Please Pop My Cherry
After barely graduating from high school, the situation at home with my parents was strained at best. I took a job in the city, and a coworker helped me get an apartment in her building. While glad to have my first real job and my very own apartment, I was lonely. I am, as some would say "Rubenesque." Others would call me chubby. But most 18-year-old boys just called me fat. Needless to say it was difficult to find dates, let alone finding someone to pop my cherry.
One day I was buying my lunch at the convenience store on the first floor of my office building. At the counter I met Sampson, the new clerk. He was tall and dark, from East Africa, here to find a good woman. His molasses colored skin and intense eyes seduced me. After a few flirty encounters, he asked me out to lunch. It was obvious to me early on that I was not who he thought I was. My mother had bought my clothes for work, and so he did not know that I wore the clothes of a punk rock wannabe on my own time. He wanted a good Methodist girl to take home and fill with babies. All of this aside, there was something about the thought of his dark skin next to mine that made me very wet. I had been masturbating since I was sixteen and still had not gotten off. That night after the lunch date, I spent hours playing with my clit, feeling good, and never climaxing. I decided that I just needed to be fucked. I did not care if I had a boyfriend, I just wanted dick. And I decided that Sampson was going to be my first.
I approached him the next day and we stepped outside to talk. I told him that he should come to my house for coffee after work. He thought that we could just meet somewhere, but I convinced him that he should come to my apartment. I was done at three, and he was of at five, so I had two hours to get myself ready. I had a dress that had belonged my mother. It was a white lace and gauze caftan, and I did not wear anything under it. When Sampson got to my house he seemed on edge. I touched his hand and leaned into him to kiss his cheek. He would not touch me. In fact, he suggested that we go for a drive into the mountains. So I reluctantly put on my black docs and grabbed a long black jacket and we took my car for a drive to the mountains. It was rush hour, and it took forever to get out of the city. All the while, I touched his arm or hand as often as I could. And Sampson just kept shrinking away from me. I couldn't understand it. He had asked me out, so I thought that he must at least find me attractive. But each time I made a move, he got increasingly polite. He wanted to get out and walk around, so I found a parking lot at a trailhead. There weren't any other cars parked, so the trail was likely empty. I left my jacket, and we headed down the closest path.
It was mid-summer so there was plenty of daylight left as we turned down the trail. We talked a bit, but mostly walked slowly. It was wonderful to feel the gentle breeze on my legs and blowing my thatch of pubic hair under my dress. We stopped to rest in the middle of a hillside meadow, and I could not take it any more. I had to know why he had not even asked for a kiss. He looked at me with my hands on my hips, staring him in the face. Grabbing my arms, he roughly pulled me to him. I loved the feeling of being smashed up against his hard body. He held me with one arm and pulled my face towards his with the other. We kissed, and his tongue was immediately in my mouth. As his tongue fought it out with mine, my hands were everywhere. I had years of teenage sexual frustration controlling every move.
Without separating our mouths, I pulled apart enough to put my hands on his chest. I ran my hands down his chest to his tight stomach, and just started pulling at his shirt. He started running his hands all over my back. I had never felt so good. My body was alive with the sensation of his big hands on my body. Kissing ang licking all over my ears and neck, he put his hands on my ass, and through the thin material of the dress, he realized that I had nothing on under it. As his lips made there way down to my breasts, I tried to take his belt off. I was shaking with so many feelings that I had no idea what I was doing. I gave up on the belt and grabbed his waist, crushing him to me. He bent his head down to my nipples, erect under the cloth, and took one in his mouth, licking and nibbling at it. I cried out, the pleasure was more intense that anything I had ever felt before. I clung to him as my knees buckled.
He pulled me off of the path and into the grass. He laid me down, and as he moved to his knees he took off his shirt, unbuckled his belt, and unzipped his pants. His pants were still on, as he lay next to me and kissed me deeply again. With his hands and mouth he worked down my body, touching and kissing me through the fabric. When he reached my waist, he slid his hand under my back and lifted me up, just enough to slide my dress up. He pushed it up to my waist and began to stoke my mound and kiss around my hips. He slid his dark hand between my white thighs and opened my legs just. He ran his long fingers over my pussy lips, teasing me, postponing contact with my wet slit. After dragging his fingers over my lips for what felt like forever, he suddenly dove his index finger into my tight little hole, sliding it in and out as I moaned and writhed on the ground. The grass was high around me, and all that I could see was Sampson, the grass, and the sky behind him. I liked the look in his eyes as he pleasured me with just a finger. He moved up my body, lifting the dress as he did, finally pulling it over my head and exposing my breasts. He kissed each one gently and then kissed me on the mouth again. He rubbed my titties, and then reached down to pull his pants off.
First I felt him. Hot and warm, it was hard and he spread my legs to rub his cock up and down on my pussy. It felt so big, I did not know if it would fit. This time, he was teasing both of us. He licked and bit at my nipples, as we ground together without penetration. He sat up and pulled me forward, spreading me at the knees as far as I could. Raising myself onto my elbows, I finally say his long, thick, black dick. He pushed me down and posted his mushroom tip at my entrance. Slowly he pushed into me and it burned as it stretched out my virgin hole. He must have known that he was my first, be cause he took his time. Sliding his cock into me a little at a time. When it seemed as though no more of its length would fit, he held me too him and thrust with a grunt. I screamed as his cock pushed past the last barrier. It was such sharp pain. I was crying, and he was kissing me, and beginning to slowly pull back out. At first I thought it was over, but as soon as his tip was resting at my slit, he pushed back in again.
I quickly learned that the longer he fucked me the better it felt. Soon, he was pounding my pussy with his cock and I was grinding into him as hard as I could. I could feel him throbbing inside me, while we licked and rubbed and bit and kissed everywhere that we could reach. We were fucking so hard that my titties were bouncing and he reached for them. He was holding my breasts and alternating licking on my nipples when I felt this feeling begin in my pussy and spread all over my body. He groaned in pleasure as my snatch tightened around him like a fist. As I bucked and spasmed in my first orgasm he shot his hot cum deep inside me. I couldn't stop convulsing as chills swept over my body. There was nothing but sensation at every place his dark skin touched mine.
We lay in the grass recovering for a while. But it was a beautiful day, and so soon we heard voices from a little way away, and so we put our clothes back on, and started walking back to the car. Neither of us said anything the whole way back to the city.
He asked me to drop him off downtown, and I drove home alone. He was never at the store after that, and we never talked again, but I would never forget how it felt to have him inside me.