I recently started to date a friend and while we were talking about what we were looking for out of a sexual thing together she mentioned she wanted to be trained to love anal, along with other fantasies and yes/no/maybe things. When I got to her place we didn’t have test results yet so we were doing all sorts of things that didn’t involve risk of sti. I kept teasing at her and groping her ass. She loves to have her butt manhandled. The next date I brought a bunch of toys and started to play in her ass. It was hours and hours of teasing her. Slowly working some lube around her hole. Gently pushing in a finger tip but not all the way in. Pushing in deeper until my knuckles blooped in and out. Adding more lube. Talking about everything as we went and teasing her for wanting to get her ass used. Putting in a plug and thumping on it while I licked her. Pulling the plug out and talking about how it was time for the next size up and then “changing my mind” and pushing the plug back in. Working up to bigger toys and more fingers. Filling her pussy while filling her ass.

I have a large toy, the square peg slink, it’s super soft and is a slow very long tapered shape. I put two fingers in her ass and opened them to drip more lube down into her. Then I introduced the soft tip of the toy and started to tease her hole with it.

I kept fucking it in and out slowly. As she got excited and reached for more I kept going in deeper stretching her out. Each time she got steady and was loving a slow fucking I would add lube and just enjoy her for a while, then when she got hungry for more I would push until she gripped the sheets and then I would back off a bit into more slow fucking. She was rubbing her clit and making such exciting sounds.

She came on that toy and had a great orgasm. She was cooing about how great anal is and how she never came like that before. Then she looked down to see the toy in her for the first time. It’s about 2 feet long and it’s a little shocking to see. She had no idea how big it was and how much she had greedily taken up her ass. I pinched the toy at her hole and pulled it slowly out to show her how deep it was and how thick it was, to show her just how far she had gone. It blew her mind. She never considered having more than a foot of toy in her.

Needless to say, she decided she likes when I fuck her ass. I’ve made her cum with my cock up her ass a lot. I sometimes struggle to cum from penetration and I get very excited to cum and fuck very rough to get off. Holding her off the bed by her ass and using her like a toy. Lucky for me she seems to like that. I do love to hear her come on my cock while I’m fucking fast and deep in her ass and all the dirty talk.

On out last date she asked if I could bring the slink back for our next date. I can’t wait to continue her training and see what we can make of her asshole.