‘tomboy’ stories

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Active tags
tomboy 

Category

The Actress

After a chance encounter I give an Oscar-worthy performance.

HW
4.89
146.1k
377
140
498
0

Football Bet FTW!

A costume reveals a new woman, and the bet is on!

HW
4.77
372.2k
339
77
453
0

Bringing the Heat

Gentle femdom between you and a tomboyish childhood friend.

H
4.74
105.9k
282
25
417
0

Rad Bird

A metro brother and his tomboy skatepunk sister fall in love.

H
4.67
80.8k
179
34
250
0

RenFest Incest

It's not incest if we don't break character, little brother.

H
4.78
48.3k
130
14
245
0

Tomboy Makeover Pt. 01

Alex asks her female friends to help her become more girly.

H
4.63
69.5k
127
16
200

Your Tomboy BFF Makes You Cum

I'm your best friend, I know exactly what you need.

H
4.8
147.6k
121
11
217
0

Quarantined...

Quarantined with your gay roommate and her bi girlfriend.

H
4.71
77.4k
115
25
202
0

The Carpenter

Max builds more than a sundeck for her rich cougar client.

H
4.56
52.9k
111
45
174
0

Your Roommate's Bi Girlfriend

Your lesbian roomie's bi girlfriend pushes your buttons.

H
4.64
62.1k
89
9
167
0

Partners

Human adventurer discovers a lot about his elven partner.

H
4.8
29.1k
86
4
142
0

Tomboy Makeover Pt. 02

Alex uses a strap-on to fulfill her friends' fantasies.

H
4.66
63.5k
80
6
97

The Adventures of a Virgin Incubus

The things one does for friends...

H
4.7
26.1k
79
10
103

Bovine-X

Flat chests? Don't worry with Bovine-X you too can have DDs!

3.99
132.7k
78
6
130

Tomboy Takes Care Of Daddy

You're a hot blooded man, daddy. Let me take care of you.

H
4.77
56.9k
77
7
155
0

Soft Submission Ch. 01: Captured

A sporty tomboy is gently bound by her cheerleader crush.

H
4.55
37.2k
72
13
148

Lucy and The Bartender

Lucy's boyfriend gets too drunk leaving her night wide open.

4.26
57.5k
67
3
102

Leanne the Lusty Lifeguard

Sexy sporty girl seduces shy guy.

H
4.54
64.8k
66
12
109
0

Tomboy Best Friend’s Perfect Pussy

He accidentally sees friend (F19) naked in secluded cabin.

H
4.52
41.3k
61
14
136
0

Free Use Sim Pt. 03

Ass to mouth with some skaters in public

4.46
48.7k
61
0
81

Confessions of a Blowjob Addict

40-year-old teacher confesses her past and present.

4.41
358.1k
60
19
83
0

Coach T... Ch. 01

She's made to bend to his will.

H
4.5
141.2k
60
5
96
0

BFF's Alt Tomboy Sis is a Cumslut

I'm a total cumslut these days.

H
4.8
55.1k
56
8
138
0

Family Reunion - Ch. 01

Shy brother reunites with his tomboy older sister.

3.93
37.8k
54
13
110
0

A Sticky Situation

Femboy and Orc-girl get their minds wiped by a slime goddess.

4.49
23.9k
53
1
91
0

Warming Freezing Tomboy Best Friend

No choice but to use every method he can to warm her (F19)

H
4.58
47.4k
53
20
108
0

The Sim - Custom Scenarios Pt. 04

Making anal porn with a very, very good friend.

H
4.62
31.6k
52
6
62

Tomboy Takes Her Best Friend

Are you a good boy, or are you going to be difficult?

H
4.64
28.7k
50
5
109
0

Summer in Dawson Ch. 01

He has an unexpected adventure in a small town

H
4.71
50.9k
50
17
71
0

Your Tomboy MILF Wife Seduces You

Don't make me push you down...you'd like it too much.

H
4.63
43.4k
49
12
100
0

Taming Fire

A tomboy desperately seduces firefighter friend.

H
4.65
54.6k
48
10
75
0

Is Your Cock Good Enough for Mommy?

bitchy big sis wants to fuck while hearing mom get railed.

H
4.69
24.6k
47
9
110
0

A T-Girl and a Tomboy Pt. 02

At the Cheerleaders' Squad Party.

H
4.85
22.4k
47
10
60

April Fools - Best Friends

Best friends conspire against his wife.

3.92
88.7k
45
57
85
0

Snatch Competition

Tomboy lesbian gym rivals make bet, loser gets feminized.

H
4.58
26.8k
44
4
84
0

First Discovery Ch. 01

Straight girl with lesbian friends meets the new girl.

4.22
79.9k
44
15
58

Something

High school romance

4.13
49.5k
44
14
58
0

The Shower Hog

He takes too long in the shower. Sis steps in.

4.37
32.3k
40
10
102
0

Jillybean

Young love in a small neighborhood.

H
4.74
50.6k
37
10
55
0

Mouse's Maiden Voyage

Astronaut loses her virginity in space to two comrades.

H
4.69
40.8k
36
7
49
0

American Phalanx Ch. 01

A sexy vision of the Post-Apocalypse.

H
4.59
26k
35
2
59

Ploughing Kate's Backyard

We get together after some hard studying.

4.18
55.2k
35
2
52
0

Someone Your Own Size

Cruel girl feminises a goth tomboy. Foot slavery ensues.

4.07
22.4k
35
3
74
0

Two Tantalizing Tomboys

One tomboy was surpisingly good, but two?

H
4.51
115.3k
35
1
54
0

Just Friends...with Benefits

Can guys be friends with a hot woman?

3.73
87.8k
35
6
53
0

Porn Heavy: T's Pool Party

When a tomboy gets tired of being one of the guys.

4.13
82.5k
34
1
52

Soft Submission Ch. 02: Breakfast

Michelle gives Sophie aftercare.

H
4.64
17.2k
34
6
47

From the Blood of the Wolf Ch. 01

Anna and her hiking party must stick together to stay alive.

4.47
23.7k
33
12
44

Hot, Nerdy Coworker Bets Her Body

Your nerdy coworker bets her body on a game of MtG.

H
4.71
23.5k
32
7
86
0

Charlie

Charlie is no longer one of the boys.

3.27
27.1k
32
12
65
0

Exposed

Dressed as a man Rose thought she was safe.

4.2
66.1k
31
7
47
0

Candid Camera

Two best friends play just rough enough.

4.4
32.4k
31
3
70

Triumph of the Dads

Mom makes son compete with dad for her; dad romps.

0
75.3k
31
0
57
0

First Discovery Ch. 04

Nikki and Taty decide to reveal their secret relationship.

H
4.63
33.1k
31
17
38

A Good Friend Stays on Her Knees

Blonde tomboy blows a group of friends at a club.

4.37
23.9k
31
3
65
0

Country Love

Step-siblings reunite on their parent's old ranch.

4.45
29.5k
30
6
67
0

Forbidden Fruit Ch. 01

An exemplary school teacher risks it all for a student.

H
4.73
15.5k
30
5
60

Allow Me In

A biracial tomboy gets an unexpected visitor who wants her.

4.23
23.5k
30
9
64

My Best Friend is Actually a Girl!?

Based on Aestheticc-meme's OC Alex.

H
4.83
8.6k
29
7
56
0

Breeding Your Yandere Tomboy BFF

I’m always horny for you… It’s okay that I admit that right?

H
4.74
14.4k
29
3
84
0

Your Sister's Hot Best Friend

Wanna see my tattoos? I just need to take my clothes off...

H
4.62
24k
29
10
63
0

Soft Submission Ch. 03: Playmates

Two of Michelle's friends join in on Sophie's teasing.

H
4.68
14.9k
28
5
40

Tomboy Bestie is Your Cum Drainer

You need to cum for your donation and I'd love to help...

H
4.7
20.7k
28
5
72
0

Alley Cat

Tough girl guides her femme lover with a heavy hand.

H
4.77
38.2k
28
4
42
0

Swirl Ch. 01

Lust is the perfect outlet for hate.

4.32
22.9k
28
9
39
0

Sharing a Bed with Your Bully

You and your bully have to room together before the game!

H
4.71
20.4k
27
6
58
0

Brandy the Cross Country Runner

To the old fellow 7 miles and 80 degrees made her delicious.

H
4.66
27.4k
25
3
36
0

A Week in the Past

A man with a memory problem revisits his hometown.

H
4.72
23.7k
25
17
30
0

In the Arms of a Friend

A stranger becomes more.

H
4.58
40.2k
22
7
31
0

He Wouldn't Let Me, Will You?

He wouldn't let me suck his cock, so I'll suck yours instead.

H
4.68
17.2k
22
8
42
0

Let Me Suck It Better

First aid for your cock from your tomboy bestie...

H
4.53
18.3k
21
5
47
0

Tomboy Sue

A tomboy flees from a rapist and world condemnation.

H
4.86
13.2k
20
23
39
0

The Hairdresser

Things get steamy when she meets a sexy hairdresser.

H
4.51
87.4k
20
3
27

Marley and Miranda

An effeminate young man gets caught playing with super glue.

H
4.59
17.3k
20
3
32
0

Dude, It's Just a Cock

Let's just do it. It's just a cock, right?

H
4.81
17.3k
20
8
44
0

Tomboy Takes Charge

Younger brother's tomboy friend is in control that night.

NEWH
4.66
8k
20
1
31
0

Two Toms and a Brain Cell Ch. 05

A pretty boy gets double-teamed by his gf and her friend.

H
4.62
16.7k
19
4
35

Sandra's New Neighbors Ch. 06

Fun in the Furry Farm.

H
4.59
29.5k
19
3
23

Just One of the Guys

She decides to prove him wrong...

4.45
69.3k
19
1
42
0

Two Toms and a Brain Cell Ch. 01

Two people meet for a date, but there's a bit of a mix up.

H
4.55
9.8k
19
5
50

A Big Man Finds Love

Tomboy falls in love with Big Guy.

3.59
195.7k
18
4
28
0

I'll Just Take What I Want

You keep teasing me. I can't take it anymore. [F4M]

H
4.58
15.2k
18
2
53
0

Candid Camera Pt. 02

Sharon's kinks are thrust into the spotlight.

H
4.6
14.4k
18
3
35

Conlan & the Tomboy Ch. 02

Liz gives herself to Conlan whether he likes it or not.

H
4.5
39.1k
18
12
19

Your Son Calls Me "Mommy" Too

Your bad-bitch girlfriend helps you get out of your shell.

H
4.65
22.3k
17
4
53
0

The Big Game

I'm fucking in love with you, dumbass!

3.73
14.1k
16
0
30
0

Forbidden Fruit Ch. 02

After weeks of painful teasing, Tom loses control.

H
4.56
10.9k
16
2
23

Duty Ch. 01

The Kingdom needs an heir...and the King moves to action.

4.34
19.5k
16
2
48
0

Truth Or Dare Clusterfuck Ch. 02

The foursome and their friends get closer.

4.35
18.5k
16
1
26

Anatomy and Fine Dining

Blind date exceeds expectations/relations in public and....

H
4.5
34k
16
2
31
0

Truth or Dare

A game of Truth or Dare will change our friendship forever.

H
4.53
16.8k
16
5
46
0

Dude, It's Just a Blowjob

The sex was good, so why not try a blowjob, too?

H
4.55
16.5k
15
3
37
0

Secret Lives Of Indian Women

Indian tomboy falls for Haitian scholar in Ottawa.

2.94
15.7k
15
6
15
0

S.L - The Pretty Boy

A gamine lesbian and a femme twink have an unlikely tryst!

H
4.58
9.2k
15
5
36

Dude, It's Just "I Love You"

It started as sex, but now it's so much more...

H
4.7
11.6k
15
8
35
0

Tanya

Old friends take things to the next level.

H
4.58
12.5k
15
0
37
0

Herman: Tomboys Grow Up

Tomboy to the bone--but eventually...

H
4.53
72.6k
15
11
27
0

The Sick Confession Of A Nympho

Introduction to sex and life filled with secrets.

4.03
37.1k
14
1
22
0

Beach House Shower for Two

A tomboy finds him in the shower . . . in her swimsuit . . .

4.44
32.9k
14
4
27
0
12
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