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‘older man younger man’ stories

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Chevy Van

My friend's father takes me home the long way.

by timmywells in Gay Male 08/24/2010
4.33
190.5k
53
8
78
0

The Tutoring

A maths tutor finds company in the form of his pupil’s Dads.

by FagWithAKeyboard in Gay Male 02/29/2024
H
4.75
12.9k
31
5
56
0

Easy Pickings

Men found Andy ready and there for the taking.

by timmywells in Gay Male 11/11/2012
4.47
54.6k
27
4
34
0

My Science Teacher, Mr. Duke

An after graduation pep talk becomes more than inspiration.

by timmywells in Gay Male 06/11/2011
4.37
92.3k
24
7
39
0

Schism Pt. 03 (conclusion)

Dane loses his anal virginity, gets a surprise.

by JasonClearwater in Gay Male 02/05/2018
0
13.9k
22
10
25

A Sissy's Journey Ch. 03

Jesse enjoys cross-dressing and Amanda's tops him.

by yukonnights in Transgender & Crossdressers 04/13/2017
H
4.67
33.6k
21
11
26

Six Dead Poets

Will shares Jesse with six other men.

by JasonClearwater in Gay Male 09/04/2017
0
18.3k
21
11
29
0

The Dressing Room

Young man has unexpected sexual adventure with older man.

by Pericles123 in Gay Male 01/04/2024
H
4.64
17.7k
21
8
35
0

Valentines for Adam

Jesse takes a girl to see Adam on Valentine's Day.

by JasonClearwater in Anal 02/20/2018
0
25k
14
3
23
0

More Spying in England 1634

The Lord and Lady find more spice but it is very hot.

by Publandlady in Incest/Taboo 10/22/2023
H
4.7
10.4k
13
3
26

A Sissy's Journey Ch. 06

After dinner out, things heat up at Rick's house.

by yukonnights in Transgender & Crossdressers 04/16/2017
H
4.65
21.6k
12
2
14

A Sissy's Journey Ch. 07

Rick and Jesse find love together.

by yukonnights in Transgender & Crossdressers 04/18/2017
H
4.68
19.4k
12
7
19

A Sissy's Journey Ch. 04

Jesse learns about makeup and models for Rick.

by yukonnights in Transgender & Crossdressers 04/14/2017
H
4.65
18.1k
8
2
10

Rogers Unit Pt. 05

A visit to Rogers neighbor opens a new experience.

by Richard_Hunter in Gay Male 07/29/2023
H
4.76
4.7k
6
2
10

A Sissy's Journey Ch. 05

Amanda and Briana get Jesse ready for a date with Rick.

by yukonnights in Transgender & Crossdressers 04/15/2017
H
4.64
20.3k
5
3
6

The Floating World Pt. 04

27 year old Jesse spends a strange night with an older man.

by JasonClearwater in Gay Male 09/17/2017
0
7.8k
2
4
2
0

Busted By My Neighbor...

Guess I was too loud... [M4F]

by DrStoney in Audio 02/20/2024
4.17
6.9k
2
7
3
0
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