Training My Ass: Breaking It In!

I’ve always wanted to try anal. Toys have never been enough.

And I’m not the kind of girl that can resist temptation. When my friends with benefits and I went on vacation, I finally got my wish. My FWB was too exhausted after traveling to join me on the hotel’s stretch of beach, so I went alone in a tiny thong bikini. I claimed a cabana for myself and stretched out, enjoying the sound of crashing waves while thinking about training my ass. I’d used plenty of toys, but my FWB wasn’t interested in anal. It had me pouting and needy. Thankfully, a sexy, tanned Cabana boy wearing nothing but bathing suit bottoms showed up and looked me over with obvious hunger. Maybe I could try training my ass the way I really wanted.

“I’m here to take care of all your needs,” the cabana boy said while looking at my perfect, round ass. I undid the ties of my top and hummed, telling him I needed some sunscreen before I could leave the cabana. He showed me a bottle and I asked him to cover me. He took his time, moving closer and closer to my ass. Then he skipped to my thighs and took care of my legs before taking a sharp breath. He cleared his throat and I realized how hard he was. He was definitely the kind of man who would be happy training my ass.

So I told him to keep going, to make sure he didn’t miss a single spot or I’d get burned. He palmed my ass, squeezing and massaging, making me wetter and wetter. I was so turned on by the idea of him training my ass that I could barely stand it. Then I moved my thong to the side a bit, tempting him and he groaned.

“I think I need help with something else – training my ass. Can you help?” I asked.

He nodded and slicked his fingers with sunscreen before working his fingers over my crack. I moaned and arched for him. I knew we had to be quiet while training my ass, but it was hard when he worked one finger into me and started teasing me. People were right outside, but it felt so good. After a minute, he worked in another finger, spreading me open and training my ass so I could take all of him.

Since he needed a little more of a hint, I tugged at the ties on his trunks. My willing cabana boy, dropped his pants and climbed on top of me. He rubbed his cock over my crack, getting closer and closer to my hole. I wanted him training my ass and that was what I was going to get. I arched until the head of his cock hit his fingers. He moved them and filled me in one sure stroke.

I moaned loudly. It felt so good, so new, so naughty. Training my ass had never felt better. His answering groan proved he felt it too. He thrusted deeper and deeper into my tight hole, over and over. My eyes rolled back and I spread my legs to have more of him. Then he gripped my hips and slammed into me again and again. He was perfect, thick, hard, and just kept working him self deeper and deeper into me.

He was training my ass the way it needed and I didn’t want him to stop.

The cabana boy fucked all memories of my friends with benefits away until all that was left was him, training my ass. I touched my clit, playing with myself while he chased his own pleasure. He groaned and grunted, louder and louder until I was sure other people on the beach knew what we were doing. I didn’t care. It felt too good. It didn’t take long for the cabana boy to come, filling my tight, used ass with his jizz. I sighed. Training my ass was better than I thought it would be and even as he got off me and cleared his throat, I was still savoring all the fun.

He fixed my bathing suit and asked if I needed anything else. I grinned. “Now that you’ve finished training my ass, I’d like a drink … and maybe more of you in a few hours.” The cabana boy hurried to do what I asked. Even if my friends with benefits didn’t want to spend time training my ass, I could find men who were more than willing to fill the fantasy and my back hole over and over again. I was sure of it. If I wasn’t gonna be a Parolee’s Slut , I was still gonna have some help training my ass.

Call Bailee 1-888-823-6127