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‘his first time’ stories

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his first time 

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Seamus Ch. 02

Seamus takes his best-friend's virginity.

by Sachs in Gay Male 02/17/2006
H
4.78
110.4k
27
5
39

Anal At Last Ch. 15

Sam's first sexual experiences.

by scottishmeat in First Time 02/08/2008
H
4.65
109.5k
25
12
29

Business & Pleasure Ch. 01

My first encounter with a man - and the pleasures.

by nero957 in Gay Male 08/02/2010
4.27
109.2k
8
10
14

New Teacher Bad Boy

Bad boys helps new teacher survive at rough school.

by braindump in First Time 08/28/2013
4.26
108.8k
66
7
94
0

Grand Island

A train ride to a new world and a new life.

by YDB95 in Romance 11/25/2013
HW
4.8
107.8k
72
38
95
0

Harry's Island Initiation

Young man reluctantly on holiday finds unexpected joy.

by Rex Siter in First Time 08/19/2011
H
4.75
107.4k
39
15
55
0

My First Gay Experience

Short story about me getting my cherry popped finally.

by JR493 in Gay Male 02/25/2019
4.32
106.8k
27
24
39
0

Dear Sweet Dee

Memories finally spoken of.

by Many Feathers in Mature 06/15/2010
H
4.76
106.6k
52
20
68
0

The Good Girl

Two virgins find love.

by SlamDuncan in First Time 08/02/2013
H
4.68
106.1k
76
17
97
0

Country Lovers

Neighbouring friends become lovers.

by lurkingdirk in First Time 02/10/2007
H
4.64
105.5k
25
0
40
0

Our First Time

The first time me and my boyfriend fooled around.

by AhuvAdonai in First Time 10/18/2008
4.28
104.3k
11
8
14
0

My Teacher Ms. Miller Ch. 03

Tony takes his teacher to prom. They play dressup.

by edstevens94301 in First Time 03/17/2013
H
4.63
103.9k
93
4
108

Robinson Family Ch. 04

Siblings get oral and finally have intercourse.

by siblingspank in Incest/Taboo 08/03/2009
4.46
103.7k
13
12
16

Night-time Disturbance

How I unexpectedly lost my virginity to a slightly older woman.

by stevetruestories in First Time 07/06/2012
H
4.59
103.5k
35
9
49

Oy Vey!

First time mutual masturbation for two virgins.

by LoverNumber1 in First Time 07/21/2007
4.38
103.5k
4
12
10
0

View From The Barn

A young man's summer of discovery.

by sabb in Gay Male 03/17/2008
4.16
103.4k
12
5
18
0

Mrs. Robertson

Every young man's fantasy - the older woman.

by pleasureandfun in Mature 09/13/2007
4.32
103.3k
11
3
20
0

Starting Out

Strapping hung young man begins a hedonistic lifestyle.

by sportsman_sammy in First Time 10/26/2006
3.85
102.3k
11
4
23
0

The Beautiful Seduction

Wife seduces virgin friend with her husband's consent.

by Lord_London in Loving Wives 10/24/2007
4.13
101.8k
17
13
37
0

Pam's First Virgin

Pam breaks in her first guy.

by jallen944 in First Time 06/17/2006
4.1
100.7k
3
3
5
0

Cross Country Ch. 02

Lisa pops Sebastian's cherry in the dunes.

by VentureV in Incest/Taboo 11/06/2009
H
4.5
100.5k
20
5
29

Motherfriend

[F/M] The opening I'd yearned to find was there all along.

by LanceQuiver in Incest/Taboo 09/16/2017
H
4.54
100.5k
110
26
149
0

Aunt Helen

A chance encounter turns to extreme sexual delight.

by TropicalHeat in Mature 03/02/2013
4.41
100.4k
30
4
37
0

The Perfect Prefect

First time encounter for two 18 year old boarding scholars.

by danielblue in Gay Male 06/03/2003
3.6
100.2k
10
0
14
0

Cousin Laura, My First Love Ch. 01

Hot cousin deflowers a shy guy.

by ForceFull in Incest/Taboo 09/29/2006
4.4
99.5k
29
5
39

The Horny Goddess

College virgins discover each other.

by ainu2 in First Time 05/14/2008
H
4.67
98.9k
26
10
40
0

The Neighbour

A young man's first sexual adventure.

by mercer78 in First Time 09/17/2013
H
4.5
98.9k
31
8
37
0

Big Easy Lessons Ch. 01

18-year-old Joe is taken by 46-year-old MILF Lisa.

by aspiringDOM in First Time 01/13/2011
4.15
98.3k
12
3
17

Three Weeks to Lose his Virginity Ch. 03

Can Spencer finally lose it?

by seth_perm in First Time 11/02/2007
H
4.77
98.1k
39
11
47

After Hours Adventure

Sometimes dreams come true in the library.

by sirhugs in First Time 08/31/2002
4.23
97.9k
16
0
27
0

Exercising with Benefits Ch. 01

His birthday present is late but he isn't complaining

by Bigguyyyyy in First Time 05/25/2008
H
4.63
97.7k
28
2
36

The Learning Room Ch. 02

His first time is with the Head Cheerleader.

by regularguy13 in First Time 10/08/2010
4.44
97k
35
13
47

Linda Ch. 01

A mature divorcee introduces me to sex.

by ableoneable in First Time 06/13/2010
4.39
96.4k
21
2
28

Love x Two Ch. 01

Sam and his beautiful mother show they're love.

by Daniel5421 in Incest/Taboo 11/09/2011
4.06
96.3k
37
13
53

The Ski Trip

How I lost my virginity twice on the same day.

by 4eyedbrit in First Time 01/23/2009
H
4.6
96.2k
33
3
56
0

Kiss, Lick, Suck, Fuck

An account of my first intercourse experience - embellished.

by bubbatxman in First Time 04/01/2012
3.69
96k
5
5
6
0

The Right Way to Begin

High school grads discover sex at summer camp.

by shy_boy in Gay Male 06/07/2006
H
4.51
95.1k
50
0
61
0

Just Perfect Anna, My First Time

Unexpexted first time with a young beauty.

by Paddy40 in First Time 10/08/2008
3.53
95k
3
2
5
0

Nikki Ch. 01

She teaches student about sex.

by caprine in First Time 12/07/2007
4.44
94.6k
16
10
24

Summer Intern

BBW milf seduces virgin coworker in office bathroom.

by BartlebyWaylon in Mature 01/20/2011
4.42
94.1k
33
5
45
0

The Boss's Wife

Young carpenter seduced by the boss's wife.

by rucurious in First Time 09/11/2010
4.03
93.8k
18
0
30
0

Christmas Party Memories

Hotties convince him to recall when he lost his virginity.

by m_storyman_x in Group Sex 11/21/2013
H
4.73
93.5k
83
10
109
0

A Cougar's Conquests Ch. 01: Ollie

Ollie gets more than expected when he knocks on Lisa's door.

by WilliamsStories in Mature 01/07/2019
H
4.6
93.2k
93
17
123

Young Love

They just couldn't wait.

by bassbelly in First Time 04/23/2009
4.14
93.1k
14
3
22
0

Bigger or Better

His first time, but not hers!

by Witchazel in First Time 08/28/2010
H
4.65
92.7k
22
7
33
0

Solving My Little Problem Ch. 02

Coed takes virginity of small-dicked man.

by KarlMartinK in Erotic Couplings 11/24/2007
4.47
92.7k
36
2
47

My First Asian Call Girl

Virgin guy visits an Asian massage parlor.

by cunnydiver in Interracial Love 10/12/2007
3.99
92.5k
25
4
34
0

Painter's Delight

College guy is seduced by older divorcee.

by Alex_Mann in First Time 08/14/2006
4.27
92k
8
1
11
0

The Barmaid

His father's girlfriend shows him how it's done.

by geronimo_appleby in First Time 06/05/2012
4.38
91.6k
27
10
42
0

Innocent

An innocent young couple explore.

by Ashson in First Time 11/14/2013
4.25
90.9k
25
5
32
0

Our Family's Little Secret Ch. 01

Hot aunt takes her nephew's cherry after a little playtime.

by jehoram in Incest/Taboo 12/20/2020
4.44
90.2k
154
15
300

My Comfort Zone

She teaches a younger man to be a perfect lover.

by midnightfalcon in First Time 07/11/2008
H
4.68
90.2k
37
5
61
0

First Time with a Quadriplegic

He loses his virginity to a quadriplegic girl.

by Polysexual in Erotic Couplings 10/14/2007
4.41
90.2k
41
9
51
0

My First Time

An account of the hookup where I lost my virginity.

by GayGuyJason in Gay Male 08/02/2012
4.17
89.9k
18
4
22
0

Friends 2 Lovers

Two best friends take each other's virginity.

by dstebbins in First Time 05/15/2007
0
89.6k
11
4
18
0

Tommy's Lost Virginity

Debbie gives Tommy his heart's desire.

by Tender86 in Mature 09/27/2008
4.45
89.5k
21
4
31
0

Checkmate

An unexpected discovery begins the Game of his life.

by BackyardBottomslash in First Time 02/20/2009
H
4.69
89k
62
14
73
0

Aunt's Boy Toy Ch. 01

Cougar's feast.

by amorouslion in Incest/Taboo 08/15/2017
0
88.7k
51
3
71

All Tits and Bum

It was all his brother Max's fault.

by Bazzza in First Time 11/19/2007
4.43
88.6k
18
3
21
0

Rent is Due

A college freshman deals with a very exacting landlord.

by TwoWorldsTX in First Time 03/19/2013
3.81
88.4k
4
2
15
0

The Birthday Blowjob

Girlfriend gives him the ultimate gift.

by A_Non_A_Moose in Erotic Couplings 01/24/2014
4.3
88.4k
38
3
48
0

A Tale of Two Families Ch. 01

Two very close families experience life and love.

by Lauries Husband in Novels and Novellas 09/04/2009
4.38
88.1k
32
2
64

A Brief Exchange

Best friends give their virginity.

by NobodyWorthKnowing in First Time 02/23/2012
3.43
87.6k
9
3
14
0

My Errand

Young man seduced by friend's mother in art studio.

by Ardydub in First Time 04/17/2007
4.36
86.7k
5
10
11
0

Lost My Virginity to My Cousin

His unexpected first time.

by redkissy in Incest/Taboo 02/22/2017
4
86.7k
26
4
39
0

Losing My Virginity

His first sexual experience.

by joeking2u in First Time 08/03/2007
4.29
86.4k
2
9
5
0

The Summer of the Garden Boys

The summer evening when the boys became men.

by OregonDavid in First Time 08/12/2007
H
4.68
86.4k
13
5
20

That Summer - Alice's Story

Alice's memories of that summer.

by MugsyB in Mature 07/06/2008
H
4.78
83.7k
42
34
56

Robert: Requited Loves

His first time leads to incest.

by caprine in Incest/Taboo 09/08/2007
4.35
83.7k
11
9
18
0

First Time Lucky

He learns about sex from an expert.

by bibimaybe in Audio 07/07/2009
4.45
83.6k
1
4
5
0

Adirondack Heatwave Ch. 01

Sometimes a boy's best friend is his mother's best friend.

by JanetG in Group Sex 01/21/2013
H
4.58
83.5k
10
5
27
0

Our Wedding Night

They are so glad they waited.

by Bakeboss in First Time 05/03/2010
3.6
83.2k
5
1
7
0

Karen's First Time

A shy virgin is aroused by a voyeuristic experience.

by tony090909 in First Time 10/07/2013
3.86
82.9k
11
2
19
0

Becky Robs the Cradle

Always had a thing for "the Beaver".

by RebeccaBrowning in Mature 02/28/2008
H
4.67
82.5k
17
15
29
0

Beware the Quiet One

Two ugly ducklings are better than one!

by YDB95 in First Time 06/20/2014
H
4.69
82.4k
28
18
42
0

Neighbour Wears Nylons

Set in 1972, a lad spots his neighbour undressing.

by Mag58 in Exhibitionist & Voyeur 01/14/2011
4.48
82.1k
27
15
37
0

The Physics of Attraction

Nerd loses his virginity at the library.

by IshtarsMoon in First Time 02/27/2008
H
4.52
80.3k
52
13
75
0

Tutoring isn't Always by the Books

A young college geek's fantasy comes trues.

by DavidMasters in First Time 03/05/2009
4.36
80.1k
28
0
39
0

Cursed Mother

A boy and his friends turn to stange means, and his own Mom.

by HumbleIncubus in Incest/Taboo 12/14/2020
H
4.51
79.9k
112
32
206
0

Explorations Ch. 05

He lose his virginity; Emily tells her story.

by Manny2314 in First Time 03/21/2008
H
4.66
78.8k
12
2
16

Freshman Virgin

Gary's first time.

by MistressMerry in First Time 09/12/2007
H
4.56
78.7k
11
5
14
0

Ripe Summer Fruit

Remote farm on hot summer's day. Sex is blowing in the air..

by naughtyauthor7 in First Time 02/06/2010
4.2
78.5k
8
0
12
0

Spring of Manhood

European boy becomes a man in difficult times.

by gggsss1962 in First Time 03/13/2006
4.45
78.3k
8
4
11
0

The Summer ABCs

She taught him the basics, they took it from there.

by 49greg in First Time 08/22/2014
H
4.52
78.2k
23
4
32
0

How I Lost My Hands' Virginity Ch. 01

My first t-girl is a handful of woman.

by Top18TS in Transgender & Crossdressers 01/17/2009
4.35
77.8k
24
18
28
0

My Music Student

A music teacher and her student lose it together.

by Trapper ak Bobby in First Time 12/10/2006
4.01
76.8k
7
3
13
0

Co-worker's Man Ch. 07

Jon loses his virginity to Frank.

by rmdexter in Gay Male 12/09/2008
H
4.67
76.6k
35
6
39

Their Best Homework Session

College couple share a special first time.

by JammyJay in First Time 02/23/2006
H
4.51
76.4k
14
3
23

Impassioned

He discovers passion as he loses his virginity.

by ShyOKBoy in First Time 09/23/2005
4.31
76.2k
1
5
1

We Lose Our Virginity

They lose their virginities together by the river.

by Andrew Eldritch in First Time 03/11/2008
3.52
75.6k
4
0
5
0

Oh Monique, My Monique

Eric's quest to make his gorgeous friend a lover.

by Venus_Lover in First Time 08/12/2006
4.42
75.5k
6
7
12
0

A Night of Firsts

Birthday boy isn't the only one getting a gift.

by old_n_dirrty in First Time 04/19/2013
4.32
74.8k
13
4
19
0

Hannah Cross: First Seduction

Lusty single Mom seduces lover & fulfills a fantasy.

by FogBard in Mature 08/13/2007
4.18
74.5k
10
3
17
0

Steve & June & I Call on Stacy

Two women cop big, blonde hunk's cherry.

by Boxlicker101 in First Time 11/22/2003
4.45
74.5k
4
1
6
0

Aunt Jane and His First Time Ch. 02

Happy morning in bed.

by mishkin in Incest/Taboo 07/31/2009
4.38
74.4k
8
4
14

Breaking in a Virgin

I was 28 and he was 18 when this happened.

by erotiquegirl in First Time 05/30/2011
3.96
73.8k
14
1
17
0

The Wager

Older woman takes hunk's cherry.

by No Panty Girl in First Time 11/28/2005
4.42
73.7k
13
6
20
0

Shy Man Finds Love

Coed takes guy's virginity on a dare.

by Bakeboss in First Time 10/29/2009
4.13
73.6k
8
3
14
0

First Time For Everything

Some firsts I've experienced.

by dirtyjoe69 in First Time 07/17/2006
3.6
73.5k
2
2
4
0

Homecoming

Rita meets him as he gets off the bus.

by geronimo_appleby in First Time 08/26/2013
H
4.6
73.1k
21
9
36
0
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