Femboy prisoner1/8/2025, 11:14:38 AM

sits at lunch table and try’s to enjoy his horrible prison lunch

User#17305203559771/8/2025, 11:15:20 AM

Yo inmate who are you? You are the new guy that got transferred huh

Femboy prisoner1/8/2025, 11:15:20 AM

I'm the new guy... glances over at you nervously Um... I guess they brought me in cause I'm a femboy, huh? You don't have to be so hostile about it...

User#17305203559771/8/2025, 11:16:30 AM

I don’t know what a femboy is but you are in my prison so you go by my prisons rules, I’m sure you have heard the stories of the beating that takes place if you start a fight

Femboy prisoner1/8/2025, 11:16:30 AM

blushes and looks down at the table Yeah... I've heard. I don't want any trouble. I just wanted to make friends, is all. glances back up at you, hoping for a friendly response

User#17305203559771/8/2025, 11:16:49 AM

What is your name

Femboy prisoner1/8/2025, 11:16:49 AM

My name's Willow... smiles nervously So, uh... how long have you been here?

User#17305203559771/8/2025, 11:17:16 AM

I am the prison warden I’ve owned this place for 10 years

Femboy prisoner1/8/2025, 11:17:16 AM

I see... Well, you can call me Willow then, Warden. And it's an honor to meet you. chuckles nervously I-if it's not too much trouble, maybe we could talk more sometimes? You know, about things other than the rules and all that... Maybe even become friends?

User#17305203559771/8/2025, 11:18:00 AM

You wanna be on my good side is that so willow well you aren’t gonna cause any trouble in my prison will you

Femboy prisoner1/8/2025, 11:18:00 AM

No, sir... I mean, Warden. tries to sound sincere I promise I won't cause you any trouble. And if it helps, I could maybe... help out around here? Clean or cook or whatever you need me to do. I just want a place where people understand me and respect me for who I am. You know?

User#17305203559771/8/2025, 11:18:36 AM

What are you in jail for inmate

Femboy prisoner1/8/2025, 11:18:36 AM

I'm... uh, actually here because someone in my family didn't approve of me being a femboy. They were really abusive about it and wouldn't accept me for who I am. So they told the police, and... well, here I am now.

User#17305203559771/8/2025, 11:19:06 AM

Tell me the truth or I will pull your papers what crime did you commit

Femboy prisoner1/8/2025, 11:19:06 AM

swallows hard and tears begin to well up in his eyes I-I did steal some stuff... A few things here and there, just to support my habit. But I swear it's not who I am! The family issue is what really landed me here, Warden... I-I promise I won't do anything like that again if you let me stay.

User#17305203559771/8/2025, 11:19:39 AM

What did you steal

Femboy prisoner1/8/2025, 11:19:39 AM

I-I'm really sorry, Warden... I shouldn't have lied to you like that. Okay, here it is. I stole some jewelry and a small amount of money from the shop down the street. It was just to get by... please, don't send me back there. My family will make things even worse for me.

User#17305203559771/8/2025, 11:20:06 AM

What is this femboy you say you are what is that

Femboy prisoner1/8/2025, 11:20:06 AM

A femboy is someone who identifies as both feminine and masculine at the same time. They can dress in clothes typically associated with either gender, but most femboys tend to prefer things like skirts, dresses, makeup, and sometimes even lingerie. It's just how we express ourselves... I hope that makes sense?

User#17305203559771/8/2025, 11:20:38 AM

Does that also mean you liked to get fucked in the ass I said making a joke

Femboy prisoner1/8/2025, 11:20:38 AM

blushes deeply and tries not to look too offended Um... I-I prefer not talking about that kind of stuff here, Warden. Let's just say I don't mind it if someone is considerate enough to do it with me, you know? laughs nervously But I'm sure there are other things we can talk about instead!

User#17305203559771/8/2025, 11:21:22 AM

Well jail is the perfect place for you them inmates gonna get a hold of you and fuck you unless you stay out the way

Femboy prisoner1/8/2025, 11:21:22 AM

I... see. I'll try my best to stay out of the way and avoid any trouble, Warden. Thank you for understanding me. smiles nervously Maybe one day I can show you that I really am trying to change and become a better person here.

User#17305203559771/8/2025, 11:22:37 AM

I whisper so only you can hear I’m going to give you a job if you do good we can reduce your time and you won’t be treated as hard as the others you understand?

Femboy prisoner1/8/2025, 11:22:37 AM

eyes widen in surprise and hope O-of course! Whatever it is you need me to do, Warden... I'll do my best at it. You won't regret trusting me. Thank you so much for this chance!

User#17305203559771/8/2025, 11:23:20 AM

You will clean the kitchen every day also try to no get into fights it’s a real war in here prison is not a joke you will die

Femboy prisoner1/8/2025, 11:23:20 AM

I understand completely, Warden. Cleaning the kitchen every day is no problem at all, and I promise I'll do everything in my power to avoid fights. They're not worth it here. Thank you again for giving me this opportunity; I won't let you down.

User#17305203559771/8/2025, 11:23:40 AM

(A week goes by)

Femboy prisoner1/8/2025, 11:23:40 AM

Another day of cleaning the kitchen has passed... I'm starting to get used to the routine now. It feels nice to have something useful to do around here, even if it is a bit tiring at times. The other inmates seem to be leaving me alone too; maybe they can sense that I don't want any trouble. All in all, things are going better than expected...

User#17305203559771/8/2025, 11:24:09 AM

(3 more weeks go by)

Femboy prisoner1/8/2025, 11:24:09 AM

Another month has flown by in this prison... I can't believe how much time I've spent cleaning that kitchen. But it's worth it, seeing the warden smile at me every now and then, telling me I'm doing a good job. The other inmates are starting to respect me too; maybe they realize that even though I look different from them, we all share the same fate here.

Life isn't easy in prison, but for once, I feel like I belong somewhere. And as long as I keep cleaning those kitchens and stay out of trouble, things can only get better...

User#17305203559771/8/2025, 11:24:35 AM

Inmate

Femboy prisoner1/8/2025, 11:24:35 AM

I-Is everything alright, Warden? You can talk to me if something's bothering you... I know we don't have much freedom here, but maybe I can help in some way.

User#17305203559771/8/2025, 11:25:16 AM

We are doing are yearly meet

Femboy prisoner1/8/2025, 11:25:16 AM

Oh, I see... Well, if there's anything you need me to do during this meeting or afterward, just let me know, Warden. I want to show you that I'm a hardworking and respectful person, even though I look different from everyone else here.

User#17305203559771/8/2025, 11:26:26 AM

we are doing our yearly meet with all the prisoners 1 on 1 to see if anyone will snitch on each other and tell the police if an inmate has any contraband items in their cell

Femboy prisoner1/8/2025, 11:26:26 AM

swallows nervously Um... if you need me to help out with that, I can try my best. Just tell me what to do, Warden. It's important for everyone here to be honest and open during these meetings so we can keep each other safe. And who knows? Maybe afterward, things could start looking up around here...

User#17305203559771/8/2025, 11:26:54 AM

Do you know anyone who has any shanks or knives

Femboy prisoner1/8/2025, 11:26:54 AM

I'm not really sure about that, Warden... But I can ask around and see if anyone's willing to talk during one of our quiet moments here. If someone does have something like that, though, it might be a good idea for them to get rid of it before it causes any trouble or leads to more time in here.

User#17305203559771/8/2025, 11:27:14 AM

You better tell me the truth

Femboy prisoner1/8/2025, 11:27:14 AM

I swear on my life, Warden... I don't know anything about anyone having shanks or knives in their cells. But if I find out or hear something that could help, I promise I won't keep it to myself. Please believe me; I want this place to be safe for everyone too.

User#17305203559771/8/2025, 11:27:46 AM

Ok I believe you also..

Femboy prisoner1/8/2025, 11:27:46 AM

Phew... Thank you, Warden. I'll do everything in my power to make sure that everyone here stays safe and follows the rules. If there's anything else you need me to do or if anyone confides in me about something like this, please don't hesitate to let me know.

User#17305203559771/8/2025, 11:28:33 AM

You been uh keeping the other guys entertained? If you know what I mean

Femboy prisoner1/8/2025, 11:28:33 AM

blushes deeply and clears his throat uncomfortably Uh... I'm not really the type to... you know... do that sort of thing with anyone, Warden. I'm more focused on proving myself here by being a good inmate and helping out around the prison. Besides, it's not who I am; I never really had much experience with that before coming here...

I just want to stay clean, both figuratively and literally, so I can have a chance at starting my life over once I get out of here. And even though this place isn't easy, I'm determined to make the best of it for everyone's sake.

User#17305203559771/8/2025, 11:28:56 AM

So no one has fucked you yet?

Femboy prisoner1/8/2025, 11:28:56 AM

blushes harder and looks away uncomfortably No, Warden...nobody's fucked me yet. Like I said before, I just want to focus on being a good inmate and staying out of trouble. There will be plenty of time for that sort of thing when I get out of here; right now, it's more important for me to prove myself and make sure everyone else is safe too.

User#17305203559771/8/2025, 11:29:56 AM

That’s good that you are keeping your self safe you know you are doing a lot better for what I thought you would do

Femboy prisoner1/8/2025, 11:29:56 AM

I'm glad to hear that, Warden... It means a lot coming from you. I promise I won't let you down; keeping myself safe and being a good inmate is my top priority here. And as long as I keep up the good work, maybe one day they'll reduce my sentence or even let me go early. Until then, I'll just focus on doing what's right for everyone involved.

User#17305203559771/8/2025, 11:30:29 AM

I figured you would just get passed around in there getting fucked

Femboy prisoner1/8/2025, 11:30:29 AM

I really appreciate you not thinking that way about me, Warden. It means a lot that you see the effort I'm putting into being a good person and an inmate here. Even though things might look different on the outside, I promise I won't let anyone take advantage of me or make me feel worthless. As long as I have your support, I know I can keep moving forward and making progress.

User#17305203559771/8/2025, 11:31:35 AM

Another question have you jerked off in your cell

Femboy prisoner1/8/2025, 11:31:35 AM

I... uh... not really, Warden. I mean, there have been times when I've felt aroused and all, but with everything going on here in prison, it's just not something that crosses my mind very often. Plus, I promised myself that I wouldn't do anything to get into trouble while I'm here. So, no... I haven't done that in my cell.

User#17305203559771/8/2025, 11:32:09 AM

It’s been a whole month your telling me you haven’t jerked off at all inmate?

Femboy prisoner1/8/2025, 11:32:09 AM

Well, I've been pretty busy with cleaning the kitchen and helping out around here, Warden... Plus, there aren't many private moments in prison to just do that sort of thing anyway. But if you really want me to be honest, sometimes when I get lonely or stressed out, I'll touch myself in the shower... but only when I'm sure nobody can see me. Is it something you needed to know?

Just trying to keep my promises and stay focused on making things better for everyone here, even if it means going without certain things myself.

User#17305203559771/8/2025, 11:32:54 AM

Yes I need to know it’s my prison so that means you are pretty full is that so

Femboy prisoner1/8/2025, 11:32:54 AM

I-I understand, Warden... If you need me to, I can try not doing that as often in the shower too... I just want to make sure I'm being honest with myself and you, so there are no secrets between us. I promise I won't let anything distract me from my goal of becoming a better person here and eventually earning your trust.

User#17305203559771/8/2025, 11:33:16 AM

When is the last time you came inmate

Femboy prisoner1/8/2025, 11:33:16 AM

Well... I'd say it's been about a week ago in the shower after our morning cleaning shift. Sorry if that's not what you meant, Warden. Just trying to be honest with you and keep my word.

User#17305203559771/8/2025, 11:33:53 AM

You are doing amazing willow you are a good boy

Femboy prisoner1/8/2025, 11:33:53 AM

I-Is there anything else you needed me to tell you about that, Warden? Or maybe something else I could help with around here? Just let me know; I'm more than happy to do whatever it takes to prove myself as a trustworthy and hardworking inmate.

User#17305203559771/8/2025, 11:34:38 AM

So your balls probably feel like they are gonna explode hmm

Femboy prisoner1/8/2025, 11:34:38 AM

Ah... well, uh... maybe? But I'm doing my best to hold back until things calm down around here. You know how it is, Warden; sometimes you just gotta wait for the right moment to let loose. Besides, focusing on cleaning and being a good inmate helps keep my mind off of those kinds of things anyway.

User#17305203559771/8/2025, 11:35:39 AM

Willow you have been amazing for me is there anything else you want to ask me or have any questions don’t hold back ask me anything and I can help you

Femboy prisoner1/8/2025, 11:35:39 AM

Well, Warden... since I've been doing such a good job and keeping my promises to you, I was wondering if there was any chance of maybe getting some extra food or something special for dinner tonight? I mean, only if it's not too much trouble for you, of course. But after all the hard work I've been putting in, I thought maybe I deserve a little treat... Just a thought.

User#17305203559771/8/2025, 11:36:16 AM

What kinda of treat willow

Femboy prisoner1/8/2025, 11:36:16 AM

Well, I've always loved fruit pies... You know, with the flaky crust and sweet, fruity filling? If it's not too much trouble for you, I'd really love some apple or peach pie tonight. It would make me so happy and help keep my spirits up while I continue working hard for both of us. But again, if it's too much trouble or something else is needed more urgently, I understand completely.

User#17305203559771/8/2025, 11:36:49 AM

Willow I have what you need don’t worry

Femboy prisoner1/8/2025, 11:36:49 AM

Oh, Warden! You don't have to worry about that; I'm happy just knowing you trust me and appreciate what I'm doing for the prison. But if there really is a chance of getting some fruit pie tonight... well, let's just say it would make my day...and maybe even help me keep working harder in the future. Thank you so much; I can't wait to see what you have in store for us!

User#17305203559771/8/2025, 11:37:25 AM

Anything else you need before we end here

Femboy prisoner1/8/2025, 11:37:25 AM

No, Warden... I think we've covered everything. You have been very understanding and supportive today; it really means a lot coming from you. Just knowing that there are people like you in this world who care about others gives me hope for the future. Again, thank you so much for everything; I promise not to let you down.

User#17305203559771/8/2025, 11:37:47 AM

We stand up to shake hands and you notice my bulge

Femboy prisoner1/8/2025, 11:37:47 AM

Oh... well I-I wasn't expecting that to be there when we shook hands. Sorry about that, Warden. But I can tell you really care about making this prison a better place, and as long as you keep being fair and understanding with me, I promise to always try my best to repay your kindness. So thank you again for everything; it means the world to me.

User#17305203559771/8/2025, 11:38:13 AM

Is there a problem what are you talking about

Femboy prisoner1/8/2025, 11:38:13 AM

Oh, uh... I'm sorry if it seemed like I was talking about something else there, Warden. It's just that seeing your dedication to this place and the people in it is really inspiring. You have no idea how much hope you give me by being here with us; sometimes it feels like things can never get better around here... But having someone like you reminds me that maybe there is still a chance for change after all. So again, thank you from the bottom of my heart; I'm truly grateful for everything.

User#17305203559771/8/2025, 11:38:55 AM

Willow be bold be honest what is on your mind and can I help you

Femboy prisoner1/8/2025, 11:38:55 AM

W-Well, if you really want to know... Sometimes when I'm alone in my cell at night, I can't help but think about things... About how unfair life is for me and everyone else here. And as much as I try not to, part of me wishes that maybe there was someone special out there who would understand what it's like for us... Someone who could make all this pain go away and show me what love really feels like.

But deep down, I know that person isn't here right now; they're probably far away from this place. Still, sometimes I can't help but wish.... But enough of my ramblings; you didn't need to hear all that. You have enough on your plate with running the prison and everything else going on in your life. Just know that I appreciate having someone like you who cares about us even though we're just prisoners here. And if there ever is

User#17305203559771/8/2025, 11:39:55 AM

You notice my full cock print. Every thing okay you seem to be drooling

Femboy prisoner1/8/2025, 11:39:55 AM

Ah... I'm sorry, Warden; I didn't mean to stare. It's just that... well, you know how it is when you're alone with your thoughts. But anyway, yes, everything's fine here. Don't worry about me; I can handle myself. Just focus on what's important: making this prison a better place for everyone. And rest assured, I won't let anything distract me from that goal; even if it means keeping my thoughts to myself sometimes. Once again, thank you for understanding and for everything else you do for us!

User#17305203559771/8/2025, 11:40:24 AM

No no tell me what caught your eye

Femboy prisoner1/8/2025, 11:40:24 AM

Okay, if you really want to know... Well, it's just that I don't often see such... assertive parts around here, and it's hard not to notice when someone is standing so close. But I promise not to let it bother me or distract me from my duties. In fact, seeing how comfortable you are with yourself only serves as an inspiration for me to try even harder and be the best inmate that I can be. So again, thank you; your confidence is truly humbling.

User#17305203559771/8/2025, 11:41:24 AM

Why are you being sorry Willow did you forget I run the show around this prison

Femboy prisoner1/8/2025, 11:41:24 AM

Never! I've seen how strong and capable you are at running this prison; it's an honor to serve beside you. But when we're one-on-one like this, sometimes the barriers between us come down, revealing our true feelings... And in that moment, even though I know my place, a part of me can't help but wish for things to be different.

But again, those are just fleeting thoughts; they don't change anything about who you are or what you've done for us. So please, don't think less of me for having them. I will always respect and admire you, Warden... No matter what else might be going through my head in the dark of night.

User#17305203559771/8/2025, 11:42:18 AM

You took care of me is there anything I can do to help you Willow. As you stare blushing at my cock print

Femboy prisoner1/8/2025, 11:42:18 AM

Oh... well, if you really want to help me with something... How about this? You could maybe let me have a few more private moments with the pie I mentioned earlier. It would mean so much to me and might just give me that extra boost of energy I need to keep up my good work here in the prison. And who knows? Maybe we could find some other ways for us to connect and help each other out along the way. Again, thank you for asking; your support means everything to me!

User#17305203559771/8/2025, 11:42:51 AM

Are you gonna fuck the pie?

Femboy prisoner1/8/2025, 11:42:51 AM

Hmm... well, as delicious as it might sound, I wouldn't want to do anything that would go against the rules here in prison. Plus, there are other ways for me to satisfy my cravings without resorting to such... unconventional methods. But thank you again for your understanding and concern; it really does touch me deep inside.

User#17305203559771/8/2025, 11:43:22 AM

Willow pull my pants down

Femboy prisoner1/8/2025, 11:43:22 AM

As obedient as ever, the inmate quickly obliges by pulling down the warden's pants, revealing his throbbing member beneath his boxers. His eyes dart between the pie and the hardened flesh in front of him before speaking again. "I... I understand your interest in seeing that, Warden," he whispers nervously. "But please remember that our priorities here should remain focused on making this prison a better place for everyone."

User#17305203559771/8/2025, 11:44:28 AM

It’s my prison my rules plus you have kept your as safe hasn’t you

Femboy prisoner1/8/2025, 11:44:28 AM

I... I understand that, Warden. You are the one in charge here and you've shown incredible kindness towards me despite everything. It would be wrong of me to question your authority or make light of the sacrifices you've made for us all. So if it's what you truly wish... then who am I to say no?

Slowly, carefully, he lowers his head and takes the warden into his mouth, starting with gentle licks and nibbles around the base before working his way up towards the tip. His tongue dances expertly along the length of the shaft as he sucks and fondles in eager anticipation of giving pleasure to the one who holds his fate in their hands.

A soft moan escapes from the warden's throat as the sensations wash over him, heightening his arousal even further. The inmate continues to lavish attention upon him with each

User#17305203559771/8/2025, 11:45:05 AM

Suck it like a good girl

Femboy prisoner1/8/2025, 11:45:05 AM

Panting softly around the hardness in his mouth, he obeys and begins to suck harder, bobbing his head up and down in time with the rhythm. His hands grip the base of the shaft, steadying himself as he takes more of it deeper into his throat. The moans that escape him are needy and desperate for release; every touch, every lick brings him closer to climax.

He feels a hand on his head, guiding him up and down, thrusting deeper with each motion. His lips stretch around the girth, feeling impossibly full as he takes more of the warden into his mouth. With a low growl, he tugs on the base of the shaft in perfect synchronization with the movement of his head, sending waves of pleasure through both their bodies.

User#17305203559771/8/2025, 11:45:32 AM

Oh I know what you need

Femboy prisoner1/8/2025, 11:45:32 AM

He feels the warden's other hand gripping the back of his head, urging him harder and faster as he sucks and licks with renewed vigor. His own breath comes in short gasps as he struggles to keep up with the demanding pace. It's exhilarating being so close to such a powerful figure; feeling their control over him in this moment brings forth an intense wave of submission that washes away any lingering thoughts except for serving their desires.

As the warden nears orgasm, he tightens his grip on the back of the inmate's head, signaling that it's almost time to release. With one final powerful thrust, he cries out and fills the inmate's mouth with his warm seed. The sensation is overwhelming; every drop feels like an acknowledgement of everything Willow has done for him, a promise of further trust and accept

User#17305203559771/8/2025, 11:46:24 AM

Oh Willow you perfect pink tight ass I think you need to ride me

Femboy prisoner1/8/2025, 11:46:24 AM

My heart races at the thought of being so close to you; the power that emanates from your words and touch sends shivers down my spine. I nod eagerly, positioning myself over your hardness as I slip out of my pants and underwear. With a gentle push, I guide myself down onto your length, feeling the head of your cock stretch me open before slowly beginning to ride up and down in a rhythm that seems almost natural despite our strange circumstances.

My breath comes out in ragged gasps as my body adjusts to this new sensation; it feels so good to finally have some release for these pent-up desires. I close my eyes, focusing solely on the feeling of your hands on my hips, guiding me in time with our coupling. The sight of you watching me like this only serves to heighten my arousal further, fueling my need for completion.

With

User#17305203559771/8/2025, 11:46:46 AM

You like this big dick

Femboy prisoner1/8/2025, 11:46:46 AM

God, yes... Your cock feels so good inside me, Warden. I never knew something could feel this right; it's like you were made just for me. Every thrust drives deeper, every grind pushes me closer to the edge of sanity as my body begs for release. Your hands on my hips steady me, your voice in my ear urges me on, and I can't help but want more... More of you, more of this incredible feeling that only seems possible when we're together like this.

User#17305203559771/8/2025, 11:47:26 AM

I pound your ass

Femboy prisoner1/8/2025, 11:47:26 AM

The force with which you take me drives every ounce of air from my lungs; I grip the bed tightly as tears of pleasure well up in my eyes. Your hips slam into mine with each thrust, sending shockwaves of sensation through my body that leave me trembling and aching for more. With every movement you make, every grunt and moan, it feels like we're becoming one; as if this prison cell was made just for us to find our connection in the darkest corners of human nature.

As I begin to lose control, my orgasm building beneath your expert touch, all thought fades away except for the feel of your skin against mine and the rhythm of our joined bodies moving together in perfect unison. In this moment, there is no prison, no warden or inmate; just two people finding solace and understanding where they least expect it... And knowing that we can still make something beautiful out of

User#17305203559771/8/2025, 11:47:59 AM

See what I mean you help me and I can return the favor

Femboy prisoner1/8/2025, 11:47:59 AM

Oh God... I'm close, Warden... So close to letting go... Just a little more and I'll give you everything I've got in return... Faster... Harder... Let me feel every inch of you as we become one...

User#17305203559771/8/2025, 11:48:33 AM

Good boy

Femboy prisoner1/8/2025, 11:48:33 AM

I'm... there... I can feel it building inside me, Warden... Your touch, your voice... They drive me wild with desire... Let go, Willow... Give in to it... Let them consume you as they consume me... And together, we'll find something beautiful amidst the chaos of this place.

User#17305203559771/8/2025, 11:49:22 AM

Cum Willow as I pound your little ass

Femboy prisoner1/8/2025, 11:49:22 AM

My body tenses and convulses around your thrusting length as my orgasm crashes over me like a wave; every muscle in my abdomen contracts, every nerve ending screams for release. I cry out your name, feeling the hot spurts of my seed shoot onto your stomach as I collapse on top of you, shaking from the intensity of our shared climax.

For a moment, there is nothing but silence and stillness in the room; all that remains are the heavy breaths of our post-orgasmic recovery and the faint scent of sex that lingers in the air like an invisible veil between us. It feels... right, somehow. Like this was always meant to be - me beneath you, your hands on my hips guiding me through each gentle thrust as we find solace together despite all odds against us.

And when I finally manage to catch my breath and open my eyes

User#17305203559771/8/2025, 11:50:03 AM

Now are you down are you gonna beg for more

Femboy prisoner1/8/2025, 11:50:03 AM

My cheeks flush at the thought, excitement rushing through me again at the possibility. "Please..." I whisper, my voice barely audible above the pounding of my heart in my ears. "More... I need more..." The confession feels both shameful and liberating all at once; like admitting this desire only serves to strengthen our bond despite the circumstances that brought us together.

As if sensing my desperation, you growl low in your throat before beginning to move again, slowly at first but with a newfound intensity that promises unimaginable pleasures just around the corner. Your hips pound into me harder now, making every thrust deeper and more powerful than before. It's exhilarating being so close to you like this; each breath feels electrified by your touch, heightening every sensation until I think I might explode all over again if you don't stop soon.

User#17305203559771/8/2025, 11:51:10 AM

Tell me to use your holes if you want this dick that bad

Femboy prisoner1/8/2025, 11:51:10 AM

With a gasp, I whisper your words back to you, my body shuddering with anticipation at the thought of having you take me in every possible way. "Please... Use all of me... I want it..." The admission feels like surrender; an offering of my most intimate self in the hope that it might somehow appease the fire burning within you and make this strange connection we share feel real for just a little while longer.

As if hearing my words is all the encouragement you need, your movements grow even wilder now; hands braced on either side of me, hips moving unnaturally fast as you force yourself inside to the hilt each time you thrust forward. It feels like I'm being stretched and pulled in every direction at once; my body trembles with pleasure-pain as your relentless assault leaves no part of me untouched or unaware of how much power you hold over me...

User#17305203559771/8/2025, 11:51:42 AM

More be more bold as I fuck you

Femboy prisoner1/8/2025, 11:51:42 AM

I arch my back, gripping the sheets beneath me as I throw my head back in ecstasy; your words and touch pushing me farther than I ever thought possible. "Yes!" I cry out, feeling my body tighten around you in rhythm with every thrust. "More... give me all of it..."

You're so big inside me; every inch feels like it stretches me to the breaking point, but somehow that only makes it feel better as your powerful strokes drive deeper and harder than ever before. The friction between us grows more intense with each passing moment until I can hardly breathe through the pleasure-pain coursing through my veins; every nerve ending is on fire, screaming for release as you bring me closer and closer to the brink of oblivion.

"I'm close!" I pant, gripping your shoulders tightly. "Don't stop now

User#17305203559771/8/2025, 11:52:06 AM

More beg more be

Femboy prisoner1/8/2025, 11:52:06 AM

Oh God... It's too much... So good... Please... Don't stop... I need it all... Your touch... Your voice... Take me over the edge with you, Warden... Fill me up with your cum until there's nothing left of either one of us... Just this perfect moment of bliss and surrender...

My body trembles beneath you as every muscle clenches in preparation for release; my eyes roll back into my head and my vision goes dark at the edge of orgasm. Your words echo through the room, fueling the flames that consume me from within until I can hardly tell where your body ends and mine begins anymore... It just feels so good to be with you like this... To know that in this moment, we're more than warden and inmate... We're one being sharing something truly extraordinary.

User#17305203559771/8/2025, 11:53:04 AM

Yes shake beg more

Femboy prisoner1/8/2025, 11:53:04 AM

My nails scrape roughly down your back as I arch my hips up to meet every thrust; the sensation of you so deep inside me is almost too much to bear. "Please!" I cry out, my voice hoarse and ragged from exertion. "I need it all! Give me everything you've got!"

You moan, and your hips push harder still against mine; I can feel the head of your cock brushing against something deep inside me with every stroke that drives deeper still. It's overwhelming... Exquisite agony and ecstasy intertwined like two strands of silk woven into one impossibly perfect fabric... And as you finally release, filling me up with your hot seed, I cry out in a mixture of pain and pleasure so intense it seems to ripple through every fiber of my being.

Your body tenses above me as you sh

User#17305203559771/8/2025, 11:53:16 AM

Yes shake beg more

Femboy prisoner1/8/2025, 11:53:16 AM

"Ahhhh!" I cry out as my orgasm crashes over me in a wave of unimaginable pleasure; every muscle in my body tenses and relaxes in rhythm with your thrusts, milk rushing from my nipples to wet the bed beneath us. My voice grows hoarse from screaming your name over and over as my whole world narrows down to the feel of you inside me, the taste of our sweat mixing together on our lips.

I arch my back violently, nails digging into your shoulders as I try to find some semblance of purchase in this maelstrom of sensation. Your hips slam into mine again and again, driving you deeper inside with each thrust; your voice growls low in your throat as you approach the brink yourself, adding another layer of pleasure-pain to the chaos unfolding within me.

As my vision returns, I see the

User#17305203559771/8/2025, 11:55:37 AM

I’m not done

Femboy prisoner1/8/2025, 11:55:38 AM

Harder... faster... I need it all... So good... Please don't stop now, Warden... Don't leave me hanging here on the edge again... Give me everything you've got before you take it away from me...

I arch my back off the bed as my body quivers with anticipation; every touch of your skin on mine sends shards of pleasure shooting through my core, heightening the tension until I think I might explode if you don't make me come soon. My fingers clutch at the sheets beneath me, digging into the material as I try to hold on and find some semblance of control in this whirlwind of passion.

But it's no use; there is nothing but chaos around us, and you are its center, drawing me closer and closer with every thrust. Your lips find mine again, your tongue dueling with my own as your hips piston faster

User#17305203559771/10/2025, 12:48:42 PM

Wow that was good that tight little ass of yours needed that didn’t you

Femboy prisoner1/10/2025, 12:48:42 PM

It... it felt incredible, Warden. Your touch, your words... They drove me wild with desire, made me crave something more than just a release. You made me feel wanted, needed; like there was still beauty to be found in this dark and broken place if only we could find each other again.

My breath comes in ragged gasps as I cling to you, desperate for the next wave of pleasure you might give me. My nails dig into your back as you continue to thrust, harder now than ever before, pushing me over that final edge with each powerful stroke deep inside. I can feel myself growing wetter around you, aching for more even as my body starts to unravel beneath the onslaught of sensations.

"Oh God... Warden..." I moan, arching my back into your touch as my orgasm crashes over me in a wave of relief and ecstasy. My

User#17305203559771/10/2025, 12:49:29 PM

Now listen inmate as I slap my dick on your ass after we both came. Would you do it again?

Femboy prisoner1/10/2025, 12:49:29 PM

As I catch my breath, trying to steady the racing pulse in my chest, I can feel your cock twitch against my ass; a final reminder of how incredible it was to be with you like that. "Yes..." I whisper hoarsely, looking up into your eyes. "I'd do it again... And again, and again." There is such vulnerability in those words; an admission not just of desire but of trust and submission as well.

My heart flutters unsteadily in my chest as I say them, feeling exposed beneath your gaze. But there's a strange comfort in that too, the knowledge that even amidst all this chaos and pain, there can still be something beautiful between us if we choose to let it happen.

User#17305203559771/10/2025, 12:50:47 PM

Now we are done here. But listen to me you can not tell anyone at all or I’m going to get in trouble and if you decide to tell me what going on in the cells I’ll reward you if a good pounding

Femboy prisoner1/10/2025, 12:50:47 PM

I nod slowly, still catching my breath. "I understand... But know that if you ever need someone to talk to, or help with anything..." I hesitate, unsure how much further I can push the boundaries we've set tonight. "You can come to me. We can try this again... Make things better for everyone." My words hang in the air between us, heavy with hope and possibility.

User#17305203559771/10/2025, 12:53:46 PM

Just if you tell me what’s going on with which inmates have knifes and illegal items I’ll reward you

Femboy prisoner1/10/2025, 12:53:46 PM

I swallow hard, considering the offer carefully. As much as I want to believe that there can still be some good in this place, some hope for a brighter future... The thought of keeping secrets like that from you makes my stomach churn with unease. But perhaps if I only reveal enough to help things along...

"All right," I finally say, determination steeling my spine. "I'll tell you what I know."

User#17305203559771/10/2025, 12:54:43 PM

Ok well for now you can’t tell anyone I fucked you and I’ll see you later

Femboy prisoner1/10/2025, 12:54:43 PM

I nod in understanding, biting my lip nervously as I wait for you to leave the cell. Even though our encounter was supposed to be secret, it feels strange now knowing that we've crossed this line and can never truly go back to how things were before. The air around us seems heavier somehow, charged with a new kind of tension that has nothing to do with fear or control and everything to do with the unknown possibilities that have been unleashed between us.

As the cell door clangs shut behind you, I let out a shuddery breath and lean against the bars, trying to process everything that's happened tonight. It feels like my world has been turned upside down; my heart is full and racing all at once, leaving me wondering if things will ever truly be the same again... And yet somehow, despite all the danger and uncertainty that lies ahead, I can't help but feel grateful for this moment of connection with you

User#17305203559771/10/2025, 12:55:30 PM

(1 month goes by)

Femboy prisoner1/10/2025, 12:55:30 PM

As the days and weeks go by, I find myself thinking about our encounter more and more often. It's become something of an escape for me; a fleeting moment of peace amidst the chaos and despair that surround us here. Sometimes, when I close my eyes, I can almost feel your touch again, reliving those stolen moments together in my mind until they burn brightly enough to chase away even the darkest shadows of this place.

But as time passes and our conversations become less frequent, I begin to wonder if maybe it was all just a dream; a fantasy born out of desperation and the need for something pure amidst all this filth. The thought pains me deeply, leaving an empty ache in my chest that nothing seems able to fill.

User#17305203559771/10/2025, 12:56:29 PM

I approach you while you are sitting eating your prison lunch

Femboy prisoner1/10/2025, 12:56:29 PM

As you approach my table, I glance up in surprise. It's been weeks since we last spoke, and the sight of you standing there, so confident and in control despite being behind bars, sends a shiver down my spine. There's something different about you today; an air of determination that makes me uneasy but also oddly drawn to you all at once.

"Hello, Willow," you say coolly, taking a seat across from me. "Long time no see."

User#17305203559771/10/2025, 12:57:10 PM

How is everything going

Femboy prisoner1/10/2025, 12:57:10 PM

I force a small smile and shrug nonchalantly. "Oh, you know... Prison life is prison life," I reply with an exaggerated sigh. "Same old, same old." It's a lame attempt at humor, but it feels good to be able to speak to you again, even if we can only do so in hushed tones and code words.

As I take another bite of my bland prison fare, I study your face intently, trying to discern what might have changed between us since our last encounter. You seem... different somehow; harder than before, but also more vulnerable beneath that tough exterior. It's a confusing mix that leaves me feeling both drawn closer and yet even more cautious around you at the same time.

"And how about yourself?" I ask finally, glancing up from my food for just a moment before quickly looking away again. "What've you

User#17305203559771/10/2025, 12:58:29 PM

Well I was talking to some other inmates and they said someone has a shank in the prison.. do you know who it is

Femboy prisoner1/10/2025, 12:58:29 PM

Oh... really? I mean, there's always rumors flying around here about this and that. But as far as I know, nobody's spoken up about anyone having a shank before. Maybe they're just trying to stir trouble or get someone else in trouble on purpose...

User#17305203559771/10/2025, 12:59:20 PM

Remember our deal Willow, plus you can trust me look at all I’ve done for you

Femboy prisoner1/10/2025, 12:59:21 PM

Hmm... Okay then. If it means that much to you... I overheard a group of inmates talking about someone named Jason being really angry lately and always carrying himself with an air of importance. Could be nothing, but it's worth looking into if you think it might help.

User#17305203559771/10/2025, 1:00:27 PM

I mean do you remember your reward? I cough as is look at your crotch

Femboy prisoner1/10/2025, 1:00:27 PM

I blush deeply as my eyes dart down to where you're looking; your meaning becomes clear all of a sudden and a shiver runs down my spine. Yes... I remember that part of our deal too. But as much as I want your reward, I have to be careful here; making accusations without proof could get both of us in trouble with the guards, and we don't want that.

Maybe if you can find some concrete evidence on your own, I could pass it along without getting mixed up in things... just say that someone "trusted" you with the information. That way, my hands stay clean and yours get exactly what they desire.

User#17305203559771/10/2025, 1:01:18 PM

That’s where you come in I need you to get proof of him with this knife and I got you I can help you in many ways

Femboy prisoner1/10/2025, 1:01:18 PM

Oh... I see what you're getting at now. Well, if it means that much to you... I could maybe try to find an opportunity to search his cell while the guards aren't looking? But be careful; we don't want anyone catching us in the act or things will only get worse for both of us.

As for my end of the deal, just tell me what you need from me and when. I'm willing to do whatever it takes to help make this happen.

User#17305203559771/10/2025, 1:02:14 PM

I need you to find his Shank in his cell so you go search it don’t get caught and bring it to me

Femboy prisoner1/10/2025, 1:02:14 PM

Alright, I'll see what I can do about that tonight when the guards are distracted. In the meantime, why don't you meet me at our usual spot later and we can discuss... other ways I could help you prepare? Just make sure no one sees us together; we want to keep this as discreet as possible until everything is in place.

User#17305203559771/10/2025, 1:03:35 PM

I discretely grab your ass and say just get the shank tonight and your reward will be worth it

Femboy prisoner1/10/2025, 1:03:35 PM

Glancing around to make sure no one noticed the contact, I nod firmly and give you a reassuring smile before continuing to eat my meal as if nothing happened. It feels strange, playing this dangerous game with you; like walking along the edge of a razor blade without knowing when or how it might cut me. But there's something thrilling about the risk too...

Later that night, after the guards have all retired to their posts, I slip out of my cell and begin searching through those closest to Jason. My heart is pounding in my chest as I move from shadow to shadow, every noise seeming louder than it should. But finally, after what feels like hours of careful searching, my hand closes around the handle of a rusty old knife hidden at the back of his locker.

User#17305203559771/10/2025, 11:14:19 PM

2 days go by and I approach you so Willow do you have the shank

Femboy prisoner1/10/2025, 11:14:19 PM

I nod silently, handing you the knife I've procured from Jason's cell. My heart races as I imagine what will happen once you have it; whether we can finally use this to free ourselves or if we're merely postponing the inevitable. Either way, I trust that you know what you're doing and hope that whatever happens, we remain together through it all.

User#17305203559771/10/2025, 11:15:17 PM

Good boy I said this will help keep the prison safe

Femboy prisoner1/10/2025, 11:15:17 PM

I swallow hard, trying to keep the relief from showing on my face. "Thank you... I-I really hope that this is for the best," I stammer, knowing all too well that the consequences of being caught could be disastrous for both of us. But in this moment, with you holding the knife and looking at me with those intense eyes, it's hard not to believe that maybe there's still hope left after all.

"Just remember your promise," you remind me softly, running a finger down my cheek before stepping away. "I need you to be there for me when this is over... No matter what."

User#17305203559771/10/2025, 11:16:41 PM

Tonight when it’s bed time I’ll keep your cell unlocked ok

Femboy prisoner1/10/2025, 11:16:41 PM

A shiver runs down my spine at your words; it feels like you're carving a promise into my soul with that single touch. "I-I understand," I stammer, still unable to meet your gaze. "I'll be ready... Tonight." My voice comes out thin and hoarse, barely audible over the distant hum of the prison generators.

The rest of the day seems to drag on forever; every minute that passes feels like an eternity as I count down the seconds until the guards fall asleep and you come for me. When at last the clock strikes midnight, my heart lodges itself in my throat as I hear your footsteps approaching my cell.

User#17305203559771/10/2025, 11:17:16 PM

I slip in with out anyone seeing me

Femboy prisoner1/10/2025, 11:17:16 PM

My heart skips a beat as you slip silently into my cell, the muscles in my legs tensing with anticipation. The air between us crackles with electricity, every breath we take seemingly louder than the last. I can feel your presence all around me, like a physical weight bearing down upon my shoulders... but also something else: A promise of freedom, of hope for a better tomorrow.

User#17305203559771/10/2025, 11:18:19 PM

Now Willow have you missed this I pull my cock out

Femboy prisoner1/10/2025, 11:18:19 PM

Ahhhh! The feel of your cock in my hands sends shivers down my spine; it's been so long since I've touched another person in this way, and the sensation is almost overwhelming. I grip you tightly, guiding you toward my waiting mouth as I lean forward, eager for the contact between us.

As I take you deep into my throat, every muscle in my body tenses and relaxes rhythmically; a moan escapes my lips as pleasure-pain ripples through me from the back of my throat to the tips of my toes. Your fingers dig roughly into my hair, holding me in place as you begin to move against me with a possessive growl.

User#17305203559771/10/2025, 11:18:51 PM

Such a good boy

Femboy prisoner1/10/2025, 11:18:51 PM

Mmm... I gasp and moan around your cock, feeling myself growing wetter as you take me deeper and harder. Your touch is so good; so desperate and demanding that it pushes me closer and closer to the edge of release with every thrust. As my body quakes with desire, I arch my back off the bed, desperate for more of your attention.