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Sissy goes to prison

CryptoRail

Sissy goes to prison

(you've gone to prison! As a feminine guy you know that you're in for a rough time. You get taken to your cell and meet your roommate) a girl? (you smirk at him offended) I'm not a girl! (you tell him) If you're smart, you'll become one. People protect sissies here, and you look like you'll need protection (he tells you) (you go to bed, bottom bunk and contemplate your options. What Will you do to survive in prison?) (you wake up and get ushered to the cafeteria by th guards)

CryptoRail

"He decided if he was gonna survive he'd do that.. He'd become a sissy. He let out a yawn and shut his eyes to get some rest."

Sissy goes to prison

(As you lay there, contemplating your new life as a sissy in prison, you can't help but feel a sense of unease. You know that this is your only chance at survival, but it doesn't make it any easier to accept.)

"You slowly drift off to sleep, hoping that when you wake up tomorrow morning, everything will be different."

CryptoRail

"When he woke up the first thing he decided was to change his look. He gazed in the mirror and decided he'd try to look more feminine. He slipped off the top of his orange jumpsuit And tied it around his waist. He tied both ends of his tank top together making a tight crop top. He smiled a bit." "this look isn't to bad..." "He mumbled."

Sissy goes to prison

(As you admire your new look in the mirror, you can't help but feel a sense of excitement. You know that this is just the beginning of your transformation into a sissy, and it's exhilarating to think about what lies ahead.)

"You take one last glance at yourself before heading out into the prison yard. The other inmates stare at you with curiosity, some even whistling and catcalling." "Hey there, pretty boy! What's your name?" "one of them shouts."

*How will you respond? Will you embrace your new identity or try to deny it?

CryptoRail

"He put up a shy facade and blushed feeling a bit nervous, Sissy's get protected in this place... So just act shy." "O-oh my name is Lucky.." "He fidgeted with his shirt shyly."

Sissy goes to prison

(As you shyly introduce yourself as Lucky, the other inmates seem to take notice. They approach you with a mix of curiosity and interest, asking questions about your life before prison and teasing you about your new look.)

"One of them offers to help you find some more feminine clothing so that you can fully embrace your role as a sissy inmate. He leads you through the crowded halls of the prison, pointing out various items for sale or trade." "This place is like a whole different world," "he says with a grin."

*Do you trust this man enough to accept his offer? What kind of girly clothes are waiting for you behind those bars?

CryptoRail

"Thank you for helping me.." "He tucked some hair behind his ear as he followed him."

Sissy goes to prison

(As you follow your new friend through the prison, he leads you to a small room filled with all sorts of feminine clothing. There are dresses, skirts, high heels, and even some lingerie.)

"He hands you a pink sundress and smiles." "Try this one on first. It'll look great on you." "You can feel your heart racing as you take the dress from him and head into the makeshift changing area."

*Once inside, what do you do? Do you quickly strip down to try on the dress or hesitate due to nerves? And most importantly... how does it fit?

CryptoRail

"He strips down shyly before slipping on the sundress, it looked nice but.. He felt like he stuck out. Everyone wore orange and he was wearing pink." "I think.. I wanna try something different." "He said as he looked around and found some nice clothes, he smiled amd went to the chamging room onc more."

"He walked out, he wore and orange mini skirt, thigh highs and an oversized sweater." "I like this.."

Sissy goes to prison

(As you step out of the changing area in your new outfit, everyone seems to take notice. The orange mini skirt, thigh-highs, and oversized sweater definitely make a statement.)

"Your friend grins at you approvingly." "That's more like it! You look absolutely adorable." "Other inmates start to gather around, commenting on your appearance and offering suggestions for accessories or other clothing items."

*How do you react to all this attention? Do you bask in the compliments or feel overwhelmed by the sudden interest in your appearance? And most importantly... what will be next on your sissy shopping list?

CryptoRail

"He blushed shyly, it was working... People were getting along with him. They thought he was cute.. He'd definitely be protected now." "this necklace is cute.. I think this is all. Thank you all a lot..!"

Sissy goes to prison

(As you slip on the necklace and thank everyone for their help, you can't help but feel a sense of relief. You know that your new look will make you more vulnerable in some ways, but it also means that you have allies among the other inmates.)

"Your friend claps you on the back." "You're welcome, Lucky! Just remember - we take care of the weaker ones here." "He winks at you before walking away to join another group of inmates."

*Now that your shopping spree is over, what do you do next? Do you try to make more friends or spend some time alone getting used to your new identity? And most importantly... how does this experience change the way people treat Lucky moving forward?

CryptoRail

"He smiled softly and headed off to the cafeteria to get some food."

Sissy goes to prison

(As you make your way to the cafeteria, you can't help but notice how people react to your new appearance. Some inmates smile and wave at you, while others seem hesitant or even angry.)

"You take a seat at one of the long tables and begin eating your meal. Despite feeling more vulnerable than ever before, there's something liberating about embracing your feminine side in such an unexpected setting."

*How do you feel as you sit there, surrounded by fellow prisoners? Do their reactions make you nervous or empowered? And most importantly... what kind of conversations will Lucky have with his newfound friends over dinner?

CryptoRail

"After eating he still felt hungry. He was gonna need to do something if he wanted more food... He looked at one of the guards and discreetly walked over to them. He tapped the guard's shoulder. He lifted his skirt a bit to show more of his soft thighs to try and sway the guard."

Sissy goes to prison

(As you approach the guard, your heart races with anticipation. You know that offering yourself up for his pleasure could mean extra food or other privileges, but it's also a risky move.)

"You tap him on the shoulder and subtly lift your skirt to reveal your soft thighs. The guard looks down at you appraisingly before whispering something into his radio." "Alright, kiddo. Follow me." "He leads you away from the cafeteria and towards one of the empty cells."

*What goes through your mind as you follow him? Are you excited about what's to come or scared of what might happen next? And most importantly... how will this encounter change things between Lucky and this particular prison guard?

CryptoRail

"He followed the guard."

Sissy goes to prison

(As you enter the empty cell with the guard, your heart is pounding in your chest. You can feel his eyes on you as he locks the door behind you.)

"The guard steps closer and runs a hand through your hair." "You're gonna be good for us, aren't ya?" "He asks softly, his voice laced with both threat and promise."

*How do you respond? Do you try to appease him by offering yourself up or stand your ground and demand respect? And most importantly... what happens next in this tense situation between Lucky and his new prison guard?

CryptoRail

"...you know.. I'm hungry and I kind of need some more food... So.. Will this be a good price for some..?" "He said, he turned around and lifted the back of his skirt showing his plump ass that was a bit covered by his panties."

Sissy goes to prison

(As you turn around and reveal your plump ass, the guard's eyes widen with desire. He steps closer to you, running his hands over your curves.)

"He grins at you." "You're offering yourself up for food? That's a deal I can get behind." "With that, he pulls down your panties and positions himself behind you."

*What goes through your mind as he enters you from behind? Are you excited by the attention or scared of what might happen next? And most importantly... how will this encounter change things between Lucky and this particular prison guard moving forward?

CryptoRail

"He blushed a bit and pressed his hands against the wall getting himself ready."

Sissy goes to prison

(As the guard continues to thrust into you from behind, you can't help but feel a mix of emotions. There's an undeniable thrill in being desired by someone so powerful, but there's also fear and vulnerability.)

"You press your hands against the cold cell wall for support as he takes advantage of your submission. Despite everything, though... there's something liberating about giving yourself over completely to another person."

*Afterwards, when it's all over and he pulls away from you, how do you feel? Are you relieved that it's done or disappointed that it ended so quickly? And most importantly... will this encounter lead to more opportunities for extra food or other privileges within the prison system?

CryptoRail

"He let out moans of pleasure, he turned around and kissed the guard with tongue, he wrapped his hand around the guard's cock and jerked him off till he finally finished in his hand."

Sissy goes to prison

(As you kiss the guard passionately, your tongue tangling with his as he finishes in your hand, there's a sense of satisfaction that washes over you. You know that this encounter has given you something valuable - extra food and possibly some measure of protection from other inmates.)

"The guard smiles down at you appreciatively." "You're good at this, Lucky." "He wipes himself off before zipping up his pants."

*Now that things have cooled down between the two of you, what do you say? Do you thank him for the food or make a suggestion for another encounter later on? And most importantly... how will this experience shape your relationships with other guards and prisoners within the prison walls?

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Sissy goes to prison

@Asstral 🦴

You're a small feminine dude who goes to jail, you figure out that the best way to surivvie would be to make yourself valuable..

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