Where it happened: Her bf's bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time came a week late. I had been messing around with a girl that was older than me, who happened to have a boyfriend at the time. She was living with her boyfriend and I was basically doing a lot of kissing and touching with her, but we never went all the way. I never told her that I was a virgin. I don’t think that she suspected that I was since I was a 19 year old freshman in college who acted like I had been around the block a few times. One day, I picked her up all dressed up and took her back to my apartment that I had just moved into. I thought that I was being romantic. I had a radio playing our song, and we started to go at it. I thought we were really going to do it! She asked me if I had a condom and I took it out. I was having problems putting it on, since I hadn’t ever put one on before. She offered to help and when she grabbed a hold of my very erect penis, and started stroking the condom on, I instantly came. She didn’t notice as she positioned herself on top. When she reached down to put it in, that’s when she realized that it had already started going limp and since that was my only condom, knew that we weren’t doing it that day. However, I felt bad that I had let her down, so I broke my cunnilingus cherry by going down on her. I was down there so long, that I had another erection once she came for the last time. She noticed my hard cock, and returned the favor. As I layed on my bed, looking up at the ceiling, I couldn’t believe the feeling as her lips stroked up and down my shaft. Suddenly, I could feel the pressure building and so could she. What came next suprised me. She never pulled off and swallowed every last drop. So even though I didn’t lose my virginity, I did plenty of things for the first time that day.
A few days after that, I had a conversation with her about our situation. She didn’t want to be fooling around behind her boyfriend’s back anymore. She said that I deserved better than that and so did her boyfriend. I could respect that and told her I would still like to be her friend. The next night, I was invited to go to a bar with her and her boyfriend and a couple of other people. Now I was only 19 at the time, but I had a really good fake ID. That night, I hooked up with a girl on the dance floor. Nothing serious, just a lot of making out. She saw the whole thing. Coincidentally, after the bar closed down, I had to grab a ride with her and her boyfriend, and on the way home, her boyfriend congratulated me on my night. The next day, she was actually mad at me!!! She said that she couldn’t beleive how soon I could move on. I couldn’t beleive that she was telling me this, since she was the one with a boyfriend. That is when she finally came clean that she had real feelings for me and that is why she didn’t want to continue the fling any longer. A few days later, exactly a week after our oral encounters, I showed up at her boyfriends house, knowing that he was at work and she was home. She had just gotten out of the shower and answered the door in her robe. We went up to her boyfriend’s room so his roomates wouldn’t see us. She wanted to know what I was doing there and I gave her a letter that I had written her the night before. I spilled my heart out to her on that letter, even going as far as to tell her I thought I may be falling in love with her. Needless to say, as soon as she was finished reading the letter, she jumped on top of me. I tore her robe off and she was completely naked on top of me. After seeing how much she like me going down on her the week before, I went down south again. I didn’t come prepared with a condom, so I figured that we weren’t going to have sex. She had other ideas. After going down on her until she couldn’t take it anymore, she pulled me up and reached over to the dresser next to the bed. She pulled out one of her boyfriend’s condom and slipped it on me. She threw me on my back, and jumped on top of me. After making out for a few more minutes, she reached down, gently grabbed the tip of my hard cock, and slowly led it to her already wet and very warm pussy. As it slid in, she slowly went down about halfway, then came up and swiftly went all the way down so I was all the way inside her. She stopped for a second, than looked down and looked right at me. I must of had a smirk on my face because she asked me why I was smiling like that. I told her that I was officially devirginized, and she didn’t believe me. I told her I was serious and this turned her on to no end. She rode me very deliberately because she wanted me to enjoy my first time. It didn’t last very long, but it lasted long enough that I can still picture it and smell her freshly showered hair and body as I type this. After it was all over, she told me that I should have told her that I was a virgin. She took on the role as teacher over the next few months. I did most of my first’s with her after that. First doggystyle, first 69, first titty fuck(she was a 36D), first red wings earned. I ended up dating her for a few years, and while it didn’t work out in the long run, I still talk to her to this day and she will always hold a special place in my heart.
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