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‘his first time’ stories

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his first time 

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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

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

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

The List Ch. 01

Hung 18-year-old nerd uses his tool for the first time.

by handsomeyetnice in First Time 04/11/2008
4.37
353.5k
212
14
314

Mr. Nice Guy vs. The Mall Rat

Jason Lakes loses his virginity.

by EsotericNiceGuy in First Time 11/12/2010
4.37
67.7k
35
7
44
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
154.2k
30
4
44
0

Doing Mr Pepperoni

He was hairy, hefty and hung and he wanted Jake and me.

by danielblue in Gay Male 10/11/2011
4.37
34.1k
37
0
43
0

My and My Wife's Journey Pt. 01

A story of a virgin guy and his virgin wife.

by elephanted in First Time 02/13/2024
4.37
13.1k
9
1
21

A Fond Farewell

Young man's first time with a beautiful colleague.

by free1radical in First Time 07/15/2016
4.37
42.5k
14
3
23
0

It Started with Coffee

Two mothers discuss helping their sons become men.

by PMDlite in Incest/Taboo 12/23/2016
4.37
121k
95
7
117
0

Thankful For What?

Fun Thanksgiving first time gay male.

by APRILBLOSSUMS in Gay Male 11/20/2017
4.37
30.3k
6
2
10
0

Jack's Education Ch. 01

The events leading to Jack's encounter with Tina

by rovijack43 in Novels and Novellas 03/10/2006
4.36
111k
38
1
54

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
10
0

Al Gets Lucky

Man stumbles through his first time.

by I-WISH in First Time 04/07/2006
4.36
22.3k
1
4
1
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

When the Levee Breaks

The story of my husband and his first threesome.

by StackedAction in First Time 05/26/2017
4.36
45.3k
14
6
23
0

Davey and Mommy: Snowed In

Son discovers sex with his mom while snowbound.

by redkissy in Incest/Taboo 08/21/2017
4.35
232.2k
150
28
193
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

Moans Veneris Ch. 01

Twins: He hears her jilling; she catches him jacking.

by CarlusMagnus in Incest/Taboo 05/02/2014
4.35
154.3k
141
11
198

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

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

Young James is Seduced

Older woman gives lessons to an English teenager.

by FitJim in First Time 09/17/2007
4.35
114.3k
8
6
11
0

Egyptian Massage

Student participates in an ancient rite.

by Bosq in Toys & Masturbation 05/10/2007
4.34
45.8k
11
6
13
0

Rita, My First

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

by Homebrew66 in First Time 08/19/2022
4.34
19k
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

An Unlikely Couple

Former H.S. Jock is taught the ropes.

by theunknown2000 in First Time 04/24/2009
4.34
47.4k
9
6
17
0

College Try

Romantic first time - for both?

by Sandman8314 in First Time 08/01/2014
4.34
63.2k
13
5
24
0

Virginity Sale

Making money off the first time.

by KeithD in Gay Male 02/23/2022
4.34
18.3k
14
10
28
0

Big Easy Lessons Ch. 04

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

by aspiringDOM in First Time 01/16/2011
4.33
55k
5
1
6

Indian - Housemaid Lakshmi

18-year-old boy has his first ejaculation.

by Bandra in First Time 08/19/2006
4.33
309.9k
64
10
78
0

A Hand Down His Shorts

Widowed lady loves the delivery boy.

by VeryDirtyMind in Mature 09/12/2016
4.33
131.6k
69
11
87
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

My First Gay Experience

Short story about me getting my cherry popped finally.

by JR493 in Gay Male 02/25/2019
4.32
106.7k
27
24
39
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

After School Adventures Ch. 03

When the school bell rings, the rules change...

by Slash_Raptor in First Time 08/22/2011
4.32
66.3k
6
0
10

Mrs. Robertson

Every young man's fantasy - the older woman.

by pleasureandfun in Mature 09/13/2007
4.32
103.3k
11
3
19
0

From Virgin to Stud, My Evolution

Tom is seduced by older woman, continues his education.

by NerdySex in First Time 04/13/2018
4.32
46.7k
40
0
66
0

Tiki Trouble

Colin makes an unusual purchase.

by sourdough999 in Incest/Taboo 10/13/2006
4.31
125k
50
11
61
0

Impassioned

He discovers passion as he loses his virginity.

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

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
39
0

Chocolate Coffee Beans

He loses his virginity to his friend's mom.

by rolandofgillead in First Time 01/06/2008
4.31
131k
9
10
23
0

Fun at a Pioneer Camp

The first time can be the best in the whole life.

by russianguy30 in Group Sex 08/03/2011
4.3
47.1k
4
2
7
0

Fireside First

College sweethearts lose virginity.

by On_Impulse in First Time 01/13/2013
4.3
54.8k
4
3
6
0

Educating Gary Ch. 01

Step sister takes her new step brother's virginity.

by ramma618 in Incest/Taboo 07/13/2010
4.3
135k
37
9
51
0

The Birthday Blowjob

Girlfriend gives him the ultimate gift.

by A_Non_A_Moose in Erotic Couplings 01/24/2014
4.3
88.3k
38
3
48
0

My Brother's Baby

18-year-old virgin finally succumbs to twin brother.

by twincest in Incest/Taboo 04/23/2008
4.3
736.8k
368
40
489
0

Losing My Virginity

His first sexual experience.

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

Annie

Have you ever had a dream?

by artiepuy in First Time 02/23/2010
4.29
30.3k
1
4
2
0

Making Him an Example

Guy is caught peeping into a girl's cabin.

by BigOGeek in First Time 12/10/2007
4.29
146.5k
19
2
33
0

Crying Mom

Son consoles his mother.

by standingstones in Incest/Taboo 07/24/2007
4.29
484.9k
138
1
180

The Virgin and the Veteran

A middle aged woman is seduced by a teen.

by jasonnesbit in Mature 04/28/2009
4.28
62.7k
12
2
20
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 New Girl

The tentative first time for two lovers.

by Gizzmotick in First Time 06/13/2006
4.28
57.3k
7
3
10
0

Sex, Step By Step

Young couple learn from each other.

by ainu2 in First Time 10/10/2009
4.28
60.9k
5
0
11
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

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

Posh James. First Virgin Guy

For once a guy that kept his word.

by alexcarr in Gay Male 06/29/2012
4.27
54.6k
4
3
4
0

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

I Fucked My Mom Up the Ass

Son gets discovered when he tries to fake a sick day.

by FeverDreamer in Incest/Taboo 10/10/2010
4.27
1.68M
372
62
535
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
10
0

Best Friends

Best friends experiment for first time.

by Patrick2380 in First Time 11/25/2006
4.27
298.8k
72
12
105

Older Male Virgin

Virgin Michael learns sex from surrogate.

by MackRet in First Time 01/30/2017
4.26
27.8k
12
0
19
0

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

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

Gina Ch. 01

Tommy loses his virginity & meets an older woman.

by Tommy1982 in Mature 08/12/2006
4.26
131.3k
22
3
41

For the First Time

A young man in good hands.

by RufusLeMont in First Time 04/04/2011
4.26
69.3k
5
4
8
0

Nynke Ch. 05

Brother got properly laid at his 18th birthday.

by dutchpantyraider in First Time 06/13/2008
4.26
39.7k
3
0
5

Sexual History of a Man Pt. 01

First sexual experience of two virgins.

by oldlover40 in First Time 11/28/2009
4.26
41.7k
4
3
6

Aunt's Boy Toy Ch. 01

Cougar's feast.

by amorouslion in Incest/Taboo 08/15/2017
0
88.6k
51
4
71

Educating a New Neighbor

Inexperienced new neighbor gets a lesson in sex ed.

by happybirthday in First Time 07/16/2006
4.25
181.4k
9
9
17

Duet

19-year-old man learns a love song.

by Hornsup in First Time 03/18/2006
4.25
36.5k
3
2
3
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

Ethan's First

The pool boy loses his virginity to a college girl.

by alupine in First Time 06/18/2012
4.25
160.5k
85
15
117
0

Mom's Friend Helps Me Out

Virgin has sex at last.

by goodnnnight in First Time 11/05/2008
4.25
188.2k
33
5
43
0

The Virgins

Two college freshman find each other.

by tommcgee in First Time 07/26/2008
4.25
49.2k
8
2
14
0

Camping with My Girlfriend and Family

Sometimes animal instincts takeover - even when it's mom.

by caughtsinning in Incest/Taboo 10/04/2017
4.25
284.1k
216
18
346
0

The Anniversary

An engaged couple finally release their virginity.

by NadiaLove17 in First Time 07/07/2012
4.25
29.4k
7
1
14
0

Black Teacher

Lucky guy loses his virginity to his ebony English teacher.

by RandomStorywriter01904 in First Time 05/26/2013
4.25
132.3k
56
5
67
0

Innocent

An innocent young couple explore.

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

Take My Advice

Young man seeks advise on losing his virginity.

by Ashson in Humor & Satire 02/17/2013
4.23
16.1k
1
1
5
0

Angelique

A young man comes of age.

by andrewxx in First Time 11/18/2008
4.23
32.5k
4
3
7
0

Mom's Insatiable Hunger

Mom fulfills her insatiable hunger with son.

by football_stud in Incest/Taboo 05/26/2007
4.23
352.6k
70
6
105
0

Showing Him The Ropes

Ave's first night with a real woman, and he learns quickly.

by menensia in First Time 04/24/2017
4.23
27.9k
10
1
11
0

Learning to Love Ch. 02

Three guys continue their first sexual encounter.

by bigk1w1 in First Time 05/03/2008
4.23
33.1k
5
1
5

The Big Day

Online lovers meet for his First Time.

by DreamFinder in First Time 08/14/2007
4.23
19.6k
1
1
2
0

Just Say No, Expanded

Virgin meets Vampire (twice).

by Mark2 in NonHuman 12/21/2006
4.23
29.8k
8
5
13

After Hours Adventure

Sometimes dreams come true in the library.

by sirhugs in First Time 08/31/2002
4.23
97.8k
16
0
27
0

We were Just Kids in Love

True story of two teens losing their virginity together

by Lingerielover1434 in First Time 03/12/2012
4.23
67.6k
9
10
10
0

Lost Virginity

Class reunion unites him with his first love.

by AGreyFoxxx in First Time 05/30/2008
4.22
62.5k
1
3
5

Teacher Becomes The Student

Mid-20's virgin teacher gets schooled by sexy colleague

by TheOxRocks in First Time 02/11/2016
4.22
55.6k
41
1
52
0

Hitting the Right Notes

Gordon loses his virginity to his piano teacher.

by Blacksheep in First Time 07/22/2023
4.21
17.8k
5
0
14
0

My Summer with Auntie Ch. 01

Young man and his aunt become "close relatives".

by mistertucson in Incest/Taboo 09/29/2006
4.21
216.3k
65
0
102

A Virginal Challenge

Guy wants sex, and gets it - but not how he expects it.

by HeroFizzer in Transgender & Crossdressers 12/25/2017
4.21
53.1k
41
2
59
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 Menu

Jeremy's sexuality is awakened.

by Bad2Bone in First Time 05/26/2013
4.21
40.8k
8
0
12

Baby Sitting

First time with a woman.

by Koreangal in First Time 01/31/2009
4.21
207k
18
8
28
0

Logical Mom

A mother & son story.

by Momstheboss in Incest/Taboo 05/20/2012
4.21
254.6k
90
16
117
0

My First

Young couple attend a dude ranch.

by Ashson in First Time 12/24/2012
4.21
52.8k
2
2
10
0

Ridden with a Smile

A short haired beauty rides me, smiling all the while.

by AStabInTheDark in First Time 12/01/2012
4.2
35.8k
5
3
8
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
78.4k
8
0
12
0
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