As I kept tongue-fucking Dana’s asshole and Deb finger-fucked her pussy while nursing on her clit, I decided to find out just how much into pain Dana was. I reached under her slim frame and cupped both her perky tits in my hands, feeling their firmness in my palms. Then I pinched her nipples, hard. Dana yelled out and her whole frame shook as I squeezed her pebble-hard buds. I felt her sphincter tighten around my probing tongue while she mewled brokenly.
“More… Please… Pinch my nipples, Jeff… AAAAHH YES! Like that! Pinch me, hurt me, pleeease!”
I turned slightly, meeting Deb’s gaze. She had her nose pressed into her sister’s sopping cunt and her tongue extended, flicking over Dana’s clit. Her face was shiny with pussy juices as she arched an eyebrow and winked in response to my baffled look, wordlessly saying ‘I told you so!’
I kept rimming Dana’s asshole with all I had as I tortured her long hardened nipples, twisting them and pulling on them mercilessly, sinking my nails into their knotted, thick flesh. It felt intoxicating to hear Dana cry out every time I hurt her sensitive nubs. I honestly couldn’t tell if she was yelling in pleasure of pain. But then, apparently it was the same to her. It didn’t take long of this additional rough treatment for Dana to crest over a massive orgasmic wave. Her body shuddered so violently that she seemed to be having a seizure and her scream of release was so high-pitched and loud that I feared the neighbors would call the cops to investigate on a freaking murder.
Dana’s ass was still perched up in the air and she was whimpering into the bed sheets even after Deb and I finally let go of her pussy and asshole, allowing her to descend from her intense orgasm. Reaching into the nightstand drawer, Deb grabbed the bottle of baby oil we kept there. Moving beside her sister’s surrendered body, Deb started dribbling the slick fluid into Dana’s well-rimmed asshole, sliding one finger into her ass to grease up her virgin rectum. I positioned myself right behind Dana, my gaze focused on her pink little rosebud and on my girlfriend’s glistening finger sawing in and out of that tight crinkled hole. Deb poured a generous amount of oil on her other hand and grabbed my hardening dick, slowly jacking me off and coating me in lube. Filling my palms with Deb’s plump ass, kneading and massaging that masterpiece among bubble-butts, I pulled my amazing girlfriend closer, squashing her large boobs between us.
“I love you Debs,” I murmured into her hot mouth, “this is amazing. You’re amazing!”
“Mmh… Love you too, baby! I love doing this with you, it’s so hot! I’m so turned on, baby!”
We kissed passionately as Deb fisted my stiff meat and masturbated her sister’s asshole, preparing us both for Dana’s first assfuck. After a while, overstimulated and crazed with arousal, Dana turned her groans of anticipation into actual words, pleading brokenly. “Aaaahh… Enough teasing! I can’t take this anymore! Oooh… Give me your cock, Jeff, please! Stick your cock up my ass, now!”
I was rock-hard as my girlfriend guided my thick cock to her sister’s asshole. Giving me one last slurping kiss, Deb placed her hands on Dana’s supple little buttcheeks and spread them open for me, gaping Dana’s oily anus with her fingertips. I pressed my spongy glans to Dana’s asshole and gave a tentative push, then another, harder, while Deb pulled the crinkled edges of her sister’s butt-ring further apart. Dana whimpered as her mollified sphincter yielded and the tip of my dick slid into her virgin ass. Encouraged by her moans, I kept easing myself into her anus, watching her muscular little ring widen obscenely, stretching out around my invading pole.
Dana was trembling all over as I slowly pushed deeper and deeper into her rectum, enjoying the incredible pressure of her warm anal channel enveloping me. She was barely breathing, just the smallest of whimpers escaping her parted lips whenever I moved further into her tight, untouched ass. I had half my cock embedded into her snug little butthole when I simply couldn’t move anymore, she was just too tight. Her sphincter was clamping around my pole and her rectal passage seemed to be cramping, constricting my cock so hard that it almost hurt. Surely it must be hurting her more, I thought. And yet, despite her obvious discomfort, Dana wasn’t protesting nor asking me to relent. She just breathed in and out, fast and raggedly, her eyes shut and her hands clawing at the sheets. I turned to Deb and we shared a meaningful glance.
“Dana, I can stop if you need to adjust. Just try to relax, it will make it easier,” I said. She just shook her head no, moaning as she wiggled her tiny butt, signaling me to keep sodomizing her.
Letting go of her sister’s ass, Deb grabbed the bottle of baby oil again. “Maybe with more lube…”
At that Dana finally spoke up, her voice trembling, her eyes still closed. “No-oooohh! No, Debbie… No lube… Uuuuh! I want… To feel it… Uuuuuhhh! I need to feel his big cock splitting my ass! It hurts but… Uuuuhh! It hurts so good! Give it to me, Jeff! Oooohh my god… More, Jeff! Give me… Uuuuhhh!… More!”
Deb and I looked at each other, puzzled but grinning slightly. “Well,” she said with a shrug, “I think I know something that might help you enjoy this even more, sis.” Deb knee-walked until she was in front of her twin then she lay down on her back right before Dana’s face. Spreading her legs open, my babe parted her pussy lips with her fingertips for her sister to lick.
“Aaahh yes, Debbie! Give me that sweet pussy… Mmmhh!”
Cooing as she clamped her lips on Deb’s soaked folds, Dana reached a hand to her own needy cunt and started fingering her clit. Her constricting rectum seemed to unclench a little, just enough for me to start plunging into Dana’s unexplored depths again. To the sound of Deb and Dana’s mewls and moans, I grasped Dana’s tiny butt in my hands, filling my palms with her toned ass-flesh. Pulling her to me as I pressed into her, I started fucking her ass with hard stabbing thrusts, forcing her rectum to accept more cock at each firm push. Dana gasped into her twin’s pussy at each in-stroke, but she took it all without protest, until my whole pole was crammed up her ass.
Doing as she asked, without waiting for her anal channel to adapt, I pulled out of Dana’s snug butthole then slammed all the way in again, stretching her tight rectum open before it could clamp down. She shivered, yelping into Deb’s pussy. Undeterred, I set a nice rhythm right away, pushing hard to jam myself balls-deep inside that gripping anal sheath and then sliding out as Dana’s resisting bowels clung to my meat. I was mesmerized by the sight of her reddening butt-ring dragging out along my shaft as I exited her asshole almost completely at each pass. In a matter of minutes I was pounding her ass for real, reaming her virgin anus hard and fast while I held her butt in my hands, slamming her lithe body back onto my impaling cock while I plowed into her.
Dana’s deep groans were squishy pussy-muffled sounds coming out in time with my punishing strokes, followed by slurping mewls when I pulled out. I had no doubt that I was hurting her a bit. Maybe more than a bit. She was diddling her clit furiously and she was distracted by the oral assault she was treating her sister to, sure, but there was no way that an anal novice like Dana could take this sort of brutal assfucking without pain. But then, that was exactly what she wanted. Amazingly to me, she was liking it, as demonstrated by the fact that I felt her quiver under me in a series of quick peaks while I kept mercilessly pillaging her ass.
The friction and pressure around my raging hard-on were incredible, much greater than what I had felt when I buttfucked Deb for the first time. Even after minutes of heavy ass-pounding, when I had loosened her rectum and reshaped it to fit me better, the muscular tightness of Dana’s virgin asshole persisted, as if it still wanted to prevent my intrusion. It was the opposite of Deb’s snug yet welcoming ass, whose surrender was always swift when I fucked it, to our mutual pleasure.
I wasn’t usually into domination and rough stuff, but Dana’s submissive and slightly masochistic streak egged me on to give it to her hard, using her ass for my own pleasure with no regard for her. Soon I lost myself in a primal sodomizing haze. I was so intent in watching my cock fly in and out of Dana’s sculpted little hiney that I was caught by surprise when I raised my gaze to find Deb kneeling on all fours before her sister, her plump round ass in the air. My mouth watered and I humped more viciously into Dana’s violated butthole while I watched my girlfriend pour rivulets of lube all over her own pink rosebud, gaping her little hole with two slender fingers to let the slick liquid dribble in, coating her anal tunnel.
With my eyes glued to Deb’s greasy fingers sawing in and out of her glorious bubble-butt, I kept brutally fucking Dana’s tight ass until I felt her tremble beneath me. “UUUUH!… Yeeeahhh! AAAAH!… Stretch me open, Jeff! Rip my asshole! UUUHHH!… Yeahhh, ram your cock up my ass! Haaard, hardeeer! UUUHH!… Hurt me! Use me! AAAHH yes, wreck my aaaAHHAAHASS!”
Dana thrashed and gasped like a stranded fish as her violated asshole clamped around me, choking my throbbing hardness, forcing me to stay buried deep into her cramping bowels as she screamed out her orgasm. I groaned, trapped in the vise-like grip of Dana’s constricting rectum. I winced from the intensity of the friction when I tried to move, so I just stayed perfectly still until Dana’s cries of release gradually died out in a throaty, gasping sob. All the while though, my eyes were locked on Deb’s juicy ass, my stare zeroing in on that delicious little asshole of hers glinting with lube right before me. As soon as Dana’s anal muscles started relaxing their stranglehold on my cock, I swiftly slid out of her still pulsing ass, eliciting a sharp mewl from her as I escaped her ravaged butt-ring.
Deb squealed when I lunged forward and grabbed her fleshy rump, pulling her to me until she was face down on the bed and ass in the air right beside her well-fucked sister. My girlfriend moaned in anticipation as she wiggled her awesome ass, looking over her shoulder at me with lust-glazed eyes. I sank my fingers into Deb’s juicy jiggly buttcheeks and pressed my aching boner against her oily anus. I slid past her elastic sphincter and into her fabulous ass with almost no resistance, plunging deeper in the familiar snugness of my babe’s eager asshole. My eyes rolled back in my skull as Deb’s warm slippery rectum accepted my length inch after inch, hugging me in that buttery tightness that I had come to crave like nothing before.