For a few months in 2018 I was hooking up a guy I had met on Bumble. I’ve always been attracted to personality and vibe more than if the guy was “hot or not”, but he was very conventionally attractive. Tall, fit and a cute face, and later found out a big thick cock.
He would come over, we would chill for about 30 minutes and then hook up. He’d never been with anyone who was willing to try anal before, because of his size. I volunteered to give it a try. I’d only done it a few times before, and guys much smaller than him would struggle trying to squeeze in. So I figured it would be best to do some prep work before he even got there (which I’d never done before). In the shower, I started fingering my ass, and realized why it had always been such a struggle. It hurt my finger more than it hurt my ass lol.
I tried using just my fingers, but it was useless. So after the shower, I took my slimmest dildo, some lube and tried to make it work. The tip to the dildo was skinny, so putting it in initially wasn’t too hard. The hard part was actually getting it inside me. But I managed. It was so tight, I’d wondered if it had hurt partners in the past.