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Wingman
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Wingman Jim was my best friend in my teens and early twenties. He was happy to be my wingman and go after the second-place girl when we went out trying to hook up; it became a running joke that he would probably wind up with the girl who drove, and I'd get the better-looking one who got the ride. Jim was about 6'3" and anywhere between 250 and 300 pounds at any particular time. He also had a monster cock, and knew it. One night we were at a club where we both worked, checking out the women and he pointed to a woman who was built a lot like him. She was tall, medium-brown skinned, with huge tits and a big onion of an ass. He handed me my drink and said " gonna fuck that black chick...". I chuckled and said "Sure you are," and he told me to just be patient. "What makes you think that?" I said, and he told me that she and her friend were checking out guys' bulges, and that he could tell she was looking at his. It wasn't long before I was out on the dance floor and here comes Jim being dragged out to dance. He gave me the eyebrow and smiled, and started doing his "way-too-big-and-white-to dance" dance, which is basically what it sounds like - an offensive lineman shaking it to Keith Sweat, Bobby Brown, or whatever was bumping back in the late 80s. After another few drinks he came over and handed me his car keys (he was OUR driver), and said "time to go." She was standing at the door waiting for him. The three of us walked out to his car- it was summer, so no coats- and they got into the back seat. I was happy to be HIS wingman for a change, and curious where this was going. In the rear view mirror I could see them making out, her huge tits out of her black bra, and eventually lost sight of her because she was down sucking his cock while I drove. We went to her small apartment; her cousin was babysitting her very young baby, and quickly left so it was the three of us and the baby in the other room. She and Jim went into her room while I got a beer from the fridge and watched TV. I could hear her moaning and telling Jim to give it to her, to fuck her hard, and I drank my beer feeling glad for him but also had half a hard-on wanting some pussy myself. He came to the living room in his boxers holding a beer and said "Your turn, bro." "What?" and he said "Go on man, your turn..." I climbed out of the recliner and brought my beer into the bedroom, where in the moonlight I could see her reach over for my belt and start to unbuckle without a word. I let her take my cock out while I took another swig and began to feed her my hard dick. I started to suck and squeeze her nipples... and milk shot out between my fingers. Ah, the babysitter! Those huge tits! I was naive about some things, but I was starting to piece this together. If it happened today I would have gone down on her immediately to eat her out and get that<b> cream pie </font></b>that Jim had left in her, but back then I was skittish enough about sloppy seconds. Looking down at her well-fucked cunt lips I easily slid my entire hand inside while she fed on my cock. Soon I buried it inside her gaping pussy and began riding that big girl, with her again telling me to fuck her and that she wanted both of our cum that night. Before long I looked up and Jim had come back in, rubbing his dick over her face and telling her to beg him for it if she wanted it again. Needless to say, she did- very much. I came inside her and headed back to the living room, satisfied and giving the honor back to my man Jim to finish things up. A little while later he emerged with a shit-eating grin on his face and we headed out. He went back a handful of times that fall and winter and gave her the big cock that she needed. Who knows how many others she was getting too, but maybe that's none of our business. It's good to have a wingman, but nice to return the favor sometimes too! |
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