Author's note: This is a work of fiction. All characters involved in sexual activities are eighteen years or older. This story contains sister/sister action, but the main theme is anal. If that's not your cup of tea, don't waste your time here. This is a direct sequel to chapter one, so reading that first is recommend. Don't expect realism, and you won't be disappointed when you don't find it! Enjoy!
*****
Sex with Deb had always been awesome. After our first assfuck, it got even better. A week had passed since I took my girlfriend's anal virginity, and not one day went by without me fucking her beautiful plump ass and pumping it full of cum.
For reasons beyond my understanding, Deb's initiation to anal sex had sent her libido into overdrive. Deb always had a major oral fixation, much to my enjoyment. It was a sort of daily ritual for her to give me one of her incredible blowjobs, slurping and sucking and deep-throating me until I shot a big load down her well-trained gullet. Now, beside that, she added her newfound passion for anal to our nightly menu of carnal delights, demanding that I fuck her ass and cum deep inside her, flooding her bowels with semen.
I was very happy to comply. It wasn't unusual for my sweet Deb to unleash her inner tigress in the bedroom, but her recent libidinous spree was unprecedented. Needless to say, I matched her enthusiasm with my own. Ever since I had first entered the tight confines of her rectum, all I wanted to do was bury my cock inside those warm depths again and again and again. And, lucky bastard that I am, I got to do exactly that, at my girlfriend's persistent request no less.
Lost in a week-long buttfucking haze, I was caught by surprise when Deb brought up something that I hadn't thought about since the night we first tried anal.
I had just ejaculated deep inside her insatiable asshole after my babe had ridden me cowgirl style for long amazing minutes, bouncing her jiggly ass relentlessly on my cock and sliding her clinging butt-ring up and down my pole until I sprayed her insides with cum. Finally sated, she was now lying on top of me, cooing, contentedly tired. Her head rested in the hollow of my shoulder and I had my nose sunk in her sex-tousled hair, inhaling her signature scent, as we both caught our breath. My deflating cock was still embedded in her hot cum-sloppy rectum while I held her curvaceous frame tightly in my arms, reaching my hands to caress and massage her fabulous ass. I loved the feel of her big pillowy tits squashed against my chest and bulging out from the sides beneath her gorgeous body, not to mention the slippery hugging grip of her asshole wrapped around my dick.
We had been snuggling in silence for a while, luxuriating in the afterglow and recuperating, when Deb turned her pretty face to look at me. After giving me a long wet smooch on the lips, she said: "So, baby, have you decided yet?"
"Decided?" I said, taken aback. "About what?"
"About Dana, silly," Deb chuckled, rolling her eyes. "Are you going to let me lend you to her so you can fuck her ass, or not?"
My eyes popped open as I recalled the text message that Deb had got from her twin the night of our first assfuck. High on sibling rivalry, drunk on a sense of superiority over her flirty sister, Deb had sent Dana some pics of her gaping, cum-leaking, freshly deflowered asshole as proof that she had tried anal before Dana, getting a major sexual 'first' over her twin. Much to my surprise, Dana's reaction was to request that I pop her anal cherry too, like I did for my babe.
I thought that she was kidding, that they both were. Clearly I was wrong. The calm, questioning look in Deb's eyes told me as much. "Debs, seriously? I mean... Wasn't that just some kind of inside joke between the two of you?"
She shook her head no, adding: "Dana and I talked about it. She's very serious, Jeff. She wants to catch up with me, sort of, since I got first anal on her."
I couldn't believe it. Deb and Dana always had a lot of strange sisterly quirks going on between them, and I was pretty much used to it. But this? This was way beyond weird, even for the two of them. "Debs," I said, as serious as anyone can be with his cock up his girlfriend's ass while discussing buttfucking the aforementioned girlfriend's twin. "You really want me to have anal sex with your sister?"
Deb looked at me intensely, somehow sympathetically, as if she could finally see this whole thing from my perspective. Biting her puffy lower lip and furrowing her brow, she murmured: "Well, baby... It's not like I want you to, not exactly. It's just that... See, I sort of owe her..."
Looking into my stupefied eyes, Deb told me about her first time. Specifically, she revealed that it was Dana's boyfriend who took her virginity. It was back in high school, when Deb was a nerdy chubby loner and her twin was a super popular cheerleader. After they both decided that they wanted to have sex, Dana had no problem getting her jock boyfriend to pop her cherry. Insecure and awfully uncomfortable with her body, plagued by the feeling of being sexually inferior to her bubbly twin, seeing her virginity as a sort of burden to be rid of, Deb eventually asked Dana to help her out. Dana agreed.
One night, after giving him a handjob to get him hard, Dana blindfolded her boyfriend and tied him to her bed with the pretense of kinking things up a bit. Then, unbeknownst to him, she let Deb into the room. With Dana guiding her boyfriend's stiff dick into her sister's virginal vagina, Deb straddled the guy and slowly took her first cock inside her. Since Deb's hymen was already broken and Dana's boyfriend was quite high to begin with, he never knew what really happened that night. Deb fucked him in silence for a while, until Dana motioned for her to get off him so she could have her own fun. Deb left the room, no longer a virgin thanks to her twin sister.
"Holy shit, babe!" I croaked, my semi-hard cock stirring inside Deb's snug asshole as her story sank in. Sharing a guy back in high school, I thought, that's hot."Why didn't you ever tell me that!?"
"Because it's embarrassing, Jeff. I was such a loser back then," she said, clearly uncomfortable as she remembered her far from happy high school years. "I even had to ask my sister's help to lose my virginity, it's not exactly something I'm proud of... But," she added, "Dana did help me after all, and that meant a lot to me. I know that she comes off as a ditzy plastic doll most of the time, but she's really not that bad. And sure, we fight a lot, but we do love each other, you know. We really do."
I nodded, knowing that, despite their frequent bickering, Deb and Dana were very close, surely closer than my siblings and I. "So," I said, hesitantly "I guess she told you that now it's time to return the favor, lend her your boyfriend like she lent you hers back then?"
Deb shrugged, tilting her head. "Yeah, pretty much. Will you do it?"
Her eyes were piercing into mine. Those beautiful, soulful hazel eyes that I never tired to look into. I was so enveloped in Deb's warmth and her scent and our closeness, not to mention my cock still buried in her ass, that I didn't even need to think about my answer. The words flowed freely as I held my babe closer.
"No," I said, "I don't want to, Debs. I don't want anyone else. And yes, I realize it's okay with you and all, but I can't cheat on you, babe. Not even if you're asking me to. I love you, Debs. I won't do anything that could ruin things between us. Plus, why would I ever want to fuck another ass? You have the ultimate bubble-butt, babe, and you let me, no, you make me fuck it all the time!"
Deb just looked at me for a second, her lips quivering and her eyes shining. She made a little laughing sound, then she smashed her soft mouth into mine and kissed me furiously, pressing her body against mine and tightening her anal muscles around my length. I groaned as Deb devoured my lips, holding my face between her tiny hands.
I know what you're thinking. I'm an idiot, right? That's what most of my buddies would have thought of me if they had known that I had turned down the offer to fuck my girlfriend's sister in the ass. In fact, they already told me I was an idiot on a regular basis, insisting that I had picked the wrong twin because sure, Deb was okay, but Dana, oh boy, Dana was such a smoking hot chick with that super model figure of hers and blah blah blah. I just shook my head and laughed whenever I heard that kind of nonsense. They could keep flirty, fit, forever-on-a-diet Dana, the poor fools. She couldn't hold a candle to my sweet Debs. My smart, curvy, loving Debs that was currently trying to suffocate me with kisses while she milked my cock with her sperm-coated bowels.
When she finally came up for air, Deb had a beaming smile on her lips. "Oh Jeff! I love you so much, baby! I knew you were the real deal! Any guy I ever dated would have jumped at the chance to fuck Dana, they always looked at her, the jerks! But you... Oh, baby!"
She went on kissing me and squeezing my cock inside her rectum for a while, and I just let her. What do you know, apparently I had just passed some sort of test! As we made out, I massaged and grabbed and kneaded Deb's juicy rump. All the while, she slowly sucked me hard again with her slippery asshole, whimpering in my mouth as she teased the both of us into another assfuck.
