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‘his first time’ stories

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his first time 

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Robbie Loses His Virginity

Robbie's first time with older guy.

by robbie_krt in Gay Male 01/04/2022
H
4.51
72.7k
64
19
95
0

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

Amanda's First Time

When Matt's parents go out of town they have birthday sex.

by quietlycrazy in First Time 05/01/2013
4.11
72.4k
13
6
20
0

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

The End of Summer

It was their first time. It changed them.

by AutumnWriter in First Time 05/01/2006
H
4.58
71.9k
14
9
18
0

True Love

Brian loves the girl of his dreams- his best friend.

by toast37 in First Time 03/18/2010
3.2
71.3k
10
36
11
0

Costumes, Drinks, and My Foreskin

Close friend takes his virginity at a party.

by TakeEight in First Time 06/16/2007
3.99
71.2k
1
5
5
0

Richie's First Time

Art and sex on a hot summer's day.

by ltmepoz4u in First Time 04/16/2007
4.45
70.8k
4
2
6
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

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

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

Studying with Sarah

A study session turns into something a little more.

by Jimmy45 in First Time 08/24/2007
3.88
69.7k
10
0
11
0

For the First Time

A young man in good hands.

by RufusLeMont in First Time 04/04/2011
4.26
69.3k
5
4
9
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

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
14

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

Lessons from Days Gone By Ch. 01

College bound guy meets older woman.

by nosebone in First Time 03/16/2018
H
4.79
67.8k
105
20
150

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

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

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
29
7
31

Valuable Commodities

Well, sometimes you just get lucky! Don't fight it.

by Sailor1 in First Time 02/21/2006
H
4.74
67.4k
4
6
9
0

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

Deflowered

She deflowers her attractive friend.

by TrillianSorbet in First Time 12/26/2008
3.82
66.6k
2
0
5
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

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

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

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

Convenience Store Encounter

Joe's luck is about to change while shopping.

by StoneyHill in First Time 08/21/2010
3.9
66.2k
5
3
7
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 Tutor

Young woman is hired to teach a young man about life.

by midnightfalcon in First Time 01/26/2009
4.48
65.7k
17
2
30
0

Virgin Blood

First time for both of these lovers.

by Acal in First Time 03/27/2009
3.95
65.6k
9
1
12
0

Big Virgins

Big man loses virginity to large & sexy girlfriend.

by Samuelx in First Time 09/26/2006
3.56
65.4k
5
0
6
0

Tokyo Health Spa

Virgin guy seeks relief at a sketch massage parlor.

by TrueMouse in First Time 09/25/2006
0
65.3k
16
5
21
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

Joyce

Coming of Age.

by Markdown72 in Incest/Taboo 11/25/2012
3.84
65k
5
1
9

It Was One Elf of a Night

Santa loves his little helper.

by BabyJamesBoy in Gay Male 11/21/2007
4.08
65k
6
1
9
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

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

The Governess Ch. 02

Miss Pauline introduces herself to Jack the Stable Boy.

by Shamrockk in Lesbian Sex 08/13/2011
4.43
64.7k
14
4
21

When Did It All Start?

A-level students explore sex for the first time.

by LucyCanyon in First Time 05/06/2008
3.93
64.4k
8
0
11
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
63.9k
43
6
59

Learning by the Pool

Young man remembers his first time.

by Laid71 in First Time 05/11/2012
4.38
63.6k
7
1
11
0

Nature's Calling

Ethan and Kieran find an everlasting love in the outdoors.

by VampGirl1991 in Gay Male 04/04/2012
H
4.75
63.5k
133
40
148
0

Mrs Lamb

She wears silk scarves and is his fantasy woman.

by oggbashan in Fetish 09/11/2006
H
4.54
63.3k
16
8
26
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

College Try

Romantic first time - for both?

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

The Cowboy

Call for help results in loss of his virginity.

by wyvernwand in First Time 04/01/2013
4.44
63.1k
12
7
18

It is Snowing

A sailor on liberty around Christmas in Connecticut.

by Alpheratz in First Time 02/25/2006
H
4.67
62.7k
6
14
12
0

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

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

Eighteen Holes Ch. 03

On the last day of summer, it gets even hotter.

by lusthammer in First Time 04/10/2010
4.44
62.2k
5
1
7

The Box

His first time.

by lsa3 in First Time 08/24/2012
0
61.7k
13
2
17
0

Big Easy Lessons Ch. 02

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

by aspiringDOM in First Time 01/14/2011
4.09
61.5k
3
3
5

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

Jessica

Aunt introduces me to Jessica.

by historycup in First Time 10/15/2012
3.86
61.4k
12
1
15

The Domestic Plumber

A plumber's apprentice is initiated.

by Moondrift in First Time 08/03/2008
4.07
61.3k
6
5
11
0

The First Time

18-year-olds give each other their virginity.

by Chaton in First Time 04/13/2007
3.99
61.1k
10
2
13
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

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

A Gentle Awakening Ch. 02

They consummate the relationship.

by julia so sweet in First Time 11/07/2007
4.19
60.6k
4
4
4

Charlie's Way

Charlie's a girl with a lot of surprises.

by Curious_Chick007 in First Time 08/01/2008
4.13
60.4k
12
3
20
0

Losing It At The Pool Ch. 01

How I lost my virginity.

by heyjay1983 in First Time 04/30/2013
4.06
60.3k
7
3
9
0

Jesse

Young male/older male first time oral anal.

by xdress2nite in Gay Male 08/23/2013
4.17
60.1k
10
4
11
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
15
2
23
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
59.6k
98
4
181

Being Caught Isn't So Bad

Young man's surprising adventure in voyeurism.

by night41 in Exhibitionist & Voyeur 09/08/2006
4.12
59k
4
1
9
0

Big Easy Lessons Ch. 03

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

by aspiringDOM in First Time 01/15/2011
4.18
58.9k
3
3
5

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

Through Changed Eyes

His high school crush's older sister becomes intrigued.

by ableoneable in First Time 07/14/2008
4.15
58.3k
12
1
18

Virgin Departure

Seduced, but not really abandoned.

by R. Richard in First Time 10/26/2003
4.14
58.3k
1
0
3
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

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

Swing Time Ch. 02

Two virgins lose it.

by l8bloom in First Time 12/08/2007
4.2
58k
2
5
2

Nurse's Aide

A disabled guy finally loses his virginity.

by WHEELLOVE in First Time 12/08/2012
4.15
57.6k
10
8
17
0

My New Girl

The tentative first time for two lovers.

by Gizzmotick in First Time 06/13/2006
4.28
57.4k
7
3
10
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

Heartbeat

Young lovers discover the joy of sex.

by bassbelly in First Time 05/22/2009
3.84
57.1k
3
3
5
0

Surprise Encounter

Girl is surprised he is a virgin.

by Ladyhespa in First Time 07/09/2010
4.46
57k
4
3
6

Simple Simon

Sweet story of a geek finding his dream girl.

by TheDarkestPlace in First Time 03/31/2010
4.44
56.6k
17
2
26
0

Summer Job Leads To More

Fixing houses with twin sister leads to awkward situation.

by redfox40 in Incest/Taboo 04/23/2022
4.4
55.9k
83
9
147

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

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
55.1k
5
1
7

Fireside First

College sweethearts lose virginity.

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

Posh James. First Virgin Guy

For once a guy that kept his word.

by alexcarr in Gay Male 06/29/2012
4.27
54.7k
4
3
4
0

Kerry

His first time was not expected.

by ThomasMagica in First Time 05/18/2008
4.03
54.5k
1
3
3
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

First Timers Sara and Billy

High school crush comes to fruition in college pool.

by Mistrisa in First Time 09/19/2010
3.79
54.1k
3
1
4
0

Fiona

Jeremy comforts Fiona when she needs it most.

by Nehkara in First Time 12/29/2010
4.41
53.7k
12
4
21
0

Cliffhanger

The Earth moves as Barry enjoys his first slice of Heaven.

by sirhugs in First Time 04/11/2006
4.03
53.6k
3
10
8
0

College Chancellor and Male Virgin

University visit leads to virgin guy's one-night-stand.

by stoneypoint in First Time 10/28/2006
3.81
53.4k
9
2
14
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

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

My First

Young couple attend a dude ranch.

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

Corky and Billie Ch. 01

Blind student meets student nurse with a plan.

by corcyra in First Time 10/04/2006
4.42
52.1k
5
1
9

Tim's Greatest Desire

Johnny shares his girlfriend with his best friend.

by Dream Seeker in Group Sex 05/13/2006
4.02
51.7k
16
3
24
0

The Field Trip

The field trip gets interesting for Sheli and Mr. Timson

by nancyallen in First Time 12/11/2009
3.82
51.7k
8
4
12
0

Cookie was My First

New lessons in the ways of sex with an older woman.

by Toolmo in First Time 07/25/2008
4.2
51.4k
11
6
14
0

The Unexpected Loss of Virginity

My girlfriend and the weird girl from class help me out.

by frankland in First Time 03/20/2016
3.71
50.9k
16
6
25
0

One To Remember

18-year-old guy finally gets a year to remember.

by MonkeyMan1988 in First Time 08/19/2006
4.18
50.5k
4
2
8
0
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