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The next day, we did nothing but lounge around the pool and drink cocktails. As the sun set, we knew it was time to clean up and get ready to go to dinner. I had already fucked my wife that day when we returned to the room for lunch. I wanted to fuck her again before we had dinner. She was feeling frisky, so it did not take much to convince her to strip down and spread her legs for me. After our little fuck session, we showered together and got dressed. There was a knock at the door. We looked at each other slightly puzzled. She went over, and opened the door to find our new friend Whitney. He apologized for not calling first, but he realized his suite was just a couple of doors down from his. He wanted to see if we would join him for dinner. We accepted his offer and he told us that he would like to take us to one of the best seafood restaurants on the island. A place where the locals go to eat. We jumped in his jeep and off we went. The drive along the coast was beautiful. We. "I pulled his hips back as I pushed my ass forward and as I gave another thrust I was almost buried."Jim. I am almost all the way in you. One more push will do it."By now he wasn't just sobbing but he was all out crying. "Ok, go ahead" he shuddered.I gave another light push and was in him to my full seven inches. I waited a minute to see if his crying would stop or at least slow down but it didn't. I was damn sure not going to waste this penetration so I began to move ever so slowly. "Jim, would you like it better if I pulled it out of you for a minute and let you turn over on you back so you could put your legs up in the air as I slipped it back into you. That way you could see my face as I was fucking your ass and watch me as I had my orgasm?"He thought that would be a good idea and it didn't take very long before I was slipping back into him with one long smooth thrust. He had stopped crying when I had taken it out of him but the reinsertion brought the pain back and his tears.
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