Amanda and Jeff Ch. 15

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"Mmm, you taste good lover, I just had to share," Sierra purred. She was surprised that Jeff didn't pull away upon tasting his cum. The taste of cum didn't bother him; she liked that.

They continued to kiss, and Jeff was feeling her tits. They were nice-sized and firm. She stood up to remove her shirt and bra. Meanwhile, Jeff finished getting undressed. Sierra still had her skirt on. She hugged Jeff and kissed him. Jeff broke away and craned his neck down to suck her nipples. He moved from one to another; her nipples were stiffening. Sierra was moaning. Jeff had one hand on her ass; he was fumbling with the zipper on the back of her skirt.

She broke away from the hug and looked at Jeff.

"Did I do something wrong?" Jeff asked, "I didn't mean to rush things; I thought we were getting on well."

"No, you've done nothing wrong. Before we go further, I have to tell you something. I hope you won't freak out or anything," Sierra whispered. She reached behind herself, unzipped her skirt, and let it drop. Jeff looked at her panties, which were unbelievably tight on her. Sierra bent over and pulled the waistband of her panties down; she stepped out of each leg. When she stood back up, Jeff was treated by a view of a penis that was as big as his if not larger.

Jeff stood still, barely breathing.

"Are you alright?" Sierra asked.

"Surprised," Jeff answered. He thought about what would happen if he freaked out, Stan would probably kill him, Amanda had threatened castration.

"Are we good?" she asked nervously.

Jeff wrapped her in a hug, "we're good, we're good," he whispered in her ear. And he kissed her.

She melted into the kiss more than she had in any of their previous kisses. They fell onto the bed. Jeff had Sierra on her back. His cock hadn't recovered from her previous efforts. He resumed kissing her breasts and worked his way down to her navel. He looked up at her face; she was looking back at him expectantly.

"May I return the favor?" he asked.

"Please," Sierra purred.

Jeff licked a drop of pre-cum from the tip of her penis and then licked his way up and down her cock. Her cock was beautiful, and Jeff took it into his mouth and started sucking on it in earnest. Sierra was playing with his hair and writhing underneath him.

"Your mouth is like heaven. You're very good at this," she said with a raspy breath.

Jeff was encouraged by her banter. Her cock had reached full erection; he had no trouble deep throating her. After several minutes, Sierra clutched his head and forced her cock deep in his mouth, past his throat.

"Fuck, I'm going to come," she panted, "don't swallow it all, save some for me." She lifted his head a little, so she wasn't injecting her cum straight down his throat. Jeff felt her stiffen and her cock pulsed, and he was left with a mouth full of cum.

When her cock was done cumming, he looked up at her; she smiled back at him. "C'mere lover, I want some of that," she said breathlessly.

Jeff crawled up her body and joined her in a cuddle, swapping her cum in a sloppy kiss. The kiss lasted a long time, during which they groped each other.

"Your wife is crazy. If you were my husband, I wouldn't let you out of the house without chastity," Sierra whispered.

"Well, actually, she keeps me in chastity. She let me out tonight as a favor to Stan," Jeff said as he licked Sierra's ear.

"I'll have to thank him for that. Hell, if she's going to get his cock, I don't see why I can't keep getting yours," Sierra purred.

"You're an exceptional lady, Sierra," Jeff complimented.

"You aren't kidding. I was a confused boy, but now I'm growing into a confident woman. I thank you for your help," Sierra said, kissing his neck.

"Stan told Amanda that you don't get out much," Jeff said.

"It's a scary world for a transgender person; Stan looks out for me," Sierra said.

"My wife threatened me with castration if I broke your heart," Jeff said.

"Is that why you've been so nice to me?" she asked.

"No, you're quite fascinating and exciting. I would have never known you were different. This has been my best evening since my wife started this lifestyle. I hope her relationship with Stan continues so we can be friends," Jeff explained.

"You mean lovers," Sierra laughed. "I feel something stirring down there."

"You bring it out in me," Jeff said, kissing her.

"Let me get the lube out of my purse," Sierra said as she crawled out from underneath Jeff and sashayed to the dresser where her purse landed. She pulled out a tube and returned to the bed.

"Now, this is how this is going to work. You get to fuck me in my sissy pussy, but then I get my turn on your ass," Sierra said.

"Ok," Jeff said. "We switch as top and bottom."

Sierra pushed Jeff onto his back. She lubed up his penis. As she stroked, it became fully erect. She squatted over him and sat back on his cock in a forward cowgirl position.

"Damn, Jeff, your cock is a perfect size," she moaned as she bottomed out on him. "It touches me everywhere."

Jeff got excited as everyone else thought his cock was small. He put his hands on her hips and worked her up and down. Sierra's cock was coming back to life. Pre-cum was leaking from the tip. Jeff pivoted his pelvis up, forcing Sierra forward. He craned his head up towards her pelvis and took the head of her cock into his mouth.

Sierra pushed his head back to the pillow. "Don't be trying to suck me off; I get to fuck you after this."

"I wouldn't cheat you out of it; I'm looking forward to it," he groaned, edging closer to a climax. Sierra was bringing out the man in him; he very seldom came twice in a night.

Sierra felt him getting closer, so she plunged down on his crotch, burying him in further than before. She was rewarded by a convulsing penis shooting ropes of cum into her ass. She squeezed her sphincter in time with his cock throbs, milking him of his cum.

Jeff was gasping for air. Sierra unmounted from him, moved up, and sat on Jeff's face. "Clean me, don't worry, the lube is edible."

Jeff was taken by surprise, but he complied. He was rimming her stretched rosebud and gently fucking it with his tongue.

"That tongue feels like heaven; I'm in love!" Sierra shouted.

Jeff enjoyed the encouragement. Sierra's cock was as hard as a rock. She got off of his face.

"Enough, foreplay, Jeff. It's time you got fucked," Sierra moaned. "Get on your hands and knees."

Sierra stood up and lubed her erect cock. It wasn't the largest Jeff had taken, but Jeff felt it would be his most enjoyable yet.

She knelt behind Jeff and ticked his asshole with the head of her cock. "Ready to my bitch, Jeff?" she whispered in his ear.

"Yes, ma'am," Jeff said.

"Good answer," she said as she started pressing forward into his ass.

"That feels so good," Jeff moaned.

Sierra pressed all of the way in until she bottomed out. She withdrew and then started sawing back and forth. She was rubbing up against Jeff's prostate. Most of the time, when Jeff had been fucked, the cocks were much larger, and his prostate didn't get the attention it was with Sierra's cock. The pressure and friction were driving him wild; his penis was steadily leaking.

Sierra reached forward and pinched Jeff's nipples, giving them a slight twist. She kissed the back of Jeff's neck, "Your ass is making me feel great," she said.

She kept sawing in and out of his ass. She kept attacking his nipples; she was approaching another orgasm. She let go of Jeff's nipples and grabbed his hips. Jeff felt a warm, burning sensation as the blood returned to his nipples.

Jeff realized he was approaching another orgasm himself. He tried to time it with Sierra's approaching ejaculation. As Sierra buried herself in as far as she could go, her orgasm hit. Jeff practically collapsed underneath her, experiencing an extended dry orgasm; he was positively drained.

The spasms and constrictions milked an extra rope or two from Sierra. When they both finally stopped quivering, Jeff was lying face down in a puddle of their juices. Sierra laid prone on top of his back, her shrinking cock, retreating from his asshole.

They fell asleep like that in a state of bliss. The movie faded to black, and the credits rolled.

Instead of the usual insults, the attendees applauded Sierra and Jeff. The socializing continued into the night. While Amanda entertained a few of her lovers, Sierra and Jeff enjoyed some private time. They discussed the future potential of working together.

The following week work started on the next film. In the movie, there was going to be more hotwife cuckold action. Jeff wasn't approached with the entire script as Vince thought some surprise element might be manageable on the set. Yvette was working on Amanda to consider some anal action for the film. The two had coffee one day at Yvette's.

"I don't know, Yvette. I'm afraid it will hurt," Amanda complained.

"I've done it with Vince, it's not my favorite, but it's not bad. It takes a little prep, some cleanup before, but it's ok. We can start with a small butt plug and work our way up," Yvette coaxed.

"I've always refused Jeff when he's asked," Amanda said, "does he know yet?"

"No, it's not in his script. The scene calls for you to be taken "doggie style," and then Stan will pull out and insert it in your ass. You'll be cleaned and lubed ahead of time. We think the element of surprise will enhance Jeff's actions," Yvette said.

"Then what?" Amanda asked.

"Well, the usual except Jeff will have a 'cleanup on aisle two,' we'll be adding some chocolate pudding to the creampie. Jeff will be a little messy, and your character will go off on him being disgusting," Yvette said.

"I have to think about it, I'm willing to try the anal, but I don't want to turn Jeff into a head case; we've been stretching him every film," Amanda fretted.

"We'll be able to smooth it over with him; he's been professional before when surprised. We don't have much of a storyline left with you two. Our last film will have you two splitting up; we don't know how yet; after that, you can work on individual projects if you want to work past the contracts," Yvette said. "I've got a butt plug kit for you to work with; it has three sizes; obviously, you have to start with the smallest one."

"I'll give it a try. When we broke Jeff in, I just used the largest. How are we going to work our planned sabbatical in?" Amanda asked.

"Well, in the next film, there's going to be broad hints about an IR pregnancy after having lost the first one. Then when you and Jeff get pregnant for real, we'll be filming, just gentle stuff as long as we can, most of the story will be Jeff being humiliated, getting 'nanny' training and stuff," Yvette explained.

"You've got it pretty well mapped out," Amanda said.

"You guys are hot; we get a lot of viewer and subscriber feedback on your films. Going into this project, we said that most of the films in this genre are one ops, where a white boy is humiliated by a black man taking over his woman. Tying a couple together for a series was genius; when we add in the feedback from our regular pervs, each movie gets hotter. Ask Jeff about the financials; we're killing it," Yvette said.

"Jeff said we could all retire any time. He's pushing me to quit after the contract's over. I told him if I quit, I could never go back to just vanilla sex again," Amanda said.

"I hope not; I'd miss my flings with you, girlfriend," Yvette said, planting a kiss on Amanda's lips. Amanda responded by kissing back with an extended French kiss and groping hug.

12
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  • COMMENTS
3 Comments
AnonymousAnonymousabout 3 years ago

Great story. Don't mind bigoted haters. Can't wait until we see Jeff as a real sissy.

gw3ngw3nabout 3 years agoAuthor

I appreciate all comments, even the negs. I am not Julia, if I was I would write in 1st person. The story was written completely before anything was posted, I don't like being ghosted by authors and unfinished stories. There are 19 chapters to this tale. I will not be changing the direction.

Your comments assist me in future writings.

mCyclademCycladeabout 3 years ago

Okay, I'm calling it now. The writer gw3n is Julia, the man hater who wants to fuck Jeff up completely. I see no good ending for Jeff considering how this is going.

No justice in this story, the bad guys always win.

From how I see it he's going to end up castrated, feminised and raising someone else's baby or commit suicide. I would prefer the suicide ending to his continued suffering.

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