Ashley was in the window seat next to me. Madison was across the aisle and luckily had no one sitting next to her. Since we were on a redeye going Eas..., I was happy to have the extra room.After the crew had served the drinks and dimmed the cabin lights, I felt Ashley pull the blanket over me. She leaned over the armrest to whisper in my ear, “This is Madison’s first flight, ever.” I looked over at Madison who was staring at me and looked like she might be shivering. I unbuckled and moved over. Jerking off to regular porn wasn't doing it anymore, I needed something more exciting. I started to watch more and more sissy and shemale porn and had bought some toys to mess around with, a couple of different sized butt plugs and a 5 inch slim dildo. Every night when I had time, I would strip naked and lay down watching sissy porn, while I trained my tight little virgin boi pussy. Each night I tried to take a bigger butt plug, until I was comfortable fucking myself with the 5 inch dildo. It. More

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