‘first time anal’ stories

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Active tags
first time anal 

Category

Scoring Points

A macho hetero boy on holiday get used.

4.24
6.6k
11
4
19
0

Ready for My Close-Up

Jake and Ethan's movie scene rehearsal goes off-script.

H
4.83
10.7k
26
6
44
0

The Birth of a Size Queen

I wanted it, and I got it.

H
4.76
12.4k
35
3
53

That Empty Colon Feeling

Joanie gets relief and goes out to celebrate.

4.42
4.3k
1
6
11
0

Purity Ch. 06

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

4.46
9.1k
6
0
12

Rescuing Sweet Olivia 02

RESCUING SWEET OLIVIA 02.

H
4.75
5.6k
6
0
23

Anna's New Business Ch. 03

Anna faces her own sexuality and her risks.

H
4.69
3.5k
6
4
22

Gina Helps Joey Become Julia

Gina gives Joey a makeover, turning him into Julia.

H
4.74
16.8k
32
7
69
0

Late Night Lesson Long Ago Ch. 04

Gary gets a big surprise morning after pool party with Al.

H
4.71
3.3k
3
3
5

Realtor Saw me Dressed Pt. 03

Realtor& friend, take CD’s virginity.

H
4.71
6.6k
20
3
32

Starting Over Pt. 02

Joe's bed has a surprise guest.

H
4.81
8.1k
15
7
27

My Queer Cousins Ch. 04

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

H
4.84
2.9k
5
2
7

My Queer Cousins Ch. 02

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

H
4.85
4.5k
12
5
18

Caught on Nanny Cam Pt. 02

Johnny gets caught on nanny cam in a french maid dress again.

H
4.77
10.5k
26
2
36

My Muse

A massage turns into something more.

H
4.6
8.7k
8
1
14
0

Why Can't I Resist My Ex

My Ex visits and sexual sparks fly.

4.44
5.7k
2
1
12
0

Oz Beach Boy & Odessa Try Anal

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

H
4.57
12.6k
6
1
15
0

House Call

A sick man finds he has really good insurance

H
4.58
19.5k
13
29
34

She is Tied Down & Taken

He fulfills her deepest fantasy of being tied down and taken.

H
4.59
19.6k
20
1
39

The Experiment - Redux Ch. 04

Rebecca has her second round of group sex.

3.85
5.4k
4
0
9

The Visitor Returns

A whole new experience with the nameless stranger.

4.29
8.2k
9
1
13

The Perfect Fuck Buddy Ch. 07

Ariel wants to try something new.

H
4.58
11.3k
22
1
28

Do You Want to Hold My Cock? Pt. 02

Straight guy ends up liking having his ass eaten.

4.43
22.3k
25
2
42

Lisa, Scott and Me Pt. 02

At our next meeting Lisa and Scott surprise me.

H
4.75
11.2k
24
6
29

Her Body, Your Choice Pt. 03

Aoi gets a job and her dynamic with her friends evolves.

H
4.79
5.1k
5
1
10
0

Honeymoon Dee-Lite

Newlyweds discover anal sex together.

H
4.58
27.9k
21
7
43
0

Into the Woods Ch. 03

The fun continues.

H
4.72
6.6k
11
4
13

A Couple's Fijian Vacation Ch. 06

Caitlin is keen to have a threesome.

H
4.57
9.8k
13
2
19

Happy Birthday, Erica Pt. 02

Happy birthday, Dominic.

H
4.66
7.8k
4
0
8

How I was Trained Pt. 05

Amy gets mad at me but sets me up with my first man, Mike.

H
4.83
12.2k
21
5
27

Holes in the Wall

Evie and Dana become unwilling party sluts.

H
4.52
100k
171
9
322
0

Raped by Her Loving Boyfriend

Boyfriend comes home from university, takes her anal cherry.

3.74
43.9k
36
2
61
0

Double Entry

Ros meets her husband's friends and makes them feel at home.

4.46
26.3k
16
0
35
0

Customer Service

Looking after her customer’s needs.

H
4.52
23.9k
14
2
25
0

Kiera's Passion

A conservative housewife discovers the joy of anal sex.

H
4.77
107.5k
68
17
134
0

My New Personal Assistant Ch. 08

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

H
4.72
11.4k
12
3
22

Asexual Wife Whores Herself Out Ch. 03

She surrenders her ass, her last unused hole.

3.71
16.2k
8
0
11

My Friend's Brother Pt. 04

10 Yrs Later - My Ultimate Threesome Comes True.

H
4.8
13.3k
22
4
36

My Name is David

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

3.89
27.6k
13
0
32
0

Collecting The Rent Ch. 03

Troy and Colin ae inseparable. What about Toby?

H
4.5
3k
2
2
5

The (slight) Feminization of Tommy Ch. 03

Role playing comes with a cost. We need to talk.

H
4.53
5k
3
1
5
0

Visiting My Mormon Friend 03

Tending to an Expanding Flock.

H
4.6
18.1k
8
1
12

Donald Comes to Town Ch. 04

Logan takes Sebastian's 18 yo cherry ass, Jeremy joins in.

H
4.86
13.8k
33
8
47

Tough Loss

Consoling my bf after a tough loss.

3.81
12.5k
7
0
12

Charlotte's Free Weekend

All's fair in love, war, failing marriages and business.

H
4.55
17.1k
15
1
38
0

Straight Roomies during Lockdown Ch. 06

Monty finally gets Chase’s ass… and his heart.

H
4.84
20.4k
61
26
88

A Friend in Need is a Friend Indeed

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

4.24
9.2k
6
0
16
0

Anal in the Age of Grunge

Inexperienced girl seeks gay guy for anal initiation.

H
4.77
31.5k
26
3
45
0

It Started with 2, X-Mas Day

Christmas Day has arrived for the Martins and their guests.

H
4.72
23.4k
58
13
109

Love without Limits - Date Night Ch. 01

Harry and Sam have a night out on the town.

4.47
8.8k
5
0
11

I Hate Him...

Can straight Texan jock lust for a pesky feminine activist?

H
4.77
38k
116
53
182

The Widowers Solace Pt. 02

A widowers love of crossdressing leads him to find comfort.

H
4.66
6.6k
8
1
8

Mystery Girl

Jake gets a mysterious call from a stranger.

H
4.54
23.2k
26
2
39
0

Virgin Babysitter Becomes My Slut Ch. 04

As Annie makes up her mind, I remember becoming Master.

4.47
41.4k
26
10
41

Sundays

Sensual Sunday stroll down memory lane.

4.4
3.4k
6
3
7
0

Our Bed and Breakfast Guest Ch. 03

Becoming more comfortable with Herman.

4.49
11.4k
16
3
29

Teasing the Newly-Weds Ch. 06

MsV and Anna take Harry, as Harriet, shopping.

4.43
4.6k
3
0
4

A Summer with Ali Pt. 02

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

H
4.82
4.9k
7
2
11

Road Tripping Pt. 09

Molly and Sara get some new toys.

H
4.5
10.6k
4
1
18

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

The best three day fuck fest of my life.

H
4.61
11.7k
12
1
31

Remedial Medical

Doctor stretches the new novice's anus for advanced anal.

H
4.55
61.8k
35
5
83
0

Boy Toy Ch. 01

Stephen is dominated by a married couple.

H
4.54
65.3k
106
8
203

Mom Sucks Dick! Pt. 03

You would not believe the weekend I had!

H
4.77
86.3k
190
23
269

The Journals of ███ ████: Ch. 01

A Hollywood producer's greatest Christmas memory.

H
4.77
16.9k
28
6
45
0

Nate's Birthday Surprise Pt. 01

Nate and Marianne's mundane sex-life gets upended.

4.17
35.8k
27
33
48

The Bet

My girlfriend puts her ass on the line.

H
4.79
490.4k
461
44
734
0

I Want To Make You An Offer

Giving you my anal virginity.

H
4.59
32.2k
17
4
49
0

Peter the Neighbour

A young man and his older neighbour.

H
4.5
66.5k
55
11
78

My First Time Man

Tony takes my anal virginity.

4.08
25.7k
7
1
12
0

First Sex Experiences Pt. 04

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

4.29
10.2k
7
0
8

Fake Agent

Lisa is fucked in the arse at a hardcore casting.

H
4.5
64.1k
60
6
108
0

Red Lips

After years of waiting, Klaus finally gets his red lips.

H
4.62
24.3k
26
3
37
0

Beach Innocence

Romantic get away turns into a loving wife opening up.

4.12
24.5k
18
11
30
0

Julia, Her First Time

Julia and her Boyfriend go to their first swing.

H
4.59
38.6k
57
2
99
0

On Demand Ch. 02

Brad introduces Michael to some of his jock buddies.

H
4.58
15k
15
4
22

In Plain Sight Pt. 03

Continuation from Chapter 2, buttsex (finally) ensues.

H
4.7
9.2k
11
3
18

In Plain Sight Pt. 02

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

H
4.75
10.7k
7
2
16

Behind His Back

A young woman fucks her passed out boyfriend's best friend.

4.36
70.4k
87
11
136
0

A Game of HORSE Pt. 04

Brandi plays with toys and decides she wants the real thing.

H
4.82
19.2k
27
2
32

Bubble-Butt Gym Whore

Her ass wasn't for sale. Or was it?

H
4.68
116.9k
211
20
384
0

Rasika's Surrender Ch. 03

Humiliating first time anal experience.

4.33
53.9k
21
3
36

Teacher's Pet Pt. 08

Continuing my sexual education with HS teacher's roommate.

H
4.77
8.5k
10
0
17

Control in the Hotel Pt. 03

Jeff and Shelia are joined by her best friend.

4.13
10.3k
5
1
9

The Principal's Turn - Sam's Fall

With Maggie's turn complete, Taisha puts Sam in his place.

H
4.72
19.4k
23
4
37

Sarah

Unlocking an older woman's anal desires.

H
4.74
79.5k
58
17
107
0

My New Gym Buddy Pt. 03

I give all of myself to him for the first time.

H
4.61
31.8k
48
8
69

Oslo

An unusual adventure when I was a young man.

4.07
12.7k
4
1
10

The Stranger Who Stole My Wife

I watched my wife cheating on me with a complete stranger.

2.52
110.7k
74
37
140
0

12 Months a Slave 03: March

A wife is held as assurance until his debt is paid.

4.44
58k
68
0
100

Gold Digger Wife Wants It All

She wants his money and her boyfriends.

H
4.52
122k
153
94
248

Samantha on the Swing Pt. 02

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

4.38
13.1k
8
3
10

Coach Gets Used by Senior Class

New coach gets gangraped by his seniors for their graduation.

3.41
33.4k
12
1
32
0

The Deal Pt. 02

The awakening - it's not over yet for Freddy & Carolyn.

H
4.75
49.3k
151
39
208

To the Last Knuckle

Heartbroken guy finds a new lover. She finds his prostate.

4.31
38.4k
61
7
91
0

A Surprise Stretching

The church prepares a girl's anus for her boyfriend.

4.25
99.1k
68
6
108
0

Two, Three, Four or More Pt. 02

Morning after revelations and getting busted.

H
4.62
5k
3
1
4

Trust

A man takes a dragon in trust and love...

4.41
5.4k
3
1
11
0
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