This is a completely true story.
I'll call her Tammy. I knew her in high school. Neither of us was popular, but for different reasons. Since we didn't have many friends we hung out with each other a bit. I know I could have fucked her, and maybe even her friend, but I wasn't horny enough to become the butt of even more jokes. I did go through a lot of tissues thinking about having threesomes with them. They were both a year behind me and after graduation we lost touch.
Now fast forward about 18 years. I got back in touch with Tammy on that social network site that everybody uses. We exchanged numbers and met for drinks. She was divorced with a few kids and had put on some weight. She'd had a good figure back in school but it was long gone. We met like this a couple of times and then Halloween came along.
She wanted to go with me to one of the big clubs in the area. I didn't have anything else to do, still not popular, so I figured why not. I picked her up at her mom's place and it turned out she wanted her mom to come with us. When we got there I had a bit of deja vu from my younger days: loud music and hot girls that didn't want me. One girl did approach me, and I'm still kind of kicking myself for not going for it, but I had Tammy and her mom with me and I was their ride home.
Her mom spent the whole time sitting on a stool smoking while Tammy danced by herself a bit, I don't dance at all. She did come by me a few times and grind up against my crotch, I kissed her after the first couple times.
We finally left about 1:00 in the morning. I spent most of the drive with my hand on her thigh. When we got back to her mom's house her mom got out and went straight inside. Me and Tammy started kissing some more and she didn't care at all where I put my hands. She stopped me after a minute because she wanted me to drive somewhere else, the parking lot at the apartment was too well lit.
I drove a couple blocks away and went back to work. I got my hand inside her panties and after a couple minutes of rubbing her clit and finger-fucking her she had herself a nice orgasm. She'd barely finished it before she started undoing her top. I pushed her bra down and one of her massive tits popped out. After I'd sucked on it for a couple minutes she told me she couldn't take care of me with my pants done up. I got out of the top half of the coveralls I was wearing as part of my costume, unzipped my jeans under them, and she went to town. It felt great, of course, but I couldn't come. Even though I'm not a kid anymore I still don't know why I couldn't, she would have swallowed every drop if I had. After several minutes of her gobbling me up I told her I wanted to fuck her. After a quick discussion of what it might do to our "friendship" I started the car up and drove to my place.