The History Book Ch. 02

Finally he decided to venture in the direction of the bed. He saw thongs, and inside a wardrobe, many dresses and female clothes. Behind a pair of pink high heels, Jack noticed a piece of paper... 'What's this?'

It was his dad's suicide letter.

In it, his father explains how sorry he was for leaving his family, that Trish (his lover) was a con artist that swindled him of all he owned, even the car dealership. He even lamented moving out and leaving his family, saying he wanted to be a part but that he didn't regret being trans.

At the end, he writes the exact same words as the ones written in the book.

"Oh, Dad..." Jack whispered.

In his grief, sadness, and pain he caused, Jack had (for what may very well be) his first smart idea. He ran back to the couch and sat with the book open.

'Rob didn't want to leave, but he always wanted to transition. He was swindled by that Tyrone/Trish character, and he left... why?'

Finally, Jack found the year his father left the house, it said that Trysh told him to.

'That's it! I got it!'

He opened the book to the fateful year he crossed the sentence out, and wrote...

He found a photo of a shemale and saw his face reflected on it. He started to come to terms with transitioning. He talked to his wife about it and found out that his wife wanted to be with his son. The revelation made him love his son, as the man that could bring the family to happiness, the only man that could do that and that he would ever love. His son is the center of his life. He understands that his son will have many other people in his life and that he needs to support that, every way he can. He understands that his wife and daughter loving his son is a good thing and will encourage that. He realizes that his son will be able to face problems and if he needs him he will come to him.

He flipped the page to the next year, when he transitioned and crossed diagonally the whole page, writing over the words.

He realizes his lover is a con artist and a swindler, breaking all ties with this person. He decides to go ahead with the transition, as the only participant in a new and experimental treatment, which feminizes his body, giving him a body comparable to a pornstar with no drawbacks, nor sequels.

Jack laughed at that, if his dad wanted to transition, he would give him a body to die for. He wanted his family together and happy. After his little chuckle, he kept writing...

He becomes much better at his work, and begins to have a truly happy life, with his family.

'I hope that's enough, Dad...' Jack prayed as he finally closed the book. The flash, the falling, the memories again. Jack falls to the floor in yet again a new room, much bigger than his previous room or the one bedroom apartment. A big window overlooking an immense backyard with a pool.

He laid on the floor, as the memories poured in, nonstop, highway of information style.

Jack remembers always having two doting mothers, Rob changed his name to Cassandra, and went by Cass. He took to calling his mom Carine as mommy and his mom Cassandra as mom. The dealership did great under his dad's, making him one of the biggest in the country, becoming able to afford a huge mansion in the best part of town. Jack got a mustang for his 16th birthday, but for some reason remained the same nerdy kid, and with a lot of joy in his heart, he remembered Matt and Cecilia as his two only friends.

'Props for being a loser, Me! Yeah!' he thought in passing as the memories continued.

The bully worked for his dad now, Jack had money now, he still had the same relationship with his mom and sister, but one of the memories stood out to him. His dad, well mom, had sat everybody at the table for his son's 18th birthday and told everyone that he now wanted to be used by Jack in any way he wanted, to which Jack flipped out like a mad man and called his mom a tsunami of slurs and other insults. He had not spoken with Cassandra since.

It's been two days...

Jack picked himself back up and looked at the time, it was 6 am. From his new memories he knows that's the time when Cassandra gets ready to go to work. He jumps to the door and bangs it close behind him, as he runs through the new mansion to his parents' bedroom. He sees Carine still sleeping, but hears noise from their private bathroom.

He hesitates before he opens the door, but does so quietly and slowly.

XXX

Cassandra came out of the shower, catching herself in the steamy mirror as she did. At 36 she looked more than great. When she was still Rob and decided to go through the experimental treatment, he was scared. After the first month, he did not regret it.

Now, Cassandra stood at 5'7 and a body to die for. Big double D tits that hanged, yet maintained their perkiness. She had a small waist with big hips that gave way to one of the most amazing asses she knew, only surpassed in size, curve, and perkiness by her wife and daughter, thick and creamy thighs, and an all around feminine body. She looked at her groin and with a finger touched her little penis. As a man, she had a 6 inch penis that was not very thick, when the process finished she had the most feminine, pink, hairless, 3 inch peter, that she called clitty or dicklete. The experimental treatment she went through, ended up being so thorough, her testicles lifted back, transforming them into these little bubbles of bold, terse skin that housed his quail sized testicles. She had soft, terse, and bald skin where her little balls were, with no wrinkles there or any part of her body. Another side effect that surprised her was that her balls didn't hang, the scrotum was always tight, meaning that her new smaller genitalia would not bother her in between her new thick and supple thighs.

The hairlessness was an added perk also, not even the scientist expected, but she guessed that's what happened when you lose all your testosterone. Cassandra still wondered sometimes about the hair on her head. A luscious, soft, black mane that fell to her butt and never seemed to wane in it's healthiness or vigor.

Still, she never really worried about it, not looking at a gifted horse in the mouth and all that. Cassandra was living her best, most happy life, she could possibly imagine.

One little problem, though. She loves her son, more than anything, even her own life, and she could not conceive a life where she could not love him as a mother... and as a lover.

She understood this very well. When her son was born, her wife had decided to love him as a man when he turned 18, it didn't take long for Cass to do the same later when she transitioned, her daughter had decided the same, and all of them knew there was nothing wrong with that.

It was not weird at all for her and Carine to lay in bed, legs open just to finger themselves while moaning their son's name.

In fact, Cass had even found her daughter doing that before.

Jack's 18 birthday was a momentous occasion for the family. First came her wife, then her daughter, but everyone knew Cassandra would be a touchy subject. As the loving family that they were, they agreed to break the news to Jack in a family meeting. Her son didn't take it well.

Cassandra was deeply hurt by his comments and insults, so hurt in fact, she cried herself to sleep in her wife's arms that night. Jack had not spoken to her since then. Still, she loves her son, so she will abide by his wishes.

The door opened slowly then, and Cassandra thought Carine needed to use the toilet.

"I'm almost done Carine, I'll be right out." She said in her feminine voice, wrapping a towel over her body, but Carine didn't reply.

"It's not mommy, mom."

Cassandra opened her eyes wide and turned to her son, clutching her towel to her body. She wanted to ask what happened but his face scared her.

Jack looked tired, scared, weak... 'What happened to my baby boy!' she thought, terrified.

She aimed to say something, but Jack closed the distance and hugged her tight. Cassandra's features softened at that and returned the gesture in the most loving manner she could muster, her baby boy still loved her, she didn't need to worry.

"I'm sorry, mom. I... don't know what came over me."

She caressed his head and looked into his eyes as she told him that it was ok, that he could do whatever he wanted, that she would never push him to do anything.

Jack seemed to smile, but he started crying. Now Cassandra was confused. She hugged him and gave him space to let it all out. Finally, after some time, he looked back up into her pale-green eyes.

"You said on my birthday that..." he aimed to say something else, but a very scared Cassandra hugged his head to her ample chest and shushed him.

"Don't worry about that baby, mom is here and she won't force you to do anything, these type of things-" she was cut off by Jack, telling her that she didn't understand, she didn't want a repeat of that family meeting so she kept trying to tell him that everything was alright, these back and forths happened for a while, both of them talking over the other, until Jack in frustration, held both her hands and shot his head forward, kissing Cassandra full on the lips.

After the initial shock, her eyes fluttered and she melted into the kiss. As she relaxed her hands, Jack placed his hands on her cheeks to hold her face in place, Cass placed her own hands on his chest.

After a moment, Jack let go of her. "Wow..." she whispered, her towel falling to the ground in the moment. Jack stepped back and looked at Cassandra's body, taking it in. He was surprised by how hairless she was, bald pelvis over a small, pink, foreskin-covered penis, that hid a small pair of pink quail sized eggs behind.

He fumbled with his belt and dropped his trousers, not waiting for them to fall when he started to pull his shirt off. Cassandra stood there, still a little fazed by the kiss, when she noticed her son striping. She gasped at the sight of his big, virile, hairy member and his two fist sized hanging testicles.

He was lanky, but Cassandra could only see him as handsome. Jack kicked his pants and shoes off, and stood straight in front Cassandra. They stared hungrily at each other, the tension built until they jumped at each other's mouth.

Locked in a passionate kiss, their hands roamed their bodies, Cassandra could not believe how big her son was, one hand roamed down his chest to his abdomen, and finally she grasped his cock. She could not wrap her hand around it, so much bigger than her clitty, even before she transitioned.

His erection grew in her hand, almost as if Jack was controlling it, she attributed it to her son's virility and began jerking him, her fingers would brush against his heavy and immense testicles, and it aroused her further.

Jack cupped her double D's and massaged them, as Cassandra shifted her hand to cup his sperm tanks, he squeezed his hands and made her gasp.

"Yeah, baby! Don't worry about it, be rough!" She ravenously moaned, and her son didn't hesitate. Cassandra then dropped to her knees and looked into his eyes with a mischievous smile. She opened her mouth and engulfed his head in a sloppy kiss that turned into a blowjob.

XXX

Carine opened her eyes to see her son waking into the bathroom where her trans wife was. A smile crept up her cheek, now the family would be happy together.

A hand snaked under the covers and two exploratory fingers rubbed over her mound before probing her moist entrance.

"Jack deserves anyone he wants..." she mumbled under her ragged breath.

XXX

Jack looked down at Cassandra, as she bobbed her head up and down, maintaining eye contact with him, as she tried to smile with his huge cock in her mouth. She truly was happy, Jack is the center of her life, and she loves him more than anything. To give Jack anything he wants was so natural to Cassandra and the family, they didn't see a limit to it, to give themselves to him was just an extension of that line of thought.

Jack tilted his head back in pleasure, moaning every time Cassandra rolled her tongue around his head in every backstroke. His hands caressed her head and combed her hair back until he took a hold of it.

'Mom wanted it rough, she is going to get it rough.'

He clenched his fists in her hair, and violently pushed her head towards him, shoving ¾ of his girthy length down her mouth, lodging part of his cock in her throat. Cassandra lost balance at that, moaned into the blowjob, and had an orgasm.

Jack felt her shaking under him and looked down, her little pink penis was erect and bobbing as a very clear liquid streamed down it's foreskin covered tip.

"You like that?" He asked her challengingly, and as tears streamed down her smiling face, he pulled her head back and and pushed forward as he thrusted his hips toward her at the same time.

He bottomed out instantly, and felt her wet throat house his cock, he could see the outline of his cock pushing down under her neck, her nose flat against his pubic hair cover pelvis. He chuckled in between gasps, promptly resuming her throat fucking.

He bucked his hips and moved her head on his cock fast, with no pretense of rhythm, Cassandra gasped for air every time he pulled her head back. Her tears, snot, and phlegm covered face only showed true happiness and joy at what was happening to her.

Jack remembered the time, and that Cassandra had to go to work, so he decided to up the ante and focused on reaching his climax. Cassandra had released three of those clear discharges, and a little puddle, not bigger than her palm, was formed under the tip of her clitty on the floor

It wasn't long after that Jack felt himself peaking over the edge and simply let loose. His mom didn't understand what was happening as rope after rope of his cum started shooting down her throat directly to her stomach. Her hands, that had laid hanging next to her body, as she was flushed with the pleasure of the moment, regained their life and climbed his legs to his balls to cup them and lightly squeeze a little more of his cum out.

He pulled, halfway through his orgasm, her head until his cock was housed inside her mouth, and the final rope of cum filled it. She remained there, sitting on her heels, with her knees spread apart, her little dicklete bobbing as it dripped it's salvos.

"God! That was great!" Jack exclaimed, as he willed another erection up. Cassandra remained with her mouth open, closed it, swallowed twice, then opened it again to show she drank it all. However, when she opened her mouth, she could not help but exclaim, "how are you still hard!?"

From the other side of the door, Carine giggled as she rubbed her pussy, she became familiar with her son's virility when he took her for the ride of her life on his birthday, and hearing the same surprise she had from her partner was hilarious.

Cassandra's small penis was flailing down now, unable to maintain its hardness after the most enjoyable sexual experience of her life, but seeing her son was up and ready for more was beyond her expectations.

He held his cock by the base and lightly slapped her cheek with it, "do you have time for round 2?" he said. Cassandra was not sure she could keep up, but the center of her life wanted more, who was she to deny him, so she nodded.

"I'll call in sick today... the business works without me anyways."

He walked around her and placed a hand on her back, lightly pushing her. She understood what he meant and placed her hands forward on the floor, lifting her butt in the air.

Jack admired her ass, two perfect perky bubbles of springy flesh, not hard muscle, that sank into a waist that seemed to disappear behind her ass. He placed a hand on one of her cheeks and felt it, then slapped it, making Cassandra yelp and then moan. He found that fun, so he slapped her harder this time, to which she yelped back, "thank you, baby!"

Jack laughed at that, and slapped her again, this time harder, she thanked him again. Then he used both hands to spread her thick cheeks apart.

Her flower was tight and pink, clean and hairless, almost taken out of a porn film, there was no difference in the skin color, as he opened them also, her little testicles appeared, almost bobbing back in her new position. His cock was hard and wet and he placed the tip against the entrance.

"Yeash, baby! Please!" She moaned out loud, and Jack smiled.

He pushed forward and as his cock penetrated her she climaxed again, her dicklete soft yet squirting drops. He slowly pushed further, not stopping. Her moaning shifted in tone to a joyful scream as she arched her back, and lifted her head with a huge smile on her face. Jack tightened his abdomen and bottomed out inside her tight boipussy.

"Damn! You are tight!" He exclaimed, clenching his eyes tight. She laughed into a moan and replied, "the tightest for you, my big perfect Man!"

Jack pulled and when only his tip remained inside, pushed back in, then repeated until he reached a leisurely yet fast rhythm. Cass's tits dangled pendulously, just like her clitty under her in the doggy position her son placed her in.

Jack held her hips in his hands, his fingers digging in her pliable flesh. He marked the pace, moving her as he liked, Cass helped twerking her ass back at him with his motions.

Jack's hand shot up and took hold of her hair once again, "Yeah! Keep doing that! Rougher! Rougher!" She yelled.

Jack forgot himself and started jackhammering her ass on the bathroom floor. He cared not about her at all, but from the look of things, she was having a great time.

XXX

Anne woke up, rubbed her eyes and stood from the bed. Since her brother had sex with her, she took to sleeping naked in the hopes Jack would feel frisky at night and wanted to have her. Last night she went to bed a little sad.

Her brother was a little angry at her mom, when she offered him what Anne and Carine thought was the most normal thing in the world. She remained sad when she woke today, thinking of ways to fix things, but ultimately it was Jack's decision and she could not interfere.

As she left her room for the bathroom, the sound of screaming and loud clapping called her attention.

She curiously followed them to her parents bedroom, and when she got in she found her mommy Carine, naked in bed, rubbing her pussy furiously.

"Mommy, what's that?" She asked, combing her bed hair a little. Carine placed a finger over her luscious lips and replied, "get over here honey, your brother is in the bathroom with Cass."

Anne smiled her 1000 watt smile and jumped to bed next to her mother. The door to the bathroom was closed but the sounds coming from the inside told her everything she needed to know.

Anne laid her head on the mother's shoulder, looking at the bathroom, opened her legs wide and began rubbing her pussy like Carine was doing.

XXX

"Do you like that?!" Jack screamed. Cassandra only replied "yes," over and over, screaming with a big smile on her face.

Jack remained pulling her hair hard, she arched her back in a perfect U, her tits dangling wildly.

He spanked her ass as hard as he could in that position and Cassandra thanked him again and again.

Jack's jackhammering never ceased, bottoming out in every forceful thrust. Cass started babbling nonsense as she squirted in her constant orgasm.

"This ass is mine!" He barked, to which Cassandra agreed with every thrust.

"Only yours! Only yours!"

His testicles tightened and Jack welcomed the familiar sensation, fast approaching his climax, his abdomen tightened as well. His rock hard cock throbbed as he thrust forward as deep as he could go, Cass's cheeks flat against his pelvis.

The force lifted her from her hands, and in his orgasm he pulled her hair back, lifting her body up on her knees as Jack let loose his deluge of cum inside her ass.