I (F22) have been doing anal training with my FWB, we'll call him K (M36) for most of the summer. He wore a condom at first in case I had any accidents. Lately I have been pretty good figuring out how my body has been working.

I needed to take breaks after doing anal from being sore. K told me when I was ready for anal or anal play again, I can put in my butt plug to say I'm okay to go for butt stuff again.

I put in my plug and went over to his boat he lived on in the summer. We started off with making out, taking off my shirt and playing with my nipples, pinching and rubbing one and licking and sucking the other. He picked me up by my butt, carried me to the front cabin and dropped me on the bed. Undid my pants and pulled them off. I spread my legs out revealing the plug and his eyebrows raised saying "Oh, okay!"

He went through his cabinet of toys and pulled out a vibrating egg, he pulled out my plug, lubed the egg up and turned it on and started rubbing the end against my asshole. It gave me a tickling and tingling sensation in my whole lower area and my legs. He slowly put the egg in my ass and stopped about midway letting my ass push it out a bit and he would push it back in little by little. I love the feeling of it expanding my ass while it was vibrating. As it went past half way my asshole swallowed it inside me. The vibrating made my insides tingle all over and my pussy was getting more wet. K lifted up my legs and started licking my clit. The tingling sensation was now from my legs up to my stomach. I raised my head off the bed and moaned out loud grabbing the back of his head. He started licking harder and it was like someone turned the dial up on me. I moaned louder the sensation was getting higher and higher until I felt the release as I came. He pulled out a mini vibrator and worked on my clit until I came again.

He put the vibrator down and pulled the egg out gently moving it in and out of my ass a couple times, I moaned some more and giggled as it was pulled out. He grabbed the back of my head and pulled me towards him, he put his tongue my mouth and I exchanged mine into his mouth as I felt his tip rub against me clit. He had me lay back down as he lubed up his hard cock. He lift my legs and rested my feet on his chest. I felt his tip on my asshole, he told me to relax and I just let my lower body sink into the bed. I felt more and more pressure on my ass until I felt his tip pop in. My asshole stretching gave a nice tingling feeling. He kept his tip in as he rubbed my clit with his thumb. He pushed his cock in more massaging my asshole as he slowly went in and out going further in each time. Once he was able to go all the way in he used the wand on my clit again. I was moaning so hard until my clit started hurting, "yellow, yellow!" I said really fast which was our safe word to slow down. He put the vibrator down and rubbed my clit with his thumb. He made me came a third time, He stuck his cock all the way in as I came. I realized I was pushing my feet into his chest until I climaxed.

I could feel his cock get extra hard and kind of a small pulsing feeling when he's about to cum. "Can I cum in your ass?" He asked as he was working me harder, I nodded while moaning. He put his cock all the way in me and could feel it throb, pumping cum in me. He moaned and tried to stay upright, I could hear his knees hit the wall of the bed. He gently pulled out and laid beside me, stroking my hair back. His cum inside me made it feel like I had to go to the bathroom urgently but it wasn't unpleasant feeling. I went to the bathroom to clean up and he went in after asking me if everything was okay and nothing was hurting.

We laid together for the rest of the afternoon enjoying the breeze coming through the top hatch, hearing seagulls, and lines clacking against other boats' masts.