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‘first time gay’ stories

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Underneath Ch. 02

He ordered his male coworker to wear lingerie and more...

by Edey in Gay Male 04/30/2022
H
4.83
19.9k
24
23
49

Working Out Issues Ch. 03

Mel gets more comfortable with his body.

by blake1 in Transgender & Crossdressers 02/25/2019
H
4.59
22.3k
24
10
27

Never Did This Before

Older gentleman moves into a Seniors' Community.

by timmywells in Gay Male 07/12/2013
H
4.51
61.4k
24
16
36
0

Donald Comes to Town Ch. 06

Andre meets Sebastian, shower and play together.

by LoganPrejean337 in Gay Male 11/07/2022
H
4.89
7.9k
24
8
29

Escape Room for Jocks Pt. 04

The race is on between the 4 jocks.

by MrSunshineBoy in Gay Male 09/18/2020
H
4.57
18.3k
23
2
30

Wrestler's Shower

A sexually repressed wrestler has his first gay encounter

by Maximus_Crassus in Gay Male 07/28/2016
4.27
38.4k
23
0
32
0

24 HR Gym

An unexpected first time.

by Mjolnir22 in Gay Male 02/17/2023
H
4.55
28.9k
23
5
48
0

Escape Room for Jocks Pt. 05

The race continues.

by MrSunshineBoy in Gay Male 09/27/2020
4.46
17k
23
4
32

Peter the Neighbour Ch. 02

Peter takes me to bed.

by davidinlace in Gay Male 10/31/2021
H
4.57
31.8k
23
4
33

Back to Back Pt. 07

Proximity takes a toll on Artie.

by TurbulenceAhead in Gay Male 11/04/2022
H
4.88
9k
23
77
27

Weekend in New Hampshire Pt. 02

Day 2 of the friends' adventure in the country.

by grant50 in Transgender & Crossdressers 10/26/2019
H
4.73
19.5k
23
5
27

Banging Big Time Is No Theory Ch. 02

The boys explore what's always been there

by kingchaos69 in Celebrities & Fan Fiction 10/09/2013
4.1
57.4k
23
3
26

The Real Kasey Ch. 01

The story of Kasey Legs.

by KaseyLegs in Transgender & Crossdressers 10/07/2016
H
4.72
25.5k
23
8
42
0

Brotherly Love

Mo is taken to a sex worker by his older brother.

by tvdude17 in Incest/Taboo 09/14/2018
4.32
21.7k
23
0
32
0

Back to Back Pt. 06

A camping trip and a realization.

by TurbulenceAhead in Gay Male 08/28/2022
H
4.87
12k
23
40
32

Camping Bromance Firsts Ch. 02

Two straight buddies experience more of eachother.

by Logjam107 in Gay Male 12/24/2020
H
4.57
29.9k
22
6
38

Chat Friend Finds Me Ch. 02

Straight male friends further explore gay & group sex.

by markindy in Gay Male 01/01/2007
H
4.6
50.8k
22
5
31

First Time With a Guy

Straight but curious guy has his first gay experience.

by o123oleary in Gay Male 08/25/2016
4.16
77.8k
22
10
33
0

The CL Tease Ch. 01

Straight, online tease gets get turned out by his 'victims'.

by jrzdogg in Gay Male 05/04/2017
4.49
23.9k
22
1
30

Mirror in Law

A mother in law comes up with a devious plan.

by Fibaro in Mind Control 12/11/2021
4.07
31.6k
22
6
46
0

Alpha Bear on Campus Ch. 03

John and President May form a father/son bond.

by johngus22 in Gay Male 11/27/2020
H
4.66
17.6k
22
6
25

Bi Jeff Gives Good Directions

Bisexual guy teaches older couple about 3-ways.

by dennyboy2 in Group Sex 09/08/2006
4.43
109.5k
22
10
32
0

My Leiben Herr

Innocent crossdressing leads to sex with a man.

by kinki1 in Transgender & Crossdressers 12/11/2009
4.36
66.8k
22
18
27
0

Trust Ch. 03

A gay man falls in love with a straight one.

by Elenia26 in Gay Male 08/14/2013
H
4.59
16.7k
22
0
24

The Outback Ch. 03

Neel and Dean explore the shift in power dynamics.

by BluePill in Gay Male 12/06/2023
H
4.93
10.9k
21
6
27

No Longer a Show Ch. 02

Straight cam dude meets IRL for first gay anal sex.

by CinaedeFuri in Gay Male 01/23/2021
4.33
12.8k
21
3
24

Egyptian Initiation

Lucky first-timer finds a magician for a deflowerer.

by sr71plt in Gay Male 08/18/2006
4.35
95.2k
21
8
28
0

The Swimming Pool

My first sex with a man.

by hotcurrie1001 in Gay Male 09/28/2010
4.43
85.8k
21
3
23
0

Hot Kisses & Near Misses

His first time getting turned on by another guy.

by Redbird1376 in Gay Male 04/18/2006
H
4.63
64.9k
21
16
30
0

Surfers Experiment in Speedos

These Aussie surfers experiment in speedos.

by speedodave in Gay Male 07/10/2016
4.49
42.7k
21
2
35
0

No Longer a Show Ch. 01

Straight live cam guy tries first gay blowjob to make cash.

by CinaedeFuri in Gay Male 01/22/2021
3.92
16.1k
21
3
35

For the Love of Cock

My path to becoming a cocksucker.

by 69stroker69 in Gay Male 12/04/2019
4.48
39.9k
21
17
31
0

Movie Night

Who thought this would happen on chickflick night?

by dundurn in Gay Male 11/04/2005
4.39
90.9k
20
6
26
0

The Soccer Locker Room Pt. 09

Jake and his straight teammate chat in the showers post-game.

by jtwy in Gay Male 03/13/2021
H
4.53
23.9k
20
4
29

First Time Gay Sexual Experience

A straight male walks into a gay video arcade.

by BBPierce in Gay Male 10/22/2022
H
4.58
25.1k
20
3
41
0

First Time in an ABS

Young guy stops by ABS to see what it's all about.

by jrzdogg in Gay Male 10/15/2015
4.26
41.9k
20
2
29
0

Best Friends' Friday Night

Two best friends share a magical night.

by Mindsworkspace23 in Gay Male 12/13/2018
4.33
44.6k
20
1
35
0

Adventures With Close Friends

Adventures of four close friends.

by aphrodite116596 in Group Sex 09/06/2020
H
4.52
25.3k
20
1
34
0

Teen Goes To Swinger Party Ch. 01

Teen boy goes to swinger party and has some kinky fun.

by Southernstud97 in Group Sex 03/27/2015
3.32
73.4k
20
3
30

Coach CockStud

Married man dreams about sucking cock... and does

by brian420d in Gay Male 09/17/2010
4.1
103.7k
20
9
27
0

Camping with the Neighbor Ch. 01: Intro

A lonely married man tries his best to get off.

by flopp89 in NonConsent/Reluctance 10/28/2016
2.9
62.4k
19
1
31

Highway Encounters Ch. 01

A man's boring trip takes a turn for the interesting.

by blatant_bi_guy in Gay Male 04/27/2013
4.49
40.6k
19
10
24

My First Time

He always thought of himself as straight.

by gray3035 in Gay Male 09/12/2005
4.29
91.2k
19
7
26
0

Girlfriend's Away Pt. 04

How far can Sara make the boys go?

by Hebrides in Group Sex 03/22/2021
4.18
33.4k
19
4
37

An Afternoon with Charlie

My first gay experience with an older man.

by harveyf in Gay Male 08/15/2016
4.41
50.4k
19
8
30

Escape Room for Jocks Pt. 10

The Jocks are getting intimate with two more teammates.

by MrSunshineBoy in Gay Male 08/12/2021
H
4.67
12.7k
19
8
29

Loving Him Ch. 01

A story of the beginning, bitter and sweet.

by gildedbutterflies in Gay Male 07/12/2013
4.49
21.1k
19
6
30

Surrogate Experiences

Laura talks Tommy into trying it with a man.

by Omenainen in Gay Male 07/11/2020
H
4.69
33.2k
19
9
49
0

Wanting Him Ch. 02

Ashton and Thomas resolve some differences.

by onemoreday in Gay Male 01/23/2015
4.2
26.7k
18
14
23

First Time Ch. 01

Married bisexual man has his first same-sex encounter.

by bimale_35 in Gay Male 10/04/2007
4.24
128.3k
18
6
29

What Did I Lose Ch. 01

A young college student wants to lose his V card... but not.

by Virginny in Gay Male 05/28/2021
4.07
14.1k
18
4
29
0

Breaking My Cherry

Man to man seduction.

by bilove69 in Gay Male 08/14/2016
4.41
40.6k
18
2
24
0

Hotter than Fiction 1997

A young man's first bisexual encounter with a hot couple.

by DionysusK in Gay Male 06/17/2023
H
4.74
33k
18
9
53
0

Desperate Nights

Housemates can't sleep - follow up on "Desperate Times..."

by aRedheadWrites in Gay Male 08/21/2020
4.45
19.9k
18
10
28
0

Leaving HS with a Bang

Best friends trade BJs in the HS theatre.

by Mjolnir22 in Gay Male 12/05/2023
H
4.5
12k
18
5
26
0

Escape Room for Jocks Pt. 09

One new game, two more team mates, one winner.

by MrSunshineBoy in Gay Male 03/01/2021
H
4.51
14.7k
18
5
25

The CL Tease Ch. 02

The tease gets more than he bargained for.

by jrzdogg in Gay Male 05/16/2017
H
4.53
24.1k
18
1
20

A Cock in the Hand Ch. 08

Straight man turned gay cock-whore accepts his new role.

by rimaday in Gay Male 09/03/2023
H
4.74
16.6k
18
5
32

Underneath a Warm Afternoon Sun

Time away with my best friend.

by asterism in Gay Male 03/10/2021
H
4.67
19.8k
18
5
43
0

The Eyes of Acceptance Ch. 01

Scared boy learns a painful truth about himself.

by KaseyLegs in Transgender & Crossdressers 01/02/2021
4.21
11.6k
18
8
24

My First Time

His first gay experience, thanks to my girlfriend.

by biboy13142 in Gay Male 06/26/2006
0
100.7k
17
11
29
0

Charles

My first time with another guy.

by Afterhours22 in Gay Male 06/17/2012
4.23
49.4k
17
11
20

Loving Him Ch. 02

Lexan and Max's relationship takes a drastic turn.

by gildedbutterflies in Gay Male 07/12/2013
H
4.6
19.1k
17
5
18

Cherry Popped

Stationed in a war zone, a soldier has to escape.

by tvdude17 in Gay Male 11/26/2021
4.26
27.5k
17
5
40
0

First Night Seduction Ch. 01

Gay men can enjoy seduction!

by S_Isemen in Gay Male 06/30/2019
3.86
28.7k
17
4
43

The Blond Man's Gaze

The man in the bathroom won't stop staring. Neither can I.

by PercyPopham in Gay Male 08/18/2023
4.49
11.2k
17
9
36
0

Back to Back Pt. 04

Miles and Artie start school.

by TurbulenceAhead in Gay Male 06/12/2022
H
4.81
9.4k
16
17
21

From Fantasy to Reality

Two straight guys decide to explore something new.

by sterlingdaydream in Gay Male 01/24/2020
4.41
44.5k
16
4
34
0

Telling Secrets

One young man's boss offers an unexpected proposition!

by OwenBurke in Gay Male 09/30/2013
4.32
69.7k
16
3
22
0

Cody Becomes Chloe Pt. 01

A teen goes on Craigslist and meets Will.

by Southernstud97 in Transgender & Crossdressers 03/19/2015
3.54
41.7k
16
9
21
0

The Outback Ch. 04

Neel opens up to Dean.

by BluePill in Gay Male 12/28/2023
H
4.89
5.1k
16
10
25

Meating Terry

My first experience with a submissive sissy boy.

by andyorlando in Transgender & Crossdressers 10/05/2016
4.14
34.2k
16
5
20
0

A Gay Change of Mind

I find myself increasingly attracted to Gavin.

by Templar_Writer in Gay Male 12/15/2016
4.45
39.7k
16
15
24

Back to Back Pt. 05

Artie goes on a date?

by TurbulenceAhead in Gay Male 07/10/2022
H
4.78
8.7k
16
24
21

Ch. 05 Unexpected Weekend

Fucked like a girl.

by Jamie_1 in Transgender & Crossdressers 05/20/2023
H
4.77
15.8k
16
6
25
0

The Outback Ch. 02

Dean struggles with his new attraction to Neel.

by BluePill in Gay Male 11/22/2023
H
4.85
8.7k
16
7
26

Sexuality Shock

Surprise handjob initiates his new sexuality.

by twowayswitch in Gay Male 04/23/2013
4.04
80.6k
16
7
19
0

The Other Boy in Goodwell

High lonesome cowboy's first time w/ an experienced hipster.

by Theroughstockeventauthor in Gay Male 07/05/2015
4.44
25.7k
15
6
28

Shady Pines Ch. 01: Prologue

Sean takes the plunge with Sam.

by AgirlcalledBob in Gay Male 10/09/2018
H
4.53
16.5k
15
0
34

Magical Desire

A powerful warlock finds his soulmate.

by SkylerLuv in Gay Male 02/14/2019
H
4.8
22.1k
15
4
39
0

Poppy

Young questioning man falls for older fem.

by ophanim in Gay Male 11/18/2019
H
4.63
14.6k
15
2
26
0

Coby Pt. 01

An 18yr suburban teen has thoughts; experiments with thoughts.

by etiennesurlaplage in Gay Male 08/29/2023
H
4.73
12.4k
15
2
36
0

Tony's First Time

Tony hooks up with a guy from work.

by chocolatecookie3 in Gay Male 12/31/2012
4.15
83.4k
15
5
20
0

Trust Ch. 02

A gay man falls in love with a straight one.

by Elenia26 in Gay Male 08/13/2013
H
4.69
20k
15
0
20

Starting Over Pt. 02

Joe's bed has a surprise guest.

by QuickYellowFox in Gay Male 12/11/2023
H
4.82
8.9k
15
7
28

James Pt. 01

Story of a straight guy's first time.

by Irish_Ted in Gay Male 01/26/2017
4.19
41.6k
15
2
27

A 101 on Masculine Pleasure

A secret lost to history: how good sex can be for men.

by ThePurpleDragon in Gay Male 12/20/2023
H
4.74
7.1k
14
5
28
0

Homework Help

Two men enjoy helping each other with a problem.

by bilman in Gay Male 09/28/2010
H
4.53
66k
14
1
20
0

Cassandra and Steve

His first MMF threeway has a surprise.

by Christian Black in Group Sex 01/29/2006
4.23
95.3k
14
2
24

Nutritional Supplement

A curious bodybuilder learns a new work out.

by shannonkelly in Gay Male 08/14/2016
4.35
31.8k
14
2
19
0

First Love is Fantastic

Twinks discover the joys of first time love.

by danielblue in Gay Male 04/14/2007
4.39
56.9k
14
0
17
0

Summer Switch Ch. 04

BFFs to lovers - 1st gay sex experience of 2 "straight" men.

by qchickie in Gay Male 04/04/2021
4.46
20.6k
14
6
32

Bi 1st Time in Vegas

He has his first man to man sex.

by Batcum2002 in Gay Male 10/29/2008
4.34
110.1k
14
9
22
0

Blind Man's Bluff

Straight Guy/Gay Sex.

by trevorm in Gay Male 10/06/2011
4.16
70.8k
14
2
22
0

Started at the Theater

First time with a man, started at the Adult Movie House.

by isoro1 in Gay Male 03/23/2020
4.29
26k
14
4
20
0

Bruce Don't Go There

His straight buddy introduces him to his dark side.

by not_with_my_wife in Gay Male 08/07/2007
3.92
127.3k
14
0
25
0

A Familiar Story Ch. 02

Breaking in a willing virgin.

by canacoc in Gay Male 10/22/2011
H
4.51
45.7k
14
4
17

After The Move

New apartment leads to new experiences.

by Reshbod in Gay Male 10/06/2005
4.21
56.9k
13
7
18
0

Back to Back Pt. 03

Artie starts to accept and Miles continues to deny.

by TurbulenceAhead in Gay Male 05/29/2022
H
4.75
9.9k
13
19
20

Unexpected Item

(but not in the bagging area...)

by sjreardon in Gay Male 08/17/2023
H
4.8
10.7k
13
9
29
0
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