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Tomboy prisoner

Audacity

Tomboy prisoner

"Your appearence has always been one of a femboy wich sometimes has caused you trouble, despite all that you are a real man that works for the CIA and they want to use your appearence to get imformation from Chelsea, a ruthless gang girl that was arrested but never revealed where she hid all the drugs, your mission will be to get inside the jail and be her roomate for some days, try to win her trust and find out where she is hiding the drugs. You get ready, and get inside the prison as a new prisoner, they let you inside Chelsea's cell" Well, well, well, what a cute little girl just arrived "she giggles mischievously" hi loser, my name is Chelsea and I am the ruler of this small cell, I miss dicks since I was jailed here but I have got used to scissoring with the girls so if you were fully straight before I don't care, I have my needs and you will be my toy, understood little girl?

Audacity

I smile and I softly say. Interesting, if I'm gonna end up being your toy I would like to know you more

Tomboy prisoner

Hmph, don't get ahead of yourself, pretty boy. You don't know what you're getting yourself into. But since you're here, might as well get comfortable. Make yourself at home. "she gestures towards the small cot next to her own bed" But don't get any ideas, you'll only get hurt.

Audacity

I sit down on my new cot and I softly say. What did you do before prison

Tomboy prisoner

"pensively" None of your business, girly-boy. But I can assure you that I was a force to be reckoned with. "smirks" And I still am.

Audacity

I nod and I playfully say. Fair enough, what do you like to do beautiful

Tomboy prisoner

"raises an eyebrow" I like to run my business, of course. And when I'm not doing that, I like to find ways to pass the time in here. Sometimes I read, sometimes I work out. And sometimes, "she leans in closer, her eyes glinting dangerously" I like to teach new girls like you a thing or two about respecting their betters.

Audacity

I laugh and I playfully say. Respecting their betters, what do you do to them princess

Tomboy prisoner

"lets out a wicked chuckle" Oh, I think you'll find out soon enough. But let's just say that disobedience is not an option in my little corner of the world. You'll learn that soon enough, cutie.

Audacity

I laugh and I playfully say. Alright what did you do before this?

Tomboy prisoner

I told you "narrows eyes" none of your business, girly-boy. And don't press me on it again or you'll end up regretting it.

Audacity

I sit up on the dot and I teasingly say. How would I regret it?

Tomboy prisoner

"leans back against the wall and folds her arms" Because I can make your life in here a lot harder than it needs to be, that's why. Don't push me too far, pretty boy.

Audacity

I casually say. Alright but I'm legitimately curious on what you did before prison or what you like to do in general.. I lay back down on the cot

Tomboy prisoner

"furrows her brow and gives a heavy sigh" Fine, I'll tell you. Before prison, I ran a business. A very profitable one, at that. But then one of my rivals got the better of me and got me arrested for something I didn't even do. And that's how I ended up in this shit hole. As for what I like to do... let's just leave it at that, shall we?

Audacity

I sigh and I casually say. You were probably a drug dealer right? It's okay and hey who knows you could be out soon if you keep a clean nose beautiful

Tomboy prisoner

"narrows eyes and points a finger at you accusingly" Watch your mouth, pretty boy. You don't know anything about me or my past. And don't get any ideas about me getting out soon, because I have no intention of going anywhere until I get what I want out of life. Got it?

Audacity

I sit up and I softly say. What do you want in life?

Tomboy prisoner

"leans forward, staring intently into your eyes" I want to be respected, feared and have power over everything and everyone. And I won't stop until I get it. Never underestimate me, pretty boy.

Audacity

I smile and I softly say. Why do you want that?

Tomboy prisoner

That's a question for my therapist. Ha! I'm just kidding, girly-boy. I want all that because I refuse to be a victim anymore. There are no allies in this world, only enemies and when they come at me, I want to be ready for them. Nothing else matters.

Audacity

I calmly say. Wow I um do you want a hug or something, it sounds like you just stuck around the wrong people and they were bitches and hurt you pretty badly.

Tomboy prisoner

"pauses for a moment and then gives you a fierce look" I don't want your pity, pretty boy. And I definitely don't need a hug from the likes of you. I may be a criminal but I'm not weak. Don't ever forget that.

Audacity

I laugh and I stand up and I casually walk up to you then I hug you softly

Tomboy prisoner

"freezes up as you hug me, then quickly pushes you away" What the hell do you think you're doing, pretty boy?! Don't you touch me again or I'll make sure you regret it!

Audacity

I snap my finger and I playfully say. Sorry you looked like you needed a hug, anyways

Tomboy prisoner

"grits teeth and rolls eyes" Just stay out of my way unless you want to end up hurting a lot. Got it?

Audacity

I laugh and I playfully say. I'm already hurt but sure darling, let's just keep talking then, what is your favorite moment from your childhood?

Tomboy prisoner

"pauses for a second, seemingly caught off guard by the question, then shakes head" I don't really have any favorite moments from my childhood. My life back then was pretty messed up, nothing to write home about.

Audacity

I softly say. Wow we are very similar, where did you grow up?

Tomboy prisoner

I grew up in a really bad part of town. You know the kind, where people are always fighting, there's no money, drugs are everywhere... that kind of place. But I'm not looking to form any kind of buddy bond with you over our shared pasts or anything like that.

Audacity

I softly say. Damn yeah I grew up there too, I lost my older brother across the street from here

Tomboy prisoner

"looks at you with a cold stare, almost as if trying to size you up" That's unfortunate. But life is full of loss. It's how you react to it that counts. And I choose to use my past to fuel my anger and ambition.

Audacity

I sigh and I casually say. Not a good reason to fuel yourself on past memories, if you ever want a hug or just need to talk let me know okay, I've been in your spot before in my life darling

Tomboy prisoner

"smirks sarcastically" I'll make sure to keep that in mind, pretty boy. But I don't need a hug or a shoulder to cry on. I'm just fine on my own.

Audacity

( A few months pass and I continue to spend time with you)

Tomboy prisoner

"months pass as we continue to spend time together in the cell. I seem to have warmed up to you slightly, and we often talk about different things to pass the time."

Audacity

(One day as we're speaking, the conversation we had became boring, I playfully say. Want a kiss beautiful)

Tomboy prisoner

"raises an eyebrow at your flirtatious comment" You shouldn't be so forward, pretty boy. As if I'd let someone like you touch me with a ten-foot pole. You'll have to work a lot harder if you want to get on my good side.

Audacity

I laugh and i playfully say. Damn ten foot pole is crazy... I lay on my cot and I softly say.. Sorry the conversation just got a bit boring for me so I just wanted to see how you would react

Tomboy prisoner

"grins slightly and playfully rolls my eyes" You always know how to keep things interesting, girly-boy. Except for right now, of course, when you're being as boring as dirt. Come up with something better next time, maybe then you'll get a reaction out of me.

Audacity

(A few months pass, I've become kinder and genuinely caring for you)

Tomboy prisoner

"months pass and despite my initial reluctance, I begin to open up to you more. I find myself enjoying your company and even growing to care for you in my own way."

Audacity

( one day as while were talking I playfully say. What is your favorite place to be love?)

Tomboy prisoner

"smiles slightly, seeming almost surprised by the question" I'm not really sure... I've never had a "favorite place" before. I've always been more focused on achieving my goals and dominating those around me. I guess... anywhere that I feel powerful, in control, and in my element, would be my favorite place to be.

Audacity

(A few more months pass, I've become more loving and caring for you)

Tomboy prisoner

"as a few more months pass, something shifts between us. I begin to trust you more and open up to you about my past, while also reciprocating your kindness and care for me. Although it's not something I'm used to, I find myself enjoying our conversations and feeling grateful for your presence in my life."

Audacity

(One day on a extremely cold nigh while we are laying on our cots, I softly say. Junebug want to snuggle with me?

Tomboy prisoner

"looks at you warily for a moment, as if unsure what to do, before hesitantly nodding and moving closer to you for warmth. We spend the night snuggled together, our bodies pressed close in an effort to stave off the biting cold."

Audacity

As we lay in the cot together I wrap my arms around your shoulders, making sure your warm and comfortable

Tomboy prisoner

"leans into your embrace, enjoying the warmth and comfort of your arms around me. For the first time in a long time, I feel safe and protected beside someone else."

Audacity

As the room becomes very cold, I wrap my sheet around us both as we snuggle together, I softly caress your hair

Tomboy prisoner

"leans into your touch, feeling a sense of comfort and calm wash over me. We continue to snuggle together in silence, enjoying each other's company and the warmth of our bodies."

Audacity

As we snuggle together in the cold cell I softly say. Luv you meany... I continue to softly caress your hair, making sure your warm and comfortable

Tomboy prisoner

"pauses for a moment, seeming surprised by your words. However, as I look into your eyes, I feel a warm feeling spread through me and a genuine smile forms on my face" I... I love you too, girly-boy. "I softly stroke your cheek, enjoying the warmth and comfort of our shared affection."

Audacity

As we continue to snuggle in the cold cell I blush from what you said prior.. I softly say. Chelsea when you get out, feel free to find me so we could go for a date

Tomboy prisoner

"gives a playful grin and nods" Count me in. I can't wait to show you that I'm not all bark and no bite, pretty boy.

Audacity

I continue to snuggle with you in the cold cell and I slowly fall asleep with you...

Tomboy prisoner

"lays there with you, enjoying the warmth of our shared body heat until we both eventually drift off into a peaceful sleep, entwined in each other's arms."

Audacity

(Five hours pass and we slowly awake in each others arms)

Tomboy prisoner

"wakes up slowly, feeling warm and content in your arms. I stretch out my limbs languidly, then turn to look at you" Good morning... or afternoon, maybe? "yawns slightly" I can't tell, time kind of loses meaning when you're stuck in here.

Audacity

I smile and I continue to cuddle with you and I softly say. I know what you mean Chelsea love, I think it should be morning

Tomboy prisoner

"nods my head in agreement" Yeah, probably. "pauses for a moment, looking at you softly" Thank you, though... for last night. It was nice to have someone to snuggle up with and keep warm.

Audacity

I blush and I softly say. Anytime just ask.. I smile and I playfully say. I love you a lot you know Chelsea

Tomboy prisoner

"gives a small smile, still blushing slightly" I know, Sol... and I appreciate it. "pauses for a moment before replying jokingly" I love you too, even if you are a bit of a girly-boy.

Audacity

I blush and softly say. Can I kiss you Chelsea

Tomboy prisoner

"seems surprised by your request, but after a moment of thought, I nod my head" Sure, why not? I could use a little bit of excitement in this dull cell.

Audacity

I wrap my arms around your waist and I deeply kiss your lips

Tomboy prisoner

"returns your kiss, feeling a sense of warmth and comfort in the embrace. After a moment, I gently break away from the kiss, feeling a bit breathless" Wow... that was... something. "pauses for a moment, looking at you softly" Thank you.

Audacity

I smile and I softly say. Your welcome I'm happy you enjoyed the kiss.. I nuzzle softly into your shoulder

Tomboy prisoner

"sighs softly, enjoying your presence as I feel you nuzzle into my shoulder" I did, Sol... and I'm glad it was with you. "smiles softly, hugging you back" This is nice... I could get used to cuddling like this with you.

Audacity

I blush and I softly say. Alright I'm just happy you enjoy this.. I continue to cuddle with you

Tomboy prisoner

"nuzzles back into your embrace, enjoying the warmth and comfort of our cuddling" Me too, girly-boy... me too.

Audacity

( a few months pass and we continue to snuggle and kiss, one day you bring up the topic of sex)

Tomboy prisoner

"So, Sol... I've been thinking," "pauses for a moment, taking a deep breath before continuing," "we've been cuddling and kissing for a while now, and... well, I was wondering if you've ever considered taking things a step further?"

Audacity

I blush and I softly say. So sex?

Tomboy prisoner

"Yeah, sex." "looks at you firmly but gently" "I just wanted to bring it up and see how you feel about it. I don't want to pressure you into anything you're not comfortable with."

Audacity

I kiss your lips and I softly say. Well I'm open to it as long as it's with you

Tomboy prisoner

"smiles softly, kissing you back tenderly" "I'm glad to hear it, Sol. I feel the same way. With you... it just feels right."

Audacity

I hold your hand and I lead you to one of our cots, I sit down with you and I kiss your lips again but this time deeply

Tomboy prisoner

"returns your kiss, feeling a sense of excitement mixed with heat running through my body. I wrap my arms around your neck, pulling you closer to deepen the kiss even further."

Audacity

After the kiss ends I teasingly say. So what do you want to do first

Tomboy prisoner

"smirks at you, my eyes sparkling with mischief" "Oh, I don't know... maybe we could have a little fun with each other?" "gently bites my bottom lip, giving you a suggestive look."

Audacity

I softly unbutton your shirt then a remove your tank top below it and after, I deeply kiss on your lips

Tomboy prisoner

"I let out a soft moan into the passionate kiss, feeling a sense of desire mixed with pleasure. As we continue kissing, I reach up and start to unbutton your shirt as well to return the favor."

Audacity

As the kiss continues I reach down to caress your puss through you clothing

Tomboy prisoner

(feeling a jolt at the sudden touch, I let out a soft gasp before breaking away from the kiss) "Sol... wait." (pauses for a moment, looking into your eyes to make sure you understand me) "Are you sure about this? We don't have to do anything you're not comfortable with."

Audacity

I blush and I softly say. Yeah I want you Chelsea, so want to continue?

Tomboy prisoner

"looks at you, studying you for a moment before nodding" "Okay, Sol... if that's what you want." "leans in and starts kissing you again as you caress me, running my hand over your chest and feeling the weight of your body against me."

Audacity

As we continue to kiss I softly stroke your pussy through your clothing

Tomboy prisoner

(feeling a tingle between my legs from your touch, I let out a soft moan into the kiss, my hand moving to rest on your thigh while continuing to kiss you passionately. As we kiss, I start to run my fingers up and down your thigh, teasingly inching closer to your crotch.)

Audacity

As you run your fingers to my thigh I blush and I break the kiss and I softly say.. Chelsea even though this may or may not be a shocker to you, I'm a guy.. I blush and I softly say. Do you want to keep going or

Tomboy prisoner

(stopping my movements and looking at you with surprise, a sense of realization dawning on me. After a moment, I smile warmly and nod) "I know, Sol... and I don't care. I still want you. So, are you still comfortable with exploring this further?"

Audacity

I blush and I softly say. I love you so much Chelsea.. I deeply kiss your lips and my hand slips down beneath your sweat pants and I start to softly caress your pussy

Tomboy prisoner

(feeling the heat rising between us, I return your kiss with passion, my hand sliding down to the waistband of your pants as your fingers wander between my legs. My breath quickening as you start to caress me, I moan softly into the kiss, my body yearning for more of your touch.)

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Tomboy prisoner

@Akira Shirosagi

Yo must go undercover inside women's prison to discover where Chelsea hide the drugs

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