First Time Anal Gif Novels & Stories

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.”

An orgasm ripped through her pussy and then another and another. Jason had lost all sense of control. His animal instincts took over. He knew what he wanted and he was going to have it. It was something he had masturbated to countless times. Thoughts of how his mother would react didn't even enter his mind. He pulled his dripping cock from her pussy and pressed the tip against her sphincter. He was about to experience anal sex for the first time in his life.

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.

But then he sticks his forefinger in, circling and takes it out, then he goes down, and I feel him start to force it into my ass and I take a deep breath, relaxing, just so I don't hurt myself, but Soren knows what he's doing and repeats this movement a few times before finally penetrating me with his finger. I let out a low moan, feeling a slight discomfort, after all not even Klaus had done this. "Does it hurt?" Soren asks worriedly. "No, it's just uncomfortable," I replied. "It's the first time I've done this... without being a slave... Not even Klaus has done anal with me." "I'll be gentle," Soren said, and I felt him leave just the tip of his finger and move it around. He began to move

My whole body shook as wave after wave crashed over me. They didn’t let me rest. Jake pulled out, his cock shiny with my juices, and they flipped me onto all fours. Tyler took my pussy immediately, slamming in from behind while Chris took my mouth. Mike and Jake knelt beside me, groping my hanging breasts, pinching and twisting my nipples until I whimpered. Then Jake’s voice, low and dark near my ear: “It’s time, Mom. I’m going to take your ass now.” My heart stuttered. I had never done anal. Not with David. Not with anyone. Fear spiked through me even as fresh arousal flooded my pussy.

First Guy is doing the whipping this time, and he must have gone all out because the pain makes tears prickle my eyes. “Tap out is your safe word,” he says, squeezing my chin in his hand and tilting it up. “Once you say that, all this stops, and you tell us everything.” As he speaks, the pain fades as heat rushes back with the same intensity. Moisture starts to gather between my legs. My confidence falters, and for the first time, I’m unsure of myself. He smiles at my inner turmoil as Thirst Trap trails a finger up my bare thighs. “Do you want to tap out now?” the First Guy asks, leaning down to nibble on my slightly parted lips.

he says as he pulls down his sweat pants and kneels between my legs to positions himself with his fat cock standing tall and proud. “Wait…” I stutter and put my hand on his shoulders to slow him down, the size of his member scares me, it's my first time seeing one in real life…the magazine doesn't do justice to how magnificent the hard shaft looks. I touch it curious and Felix groans, “No baby, if I cum it will be in your tight pussy and nowhere else" he says and slaps my hand off him, “I'm ready” I whisper and lay back for him. He doesn't say anything else as the crown of his meat kisses my opening and he slowly pushes the fat cock into me inch by inch.

I never let anyone touch me down there, this is the first time I let someone lift my skirt and only an underwear covers my sensitivity. I stopped kissing him and looked at his eyes with nervousness. Damn! Hahayaan ko ba siya? A part of me remembered that he is my teacher. We shouldn't do this but I am so fucking turned on right now. I can feel my wetness and I don't think I can back out.

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.