It was my Junior year of High School and I was not a little virgin anymore, at least not in the biblical sense. I had a taste of sex, and I knew I wanted more. So I did what any rational girl would do, I found myself a yummy boy toy to play with. I have always had a thing for unattainable men. All the girls lusted for him, and I made him mine. He knew the deal and was kinky enough to fulfill my very dirty desires. Nick was a 6’ foot Senior, Sicilian, dark and handsome, and on the hockey team. He drove a sexy blue Mustang that purred just like my pussy did for him. As a quick reminder, I am 5’0, very petite, have perky 32C tits, and a very tight ass.
They say the freaks come out to play on Halloween, and I was no exception. It always made my pussy quiver when Nick’s name popped up in my notifications. We had been texting back and forth for days and decided that Halloween was the perfect night for me to lose my anal virginity to him. The build-up to that day was so intense. When the day came he teased me all day. Finally, the clock struck 5:00 PM and I could hear my mom and little sister shuffling out the door to go trick-or-treating. I knew I had a few hours of the house to myself so I sent him the text to head over, and I quickly scrambled to make sure I was ready. I was so horny and very nervous. I lotioned up my body and prepared the lube, which I gathered from porn was important to make it an enjoyable time. I put on a casual, but sexy, outfit that made me look more confident than I was.
After what felt like years, his text came through. He was here. I ran downstairs to let him in and guided him to my room. He looked incredibly hot, and my pussy gushed at the sight of him. I made my best poker face impression, however, as I didn’t want him to know that inside I was desperately anticipating his thick cock in my virgin asshole. I was so ready to experience him. It didn’t take long for him to get me out of my clothes, and he told me to get on all fours on the bed. The submissive in me was salivating, I could feel him nearby, as he made me wait full of anticipation.
I was on display for his enjoyment, and he took his time. Nick looked into my eyes and they burned into my soul. I could feel the wetness from my soaked pussy beginning to run down my legs. I was exposed, innocent, and yet I was extremely desperate for him to take me. He began to stroke his cock, he told me how sexy I was, and that he was now going to fuck my tight little ass. No warm-up, just taking exactly what he was here for. Fuck, he knew what I needed from him.
I closed my eyes, as he moved around me. I remember telling myself I was ready. He came up close and teased my ass with his hard cock. Feeling his head pressing on my ass made me question how he would possibly fit inside me. Would I be able to handle the pain? Would it stretch me out? My mind was going a million miles a second. Nick continued to press his head firmly on my ass and I could feel myself tense up and my asshole trying to reject his cock. This wasn’t going to be easy! He didn’t care one bit, he knew what he wanted and was going to make himself fit no matter what and I was happy to be a good little slut for him. After a few seconds, my ass stretched out for him and he was in. I may have let out a mild scream, as the pain and pleasure were unimaginably orgasmic. Oh my fuck! My pussy tingled as I felt my asshole wrap tightly around his throbbing cock. Nick pushed himself deeper with every thrust until he started to let loose and take my ass. It threw me into one of the most intense orgasms I have ever had in my life. I couldn’t believe it, here I was losing my anal virginity and I was absolutely hooked.
We weren’t fucking for too long before we heard the dogs barking, and the front door open. Shit, I hear people! Nick quickly removed himself from my ass and jumped into my closet. I grabbed a towel as I quickly rushed to see who had come home. My mom met me halfway up the stairs to let me know my best friend Nash was there. Oh Nash, what great timing! I could overhear him telling my mom he planned to whisk me away to a haunted house on the other side of town. You could say Nash was the ultimate cock block that day. I rushed back upstairs to get dressed and told Nick through the closet door to check his phone.
I went downstairs to meet everyone as I pushed them outside to talk. Of course, the topic of conversation was the random blue Mustang in front of our house. Nash proceeded to say that it looked a lot like Nick’s car from school. While I played dumb about the car, I nervously text Nick to go out the back door now. The coast was clear. Thinking he surely read my text and followed my instructions I was pushed into Nash’s car to head out to our spooky adventure. I kept checking my phone, waiting for Nick to confirm he had made it out safely.
Instead, I received a call from my mother asking me why someone just jumped out of my second-floor bedroom, and why the blue Mustang was no longer there. Naturally, I played stupid and eventually, I was told that after we left my mother heard a big bang and she rushed upstairs to find the window completely open, and the screen knocked out. I had to return home immediately as I was in some serious trouble.
While I got in trouble that Halloween night and Nick didn’t get to cum, he did help open up my world. I love anal sex thanks to Nick. The ironic part is that Nick became a firefighter. I saw him years later on a job site I was working at. A blast from the past that made me blush. I can admit I got quite wet seeing him again and remembering his big Sicilian cock. We had a few more kinky adventures together that I’m happy to write more on before we parted ways and I was on to my next boy toy.
Source: reddit.com/r/gonewildstories/comments/10s862m/fm_halloween_night_and_my_first_anal_experience
This story has everything! Incredibly hot!