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‘his first time’ stories

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Holiday #195

Celebrating their 195th consecutive holiday tests friends.

by WatchingCloud in First Time 06/22/2017
HW
4.84
163.2k
294
65
379
0

Rose: My First

An older woman teaches 18-year-old virgin.

by hjames1950 in First Time 05/13/2006
H
4.57
162.4k
18
6
25
0

A Cousin Ch. 01

Durnk cousin takes his virginity.

by making_upper26 in Incest/Taboo 12/14/2007
3.66
161.1k
52
12
64
0

Ethan's First

The pool boy loses his virginity to a college girl.

by alupine in First Time 06/18/2012
4.25
160.6k
86
15
119
0

Clark's Story Ch. 01

Clark gets football jock Gordie for his lab partner.

by robcub32 in Gay Male 02/04/2010
H
4.61
159.5k
160
22
213

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

Lost My Virginity To My Sister

Mutual sacrifice of our virginity.

by vikraman in Incest/Taboo 05/12/2008
3.57
158.5k
18
5
28
0

Pederastic Eromenos

18-year-old's sexual awakening by man is his 60s.

by RobXXX in Gay Male 08/22/2007
H
4.67
158.4k
45
24
60

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

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

Auntie Mabel Ch. 01

18-year-old virgin gets help from sexy older woman

by drsnip in Novels and Novellas 10/21/2006
H
4.68
154.3k
68
5
110

Lust for an Older Woman

Fit young farmboy is initiated by his sexy boss.

by Jamie_in_dresses in First Time 06/08/2012
H
4.5
154.3k
65
8
98
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

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

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

A Very Special Spring

He is shown the ropes by the Woman next door.

by Joe F. in First Time 12/11/2003
4.47
150k
16
5
23
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

Cougar and her Five Virginal Cubs Ch. 01

Kathleen matures five, young men with hands on sex ed.

by SusanJillParker in Mature 06/30/2012
4.47
149.2k
93
16
158

Eric the Geek

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

by Nice_Guy_Done_Last in First Time 06/05/2006
3.63
149k
26
6
32
0

Forbidden No More

Secretary acts on her crush on boss's 18-year-old son.

by FlightyFaerie in First Time 02/21/2007
4.46
148.8k
14
2
21
0

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

Claire

My teacher takes my virginity.

by AGreyFoxxx in First Time 02/22/2010
4.4
146.7k
17
3
25

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

Mrs. Bonnie Ch. 01

Marture woman breaks in a virgin

by sghoul in First Time 02/27/2008
4.47
144.1k
34
10
44
0

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

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

How Hannah and I Got Together

Two friends explore each other's sexuality.

by sex4every1 in First Time 01/12/2011
H
4.53
141.6k
96
16
131

Sex Education with Lisa

A young man and his teacher become lovers and create life.

by Patrick7 in First Time 03/28/2016
4.18
141.5k
118
9
188
0

A Gentle Awakening

18-year-old guy's first time is with an older woman.

by julia so sweet in First Time 11/03/2007
3.89
139.5k
11
7
14

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

How I Lost My Anal Virginity

My first time losing my anal virginity to a 9 in cock.

by silverbullet2211 in Gay Male 11/02/2016
H
4.51
139.4k
52
18
69
0

Jimmy meets Miss Victoria

A young man is introduced to sex and femdom.

by Rocytman in First Time 12/13/2008
H
4.57
139.1k
83
9
122

Older Women at the Farm Store

An older customer "teaches" a young counter clerk.

by maninconn in Mature 11/07/2008
H
4.53
137.9k
40
0
60
0

Words I Shall Never Forget

Encounter with a stay at home mom.

by JimAfflictioN in First Time 04/12/2008
3.51
137.8k
3
8
6
0

New Neighbour Ch. 01

New neighbour takes spying young man under her wing.

by smithE101 in First Time 09/05/2009
H
4.55
136.7k
40
7
63

A Virgin Seminar

24-year-old virgin guy finally finds the right time & place.

by Many Feathers in First Time 04/18/2008
H
4.62
136.7k
82
27
102
0

Tammy asks Jimmy for Help

Young lovers learn about each other.

by Charles Petersunn in First Time 05/13/2006
4.48
136.6k
10
9
17
0

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

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

Educating Gary Ch. 01

Step sister takes her new step brother's virginity.

by ramma618 in Incest/Taboo 07/13/2010
4.3
135.1k
37
9
51
0

Three Weeks to Lose his Virginity Ch. 01

Young man is given a helping hand.

by seth_perm in First Time 09/29/2007
H
4.62
134.7k
103
5
145

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

Poker was the Start

Strip poker was the spark for virgins.

by Bigchicklover in First Time 02/08/2010
3.8
133.8k
8
5
16
0

18

Two young 18-year-olds discover the battle of the sexes.

by greystardust in First Time 01/11/2010
3.03
133.5k
49
5
51
0

Mom's Estranged Son Ch. 02

Mother and Son are reunited and cross the final line

by curlyspurs in Incest/Taboo 03/30/2013
H
4.52
133.4k
100
16
120

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

A Couple's First Time

18-year-old loses virginity to his girlfriend.

by XX_vampirekindred_XX in First Time 11/14/2006
2.7
133.1k
11
7
12
0

Best Summer Ever

Nineteen and haven't been laid, starting college soon.

by DG Hear in First Time 08/25/2011
H
4.53
132.4k
34
38
55
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

A Hand Down His Shorts

Widowed lady loves the delivery boy.

by VeryDirtyMind in Mature 09/12/2016
4.33
131.7k
70
11
88
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

Chocolate Coffee Beans

He loses his virginity to his friend's mom.

by rolandofgillead in First Time 01/06/2008
4.31
131.1k
9
10
23
0

Through The Lens

Telescopic Voyeur has dreams come true.

by Millsy in First Time 07/31/2009
H
4.77
131.1k
57
25
74
0

Family Ties: Cumming of Age

Sexy aunt tutors nephew on finer points of sex.

by JMiller69 in Incest/Taboo 01/29/2007
4.47
129.8k
34
0
54

Water Park Fun Ch. 01

Ryan meets a beautiful girl at the water park.

by storyteller19 in First Time 09/07/2017
H
4.75
129.6k
236
28
339

Friendly Massage

Two 18-year-olds' first time.

by marklz1021 in First Time 08/19/2007
0
128.9k
16
8
19
0

Trip to Village

Trip to village become new experience for a young man.

by mpsaab in First Time 05/23/2008
3.88
127.8k
39
23
47
0

At Last

College students lose virginity during a private spring break.

by secrets2729 in First Time 03/09/2007
3.94
127.7k
6
1
12
0

Home Delivery

Beautiful MILF was my first lover.

by Swilly in First Time 05/20/2013
H
4.54
127.7k
41
9
54
0

My Unusual First Time Ch. 03

He rushes to lose his true virginity.

by djeroticon in First Time 03/26/2006
H
4.74
127.5k
9
21
11

The Touch Ch. 01

Jamie's Story (Revised).

by GreenFingers2015 in Novels and Novellas 02/09/2012
H
4.64
127.3k
215
19
314

Windy View Introduction

18-year-olds explore their sexuality.

by Tender86 in First Time 04/05/2007
3.85
125.9k
9
4
9
0

First Time Stud

Study hard, then get a pussy reward.

by R. Richard in First Time 12/07/2004
3.91
125.6k
2
0
6
0

Amie's Games

Teen looses his virginity to his dream woman, but how!

by Jamie_in_dresses in Transgender & Crossdressers 04/09/2011
H
4.6
125.3k
74
16
101
0

Tiki Trouble

Colin makes an unusual purchase.

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

Eighteen

Virgins finally do it.

by jasliz in First Time 12/24/2009
4.48
124.6k
43
3
52
0

Professor Lumpkin

College teacher takes advantage of a bright student.

by stoneypoint in First Time 08/23/2006
3.23
122.9k
10
0
18
0

Mom Solves My Problem Ch. 03

Mowing the lawns at Mom's friends, and more.

by Dirkstimson in Incest/Taboo 08/21/2009
4.49
122.5k
46
9
56

An Unlikely Valentine

A slutty coed and a well hung virgin give in to lust.

by tk5555 in First Time 02/02/2013
H
4.59
122.1k
93
15
122
0

Senior Seduction

An old friend becomes much, much more.

by pleasureandfun in Mature 09/13/2007
4.49
121.5k
11
7
16
0

Cindy Lou Seduces the New Stockboy

She gives him the best introduction to sex.

by Boxlicker101 in First Time 08/20/2005
4.45
121.2k
16
11
19
0

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

Davin's Teasing Sister Ch. 03

Davin finally loses his virginity - to his sister.

by Madmax77_1977 in Incest/Taboo 05/31/2009
H
4.62
121.1k
39
9
51

It Started with Coffee

Two mothers discuss helping their sons become men.

by PMDlite in Incest/Taboo 12/23/2016
4.37
121.1k
95
7
117
0

August Rain

Peter loses his virginity during a summer rainstorm.

by The_Unicorn in First Time 08/25/2009
H
4.56
120.6k
37
10
67
0

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

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

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

Night Swim

A nude swim at the reservoir

by Silvermouse in First Time 01/20/2011
H
4.6
119.1k
33
11
54
0

Chemistry of Love

Jealousy sets off a bad reaction.

by YDB95 in First Time 03/01/2017
HW
4.72
117.1k
63
17
94
0

My Aunt is a Helluva Teacher Ch. 01

A life lesson from auntie Shelly.

by WiseArms in First Time 02/23/2006
4.16
116.4k
11
0
20
0

Persuading Amy

He has to lie to get inside her.

by pineseedling in NonConsent/Reluctance 12/17/2008
3.98
116.2k
49
0
63
0

Listen with Your Heart

Jordan finds a way to communicate with his deaf friend Kevin

by robcub32 in Gay Male 02/04/2010
H
4.77
115.8k
260
68
293
0

Jack and Jill

Salesgirl at Fur Salon seduces him.

by FurLove in Incest/Taboo 05/26/2006
H
4.65
115.5k
40
6
53
0

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

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

The Other Side of the Window

18-year-old guy ia fascinated by older neighbor.

by furryfan in First Time 09/26/2008
H
4.71
114.5k
46
13
67
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

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
12
0

Gentle First Time

Whispered taking man's virginity. More for the girls soon! :)

by littlekitten738 in Audio 09/22/2015
4.41
114.1k
34
16
43
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

The Bus Ride

First sexual contact with another person.

by tightwaddd in Gay Male 04/02/2011
4.46
113.8k
48
16
55
0

Young Wolves Ch. 01

Guy bit by a beautiful girl goes through changes.

by sirreadsalot10 in NonHuman 05/04/2010
H
4.72
112.5k
229
14
259

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

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

Consolation Prize

Consoling a friend leads to first-time experience.

by oldrgent in First Time 07/21/2002
4.18
111.2k
13
0
18
0

Nurse Jenny Experiences Midway Ch. 02

Nurses find themselves on the front line of the war.

by BlewWater69 in First Time 01/14/2007
H
4.6
111.2k
15
4
19

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
56

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
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