Subverted Expectations Ch. 04

"I know," was all he could say in response. He was hurt, but he couldn't deny he was having fun. A sudden worry did cross his mind though. His wife was now in her favorite position "the mating press" which reminded him that he wasn't actually sure if she had taken her birth control that month.

"Please, Olive," Diana begged, "I need your huge cock! Please fuck me like this! Fuck my slutty pussy!"

"Mmm you got it, slut," Olive didn't need much convincing. She strode over to the foot of the bed and climbed on toward the naughty wife who was presenting herself to her new lover. On her knees now, she taunted her prized fuck-toy by rubbing the head of her cock all over Diana's outstretched womb.

"Oh fuck," Diana said laughing, "Please don't tease me, Mommy. I'll do anything!"

"Anything?"

"Anything! I need you inside of me!"

"I know what would be fun," Olive had an evil grin on her face, "How about you let Kat take your ass while I take your pussy?"

"Ooooh my god that would be hot!" Diana agreed, but then she paused for a moment to consider. "But I have a better Idea."

She turned to look at Steven. "I want Steven to have some fun as well. He needs to know what he's been missing," she paused, smiling at him, letting her words sink in before elaborating further. "I want to watch Kat fuck my poor little hubby. I want him to feel what it's like to be completely filled."

As she spoke, she stared right into his soul. They knew each other better than anyone else did, better than themselves. And she knew what this was doing to Steven. They had never brought up the subject of anything going near his ass, but somehow she knew he wanted it. Needed it. That he would love it.

Steven's heart began to race even faster. Was it dread? Excitement? He realized too late to hide it, that he was squirming and panting in helpless excitement. His dick was visibly throbbing and oozing a comparatively small gob of precum. He glanced down at his boss Kat, standing at the foot of the bed. Her own cock was throbbing and leaking precum as well, far more than Steven produced.

"Oh fuck," he said fearfully, staring at his boss. The woman that signed his reports, approved his office's expenses, gave him performance evaluations, was now going to fuck him?

"Are you sure, Diana?" Katie asked, "You sure I can fuck your husband? He won't be the same after..."

"Um, hello?" Steven asked, a desperate laugh escaping him, "Shouldn't you be asking me?"

"Yes Kat," his wife answered for him, "He wants it. Look at his poor little dick throbbing!" She then looked at him smiling, and raising both of her eyebrows. There was a knowing look there like, "Come on dude, I'm doing this for you. This will be fun! Get with the program!"

"Oh yeah," Shelby said, kneeling down beside him and gripping his cock hard at the base. "He definitely wants it! His boy-cock is so hard! Give it to 'em good, boss!"

"What, what? Hold on!" he pleaded, trying to wriggle out of Shelby's grip.

"Steven stop," his boss commanded. Olive and Diana looked on in excitement as they continued some teasing foreplay, clearly waiting to begin.

Katie continued, "I am your boss, Steven. There is a chain of command here, and you," she laughed, "You are at the bottom. You are THE bottom. Haven't you noticed what has been happening tonight?"

The dread or excitement, or whatever he was feeling, was amplified now. He stared in wide eyed amazement at Katie, before looking to his smiling wife, and back.

"We have been grooming you. We want to make you and your wife, ours. And we want you to WANT it. And you are going to obey all of us. Even Shelby, your 'subordinate' haha!" Katie's laugh was over quickly and now she simply stared at him and stroked herself.

"Mmm that's right hun," Shelby assured, "Just give in, and you'll enjoy it! Now I'm gonna free your legs so our boss can get good access, and you aren't gonna fight it. You understand? If you fight me, I'll have to sit on your face!" she smiled at that last part.

He nodded, his heart pounding in excitement. The feeling of tightness and stretching around his prostate came back. This time even more intense and pleasurable. He could feel his rectum widening somehow. That same magic turning HIS body into a "cocksleeve" as Katie had put it. Despite his fear and apprehensions, the thought aroused him immensely. He wondered if it was BECAUSE of his apprehension and fear, that he felt so turned on.

Shelby undid the straps around his ankles and grabbed on to them herself. Steven then kicked gently and shouted, "No! Please don't, Katherine! Your cock is too big! It won't fit!" He felt he could have won an oscar for his performance.

"That's it!" Shelby said, in a "I told you so" tone. Still grabbing his ankles, she mounted him. On her knees facing the foot of the bed, she slid her calves under his shoulders and skootched back until she was hovering over his face. "You asked for it," she said before sitting down onto his already open mouth, his tongue sticking out eagerly.

She buried his face in her ass cheeks and wiggled slightly, seating herself down comfortably. Steven's tongue was forced to explore deep into her gaping ass hole. She tasted delicious. Shelby suffocated him for a little longer, feeding him more and more of her ass hole as she leaned into him.

"Oh yes!" he heard Diana say, "Make my poor husband eat your ass! Oh fuck..."

He was helpless to resist, with his arms still tied up above his head and his nose buried in her crack, he could do nothing but hold his breath. After about a minute she finally relented and pulled away from him. His face was wet from his own spit that his dainty little subordinate had smeared all over him with her grinding.

"You get it now?" Shelby asked him, "At work I kissed your ass, but now you eat mine! Now you're gonna take Boss's big dick!"

"Oh god," it was easy for him to feign fear. Almost too easy. "Please Katherine!"

"I can see your ass winking at me, and your dick is throbbing like mad," she explained, "I know you want this. Besides, your wife already gave me permission. Your ass belongs to me now, Steven. Don't worry, you will love it!"

He was sure the winking she was referring to, had something to do with his pulsating prostate. On and on it stretched and swelled up inside him, growing in size and radiating warm, tight, pleasure.

Holding his legs wide, ankles up, Shelby had a clear line of sight to the reaming he was about to receive. She let a long strand of spit drip from her mouth onto his puckered ass hole

Keeling in between his legs, Katie rubbed the head of her cock up and down his ass crack, spreading Shelby's spit and her precum. Then she began just poking and prodding at his ass hole with a smile.

"Oh yes! I'm so excited for you, Steven," Diana exclaimed, "I want you to fuck me when Katie fucks him." She was now staring into Olive's eyes, still holding her knees and spreading herself wide open for her new dom.

"Mmm you got it," Olive replied. She was still rubbing her slick cock-head around Diana's prolapsed womb.

Shelby sat up on her knees just enough to give Steven a view of his spread legs, throbbing penis and normal sized balls. Below them a massive rod of flesh, not just a penis, but a real cock, was poking back and forth. Katie was smiling as she prodded him, just enough to open his sphincter slightly.

Now with each thrust, she pushed just a little further. Steven could feel warmth as her tip gently penetrated him, and squirted out its own lube inside of his ass. That was clearly the key to unlocking him, as the thick, warm, tingly futa precum spread itself around inside of him, filling his ass.

"Oh fuck!" Steven shouted and gasped, as he instantly loosened and with the next gentle-as-ever prod, Katie's immense head popped inside of him. Reactionarily, he tightened down as if to block it or push it out.

"Oh shit! Oh my fucking god!" he shouted, realizing his mistake too late. Instead of forcing it back out, his sphincter clamped down tight below the head, locking it in place. And the instinctual clenching of his anal muscles also squeezed his prostate up against the welcomed intruder.

His actual prostate wasn't directly touching anything in his ass, but the swollen gland had expanded and wrapped itself partially around what used to be his one-way-street of an anal passage. It was forced in tight against the outside of his stretched rectum, which itself was tightly gripping Katie's head. Even though she had only penetrated him with a fraction of her length, her head was big and long enough to reach his P-spot, and now Steven had started something he couldn't stop.

As if he wound up an old child's toy that was now moving on its own, his prostate throbbed and throbbed along with the muscles surrounding it. Without his control, he was now desperately milking his prostate on his boss's huge head.

"Oh holy shit! What the fuuuuuck!" he shouted, "That feels so fucking good!"

Diana moaned while gazing at the sight of her husband shaking in pleasure. Katie just knelt there with her hands on her hips. Smiling, she let Steven milk himself to orgasm on her dick.

At that moment Olive grasped Diana's Womb with both of her hands and forced the tip against her head.

"You ready slut?" she asked.

"Oh god yes, Mommy!" Diana's attention was immediately on her. "My pussy is always ready for your fucking amazing cock! Mmmm fuck, I belong to you now, Olive!"

At that Olive pushed her head into Diana's already lubed up womb. Diana's new hole opened up to her like a flower would to sunlight, letting her penetrate as if it was always meant to. For a time Olive did nothing but squeeze down on Diana's womb as it wrapped around her fist sized head. Simulating the experience that her husband was having.

"Oh fuck yes! Oh my god Olive that feels so good!"

"Mmmm you like that?"

"Yeees! Use my womb like a fucking toy! Oh god!" she was already cumming as Olive squeezed, twisted, and stroked Diana's exposed womb around her head.

Hearing the high pitch moaning and swearing coming from his wife, Steven knew she was already cumming again. Something that usually took him an exhausting twenty or so minutes of foreplay followed by hard pounding to get out of her.

His wife didn't orgasm easily, compared to his former lovers. It was usually hard work for Steven, but Olive didn't even have to break a sweat. Her beautiful cock was so amazingly large that it's existence alone was enough to draw more pleasure out of Diana than Steven ever could.

The thought of Olive so easily bringing his loving wife to orgasm, filled him with lust. But right now the feeling of the prostate milking he was unintentionally giving himself was competing for his attention.

"Oh fuck! Katie!" he cried, "I'm gonna fucking, oh god, I'm gonna fucking cum!" His orgasm closely followed his wife's, and in unison the couple entered orgasm nirvana together.

Shelby sat down hard on his face again, muffling his screams with her ass cheeks. This did little to quell his full body orgasm, if anything, his cruel treatment by his subordinate expounded his pleasure. He thought briefly that this was the intent.

To make things "worse", Katie timed her relentlessly fast stroking of his wet cock to coincide with the gradual dulling of his prostate orgasm. Just when the throbbing and convulsing were slowing down, she wrapped her thin, nimble fingers around his disappointingly normal sized "manhood", and began stroking with the pace of a jack hammer.

Steven was instantly brought to another crippling orgasm. He bucked wildly and squirted rope after rope of cum, as he orgasmed from his cock and ass all over again. His muffled screams only serving as a vibrator for Shelby.

After a minute or so, Steven finally returned to earth and woke up. He had fainted from either the oxygen deprivation Shelby gave him, or the earth shattering orgasm Katie had. As his senses returned to him, he realized that Olive was now balls deep in the mating press with his wife, pistoning in and out of her eager, squirting pussy.

Diana was a mess. Tears of joy and agonizing pleasure were rolling down the sides of her face as she stared up into her lover's eyes. Her cheeks were flush and wet with drool, and she still wore the choker collar that labeled her as Olive's property. The same choker collar that had once fit snugly around Olive's immense shaft.

Sound had not returned, but Steven could see and now feel that Katie had pushed herself deeper inside of him. He clamped down again in reaction and felt an indescribable sensation of being full. Being complete. Katie had used the time she was given when he was passed out to ease in and out deeper and deeper into Steven's tight ass. Shelby was lying down to his left and gently teasing his overstimulated cock.

He looked up into his boss's eyes as she continued slowly thrusting, and the ability to process sound returned to him.

"Oh my god, Katherine," he said, sighing, "I want to be honest, but this is embarrassing."

His words were made harder to hear by the sound of wet slapping and ceaseless moans coming from his wife and roommate.

"Oh sweety," she looked down at him with a motherly expression, as she gently reamed him deeper and deeper. "It's okay. We are well past inhibitions and judgements at this point. Mmm, fuck me your ass feels good," she paused to mention before continuing, "You can tell me anything, Steven."

Steven's heart skipped a beat at hearing Katie tell him he felt good to her. He was being a good little toy, and he was making his boss feel good. He felt...proud. Not to mention satisfyingly full. Like he had lived his whole life empty and he never knew true happiness. Was this how his wife felt? He knew she loved him, but he couldn't give her this.

He wanted Katie to know how he felt. Just like his wife was giving herself to Olive, giving in to the pure rapture, he wanted to give in to Katie. He wanted to confess how amazing she made him feel, and how he wanted to pleasure her. That wasn't quite it though. More accurately, he wanted Katie to take pleasure from him. In him. He wanted her to use him, and he wanted her to love doing it.

"I, but," he stammered, glancing at Shelby. He might now feel comfortable sharing his feelings with Katie, but he didn't want to give Shelby the satisfaction.

"Oh don't worry about me, hun," Shelby said, noticing his discomfort. "I know exactly how you feel. Trust me!" The look in her eyes said she was clearly telling the truth. And of course she was, who else would know better how it felt to have Katie inside you.

"It's just that," he paused again, trying to think of the right words. But the longer he waited, the more he felt Katie inside of him. He wanted to describe how he felt in a way that would allow him to maintain some semblance of dignity. He still wanted to remain strong, he wanted to remind everyone that this was a one-time-only event and that he still wanted to have a real cock of his own. He didn't want to forever remain the "bottom" for Katie or Olive to use as they pleased.

Despite the growing part of him that was completely accepting of his new role, he didn't want to outwardly appear as he felt inside. He didn't want anybody to know that he was falling utterly, head-over-heels in love with Katie's cock. The only problem was, as he was pondering what to say next, he was perpetually distracted by just how good it felt to be Katie's "bottom". She was being so gentle, slowly and steadily sliding half way in before pulling all the way out, pausing to go even slower when Steven's sphincter opened and closed around her thick cock-head.

Every time she was completely out, time seemed to slow down as Steven found himself anxiously awaiting the return of the thick, warm, precum oozing mass. And every time she gently prodded him, she waited for Steven to reflexively loosen his ass hole and invite her in. The fact that he was doing this without his complete conscious control was also arousing to him. Just like his beautiful wife's pussy was mindlessly reacting to Olive, his ass was mindlessly reacting to Katie. And it felt so good to let it.

Katie's delightful thickness, repeatedly pushing past his hyper sensitive and enlarged prostate, was finally too much for him. The part of him that wanted to maintain his façade of modesty, lost out to the part of him that wanted to be truly honest about what this was doing to him, the part of him that wanted more!

As Katie once again slid into him with another teasingly gentle and shallow thrust, Steven wrapped his now unbound legs around his boss's waist and pulled her in deeper. He cried out in pleasure as he finally filled the void inside of him with her long, thick cock.

"Oh fuck it!" he shouted, "Katherine, you make me feel so good! You are so fucking big!"

"I knew you were enjoying this, Steven," she replied with a knowing, loving expression as she stared at him. "You almost took me to the hilt. You want more?"

"Yes! Oh god yes!"

"Beg," she said as she grabbed the underside of his knees and forced his legs back as far as they would go on either side of his torso. He was now in the same position as his wife, if not quite so flexibly bent, completely and helplessly opened up for his master to plunge as deep as she pleased.

"Oh please, Katherine," he was too used to using her full name, "Please fuck me as deep as you want! My ass is yours! God your big, fat dick feels so good!"

"As you wish," she quickened her pace slightly and didn't fully pull out with each thrust. But now she was bottoming out inside of him. Reaming his ass thoroughly with her entire incredible length.

"Fuck me!" was all he could get out as his eyes rolled back in pleasure. It felt so satisfying. This is what he was missing his whole life, and now he understood what his wife was feeling. Steven now squeezed down willingly, multiplying the pleasure for him as well as his boss.

"Oh yes!" she responded to the tightness, "Be my good little boy and squeeze my cock with your ass! Fuck yes, milk your boss's cock, Steven"

It was like she knew just what to say. She leaned into the boss, employee power dynamic, and forced Steven to remember his place. Thus began the perpetual bliss of his prostate orgasm. Her command bypassed any hesitation or resistance Steven had, and he eagerly obeyed, squeezing down even tighter. His prostate gripped tightly between his anal muscles and Katie's rigid futa-cock.

"Yes Katherine," he was able to say, before incoherent grunting and swearing were forced through gritted teeth. He threw his head back and strained his quivering muscles in his full body orgasm.

To amplify his pleasurable torment, Shelby decided to lean her head in between the two writhing bodies and suck on Steven's cock. Allowing the now rapid pounding he was receiving to rock his cock in and out of her warm, moist mouth. Steven entered another dimension of pleasure, as the endless throbbing of his prostate matched the rhythms of Katie's thrusting, and his own spasming and cumming cock.

"Oh fuck yes. Good girl, Shel. He just got even tighter!" mentioned Katie, before continuing the dirty talk. "Tell me how much you, Ugh, love my cock, Steven! Fuck! Tell Mommy how much, ooh, bigger she is than you! I wanna hear it!"

Miraculously, Steven was able to regain enough conscious control over his body to reply, "Oh my god I love it. I'm in love with your dick! It's so fucking huge! Ugh fuck me, you are so much bigger than me and I love it! Ugh! My boss is a fucking girl, and her huge cock makes mine look so small!"

"Mmmm, yes! That's it! That's what I like to hear!" she said, biting her lip and rolling her eyes.

Shelby had detached herself from Steven's oozing cock and was untying his hands now. "I don't think we need these anymore, do we Steven?" she asked.