First Time Anal Gif Novels & Stories

Later, curled on a rug in front of the fire with cheap red wine, he kisses my shoulder and asks softly, “There’s something I’ve wanted to try with you… if you’re open to it. Something new.” I turn in his arms. “Tell me.” “Anal,” he says gently. “I want to be careful. Slow. Only if you trust me completely.” I bite my lip, a thrill of nerves and excitement mixing. “I do trust you. Completely.” He spends a long time preparing me, lots of lube, gentle fingers circling my tight ring, pressing in millimeter by millimeter while his other hand rubs slow circles over my clit. I moan into a pillow, hips rocking back, guiding his pace with soft words.

she whispered, her voice strained and full of need. "So do I, sis.. So do I.." I whispered back. We had crossed an irreversible threshold that night, and there was no way I wanted to go back to being just normal brother and sister anymore. She was mine and I was hers. I think we could both feel that this was but the first of a thousand loving encounters to come, as our hearts seemed to beat together in sync. Her butt kept squeezing around my cock, as if she wanted to feel me even deeper within her, with every part of her possible. The pleasure was clearly visible on her face. "It doesn't hurt?" I asked, a little surprised, because I had heard people say that anal sex was painful the first ti

So, instead of pulling out of me in that second, he flips me over so that I was laying on my stomach before plunging his hard member into my ass. I screamed as the pleasure mounts. This was the first time he’s gone anal with me, and to be honest, I thought it’s not that all bad. My eyes roll to the back of my head, and I feel him push his palm against my skin, urging me to arch my back lower to the bed. I followed his silent request, grabbing the pillows above me then burying my face right between them. Alex never let me go until another hour later, and I collapsed on the bed powerless. My breathing fast and restless.

he snarled from behind her, gripped her hip hard and pushed further into her, easing his length in and out of her in gentle strokes while massaging her clit with his other hand until she was writhing under him, begging for release. Casey spared a few precious seconds to realize the care he was taking to make sure her first-time anal didn't suck. That she was indeed building toward release and not being torn in two from a cock that could do real damage to her pussy let alone her virgin ass. She could tell from the tension in his body that he was having trouble holding himself back from just slamming into her; gripping her hips in both hands and pounding her hard. "Come for me, cari?o," he gro

Leaning forward, he placed his lips against my back, softly kissing it. He repeated it twice before he sucked and bit every part of my back as if he was marking me as his territory, he slid his hand down to my bum. I suddenly blushed as his hands slapped against my butt. He rubbed it like dough, planting kisses on it occasionally. I felt a light breeze on my hole followed by something long and stiffened against my butt. I had never done this anal before. He inserted it and I winced a bit before letting out a moan. Spreading my legs apart and wrapping them securely around his hips, he went deeper.

Without waiting for a response, he thrusts into her tight hole. "Aahhhh," Sariel cries out. He groans, "Damn, baby, you’re so tight." "Yeah, don’t stop, please," Sariel begs. Maddox follows her instructions, thrusting hard and fast into Sariel's tight hole. It’s incredible, he thinks. He hadn’t expected to experience this for the first time. He had never had anal sex before; only now with Sariel. If he’d known it could be this pleasurable, he’d be willing to do it again, just with her.

My vision blurs, pleasure spiking. ‘Ahh, yes, fuck me!’ Orgasm builds a third time, crashing as he growls, spilling hot inside, pulsing ropes coating my walls. We collapse, tangled, breaths syncing. But I’m not done. Minutes later, I’m on top again, facing away...reverse cowgirl. His hands spread my ass, thumb teasing my tight hole while I ride slow, deliberate. ‘Ever done anal?’ I ask, glancing back. ‘Not with you. Yet.’ Voice strained, excited.

You'd think I'd get a change of heart when I think about the fact that I'm preparing my hole for my best friend, but just the thought of prepping myself for Chase had my dick standing rock hard, leaking pre-cum onto my sheets. “There really wasn't any going back,” I muttered as I stretched my hole even more and added an extra finger. I let out a soft moan which surprised me. I heard that not everyone feels good for their first time doing anal, so I didn't expect to feel this way. “Maybe I'm just a born slut.”

"Uuuh!... No, I'm fine just... Aaaahh fuck! Gimme a second... You feel so big, baby, you open me up so good! Don't stop, it feels weird, but nice... So stretched... So full... Uuuuhhh god! Give me more, baby, I want to feel all of you... Deep in my ass... Just... Uuuuh! Just go slowly, please." Her whimpering voice and her gasping, broken breaths were so hot. I was thrilled to hear that she was liking her first assfuck and she actually wanted me to give her more cock. I wondered what did I ever do to deserve this sweet, hot, gorgeous girl who had just gifted me with her anal virginity.

My body burns, my sex is screaming, my insides know his shape, my flesh is twitching, but my heart’s ache supersedes all of them. I want to cry, laugh, and scream at the same time, but instead, I moan at his fingers that widen my second hole because my sex is too bruised for more. The sound of a condom wrapper echoes the room; I didn't even know he had one. I've never had anal before; I mean, I have with a toy, but not with him. Perhaps I am doing this wrong… I don't know if I'm supposed to be thinking of the baby I carried and lost as he adjusts me to my side for better access— I'm all too new at this.