Mandy looks at me and says "Glad you are up now, wanna take a turn on the sissy?" I said "Sure, If you want" She pulled the 10" dildo out of Lilly's a...s and tells me that she is good and lubed up and to take her hard. I grab a condom, skin it on and get behind Lilly doggy style and start pounding her ass. The Strap on was a bit thinner in girth than my cock, so she had to stretch a bit to allow me to thrust the whole way in. She was tight. Mandy got up and in Lilly's face and stuck the strap on. She was now pushing with force, in-spite of all the foreplay, I was feeling excruciating pain. I shouted stoppp, and took a few breaths. This repeated a few times. I later learnt the trick of anal penetration. While penetration, I was trying to suck in or hold my anal muscles tight which was causing the pain and blocking penetration. I stopped holding tight, instead relaxed and went myself pushing towards her dick. The dick slowly, very gently slipped into and ohh my Goodness, it was absolute. More

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