‘first time anal’ stories

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first time anal 

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"Wonder Woman" Takes it in the Ass

A costume party leads to first time, anonymous anal sex.

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4.75
411k
778
48
1.1k
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The Bet 11: Friday Shenanigans

The fun begins for Sarah, Henry and John.

H
4.66
5.9k
9
0
19

Working With Rex Ch. 05

Becki and Rex make a wager that leads to the unexpected.

4.3
5.1k
2
0
4

The Monster under The Bed

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

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4.71
62.2k
297
17
472
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Finding Ivy Ch. 13

Ivy has fun with cousins.

4.45
4.3k
6
0
7

20 Years in the Making Ch. 02

Round two with Rachelle means I take her ass.

4.03
26.9k
12
0
13

Prom Night Pegging

Prom date reveals how naughty she really is...

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4.79
202.8k
618
50
937
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The Swallow

Rachel goes undercover to catch a traitor.

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4.54
9.9k
8
3
20
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3rd Time with a Guy/1st Time Anal

Used Online Personals to Hookup, 3rd times the charm!

4.32
14.6k
3
3
6
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Surrogate Experiences

Laura talks Tommy into trying it with a man.

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4.69
32.8k
19
8
49
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The Seduction of Roger Ch. 03

He gets unexpected help in pushing Roger to explore.

0
6.4k
16
3
23

Buttermilk Pancakes Pt. 02

First time anal, boyfriend offers comfort & care.

4.09
21.6k
5
1
14

Buttermilk Pancakes Pt. 01

First time anal, boyfriend offers comfort & care.

4.07
21.8k
7
2
18

Cathy's Summer Pt. 07

Cathy and Ron enjoy another 'first'.

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4.52
7.7k
5
1
9

From Best Man to Craving Cock

My brother's bachelor party leads to me wanting my cousin.

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4.72
91.1k
242
18
345
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Cherry

There's a first time for everything.

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4.6
59.9k
41
5
68
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I became my girlfriend's slave Ch. 02

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

4.34
34.4k
29
3
42

My Prescriptions Please

A beautiful customer service attendant spurs my sexuality.

4.33
9.3k
3
1
4
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Lydia, Oh Lydia Pt. 01 (corrected)

Woman discovers her sexual self.

4.32
9.1k
2
0
9

That Money Spinning Idea

Two hard up students have an idea for extra income.

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4.51
20.5k
29
4
39
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A Tale of Two Brothers

Different Career Paths, Same End Result.

4.47
34k
21
2
45
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Just Friends?

She thinks they're just friends. He proves her wrong.

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4.77
194.5k
391
30
591
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Job Interview, Anal Intentions

Her loving sister arranged the anal meeting.

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4.54
83.9k
111
8
164
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Little Red Pill Ch. 02

Noah continues to grow, and returns to the gym.

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4.6
39.2k
34
4
47

Gwennalyn's Sexual Awakening Ch. 15

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

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4.56
9.3k
10
3
21

One Ordinary Day, with Penis Ch. 01

Voice training really pays off.

4.41
20.2k
23
0
44

Asleep

She pretends to be asleep while he fucks her ass.

4.27
68.1k
40
4
66
0

Skin Deep Loathing Pt. 02

Will Micha's comeback sign an end to the feud?

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4.65
3.8k
4
3
5

My Trans Sex Life Ch. 02

My adventures continue with my first anal experience.

4.38
19.5k
14
2
20

My Sexy Wife Jennifer Ch. 06

Jennifer Continues Kate's Sexual Education.

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4.64
23.7k
19
0
34

Just the Tip

He's too big for her tight backdoor, but just the tip...

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4.73
681.3k
1.1k
59
1.5k
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Daddy's New Girlfriend

Sneaky daughter gets more than she bargained for--in her ass.

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4.81
426.6k
730
38
1.1k
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Battered & Bruised

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

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4.59
63.8k
108
10
181
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Trucker Turned Me Out Pt. 01

Young man meets a trucker online.

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4.58
46.9k
52
8
73
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A Very Fun School Trip Pt. 02

The excitement continues, and new things are tried.

3.57
9.3k
1
0
4

The Caregiver Ch. 03

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

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4.61
27.3k
10
1
10

Making of a Slut

From the Kohala coffee fields to Waikiki hotel rooms.

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4.52
16.5k
13
3
22
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Liliah Willowmist Ch. 04

Korinne copes, Zan devises a plan, Corellion and Lili adjust.

4.56
2.7k
2
0
2

Mr. Grinch

Fred's Christmas was stolen it comes back.

4.07
38.9k
32
57
34

Anything I Want?

A poker bet puts Jackie's tight ass in the pot.

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4.73
587.5k
840
44
1.2k
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Rebecca's Rebirth Ch. 01

A young woman finds her true self.

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4.75
21.2k
31
0
54

The Devil Comes Out at Night Pt. 07

The neighborhood is friendly, so the Devil settles in.

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4.84
25.7k
16
0
28

Three Toppings

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

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4.53
42.3k
52
3
66
0

Harry and Maggie

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

4.48
37.3k
38
2
49
0

Domestic Wife Ch. 08

Husband punishes submissive wife with first time anal.

4.34
111.9k
41
9
68

Feet on the Ceiling Pt. 03

Discovering that my fuck buddy is the love of my life.

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4.56
11.5k
15
1
18

How Did This Happen?

Naïve housewife gets screwed repeatedly.

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4.58
418.3k
338
16
537
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Out of Control

Sometimes a wife needs a good belt.

4.05
90.9k
60
33
113
0

It Has Led to Dancing

College roommates of circumstance learn from each other.

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4.76
144.8k
163
19
221
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Coming Out to My Stepdad

My Step Dad fulfilled my fantasy of losing my cherry to him.

H
4.66
166.9k
219
12
339
0

Breakfasts with Tiffany

Relaxing naked is one thing, but with company...

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4.77
406.6k
382
34
510
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The Making of an Ass Man

Changing his perspective.

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4.72
123k
114
7
176
0

Dani in the City Pt. 03

An abusive client subjects Dani and Bianca to an ordeal.

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4.6
24.1k
15
8
24

Rob, Robin and Darin Ch. 02

Darin takes Rob's cherry in a weekend of threesome sex.

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4.73
32k
25
2
29

Morning Coffee with Jeannie

Morning coffee makes everybody crazy, including the author!

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4.53
89.2k
71
18
128
0

Five Trailers, Lot A

Handsome landlord shows young mommy the pleasures of anal.

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4.53
94.1k
66
17
101

Client Satisfaction: Anal Play

Secretary gets trained for her new (anal) position.

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4.56
259.2k
294
20
443
0

Rohit's Dilemma

Rohit receives a mysterious sex tape.

4.45
35.1k
39
4
63
0

This is Out of Control!

Hot sister is too much to resist, but mom...

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4.71
582.5k
870
67
1.2k
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Spinal Meningitis is No Joke Ch. 04

Jeannie and Charlene get rear-ended.

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4.78
238.9k
244
13
305

D.O. Wilson Ch. 02: Recalcitrant Wife

D.O. Wilson punishes a cheating wife.

4.41
68.5k
20
4
35

Alyson's First Anal Experience

Alyson's friend and her boyfriend show her the joys of anal.

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4.58
130.5k
115
5
172
0

First Experience Topping a Couple

My first time as a Dom to a couple.

4
17.3k
9
1
13
0

Sydney Cox - The Beginning

Naive girl leaves the farm for the first time.

3.35
23.6k
8
0
8
0

Thai Girls are the Best

Discovering all of my fantasies in Bangkok.

4.13
64.9k
18
0
32
0

Reunion in the Pines

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

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4.5
18.6k
13
2
19
0

The Very Fortunate Accident

An unexpected special treat after a night out.

4.42
48.6k
18
3
29
0

He was My Boss Ch. 02

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

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4.6
24.4k
23
14
24

A Road Trip Fantasy

Doctor and nurse find love on a move across country.

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4.84
28.5k
44
7
59

Losing My Virginity to BBC

The story of the time I lost my anal virginity to BBC.

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4.53
148.4k
168
27
212
0

Belated Birthday Present

Good things cum in those who wait...

4.22
29.9k
26
5
34

My Roommate Mark Pt. 02

Mark wants to try something new.

4.47
34.4k
30
3
40

Ms. Morgan's Dilemma

Christa tries to seduce her teacher, tries something new.

4.1
38.5k
8
2
13
0

A Blessing in Disguise

Rough anal sex can, sometimes, save a relationship.

4.04
51.4k
32
2
40
0

The Blue Life Ch. 39: On the Phone

I begin seducing a virgin teen over the phone.

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4.66
12.8k
13
3
22

Archived Memories

An older woman learns from a young teacher.

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4.62
47.3k
39
9
53
0

Learning to Surrender Pt. 01

Rick loses his virginity to his new older lover.

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4.73
113.6k
170
19
230

Allison

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

4.33
16.4k
8
0
14
0

How to Have Anal Sex

Roommates explore anal sex with a Doctor’s cock.

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4.66
146.5k
129
13
181
0

Time for a Change

A man moves to a new town and becomes the neighbor's sissy slave.

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4.71
125.5k
163
17
229
0

Good Guy all the Bad Girls Want Pt. 04

Sharon teaches Ben best Anal practice.

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4.69
35.8k
35
4
41

Borrowed Dreams

A chance encounter in a store lead to new experiences.

3.62
8.5k
2
0
2
0

Cock Sucking Club Ch. 03

Tony calls again and is looking for more from Mike.

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4.61
42k
41
20
50

Damsel in Distress

My first story, please tell me what you thought of it.

3.8
12.5k
4
10
5
0

The Snowman Experience

Hot housewife gets ass drilled by demonic snowman

3.9
13.1k
11
2
16
0

Losing Our Anal Virginity Together

We've never tried it--until now.

4.11
78k
15
15
20
0

The Palace

A virgin is initiated as a slave at the mysterious Palace.

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4.51
135.6k
111
8
191

Insatiable Rob & Eric Ch. 10

Eric and Jay satisfy Rob, but Jay wants.

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4.57
10.3k
4
0
5

Sharon Takes It in the Ass

This time, no is not an option!

3.9
89.7k
27
7
41
0

Are You Sure About This?

He joins his lesbian Mother and her gf in a threesome.

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4.57
388k
625
45
910
0

High School Beautiful Ch. 03

Maddy does more for an A on an exam.

4.3
56k
21
5
22

Back End Love

A couple tries anal for the first time.

4.09
41.9k
8
1
10
0

Alicia's Descent Ch. 02

A gentlewoman and her maid whore themselves to sailors...

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4.66
18.7k
23
0
27

The Removalist

Removalist gets more than he bargained for from a client.

4.29
15.2k
4
0
5
0

Pleasure Spots: Anal Education

Sex therapist helps a wife explore unique pleasures.

H
4.74
144k
143
22
202
0

The Making of a Real Bathhouse Slut

A mature married man finds his true calling.

H
4.6
61.8k
64
19
79
0

Texas Trio Ch. 24-End

Cat, Colt, & Jem- the final resolution.

H
4.81
21.3k
22
11
32
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