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The Road to Freedom The first thing you notice about the Okaloosa Correctional Institute is that, no matter where you are, it's a long way away. The desolation of interstate I-10 was overwhelming. Scrub trees and billboards. Every now and then, there was a gas station. But except for that, there was just highway. Lilly Newman had been driving for two days now. She had traveled from her home in Fort Lauderdale to Tallahassee yesterday, and she was up early to travel the rest of the way to Crestview. Frankly, she resented having to make the trip, but evidently she was still the outside contact for her ex-husband Michael, who was getting out today after seven years inside. Lilly couldn't wait to unload on him. The bastard had screwed up her life by going to prison. He deserved what he got. Most of those had been at Mule Creek in California, but there was no way she could get to California on a secretary's salary. So those who run things at Mule Creek had transferred Michael to Okaloosa. That a way she could pick him up. What to do with him then? She had no idea. They had been divorced since his third year inside, but she hadn't seen him since the courts found him guilty of stealing the car, which had drugs in the glove compartment and a loaded pistol in the trunk. Michael swore he didn't know about the drugs or the gun, but they found him guilty, and they hauled him away from freedom and away from Lilly's life. She wasn't trying to be a snob. Hell, her father had done time. But California was just too far away, and she had a life. So they drifted apart, and eventually, she got a divorce notice in the mail. These days, she rarely thought about him except as a mistake of her past. But the phone call came a week ago. Michael was getting out. He needed to be picked up. She couldn't find his brother. His folks had long since moved away. She was still listed as a contact. So Lilly headed north. And then west. Now, she was looking fo exit 59. From there, it was just a few miles to the prison. All prisons look ominous. Okaloosa wasn't Angola, and it wasn't Folsom. But it did look threatening. Barbed wire. Guard towers. Badges everywhere. Guns, Lilly parked in visitor's parking and walked to the check-in stand. There, they x-rayed her purse. And a female guard escorted her to the warden's office. It looked more like an office building, to tell the truth. The Warden, Jimbo Matthews, stood and shook her hand. She exchanged pleasantries. He offered her coffee. She declined. "Mrs. Jenson," he said. "I appreciate you coming to collect Mal ... Michael. He's been a good prisoner. No violence, no trouble. We think he'll do okay in the world." "I understand," Lilly said. "What I don't understand is why I had to come get him. Why not just put him on a bus? I mean, we aren't together anymore." Matthews paused, something on his mind. Then he said this: "Mrs. Jenson, have you heard about the Joyce Newberry Program at Mule Creek?" "No. Should I have?" "Mrs. Jenson ... let me talk frankly to you. In 2012, Mule Creek set a prison record for rapes. Male on male inmate rapes. Joyce Newberry was a warden then at Chino, and she decided there would be a lot less violence if we could change a few things. Same sex marriage is legal know, as you know. The Joyce Newberry Program not only lets inmates marry, it lets one of them start the process of transgenderism." "I don't understand," Lilly said. "Mrs. Jenson, your husband signed up for the program. He got married . to another inmate... He has a husband. He's presenting as a woman named Mallory these days. Because of that, we like to have them picked up by people they know. Lilly almost burst into laughter. Michael? As a woman? She imagined how comical he would look. She had met Michael in high school, and they had fumbled around in his Buick by the lake a time or two.For crying out loud, he was her husband. Michael had a lot of flaws, but he was certainly masculine enough. No question about that. They were married right out of high school. He was going to be a lawyer. But he drank a bit, and one night, he hopped in a car that wasn't his. The door opened, and a matronly woman with red hair stepped in first. A parole officer, perhaps. Two guards entered. And then a blonde woman who shuffled her feet. She walked with her head bowed on black high heels. She had on a black patterned dress. Her makeup was good. . She looked up, and her eyes flashed in recognition. Lilly's hand went to her mouth. "...Michael?" she said. "It's Mallory now," the response came. * * Lilly drove in silence for the longest time, not know what to say to this woman who sat beside her. Lilly glanced at her. Her made-up was good. She sat like a woman with her hands in her lap. Her hair looked as if she had come straight from the salon. She had a gold band on her ring finger and chandelier earrings. She wore a small woman's wristwatch. Her boobs looked real enough. "It's good to see you, Michael..Mallory," she finally said. She kept her voice small, pleasant. "Is it?" Mallory said. "I imagine it's a little shocking to see me like this." "That's true. They didn't give me any warning. I didn't know." "It doesn't matter," Mallory said. "What's done is done." "Mallory? Can I ask some questions? Not to pry...just to understand." "Of course, Lilly. You were my wife, remember. You're allowed questions." Mallory laughed softly, as if the idea of having a wife was preposterous. "When did you ... change? I mean, you look good. Don't get me wrong. But how did this all come about?" Mallory shrugged. "It wasn't long after I went inside," she said. "I mean, I was taken ... what was it...my third night there. Raped, I guess, although it was kind of a seduction. And I gradually became his sissy, then his woman, then his wife. Remember when you got the divorce papers. that was so Bobby and I could get married. There was this prison reform bill that allowed dit.." "You were ... raped?" Lilly said. "God, I'm so sorry." "You couldn't be there," Mallory said. "Prison rape happens every day. The prisoners surround the newbies and pick them off, one by one. You have to be pretty tough to fight it off. I wasn't." "When, um, when did you get a sex change?" Lilly said. "Can I ask that?" Mallory smiled. "I didn't get a sex change, Lilly," she said. "I mean, not a complete one. I still have my ... thing. They'll approve that kind of operation at Mule Creek, but then you're a woman, and you have to go to the women's prison. I wanted to stay with Bobby. So I shot myself full of hormones, and I started wearing women's clothes. Bobcat is my man, Lilly. I love him." "Bobcat?" "Just my nickname for him. He's very good in bed." "Oh." They drove quietly for a while. Lilly was trying to absorb everything Mallory had told her. She didn't know much about women becoming men. But she knew from the news that it happened. "Mallory, do you consider yourself gay?" "Labels, huh," Mallory said. "Some would say I'm gay. My partner and I both have cocks. But I think of myself as female. I know I haven't earned the respect due truly gay people. They've taken so much crap. But I like the sex. I grew to love giving oral sex. Or having anal sex. It's good." Lilly considered his words. She was quiet. Finally, she asked another question: "What now, Mallory?" "You mean with my gender? I assume I stay female. I've been a woman for a long time, Lilly. I like it. I'll get a job as a waitress or something. Hope that Bobby gets out soon so we can be together." "You're going to wait for Bobby?" Lilly asked. "I have to," Mallory said. "I have his name tattooed on my ass." Mallory laughed softly, the first time she had laughed all day. * * It was 2012 when Michael Jenson rode on a blue bus through the gates of Mule Creek. It was hot, and you didn't have to try very hard to smell what life was going to be like. It was sweat and oil and dust. Michael was photographed -- again -- and had his fingerprints taken -- again. He was hosed down. Mule Creek was bigger than he thought, a two-story prison with inmates assigned two to a cell. Cold. Hard. It smelled of antiseptic, Some prisons have gone to dormitory style bunks, but not Mule Creek. Prisoners were in a small cell, locked away from decent people. Throughout his trial, Michael had been warned of rapists. But no one messed with him that first day. Or the second one. He felt claustrophobic in the cell, two by two, and his cot smelled like someone else's sweat. His cellmate was Bobby Mason, from Arkansas. Across the wing for those two nights, Michael could hear the cries of the weak as they were plucked from their worlds by other inmates. There was screaming, and weeping, and moaning in pain. It felt sick and lonely and helpless and depraved. "Why don't the guards do anything?" Michael wondered aloud. "Guards are doing something," Bobby said. "They're laughing their asses off. Guards like the noise of fresh meat being broken in." "Well, I'm glad you're not like that," Michael said. Bobby grinned. "Maybe I am like that," he said. "Don't assume. But some people like rape, and some of us wait and use seduction. Some of us let you get used to the idea. It makes the sex better." Michael looked at Bobby, who shrugged and smiled. "You're going to ..." Michael said. "I am, chicken," Bobby said. "Just not yet." Michael slumped down on the floor. He didn't want to cry. But there was no hope for him at Mule Creek. Bobby was 6-2, about 220. He had no chance of defending himself. "Sweetheart," Bobby said. "It's how prison works. If you have a good man, he'll keep the other inmates off of your ass. He'll take care of you. He'll be your bull. And there is some comfort to be found in the sex. It isn't all just primal need. It's survival." Michael crawled into his cot and faced the wall. Sleep did not come. He thought about his future. Worse, he accepted it. The next morning, when Bobby woke, the first thing he saw was Michael's face. It was the face of the hunted, and his eyes were red and wounded. As Michael kneeled beside of the bed, it was the look of acceptance. Of surrender. Bobby nodded. He shifted in his bed until his back was against the wall. He spread his legs. His large sick stuck through his pants. Michael sighed. He leaned forward and rubbed Bobby's hardening cock against one cheek, then another. He kissed the tip lightly. He licked down the shaft, then up it, then swirled his tongue on the bulb. He gripped it with his right hand, then wrapped his lips around the knob. He sucked gently, then harder, yo-yoing his face up and down. This was his life now. He was a cocksucker, and no one had to hit him to make him one. He felt lust and shame and submission. When Bobby came, it was like most things in his short life. It was violent. Ribbons of come shot into Michael's mouth, and on his face. He stayed so hard that Michael thought he was going to come again, but he didn't. Finally, he softened, and he reached out and touched Michael's head. It was a tender movement, and in a moment of self-loathing, Michael appreciated it. "Good girl," Bobby said. "Good girl." * * They spent the night in Tallahassee, at a Courtyard, sleeping in twin beds in the same room. Lilly noticed that Mallory wore a nightgown to bed. It accented her breasts. She watched as Mallory removed her makeup. Lilly slept in a t-shirt and shorts. Throughout their stay, Mallory told her that it took her more than a year to grow her boobs. She was proud of them. She told her she had been with three men while on the inside. An inmate that Bobby had loaned her to, a guard forced her while she was doing laundry, and Bobby. She told her how much she grew to love heels. Bobby had hurt a guy on the outside, she said. He was in a bar, and an off-duty cop was trying to bully him, and Bobby had broken his jaw in three places. He was already on probation, and his lawyer was for shit, So he pulled a 10-year sentence. A couple of years were added on when he had fight in the yard, but he hoped to get those expunged. There was a lesson here, Lilly thought. The wrong place, the wrong time, the wrong circumstance, and we could all go down, Michael stole the wrong car. Bobby hit the wrong cop. Some people get the wrong lawyer, or the wrong judge. Knowing what she knew about the system, some people were simply the wrong color. Mallory came out of the rest room, and she was wearing a simple blue sundress, cheap but clean. She looked fresh. Lilly imagined that sleeping on the outside was nicer. "Mallory," Lilly said. "Did you have any ...tendencies when you were young. Did you wear dresses." Mallory laughed. "You want to know if I was transgender? Or a cross- dresser? No, I really wasn't. I might have been if I knew how good it felt, though. Bobby always said it's just cloth, you know? In the early days, I used to dream about wearing guy's clothes again. But even before reform, guards looked the other way when an inmate wore a dress. No one said a word." "Okay. Were you ever gay?" Mallory shook her head. "That would be easy for the word to understand, wouldn't it? There would be no forced sex with men if you wanted men. But I didn't. Not then. Look, I surrendered quickly. Maybe too quickly. But gay wasn't my nature. If I had never gone inside, I never would have, well, sucked a cock. But prison changes you, and it changes everyone around you. You become a animal trying to see one more sunrise. Even after you get used to it, even after you start to enjoy it, you know what the system has done to you." "Mallory, do you miss him?" Mallory looked out the window. She smiled. "Oh, yes," Mallory said. "Bobby was sweet to me. He was gentle. If I had a choice of release or staying inside with Bobby, I would have stayed. After all, it was Bobby who put the hard in hard time." * * That first morning was sweet for Michael and Bobby. She had sucked him off, and they lay intertwined on his cot. Every now and then a guard would look in the cell, see what was happening, and keep walking. You didn't mess with a man who was getting pussy, even if it was ass pussy. "Michael," Bobby said softly. "Yes?" "Michael, I'm not gay. That's important for you to know. I believe in sex between a man and a woman." "Yeah, me, too." "Michael, listen to me. There are sissies in this prison. I mean, real honest-to-god sissies. You couldn't tell the difference between them and biological women. Well, in this cell, you're the sissy. The woman. I'm the man. I expect you to be fully feminine as long as the guards look the other way. Panties. Dresses. Lipstick. Can you do that?" Michael looked at Bobby. He had already performed gay sex on him. What was wearing a dress? He swallowed hard. "Do I have to?" he asked. "You have to. You have to be pretty for me. All the time." Michael felt his stomach flip. He had most of his seance ahead of him. He was evidently going to spend it as a female. Michael had to work in the laundry later that day, but before he reported, Bobby sent him down the Cell Block to meeting with Big Anthony and Rachel, his bitch. Rachel, of course, was male by birth, too. But she was with Anthony and, as such, she was the Queen Bee of Mule Creek. Rachel ran the girls of the prison, the guys who wore makeup and dresses and high heels. There were a couple of hundred of them, even in those days, birdies who found love and protection in a same-sex relationship.No, the prisoners weren't gay. Not technically. But people couple for their emotional needs when they're locked away. Two guys on a deserted island? Sooner or later, they're going to sleep together. That's just the way it is. Two men in an iron cell. Them, too. Rachel was Hispanic. She had olive skin and a big rear end, and she like to wear long blond wigs. No on ever saw her without makeup. It was Rachel who organized a sissy inmate beauty contest. A singing competition. A dance off. She fixed up this stud with that sissy. She ran the beauty salon. She dispensed hormone pills. She ran things. Mallory admired her greatly. That day, Michael showed up and told Rachel that Bobby wanted her to take care of him. Rachel smiled and nodded her head. She knew. Rachel got her a red dress and a black one, four pair of panties, three bras, and three pair of hose, a set of heels and a makeup kit. Michael would get more stuff in the weeks to come, she was told. She took the clothes back to her own cell. A guard walked by and looked and laughed. "I knew you would be one, sissy boy," he said. "I can tell which ones of you will open your mouths and swallow." Bobby glared at the guard. Michael just looked at the floor. Just like that, he was a sissy. * * It was late in the day when Lilly and Mallory arrived in Fort Lauderdale. Lilly left I-95 and drove past the beach. She figured Mallory would want to see it. They talked. Lilly had dated three men and one woman seriously in the seven years Michael was gone. The longest was Lenny, an attorney. They had gone out for four years, and at one point, they had talked about getting married. But it turns out that Lenny was already married, so that went up in smoke. They talked about sex, as two women often will. Mallory said that Bobby was very well equipped, although that wasn't good at first. Lilly talked about dating Miriam because she was fed up with men, but she wound up having a sweet relationship. And Miriam could do more with a dick than any man she had dated, even if it was a rubber one. Lilly then paused and said ... "well...any man but you." Lilly said that now she was dating a vibrator she nicked "Thor" after the guy in the movies. They were very much in love. They laughed. Two girls on a road trip. It was nice. Funny, Lilly said. On the other side of the clothes and the makeup and the female mannerisms, they got along better than they ever had. Lilly decide that she liked Mallory better as a woman than she had liked Michael. He was softer. Sweeter. "Mallory," Lilly said, "I know you'll have to look for an apartment, but why not say with me for a while? There is a lot of crowding in South Florida. Just take your time and look around." "Why are you being so nice to me?" Mallory said. "When I was with you I was a bad guy. I stole a car." "We all grow up, Mallory," Lilly said. "You've been jailed for years. But, maybe, before that, you were jailed by being a man. Maybe you were supposed to be female all the time." Mallory shrugged. She looked outside the window, where young men were throwing a Frisbee on the beach. A scruffy guy with blonde hair made a nice catch. "Don't tell Bobby," she said, joking. "But I might take that one home." * * Two. years after Michael went to prison, so did his dick. As it turned out, some sissy named Sammie was cell mans with Joshua, a man from Fresno. Well, Sammie had a wandering eye, and she ended up having an affair with another inmate named Donna. Sissy sex. Well, Joshua went after Jamie, Donna's boyfriend, and all hell broke lose. There was tear gas and solitary and someone got stabbed. The warden was pissed, and he threatened to stop all of the sissy activities which, in turn, had all of the inmates irate. Their relationships were about the only thing that the system hadn't stripped away. Finally, a delegation of prisoners met with the warden and promised the violence would stop. They promised they would control their women -- or their pseudo- women -- better. They would bring peace. The next day, the sissies were gathered in the gymnasium. One by one, they were handed chastity belts. If a sissy couldn't make love with another sissy, then what was the point. A bull prisoner still could stray on his sissy, but wasn't that like free society. So Michael was caged ... again. And she hated it. It felt big and bulky -- it was neither. It felt like someone had attached a computer mouse to his dick. The truth was, of course, that most sissies didn't use their dicks anyway. Certainly not often. The illegal estrogen that flowed through the prison prohibited that. But just because you don't use a lawnmower doesn't mean you want to take it away. Every cell block elected their own key holder, and peace was restored. "It's cute," Bobby said, playing with the lock. "I kind of like it. It's a symbol that I'm the one in charge around here." And he was. No one messed with the Bobcat. He was the best fighter on the block. If you went after Bobby, you better pack a lunch. One day, an inmate named Blade thought he could earn a rep by going after Bobby. He jumped him from behind, and he had two guys with him. I screamed and tried to pull one of them off, but he backhanded me across the room. And then there was a blur, and one of the creeps was gone. Another inmate, Jefferson Parker, didn't like three guys jumping Bobby, and he helped out. They were still outnumbered, but Blade had no chance. He went down hard. Of course, Bobby was called up on charges -- again -- and he went into the hole for four weeks. But before he left, he pulled me aside. He kissed me. Then he looked me in the eye and said "you take care of Jefferson, and he'll take care of you while I'm in the hole," he said. "You can have sex if he wants it. Treat him like he was me. That's the rule of the yard." "No, Bobby," Mallory said. "I won't cheat on you." "It isn't cheating if I'm not there," Bobby said. "I could die in the hole, and you'll need protection. Hell, we both know you'll get out before me. It's okay if you play around, at least until I'm out. I'm not jealous...much." The guards took Bobby away then. Jefferson stood beside Mallory, and his big black hand fell on her shoulder. "We don't have to do nothing," Jefferson said. "Bobby's a good guy. I'll look out for you either way." Mallory looked at Jefferson. She stood on her tiptoes and kissed him. "Thank you for helping him," she said. That night, in the laundry, Jefferson came to see her. He touched her hand, and she looked down to the floor. He kissed her for the second time. "Okay," he said. There was honor to Jefferson. He had saved her man, and he had no demands on her. But Mallory knew she had to be honorable too. She touched his cock through his pants. He rubbed her growing breasts. Mallory started to kneel, but he shook his head. He spun her, and he bent her over. He tugged down her panties. Oh, she had had anal sex before. Bobby liked it a lot. But Jefferson was bigger, and he hurt more. But when he found his rhythm, it was glorious. He fucked her for almost an hour, pumping in and out, sliding his skin into her hole. He came with a primal grunt, and she thought he would never stop. Word had it that Bobby was still a target, and Mallory with him. But Jefferson was there. No one ever touched her. * * By the time Bobby got out, the prison reforms had begun. Marriage was now legal among inmates. Sissies could live openly. Mallory continued to work in the laundry, and one night, Tom Haller, a guard, walked into the room. Testosterone Tom, they called him. He didn't say a word. He simply walked up to her and dropped his trousers. "I could use a little attention," he said. Mallory looked for a place to run. There wasn't one. She looked for something to hit him with, but he grabbed her wrist and forced her to her knees. He raped her orally, sticking his dick into into her mouth, manhandling her skull until he got his way. She bit him, and he punched her. "Try that again, bitch, and I'll turn you off." He started forward again, and suddenly, the air in the room changed. Bobby had come into the room, and Jefferson with him. Rachel had seen Tom enter the room, and she smelled trouble, and she ran to get Bobby. Tom stood up and straightened his pants. "You boys better back off," he said with the self-assurance of a guard. "Or?" Bobby said. "Hey, I was just having fun with the sissy. Isn't that why God invented sissies?" Bobby hit him -- one time -- and he fell like a sack of onions. Jefferson stepped on his neck and said "I don't think I'd move if I was you." When Jefferson lifted his foot, Tom scurried away. Coward. Bobby took Mallory home -- if you can call a cell home. He put his arm around her and he rocked her for most of the night. She couldn't stop crying. She couldn't stop apologizing for Tom's dick being in her mouth. "Hush, baby," Bobby said. "You're a mouse in a cage full of snakes. It's not your fault." Mallory holding him. "You wanna get married?" Bobby said in a whisper. "What?" "To me," Bobby said. "I think we could get married. Jefferson would be our best man. Rachel would be your maid of honor. We get three days off work. I've been illegal for a long time. IT would be great if our relationship was legal." Mallory looked at him. She wasn't crying anymore. "So what about it, Mallory?" he said. "You want to be my wife?" "Yes," She said said. "YES." That's when Mallory sent her letter to Lilly and asked for her divorce. She and Bobby were married on a Sunday. Rachel found her a proper wedding dress. Even Jefferson cried. * * Mallory could not get over Lilly's wardrobe. There were red dresses and green ones, blue ones and white ones, yellow ones and black ones. There were sundresses and skirts. So many dresses. To Mallory, it was the splendid wardrobe in the history of clothes. Mallory and Lilly were roommates now, at least temporarily. Mallory found a job waiting tables, and then a better job, working for a property rental firm. No one asked about her gender, and she wasn't going to lift her skirt to show them. "Lilly, were you angry with me when I want to prison?" Mallory asked one evening as they sat on a seawall, watching the waves of the Atlantic Ocean lap the sand. "That doesn't matter now, Mallory," Lilly said. "We're friends. I like you better as Mallory." "I like you, too. But just for the record, how did you feel about Mike? The arrest? The trial? The friends? The prison?" Lilly was quiet for a moment. She watched a seabird dive for a fish. Finally, she exhaled and began to speak carefully. "Mallory, I was pissed," she said. "I won't lie to you. You ripped my life apart with that stupid stunt. I was a married woman, and then I wasn't. The neighbors knew you were in jail. Your family stopped calling me. "Hell, Mallory, we were going to have a family. We were going to be normal. Then you have a number instead of a name. It tore me up. It would tear anyone up. And now I look at you, and you're so beautiful, and your tits are bigger than mine. Sure, it hurts. But I've learned a lot about you, and I like Mallory. She's a good woman. I'm glad to be her friend. But yeah, it was hard." There were tears in Mallory's eyes. How could she -- he -- have been so thoughtless. "I'll leave," she said softly. "No, don't," Lilly said. "It's important we get this out in the open. But I don't want you to go. I don't want you to leave me again." Mallory reached out and grasped her hand. Lilly opened her arms and they were hugging and crying and talking all at once. They had become Thelma and Louise, or Betty and Wilma, or Ginger and Marianne. Lilly looked her former husband in the eye and, without thinking about it, leaning in and kissed her. It was soft, and it was sweet, and it was right on the lips. Mallory pulled away. "Bobby..." she said. "I was here before Bobby," Lilly said. She kissed Mallory again, and she touched her breasts. Mallory stroked her cheek. Lilly took her by the hand, and they drove home in silence. Once they reached the apartment, Mallory looked at her again. "We shouldn't..." she said. "We should," Lilly said. "You're free. After our conversation, I'm kind of free, too. Bobby would understand. He said you could play. Lilly kissed her for the third time, and all of Mallory's resolve disappeared. They were tearing at each other's clothing, and they were trying to kiss every inch of each other's bodies. Mallory tasted Lilly -- the first vagina she had touched in seven years -- and found it wonderful. Lilly kissed Mallory's penis and found it, well, useless. They took turns with Thor the vibrator afterward. Lilly pegged Mallory in her ass. Mallory used it for vaginal sex. It was great both times. They lay together afterward. There were unanswered questions, as they are in life. What happened if Bobby got out? Lilly said he could live with us in a poly relationship, but would he want that? What about Lilly and other men? But the answers would come tomorrow. For the moment, they were together, and the lost time had been found. Copyright, Cassandra Morgan