John’s life as a female inmate

John’s life over the next few weeks was fairly static. His aerobic workouts increased in intensity. His weight dropped and his legs became toned. His stomach flattened. His ass become rounded... perky.

Heidi was released. The rumor mill said the computer gagged her with a ball gag, clipped a patronizer on her, trussed her up like a turkey, and shipped her off in a wooden crate. John honestly felt sad for her. If the prison had turned her into a mean girl, then the prison was to blame for his entrapment in the bridal pool. Still, he wasn’t sad to see her go. Her sudden removal left a power vacuum. John just wanted to stay clear of whoever rose to power with Heidi gone.

He experienced his first week of wearing a pad in his panties during “menstruation.” That was awkward for John. It felt like he was wearing a diaper and crossing his legs was always an awkward reminder that he was somewhat experiencing something most men never do.

He graduated to 5 inch heels with a platform. It took a short time to master those. John reluctantly realized he was wishing for 3 inch heels and was startled to realize he was wishing for heels at all.

One morning as he and Holly were awaiting their daily clothes presentation, John realized things were changing. “My nipples itch.” He said to Holly.

She smiled. “Looks like the boobie fairy may have visited you, Joanie. I bet now that your hormones are balanced your boobs will probably start to develop like they should have.

“Either that or you’re pregnant,” she said with a laugh.

John cringed. He definitely did not want breasts. As if listening in on the conversation, John’s clothing pile that day included a purple satin thong and matching push up bra. Apparently the computer knew his favorite color.

“Oooo!” Holly teased, “Big girl undies! Looks like you’ll be joining Lisa and me soon!”

Within a few days, John was consistently wearing very sexy lingerie under his jumpsuit and joining the other women in general training. He was showering in the communal shower with Lisa and Holly. He received several painful shocks for arousal the first several times doing so when he saw Lisa showering. He learned to not look at the women he was showering with. He hated associating the sexy women around him with painful shocks. He truly was being converted.

After showering, the women congregated in a large many-vanity-filled room to do their makeup. He was assigned a station and had to apply his own makeup. It was inspected upon completion and after several powerful shocks, John learned how to apply it perfectly. The computer selected a particular look for that day, and the ladies had to apply their makeup in that manner. John’s hair was now down to his shoulder blades and typically styled in soft waves that screamed “bed head.” Looking in the mirror was still unsettling for John, as he was now definitely a woman he would have hit on outside of prison.

A few days after starting to wear very decidedly “attractive to men when worn by women” underwear, John was directed to report for new training. This worried him as it was simply described as “compliance training.” None of his friends would tell him what to expect.

As in the past, he stepped through the door he was instructed to enter into a small antechamber. There, he was instructed to disrobe. After feeding his soiled clothing down the chute as usual, new clothing appeared. A lacy black bustier that pushed his budding breasts up, black stockings, and an almost non-existent black g-string. John did not like the looks of this.

He was instructed to sit as his heels were removed. By now, it felt weird for John to be without heels on. He hesitated a bit too long before donning the presented lingerie and was punished for it. He was soon in the lingerie, and maribou pumps were attached to his feet. A mirror descended. He looked at himself. He looked attractive. Hot. He looked like he was ready for sex. The wrong kind of sex. Sex with a man.

The mirror changed to a video screen. An attractive woman with a British accent filled the screen. “As a straight woman, you will learn that it is your duty to accommodate your man’s every desire. For instance,” the video vanished and the surface reverted to a mirror, “You have been attired in such a fashion that a man would find you desirable.”

John did not like where this was going.

The video of the woman returned. “And if your man wanted to you in lingerie such as this, you would comply.

“In fact, it is your duty to do as your man desires, no matter what he desires.

“Please stand on the marked spots on the floor.”

John hesitated and received a strong shock.

“Please stand on the marked spots on the floor,” the British woman repeated.

John tentatively walked over, his heels coming to rest on the yellow footprints painted on the floor. Clamps locked john’s heeled feet in place. A padded beam rose from the floor and stopped at about waist height. An arm began pushing on the back of John’s neck, forcing him to bend at the waist over the bar. The arm on his neck remained, but something wrapped around his hair and pulled backwards, forcing John to look straight ahead into the mirror while bent at the waist.

“If your man decided that he wanted you attired as such and wanted to have sex, you would do so.” John began to struggle. His hair was pulled back tighter and he was shocked multiple times. “Although your vagina is covered by a chastity plate, it will not always be so. Until then, you will learn that there are other ways to sexually satisfy your man, such as when your menstrual cycle is upon you.

“Just remember, stay relaxed, do not fight your husband, boyfriend, dominant... whoever you serve. It is about his pleasure, not yours, although you can learn to enjoy it.” The woman winked and the screen returned to a mirror.

A mannequin had been placed in position behind John, and he knew what was in store. He felt his g-string being pulled to the side and lubricant being applied. He struggled mightily, earning him a shock. The mannequin was male, VERY male, and on rollers of some sort. John could see it approach him, its mechanical arms locking into his hips. He felt it making several teasing thrusts. Eventually came what John dreaded. The mannequin plunged deep into his ass. The pain was intense. The mirror that John was being **** to look at changed to videos of muscular, naked men.

John was crying out in pain as the mannequin fucked him. He didn’t want to see the naked men, but if he closed his eyes, he was shocked. After what seemed like an eternity, the pain subsided and John began to feel a tickle. A... spot. God, that spot. When the mannequin hit that one spot...

He realized what was happening. He tried to resist it. But it wasn’t long before he was moaning with desire. He hadn’t had in orgasm in weeks. He was so horny.

Suddenly liquid was dripping out of his plate onto his g-string as he had an orgasm. He was panting, hating himself for what happened. Feeling disgusted with himself. And the mannequin pumped several more times before John felt something squirt into him. The mannequin slowly stopped pumping, then pulled out of John’s ass with an audible pop.

John waited to be released, but it didn’t happen. The British woman appeared again. “That wasn’t so bad, was it? But as a woman, there are also other ways to pleasure a man.”

The mirror raised up out of sight, and another mannequin, very male, with an erect cock and pubic hair, rolled towards his face. John tried to turn away, but his hair was still held tight. Again, several testing thrusts, and John soon found the cock in his mouth. “Oral pleasure of your man is a skill you should be proud of,” he heard the British woman’s voice. “You will be timed to see how long it takes for you to bring the practice subject to orgasm. You sill be punished for using teeth, causing it discomfort, or taking too long.”

The mannequins hands clamped onto the side of John’s head. The mannequin began pumping into John’s mouth. John tried to cry out, but the mannequin’s cock drove into the back of his throat. John quickly learned that if he kept his lips in place, he could control the depth of the mannequin’s thrusts.

“Don’t be afraid to use your hands,” the woman said. “Some men enjoy having their balls played with.” John couldn’t do that. He accepted the pounding, but just sat there, not doing anything. The mannequin eventually squirted a salty viscous liquid into his mouth and kept john’s mouth plugged until he swallowed it.

“A woman never lets her man’s semen go to waste,” the British woman said. “You will always swallow your man’s semen.”

John sighed. There was semen dripping down his leg. His ass was leaking. He waited to be released.

Instead, the mannequin behind him returned. The mirror came back down showing naked men, the hands clamped onto his hips, and he was soon being fucked again. It took longer for him to orgasm this time.

He was then giving a blowjob to the other mannequin again. This time, he was getting shocked if he didn’t actively participate. He was instructed to use his tongue, move his hand up and down the shaft. Each time, he was learning how to better please the machine. Each time, he had to make the mannequin orgasm in shorter and shorter periods of time. And each time, he was **** to swallow.

The anal/oral training continued, and each time, each cycle, John’s psyche was damaged a little more. What was he doing? He’d done it before.... Why not give in? He’d already had an orgasm. Why not just accept it?

Eventually, he was released. He stumbled a few steps in his heels, was corrected, and then sexily strode into the next room, where he disrobed and showered. His itchy nipples really were bothering him. They were sore, and his nipples were always sticking out now. After cleaning himself off, and for once it was just nice to clean out his chastity plate with warm pulsating water, he put on his new lingerie and jumpsuit, and his heels were locked back on. He redid his makeup and was released to lunch.

John found the amount of “semen” that he had been **** to swallow had really diminished his appetite. When he saw his friends, he glared. “Why didn’t you warn me?” He said angrily.

Anna smiled a sad smile and gave him a gentle side hug from her seat next to him. “If we had warned you, Joanie, you would have been terrified for your first time. You faced it. You know what to expect. And you can do it now, knowing that you did it before.”

John grumbled, but he knew the girls were right. If he had known, it would have been worse.

Then there was aerobics, main room time, and grace training.

This became John’s life for the next several sleep cycles. Sometimes he would be dressed in sexy lingerie for compliance training. Sometimes he wore tight little dresses. Other times he just was naked except for his heels. It was just humiliating to John. But like everything else in the prison, there wasn’t anything he could do to stop his conversion. He was beginning to associate orgasms with naked men. With being penetrated.

One day, after awakening, John and Holly’s clothes for the day were disposable blue hospital gowns.

“Yay,” Holly said dryly. “Pelvic exam day.”

John almost cried with happiness. He had endured the compliance training. He had endured his itchy nipples. He had endured the makeup, the hair, the hormones, the birth control. He had even endured that morning’s enema.

Today was the day he’d be getting out of this nightmare.