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‘his first time’ stories

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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
138.9k
52
17
69
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
65.9k
31
2
43
0

A Hand Down His Shorts

Widowed lady loves the delivery boy.

by VeryDirtyMind in Mature 09/12/2016
4.33
131.3k
69
11
86
0

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

The Fallen Ch. 04

Erykah tries new things and gets a surprise or two.

by RubyStorm in Sci-Fi & Fantasy 07/15/2016
H
4.89
18.2k
49
32
54

Best Sex Ever

Sex at the beach with a stranger.

by blackjack17 in Erotic Couplings 06/09/2016
2.87
29.4k
3
2
9
0

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
141.1k
118
9
187
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
50.8k
15
6
24
0

Practicum

You can only learn so much in the classroom...

by YDB95 in First Time 03/01/2016
H
4.69
64.9k
23
1
44
0

Teacher Becomes The Student

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

by TheOxRocks in First Time 02/11/2016
4.22
55.5k
41
1
52
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
32.3k
24
2
34

Gentle First Time

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

by littlekitten738 in Audio 09/22/2015
4.41
113.7k
34
16
43
0

The Summer ABCs

She taught him the basics, they took it from there.

by 49greg in First Time 08/22/2014
H
4.52
78.1k
23
4
32
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

College Try

Romantic first time - for both?

by Sandman8314 in First Time 08/01/2014
4.34
63.1k
13
5
24
0

Beware the Quiet One

Two ugly ducklings are better than one!

by YDB95 in First Time 06/20/2014
H
4.69
82.3k
28
18
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
154.2k
141
11
197

Something Lost

It should have been a gift, but it left him troubled.

by MSTarot in Audio 02/26/2014
3.83
29.8k
0
3
00

New Adventures

A tale of first time, masturbation, voyeur.

by Starkraven in Exhibitionist & Voyeur 02/19/2014
4.47
52.2k
19
4
29

Weekend Antics

A young man and woman have an enjoyable weekend alone.

by storywriter123 in First Time 02/13/2014
3.89
38.8k
3
3
6
0

My Sexual Awakening

A college couple's slow discovery of sex.

by jr0berts in First Time 02/07/2014
4.13
42.1k
5
1
12
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
43.1k
15
3
21
0

The Birthday Blowjob

Girlfriend gives him the ultimate gift.

by A_Non_A_Moose in Erotic Couplings 01/24/2014
4.3
88.2k
38
3
48
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
72.2k
31
7
34
0

Seduced by Innocence

A psychopathic woman seduces a virgin and brags about it.

by Mardell in Mature 12/25/2013
3.66
57.2k
28
4
38
0

Alice Ch. 05

Alice begins teaching Charlie.

by yesterdays in Incest/Taboo 12/19/2013
4.49
46.6k
19
1
27

No Regrets Ch. 11

Ryan's Story – Liberation.

by martin_x59 in Gay Male 12/03/2013
H
4.63
14k
12
7
13

Streaks

He forgot the windows were being washed today.

by CuriousThroat2 in Gay Male 11/26/2013
H
4.54
58k
33
6
43
0

Grand Island

A train ride to a new world and a new life.

by YDB95 in Romance 11/25/2013
HW
4.8
107.6k
72
38
95
0

The Summer of '47

First Time: A "Voluntary Rape".

by OldAndNew in Gay Male 11/24/2013
4.13
25k
6
4
8
0

Christmas Party Memories

Hotties convince him to recall when he lost his virginity.

by m_storyman_x in Group Sex 11/21/2013
H
4.73
93.4k
83
10
108
0

Innocent

An innocent young couple explore.

by Ashson in First Time 11/14/2013
4.25
90.8k
25
5
31
0

First Resort

A young man comes of age with an older woman.

by byronbert in First Time 10/11/2013
4.43
114.7k
29
9
40
0

Karen's First Time

A shy virgin is aroused by a voyeuristic experience.

by tony090909 in First Time 10/07/2013
3.86
82.8k
10
2
18
0

Rough Velvet: Alternative

Frustrations of a gay virgin man after hours.

by Purple_Raven in Gay Male 10/07/2013
4.12
23k
1
2
1
0

No Regrets Ch. 03

Tommy's Story – Another Chance.

by martin_x59 in Gay Male 10/05/2013
H
4.64
15.2k
10
2
10

The Neighbour

A young man's first sexual adventure.

by mercer78 in First Time 09/17/2013
H
4.5
98.8k
31
8
36
0

Jared Ch. 01

Jared meets a man from the Internet how will it end?

by andrew1990 in Gay Male 09/13/2013
3.85
33.4k
11
2
14

Female Orgasms

A young man learns patience from his hot dominant neighbor

by Larysa in BDSM 09/07/2013
H
4.55
72.5k
37
9
54
0

New Teacher Bad Boy

Bad boys helps new teacher survive at rough school.

by braindump in First Time 08/28/2013
4.26
108.6k
65
7
89
0

Homecoming

Rita meets him as he gets off the bus.

by geronimo_appleby in First Time 08/26/2013
H
4.6
73k
21
9
35
0

Jesse

Young male/older male first time oral anal.

by xdress2nite in Gay Male 08/23/2013
4.17
60k
10
4
11
0

The Good Girl

Two virgins find love.

by SlamDuncan in First Time 08/02/2013
H
4.68
105.9k
76
17
96
0

My Sister's Friends

A young man with CP finds love through his sister's friends.

by Callicious in First Time 07/01/2013
H
4.63
202.6k
150
11
203

Some Help From Mom

Son gets a helping hand from his mother.

by carson2658 in Incest/Taboo 06/05/2013
4.13
165.8k
61
11
76
0

The Menu

Jeremy's sexuality is awakened.

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

Black Teacher

Lucky guy loses his virginity to his ebony English teacher.

by RandomStorywriter01904 in First Time 05/26/2013
4.25
132.1k
56
5
67
0

Home Delivery

Beautiful MILF was my first lover.

by Swilly in First Time 05/20/2013
H
4.55
127.5k
41
9
53
0

Family Plays Together Ch. 01

Dad and Mom seduce their 18-year-old son into having bisex.

by tonyl65 in Incest/Taboo 05/20/2013
4.19
349.1k
230
10
358

Their First Toys Ch. 06

They find him! A virgin! But he won't be after this day!

by leBonhomme in First Time 05/15/2013
3.86
22.4k
5
0
6

The Lesson

Young man gets seduced by 18-year-old for his first time.

by DelightfulNikki in First Time 05/13/2013
4.21
63.2k
20
5
27
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
72.3k
13
6
20
0

Good Boy Ch. 02

She takes him...

by Maddiegirl in First Time 05/01/2013
4.14
44.7k
3
3
3

Losing It At The Pool Ch. 01

How I lost my virginity.

by heyjay1983 in First Time 04/30/2013
4.06
60.2k
7
3
9
0

Smithson Ch. 01: The Forge

The son of a blacksmith must find his own path in the world.

by Sinisterinfant in Sci-Fi & Fantasy 04/25/2013
H
4.64
30.6k
22
10
36

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

The Cowboy

Call for help results in loss of his virginity.

by wyvernwand in First Time 04/01/2013
4.44
63k
12
7
17

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
4.51
133.2k
99
16
116

Rent is Due

A college freshman deals with a very exacting landlord.

by TwoWorldsTX in First Time 03/19/2013
3.81
88.2k
4
2
14
0

My Teacher Ms. Miller Ch. 03

Tony takes his teacher to prom. They play dressup.

by edstevens94301 in First Time 03/17/2013
H
4.63
103.7k
93
4
107

Sara

Young man and his friend's mom.

by arjunsharma in Mature 03/15/2013
4.44
232.3k
51
15
82
0

First-Timer

Teacher takes her young student's virginity.

by MaryGirard in Mature 03/14/2013
4.15
170.9k
19
6
27
0

Grandma was a Teacher

A grandma/grandson story.

by Momstheboss in Incest/Taboo 03/07/2013
4.44
254.4k
101
15
151
0

Aunt Helen

A chance encounter turns to extreme sexual delight.

by TropicalHeat in Mature 03/02/2013
4.41
100.3k
30
4
37
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

Raven

A shy young man gets a lesson in loving from big sister.

by BrettJ in Incest/Taboo 02/06/2013
4.48
167.9k
131
31
185

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
122k
93
15
122
0

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

Chad and Blaine Ch. 06

Will Chad and Blaine get their happily ever after?

by Baby789 in Gay Male 01/31/2013
H
4.77
16.7k
27
0
30

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
64.7k
26
13
42
0

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
83.4k
10
5
26
0

Fireside First

College sweethearts lose virginity.

by On_Impulse in First Time 01/13/2013
4.3
54.7k
4
3
6
0

My First

Young couple attend a dude ranch.

by Ashson in First Time 12/24/2012
4.21
52.7k
2
2
9
0

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

Friend's Hot Mom

He loses his virginity to his friend's hot mother.

by nobigwillie in First Time 12/06/2012
4.14
350.9k
75
14
96
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

Joyce

Coming of Age.

by Markdown72 in Incest/Taboo 11/25/2012
3.83
64.9k
5
1
8

Love On The Hill

He has a favorite pair of jeans locked up, unwashed!

by romeoindian in First Time 11/20/2012
3.72
16.5k
3
0
4
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
64.8k
23
7
30
0

Jessica

Aunt introduces me to Jessica.

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

Losing It

Daryl feels the pressure of virginity at 18.

by Storiest in First Time 10/10/2012
3.19
44.2k
2
2
5
0

College Fun: Alexis

Some fun in Decatur, and a surprise confession!

by Arraiga in First Time 09/27/2012
3.96
22.9k
1
0
1

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
67.5k
29
7
31

The Box

His first time.

by lsa3 in First Time 08/24/2012
0
61.6k
13
2
17
0

High School: Zero to Hero Ch. 00

Prologue: an 18-year-old begins his journey into manhood.

by yoursilentknight in First Time 08/10/2012
H
4.66
218.4k
283
11
380

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
38.7k
17
3
23
0

My First Time

An account of the hookup where I lost my virginity.

by GayGuyJason in Gay Male 08/02/2012
4.17
89.7k
18
4
22
0

Empowered Ch. 02

The party night is eventful.

by failedlove in First Time 07/23/2012
3.68
23.7k
1
3
1

Frankie & Mrs. Young

She gives him a summer he won't soon forget.

by NymphWriter in Mature 07/22/2012
H
4.75
213.4k
87
27
112

The Devil and Me Ch. 01

Tomas makes a deal, but at what cost?

by johnbrown65 in Novels and Novellas 07/19/2012
4
17.3k
16
2
20

His Debut

His initiation, as told to my shrink.

by estragon in Gay Male 07/17/2012
3.54
23.2k
3
3
3
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

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
103.4k
36
9
49

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
149.1k
93
16
156

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

Ethan's First

The pool boy loses his virginity to a college girl.

by alupine in First Time 06/18/2012
4.25
160.3k
84
15
116
0

Overpowered

How an athletic 25-year-old took control of me at age 18.

by oxfofo in Gay Male 06/14/2012
4.07
200.9k
96
16
137
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
333.3k
289
51
398
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
154k
64
8
95
0

Empowered Ch. 01

A story of three friends.

by failedlove in First Time 06/08/2012
3.1
36.5k
4
2
6
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