First Time Anal Gif Novels & Stories

Incredibly detailed. The kind of detail that makes me pause. The kind of detail that tells me they’ve done this before, not casually, not for fun, but with care, structure, and deliberate intention. I scroll to the beginning of the list. The first section is Anal, with subcategories I wasn’t expecting: fingers, toys, penetration, rimming. I stare at the list for a moment, then start slowly.

His hand moves from my waist around my back to grip my ass again, grinding me down against him harder. “I want this,”He moans, lifting his silver gaze to me while his finger brushes and circles the pearl of my ass. My stomach knots, I’ve never considered doing anal before. No one has ever touched me there. “Have you ever tried it?”Finn whispers, sucking on my bottom lip while his fingers continue to stroke me teasingly as I rock against him. “No,” I sigh, closing my eyes when his lips travel down my throat, feathering hot and wet kisses that make my head whirl. I’m nervous, but too aroused to actually be concerned that the pressure of his finger on my ass is increasing.

“For both of you to fill me up at the same time, and my mouth is off-limits for this.” Shock, surprise, and lust hit the bonds in that specific order. This was going to be a first for us. Both of them have taken turns with my ass, but we have never tried double penetration before. They were very well-endowed men, so they wanted me to be comfortable with anal first. They pounced on me, causing me to giggle at their eagerness. That turned into a deep moan when their canines pierced into their marks. Heat pooled in my core. It clenched with need, arousal pouring from it.

I was going to do it, I was going to have anal sex with a guy I met hours ago. I ran my hand through my pussy, coating it in my thick juices, then I spread them over my asshole. Noah’s dick was already soaked in my fluids, so there was no need to apply anymore. I finally placed the tip of his penis on my asshole, pointing right towards the entrance. “Slowly,” I warned, remembering when Felicia had done it. Freya and Ethan kept fucking, but they were watching without blinking. Neither one had ever had anal sex, and watching it happen right in front of them was intriguing and exciting.

Daniel turned around so that his chest was pressed to the wall and his hand guided the stiff rod to his Bussy. Daniel felt as his inside stretched, and a sharp pain shot up to his brain. Daniel cursed under his breath, it was his first time having anal sex. He placed a soft peck on Daniel's neck. He felt the peck wasn’t enough to tell Daniel how much he enjoyed being inside of him. He bit on Daniel's neck, it was like claiming the human for himself alone, he couldn’t share him with his brother, never. He thrust slowly in and out, the soft moans Daniel gave were like music to his ears. The sloppy sound of their body hitting against each other added to the rhythm of the music.

He points his tip against the cheek of my ass. "I wonder which hole." He moans. "Liv p-please..." I stuttered in fear. I have never tried anal before and he said he never dreams of doing it to me because it makes him look like he's disrespecting me as a woman. He suddenly inserted his fingers. "Liv... no... please.." I begged but he cannot hear it. "You're not wet yet. That's more like it." He holds me down tight and slams himself inside me. I moaned loud as he pounds on me repeatedly and mercilessly. I grip tight on his arm which was rubbing my nub as my eyes rolls back while my tears were streaming down my cheeks.

In a few minutes I felt his waist tighten and he grunted hitting the back of my throat constantly and hard with his cock before he came in my mouth. I thought it was over until he flipped me over on the bed. I laid on my front and he held my waist pushing it backward with my ass up. I shuddered realizing what he wanted to do. His rod was on my ass and he was slapping it against one of my ass cheeks. “W-what are you...doing?” I asked and soon begin to have labored breathing. I had never had anal sex before and I heard it was painful. I recalled Celine telling me about her first anal sex and how brutal it was for her.

Master D groaned, filling her ass with his hot seed. He untied her, laying her on a padded table. “You took that well, pet. But we’re not done yet.” Ana looked up at him, her body aching but eager for more. He lubed up his fist, rubbing it against her sensitive hole. “I’m going to fist this ass,” he said. “Break you open.” She nodded, biting her lip as he pressed his fist inside her. The burn was intense but she relaxed, letting him work his way in. He pumped his fist, stretching her impossibly wide. Ana screamed, her eyes rolling back in ecstasy.

He tensed and stopped moving inside of me as a low growl escaped his lips. “Easy, my friend. It is also my first time trying this,” Eliphas leaned and whispered in his ear while his finger was exploring his anus. I took Kieran’s face and held it in place for him to look at me as he resumed pushing in and out of me while Kieran was getting him ready to receive him. With a small rub in his back, Eliphas entered Kieran’s anus inch by inch, making him close his eyes and groan in pain and pleasure, until he was all in.

“You’ll see. You trust me, don’t you?” “Yes, sir.” “Do you trust that anything I do will make you feel good?” He asked. “Yes, sir,” I said without hesitation. I watched as he thrust the silver item into my pussy, took it out, and teased the entrance of my puckered hole. I had never had anal sex, but Nero had fingered me there a couple of times as he fucked me from behind. I couldn’t even deny how good it felt when he did that. The item he was teasing me with looked like a small egg and was undoubtedly larger than his fingers. It scared me. Anal fingering could be uncomfortable at first.