He is Your Master Now Pt. 13

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When the moment came, he encircled the big cock tightly with both hands, worked up some saliva and coated it thoroughly. He then slid them down the length of the shaft while squeezing. This enlarged the cock slightly, but it also made it harder and sleeker as the skin was now taut.

Ambrose licked his lips, tucked his upper lip under his upper teeth and draped his tongue over his bottom teeth. He took the plunge. When he had most of the prick swallowed, he had to force himself the rest of the way. There was some discomfort from his throat being expanded, but it was mitigated by the pride he felt.

"GOD DAMN!" exclaimed Manuel.
Ambrose' response was to slip out as much of his small, pert tongue as he could and expertly lick what little he could of Manuel's balls..

"Ohhhhhhhhhhh shit!" Manuel yelled.

Ambrose pulled away and smiled at the big man. A string of saliva connected his lips to the large cock.

"Was that OK?" he asked coyly.

"Shit, baby, you know it is," Manuel smiled back. "No one's ever been able to do that. I didn't even think it was possible. And on top of that, you looked gorgeous doing it baby. My sweet, little Miss Amanda can deep throat. How about that." He sat up to kiss Ambrose.

As Ambrose went to meet him, the string of connective saliva disengaged from Manuel's cock and stuck to Ambrose' chin. Manuel licked it up before they kissed.

The passion was so strong and genuine that Ambrose had a disturbing thought.

Shit, I think I'm falling for him for real. But now that he had that thought he wondered, would that really be so bad?

He went back to deep throating Manuel, working up to as quick a pace as he could. He was fucking his own throat with Manuel's cock, to the big man's increasing pleasure, judging by his delirium-like moans.

It was Manuel who put a stop to it when he disengaged and softly positioned Ambrose onto his back.

Oh my god. It's going to happen. He's going to make me a woman.

He panicked when he realized that they hadn't lubed up.

And once again, Manuel shocked him by lifting his ass and jamming his tongue into Ambrose' asshole. No one had ever rimmed him before. It was a wholly different sensation than anything he'd ever experienced. If it were anyone other than Manuel, Ambrose wouldn't have feared that he hadn't cleaned himself well enough. But since it was Manuel and the sensation was so wickedly pleasurable, the thought never even crossed his mind. It wouldn't have mattered anyway; he had cleaned himself thoroughly precisely because he planned to be with Manuel.

Ambrose closed his eyes and instinctively pushed his ass closer to Manuel's face. Manuel dived as deep as he could and wiggled his tongue wildly.

"Oh my god!" Ambrose moaned.

As was the case when he went down on Ambrose, Manuel varied his technique, sending waves of pleasure up and down Ambrose nervous system.

After a while he had to put a stop to it.

"I need to be fucked right now," he said with urgency.

He peeled away from Manuel, crawled to the nightstand and came back with lubricant.

"We'll lube each other," said Manuel. "Lube my cock and I'll lube your sweet little honey pot."

"Honey pot," Ambrose repeated. "I was thinking of it as my boi pussy but I like honey pot better."

They lubed each other with great urgency. Ambrose was so primed for being penetrated that he hardly gave any thought when Manuel penetrated his asshole with his fingers in order to lube the passage. For his part, Ambrose enjoyed the slick sensation of lubing a big cock that was about to penetrate him.

"OK," said Ambrose breathlessly, "we're ready. Kiss me for good luck."

After they kissed, Ambrose had forgotten his prophetic vision and tried to turn to around on all fours, but Manuel stopped him.

"I know I'm going to be your first, I want to look at your beautiful face when that happens."

Ambrose felt a wave of emotion. He could almost feel tears in his eyes.

He held a hand to Manuel's cheek and shook his head in assent.

He jumped when he felt the head of Manuel's cock pressed against his anus.

"I'm sorry," he told the big man.

"Don't be. It's normal. I know this is scary for you. I want it to be memorable."

God damn. What a fucking man. Ambrose couldn't believe his luck to be with him.

When Manuel pressed ahead again, Ambrose controlled his urge to jump.

He felt increasing pressure as Manuel slowly pushed. Just before the head was about to push in past Ambrose' O-ring, Manuel pushed a little too hard. Instinctively, Ambrose reached out a pale white hand towards Manuel's dark abs. "Slower. Slower."

"OK. Geez, I'm sorry."

Manuel slowed to glacial pace. Ambrose kept grimacing as his asshole stretched wider and wider to accommodate the knobby cock head. Then, before he could even expect it, the head popped in.

Ambrose' eyes flew wide open in shock accompanied by an uncontrollable gasp followed by breathlessness that lasted so long, he nearly passed out. He jumped and bucked which made matters worse. When he was finally able to breathe again, it was a huge, ragged indrawn breath. His body settled into writhing pain when he was finally able to breath in and out, though raggedly.

"Are you OK?" asked the big man worriedly.

"I'm fine," he answered hoarsely. In spite of the pain, which was now diminishing, he was still highly aroused.

When Manuel shifted his weight Ambrose feared he'd get no time to recover. "Wait! Wait!"

"I'm sorry" said Manuel worriedly. "I was trying to make it easier. We can wait as long as you need baby. I can pull out and we can try ag---"

"NO!" he yelled louder than he meant to. "I need this. You wanted it badly, I want it even more. It's my fault. I should have prepared with a toy." He said in a pained tone.

"Shit, I didn't even think about that either."

Ambrose smiled up at him; the pain subsided noticeably. "You wanted to fuck me so bad that you forgot to be considerate?" he asked jokingly.

Manuel turned red and smiled. "I guess I did. But I don't think you really know how cute you are."

Ambrose looked down to where Manuel's large cock head was buried in his ass; his small erect penis was in the way. "My clitty never got soft," Ambrose noticed aloud. "I guess this is what they mean by the sweetest of all sweet pain."

Manuel guffawed.

"I'm ready," said Ambrose with great seriousness and placed his hands on Manuel's arms as the big man supported himself above Ambrose.

"Are you sure?"

"This is the most ready I've ever been for anything." Ambrose moved his hips for emphasis and closed his eyes. He already knew he was going to enjoy it.

He moaned as Manuel slowly started rocking an inch back and forth, accustoming Ambrose' ass to this activity which was new to him. It was nothing like when Cassilda fucked him, even with her magic, zombie-dick dildoes and the intoxicating smell of her cunt fresh in his nose to make him docile and receptive.

When the pain was completely overcome by the sensation of a living, beautiful cock sliding in his ass, a new world opened up to him.

"Deeper," he groaned.

"Just a little. We'll take it at your speed."

"I trust you."

Over time, Manuel moved deeper and deeper until he could fit nearly two thirds of his cock in.

"Oh my god." Ambrose nipples hardened and he began grinding his hips sensuously. Each swirl of his hips seemed to alternatingly amplify his pleasure.

Manuel took his time, slowly inching in deeper. But the big man was also riding his own high and found it difficult to completely control himself. With just a little bit left before he was buried to his balls, he couldn't help but drive it home a bit too quickly. Ambrose yelped unexpectedly. He clenched his asshole and dug his nails into Manuel's arms.

"Shit I'm--"

"Stop saying you're sorry. Just fuck me, big daddy." He hadn't planned on saying big daddy; the words were just naturally wrenched out of him without a thought.

With Manuel balls now deep into his boi pussy, they kissed again and stared into each other's eyes. Then Manuel began fucking him in earnest.

Ambrose' suspicion that he would enjoy getting fucked was verified. He never really believed anyone could derive true pleasure from anal sex; he certainly hadn't with Cassilda. He assumed that any enjoyment he derived would be emotional; due to another man making him his bitch or, as with the Masked Man when Pippi was manipulating the plug in his butt. But even there, he just assumed the humiliation of sucking a supernaturally large cock had done it for him. He now knew it was possible to feel pleasure from anal sex.

The big man lowered his body onto Ambrose', being careful not to fully rest on the little man and crush him, making it harder to breathe.

It seemed to Ambrose that every little thing that was new to him added a new dimension to his pleasure. Of all the things he imagined, he hadn't thought that the weight of a man pressing down on him as he was anally penetrated would provide its own unique sense of gratification. In addition, his small cock tumbled and slid along Manuel's abs. The sensation was almost like that of being masturbated.

All the while, Manuel kissed Ambrose' face and cradled his head while propped up on his elbows. He rocked back and forth while Ambrose embraced him. The man wasn't just fucking him, he was truly making love to him.

"Faster," Ambrose encouraged.

Manuel complied and before long, he was dripping sweat onto Ambrose.

Ambrose "oohed", "aahd" and squealed like a teenage girl. It came to him naturally and seemed convincing because of that fact. There was a point when Manuel pumped into him as fast as he could. In response, Ambrose repeated "Oh my god!" many times with increasing urgency and volume.

He transitioned from "Oh my god!" to a soulful wailing.

He started calling out whatever came to mind. "Fuck me big daddy. Make me your bitch. Oh baby! I had no idea--- how---. You're so fucking hot, my beautiful stud." Plus a few other things he reasoned would embarrass him when he came down from his incredible high.

Manuel shifted slightly. "Holy mother! That's the spot! That's the spot! That's the spot! Hit like that. Keep hitting it like that."

He wrapped his legs tightly around the big man and kissed him on the cheek before closing his eyes and resting his chin against Manuel's shoulder. He found himself lost in some strange world and wondered if this could all be real.

In the darkness, he envisioned his past self in his ballerina outfit staring down at him as he was being held by Manuel in an enticing pose. With this new reference point by which to fully realize his vision, he was now simultaneously that past self and his current self. He was every version of himself going all the way back to when he first met Cassilda.

Because of the mansion's ability to play with time, allowing the present to change the past and undo the present and the future, Ambrose was now presented with a second opportunity to change his past and erase this moment. He couldn't help but interpret the joy he was feeling now as the true reason why this life was always inevitable.

Just as was the case in that magical moment in the recent past, he knew with a certainty that if he rejected this destiny, this version of himself would be undone, his past would have been reordered, he would have never met Cassilda and be none the wiser.

He'd be miserable and angry again to his dying days.

That unpleasant young man on Fifth Avenue deserved better. He deserved to become the sissy who voluntarily surrendered his masculine agency and was now being passionately fuck by a man he would have assumed was a dangerous thug without even bothering to get to know him. He smiled at the ballerina he was and shut his eyes tight.

His cried tears of joy.

He became more sensitively attuned to the feel of Manuel's cock. It was almost as if he could feel every bump and pulsing vein. Something began happening to him as his little penis rolled and rubbed against Manuel's body. It was a dull buildup of pressure from within that was vaguely familiar and yet unfamiliar at the same time. The more his penis rubbed against Manuel and the more he became cognizant of the deliciousness of the cock in his ass, the more the pressure built up. He embraced Manuel even tighter.

When he finally came, it too was both familiar and unfamiliar but extremely intense. What he had was a regular climax enhanced by a sissygasm. He would later realize that he had a sissygasm as he sucked the Masked Man's cock while Pippi manipulated the butt plug.

This time, the sensation was well beyond what could be described as "pleasurable." It was literally ecstatic.

His rectum flexed and his body shook so rapidly that the sensation affected Manuel and took him over the precipice. His own experience, while falling short of Ambrose' was still the most intense he had ever felt. He shot a copious amount of semen into the smaller man's ass.

"Wow," Manuel exclaimed. He looked down at Ambrose in the afterglow of what they had just shared and became worried when Ambrose appeared to be in a catatonic state.

He pulled out of Ambrose releasing a flood of semen from the smaller man' ass.

"Miss Amanda," he frantically tried to rouse Ambrose.

"Wake up, wake up!" He was on the verge of panic. The fact that he was in Carcosa and insulated from the outside world by whatever magic ruled there, could not overcome a lifetime of his own paranoia in regard to himself as well as those of many of his friends and family. No good could come from a black man fucking a white man in drag into unconsciousness.

If it were anyone else, he would seriously consider abandoning them. He'd never do it, but he'd think about it at the very least. His freak out was very brief precisely because he could never abandon Miss Amanda; he collected himself and continued to rouse Ambrose.

He shook Ambrose lightly. "Miss Amanda, wake up!"

After a few moments, he tried again. His panic began to ebb when it appeared that Ambrose was coming to.

Ambrose opened his eyes to a worried Manuel. He knew that he blacked out and that it was from the most intense climax he'd ever experienced.

He began crying over its ferocity and also because he was happy, all the while kissing Manuel frantically in gratitude. When he relented Manuel stroked his face gently, wiping away his tears.

"I was really worried about you. I was afraid I hurt you."

"I've never been so scared and felt--- so much pleasure--- at the same time." Said Ambrose breathlessly, "and--- each--- the fear and pleasure was so intense. Too intense. It was just too much. I'm not sure that I ever want to feel that again."

What does that mean for us? A worried Manuel wanted to ask but it was inappropriate at the moment.

"But don't worry, I don't think it'll ever be that intense again." Then, exactly as a woman might, he felt the need to reassure Manuel. "But it'll be great. I mean, how can it not be. You were wonderful. I'm glad I chose you."

They both laughed a genuine, but awkward laugh.

"I'm glad you chose me too. You were out cold, so maybe you didn't hear me--- that was the best sex I ever had."

Ambrose laughed again and covered his face with one hand to hide his bashfulness.

When the moment passed, he became conscious of a cooling clammy sensation on his belly. He had never shot so much cum in his life. Some of clung to Manuel.

He felt the need to crown the moment with a gesture of some kind. He surprised himself by scooping up as much of Manuel's cum as he could from his ass and mingling it with his own. He bought the mixture in his mouth and ran it over his tongue. Manuel surprised him yet again by kissing him. They passionately shared their combined semen.

"Oh my god," Ambrose hid behind a hand again, "that is the least likely thing I would have thought I'd ever do."

"I think that means we're married now," joked Manuel.

"Well it's certainly hotter than exchanging vows."

"Any regrets? Think before you answer ."

"Fuck no." Ambrose kissed him. "I'm really thirsty."

"Point me to the kitchen and---"

"No. You lay back and relax like a king; I'll go get us a couple of colas, unless you want something else."

"No, cola's fine. I hope you don't mind if I stare at your fine ass when you leave."

"Do you want me to come back walking in backwards?" he asked humorously.

"Nah. I want to see that gorgeous face when you return."

He rolled out of bed and yelped when more semen poured out him,

"I need to drain your daddy juice first."

He awkwardly walked to the bathroom with his buttocks clenched and sat on the toilet. When he was done, he wiped any residual cum and proceeded to the kitchen. As he passed Manuel, the big man leaned toward him and gave his ass a light spank.

"I couldn't resist."

"You don't ever have to resist. You can spank me later if you want," he added teasingly.

Ambrose returned with two glasses filled with ice and soda.

Both drinks were downed quickly.

"We really were thirsty," said Manuel.

"You did most of the work, should I get you some more?"

"In a while. I want to snuggle."

When they lay back together Manuel referred to Ambrose calling him a king. "That would make you my queen."

"In more ways than one I guess."

That elicited more laughter from both.

Then Ambrose had a thought that diminished the high he was on.

Manuel noticed. "What's wrong?"

"I'll never feel that again." he lied.

"You said you might not ever want that."

"No. You're right. It was so great that I just forgot about the frightening part. Don't pay any mind. I guess I'm becoming ditsy from your awesome cock." He brightened up and hoped it was convincing. "It'll still be great. I know it will."

He kissed Manuel again and fell into his arms.

He had never felt so sure about someone as he did Manuel and yet, in spite of the literally, mind blowing intensity of his sissygasm, he didn't see the Yellow Sign that he so desperately wanted to see while Manuel was fucking him.


12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
FranziskaSissyFranziskaSissyalmost 2 years ago

Im sure princess had been lucky, lucky because so well trained before hand and prepared for the submissive part of cocksucking or doggy style analsex ..... And thats another 100% the first time sex is for everybody some you will never forget doesn't matter how good bad or may evil it was ..... But becoming a sissy, getting truly fucked, breed and pregnant, is soooooo extraordinary and it really doesn't matter in a sissy content if its happen in consens or kind of rape, it will change your mind in total

Thank you Master for this tale and this long way with all the mind crashing details

💝💝💝💝💝💝💝💝💝💝🍀

enwaluenwalualmost 3 years ago

Wonderful story.I really enjoyed ,but have some questions.

Who is Casilda ? A separate chapter could explain.

Also i would like to put Ambrose or Amanda, i my self prefer

the second name , on hormones to shrimp his penis to half size ,

reduce his nuts to almonds and get some lemon size tits.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Queen of the Full Moon: Rising Pt.1 Series about a magical medieval Queen.in Transgender & Crossdressers
Clerical Conundrums Ch. 01 Grace's adventure for the fertility goddess begins!in Transgender & Crossdressers
The Thorns Upon the Roses Ch. 01 Joshua finds himself the subject of a strange study.in Transgender & Crossdressers
Femboy to Fembot Ch. 01 Casey's unwilling conversion into a robot catgirl begins.in Transgender & Crossdressers
Princess of The Elves Ch. 01 A shipwrecked prince is taken by mysterious elves.in Transgender & Crossdressers
More Stories