First Time Anal Gif Novels & Stories

“I’m going to fuck your ass. Right here where we used to do homework. Consider it the next installment on the debt.” Lila’s breath caught, a mix of fear and dark excitement flooding her. She had never done anal before. But as Kai’s fingers, slick with their combined release, began circling her tight rear entrance, she knew she wasn’t going to say no. Lila’s breath came in short, shaky bursts as she remained bent over the wide granite kitchen island, her bare breasts pressed against the cool stone. The remnants of their breakfast still sat on plates nearby, but all she could focus on was the slick slide of Kai’s fingers circling her virgin asshole, spreading their combined cum as natural lube

One day I was bent over looking for a beautiful black and white shot of my city in the photo drawer. When I felt a hard thing touching my bottom. I didn't understand. I tried to turn around, but my Sir's strong hand held me steady. Then, he slipped his member in and started to fuck me anally. He spanked me and went up and down, in and out. I was completely shocked by this at first, but the real reason why I didn't tell anyone about this, was that I actually was too ashamed to admit that I enjoyed it! So much!

Without waiting for her to get back herself and without preparing or warning her to be ready for what is about to happen, Ryan at one go pushes half of his length into her butthole and at the same time begins going in and out of her. Ariella's eyes roll into her head as her butthole tears open and she begins wailing out. This is her first anal sex. She feels like she is breaking apart. Her ass is on fire. It's scorching her. "No, no, no!" She exclaims and starts pushing him really hard, tears streaming down her cheeks. But the more she pushes him, the faster he goes. The bed is twitching as her body shakes violently in response to his rough, fast strokes.

“You trust me?” Amy nodded, heart racing. She’d never done anal, but with Jeff, the fear mixed with excitement. He took his time—kissing her deeply, fingering her pussy first, then teasing her tight back hole with a slick finger. Gentle circles, then slowly pushing in, stretching her carefully. “Relax, baby. Breathe for me.” She did. The burn was strange at first, but when he added a second finger and rubbed her clit at the same time, pleasure started to overtake it. Jeff replaced his fingers with the head of his cock, pressing in inch by inch, murmuring praise the whole time.

Then he pulls out suddenly and I make a sound of protest at the emptiness. "Turn over." He helps me out of the stirrups. "Hands and knees on the table." I comply, my legs shaking, my body still buzzing from the aftershocks. He positions himself behind me and runs his hands over my ass. "I need to examine you from this angle as well." He spreads my cheeks, looking at me. "Very nice. Have you had anal penetration before?" "No." "We won't do that today then. But your pussy..." He pushes back inside me and I moan. "Your pussy can take much more."

She trails off seeming nervous. "What is it?" "I want you to fuck me... in the... in the ass." She buried her face in her hands to hide the redness in her face. "Have you ever done that?" I ask her already knowing the answer. She shakes my head and I smile. I've had anal sex only once since women didn't really seem to enjoy it too much. I turn her over and bring her hips back into the air and spread her ass cheeks. "You want me to fuck you here?" I say, pressing the pad of my finger against her anus. She tries to hide her moan and nods. "You know how to get what you want. Use your words."

“You’re doing so well, baby. Think you can handle both of us inside you?” I could barely speak, trembling and wrung out. “I need—I need you inside me. Both of you. Please.” Talin's eyes darkened. “Both of us? You want both our cocks filling you up at the same time?” “Yes,” I whimpered. “I’ve never done it before, but I want to try. Want to feel you both fucking me.” “Jesus Christ,” Douglas breathed. “We need to prep you first. You ever done anal?” “A few times,” I admitted. “But never while—”

“You want to feel a fat, swollen cock brushing that sweet spot deep inside you?” “Fuck… fuck… fuck…” He whimpered, hips rolling back instinctively. “Please… give it to me.” I groaned. “Need to open you more. I’m bigger than that dildo.” It took everything in me not to slam home right then. This was both our firsts—my first time inside anyone’s ass, his first time taking a real cock. I wasn’t going to rush it and hurt him. I grabbed the lube again, slicked the toy generously.

I grunted, spreading my legs and lifting them up, offering my pussy to them. “Fuck, it's so pink,” a finger runs over my slit, down to my anus. “We're going to take here too baby girl.” Oh. “Yes, please. Everywhere.” I feel someone's body on top of mine. He doesn't speak, no one does, and I feel the head of his dick at my entrance. “Breathe,” he hushed. I took in a deep breath and I felt the cock slip past my folds. “Ohhh,” I gasped as I felt the dick go into me, for the first time in my life.

Slow sex was only used when we were romantic. "I'm going to make this quick!" Asher impaled himself on mine, and he made a circular motion of his hips and then impaled again vigorously until I sighed loudly. I covered my mouth as I felt a strange sensation in my stomach. Asher's big, long shaft pierced my womb and made a very strange sensation. "Baby!" I screamed again as Asher removed his own. He was trying to get it into my anus. I had never done anal in my life. "I can't," I told Asher with a sad look in my eyes. Asher seemed to understand, and he didn't try to force it because anal sex for the first time caused a lot of pain.