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‘his first time’ stories

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his first time 

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Amber's Mother

Ryan plans to see his girlfriend, but meets her mother.

by Pindaflash in Mature 03/24/2011
4.39
208.5k
66
9
88
0

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

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

Robbie Loses His Virginity

Robbie's first time with older guy.

by robbie_krt in Gay Male 01/04/2022
H
4.51
72.8k
64
19
95
0

Indian - Housemaid Lakshmi

18-year-old boy has his first ejaculation.

by Bandra in First Time 08/19/2006
4.33
310k
64
10
78
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

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

First Cum Swallow

Swallowed my first load.

by garyr43 in Gay Male 06/14/2018
H
4.59
238.3k
61
108
81
0

Some Help From Mom

Son gets a helping hand from his mother.

by carson2658 in Incest/Taboo 06/05/2013
4.13
166k
61
11
77
0

Bum Chums Have Fun In The Sun

A virgin stud loses his cherry to 4 hot men on the beach.

by danielblue in Gay Male 06/17/2006
H
4.56
211.5k
61
0
85
0

My MILF

His mother lovingly guides him in the ways of sex.

by darkstar04 in Incest/Taboo 03/18/2006
4.47
238.9k
60
0
82
0

In the Basement with My Sister

Older sister take in charge her brother's virginity.

by alone4years in Incest/Taboo 05/09/2007
3.76
525k
60
24
94
0

Learning to Kiss

Mom teaches her son how to kiss.

by History Nut in Incest/Taboo 09/24/2008
4.2
321.8k
59
13
87
0

2927 Vadodara Express Ch. 01

Virgin young man runs into a willing woman.

by prahaar2006 in First Time 02/17/2006
4.19
324.9k
59
19
73

Str8 Sex to be near Gay Dream Ch. 01

A closeted gay teen has straight sex to be near his crush.

by nygayguy in First Time 09/25/2017
H
4.61
32.3k
59
8
98

Brotherly Love

It was the first time for both brother & sister.

by countrycal in Incest/Taboo 02/25/2006
H
4.62
241.6k
59
24
90
0

Tyler, My Brother, and Me Ch. 04

I resign myself to losing my virginity to Tyler.

by datura48 in Gay Male 05/03/2018
H
4.61
42.3k
58
5
74

Aunt Anjali Ch. 01

Aunt seduces a nephew. Nephew seduces an aunt. You decide.

by prahaar2006 in Incest/Taboo 12/28/2002
4.04
342.9k
58
9
80

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

Mary, The Vicar's Faithful Wife

Mary obliges to sin on behalf of her daughter.

by Libertine in Mature 02/20/2009
4.48
177.6k
57
11
70
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

Sara

Young man and his friend's mom.

by arjunsharma in Mature 03/15/2013
4.44
235.7k
55
15
87

Mom's Panties

His road to happiness began with Mom's panties.

by highpowererot in First Time 04/07/2023
H
4.57
37.6k
55
8
97

Discovering Sex

First sister, then a lot more.

by ainu2 in Incest/Taboo 04/24/2008
4.47
225.7k
54
14
77
0

Natalie

Two 18-year-olds lose their virginity together.

by CheeseSandwich222 in First Time 01/02/2020
H
4.61
70.8k
53
14
75
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

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 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

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

Aunt's Boy Toy Ch. 01

Cougar's feast.

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

Oh Mrs Scott

Terry's surprise first time and a bigger surprise, who.

by Harvey_32 in Incest/Taboo 05/12/2018
4.44
66.7k
51
6
72
0

Tiki Trouble

Colin makes an unusual purchase.

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

Fucking My Aunt

Younger guy fucks his mature aunt.

by b0ner in Incest/Taboo 07/12/2008
4.09
741.6k
50
31
80
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

Losing My V: A Bisexual Awakening

A story of how I lost my virginity in a bisexual threesome.

by RichRR in Group Sex 09/25/2021
H
4.77
42.3k
50
8
86
0

The Fallen Ch. 04

Erykah tries new things and gets a surprise or two.

by RubyStorm in Sci-Fi & Fantasy 07/15/2016
H
4.88
18.3k
49
33
54

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

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

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

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

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

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

Ali's Art Ch. 03

Tom finally gets laid, but with an unexpected partner.

by harding in Novels and Novellas 07/01/2010
H
4.83
61.5k
45
14
54

Mother of My Best Friend

Story of seduction by a mature lady.

by kinkydreams667 in First Time 12/19/2011
3.76
281.2k
45
12
67

Mrs. Anderson and the Boy Next Door Ch. 03

Mrs. Anderson and Nick enjoy risky pleasure.

by DeliciousD45 in First Time 11/17/2017
H
4.6
63.9k
43
6
59

Forbidden Fruit Ch. 06-10

Hunky quarterback trying to score with his cheerleader sister.

by GoldRogue in Incest/Taboo 01/29/2020
4.49
35.9k
43
1
63

Eighteen

Virgins finally do it.

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

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

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

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

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

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

Here's to you Mrs. Robinson Pt. 01

My Mother's Friend.

by BenLong in First Time 10/16/2021
H
4.61
41.8k
40
9
71

Anthony's 18th Birthday

A crime boss gifts his son a stunning present.

by Bazzza in First Time 02/03/2006
H
4.61
171.4k
40
10
54
0

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

Mature Afternoon Delight

Young man gives cherry to mature aunt.

by Rapide in Incest/Taboo 01/08/2009
4.11
250.8k
40
6
63
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

The Slow Bowler

19-year-old virgin cricketer seduces school friend's mum.

by mangrove jack in First Time 06/29/2006
H
4.65
166.6k
40
0
56
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

Mrs. Anderson and the Boy Next Door Ch. 04

Lola helps Kate with a sexual favor. Kate makes a confession.

by DeliciousD45 in First Time 12/15/2017
H
4.61
41.4k
40
6
54

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
67
0

When Red is Golden

Sparks fly when shy boy meets shy girl in college.

by techsan in Romance 11/03/2006
H
4.71
68.9k
40
14
64
0

Fat Bottomed . . . Girls?

How a callow youth is deflowered by a larger lady.

by The Mouse in First Time 02/22/2019
H
4.66
58.8k
40
1
58
0

To Love and Be Loved Ch. 01

Seduction by an older woman leads to love.

by NerdySex in Novels and Novellas 11/15/2016
H
4.59
28.3k
39
2
58

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

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

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

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

College Moving-In Day Ch. 02

His roommate's mom comes back for Parent's Day.

by sb69 in Mature 03/13/2005
4.49
189.5k
39
9
48

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

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

Marian and Ryan

He goes from mowing her lawn to plowing her pussy.

by Boxlicker101 in First Time 04/12/2006
H
4.52
228.4k
38
3
59

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

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 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

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

Female Orgasms

A young man learns patience from his hot dominant neighbor

by Larysa in BDSM 09/07/2013
H
4.55
72.6k
37
9
54
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

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

Chad and Blaine Ch. 07

They got their happily ever after.

by Baby789 in Gay Male 01/31/2013
H
4.71
18.4k
36
10
38

Sexual Education

Nurses know it all.

by shambles in First Time 04/27/2007
4.46
201.1k
36
3
52
0

The Thunderstorm

Inclement weather leads to an unexpected encounter.

by thezinger in First Time 04/10/2011
H
4.68
70.2k
36
11
50
0

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

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

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

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

My Adoptive Family are Succubae Ch. 02

John learns the truth.

by HumbleIncubus in NonHuman 12/22/2022
H
4.62
16.5k
35
14
62

Taming the Tsarevich Ch. 01-02

A whipping boy returns years later to tame his former master.

by Nameless_Rose in Gay Male 07/14/2009
H
4.73
44.8k
35
13
43
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

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

Afternoon Lessons

Meredith deflowers her next-door neighbor.

by Charles900 in First Time 12/31/2022
H
4.59
45.1k
34
8
59
0

In The Tutelage Of Ms. Kline

Ms. Kline has a special summer job for Kevin.

by LustyQuill in First Time 12/12/2016
4.38
54.2k
34
4
45
0

The Seduction of Emma

A couple finds themselves and explores their relationship.

by RichardLeslie in First Time 04/18/2018
H
4.69
38.5k
34
9
46
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

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

Streaks

He forgot the windows were being washed today.

by CuriousThroat2 in Gay Male 11/26/2013
H
4.54
58.1k
33
6
43
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

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 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

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
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