Where it happened: Mothers House
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I will call her Rachel. She was my first girlfriend. We dated in high school (she was a freshman and I, a senior.) She was a little more experienced than I was, but we were both still virgins. We dated for about 3 months, then broke up. We remained friends for the next 4 years. She just graduated high school and I was entering my senior year in college. She was still cute as ever and I had always held a special place in my heart for her. We started dating again during that summer. She would come to my work, say hello, and then get my key to let herself into my mothers house. I would meet her there. We would make out for hours until my mother got home. She was still a virgin (amazing) and I basically was. At school I had sex with this girl named Melissa for about 5 minutes. I didn’t know what the hell I was doing and neither of us came. I don’t really count that as my first time.
Anyway, Rachel and I were dating for about 2 weeks when we started talking about having sex. She said she was ready and I definetly was. We were going to do it at my monthers house one evening when my mother was out of town. Rachel agreed to wear something sexy.
We got to my mothers house that night and immediately started making out. I could tell she was nervous…so was I. She said she wanted to go change into her little outfit. A few minutes later she came out in a maroon teddy with her very white silk panties on. She said she went to Victoria’s Secret the other night to get the teddy. I thanked her and told her she looked damn sexy. She looked so good, I wanted to rip her teddy off and screw the crap out of her. But the bigger part of me wanted to make love to this women that I had loved for so long. We made out and rubbed each other until the clothing eventually came off. While I now know that I should have gone down on her, I was inexperienced back then and didn’t have a clue how to do it.
I told her that I needed to get a condom out of my bag. She was glad that I brought one because she didn’t. I came back to the bed, put on the condom. (they are so uncomfortable)and turned around to face her. We kissed some more and then I asked her if she was ready. She nervously shook her head yes. I positioned myself on top of her and I felt my penis in between her legs. Her legs slowly parted wider and my penis was touching the outside of her vagina. We were kissing this whole time. I took my penis in hand and rubbed it up and down her lips. I withdrew my hand and slowly pushed forward. She looked minorly uncomfortable. I asked her if she was OK and she said yes. I pushed some more and knew I had reached her hyman. She was now in more pain than before but wanted to keep going. I slowly pushed more of my penis into her vagina and broke her hyman. Slowly in and out, in and out. She said it really hurt, so we stopped to rest. After some more minor pushes, and then more pain, we decided that maybe it would be better if she was on top. She climbed over me and placed the tip of my penis at the opening of her vagina. She lowered herself down, but stopped with intense pain. She started crying but was able to keep going. She was frustrated with the pain. I told her this was normal for somebody’s first time.
We eventually finished. I came a little and she didn’t. I did make her come manually though. As we rested, she thanked me for deflowering her.
We ended up having sex 6 more times, everytime I came, but she didn’t. I helped her everytime afterwards though.
We have remained friends all these years. I went to her wedding a few years ago. WIth my future wife next to me, I still was thinking that I had deflowered the bride.
Processing your request, Please wait....
