I continued kissing Emma wildly and Trudy was now on her knees between Emma’s legs and right behind me. I knew what was coming up next.I closed my eyes and hoped for the best as my tongue swirled Emma’s tongue. I felt the head of the dildo on my anus as Trudy started circling it on my arse. I was never fucked in my ass and this was my first time. I guess Trudy knew it since she was good at reading people.She took some lube and started to finger my asshole a bit, stretching and preparing it for the dildo. She fingered me in my ass with two of her fingers for a few minutes as I moaned into Emma’s mouth.Emma’s face was completely covered in my saliva since I was spitting and licking it continuously. As Trudy was done stretching my asshole, she finally decided to go with it. She placed the dildo on my ass and pushed it, inserting about 2” of the head in my hole. It was excruciatingly painful and I screamed.“Stoppppppp,” I looked at her.Emma pulled my face and continued sucking my mouth. Every year they had a big Halloween party, and on that night everyone was welcome - straight, gay, shemale. I had consumed quite a bit of white zin, and I allowed the girls to "persuade" me to go along with their plans. So I sat there on a bar stool while they did my makeup and teased up my blonde wig and fit me back into the spandex minidress. "But what about high heels?" I found myself asking. Without a word, Terri went into our bedroom and came back with the red 4 inch pumps I had been hiding in our closet. I blushed beet red. "You mean these, darling?" she said smirking. "Don't worry, I found these when I was looking for my stuff a few months ago. It's ok - lots of guys like to dress up!"Go ahead, Keven, try them on!" Jinky squealed, sipping her wine.I pretended to be uninterested, but as the girls teased up and sprayed my blonde hair up really high, and then applied green eyes shadow and red lipstick, I began to get really excited. Fuck! I looked so fuckin SEXY!When I saw myself.
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