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‘his first time’ stories

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Sunbathing - Nude

Older woman teaches virgin guy about sex.

by joan658 in Mature 12/16/2007
H
4.62
212k
67
11
94
0

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
103
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
121.2k
39
9
51

Brotherly Love

It was the first time for both brother & sister.

by countrycal in Incest/Taboo 02/25/2006
H
4.62
241.7k
59
24
90
0

The Girl Next Door

Best friends consummate their longheld friendship.

by Martins in First Time 12/07/2008
H
4.62
223.1k
78
12
118
0

Doing Mrs. Hanson's Yard

...and doing Mrs. Hanson!

by susurrus in Mature 09/03/2009
H
4.62
261.4k
68
6
106
0

Memories of Nora

Recollections of a sexy older woman.

by mussorgsky in First Time 11/08/2006
H
4.62
66.4k
7
2
10
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
134.8k
104
5
147

My Adoptive Family are Succubae Ch. 02

John learns the truth.

by HumbleIncubus in NonHuman 12/22/2022
H
4.62
16.7k
35
14
61

Lucky

Lucky has a bad night, till she finds a champion.

by jackell99 in Erotic Couplings 07/02/2008
H
4.62
23.2k
8
3
12
0

Lisa’s Summer Vacation Ch. 02

Lisa's second assignment.

by Reefkeeper in First Time 07/15/2009
H
4.62
42.1k
6
5
13

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
41.6k
40
6
54

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
32.4k
60
8
99

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
42.4k
58
5
74

First Time (with an Older Woman)

His first time is with an older, hairy woman.

by j_zep2001 in Mature 08/29/2008
H
4.61
232.5k
86
32
117
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
159.7k
161
22
213

Lawnmower Boy Ch. 01

A young man's education begins.

by DeepBlueC in First Time 10/08/2007
H
4.61
241.9k
115
0
159

High School Harem Ch. 01

Horny teens explore their sexuality and each other.

by fittucker87 in Group Sex 03/21/2009
H
4.61
1M
1.4k
24
1.9k

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

Here's to you Mrs. Robinson Pt. 01

My Mother's Friend.

by BenLong in First Time 10/16/2021
H
4.61
42k
41
9
72

Natalie

Two 18-year-olds lose their virginity together.

by CheeseSandwich222 in First Time 01/02/2020
H
4.61
71.1k
53
14
75
0

Homecoming

Rita meets him as he gets off the bus.

by geronimo_appleby in First Time 08/26/2013
H
4.6
73.2k
21
9
36
0

Jono's Journey Home Ch. 01

An Arab orphan returns home.

by Shy_Bottom69 in Gay Male 04/19/2017
H
4.6
20.6k
25
3
42

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

Tommy's Graduation Present

The best grad present a guy can receive.

by Tender86 in First Time 05/28/2007
H
4.6
133.3k
29
4
40
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
125.4k
75
16
102
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
93.3k
93
17
125

Night Swim

A nude swim at the reservoir

by Silvermouse in First Time 01/20/2011
H
4.6
119.2k
33
11
54
0

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
64.2k
43
6
59

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

Lost Innocence

Every one has a story. This one is mine.

by Many Feathers in First Time 05/02/2008
H
4.6
110.5k
22
12
29
0

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
103.6k
35
9
49

The New Slave Ch. 01

Daniel gets abducted.

by martin_x59 in Gay Male 08/09/2011
H
4.59
182.9k
200
21
263

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
122.2k
93
15
124
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

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
59

First Cum Swallow

Swallowed my first load.

by garyr43 in Gay Male 06/14/2018
H
4.59
239.7k
61
108
81
0

A Mother's Love Ch. 01

Mom helps Elliot overcome his sexual problems.

by michaelg1 in Incest/Taboo 06/03/2022
H
4.59
59.7k
98
4
182

Afternoon Lessons

Meredith deflowers her next-door neighbor.

by Charles900 in First Time 12/31/2022
H
4.59
45.3k
34
8
59
0

Playing With My Sister Ch. 01

Big sister takes her brother's cherry.

by KenJames in Incest/Taboo 11/17/2005
H
4.58
422.3k
296
15
442

The Theater Student

Young man is seduced by an eccentric girl next door.

by CAP811 in Humor & Satire 03/17/2007
H
4.58
44.2k
18
3
21
0

Mom's Panties

His road to happiness began with Mom's panties.

by highpowererot in First Time 04/07/2023
H
4.58
40.4k
62
8
108

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
83.6k
10
5
27
0

The End of Summer

It was their first time. It changed them.

by AutumnWriter in First Time 05/01/2006
H
4.58
72k
14
9
18
0

Little Brother's Lesson

Cindy teaches her shy brother about how to treat a girl.

by InBrightestDay in Incest/Taboo 06/12/2012
H
4.57
334.1k
291
51
401
0

Lady Next Door

Young man gets lessons from the lady next door.

by LynnGKS in First Time 02/13/2010
H
4.57
293k
66
15
100

Rose: My First

An older woman teaches 18-year-old virgin.

by hjames1950 in First Time 05/13/2006
H
4.57
162.5k
18
6
26
0

How Did You Learn To Love Fellatio? Ch. 04

Mark tells how it starts with Peggy, concluded in chapter 5.

by leBonhomme in First Time 08/03/2014
H
4.57
21.1k
5
1
5

Jimmy meets Miss Victoria

A young man is introduced to sex and femdom.

by Rocytman in First Time 12/13/2008
H
4.57
139.3k
83
9
124

Lessons at Poolside

I introduce a young man to the pleasures of sex.

by WayneGibbous in Mature 09/20/2010
H
4.57
136k
35
1
60
0

First Virgin Boy

He was my first declared “Virgin Boy” - Start of a fetish?

by April602 in First Time 04/04/2024
H
4.56
10.4k
5
12
14
0

Our Last Party

Everyone was young once!

by YDB95 in Erotic Couplings 08/21/2017
H
4.56
19.6k
2
1
7
0

August Rain

Peter loses his virginity during a summer rainstorm.

by The_Unicorn in First Time 08/25/2009
H
4.56
120.7k
37
10
67
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
143k
32
0
45
0

Freshman Virgin

Gary's first time.

by MistressMerry in First Time 09/12/2007
H
4.56
78.8k
11
5
14
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
211.6k
61
0
85
0

Girlfriend's Son Ch. 03

Son loses his virginity.

by lonesomejones in Gay Male 05/17/2010
H
4.55
124.8k
31
4
36

Home Delivery

Beautiful MILF was my first lover.

by Swilly in First Time 05/20/2013
H
4.55
127.8k
41
9
54
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
136.9k
41
7
65

Female Orgasms

A young man learns patience from his hot dominant neighbor

by Larysa in BDSM 09/07/2013
H
4.55
72.7k
37
9
54
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
154.1k
30
6
40
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
114.4k
23
6
37

Cum Hungry

Virgin guy has wild sex with three women.

by Grandflasher C. in Group Sex 04/29/2002
H
4.55
290.9k
169
0
254
0

In Uniform... In Mom

He takes father's & grandfather's place inside his mom.

by scouries in Incest/Taboo 08/26/2008
H
4.55
425.6k
340
79
508
0

Mrs Lamb

She wears silk scarves and is his fantasy woman.

by oggbashan in Fetish 09/11/2006
H
4.54
63.4k
17
8
28
0

Loved by Late Mom's Dear Friend

Brad loses virginity to late mom's friend.

by Oldlover69 in Mature 11/06/2006
H
4.54
376.4k
104
0
139
0

Jessica Loses Her Virginity

A crossdresser's coming of age.

by DCJessicaCD in Transgender & Crossdressers 04/16/2007
H
4.54
120k
29
13
32
0

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
100.6k
110
26
149
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
65k
24
7
32
0

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

Sexual Seduction My Way Ch. 06

Sex education classes by Aunty

by feelsgood in Mature 09/25/2008
H
4.53
68.5k
11
0
15

How Hannah and I Got Together

Two friends explore each other's sexuality.

by sex4every1 in First Time 01/12/2011
H
4.53
141.8k
96
16
133

Best Summer Ever

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

by DG Hear in First Time 08/25/2011
H
4.53
132.5k
34
38
57
0

Sexual Beginnings Ch. 03

Sabrina and Sam have new adventures.

by allen1960 in Mature 04/24/2008
H
4.53
21.9k
1
2
2

Older Women at the Farm Store

An older customer "teaches" a young counter clerk.

by maninconn in Mature 11/07/2008
H
4.53
138.1k
40
0
60
0

Life's Eternal Struggle Ch. 01

He finds woman of his dreams.

by smj54ap in First Time 03/18/2006
H
4.52
36.5k
4
5
7

Marian and Ryan

He goes from mowing her lawn to plowing her pussy.

by Boxlicker101 in First Time 04/12/2006
H
4.52
228.5k
38
3
60

Shauna Ch. 01

Shauna takes her 18-year-old son as lover.

by mostanything in Incest/Taboo 12/20/2003
H
4.52
299.1k
107
5
153

One of These Nights

Virgin gets over his sexual inhibitions, with help.

by Eagle1 in Group Sex 03/20/2001
H
4.52
58.1k
5
1
8
0

The Science of Sex Ch. 01

Student and friend find a fun way to experiment.

by shadywriter in First Time 01/12/2008
H
4.52
59.9k
16
2
24
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 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

Mrs. Claus! Ch. 01

A suprise visit from Mrs. Claus.

by royhoffman in Incest/Taboo 11/15/2007
H
4.52
271.2k
209
17
319

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
133.5k
100
16
120

The Physics of Attraction

Nerd loses his virginity at the library.

by IshtarsMoon in First Time 02/27/2008
H
4.52
80.4k
52
13
76
0

The Markenton Boy Ch. 01

An upper class woman falls in love with a stable boy.

by devinn in First Time 08/10/2012
H
4.52
38.8k
17
3
24
0

Auntie Amanda Receives a Gift

Nephew leaves cum in her panty drawer.

by AuntAmanda in Incest/Taboo 08/16/2010
H
4.51
189.3k
107
17
147
0

Robbie Loses His Virginity

Robbie's first time with older guy.

by robbie_krt in Gay Male 01/04/2022
H
4.51
73.3k
64
19
95
0

Levi Ch. 03: The Loved Boy

Levi finds a boyfriend. Nathan and the good Doctor continue.

by jdylanh9 in Gay Male 12/28/2011
H
4.51
17k
10
5
10

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
139.7k
52
18
69
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

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
80.2k
112
32
208
0

Their Best Homework Session

College couple share a special first time.

by JammyJay in First Time 02/23/2006
H
4.51
76.6k
14
3
24

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
95.2k
50
0
61
0

Cross Country Ch. 02

Lisa pops Sebastian's cherry in the dunes.

by VentureV in Incest/Taboo 11/06/2009
H
4.5
100.6k
20
5
29

Employee Relations

Cara and Matt make the complications work for them.

by Angelindisguise223x in Romance 01/29/2006
H
4.5
23k
4
2
7

The Neighbour

A young man's first sexual adventure.

by mercer78 in First Time 09/17/2013
H
4.5
99k
31
8
37
0

Yolanda goes to Jiffy Lube

After fixing her car, she takes his virginity.

by kholoblicin in First Time 01/29/2014
H
4.5
43.2k
15
3
21
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
154.5k
65
8
98
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
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