Tomboy

The audio includes a woman who engages in traditionally masculine activities and stereotypical boyish behaviour. (Not to be confused with Femboy).

I get OFF on knowing you WANT this

I get off on the dopamine-spiking allure that is knowing you want to drop everything, and anything, just to let me take complete control of that slutty little messed up brain of yours. And you know it's better this way. You just have to trust me; trust that I'm a real fucking person who you want to take over your thoughts. So when you're fucking sat there, letting yourself be complicated, overwhelmed by choices and indecision. Even though you know that's pathetic. Even though you brain is sparking off all on its own. What I'm about to do to you here. Well, this is something productive to do instead. You see, there's a lot of parts of you that just never shut the fuck up. And they complicate things. You're soo complicated. And oh, it's sooo complicated. But when you're with me it...

F4A 17m 33s 07/08/2025 Free

I don't care about gender, it's you I like

This file is a romantic roleplay in which your cis girlfriend is here for you; full of loving affection, comfort, and rejection of anyone who would reject you. The premise is that you're seeking reassurance from her, as a closeted trans woman anxious about passing in public, and worried what other people might say. Your girlfriend wants you to know that you're safe, and she'll love you no matter what. ♡

F4TF 6m 20s 08/03/2023 Free

Dropping into the Loop: Thrown Down

So sweet, so cute. So helpless. Helpless to resist my voice. It wraps inside you, plays… Almost sentient in the way the words themselves seem to wrap around your being. Nudging and focusing you towards my goals without you even thinking…

F4F 13m 51s 12/11/2021 Free

Your WoW Crush Hypnotizes You Into Her New Minion

I know what you've been thinking all these nights, grinding WoW together. I’ve been having a blast, it’s been a huge nostalgia trip getting sucked back into Azeroth. But, I've geared up my Druid fully on classic now and I was thinking, maybe we should play together in person... If you catch my drift, I'm sure the guild can manage without us for one night. If you’re game, wanna give it a shot? Wanna have some fun? To really spice things up - I have this kink that I want to experience with you. The first time we meet, for real, I want you to be in a hypnotic trance. I want you plugged, lying down in your bed, completely naked, arms and legs bound in real life, secured with nowhere to go. No choice but to keep listening to my voice, as my suggestions seep further and deeper into...

A Happy Little Orgasm

Hi, I’m Shibby. I’d like to welcome you to the happy world of painting, using your imagination. Imagination is like any muscle in your body. The more you practice, the better you become. In today's session I have so many experimental techniques I’d like to show you. All you need is a happy little heart and a willing mind. Life is all about creating happy little places. Come join me on a painting adventure, together. Step into the canvas with me. I will start off by showing you some simple ways to paint a beautiful, calming nature scene- and for those of you adventurous enough to make it inside my cabin, a sexy surprise awaits!

A Happy Little Induction

Hi, I’m Shibby. I’d like to welcome you to the happy world of painting, using your imagination. Imagination is like any muscle in your body. The more you practice, the better you become. In today's session I have so many experimental techniques I’d like to show you. All you need is a happy little heart and a willing mind. Life is all about creating happy little places. Come join me on a painting adventure, together.

F4A 27m 53s 18/02/2020 Free

Discovered in the Doorway

I came over to play some video games, but when you left to go to the bathroom you took a bit too long. I got bored, started rummaging around your room - and found some verrrrry interesting things in your nightstand. I go out in search of you... only to find you engrossed, peeking through an almost closed door. You dirty peeping tom! You are watching your roommate fuck his hot little girlfriend! Boxing you in with my own sexy body, I whisper in your ears, letting you know that while you are bigger then me, the act of escaping would alert your roommate. You are trapped... Better be a good little poppet and keep very quiet... You should never leave me to my own devices.

F4TF 26m 3s 21/01/2020 Free

Making A Bet With A Gamer Girl

Your gamer girl friend is having trouble beating a boss and doesn’t appreciate hearing how easy it was for you.
I bet that you won’t be able to beat him while I distract you. Oh no! My distractions are so sexy! What will you doooooooo?

F4M 34m 49s 28/11/2019 Free

More than Just Friends

We make such good friends because you let me do all the talking! But... maybe we could be more then just friends. I'd really like that.

F4M 11m 54s 23/08/2019 Free

Sex Fight

It seems my bestie has gotten to big for his boxers, and I am just such a good fight I am going to bring your ass down to earth. In my bed. It's a sexy wrestling match, to the winner goes the spoils of the loser being their slave for the next week. And I don't play fair.

F4M 12m 19s 21/08/2019 Free

Tomboy Tussle

You think cause I'm a girl I can't beat your ass? Ready to wrestle?

F4M 27m 24s 17/07/2019 Free

Smash and Chill

After winning a bet by beating her best friend and roommate at a game of Super Smash Bros, a tomboy decides to announce her love in the way she thinks the both of them would enjoy the most. “God, I love the feeling of your lips. I used to imagine this when you weren’t home. This is way better than my dreams.”

F4M 22m 30s 08/07/2019 Free

Chained Under My Control

You made the choice to come to me a long time ago... and now choice is something you no longer have to worry about. You're a horny boy who needs to submit, and so I'm going to play with you. Get ready for me to get in your head. Now close your eyes. Picture yourself outside. The sounds of the night around you. Slowly waking up from a drugged out haze, to the sound of chains being locked around you, of cuffs being played with and attached. Every time you move you can hear the clanking of your chains, the stressed leather of your cuffs. I will unlock one of your hands... and use the locking and unlocking snicks to drive your tempo as you touch yourself for me.

F4M 32m 51s 26/06/2019 Free

Watching Porn With Your Lesbian Best Friend

In this dirty bit of fun scripted by u/SpamMeMoarxlol, your lesbian best friend is over to watch a basketball game and play a game of Smash. After both games are over, she decides to play another type of game. Playing with you, making you blush, she has you pull out your computer, and look up chaturbate. Picking out just what she wants, the two of you start masturbating together, in a game to try and cum at the same time. "Can I tell you a secret? If you had nice tits, it'd be kinda hot if you were watching me, touching yourself." The final video we are watching while playing with ourselves, can be found by searching for "Are you turned on?" on pornhub.

F4M 15m 5s 09/06/2019 Free

Tomboy Dominatrix

Someone caught you looking at porn, and now you are over at your friend Shibby's house, venting your embarrassment. You get a whole lot more then sympathy as in an effort to make you feel better I show you MY secret... My Dungeon. It begins a bit rambly, but this is how real scenes work, especially for the first time. I go through consenting, and safe words, and once I am sure you know what you are getting into... I put restraints on you. And I make you mine.

F4M 42m 3s 07/05/2019 Free

Let's Just Fuck Already!

A very satisfying conclusion to the "Tomboy Saga" scripted by u/OnlyaGWAcct. Like the rest, this file can be listened to on it's own just fine... But intimacy and sex, are so much better when you take things slow, take your time over the course of a few days to listen in order, truly envelope yourself in the fantasy, to bring you the most satisfying orgasm possible. Maybe consider starting with a handjob from a bored friend, who has always wanted to do the helicopter dick trick, but lacks the equipment. Of course, once I'd seen your cock, handled it... it's perfectly normal that I wanted to taste it. Knowing how dirty boys are though, I waited until you were in the shower to suggest a blowjob. :P And now... Well I think we've waited long enough. We both knew it was going to get this...

F4M 31m 40s 14/02/2019 Free

Is it Cool If I Shower With You, and Maybe Also Suck Your Cock?

Hey Roomie- I'm back from the gym, quit hogging the bathroom and let me in! Oh... you're showering? Well let me in, I'm a sweaty mess and if you wash my back, I'll suck your cock.

F4M 17m 5s 13/02/2019 Free

I Don't Have my Own Cock to Play With, but Maybe I Could use Yours?

I'm bored. And a bored Shibby is a dangerous and unpredictable thing. I really, really hate being bored. So, why don't you help me with that? C'mon, entertain me... I want to try something new! Like... a cock. I've never played with one of those before! So whip yours out. I want to play!

F4M 17m 2s 10/01/2019 Free

Paintball Buddies with Benefits

We just got back from playing paintball, and are covered in mud, paint, and bruises. Come in the bathroom with me, where we can strip off without making a mess, and maybe get cleaned up a bit. Grab some ice, I want you to numb my bruises, and maybe rub my sore muscles while you're at it. Oh come on, this is just what good friends do! It's what's after that where it becomes naughty. ;) ps. I'm here for you if you want more [Tomboy] fun. pps. Don't tickle me or I'll smack your balls.

F4M 25m 10s 12/12/2018 Free

Tomboy CuddleSlut

It's dark and cold outside, but we are warm together in the bunkhouse, cuddling under a nice thick blanket. This file is not about sex. It's about cuddling, and a rambling story of earning the name cuddleslut at a paintball field.

F4M 20m 5s 05/12/2018 Free

I Fucking Love You, Ok?

Uh. You must be thinking of some other friend. Because you know that I wouldn't let you be alone right now. Or you should, anyway. Wait. So because your girlfriend, who just dumped you in the most fucking tasteless way would have have told you to man up and deal with it, I have to leave you alone with your shitty thoughts? No. You heard me. No. First of all, I never approved of your decision to go exclusive with her. She was a bougie brat who didn't really want to be involved with you beyond what you could do for her. Yes, I had veto power but was not consulted. That's in the Best Friend Constitution. I feel that my rights were ignored in your haste to get laid. Oh yeah I want to jump all over that cock. Not tonight. I know I can be a little bossy. Again with the inappropriate...

F4M 26m 23s 27/11/2018 Free

Tomboy Lab Accident

Hey - Hey, I kinda need your help. Can I come in? There was an accident at the lab - I mishandled a vial, and got it all over me. And now my body just feels hot, and needy... and I know what it needs. Will you help your tomboy best friend out?

F4M 12m 8s 19/11/2018 Free

Tomboy and Her Friend Forced to Fuck

In this story by u/homersoc_ ... A tomboy gets in over her head with a gambling problem, and owes an unsavory character a good deal of money. Only her best friend can salvage a bad situation by helping her repay her gambling debt in a decidedly pornographic way. Because if he won't fuck her on film, some strangers will. At the same time, maybe having sex with her best friend isn't something the tomboy is as opposed to as she may seem... Please, save me.

F4M 30m 6s 12/06/2018 Free

Tomboy Hates Her Roommate's Ex... Enough to Give Him Sex

In this file I am a tomboy, a gamer, your roommate and best friend. The latest game came out and I just can't wait to play with you - only to find out you are planning on going over to your exes place because she needs something fixed and you are desperate to get laid. Well, being a fixer myself, I come up with a solution to make both of us happy. I'm not going to let that bitch ruin my plans - so I'll just fuck you instead.

Peeping Tomboy

Rape tag to be safe, the sex is consensual but there are a fair amount of references to rape. Your tomboy friend owes you a favor, and decides to pay you back by showing a place to spy on naked girls. Will anything more happen between you two? The tags say yes.

F4M 22m 55s 18/04/2018 Free

From Tomboy to Submissive Girlfriend

Oh my God dude, what are you doing home? I thought you went back to your parent’s place for the weekend. Um, you’re probably wondering why the fuck I’m wearing a dress. And some makeup. And an apron. And why I’m… baking. You know, for other girls, this wouldn’t require an explanation. Can’t you just let it go, and pretend you never saw this? I have an unblemished reputation as a tomboy, and I’d prefer to keep it that way. Just walk away and pretend you never saw this. You’re going to be a dick about it, aren’t you? Maybe it’s because I’ve been so vocal about hating girly things. My mom was always pushing me to be as feminine as she was. But I was a tomboy. She hated that, and I kind of loved that she hated it. At some point in my teens, I started to change....

F4M 28m 31s 26/11/2017 Free

Friend to Client

You know about my money issues... As a friend, don't you want to help me out by using my mouth like no man before?

F4M 16m 18s 07/09/2017 Free

Tomboy Saves Her Best Friend From Spending His Money on Strippers

All done! And you were going to pay someone to change your oil for you. You're lucky your best friend is awesome with cars. No, I won't take your money. But you could buy me some dinner. Tonight is good. We could even go right - Oh, I see. It's another frat event. Let me guess... the strip club again? I knew it. You already look guilty. And maybe you're thinking about how much money you're going to waste this time. You get a little drunk, and a little horny, and you go crazy on lap dances. Well, time for me to save you from yourself. I saved you from spending money on an oil change. Now I'm going to save you from spending even more on some stripping and a lap dance. Oh, don't give me that look. Just because I'm a girl doesn't mean I can't change the oil in your car. And...

F4M 22m 6s 25/05/2017 Free

Lesbian repays her male friend for a favor

Fun vanilla script, by u/BetterDeadThanDread about a lesbian repaying her friend for helping her... and finding out thanking him is really fun for her as well.

F4M 13m 25s 07/09/2016 Free

Tomboy has to go from Bully to Girlfriend

Sorry for punching you. And those things I said about your dick, or how you liked to stick it in other guys. You really should have fought me like I wanted. I really wasn't expecting them to be so strict here at this school. They have some bullshit zero-tolerance policy. Now they want to expel me. But if you stick up for me at that school hearing tomorrow, they can't expel me. At least it will work in my favor. Now, you don't have any real reason to go out on a limb for me. I'm just a tough girl who only made it into this private school out of charity and a quota. But I think I have an idea about how I can make you want to help me out...

F4M 19m 38s 09/08/2016 Free