The first time I tried anal was shortly after I had lost my virginity to my first boyfriend at 17. We lived far away from each other so we hardly ever saw one another. Being in High school still we also were hardly ever alone. Sometimes we would be able to say we were going to watch a movie and shut our bedroom doors or stay in the living room. Anytime this would happen we would be all over one another. I remember giving many blow jobs on his parents couch while the tv was turned up to drown out his moans. It was really fun sneaking around! I almost miss that excitement when you are so young. But anyways, one night we were at my parents house in my room. It had been 2 weeks since we had seen each other so it was blissful being able to touch him and be touched. For weeks before we had been sexting about how he really wanted to try butt stuff. I remember him saying he had really wanted to eat my ass and try anal because it was so tight. I was so excited to try something new so I propositioned him that we could do it that night. He was really excited and got my lube from my hiding place as I took my clothes off. I could hear my dad watching tv out in the living room and it was exhilarating. My house has very very thin walls so I am surprised to this day my parents thought I was still a virgin. After I took my clothes off he flipped me over so I was on my stomach. I lifted up my butt a bit as he grabbed my ass and started kissing around my hole. He licked softly at my O ring and traced the skin around. It felt so sensual and nice. I felt safe and ready to try what we both knew was next. Then he put some lube on his finger and slowly went in and out. At first I was confused as to how it felt. I froze unsure of if I wanted to continue. Then he put more lube and slowly put two fingers in. It started to feel really good. I loved how slow but sure he persisted. Then he barely put three fingers in and let it get used to be expanded. I got up and went down to the ground on my hands and knees and begged him to put it in. He quickly got up and took his pants off. He put just the right amount of lube on his dick. I could feel him at my entrance and he slowly slid in. I moaned deeply because it felt so amazing. He grunted and said I was so tight. Then I remembered he didn’t have a condom on! We always used condoms but forgot this time. At first I was going to say something but instead I was so happy he didn’t. It felt so amazing having him raw inside of me. I felt myself get wetter and wetter with the thought of how dirty we were being. He started to go faster and at first it started to get a bit painful but then I eased into it. He started breathing really hard saying I felt amazing. I was so excited I started touching myself. After a couple more pumps he said he was going to cum. Before I could do anything I felt his warm load fill me up. It felt so amazing with his throbbing cock filling me up and making me feel warm. He stayed inside me for a little while moaning. Then he pulled out and his cum came rushing out. He quickly put his shirt to stop it from getting all over. I reached down and I swear I had never been that wet before. Since then of course I have had better sex but this moment was certainly memorable.
Source: reddit.com/r/gonewildstories/comments/fv84rb/f_my_first_time_trying_anal_and_the_wettest_i_had
Other people’s stories always bring back memories of our own experiences. Your writing was fun to inspire my desire.