I always liked Jeff’s cute ass. Ever since we started dating I couldn’t take my eyes off of it, it was just so good. No matter what he was wearing, shorts, pants, nothing, I just wanted to touch it and feel it, because it was just so full and looked almost delicious. I would smack him jokingly sometimes, but it wouldn’t go any further, until one time.
We had a silly argument about my clothes. He was trying to make a point that I have too many and I was trying to prove him wrong, so Jeff went through my closet, asking me about the items there. I was laughing along with him, trying to stop him, until I saw Jeff holding up a skirt that I used to wear a long time ago.
“Why do you even have this? It’s huge!” he said, holding it to his chest. “It’s so big I can probably wear it. Hold on, wait a moment!”
Not listening to my protests, Jeff went into the bathroom and closed the door. When he came out I saw him wearing my skirt, which barely covered his plump ass. He took off his pants and I wondered if his underwear was off too. I couldn’t take my eyes off his butt, while he was still laughing at how big the skirt was and that he probably wore it better than me.
Still concentrating on the part of his body that was important to me, I moved closer, put my hand under the fabric, and squeezed him lightly. He looked at me with surprise but didn’t ask me to stop, so I did it again, this time grubbing his plump flesh with both of my hands.
“Do you like my ass this much?” he asked and I could hear that he was a little breathless. Maybe he liked it too.
“Yes, it’s so soft and tempting,” I smiled. I squeezed him again. “I wonder if you’ll let me fuck it one day”
Jeff moved away and I was afraid that he would berate me, saying that this would never happen, but instead, he turned to me, looking shy, his cheeks slightly red.
“Maybe we could try it”
And that’s how our story began. That same night I asked Jeff if he wanted to try it and he agreed. We started slowly, with us just kissing and teasing each other as usual. I let him play with my tits and nipples, while I was stroking his cock but not letting his cum yet. Then I asked him to go on his fours and he did it, looking so shy and vulnerable. I loved it and I wanted to make it feel good for him so he would ask me for more.
I kept slowly stroking him, while I enjoyed the look of his ass, which was about to become mine.
His cheeks were full and I needed his help in spreading them before I saw his tight little asshole. I put my finger against it, massaging it slowly, but not pushing inside. Jeff was moaning and his cock was rock-hard, so I knew he loved it. Once my finger was inside the sound only intensified and I could feel that he would finish soon. I left his cock hanging in the air, while I kept fingering his asshole, feeling how tight it was around my finger, how he was struggling to take it in and yet wanting it.
I finally found the right spot inside him that needed stimulation and soon Jeff was cumming on the sheets without me even touching his cock. He was groaning, saying how good it felt and I knew that it was only the start of what was about to become his ass-training.
After that day I started to introduce the idea of toys to Jeff. At first, he demanded that there would be only my fingers inside him, but soon things changed. His asshole wasn’t as tight anymore after I was loosening it up with my fingers and he needed more, or his orgasms wouldn’t be as amazing as they were.
That was when he agreed to try something else for the first time. I started with small toys and I enjoyed the way they looked going inside his ass that was all lubed and shining. He looked so cute with his cheeks spread wide and moaning, while I had my way with him, I just knew I needed to fuck him and soon.
Slowly, small toys were replaced with anal beads, that would spread his asshole even more. I was starting to try new things too – I was calling him my good girl, a slut, a hole to fuck and use. He seemed to enjoy it, maybe even too much at times and I knew the day was coming when he would allow me to fuck him.
Jeff was the one to buy his first butt plug. He just brought it home one day, asking if I could put it in and I smiled, knowing that I trained that little slut well. I put it in that night, watching how he was fighting overwhelming sensations that were so new to him. When it was fully on, I sucked him off, making it an even better experience. I told him how good he was doing and that I had an even bigger toy for us to use soon.
It was a big night. I wore a harness with a strap attached to it and I knew it was going to be glorious. I was wearing a silky robe and at first, when I first got into bed, Jeff didn’t know what I was hiding, but as soon as we started kissing and he undressed me, I showed him the strap.
He seemed startled at first, too shocked to even say anything and I was afraid he would turn me down, but instead, he got on his fours, showing me his ass once again, and letting me take him.
I started by spanking him, making his ass all red and covered with my palm prints.
He was whimpering as I did it, his cock becoming hard as he knew what was coming. This time I was considerate enough to get lube and I spread it over his asshole and on the strap. I moved the tip of the toy over his entrance, knowing that he was anticipating the feeling of it inside him.
I moved my hips, pushing inside Jeff, hearing him groan as I was deeper and deeper. He was grabbing the sheets, moaning my name and I knew that he loved it. I started moving my hips, looking at him, spread in front of me, so helpless and so plump. His ass was made to be fucked, he was meant to be my bitch and I was just making things right.
I started stroking him, telling Jeff how good he was, how sweet his ass is, how much I loved fucking it, and seeing his tight asshole take the whole length of the strap. He groaned, spilling in my palm, but I kept going. I fucked him hard until he was crying and whimpering, tears streaming down his face from how good it felt.
I moved away, looking at his asshole which was gaping now. It was the most beautiful picture and I knew that we were going to repeat it and very soon.