‘anal virgin’ stories

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anal virgin 

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An Admirer

A long term Admirer meets a real TGirl.

H
4.63
21.3k
35
4
43
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Three Models in a Vegas Hotel Room

Post photo shoot, I relax with hot bathing suit models.

H
4.58
27.3k
15
0
30
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I Need... Pain

She must ask her master for what she needs.

4.32
20.6k
16
1
27
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Connor on Campus Ch. 01

Connor takes a fresh-faced virgin back to his dorm.

0
34.3k
55
9
76

Salt's Quest for Charisma

Salt loses his anal virginity on Halloween.

0
28.5k
10
7
19
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Sharing My Friend's Wife

Marie has sex with another man while her husband watches.

4.48
128.8k
122
32
185
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That Was The Week That Was

I have more ass (almost) than I can handle. I'm kidding!

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4.63
20.8k
13
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18
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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
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That Was The Weekend That Was

Details on my affair with Lisa and other ladies in Vegas.

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4.56
17.4k
13
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19
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The Affair Continues in Las Vegas

Lisa and I spend a very hot weekend in Las Vegas.

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4.65
24.1k
18
1
25
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Monica the Maid's Three Hole Day

On her third day, I take her ass for the first time.

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4.56
29.2k
18
1
29
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Borrowed Dreams

A chance encounter in a store lead to new experiences.

3.62
8.5k
2
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2
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Bi-College Girls 02 - With Toys

Bi-curious girls' first anal.

4.38
35.5k
13
1
18
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Castle Slave Ep. 01: Rose Girl

A new life of chastity for Belinda.

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4.55
59.3k
53
3
127

Jennifer's Twisted Fate

Jennifer gets anal gang banged by a group of unknown men.

4.45
142.7k
117
5
167
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Drunk Samantha

Drunk Samantha is way naughtier than sober Samantha.

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4.65
188.3k
177
9
267
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Reports Ch. 03: Mr. Bradford

Mr. Bradford spanks me and dominates my ass.

4.4
15.6k
8
0
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Bartender and Strangers

You and the bartender meet me in my room.

4.34
19k
10
1
14
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Dad My First Lover Pt. 01

Father and his CD daughter with occasional sexual encounters.

4.32
85.7k
45
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57

Late Night First Time Anal

Forbidden friends reunite for her first anal experience.

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4.66
111.6k
94
8
125
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The Shadow Doctor Ch. 02

The Flying Darkness - Craving Release - Tam Loses his Temper.

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4.75
35.4k
39
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Straight Guy Asks Me To Use Him

A query from an online newbie who wanted me to use him.

4.23
37.9k
19
5
23
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A Weekend to Remember

Romantic weekend after a busy time.

4.23
51.6k
21
19
28
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Play Time is Over

A young girl loses her anal virginity to an older man.

4.27
60.6k
11
0
21
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Caught & Rewarded

Who knew finding your wife cheating could be so rewarding?

4.11
78.7k
55
13
84
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His Sweet Girl Ch. 04

Boss takes young secretary's ass publicly.

4.49
63.3k
34
2
38

Lily’s Anal Curiosity

She loses her anal virginity (on film).

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4.62
207.7k
236
15
318
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Submissive Sally Ch. 02

More submission for Sally.

4.35
29.9k
12
0
17

A Trip not to be Forgotten

Family trip to India for me, my wife and sister takes a turn.

3.61
58k
12
3
21
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Ashley’s Anal Curiosity

Threesome with husband and her sexy best friend.

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4.63
375.3k
353
40
528
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Mia's Anal Cherry

Mia loses her last cherry to Alex

4.35
52.6k
42
1
50
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Sally’s Wish, Anal Education

Her anal virginity is pushed to the limit.

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4.69
240.9k
146
11
217
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Cara, Daddy, and Uncle Johnny Ch. 04

Daddy helps Uncle Johnny teach Cara about anal sex.

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4.55
352k
360
17
454

Sex Therapist Ch. 01

Couple wanting to revive their sex life get abused.

4.32
58.5k
34
2
56
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Fucking Anal or Anal Fucking

At last I give my bum away.

4.4
84.1k
29
15
38
0

Anal Invaders

Throwing caution to the wind. Not always the best of ideas.

3.04
28.1k
7
4
9
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The T(h)rustful Voice Pt. 01

51% incestuous, 49% T-girl enthusiast. Also, hearing voices.

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4.5
39.5k
41
8
56
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Buttfuck Buddies Ch. 01

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

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4.75
680.6k
1k
62
1.3k

Taken for the First Time Ch. 01

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

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4.65
459.1k
414
111
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Toying With a Fantasy

My imagination runs wild and takes you along for the ride.

4.29
12.6k
1
0
4
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Teenage Fantasy Cums True Ch. 03

Both of them lose their anal cherries.

4.46
58.4k
30
3
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Enjoying My Brother

Straight guy finds his bi side with his brother.

H
4.54
120.9k
148
13
198
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He Did What He Did To My Rear

The very painful truth about her first anal. And a song.

3.65
74k
16
4
17
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Stuck in the Middle Ch. 02

They take his anal virginity.

H
4.73
60.9k
55
6
72

Birthday Bondage

Girlfriend's first time in bondage for boyfriend's birthday.

4.09
101.7k
82
11
117
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Hot & Bothered

Wife wants sex after her run; he has a surprise for her too.

4.35
99k
40
11
53
0

Me and My Neighbor, the Married Man

My neighbor gets a little drunk.

4.05
60k
23
1
36
0

A Thorn in the Rosebud

An older man takes my anal virginity.

4.06
106.4k
18
2
22
0

Gabby Fucks Three Strangers

Gabby pays off a drink with something more than money.

3.59
69.6k
23
0
39
0

Norse Myth Models

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

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4.5
74.4k
24
9
37
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Mira Ch. 01

A girl upgrades to a new version of her favorite game.

4.35
61.2k
45
1
65

Corporate Whore

Abbey becomes anally submissive to her boss.

4.36
388k
364
18
513
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Karen and Me

An uncle and his t-girl niece celebrate her birthday.

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4.5
96.2k
89
11
105

Mustang Claire's Gift

A career change had separated Clair and Jack. Reunion time.

4.45
20k
6
2
11
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The Breeding Bitch

Mother Superior trained her well.

4.09
110.2k
36
5
51
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Jen's Revenge

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

4.07
45.6k
15
2
25
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Sweet Temptation at the Workplace

Taken man can't resist when dream girl suddenly wants him

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4.58
87.6k
89
6
115
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His Cum Is Mine

Ali is Mistress for a day

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4.57
42k
22
2
33

Anal Along the Bosphorus

A harem recruiter gets to test run the Sultans concubines.

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4.64
87.2k
104
12
134
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Taken by the Wolf Ch. 14

Bella loses her anal virginity

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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

Guess What I Saw? Ch. 05

Monica, Kelly, and Tony finish what they started.

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4.8
37.4k
14
10
16

Revenge is a Dish...

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

4.46
55k
12
2
21
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First Time For Everything

Anal virgin has the perfect next door neighbor!

4.21
88.1k
14
3
20
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Garden Pleasure Ch. 02

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

4.34
45.2k
10
1
17

Erika Blossoms Ch. 12

Erika makes a date; Tells Jana her fantasy.

4.39
18.2k
5
6
6

Once Upon a Hotel Room

Buisness woman is taken and forced by hotel staff.

3.88
161.9k
29
1
50
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Erica's Journey of Discovery Ch. 02

Erica gives her last remaining virginity to Alan.

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4.68
14.9k
7
0
10

Dreaming of You

Katie dreams of losing her anal virginity.

3.86
32.5k
4
2
6
0

A First, My Friend's Sister Ch. 06

They enjoy their roller coster ride of a summer together.

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4.73
253k
131
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Of Lords and Ladies Ch. 04

Allys proves enthusiastic and a new day dawns.

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4.5
48.8k
17
7
19

90% True Ch. 09

How Jen lost her anal virginity.

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4.65
104.9k
27
3
34

An Ass for Valentine's

Katrina gives her virgin rear to her lover.

4.28
73k
16
4
22
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Experimental Anal

First-time anal among young lovers.

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4.55
97.3k
27
8
42
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Frozen in Time Ch. 02

He freezes time and makes Lorena his lover.

H
4.51
113.4k
84
7
101

The Night I Lost My Virginity

Tale of a big woodsman being taken by a small woman.

3.95
57.8k
9
4
16
0

Cocking a Virgin Ch. 02

Taking her virgin ass.

4.24
58.6k
20
1
23

Deepest, Darkest.

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

4.46
56.9k
26
3
33
0

Matty Meets Kimmy Ch. 03

Matt and Kim's relationship continues to grow.

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4.67
26.8k
11
4
13

Emmanuel and Anna Ch. 03

Anna's torment continues as John takes her.

3.86
38.4k
6
5
8

Ally Ch. 01

A senior has her boundaries pushed.

3.42
52.7k
16
2
19

Mr Valens Back Door Policy

Lawyer has anal sex with young cleaner.

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4.55
122.9k
62
9
84
0

Bend Over For Me..Just Like That..

He has his first experience performing anal sex.

3.92
97.3k
16
2
21
0

Her Toy Takes My Cherry

The wife shows me the joys of pegging.

H
4.53
182.4k
126
21
184
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Shortening His Sentence

All he has to do is date the worst shemale inmate.

H
4.65
185.1k
249
20
313

Breaching Gloria

Wife enjoys first anal sex.

H
4.63
186.4k
129
13
172
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Submission Ch. 12

Master takes her anal virginity.

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4.75
140.8k
83
6
96

Taking the Good Girl

He overcomes her reluctance and takes her virgin ass.

4.43
262.4k
195
13
256

Snapped: A Shemale's Story

Reject her at your own risk.

H
4.51
254.7k
205
15
249
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Rekindled Ch. 03

The first morning, first lessons, first surrender.

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4.65
21.4k
12
6
13

The Handyman is a Real Handy Woman

While the girlfriend's away, the handywoman and I will play.

H
4.7
195.5k
358
29
423
0

New Neighbour Ch. 02

Jacob and Natalie involve a young blonde in their adventures.

H
4.68
69.4k
27
1
36

Kim's Story Ch. 03

Kim and Summer meet the Principle.

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4.53
24.4k
14
2
16

Kim's Story Ch. 02

I get my anal cherry busted.

4.4
52.4k
20
6
24

A Fishing Trip, But I'm The Bait Ch. 03

Jane finds the road to lust can be bumpy.

H
4.54
41.1k
21
5
26

Snowball's Chance

Valentine's Day snowstorm brings us all together.

4.3
77.2k
19
5
29
0

A Fishing Trip, But I'm The Bait Ch. 01

A day of many firsts promises a future as Jane.

4.44
96.9k
63
16
89

Dainty Daphne Ch. 02

Daphne gets Daddy to introduce her to anal.

H
4.52
105.2k
53
12
65

Sissy's New Toy Ch. 02

A sissy and his girlfriend take panty-time to a new level.

H
4.51
56.9k
24
10
30
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