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Taking it to a new level

Date: 11/13/2015, Categories: True Story, Transsexual, Author: Nomad14, Rating: 90, Source: sexstories.com

This story cover what happened about 2 months after my third date with Rita, this was not our forth date. We had seen each other about 6-7 times since our third date. I had not seen Rita in two weeks and agreed to meet for dinner and then go to our favorite bar, and then later her place. When we got to her place she turned on some music and then we started making out. She then said, lets go to bed. We walked into her her bed room and she started undressing me. She had been wearing a short dress and I lifted it up over her head. Her dick was straining to get out of her panties. I pulled her panties down and started stroking her dick. She then turned around and bent over to her nightstand and opened it, she pulled out her bottle of lube and handed it to me. She then said, make love to me baby. She is tall and I told her to get on the bed doggy style. I lubed up and slowly slide into her, and she gasped as I went deep. She then said fuck me baby. I started pumping her and it felt so good. I leaned over her going deep and grabbing her tits. It did not take long for my cum to start to rise from my balls, and I felt the pressure that I needed to cum. I asked her if she was ready and she said, yes baby, just let it flow. I came very hard and throbbed in her ass. She groaned and said, yes baby, shoot it deep. My dick softened and I fell out. She rolled to her side looking at me and told me how good that felt. She then went to the bathroom and cleaned up. While she was in there she ... said, maybe tonight you will let me play with your ass. I said that I had been thinking more about it, but was really afraid she would hurt me, being so big. She laughed and said, tell me the truth, do you ever have a really big shit some times that looks like a log? I guess that was not the sexiest thing she could have said. I said yes, she laughed and said if you really relax you would be fine. She walked back in and pushed me down on the bed on my back. She had a towel with her and cleaned up my dick. I was on my back and she was between my legs. I looked down and her dick was very hard, she looked wonderful. Next she started stroking her dick and she looked at me and said, trust me baby, I will not hurt you, and I will only go how far you want me to. I said ok, and watched as she lubed up her beautiful dick. She then took some lube and rubbed it on my ass. It felt really weird and I was really nervous. She then took her dick head and started rubbing it on my ass hole. I said to my self, just relax, just let go, just let this happen. She started kind of pumping forward and backwards each time pushing harder into my ass. This felt good but I could feel my asshole trying to open up each time she pushed harder. She then pulled back and added more lube to my asshole and her dick. Then she went back to pumping against my asshole. As she did this she held her dick in her hand to keep guiding it to the right place. It was so hot watching her do this. She the pushed hard a few times ...