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I felt so bad for her but was too cowardly to tellher the truth. I just didn't want to lose my only friend.During the time leading up to summer break, I had begun crossdressing. Itstarted with the clothes from the Halloween party. The thought of wearingthem again grew and grew in me until one day, when I knew Jessica wouldn'tbe coming over, I put them on. It was instant stress relief andrelaxation. It just felt good to be in them again. I felt more at peaceand better about myself when wearing them. Over the next few weeks, Istarted dipping into my saving to by an item here and there. I alsostarted perusing the internet to learn how to apply makeup and walk inheels; as well as trying to develop my female voice. I felt better andbetter as I dressed more and more often. I had a nice little collectionof clothes and shoes by the time the summer break rolled around.Back to the main story, it was two nights before our planned vacation. Ihad already finished my finals for the. I stood up as he signalled me to do so and followed his lead. The bed was right beside us and he guided me into a doggy style position. I had my hands and knees resting on the mattress towards the edge of the bed. He gently pushed my head down. My ass was facing upwards as he dropped to his knees. Again he licked my asshole and prepared it for penetration by lubing it up with his saliva. After a little teasing with his tongue he teased me a little more with his fingers. He stood up and a few seconds later I felt the tip of his dick touch my asshole. He slowly inserted it into the hole and I immediately pulled away. This was mainly due to nerves and the slight pain I felt. He wasn’t fully in yet I felt pain. He calmed me down a little by convincing me it will be fine. Of course he also reminded me that nobody else knows about the toys he found. He had an advantage and so I had to obey. He tried again and got it further in past the tip until I retreated again. After gathering my.
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