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‘anal first time’ stories

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Picture Perfect Ch. 03

After some unfinished business, Jason finally bottoms.

by tamgreen in Gay Male 10/14/2014
H
4.87
57.5k
107
29
122

Sugar Heart Ch. 05

Richard and Buddy go deeper, at last.

by tamgreen in Gay Male 11/24/2015
H
4.87
38.3k
73
35
85

Nellie and the Diamond Gala

She needs a date, but he wants something in return.

by MsCherylTerra in Anal 07/09/2020
H
4.81
383.2k
243
47
355

Her Brother Ch. 01

I thought I was in love... then I met her little brother.

by tamgreen in Gay Male 03/02/2015
H
4.79
221.8k
525
78
685

An Offer He Can't Refuse Ch. 07

Lyla and Mike have a talk, and more.

by ZenZerker in Incest/Taboo 06/30/2018
H
4.78
78.6k
131
9
194

Braining Ch. 05

Blair and Jenn.

by TexRiffraff in Mind Control 04/02/2013
H
4.78
42.5k
19
6
22

Loopholes Ch. 02

Tessa has an amazing surprise for Nick...

by ZenZerker in Anal 02/15/2018
H
4.78
270.6k
194
12
232

Seamus Ch. 02

Seamus takes his best-friend's virginity.

by Sachs in Gay Male 02/17/2006
H
4.78
110.3k
27
5
39

Lariats and Lacrosse Sticks Ch. 04

A spring break camping trip.

by reddirtwriter in Gay Male 01/28/2013
H
4.77
37.4k
32
8
36

Weird Sisters Ch. 02

His girlfriend's twin sister has a weird request.

by ZenZerker in Incest/Taboo 08/15/2014
H
4.77
262.2k
396
17
487

Submission Ch. 12

Master takes her anal virginity.

by Goldeniangel in NonConsent/Reluctance 06/10/2012
H
4.75
141.2k
84
6
98

CvsN 16: Beth's Last Virgin Hole

Sisters, Amie, and Beth's last hole - what a night.

by Tx Tall Tales in Anal 07/01/2010
H
4.75
424.2k
113
11
132

Buttfuck Buddies Ch. 01

Nick and Mia's passion for anal sex inspires Ashley...

by ZenZerker in Anal 05/08/2015
H
4.75
682.8k
1k
62
1.3k

Tommy Awakens Ch. 01-04

Priscilla awakens Tommy; Tommy loves Sarah.

by HotTommy777 in Erotic Couplings 10/24/2007
H
4.73
13.2k
2
0
3

Taken by the Wolf Ch. 14

Bella loses her anal virginity

by Goldeniangel in NonConsent/Reluctance 02/15/2014
H
4.72
109.1k
75
9
89

Valuation

Unexpected visitor gives a cd her first time with a man.

by Jamie_in_dresses in Transgender & Crossdressers 02/07/2013
H
4.72
73.7k
66
17
81
0

I Bet You'll Like It

His roommate is sweet, cute and she's into butt stuff...

by ZenZerker in Anal 11/18/2014
H
4.71
1.42M
2.4k
117
3.2k
0

Weird Sisters Ch. 01

Weird consequences of his girlfriend's fight with her twin.

by ZenZerker in Anal 08/14/2014
H
4.71
358.1k
622
16
947

Backdoor Sweetheart Ch. 01

She's his neighbor, his best friend and so much more...

by ZenZerker in Anal 02/21/2015
H
4.7
577.6k
965
39
1.3k

Cousin Lacey

Mark & his cousin share many firsts.

by slyc_willie in Incest/Taboo 09/26/2006
H
4.7
367k
209
59
281
0

Little Sister's Big Butt Ch. 02

Michelle and Tyler get much, much closer...

by ZenZerker in Incest/Taboo 09/24/2018
H
4.69
205.9k
328
19
420

Horsemaster's Captive Pt. 03

A need met, a reward given, as told by the Horsemaster.

by amberrenard in Anal 07/12/2018
H
4.69
21.3k
16
8
22

Barcelona Beauties Ch. 08

A group encounter leads to Lisa's first time with a man.

by Artist1 in First Time 04/13/2009
H
4.69
45.4k
2
3
2

Jeff and Paige

Love between and older man and a young woman.

by Kalavo in Anal 10/12/2016
H
4.68
91.5k
82
0
100
0

Daddy's Anal Virgin

I'm ready, please be gentle.

by theangeloftemptation in Audio 06/08/2022
H
4.68
40.4k
32
1
68
0

Courting My Sister Ch. 03

Jill seduces dad with a little help from Jim.

by Erlikkhan in Incest/Taboo 09/17/2007
H
4.68
121.7k
55
0
66

Because I'm Your Sister Ch. 02

Loving siblings wake up to a dream come true.

by ZenZerker in Incest/Taboo 10/04/2014
H
4.68
206.9k
258
30
306

An Ordinary Man's Life Ch. 09

Donna offers Todd her anal cherry.

by FrankjrBauer in Romance 11/20/2013
H
4.68
21.4k
9
0
10

Whatever Didi Wants Ch. 04

Plans for the summer and a new experience for the siblings.

by ZenZerker in Incest/Taboo 09/18/2014
H
4.66
77.7k
114
15
131

Drunk Samantha

Drunk Samantha is way naughtier than sober Samantha.

by Goldeniangel in Anal 03/01/2017
H
4.66
189.2k
178
9
269
0

Way Too Easy

Young nurse is helped over her fear of anal sex.

by Ton8ty in Anal 08/08/2007
H
4.66
422.6k
96
20
116
0

It Started With a Kiss

A tale of longing, insecurities and sibling love.

by ZenZerker in Incest/Taboo 11/19/2014
H
4.66
181.2k
193
14
291
0

Taken for the First Time Ch. 01

An older man takes a willing first timer all the way.

by CandleLit in Gay Male 04/17/2015
H
4.65
462.6k
418
111
515

90% True Ch. 09

How Jen lost her anal virginity.

by rhev in Anal 03/06/2013
H
4.65
105k
27
3
34

Finding a Jewel

Jaded 22-year-old has his fantasy fulfilled.

by MerryPrankster in Anal 01/24/2008
H
4.65
162.5k
43
10
49
0

Unfolding Ch. 01

Couple experiments with first time anal sex.

by Selena_Kitt in Audio 03/13/2006
H
4.65
1.16M
232
51
274
0

Devil's Feast

Hot friends enjoy a Halloween dinner theater orgy.

by chloehunt in Group Sex 10/23/2020
H
4.65
36.2k
30
6
56
0

A Courtesan and an Assassin

An erotic space adventure romance.

by lordofthewords in Sci-Fi & Fantasy 08/03/2008
H
4.65
55k
42
7
48
0

Halloween Odyssey

Hot blonde tricked into foursome by possessed garden gnome.

by chloehunt in Group Sex 10/19/2020
H
4.64
25.7k
37
6
69
0

Ethan's Grace - Anal Edition

Ethan introduces Grace to anal play.

by D_Lynn in Anal 05/12/2013
H
4.64
93k
40
8
56
0

Ashley’s Anal Curiosity

Threesome with husband and her sexy best friend.

by HeyAll in Anal 01/26/2016
H
4.63
377.5k
356
40
533
0

Shemale Bar

Straight guy goes into a shemale bar and is forever changed.

by silkstockingslover in Transgender & Crossdressers 03/08/2016
H
4.62
574.5k
984
114
1.2k
0

Sex and a Single Girl Ch. 14

A bum ride!

by sue_in_surrey in Anal 07/29/2008
H
4.6
62.1k
11
2
13

He was My Boss Ch. 02

A sequel to the original story, I did go back to work.

by texasautumn in Gay Male 02/14/2018
H
4.6
24.5k
23
14
24

Portia's School of Anal

She teaches a few friends how to take it.

by neargraduate in Anal 09/28/2007
H
4.6
286k
117
19
143
0

The Doctor Diaries Ch. 03

Patient introduces doctor to the delights of anal sex.

by The Big Bopper in Anal 01/23/2009
H
4.6
126.1k
36
1
50

Cherry

There's a first time for everything.

by WritingForToffee in Anal 03/14/2020
H
4.6
60.3k
41
5
68
0

My First Gay Experience

A gay roommate uses his straight roommate.

by creativeboyinspring in NonConsent/Reluctance 05/11/2021
H
4.59
76.3k
126
12
198
0

My Hot Wife Katie Ch. 02

Katie's anal experience.

by Freddyj881 in Loving Wives 10/01/2007
H
4.59
311.9k
108
11
141

Trust Ch. 03

A gay man falls in love with a straight one.

by Elenia26 in Gay Male 08/14/2013
H
4.59
16.7k
22
0
24

Unexpected Awakening

Married guy finds his bi side when wife's back is turned.

by Jamie_in_dresses in Gay Male 02/04/2015
H
4.59
104.2k
68
19
82
0

The Making of an Anal Erotic Ch. 01

How his lady discovered the joys of anal erotica.

by Matty_Walter in Anal 06/13/2008
H
4.58
37.5k
6
6
9
0

Revenge is Sweet

Young woman sleeps with best friend's father.

by lily_ann in Mature 06/20/2008
H
4.58
290.6k
290
19
421
0

Kate Puts Herself on the Menu

19-year-old's stranger takes her final prize.

by knownobounds in Anal 04/13/2007
H
4.58
184.9k
37
7
51
0

School Girl Blackmail Ch. 02

The night continues.

by BradGarrettStories in NonConsent/Reluctance 03/20/2013
H
4.58
257.4k
225
29
263

Spitroast

Phil and Ben help Linda keep her chastity vow, technically.

by CandiNyse in Anal 03/28/2017
H
4.58
78k
85
4
105
0

Anal Summer Ch. 01

An erotic coming of age tale of sexual awakening.

by erotica881988 in Anal 10/27/2014
H
4.58
152.1k
147
16
205

The Great Leap Forward

My desires are altered forever by a manipulative older TV.

by lilblkboy in Transgender & Crossdressers 01/27/2011
H
4.57
37.9k
18
5
23
0

Educating Laura: Anal Time

She plays with toys and Richie. Experiments are fun.

by Kumquatqueen in Anal 08/11/2022
H
4.57
21.5k
8
7
19
0

Straight Teacher Turned

Straight teacher is turned by two ex-students.

by silkstockingslover in Gay Male 09/24/2014
H
4.56
224.2k
262
28
342
0

Old Man Discovers... Ch. 12

...hopefully it won't be virgin long.

by tnwriter in Gay Male 04/24/2013
H
4.56
22k
4
2
4

Maggie May Ch. 04

Maggie eagerly accepts her maiden anal voyage.

by johnnieblue44 in Mature 10/05/2009
H
4.56
99.3k
15
1
17

Passing the Torch Ch. 02

Ben is left alone with Bella. And with her ass.

by tomlitilia in Loving Wives 11/14/2018
H
4.56
44.2k
66
22
97

Adventures of Wiley Coyote Ch. 01

I wondered what it would feel like to be fucked in the ass.

by wiley4377 in Gay Male 10/22/2009
H
4.56
130.1k
71
4
96

Experimental Anal

First-time anal among young lovers.

by princessmaryann in Anal 01/20/2013
H
4.55
97.5k
27
8
42
0

Revenge of the Nerd: Ex-Bully's Mom

Nerd dominates bitchy MILF and takes her virgin asshole.

by silkstockingslover in Mind Control 05/27/2015
H
4.55
687.4k
797
43
1k

Sis's Anal Awakening

My sis finds out she likes butt stuff, and I lend a hand.

by TheBadHatter in Incest/Taboo 06/05/2013
H
4.54
450.5k
396
29
478
0

The Flower Girl Ch. 01

An older man teaches Yuuka what she likes.

by Rob_mDear in Anal 05/19/2008
H
4.54
98.5k
52
9
72

Homework Assignment Ch. 01

The "full report" Master requested- at least, the first part.

by coleswhore4 in BDSM 04/18/2018
H
4.53
19.5k
6
0
11

Blackmailed: Cheerleader's Cherry

A Principal disciplines a stuck-up hot bitch cheerleader.

by silkstockingslover in NonConsent/Reluctance 03/16/2012
H
4.53
2.53M
2.6k
82
3.5k
0

Take Two

She wants to try anal, but why should her pussy miss out?

by Otazel in Anal 07/12/2013
H
4.53
150.2k
60
6
90
0

An Awakening

New book leads to exploration.

by Wish4me in Anal 05/09/2007
H
4.52
51.4k
10
2
12
0

Amber Valentines Day 1984

Amber turns into my private slut.

by mysreader in Anal 12/02/2010
H
4.52
45.3k
12
2
20

Slut-2-Fuck Ch. 02

Domme assembles the cast.

by realvelvetglove in BDSM 02/03/2012
H
4.52
54.6k
18
0
22

The Hard Hit

A hitman is surprised by his attraction to his target.

by Mr_Owlow in Transgender & Crossdressers 11/24/2013
H
4.52
64.6k
51
11
71

Our Story Ch. 02

He takes my ass.

by amberrenard in Anal 08/06/2017
H
4.51
58.1k
27
4
34

Misty Acres

Joy meets a group of much older men who show her a good time.

by CatoriSinopa in Group Sex 01/27/2024
H
4.51
12k
9
2
26
0

The Crazy Sexy Cat Lady Ch. 02

Sasha Gibson is back with a new pleasure to explore....

by Quasaar in Mature 06/14/2019
H
4.51
11.8k
7
3
11

Enslaved to the Mob Ch. 03

Angelique's first anal experience.

by darkknight0307 in BDSM 04/30/2009
H
4.5
117.8k
39
4
46

Norse Myth Models

Nude modelling isn't about sex. Honestly...

by TimothyM in Anal 06/26/2014
H
4.5
74.5k
24
9
38
0

Good, Clean Fun

Young couple discovers anal pleasure.

by RailRoader in Anal 06/30/2015
H
4.5
52.4k
17
4
22
0

Italian Teases/Pleases Black Ch. 08

Carmina's sexuality unleashed.

by BlkRainbow in Interracial Love 03/17/2012
H
4.5
22k
8
3
14

Gina Ch. 06

Tommy fucks Gina's ass for the first time.

by Tommy1982 in Anal 08/17/2006
H
4.5
119.8k
18
1
22

Anal Peep Show

Young man discovers anal sex for the first time.

by wiley4377 in Gay Male 09/20/2017
4.49
62.8k
64
1
86
0

The Audit Ch. 03

Accountant gets everything from Amy, including anal virginity.

by SandmanNC in NonConsent/Reluctance 12/01/2008
4.49
84.8k
14
7
21

Tonight Ch. 01

She has all day to think about his anal intentions.

by live2write in Anal 10/18/2007
4.49
43.5k
8
4
10
0

He Fucks My Virgin Ass

He takes her anal virginity.

by Slut2theHeart in Anal 04/14/2007
4.49
432.6k
142
21
171
0

A Russian Rose Ch. 07

Anya's desire to care for her man leads to something new.

by AedanSayla in Anal 06/03/2021
4.48
13.8k
11
2
20

Daria and Jack Pt. 01

Babysitter gets caught with her hand in her pants.

by Bliss2Kiss in NonConsent/Reluctance 06/21/2019
4.48
111.8k
157
14
219

A New Awakening

Ben takes a young man under his wing.

by PhantomOfMoonlight in Gay Male 12/23/2010
4.48
57.8k
23
4
31
0

Taking My Ass

I want you to take me, there...

by towhead in Anal 07/04/2009
4.47
99.9k
24
4
39
0

Harleys Surprise

Identical twins surprise Harley for her birthday.

by CaseyMathis in Erotic Couplings 08/03/2021
4.47
15.9k
14
0
29
0

Shelby's Troubles

Shelby gets more than she bargained for at the chiropractor.

by dirtygirljenna in Anal 04/09/2013
4.47
105.5k
33
9
44
0

Ali Teaches Anal

Our delectible neighbor has a request.

by onlyinmydreams in Anal 09/04/2012
4.47
77.1k
42
2
48
0

Chloe's List

A first time anal story featuring a man and woman.

by AlexSlaine in Anal 11/19/2017
4.46
33.4k
11
4
18
0

Education of Chelsea: New Lesson

chelsea's Master takes her into "virgin" territory.

by simply_cyn in Anal 11/05/2005
4.46
135.8k
17
1
18

Birthday Anal

His birthday wishes come true as my ass stretches around him.

by Goey in Anal 06/22/2012
4.46
115.2k
35
4
54
0

Wrong

A short foray into anal.

by Twisted_Mistress in Anal 06/24/2012
4.46
105k
41
11
53
0

In-Depth Anal Research

My BFF and me get our anus stretched.

by Leezy in Anal 07/21/2018
4.46
111k
68
0
98
0

Flexible Booty

18 year old gives up her virgin ass.

by Goldeniangel in Anal 04/04/2011
4.45
185.9k
95
6
122
0
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