As I saw her brown eye push outward, I pushed in to meet her. The first segment of my finger slid into her and I felt her sphincter grasp tightly around it.
“You ok?” I asked.
Nancy exhaled. “Yeah,” she said. “That’s not bad.”
“That’s a finger,” I reminded her, “not my penis.”
“Penis?” she giggled. “My, aren’t we formal, especially considering where your finger is. Really, I’m ok. What’s next?”
I pulled my finger slightly out, twisted it, and slid in, farther this time. “That.”
“Mmm-hmmm,” she hummed through gritted teeth.
“And that.” Farther in this time.
“Unnnnn.”
“And this.” Out, twist, twist, in. And out. And in again.
“Mmm-hmm.”
And then I was sliding my finger in and out of my sister’s asshole, feeling her clasp and writhe as she tried to get used to the penetration. She clutched handfuls of sheet as she pressed her face into the pillow. Give the girl credit, she pressed her ass back to me, giving her all to her anal deflowering.
I moved my other hand to her pussy, rubbing the side of my index finger up and down along her slit. Nancy’s painful grunts alternated with noises of pleasure as I worked her neighboring holes simultaneously. As I began to slide two fingers in and out of her pussy, she turned her head to the side, making that sexy high-pitched sound she makes when she gets excited.
I felt my fingers glide against each other, only a thin membrane separating them as I alternated penetrating her holes. In and out, back and forth, giving my sister her first DP. Nancy cooed and ooh’d, biting her lower lip as her eyes slipped into sexy, half-lidded closure. “Oh, fuck, Jim. Yeah, that’s good. Oh, baby brother, I fucking love this. Oh fuck. I think I like the ass fucking almost as much as the pussy.”
Nancy wanted me to get her close to orgasm, then to remove my fingers from her cunt. She wanted to see if anal penetration would take her the rest of the way. Who was I to say no?
Nancy told me when she felt close, and I pulled my goo-coated fingers out of her, and into my mouth they went. I sucked my sister’s juice from my fingers as I fucked her ass with my other hand. Fast, deep, and hard, I fingered her as she bucked beneath me, fucking back against me as she moaned wordlessly.
“ohh – ohh – ohh – ohh…” Nancy’s tone got higher and higher as I felt her sphincter tighten around my finger, squeezing and releasing, pulling my finger deeper into her. Suddenly, Nancy’s entire body tensed, shuddering, and Nancy intoned “Ommmmmmmmmmmmmmmmmmm” for about 10 seconds before her entire body relaxed, collapsing to the bed with a big smile on her face.
“Wow,” she breathily exhaled. “That was fucking incredible!”
“What the fuck was that?” I asked. “I’ve never seen you have an orgasm like that before!”
“Whoo! I’ve never had an orgasm like that before. That was completely different than a pussy cum. Wow!”
I pulled my finger quickly out of her asshole, saying “THWACK!”
“Thwack? What the hell is that?” Nancy asked, laughing.
“Oh, that? Thwack is the sound your asshole would make slapping shut if shit wasn’t tapered.”
“Oh my god! That is so vulgar. You are disgusting!” Nancy was shaking with laughter, tears rolling down her cheeks.
“Oh no… am I too disgusting to fuck you in the ass?”
“Of course not, baby. Come stick your dick in my butt.” Nancy wriggled back to her knees and put her forehead against the pillow. “Just go slow, ok?”
“I promise, love. I don’t want to hurt you.”
“Don’t worry. I expect it to hurt some. But I want to see if I can cum like this, so come on in!”
I slipped off my shorts, positioning the head of my cock at her anus. I pressed forward, pushing the tip of my cock against her, then rubbed up and down to gather lube.
“Mmmm…. don’t take it away, baby. Put it in me, brother. Fuck your big sister’s tight ass.”
I pressed again, spreading her open, then paused. I waited a couple of breaths, then pushed again. Nancy inhaled sharply as most of my cockhead worked in, opening her sphincter. She breathed again, then pushed slightly outward on the exhale, just like I’d told her.
I didn’t move, giving her time to adjust to her new friend. “Take your time, sis. Let me know when you’re ready for a bit more, ok?”
“Ok,” Nancy panted. “Give me…” I felt her push outward again, then move back against me. “…just a second.”
“No problem,” I said, feeling Nancy inhale deeply. “You’re in charg-” I was cut off as Nancy wiggled, then thrust fully back against me, impaling herself fully on my hard shaft, grunting in pain, but holding firm.
“Uff – uff – unghh” Nancy groaned, her ass clamping hard. “Oh fuck that hurts! Don’t… please don’t move, ok!?”
“Jesus, Nancy! What the fuck?”
“Like… unngh… ripping off a band-aid, I thought,” she grunted through gritted teeth, “you know, like, just get it over with. It was gonna hurt no matter what. Oh… owww! Pull back out a little, ok?”
What a team we made, my sister and I, adjusting ourselves to get her used to getting ass fucked by her baby brother. And she did get used to it, eventually moving slightly as I slowly eased back and forth, sliding in and out as I held her hips steady. We found she could easily take about half my shaft at a moderate pace, and we moved together, me feeling pressure so tight, and love so intense, that it wasn’t long before I felt myself on the edge of filling her backdoor with a big load of brother-juice.
“Oh, yeah!” Nancy encouraged me. “Oh, brother, do it! Put your load in me. Boldly go-” She panted a few times. “Oh-oh-oh! Ommmmmmmmmm!”
My sister’s anal climax caused her ass to squeeze my cock even tighter. I felt the mushroom head of my cock pulled back and forth, the fleshy ridge rubbing against her constant pressure. I could take no more! “Oh fuck Nancy, yes! Oh fuck, love, I’m…. oh fuck I’m so… so close…. oh… fuck! Here I cum, sister! I’m going to fill… your… ass!” And I sprayed her ass, the inaugural painting of her rectum with semen. I thrust forward, driving the entire length of my cock back into her. Nancy roared, arching her back and throwing her head back, her long, wavy hair reaching the center of her back. It was an image I’d never forget, my cock inside my sister’s ass as we came together.
My cock twitched inside her as we lay sprawled, collapsed on the bed, gasping incredulously at this new shared experience.
“Never…” Nancy panted out, “ever doubt how much I love you! That was amazing, but please pull it out.”
I slowly lifted my hips, drawing my cock out. My cockhead pulled out with a slimy sound.
“Thwock!” Nancy laughed.
“THWACK,” I corrected, laughing along with her.
“Whatever,” she said. “I can’t believe I just got my last cherry popped… or my last cherry THWACKED, should I say?”
I kissed my sister between the shoulder blades, small, quick pecks over her tanned skin. “You know,” I said, “you’ve definitely more than repaid me for last night. You don’t ever have to do this again, you know.”
“Screw you!” she said. “This was fun! It hurt, but I loved it. I loved getting to give something to you that no one else has ever had. You are my one and only anal love.” She turned onto her back beneath me, wrapped her arms around my neck and pulled my face down, kissing me lovingly. “See? I can be your dearest love, and your slut! Tell me what I am, baby brother.”