‘playboy’ stories

Active tags
Active tags
playboy 

Category

Prom Night

Stood up on prom night, she finds a replacement.

4.27
11.3k
6
0
19
0

Playboy Killed My Marriage Pt. 02

The conclusion to the Rocco/Amber Lynn saga.

3.92
10.9k
24
43
41

The Amazing Randy Plays a Party

After playing a benefit, Randy accepts a private party gig.

H
4.85
11.4k
12
9
27
0

The Amazing Randy Hits the Slopes

Randy's gig is interrupted by a fire at the venue.

H
4.83
6k
4
8
14
0

Old Playboys

Revisiting a past memory with pornography and mother.

4.05
22.8k
30
3
69
0

Bangkok Assignment Ch. 02

Andre is introduced to his new secretary Rita.

H
4.56
17.6k
9
0
20

The Playboy Hotel 01

Kinky fun at The Playboy Hotel.

0
11.2k
7
1
17
0

...Just Some Old Magazines

Old magazine provide a new experience.

4.11
7.8k
3
2
5
0

Playboy Goes Trashy Ch. 01

Taking over the Playboy empire... In my own trashy way.

2.48
11.9k
6
0
15
0

Our Practice Honeymoon

I met the love of my life in the third grade.

4.45
14.6k
12
2
25
0

Reunited Ch. 01

When two young lovers meet again.

H
4.62
6.3k
5
4
8
0

Professor Goodlovin Pt. 01

A sexy professor blows her well-endowed student.

4.48
20.2k
15
0
26
0

Getting Her Autograph

I wanted Jenny McCarthy's autograph. I got way more.

H
4.6
12.3k
19
0
32
0

Blackmailed in China Pt. 01

Alex gets blackmailed by a Chinese playboy.

H
4.6
32.7k
43
9
61
0

Another Beach Holiday

A company retreat that ended up hot and steamy.

3.69
28k
4
1
10
0

Scorching Hot Sweetness: The Fence

A hot day, an intense storm, a friendship forged

H
4.63
18.5k
8
4
16

Not Just a Boss Ch. 04

Matt takes Annie to his apartment & feelings start brewing.

4.19
9k
1
0
1

Swing Goes Aussie

Aussie couple changes their life in the USA.

4.21
22.6k
10
1
17
0

Country Gin

High tech virgin meets country for a little party magic.

H
4.51
13.1k
3
1
11
0

Miss August 2001

Jennifer Walcott and a friend relive old times of kinky fun.

H
4.74
13.8k
43
3
49
0

New Wife

Their friend's new wife was a surprise.

4.15
84.3k
33
25
45
0

Former Playmates Pt. 10: Alyssa's Family

Reunited with her son, nothing will keep them apart.

H
4.59
35.9k
49
1
64

The Circle Ch. 33

Renee does Playboy. Ellen does more.

H
4.8
19k
10
1
12

Former Playmates Pt. 09: Tiffanie's True Desire

Former Playboy Playmate succumbs to desires for her son.

H
4.53
36.9k
42
8
53

Party to the Cemetery

Taking pinup girl for the ride of my life.

4.11
22.8k
8
4
13
0

Former Playmates Pt. 08: Tiffanie's Year

A mom sleeps with black men to hide her incestuous desires.

H
4.54
25k
29
3
36

Former Playmates Pt. 07: Alyssa’s Journey

Leaving abuse, letters to her son, loving black cock.

H
4.52
22.6k
29
4
35

Former Playmates Pt. 06: Julianne's Medicine

Womanizing son changes by caring for depressed mom.

H
4.68
29.5k
53
7
72

Former Playmates Pt. 05: Stephanie and Son

Stuck with mom in a wintery cabin.

H
4.57
85.9k
83
7
112

Smitten by the Playboy: Crush

Tori meets the playboy who is keen on seducing her.

1.67
17.1k
4
0
11
0

Playing with Playboy Ch. 01

Victoria Justice does Playboy. And her photographers.

4.38
34.6k
42
3
59

Deborah Reel from Agnes Scott

Playboy's Women of Women's Colleges Issue.

4.71
7.7k
4
0
4

The Sex Therapist

Starring Playboy Playmate Sharry Konopski.

4.41
10.7k
4
0
7
0

The Challenge Ch. 04: Origins

Bob's origin and history, along with some revelations.

H
4.6
39k
43
1
57

New Maid

Man hires a new maid service.

4.3
92.3k
34
2
53
0

A Hot Day

Family love.

4.4
130k
33
0
41
0

Playboy Magazine My Daughter And Me Ch. 02

Daughter comes over after hometown photo shoot to dads.

4.33
72.4k
38
2
49

Office Manager Is a Playboy Playmate

A Playboy Playmate who was office manager.

4.38
31.8k
17
2
21
0

Lai Ch. 01: Barb

Elegant beauty seduces wealthy bachelor on first date.

3.98
21.4k
13
0
15

From Self Love to Playmate Love

Ms. October 1985 Cynthia Brimhall walks in on me

H
4.5
12.3k
4
0
7
0

Erica's Journey of Discovery Ch. 03

Fro the 1st time Erica comes alive in front of the cameras.

H
4.57
15k
3
0
8

One Glorious Day

A special day in the life of a handsome, promiscuous playboy

4.06
11.7k
1
0
4
0

A Miracle at the Cabin Ch. 12

What do you mean funny? This is not funny.

H
4.77
24.9k
6
2
7

A Miracle at the Cabin Ch. 08

I always wanted to meet a Playboy model.

H
4.72
31k
5
5
6

A Hot And Steamy Daydream

A roof workers daydreams about an ebony beauty next door.

3.56
20.4k
4
1
6
0

Three Men, a Boat, and Naked Women

Be careful what you wish for, because you may get your wish.

3.67
83.1k
20
11
24
0

He Meets His Match

Henry meets a fiery woman.

3.26
19.4k
1
6
5
0

Black Women and Me

My fantasy of black women, from childhood to reality.

0
63.4k
40
0
56
0

Paul Ironwood Ch. 02

Paul fucks a 'secretary' hard up the ass.

4.2
98.8k
13
0
17

Holly's World

Holly Madison and Kim Kardashian teach a slut a lesson.

2.93
40.8k
3
1
4
0

Dream About Me

She visits a wealthy gentleman known for his playboy habits.

3.45
11.3k
0000

America's Playboy Ch. 05

Anthony finds out what he must do for Boss Russo.

3.45
20.3k
4
2
4

America's Playboy Ch. 01

An old man get beautiful, buxom, big boob, blonde bombshells.

3.35
107.4k
20
5
36

Playboy Files: Nurse Gets Treatment

WWE diva has sex with playboy employee.

3.95
35.6k
8
0
12

The Getting Lucky Guy

A video gone viral changes his life - big time.

4.46
18.1k
7
4
8
0

Earth Day, Sioux Indian Style Ch. 11

Earth Day party turns into a CFNM review.

4.29
49.9k
3
7
12

C43 Ch. 01

When a mysterious card arrived in a brown envelope...

3.91
25.9k
2
2
5
0

Playboy Files: Sable Gets Her Wish

He gets a perk as horny Playmate seeks company.

H
4.71
38.1k
8
1
18

Iris Jinger-Santos

P.B Model Iris Jinger-Santos plays an eager to help stylist.

4.2
19.4k
4
0
7
0

My Playmate Ch. 01

Trying to keep up with my wild nymphomaniac.

H
4.69
248.7k
101
8
172

The Pissboy Mansion Ch. 03

Wet lesbian lovers - the next stage.

4.49
50k
8
2
8

The Pissboy Mansion Ch. 02

Her first lesbian eperience is all wet.

H
4.56
73.5k
14
0
18

Playboy Magazine My Daughter And Me

Daughter wants Dad's advice.

H
4.54
241.2k
51
8
91

Daughter Is The Centerfold Ch. 02

She asks Dad to help edit nude photos.

H
4.54
133.5k
29
6
51

Daughter Is The Centerfold Ch. 01

Daughter asks his advice about posing nude.

4.44
191.1k
64
8
114

Miki Garcia

Miss January 1973 conquers D.C. in the Love Machine.

H
4.71
19.3k
2
0
5
0

Heather Kozar

Playmate, sexy nun's costume, trick or treat.

H
4.65
46.9k
18
0
21
0

Gaye Rennie

The beautiful Miss April 1968.

H
4.68
20.3k
2
0
4
0

Corinna Harney

Miss August, 1991 wins at cards.

H
4.64
17.7k
1
0
2
0

Lisa Baker & Dianne Chandler

Two classic playmates, one bunny costume, and a horny guy.

4.33
17.8k
00
3
0

Doing Anna Nicole Smith

The buxom blonde takes a bath.

H
4.57
52.4k
9
0
13
0

Dolly Read

British playmate and bunny conquers America.

H
4.82
31.9k
4
0
7
0

Julia Schultz & Tiffany Taylor

Two playmates, a pair of cuffs, an angry cop.

4.31
40.5k
5
0
7
0

Million Dollar Baby

Playmate Karen Price in the gym.

4.41
36.5k
4
0
6
0

Amber Campisi

Miss February 2005 makes a conquest.

3.82
23.9k
5
0
7

The Playmates of 1969

12 beautiful girls have a party; Wilt Chamberlain scores.

4.41
25k
3
0
5
0

Candy Loving in White

The playmate models a sheer white outfit.

H
4.56
38.2k
3
0
6

Stella Stevens

A Southern Belle spreads her charms.

H
4.5
28k
6
2
8
0

Lillian Muller

Playmate of the Year's movie audition.

4.33
25.4k
3
0
5
0

Kathy Shower

The beautiful blonde comes out of the rain.

4.48
49k
3
0
4
0

Nancy Cameron's Prom Night

Young buxom beauty loses her virginity.

H
4.53
46.9k
5
1
11
0

Hope Olson Ch. 03

Hope meets a famous publisher.

H
4.58
27.1k
1
0
1

Lindsey Vuolo

She's a little drunk and very horny.

4.34
54.8k
5
0
6
0

Kimberly McArthur Meets a Fan

Kim McArthur has a chance encounter in NYC.

H
4.64
25.1k
2
0
3
0

Hope Olson Ch. 02

Hope continues her sexual awakening.

H
4.74
26.4k
1
1
1

Kim McArthur's Busy Day

Kim is kidnapped on her birthday.

H
4.74
41.6k
4
0
6
0

Shannon Stewart

Playmate takes fan on a wild ride.

H
4.6
37.8k
5
0
10
Active tags
Active tags
playboy
Separate tags with commas. More info in the FAQ