And we didn’t have any lube so she was afraid. My dick isn’t all that big in my opinion but she was afraid of how’d it hurt. We agree to just wing it and try. So she lays on her side. Spits in her hand and massages her asshole with her saliva. She does the same with my dick. I lay next to her and position it against her asshole. I very lightly start pressuring her asshole with the tip of dick. As I started to get inside her, her left hand swung around and started pushing me away. She started to yell into the pillow. My barley get the top of my dick inside when she lets out a painful scream into the pillow. She pulls her hips way and my dick pops out. She looked at me. Her eyes watering up. She mentions she not ready and we’re gonna have to wait till we’re better prepared. She apologizes but says she make me feel better. So jumps down to the edge of my bed and starts to work my dick again. She was a head master so I just go with it. I really wanted to smash but I knew it’d happen. ." Surprisingly, I was suddenly shy andcouldn't tell her what I was thinking."Um.... Just spill it girlfriend." She smiled at me."I think I want to get him turned on enough to fuck me." I saidquickly."Oh, well okay. So, definitely a wig, heavy makeup, and we need to makesure you are curvy in the dress. And I am thinking some lacy, hot,white lingerie underneath. Probably a pair of white heels. We need toget going to get all that." She was bubbling with energy now."Okay. Thanks for you help."We left my car in the Panera lot and Anne drove us first to a uniformstore. When she went through her paramedic school, she had boughtscrubs there and remembered seeing old fashioned traditional uniforms.Embarrassingly she told the saleswoman why we were there, and she pickedout a couple different ones for me to try on and they picked the onewith the shortest hem line, it stopped a couple of inches above myknees, and my ass looked the best in. They both complimented me on mybutt, saying.
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