Where it happened: His house
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I was 16 when I first had sex, I wanted to wait untill I was atleast out of school but things didn’t turn out that way. I had been dateing Dylan for three months when it happend. He was always more sexually experienced then I was. I was just never much of a sexual person I suppose, It always made me uncomftorble. But Dylan would help me relax when we first started hooking up. After about one month of dateing, we had our first seriouse sexual experience together. I already had told him that one thing I would never do is give head. I thought it was just, not right and I had a very sensitive gag reflex. But we talked about it and he told me he wanted to lose his virginity to me, I also wanted to lose it to him. But not any time soon. We didn’t want it to hurt me, we wanted the first time we had sex to feel good for him and myself. So Dylan suggested fingering me everytime we felt frisky to well, losen me up a bit. I acually had this thought myself but I was still scared of the pain. Anyways, it was about a month into our relationship when I was fingured for the first time.
We were at his house on a friday night, we watched family guy then started fooling around on the couch. He said just incase his parents come home early we should go into his bedroom. I made sure I shaved before I went to his, and convinced myself being fingured wouldn’t hurt. But I started to feel nervous. I layed down on his bed and he layed ontop of me. We were kissing and He took his shirt off and mine aswell. Eventually we were both naked. To relax me he just kept making jokes to get me to laugh, it worked I felt more eased then. He asked me If he wants him to put lube on his fingers. He did and told me to lay back and to not be stiff, just relax. I almost felt bad that I wasn’t doing anything for him when he was the one with the boner. But Dylan seperated my legs and got in the middle of them. I felt his hand touch my vagina then I felt a sharp jab inside me. He told me to sit up so I could watch what he was doing. He only had one fingure in and it wasn’t all the way. He started thrusting his finger in and out. He put his finger all the way in and started going a bit faster. It stopped hurting and started to feel kind of good. He told me that he was going to put a second finger in and warned me it was going to hurt a bit. I layed back down for this. He layed over me a bit to kiss me when he did it so I wouldn’t scream or anything. I could feel it stretching my vagina, it hurt so badly I stopped kissing him but he kept kissing me. He kept saying just relax, but it was hurting so much that I couldn’t. He took his fingers out and we tried again about two minutes later. It didn’t hurt as much anymore.
Fingeing became a common thing for us, It didn’t hurt at all anymore and acually felt great. One night when I was at his we did it again and I moaned infront of him for the first time. I was kind of embarrassed so i laughed it off but he told me to keep doing it and not be shy about it. He kept finering me and I eventualy orgasmd for the first time. It felt amazing. My heart stopped for a second and I couldn’t control my body or my moaning. He became so turned on that he started to stroke his penis aswell. Instead of giving head, I helped him masturbate. He came on his chest.
Okay, so it was a few days after our three months and we had his house all to ourselves on a saturday night because his parents were at a work thing and had to stay over night in a hotel. This was it, we had talked about it the night before over the phone. When I got there, he couldn’t keep his hands off me, he hugged me when we were standing up and when we were on the couch. He put my legs over his lap and I could feel his boner. We went into his bedroom and started hooking up. When all our clothes were off we turned off the lights but we had the light from his laptop that was on the floor so it wasn’t completly dark. He got a condom and we started having sex. At first it didn’t hurt but I wasn’t getting any pleasure. Untill he layed over me more to kiss me and the way he was positioned hit me just right. He thrusted faster and more evenly. It felt so good that I started moaning more then ever. I even said his name over and over again a few times, which made him go faster. He came after about ten to fifteen minutes. He put his shirt back on and fingerd me, I came so intensly that I grabbed his shirt so hard I almost ripped it. We dated for a year after that and our sex got better and i was eventually able to achieve orgasm’s through intercourse. We broke up after formal in year 12 because I had to move away for Uni, and him and his family were moving aswell. I missed him alot, we were going to keep talking as friends but we just drifted apart. I havn’t had a boyfriend since and I have never slept with anyone else. He has a new girlfriend at the moment which is one of the reasons I chose to stop talking to him because it did make me feel upset and jelous. I don’t regret my first time because It was with a guy I really cared for and i luckily avoided the painful side of sex.
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