The old trailer trash waitress in the small town

I was working in the small town of only about 600ppl for about 6 months. I was 22 and in good shape, decently long and thick cock and sure of myself. Darlene was the waitress at the only diner in town. There was a restaurant just outside of town but this was much more convenient and I ate their almost 3 times a day everyday. Darlene and the cook, and occasionally the owner were the only ones that worked. She was there on the counter and the few tables everyday, 6 days a week. She was plump, not really fat, still had a shape to her body, but just bigger all around I guess. She was dyed a reddish blonde on her head, with a set of what I found out were EE cup tits. She had a bit bigger ass, not too bad. The whole package just sort of jiggled when she walked. Soon I was wondering what it did when she got fucked. If I went later in the evening the cook would be gone, the owner too. Most people were turned in by 8 or so, it was just the two of us. I found out she was 58 years old, I believed it but told her I thought maybe she'd be in her 40s. She'd been married to a guy who was her high school boyfriend. He drank a lot, even beat her, and at times made her have sex with him and some of his friends, in front of whomever was at their house getting drunk. She was passed around by them all and he didn't care. He took to using his belt on her back, tits and ass to punish her. We told each other all about our histories. Before her highschool boyfriend she sucked one of her uncles many times. Then her boyfriend and he fucked her for her first time. While with him he'd let 21 other guys fuck her, he saved her ass for himself, so only BJs and pussy for them. Then when she knew it was all over, he brought in 8 guys and with him it was 9 and he made her lay down on the bed on her belly as each guy buttfucked her. She said it was months, and two trips to the docs to get right "back there".

It was a sad story, now she fucks guys when she get the opportunity but with her age it doesn't come by often. I expressed my interest and she immediately agreed. At her place, taking off her uniform dress, she unleashed those massive tits with pink nipples and pulled down her granny panties revealing a shaved pussy, wide hips, and a wide but nicely shaped ass. She immediately got on her knees, freed my cock and blew me, swallowing it all. Then on the bed, I ate her bald, big lipped pussy and her 2 inch long clit. Then we fucked. It was good all around, she was tight for someone who admitted to 53 guys fucking her. While I was eating her I finger fucked her pussy and her ass too. After, holding her, kissing and playing with her tits, she told me she liked them pinched hard, twisted, pulled, yanked, really really hard. As I was doing that, we were kissing and I moved my hand to her big ass. I stuck in a finger and started finger fucking her ass while staring her in the eyes. "You like to do that, I mean do it back there? You wanna do it that way? I'll let you" she whispered. "yeah, sue, I love anal" I told her. "Just give me a sec" she said and got up, out of a drawer in her dresser she brought out a tube of lube. She put some on my cock, covering it all over, then got on all fours, handing me the tube "Get my ass ready" she told me. I lubed her ass and she laid down with her tits and head off the bed, and I got on top of her. I did see some scars on her back and her ass from the belt her husband used to use on her. She was grunting as I pushed into her slowly, then started bucking back and forth. So I started fucking her, quite tight ass for all I was worth. I would reach around and pinch, twist and pull her nipples so damn hard I swear they were pulling off. She actually had another orgasm while being titty twisted and buttfucked. I asked if it was ok to cum up her butt and she said it was fine, she wanted me to. So I deposited my third load of cum for the night up her ass.

She begged me to spend the night, she said that way if I wanted to fuck her butt during the night, or at least the next morning, she'd be ready. I told her it doesn't have to be up her ass I would fuck her pussy too. She told me that it's whatever I wanted but she realized I liked buttfucking better so she was available to do anything I wanted, whenever I wanted. She reminded me she can cum from getting it up her ass as long as I do the tit thing, and she'd not mind if I ate her pussy sometimes too.

So basically I had my dream woman. Not good looking, definitely not a hardbody, a jiggling, chubby with huge melons that hangs them over the edge of the bed when I buttfuck her so she can get off too with my abuse of her tits. She doesn't give a shit about romance, about kissing, or having to do special things for what she wants, it's all about what I feel like doing. I took her to the beach at a resort for a long weekend and it was there I discovered that after about a week of buttfucking, she started buying kotex to put in her panties, but more towards the back as she was leaking these days.

I look back at that 20 years later and wonder just how many times I fucked Darlene up her ass, how much cum I must have shot inside her. I still did fuck her pussy as a change, she even let the hair grow in on her pussy (dark brown with some gray starting to grow in). She took cum in her pussy, her mouth, and up her ass. Sometimes I'd cum on her face (she actually LIKED facials), her tits, her big ass, and in her pussy hair.