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‘his first time’ stories

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Senior Seduction

An old friend becomes much, much more.

by pleasureandfun in Mature 09/13/2007
4.49
121.7k
11
7
16
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

Annie's Gift

Annie keeps her Christmas promise to Greg.

by Chiara23 in First Time 07/19/2011
4.49
41.2k
17
6
23
0

Forbidden Fruit Ch. 06-10

Hunky quarterback trying to score with his cheerleader sister.

by GoldRogue in Incest/Taboo 01/29/2020
4.49
36k
44
1
64

Crashed

Two young men and I land on a desert island.

by DawnR in Erotic Couplings 04/04/2024
4.49
13.9k
19
4
33

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
122.6k
46
9
57

Alice Ch. 05

Alice begins teaching Charlie.

by yesterdays in Incest/Taboo 12/19/2013
4.49
46.8k
20
1
30

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
189.6k
40
9
50

Mary, The Vicar's Faithful Wife

Mary obliges to sin on behalf of her daughter.

by Libertine in Mature 02/20/2009
4.48
177.8k
57
11
70
0

The Tutor

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

by midnightfalcon in First Time 01/26/2009
4.48
65.8k
17
2
30
0

Tammy asks Jimmy for Help

Young lovers learn about each other.

by Charles Petersunn in First Time 05/13/2006
4.48
136.7k
10
9
17
0

Tannah The Warrior Pt. 02

Tannah helps a young warrior discover his passion.

by yembrose in Sci-Fi & Fantasy 06/25/2018
4.48
10.4k
8
2
10

Eighteen

Virgins finally do it.

by jasliz in First Time 12/24/2009
4.48
124.8k
43
3
52
0

Discovering Sex

First sister, then a lot more.

by ainu2 in Incest/Taboo 04/24/2008
4.47
225.8k
54
14
77
0

Mrs. Bonnie Ch. 01

Marture woman breaks in a virgin

by sghoul in First Time 02/27/2008
4.47
144.2k
34
10
44
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

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

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

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
150.1k
16
5
23
0

Raven

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

by BrettJ in Incest/Taboo 02/06/2013
4.47
168.2k
132
31
187

A Sixties Story

A shy young man finds a sexual solemate.

by Norfolkboy in First Time 01/02/2009
4.47
45.1k
7
4
8
0

Neighbour Wears Nylons

Set in 1972, a lad spots his neighbour undressing.

by Mag58 in Exhibitionist & Voyeur 01/14/2011
4.47
82.2k
27
15
38
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
149.3k
93
16
159

My MILF

His mother lovingly guides him in the ways of sex.

by darkstar04 in Incest/Taboo 03/18/2006
4.47
239k
60
0
82
0

Robinson Family Ch. 04

Siblings get oral and finally have intercourse.

by siblingspank in Incest/Taboo 08/03/2009
4.46
103.8k
13
12
16

The List Ch. 03

Does the nerd get the cheerleader at homecoming?

by handsomeyetnice in First Time 04/17/2008
4.46
241.3k
70
8
93

Discovering my Step-son

A 51-year-old wife is surprised by her 18-year-old stepson.

by donnamwf50 in Incest/Taboo 06/07/2017
4.46
284.3k
183
24
253

Jake Loves Kate

Their eyes are bright and her skin, electric.

by nomoreundies in First Time 09/06/2008
4.46
33.5k
6
5
7
0

The Peachwillow Chronicles Pt. 01

A male elf and female dwarf meet each other and sparks fly.

by SGLevy in Sci-Fi & Fantasy 01/29/2021
4.46
4.3k
10
1
22

Big

He finally meets his match.

by misterpinch in First Time 09/21/2022
4.46
22.1k
15
4
24
0

Surprise Encounter

Girl is surprised he is a virgin.

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

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
22
0

Sexual Education

Nurses know it all.

by shambles in First Time 04/27/2007
4.46
201.2k
36
3
52
0

The Sober Young Man

Two first-timers give it a go.

by AnAmericanDarling in First Time 05/15/2007
4.46
33.3k
4
2
4
0

The Bus Ride

First sexual contact with another person.

by tightwaddd in Gay Male 04/02/2011
4.46
114k
48
16
55
0

Camp Work Bee

Work Bee at a camp when I was 18 and a virgin.

by Had2write in First Time 01/16/2023
4.46
26k
10
8
24
0

The Divorcee and the Yard Boy

30-year-old divorcee seduces her virginal yard guy.

by SpartanWitherby in Mature 05/06/2009
4.45
168.7k
110
0
147

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
44
0

First Time Lucky

He learns about sex from an expert.

by bibimaybe in Audio 07/07/2009
4.45
83.7k
1
4
5
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
20
0

Spring of Manhood

European boy becomes a man in difficult times.

by gggsss1962 in First Time 03/13/2006
4.45
78.3k
8
4
11
0

Tommy's Lost Virginity

Debbie gives Tommy his heart's desire.

by Tender86 in Mature 09/27/2008
4.45
89.6k
21
4
32
0

Steve & June & I Call on Stacy

Two women cop big, blonde hunk's cherry.

by Boxlicker101 in First Time 11/22/2003
4.45
74.5k
4
1
7
0

Peeking on Mom

Just trying to see mom naked, and wow.

by stevnmom in Incest/Taboo 04/03/2007
4.45
608.4k
161
16
219
0

Richie's First Time

Art and sex on a hot summer's day.

by ltmepoz4u in First Time 04/16/2007
4.45
70.9k
4
2
6
0

Deja Vu

Tom relives losing his virginity - twice over.

by Pussyrider in Erotic Couplings 11/30/2007
4.45
21.1k
0
2
1
0

The Learning Room Ch. 02

His first time is with the Head Cheerleader.

by regularguy13 in First Time 10/08/2010
4.44
97.1k
35
13
47

Grandma was a Teacher

A grandma/grandson story.

by Momstheboss in Incest/Taboo 03/07/2013
4.44
255.1k
101
15
152
0

Our Family's Little Secret Ch. 01

Hot aunt takes her nephew's cherry after a little playtime.

by jehoram in Incest/Taboo 12/20/2020
4.44
90.5k
154
15
303

Simple Simon

Sweet story of a geek finding his dream girl.

by TheDarkestPlace in First Time 03/31/2010
4.44
56.7k
17
2
26
0

Eighteen Holes Ch. 03

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

by lusthammer in First Time 04/10/2010
4.44
62.3k
5
1
7

The Cowboy

Call for help results in loss of his virginity.

by wyvernwand in First Time 04/01/2013
4.44
63.2k
12
7
18

Sara

Young man and his friend's mom.

by arjunsharma in Mature 03/15/2013
4.44
236.1k
57
15
90

Panama Ch. 01: The First Stop

A young sailor and a jaded whore find a night of happiness.

by mikey2much in First Time 06/12/2007
4.44
37.6k
4
3
7

Nikki Ch. 01

She teaches student about sex.

by caprine in First Time 12/07/2007
4.44
94.6k
16
10
24

Oh Mrs Scott

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

by Harvey_32 in Incest/Taboo 05/12/2018
4.44
66.8k
51
6
72
0

The Governess Ch. 02

Miss Pauline introduces herself to Jack the Stable Boy.

by Shamrockk in Lesbian Sex 08/13/2011
4.43
64.8k
14
4
21

All Tits and Bum

It was all his brother Max's fault.

by Bazzza in First Time 11/19/2007
4.43
88.6k
18
3
22
0

Before He Goes

Sister helps her brother before he ships out.

by randyolegoat in Incest/Taboo 09/12/2008
4.43
195.2k
75
11
102

Learning

A young man can learn a lot about sex in three weeks.

by R410a in First Time 04/23/2022
4.43
29k
18
14
34
0

First Resort

A young man comes of age with an older woman.

by byronbert in First Time 10/11/2013
4.43
115k
29
9
40
0

Memoirs of an Old Man Ch. 01

Old man telling about his sexual exploits when he was young.

by goliathslawyer in Incest/Taboo 11/06/2017
4.42
27.1k
20
1
28

A Virgin in Paris

A virgin with a huge Dick losses his virginity in Paris.

by JimmieYoungxxx in First Time 03/07/2024
4.42
14.2k
11
2
16
0

Across the Ages 01: 1979 Peggy

Peggy gives Jack an early Christmas present.

by rothning in First Time 11/30/2019
4.42
16.3k
11
1
15

Summer Intern

BBW milf seduces virgin coworker in office bathroom.

by BartlebyWaylon in Mature 01/20/2011
4.42
94.2k
34
5
47
0

Oh Monique, My Monique

Eric's quest to make his gorgeous friend a lover.

by Venus_Lover in First Time 08/12/2006
4.42
75.5k
6
7
12
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

Jeffrey's First Time

An afternoon with a hooker becomes a lesson in life.

by Anschul in First Time 03/02/2008
4.42
42.3k
8
7
11
0

Corky and Billie Ch. 01

Blind student meets student nurse with a plan.

by corcyra in First Time 10/04/2006
4.42
52.2k
5
1
9

First Time For Us Both

Losing our virginity together.

by EroticExperience69 in First Time 09/18/2017
4.41
66.7k
26
4
37
0

First Time with a Quadriplegic

He loses his virginity to a quadriplegic girl.

by Polysexual in Erotic Couplings 10/14/2007
4.41
90.3k
41
9
51
0

Gentle First Time

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

by littlekitten738 in Audio 09/22/2015
4.41
114.4k
34
16
43
0

Fiona

Jeremy comforts Fiona when she needs it most.

by Nehkara in First Time 12/29/2010
4.41
53.8k
12
4
21
0

The Wager

Older woman takes hunk's cherry.

by No Panty Girl in First Time 11/28/2005
4.41
73.8k
14
6
21
0

Ms. Puckett's: Emily

Send me your boy, I'll send you back a man.

by Collectable in Mature 09/04/2009
4.41
44.6k
9
2
12

Aunt Helen

A chance encounter turns to extreme sexual delight.

by TropicalHeat in Mature 03/02/2013
4.41
100.4k
31
4
39
0

Oh, Jan!

Losing my virginity to my friend's mom.

by JerryDancer in First Time 01/31/2024
4.41
29.3k
21
3
45
0

Crossdressing Brother

Sister catches her brother dressed in her underwear.

by Nomansland69 in Incest/Taboo 08/04/2006
4.41
227.2k
74
3
92

The Best Blow Job Ever

A present for his birthday.

by Anne08 in First Time 03/12/2008
4.41
194.3k
22
16
35
0

My Sister

Brother loses his virginity on his 19th birthday.

by LordHorny in Incest/Taboo 06/13/2008
4.4
163.8k
67
6
99
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
56.1k
83
9
147

Boy Scout Mothers Ch. 01

18 year old scores brownie points with bored boy scout mums

by mangrove jack in Mature 04/06/2003
4.4
652.4k
246
0
315

After Dinner

Part two of 'Wooded Wonderland'.

by missdee1967 in Erotic Couplings 04/28/2006
4.4
10.8k
0
1
00

The Ledge Rocks

18 year-old homo-hetero virgins finally get it.

by lionel_collins in Gay Male 02/12/2007
4.4
50.2k
10
2
14
0

Cousin Laura, My First Love Ch. 01

Hot cousin deflowers a shy guy.

by ForceFull in Incest/Taboo 09/29/2006
4.4
99.6k
29
5
39

Older Women are The Best

18-year-old guy meets two hot MILFs.

by James_Brown in Mature 04/24/2008
4.4
284.4k
68
0
93
0

Claire

My teacher takes my virginity.

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

My Mother, My Teacher Ch. 01

Mother takes her son's virginity.

by Sinful_whispers in Incest/Taboo 01/29/2010
4.4
239.3k
82
6
118

A Touch of Gentleness

A call girl visit.

by whatidreamt in Erotic Couplings 04/10/2009
4.4
27.3k
3
3
9
0

My Teacher Ch. 01

He gets to fuck the hottest teacher in school.

by ZotDragon in Mature 05/25/2007
4.39
303.2k
131
4
173

A Backwoods Tale

Sister gives virgin pussy as birthday present.

by MrJack in Incest/Taboo 08/21/2009
4.39
594.3k
249
30
314
0

Linda Ch. 01

A mature divorcee introduces me to sex.

by ableoneable in First Time 06/13/2010
4.39
96.4k
21
2
28

Summer '82

Remembering his first time.

by Blondefeet in First Time 08/21/2022
4.39
21.6k
8
2
20
0

The Barmaid

His father's girlfriend shows him how it's done.

by geronimo_appleby in First Time 06/05/2012
4.39
91.7k
27
10
42
0

Heather's Desire

A mother arranges her son's deflowering.

by HeathersDesire in First Time 05/20/2008
4.39
120k
30
0
46
0

Amber's Mother

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

by Pindaflash in Mature 03/24/2011
4.39
208.7k
68
9
91
0

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

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
54.3k
34
4
45
0

A Tale of Two Families Ch. 01

Two very close families experience life and love.

by Lauries Husband in Novels and Novellas 09/04/2009
4.38
88.2k
32
2
64

Aunt Jane and His First Time Ch. 02

Happy morning in bed.

by mishkin in Incest/Taboo 07/31/2009
4.38
74.5k
8
4
14
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