The History Book Ch. 05

'He is a hot head, he won't hold out...' Jack thought, and was proven right when he stepped to a corner and Stephan rushed him with a one last hail Mary straight.

Jack stepped forward, leaned to the side, easily evading the punch and drawing the crescent moon with his arm up and around the straight from his opponent and landing the hit from above. Before Stephan realized what happened, Jack threw the uppercut from underneath the guy's guard and struck him dead in the jaw, and just like that, Stephan fell.

XXX

Jack walked to the corner even before the referee finished the count, and began to fumble with his gloves. The coach helped him and everyone looked at the scene silently for ten seconds. No one said anything, but when the referee called the knockout, the entire school building jumped in cheers. It was a fight worthy of the movies, it almost looked choreographed.

The cheerleaders, the coach, and some students flooded the ring, all cheering for him as the doctor they hired for the match checked on Stephan in the corner.

Jack made his way through hugs from horny cheerleaders and pats on the shoulder from students to his opponent.

"Hey man! Are you ok?"

The guy was conscious enough to reply, he had one black eye, and the other looked at him with sheer hate.

"Fuck you! You played with me the entire time! Is this a joke to you?!"

Jack was taken aback a little but decided to not play into the anger, "yes, it is a joke to me! Why, you didn't get it?" He laughed as he walked away quickly finding Cecilia and Maty and kissing them deeply.

XXX

Once home, Jack sat on the couch, he wanted to get intimate with his girlfriends but quickly fell asleep. He was more tired than he thought.

Carine, Anne, and Cassandra kissed his sleeping face and went to bed, telling the other two good night.

Cecilia and Maty sat on the couch on Jack's sides, leaning against him and watching him snore. They were rubbing their hands on his chest and hair, an intimate moment where the two girlfriends could feel how much they loved the man.

"Hey, Ceci..." Maty asked the Latina. She nodded back at him in reply, "today was amazing, wasn't it?"

Cecilia giggled a little and agreed, adding "it was, Jack was untouchable!" She held her hand to her mouth when she realized she spoke too loud.

Maty giggled back at her, "I know... he was so... I don't know, dominant in the fight."

"It made me wet..." Cecilia confessed, and Maty agreed, sharing their stifled giggles.

"He is always like that, right?" Continued Maty again, "the cheerleaders were fawning over him like crazy!"

"I know right!" Cecilia covered her mouth again, the two saw how Jack grunted and moved slightly.

She then seemed to deflate a little, she got serious as she kept on caressing the body of her lover.

"Maty, look... last time Jack was at my place we talked about something..." She wanted to explain it in the least embarrassing way possible, but words escaped her. Luckily, Maty was aware of what they talked about.

"I know, he talked with me as well..." he opened his mouth, to say something more, to get things moving forward, but he was equally embarrassed, so he kicked the ball back to Ceci, "we talked about what happened at your place..."

"About my sisters? No way!" She replied loudly again. Maty immediately had a flashback to his first erection in so long, he blushed and became aroused, without realizing it, his hand slid down Jack's torso to his crotch, where he grabbed the cock over his pants, "he didn't say anything about them..."

"Oh, God! I outed myself..." Cecilia whined when she saw Maty doing that.

"What? Yes. No! I mean... I don't know..." Maty replied confused, his hand pressed against Jack's member.

The two looked into each other's eyes, a glance that spoke volumes in what they were thinking. They meant a lot to each other, since Jack brought them together, the friends started becoming more intimate with each other, the closer they got, the more they could trust one another like how they implicitly trusted Jack.

"He whispered to my ear, what he would do and it drove me wild..." Maty finally added.

Their eyes were locked to one another, slightly getting closer as they breathe the other's air.

"Me too..." whispered Cecilia.

XXX

Jack dozed off, he was half asleep when he heard Ceci and Maty talking, amused at what they talked about, he decided to listen.

"It made me wet..." Cecila confessed, Jack tried his best to still pretend he was asleep and hide a chuckle.

"He is always like that, right?" Maty said, "the cheerleaders were fawning over him like crazy!"

Jack realized he hadn't thought about the cheerleaders like that before, maybe in the future, when he cleaned up his act and came clean to everyone he was involved with, he would do something about the cheerleaders.

"I know right!" Cecilia covered her mouth for the second time, Jack felt like chuckling again, but successfully pretended to still be asleep.

The two got quiet now, and Jack focused on his hearing.

"Maty, look... last time Jack was at my place we talked about something..." Cecilia said all of a sudden. Jack heard the hesitation between the two, he felt very happy his girlfriends discussed what he wanted without him in such a way.

"I know, he talked with me as well..." Maty replied, "we talked about what happened at your place..." there was an awkward silence.

"About my sisters? No way!" Cecilia replied, Jack getting anxious about the result of this conversation, he wanted it to go forward in a positive mood, yet he didn't want to show he was awake.

"He didn't say anything about them..." Maty replied.

Jack almost jumped when Maty placed his hand on his crotch, he hid by pretending to snore louder and shuffling a little in his place. He realized it would be hard to pretend to be asleep with Maty stroking his dick over his pants.

He felt Cecila perk up at that, and he could see her latina playfulness coming out through her voice, "Oh, God! I outed myself..."

"What? Yes. No! I mean... I don't know..." Maty replied, clearly bashful and unsure of what to say or do.

The silence that came after was nerve-racking for Jack, he wanted them to continue but he also didn't want to push them, if in the future he could be open about the relationship he had with everyone he needed his girlfriends to be the one to come out with it, he felt pushing things forward to fast would be a painful transition that could be avoided.

"He whispered to my ear, what he would do and it drove me wild..." said Maty, breaking the silence.

"Me too..." added Cecilia, in a quiet whisper.

He felt the two of them getting closer together, as he felt Maty's hand rubbing on his cock harder.

Jack peeked through a half closed eye and saw that his girlfriends met in the middle and shared a very slow kiss.

Jack willed his erection up at that moment, making Maty moan when he felt the snake moving under Jack's pants.

Maty cut the kiss short, and Jack felt Cecilia leaning forward, in pursuit of Maty's lips, only to find him shuffling with Jack's pants.

"I don't know where he gets the strength!" Maty whispered, Cecilia giggled back, "and he comes from the fight as well... look at him!" She whispered back, caressing his face, "he's dead asleep and can still get it up, we will definitely need more people to keep up with him..."

The two giggled quietly at that but suddenly realized this was the first time they talked about this by themselves, and in a serious manner.

"Would you... be ok with that?" Asked Maty.

"I don't know... probably? How many people would that be? There are too many questions..."

Cecilia wondered about that as her hands joined Maty's in pulling his cock out of Jack's briefs.

"Oh, he talked about doing my mom..." Maty replied, once he had Jack's cock in his hands, his concentration floated away and he got more honest.

Cecilia gasped, "that would be so hot!" And she added, "he talked about my family... and my sisters jerked him in the pool!"

Maty stifled a whimper as he jerked the man, Cecilia's hands joined her partner in crime sissy and accompanied the motions.

"How would he do it?" Asked Cecilia, Maty shrugged, "I don't know, but it feels like he could, right? He said..." Maty giggled before he continued now imitating Jack, "I'll start seducing the people, and when I want to have sex with them, I'll call you and Ceci."

Maty giggled and Jack could not help but groan, he covered up by reclining further on the couch as if he was simply moving asleep.

The two looked at him then at each other, "I'm so wet right now..." Cecilia whispered, Maty giggled back, he noticed his own erection.

"So your sisters jerked him at the pool in front of you? How did they get around to doing that?"

Cecilia blushed a little more, "I wasn't there... I went to get..." she caressed his cock, "some drinks, and when I came back they were just..." she wrapped her hands around his girth, "and I hid, didn't want to face it because of how aroused I got."

They jerked him together, the two gasping, as they shared that moment in confidence, "he then played with that when we were in bed together."

"Is it wrong that I'm hard right now?" Maty asked.

Cecilia smiled back at him, a little surprised, "I thought you didn't get hard anymore!"

"I know, right?"

The two now rubbed their hands up and down rapidly, they could not help but kiss again, now moaning as their tongues danced together. The two had developed a deeper relationship, kissing and losing their inhibitions about being intimate with each other, even when Jack is not there.

"I kinda liked it..." Cecilia said, and Jack perked up at that.

The two shared more of their fantasies and feelings towards Jack and including other women, until the man cummed in his "sleep" bathing the two girlfriends in his cum.

XXX

Jack woke up on the couch with the morning sun shining in his face, his cock was back in his pants. Last night they only jerked him to completion and he willed his erection away, before falling truly asleep, he lost most of the conversation after that.

The smell of breakfast wafted to his nose, and with a stretch he stood and walked to the kitchen, where he found his two girlfriends making him some bacon and eggs.

"Smells delicious!" He pointed out with a smile, last night's conversation had really encouraged him to push forward with bringing all the women together, 'It feels like it's time.'

The two received him with good morning kisses and enthusiasm, promptly being joined by Carine, Cassandra, and Anne.

Cecilia joked it looked like the three slept together, and they laughed nervously back at Ceci, who didn't really think twice about the exchange.

Jack offered to drive them home, but his girlfriends offered to spend the day together.

"That sounds nice..." he added, looking at his sister and mommy, as Cassandra sat at the table with a coffee in hand, the T-MILF looked up from her phone and raised eyebrows. Carine almost jumped and Anne started smiling from ear to ear.

Maty and Ceci didn't realize because they began wondering what they would do today.

XXX

After breakfast, the girlfriends went to the backyard to enjoy the rest of the morning, they invited Jack over and he explained he needed the bathroom. On his way he looked back from the hallway to his mommy and his sister, the two skipped to him and whispered by the bathroom door.

"Ok, here's the plan..." he began, "I want you two in your sexiest, skimpiest swimsuits. Today is supposed to be a very sunny day, I will chat with them for a while and then you two will come down and ask me to put sunscreen on your bodies..."

"I'm already liking the plan..." mentioned Anne, with a mischievous smile on her face.

"We do a little foreplay, and then I do the same to Ceci and Maty."

The girls nodded but Carine had concerns, "but, they don't have swimsuits..."

Jack gave her a half smile and continued, "when I'm applying sunscreen on them you come over and we lay the erotica hard... and I mean hard. I'll guide you guys from there."

Jack came to the backyard and found his girlfriends sitting on a lounge chair talking, he sat between them and hugged them tight, they melded their bodies to him almost instinctively.

"What were you guys talking about?"

XXX

Ceci and Maty needed to get ready, last night after jerking their man while he was asleep, they needed to talk more about their new found fetishes.

"What do we do then?" Ceci asked as she placed Jack's cock back in his pants.

Maty cupped his sleeping cheek with one hand as he pondered, "maybe... he is not moving forward because he wants to respect our boundaries, or he feels we are not yet ready..." he whispered back to her.

"Do you think he already has other women, but is not including them because he feels we would be scared or hurt?" Ceci replied and Maty nodded.

"I feel that I've been ready for a while, maybe since he took my virginity..." Maty followed.

Ceci explained that since she began having feelings for Jack, she's been fantasizing about it all the time.

"I don't know... it's so hard to explain, it's as if I subconsciously knew being with him meant sharing him... and I suppose I've been ready ever since."

The two shared a moment of silence, holding their man together, their fingers interlocked over his chest.

Maty was the one to break ice, "if he presents an opportunity, we should be open to it... open and ready."

Cecilia nodded and rested her head on his shoulder, "I don't know when that would be, but I'm sure soon enough..."

Maty now rested his head on his shoulder, and falling asleep he agreed before he dozed off, followed closely by Cecilia.

XXX

"What were you guys talking about?" asked Jack, as he held the two of them together.

"Not much, just you... and us, and everything in between," replied Cecilia.

"So, nothing?" Asked Jack.

Maty giggled, "I guess. Why? You got anything to share with the group?"

Jack laughed and kissed the sissy's forehead, turning and kissing Cecilia's right after.

They shared some words about the fight and everything, when Carine and Anne waltzed to the trio in the skimpiest swimwear the latina and the sissy had ever seen.

They wore a matching set of micro bikinis in red and blue, their ample flesh spilling from the sides of the string attached to the triangle pieces of cloth covering their nipples and puasies.

"Hey, guys! Sorry to bother you, but it's such a nice day we wanted to get some sun!" Carine explained as the two dropped towels on the sun chairs and laid flat on their backs.

"Jack? Could you maybe help us out with this?" Anne asked as she waved a bottle of sunscreen at him.

The brother turned lover replied in the affirmative and walked to her.

XXX

Chapter 22, the more the merrier.

XXX

Jack spilled a healthy amount of cream on his hand and began to caress his sister's body slowly. He began at the shoulders and worked his way down her back. Cecilia and Maty looked at him intently.

He took his time as he spread the lotion on her back, then reapplied more on his hand and went to her ankles, where he began to work his way up.

Cecilia and Maty looked at each other, their breathing intensifying, 'is this the moment?' Cecilia asked with her eyes, Maty didn't know how to reply, but their thoughts were pulled back to the scene when Anne moaned loudly.

Jack had reached her upper thighs and without hesitation placed both hands on her huge, bubble butt, grabbing the globes hard until her meaty buns spilled from between his fingers.

"I love it when you do that, Jack..." Anne finished with a sigh.

'What do we do now?' Maty asked Cecilia with urgency in his eyes. Ceci shook her head.

When he was done, he turned to his mother turned lover and proceeded to do the same, Carine moaned louder than Anne, and he spanked her once when he was done.

Jack had forgotten about the plan when he began working his sister's body, when he turned to Carine, he was wondering why he wasn't fucking them already, until he spanked her and he heard Cecilia gasp.

'I should probably turn this up a notch...'

"Ok, girls! Let me do the front!" He said, standing up and clapping his hands once, his mommy and sister giggled and turned, pulling the strings on their tops to let them fall, presenting their EE, and E cups for everyone in that backyard.

Their nipples were hard already protruding forward from their perky, free-hanging tits. Ceci, Maty, and Jack thought at the same time that the two don't probably need bras, and they were right.

Jack didn't even pretend he was doing something else, he poured a big dollop of sunscreen on his hand and went straight to fondling their breasts, rubbing his thumbs over their nipples as he drew circles with his hands.

Both Anne and Carine moaned loudly as Jack massaged their bodies, Jack willed his erection up, simply because he felt terribly aroused and it helped to stifle his body's reaction, holding onto control as he manhandled his mom and sister turned lovers.

"Oh, God!"

"¡Dios mío!"

Exclaimed Maty and Cecilia at the same time. That took Jack out of the almost hypnotic hold he was under by the massive tits in his hands, he remembered the plan and now it was time to act.

He stood and walked away from his mommy, straight to his girlfriends; who watched him with wide eyes.

"It's your turn, pets." He said, confidently. Maty and Cecilia looked back at each other without knowing what to do, then back at Jack who kept approaching them.

He wasn't forceful with Cecilia, he peaked down and kissed her, knelt in front of her and held her top.

"Did I tell you guys that I love your matching outfits?" He commented, making Cecilia giggle before he kissed her again. Gentle, kind, yet forward, Jack finished pulling her top and kissed her on that place between her neck and jaw, eliciting another moan from the latina.

He then began to smear the cream on her shoulders and down her arms, massaging her, relaxing her for what was to come.

Carine was the first to stand, she went to Maty and helped the sissy out of his clothes, Anne joined Jack behind Cecilia.

"Oh, God..." Cecilia gasped, she turned her head to look back as Jack kissed her clavicle, only to meet Anne who placed her lips on the latina's in a tentative kiss.

She felt the arousal rising, heating her body. Electricity ran through her body up and down; the same as Anne, whose hands began roaming the tanned body of the latina.

Carine for her part, had Maty naked in a flash, but he was too confused to know what to do next, she sat next to him and in a motherly gesture wrapped her arm around the sissy's shoulder.

"Are you ok, darling?"

Maty bumbled a quiet reply, and Carine leaned in and kissed him, "should I call Cass here?"

Maty looked up, surprised, then back at Jack who was pulling his shorts down, as Anne kissed Cecilia's neck.

Carine began massaging the sissy, eliciting small moans and relaxing him further. Maty was as hard as he could be, this was exactly one of his fantasies. Carine snaked her hand down to his boy clit, and just like how she does it with Cassandra, she used two fingers to jerk him slowly.

"Look at Jack..." she whispered to the sissy's ear, "look at how he takes what he wants," Maty moaned, "see how manly he is as he takes Cecilia and Anne..."

Jack was fondling Cecilia's C cups from behind as Anne french kissed the latina from the front. Anne snaked her hand downwards to Cecilia's shaved pussy, rubbing two fingers over her flower down and up, before pressing the two fingers over her clitoris and drawing a circle, then going down once more to probe her entrance.