Jimmy, a drinking buddy of my cousin said to me, "I heard you decided to dump Cheryl." I'd been in a relationship with the cute middle-age woman for a long time, but planned on leaving her for a much younger blonde beauty who really turned my crank. An intention confided to my cousin, who probably let it slip to Jimmy in a drunken binge together. "I'm gonna take over Cheryl's account," he added. "I need you to help hook me up with her."
I didn't think she'd go for Jimmy. Ugly to begin, the squat man is pudgy with a beer gut loping over his waistband. His big belly typically strains against a wrinkled shirt, half unbuttoned, which hangs un-tucked outside his pants. Those droop to expose his asscrack when he bends. Jimmy's let it be known he's got thick hair all over--arms, legs, chest, butt, shoulders, and back--along with bristles that sprout from his nose. Shaggy-haired, he has a walrus mustache and a heavy five-o'clock shadow. Add smeared pop bottle eyeglasses and what can be a self-centered personality, often over-bearing, and Jimmy is not an attractive package.
That said, Jimmy is not a marshmallow fat body. Underlying his layers of fat is muscular strength. Jimmy's strong; plus a malicious street brawler on top of it. Which based on his looks is a rude awakening for some in a barroom fracas. He's a latent menace willing to fight at the drop of a hat.
I've also learned he can often become obsessed with things that come to mind. With my impending break-up with her, Jimmy now viewed Cheryl as "free for the taking". He'd pursue her with a dogged determination.
"That can be arranged," I said. "But up front, I'm not sure Cheryl will go with you." The possibility of my soon-to-be ex-girlfriend becoming Jimmy's "main squeeze" as he put it, created dual emotions. One was a twinge of jealousy, envisioning the cute thirty-eight year old brunette with another man.
The other was a perverse thrill imagining exactly that! Cheryl naked, flat on her back, thick thighs spread wide, being banged by a hard dick of someone else. Only until that moment, I'd never considered the guy to be Jimmy. A thought which struck me as just nasty!
A few days later in sex role play I prodded Cheryl about her fantasies.
"Being double penetrated is one I've had awhile. You know that," she breathed, bucking her wide hips, trying to take my stiff cock deeper into her curvy body as we fucked missionary style.
"Want me to make it real?" I plunged my shaft balls deep into her soft gooeyness. A large wet spot marked the bed sheet from pussy juice trailing down.
"Ohhh...I dunno," she said in the heat of passion.
"Tell me, babe."
"Y-yes, if you'll still respect me afterwards."
"Sure. I will," I said, locking-up and spurting jet after jet of hot cum into Cheryl. Not that what I told her mattered. I'd already decided on being gone.
I made her fantasy come true a week later. After fucking my new girlfriend Amanda, I left her apartment late evening and headed to Cheryl's house. It was a hot summer Friday night. When I got there my soon-to-be ex-girlfriend was in a sleeveless scoop-neck blouse exposing the deep cleavage of her melon size breasts. Her faded denim jeans had been hacked short, the bottom curves of her plump butt-cheeks visible and enticing beneath the frayed edges. The outside of Cheryl's thick thighs were slightly dimpled from cellulite. A bit overripe I thought, but at thirty-eight, still very sexy. I felt a tug of regret at the loss of her.
"It's late. I didn't think you'd be by tonight," she said.
"I figured to surprise you."
In the aftermath of our previous love-making Cheryl had simply dropped the subject of sharing her. Her silence had made me unsure if she truly meant it to happen.
"You look hot, babe." I kissed Cheryl, my tongue probing past her parted lips as I reached beneath her blouse to squeeze the large mound of a bra-covered tit.
We both looked toward the sound of her front door opening to see Jimmy stepping inside. "Looks like the start of fun," he said with a smile. "Think I'll help feel Cheryl up." As he spoke Jimmy quickly stepped our way.
"What?" Cheryl said, surprise on her cute face. "I⸻"
Whatever she planned to say was prevented by Jimmy pressing his lips to hers and thrusting his tongue into her mouth. He jerked her blouse along with bra up and over Cheryl's large tits, freeing them to spill down.
Jimmy broke off the kiss and grabbed a breast drooping from its own weight. "Fuck, yes. I've wanted to play with these big babies for a long time. From the day I laid eyes on you."
Cheryl half turned her face toward me. "This is something you wanted," I whispered into her ear. I nuzzled her neck, smelling a pleasant fragrance of perfume, and reached down to unbutton her jean shorts.
Fingers digging into the soft flesh of a clenched tit, Jimmy lowered his head to lick Cheryl's pert nipple followed by sucking it into his mouth.
Cheryl leaned back into my chest, cute face tilted upward to receive a kiss. I pressed my lips to hers while unzipping her shorts. I ran my hand beneath the waistband of Cheryl's panties to her pubic bush. The furrow of her pussy lips was wet to the touch of my middle finger.
One of Jimmy's hands slipped into her panties and nudged mine aside to replace me in fingering her wet pussy. "I'll take over," he told me.
I removed my hand to peel Cheryl's blouse up and over her head while she lifted both arms to help. Next I unfastened and tossed her bra aside. Her denim shorts followed. I worked them past her rounded hips to fall in a pool at her feet, leaving Cheryl naked except for skimpy red panties barely covering her plump white ass. "Nice," I said, reaching out to rub a soft butt cheek. Cheryl looked over her shoulder and smiled.
Her easy acquiescence to being stripped and fondled by both me and Jimmy was somewhat of a surprise. Even though it was her fantasy I'd expected mild reluctance of feigned modesty. Maybe, I thought, she was a whore at heart as Jimmy once contended in the past. And the only reason she hadn't spread her legs for him was he'd refrained from trying to fuck her out of respect for me. The way he saw it Cheryl was my steady girlfriend at the moment, so hands off. That, of course, was no longer the case.
"Keep her occupied," Jimmy said, stepping away from Cheryl and beginning to disrobe.
I kissed her, tongues dueling, and cupped the damp crotch of her panties.
Cheryl broke off the kiss to breath, "Don't leave me... after this."
Jimmy hastily shucked his clothes except for black socks to bare his overweight, thick body covered with hair. Underneath his hanging belly fat was a huge semi-erect veined cock. Fully-hard my guess was it would be near ten inches long and thick as my wrist. A hairy nut sac with golf ball size testicles drooped below it. A stunning discovery; I had no idea Jimmy was so well-hung.
Appearing transfixed by the sight of his enormous uncut penis, without word Cheryl unconsciously reached out to grasp it.
"Like the looks of that cock, Cheryl? Want it?" he asked with a grin, looking down to see her hand softly stroking his prick. Not waiting for her answer, he added, "Which way to the bedroom?"
Cheryl released her hold on his thick shaft and turned to begin walking down a hallway, the looming hulk of Jimmy following. For me, it was a hot view, seeing the saucily moving cheeks of my ex-girlfriend's panty-clad ass as Jimmy put a possessive hand on it. My cock was rock-hard!
Coming to her bed, Jimmy waggled his big cock and said, "Down on your knees, Cheryl. Suck this bad boy."
Without hesitation, the curvy woman dropped to her knees and taking Jimmy's dick in hand began sucking it.
"Ohhh, that's it, Cheryl," Jimmy groaned. "Suck it, slut."
Jimmy's comment made my stiff rod flex upward. It wasn't the name calling, I'd spoken the same to her before in role play. But it was seeing the ugly man demean my cute ex-girlfriend who had previously considered him to be gross. "There's no way I'd let your cousin's beer buddy... or a slug like him, which includes your cousin... touch me," she'd once remarked, eyeing Jimmy with distaste. An apparent lie, I mused, observing Cheryl's head bob up and down, lips skinning the short length of Jimmy's rigid shaft her lips managed to encircle. Most of his long penis was still visible.
"Enjoying yourself, Jimmy," I asked with the knowledge Cheryl was good at giving a blow-job.
"Oh, yeah," he answered, entwining fingers with Cheryl's brunette hair at the back of her head to hold it in place. He rammed his thick cock to her throat, causing the curvy woman to gag.
He looked at me with a big smile as Cheryl struggled to breath. Pulling his cock back from deep in her throat, he said, "Sorry, Cheryl. I didn't intend to choke you."
I could tell from his expression Jimmy didn't mean what he was saying.
"Get your fat ass on the bed, bitch," he said, moving to let her rise.
Cheryl complied, lying on her back on the neat made bed, legs slightly apart and big breasts lolling on her chest.
"Lift your big butt, Cheryl," Jimmy said, hooking his fingers in her panty's elastic waistband at the hips. Feet flat to the mattress, back arched to raise her plump ass, Jimmy jerked the underwear to Cheryl's knees, past them, and ripped them off to the floor. He gripped her thick thighs to spread them wide, fully exposing her pussy to his gaze.
"This is mine now," he muttered, positioning his hairy hulk between her legs and keeping them parted wide with wrapped arms.
My nerves were buzzing and my cock was so stiff it hurt seeing Jimmy mash his face against Cheryl's crotch, eating her pussy. Her eyes were closed, a look of ecstasy on her cute face as she lightly palmed the back of his head in amorous encouragement.
Cheryl sighed. Her curvy body tensed and I knew she was having an orgasm. Jimmy increased his hold on her legs as she lifted her pelvis upward, pressing her pussy mound tight to his lips. Nose buried in Cheryl's dark pubic hair, tongue probing her hole, he had her in the throes of passion.
She shuddered as her orgasm peaked. Opening her eyes, she rubbed Jimmy's head affectionately.
That didn't take long for her to get off, I thought. And she's certainly changed her tune when it comes to Jimmy. I stripped off my clothes and moved toward the bed as the hairy man arose.
I had the idea she could suck me as Jimmy fucked her. I moved to bring my hard cock to her lips as Cheryl turned her face to take it in her mouth.
"Stop. Don't do that," Jimmy said. "I intend to kiss Cheryl while I fuck her. Meaning I don't want it to be follow-up to her giving you a blow job."
"Understandable," I agreed.
"Cheryl's been your woman to use for years. This is my first go with her. I want to seal the deal alone."
"Sure," I said, backing off.
Jimmy rose to align his huge cock with Cheryl's pussy, the mushroom head barely touching it. "Put it in, slut."
Cheryl reached between their bellies and grasped his wrist-thick member to run the tip up and down her slick wet slit to lubricate it. She stopped with his cockhead poised at her hole, then urged him forward with her guiding hand.
His cockhead, shiny from Cheryl's pussy juice, was too big to enter the middle-age woman's cunt despite its wetness. Jimmy pushed harder with his huge cock, depressing the labia around her hole.
