First Time Anal Gif Novels & Stories

He slammed into my pussy from behind, fucking me hard and deep while the water splashed around us. “Yes…fuck me!” I cried out, the exhibitionist thrill pushing me closer to the edge. He pounded me mercilessly, then pulled out and moved us to one of the wide sun loungers. He laid me on my back, spread my legs wide, and pushed his thick cock against my tighter hole. “Wait… Damon, I’ve never done anal before,” I gasped, eyes wide. “Today you will,” he growled, slowly pushing the head of his cock into my ass. “Relax, baby. Take it.”

“Not yet, nasty girl. We’re just getting started.” He reaches into a nearby drawer. He pulls out a small vibrator. The toy buzzes to life with a loud, insistent hum in the darkness. He presses it firmly against my clit. The intense vibration rips a scream from my throat. My entire body convulses. He holds me right there on the precipice. The first wave of orgasm builds higher. It promises an even deeper, dirtier descent into the night ahead.

Alexia looked up at Melvin, to see if he was displeased or uncomfortable by her being called 'big sis', but her expression was immediately sore when she noticed Melvin wasn't even paying any attention to her, Melvin's gaze was directed down towards where a stood, when I locked eye contact with him, I wanted to move my eyes away from his, but it was impossible because every time I locked my eyes with his, attempting to unlock myself from such gaze has always been futile because I never seemed to have the heart to do such.

"I need you inside me." He removed the butt plug slowly. I felt the strange, empty pop as it came free. Then I heard the squirt of more lube. I felt the broad, slick head of his cock press against my asshole. "Wait, there?" I asked, my heart hammering against my ribs. Actual anal sex. Another first. Another frontier I had never planned to cross. My body was alight with nervous anticipation. "Yes, baby," he said, his voice a calm anchor in my dark world. "Relax. Just breathe."

That was the first time the couple had anal sex. Though she was tight and cried in pain when he penetrated her for the first time, he eased it by going slow, holding her hips and putting in only a little of him at first and increasing the erotic thrusts over time. He nibbled and licked on the nape of her neck and ears making her moan loudly and enjoy every second of the love making as ecstasy flooded through both of them, culminating in her having multiple orgasms and him exploding his complete load into her.

he repeats. I shake my head, and his features relax, the tightness in his shoulders loosening. “Then what’s wrong? I’m pretty sure I was reading the signals right, and you enjoyed it.” His lips curve up a little, a hint of smugness showing through. I press my hand over my eyes. “I’ve never done that before,” I mumble. Like earlier, he takes my wrist and tugs my hand away. His brow is furrowed. “I already know that was your first time doing anal, so I assume you’re saying you never squirted before?”

I remember my first time. “We will do this slow. And we will only do what you feel comfortable with” - I say and Mike nods his head. I pass get up and grab a condom from the pocket of my jeans and I slide it on his cock. His eyes dart open looking at me. I smile at him - “have you ever done anal with a woman before?” - I ask Mike nods his head. “It’s the same, stretch me first, tease my ass and slowly fuck me” - I say and I can see redness appearing on his face.

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.