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My fingers probed his hole “feel good sweetie” all he could do was nod yes . “How about now” and I slide all my fingers inside him. He let out a moan and pushed back. I twisted and turned my hand as it went inside and he responded by pushing back harder. “Ever been fist fucked slut” I asked “NOOOO” he sighed and I rammed my fist deep inside opening my hand and wiggling it . My wrist and part of my forearm inside I pulled my open hand up inside him and pushed out his belly. I pulled him up a little and took his hand rubbing it over his belly so he could feel the budge. OMFG he yelled and he unload a massive load of cum the condom filling as he came. I pulled my hand out and laid him on his back leaned down kissing him as he neared his orgasm. I knelt up and rubbed my dripping clitlit to his lips he took it in his mouth as I flowed. “little cum dump” I said and turned and stoked his cock pulling off the full condom as I did. Once off I went down on his cock licking and sucking up all. There was one place he liked a lot so we frequented it a lot. I started to like it too for a few nice reasons. It had been around a while and was well known however, it was past its prime. Still, it was clean and, not only had good food but the staff was very nice. Most of the waitresses were in the 40 to 50’s age group, nice pleasant gals. There’s a vibe you pick up with people…we went there with me in the male role a few times but, rolled the dice once (because of a semi-special occasion) and nothing changed. They even seemed a little warmer, friendlier and totally accepting of us both – mostly me.This was a fairly important ‘date’ and I wanted everything to be right. I didn’t want to embarrass Jack or get laughed at. I really wanted to get very close in a public setting – not just be a guy in a dress!It was one of the times that I really put my heart into it. I went as far as getting a cut and style (casual) a few days ahead of time. Every item of clothing was chosen well ahead of.
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