‘anal first time’ stories

Active tags
Active tags
anal first time 

Category

Misty Acres

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

H
4.52
11.3k
9
1
26
0

My First Time - Anal Sex

Finally take the plunge loosing my anal cherry.

4.42
17.8k
7
4
15
0

Your Love's Whore

Megan could be Matt's perfect girl.

4.26
10.9k
4
31
21

The Cupid's Arrow Challenge

A viral Valentine's Day love spell backfires.

4.32
15.3k
14
8
33
0

Educating Laura: Anal Time

She plays with toys and Richie. Experiments are fun.

H
4.55
21.1k
8
7
18
0

Daddy's Anal Virgin

I'm ready, please be gentle.

H
4.67
39.4k
30
1
66
0

Sundays

Sensual Sunday stroll down memory lane.

4.4
3.4k
6
3
7
0

Roxanne and Her Mother's Boyfriend

Daughter has sex with mother's boyfriend.

3.9
12.3k
19
0
30
0

The Connoisseur Ch. 15

In Which I Take Sarah's Last Virginity.

4.45
14.6k
11
3
17

Harleys Surprise

Identical twins surprise Harley for her birthday.

4.46
15.7k
14
0
29
0

A Russian Rose Ch. 07

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

4.48
13.7k
11
2
20

My First Gay Experience

A gay roommate uses his straight roommate.

H
4.59
75k
125
12
196
0

Gangy's Gap Ch. 06

The Tale of Agnetha and Draxas.

4.2
6.5k
8
11
15

Tiny Asian Cocktease - He

Asian girl wants to be taken by a white stud or does she?

4.18
35.2k
38
8
87
0

Jazzy's Cunnilingus Quest

Jazzy goes bowling and balling.

3.36
7.6k
4
0
10
0

Modelling for the Church

No one told her she was required to gape for the camera!

4.14
75.9k
81
8
128
0

My Dream

A girls visit to a sex club turns into a very wild night.

3.43
25.7k
6
4
20
0

Three Sons Pt. 05

Tara comes to terms with Daniel's cuddling with his mom.

4.33
18.9k
24
1
35

Mistress K Letters 12: Anal V Card

Mistress claims reluctant male slave's anal virginity.

4.36
14.1k
12
3
18

Devil's Feast

Hot friends enjoy a Halloween dinner theater orgy.

H
4.65
36.1k
30
6
57
0

Halloween Odyssey

Hot blonde tricked into foursome by possessed garden gnome.

H
4.65
25.6k
37
6
68
0

Nellie and the Diamond Gala

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

H
4.81
378.8k
240
47
351

That Time I Lost My Virginity

Losing my anal virginity.

3.92
34.9k
5
1
9
0

Cherry

There's a first time for everything.

H
4.6
59.9k
41
5
68
0

Daria and Jack Pt. 01

Babysitter gets caught with her hand in her pants.

4.48
111.3k
157
14
219

The Crazy Sexy Cat Lady Ch. 02

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

H
4.51
11.8k
7
3
11

Taking Your Ass

A first time pegging story

4.33
79.1k
39
6
77
0

Passing the Torch Ch. 02

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

H
4.56
43.8k
66
22
95

Little Sister's Big Butt Ch. 02

Michelle and Tyler get much, much closer...

H
4.69
204.5k
325
19
418

In-Depth Anal Research

My BFF and me get our anus stretched.

4.46
110.5k
68
0
98
0

Horsemaster's Captive Pt. 03

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

H
4.69
21.2k
16
8
22

An Offer He Can't Refuse Ch. 07

Lyla and Mike have a talk, and more.

H
4.78
78.1k
127
9
190

Homework Assignment Ch. 01

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

H
4.53
19.4k
6
0
11

Loopholes Ch. 02

Tessa has an amazing surprise for Nick...

H
4.78
269.7k
192
12
231

He was My Boss Ch. 02

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

H
4.6
24.4k
23
14
24

Lifestyle of a Housewife

A housewife cheats to get anal.

4.21
66.3k
25
0
36
0

Back Rub

A husband's back rub turns into something unexpected.

4.32
93.5k
39
5
52
0

Chloe's List

A first time anal story featuring a man and woman.

4.46
33.3k
11
4
15
0

In The Playroom

Pleasure, punishment and first-time anal

4.35
67.8k
34
1
60
0

Anal Peep Show

Young man discovers anal sex for the first time.

4.49
62.5k
63
1
84
0

I Want Your Anal Virginity

I promise to be gentle.

4.39
114.7k
40
6
60
0

Borrowed Dreams

A chance encounter in a store lead to new experiences.

3.62
8.5k
2
0
2
0

Our Story Ch. 02

He takes my ass.

H
4.51
57.9k
27
4
34

My Anal Questions Answered

I learned how anally erotic I am.

4.35
38.2k
13
0
17
0

Back End Love

A couple tries anal for the first time.

4.09
41.9k
8
1
10
0

Spitroast

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

H
4.58
77.7k
83
4
103
0

Drunk Samantha

Drunk Samantha is way naughtier than sober Samantha.

H
4.65
188.2k
177
9
267
0

Grandpa Wants My Ass

Grandpa fucks grandson.

3.82
136.4k
35
10
43
0

Jeff and Paige

Love between and older man and a young woman.

H
4.68
91.3k
82
0
100
0

Shemale Bar

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

H
4.63
568.8k
980
113
1.2k
0

My Loss to Arabia

Janet seeks an Arab lover and suffers the consequences.

4.39
27.1k
16
6
23
0

Ashley’s Anal Curiosity

Threesome with husband and her sexy best friend.

H
4.63
375.2k
353
40
528
0

Sugar Heart Ch. 05

Richard and Buddy go deeper, at last.

H
4.87
38.2k
73
35
86

The Groom's Tale

Shy stablehand recounts first time and how it changed him.

4.22
34.1k
8
6
12
0

Good, Clean Fun

Young couple discovers anal pleasure.

H
4.5
52.3k
17
4
22
0

Revenge of the Nerd: Ex-Bully's Mom

Nerd dominates bitchy MILF and takes her virgin asshole.

H
4.55
683.1k
794
42
1k

Buttfuck Buddies Ch. 01

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

H
4.75
680.5k
1k
62
1.3k

Taken for the First Time Ch. 01

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

H
4.65
458.9k
414
110
509

Her Brother Ch. 01

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

H
4.79
220.6k
519
78
678

Backdoor Sweetheart Ch. 01

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

H
4.7
574.1k
960
38
1.3k

Unexpected Awakening

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

H
4.59
104k
68
19
82
0

Sweet Baby James

Argument leads to a first.

2.88
35.7k
6
5
8
0

It Started With a Kiss

A tale of longing, insecurities and sibling love.

H
4.66
180.7k
192
14
285
0

I Bet You'll Like It

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

H
4.71
1.41M
2.4k
115
3.2k
0

Anal Summer Ch. 01

An erotic coming of age tale of sexual awakening.

H
4.58
151.6k
147
15
205

Picture Perfect Ch. 03

After some unfinished business, Jason finally bottoms.

H
4.87
57.4k
106
29
122

Because I'm Your Sister Ch. 02

Loving siblings wake up to a dream come true.

H
4.68
206.3k
256
30
305

Straight Teacher Turned

Straight teacher is turned by two ex-students.

H
4.56
223.3k
262
28
338
0

Whatever Didi Wants Ch. 04

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

H
4.66
77.5k
113
15
130

Weird Sisters Ch. 02

His girlfriend's twin sister has a weird request.

H
4.77
261.2k
393
17
483

Weird Sisters Ch. 01

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

H
4.71
356.1k
617
16
931

A Birthday Butt Plug Surprise

She's new to anal, and she gets a surprise on her brithday.

4.2
127.9k
44
3
65
0

Norse Myth Models

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

H
4.5
74.4k
24
9
37
0

Sensual Anal

A young woman's first experience with back door love.

3.87
79.9k
19
4
21
0

Taken by the Wolf Ch. 14

Bella loses her anal virginity

H
4.72
108.8k
75
9
89

AnnaSophia Goes Anal

AnnaSophia Robb asks friend to take her anal virginity.

4.45
37.1k
40
0
49
0

My First Anal

Nicole begs for reconciliation by offering her Anal cherry.

4.14
141.1k
49
4
62
0

The Hard Hit

A hitman is surprised by his attraction to his target.

H
4.52
64.5k
51
11
70

An Ordinary Man's Life Ch. 09

Donna offers Todd her anal cherry.

H
4.68
21.4k
9
0
10

Revenge is a Dish...

A "what if..." fantasy story about me losing my anal virginity.

4.46
55k
12
2
21
0

First Time For Everything

Anal virgin has the perfect next door neighbor!

4.21
88.1k
14
3
20
0

Garden Pleasure Ch. 02

Victorian widow Grace runs away and ventures in a New World.

4.34
45.2k
10
1
17

Shower One-on-One

She eagerly gives him her anal cherry in the shower.

4.32
56.6k
21
2
24
0

Trust Ch. 03

A gay man falls in love with a straight one.

H
4.59
16.7k
22
0
24

Take Two

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

H
4.53
149.9k
60
6
90
0

Three Cheers for Aldo

Couple breaks in wife’s new shoes, and her ass.

4.28
38.1k
2
1
4
0

Anniversary Present

A loving wife gives her husband her anal virginity.

4.29
87.7k
24
3
32
0

Sis's Anal Awakening

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

H
4.54
449.1k
396
29
476
0

Fuck My Ass!!

A mature woman knows what she wants and what she needs.

3.95
205.2k
21
2
35
0

Dreaming of You

Katie dreams of losing her anal virginity.

3.86
32.5k
4
2
6
0

Ethan's Grace - Anal Edition

Ethan introduces Grace to anal play.

H
4.64
92.8k
40
8
56
0

Old Man Discovers... Ch. 12

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

H
4.56
22k
4
2
4

Shelby's Troubles

Shelby gets more than she bargained for at the chiropractor.

4.47
105.3k
33
9
44
0

Braining Ch. 05

Blair and Jenn.

H
4.78
42.5k
19
6
22

First Time Swinging

Blonde Dayna and her BF Georgia share Georgia's hubby.

4.24
71.4k
24
6
37
0

Whore Elle: Gives up Anal Cherry

Before I became a whore, I had to lose my anal virginity.

4.02
91k
30
5
46

90% True Ch. 09

How Jen lost her anal virginity.

H
4.65
104.9k
27
3
34

Chains of Fire

A slave learns to love anal.

3.47
67.7k
9
0
12
0

Valuation

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

H
4.72
73.5k
66
17
80
0
Active tags
Active tags
anal first time
Separate tags with commas. More info in the FAQ