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‘first time anal’ stories

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Out of Control

Sometimes a wife needs a good belt.

by AlinaX in Loving Wives 07/20/2018
4.05
91.9k
61
33
115
0

It Started with 2, X-Mas Day

Christmas Day has arrived for the Martins and their guests.

by CB_Grl_Dani in Incest/Taboo 08/07/2022
H
4.73
23.8k
60
13
115

Sarah

Unlocking an older woman's anal desires.

by Lancerlott in Anal 07/18/2021
H
4.74
80.3k
60
17
110
0

Tony and Alicia Celebrate Halloween

Tony is dressed as a hooker, but the real surprise is later

by Ice_Tease in Fetish 10/31/2009
H
4.71
88.1k
59
10
78
0

The Babes on Brentwood

The follow-up to the story 'The Bitches in the Basement'.

by Dancing_Doll in Group Sex 07/27/2011
H
4.54
92.1k
59
8
94
0

Julia, Her First Time

Julia and her Boyfriend go to their first swing.

by Jessie92 in Group Sex 09/11/2021
H
4.59
39k
58
2
101
0

Bar Banged

Husband takes wife out for a night out.

by EaglesNyte in Group Sex 03/21/2013
4.24
108.6k
58
4
74
0

The Call of the Wife Ch. 02

Amy has more new experiences on Saturday night.

by meddlesome in Group Sex 05/14/2011
H
4.63
100.7k
57
0
77

Astarte Ch. 04

Deon has some fun with his power.

by julybear7 in Mind Control 01/07/2012
H
4.69
95.8k
57
11
72

Peter the Neighbour

A young man and his older neighbour.

by davidinlace in Gay Male 10/24/2021
H
4.5
67.5k
56
11
78

Pizza Boy at the Door Ch. 02

Josh discovers what all 'being a delivery boy' can include.

by JKendallDane in Gay Male 12/08/2013
H
4.65
73.6k
55
6
67

Bending the Straight and Narrow Ch. 02

Two men continue to play after college and marriage.

by markindy in Gay Male 06/21/2015
4.45
41.4k
55
4
76

Adventures

"Straight" boys test their limits.

by what_mommy_isnt_telling_you in Gay Male 07/20/2016
H
4.54
88.9k
55
3
84
0

Friends with Benefits Ch. 02

The adventure continues the next day.

by jt123 in Gay Male 12/18/2006
H
4.71
74.7k
54
0
57

Sunday Morning

Jack crosses a line.

by LookingGlassLicker in NonConsent/Reluctance 06/13/2019
4.43
76.2k
54
4
86
0

The Promotion

An anal awakening.

by rioesmarex in Anal 09/06/2007
H
4.58
137.6k
54
7
73
0

Trucker Turned Me Out Pt. 01

Young man meets a trucker online.

by homewreckingpizzaboy in Gay Male 05/15/2019
H
4.58
47.3k
52
8
77
0

First Time for Old Friends

A girl asks her best friend to take her anal virginity.

by sylviamarlowe in Anal 09/02/2013
H
4.56
124.1k
52
12
66
0

Three Toppings

A pizza delivery college girl takes a break with two studs.

by darktigerroar in Anal 10/10/2018
H
4.53
42.5k
51
3
65
0

Reverting to Type

Making a deal with the girlfriends Mother is rewarding.

by byronbert in Mature 02/21/2013
4.47
208.6k
51
21
79

Seduced by a Stepdaughter Ch. 05

Stepdaddy introduces her to anal sex.

by blondesubmission in Incest/Taboo 05/03/2010
4.37
179.5k
51
5
63

From Sweetie to Slutty Ch. 03

Katie is true to her word and then some.

by meddlesome in Group Sex 04/06/2011
H
4.61
136.3k
51
0
68

Chastity is Seductive

She helps her boss seduce his secretary into chastity.

by AlinaX in Fetish 07/27/2016
H
4.62
88.1k
51
22
103

The Imperfect Storm Ch. 02

Asserting his dominance, she loves it

by mojavejoe420 in Incest/Taboo 04/07/2014
H
4.69
65k
50
5
60

My First Anal

Nicole begs for reconciliation by offering her Anal cherry.

by samaelbeckett in Anal 01/21/2014
4.15
142.1k
50
4
64
0

My New Gym Buddy Pt. 03

I give all of myself to him for the first time.

by TheQrious1 in Gay Male 07/17/2021
H
4.61
32.1k
48
8
70

Using The Back Door

Two anal virgins want to do it together.

by Otazel in Anal 03/13/2006
H
4.66
296k
48
10
62
0

A Best Friend's Revealation

Shannon reveals his true feelings for Paul.

by bbw4youngercocks1 in Gay Male 08/01/2007
4.29
93.8k
47
1
54
0

Master Takes Her

Master takes his new virgin for a ride.

by winged_rose in NonConsent/Reluctance 01/04/2006
4.04
159k
47
3
64
0

The Anal Bride

A wife gives her arse to her husband on their wedding night.

by OneLife00 in Anal 04/22/2024
H
4.71
33.5k
45
3
78
0

Victor's New Slave Ch. 03

Slave learns to enjoy a man in her ass.

by fredricka in Anal 01/01/2006
4.49
184.2k
45
3
51

Preserve Whore Pt. 01

Part one of a three-part sequel to Predators.

by majicman21 in Celebrities & Fan Fiction 04/28/2016
H
4.67
25.5k
44
5
65

A Road Trip Fantasy

Doctor and nurse find love on a move across country.

by QuietDog in Novels and Novellas 02/11/2018
H
4.84
28.6k
44
7
60

My Wife Now Loves Big Dicks Pt. 02

Getting my wife a big one and I get something special too.

by dudeindallas in Loving Wives 10/31/2016
3.95
81.4k
43
22
56

The Blue Life Ch. 05: After Jillian

Revelations about Jillian, plus spanking & butt-fucking Mom.

by GrantLeeStone in Incest/Taboo 01/18/2015
H
4.66
41.6k
42
3
54

Angel in Heat

A woman in a sauna is seduced by three strange men.

by cbsinclair in Group Sex 01/28/2016
4.36
60.6k
42
6
55
0

Cock Sucking Club Ch. 03

Tony calls again and is looking for more from Mike.

by bigaxe72 in Gay Male 08/05/2017
H
4.61
42.3k
42
20
51

Cherry

There's a first time for everything.

by WritingForToffee in Anal 03/14/2020
H
4.6
60.5k
41
5
69
0

The Birth of a Size Queen

I wanted it, and I got it.

by pdiddyd55 in Gay Male 02/26/2024
H
4.73
16.8k
41
4
66

Domestic Wife Ch. 08

Husband punishes submissive wife with first time anal.

by pinkcandy99 in BDSM 08/16/2018
4.34
113k
41
9
68

Asleep

She pretends to be asleep while he fucks her ass.

by Fell_Tempest in Anal 10/18/2019
4.27
68.6k
40
4
69
0

Hot & Bothered

Wife wants sex after her run; he has a surprise for her too.

by dark_entries in Anal 08/03/2014
4.35
99.2k
40
11
53
0

Cat Burglar

Lisa gets fucked next to her sleeping boyfriend.

by pixie2002 in Toys & Masturbation 09/06/2005
H
4.55
201.6k
40
24
51
0

First Time (Going All The Way)

A sucking turns into losing my Anal Virginity.

by gregshaw in Gay Male 02/03/2014
4.47
80.1k
40
12
50
0

Rohit's Dilemma

Rohit receives a mysterious sex tape.

by BeastMan69 in NonConsent/Reluctance 06/08/2018
4.45
35.4k
39
4
64
0

Hutch's Property Ch. 02

Lorna’s decent, Ken’s crash landing. Hutchinson’s repair.

by bucksilver in Loving Wives 03/13/2011
4.11
79.3k
39
72
45

Archived Memories

An older woman learns from a young teacher.

by byronbert in Mature 10/15/2017
H
4.62
47.5k
39
9
54
0

Harry and Maggie

Picking up a classmate hitchhiking leads to fun in a van.

by Mr_Owlow in Anal 08/28/2018
4.47
37.5k
38
2
49
0

A Dutiful Husband

Wife asks him to do her a favor...

by susurrus in Loving Wives 11/18/2001
3.9
243.2k
38
0
51
0

Hostage of my Heart Ch. 04

Who survives the rescue?

by SteffiOlsen in NonConsent/Reluctance 04/29/2016
H
4.81
40.7k
38
25
45

Big Dick Gay Sex

Hitch Hiker and gay sex.

by cut7nchlookn in Gay Male 05/04/2016
4.33
68k
37
4
40

The Island: Emily

Sir meets his newest slave.

by maddiebarry in NonConsent/Reluctance 06/08/2016
H
4.5
69.4k
37
6
57

The Entertainment Ch. 02

Sissy gets used by the inexperienced guests.

by econut in Fetish 01/12/2015
H
4.69
59.1k
37
4
59

My Only Time With Another Man

Invited to my airport hotel room.

by Cuckvoyeurfan in NonConsent/Reluctance 05/23/2021
4.25
40.5k
37
3
57
0

Raped by Her Loving Boyfriend

Boyfriend comes home from university, takes her anal cherry.

by LittlePeach92 in NonConsent/Reluctance 03/30/2023
3.77
45.5k
37
2
66
0

Finding Himself in Her Ch. 05

Jaime and Kara share a loving morning, yoga, then The Dinner.

by Mr_Owlow in Fetish 03/05/2013
H
4.74
50.3k
37
26
38

Life's Surprises

When Luka starts over he learns more about himself.

by XXNoraJeanXX in Gay Male 02/21/2015
H
4.5
25.5k
36
10
43
0

Dee's First Porn Shoot

Mature woman agrees to shoot scene.

by Vitorio in Mature 04/27/2009
4.34
133.2k
36
9
48
0

Remedial Medical

Doctor stretches the new novice's anus for advanced anal.

by Bailey_R_Britton in Fetish 02/18/2022
H
4.54
63.6k
36
5
84
0

Dee's Anal Tease

She decides to explore anal sex and teasing.

by marriedpervs in Anal 05/06/2006
H
4.56
150.1k
36
9
62
0

Megan's Secrets Revealed

Some secrets are just meant to be shared.

by Belegon in Anal 06/26/2005
H
4.56
129k
36
16
64

Good Guy all the Bad Girls Want Pt. 04

Sharon teaches Ben best Anal practice.

by Ian56 in Mature 08/12/2017
H
4.69
36k
35
4
41

Little Red Pill Ch. 02

Noah continues to grow, and returns to the gym.

by MattyTanner in Gay Male 11/22/2019
H
4.6
39.5k
35
4
50

Tom Boy Tom Girl

Sissy takes anal cum first time.

by Alluring_Crimson_Shifter in Gay Male 05/14/2016
4.24
49.4k
35
3
44
0

Rescued by the Bartender

Hannah wants Joel to watch another man fuck her, and more!

by SwitchMami in Group Sex 12/19/2014
4.4
72.9k
35
6
43
0

The Island: Caroline

An island of sex slaves.

by maddiebarry in NonConsent/Reluctance 06/03/2016
4.44
104.5k
35
7
75

Donald Comes to Town Ch. 04

Logan takes Sebastian's 18 yo cherry ass, Jeremy joins in.

by LoganPrejean337 in Gay Male 09/20/2022
H
4.86
14.1k
34
8
48

Sandra Goes Slut

Middle-aged good wife goes bad - with husband's blessing.

by Nylontease in Loving Wives 12/14/2012
4.05
123k
33
9
44
0

Gina Helps Joey Become Julia

Gina gives Joey a makeover, turning him into Julia.

by Devilsoctane in Transgender & Crossdressers 12/20/2023
H
4.73
17.8k
33
7
74
0

Mr. Grinch

Fred's Christmas was stolen it comes back.

by prinnavea in Loving Wives 01/01/2019
4.07
39.1k
32
57
34

A Blessing in Disguise

Rough anal sex can, sometimes, save a relationship.

by Maria24 in NonConsent/Reluctance 12/22/2017
4.03
51.7k
32
2
40
0

Rebecca's Rebirth Ch. 01

A young woman finds her true self.

by Kalavo in Erotic Couplings 10/19/2018
H
4.74
21.4k
32
0
58

My First Time

The first time I had sex with another man.

by K_Martini in Gay Male 06/12/2015
H
4.5
81.4k
32
11
39
0

Girlfriend's First Anal

He gives her a new experience.

by standingstones in Anal 04/04/2006
3.89
251.9k
31
0
39
0

A First In The Rear

Newfound friend gives her what hubby won't.

by Art in Anal 01/11/2002
4.15
371.9k
31
16
39
0

Close to the Phone Ch. 02

His wife refuses her lover's friend, so he must fill in.

by LesGermane in Gay Male 09/21/2009
4.18
64.5k
31
12
38

Janet's Birthday Surprise

Janet gives her husband a 40th birthday gift.

by jomomma141 in Group Sex 01/15/2009
4.28
97.6k
30
2
44
0

I became my girlfriend's slave Ch. 02

I became my girlfriend's slave, she came bearing gifts.

by KittyAshleyy in BDSM 03/13/2020
4.35
34.7k
30
3
41

Fucking & Punishing A Slut Ch. 01

Ass fucking Shelly.

by Abeja in Anal 02/07/2007
4.1
233.1k
30
9
36

My Roommate Mark Pt. 02

Mark wants to try something new.

by vulkansnsfw in Gay Male 01/09/2018
4.46
34.6k
30
3
40

Carol's Anal Introduction

She helps boss to introduce wife to first anal.

by regina_allen55 in Anal 09/13/2005
3.79
161.7k
29
5
44
0

That Money Spinning Idea

Two hard up students have an idea for extra income.

by contactsteph77 in Transgender & Crossdressers 02/18/2020
H
4.51
20.6k
29
4
39
0

Ready for My Close-Up

Jake and Ethan's movie scene rehearsal goes off-script.

by QuickYellowFox in Gay Male 03/01/2024
H
4.86
13.3k
29
6
53
0

Saving the Sexy Parts: Anal

Nina experiences anal sex for the first time.

by steves_mom in Audio 12/24/2014
4.4
104.7k
28
4
42

The Journals of ███ ████: Ch. 01

A Hollywood producer's greatest Christmas memory.

by Just_Call_Me_Garlic in Celebrities & Fan Fiction 12/29/2021
H
4.77
17.2k
28
6
46
0

Melissa's Gorgeous Ass

Melissa asks him to take her gorgeous ass.

by Boxlicker101 in Anal 09/02/2005
4.4
168.6k
28
8
35
0

Julia Becomes a Whore

Respectable lady decides to pep up her sex life.

by J G Parkes in NonConsent/Reluctance 02/12/2006
4.32
122.7k
28
0
44
0

Granting Castle a Wish

Kate experiences a first with Castle.

by lautloseswort in Celebrities & Fan Fiction 03/25/2015
H
4.66
33.7k
28
1
32
0

Plump and Plain

Losing her virginity takes awhile - & an audience.

by tarkatony in First Time 01/19/2006
4.49
171.4k
27
12
32
0

Your Ass Is Mine

She wouldn't give it up, but he wanted it.

by seceretwriter in NonConsent/Reluctance 09/07/2006
4.04
305.5k
27
16
42
0

Hostage of my Heart Ch. 03

The situation worsens & Opal is in the middle.

by SteffiOlsen in NonConsent/Reluctance 04/14/2016
H
4.74
42.5k
27
8
29

When Love Comes to Town: Audio Interpretation

A sweet and sexy anal first.

by theravenfox in Audio 06/29/2010
4.36
129.9k
27
15
38

Subhash Takes His Maid Anal

Indian Maid gets a lesson and anal.

by man_india in Anal 08/15/2007
3.57
214k
27
7
33
0

Family Matters

Mick and his no-biological Niece have anal sex.

by Eldon132 in Incest/Taboo 10/03/2015
4.21
74k
27
5
39
0

Used

She has a fantasy to be used. He MAKES it come true.

by Tinolt in NonConsent/Reluctance 01/29/2010
4.17
149.1k
27
5
55
0

Sharon Takes It in the Ass

This time, no is not an option!

by sexyinmexico in NonConsent/Reluctance 04/26/2017
3.89
90.1k
27
7
41
0

Seamus Ch. 02

Seamus takes his best-friend's virginity.

by Sachs in Gay Male 02/17/2006
H
4.78
110.4k
27
5
39

A Game of HORSE Pt. 04

Brandi plays with toys and decides she wants the real thing.

by emelle78 in Transgender & Crossdressers 08/03/2021
H
4.82
19.6k
27
2
34

Nate's Birthday Surprise Pt. 01

Nate and Marianne's mundane sex-life gets upended.

by GentlemanFlynn in Loving Wives 12/16/2021
4.16
36.1k
27
33
51

Mystery Girl

Jake gets a mysterious call from a stranger.

by JakeRockwell in Anal 06/20/2022
H
4.54
23.4k
27
2
41
0
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