The BBW's Bottom Boy: A Pegging

Ivan obediently reclosed his eyes, but he couldn't apologize because he had a dick in his mouth, although he'd caught a glimpse of some red lingerie... his favourite colour.

"Good faggot," Angela soothed, her tone flipping 180° in a heartbeat. Having been a submissive her entire life, but recently having been intensively trained in dominance by Jen, she was just roleplaying being his ex-wife for now, but more viciously. "Now suck my cock, faggot."

Ivan was completely confused. But hard. And excited. He had a dick in his mouth! Sure, it wasn't a real one, but nevertheless he had a dick in his mouth. But then he recalled the things he'd read about intimate pegging and how it could build communication and love in a relationship, and he relaxed. He wasn't gay. He wasn't actually a faggot. He was with a woman for Christ's sake, you call that gay? He was with the woman he loved. He was simply complying with a proven therapeutic reversal of roles... he was just being the wide receiver instead of the quarterback... he was likely about to become the fuckee instead of the fucker... and this entire scenario was turning him on.

As Ivan began to bob on the cock, Angela encouraged him with some positive reinforcement, "That's my good boy, faggot. You're a natural little cock sucker."

Cock sucker. That was a new term, at least when it was being applied to him. Just another term intended to humiliate him. Yet although it did indeed humiliate him, it also excited him... it encouraged him... and he began bobbing faster, and methodically trying to take more and more of that cock into his mouth.

"Shit, you look so hot sucking my dick," Angela said, as she filmed him with her phone.

He was unaware of the phone, but her words encouraged him even more, since his untrained efforts seemed to be impressing her.

"Now get my dick nice and slick for that virgin ass of yours, my pretty cock sucking faggot," Angela listed, finally removing for him any shadow of doubt about what her immediate plans were for him.

Pretty. Cock sucker. Faggot. Each demeaning term a humiliation. But each of them also a stimulation. Ivan continued bobbing, not at all protesting... neither inwardly nor outwardly... what was being portended for him.

"Do you like sucking my dick?" Angela asked, pulling out of his mouth.

He didn't hesitate, being so consumed with obedience as he answered, his eyes still obediently closed, "Yes, yes, I love sucking your dick."

Angela smiled at his attitude's complete about face in only a day. "And you long for me to fuck that pretty virgin ass of yours, don't you, faggot?"

"Yes, yes, please bend me over and fuck my ass with your dick," Ivan replied earnestly, feeling so desperate to please her, and so curious to know the experience of being fucked.

"You're sure?" Angela asked, as she anchored her hands around his head, slid the cock into his mouth and roughly face fucked him, forcing him to gag, as all six inches slammed completely into his mouth.

Ivan tried to breathe through his nose and to resist gagging, as he was used in a way he'd never stooped to using a woman. He gagged a couple of times, but he didn't back away...like the good cock sucker he now aspired to be.

"Learn how to breathe through your nose, cock sucker," Angela advised, then foreshadowed, "you'll soon be taking dicks a lot larger and beefier than this puny beginner's toy between your cute cock sucking lips."

Ivan couldn't believe how her torrent of humiliation just kept coming and coming, nor how it continued to turn him on, while he didn't catch her mention of some larger, and perhaps even real dicks a bit later.

"Ready for me to break in your back door, bottom boi?" Angela asked, trying to come up with as many derogatory names as possible.

"Yeah," Ivan said from a complete daze, as the cock was pulled out of him, thus freeing him to speak.

"Yeah, what?" Angela queried, slapping his face with her cock.

"Yeah, I want you to take my anal virginity and turn me into your faggot slut," Ivan said, struggling to believe those self-compromising words spewing from his mouth.

"I know you do," Angela smiled. "And your humble request is granted. So spin around and offer me that asshole of yours."

"Okay," Ivan agreed, so excited at what was about to come, the inevitable and imminent pain didn't faze him at all.

"Okay, Mistress," she corrected, thinking it would be cool to be called that... usually that was the term she used when addressing Jen.

"Yes, Mistress," Ivan said, this new belittling requirement only adding to his excitement. "Please fuck my ass."

"You're sure?" she asked once again, strolling over to her dresser and retrieving the lube she'd considerately bought for tonight.

"Yes, Mistress, I'm sure," Ivan said, adding, "I'm here to obey your every order."

"Good answer, faggot," Angela approved, as she generously lubed her dick. She didn't want to tear his ass apart, which was why she was wearing a short, narrow cock; she wanted him to enjoy it, to love it, to beg for it, and then she could begin advancing her challenges for him to longer and fatter ones.

"Anything for you, Mistress Angela," he said, wondering at that moment how Angela had become such a different person. She sounded more like Jen than herself. Was there any way she might have put her up to this?

"Remember that pledge," she advised, as she placed herself behind him.

Ivan tensed up as she climbed onto the bed... the mixture of excitement and fear still swirling inside him. He'd already agreed to what was about to happen, and yet his excitement was tempered by nervousness.

Angela felt a rush of excitement as she positioned her dick between his ass cheeks. She ordered, "Pull your ass cheeks apart and offer up that asshole, bottom boi."

Ivan obeyed, "Yes, Mistress."

She experienced another rush of excitement at his obedience. She placed the cock against his asshole and slowly pushed forward.

"Oooooooooooh," Ivan whimpered in a voice that wasn't particularly manly, as intense pain coursed through his entire body.

"Your asshole is now swallowing my dick," Angela reported, and she watched in awe as the dick disappeared into his ass. She'd always before been the one whose ass was being filled and she loved it, but now it was also pretty exhilarating to be the delivery guy.

"Oh, fuck," Ivan groaned, as the dick continued drilling deeper into his ass. It seemed to keep going and going endlessly.

"No fucking yet," Angela smiled, "but soon," once the entire cock had been engulfed, and her flesh was resting against him.

Ivan let out an indistinguishable sound as he felt her leaning against him. The dick was all the way inside him. Pain burned in his ass, yet his cock remained rock hard.

"Remember to breathe," Angela encouraged, knowing that was important, remembering the initial pain she had felt when she was first ass fucked, or when she'd first taken a ten-inch cock, or even the crazy twelve-inch living BBC she'd once taken... but every single time the pain would fade and the pleasure increase, while she was ass fucked with growing vigour.

"Okay," Ivan said through gritted teeth, and he did indeed breathe.

"Now I'm going to begin pounding this pussy, and you'll begin to feel pleasure you've never felt before," Angela said, as she began slowly to fuck him... calling his ass a pussy for the first time, but far from the last.

Ivan noticed the reference to his ass as a womanly orifice, but he couldn't spare the attention to process it, as he focused entirely on Angela beginning to fuck him.

"Just relax, Ivan," she encouraged gently, seeing him stiffen, which would only increase his pain.

"Okay," he said, his head light, and noticing her using his name for the first time during this humiliating yet stimulating experience.

"Soon, as soon as your body adjusts to this violation, you're going to love this," Angela said, wishing him to enjoy this journey, wishing him to receive the pleasure she'd read men could experience... and also beginning to train his ass for the future, which almost certainly would include his accommodating some actual big black cock.

"Okay," Ivan repeated, this dick sliding in and out of him the weirdest sensation ever. It was unnatural, yet natural. There was pain, but a slowly decreasing pain.

Angela slowly fucked him, enjoying listening to his whimpers and moans, which weren't feminine per se, but neither were they very manly.

This went on for a couple of minutes... no talking... just slow fucking....

His pleasure continued rising as the cock continued to slide in and out of him... and as the pleasure overtook the pain, Ivan wanted more. He wanted to be fucked harder. Faster. Rougher. He now desperately needed to get fucked! "Harder, please," he moaned sheepishly.

"What did you say?" Angela asked, even though she'd heard him. He'd persevered to the next stage, so now she wanted him to beg.

"I asked you to fuck me harder," Ivan said more loudly, his humiliation quelled by his lust.

"Fuck which part of you harder?" she asked, pausing deep inside him.

"Fuck my ass harder, please," Ivan pleaded, desperate to feel her cock slamming into him.

"Are you saying you want to be my ass slut, faggot?" Angela asked, as she bucked her hips into him, but only once.

"Yesssss," Ivan moaned, as with that single thrust the cock had somehow plumbed a newer depth inside him, creating some new pain that somehow delivered more pleasure as well.

"Tell me Ivan, tell me what you want, and what you are," Angela demanded, as she gave him five hard, deep thrusts, before once again holding herself rock steady deep inside him.

"Oh fuuuuuck," Ivan moaned, as he was fucked hard as if he were a she. She stopped yet again, frustrating him immensely, but he only said with the pleasure still consuming him, "I want you to fuck my ass hard, and to use me like a cheap slut."

"And what are you?" Angela asked, generously bestowing upon him another five hard, deep thrusts.

"I'm a faggot, a bottom boy, a slut for cock," Ivan listed, each term humiliating, and yet each one of them sending pulses to his penis.

"And I have your assurance I can fuck this ass whenever I wish?" Angela asked, followed by seven rough thrusts.

"Yeessssssss," Ivan moaned, knowing that now he'd experienced this pleasure, he could never go back to a life without sodomy, "you may certainly fuck my faggot asshole anytime you like."

"And henceforward you'll be my bottom boy pet who obeys every order his Mistress demands?" Angela queried, lovingly slamming into her pet's ass ten conditioning times.

Not thinking at all straight, nor using the head on his shoulders but his other one, he agreed with nary a thought of consequences, or of Angela's long-term plan (which he was totally unaware of), or the knowledge of his declarations being recorded for later use (nor that either, sorry Charlie), such as blackmail and further humiliation, responded, his voice sounding disconcertingly high (to any real man, but not disconcerting at all to any real woman), "Yes, I'll obey, Mistress."

"Because I own this ass, don't I?" Angela asked, giving her newly acquired ass a resounding slap! followed by ten more powerful plunges into it.

"Yes, yes, yes," he declared, his cock throbbing and feeling ready to burst at any moment.

"Good faggot," she smiled, as she began to fuck him hard, loving to be told of his desperate desire to be fucked, and loving the very unmanly moans emerging from his mouth.

"Oh yes, fuck me, fuck my ass," Ivan moaned, feeling intense pleasure unlike anything he'd ever felt before. He couldn't believe how getting ass fucked was even more pleasurable than getting a blow job or fucking someone. The helplessness of his being completely unable to control his (hopefully upcoming) orgasm, and his throbbing willy bouncing about willy-nilly, added to the uniqueness of the situation.

"You like it rough?" Angela asked as she slammed into him. Even she was surprised by how quickly he'd become a lustful cock-taking faggot. She should have bought him a bigger strap-on.

"Yesssss," he moaned, his cock really throbbing, feeling ready to erupt at any moment.

"How's your baby dick feeling?" Angela asked, unable to see if it was still hard.

"So hard," he answered, hating her constant reminders of his dick being so small and referring to it as a 'baby dick'.

"Because you've discovered the inner you is a faggot who loves dick, haven't you?" Angela taunted him some more, feeling so stimulated by degrading him. She couldn't explain it, but tonight's constant rush of adrenaline was way more exhilarating than any drug (and she'd experimented quite a bit in her younger days).

"Yes, I do love dick," Ivan moaned, his mind a muddled mess, since all he could think about was the pleasure flowing inside him, and his dick that was admittedly tiny, but was still desperate to come.

Angela got to drilling his ass, listening to his growing moans and whimpers, and she wondered if he could actually come just from getting ass fucked. It was possible, since she herself had her most intense orgasms from getting dicked in the ass. But she had no idea whether men could manage that. She realized, as she was getting tired from fucking him, that being the giver instead of the receiver was a lot more work, and also now that she'd fulfilled everything Jen had ordered her to do, unless he came, she had no idea when to stop.

Her quandary was resolved for her when a few rough strokes later, as her big body slammed into his one more time, he grunted and began trembling wildly.

"Are you coming?" Angela asked, surprised.

"Yesssssss," he moaned, with the most intense pleasure ever coursing through him... he couldn't believe any orgasm could be this intense... usurping every ounce of energy in his body, so he collapsed forward, even as cum continued spewing out of his dick and onto the bedsheets.

"Wow, you really are a born faggot!" Angela exulted, as her dick slipped out of his ass and she admired the gaping hole she'd molded.

"God," was all Ivan could muster as he continued to come... this easily the longest orgasm he'd ever had... way longer than his usual three-second pleasure.

Angela slipped out of the strap-on, her pussy on fire, flipped her faggot boy onto his back and sat on his face... even though he ended up lying in his own cum. "Since your baby dick never gets me off, use your lone extremity that does please me."

Ivan hated knowing she was right: his dick was too small to satisfy her... which is why he'd always been eager to go down on a woman... something he'd done for Jen a lot... she having told him early on she only came from oral... and only when she broke up with him had she revealed that wasn't exactly true... it was only his dick that did nothing for her. She didn't even say it in a deliberately mean or hurtful way, she was just finally telling him the truth. He'd hoped Angela was different, since until last night she'd seemed to really enjoy being fucked by him... but alas, that too was all a charade.

However Angela did enjoy his tongue... he was pretty good at using it... and in just a couple minutes, she was coming on his face.

Once her orgasm had run its course she got off of him and asked, now in a sincerely sweet manner, "Did you really enjoy all that? I kind of got a little wild."

"Yeah, you did," Ivan agreed, sidestepping answering the question.

"You didn't answer my question."

"I'm a little embarrassed by my answer."

"Well, your spewing cum all over our sheets while I pounded your ass and called you a faggot, kind of speaks for itself, doesn't it?" Angela smiled.

"I guess it does," he sighed.

"Then don't be ashamed," Angela said. "I think it's cool."

"What... exactly... do you think is cool?" Ivan asked, still confused by how his body had reacted, and how he'd just given in completely to the super aggressiveness of a fiancée he'd thought until recently was rather submissive.

"That you go for dick."

"To be perfectly clear, I only go for your dick."

"If you say so. For now," she shrugged, getting off the bed and heading to the washroom to take a shower.

Ivan lay... still in the wet stickiness of his own cum... trying to understand the ramifications of what had just occurred, the things he'd recently promised, and her ominous words 'for now'. Shit... he was in so deep... he then he laughed to himself as he got up to change the sheets... like she'd been just now.

.....

"Ivan actually came from being ass fucked?" Jen asked a day later, even though she knew he had, as she'd watched the new livestream that was set up just for her last night.

"Yeah, and he came buckets," Angela said, still living in the afterglow of her very first pegging.

"It was pretty hot to watch," Jen said, adding, "I came on some cute high school girl's face twice while I was watching."

"I don't know how you manage to get so many girls agreeing to eat your pussy within a few minutes of meeting you," Angela said, as she watched the chubby older woman licking Jen at this very moment.

"It's a gift," Jen shrugged, having picked up this particular grandma at the mall. She'd never before seduced a woman in her sixties, and thought why not. Fifteen minutes later she was back home, and the grandma, who'd never eaten a pussy before, was lapping away, and had now been doing so for fifteen minutes nonstop.

"Oh, I know it is," Angela agreed, knowing Jen's cunt was the addictive gift that kept on giving and giving.

"So next, we make him watch hypno sissy videos," Jen said.

"What are those?" Angela asked, as Jen snapped her fingers. "Go eat my friend," she ordered.

"I should go," the elderly woman demurred. She still couldn't believe she'd not only come home with this stranger, but had then willingly crawled between her legs and licked her first-ever pussy endlessly.

"Do you really want to leave?" Jen asked, already knowing the answer.

After a brief pause, as she looked back at the inviting pussy she'd been unable to resist, she admitted, "No."

"Then crawl over there and eat my friend's cunt; her fiancé's dick is too small to get her off, the poor thing," Jen instructed.

"Okay," the elderly woman said, turning around and approaching the nether region of another BBW.

Angela spread her legs and ordered confidently, "Get licking, slut." (She wasn't really all that confident, but she was getting into the habit of imitating Jen, who always was.)

The elderly woman hadn't been called a slut in over thirty years, back when she was one, but she obeyed, crawling between the woman's big thighs, and right up to her pussy.

Jen explained. "Hypno sissy vids are a strange genre of porn, where a woman provides a sexy voiceover for the visual of an endless series of girls sucking cock, getting fucked, taking facials, whatever... and the narrator speaks seductively to the viewer, as if he's each one of those women, " Jen explained. "She both tells him how much he loves doing all those things he's seeing, and entices him to parrot back phrases such as, 'I'm a faggot for big dick,' or 'My ass is always available for a nice cock,' 'I love the taste of cum,' and numerous other post-hypnotic suggestions."

"There is such a thing?" Angela asked, wondering not only that, but what the purpose of such suggestions might be.

"Yeah, they're surprisingly popular, and quite effective in training a straight man into seriously considering how much he wants to serve dicks."

"How would that even work?" Angela asked with a moan, as this elderly stranger licked her.