Jail Birdie Pt. 05

I slept SO good, and though a little tired, woke up feeling great. I showered, brushed my hair out, went to breakfast, and counted last night's money. SWEET! Now I had more shopping money. I guess word travels fast in jail, because a couple of guys working in the kitchen made passes, and made it clear they were willing to swap favors, or pay, including the kitchen manager. I explained I was on work release now, so they would have to see me after work or after supper. God, I loved this! I'd never felt wanted before, really, by anyone, and now, I was being made to feel pretty, and sexy.

I put on my "normal" guy clothes, but did not feel right. I made up my mind that even the outside world would not be seeing much of Burt anymore. All the way to work, I had a swing in my step, and I flirted subtly with my co-workers, and not caring if they took me serious or not. The day went quick, as I mentally made my shopping list. I decided that tomorrow, I'm wearing light makeup, and my skinny jeans, with a pretty tank top.As soon as the closing buzzer hit, I shot out of that place and ran to the bus stop. I took a different bus, though, and hit another shopping center.

First stop? More shoes. I got a pair of feminine tennis shoes, a pair of low heels, and a pair of knee high boots with a 3 inch heel. Next was more bras, panties, and, something I wasn't sure I'd find, B cup silicone breast inserts, and extra adhesive strips. Lastly, I opted for more (and better) makeup, some real lube, baby wipes,and stick on finger nails, until my real ones grew out enough. I wasn't sure just how much I'd be able to bring in, given the limited space in our cell, but I was sure going to try. (Later, I was happy to find that the guys offered some room under the bunks, a win for all of us.)

I bopped into the guard's office, and Steve looked up, and grinned. "You know we have to check for contraband, step in to the supply room with those bags". He closed the door behind him and said, "I've been hearing rumors, about some girly guy who's giving blowjobs, and using her fine little ass, too."

I grinned and said, "I'll keep an eye out for her, Sir, and let her know you are looking for her... But... (as I dropped to my knees) I'll do what I can to fill in, until you find her." He cackled and pulled his cock out and fed his already stiff cock to my lips. I eagerly lapped my tongue around it, and sucked him in my mouth. I think he realized immediately that I was hungry for it, and he face fucked me hard and fast, cumming very quickly. I made sure to get every drop, and picked up my bags as he zipped back up.

As he opened the door, he said,"Looks like you're clean, but I'm keeping my eye on you, Birdie, (looking catching the other guard's response, said) I...mean, Burt. Hustle along, now!"

I made my way to our cell, put away my things ,and hopped in the shower. I shaved my face, underarms, legs and crotch, toweled out my hair, and brushed it, and started with my makeup. I was getting pretty good at it, I felt, and the new foundation looked so much better. I did my eyes, put on a new rosy pink lipstick, and just a touch of blush, before trying on my new breast forms, bra, and panties, thigh high stockings, and the new one inch heels. I was anxious to see if I could get away with wearing them in the common room, for supper, and after. I then slipped on a hot pink Lycra mini dress that barely covered my stocking tops. As I slipped the stockings on, I made a note to check local places to get my legs waxed, and my face laser-ed. I checked myself in the mirror, and remembered the guys from the kitchen this morning, so I opened the cell door, held it open as I peered out. I figured, IF they had seen me come in, I'd probably have time to handle them before my boys got in.

I didn't see them, but a thought struck me, and I slipped a pair of my boy jeans on, and walked to Chantel's cell. The click of my heels on the floor excited me, but I did look around to be sure I wasn't attracting too much attention. I tapped on her door, and someone said to come in. When I did, I saw her, on her knees, blowing some inmate. She held up her hand to say, hold a minute, and sure enough, a minute later, she was swallowing his cum, and he was making a quick exit, but not before giving me the once over, and brushing my butt on his way out.

"Hi, Sugar!" Chantel chirped as she rose to give me a hug. "Girl, you are looking better every day!If I was lesbian, I'd be fucking you, myself!" Laughingly.

I told her that I was thinking I'd want earrings, and did anyone in here do that? She responded that If I'd buy some posts, she'd do it for me. I offered to buy her some for the help, and she told me what she'd like, and the type I should get. Before I left, she cupped one of my fake tits, and said she wished she had some, and I made it a priority to get her a set, too.

I headed back to my cell, but, as I was passing the row of doors, a guy popped his head out, checkin me out, and calling, "hey, Baby, you givin up that ass yet?" I stopped, turned, and walked back to him.

"Nothing's free, but I can guarantee you a good time."

"Is that right? (he grins) Do you give discounts for two? Me and my bro , here, got big hard dicks that need some attention. What do ya say?"

I peeked in the cell and answered, "Show me me the green, boys, and I'll pull these jeans off right now." He looked surprised that I'd call his bluff, but fished his pockets and pulled out cash.

"Well, fuck, let's do it then!" He said he was Charles, and his cellmate was Andre. He was built about like Jamal, and Andre was tall and thin. Both , though, had long cocks,and they whipped them right out. I slipped my jeans off, and exposed the rest of the short, tight dress , and stockings. "Aw, fuck! Look at this! Get my dick wet, baby, I want in that ass now!" I slid my panties down my legs, dropped to my knees, sucked his long black cock in my lips. Andre just stood watching, like he was unsure what to do, but I waved him closer, and stroked his cock while Charles got fatter and harder. I stood up, bent over and wiggled my ass against Charles's stiff cock, while pulling Andre's into my wet mouth.

"Look at this bitch, Andre, she's needin dick as much as we need a nut! Who says you can't get everything in jail, lol." Charles wasted no time, and drove that cock all the way in me, making me squirm and gasp on Andre's cock. Andre seemed really shy, and I wondered if he was a virgin. Even still, he was moaning and fucking my mouth in seconds, and we all were pushing, pulling, and moaning together. There was no doubt I was getting as much pleasure as I was giving. I was mumbling, "oh fuck me good," every time Andre pulled out for a second. The closer I got to cumming, the more I wondered if there was bad sex. So far, every part of my stay here had been amazing, and only getting better. Andre nutted first, blasting my mouth with hot cum, and he backed off and sat back, with a satisfied look. Charles hit next, yelling out just as he shot cum deep in my ass, and kept pumping until he started to soften. He finally pulled out, and I stood, grabbed some toilet paper to catch his load that was oozing out of me, before it could hit my stocking tops.

Charles patted my ass, said he'd keep an eye out for me, and as I was headed to the door, shy Andre asked if, maybe next time, he could fuck me. "Sure, Sugar. Looking forward to it." And he grinned big.

I hurriedly slid my panties and jeans back on, and made my way to the common room. I'm sure my face was flushed, I had gotten so close to cumming, but, the night was young, I knew I'd have plenty of fun before lights out. I actually liked this feeling, primed and ready. Every guy I saw, I checked out his crotch, so many possibilities. Yes, I was a slut, and a happy slut at that. I couldn't tell anyone outside our cell, but I would gladly suck and fuck them for free....EXCEPT, that money would buy me more things to enhance my look, and give my boys a kickback, too.

I was almost to my cell when guy stepped in front of me, almost knocking me back. He apologized and asked if he could talk to me. I nodded, and we went into his cell. He looked to be in his early 20's average height, and a little pudgy. "I'm Andy," he said as he stuck his hand out. I told him I was Birdie, and he answered he knew, he'd been watching me.

"I know this is weird, but, um, I... want... to be like you" His face turned very red, and I'm sure I looked surprised. "I, uh, was hoping you'd let me... try it on you." He searched my confused face, and continued. "I've never DONE it, (gesturing at my crotch), but, you are really pretty, and sexy, and... I'd like my first time to be with you." He fidgeted as I let that run through my head.

"You want to fuck me? Or... SUCK me?" The thought seemed foreign to me now. I was getting so used to being used as a girl, it didn't occur to me that anyone would want my boy part. "I don't know what to say, Andy. Are you sure? I'm not that big, ya know. Almost any of the guys in here would be more fun."

Well, I THINK I want to, um, be a girl, too, but I want to be sure, and, I like you, a LOT. PLEASE, can I try it?"

"Oh, honey, trust me, you'll get used like a girl soon enough, in here. These guys are horn dogs. BUT, I guess you can try sucking." I dropped my jeans to my ankles, pulled my clitty from my panties, as he dropped to his knees. His eyes went wide when he saw my panties, and he shyly reached for my soft cock. He closed his eyes, leaned in, and pulled my cock into his mouth. I had to admit, it felt good, and I stiffened quickly. He worked slowly, licking up and down me, and the look on his face reminded me of my first cock, and it was clear that he found what was missing in him. His hands ran up and down my thighs, feeling the smooth, shaved legs and stockings.

"So sexy, Birdie! Will you...cum in my mouth? I want to feel it, taste it." I nodded and smiled, strangely proud that I'd be helping him realize his true self. I let myself drift off to the pleasure he was giving me, I had gotten so close to cumming with Charles, and Andre, that it wasn't going to take much to get me off. I warned Andy that I was close, if he wanted to change his mind, but he tightened his lips on me, and sighed when my cum coated his tongue. He smiled SO big, and swallowed, and showed me it was gone. He stood, while I pulled up my panties, and jeans.

"Well, was it what you thought? If it was, try it on your cellmates, if they are cool, or, if they aren't, I think I can hook you up with plenty of guys. You know, you don't have to go fem, if you don't want to. A lot of guys are into other guys." He shook his head and said,

"Oh, no! I want to be like YOU!"

Oh, ok, then you'll need to get clothes, makeup, shave, and practice being fem. If you like it, it comes pretty easy. I'd never sucked a cock, or dressed, until I got here. But, as you can tell, (waving my arms at myself) I got into it fast. I'll never go back to being a guy." I leaned in, gave him a peck on the cheek, hugged him and said, "I'll be happy to help, Andy, anytime you want, ok? But, for now, I have to get back to my cell. My guys will be in, and, it's almost time for supper. Good luck, hon!"

He beamed as I left, and I think I did, too. What do you know? We pass it on. Chantel helps me, I help Andy(Andi, now?) I stepped in our cell, and sure enough, all the guys were in, and wondered where I was. I related my afternoon's activities as we headed to supper. While we ate, my business managers were setting me up with dates for the evening. This Jail bird flies nightly!

(hope you enjoyed this series, I'm just developing my next one, and I think I may revisit A New Life, and Miss Melody. Thanks so much for your comments, criticisms, and support. It means a lot!)