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Philip's dick was erect, and while I didn't know it then, about six and a half inches long. There was no doubt that today would be the day, and Philip had come prepared. He fished a pack of condoms from his pocket, and showed me how to help him roll it onto his cock.At my touch, it twitched and I was surprised to feel how hard and warm it was. I spread my legs so he could gain access to my slick, hairy sex. He placed the head of his cock at the entrance of my virgin cunt, and slowly pushed in.It was, sheer pain. I could feel tears welling up in my eyes as he pushed farther and farther into me. My hands squeezed his shoulders to keep myself from screaming out. He looked down upon my pain contorted features, and asked if I wanted him to stop.I shook my head, no. I wanted him to go on. In one quick motion he broke through my hymen, and a sharp bolt of pain shot through me. I didn't utter a sound, my eyes were glazed over and I still clutched his shoulders. Once all of his dick was. Next day night, I got a message from her, she was bored and wanted to do something exciting. I jokingly said, go and watch some porn. She refused saying that nope, it doesn’t turn me on anymore. I decided to take a bold step, and asked her : I can get you wet, wanna try.She : Really? How ?Me : Wanna be my sub?She : ummm, what if am not wet by the end.Me : You can punish me in whatever way you want.She: Fine, let’s start.So that night we had an amazing roleplay on text, I elaborately described how I would feel her, lick her etc. By the end, she had completely submitted herself and finally messaged.She: You win, please let me go and finger. I am dripping down there. I was really happy and allowed her to leave. It became a routine for us to chat at night, we talked in real in front of others like nothing was happening. Every night we had some session, she was getting more and more submissive, but never sent pictures. One such weekend, she was alone in the flat for the weekend. My.
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