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‘older male’ stories

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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
16.4k
15
3
24

Neighbors Sissy Son Ch. 01

Rewrite of Neighbors sissy son. Same premise!

by newfield1981 in Transgender & Crossdressers 12/11/2022
H
4.65
49.2k
83
10
145

Amanda

Young Amanda gets the older man of her dreams.

by wyo66 in Mature 10/17/2010
H
4.65
63.7k
19
6
39
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

Lauren the Bridesmaid

I became a close friend of my new sister-in-law.

by Notorious_PhD in Erotic Couplings 04/09/2023
H
4.64
29.5k
34
1
64
0

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
15
6
20

This Can’t Be Happening Ch. 19

Why is sex so complicated.

by Str4ng3rth4nf1ct1on in Gay Male 11/11/2022
H
4.64
3.1k
5
3
6

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

Amy Ch. 02

Graduation day like no other.

by Notorious_PhD in Erotic Couplings 02/05/2023
H
4.64
10.1k
7
1
17

Lucky Over 40 Ch. 04: The Waitress

45ish guy on loan to a 25ish girl to teach her a few things.

by Lucky in Erotic Couplings 11/26/2021
H
4.64
7.2k
7
2
14

Man Disciplines Sissy Ch. 04

In the shower, sissy learns about involuntary reflexes.

by LanaBehave in Transgender & Crossdressers 09/24/2018
H
4.64
30.3k
22
11
32

Mackenzie's Accident

My student has an accident in class. I get excited.

by SubtleDeviance in Fetish 07/13/2018
H
4.63
70.8k
74
5
129
0

Jack and The Fat Man

Jack gets drunk and has to face the consequences.

by Str4ng3rth4nf1ct1on in Gay Male 02/17/2024
H
4.63
8.4k
21
7
34

Faking Forever Ch. 05

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/20/2023
H
4.63
3.6k
2
3
5

My Favorite Cashier Ch. 01

A local cashier goes above and beyond...

by outdoorhorny in Erotic Couplings 07/28/2018
H
4.62
31.4k
38
2
44

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

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
10
4
19

Daddy's New Toy Ch. 05

Larry and Alex have a chat in the office.

by AnonymousOmega in NonConsent/Reluctance 11/18/2021
H
4.62
70.5k
108
15
164

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

Hannah Halloween

Frustrated husband succumbs to his daughter's friend.

by UAlbanyGirl518 in Mature 11/04/2019
0
88.5k
164
48
253
0

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

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
10
5
14

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. 03)

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

by buckneckid2000 in Mature 01/14/2022
H
4.6
28k
27
6
29

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 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

Caged in Chastity

I experience chastity for the first time...

by azink in Gay Male 12/13/2023
H
4.6
14.2k
17
8
37
0

Man Taken Ch. 02

Tom learns what led the women to kidnap him.

by tonykrane01 in NonConsent/Reluctance 06/13/2023
H
4.59
4.5k
3
1
6

This Can’t Be Happening Ch. 08

Phillip continues my education. Leading me to submission.

by Str4ng3rth4nf1ct1on in Gay Male 07/27/2022
H
4.59
7.3k
7
1
9

Tempted By A Chubby Teenage Slag Ch. 02

The sequel to Tempted By a Chubby Teenage Slag.

by bigwomenrule in Erotic Couplings 10/06/2013
H
4.59
109.8k
102
11
124

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

In Her Blessed Name

An Anointed Healer conducts worship with his quarry.

by bucknife28 in Sci-Fi & Fantasy 05/23/2020
H
4.58
2.5k
1
0
3
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

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

Mark Made Me a Bottom Ch. 05

Mark completes his domination of me, turning me gay.

by KHndz595 in Gay Male 06/08/2022
H
4.57
38.2k
50
12
74

My Best Friend Blaine

18-year-old gets closer to her roommate & her boyfriend.

by WarmMilk in Group Sex 09/01/2009
H
4.57
116.2k
32
9
49
0

Faking Forever Ch. 09-10

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 09/03/2023
H
4.57
2.9k
4
1
7

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

Young Again Ch. 07

It's too soon.

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

Faking Forever Ch. 08

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/31/2023
H
4.56
2.8k
2
3
5

Santana's Surprise

He had known her all her life. She grew up nice.

by blackrandl1958 in Mature 10/09/2018
H
4.56
57.2k
57
14
81
0

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
18.3k
14
4
14

Faking Forever Ch. 04

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/17/2023
H
4.56
3.8k
4
2
8

Santaphilia

Sorority Slut gets more than she expected from mall Santa

by randymeans in Mature 12/04/2020
H
4.56
46.7k
61
9
104
0

Mark Made Me a Bottom Ch. 02

Mark tries to get me alone again.

by KHndz595 in Gay Male 05/22/2022
H
4.56
40.9k
50
9
73

What's in a Dry Old Fuck? Ch. 06

Last part of the story about an ageing skirt chaser.

by TallManReinvented in Erotic Couplings 08/03/2016
H
4.56
6.3k
7
0
9

Of Lords and Ladies Ch. 07

Lady Allys submits to anal training.

by peachesmelba in BDSM 04/23/2014
H
4.56
85.5k
30
10
37

Bad Dolly Ch. 04

Dolly and Mr. Wells take bigger risks.

by bad_kitty22 in Erotic Couplings 07/20/2012
H
4.54
77.3k
57
19
63

A First Time like No Other - Sonya Pt. 08

Silver Bullets.

by Healwsteel in First Time 10/27/2021
H
4.54
5k
2
0
4

Eric and I on Holiday in the Lakes

Holiday fun with a group of guys in the Lake District.

by Annatartywife in Group Sex 11/25/2013
H
4.54
63.1k
47
9
71

You Never Even Wrote Ch. 03

Chloe ignores her gut feeling, and pays dearly for it.

by sucker4romance in Romance 04/09/2012
H
4.54
13k
7
2
7

Intimacy with Songbird Ch. 03

Things crumble.

by Momstheboss in Romance 06/21/2014
H
4.54
10.8k
1
1
2

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
10.2k
11
2
21

A Foot Up

A discovery of newfound passion.

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

Mark Made Me a Bottom

First time oral as I go from straight to gay.

by KHndz595 in Gay Male 05/19/2022
H
4.53
78.7k
122
21
211

Captivating Sin

A father and daughter try to fight their attraction.

by XXNoraJeanXX in Incest/Taboo 02/24/2015
H
4.52
149.7k
180
29
238
0

Faking Forever Ch. 11-12

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 09/08/2023
H
4.52
2.3k
3
3
6

Mutual Rescue

An older man and a younger single mom heal each other.

by Lucky Mann in Romance 01/30/2017
H
4.52
33.6k
41
11
58
0

A New Friend Pt. 04

I spend the night at Al’s.

by Dalcass in Gay Male 03/11/2023
H
4.52
3.8k
2
1
5

Intimacy with Songbird Ch. 02

Story expands.

by Momstheboss in Romance 06/20/2014
H
4.52
8.7k
0
1
1

Abby Ch. 01

Abby, a young divorcee, encounters her first black man.

by Naughty_Housemom in Interracial Love 02/10/2021
H
4.52
14.9k
35
5
52
0

Faking Forever Ch. 06

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/23/2023
H
4.51
4k
4
5
8

An Apprenticeship

Something's not quite right about her new apprenticeship.

by afogatto in Mind Control 05/08/2022
H
4.51
21.2k
30
4
54
0

In the Garden

First time experience

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

Caught In Pink Panties

Caught in panties by muscular older neighbor.

by NikkiCD in Transgender & Crossdressers 09/26/2010
H
4.51
257.4k
115
34
156
0

Fall Break

Kelly and Lisa discover neighbors secret during fall break.

by Mau5keteer in Erotic Couplings 08/19/2023
H
4.51
10.2k
8
4
15
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 Nanny Ch. 01

White fingers tease this brown pussy.

by PoeticallyPersonified in Interracial Love 10/06/2022
H
4.5
25k
42
3
79
0

USAF Lawyer Finds Love with DIL

Air Force Lawyer sleeps with his hot Daughter-in-Law.

by JohnLaw1950 in Incest/Taboo 03/25/2021
H
4.5
43.4k
92
7
149

Corona

A cab driver helps a young lady do her job, well.

by HarryOrwell in Exhibitionist & Voyeur 04/23/2011
H
4.5
19.2k
2
0
4
0

What Mom Doesn't Know Ch. 04

Daddy shows her off and makes some cash.

by VixieFox in Incest/Taboo 09/02/2018
H
4.5
91.7k
61
8
93

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

Dad and Uncle Bobby

I find out that Dad and my uncle like to pleasure each other.

by ChickenFried in Gay Male 04/20/2023
4.49
23.2k
32
4
65
0

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

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

This Can’t Be Happening

A stolen pack of cigarettes leads to punishment and joy.

by Str4ng3rth4nf1ct1on in Gay Male 07/04/2022
4.49
26.6k
29
15
69

Sugar Cube Ch. 06

"Lots and lots of sugar cubes."

by JimBob44 in Mature 07/28/2016
4.49
11.7k
3
2
4

Of Lords and Ladies Ch. 05

Lady Allys gets examined.

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

My Neighbor, His Slut

She notices her neighbor watching her through bedroom window

by SamanthaEros in NonConsent/Reluctance 12/21/2023
4.48
31.3k
28
2
53

You Never Even Wrote Ch. 02

A surprise for James, and some fun after the restaurant.

by sucker4romance in Romance 04/04/2012
4.48
14.5k
5
4
5

My Geek Slavegirl

A nurse lusts after a teenage geek, and has his way with her.

by Gentlemanrelish in NonConsent/Reluctance 01/12/2016
4.48
93.9k
108
6
146
0

I Give My Niece a Ride

Man gives into temptation from his niece.

by rutger5 in Incest/Taboo 07/01/2017
4.48
198.4k
191
19
223

Lizzy, Queen of Blow Jobs

His boss' hot daughter reveals her special talent to him.

by morninwould in Mature 12/16/2012
4.48
95.4k
81
10
102
0

Black Demon

Wife given to neighbor over a misunderstanding.

by rich0524 in Interracial Love 07/07/2015
4.47
156.2k
150
13
218
0

Faking Forever Ch. 02

Faking forever with my brother's best friend.

by OMichaels in Novels and Novellas 08/10/2023
4.46
4.4k
3
2
9

Well Balanced

A photographer repairs his equipmet.

by bigthrow in Gay Male 03/31/2023
4.46
4.1k
3
2
3
0

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
9k
12
1
19

The New Neighborhood Pt. 04

Max becomes more sexual and starts to explore his kinks.

by EliasxM in Gay Male 11/01/2023
4.45
3.9k
4
2
5

Serving Frank and Stacy

Early morning blow job for our bull.

by DuzzErotica in Gay Male 07/08/2020
4.45
17.6k
20
4
33
0

Dressing for Grandma

A young male's secret is discovered by his grandmother.

by goodsonformom in Incest/Taboo 07/03/2019
4.45
88.8k
52
17
91
0

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

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

Santa's Perverted Helper Ch. 02

Santa's Perverted Helper acquires an assistant.

by rutger5 in Erotic Couplings 12/19/2019
4.44
7.8k
5
0
8

The New Neighborhood Pt. 02

Max continues his advances with David.

by EliasxM in Gay Male 11/20/2022
4.44
7.4k
7
3
12

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
12k
12
3
19
0

Kindness of Strangers

Initial reluctance leads to memorable encounter.

by MeredithEighty8 in NonConsent/Reluctance 11/13/2016
4.43
42.5k
44
1
67
0

My First Time with Another Man

Years of frustration has forced me to action.

by goldigga in Gay Male 02/21/2014
4.43
73.7k
39
14
46
0
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