Jail Bait

byDeborah©

by Amazing Grace (a/k/a Deborah)

My entire family has spent at least some time in the slammer, except my mother; she's dead. My older brother James is a transvestite and got busted for soliciting which caused him to become the black sheep of the family (see the story “A Maze & Grace”). Doing hard time is one thing, dressing up like a girl and sucking cock is quite another, at least to my father.

Daddy, he did a year for income tax evasion, a very reputable crime, according to him. “Who doesn’t try to fuck the IRS?” he asked when questioned about his criminal record.

I only spent one night in jail, for drunk and disorderly and resisting arrest. A wild party had gotten even wilder. The neighbors got pissed about all the noise, but what really ticked them off must have been when we all got naked and went outside and played volleyball. Something about corrupting the morals of their kids so they told the cops. What I can’t understand is why the dude who called the police watched us for an hour with binoculars before he made the call. And then the same guy offers to bail me out of jail if I promised to give him a blowjob. I told him to fuck off.

My sister Camille is a high-priced call girl. She only got nabbed once. She spent some quality time with a famous celebrity who had been in trouble with the law for drugs and such. Someone tipped the narcs and they got busted in a luxurious hotel suite with some illegal substances.

“Totally stoned,” Camille related, “and naked, that’s how they found us. And Bobby, the famous dude in that TV show and those movies, starts mouthing off about how all cops have little dicks and no balls.”

Now my younger brother, Billy, he did some serious shit. He started with stealing bikes and moved on to grand theft auto. He really had a thing for Corvettes, particularly those several decades old, and they brought the most money.

“I love this one, Billy!” I raved about a 1967 Corvette convertible, red with a black interior and top. It had a 350 horsepower 327 and four speed. “Get a white one like this and I might buy it,” I offered, “if you give me a good deal.” He found a 1963, white with black interior and top. Great years for Corvettes, more like sports cars than those dogs they made in the 1980’s.

Billy would comb the entire country looking for the prime stuff. Finally he took one too many chances and got nabbed by the state police in a certain northeastern state while driving a 1961 Roman Red with White Cove, you guessed it, Corvette convertible that didn’t belong to him. The gun and dope he had in the car didn’t help matters much either. Five years in a maximum security joint is what he got.

“Sis, you wouldn’t believe the things that go on in here,” he said so many times in different words in his letters. Such sad and shocking letters he wrote me. I couldn’t stand it, I had to go and see him.

Visiting Billy in prison became a little more involved than dropping in on my clients in their hotel rooms. I worked for an escort service for a short time to come up with the cash to pay my college tuition.

The prison bureaucratic red tape that must be endured before you visit your loved one is long and difficult. You have to turn in an application to a counselor who sits on it for awhile before passing it on to the department that does the background checks. They don’t even tell you if you’ve been granted permission. You just have to call and call and call.

At long last on the day you show up at the prison, it’s random searches of vehicles, registration, metal detectors, drug dogs, the guards feel you up real good and you even have to take off your shoes for inspection.

“Billy!” I hugged and kissed him when we at long last met. He cried and cried and cried.

The visitation has some privacy, taking place in small cubicles with panels about five foot high. But if a convict or guest violates the rules, the visitor is quickly escorted from the premises.

“That guard, Roland, watch yourself with him,” Billy warned. “He’s the one who stuck the billy club up my butt my first day here.”

“What’s it like in here, Billy? The truth, tell me the truth.”

“If you’re pretty like me, you get along. I’m a girlfriend. My main man is a lifer; he split a hooker’s head open with a shovel he had in the back of his pickup. Jethroe is his name and he’s from West Virginia. I’m just another sheep to him.”

“Tell me more, Billy,” I begged.

“Well, Roland does me special favors if I do him special favors; a pack of smokes, generic though, for a blowjob. When he’s checking the cell blocks he’ll stick his dick through the bars when he knows I’m out of cigarettes.”

I gave Roland the once over the next time he passed by our cubicle and leered in. He looked like a fucking slob; about forty, pot belly and bad teeth, and he looked mean as a snake.

“Hey cunt,” Roland snarled at me, “time to go, get your sweet ass out of here.”

“Billy,” I asked as I rose to leave, “is there anything I can do for you, I mean anything, to make your life more tolerable in this awful place?”

“Yeah, Sis, next time you come don’t wear jeans and a sweatshirt. Get all dolled up. You know, a dress or something. It’s been so long since I’ve seen a real woman. Sis, do you think, I mean would you consider, if I could arrange it, uh, I mean, oh never mind.”

“Spit it out, Billy.”

“Would you let me fuck you? I don’t even remember what pussy looks like. I could probably make a deal with Roland so he’d kind of look the other way while we’re doing it. I’ll probably have to have his dick for breakfast, lunch and dinner, but it would be worth it.”

“I’ll think about it, Billy.”

“One more thing, Sis?”

“What, Billy?”

“Bring me a wig.”

“No problem, Billy, whatever you want. I’ll bring some lipstick, mascara and other stuff too.”

We embraced briefly and I left. Roland pinched my ass when I walked out. I made like I didn’t even notice because I didn’t want Billy getting any more shit than necessary.

A month later I came back to the prison for another visit. This time I got dressed to kill, just like Billy asked. I dressed totally in black leather, and I mean everything. First, I put on a braid zip front leather halter with an adjustable neck and sure fit stretch panels. I didn’t bother with a bra. Then I slipped on the black leather thong and 17 inch lambskin mini-skirt with a zippered closure. I have a shorter one but this seemed more appropriate for the occasion. In view of my long legs, it came down to about mid-thigh.

“Where are you going dressed like that?” my father asked as I paraded around the kitchen in bare feet.

“I’m going to see the son you pretend no longer exists.”

“Which one?” Daddy asked quite seriously.

“Billy!” I screamed at him.

“Isn’t that nice. I wonder what he’s up to in that prison. No doubt he turned out to be a cocksucker just like your other brother. What did I do wrong?”

“Nothing, Daddy,” I reassured him. “And they are both good guys despite getting in a little trouble and being sexually promiscuous with both men and women. You know, Daddy, I’ve had sex with other women.”

“That’s different. I know what you and your girlfriends used to do up in your room. I could hear the vibrators and the moaning. A guy sucking another guy’s cock is something else, very sick and disgusting.” “Whatever, Daddy, father knows best.” With that I stomped off upstairs and finished dressing.

I struggled with the 11” black elk tanned leather cowgirl boots. As a final touch I decided on my designer cowhide blazer. It is satin lined with a 3-button closure and looks great with anything, from an evening dress to jeans.

Since I didn’t own a wig, I stopped at the mall and picked one up. I covered my blonde hair with a long straight black wig with six-inch bangs. It fell to past my nipples and I rather liked the look.

“Nice wig, Sis! Is that for me?” Billy asked as I entered the cubicle and greeted him.

“Yes, dear brother. You can have it when I leave. But what about my outfit? You asked me to get all dolled up.”

“You look awesome, Sis! Did you think about what I said, you know, the fucking?”

“Yes, dear brother. You can have it when I leave, no on second thought, let’s make that now. Let’s fuck and get it over with. Then we can talk. Did you make a deal with Roland?”

“Uh, well, sort of. I think he wants to watch.”

“OK, he can watch. I thought it would be worse than that.”

“Uh, well, I think he wants your panties? What are you wearing?”

“Black leather thong,” I replied as I lifted my leather mini-skirt and showed him. “What the hell does he want with these?”

“Roland wants me to wear the panties and the wig when I blow him. Something about he’s not queer and the idea of a guy sucking his cock kind of embarrasses him.”

“Whatever,” I responded nonchalantly. “You can have my top also if you want. See, you can zip down the front and reveal as much cleavage as you like. I’m not wearing a bra as you can tell.”

“That would be great, Sis! There is one more thing that Roland demands. He says you have to suck his cock while I’m humping you from behind.”

“Wonderful,” I groaned.

“Yeah,” he says his wife won’t blow him, and you should see her, what a dog. She’s the warden’s sister. But she is one rich bitch and got Roland this job. He says he has to go to those adult bookstores that feature the booths with the glory holes to get good head; or else negotiate with a convict like me to do him.”

“What a fucking pervert!” I snarled sarcastically.

“So you’ll do it then, Sis?”

“I guess so, but I’m not getting down on this tile floor. I’ll just bend over and you can slip it to me from behind. I’ll pretend Roland is Mel Gibson and have him shooting his load in about two minutes. Won’t be that bad I suppose.”

“Whatever you say, Sis!” Billy agreed gleefully.

I pulled the dual speed vibrator out of my purse.

“What are you going to do with that?” Billy inquired moronically.

“You don’t really think you or that fat pig Roland could make me wet, do you? I need to get it warmed up.”

“I’m surprised they let you bring that thing in here.”

“Yeah, well, I told them I had a prescription for it. You know, my doctor deemed it necessary for gynecological heath, much like jerking off is good for prostate health. I even have a phony note from the doctor and used a bunch of big medical terms. They didn’t have a fucking clue what I blabbered about.”

“This vibrator is called a Deluxe Foreplay to Love Kit. Check out all the attachments I got for it, and for only $45.99.” I removed my thong and flung it at Billy, sat on the chair, snapped in my favorite attachment and began to do myself with the vibrator. Five minutes later I got a real nice buzz.”

“OK, get Roland in here, Billy.”

While Billy went to get the fat pig, I set up the MVC 3000 Miniature Tube Color Lipstick Video Camera to record. The lens barely protruded through a one inch hole in my purse, which also contained a power pack to which I connected the wires.

When they both returned, I had slipped off the mini-skirt and unzipped the halter top all the way, displaying my voluptuous breasts.

Both Billy and Roland had lust in their eyes and I could see the protrusions in their pants.

“Hey, cunt, your name is Grace, right? Well, Grace, I’m going to cum all over your pretty little face,” Roland spat sarcastically. “You are one pretty little bitch.” He began to drool.

“OK, let’s get it over with,” I sighed as I bent over. Billy quickly dropped his pants and entered me from behind, put his hands on my hips and started humping away furiously. Roland also quickly dropped his. He had a thick but short dick. I could get it all down my throat.

With one hand I cradled Roland’s balls and I played with his butt with the other, fingering his hole. I went down on him hard and fast, deepthroating him. He pulled off the wig, threw it on the table and grabbed my hair and pulled it roughly.

Roland didn’t even last the two minutes. He forced his cock as far down my throat as he could and put his hand over his mouth to stifle his cries of orgasmic pleasure. Then he pulled out of my mouth and shot his cum all over my face, just like he said he would, singing “Amazing Grace” all the while in the worst voice I have ever heard.

“You little fucking cocksucking whore, this is what you wanted,” Roland muttered over and over as he painted my face white and sticky.

It didn’t take Billy much longer to shoot his load either.

“Pull out Billy, pull out!” I cried as I knew he was close. I hadn’t been too conscientious with my birth control pills lately and I didn’t make him use a condom.

I turned around, got down on my knees and let my little brother cum in my mouth. He chewed on my thong as he got off so as not to cause too much noise and attention. I swallowed most of his cum and held him all in mouth until he stopped quivering.

When I finished I stood up immediately and got dressed.

“Roland, do you have an e-mail address?”

“Sure, honey, you like my cock so much you want more, huh?”

“Sure do, Roland,” I cooed as he handed me a slip of paper with the address scribbled on it, and then he swaggered out of the cubicle.

Billy and I talked for half an hour and then I got up to leave.

“When are you coming back, Sis? Can we do this again?”

“I won’t be coming back, Billy,” you’ll just have to do without pussy. It won’t kill you. Besides, you have the wig and my thong. And here’s some lipstick, mascara and various other assorted beauty items. Make your own pussy.”

“But, Sis …”

“No buts, Billy, except your butt maybe being the substitute for pussy around this despicable place. But only if you want it to be. Roland will be protecting your ass from now on, not fucking it, or your big mouth either. I’ll make sure of it.”

“How, Sis?”

“Never you mind,” I got close to him and whispered as I turned around and left.

The next day I had a photographer friend of mine make some stills from the film. I scanned the best two shots of Roland’s cock in my mouth.

In the e-mail message to Roland I said, “Did my brother tell you I’m jail bait? Rumor has it the reason you got the job at the prison is because you married the warden’s sister. Don’t fuck with my brother and don’t let anybody else fuck with him either. We wouldn’t want your rich wife or her brother the warden to see these pics attached, now would we Roland? We wouldn’t want them to find out what you are really doing while you are supposed to be hard at work. Your days of being ‘hard’ at work are finished, you fat, ugly, disgusting worthless piece of shit pig. And if Billy asks you to, you better wear that fucking wig I left him; and the lipstick, and the mascara.”

From then on, Billy’s letters indicated he actually enjoyed prison life. No, I didn’t ask why. I didn’t really want to know.

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