Weird Sisters Ch. 02

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His girlfriend's twin sister has a weird request.
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Part 2 of the 4 part series

Updated 08/22/2023
Created 08/14/2014
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ZenZerker
ZenZerker
5,005 Followers

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.

I was ready for round two when Deb broke our lip-lock. She sat up straight, her hands on my chest, her back arched, her hips rocking as she began grinding her round meaty ass on my recuperated pole. She surprised me when she said between squeals of pleasure: "Mmh... Your cock feels so good in my ass, baby... Mmmh... I'm so glad you said no, Jeff... Oooh yeah, touch my big titties while I ride your cock with my ass... Aaaahhh yeah, like that!... Mmh... Now I know for sure I'll have nothing to fear when we fuck Dana together."

"What!? What do you mean 'we' fuck her? Plus, I just told you I don't..."

Deb laughed and leaned down to give me a swift kiss before returning to stirring her bowels with my hard shaft. "Yes, I know what you said, baby. But don't you see? That's exactly why I can agree to Dana's request. Now I know for sure. I can let you do it BECAUSE you don't want to. Get it?"

I nodded my head, puzzled, focusing on my cock up her ass and my hands on her buxom tits, the only things that still seemed to make some sense. "Sure," I mumbled, "there's some twisted logic to it. But babe, I was serious. I don't want to cheat on you!"

It felt somehow absurd to have to say something like that to my girlfriend, but then I should have known better than to try and reason out anything at all that involved her relationship with Dana. As expected, Deb was unperturbed by my renewed profession of fidelity.

"Aww Jeff, I know. And believe me, I love you for it," she said, sitting still on my dick, resuming her cock-milking routine as she spoke. "But I never meant to let her have you all to herself. My only condition to lend you to her was that I'd be involved too. And of course Dana agreed, little lesbo slut that she is!" Deb smirked at that, then she calmly concluded: "You don't have to worry, baby, it's okay. I'll fuck her too. It's not cheating if it's a threesome, right?"

Deb was smiling. Me, I was panting. And not just from the amazing anal suction she was treating me to. "Whaaa?! You mean... You and Dana!?"

Deb just gave me a thin smile and cocked an eyebrow. She raised her hips up, sliding her asshole all the way along my pole until only my mushroom head was still snugly gripped within her anus, then she slid down, moaning, cramming my boner balls-deep inside the buttery tightness of her ass. As she impaled herself on me in a slow tempo, she began speaking in a mewling, pleasure-thick voice.

Apparently, Deb and Dana had experimented a bit when they were younger. They had never had issues being naked around each other or touching one another's body. Dana in particular was quite taken with Deb's tits, which blossomed earlier than hers and were always way bigger. They had practiced kissing with each other way before either of them ever kissed a boy. They had often masturbated together, mostly just watching each other. Sometimes though, they fingered the other's pussy to climax. It didn't happen all the time, but it did happen.

Deb related all this as we fucked. I listened in a daze. Her voice was broken by throaty moans as she persistently stuffed her ass with my hard-on, but her manner remained very nonchalant, as if she didn't really think much of her incestuous encounters with her twin.

My cock twitched inside Deb's slippery rectum when she told me about their first year of college, when their lesbian activities reached their peak. Dana had always been interested in having sex with a girl, and she did it repeatedly during their freshman year. Deb wasn't as drawn to lesbian sex as her sister seemed to be, but she was curious and she didn't want Dana to be more sexually experienced than she was.

Once again, Deb requested Dana's help. Deb's idea was that Dana might hook her up with one of her new girlfriends, someone suited for her, gentle and discreet. Dana wouldn't have any of that. Since Deb wasn't really into girls and she didn't want people to know about her experimentation, Dana convinced her that the best course of action would be for the two of them to have sex. After all, they had done stuff before. Knowing she could trust her twin, Deb accepted.

My head was spinning as my babe told me about licking her sister, getting her pussy thoroughly and voraciously eaten out by Dana and getting each other off while locked in a sixty-nine. She chuckled as she said that Dana really got off on licking pussy, just like Deb herself did on giving blowjobs.

"So... Aaaah fuck! So how was it, babe?" I asked, throbbing hard and gasping with arousal.

Deb shrugged, making her heavy tits jiggle as she bounced her ass on my cock. "It was okay I guess... Oooohhh! Dana was really into it, way more than me... Uuuhhh fuck! We did it a few times, and that was good enough for me, but... Ooooh yeah, baby, push your cock up my ass aaaahhh! But she kept offering to lick my pussy if I wanted, until I started dating... Uuuhh!... She seemed upset whenever I brought home some guy... Aaahhh fuck yeaaahh, you're so deep in my ass! But by our second year she was back to boys too, so... Uuuuhhh yeah, harder, fuck my ass hard, baby!"

Now, I like to fantasize about two girls going at it as much as the next guy, and I've read my fair share of incest stories too. Still, I never thought I'd actually get so close to the real thing. I wasn't lying to Debs when I told her that I didn't have any interest in fucking her sister. But this was quite different. My girlfriend and her twin dyking out? It was hot. Incredibly hot. My pulsing dick testified to my increasing arousal.

Deb obviously felt that her tales of sisterly incest were turning me on. As she kept sliding her asshole up and down my hard meat, she smiled sultrily and said: "Mmmh, it seems like you're enjoying my stories, baby... Would you like to see us eat each other out, right here, in front of you?Uuuhhh yes, keep fucking my ass!... Would you like to see my sister licking my pussy, baby? I know she'd love to. I bet she wants to eat my pussy just as much as she wants your cock in her ass, even more maybe. Aaaahhh fuck yes, faster, like that, long and deep!... Wouldn't you like to stick your big fat cock up Dana's tight virgin asshole after I licked it and made it all wet and ready for you, baby? Mmmh... I'd love to have her eat my pussy out while you fuck me in the ass... That would be so ooooooh fuuuck!... Sooooo hot! UUUUHHH!"

That was just too much. I bucked my hips up into Deb's pliant anus as hard and fast as possible while she frantically tortured her clit with her fingers, whimpering and pumping her hips to meet my thrust. I pistoned full force into her rectum, sinking my hands into her juicy buttcheeks, until I felt my balls draw up and I started spurting jet after jet of cum deep in her ass. The feel of my cock swelling up and sending ropes of cum splashing against her anal walls pushed Deb over the edge. With a choked squeal she impaled her asshole one last time on my ejaculating shaft, shivering all over, gasping and crying out in orgasm while her rectum pulsated and contracted around me, milking me until I was drained of every last dribble of seed.

*****

In the following days, Deb never lost a chance to conjure up naughty lesbian scenarios for me. She was obviously getting a kick out of the idea of us having a threesome with her sister. And now she knew that, despite not being interested in Dana herself, I had a weakness for the idea of the two of them dyking out.

Either when we were having sex or to tease me into having sex, my babe described all sorts of lesbian acts involving herself and her sister. I wasn't sure if what she told me was a recollection of past events between them or just some hot incestuous fantasy she concocted at the moment, but I didn't care. My reactions to Deb's tales were always very enthusiastic. It was insanely hot to pound my girlfriend's pussy or ass while listening to her murmur about the two of us fucking her twin sister and making her service us like a good bisexual slut. That was hands down my favorite fantasy involving Dana and I came like a geyser whenever Debs evoked it.

When I finally asked Deb if she was kidding about Dana having a submissive streak, she just shrugged and said: "I think so. She's sort of into pain, I can tell you that. She likes to be spanked, hard. And when I played with her tits, she didn't just want me to tweak her nipples. She asked me to really pinch them and twist them, pulling on them until it hurt. It was a bit weird, but she always went crazy when I did that. So yeah," she concluded with an impish grin, "my guess is that we could easily make her into our little fuck-toy. Just say the word, baby..."

And of course I did. After three days of animalistic fucking fueled by fantasies of sisterly incest and whatnot, I caved. I agreed to have a threesome with my girlfriend and her twin so that I could pop Dana's anal cherry without technically cheating on my babe. Funny thing is, at that point I didn't even found it too strange anymore. Just a bit.

*****

The night after I accepted to go through with it, I met the girls at their family's art gallery after work. Deb was wearing a dark pencil skirt that hugged her magnificent ass amazingly and an elegant white blouse that strained to contain her bodacious boobs. Dana had opted for a stylish crop top and a pair of tight fitting jeans that showcased her long toned legs and taut butt. She had dyed her shoulder-length hair ash blonde since the last time I saw her the previous week, while Debs had her own long light brown locks tied in a ponytail. They were both wearing heels.

The plan was to go get dinner together at an Italian place the girls liked, as we usually did at least every over week, and then return to our place for 'dessert'. That part was definitely new and more hazy as to the details. Deb had made it sound very easy when we had picked the night and I asked her how exactly this was going to work. She had just laughed and said that I shouldn't worry about anything, she'd handle Dana and all I had to do was follow her lead.

All through dinner we chatted and traded morsels of our orders as usual, commenting on the food and talking about friends and work. As always, Dana was the center of the conversation, with Deb and me remarking here and there. That night though, Dana's frequent laughs sounded a bit strained, her typical bubbly enthusiasm appearing forced and somehow fake. I noticed her stealing glances at me more than once when she though I wasn't looking. She also seemed to be touching Deb way more often than she usually did, lingering every time their bodies brushed together accidentally and resting her fingers on the back of Deb's hand for long seconds to attract her attention.

ZenZerker
ZenZerker
5,005 Followers