I could tell it hurt a little but i made my move anyway. I told her she shouldn't leave just yet because i think she deserves better than what she had right. Jessica smiled at me and picked up on what i was driving at and proceeded to walk right up on me and asked if i thought this was a good idea and my response was it was the best idea i had! We embarrassed in each others arms sharing a sweet lovingly passionate kiss while our hands softly explored each others body. After our lips unlocked we looked into each others eyes and i said we should move to the bedroom and continue this before someone comes home. With a smirk she took my hand and lead me to my wife and i's bedroom wear we began to undress one another as we enjoyed all that we seen upon each other! Jessica put her hands on my shoulders and sat me on the edge of the bed while she knelled down in front of me with my rock hard cock was ready for her full attention! With as many years we had between us it was almost wrong, but. Finally, her cock was rock hard and she was ready to assault my asshole. She took a condom from the glove box and wore it. She poured some lube on my asshole just to make it easier.My Trans friend then made me bend on the backseat and started to put her cock inside my ass. I could feel her cock pushing against my hole. The lube was helping to an extent but not all the way through. She started to apply pressure and slowly her cock head is making its way inside my ass.I could feel a burning sensation followed by a sharp pain around my ass. The pain gradually increased and I jumped forward to avoid the cock. My Trans friend called the constable for a little help and she happily agreed. She came towards the other end of the backseat and held me there.Now she started to push her cock inside again. I could feel a lot of pain but I could not escape from it this time. After a lot of effort, she finally got her cock head inside me. Tears were rolling from my eyes and I was asking her to take.
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