First Time Anal Gif Novels & Stories

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.

“Oh. You mean…” I nodded. “One of you… put it in her butt?” “That would be Andre, by virtue of his girth. No offense.” “None taken. I’m very happy with my hardware.” “Wouldn’t that… hurt?” Melissa asked. “You have to work up to that, from what I understand,” I explained. “This woman was no stranger to anal sex, though previously it was with a single man. What the three of us did was her first time. I seem to recall her enjoying it quite thoroughly.”

Lucy nervously adjusted her skimpy lingerie as she waited backstage, her heart pounding with anticipation and anxiety. At just 19 years old, she had never even considered doing p**n, but desperate times called for desperate measures. Her college tuition was due, and her part-time job barely covered rent. When the opportunity to be in an adult film presented itself, she jumped at the chance, despite having no experience in the industry or with anal sex.

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.

Licking his lips and looking sort of unsure, he started to move again, grinding mind-blowing slowly and moving his hips in thrusts that sent me toppling over the edge a thousand times until he was sure that I was completely fine and he started hitting me in rhythmic thrusts. This was it, my first time.

However, he pulled out, regained control, and after a few seconds I could hear his breathing return to normal. We took a few moments to catch our breath and recover. But it wasn't long before I felt the head of his cock press against my asshole. "Relax, baby," he said in a deep, husky voice. I took a deep breath and attempted to prepare myself for what I knew was coming. I was a bit nervous because this was the first time he had ever attempted anal sex without some type of bottled lube. His bulbous head hesitantly slipped into my bottom and produced an instant discomfort when it met my tight ring, which thwarted his progress. Cautiously, he eased himself forward, my body gave way, and he sli