Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows?

As my regular readers are aware, I enjoy writing about the transgender experience from different perspectives.

Here I write about a transgender woman whose experiences in prison were quite different than she expected them to be.

~~~

Chapter 1.

Jeri's jaw dropped open when she saw the big black cock hanging between Bubba's legs. As she laid there in her bed that night, she thought about the irony of the decision she'd made to accept Warden McQueen's gift, thereby exposing herself to the one thing that had scared her most about going to prison.

She was snapped out of her daydream by the creak from her bedroom door when the big muscular professional football player closed it behind him. He put a finger to his lips to shushed Jeri before pulling back her covers and signaling her to shift her body so her ass was on the edge of her bed. He then squirted a dollop of lube on her pucker before using his thumb to loosen her rear entrance.

When he felt she was ready he began to push the head of his big dick into her outer ring. Jeri hadn't been fucked by a cock that size before; therefore it took Bubba a few minutes to get a good amount of his thick dick inside of her. While he was hunching he was also pumping Jeri's cute little cock with his hand. The pleasurable sensation helped her inner ring relax, and it was only a matter of minutes before his nine inch cock was in her asshole up to his balls. The deep prostate massage he was giving her soon caused her to shoot her load all over her stomach. Bubba then shot his wad deep into her bowels before leaving the room without saying a word.

~

The very next day Jeri was released from prison. As the limo took her to her new apartment she looked back at the time she'd spent at Chateau Elegance.

~

Jeri's flashback.

A year ago as Jeri Hall sat in a male's housing unit in county jail, he was careful not to get caught as he stole a look at a really cute inmate. During his brief time in lock-up he'd learned not to get caught ogling anyone. For most prisoners it was the best way to avoid a fight, but for Jeri it was a matter of survival.

His short hair was permed and styled, both ears were pierced, and his eyebrows were arched. As a result of his feminine appearance, keeping to himself was the best way to avoid the ire of a homophobic inmate who might get angry if he thought Jeri was a gay man hitting on him. It also helped him avoid predatory inmates who would have their way with a sissy.

The reality was he wasn't gay; he was actually a woman inside a man's body.

He'd been in jail since he'd been sentenced, but today was the day he was headed to big boy prison, and he was terrified at the thought of what might happen to him. He enjoyed sucking hard cocks and having his backdoor sex pounded by dominant men, but he wasn't interested in being forcibly taken by some sadistic brute while he was in prison.

~

He didn't know it, but destiny was about to bring Jeri together with Warden Barbara McQueen. Barbara grew up as an effeminate boy named Darius. She transitioned, and then married her husband Ethan.

He ventured into politics and was eventually elected to the United States Congress.

She concurrently worked her way through the ranks of the nation's penal system to become a Warden.

Witnessing the plight of transgendered prisoners inspired her to seek a more humane way of incarcerating them. She then successfully lobbied her husband and his colleagues to appropriate money for the creation of a co-ed for profit prison that would be modeled after Bastoy Prison, which is the Norwegian institution with a humanistic approach to prison life.

Thus, Chateau Elegance minimum security prison was born.

~

When the time came to be transported from county jail to a federal penitentiary Jeri was loaded into a luxury cruiser instead of a bus with caged windows. The courteous driver told him that he was being transported to an exclusive minimum security facility.

A few hours later he knocked on the door of the Warden's office at Chateau Elegance. "Come in inmate Hall," said Warden McQueen as she looked over the rim of her reading glasses at the effeminate man. "Please have a seat."

"Thank you Warden McQueen," Jeri responded speaking as humbly as he could.

It was his first day in the joint, if you want to call the minimum security facility modeled after Bastoy Prison, the joint. He was already too scared to talk or look at anyone, and now he'd been sent to see the warden. He wondered what he could have done wrong already. As he walked into the office he was feeling more emotions than your humble storyteller can imagine for him.

When he sat down he made himself as small as he could by crossing his legs and folding his hands on his lap. His heart was racing and his mouth was dry. All in all he was prepared for the worst.

The warden looked like a tall, attractive Cisgender woman in her forties. Dressed in a starched white blouse and a blue pleated skirt, she was the antithesis of the caricature of prison wardens portrayed in movies. In fact she was more like a CEO than a warden.

Warden McQueen actually smiled when she heard how soft and feminine Jeri sounded. "Hi Jeri," she said warmly. "I'm Barbara. How're you doing?"

Her welcoming tone certainly wasn't what Jeri was expecting. He bit his bottom lip nervously as he tried to make sense of it before stammering out, "I'm good, Ba, Barbara, how are you?"

"Oh come on now, stop being so nervous. There's nothing to be afraid of here," Warden McQueen said reassuringly. "I'm sure you're wondering why I asked to see you." She said as she sat back in her comfortable office chair and crossed her long legs.

Warden McQueen then told Jeri what was going on. "You have been accepted to serve your time at the most exclusive penal facility in the country. We provide a safe space for select transgender people to serve their sentences," she explained. "You're here because Mr. Mooney Baggs paid for your tuition."

Hearing his name stirred Jeri's emotions before he told Barbara the sordid story leading to his incarceration, "He's the owner of the company I worked for, and also the person responsible for the fraudulent document he paid me a bonus to sign. Then he swore on a stack of bibles in court that it was all my doing. That's why I was sent to prison."

"Apparently he grew a conscience after framing you," stated Barbara. "The bastard."

Her comment about Mr. Mooney Baggs caused Jeri to smile weakly.

Warden McQueen then read her computer screen, followed by an inquiring glance before saying, "In your file states that you're a male named Gerald, but according to your physical evaluation you have a cute little cock, a great ass and small perky breasts."

After looking at him inquiringly she said, "Your file doesn't say you're transgender, but I can see from looking at you that you are in fact a woman."

Jeri hesitated before talking about his personal business, but he finally said, "I've transitioned as much as I could without taking hormones. When I got the bonus from Mr. Mooney Baggs, I planned to use it to change my gender marker, pay for doctor visits, and buy a year's worth of HRT. But I had to spend the money to pay my lawyer."

Warden McQueen looked at him sympathetically before saying, "Aww hunni, I'm so sorry to hear that. Your face is almost passable already, and you have the beginnings of a nice figure. Your titties may be kinda small, but more than a mouthful is a waste isn't it.

"Stand up and turn around, let me see your booty. Hm, i can see you have an apple bottom there even though you're wearing that hideous orange jumpsuit."

Once again Jeri didn't know how to take the Warden's comment, so he kept quiet.

After a pause to gage Jeri's reaction, the warden continued, "Our facility is primarily for transgender women, but we charge a fee to certain people with political connections, who can afford to serve their sentence in here."

We use those fees to provide for a number of special perks for our transgender ladies. We pay to have their gender marker changed, and we also provide HRT treatment for free."

Hearing her say HRT would be free made Jeri's heart skip a beat and he might have stop breathing momentarily.

Warden McQueen then added, "We also pay for every transgender lady to have a makeover, and we take all of them on a shopping spree from time to time."

Then she looked into Jeri's eyes and said, "Jeri, as long as you are at this facility you'll be treated like the beautiful woman you are."

Warden McQueen smiled again then continued with her presentation of the virtues of Chateau Elegance, "I'm sure you'll find the accommodations here to your liking, and your sentence will be over before you know it.

"You'll share a cottage with three other patrons. We have amenities like tennis courts, horseback riding, gourmet cooking classes, and many more fun things to do."

"If you're interested in working we offer our patrons the opportunity to assist our employees as they work in our vineyard, in our winery, and in our gourmet kitchen, etcetera."

By that point Jeri's expression was blank. He couldn't believe the things he was hearing.

"Now if you'd excuse me for a moment, then I'll give you a tour of the facility and show you to your cabin."

Warden McQueen then went into her bathroom, stood in front of the commode, lifted her skirt, then took her big cock out of her panties and tinkled.

~

Chapter 2.

For the first time in his life Jeri is viewed as a woman.

As Warden McQueen strode along with Jeri in route to her cabin, the Warden sounded perky while pointing to the bowling alley, tennis courts, putt-putt golf and numerous other sources of amusement available.

She also gave Jeri a few survival tips. "You're in prison, but you're not," she explained. "There aren't any walls or fences here, and you can even leave our village with prior permission. Weapons aren't allowed and neither are gangs, but some of the transgender women get possessive of the men who spoil them.

"All in all its the best detention facility you could ever serve time in."

Jeri was still speechless. The property the warden had shown her looked like a small community rather than a prison.

When they reached the cabin that would be Jeri's home for a while, one of her male housemates was outside sunning himself while wearing a Speedo. When he heard them come up he uncovered his eyes and studied her for a moment. Though Jeri was still wearing an orange jumpsuit, the older man suspected there was more to her than met the eye, but he used the pronouns that matched the way they looked when he greeted both of them. "Hi Barbara, how ya today?" he said while shading his eyes.

He then looked at Jeri and spoke in his best southern drawl. "Hello dahlin. Welcome to paradise." He said before licking his lips in an overtly sexual way.

Warden McQueen giggled and touched Jeri's arm before warning her about the older man, "Always keep an extra pair of panties handy when you're around Senator Kemp, because he'll charm you out of the ones you're wearing. She then made official introductions, "Jeri, this is Senator Bradford Beaumont Kemp. He's a politician who was caught defrauding all of us, now he gets to serve out his sentence at our upscale detention facility.

"Senator, this is Jeri Hall. That's Jeri with an 'I'. She's your new cabin mate."

Jeri glanced at Warden McQueen before saying, "Hm, pleased to meet you Senator."

When the Senator heard just the slightest masculine pitch to her soft voice he knew his initial speculation had been right, and his cock started to get chubby. It quickly swelled to about half mast, making the ridge of its crown clearly visible to Warden McQueen and Jeri.

Being that the senator was an exhibitionist in addition to being willing to sell his vote on legislation, he made no attempt to hide his arousal. In fact there was a hint of a smile at the corner of his lips when he saw Jeri staring at his cock before he asked her what she was in for.

When he did Warden McQueen smacked her lips and huffed. "Now Senator you know that's not polite," she chastised him. "I'm the only one who gets to talk about our patron's business."

By that point in their conversation the Senator had put his feet on either side of his lounge chair and sat up straight. His new position made his package even more visible in his banana hammock. He looked at Warden McQueen, then at Jeri to see if either one of them was looking at the print made by his pecker before he responded, "Barbara, dahlin you know the inmate code. We need to know what kinda criminal we have amongst us."

Warden McQueen fluttered her eyelashes at the Senator then shook her head while laughing. "Jeri, some of our residents think of themselves as convicts doing time in a high security prison, and that I'm an abusive warden."

At that point the Senator interrupted and corrected her, "Barb, how many times have I told you we're a hardcore group." The Senator then winked at Jeri before he said, "We're true to jailhouse rules around here."

Jeri smiled before taking one longer look at the Senator's cock before following Warden McQueen inside."

~

Moments later they were in Jeri's private room that was complete with a desk, a bookshelf, a 32 inch flat screen TV, and a reasonably comfortable bed. Her prison digs were more comfortable than her dorm room had been during her freshman year in college. She couldn't believe she was in prison.

As she was taking it all in Warden McQueen said to her, "I saw you staring at the Senator's cock.

Jeri's jaw dropped and her mouth opened when the warden said that. A lot of the things she'd seen and heard so far had surprised her, but she couldn't believe the warden was talking so openly to her about sex.

Warden McQueen grinned knowingly before she licked her lips and said, "Tell me, do you take cock up your ass?" She sounded so casual it was easy for Jeri to say yes. When she asked just as nonchalantly if Jeri sucked cock, the answer was yes she did. When Warden McQueen asked her if she swallowed cum, Jeri finally blushed, but she answered yes after hesitating for a couple of seconds.

After Jeri answered affirmatively, Warden McQueen continued, "In that case you'll fit in wonderfully.

At that point Jeri noticed the tenting of Warden McQueen's skirt and her eyes bugged out. She'd had no idea that the Warden had a cock. When Jeri looked up at her face the two of them looked deeply into each other's eyes. Without saying a word, Jeri dropped to her knees, reached underneath the Warden's skirt and pulled her panties off. She then held the Warden's big cock in her hand. "Sweet lord Barbara, you're hung like a pony," she exclaimed before putting the head of her cock into her mouth and sucking it with vigor.

Warden McQueen let her suck her peter until she was ready for some ass. She smiled big before saying, "Here hunni, put some of this lube on my cock then get naked and bend over the desk. I'm gonna fuck you in that big juicy ass of yours."

Warden McQueen plowed into Jeri's asshole with abandon for a couple of hot minutes before busting her nut inside Jeri's guts.

~

After their hookup in Jeri's bedroom, Warden McQueen called out for the other people who lived in the cabin to come into the living room. She looked in each person's direction as she introduced them. The female judge was in for real estate fraud. The Senator had sold his vote in Congress. The big manly football player nicknamed Bubba was spending his off-season cooling his heels for stock market insider trading. She then smiled big before saying, "Everyone, please welcome our newest member Jeri Hall to your group.

Jeri was nervous and excited as she looked around the room at the faces of the people who would be her housemates for the next few months. "Hello everybody," she said.

Warden McQueen then continued, "I ask everyone to think of themselves as members of a social club, rather than an inmate. We also don't assault our fellow patrons at any time." Then she paused giving her presentation, looked at the big professional football player and bit her bottom lip before licking them seductively and saying, "But some in our group are more dominant than others and they might have their way with you."

Warden McQueen then reminded them that it was up to each of them to make Jeri feel at home.

~

Jeri was awakened the next morning by a tap tap tap on her door, followed by Warden McQueen's voice saying, "Jeri, you better get up if you want some breakfast. The dining hall closes at 10 am. Then we're going shopping."

"Ok," responded Jeri. "Give me a few minutes." She then went into the bathroom, did her business, showered and got dressed.

~

Chapter 3.

As the weeks past Jeri's confidence rose to an all time high, and she was so excited to finally be free to be her authentic self she almost forgot she was in prison.

During the same weeks she adopted a long straight style for her dark hair to go along with her blue contact lenses and full lips. After getting on HRT, she developed a subtly curvy figure, and she finally looked like the woman who'd always been inside of her.

However, it was quickly apparent to her that the other transgender women at the facility had been chosen by Warden McQueen for their beauty. The fact was, every one of them could easily pass as a Cisgender woman. As a result the competition for cock was fierce and Jeri wasn't able to pull a man.

However the judge made it very obvious that she was definitely interested in getting to know Jeri intimately.

Then there was the grandfatherly Senator Kemp who'd been chasing after her since the jump. She would always smile and say something dismissive, or make a gesture with her hand to let him know she wasn't taking his flirting seriously, but secretly she was getting so horny till she was considering saying yes to the sexagenarian.

The Senator had suggested many times that she leave the door to her room unlocked at night, but she'd heard rumors that some of the people played the role of convict too literally. She still hadn't gotten past her fear of what would happen to her in a real prison, so she was about to say no again. But it was her third month at the facility, and she was horny as a goat, so she decided to take a chance and leave it unlocked with the hope of getting a good fucking."

~

Chapter 4.

Jeri gets more sex than she expected. Later that day the Senator sat beside her at the dinner table and greeted her, "Hello dahlin," he said before getting right to the point. "Are you going to leave your door unlocked tonight?"

Jeri smiled nervously as she responded, "Yeah I think I am. It's kinda scary though. The way some people look at me makes me nervous."

"You're pretty and the convicts like you," said the corrupt old Senator. "One of them could come into our cabin at anytime and take that tight little ass of yours, unless everybody thinks you're mine,"

Jeri giggled at the genteel old Senator's tough guy act, and politely declined. It was highly unlikely anyone would sneak into their cabin, but she didn't want him to cockblock her when she was around other people.

A short time later she was walking back to her cabin and past a couple of people. When one of them said they liked her ass, she smiled to herself but she ignored them and walked a little faster.

The rest of the evening passed peacefully and Jeri turned her TV off around midnight as she usually does. She soon drifted off to sleep, feeling both relieved and disappointed that nothing had happened to her.

She was awakened around 7 am by someone moaning and groaning and talking filthy. There was also screaming that sounded like it was coming from a female that she suspected was the lady judge's voice. Listening to the fucking got her so fired up till she took her modest sized cock into her hand and whacked off.
Things got a bit more interesting the next morning when the lady judge got into the shower with her. She looked to be around fifty give or take a couple of years, with a petite body, big titties, and a smallish triangle of dark hair between her legs.

Jeri tried to back away but the lady judge pinned her against the wall, then put her hands on either side of Jeri's face. "Good morning sweetie," said the lady judge in her usual authoritative way, while holding eye contact with her. "My my, don't you look cute," she added as her eyes scanned Jeri's body. "Hm, you have a cute little cock there. I have somewhere I want you to put it, but first I want to taste you."

Jeri was biting her bottom lip, and also breathing heavily from arousal. When she felt the lady judge begin to kiss her way down her body, she gasped. The lady judge stopped for a minute or three to suck her titties before working her way down low enough till she had to get on her knees.

She then held Jeri's cock in her hand and wrapped her fingers around it. "This little guy will do quite nicely for anal," she announced before putting all of it into her mouth. She then sucked it vigorously while also cupping Jeri's small nuts in her hand.

Even though Jeri beat-off only a short time ago, it had been months since anyone had touched her part that way, and she knew she couldn't last long considering how well the judge was sucking her cock.

Fortunately the lady judge had had plenty experience giving head, and she knew when to get off of Jeri's dick. "Hm, I think your she-cock is ready to bugger me," she said as she turned around, bent over and braced herself.

When Jeri looked down at the judge's backdoor she noticed that her pussy was gaping open. "Sweet lord Jesus, judge I can see your cervix," she said in disbelief. She knew that only a monster cock could have cause that kind of damage and she had to find out who had fucked her. "Who or what has been up in you?" she asked incredulously.

The lady judge looked over her shoulder and said, "It was Bubba. Girl, he's got a third leg down there.

"I love his cock and I love anal sex, but I can't take that thing of his up my ass. Barbara told me that your cock was perfect for ass fucking. That's why I came to see you."

"Now fuck me."

Topping wasn't Jeri's preferred way of sexing, but she was turned on by the lady judge's aggressive behavior, and after seeing evidence of the fucking that had been going on right there under her roof, she decided to make an exception and fuck her cute little pucker. She then positioned her she-cock at the entrance to the judge's backdoor and pushed her smallish peter into her well lube poop shoot to the hilt. Meanwhile the lady judge was playing with her own clitty as Jeri stroked her with a slow easy rhythm as she got closer to busting her nut. When the lady judge started whooping and hollering Jeri recognized her voice as the same one she'd heard that morning.

The shower was filled with the smell and sound of sex as they fucked in earnest for a few minutes before the lady judge got herself off, and Jeri shot her load into her asshole.

The lady judge then showered with her and thanked her before going to her own room. Jeri wasn't sure which one of them was the submissive.

~

Chapter 5.

Jeri finally becomes the Senator's Prison Bitch. Later that night the crooked old Senator came to her room while she was sleeping. She heard a light tap on her door, then a second later the Senator said "Jeri dahlin, are you sleeping?"

"No, I'm awake," she said while half asleep. It was pitch dark in the room until he opened the door. The Senator glanced at her with her head still lying on her pillow, and Jeri could see that he was naked and his cock was hard. He quickly closed the door then made his way to her bed and sat on its edge.

Without saying a word Jeri sat up, wrapped her upper body around his and took his cock into her mouth. It had been months since she'd been with a man and her thirst showed it.

The Senator hadn't expected her to attack his dick with such enthusiasm and he quickly found himself on the verge of coming. When Jeri felt his nuts tighten and his cock grow even more rigid, she sucked his dick so hard till her jaws sunk in and pushed him over the top. "God damn dahlin," he bellowed, apparently unconcerned that their cabin mates could hear him and would know who he was fucking. When he shot his load she swallowed every drop.

Jeri then laid her head on her pillow feeling very pleased with herself until the Senator said, "Turn over dahlin, the Senator wants some of your ladyboy-pussy.

Jeri frowned from surprise, then smiled at the fact that here was a sixty something year old man about to go a second time just minutes after busting a nut. She had been squirting lube into her sex on the nights that she left her door unlocked, just in case someone stopped by to fuck her, so there was no problem doing what he asked.

A moment later he was in her balls deep with his solidly average cock. The ridge around the crown of it that Jeri had seen through the Senator's Speedo the first day they met was doing a number on her prostate on every in and out stroke. Maybe it was because it was his second nut or maybe it was the pill he'd taken, regardless of the reason the older man put a good fucking on Jeri and made her cum from fucking her in the ass.

Once the Senator shared what he'd done with her with his friends, who were a CEO, a Hedge fund manager, and a Wall Street Banker, the flood gates opened. From that day until she got paroled, the Senator buggered her several times and his friends regularly asked her to give them head. The blowjobs didn't last long and there wasn't intimacy or passion, just the raw animal lust that Jeri desired.

~

As a result of the nurturing atmosphere at the facility, and the satisfying sex Jeri was getting, time seemed to fly. The months quickly turned into a year, and before she knew it, it was time for her to be released from Chateau Elegance.

By that time she'd become so completely passable, she had to show a couple of new inmates who hit on her that she actually had a cock before they believed her.

~

Chapter 6.

Jeri had just walked into the dining hall her last full day at Chateau Elegance when she saw both Warden McQueen and Bubba having breakfast together. Her asshole immediately started winking from the thought of being violated by him.

Warden McQueen greeted her warmly as she beckoned for her to sit with them. "Morning hunni," she said.

Jeri looked at her then looked at Bubba before saying, "Good morning Barbara, good morning Bubba."

Bubba greeted her by bobbing his head upward.

Warden McQueen smiled big, then said, "Tomorrow is your big day isn't it?"

Jeri grinned back at her then glanced at Bubba before responding, "Yes ma'am, I'll be a free woman in a little while." Then she got misty eyed before adding, "I can never thank you enough for everything you've done for me."

Warden McQueen looked at Bubba sensuously before looking back at Jeri and said, "Seeing the wonderful woman you've become is thanks enough. In fact I have something special for you. Actually I should say Bubba does, if you think your booty-hole can take all of his big delicious cock?"

Jeri gasped and covered her mouth before she started to blush.

"If you think you're up to it," Warden McQueen continued as she looked in Bubba's direction and bit her bottom lip again, "A certain Mr. Bubba Smyth will come see you tonight."

~

That was the conversation that led to Bubba sending Jeri back into the free world with a bang.

Now as she sat in the limo that was taking her home, she was a completely different person than she was on the day she entered Warden McQueen's office a year ago. Gone was the scared and confused fledgling transgender girl. In her place was a confident fully formed transgender woman.

She looked forward to a brighter future as a result of the time she'd spent at Chateau Elegance. The wealthy inmates she'd pleasured had showered her with monetary gifts, and as a result of the contacts she'd made she had her choice of firms to work for. There was even a possibility that Warden McQueen's husband would help her get involved in politics.