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‘gay first time’ stories

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30 DaysAll Time

My Old Pal Charley

Feeling out an old high school friend.

by MrSperm in Gay Male 08/07/2014
4.18
29k
11
3
12
0

To Have and to Hold and -- to Blow

She lets him explore his own bi-side.

by truamethyst in Group Sex 01/29/2007
4.16
72.4k
11
4
19
0

Mr. Right Now Ch. 03: Dave

Dominating a hot cop.

by KenJames in Gay Male 02/17/2020
H
4.69
11.7k
11
5
20

Sweet Infatuation

My first encounter with an exciting man.

by SmoothandLovely in Gay Male 04/22/2021
4.3
21.8k
11
13
18

The Pretender Ch. 10

Genesis; A New Beginning

by JaycobMatthews in Gay Male 09/14/2012
H
4.78
14.1k
11
4
11

Park Cruising Ch. 02

His adventure continues to deepen.

by Bttmboi in Gay Male 02/04/2006
4.47
105.2k
11
7
12

Dreaming Away My Virginity

Guy has a recurring dream of losing his virginity.

by shy_boy in Gay Male 07/11/2006
4.2
44.6k
11
0
12
0

Southern Magic Ch. 02

Derek learns that magic can be fickle.

by PhoenixKing in Gay Male 09/23/2014
H
4.64
13k
11
1
12

Backache

He savors a full massage.

by julianblake in Gay Male 02/01/2007
4.25
141.1k
11
3
14
0

First Times are the Best Ch. 02

First time having gay sex.

by jx88 in Gay Male 07/15/2011
4.3
44.9k
11
11
12

My Journey into Bisexuality Ch. 01

First step into my bisexuality with more to come!

by kinkymmale in Gay Male 01/16/2012
4.33
66.2k
11
14
21

MWM Bisexual Musings Ch. 01

My reality blended with gay fantasy with bestie.

by fitfidelityfifty64 in Gay Male 01/11/2024
4.32
12.6k
11
4
27

The Pretender Ch. 09

Complications.

by JaycobMatthews in Gay Male 08/27/2012
H
4.64
13.9k
11
12
11

Trawler Initiation

New deckhand alone at sea with a trawler full of randy men.

by sr71plt in Gay Male 11/02/2012
4.18
60k
11
2
14
0

Jared Ch. 01

Jared meets a man from the Internet how will it end?

by andrew1990 in Gay Male 09/13/2013
3.85
33.4k
11
2
14

Nickolas and Jason Ch. 02

Lead up to Nick's 19th birthday party.

by RobMontague in Gay Male 04/03/2009
H
4.7
31k
10
3
13

Hatred and Love

Hetero guy's homophobia leads him on a journey.

by Lion24655 in Gay Male 09/11/2006
4.25
44.4k
10
5
14
0

My First Place Ch. 01

Solo for the first time, he experiments with the other side.

by velokev in Gay Male 09/23/2009
4.25
29.7k
10
1
13
0

Somethin' U Wanna Know

Curiosity gets the better of a married couple.

by Kapricorn71 in Gay Male 10/14/2006
4.41
116.1k
10
7
17
0

Old Friends

One confession leads to passion in the bedroom.

by Gothickun in Gay Male 03/07/2010
3.95
60.1k
10
3
16
0

My First Time With A Man Ch. 01

Installer educated him after installing the new furnace.

by FUNFORUS2 in Group Sex 11/24/2010
4.4
46.7k
10
4
14
0

Northern Country Boy Finds Himself

A young college man figures out who he is and what he wants.

by MichBearGuy in Gay Male 08/01/2017
4
17.1k
10
3
12
0

Levi Ch. 03: The Loved Boy

Levi finds a boyfriend. Nathan and the good Doctor continue.

by jdylanh9 in Gay Male 12/28/2011
H
4.51
17k
10
5
10

Cairo Surrender Ch. 02

Rawest Cairo: Michael captured.

by KeithD in Gay Male 06/06/2019
4.46
12.4k
10
1
10

The Cafeteria

One look at Kyle and Ryan begins to change his ways.

by trikon309 in Gay Male 09/01/2007
H
4.51
31.6k
10
2
14

Blow Job in San Francisco

This was my first experience with sex with a gay man.

by Boxlicker101 in Gay Male 05/14/2012
4.13
64.7k
10
11
13
0

The Pretender Ch. 08

Daniel and Westley finally meet; The start of Complications.

by JaycobMatthews in Gay Male 08/12/2012
H
4.67
13.5k
10
5
10

My First Anal

The first time I was entered and what it made me understand.

by Talonspryde in Gay Male 10/23/2021
4.2
42k
10
15
20
0

The Cavern

A fantasy finally fulfilled.

by DomRick in Gay Male 03/24/2006
H
4.57
47.7k
10
7
13
0

No Regrets Ch. 03

Tommy's Story – Another Chance.

by martin_x59 in Gay Male 10/05/2013
H
4.64
15.3k
10
2
10

The State of Being Gay

A gay beach encounter.

by chuckster67 in Gay Male 05/01/2009
4.41
42.6k
10
5
12
0

Curious

Curiosity did not kill this cat.

by mikec1010 in Gay Male 10/25/2006
4.37
61k
10
4
14
0

Led to Temptation

He is gently persuaded to give in to his desires.

by millhouseBob in Fetish 01/12/2011
4.38
50.9k
10
1
15
0

A Long, Long Time Ago

Straight man tries guys for the first time.

by OhioCurious in Gay Male 03/19/2007
3.56
74.6k
10
0
11

Salt's Quest for Charisma

Salt loses his anal virginity on Halloween.

by JasonClearwater in Gay Male 10/02/2017
0
28.7k
10
7
19
0

My First Time

He tries men for the first time.

by BigWig69 in Gay Male 08/08/2007
4.14
56.9k
10
1
12
0

Declin's Awakening

Evan pushes Declin a little too far.

by hellburns0328 in NonConsent/Reluctance 12/20/2019
4.36
19.3k
10
1
20

Three

A man leaves wife for first boyfriend.

by Dawns in Gay Male 10/24/2007
3.9
42.8k
10
0
14
0

The Pretender Ch. 06

Recovery and Temptation.

by JaycobMatthews in Gay Male 07/23/2012
H
4.61
14.6k
10
10
11

Insatiable Ch. 01

Kevin exploring gay lifestyle from straight.

by RandyAlabama in Gay Male 09/03/2020
4.06
20k
10
3
21

Vacation Pt. 02

Story of Micheal's adventure from the waiter's point of view.

by hockeyfan2 in Gay Male 06/02/2021
H
4.59
11.5k
10
5
14

First Time Twice

Doubling first time pleasures.

by glory_first in Gay Male 07/15/2008
3.84
90.7k
10
2
12
0

My First Suck

College guy and older man each suck for first time.

by Wolf of Mibu 69 in Gay Male 02/24/2006
4.44
90.6k
10
13
13
0

My Neighbor's Secret Ch. 02

My neighbor & I discover even more about one another.

by Caliber345 in Gay Male 12/01/2008
0
67.2k
10
2
15

My Older Masseur

Willing first timer gets massage & more

by emittsrif in Gay Male 04/02/2013
4.08
82.7k
10
6
15
0

The Student

Even dressed Rickie had poise, but in the nude!

by Cumfusion in Gay Male 05/08/2006
4.24
49.9k
10
3
16
0

A Curious Man's Fantasy Ch. 01

"I want to be your first."

by luvcurious in Gay Male 07/12/2006
4.25
81.8k
10
7
16
0

My First Bathhouse Experience

His first time sex with a man face to face.

by cuminmyasss in Gay Male 06/18/2009
3.85
159.6k
10
10
15
0

The Pirate and the General

My true accounting of how I became a pirate.

by OregonDavid in Gay Male 01/11/2010
H
4.58
24.3k
10
1
12
0

Guy's Night Out Ch. 04

A trip is taken and a plan is formed.

by jrzdogg in Gay Male 12/02/2015
H
4.66
19.1k
10
6
13

The Ledge Rocks

18 year-old homo-hetero virgins finally get it.

by lionel_collins in Gay Male 02/12/2007
4.4
50.2k
10
2
14
0

Drag Queen and the Indecisive Guy

A guy with questions meets a drag queen - and change his life.

by jim_janes in Gay Male 01/12/2019
4.43
25.3k
10
0
16
0

When I Met Ryan Ch. 03

Mine and Ryan's relationship progresses.

by chapmad91 in Gay Male 03/19/2012
4.48
17.3k
10
3
11

Kimmy the T-girl

A transvestite gets dominated by a stud.

by sissy_in_denial in Transgender & Crossdressers 01/07/2009
4.15
74.5k
10
8
12
0

Uncovered Desires

Paula & Eric make friends while dancing.

by Dakota Ryan in Group Sex 07/01/2006
4.37
58.9k
9
0
10
0

Falling

A trip to the farm goes well.

by OwenBurke in Gay Male 11/24/2013
4.21
36.4k
9
1
11
0

Southern Magic Ch. 04

Derek learns that magic can be fickle.

by PhoenixKing in Gay Male 09/27/2014
H
4.64
10.3k
9
1
10

Nirvana Ch. 02

"Matthews, what are you doing to me!"

by MoonBeetle in Gay Male 12/12/2015
H
4.51
17k
9
5
10

My Brother and Me Ch. 02

My brother and I become closer, sexually & emotionally

by cutandhorny in Incest/Taboo 03/10/2007
3.74
84k
9
3
16

Miseries in Mauve

Rooftop, sun, and umbilical seduction of straight youth.

by CalHollows in Gay Male 01/26/2011
4.24
39k
9
5
13
0

Chuck and John's Public Pool Fun

Recent high school graduates discover underwater fun.

by tomnielsen54 in Gay Male 06/20/2007
3.75
59.7k
9
5
11
0

First Time with Friend

Two guys realize they've got what they other needs.

by MikeDelaware in Gay Male 09/04/2008
4.07
108.5k
9
4
12
0

The Fallen Ch. 04

Full Moon brings out inner desires.

by Acacia_wolf in Gay Male 03/25/2013
H
4.58
9.9k
9
4
9

Internet Anal Sex

Having sex with a bottom male after meeting him on internet

by fox-for-fun in Gay Male 01/31/2009
3.93
56k
9
0
12
0

Posing Strap Trio Ch. 03

Hidden passions burst out between three muscular buddies.

by posingstrap1 in Gay Male 03/21/2024
H
4.78
2.3k
9
2
9

More Than a Meet Ch. 01

Dave invited me to meet after online chat.

by bendigoboy in Gay Male 12/29/2013
4.44
22k
9
4
13

My Journey

Heteroman takes a leap of faith.

by mdp_2004 in Gay Male 10/14/2009
4.4
34.6k
9
0
13
0

A Special Night

A new beginning for one man.

by PhantomOfMoonlight in Gay Male 04/03/2010
4.44
57.8k
9
6
13
0

A First Encounter

A discreet massage ends up being life-changing...

by sakall2009 in Gay Male 02/18/2015
3.84
104.7k
9
14
12
0

Pathetic Ch. 06

Luca gets a helping hand to deal with his pain.

by kipp412 in Gay Male 12/28/2015
4.48
12.1k
9
6
10

Summer Lovers

Two college friends share their first times.

by dreamcatcher549 in Gay Male 01/24/2008
4.28
67.9k
9
3
12
0

Believe Me Nora Ch. 01

A bi-sexual couple explore pregnant sex options.

by jackredd in Fetish 08/17/2012
H
4.57
35.3k
9
0
14

Stranger on the Train

Straight but curious guys seduce each other on the train.

by _V_ in Gay Male 09/18/2006
4.45
78.8k
9
7
19
0

Southern Magic Ch. 03

Derek learns that magic can be fickle.

by PhoenixKing in Gay Male 09/25/2014
H
4.7
10.4k
9
0
10

Partners

A lonely man discovers he trusts his partner in every way.

by Elenia26 in Gay Male 06/20/2010
H
4.53
37.7k
9
0
13
0

From a Finger to Fucking Ch. 06

Paul experiences full gay sex for the first time.

by the_apocalypse in Gay Male 01/08/2011
4.29
49.7k
9
5
9

Mirror Image

I explore my other self.

by fuckmethere in Gay Male 10/31/2016
4.42
18.3k
9
8
11
0

Chris and Brad Ch. 01

Insecure Chris has an unbelievable night with sexy Brad.

by PeacesignMcPug in Gay Male 05/18/2007
3.96
41.1k
9
8
13

Times is 'ard

Two young Englishmen defy the times and do what feels right.

by brunopuntzjones in Gay Male 10/22/2011
4.36
19.3k
9
2
13
0

Internet Connection Ch. 01

A first timer's experience with an older man.

by idtaboo in Gay Male 08/16/2007
4.43
50.5k
9
1
13
0

The Pretender Ch. 07

Resolutions.

by JaycobMatthews in Gay Male 08/01/2012
H
4.52
13.7k
9
7
9

Secret Santa

Played a secret Santa

by Never_know_20 in Gay Male 11/27/2020
4.39
16.7k
9
8
15
0

Someone Else's Hand

First visit of a straight guy in a gay bath.

by Donatien in Gay Male 03/08/2008
4.3
58.6k
9
6
12
0

True Love Lost

When you admit to love.

by luvkitten in Gay Male 08/05/2008
4.35
23.9k
9
12
13

The Liberation

Two 18-year-olds change each other's lives forever.

by TheEnigmaticOne in Gay Male 03/10/2006
4.46
58.8k
9
2
14
0

Sophomore Year Pt. 04

First time anal for Ian and Mark, then Brian comes to play

by LoveScribe62 in Gay Male 03/01/2024
H
4.89
7.2k
9
1
27

Virgin Hardwood

Chance encounter leaves a man forever changed.

by SensualGnostic in Gay Male 11/17/2007
4.49
63.6k
8
4
9
0

That Moment

The beginning of a new lifestyle.

by bendmeovr69 in Gay Male 03/29/2008
4.39
47.6k
8
7
8
0

Naked Gymnast Weekend - Pt. 02

Hidden passions burst out between three gymnast buddies.

by posingstrap1 in Gay Male 12/25/2023
H
4.83
10.3k
8
12
13
0

Waikiki Curious

He has his first expereince with a man while in Hawaii.

by racecardriver in Gay Male 09/15/2006
4.47
90.6k
8
4
12
0

Let's Go

We'd been dancing for a few hours...

by genorlov in Gay Male 09/27/2012
4.35
23.8k
8
5
11
0

Trio of Non-Monogamies

Showing old friend he's cared for, via unexpected threesome.

by Kumquatqueen in Group Sex 04/09/2023
4.35
11k
8
0
16
0

No Regrets Ch. 04

Tommy's Story – Missing in Action.

by martin_x59 in Gay Male 10/06/2013
4.47
16.3k
8
5
9

Cortland Decker Crawford

Zach teaches rich, young newbie Cortland.

by lionel_collins in Gay Male 01/15/2007
4.48
26.3k
8
4
8
0

My First Time with Conor Pt. 01

I was nervous, but Conor showed me the joys of sucking dick.

by JamieLeeRook in Gay Male 01/30/2020
4.48
19.1k
8
3
18
0

The Navy Lieutenant

Officer visits his boyfriend.

by Dawns in Gay Male 10/13/2007
3.91
39.7k
8
0
10
0

Swim Team Ch. 02-03

Bret considers his feelings for Stanley & Keith.

by FINLEYDIXON in Gay Male 09/24/2021
H
4.7
15k
8
1
16

The Mighty Sword named Flame Tongue

An erotic DnD adventure, Gangbang, Wife Sharing, bisexual.

by mydeepsix in Group Sex 09/27/2023
4.2
9.2k
8
3
24
0
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