Jail Birdie Pt. 07

Ok, I'm not fooling myself, I'm NOT a female. I haven't deluded myself, yet. BUT, I am a fem guy who is very passable, and who knows what guys like, and how to please them. I'm fairly sure, if I wasn't in jail, where guys are desperate for sex, and, working with guys whose wives aren't taking care of them, I'd never have gained that knowledge. I also would never have found out just how good it feels to suck a guy dry, or have him fill my ass full of cum.

The next week went well, blowjobs to the boss, along with my other office duties, and getting fucked at night with my cellmates, and other inmates, who seemed happy to pay for the sex they were missing. My wardrobe had expanded so much that I had to keep several outfits at work, in a supply closet. My skirts and dresses were getting shorter, while my heels were getting taller. I was addicted to the attention I was getting, and to the feel and look of the clothes I was wearing. I 'm taking hormones, and have an appointment for implants. Nothing big, of course, just a size to enhance my A cup.

One morning, just as I was about the leave the bathroom, just re-applying my lipstick, Avery steps in, and pushes right up behind me, pushing his crotch against my ass. "Has the boss tried this ass yet, Birdie? I'm pretty sure I want some. The way you shake that thing, lately, it's hard to resist." With that, he slid his hands up and down my waist and thighs, and continued grinding into my ass. I pushed back a bit, wiggling, and giggling.

"Are you sure that won't make you a fag?" Winking as I said it.

"Fuck you, Birdie! You don't look like a guy, and you SURE don't act like one." With that, he pulled my skirt up around my waist, yanked my panties down, and cupped my bare ass. "Tell me you don't want a hard dick ."

I didn't answer, but my hands rubbed over his now very hard cock, and unzipped him. I pursed my lips and pushed my ass out more while I pulled him free. "We'll have to hurry, before the boss wonders why I'm not at my desk." It took him only as few seconds to line up to my star, and push in.

"Aw, yeah, THAT'S what I'm talkin about. Fuck, Birdie, you feel good. I'm not gonna last long. Damn, Baby, I wish I'd done this sooner." He was grunting loud, and I was bucking against him, one, because it felt good, and ,two, because I needed him to come, so he would be quiet.

"Shhh, Avery! We don't want everyone here to hear you. Come on, give me that big load of cum you've been saving for me. I know your wife isn't helping you. Breed me, Honey!" This was the first morning fuck I'd had in over a week, and it was starting my day off sweet. Even a quickie gets me going. I was biting my lip not to moan, myself, and I felt Avery shake and blast his cum inside me. He gave a few more pumps, before easing out. I grabbed a couple of tissues to keep his cum from running down my legs, and handed him a couple to wipe himself. "Just let me know if you want a repeat, Avery...but, maybe longer, next time, ok?" I pulled my panties back up, smoothed my skirt down, and opened the door enough to peek out, before stepping out. For the next two days, every time I saw Avery, he'd blush, and look away, but I'd catch him watching me, and saw him saying something to the other guys.

After that, all the guys were more flirty than they had been before, and it was clear that I'd soon be getting more action at work, we would just have to be careful not to let the boss know. I sure didn't want to mess up the sweet deal I had with him. Even if, so far, he only wanted blowjobs, he had started caressing my legs, sliding his hands up and down my stocking thighs, which were on display, at my desk, or in the chair in front of his. I could tell the wheels were turning in his head, wondering what it would feel like. I'd seen his wife. She probably was attractive enough, when he married her, but she'd added almost her full weight again, and didn't bother trying to dress nice, and, I'm guessing, no fun under the sheets anymore. Things like that work in my favor.

All this week, on our rides back to the jail, he would massage my ass while I sucked his cock. He would inch my skirt up enough to expose my panties, and even slid his fingers under them. I expected any day now, for him to bend me over his desk

Things at the jail were just as good. I had all the cock I could handle, and, now, at least once a week, while I'm giving head and getting fucked, my little protege, Andi, would kneel under me, and suck me. WHAT AN ORGASM! Getting a hard cock in the ass, and mouth, AND getting a blowjob? I'm not sure it can get any better. Usually, after those romps, I was done, and would crash early. I rarely used my own bunk anymore, I took turns sleeping with my roomies. I was still cutting them in on my profits, and making sure their sexual needs were met. Maybe once every couple of weeks, we'd do another gangbang, just like when I first got here.

Andi was coming along nicely, He was losing weight, exercising, and doing his best to do his makeup. He wasn't there, yet, but he was doing everything he could, and his cellmates popped his cherry as soon as he told them about wanting to go Fem. He was giving his mouth and ass away, so he was plenty active, and I think the sex was helping with his weight loss. I was a proud big sister.

Wednesday evening, Jut and Nat sat me down, telling me they got their notice. At the end of the week, they'd be getting out. I was sad, I've really grown to think of them as big brothers. (With benefits, but yeah.) They promised to stop by and give me and Jamal their cell phone numbers, as soon as they could buy one. Fortunately, Jamal (for me, maybe not him) would be in as long as me, which, as I thought about it, was only a month away. Jamal told me not to worry about new roomies, he'd handle them if they weren't nice to me. I DID worry a little about who might be sharing our cell, though, I had a sweet arrangement, and hey, there are STILL some assholes out there that hate "girls" like me. Saturday night, we had a cell party, and Sunday, my boys hugged us, and made their way to freedom. I flitted around, trying to stay busy, just so I wouldn't have to think much about it. That night, I slept with Jamal, and moved my things to the other lower bunk, as I had seniority over whoever was coming in.

Monday after work, when I walked into the jail, Perry, one of the guards, walked me to our cell. He explained the new guys were there, and he was coming in just to make sure everything was ok. He had shown them the cell earlier, and told them they would be on the top bunks, and that one of them saw some of my clothes, was puzzled. Perry told him things would be obvious in a few hours. He asked me if I wanted to wait for Jamal to get "home", but I decided to brave it, and size the new guys up. We stepped in, and Perry, said, "Boys, this is Birdie. She is one of your cellmates. (pregnant pause) I don't know what your thoughts are on girls like Birdie, but I'll warn you now. The other cellmate, the guards, and, well, MOST of the inmates here? Will mess you up, if you bother her. Are we clear?" He stood straight, staring them in the eyes, and honestly, I teared up. Wow, Perry had always been kind to me, but he was like a guard dog with them. Both of the quickly nodded and answered , "Yes, Sir!" It was obvious this was their first time in jail, and they were intimidated as much as I was, the first day.

The tall, lanky guy stuck his hand out and said his name was Paul, and the shorter, pudgy one, more shyly extended his hand, and just said, "Gordon."

I answered, "welcome to jail, guys, it won't be as bad as you imagined. I was scared to death, when I got here, but, now, it's the best home I've ever had. I hope my ...appearance won't make you too uncomfortable. My roommates helped me realize my feminine side, and, the guards give me a lot of leeway, in my clothes...and...actions" I grinned, not sure if they got my meaning. I hugged Perry and thanked him, and he went back to his duties. I turned back to still nervous looking guys, and said, if you have questions about anything here, just ask me, or Jamal, when he gets in.

They sat there, fidgeting, so I thought maybe I could break the ice a bit. "You guys will hear talk about me, and see things, so, I might as well tell you, myself. I, um, do... sexual favors for guys here. They get horny, I like it, and, it helps provide me a little money for clothes, makeup, trinkets. When you have this many horny guys in one place, they need release. If it wasn't me? It might be one of you...understand? I was forced, at first, but I quickly found out that I'm happier this way, than I ever was as a guy. SO, you'll see me... doing things that might make you uncomfortable. I hope not, but, I wanted to warn you, ok?"

Their eyes got even bigger as they nodded, and they had been scanning me up and down since I walked in. They still didn't say anything, though, so, I stood, and announced I was going out to "socialize," and, if they felt comfortable enough, they could go out to the common room, to play cards, or chess or checkers, if they wanted. They again nodded, and thanked me. I stepped out, trying to decide if I'd settled them at all, or if I made things worse. The first day is stressful enough, without having some swisher giving you the lowdown. I grinned at that thought. I had only sat down, maybe 5 minutes, when Paul stepped out, scanned the room, and came over to me.

He leaned down and in a nervous whisper, stammered, "hey, um, those F-favors... wh-what are they? I mean, um... do you, um, d-do things... for... anybody?" He was so damned cute. Scared silly, but horny enough, and curious enough, that he grew some balls, to ask me. Bless his lil heart. I pulled his head closer, kissed his cheek and answered," Why don't we find out, Sugar?" So, at least ONE of the guys was interested. I had a feeling that Gordon was, too, but was the even more shy one. If I were betting, I'd say he was still a virgin. I took Paul's hand , led him back to the cell.

"Gordon, Honey, Paul here is curious about what things I might do with guys. If you are curious, too, you can stay, or, if you are too shy, you can wait in the common room for a bit, while I 'talk' with Paul. What do you think?" They looked at each other. Obviously, they had discussed me before Paul got brave enough to ask. "Can I...is it... ok, if I um, watch?"

"That's between you and Paul. I'm ok with it." I looked at Paul, he swallowed and nodded , asked what he should do. I told Gordon to sit on my bunk, and told Paul to stand in front of me. I leaned in close, tiptoed, and kissed his neck, and slowly ran my fingers down his chest, to his belt. I unbuckled it, unsnapped his jeans, and unzipped him slowly. His face was beet red, and he was breathing so fast, I hoped he wouldn't pass out. "Relax, Paul, everything is fine, you'll see."

I dropped to my knees, pulled his long, thin cock free, while his legs shook. My fingers curled around him, and he whimpered. I had to seriously try to stifle a laugh, and flicked my tongue on his head, which was already leaking precum. He grabbed my shoulders, I think more to steady himself than anything else. I breathed warm breath on him, and licked the underside of his cock. My free hand cupped his balls, and I looked up at him and winked, letting his cockhead slide into my mouth. I already knew that my lipstick lips had a good effect on guys, and feeling his cock throb on my tongue was sweet. He MIGHT not be a virgin, too, but if not, he wasn't used to this. I swirled my tongue around him, over and over, as he swayed and moaned. Gordon, at this point, wide eyed and sweating, was rubbing his crotch. Paul grabbed my head, and yelled out, "OH GOD!" and blasted my mouth with warm, creamy cum. I didn't think he was going to shoot THAT fast, and I almost choked on it. He spurted 3 more times before he sank to his hands and knees.

I leaned back and said, "That, Boys, is one of the 'favors' I do." He slumped on his knees, and with heavy breath said, "wow." Gordon immediately jumped up and shouted, "Me? Can I be next? Please? Damn, Paul, that looked like you were gonna pass out. I-I heard about..guys, uh, girls, uh...you know, people that do that, but, honestly, thought someone would be making ME do it, not getting it done. " He was shifting from one foot to the other, like a lil kid waiting for a carnival ride. He nervously unbuckled his jeans, and pushed them down, with his boxers, and his cock sprang out. It wasn't a full 5 inches, and not too fat, but it was hard as it could be, and stood, shaking it, grinning from ear to ear, I scooted on my knees to him, and engulfed him. He yelped , and grabbed my head. In seconds , he was shaking so hard, his legs were bumping into me. I was positive he was a virgin, now. I mean, yeah, I know how to get guys off, but he was freaking out. ""Oh, God, Oh GOD, YEAH!!! Fuck me, I'm gonna CUMMMMM." And, in LESS than a minute, he did!

I wanted to laugh, but, come on, I remember what a big deal that first blast that WASN'T from your hand, does. I patted him on the ass, and told them it was fun for me, but, that one was free, there would be favors owed, if we did it , or anything else, next time. They both nodded, and climbed up on their bunks, grinning like cats. I'd opened up a world for them, just as Jamal, Jut, and Nat, had done for me.

(I had planned on ending this series, but I think I will add one more part, at least, to make the jump from jail to outside life. Thanks for reading, and, as always, comments, good or bad, are welcome)