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‘his first time’ stories

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Lessons at Poolside

I introduce a young man to the pleasures of sex.

by WayneGibbous in Mature 09/20/2010
H
4.56
135.9k
33
1
55
0

First Lust: First Love

18-year-old twink loses his cherry & falls in love.

by danielblue in Gay Male 03/16/2010
H
4.56
142.8k
32
0
45
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

My Sister and I

Older half sister, shows younger brother the ropes.

by Angelscuck in Incest/Taboo 12/24/2009
3.94
135.5k
32
0
48
0

Girlfriend's Son Ch. 03

Son loses his virginity.

by lonesomejones in Gay Male 05/17/2010
H
4.55
124.7k
31
4
36

Paul Solves a Problem

College virgin who's horny all the time, so he solves it.

by Underwater2 in NonConsent/Reluctance 12/27/2013
3.97
72.3k
31
7
35
0

My Sex Life: School Play

I lose my virginity backstage in high school.

by Templar_Writer in First Time 09/16/2016
4.28
66k
31
2
43
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

Boy Turns into a Man

Guy loses his virginity to his mom.

by football_stud in Incest/Taboo 03/24/2007
3.74
233.4k
31
3
43
0

The Cover is not the Book

New neighbors become the story for the nerdy boy next door.

by RonCabo in First Time 10/12/2021
H
4.74
22.4k
31
8
50
0

Night-time Disturbance Ch. 02

Can we do it without a condom this time?

by stevetruestories in First Time 08/30/2012
H
4.63
67.6k
30
7
32

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

Inside Eve's House

A young man and a building full of women.

by Mr. ComeBiteMe in First Time 07/13/2005
H
4.55
154k
30
6
40
0

A Very Hot Sauna

He had no idea how fun sharing a sauna could be.

by SweetPeril in Mature 08/16/2009
4.37
154.3k
30
4
44
0

A Long, 'Boring' Summer

Young man discovers sex with best friend's mom.

by writerjab in First Time 09/30/2011
4.31
158.1k
30
4
40
0

Heather's Desire

A mother arranges her son's deflowering.

by HeathersDesire in First Time 05/20/2008
4.39
119.9k
30
0
46
0

Pink Panties in the Library

Two college virgins explore each other over Christmas break.

by JRLover in First Time 11/26/2010
4.32
112.1k
30
15
45
0

My First

New Guy Loses his virginity to an African Queen.

by ramoredrake in First Time 09/02/2017
4.25
53k
29
5
49

Teacher Experience

English teacher taught him about hot wives as well.

by Joatster in First Time 09/17/2007
4.45
121.2k
29
8
42
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

Best Friend Turned Lover

Long time friend takes my virginity at my 19th birthday

by PurpleParadise in First Time 02/09/2017
4.26
70.2k
29
7
43
0

Tommy's Graduation Present

The best grad present a guy can receive.

by Tender86 in First Time 05/28/2007
H
4.6
133.1k
29
4
39
0

The First Time

Black man reflects on losing virginity to an Asian stripper.

by AuthorMLongmyre in Interracial Love 03/15/2020
4.49
17.3k
29
1
46
0

First Resort

A young man comes of age with an older woman.

by byronbert in First Time 10/11/2013
4.43
114.9k
29
9
41
0

Jessica Loses Her Virginity

A crossdresser's coming of age.

by DCJessicaCD in Transgender & Crossdressers 04/16/2007
H
4.53
119.9k
29
13
32
0

Stepmother's Tale

How husband lost his cherry to his stepmother.

by NaughtySamantha in Incest/Taboo 03/22/2008
4.35
134.5k
28
7
40
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

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

Seduced by Innocence

A psychopathic woman seduces a virgin and brags about it.

by Mardell in Mature 12/25/2013
3.66
57.3k
28
4
39
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

Spin the Bottle

College kids play spin the bottle - of a different kind.

by a_wilson29 in First Time 08/19/2007
4.1
215.2k
27
5
47

Lessons from Days Gone By Ch. 02

Laura and Michael's relationship continues to develop....

by nosebone in First Time 05/02/2018
H
4.78
30.2k
27
14
33

Chad and Blaine Ch. 06

Will Chad and Blaine get their happily ever after?

by Baby789 in Gay Male 01/31/2013
H
4.77
16.7k
27
0
30

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

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 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

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

The Perils of Love Ch. 01

The Tale Begins.

by WillDevo in Romance 12/12/2019
H
4.7
17.4k
27
8
42

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

Warren Baker's Valentine

His rent is due and he gets a job offer of a different kind.

by geronimo_appleby in First Time 01/22/2013
H
4.59
64.8k
26
13
42
0

Sir Willy Comes of Age

My summer of languages learned, and innocence lost.

by Tall78701 in Mature 12/15/2021
H
4.8
24.6k
26
7
47
0

Perry's First Time

Perry loses his cherry to a football jock on a camping trip.

by danielblue in Gay Male 04/27/2007
3.99
150.3k
26
0
36
0

First Time For Us Both

Losing our virginity together.

by EroticExperience69 in First Time 09/18/2017
4.41
66.5k
26
4
37
0

Lost Virginity

How I lost my virginity.

by ratfink802 in Incest/Taboo 03/23/2021
3.77
49.9k
26
3
44
0

Eric the Geek

18-year-old nerd has sex for the first time.

by Nice_Guy_Done_Last in First Time 06/05/2006
3.64
149k
26
6
32
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

Aunt Jane and His First Time

He risks telling his aunt he heard her fucking, and...

by mishkin in Incest/Taboo 07/23/2009
4.04
159.3k
25
2
37

Innocent

An innocent young couple explore.

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

Teacher's Pet

Chad overcomes his disability.

by Many Feathers in First Time 06/09/2006
H
4.68
114k
25
9
34
0

Abbey's One Night Stand

Abbey has a one-night-stand with her college study partner.

by pregnantlover in First Time 09/19/2006
0
149.8k
25
0
40
0

Country Lovers

Neighbouring friends become lovers.

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

Jono's Journey Home Ch. 01

An Arab orphan returns home.

by Shy_Bottom69 in Gay Male 04/19/2017
H
4.59
20.6k
25
3
42

Caren with a C

Tommy loses his virginity in the summer of 84.

by Obiaha in First Time 09/08/2017
H
4.63
40.7k
25
17
30
0

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

Sweeter than Candy

Guy loses v-card to hot blonde.

by LoneloverX23 in First Time 07/26/2017
4.09
34.5k
25
2
29

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

Boy Training

She teaches 18-year-old hunk to be her lover.

by midnightfalcon in First Time 04/17/2006
4.42
143k
25
8
30
0

Game Night

Best friends become lovers.

by Ravlicious in First Time 09/15/2006
4.15
169.7k
25
4
32

Aunt Em Ch. 01

How my aunt and I lost our virginity together.

by Falling4U in First Time 01/23/2012
3.89
112k
24
8
30

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

Back for More

Kara takes Joe's virginity - but whose favor is it?

by Scheherazade73 in First Time 11/02/2012
H
4.54
64.9k
24
7
32
0

Tom Gets Lucky

Virgin gets seduced by older woman.

by DurtyWriter in First Time 03/11/2019
4.2
41.9k
24
0
31
0

Terry Ch. 01: Losing Virginity

Losing my virginity to a mature foreign lady with piercings.

by Harvey_32 in First Time 12/25/2015
4.27
32.4k
24
2
35

Me and Blaise on a School Bus

It is hot with me & her & her sister in the front row.

by Micheal82 in First Time 11/25/2008
3.91
147k
24
0
31
0

Ashley's Prostitution Ventures #02

Ashley takes the virginity of her second client.

by Kveldulf in First Time 03/05/2019
H
4.67
31k
23
6
24

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

His First Prom Ch. 01

An inexperienced teen is taught the basics of sex.

by TalonDigital in First Time 09/23/2011
H
4.55
114.3k
23
6
37

A Secret Life Ch. 05

An end to the secrets.

by ingarlm in Gay Male 11/17/2008
H
4.81
39.6k
23
10
26

Metamorphosis Ch. 01

Toy boy reminisces affair with mature female professor.

by avatar_roku in Mature 08/15/2021
H
4.7
35.9k
23
10
53

Rita, My First

A friend's mother wants more than her daughter knows.

by Homebrew66 in First Time 08/19/2022
4.34
19.1k
23
1
35
0

The Gift of Abstinence

A college freshman befriends an inconceivably hot woman.

by rpsuch in Romance 07/06/2010
4.34
66.4k
23
28
37
0

Practicum

You can only learn so much in the classroom...

by YDB95 in First Time 03/01/2016
H
4.69
65k
23
1
46
0

A Stroll in the Woods Ch. 02

Glenn discovers new sensations.

by martin_x59 in Gay Male 07/02/2011
H
4.52
44.2k
22
4
28

The Best Blow Job Ever

A present for his birthday.

by Anne08 in First Time 03/12/2008
4.41
193.9k
22
16
35
0

The Woman on the Bus

First time seeing and touching a naked woman up close.

by Chippyminton in First Time 12/30/2020
4.38
27.9k
22
2
35
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

The Railroader and the Bank Teller

A young railroad man has a mad crush on a bank teller!

by SXDispatcher in Loving Wives 02/17/2020
0
19.4k
22
18
29
0

Smithson Ch. 01: The Forge

The son of a blacksmith must find his own path in the world.

by Sinisterinfant in Sci-Fi & Fantasy 04/25/2013
H
4.64
30.7k
22
10
36

The New Guy

Ansel meets the girl of his dreams in a new town.

by epiphany65 in First Time 01/23/2009
H
4.65
46.2k
22
0
28
0

Gina Ch. 01

Tommy loses his virginity & meets an older woman.

by Tommy1982 in Mature 08/12/2006
4.26
131.4k
22
3
41

Lost Innocence

Every one has a story. This one is mine.

by Many Feathers in First Time 05/02/2008
H
4.6
110.4k
22
12
28
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

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

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

Memoirs of an Old Man Ch. 01

Old man telling about his sexual exploits when he was young.

by goliathslawyer in Incest/Taboo 11/06/2017
4.42
27k
20
1
28

Work Experience Ch. 02

More training with Mrs Gregory.

by Calorific in First Time 01/04/2024
H
4.75
14.9k
20
6
33

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

Liz Ch. 01

A beautiful widow meets her late husband's son.

by Hot_Vanessa in Mature 12/04/2010
3.81
60.6k
20
14
27
0

Alice Ch. 05

Alice begins teaching Charlie.

by yesterdays in Incest/Taboo 12/19/2013
4.49
46.8k
20
1
29

Oh, Jan!

Losing my virginity to my friend's mom.

by JerryDancer in First Time 01/31/2024
4.41
28k
20
3
43
0

Lusty Love in the Afternoon

Killing time at the mall Danny meets the man of his dreams.

by danielblue in Gay Male 12/20/2009
H
4.51
68k
20
0
23
0

The Lesson

Young man gets seduced by 18-year-old for his first time.

by DelightfulNikki in First Time 05/13/2013
4.21
63.3k
20
5
27
0

The Building Bombshell Pt. 01

Coming of age story. This is how I lost my virginity.

by HornyHermit in Mature 01/28/2020
4.07
38.5k
19
3
32

The Cleaning Lady

The cleaning lady gets dirty with horny high schooler.

by mnav8or in First Time 05/26/2012
4.15
120.3k
19
2
27
0

Learning

A young man can learn a lot about sex in three weeks.

by R410a in First Time 04/23/2022
4.43
28.8k
19
14
34
0

New Adventures

A tale of first time, masturbation, voyeur.

by Starkraven in Exhibitionist & Voyeur 02/19/2014
4.47
52.2k
19
4
29

Susie Ch. 02

Susie has sex with her best friend's virgin brother.

by Susie_O in First Time 09/12/2007
H
4.66
139.4k
19
5
28

First-Timer

Teacher takes her young student's virginity.

by MaryGirard in Mature 03/14/2013
4.16
171.1k
19
6
30
0

Crashed

Two young men and I land on a desert island.

by DawnR in Erotic Couplings 04/04/2024
4.46
13.5k
19
4
31

Inch By Inch

Soldiers capture a young female warrior.

by BrendanX in NonConsent/Reluctance 11/11/2006
3.75
115.3k
19
3
35
0
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