Deb turned her face to look at me. “Well,” she said with a smile, “I win. Dana is still an anal virgin.”
That was unexpected. “Oh? Mad as she was, I thought she was gonna have Rodrigo fuck her ass the second he landed or something. Actually I imagined she would go further, you know, to get another first on you in retaliation, like maybe…”
“Rodrigo didn’t come,” Deb interjected. “She went to the airport to pick him up and he wasn’t even there, so she called him and he said he’d decided he wasn’t flying in tonight after all. Long story short, they had a huge fight and kinda broke up. So Dana didn’t get her ass fucked in the end.”
There was still more than a hint of gloating in Deb’s voice, but I detected a note of concern for her sister too. After all, they weren’t has hostile as they sometimes seemed to be, I knew them enough to know that. But there was more to it, I could almost see the wheels in Deb’s head turning as she elaborated on something she wasn’t saying.
“Well, there goes another one,” I said, not really surprised about Dana breaking up with yet another guy. Still, I asked: “Is she okay?”
Deb shrugged as she hugged me tighter. “Yeah, I guess. She was still freaking out, but not about Rodrigo. She never loved him or anything. You know how she is, she just wants to look awesome beside a supposedly cool guy. But she’s still super upset about the ‘first anal’ thing.”
“I bet she is,” I said, feeling Deb’s shapely thigh straddling mine, brushing softly along my leg.
“She said she’s been watching our pics all evening. She liked them a lot, apparently” Deb said, nuzzling my cheek. There was a strange edge to her tone as she pressed her body against mine, murmuring into my mouth. “She said she’s jealous, you know. Very jealous, actually.”
“Uh-hu…” I mumbled, feeling suddenly alert. Deb’s mood had definitely shifted toward a sort of sexy vibe, but not one of her usual sexy vibes. This was subtler, new. As she rubbed her warm, curvy body against mine, I could feel her erect nipples poking into my chest through the thin cotton of an old Sublime T-shirt of mine that she wore to bed.
Her voice was tinged with mischief as she giggled: “Dana said she did nothing but play with the buttplug and finger her pussy since she got back from the airport. Looking at our pictures all the while, of course…”
“Of course,” I croaked, imaging my girlfriend’s twin masturbating both her holes to the lewd pics of Deb’s gaping anus oozing my cum, not to mention the close-ups of my dick pushing gobs of gooey sperm back into Deb’s ravaged asshole. I felt my pulse quicken and my cock stir as Deb’s tiny hand caressed my chest in slow circles, patiently moving lower toward my abdomen.
She brushed her mouth against the corner of mine as I lay there, motionless. She was biting her lips as she said: “In her last text she also asked me something, baby. Something kinda weird…”
I had to swallow the lump in my throat before asking: “Yeah? What is it?”
“She asked me if she could borrow you to pop her anal cherry.”
“What!?”
Deb just looked at me as she snaked her hand into my boxers, her lips upturned in a thin, unreadable smile.
*****
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!?”