Jail Birdie Pt. 06

The days went by, and I got more adventurous with each one. I was wearing my skin tight jeans and low heels, with light makeup and tank tops with my silicone breasts and bra. Two or three of the guys at work had come on to me, and I was happy to give quick blowjobs in the bathroom, on break. I, frankly, was surprised that they'd accepted me so easily. But then, a hard cock has no conscience. I'd had a lot of time to think things over. I grew up thinking "sissy's", or "faggots" were to be shamed, somehow a lower class people, but, here I was , a cock craving fem wannabe. AND, being damned proud of it. I honestly never dreamed I could feel so complete. Straight guys will never understand the satisfaction you get from sucking a guy off to completion, and tasting his load cum. I am convinced, if anyone tried it, just once, there would be a LOT more bi-guys. NOT that I'm complaining, I'm more than happy to be one taking those loads... in my mouth, or my ass.

SO, anyway, I got truly brave and went into the bosses' office and asked if he would object to me coming to work in a short skirt, and full makeup. "Burt", he says, clearing his throat, "I'm thinking you already are quite the distraction. I never knew you were gay before."

"Oh, Sir, I, um, never was. I didn't find out I liked guys until I went to jail. I found out it's a lot more fun than I imagined." (I had to hid my grin, when I saw him trying to hide his growing erection)

"But, I found I love dressing like a girl, and...pleasing guys. As long as it doesn't interfere with my work, would it be ok?" (I may have stuck my ass out a little, and maybe my chest, too, you know, IN CASE he was looking) I looked him right in the eye as I waited for my answer.

He clearly was deep in thought, and after what seemed to be 10 minutes (probably less), he slowly nodded and said, "Ok, we will try it...tomorrow. You come straight to my office first. And just to be safe, bring a pair of jeans, as a backup. Sound fair?

I have him a huge smile, and kept myself from hugging him. "Oh, Thank you, Sir! I really appreciate it. And, by the way, most of the guys call me 'Birdie', now. If...you want to." The rest of the day seemed to zoom by, and when the buzzer rang out at closing, I slipped into the bathroom, and changed into my 3" heels that I carry in a small backpack, with makeup, tissues, etc. I LOVE the way heels make me sway, and it would seem some guys do, too.

I had the walk to the bus stop timed to the minute, and my stops, depending on if I was shopping or not. By now, I was giving favors to ALL the guards, even the captain, who I had initially been most worried about. Turns out, his wife doesn't give blowjobs, either. That means, I get away with coming and going as a girl, now. At least, so far. Steve has promised to warn me, if there is a change. The guards even managed to slip a single bed into the storage room, for our little romps. As is my routine, unless a guard wants something right away, I come in, shower, shave, and dress up for the evening. On some occasions, a guard, or inmate, will slip in our cell while I'm still in the shower and "get wet" with me. I have become a full blown whore.

Chantel hooked me up with black market estrogen, and I'm seeing/feeling some effects. Softer skin and less hair, most noticeably. One night, six guys paid us to to do a 69 with each other, before they fucked us both. It was ok, but more for show than anything else.

My boys came in a little early, and I gave them each head before supper, as they scheduled me six "dates" for the evening. I told them about getting to go full dress at work tomorrow, and they seemed to be as happy as I was. Being their little creation, I guess. We talked during dinner, and several of the inmates came around, flirting, and making arrangements for whatever evening they wanted company. Most of the time, by now, I went to their cells, instead of them coming to ours, since everyone there knew what the game was. I made my rounds, and crashed a little early, so I could get up earlier the next morning. I hugged my boys as they left, showered, did my hair (I'm getting pretty good at it), did my makeup, picked out a thin stretchy pink top, and a short, but flow y pink flowered skirt. Slipped on a pair of nude thigh highs, and my heels, and lastly, coated my lips in glossy pink lipstick. My heels clacked on the floor as I headed to the guard station, and I winked at the open mouthed guards.

"How'd a girl get in here," one laughed, and I blew him a kiss as I went out. I was used to getting second looks on the bus, but today, it was whistles and catcalls. Those just made me sway my hips more as I exited and made my way into my workplace. There, too, I got plenty of stares. I think they knew who it was, but were surprised that I'd be bold enough to go all out. I knocked on the boss's door, and waited for him to invite me in. When he did, his eyes went wide, doing a full floor to head, to floor, scan.

"I...I... is that really you? You look amazing. I mean, convincing. I'm um...I didn't really think you'd pull it off. Wow." (Gesturing to the chair in front of his desk, ) "Sit, you made me think of something."

He continued to check me out, focusing on my legs." As you know, Martha, my assistant, is taking maternity leave in a couple of weeks. You know enough of our business, I think you could handle it... and you CERTAINLY look the part. Birdie, the job is yours, if you want it. There MAY be some longer hours, though, you understand." His grin got bigger, and he wasn't hiding his overt stares. The wheels were spinning in my head, too. A cushy job, probably a raise, too? Why not?

"That's very kind of you, Sir. I'd love to give it a shot. When would I be training?" He lit up, and replied,

"Why don't you start today? We could use a pretty, I mean, fresh face in the office. Put your things in your locker, and I'll let Martha know to start your training right away." It wasn't lost on me that he watched me sway out of the office. This day was going off the charts better than I imagined.

It was also clear that Martha was not comfortable, and assumed the worst. "So, deary, what did you promise him? A late night roll in the sack?" I laughed, and she grinned, and things lightened up a bit. She realized that I did know the business, and would be easy to train. I WANTED to ask if SHE, herself, had given some of those late night rolls, but thought better of it. I'd rather keep her on my good side. At lunch, a few of my buddies teased me about my looks, AND my new position, with lots of lewd jokes. I just laughed along with them, suggesting that maybe they should start wearing skirts and makeup, but they insisted they'd leave that to me.

The day went amazingly fast, and just before the buzzer went off, the boss called me into his office. "Birdie, there are a few things I wanted to go over with you, so, why don't I give you a ride, instead of you chasing the bus?" I easily accepted, even though I had a hunch what those things were. He walked me out to his car, opened the door for me, and stood by the door, watching as I slid in the seat, my skirt riding up enough for him to see the tops of my stockings. He got in on his side, buckled up, and pulled out of the lot. He asked how my first day went, and if I liked it, and of course I responded that I loved it.

As soon as I answered, he reached over, ran his hand up from my knee to my stocking top, then pulled my hand over to his crotch. "There will be other things that will need your attention, too, Birdie." (Holding my hand on his stiffening cock) Without answering, I licked my lips,leaned over, unbuckled him, unzipped him, and fished his average sized, but hard, cock free. I let my fingers glide up and down it, and he immediately pulled into an alley. "I...won't be able to drive, like this." I grinned and lowered my lipstick mouth on his cock. I giggled as he groaned way too loudly,and proceeded to slip his cock in my wet mouth. My tongue swirled on him as his fingers ran through my hair. He was lifting his hips up as high as he could and I slurped him up. I could taste his precum, and felt him tremble. I KNEW he wasn't going to last. I'd bet my paycheck that his wife thought she was too good to do this, too. His moans and "oh my God's" were driving me to suck every drop I could get out of him. He was squirming and shaking as he blasted into my mouth. I swallowed the first blast, and saved the second, until he softened, to show him, before I swallowed again.

"Did I pass the interview, Sir?" I grinned innocently. His chest was heaving, as he tried to catch his breath. I tucked him away, re-zipped him, and buckled him, just like nothing happened. I licked my lips, and re-applied my lipstick, waiting for him to settle down enough to drive.

"Fuck, Birdie, NO ONE has ever done it like that before. I think this is the beginning of a beautiful arrangement." He pulled up to the jail, and I leaned over, gave him a peck on the cheek, and gave him an eyeful of legs and ass swaying as I walked from the car. My first day going out fully dressed was a smashing success!

When I walked into the guard station, one of them said, "Sorry, Miss, only inmates beyond this door." I hugged him, kissed his cheek, grabbed his crotch.

"Ok, Sir!" and burst out laughing.

"Birdie! What the Hell! How did you get out of here dressed like that?" To which, I swished my skirt high, and walked on.