The History Book Ch. 03

The tension eased some and that gave Jack leeway to speak his mind.

"Look guys, I don't know what you think about tonight... but I love you, and I want to be loved by you. I know I'm being selfish, I get it... but... I don't know..."

The two sat there looking at him. He was trying his hardest and the two could tell, it warmed their heart to see their friend like this. Matt extended his hand and grabbed Jack's, then he took Ceci's.

"I get it. I'm not too sure either, but I guess it's not something you can choose, right?"

Now it was Jack's heart that was warmed, a tear welled up in his eye and he blinked so it wouldn't fall.

"Thank you, Maty." He said and the blond nodded with a smile on his face.

"Oooh, Matyyy! Have you two been seeing each other behind my back?" Commented Cecilia, still feeling a little awkward about this but the warmth from his friends allowed her to brave this great unknown and joke openly.

They chuckled, and as if on cue, both Matt and Jack held her hand.

"I'm not joking, I can't... risk it, I guess. I can't be without either of you." Jack finished.

Cecilia tightened her grip, "you've made yourself clear by now Jack, I get it... I think WE get it." She finished pointing her head at Matt, who nodded and smiled more broadly.

"Soooo, what's next in your super awesome three-way date?" Asked Matt.

Jack took his hand and searched his pocket before he pulled a key card with a slight of his wrist.

XXX

The three friends waited for the elevator to reach the floor, Matt and Cecilia stood on the corners and Jack in the middle. This is not how he thought the situation would feel. The two were nervous and not the least bit eager, he thought the wording was precise enough, but he guessed wrong.

In fact, the two were so nervous that Cecilia was shaking and Matt was getting nauseous.

When they reached the room, neither said a word and Cecilia went straight for the bathroom.

Jack and Matt sat on the bed. When Ceci walked out, Matt went in.

The time passed as the trio sat at the feet of the bed in quiet contemplation. At some point, Jack had enough. He turned, held Ceci's hand and leaned in to kiss her, she froze for a moment until she returned the kiss, relaxing into his hold.

When Jack turned back to Matt, Cecilia followed his lips for a little before she realized he was looking at Matt, she placed her hand on his shoulder to look at them kissing.

Matt looked at his friends kissing with wide eyes, until Jack turned to him.

'OhmigodOhmigodohmigodohmigod' and Jack's lips touched his, and everything was right in the world.

Jack turned back, and loosened his tie.

He stood and turned to the chair by the wall opposite of the bed, where he dropped his tie and suit jacket, then began unbuckling his belt. The two partners still sat on the bed with wide eyes.

"I guess it is a little awkward, right?" Jack commented.

"You guess?" Shot Cecilia back. Matt laughed at the interaction.

"What's so funny?" Ceci now shot at Matt.

He tried to explain between laughs that it was just funny and that this was their normal dynamic, but he was surprised when he turned and saw Jack without his pants, Ceci followed his gaze and shared his expression of bafflement.

"¡Maldición! ¡Que gigante!" She yelled.

Matt, always the better student than Jack, understood what she said and nodded in agreement.

"What?" Jack asked, opening his arms to the sides, his cock up and bobbing with his heart beat.

"Where in hell did you hide that, Jack?" Asked Matt. Jack looked down and shrugged, as he walked towards them.

He knelt in front of the two and, first Matt then Ceci, he took their shoes off, kissing each foot as he went, then he kissed their knees and after that he loomed over them. The three slid up the bed, Jack reaching out to caress their hands and kiss them as he crawled over them until they bumped against the head of the bed.

"Maty," he said, "I'll start with Ceci."

Jack then turned and began kissing her, slowly undressing her, sliding his hands over her body gently and caringly.

He hugged her and she responded, her hands hugging his neck and clinging to him tightly.

He used the chance to grab her zipper and slide it down. In the future they will hug like this every night Cecilia needs Jack to open any dress, but today was the first time.

He slid the dress off her shoulders and kissed each, then her clavicles, then her neck, then the place Casiopea loves between the chin and the neck, thinking Cecilia would like it as well, and she did.

The moan was involuntary and it made Matt jump a little. Although he watched the scene intently, the moan was so out of character for the headstrong latina, that he could not help but be surprised.

Jack cupped her cheek and looked her deep in the eyes, "are you ready?" He asked, and Cecilia nodded. He unclasped her bra as he kissed her again, he probed her mouth with his tongue and she opened it to play. When the bra was finally off, Jack played with her tits, cupping them and rubbing her nipples with two fingers.

He kissed down her body until he reached her hips, sliding his hands under her panties and dress to pull them down.

Cecilia brought her hands to her face, covering her chest with her forearms, a shyness she was not used to as she was undressed by her friend turned lover.

Jack kissed her tummy, hips, thighs, knees and sheens as he pulled the last pieces of clothing off her body. Matt could not believe the level of care, attention, and gentleness that Jack was showing Cecilia. It broke the blond's previous conception of Jack, to a whole different person.

This was Matt's first time, so from the beginning he was unsure of what to do or how to act. This new and mature Jack reassured the crossdressing teenager, 'Jack cares about us.' he realized and began undressing.

Jack held his wrist as Matt tried to slide his shoulder straps down.

"Don't. I wanna undress you too, Maty..." he said, and the blond gave a stifled whine of eagerness. Jack was paying attention to him as much as he did Ceci, and the sissy loved it. The horniness got the better of Maty and he could not help but rub his penis over the dress, as his friend resumed his ministrations on Cecilia.

The latina for her part, had her body in a knot, her legs bent under her butt, her arms hugging her body, and her face tight in a nervous grin. Jack didn't force her to open, he only caressed her body and kissed her hands, shoulders, and neck.

"You are nervous." He stated briefly. She looked away at that and he guided her face back to him with two fingers. "It's all right," he reassured her.

Cecilia relaxed some at that, "just... be gentle, it's my first time," she responded.

Jack didn't laugh or react to that in any way other than a caring smile, "I know," he added and kissed her. She kissed back and resumed the hug they shared before as Jack guided her body down on the bed, where she opened her legs for him.

She expected that he would simply thrust forward, still seeing him like the entitled teenager he was before his coming of age, but no, the American 18 year old proved to be every bit as mature as he had shown in the last few weeks, and he showed it with what he did next.

He caressed her pussy with one hand as he used the other to hold one of her hands, she clung tight to him as she relaxed more and wrapped her free arm around his shoulder.

He kissed her again and this time she didn't hesitate to kiss back, their tongues dancing together in their passionate tango.

He worked her sex until she was soaping wet and then proceeded to insert one finger in her open flower. Pushing in and out slowly, the man before her pulled moans and whimpers out of her, and when she thought it couldn't get any better, he lifted his thumb and pressed it against her clitoris gently. Cecilia let a loud moan loose and cummed, her entire body tensing and then melting under his but her hand clutching his as hard as she could.

"¡Ay Dios mío! When did you learn to do that?" She exclaimed, her confusion clear on her face. Jack shrugged with a big dopey smile on his face and explained it wasn't his first time, and followed with, "but that's not important right now. Now, I'm going to love you, until you forget your surname."

He spoke the words with such a passion and smoldering intensity as he locked gazes with Cecilia that both her and Maty whimpered a stuffeld moan, and Cecilia nodded effusively.

He slid both of his hands down her body to her shapely thighs, and wrapped them under her knees to open her for him, never looking away from her shining caramel eyes. For her part, Cecilia reached for his face to cup his cheeks, both for her own reassurance and for a small fear that he would look away.

Without looking he placed his twelve incher's head at her entrance and slowly rubbed it up and down, covering his tip with her wetness. Jack asked once more if she was ready, she nodded again and smiled, melting Jack's heart as she did.

He pushed forward, his head popping in uncharted territory to any other man and it felt glorious, he wanted to moan and lift his head up but Cecilia held his face, the meaning clear, 'Don't you dare look away!' and he understood.

A slow crude nod of warning was given before he pushed deeper, making the latina moan again, he bumped against her hymen and broke through in the same motion, not wanting to give her any more pain than the absolute inevitable.

Cecile stifled a small yelp of pain and a lone tear streamed down her cheek. "Tell me if it hurts, Ceci."

"Si, Jack."

He then pulled until only his head remained inside and just as slowly pushed back inside. The motions caused her some uncomfort but he didn't relent. Her clawed hands stabbing her long nails on his upper shoulders forcing him to arch his back, but Jack didn't want to pull his body away from her, so he threw himself at her, lowering his body so his chest mashed her perky breasts, she wrapped her arms around his neck and hung to him for dear life. So close they remained, their noses touched, sharing small Eskimo kisses that pulled big smiles out of both of them... smiles that turned to a loving open mouth kiss.

His gentleness and caring touch helped so that just as the pain began, it went away. Soon, Cecilia began to moan, the feeling welling up inside of her, waves of pleasure that only escalated with every thrust. He tucked his head and kissed her neck opening her line of sight to the ceiling, in the corner of her eyes she caught the sight of Matt, rubbing his crotch with one hand. She realized that he was as much a part of this as them, happiness welling up inside her heart, her dear friends were there for her, turned lovers in a twist of fate she could have never predicted. In a subconscious act, she made eye contact with Matt and extended her hand to him, which he promptly caught, eliciting another smile out of her open, gasping mouth.

Jack grunted, his pace getting quicker, he lifted his body again and saw his new lovers holding hands and it drove him mad with joy, mainly because they both looked at him with as much affection as he had for them.

Cecilia was getting close again, her moans rising in octaves with every couple of thrusts as the pace quickened. She felt the wave about to crash, cresting over her peak in slow agonizing pleasure, building until it finally crashed fully, eliciting another yet louder moan that turned to a yell, and then a calling for God (in Spanish).

Jack's hips became erratic shortly after and erupted inside Cecilia, thrusting forward one last time, as her velvety pussy massaged his cock in waves. This brought a silent chuckle to Jack as it reminded him of Casiopea, but he never showed it to Ceci.

The two lovers gasped for air, chests rising and falling with the exertion, he remained inside of Cecilia for the intimacy and just then he realized she had her legs wrapped around his waist.

With her arms open to her sides and still holding Maty's hand, Cecilia expressed her surprise.

"Wow! That was amazing!" She began, getting more excited as she spoke until she started ranting in Spanish without noticing, "no sabía que podía ser tan genial, es precioso Jack. ¡Es precioso!"

Jack arched an eyebrow until Cecilia realized she was talking in her mother tongue and covered her mouth in a gasp, which promptly made her two friends laugh. She followed shortly after.

"I guess we now have to wait a little, do you want to drink some water Jack?" Matt added after they all finished laughing, his friend only grabbed his other hand and kissed it.

"Wait? Wait what?" He said, willing his erection up again inside Cecilia. She gasped again and mentioned her friend was getting hard again, making Matt open his eyes like saucers.

"Aren't you full of surprises today?" Matt finished.

Jack got up, slowly getting out of Ceci's pussy.

"Wow, I didn't realize how full I felt..." she commented with a hand over her pelvis.

Her lover chuckled at that, "well, not to toot my own horn or anything, but I'm pretty big."

Cecilia snorted at the comment, before Jack continued.

"I'm gonna go clean up for you, Maty. Then I'm turning you into my girlfriend." He finished.

XXX

As Jack closed the bathroom door, the friends began talking in whispers.

"So! Maty, eh?" Started Cecilia, Matt giggled.

"I guess. I kinda like it... I mean, I know it's girly but I like it." He responded.

They shared another quiet giggle, Cecilia turning to rest her head on her elbow and face her friend.

"How was it?" He finally asked the latina, and she responded with a groan, explaining how incredible it was and how she couldn't have thought Jack would be so amazing, making Matt equal parts giddy and nervous.

"And you? What's up with all this?" Cecilia asked her friend, making a circle with her finger at Matt.

He shrugged and turned to her, resting his head on his elbow like her.

"I've always been a crossdresser, just kept it hidden well enough... I came out for him, you know? I needed to be honest if I wanted to have something real..."

"And he doubled down on that honesty, didn't he?" The latina sassed back, Matt giggled and agreed, commenting how unexpected it was when he told him that he wanted to be with the two.

"I was so angry when he told me! I prepared the perfect date, right? And he was perfect the whole time, and-and... we were in the back of his car in the lovers' groove, right? And he up and drops this bomb on me after the perfect date!"

Matt was venting his frustration when the bathroom door opened and Jack came out.

"I needed to be honest as well, Maty." He said, drying his hands with a towel, before he continued.

"I know you guys think I'm more mature and everything, but I'm still selfish... I can't help it."

He stood at the door, not wanting to move forward. He doubted the wording he wrote in the book, nothing working as he had wanted. Now he feared what would happen next.

Matt stood from the bed and offered his hand, Jack leaped the two steps to him and held them. They looked at each other for a moment before the two kissed again, their tongues playing. Jack aimed to undress him like he did Cecilia, with care and affection.

Jack caressed his soft feminine body, and Matt moaned, he slid his hands down the blond's hips and back up again to grab the zipper behind his back, but Matt grunted and placed his hands on Jack's chest, pushing him away with some discomfort and a slight frown.

"What's wrong?" Jack asked.

Matt held his arms close to his body, "I... I don't..."

Jack immediately embraced Jack and kissed his head, "relax, tell me what's wrong."

Matt took a deep breath before he replied.

"It doesn't feel right, Jack." His voice was soft and as feminine as his attire. Matt was for all intents and purposes a girl in Jack's eyes, so he mentally treated the blond like Anne. 'Maybe I'm doing this wrong...'

"How so?" He asked, trying to piece the puzzle.

"I want to be your girlfriend, but I'm not a girl... I'm a sissy, a femboi, I- I don't want you to treat me like Cecilia..."

Jack's greed flared in his mind and a sinister light flickered behind his eyes. The memories of his research about the terms he placed in the book for Matt came to the surface and the weird elation he felt when he explored his sadistic side with Cassandra accompanied them.

"I get it." He replied.

Matt responded with half sentences, trying to explain himself better and apologize at the same time, but he was stopped dead in his tracks when Jack spoke.

Before the blond resumed his incoherent rant, Jack took hold of the dress and ripped it open, eliciting a half, very girly, yelp out of Matt.

"I know what you want," Jack said, pushing Matt on the bed, "and I can give it to you."

He grabbed the tattered dreads of the dress and pulled it off his body. Matt was wearing red lace panties underneath, and Jack laughed.

"So you go all the way with the thing, right?" Jack said, talking about Matt's crossdressing to the point of wearing panties.

The blonde friend nodded in silence, but his mouth had curled up in an incipient smile. This was doing it for him.

The tall dark haired Jack felt a knot in his chest, a certain tension, like a cup about to overflow. He stepped over Matt, who laid on his side and looked at his friend with a conflicted expression.

Looming over the sissy, Jack took a handful of his blond hair and forcefully pulled him to his hard cock, smashing his cock between Matt's face and his abdomen.

The blond sissy snorted the smell and was a little disappointed that it smelled clean, but being forced onto Jack's cock was doing something right, just the same.

"Is this what you want‽" Jack felt some uncertainty, although he showed bravado for what he intuited Matt wanted, he still was doing this for the first time.

He pulled Matt away, and swayed his hips to slap his cock on the sissy's face, "open up!"

Matt opened his mouth and with crossed eyes tracked the largo cock unsuccessfully, as Jack moved the head away teasingly, until he relented and simply shoved the cock in Matt's mouth. The short blonde gagged on the cock the moment he had it in his mouth.

Jack bumped his friend's head on his cock a couple of times and then threw him away on the bed again. Looming over the blond, Jack now saw him smiling.

"You like this don't you? This is what you wanted..."

Matt gingerly nonned, as the smile grew on his face, a small boner in his panties peeking out of them. "You got hard at this, you little sissy?"

Jack growled the last word, making his friends swoon, grabbing Matt's panties and ripping them from his female hips.

Jack stopped dead in his tracks, thinking about what to do next, insecure about what he knew he had to do. 'Fuck it!'

He stood tall over the blond on the bed, his cock bobbing up, casting a shadow over the other.

"Look at you? Don't you feel sorry for having such a little girly dicklete?" Jack spouted, immediately he felt anxious, he didn't know what Matt would say. To his surprise, Matt nodded and whispered a timid "yes" while keeping eye contact.

Matt in fact was small, he was four, probably 5 inches small, and his testicles could not even be called that. Matt's thighs were so thick and meaty that you could barely see his genitals anyways.

"I didn't hear you?" Jack said, leaning down and taking hold of his friend's genitals, squeezing slightly.

Matt repeated his agreement, but louder. This explained Jack most of what he needed to know.

"I know why you don't want me to treat you like Ceci..." Jack whispered to his ear, taking his hand away from Matt dicklete and sliding it up the lean body of the blond to the feminine neck and closing his fingers just so that Matt felt the pressure, and continued.