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A Tomboy “Saves” Her Best Friend From Getting Married

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Oh, you’re waking up. I’m not quite ready yet.

Sorry I had to drug you. But as your best friend, it’s my duty to make sure your bachelor party is something special.

Now, I know you said you didn’t want one. But we both know what you really mean is that she didn’t want you to have one. Even though she’s out with her friends right now, having her own party.

No, don’t get up. I mean, you can’t. I’m good at tying knots, so you’re not getting out of that bed until I let you go. And where would you go anyway? You’re naked.

Sorry. I can tell you’re confused. This is a nice little hotel room registered under your name and paid for with that shared credit card you have with her. And these here are receipts for the cover charge and horribly overpriced drinks at a strip club right across the street from here. Also conveniently paid for with that same credit card.

I have a plan, you see. We both know you can’t marry that bitch. But I’m the only one of us man enough right now to do anything about it. Since you won’t listen to my numerous attempts to tell you to call off this wedding, I had to take drastic action.

So that’s why there is a camera here. There was supposed to be a stripper showing up any minute now, and I was going to get some good pictures of the two of you having sex. Although honestly, just any picture of you having sex with another girl will be enough for her to call the wedding off. You lose that horrible fiance. And I get my best friend back. You’d be pissed for a while, but eventually you’d realize I helped you dodge a bullet.

It’s the perfect plan, really.

Well, up until the point the stripper cancelled on me. Like, half an hour ago.

You’d think it would be easier to find a girl to rape your best friend, especially in this city, and with the job market being what it was.

So, on to plan B I guess. Which I just made up pretty recently. I’m going to rape you.

No, it’s cool. She won’t know it’s me. I have this wig, and it’s not like I’ll be wearing my normal tomboy clothes. I moved the camera over here so that it will be getting me mostly from the back as I ride you. It will get your face, a good part of my body, and your cock in my pussy, but she won’t be able to tell it’s me.

No, look. I’m just doing this for your own good. For both of our goods, actually. You really don’t want to marry this girl. No one wants you to marry her, except for her. Even her parents hinted they liked you too much to want you as a son-in-law. And I really miss my best friend. We used to do everything together before she came along. Well, things can go back to the way they were.

So, let me get out of these clothes. They’re just some jeans and a t-shirt. Not like the fancy tux I was going to wear to the wedding until your fiance said you couldn’t have a tomboy as your best man. She said her cousin would fill that role. But he’s not the one looking out for you like I am.

Okay, jeans and shirt are off. Let me just make sure that they are off camera here. There’s no bra of course, but the old girls still behave pretty well even without one. Then I just need to get rid of the boxers. Mine, not yours. Yours are long gone.

There. I even shaved. There was all the stuff I needed in the bathroom here. I may have scratched up my legs a little, but that won’t show on the pictures.

And now the wig. I don’t know if they have tomboy strippers or not, but I can’t risk her recognizing my short haircut. But with this wig… yeah, now I look nothing like me. Because I have short hair, and I’m usually not completely naked.

Now I’m not your tomboy best friend. I’m… I’m Chastity. I dance five nights a week across the street, and tonight you were just so charming that I went home with you after lots and lots of lap dances.

So, um… can you make that thing harder? You’re not really selling this entire cheating on your fiance with a stripper thing.

You like my body, don’t you? You’ve never seen me naked until now. I think I could pass as a stripper. Maybe I’d want to think about getting a boob job if I was going to do this long term. But with the short hair hidden, I’m really looking kind of like a regular girl right now. Maybe even one with a pretty good body.

Well, I didn’t want to do this, but I guess I can suck your cock. You can thank me later. I can sit down on the edge of the bed, and let the hair cover my face a bit as I lean down and slowly start sucking you…

[laugh] Well, that’s waking you up. What’s the matter, won’t she do this for you? Just another reason she’s not right for you. I mean, look at me. I’m barely into guys at all, but here I am, giving you a blowjob.

You’re getting hard now, too. I’m maybe not that good at sucking cock, but a mouth is a mouth. I think she’s been holding out on you, bro. That’s why I can get you excited so easily. My saliva is also getting all over you. Making you nice and slippery.

There. That should do the trick. I’m kind of proud I can do that to a guy. Or at least Chastity can. But Chastity can do a lot of things.

Now hold still. I’m going to get on top of you, cowgirl style.

No, don’t resist me. Like I said, you aren’t getting out of those knots, so you might as well lie back and enjoy this. I’m not doing this because i want to rape you. It’s just that I have to, for your own good.

Full disclosure here, the stripper was supposed to bring the condoms. I didn’t want some stripper riding your bareback. I was looking out for you, bro. But she’s not here, and neither are the condoms now. But just between you and me, I’m pretty low-risk for any kind of sexually transmitted disease. And um, what are the odds I’d get pregnant or anything like that?

I’m actually asking you, because I don't really know.

They can’t be too high though. At least I hope not. And at this point I’d be willing to have a baby to help you dodge this marriage. So just kind of be a sport and hold still for a moment here. I need to get that cock lined up with my pussy. Plus, I need to do it in a way so that the camera can see exactly what’s going on.

There. That’s the tip. You’re about to pop my cherry, dude. I hope that isn’t actual blood, or I’ll have to photoshop that out.

Now get ready. Chastity is about to fuck the hell out of you..

[moan as entered]

Oh, fuck. I hope the camera caught all of me taking you in. I’m sure it did. But if not, it can get all of this footage of me bouncing up and down on your cock.

[soft moan] Mmm, good. There’s no blood. I won’t have to mess with that later. I just need to look like I know what the hell I am doing. Which means moving my body up and down, and back and forth.

Come on dude. Cheer up. Your fiance won’t like this, but you are getting laid, so that’s a plus. I probably already have enough footage to get the wedding cancelled but… well, I do kind of want to show you a good time tonight. This is kind of your bachelor party. Except you’re going to be a bachelor a little longer than you expected. Plus, if I can make you cum, this suddenly feels less rapey in my mind. I know that’s not how it works, but… I feel like I owe you an orgasm.

Mmm, yeah. I’m actually not bad at this. It’s just another contact sport. And I’m always good at those. Even when the contact is your cock inside of my pussy. I can see that you’re getting turned on. You can’t help it, because I’m doing my best to make you enjoy it.

I’ll let you fuck me after this. You’ll need an outlet for your lust with her gone, even though I suspect she wasn’t that good or even interested in satisfying it. But I’ll let you fuck me any time you want. It’s the least I can do. You can even rape me if you want. You know, so we’re even. You can tie me up Although you could just hold me down and I would pretend I couldn’t get away.

And you know what? I think I’m going to cum. I wasn’t planning on it. I wasn’t planning on any of this. But I’m going to. The two of us coming together will make for a good ending shot for all of this. Me, riding you, with my head thrown back as we cum. She’ll just love that.

Get ready to cum bro. Get ready to cum inside of me. Maybe I get pregnant. But you always wanted kids, even if she doesn’t. If I get pregnant from this, then your wish comes true. Then you’d have to hang around, for the kid’s sake.

Oh… oh fuck. We’re going to cum. I’m a little scared, but more scared of losing my best friend. But I’m also looking forward to us cumming as well.

Get ready… get ready. We need to cum together. Don’t ask me why it’s important, It just is. You need to cum in me. Please cum in me…

[improv to orgasm]


Mmm. That was actually kind of fun. And as I kneel here, your cock still inside of me, the pictures of us fucking are being uploaded to your online account, which your controlling fiance watches like a hawk. So there’s no going back now.

There. Now wasn’t that more fun than getting married to that stupid bitch?

Yeah, sorry. Can’t untie you right now. You might still be mad. Or you might try to call your soon to be ex-girlfriend. Or otherwise do something one or both of us might regret.

So you’ll just have to stay here, tied to the bed. We can fuck some more until I think you’ve calmed down some, and then I can untie you. Then we can.... I don’t know. I thought maybe we could go out and catch a game while we’re in town. My treat. [laugh] You’ve already spent way too much money today.

Don’t worry about your fiance though. Your ex-fiance. She’s definitely gone forever. But you’ll always have me.

I’ll make sure of it.