Lately, though, you have had a lot more on your mind. Your parents have been struggling financially and they can no longer afford to pay your tuition. There's no way you want to lose all the work you've done at this school and miss out on all the opportunities after graduation.This brings us to your current situation. You are standing in a dimly lit room in-front of a table of the board of directors for the school. Next to you are two other boys whose parents can no longer afford tuition costs. Each of you are wearing the school uniform, except not the male uniform. You are wearing a white button down shirt with a deep navy cardigan emblazoned with the schools crest and a plaid skirt with knee high socks.See the number of female Attendants is not nearly as high as the board would like so they have hand selected male students with the most feminine features who are struggling financially. You are one of those students and you have reluctantly agreed. Your hope is that word will get. "Your reading my mind", I said. She said she wanted to experience everything with me and she knew I would be gentle and not hurt her. "Wait right here", she said as she jumped up and ran down the hall. I hope I can be gentle I thought as I laid there with my cock sticking straight up and as hard as it ever has been. With the anticipation of something I wanted, something I've never fully experienced with anyone made my cock ache. This was certainly on my bucket list, along with a few other things. I have to be gentle and I will. I love her so much I couldn't bare the thought of hurting her, besides if the experience is bad she may not want to do it again. I laid there and remembered when I tried it with my girlfriend. We never actually talked about it rather I tested the waters a little bit one time when I was fucking her from behind. As I pumped into her I put some spit on my thumb and began rubbing her crack slowly working my way to her anus. When I reached it with no resistance.
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