Chubby, unattractive fuck

It was a while ago. I was 17, in great shape, met this older woman, 55 at the nude beach. She took me back to her place and sucked and fucked me silly. I'd never even seen a pussy or tits in real life before that trip to the beach, only in pictures and videos. I have to say, her black haired bush was incredible. I loved pussy, and soon loved pussy eating, getting sucked, and eventually even buttfucking her. So leading to the fatty, ugly story. Tina, the 55 year old from the beach, had a niece who was fat, unattractive, and 23. She had never been fucked, never did anything other than suck dick for 5 guys, who came in her mouth, then dropped her off at home. That started at 17 and she was justifiably traumatized by this treatment. Tina, showed me pictures, I met her niece, Shelley several times. Tina asked me if I would consider going out with Shelley, and eventually fucking her. Shelley knew it wasn't real dating, but Tina wanted me to be kind, and respectful and treat her like a woman, not a fat girl to fuck and leave. She told me about the blowjobs and what the guys did. So I agreed.

I took Shelley out to the movies and first to a small restaurant. She was enjoying it. Shelley was indeed short, 5ft. 3in, fat 290lbs, red haired and not especially pretty at all. She had small tits for a big body. They were B cups but on her big body they looked smaller. Her tits stood out perfectly on their own, no sag at all, and her areolae and nipples were darker and puffed out from her tits. They were quite pretty actually. After we ate, waiting in the car for the start time for the movie, she wanted to talk about "what we were supposed to do". What she meant was that she knew I was taking her out because she wanted to have sex. She also told me we didn't have to do it and "date" like this if I just wanted to do it, it would be ok with her. She just wanted to break her virginity so it wouldn't be such a deal with others she might find willing to be with her. Up until then the 5 guys she sucked (2 over them over 3 months, 1 for 6 months the other two only once) two of them sucked on her tits. One just squeezed them and her ass while she blew him. He is the one who insisted that she get naked to blow him in his truck.

I explained that I was perfectly happy to have sex with her, she told me her aunt wanted me because I was gentle and after she got used to doing it, she'd enjoy it with me. I kissed her, opened the top buttons on her blouse, and lifted her bra over her tits and started sucking on them. We got in the backseat (I made her keep her tits out while moving outside the car) and I laid her down. Instead of her blowing me, I went down on her. Her pussy hair was red too, just like her head. She went berserk, she loved it and came three times, then wanted to suck me off, but it was time to go into the movie. I asked her to take off her bra and her panties while we went to the movie. I had her throw them on the front dashboard. In the back of the movie, I kept feeling, lightly pinching her nipples, and putting my hand up her skirt to her red haired pussy. She pushed my hand away saying she was about to cum again. "Then be quiet about it" I whispered and got her off again. I ate her on three more dates, she wanted to blow me, but I wouldn't let her. Finally she said she wanted to do it, I was so good to her that she wanted me to enjoy it too. So instead, I let her jack me off, and just before I came I moved her mouth to my cock to cum in her mouth and she swallowed it all.

The next date she asked me when we were going to have sex, asked if I didn't want to do it with her, she would understand and hoped we could be friends, but she would understand if I didn't. She didn't know that her aunt got us a hotel room, really nice place and I took her there. It was there that I saw she'd shaved her pussy bald, and I licked her all over, she was about to cum the second time, and when she was almost there I plunged my cock into her virgin pussy. She did have her hymen intact and I broke it for her. I fucked and came inside her. She managed to finish that one orgasm I'd started with my tongue. Later I fucked her again, and we slept. In the morning I woke up with her mouth on my cock. I gave her my cock like she'd been asking me to do for a couple of weeks now. I blew in her mouth, and ate her pussy again, mixed with my cum.

We fucked several times, but there was a big age gap, and she knew I was fucking her aunt. We stayed friends and occasionally she even came over to Tina's place and stayed the night in the guest room with me and we fucked more. It was in that guest room one night, she asked me "What is anal like?" and I showed her. Then she met two guys who like her body, and fuck her regularly, they even know about each other. Me, I stayed fucking her aunt, until I graduated and went to grad school in another state.