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‘first time anal’ stories

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Vivian's Story Ch. 03

She takes Paul's cock for the first time.

by SummerElizabeth8 in Anal 06/16/2006
4.49
126.9k
13
6
15

Ties Me Down and Takes Me

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

by hotandsexyxxx in BDSM 02/12/2016
3.09
40.9k
13
3
18
0

My Name is David

An 18yo gets wrecked by 29yo and 45yo.

by Corjix in Gay Male 11/17/2022
3.89
28.2k
13
0
32
0

A Couple's Fijian Vacation Ch. 06

Caitlin is keen to have a threesome.

by Mingemuncher in Group Sex 06/07/2023
H
4.57
10.1k
13
2
19

House Call

A sick man finds he has really good insurance

by EmilyMiller in Erotic Couplings 10/09/2023
H
4.57
20.1k
13
29
35

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

The Friendly Neighbour Dominates

New into town - The guilt trip.

by bobby888 in Fetish 09/19/2014
3.54
33.5k
13
9
14

The Lake Ch. 03

Kali and Nik entertain hotel guest and try something new.

by JamaicanMeCrazy in Interracial Love 11/15/2008
H
4.75
24.1k
13
8
15

Making of a Slut

From the Kohala coffee fields to Waikiki hotel rooms.

by ElderDirt in Erotic Couplings 01/23/2019
H
4.52
16.7k
13
3
22
0

Reunion in the Pines

Ex-lovers re-unite, and re-ignite the flame.

by JakeRockwell in Anal 03/28/2018
H
4.5
18.6k
13
2
19
0

A Young Man's Sexual Odyssey Pt. 02

The Vibrating Tranny Hooker.

by erectus123 in Transgender & Crossdressers 10/04/2016
4.24
12.1k
13
1
14

When Love Comes To Town

A young couple in their first of many firsts.

by theravenfox in Anal 06/13/2010
H
4.52
79.6k
13
4
24

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
33.8k
12
1
32
0

Ann: A Love Story Ch. 06

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

by mimaster in BDSM 02/01/2009
H
4.76
43.9k
12
3
13

Wait... What?

A rebuttal.

by HaydenDLinder in Anal 06/29/2016
4.06
46.4k
12
28
14
0

My Queer Cousins Ch. 02

A 90's transexual, sci-fi, mystery romcom.

by RoryOmore in Transgender & Crossdressers 12/02/2023
H
4.86
4.8k
12
5
18

20 Years in the Making Ch. 02

Round two with Rachelle means I take her ass.

by Nympho_maker in Anal 09/20/2020
4.03
27k
12
0
13

Purity Ch. 10

Alice is caught trying to escape her imposed chastity.

by Sexykit in BDSM 04/11/2024
H
4.62
6.8k
12
2
22

Total Hedonism Pt. 05 - Shae & Her Friends Use Me

The best three day fuck fest of my life.

by OringrGarner in Group Sex 02/19/2022
H
4.62
11.8k
12
1
31

Twenty-One & Fresh Out of School

She's seduced by older couple.

by jwc10010 in Group Sex 08/25/2007
4.3
85.1k
12
4
19
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
52.7k
12
4
27

Coconut Delight

Anal loving for him & her on the 4th.

by lord_jefe in Anal 07/12/2013
4.24
41.9k
12
5
16

Bonus for the Nanny Ch. 04

Katie and Will's relationship takes a new and final turn.

by will_4_rp in Mature 08/27/2009
H
4.54
32.7k
12
2
14

My New Personal Assistant Ch. 08

You're prey. The sooner you accept it, the less it will hurt.

by I_Dusk in Gay Male 01/06/2023
H
4.72
11.6k
12
3
22

Danica Pt. 06

Dangerous new talent; punishment for a kindness.

by Darkniciad in Sci-Fi & Fantasy 03/26/2006
H
4.83
37k
11
3
14

New Life: The Awakening

Young woman kidnapped and given a taste of BDSM.

by bondagekitten775 in BDSM 08/14/2011
4.36
48.4k
11
5
17
0

In Plain Sight Pt. 03

Continuation from Chapter 2, buttsex (finally) ensues.

by isaacdicks123 in Gay Male 08/29/2021
H
4.69
9.3k
11
3
18

College Fund Ch. 05

In love with Andy AND my latest role-playing game.

by bjmichaels in Gay Male 09/26/2016
H
4.6
13.6k
11
5
12

The Snowman Experience

Hot housewife gets ass drilled by demonic snowman

by CheekyHousewife in NonHuman 07/06/2017
3.9
13.2k
11
2
16
0

Into the Woods Ch. 03

The fun continues.

by davidinlace in Gay Male 06/15/2023
H
4.72
6.8k
11
4
13

Scoring Points

A macho hetero boy on holiday get used.

by sailor_ams in Gay Male 03/15/2024
4.22
8.9k
11
4
17
0

Marcia's Birthday Surprise

Marcia's boyfriend gives her a surprise threesome.

by xxxcutiepiexxx in Group Sex 11/25/2008
4.22
83.4k
11
2
24
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

Anal Virgin

Her first anal experience.

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

The Caregiver Ch. 03

Nana is fully 'broken in' to her new job.

by Afroscorpio in Anal 02/18/2019
H
4.61
27.4k
10
1
11

Rekindled Ch. 06

Isabeau's story; hints of what is to come.

by His_beloved_roisin in BDSM 06/02/2012
H
4.83
14k
10
6
11

Gwennalyn's Sexual Awakening Ch. 15

Debauchery & deceit abound at the prince's going-away party.

by majicman21 in Sci-Fi & Fantasy 11/21/2019
H
4.56
9.4k
10
3
21

The Semen-ator Pt. 01

The stranger knew all his fantasies? How?

by mindingutter in Fetish 10/15/2012
3.96
25.3k
10
0
17

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

I Finally Fucked Jeff

I finally have gay sex with my college friend.

by RobS1999AD in Gay Male 04/19/2024
4.44
7.1k
10
0
19
0

Teacher's Pet Pt. 08

Continuing my sexual education with HS teacher's roommate.

by azintruder in Erotic Couplings 07/23/2021
H
4.74
8.6k
10
0
18

First Experience Topping a Couple

My first time as a Dom to a couple.

by manfromvenus in BDSM 04/09/2018
4
17.4k
9
1
14
0

The Bet 11: Friday Shenanigans

The fun begins for Sarah, Henry and John.

by Midnighter_193 in Incest/Taboo 11/04/2020
H
4.66
6k
9
0
19

My Neighbors, My Angels Ch. 02

The rewards for the trainer get better and better.

by touchmate in Loving Wives 09/26/2012
4.4
37.3k
9
3
12

Our Little Secret Ch. 02

Maria and I get to know each other further...

by Midfielder86 in Group Sex 08/01/2013
H
4.65
26.7k
9
0
14

Plumber's Toy: The Quickie

Plumber stops by to play with his new toy's ass.

by plumberstoy in Erotic Couplings 02/04/2014
3.79
24.5k
9
3
11

After Dinner

A night of firsts.

by humminbean in Erotic Couplings 10/10/2009
H
4.72
30.2k
9
5
15
0

From One Story To The Next

Her boyfriend lets loose deep in her ass.

by Texas Tease in Anal 01/29/2006
3.84
187.3k
9
8
11
0

Maximum Security

Police officer loses her anal virginity.

by Samuelx in Anal 08/24/2006
3.32
158k
9
2
13
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

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

An Ordinary Man's Life Ch. 09

Donna offers Todd her anal cherry.

by FrankjrBauer in Romance 11/20/2013
H
4.68
21.5k
9
0
10

The Visitor Returns

A whole new experience with the nameless stranger.

by AstroPal99 in First Time 08/06/2023
4.32
8.6k
9
1
13

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

My Muse

A massage turns into something more.

by Melody_Iver in Gay Male 11/09/2023
H
4.61
9.2k
8
1
14
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

The Swallow

Rachel goes undercover to catch a traitor.

by SnoozyXY in Novels and Novellas 08/20/2020
H
4.54
10k
8
3
20
0

In Plain Sight Pt. 02

Another meeting with my hookup, now in school locker room.

by isaacdicks123 in Gay Male 08/26/2021
H
4.76
10.8k
8
2
17

Yes, Master

He brings in another man for her first anal.

by chelle1979 in BDSM 08/19/2007
3.79
66.3k
8
8
12
0

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
44.4k
8
1
11

Back End Love

A couple tries anal for the first time.

by jason121872 in Anal 04/03/2017
4.09
42.1k
8
1
10
0

Ms. Morgan's Dilemma

Christa tries to seduce her teacher, tries something new.

by bhanover in Anal 01/02/2018
4.1
38.6k
8
2
13
0

Untamed Longing for Forbidden Fruit

Boundaries broken & fantasies fulfilled with fiance's cousin.

by kinkybiitchx in Erotic Couplings 08/14/2013
4.37
21.9k
8
2
12
0

Samantha on the Swing Pt. 02

A girl accepts a strange offer online and finds her calling.

by BowAndQuiver in BDSM 05/23/2021
4.38
13.2k
8
3
11

The Widowers Solace Pt. 02

A widowers love of crossdressing leads him to find comfort.

by contactsteph77 in Transgender & Crossdressers 07/07/2022
H
4.66
6.7k
8
1
8

Asexual Wife Whores Herself Out Ch. 03

She surrenders her ass, her last unused hole.

by DStrrbd in Anal 12/20/2022
3.73
16.5k
8
0
11

Sydney Cox - The Beginning

Naive girl leaves the farm for the first time.

by DurtyWriter in First Time 03/30/2018
3.35
23.7k
8
0
8
0

Getting Over My Ex

Anal exploration soothes a broken heart.

by skylergirl in Anal 06/26/2005
0
99.2k
8
5
10
0

In The Kitchen

Couple tries anal sex for the first time.

by emotionalthing in Anal 05/08/2006
4.14
119k
8
4
11
0

Restaurant Passion

Two employees enjoy a forbidden anal encounter.

by Noonenkows in Anal 04/30/2007
4.3
76.6k
8
6
10
0

Visiting My Mormon Friend 03

Tending to an Expanding Flock.

by cuddlemonkey in First Time 09/27/2022
H
4.61
18.5k
8
1
12

Allison

Widowed wife's friend has a secret life and a craving.

by DurtyWriter in Erotic Couplings 09/20/2017
4.34
16.6k
8
0
14
0

A New Twist

A bottom tries the top, and the middle.

by schuwinggg in Gay Male 11/20/2011
4.19
42.8k
7
6
11
0

Rescuing Sweet Olivia 02

RESCUING SWEET OLIVIA 02.

by DEGE in NonConsent/Reluctance 12/31/2023
H
4.71
6.7k
7
0
26

My First Time Man

Tony takes my anal virginity.

by Corjix in Gay Male 10/19/2021
4.09
26k
7
1
12
0

More Twisted

A young lady's further debaucheries!

by wetfeline31 in Group Sex 11/01/2013
4.36
31.1k
7
1
11
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

Bexley Perplexity Ch. 03

Wyatt experiences two new things, and loves both!

by UnexploredYearnings in Transgender & Crossdressers 05/14/2016
H
4.66
11.4k
7
1
7

Tough Loss

Consoling my bf after a tough loss.

by BeckyOU in Interracial Love 09/13/2022
3.82
12.8k
7
0
12

Buttermilk Pancakes Pt. 01

First time anal, boyfriend offers comfort & care.

by numonebun in Anal 06/19/2020
4.06
22k
7
2
18

The Amanda Story Ch. 05

Amanda brings a friend.

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

First Sex Experiences Pt. 04

Online posts about first fuck, first oral and first anal.

by KimKim5 in First Time 10/15/2021
4.31
10.3k
7
0
8

Vacation Pt. 03: Home

Taking her in every way.

by CC1436 in Anal 03/23/2015
4.37
33k
7
1
10

A Summer with Ali Pt. 02

Our narrator goes to Ali's for dinner and goes further.

by Roland_Castle in Gay Male 03/22/2022
H
4.82
5k
7
2
11

The Movie Lovers Ch. 06

Doing Rosie's rosebud.

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

The Doldrums: the Sailor and the Virgin Ch. 08

A shocking revelation has heady consequences (mf).

by astushkin in Novels and Novellas 06/03/2016
4.47
14.4k
7
1
9

The Long Goodbye

Amelie's summer rendevouz comes to a close.

by TH_Ainsley in BDSM 04/03/2024
H
4.79
4.6k
6
1
10

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

Sundays

Sensual Sunday stroll down memory lane.

by DeLaFaye in Anal 05/22/2022
4.4
3.6k
6
3
8
0

Three-Input Lady

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

by powelldonovan in Anal 03/22/2008
4.34
39.6k
6
0
7
0

A Friend in Need is a Friend Indeed

Friends with benefits, D/s, roleplay and public play.

by CatoriSinopa in BDSM 09/03/2022
4.24
9.4k
6
0
16
0

Purity Ch. 06

She is forced to violate her own untried hole in retribution.

by Sexykit in BDSM 01/06/2024
H
4.5
11.2k
6
0
16

After Dinner

Dinner and romance lead to a special reward for you.

by hafnium10 in Anal 03/04/2009
4.21
28.9k
6
0
8

Dessert

Husband and wife enjoy a passionate evening.

by SydNancy in Erotic Couplings 03/09/2010
4.22
27.3k
6
4
9
0

Oz Beach Boy & Odessa Try Anal

Matt & Odessa go dark on Halloween with first time anal...

by MyBareTorso in Anal 10/12/2023
H
4.58
13k
6
1
15
0

Anna's New Business Ch. 03

Anna faces her own sexuality and her risks.

by DEGE in Fetish 12/25/2023
H
4.71
3.9k
6
4
22

First Time Anal

She felt like a dirty, dirty girl – and loved it.

by burmohini in Anal 03/03/2006
3.27
182.1k
6
4
8
0

Finding Ivy Ch. 13

Ivy has fun with cousins.

by Lcpce in Sci-Fi & Fantasy 09/26/2020
4.45
4.3k
6
0
7

Because You Deserve It

Sub loses her anal virginity to her Dom.

by Severance666 in BDSM 01/19/2016
3.98
21.3k
6
3
8
0

Love without Limits - Date Night Ch. 01

Harry and Sam have a night out on the town.

by LateBloomer1972 in Gay Male 07/23/2022
4.47
8.9k
6
0
12
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