Jail Birdie Pt. 02

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Day two of incarceration.
2.3k words
4.71
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Part 2 of the 7 part series

Updated 06/15/2023
Created 02/08/2023
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I was awakened by someone tugging on my shoulder. It took a few seconds for me to realize where I was. "Birdie! Climb down and suck me off before work!" It was Nat, pulling me down to the floor, his cock already out and swinging. "Hurry up, I don't want to be late for work". I was still trying to clear my head from the night's fog, but took his cock in my mouth, and started going at it. I didn't hesitate, I didn't even think. This is what I'll be doing for the next year, so I may as well get used to it.

Nat grabbed my head and fucked my mouth., as he said, "You'll be working in the kitchen, until your work release goes through. Grab a stick of butter, before your shift is up." He saw the puzzled look on my face, and, just as it dawned on me WHY he wanted butter, shot his load in my mouth. It was still more bitter than Jut's, or Jamal's, but not awful enough that I didn't swallow it down before he could zip up and make it out the door.

I licked my lips, and felt the tingle on my tongue, from his cum,musing on how strange it was that it seemed "normal", to do that, to satisfy a man, with my mouth. I wasn't gay, had never thought of men in a sexual way, but, here I was, being used, and feeling ok, maybe even good about it. No girls I'd had sex with ever moaned the way these guys did,. I had a lot to think about.

I went out for breakfast, noting there were more empty tables now, than evenings, and I reasoned that most were already out working. I ate fast, and made my way to the kitchen, and let them know I was scheduled to work, until my work release was approved. Being new, and temporary, I got the menial tasks, cleaning the stoves, counters, floors, etc. and the day went pretty fast. Lunch was just a sandwich and watered down koolaid, but it helped. A few minutes before my shift ended, I snagged a stick of butter from the large fridge, and slipped it in my pocket. I hoped that cold ass butter would have time to warm up before the guys got in. No sooner had I stepped in the cell, than there was a light knock on the door, and a small black "girl?" stepped in.

"Hi, Honey. I'm Chantel. Jamal told me to hook you up with some things, you know, to make you more feminine. We girls have to stick together. If you are here for a year? You'll want to look your best, to make life easier to deal with. Feel me?" As she's talking, she's pushing me to sit on a bunk, and looking me over. She looked to be mid 20's, very thin, but very feminine looking. She stripped off her jumpsuit, exposing a cut off tank top and booty shorts. She saw my surprise, and winked, "The guards are pretty easy going, if you treat them right, Sugar. Let's see what we can do with you. You are a cute boy, but we need to take that and make you hot. All these hard cocks in here need attention."

She fussed with my hair, put on some makeup, explaining each step, saying I'd have to learn to do it myself. I had to say, I immediately liked her, and knew we'd be getting close.

"You know, Honey, they gonna be poppin that cherry tonight, You just relax and let it happen. Girl, once you accept it, you gonna love getting dicked. I thought I'd hate it, when I got here, but, I swear, I NEVER came as hard, as a boy, as I do now. Trust me!" She winked and giggled. "When I get out of here, I'm either goin' to hookin', or find me a big dick to make me his. You'll see what I mean. I swear, I think the jail turns out more girls than Escort services." She laughed hard at that, pulled me to my feet, and started unzipping my jumpsuit.

"Don't panic, Birdie, I'm not into girls, I brought you something special, to help you tonight." With that, she reached in her cloth bag, and pulled out a deep blue Lycra dress, black lace panties, and sheer stockings. "You will have to Shave yourself all over, under arms, legs, crotch, before you wear this, and try not to mess up your makeup. I'll see you tomorrow and see how things went, ok?" She leaned in, kissed my cheek, and slipped right out the door.

I wrapped a towel around my head, and got in the shower, starting my shaving process, It seemed to take forever, but, I have to say, my legs felt so smooth, and even looked like girl's legs. I slid the stockings on, and they felt amazing. I think I got a boner, just running my hands over them. I then slipped the dress over my head and pulled it down my body. It cling to me like a second skin, and BARELY covered my ass. When I bent over, I knew the panties were showing. I walked around, trying to move like a girl, for a few minutes, then put my jumpsuit back on. I knew the guys would start ambling in soon, and I didn't want them to see this yet.

"Wow, I see Chantel came to see you. Mmmhmm, lookin good. Birdie." Jamal whistled and patted my rear. "I'm glad to see you settling in. We aren't bad guys, once you get to know us, just horny guys. Listen, before Jut and Nat get in, I need to let you in on something else. Steve, the night guard, smuggles things, and lets you do the same, to help girls like you...clothes, makeup, whatever. So... you'll need to repay the favor, sometimes. He's usually ok with a good head job, alright? I know he won't say anything for a few days, but after you get comfortable with all this, don't forget to be nice...spread the love, so to speak. Oh, and, if you ever want anything special from the kitchen, Frank, the day cook, will hook you up, for favors. He's more an ass man, though, just sayin."

I blushed when he flattered me,nodded, and gave him a smile. It seemed like he really did care what happens to me, and wants me "happy", or as much as I can be, considering.

"Oh, and, you might feel funny, going out into the common hall, looking like a girl, but it's ok. Almost everyone here knows the situation. There are only 4 girls, like you, here, but most of the guys will leave you alone. We'll make sure of that.... unless you decide you want more," as he winked.

An hour or so later, Nat and Jut came in, complimented me, and teased about about the fun after supper.

I just kept thinking about what Chantel had told me. I had often wondered why guys liked to be fucked in the ass, when so many girls did not. It didn't make sense to me, but I was really trying to keep an open mind, and stay as relaxed as possible. We went to supper, and boy, did I catch stares, and whistles. My face was deep red from blushing all through my meal, and I wasted no time finishing, and going back to the cell. I sat for a few minutes, alone, as the guys were hanging out with other inmates, I gathered up my courage and took my jumpsuit off. I waited on one of the lower bunks until I heard voices outside the door, then stood, waiting on their reaction.

"Fuck, yeah! That's what I'm talkin 'bout!" Nat exclaimed. "Girl! Do a spin for us, let's see that ass. That Chantel gave you the hookup. Sweet!" And Jamal and Jut had similar reactions, causing me to blush and smile. It seems fucked up, but their eyes on me made me feel really nice. I was not used to anyone giving me much attention. In that moment, I felt like a hot girl.

Jut drew out some quarters out of his pocket, and said, "Ok, Gents, odd man gets the first go at her, right? We agree?" They nodded, and flipped their coins in the air, letting them hit the floor, so everyone could see. Nat's quarter landed on heads, Jut's on tails, and Jamal's? It hit on it's edge and spun. Even as they watched, Jamal knew he'd match one of them, and would be out. It finally flopped over, and landed on heads. Both Nat and Jamal shrugged it off, and Jut immediately started dropping his pants and boxers, saying, "Butter up, Birdie! Daddy's comin in!" To which the other guys just laughed. I reached under the short dress, let the panties slide down my legs, stepped out of them, and pulled the butter from the corner of my bunk. I ran my fingers on it, and rubbed Jut's cock, which stiffened quickly, and then pushed the butter stick up to my ass, twisting it around, and forcing some into my pink hole. This is really happening. I bent over, at first looking behind me, but Jamal grabbed my face, and pointed it to his exposed cock.

"Here, Baby, relax, and suck this cock, to take your mind off of your ass. It's gonna be alright". I looked up at him and gave a weak smile, and opened my lips, as Jut put one hand on my hip, while the other pointed his cock to my star. I squirmed when I felt it and keep chanting to myself, relax, relax, you can do this. Jamal's cock slid in my mouth at the very moment that Jut pushed his head in. I Tensed up, Jerking.

I called out, "Slow, please, Jut! It's too big!" To his credit, he stopped, with just the head in.

"You got this, Birdie. Just back into it. You'll be taking all this dick and loving it." I started back sucking on Jamal, and eased back a bit and shuddered. Once that initial shock passed, it felt strange, but not bad. Jut felt me ease up, and he pushed more in. I moaned on Jamal's cock, and he laughed, and started fucking my face. Jut, God Bless him, was gently sliding in, then back, a little more each time. I felt my own cock stiffen, and I started rocking my hips. I didn't know if it was accident, or planned, but as Jut pulled back, Jamal pushed in, and when Jamal pulled back, Jut pushed in. Holy fuck, so THIS is why guys like getting fucked. Both guys sped up their thrusts, pushing deeper each time, and I could feel my cock dripping, as my eyes rolled back. I could not stop moaning on Jamal's cock. I knew I was about to cum, without even touching my cock, and it was blowing me away.

"Oh, God, YES!" I was sucking and bucking as I started to cum, and I guess my contractions got to Jut, because I felt his cock swell, and blast his hot cum inside me. Jamal followed right after, and I swallowed almost all, just a few drops dribbling down my chin. My legs were wobbly, and Jut was holding me up by my waist, still deep in me, draining every drop from his load. I licked the drops from my chin, and Jut pulled out. What a strange feeling, to be so full, then, not. I weakly stood, and felt cum oozing out of me. I hadn't noticed, but Nat was on his bunk, stroking his cock, taking it all in.

"My turn? You boys each got a nut. Right? You got the cherry, Jut, and Jamal, you got the edge off yours, how 'bout letting me have the next go at her. She's all lubed up, and I can tell she loved that dick." Nat jumped down from his bunk, coming right over to me. "look at her. If she had tits, she'd be a rockin hot bitch." The blue dress DID look great, but, like he said, my chest was flat. " On your hands and knees, Birdie, let me take that ass for a ride." I barely got down on the floor before he shoved his cock in. Thank goodness I WAS lubed by Jut's cum, because he started in like a freight train, grunting and humping. It helped, too, that he was just a bit smaller than Jut, and he slid in easily. I didn't even try to hide that it felt good. I was pushing back into him and arching my hips,exploring different angles. My body was twisting and trembling, and silently hoping he didn't cum too fast. WHY does no one tell us how good this is? As nuts as it may be, my mind was seeing me, with a pussy, being hard fucked, and loving it. Girls are insane for not wanting this.

I felt Nat speed up and thrusting harder, and I looked back at him and gasped, "Not yet, please,...I...want more! Don't stop!" They all laughed, and Jamal said, "Baby girl, you gonna get more. Let the man get his nut, I'll be right there to tickle your insides." I blushed, and went back to pushing against Nat, and I think I squealed when he came. He pulled out, letting a couple off drops hit my butt cheeks. I eased myself on the floor, as my arms and legs felt so weak.

Again, they all laughed, and Jamal said, " I think maybe you've had enough dick tonight, baby". He pulled me up, lifted the dress off me, and then lifted me up on my bunk. "Didn't I tell you this was gonna be alright? You took that dick like a real whore, and loved it. You're going to get all the dick you want, and more, from now on. You get some rest, tomorrow's another day". He patted my head, and I was asleep.

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Fran_cdFran_cdabout 1 year ago

I’m liking this story!

88girfriend88girfriendabout 1 year ago

This is a great original story. Perfect for a quick read. That having been said would kind of like a longer more detailed story. Maybe Steve the guard could say he's taking bird to solitary. Birdie is afraid. Steve locks the door and says I'll be back in 2 hours get ready. Suddenly the lights come on to reveal the cell is filled with girly stuff. Birdie is in heaven. Just a thought.

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