Taking Annie's Virginity

All characters involved in all sexual contexts are 18 years of age or older.

For context and clarity: Annie recently turned 18, and the main character is 21. I never explicitly state it in the story, but it is important to know, so I’m just putting it here.

Enjoy!

—

I walked into the restroom to see Annie waiting for me. I looked at her, the door hanging open as I gave her a confused look; but I said nothing. The door blocked my face from the people around me and nobody could see inside, where Annie sat. I checked behind me, then stepped in and locked the door behind me.

Annie held her finger to her lips, indicating I should be quiet. Then, she stood and gingerly approached me. Standing on her tiptoes, she whispered into my ear,

“You knew what I wanted before you closed the door.”

I stared into her pale blue eyes, considering her statement. She hadn’t asked it, she simply said it as a fact.

And she was right. I knew. And I wanted.

But it wasn’t right. My childhood friend’s little sister, how could I do something like this?

Let me explain.

—

Lucas, my childhood friend, had just graduated from college, and he and a few other graduates decided to rent out a small man-made pond venue out in the country. This venue had a large covered structure designed for people to hang out in, wet or dry. It had a kitchen area, as well as plenty of seating, and a pool table. Next to the structure was the pond and a small beachfront area with a row of lounge chairs, where some of the moms were chatting and younger children were playing.

I had just emerged from the pond, looking to grab a few chips and a cup of lemonade. After acquiring those items, I stepped over to the wooden railing overlooking the pond and surveyed the area. It appeared that there were around 60-70 people there in total; a mix of the graduates’ friends, parents, and younger siblings. I first spotted Claire and watched her as she clambered back into a half-sunken paddle boat that was getting paddled around.

I had met Claire a few years ago through Lucas, and coincidentally she went to the same college as me, just one year behind. She had a skinny frame, with shoulder-length blonde-ish-brown hair that framed her cute face. She had big brown eyes that made looking into them feel like a treat. She was wearing an orange bikini top that held her B-cup breasts perfectly. As I watched her climb in, Annie swam up next to her and tried to get in too.

Before I continue, there is something you need to know about the type of relationship Annie had with her older brother’s friends. They would tease and bully her in the way friends might, but they wouldn’t ever let up, and Lucas rarely defended Annie. To be fair, Annie filled the pesky little sister role very well as she always wanted to be involved in whatever Lucas and his friends were doing. This resulted in me often sticking up for Annie or simply not being mean to her, as I could see it really did affect her, emotionally. I had no desire to make my friend’s little sister feel bad about herself.

I didn’t consider myself to be her savior or something, and I didn’t stick up for her because I was on a high horse- it is simply what I did because I felt it was right. And Annie recognized that.

I say this all to explain why Annie had a bit of an attachment to me; because I was always kind to her. Even when we were in our mid to late teen years she always seemed to have some sort of feeling for me.

So there I was, watching Claire and Annie pull themselves out of the water and into the half-sunken boat. Claire managed to get in first and held out a hand to help pull Annie up. I watched them paddle around, running into the other boat, which was packed with boys furiously paddling to no destination in particular. I smiled at the funny sight.

Suddenly, the group of boys all jumped out of their rowboat and made a beeline for Claire and Annie. They were screaming and hollering, making their intent to flip Claire and Annie overboard very clear. This is the type of thing that Lucas’ friends would do- they targeted Annie’s boat simply because she succeeded in getting into it in the first place. Claire began paddling harder to try and evade the boys, but it was pointless. Their boat was quickly flipped over and out tumbled Annie and Claire into the water. My eyes were mainly focused on Claire (I had formed a small obsession with her chest and the orange bikini top hiding it from my sight), and I watched her head reappear above water. Annie surfaced nearby, and began swimming towards the shore.

Annie appeared to be upset as she emerged from the water and walked past me, but she gave me a certain strange look that somehow told me otherwise. I didn’t know how to react, so I did nothing and continued looking out over the water.

A few minutes passed and I had by then finished my snack. I felt the urge to pee, so I turned around and walked to the only restroom in the venue.

—

“You knew what I wanted before you closed the door,” Annie stated, and I didn’t deny it. She had stepped near me to whisper it, standing on her tiptoes to reach her mouth to my ear. She then lowered her heels back down to the ground, standing right in front of me. I looked down at her face, her blue eyes staring back at me. I could see down her bikini top, which was more of a waterproof bra than a bikini top. Her little A-cup breasts hung lightly from her chest, and I could see just the edge of her pale pink nipples adorning her teenage boobies.

I took in a deep breath as I gently placed my hands on the small of her back. I pulled her petite body into mine, holding her to me. Annie’s eyes softened as her lips parted, and I took the opportunity to kiss her. Her lips parted willingly for mine as I used my tongue to probe her mouth. Annie followed suit, using her tongue to sweeten our lips’ embrace.

I felt her utter a quiet moan into my mouth. I could tell that our age difference was having a strong effect on her. She must’ve felt special to be ‘chosen’ by me, and she was sort of right to feel that way. I was definitely aware of her interest in me, despite my being several years older than her. Not to mention the fact that she was Lucas’s little sister and was supposed to be off-limits for me.

As our soft yet intense kiss perpetuated, I slid my hands down from her back to her little tushie, holding a cheek in each hand. I had her ass in my hands, and I rubbed and squeezed it, pulling her hips closer to mine. She groaned into my mouth as I did this.

Our kiss broke off so that we could both take a breath, and her eyes met mine again as I held her close to me. Her hip ground into my thigh as we stared at each other, and her left leg rose up to try to curl around my waist. I could feel my cock rising in my swim shorts.

Then, I hoisted Annie up by her ass, and her right leg joined her left to wrap around my waist. She threw her arms over my shoulders, pressing her small body against mine, her cute boobies squashed against my bare chest.

“Graham,” she breathed. I could tell she was horny, horny for me. “Take me, I want you to. Put it in me, please. I want it.” She begged me. Her cheeks flushed a deep shade of red, her shame from the dirty request unmistakable.

My cock was fully hard by now, and I knew she felt it pressing into her scantily-clad crotch. The fabric of her bottoms rubbed against my shorts as I held her to me. I knew that I shouldn’t do it, but… I wanted it so bad. She kissed me again, and I made up my mind.

I set her on the ground again, and she quickly pulled her bikini top and bottoms off, exposing her little teenage body to me. Her tight waist led up to her perfect little boobies, on which her nipples stood with erotic anticipation. Her young pussy was dripping wet, her arousal clearly evident. My mouth dropped open for a second at the sight of her standing there, completely nude, all for me. My cock was rock hard. I couldn’t believe this.

Then, Annie tenderly reached for my shorts, and she tugged them off my hips and onto the ground. My erection popped free, bouncing with excitement. In my head, I knew this was wrong, but I didn’t care much at that point. It was happening, and there was no going back.

Annie stepped her lithe body to me, and I gently kissed her as I took her ass in my hands again, lifting her body up to press into mine. Her tits mashed into my chest as her hips pressed against me. I gulped with nervous anticipation as I looked into Annie’s eyes. Her pussy was dripping fluids onto the top of my cock, and as she reached her hand down to grip me in her hand, she let out a little gasp.

“It’s so warm!” She whispered, grasping my throbbing shaft in her delicate hand. I instinctively thrust my hips forward, and she giggled lightly. Her nipples strained against my chest, and I knew this was the moment. She stared intensely at me as she lined my hard cock up to her wet virgin teen pussy, then, I carefully lowered her onto me.

Her pussy lips slowly parted as the head of my cock entered her hot opening. Annie’s legs tightened around my hips as she wrapped both of her arms around me. I could feel her trembling against me when I slowly pushed further into her soaking sex.

I had inserted nearly two inches of my length into her virgin pussy before she tapped me, signaling that I should stop. I held her naked body tightly to my chest as her velvet opening got used to the intruder. I felt her pussy muscles clenching my cock, hard, as she lightly panted, her head resting on my shoulder. Annie tapped me again.

I continued pushing my cock into her sweet pussy as I resisted the strong urge to begin fucking her senselessly. I had driven almost two-thirds of my penis into her snug cunt when she squealed and squeezed down hard on my cock. I rubbed her ass with my hands as she panted, and she began to wiggle her hips around. Her wet insides squeezed and squished my penis as she wiggled, and her nipples rubbed against my bare chest. I kissed her neck, and she gasped.