Loving Wives 12/02/2013
4.04
54.2k
17
18
24

In the Garden

First time experience

by Flexibility in Gay Male 06/30/2014
H
4.51
34.5k
17
5
23
0

Alana and the Professor

Alana Catches Her Neighbor Looking.

by Notorious_PhD in Erotic Couplings 03/30/2023
H
4.65
9.6k
17
1
36
0

The New Hire Ch. 01

Writer/Photographer needs to find a new assistant.

by 1SharkDiver in Exhibitionist & Voyeur 12/10/2015
H
4.6
29k
17
7
26

A Young Doctor’s Cocksucker

How I Became a Cocksucker to a Young Black Doctor.

by COCKSUCKER_COP in Gay Male 06/11/2023
4.49
11.4k
17
10
21

Man Disciplines Sissy Ch. 05

Reluctant sissy tries to hide, but learns the hard way.

by LanaBehave in Transgender & Crossdressers 10/08/2019
H
4.65
21.8k
17
11
27

This Can’t Be Happening Ch. 04

Cocksucking slut? This really IS happening.

by Str4ng3rth4nf1ct1on in Gay Male 07/09/2022
H
4.69
16.4k
17
4
24

Of Lords and Ladies Ch. 04

Allys proves enthusiastic and a new day dawns.

by peachesmelba in BDSM 04/11/2013
4.49
48.9k
17
7
19

My Story, My Confessions...

A young woman finds out when she teases the wrong men...

by SamanthaEros in NonConsent/Reluctance 07/23/2023
4.37
15k
17
1
45

Of Lords and Ladies Ch. 05

Lady Allys gets examined.

by peachesmelba in BDSM 10/06/2013
4.48
77.2k
17
9
24

Anchors Away!! Pt. 08

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 01/26/2022
H
4.83
20.1k
17
14
19

This Can’t Be Happening Ch. 06

Shaved. Not even pubic hair to cover my exposure.

by Str4ng3rth4nf1ct1on in Gay Male 07/20/2022
H
4.64
13.6k
16
6
21

Santa's Yule Log

An office Christmas party is better than expected...

by azink in Gay Male 12/17/2023
H
4.56
10.8k
16
4
29
0

Beyond the Pool

George meets up with his young neighbour again.

by PixelChick in Mature 07/11/2007
H
4.5
122.5k
16
9
25
0

The Lucky Penny

A game of chance with a young woman of indeterminate age.

by greaterimp in Erotic Couplings 01/18/2011
H
4.64
32.7k
16
2
24
0

A New Burn

A meeting in a new context leads to new relationship.

by dingdongdiablo in Gay Male 09/10/2019
H
4.64
15k
15
6
21
0

The Boss of Me Pt. 01

Pete's summer job comes with lessons about alpha males.

by Dawn_Patrol in Gay Male 12/15/2021
H
4.65
16.5k
15
3
24

Never too Old Ch. 04

It's a hot day that gets even hotter...

by storyfella in Mature 02/09/2020
H
4.67
17.2k
15
1
16

Anchors Away!! (Pt. 04)

An old mans dream of sailing takes a few unexpected turns..

by buckneckid2000 in Mature 01/17/2022
H
4.61
23.7k
15
7
16

Doctor Fantasy Ch. 02

Timid submissive gets the full treatment.

by LecherousLady in BDSM 07/11/2015
4.19
95.4k
15
3
22

Anchors Away!! (Pt. 05)

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 01/19/2022
H
4.71
20.4k
14
6
14

Faggot's Delight

A young Wall Street options trader loses his anal virginity.

by CaptainCockrub in Gay Male 05/10/2018
4.45
21.2k
14
4
18
0

Of Lords and Ladies Ch. 06

Lady Allys gains some more...experience.

by peachesmelba in BDSM 01/07/2014
4.49
54.1k
14
8
18

Anchors Away!! (Pt. 06)

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 01/22/2022
H
4.56
18.4k
14
4
14

Anchors Away!! Pt. 11

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 02/02/2022
H
4.81
15.8k
14
7
14

Searching for Sasquatch

Writer on retreat has unexpected encounter w/college cutie.

by TrampsAnThieves in Erotic Couplings 12/10/2023
H
4.66
6.1k
14
9
37
0

Sweet Singaporean Ashley

Singaporean Chinese girl's encounters with older Indian man.

by RedPurple576 in Interracial Love 08/08/2019
4.19
15.6k
14
3
20
0

Jack and The Fat Man Pt. 02

Jack begins to question his sexuality.

by Str4ng3rth4nf1ct1on in Gay Male 02/28/2024
H
4.79
4.7k
14
2
16

Meeting the Neighbor

Addy was new to the neighborhood.

by Missmystery1234 in NonConsent/Reluctance 07/27/2023
4.28
16.1k
14
2
24
0

Coach and the Girls Ch. 02

Bell takes control and gives Coach an irristable show.

by Teddybearsubmissive in Exhibitionist & Voyeur 04/06/2007
4.37
46.2k
13
3
18

Teaching Amanda

Student seduces her teacher and begins a wild sexual journey.

by DiminutiveDame in Mature 01/22/2010
4.19
91.1k
13
3
26

Anchors Away!! (Pt. 07)

An old mans dream of sailing takes a few unexpected turns..

by buckneckid2000 in Mature 01/24/2022
H
4.75
17.8k
13
5
16

The Friend

Man decides to discipline the college girl that moved in.

by SilverWritesTrash in Erotic Couplings 06/19/2021
H
4.6
14.5k
13
0
22
0

The Cheatin' Side of Town

Could he see it?

by wantsomefun1951 in Erotic Couplings 05/28/2012
4.4
21.3k
12
2
18
0

New Year's Eve at a Gay Club

Virgin College Boy is masturbated in public.

by frostingoncake in Gay Male 12/21/2020
4.44
12.1k
12
3
19
0

Grace Ch. 08

Alone with Grace at last!

by outdoorhorny in Erotic Couplings 01/03/2022
H
4.85
12.4k
12
1
16

Tutoring Ch. 01: Engaging the Student

The engagement of a new student tutor.

by vesperum in Erotic Couplings 06/05/2022
H
4.69
16.6k
12
6
33

Night Manoeuvres Pt. 01: Fuck the Boss

A 50 something providing personal protection to a young wife.

by Tommy8305 in Erotic Couplings 02/08/2024
4.46
9.1k
12
1
19

Julie and Her Teacher Pt. 03

Julie tells of her experience with her biggest crush.

by sumbody777 in Erotic Couplings 08/05/2014
4.41
22.4k
12
6
17

Prey Ch. 02

Tesen goes to do what he does best.

by NeighbourhoodSuccubus in NonConsent/Reluctance 09/12/2017
4.4
19.3k
12
0
24

Coming Home

A visit home yields unexpected surprises.

by Octavius_XXX in Incest/Taboo 05/24/2010
0
114k
12
3
19
0

Goddess Helena's Wealthy slave

Goddess meets and turns wealthy older man into her slave.

by cigarashslave in Fetish 07/05/2012
0
59.7k
12
0
21
0

Desires

Aria and Clarence meet and more.

by Iread2relax in NonHuman 06/08/2014
H
4.81
17.3k
12
13
20
0

First Gay Experience at the Pool

My first time with and older man, takes place at the pool.

by steave139139 in Gay Male 01/23/2022
4.29
25.4k
12
1
18
0

Prey Ch. 06

The plan bears fruit!

by NeighbourhoodSuccubus in Sci-Fi & Fantasy 02/08/2018
H
4.6
12.2k
11
0
22

Anchors Away!! Pt. 12

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 02/05/2022
H
4.8
13.6k
11
41
12

A Hard Lesson

Jack gets punished for stealing.

by EliasxM in Gay Male 11/08/2023
4.38
9.7k
11
4
18
0

Anchors Away!! Pt. 15

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 02/12/2022
H
4.79
12k
11
6
11

Young Again Ch. 07

It's too soon.

by KarennaC in Mature 06/25/2008
H
4.56
49.4k
11
5
17

Anchors Away!! Pt. 10

An old mans dream of sailing takes a few unexpected turns..

by buckneckid2000 in Mature 01/31/2022
H
4.71
15.9k
11
6
14

Who’s Your Daddy

David changes course and decides he needs a sugar baby.

by DRobbie06 in Erotic Couplings 11/12/2023
4.35
10.2k
11
3
22
0

This Can’t Be Happening Ch. 07

My education continues and I’m forced to admit what I am.

by Str4ng3rth4nf1ct1on in Gay Male 07/23/2022
H
4.72
10.5k
11
7
14

A Foot Up

A discovery of newfound passion.

by simpletimes in Fetish 06/21/2012
H
4.53
20.5k
11
5
14
0

Grace Ch. 09

Grace and I move on to the main event.

by outdoorhorny in Erotic Couplings 01/04/2022
H
4.84
13.1k
11
3
14

Spring Break at the Cabin Ch. 08

Danielle goes back into town alone.

by abob1 in Group Sex 02/23/2023
H
4.68
8.5k
11
2
16

Appointment for Spanking

Curious male wants to be spanked by older gentleman.

by Artman4 in Gay Male 02/19/2016
4.22
42k
11
11
12
0

Anchors Away!! Pt. 14

An old mans dream of sailing takes a few unexpected turns...

by buckneckid2000 in Mature 02/09/2022
H
4.76
12.2k
11
15
11

Milked by My Bull

Master allowed me an unforgettable experience.

by CheekyCharley in Fetish 01/05/2024
4.34
12.9k
11
2
31
0

Social Isolation - Stuck at Home Ch. 03

Amanda and I continue in the guest room...

by outdoorhorny in Erotic Couplings 05/24/2020
H
4.7
13.1k
11
1
16

This Can’t Be Happening Ch. 05

The cold light of day doesn’t change how I feel.

by Str4ng3rth4nf1ct1on in Gay Male 07/12/2022
H
4.62
10.3k
11
4
20

This Can’t Be Happening Ch. 09

Cock worship and coach leaves me in shock.

by Str4ng3rth4nf1ct1on in Gay Male 07/31/2022
H
4.61
10.4k
11
5
15

Sharing Bed at Bachelor Party Pt. 04

Meeting Damon's Husband leads to new adventures.

by Just4Fun19999 in Gay Male 12/31/2022
H
4.53
10.3k
11
2
21

Nadia, My Spanish Girl

The Spanish girl I had known for some years comes of age.

by bravebombadier in First Time 08/29/2018
4.44
27k
10
0
17
0

Grace Ch. 19

Grace and I begin Spring Break.

by outdoorhorny in Erotic Couplings 03/24/2022
H
4.89
13.7k
10
12
10

College Visit Ch. 10: Time is Up

Lexi and I make the most of our last hour together.

by outdoorhorny in Erotic Couplings 01/08/2020
H
4.82
10.4k
10
5
11

Social Isolation - Stuck at Home Ch. 04

Waking up the next morning with Amanda.

by outdoorhorny in Erotic Couplings 05/25/2020
H
4.81
10.2k
10
2
15

Grace Ch. 15

Grace lets me cross a new boundary.

by outdoorhorny in Erotic Couplings 01/22/2022
H
4.86
13.7k
10
4
17

Strange Men Pt. 01

Sometimes the unknown is exhilarating.

by savvygirl665 in BDSM 06/01/2017
4.21
8.7k
10
0
15

Faking Forever Ch. 01

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/06/2023
4.29
8.7k
10
2
28

My Favorite Cashier Ch. 03

Our day of pleasure continues.

by outdoorhorny in Erotic Couplings 07/25/2019
H
4.68
14.2k
10
2
11

This Can’t Be Happening Ch. 18

A surprise throat fucking. Mr Ali has a speciality.

by Str4ng3rth4nf1ct1on in Gay Male 10/06/2022
H
4.74
6k
10
5
13

Jack and The Fat Man Pt. 03

Jack faces up to his sexuality after wanking Arnold off.

by Str4ng3rth4nf1ct1on in Gay Male 03/22/2024
H
4.81
3.1k
9
3
11

Anchors Away!! Pt. 13

An old mans dream of sailing takes a few unexpected turns..

by buckneckid2000 in Mature 02/07/2022
H
4.76
13.6k
9
11
9

Jack and The Fat Man Pt. 04

After sucking Arnold's cock, Jack's darker fantasies grow.

by Str4ng3rth4nf1ct1on in Gay Male 04/12/2024
H
4.96
2.9k
9
2
13

How a Girl falls in Love

The unexpected first experience of a blooming teenager.

by JaneDoeStuff03 in First Time 12/27/2021
4.33
24.8k
9
11
14
0

Older Stranger in the Early Morning

It amazes me how easy it is to find sex on the streets.

by KinkyKisser916 in Gay Male 04/16/2023
H
4.58
9.7k
9
2
14
0

I Love It When They Come Back Pt. 04

A stolen morning with Molly over the summer.

by outdoorhorny in Erotic Couplings 07/25/2018
H
4.53
13.2k
9
3
11

College Visit Ch. 05: Night Continues

Lexi and I finally make it to the bed.

by outdoorhorny in Erotic Couplings 12/28/2019
H
4.82
16.6k
9
0
12

Pilot in Command Ch. 03

Ki’s sexual adventures intensify.

by Maydaypilot in Mature 10/23/2022
H
4.73
4k
9
5
11

This Can’t Be Happening Ch. 26

Phillip and Mr Smith show me what it’s means to be a slut.

by Str4ng3rth4nf1ct1on in Gay Male 06/07/2023
H
4.79
4.3k
9
3
11
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