The BBW's Bottom Boy: A Pegging

Summary: Man's BBW ex-wife coaches his BBW fiancée in pegging him.

Note 1: This is dedicated to the real Ivan who requested this lengthy tale.

Note 2: Thanks to Tex Beethoven and Robert for editing this story.

Note 3: Note this is a 2021 Valentine's Day Contest story, as love comes in all shapes and forms.

The BBW's Bottom Boy: A Pegging

"He never tells me what he wants," Angela complained, sipping her wine.

"That's because he had me to tell him what he wanted to do for twenty years," Jen, Ivan's ex-wife, told his current fiancée.

"He can also be rather tentative," Angela added. It was weird, Jen was her fiancé's ex-wife so she was supposed to hate her... but the divorce was amicable, and with their kids now being adults, it had ended with the former couple remaining friends. (Actually it was a bit more complex than that: Jen had decided to send him away for various bedroom reasons, but even though he'd wooed Angela into becoming his fiancée and obviously loved her madly, she suspected he was still in love with her. Which she was fine with because... who wouldn't?)

Truth was... Jen had decided she preferred women. Ivan was a good man, had been a good provider, but was never a great lover, and he was rather small in the penis department. But now Jen could take her pick of various sizes anytime she wanted, from any of the five women she regularly fucked or got fucked by. That said, she really preferred being the one doing the fucking.

"Yeah, that tentativeness is likely my fault too," Jen said. "I wasn't easy to please in or out of the bedroom."

"Tell me about it," Angela smiled, having been seduced by Jen when she was drunk a few weeks ago, and had been regularly dining on her pussy and getting fucked by her strap-ons ever since. Sure, she felt bad about it, cheating on her fiancé... with his ex-wife of all people... yet Jen made her feel so alive sexually, and although she'd never previously seriously considered eating pussy, once she tried it she couldn't get enough.

"Hey," Jen said, as she spread her thick thighs, both these ladies BBW's, "With you, I don't think I've been too demanding."

"Hey right back! You texted me while I was in a church service to come and eat you in the bathroom," Angela pointed out, as she finished her wine and lowered her large-framed body between Jen's legs.

"You were still worshipping once you'd joined me," Jen shrugged playfully, not having much faith in religion, and viewing churches as convenient hunting grounds.

"I do love to worship this pussy," Angela agreed, as she leaned forward and began chowing down on her second helping of Jen's homemade pie since coming to visit a couple hours ago.

"And I love having a sexy pussy-craving slut willing to go down on me anytime I spread my legs," Jen added, although truth be told, she had a few gals who were more than willing to stop whatever they were doing to go down on her or to take a strap-on in their pussies. Being a nurse herself, she had three nurses, all a lot younger than she, to service her, plus Dr. Sturgess who was older, and another doctor she ass fucked on occasion... Dr. Parker... sometimes spit-roasting him with her gay black nurse colleague, and that was just when she was at work.

"I still can't believe I went from straight and engaged to not straight at all, and servicing Ivan's ex-wife," Angela mused, as she parted those big wet pussy lips to get to the really good stuff.

"Don't forget bending over to take my big cock in that pussy of yours," Jen added, belatedly musing she likely could have pegged Ivan, if she'd been into that kind of thing while they were still married. He'd always been a doting husband and did whatever she asked... for one example, going down on her way more often than she went down on him. He was good at it too, although she'd discovered since their breakup that women were just better at it then men... just like Hank, her gay black RN colleague, informed her was also true about male cock suckers... a term he loved to call himself.

Hank was completely gay (although Jen enjoyed proving that wasn't technically true), even a little flamboyant, but he had an almost nine-inch cock, and although he loved sucking dick and being fucked, he was a natural femme bottom... or rather a switch, since he also loved turning straight guys into cock sucking bottoms... something he did quite regularly.

Jen enjoyed getting her pussy licked, and after her second orgasm today from Angela's eager (and getting better each time) tongue, she queried, "Do you think Ivan would take a strap-on in his ass?"

Angela looked up at Jen, her face agleam with pussy juice, and replied, "I can't even fathom his doing that."

"Could you have fathomed becoming your fiancé's ex-wife's pussy pleaser before you became one?" Jen asked, looking down at the pretty curvy BBW, her black. And purple hair adding to her sexiness, and her 220 pound frame able to shake in all the right places whenever she took a dick in it... usually from behind, but on her back and even cowgirl... and Jen fucking loved Angela's double D tits... loving watching them bounce around like basketballs way out of control.

"Well, no I guess I couldn't have," Angela admitted, as she got up off her knees and sat back down on the sofa and reached for her glass of wine.

"Or that you'd ever take a ten-inch strap-on?" Jen added.

"No," Angela replied, ashamed of what she'd done, yet equally turned on by it.

She knew she was a big girl... and had done all the things big girls often needed to do to keep a guy... anal, swallowing cum, even getting spit-roasted... but she'd often felt used, and she'd never found a man who loved her for herself... including her large frame... until Ivan. She'd found a kindred spirit in Jen, who was also large, although 20 pounds lighter than she was and with smaller tits, and thus also who understood the challenges of being a horny BBW. Guys would still fuck you, they just wouldn't show you off to their friends (or even be seen with you around them), or take you home to meet their parents.

Jen was always confident though... she acknowledged she was chubby... but always found ways to use her voluptuous curves to her advantage. She always wore sexy attire whenever she went out, and usually wore sexy lingerie underneath her nurse's uniform... thigh highs, a garter-belt and stockings, perhaps a lace camisole... since she never knew when someone might be between her legs during a break or an extended lunch.

"Or..." Jen said, an even wickeder idea popping into her head, "I bet Hank could turn him, and get him started on sucking dick and getting buggered."

"No way," Angela said, Ivan never showing the slightest interest in same-sex frolicking.

"Then you'd both be cheating on each other, so the guilt you feel each time you leave here could be banished," Jen said, knowing Angela was always wracked with guilt after she left, yet couldn't resist her.

"I'd still be the one who cheated first," Angela doggedly insisted on castigating herself, today's guilt coming a little earlier than during her 'drive of shame' home.

"You had no choice about that," Jen made another attempt at lifting her friend's burden. "I'm fucking irresistible."

"And not at all arrogant," Angela laughed, as Jen stood up.

"Flaunt it if you got it," Jen shrugged,

"And you've got it," Angela said, admiring Jen's confidence and wishing she had the same amount.

"You do too, Angela," Jen said, pulling the pretty BBW in for a kiss. When she broke it, she slapped Angela's expansive ass and said, "Now, let's fuck that pussy, so you'll go home satisfied."

Angela, horny as hell and wishing to be punished for her constant indiscretions asked, "Why don't you fuck your nasty slut's ass this time?"

"Oooooh, fun!" Jen said, having only before this fucked Dr. Parker's ass, and once an older woman's in her sixties she'd met a bar at a nurse's conference, who took it in the ass like a champ while her husband watched and jacked off to the sight. That had been wild!

"Yeah, I used to take it in the ass a lot," Angela said before adding, "although it's been a while."

"Yeah, the things we big girls do for dick," Jen commiserated, as she put on her strap-on. Even though she herself had discovered her inner confidence at a young age, she knew that most bigger girls felt they had to be willing to do the things the skinny waifs wouldn't. And if she was being honest, she had to admit the only real difference between herself and those gals, was she didn't feel she had to, she simply loved doing them.

"Oh, you couldn't even imagine," Angela said, recalling the time she was the recipient of a golden shower, and when she'd walked along a beach with cum all over her face, and when she'd eaten a boyfriend's sister in front of him at his request.

Meanwhile Jen lubed her strap-on, although not with anal lube, she didn't have any of that, but lube for getting into a tight pussy... which she seldom needed. "Oh, we all do things we're ashamed of later," she said, as she bent Angela over the table. (Actually she couldn't think of a single time she'd been ashamed before or after; she was just trying to be kind.)

"Like being my fiancé's ex-wife's lesbian slut," Angela joked, never ashamed while she was still with her, as evidenced by her light-hearted little joke, but always ashamed afterwards.

"For example brace yourself," Jen agreed, as she positioned her cock at Angela's puckered asshole.

"Just shove it in," Angela said. "I've taken ten-inch BBC's up there."

"You really are a slut," Jen observed without rancor, as she pushed forward and watched her cock disappear between Angela's big ass cheeks.

"Always have been, too," Angela moaned, having long been used to a cock in her ass and the unique pleasure it brought her... quite different from a dick in her pussy, or a tongue on her clit. The humiliation of being sodomized, of being treated like a completely submissive slut, had always oddly stimulated her during those moments.

"That's why you make such a dynamite pet," Jen said, her big body suddenly resting against Angela's big body.

"Oh fuck," Angela whimpered, the initial deep insertion into her ass always a mixture of pleasure and pain... the pain always leading the way for a while.

"You okay?" Jen asked. She liked to fuck her pets hard, but she also wanted them to be happy... to enjoy being the submissive slut just as much as she enjoyed being the dominant bitch.

"Not really, but I will be in a minute; it always takes a little while to get used to a dick in my asshole," Angela explained truthfully.

"I imagine it would," Jen sympathised, never having actually allowed one inside her own ass. She'd had her ass eaten a couple of times in the past year and found it quite pleasurable, but even just the idea of getting ass fucked did very little for her.

"But eventually it feels fucking amazing," Angela said, as with reasonable patience she gave her ass some time to get used to being filled again.

"I'll take your word for it," Jen said.

"I can't believe no one has ever pounded that big booty of yours," Angela said.

"Many people have offered to."

"Well, count me in on that," Angela said, having always wondered what it would be like to fuck someone.

"You want to wear a strap-on?" Jen asked, as she began slowly fucking Angela.

"I think so; I've always been curious to try."

"Maybe after Hank has turned Ivan into a cock sucking bottom, you can peg him," Jen suggested wickedly, seeing the idea of pegging Ivan as a very intriguing proposition.

"I could never," Angela moaned, as after just a few strokes, the pleasure began to counterattack the pain in her rectum. Even though, truth was, she liked the idea of trying that with her fiancé.

"Yes you could," Jen disagreed amicably, enjoying hearing the soft whimpers now coming from Angela. One of her biggest turn ons since going dyke was hearing a woman moan for her.

"I don't know," Angela said, her hesitation taken by Jen as reluctant agreement.

"Oh, I do," Jen said, the idea of pegging Ivan or getting him to bottom for Hank suddenly looking very, very delicious.

"Okay, I'm good now. Do it harder, fuck my asshole harder," Angela moaned, her pleasure increasing and the idea of seeing Hank, whom she had met twice, or perhaps Jen fucking Ivan instead, was now looking very intriguing.

"You like the idea of Hank or my doing that, don't you?" Jen asked, as she obliged the request and began really slamming into the big booty.

"Yesssssssss," Angela admitted, unable to lie to her.

"Then I'll make it happen," Jen promised, Hank having a very impressive track record of turning straight men, and Ivan was a natural submissive, something she only now was realising, since she'd educated herself about the dom-sub lifestyle since leaving him. If she'd known then what she knew now, she'd have been pegging him years ago... and was 99.9% confident he'd bend over and take a strap-on in the ass if Hank worked his magic, or even if she, although his ex, ordered him to.

"Yessssssss," Angela replied, although she wasn't necessarily approving of Jen's promise, but responding eagerly to the increasing pleasure coursing through her as her ass was hammered.

"We'll spit roast him," Jen reiterated, whether it would be Hank and she, or she and Angela was still to be determined... but whichever, Ivan would soon be discovering prostate pleasure.

"Oh fuck. That's always so wonderfully nasty," Angela rejoined the conversation, wishing she could be spit-roasted right now. God, she'd love a cock in her mouth depositing a delicious load. Being a slut for all these years, being used for all these years, she'd become addicted to cum... which Ivan really appreciated... her daily blow jobs... which she knew Jen had quit doing for him long ago... way before their divorce.

"Are you going to come from my sodomising you?" Jen asked, something she'd never witnessed a woman doing, although Dr. Sturgess spewed his load all over his desk or his carpet every time she or Hank destroyed his ass.

"Yessssssss," Angela admitted, her orgasm imminent... and although she liked coming from a tongue on her pussy, and enjoyed an orgasm from a dick in her pussy, nothing made her body burn with euphoria like her anal orgasms did.

"You're such a nasty little slut," Jen praised her, as she slammed into Angela as hard as she could... loving the impacts of their bodies colliding.

"Yeah, I'm your dirty slut," Angela declared, knowing without a doubt she'd do anything Jen told her to... even though she always felt guilty afterwards during her drives of shame home, or when she was lying in bed next to Ivan. Yet she could never disobey Jen... or even resist her... ever. Jen understood her sexual needs in ways no man ever had... and she appreciated her in ways no one but Ivan ever had.

"Remember that when I turn your fiancé into a cock-loving slut just like you are," Jen said, really slamming into her.

"Oh fuck!" Angela screamed as her anal orgasm hit her from Jen's rough rear reaming, added to the strange visual of her straight-as-an-arrow Ivan getting himself dicked.

Jen watched Angela erupt and collapse forward, and then she admired the gaping hole she'd just created. A pussy closes up pretty fast, but an asshole remains wide open for the longest time, as if it's still beckoning you in.

Five minutes later, Angela and Jen were sitting down again, Angela tilted a little to the side so as not to sit on her still gaped asshole, while as a nefarious team they concocted a wicked plot to make Ivan into a compliant cock sucker, to make him into a blooming bottom, to make him into a furrowed faggot.

.....

Oddly, Angela didn't feel guilty this time as she drove home. She couldn't figure out what was different this time, other than her excitement about the idea of pegging Ivan. She wasn't as certain how much fun it would be to watch him suck a dick or get fucked by another guy, those activities still seemed a little weird, but the idea of her sticking a strap-on into his bum kind of turned her on.

.....

Jen sent Angela a porn movie for her to watch with Ivan, to plant the first seed of his pegging.

Ivan was more than happy to watch porn with Angela, that was one of the things both his ex-wife and his wife-to-be had in common with him... they all three liked porn. Although Angela, unlike Jen, often liked to act out things she saw in those movies... roleplaying sometimes... and experimenting with new positions.

Angela was wearing sexy lingerie... Ivan liked nylons, and so did she... as they cuddled in bed together watching the porn. It was the second scene, and by now Angela was slowly stroking his not even five-inch dick, while eagerly anticipating what she knew was coming.

It started pretty typically... a football player being tutored by a nerd girl, who of course is really hot, even though she has glasses on. The guy isn't getting the subject matter, so he's suggesting she just do the whole thing for him. The nerd sighs and says, 'sure why not, so long as I get to fuck you'. The jock smiles and shrugs, 'why not indeed?' So the nerd strips the jock, sucks his cock for a couple minutes, and then asks, 'ready to get fucked good?' (The subjects she excels in obviously not including English, but nevertheless she uses the language slyly.) The jock doesn't catch onto the sly wording as the nerd, who is surprisingly strong, bends him over and raises her skirt to reveal a strap-on... already securely in place and ready for action. The jock's eyes go big and he stammers, 'W-w-what the hell are you doing?!' And the nerd slides her cock into his ass.

Angela smiled at how in porn lube is never needed, even for a virgin ass. Of course this actor wasn't likely an ass virgin anyway, just his character... but still.

"Oh my God," Ivan gasped, as his cock flinched in his fiancée's hand. He certainly hadn't been expecting that!

"You particularly like seeing that?" Angela asked seductively, as she felt his small but hard cock suddenly pulsing in her hand.

"What? No!" Ivan denied, as he watched the pretty nerd fucking the guy's ass. "I just wasn't expecting it."

"Yeah, right," Angela teased. "Tell that to your suddenly wide-awake dick."

"I was already hard," he protested, even while he couldn't stop watching this guy moaning away while his ass got fucked. He'd read in some health magazine how prostate orgasms are not only good for your health, but amazingly pleasurable... but he hadn't put much thought into it.

"Did Jen ever peg you?" Angela asked.

"Peg me?"

"Yeah, as in did she used to fuck your ass with a strap-on?" Angela asked bluntly. "We both know she wore the pants in your family."

"Hey," he said, knowing it was true, but not really appreciating it being pointed out, even by his fiancée. He still hadn't got used to the two becoming such close friends. It was weird, and he always worried a bit what they might talk about while he wasn't there.

"Hey yourself, which is it? Did she pound your ass, or did you just wish she pounded your ass?" Angela rephrased her question, this time with some serious spin to it, a little surprised at how brazen she was being.

"Angela!" Ivan gasped, this unexpected interrogator not at all like his wife-to-be. Sure, she got pretty animated in the bedroom, but she'd never said anything like this... so far she'd always been the complete submissive in their relationship.

"That isn't a denial, but neither does it answer my question, so which is it?" Angela continued pestering him as she stroked his cock, and listened to the whimpering jock's moaning coming from the television.