Here’s a little background to the story:
I’m 18, half white half Asian. Very petite for a guy, I’m 5’4, thin but not super skinny. I had been confused for a girl all my life, because of my lack of facial hair, feminine face, and long straight black hair. I’m super into anime and cosplay, and I had quite the following on tumblr at the time for my cross dress cosplaying. Despite what it sounds like, I wasn’t gay and had just broken up with my ex girl friend at the time of the event. I never had a problem finding girls despite how Unmasculine I was, mostly because girls I dated were into the whole feminine anime androgynous guy thing.
I had just broken up with my ex who I had dated on and off since I was 13. I was so heart broken by her, to the point where I even contemplated suicide. Through the time dating her I had become good friends with her older brother, who was 25 at the time of me and his sister breaking up. Him and his sister were Hispanic. He was a big guy, 6’4 a little chubby but muscular. Dark skin, with hurly hair and a small beard. I would always play video games with him and watch anime. So anyway, let’s get on to the story.
It had been 2 weeks since I had broken up with my ex, her brother, which we will call Dan had texted me to see how I was doing. I told Dan that I was super depressed, and he invited me to go over. I felt awkward since my ex would be there, but I thought I would just go hang out with him. I got to his house, his sister was out at the time thankfully, and he walked me over to his room. We played video games for a little while and watched anime. I was sitting on the edge of his bed with my legs crossed and Dan looked over at me and poked my shoulder
“You should cosplay her” referring to one of the anime girls.
I laughed and said “there’s no way, I don’t have boobs and I’m not that pretty.”
He looked at the tv and in a low voice said “honestly, I think your way prettier than any girl I’ve seen”
My heart missed a beat when he said this. I laughed a lil and told him “that’s probably why your sister left me, I’m not man enough haha..”
the room got quite for a moment, and I began to tear up and cry
He reached over to me and asked me what was wrong I told him I didn’t know what else I can do without her. I kept crying. he pulled me into his arms, he felt so strong, and wraped my arms behind his neck. at that moment my heart was beating so fast I didn’t know what I was feeling I told him I didn’t know what to do without her, and he told me that there’s so many people who would love to be with me. I told him “I dont believe you” he pulled away a little bit and look me in the eyes and he reached in for a kiss. He kissed me on the lips and never kissed another guy before but I felt so good with him. he ran his hands down the side of my body and I started to feel warm. He kissed my neck and everything started to get blurry. He whispered in my ear while holding me in his lap and exploring my body. He told me how beautiful he thought I was. How I needed someone who would value me. I felt in ecstasy. He lifted me up with easy in a bridal carry. I squeaked with surprise, eyes still watery I gave a lil smile and kissed him again as he held me. He laid me down on his bed gently and began to undress me. I payed naked on his bed with my arms above my head. He told me how beautiful I looked. He touched my smooth pale legs. His hands were rough with callus. He touched my dick, I left out a small moan. He kissed my smooth chest and played with nipples. At this point I had lost all sense, and I said in a low voice “Dan, please make love to me”. He smiled, and began to undress. I looked at his big Hairy chest, and then down to his Dick. I couldn’t believe how big it was, especially next to mine. He was so much more of a man than me, I hadn’t realized until then. He grabbed a bottle of lube and started apply it to his dick. He then put some in his hand, and slowly applied it to my ass, fingering me. It was such a new sensation, but it felt right. He grabbed me by the legs and pulled me to the edge of the bed where he was standing. He told me it may hurt a little, I said “I don’t care, I want to feel you”. He smiled, grabbed his huge dick and slipped it into me. My little dick twitched, it was a little painful, but then Felt so good. He kept slipping in inch by inch, slowly until it was all in. I could feel him so deep inside me as he began to stroke in and out. It got heated, he grabbed my wrist and pinned me as he put my legs on his shoulders and pounded his large hips into my tiny frame. I was trembling and moaning, but I asked for more. “Faster! Harder Dan!!” I moaned. And he did just that. He pulled out and turned me over, putting me on my knees and placing his hand on the small of my back with my face in his pillow. He fucked me harder and faster, as my small partially hard dick swayed back a fourth with each stroke. He finally came pressing deep inside me. I felt his warm seamen flow inside me, as he pulled out I could feel it move inside me. I layed there on my stomach, I felt my ass throb, almost as if it felt empty without his dick inside, he layed down and pulled me into his aRms and kissed my forehead. I felt his dick brush up on mine, it felt so warm. He held me and I felt so safe, beautiful and wanted. From then on we had continued our relationship in secret. I would often dress up as a character he liked, and have roleplay sex. He really opened my eyes to realizing that I should have been born a woman. Sadly, it came to an end when his sister walked in on him fucking me in a school girl outfit. We cut it off to avoid family drama. I still miss him to this day.