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Introduction:

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“Hey are you on your way?” “Yeah ill be there in 20” “Nice just message me when you get here.” I’m 17 years old in high school and I had no idea what I was doing. I had matched this hot nerdy sexy guy on tinder and we hit it off and he invited me over to his place.
But before I begin this sexy scene let me give you all some descriptions. I call myself Elaina and I am a cross dresser and I am Asian. I am 5”10 and weigh 177lb and have a C cup sized bra. I am a very passable and have been called mam and miss on more than one occasion, even when I wasn’t properly dressed entirely. His name was Tim a 22 year old college student and he is 6”3 220Lb and extremely muscular. He had a nerdy kind of complexion but worked out a lot. He is also a red head and had short hair. Now that you have a visual lets continue my experience.
Driving west 20 minutes from where I lived made me nervous, especially knowing what I was about to do. We had already decided I was to wear something sexy so I had decided to wear my new white laced panties. They were open backed and gave complete access to my ass. I had on my white pencil skirt and my crop top and had put my long black hair up with a clip. 20 minutes later I arrived at the apartment complex.
Bzzzzzzzzzzzzz…. The buzzer sounded and I knew I could enter the complex. Room 3XX, 3rd floor and all the way down the hall. I was nervous. “I’m here…” I texted. As Tim opened the door I realized how tall he was and how big his muscles were. He directed me up the stairs and motioned to be quiet since his brother was living with him. I went up the spiral staircase to his bedroom. Immediately he grabbed me and kissed me rough. His forceful kiss was moist and sensual, his touch was hot and made me feel more womanly than I already felt. He had already zipped off my skirt and had let me keep the crop top. After we broke kiss he walked a foot away and sat in a leather office sort of chair. I knew what he wanted, it was what I wanted. I went to my knees and crawled to him and started working off his gym shorts. As I revealed his hard cock I almost gasped to myself at the 9” monstrosity that was revealed. It was long and extremely thick, almost as if I was holding can of mountain dew. I started licking at his balls and could smell the Irish scent that told me he had just showered. I started sucking his long membrane and started to gag, barely allowing the tip to get further. I knew the training and the methods and I put them to use. Breathing through my nose I deep throated the monstrosity. As he started moaning he started to work his t-shirt off, revealing his chiseled body and love trail that was so erotic made my own 6” cock jump. As I continued deep throating his cock he licked his fingers and started working on my ass. My virgin ass was too tight to allow even a finger in but he pushed and pushed until my ass started relaxing. He started to finger fuck me and my ass quivered and I knew no matter what, I wanted to be filled. As if he heard my mind he got up and pulled his dick out of my mouth and motioned me to his bed, about 3 feet from the chair. As I lay on my back on his bed he quickly kissed me again. We fought for what felt like an hour, more likely a minute or so, but as we wrestled tongues he pressed his monstrosity to my virgin hole. As he pressed harder and harder I couldn’t help but feel my erection grow. “Ah! Babe get the lube please!” I begged, he complied and was already applying a generous amount of lube to my hole. With a hard thrust he was in. The tip of his uncircumcised cock was inside my ass. “Please give me a minute to breath babe.” I whispered. “Babe I can’t hold it, you’re so tight!” he replied, and thrusted into my ass. It felt like nothing I could compare. He was maybe only a fourth of the way in but my body reacted and I pulled him into me. All 9 inches went in, he hit my G spot. I couldn’t control myself, the feeling was mutual, as he fucked me I could feel every vein, thrust, and throb of his cock and it only made me harder. “Fuck me harder !” I gasped and with those words he let loose. He lifted my legs above his head and fucked me mercilessly, giving me no time to adjust to his sudden speed increase. With every groan, sigh and moan the ability to tell time flew away. Using every bit of strength I had I fought back to take control and tightened my ass almost as if grabbing his dick to say you are now mine! With the sudden squeeze I gave him he moaned. “Babe, damn that’s fucking talent god you’re so tight! I can’t hold back!” with those words he picked me up and fucked me in the air. I alternated my clenches as he fucked making him fuck harder as if we were battling to make the other cum first. As we battled, I knew I couldn’t control it any more. “I’m going to cum babe!” I gasped, and he lowered me down and fucked furiously. “I can’t hold back anymore either, I’m going to cum too.” “Cum inside me babe!” and with that I came on my chest. The feeling of my ass clenching when I came was all he needed and I felt the greatest feeling I would learn later to become my drug. The warmth of his cum shooting load after load into me filling me making me feel as if a man could give birth I was going to. Exhausted he collapsed on top of me. It felt like eternity as I waited for him to regain the strength to release me. As he got up and pulled his dick out, I felt his flaccid dick sliding out and with the last of my strength I clenched, making it harder for him to pull out. With a groan he was out. After a few moments I started to dress, and with a few more embraces and a well timed exit. It was over. My virginity lost, but never forgotten.
Even though it was meant to be a one night stand it turned out to be friends with benefits and to this day we still connect whenever we get the chance. ;) I hope you all enjoyed my virginity story, please feel free to give me comments and notes and if you enjoyed it let me know and I may write more experiences or fantasies I have ! Thank you !

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