The Prison Wallet

My name is Robin Blair and this is the whole truth. These events began during the last few weeks of my senior year in highschool shortly after I turned eighteen.

I was never queer when this all began, it just sort of ended up that way.

It started far away from me with politics of all things. Someone in the state senate decided that treating prisoners better led to a reduced chance of them going back to prison once released and so a major reform of the prison system began. I had no idea at the time how this would affect the course of my life.

Two of the reforms in particular would go on to have a huge influence on my sexuality. The first reform was when the state began to crack down on corruption in prisons by getting rid of bad guards and wardens.

The second reform was to allow conjugal visits to help with inmate morale and because the state had taken a more liberal stance the past few years, the governor signed legislation stating that inmates could have conjugal visits from same sex partners.

I was blissfully unaware of these events as they unfolded being uninterested in politics or prison reform in any way shape or form. No, I was far more interested in finishing up highschool and getting into college. I was also far more interested in chasing pussy than paying attention to whatever was going on on the news.

Not that I was all that good at getting pussy. First there was my name, Robin Blair which many people mistook to be a girls name and second was my stature. I was all of five foot five and one hundred and fifteen pounds. It didn't help that I had mom's good looks but even with these disabilities, I did manage to get laid on the evening of my eighteenth birthday.

I didn't know it at the time but that would be the very last pussy I would ever get.

I still had five weeks of highschool when recruiters began showing up looking for talent. Some were looking to put kids in college and others were looking for employees. As for me, I needed both. I wanted to get into college and to find a way to pay for it so naturally I ended up sitting down with recruiters from both camps.

Now just a little background info to help you understand what happened. Not all recruiters were looking for bright, honest and law abiding kids. No, some were looking for exactly the opposite. Some were looking for girls to put on the streets and others were looking for someone to sling yayo (i. e. cocaine).

And while it's both humiliating and true that I had more than one offer from the former, It was the ladder that I found myself in front of in a small nook in the back of the student library one afternoon.

"Look kid, I know you want to pay for college, the only question is do you want to flip burgers for four years or would you prefer to do something far easier? Think about it. I can arrange it where you make just one run a week and make triple what you'd make anywhere else." the recruiter said.

Now I was no fool, or so I thought. I knew some of these recruiters were looking for kids to use and toss aside but I also knew there was good money to be made so I decided to listen.

"And exactly what would I have to do to make triple? You're not paying that kind of money for something safe or easy." I asked not necessarily because I was uninterested but more as a matter of a negotiating tactic. I was definitely interested, I just didn't want to seem like I was.

"Look its real simple kid. You look well... kinda, well you know. Like a pansy. No offense. Live and let live I always say but why not use it to make a few bucks is all I'm saying." he said.

"No thanks, I already had a few offers like that and I aint no hooker." I said angrily.

"I aint talking about you turning tricks kid. I got something better in mind for you. You might not know this but right now, the prisons are dry as a desert. That's right. Thanks to prison reform there aint no powder or pills anywhere and that my friend is where you come in. We got ourselves a fool proof way to get supply into the prisons. You following me?" he asked.

"Not really." I said.

"It's simple. Our wonderful governor had just given us a perfect way to get drugs into prison. Conjugal visits. You just pretend to be some guys heart throb and sneak in some yayo, maybe some pills and boom!!! we all get paid." he said quite a bit louder that I was expecting.

"I'm a dude, not some chick." I exclaimed in disgust.

"That's the beauty of it kid. The dumbass in the governor's mansion didn't just allow conjugal visits, he allowed gay visits too. Look it's real simple, we dress you up as a fairy and you carry something into the facility in your prison wallet and that's that. No problem." he explained.

"First, I aint no fairy and second, dont they do cavity searches and third, I aint letting anyone put anything up my ass." I said expressing more disgust and then asked, "Why not use a girl?"

"Hey, back up there kiddo. I never said you was a fairy. Just that we'd pretend you was. Girls always get a cavity search since guards love pussy. As for your cavity search, we got ourselves a fool proof way around that. We put you in a diaper. Ain't no prison guard ever gonna search a wet diaper. And as for the other thing you need to concentrate on the money. What's a little inconvenience compared to that. It's a guaranteed two grand for each trip you make and that's just for one prison. You know how many prisons are in this state kid. I'll tell you how many... a lot." he said finishing his pitch.

"Two grand? And no one would know, I mean about me dressing up and all?" I asked. I was ready to consider the job but the thought of wearing fairy clothes bothered me and then there was the diaper.

"Seriously, ain't nobody in our organization is in the advertising business kid. The less people knowing what we do, the better. It's perfect, prisoners pay more and we only need to make one delivery instead of putting you on a street corner slinging." he said sarcastically.

"Well, a lot of people said I was probably headed to prison. Might as well get paid to go." I said adding a little humor to the fact that I had just agreed to be a drug mule.

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And now we come to the part of the story where I start my actual journey to becoming... well, I don't exactly know what I am becoming.

I followed the instructions carefully, no solid food for three days to make my ass more accomodating and less messy and so with still a month to go in highschool I made my way to a nice townhouse in a surprisingly upscale part of town to get dressed and get some drugs put up inside my ass for my very first delivery. I was nervous as hell. I needed the money even more since I had been accepted to a local college and wanted a nice bank account before the fall term began.

The man and woman that greeted me at the door seemed anything but drug dealers. He looked more like a banker or business man and she showed every sign of being a trophy wife.

I was first made to strip naked so I could get my ass penetrated by a large plastic drug container. I swear it had to be at least ten inches long although I was assured it was only just over eight. And ungodly thick.

I had to stand against a wall slightly bent forward while what I assumed was some sort of dildo was used to open me up enough to take the drugs all the way up inside me.

Next came the adult diaper to make sure no one gave me a cavity search. It was absolutely disgusting and it made a hell of a crinkling sound when I moved.

This was followed by the girly clothes. Since I was supposed to be visiting a lover I was supposed to be dressed like it. Stockings and a garter followed by a stuffed bra all covered by a nice conservative underslip and then came the dress. A simple purple ladies dress. Not sexy or anything, just a normal dress.

Next I was made to step into some flats, also purple and last was to have the lady do my makeup and hair.

This proved to be more difficult than I had imagined. Not because I knew nothing about makeup or hair, no I had studied for almost a week, no the difficulty came from the fact that I had been standing the entire time since my ass had been violated by the drug container and suddenly sitting down made it quite uncomfortable.

And my dick got hard as a rock tenting both the diaper and my dress.

The last thing I was given was some fake out of state I. D. and some out of state documents saying I was legally married to some guy named Darren Compton. I was also handed a large purse to hold the documents which also had normal girly things in it like a comb and brush, makeup, condoms, ink pen, keys, tissue and other assorted things a woman might carry.

It also had several extra diapers to complete the charade.

The man whose name I still did not know then ushered me into his car to drive me to the prison. It was a forty five minute drive and even though we were in a luxury car, the slight bouncing of the seat made the plastic drug canister in my ass so damn uncomfortable and also erotic at the same time.

We arrived at the prison and just before I got out of the car, my driver handed me two small rings. One was an engagement ring with a diamond and the other was a gold wedding band.

"Your married so you need to wear this." My chauffeur/handler said.

I got out and to my surprise so did the man who drove me. He unzipped his fly and got behind me and lifted up the back of my skirt. I was too shocked to do anything and so just waited while he placed his cock down the back of my diaper and began pissing.

"No one will want to check out a wet diaper." he said. I understood but was a little upset that I wasn't allowed to wet my own diaper and that no one told me I needed to be wet in the first place. Although thinking back, the recruiter did mention a wet diaper.

"All right now sweetie, this part you have to do on your own. Good luck." he said and I was about to start walking across the parking lot when I had a thought and asked, "Wait, how do I get paid?"

"Your so called husband or his associates have already paid for the merchandise. I will pay you when your done." he answered.

And so I walked to the building and inside excited the whole time. I couldn't quite decide what was keeping my dick hard, the drugs up my ass, the stockings, the thick wet diaper, the chafing of the padded bra or the nice warm breeze rustling the skirt of my dress and gently caressing my upper thighs between my stockings and the diaper.

One thing was for sure. I was excited and it wasn't because this was my first day as a drug mule.

I signed in and was shocked by how normal everything seemed. I expected some cat calls or at least some vulgar comments about being a guy in drag here presumably to get fucked by my prisoner husband but no, nothing. It all seemed so professional.

My identification was checked and so was my paperwork stating that I was married to the prisoner I was here to visit. My name was checked against a computer list of visitors and thanks to my bosses, my name was on it. My fake name that is.

Lastly I was ushered into a room to have my things inspected. My purse was dumped out revealing my diapers and all the other stuff I carried. I was then given a good pat down for weapons and I was even more surprised when one of the guards noticed my very wet diaper but said absolutely nothing.

No one gave me a cavity search. No one.

I was then led to a so called 'family room' which was code for the room where prisoners fucked their wives or in my case, gay wives. Not that I had any plans to get fucked.

"You get settled in miss, we'll have your husband down shortly." a guard said as he led me into the room.

I did have to leave my purse behind and the guard very politely asked if I needed to take any extra diapers with me and so to maintain the charade, I took one and was holding it as we entered the room.

I decided to remain standing as it was less uncomfortable and was just holding my diaper, dressed like a housewife when my so called husband was let in by a guard.

Darren Compton was a large imposing man in his late twenties or early thirties. He stood a good six foot five and had more muscles that a bodybuilder. On his left arm was a tattoo that said "BITCHMAKER".

"Damn girl, Vincent said he was sending someone special but hot damn." he exclaimed upon seeing me standing there in a dress holding a diaper.

"I'm not a girl." I clarified not wanting his amorous attentions. "I'm just here to make a delivery."

"Yeah, I got it. Okay, lets get them goodies out of ya." he said and indicated the bed.

He laid one of the complimentary towels on the bed for me to lay on. I felt extremely vulnerable as I lifted my dress and laid my wet diapered ass on the towel so this man who was pretending to be my husband could retrieve the drugs from my ass.

It hadn't occurred to me to just bend over and instead I found myself on my back on the bed with my legs spread.

"Oh, did my sweetie pie have an accident, daddy will change you baby." he said as he examined my soaking wet diaper, a diaper that was wet with someone else's piss. He was so big and imposing that I chose not to argue when he called me a sweetie pie or baby and himself daddy.

He untaped the wet diaper and removed it tossing it in a nearby waste paper basket leaving me and particularly my erection exposed. I said nothing.

He turned his attention to the small string hanging out of my ass and said, "Time to take out your tampon baby." and he pulled it and in one solid and horrifying yank, pulled the whole thing out of me.

I screamed in pain and more than a little humiliation as my own dick which had a mind of it's own suddenly began to spurt a huge rope of sperm straight up in the air to land on the front of my dress.

My pretend husband seeing this tossed the drugs on the floor and quickly got undressed as I tried to recover from the pain of having the drug canister ripped out of me.

And then he was on me. On me and between my legs. On me and between my legs with a huge erection pointed at my hole.

The weight of his body all covered in muscles easily kept my small and slight frame from wiggling out from under him. His mouth found mine and his day old whiskers tickled my face as his tongue found its way inside me.

And I did not resist.

His chest was on my chest and my own recently ejaculated jizz was mixing with his sweat. He didn't seem to care.

He roughly pulled my legs up as high as they would go putting my asshole directly in line of his cock.

And he slid inside me. The lube leftover from the drug canister helped but it still hurt like hell and for the second time since I had arrived, I let out a scream.

He began to fuck me. Slow at first then harder and harder. Then slow again.

All I could do was to lay there and take it. I couldn't stop him if I tried and I wasn't sure I wanted him to stop.

The one and only girl I had ever had sex with had a somewhat disinterested look on her face as I busted my nut inside her but not this man, his face was all passion and madness as he fucked me the way a person who dresses this way should be fucked.

I saw in him desire and dominance, anger and frustration, power and control. I saw in him a need, a thirst that only a boy in a dress could truly satisfy and there was no denying he was damn sure gonna be satisfied at the expense of my poor asshole.

He pounded me harder than I ever imagined a man could fuck and as he did, I began to feel overwhelming pleasure. He fucked me and I felt all the bullshit of my youth slip away along with any pretense of manhood.

He fucked me because I looked fuckable, because I was fuckable. The recruiter had known it and so did the man and woman who had prepared me for this knowing damn well I would lose my cherry today.

And he kept fucking me until at long last he tensed up and there was a feeling of an explosion deep inside me as my body spasmed with another orgasm. I was being inseminated and I wanted it.

After our shared orgasm, he pulled out and collapsed on top of me. He was easily a full hundred pounds heavier than I was, maybe twice as heavy so I could do little but lay there with his weight resting on top of me. My dress was up and legs spread so like him, I fell asleep.

I awoke to find him exploring my mouth with his and I accepted his passionate kisses and soon he was again hard.

It had been my intention to stay just long enough to deliver the drugs and maybe a few minutes to make it look like we had done something but now I wanted to stay as long as I could. I knew we only had six hours together and not knowing how long we were both asleep, I spread my legs wide again in invitation.

He took the invitation and once again plowed into me. This time was more comfortable as he seemed to have spent his wild lust and now only wanted to make love to me.

His cock filled me with long slow strokes lubricated with his own sperm. I wanted it all and he delivered. He made love to me taking time to make sure I enjoyed it as much as he did and my dick showed how much I liked it.

After he came inside me for the second time, he got off of me and grabbed my extra diaper and proceeded to tape it on me filling me with more shame and humiliation but also a sense of lust.

After I was diapered I got off the bed and straightened myself up as best I could while I watched my fake husband first shove the drugs up his own ass then get dressed. No surprise, he needed to get the drugs from here to his cell block.

We left the visiting room, him in his prison clothes and me in a dress covered in my own sperm wearing badly smeared makeup and disheveled hair looking every bit the whore I knew I now was.

Life since that day has been an adventure. I never went to college. I work as a drug mule delivering to four different prisons, each with a different pretend husband with a different cock for my willing ass. I quickly took to wearing a dress full time as my handlers certainly had planned but no matter, I was happy.

In time the corruption that had led to prison reforms began to reassert itself and I was no longer just delivering drugs but also making extra money from both guards and prisoners that could afford to pay to fuck me. Well, the prisoners had to pay, the guards got me for free.

I had a different name for each prison I visited but my handlers just referred to me as a prison wallet since I carried everything up my well fucked ass.

Oh and one last thought. I did learn to love the diapers and even kept wearing them even after guards stopped searching me for drugs. I even began to delight in having men pee in my diaper to mark their territory and every man who wanted to recover his drugs and fuck me had to change my diaper.