This story is a work of fiction and all sexually active characters are age 18 or older.
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Wils hesitated, holding his rigidity between Ann's firm ass cheeks. "Are you sure this won't hurt you?"
"Only in a good way," Ann replied. "As long as your cock is well lubed and there's enough goop squirted up my ass, we're good to go. Take your time and keep it slow and steady until you hit bottom."
Wils applied his condom-sheathed prick to Ann's glistening rosebud, watching and feeling the crinkled flesh compress and gradually dilate as his hips pushed him against his girlfriend's naked ass. His glans pushed through the tight barrier, trapping the flared head as Ann contributed a steady rearward pressure.
"Atta boy, keep going!" the girl panted. "I need you to fuck my ass 'til I scream. Don't stop until you cum. Fuck me like you're trying to break me."
Emboldened, Wils grabbed the firm hips before him and steadily sodomized her tightly stretched bunghole. He felt her lubricated tunnel gradually part as he advanced, noting a furnace-like heat similar to the girl's pussy and mouth. His hips bumped against her fleshy buttocks, signalling that he was firmly seated in his girlfriend's rectum. He felt a twinge of guilt combined with perverse joy at violating his parent's religious teachings.
Wils slowly withdrew his prick until only the head was trapped in Ann's ass, then reversed course and drove himself back into her hole. Ann gasped and thrust back against the intruder, hilting him fully into her.
She reached between her legs and caressed his hanging scrotum. "I want you to hammer my ass so these lovely balls smack against my pussy." Her fingers retreated to stroke her dripping labia as the young man began to shaft her rear hole with increasing vigor.
The lad grunted as each thrust hammered home, the anal ring stretched tightly around his rampant lubricated shaft, pulling and collapsing the girl's flesh as he plundered her. He felt his orgasm approach and muttered a warning to the sweating figure beneath him.
Ann pushed back against each thrust, whimpering, panting and coughing with the effort of taking a hard penis deeply into her body. Her fingers strummed her clitoris as his nutsack contracted to strike the bottom of her swollen labia. She clamped her sphincter tight around the staff producing such incredible sensations in her rump.
Wils couldn't resist the stimulation and pounded his cock into her raw, reddened rectum. The force of his thrusts collapsed the orgasming girl to the bed with her hand trapped against her teeming twat. He continued to pound her ass as the semen raced up the length of his swollen prick and pumped several blasts into the condom.
Still cojoined, the breathless couple rolled onto their sides. "Fuck me, that was intense! Stay inside for a bit. Pull out after you go soft." Ann tilted her head back to nuzzle her lover's sweaty face. "How did you like pounding my bum?"
Wils kissed the shell of Ann's ear. "It was - is dirty, and debauched, and... powerful. I knew you wanted this and pushed back to take more, so I wasn't overly worried about hurting you." He rested his head on hers as the appropriate words surfaced. "Right at the end I didn't care that I might injure you; all I wanted to do was cum as deeply in your rectum as possible." He wrapped his arms more firmly around his girlfriend. "What can you possibly teach me about sex to surpass this?"
Ann pulled his head forward to kiss him. "Oh, I don't know, maybe a threesome?" She smirked at his astonished look. "I'm certain my brother would loan us his girlfriend to continue your worldly education."
Wils was stunned. "I, um, Alex, Janice. They wouldn't want that," he sputtered. His flagging erection slid out of the giggling girl's ass to the accompaniment of a couple of delicate queefs.
"Oops, you pumped a little air up there," she giggled. "Surely you've noticed how nice a body Janice has. I'm envious of her tits. They're so big and firm. Have you noticed how often her nipples stick out - horny bitch. We could double team her; you on one boob and me licking and sucking the other." Ann deftly slipped the slimy condom off her boyfriend's firming prick and tossed it into her trash can. Pushing the lad onto his back, she tucked her calves under his arms and lowered her face to his crotch.
Wils pulled the gaping pussy onto his mouth as Ann similarly engulfed his cock. She slurped and sucked, drooling saliva along the length of his shaft. As his trimmed pubic hair glistened with her excess spit, her hands fondled his scrotum and stroked the length of member not engulfed by her mouth.
Wils kneaded her ass as he feasted on the hole before him. It had only been a couple of weeks since this lusty girl took his cherry and introduced him to a variety of sexual practices he had barely fantasized about. As he dug his tongue deeply into her sexual cavern, he thought about the pair of them pleasuring Janice. The thought sent a pulse through the shaft buried in his girlfriend's mouth.
Ann pulled her hips free of Wils' grasp and turned to mount him. "You were thinking about Janice, weren't you?" She smiled brightly at him as she slid his cock home in her freshly licked cunt. "Can you imagine what Janice and I could do with you? I could sit on your face and she could ride your stiffy. Or she and I could sixty-nine while you fuck her from behind. I could lick your cock as it slides back and forth in her."
Wlis was dumbfounded and very aroused at the images Ann's words were creating in his mind. He warred with the thought of his good friend's girlfriend having sex with him and performing lesbian acts with Ann against the sheer debauchery and kinky aspect of the whole idea versus not betraying the trust of his friend.
Ann kegeled around his prick with a grin. "I'm going to get the 3 of us together and we'll fuck your brains out. Alex will be OK with it, trust me. I wouldn't do anything to hurt my brother. I love him a lot." She continued her tight slide on his shaft and continued, "You're going to fuck Janice senseless and I'll eat your cum out of her battered cunt while you suck her nipples."
Wils growled and pulled the girl tightly against his groin as he unleashed a second load of cum into his insanely perverted, dirty minded girlfriend. Ann collapsed onto his chest and ravaged his mouth with her agile tongue.
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