How I lost my virginity to my brother's friend

Hey guys, today I want to share a naughty story with all of you. Though it’s a little sweet too. At least I think so. It’s the story of how I lost my virginity to one of my brother’s closest friend. I was 18 and I had just finished high school, and I’d be moving out to go to college at the end of summer. I had three good friends, all girls, and they all had their first times that year or the year before. They had all done it with their boyfriends; most of them had been dating for over six months or more when it happened. And I wasn’t even dating. Now, this is not to say they pressured me into having sex, but I definitely felt like I was missing out on something when the conversation went that way and I had nothing to share. I had decided that I didn’t want to arrive in college at the end of the summer as a virgin. Back then, I thought this would matter.

I have an older brother, and that summer, he was home from college, and he and his friends from high school would hang out at our place a lot. One of them was Jason, who I had a bit of a crush on for years. But Jason had always had the same girlfriend all throughout high school, and I was pretty sure he only saw me as my brother’s little sister. I was close enough with my brother that I could get away hanging out with them occasionally, and that’s how I heard that Jason and Trish had broken up because they went to different colleges in different cities. Suddenly, I felt my feelings for him reemerging. I was still pretty sure he had never looked at me that way, but now that he was single and I was no longer a minor, I could change that.

I was never one to dress too provocatively, but I had a good body back then. I was really skinny and I had really good legs from being on the school’s track team, so I got myself a Daisy Duke style shorts and tucked in a loose tank top that let a bit of my bra out, and when my brother and his friends were hanging out in our backyard, I shamelessly joined them. I could see that my brother didn’t like my outfit, but he didn’t want to call me out on it in front of his friends, and his friends all seemed to be unable to take their eyes off me. They seemed both attracted and shocked, as if they just realized now, I was a woman. I sat down really close to Jason and made sure to brush on him and lean close at every opportunity, and before the end of the night, I felt he was doing the same. We didn’t do anything that night, but unsurprisingly, he invited me to go to the movies with him the next day.

Jason had his own car and as we left the cinema, he drove me to a lookout out of town. The sun was setting as we parked there and started making out. I reached out and felt Jason getting hard under me, and I decided I was ready to lose my V-card. So, I leaned in and asked him if he had a condom. He was probably not expecting to get lucky that night because he seemed to be caught super off guard. He didn’t. But I had one with me. He was really gentle and I have no regrets about what we did. After it was all done, he drove me home, and I would meet with him a couple more times. I made sure to tell him that I wasn’t looking for a relationship and that I was happy to have had my first time with him, and that remained our little secret. Dressing up and taking control of my sex life felt really good too, and I think that stayed with me as I went to college.

About The White Rabbit: A couple hesitatingly goes with their new ‘cool’ friends to a club, only to find out it’s a fetish club. Seduced by the exhilarating atmosphere, they eventually decide to explore new avenues of their sexuality.