My Life as a Shemale Part8

She looked down at me and I was covered in her cream. I wiped it off quickly and I saw her pulling her gown over her head and then mine. She pulled me up to her until we were eye level, she was older than I was since she had skipped a class but at this moment we were equals. She let her legs fall to the side and opened herself to me, I knew what she wanted and still thought that it was a bad idea and was about to tell her so when she placed a finger on my lips and whispered, "Just go slow, this is too special to mess up with a piece of rubber". I gave in, it wasn't a difficult decision but what was getting hard was my member. I placed it between us but when she didn't reach down, I knew she didn't know, so I did it for her. I took my penis and let the head slide up and down her vagina until it got wet, I kept holding on to it, pushing it in a little further and pulling back, trying to get as much moisture on it as possible.
After awhile I looked her in the eyes when I was ready to go deeper. She seemed a little scared but shrugged it off, she wanted to be cool. I slid in a little ways letting her body part before me in its own time, all the while looking into her, our eyes locked, every move I made instantly send signals to her eyes and I knew when to draw back. She whispered, "You must be all the way in, it hurts pretty bad right now", I smiled but didn't tell her that she only had the tip of me inside her. "Were getting there". I let my tip slide in and out a few more times, I didn't know what to do or to expect but then I slid forward and hit her hymen, this caused a little chain reaction, the pain made her pull up her legs and she tried to close them, except I was between them and she inadvertently pushed down causing my penis to run her through, it must have been bad but my penis stopped half way in, tears flowed from her eyes. I slowly backed off trying not to cause her anymore pain. I was looking down at my penis and saw blood on it and the same was dripping a little from her lips too, I guessed that that was it. She went to the bathroom and came after a while, "I think that was it, you did it". I had felt bad for hurting her and it was certainly a life experience, one I didn't care to really repeat. We huddled up together and fell asl**p again.