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‘first time anal’ stories

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The Imperfect Storm Ch. 02

Asserting his dominance, she loves it

by mojavejoe420 in Incest/Taboo 04/07/2014
H
4.69
65.1k
50
5
60

Battered & Bruised

A woman is attacked while walking home from a night out.

by majicman21 in NonConsent/Reluctance 05/25/2019
H
4.58
64.7k
109
10
184
0

Five Beautiful Words

A willing girl offers me her ass.

by sexyinmexico in Anal 12/10/2016
4.35
64.5k
24
6
32
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
39

The Monster under The Bed

Home for the summer, Laura is confronted by a childhood foe.

by majicman21 in Erotic Horror 10/17/2020
H
4.71
64.4k
306
17
490
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
64.2k
36
5
85
0

Hostile Takeover

Disgruntled employees turn the tables on their boss.

by majicman21 in NonConsent/Reluctance 12/17/2016
4.42
64.1k
74
3
105
0

A Black Afternoon

An eager submissive's first time with anal.

by Sugarhigh24 in Anal 01/23/2016
H
4.5
62.5k
26
7
42
0

An Itch to be Scratched

A gypsy's curse is a Doctor's dream come true.

by Bethyboo in Group Sex 10/04/2013
4.21
62.4k
10
4
17
0

The Making of a Real Bathhouse Slut

A mature married man finds his true calling.

by Danmo1 in Gay Male 01/14/2017
H
4.6
62.2k
64
19
80
0

One Hot Summer Day

Three strangers get hotter together.

by KeKaneAnoi in Interracial Love 07/23/2005
4.31
61.8k
4
0
6
0

Angel in Heat

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

by cbsinclair in Group Sex 01/28/2016
4.36
60.7k
42
6
55
0

Cherry

There's a first time for everything.

by WritingForToffee in Anal 03/14/2020
H
4.59
60.7k
41
5
70
0

12 Months a Slave 03: March

A wife is held as assurance until his debt is paid.

by lightsend in NonConsent/Reluctance 06/08/2021
4.44
59.7k
70
0
105

The Guy from the Internet

Rachel has first time anal with random guy from the internet.

by TheHiddenPen in Anal 06/06/2014
4.25
59.6k
24
7
40
0

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

The Movie Lovers Ch. 06

Doing Rosie's rosebud.

by marcy1238 in Anal 03/18/2008
H
4.64
58.8k
7
3
10

Deepest, Darkest.

A sordid tale of a lovers' wet and dirty reunion.

by LoveMeForMyThorns in Fetish 11/01/2012
4.46
57.1k
26
3
33
0

Naptime

Naptime ends with a welcome intrusion.

by GentlemanWriter in Anal 11/04/2006
4.21
57.1k
4
1
7
0

School Days Ch. 08

Hottub hijinx.

by Navig8tor in Anal 11/03/2006
4.31
57k
5
1
11

Nudity at English Garden in Munich

Their clothes are stolen while trying nudity first time.

by Racqel in Exhibitionist & Voyeur 07/31/2008
4.35
56.8k
13
2
17
0

Tit for Tat Pt. 01-02

Yes, she'll do anal ... for a price.

by LaBlancheTraversee in Anal 10/25/2016
4.27
56.6k
16
4
28
0

High School Beautiful Ch. 03

Maddy does more for an A on an exam.

by Ravensing in Anal 04/15/2017
4.3
56.3k
21
5
23

First Anal Encounter

Lovers engage in anal sex for the first time.

by theeyesavit in Anal 05/23/2010
3.35
55.5k
2
1
2
0

Jayne's Introduction to Anal

They meet after joking around on the net.

by duke0467 in Anal 11/28/2009
4.03
54.9k
2
2
2
0

An Interesting Awakening

Lonely young wife finds she might like it rough.

by Zerlina in BDSM 03/15/2006
4.34
54.9k
15
6
21
0

Rasika's Surrender Ch. 03

Humiliating first time anal experience.

by dugong in NonConsent/Reluctance 07/30/2021
4.3
54.8k
21
3
36

In the Cool Night Breeze

Married couple rekindle the spark by exploring new territory.

by ElizaB in Anal 07/09/2007
4.25
54.5k
13
1
13
0

Julie's New Beginning

A new start.

by rkm10 in Anal 10/17/2006
4.15
54.2k
2
4
3
0

Street Party Ch. 03

Mum and daughters find lots of sex on holiday.

by Simitoo in Incest/Taboo 08/31/2012
H
4.55
52.8k
12
4
27

Anal Virgin

Her first anal experience.

by Cindygrl72 in Anal 11/14/2010
4.11
52.7k
10
3
10
0

The Deal Pt. 02

The awakening - it's not over yet for Freddy & Carolyn.

by emelle78 in Transgender & Crossdressers 05/06/2021
H
4.75
52.2k
158
41
218

A Blessing in Disguise

Rough anal sex can, sometimes, save a relationship.

by Maria24 in NonConsent/Reluctance 12/22/2017
4.03
51.8k
32
2
40
0

Welcome to Rolennia Ch. 02

A willing secretary needs some new training.

by DrSqueaky in Erotic Couplings 05/09/2011
H
4.67
51.2k
19
5
27

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
50.4k
37
26
38

Church of Swallowing: Domination of Roxy

Roxy gets dominated into the Church.

by Silentbob in BDSM 09/09/2007
4.36
49.9k
14
1
15

Tom Boy Tom Girl

Sissy takes anal cum first time.

by Alluring_Crimson_Shifter in Gay Male 05/14/2016
4.24
49.5k
35
3
44
0

The Very Fortunate Accident

An unexpected special treat after a night out.

by JakeRockwell in Anal 03/27/2018
4.41
49.3k
18
3
30
0

Hard On the Trail Ch. 05

I get to be a daddy.

by ketup in Gay Male 03/04/2014
4.35
49.1k
19
1
26

New Life: The Awakening

Young woman kidnapped and given a taste of BDSM.

by bondagekitten775 in BDSM 08/14/2011
4.36
48.5k
11
5
17
0

A Farewell to a Friend

Courtney brings a friend to say goodbye to Alex.

by TriHockeyGuy3 in Group Sex 01/19/2006
H
4.57
47.9k
8
0
19
0

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

Pleasure on the River

A sexy Asian babe has hot sex with a stranger on the river.

by iggyspear in Erotic Couplings 01/06/2014
4.27
47.5k
23
0
37
0

Trucker Turned Me Out Pt. 01

Young man meets a trucker online.

by homewreckingpizzaboy in Gay Male 05/15/2019
H
4.58
47.4k
52
8
77
0

Sapphic Healing Ch. 07

Danni's first anal.

by fantac64 in Lesbian Sex 06/20/2008
4.49
47k
15
1
18

Wait... What?

A rebuttal.

by HaydenDLinder in Anal 06/29/2016
4.06
46.5k
12
28
14
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
46k
37
2
66
0

Jen's Revenge

Jen's boyfriend helps her get revenge on an old classmate

by NenaPatton in NonConsent/Reluctance 04/20/2014
4.07
45.8k
15
2
25
0

She Gets More Than She Wanted

April asks for more than she can handle.

by Aprilfirez in BDSM 09/26/2006
4.29
45.5k
6
0
11
0

Imprinted Ch. 07

Jacob & Mr D go it alone - a first time for them both.

by darcysweet in Gay Male 12/10/2009
H
4.73
44.6k
27
5
29

Better with Age Ch. 03

Mike & Jean go crazy on a weekend trip.

by goes4grey in Mature 11/25/2010
H
4.72
44.5k
10
4
13

Her Dirty Doctor Dreams Come True Pt. 05

The Tail End - doc introduces her to anal for the very first time.

by sabrinaH33 in Erotic Couplings 06/19/2015
4.29
44.5k
8
1
11

Ann: A Love Story Ch. 06

Neils turn to star in anal 'scene' with Dawn.

by mimaster in BDSM 02/01/2009
H
4.77
43.9k
12
3
13

The Amanda Story Ch. 05

Amanda brings a friend.

by Craig88 in Group Sex 09/16/2006
4.28
43.1k
7
0
10

A New Twist

A bottom tries the top, and the middle.

by schuwinggg in Gay Male 11/20/2011
4.19
42.9k
7
6
11
0

Three Toppings

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

by darktigerroar in Anal 10/10/2018
H
4.53
42.6k
51
3
65
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

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
42.4k
42
20
51

Virgin Babysitter Becomes My Slut Ch. 04

As Annie makes up her mind, I remember becoming Master.

by KiteFlyingElephant in NonConsent/Reluctance 05/31/2022
4.47
42.3k
27
10
42

His Cum Is Mine

Ali is Mistress for a day

by AlinaX in BDSM 02/20/2014
H
4.58
42.1k
22
2
35

Back End Love

A couple tries anal for the first time.

by jason121872 in Anal 04/03/2017
4.08
42.1k
8
1
10
0

Coconut Delight

Anal loving for him & her on the 4th.

by lord_jefe in Anal 07/12/2013
4.24
41.9k
12
5
17

First Experience with Master

First anal experience from her master.

by rathna in NonConsent/Reluctance 07/29/2011
3.66
41.8k
3
6
4
0

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

Lose Yourself

An itch that needed to be scratched.

by lonni in Anal 11/17/2006
3.74
41.6k
4
1
5
0

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

Ties Me Down and Takes Me

He ties me down and takes me in all three holes.

by hotandsexyxxx in BDSM 02/12/2016
3.11
40.9k
13
3
18
0

Anal Be Yours Forever

Elven lovers find passion in the forest.

by SlidingInSilk in Sci-Fi & Fantasy 03/01/2002
4.3
40.9k
5
0
8
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

My Only Time With Another Man

Invited to my airport hotel room.

by Cuckvoyeurfan in NonConsent/Reluctance 05/23/2021
4.25
40.6k
37
3
58
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
40.3k
53
4
93
0

Jen & Mitch's Video

A young couple make a sex video of themselves.

by Nicole99 in Erotic Couplings 07/05/2010
H
4.62
40k
22
1
32
0

Three-Input Lady

He took the sun-kissed approach to changing her mind.

by powelldonovan in Anal 03/22/2008
4.34
39.7k
6
0
7
0

I Hate Him...

Can straight Texan jock lust for a pesky feminine activist?

by Edey in Transgender & Crossdressers 07/20/2022
H
4.77
39.6k
122
54
190

Mother of the Bride Ch. 02

And mother of the groom.

by Scot1234 in Group Sex 07/21/2016
4.48
39.6k
19
1
23

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
39.6k
35
4
50

Julia, Her First Time

Julia and her Boyfriend go to their first swing.

by Jessie92 in Group Sex 09/11/2021
H
4.58
39.2k
58
2
102
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

To the Last Knuckle

Heartbroken guy finds a new lover. She finds his prostate.

by mysteryofthings in Anal 03/23/2021
4.31
39k
61
7
92
0

Ms. Morgan's Dilemma

Christa tries to seduce her teacher, tries something new.

by bhanover in Anal 01/02/2018
4.1
38.7k
8
2
13
0

On the Road

Nathan and Gabriella finally meet.

by derek33 in Anal 09/05/2006
4.11
37.8k
2
1
3
0

Gifts & Surprises

Tycoon gets 2 Valentines & 2 concubines (sequel to 'SB').

by P4U in Mature 01/31/2007
H
4.56
37.6k
7
1
8
0

Guess What I Saw? Ch. 05

Monica, Kelly, and Tony finish what they started.

by ErotickWriter in Exhibitionist & Voyeur 10/23/2013
H
4.8
37.6k
14
10
16

Harry and Maggie

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

by Mr_Owlow in Anal 08/28/2018
4.48
37.5k
38
2
49
0

My Neighbors, My Angels Ch. 02

The rewards for the trainer get better and better.

by touchmate in Loving Wives 09/26/2012
4.38
37.3k
9
3
12

Danica Pt. 06

Dangerous new talent; punishment for a kindness.

by Darkniciad in Sci-Fi & Fantasy 03/26/2006
H
4.83
37.1k
11
3
14

Limousine: Around Atlanta

Hot couple introduce new acquaintance to anal sex.

by dlawson in Group Sex 01/04/2011
4.19
36.2k
8
0
12

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
50

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
36.1k
36
4
42

Private Tutor

2 ageless guys, 1 ageless girl and "teacher" (college).

by xXxfaytalexXx in Group Sex 06/16/2008
4
35.7k
4
0
8
0

Our First Time Ch. 04

An internet date leads to first time anal fuck buddies.

by allitnil in Anal 05/14/2010
3.47
35.6k
2
0
4

Rohit's Dilemma

Rohit receives a mysterious sex tape.

by BeastMan69 in NonConsent/Reluctance 06/08/2018
4.45
35.5k
39
4
64
0

Still the Favorite Camper

Brian continues to win a senior counselor's attention.

by emittsrif in Gay Male 10/11/2011
3.97
35.3k
9
0
9
0

Lament

An evening of firsts.

by SilentRogue in Erotic Couplings 04/28/2006
4.4
35.2k
3
0
6
0

Birthday Bootie

Greg tops every other birthday with this bootie bash for Kat.

by knobgobbler in Group Sex 03/20/2008
4.36
35k
4
1
6
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
4.36
34.8k
30
3
41

My Roommate Mark Pt. 02

Mark wants to try something new.

by vulkansnsfw in Gay Male 01/09/2018
4.46
34.7k
31
3
41

A Tale of Two Brothers

Different Career Paths, Same End Result.

by kurrginatorX in Gay Male 12/25/2019
4.47
34.6k
21
2
47
0

Lori and Rick and Liz and Me Ch. 03

Liz finally takes it in the butt!

by ReedRichards in Anal 12/29/2015
4.44
33.9k
9
1
10

Coach Gets Used by Senior Class

New coach gets gangraped by his seniors for their graduation.

by Use_me_beardaddy in NonConsent/Reluctance 05/22/2021
3.42
33.9k
12
1
32
0
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