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I said “hold up a minute, don’t think I want to be seen in public with you like that”. We ultimately decided it might be fun do have a date but in another town away from where we might run into someone we know. We made plans to meet and drive south to a different county and have our date.We met at the parking lot like normal and he gets out of his car. I see him and he looks hot to me. He’s wearing a short pleated skirt with tan thigh high stockings. He has a light blue blouse unbuttoned down to where I could see the top of his stuffed bra. It looked like he was a c cup. It looked like a professional had done his makeup because you had to look real close to see if he was really a guy. When I saw him a felt that twinge in my cock.He gets in and we head out to our destination. Our plan is to go to a matinee movie then get something to eat. After about an hour drive and lots of teasing by him we arrive at our theater. Thank god for GPS.I buy tickets for a show I never heard of and we go. ..“Ohmygodcalebicantholditanymore!!” He screamed and he body jerked violently and I felt a hot stream of liquid splash upon my abs. He came, and came hard. I sat up and looked at the mess he left as I smeared it into my skin. I then placed his legs upon my shoulders and tenderly kissed his ankles before pole driving myself back into his boy pussy. I was pounding him with a fury that I never knew I had. The only sounds in the room was a rapid, loud, skin and skin slap and his loud moaning. I placed my hands on his tits and started to fuck him with all of my might, my balls swinging back and forth, hitting the groove of his ass. Suddenly felt the cum start to travel from my balls and with one last thrust, I unloaded the biggest cumblast of my life, at least 13 hard squirts. My body jerked with every shot and sweat dropped from my face onto his. I pulled out and he immediately started leaking my cum onto the bed. “Caleb, oh my, you’re amazing....”“So are you Jess...”We caught our breath.
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