Subverted Expectations Ch. 04

This is the forth and final chapter of the "Subverted Expectations" story, but it's only the beginning of Steven's saga. Sorry it took so long to finish. Feedback is very much appreciated!

Chapter Four

A wave of fear and anxiety mixed with hope rolled over Steven's mind as he watched his wife get into position above him. He knew it was all too likely that Diana wouldn't be able to resist cumming, but her sudden confident aura was putting his mind at ease. She just might make it.

He was, at least in some small way, comforted by the fact that she was going to give it her all. She was going to temper her enjoyment of her own fantasy so that Steven could get what he wanted.

Diana noticed Steven's worry as she got on her hands and knees above him. "Don't worry honey," she said, attempting to comfort him, "We are gonna get you that big fucking dick."

"She must want this too," he thought, "even if she loses, she may try to convince Olive to give me one anyway. Maybe I can relax a little. Enjoy myself?"

Again Steven was given a front row seat to the action only inches above his face. This time, however, he knew the base of Olive's fat cock at his eye level would be disappearing inside of Diana's eager pussy.

Eager was the proper word to describe Diana, who was now taunting Olive by waiving her ass back and forth. "Let's get this first minute over with so I can relax and enjoy it," she said, "Come on Olive, slide that big boy inside me."

"Oh no, that would make it too easy for me," Olive replied, "You are gonna do the work. Just like Shelby here."

Olive gestured to Shelby and Katie, but with her knees on either side of Steven's head, her thigh partially blocked his view. What he could make out was Shelby squatting over Katie, who was lying on her back right next to him.

"Oh yeah," Shelby replied with a nod, "You'll wanna go at your own pace at first. If you let her do the plowin' the first time, you will lose your mind. You're not used to cummin' like that. Not yet at least."

She was gently easing herself down Katie's shaft, squeezing her kegel muscles around it as she slid down. As if Katie's thick member didn't already create a tight enough fit. "Besides, Hahh!" Shelby moaned as she bottomed out and began grinding and gyrating. "It's our job as little sex dolls to do most of the work while our masters relax and 'unload'. Oooh fuck that dick is sooo deep!"

"Oh, ha... haha," Diana was attempting to hide her excitement at that thought, but she was already dripping onto Steven's chest.

"Well how about it, D?" Olive asked, "Want to go ahead and do your job? Why don't you be my good little slut, and make Mommy's cock feel good."

"Oh, fuck.... Fuck you!" Diana replied, "No talk like that until after I win your little...game."

"Hahaha! Alright," Olive didn't sound like she cared at all, "I won't say a thing, but the clock doesn't start until you fit the whole thing in and start bouncing. If you stop, you lose. WHEN you cum, haha, you lose. Are you ready?"

Diana had to peel her eyes away from Shelby as she bounced up and down, squat fucking herself on Katie's horse-cock. The little size queen was moaning and cussing up a storm, riding on the waves of perpetual orgasm while she swallowed the entire shaft with each thrust.

The sexy tart Shelby, that her husband wanted for himself, already had her pussy ruined for him by his own boss! It was surprisingly hot to think about how her poor hubby's little cock could never again hope to please that little slut.

Biting her lip, Diana closed her eyes and tried not to think about how that would soon be herself. "Alright," she said, "Here we go."

"Won't you need some lube?" Steven asked.

"Honey, I really don't think that's gonna be a problem," Diana answered, "Olive makes me so wet!"

WIth one hand pressed down into the bed for balance, she reached the other in between her legs and spread her luscious pussy-lips with two fingers. Her excitement was audible as well as visible, as her pussy made a squelching sound and gushed out more fluid.

"H... Hah!" Diana moaned, trying to get ahold of herself as her pussy was lubricating itself for Olive's impossibly large cock.

"You can do it ba-," Steven tried to say

"Shh! Shut up!" Diana cut him off as she began to back herself up, "I'm sorry babe, but please just don't say anything!"

She backed onto Olive's head before she had expected to and gasped with a start. Olive said nothing, just knelt there with her hands on her hips and smiled. Diana then removed her fingers, as her lips had already wrapped themselves around the tip of the thick head. All she had to do now was back up.

She took slow deep breaths as she gripped the sheets in front of her and began to ease back. The sound of that little slut, Shelby, impaling herself on Katie began to fade out as Diana focused on the task at hand. To her surprise, she didn't need to push as hard as she thought. She supposed her practice with the dildo had paid off as her vagina began to part and take in this...big, fat, amazing dick.

"Oh, wow!" she thought, "Oh shit. This feels good." She felt a slight ebb in the resistance as she pushed past the head, but the shaft quickly widened again as she slid further. It was then that something started feeling....different.

"Why does this feel so much better than the fucking dildo," she thought, "What is that?" She began to feel a radiating warmth from inside her. The pleasant warmth grew, and grew and without her control, the walls of her vagina began to tighten.

"Oh....god!" she cried, "What is happening to me?" Her pussy had grown a mind of its own, and was eagerly squeezing itself down onto it's mate and pulling it inside deeper. Inch by deliciously slow inch, she was forced back onto the cock. She could feel every tiny bump and ridge made by the thick veins. It was as if Olive was "ribbed for her pleasure".

Shelby, taking a moment to rest atop Katie, with the right side of the bed already soaked, was now smiling at Diana. "Oh... I remember my first time," she said with a sigh, "Should I tell her?"

"Go ahead," answered Katie.

"It's...hard to describe, honestly," Shelby continued, "Well you know how ridiculously long these things are right? Well, with your womb in the way, there is nowhere else to go but...ya know, in!"

"What the fuck are you talking about?" Diana asked, panting.

"You are about half way, you should feel it any second now!"

"Oooohhh!!" Diana cried out, "Oh fuck! Oh my god! Oh my fucking GOD!" She was in disbelief as Olive's thick cock-head eased into her womb. It also surprised her that instead of feeling like what she expected painful childbirth to feel like, it felt good. It felt absolutely amazing, in fact.

"Uh oh!" laughed Shelby, "Was that an org-"

"NO! No it wasn't!" Diana cut her off. "But fuck that was close," she thought, "Jesus Christ, its still going deeper! Yeeesss! Wait...no no!" She was wrestling with her thoughts and feelings.

She briefly remembered what it felt like when Steven entered her at just the right angle. His cock-head would grind against her G-spot and she would rub her clit at the same time.

After a minute or two of that, she would always have an amazing orgasm. But what she was feeling now was an order of magnitude better. Every inch of the inside of her womb felt like one big G-spot, and Olive's head was now stretching it out as it was sucked deeper inside.

Olive was clearly struggling not to express how amazing the tight sensation felt for her as well. She simply clasped her hands over her mouth and softly moaned.

"Oh. My. God," Diana was wide eyed in terror, "You didn't tell me it would be like this! My dildo didn't do this!"

"That's because this is the real thing, honey," answered Katie, "Even if you didn't clearly want this, your body is preparing for its new role as a cock-sleeve. This is what sex was meant to feel like, this is what I plan to do to your husband..."

"Oh, for fuck sake! Please don't talk about that right now."

The others simply laughed, but Steven began to feel the warm stretching sensations from earlier, and a growing emptiness inside him. He couldn't hide how hard he was from Diana, nor could he hide the precum that was being pumped out of his throbbing manhood. He hoped her eyes were still closed.

At about three quarters of the way down, Diana gasped again as Olive's head was now pressed against the top of her womb. For the briefest of moments, she mistakenly thought she had "bottomed out" and that there was no more cock left. This caused her to relax and ease whatever resistance she had given in an attempt to slow her descent.

Diana could only scream with pleasure, when in an instant, her eager pussy desperately swallowed the rest of the length, pulling Diana back with force into Olive's lap. It was like there was a small vacuum inside her, and her relaxing allowed the void to be filled all at once. Olive's fist sized head pushed and stretched into Diana's hyper sensitive womb.

A lightning bolt of relentlessly intense pleasure struck Diana, and it took all she had not to faint. Her legs shook violently and she rhythmically convulsed as her orgasm caused her pussy to repeatedly squeeze down and release its grip. With each shuddering wave from her climax, she sprayed love juice all over her husband's face, and her lover's balls.

"Ooooh!" Diana let out a high pitch squeal, "Fuck! I'm so sorry Steven! Oh god this is soooo good!"

That feeling of mixed pain and pleasure, with which he was now getting familiar, washed over Steven. "I, it's okay, honey," he said.

"Well that was quick," Olive said proudly.

"No! Please!" begged Diana, "We, we didn't even start yet! It's not fair. I didn't know that was going to happen!"

"Haha, okay sure. It's really not going to make a difference, but you can start whenever you are ready," Olive said, clearly not worried at all.

After about a minute or so, Diana's crushing orgasm finally subsided, and she took some deep breaths. "How fast, or deep do I need to...you know, th, thrust? Mmmm," she asked. She really didn't want to have to use that word. Every twitch of her body and every sexy thought she had, threatened to take her to the edge again.

"Really, it won't matter, hun," Shelby answered, "Just go ahead and try nice and slow and shallow."

Diana did just that, with a white-knuckle grip on the sheets she slowly pulled herself forward and off of Olive's lap. She barely cleared half an inch before easing back down. "Is this good?" she quickly asked in a high pitch whimper.

"Okay, clock starts now!" Olive said, holding her phone. She pressed a button and turned her phone down to face Steven, showing him the timer app running.

"She's got this," he thought, "It's already been a few seconds. She just needs to keep this pace. This can't be doing anything for her. It takes a while of hard pounding for her to cum." He was desperately trying to reassure himself, unaware of the mad desire already growing inside of his wife.

After about ten seconds had passed he noticed that Diana's pace had quickened slightly and she was now pulling out a few inches before sliding back down. "What is she doing?" he thought.

"Uh, babe?" he asked aloud.

"Ha... Don't worry. We are still good. Mmmm. This is just...." She trailed off, breathing heavier.

With a long sigh, she pressed herself back, pushing into Olive's lap with a slow deep thrust before pulling out further than she had before. She was now halfway out, about seven inches, before sliding back down a little harder. She kept going at this pace, quietly gasping.

It occurred to Steven that he would have slipped out well before this point, and Diana was only half way up Olive's incredible length. And the half that was still inside of his wife was again more dick than he could have given her, and that wasn't even accounting for the girth. He had never seen any woman stretched to this extent, let alone his wife.

20 seconds

"Ooooohh!" Diana's high pitched whimper accompanied trembling in her legs.

"Um, babe, just slow down," Steven pleaded.

"I, Mmm, I can't!" her voice sounded an octave higher than normal to Steven, "Fuck! Ugghh! I can't fucking stop! I need more!"

"Oh no," Steven thought.

30 seconds

Diana's pace had quickened and Shelby rode Katie's pole to match the depth and rhythm. Everyone in the room was moaning except for Steven.

Diana began pulling away further and just like in Steven's nightmare, her pussy was pulled inside out slightly with each thrust, like it was hugging tightly, not wanting to let go.

"Oh fuck!" Diana shouted, "She is going in and out of my womb! Ugh god!"

40 seconds

"I'm sorry Steven!" Diana cried, now sliding up and ramming herself back down a length twice that of Steven's. "I can't fucking stop! Fuck! It's so fucking good when she is fucking my womb!"

Unable to help herself, Olive reached down with her free hand to grab onto Diana's wide, childbearing hips.

"Oh yes! Oh fuck! Please fuck me, Mommy!" Diana begged, "Your cock is so much bigger than my husband's!"

"Oh my god! Your pussy feels so, ugh, fucking good!" grunted Olive.

50 seconds

"Oh shit!" Diana cried out, as she began hammering herself down onto Olive. "I'm cumming! Please don't look, Steven! Oh god! Oooooohhh!!"

Steven had never heard Diana make any sounds close to the cries and moans that were now erupting out of her. He could always get the occasional "Oh god!" or "I'm cumming!" from his vocal wife, but that was nothing like the high pitched, desperate squeals that she made now. It was made apparent by her cries and incomprehensible swearing, that Diana was having an orgasm on a whole other level compared to anything she had felt before.

Olive put down her phone so she could grab Diana's hips with both of her hands. With a firm hold on her toy, she was now able to slam in and out with her full length. She was in control now, and she didn't care if Diana was ready or not.

"Oh fuck, I'm gonna ruin your tight fucking pussy," Olive said, panting with the effort she put into ravaging Diana. "You fucking want that, don't you? You want me to ruin this pussy for any other dick?"

"Yes! Oh fuck yes!" Diana responded happily, "Claim my pussy! Oh god please claim my pussy, Mommy! It belongs to you!"

Helpless, Steven could only stare as his nightmare came to life. A satisfying, wet, slapping sound accompanied every thrust that buried Olive's third leg into his wife. Her heavy softballs rocking back and forth with the motion, Diana's endless stream of love juices dripping off of them onto Steven's face and into his open mouth.

Olive's dick looked to be almost as thick as Steven's bicep, and it was beautiful. Every time it disappeared inside of his wife, he almost felt like he missed it. Being this close, he could see every detail and shape the tight skin made as it contoured the bulging veins. The gorgeous cock itself, being tightly contoured by Diana's inside out pussy as it tried desperately to hold on to the slick shaft that was giving it so much pleasure.

For minutes Olive tirelessly continued her relentless pounding. His wife didn't seem to tire either, despite being brought to orgasm with each thrust. This too must have been due to the same futa-magic that had caused every other miraculous change to occur.

When the ravenous pistoning finally slowed and stopped, Diana fell off of her mount and collapsed on top of the squirt-soaked Steven. She laid there panting and moaning softly, her legs shaking. When Steven looked down at her straddling his chest, he could see the "damage" that Olive had done to her.

Her half-football shaped, prolapsed womb was pushed several inches out of her gaping pussy. It's entrance at the tip was swollen and loose enough that it looked like he could fit his whole cock inside without touching the walls.

"Oh fuck yeah, that is hot! Look what I did to your wife," Olive teased, "Oh and she came with only five seconds left by the way. I stopped the clock as soon as I felt her pussy start squeezing down on me."

Despite the feeling of defeat, a strange calm swept over Steven. He was in some way relieved that the "test" was over. All that was left for him to do tonight, was to give in and try to enjoy himself as best he could. Though he imagined that wouldn't be too hard. He was painfully aware of how aroused he was by the sight of his wife losing herself in a pleasure he couldn't hope to give her.

But he was still concerned for his wife, who appeared to have fainted. "Diana? D, are you alright?" he asked.

"Oh she's out, hun," answered Shelby. Her blonde hair was matted with sweat and stuck to her blushing cheeks. She had apparently also enjoyed herself and was gently grinding back and forth on Katie. When she slid her hips forward he could see the tip of Katie's insanely long cock, bulge out just below her rib cage.

How that experience wasn't painful to Shelby, was beyond him. Instead she seemed to enjoy it more than anything else, and she even pressed down on the bulge with her hand to add more pressure, massaging Katie's cock-head.

"But I know just what'll wake her up!" she continued. Dismounting Katie with a wet sloshing sound, and a small deluge of pussy juice, she knelt beside Steven and the resting Diana. She then reached down and began massaging Diana's outstretched womb with one hand.

Diana writhed and gently moaned in response. "Uh... That's. That's good!" she said, half awake.

Stroking her wet and swollen womb with one hand, Shelby pushed three fingers inside of it and began swirling them around.

With a start Diana came to. "Holy shit!" she shouted, "Did I pass out? And fuck me, that feels good!" She was now back up on her knees and smiling at Shelby as she continued to stroke and massage her "insides".

"Did I make it?" she asked, smiling.

"No, you just couldn't help yourself," answered Olive, "My dick feels too good doesn't it?"

All the women were giggling with each other and sighing in their state of euphoric pleasure. Olive and Katie were stroking themselves proudly, while Shelby stroked and now gently fisted Diana's exposed womb.

"Oh sh..shit!" Diana said, not appearing very disappointed at all. "I'm sorry Steven, but Olive's cock... It was just too much! You have no idea how good it feels to finally be filled up like that! And she could keep up that pace for soooo long. God, I've never been fucked like that."

Steven shuddered at those words. He knew he would have finished seconds into pounding that hard and fast. Especially if he could ever experience his wife's pussy squeezing down that tightly. "God what must that feel like?" he thought, "To be so big, that you can stretch somebody like that. My wife must have felt like a virgin to her."

"Oh, Steven!" Diana gasped, noticing how hard he was. "You poor thing! Your poor little cock is so hard from watching Mommy fuck me!" she spit on his cock and began stroking it, deftly twisting and teasing his sensitive head. "You liked watching didn't you?"

".....Yes," he replied.

"Did you see how hard I came? Oh fuck Shelby, that feels good! Did you see me take that big, fat dick all the way?"

"Yes"

"Thank you baby! Thank you for sharing me with Olive!" she said as she started to dismount him. "I know you want to fuck me baby, but right now I need more of Olive's cock."

She gestured for Katie to give her some room as she laid down on her back next to Steven. "I really am sorry honey," she said, as she brought her knees up on either side of her beautifully, full breasts and held onto them with a hand behind each knee. "I'm still your wife, but I'm Olive's cum-dump tonight. Oh fuck this is hot! Olive is ruining me, and you can't do anything about it!

"Oh fuck. I'm sorry but this is sooo hot!" she continued, "Please try to enjoy it! I want you to experience this with me. I still love you."