The History Book Ch. 03

"You want to be a girlfriend, but you don't want a boyfriend... you want a Daddy, you little sissy slut!"

Matt gasped and his body trembled, going through something akin to a non-sexual orgasm. Jack felt his friend trembling under him, he moved up and lifted Matt legs up, spitting on his asshole and using his now free hand to rub up and down his puckering bud.

"I'm gonna make this ass-pussy mine now." He growled as Matt began breathing hard, almost hyperventilating until Jack placed his head on the entrance, when Matt's breath got stuck on his throat.

With an exhalation, Jack pushed forward and inserted his head, opening Matt to him.

Matt groaned and then let a girly moan escape his smiling lips.

XXX

Cecilia watched Jack work Matt over, entranced and confused. It was the first time she saw two guys together (no matter how much Matt looked like a girl) and she was also confused because Jack behaved completely differently than he had with her. She could not understand how the gentle man that made love to her was now overpowering the blond and becoming a dominant, alpha, macho.

Her mouth fell open as she saw Jack sliding his hips forward, inserting his enormous cock inside the blonde. Matt curved his back, and lifted his legs up, his body strung tight with his arms to his sides gripping the bedspread in clenched fists, there was a moment of silence between the two filled by Cecilia, and her surprised gasp.

"¡Ay Dios mío!"

Jack laughed and Matt followed with his own retort.

"Oh God is right, girl! He's opening me up!"

Jack held Matt by his cheek and turned his head towards the tall's gaze, "and now I'm going to break your ass-pussy!"

He finished his growl by popping open a little shampoo bottle he got in the bathroom and smearing its contents on his dick.

After that, Jack began sawing in and out of Matt, first with a semblance of gentleness, but after his friend's first few grunts followed by moans, he decided there was no need and squirting the last of the shampoo on the base of his cock he thrusted powerfully, and then jackhammered.

Matt's little dicklete bobbed against his pelvis with every clash of Jack's pelvis on his butt cheeks. He opened his mouth and a loud, feminine moan came out, his eyes crossing as his back arched further. 'This is it! He's making me his sissy!'

Years of repressed fetishes condensed in the blonde's mind, all that porn, all those fantasies.

When he first fell in love with Jack he held little hope that the man, that his friend became, could provide him with the idea he had for a partner. He understood it was a high bar to jump, after all, the people that could be what he wanted would lack the gentle intimacy, and hurt him for real. On the other hand, those he could trust would not treat him how he wanted. Matt doubted Jack could provide him with the roughness he needed.

Matt teetered on the edge, thinking he would need to come to terms with never being the sissy he wanted to be, or looking for someone other than Jack, yet for some reason, when Jack offered this uncommon relationship, Matt hoped again that maybe... maybe...

Witnessing Cecilia and Jack together had been beautiful, it showed the gentle side Matt knew Jack had. Then again, he feared that Jack would be incapable of doing the opposite.

Then... he came out of the bathroom, and Matt despaired when he aimed to do the same as with Cecilia, and out of nowhere, Jack ripped the dress and transformed it into something that which Matt thought impossible.

Another man would've gone raw, but Jack had the gentle touch of smearing the improvised lube on his cock, to finally penetrate his friend ferally.

The culmination of so many years of fantasies and secrecy around his fetish, welled up inside the small blonde. Jack held his friend's neck more tightly now, holding the body in place for his rampage. There was little Matt... Maty could do but surrender to the moment.

With his other hand on Maty's wide, feminine hip, Jack thrusted once again, Maty shuddered under him and reached his climax. The sissy's little boi-clitt throbbed and cummed two little strings of clear, watery cum, accompanied by the clapping sound of Jack's fucking and the loud, open mouth yell of pleasure from Maty.

That brought Jack over the edge and his huge testicles rose as his abdomen tightened, his thrusting becoming irregular at the same time to finally impale his new sissy balls deep and releasing his heavy ropes of cum inside.

Maty's mouthade a big O as he felt the molting hot semen filling him up, prompting another orgasm out of him from his quickly deflating dicklete, which only released a few small drops.

"Oh God!" Finally yelled Maty.

Jack slapped the sissy's small genitals one last time, thinking correctly that his friend turned sissy girlfriend liked to blur the line between pleasure and pain.

When he was done, Jack took his cock out of Maty's ass-pussy, turned and fell on the bed.

The two lovers gasped for air as Cecilia got close to the two, amazement clear on her face.

"¡Increíble, muchachos!" She exclamed.

Jack grabbed her arm and pulled her to him, locking lips in a passionate kiss, which she returned happily. Maty looked at the two, realizing he was now Jack's sissy, and Jack was his Daddy. If he had to share him with others, it felt only natural, after all, another man like Jack didn't exist.

XXX

The three lovers laid in bed, Jack in the middle, hugging in a gentle embrace. Their future seemed more certain now, Jack was their man, and the Colombian girl and the sissy blonde were his girlfriends. The rest of their future seemed not important with Jack's composed and self assured demeanor to guide them.

Maty did not want to think of the future anyways, he was Jack's and he surrendered to the moment. Cecilia, however, understood the difficulty of the future they were choosing.

"How do we tell our families?" She asked, her head on Jack's shoulder and her hand tracing lines on his hairy chest.

The three kept quiet, Maty didn't want to speak or think about that, Cecilia knew that the answer would be difficult, but Jack just chuckled.

"Let me worry about that, for all I care, you two are mine, and I'm not sharing you with anyone, convincing your families seems like the easy part."

That was the reply from the new and smooth Jack that they fell in love with, both Ceci and Maty. The composed, serious, and mature man that seemed to fear nothing in the face of the unknown. Years later, Maty would confess to Cecilia, he found this intoxicating, and Cecilia would reply that anyone would love a man that didn't fear the future.

Just like that, the three fell asleep together, covered in their one sweat. Only woken in the middle of the night twice, as Jack maded love to Cecilia one more time, and fucked Maty's ass-pussy again, before morning.

XXX

The light of morning bathed Jack's face as quiet whispers rose him to consciousness, he pretended to be asleep and listened.

"Ew, gross! His cock was in your ass, man!" Whispered Cecilia.

"First off, I clean there regularly, second don't call me man..."

"Right, sorry. Still, are you sure?" Cecilia replied, Maty didn't answer, and Jack felt him caressing his cock gently under the blankets. Jack willed his erection up for his new sissy girlfriend, laughing inwardly at their comments on his virility and endless masculine stamina. Shortly after, he felt the sissy's lips on his cock and groaned in pleasure, another muffling sound followed and he felt a third hand on his heavy balls.

He opened his eyes and was greeted with Maty, ass up in the air, holding his dick with both hands at the base and sucking his head in his mouth, as Cecilia massaged his balls with the other.

Maty gave a muffled "good morning," at him and he replied. 'This is the right way to wake up...'

He relaxed and placed his hand on Maty's head, guiding his motions, Cecilia slowly got closer but gave no sign she would join, Jack figured he needed to give her time.

He enjoyed the blowjob to completion and thanked his new sissy.

"Thank you, Daddy!" He shot back, with a huge cumm covered smile.

They got ready to check out, and walked back to the car, the ride was full of laughter and playful banter, all over a confident sense of the future.

They dropped Maty off first, he kissed Jack as if his life depended on it and before leaving turned to Cecilia and kissed her chastely on the lips.

"Ey! What was that for?"

Maty giggled like a schoolgirl and replied, "I figured, since we are in this together, we should get used to being intimate with each other."

Cecilia seemed shocked, but smiled back, not finding any problems with that logic, giving Maty another kiss goodbye before he exited the car. Jack smiled as he looked in his rear view mirror.

When he dropped Cecilia off at her house, she thanked him for the most unexpectedly amazing night she's ever had, kissed him, and went home.

Jack sat in the car for a few moments, smiling to himself.

XXX

Chapter 14, jealousy makes the world go round.

XXX

Jack got ready to leave when the car door opening surprised him, Casiopea sat on the passenger seat and told him to drive, before he got the car in motion, another car door opened, this time Celeste sitting in the back.

Before Casiopea could ask what was going on, Celeste yelled for Jack to drive and he stepped on the pedal.

XXX

Well, folks! That 's it for now.

Hope you liked it!

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~BD