So as the title says, this is a flashback story to my early 20s (I’m 33 now, so circa 2009). I really haven’t changed a whole lot since then, but I’m pretty thin with very small breasts, thick lips, dark eyes and a runner’s body. This is my third attempt at entertaining you with some of my sex life, so I hope you enjoy what you’re about to read. I apologize in advance for the length… no pun intended.
I was in my third year of college and I had become Facebook friends with a guy in my economics class. He was a nice looking guy, taller than me, moderately athletic with a gorgeous smile. I thought he was cute, but I at first I didn’t really think he was interested in me. I was living in campus housing (i.e.; a dorm) and he lived in another house halfway across campus.
One Saturday afternoon he sent me a Facebook message and asked me what my plans were for the evening. I didn’t have any and I told him that. He got a little flirty with me and told me that a girl like me should have Saturday night plans. I wasn’t sure what he meant… girl like me? So he told me that a girl with a body like mine should spend her Saturday nights having fun with nice guys. Admittedly, at first I wasn’t sure where he was trying to go with things. But as the conversation evolved he invited me over to his room to hang out, and I played hard to get at first, but I was definitely interested. After a while I decided that I really didn’t have much to lose, he was a nice guy and I was getting to know him pretty well. So we made plans to meet up outside his dorm later that evening.
I got ready, showered, did my hair and makeup and put on a matching bra and thong with tight jeans and a t-shirt and walked across campus to meet him. He was outside the building waiting for me and led me inside right away. We went upstairs to his room and he opened the door and showed me inside. Once we were inside he looked me up and down and said “I really hope this doesn’t go badly, but I think you’re into me too” and put his arms around my waist and kissed me, slow and deep. My hands found his arms and I let them make their way up to this shoulders, kissing him back. He pushed me up against the door and held my hands above my head, kissing me again on my lips and my neck. He pushed his body against mine and it felt so hot.
After a while I took control back and pushed him toward the desk chair, sitting him down. I got down on my knees and reached for his belt, unclipping it and grabbing the waistband of his jeans pulled them and his boxers down to his knees. I couldn’t help but laugh at what I saw (and in hindsight I know that wasn’t sexy). He was sitting here, semi-hard, and still had quite easily the biggest cock I have seen in my entire life – before or since. Even semi-hard I could hold it in both hands and still have about a third of it sticking out and was thicker than a toilet paper roll. That thing had weight to it. It shook me a little bit, but I wanted to please him.
I took his cock in both hands and brought his head to my thick lips, letting it slip between them as I teased it with my tongue. I knew there was zero chance of me throating him or even getting much of it in my mouth but I worked on the head as much as I could with my tongue and lips, taking time to roll my tongue and lips down the length of his shaft to his balls, licking and sucking on them as my hands continued to work his serious cock. By now, he was completely hard and thankfully not too much bigger. I looked up at him and, being the pleaser told him “This is seriously the most massive thing I’ve ever seen”. He smiled at me and told me that he was glad I liked it. Then he asked me if I was ready to have it inside me. I admitted to him that I was kind of afraid to have it inside me, but I was determined to try it after he warmed me up a little.
I undressed for him and he sat there in the chair, rubbing his cock while he looked me over. When I was done he stood, walked over to me and kissed me again, letting his hand run down the front of my midriff to my freshly shaven pussy. He rubbed my clit and my labia with two fingers as he slipped his middle finger inside me, discovering that I was already soaking wet at the idea of him. He kept rubbing me and fingering me while kissing my neck and teasing my nipples, bringing me within inches of cumming for him.
I stepped away from him, nodded and said “Now”. He led me to his bed and laid me down while he grabbed a condom from his desk drawer. I don’t remember if it was a magnum or something else but I remember seeing it on him, and it only covered about ¾ of his cock and was tight on him. He also grabbed a bottle of lube and rubbed some on himself and me before laying down on top of me. I took his cock in my hand and guided the head between my pussy lips. When I found the spot he started to slide into me slowly. I had never experienced anything quite like it before. I felt so stretched, more and more with every inch. The pressure was insane as he passed the halfway point and was now so deep inside of me. When he got to the end of the condom he brought up pretty much right away against my cervix. And it hurt. A lot. I cried out and he pulled back. I knew this wasn’t going to work so we had to try and find something else.
I made him get up and sit on the armless chair by the desk so I could straddle him and control how deep I was. I had very strong legs in those days from soccer and running so I thought this might be good. I stepped over him and lowered myself slowly onto his massive cock. I put one hand on his shoulder and used the other to start rubbing my clit while raising myself up and down on this cock. I could control it so much better and while the stretch both hurt and felt good at the same time, the control felt amazing. It only took a couple of minutes in this position before I could feel the start of an orgasm coming. My legs got weaker and started to shake while I rubbed myself and fucked myself with his cock. I ended up taking him a lot deeper but this time the cervical contact felt good and I came so hard, screaming out in pleasure and a little bit of pain.
He wasn’t there yet, so I stood up again and got on all fours on the bed. I told him to use me to get off, but please not too deep. He listened and grabbed me by the hips, guiding himself inside me. It felt even bigger from behind and I have to admit, wasn’t 100% enjoyable. Luckily for me, this angle was very enjoyable for him because it only took a few seconds before he was gripping me tight and crying out my name as he unloaded inside the condom inside of me.
When we were done and cleaned up I went back to my dorm and told my roommate what had just happened. I was sore for days.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/swky79/flashback_to_the_biggest_cock_of_my_life_fm/
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