When Kyle first started asking me to peg him I didn’t take it seriously. I didn’t know if he was even serious and he had never shown any interest before.
When we first met I thought that he was just a cute guy that loved vanilla sex and I couldn’t imagine that he would ask me for anything like pegging. Unlike him, I had an experience like this before and wasn’t afraid to talk to him about it.
He seemed very curious and was showing a lot of interest when I told him about the things I did with my exes. I didn’t pressure him into anything, of course, I didn’t even ask if he wanted to try, but Kyle brought it up himself.
It happened when he was helping me pack my things when I was moving into his place. I was pulling out things from the closet and he found a box. I didn’t really think that he would look inside, but when he did he saw all the toys I used on my previous boyfriends. There were straps, butt plugs, anal beads – all of the good stuff. I saw his eyes go wide when he looked inside and thought he’d be disgusted by it, but instead, I saw his cheeks going bright red.
“What? Do you want to have a ride?” I laughed. He didn’t laugh back.
“Well, it could be interesting,” he said, looking shy.
“Are you sure? Because if you are, your ass better be ready for something like this,” I pulled out a strap-on from the box. It was thick and black, the biggest toy I owned. I moved it closer to Kyle’s face but, instead of moving away, he just swallowed hard.
“Will you do it?” he asked, looking at me and I knew at that moment how much he wanted it. He wanted me to take him and to use his ass. Well, he wasn’t as vanilla as I thought after all.
He would ask me once in a while if I was still thinking about it and if I was trying to change the subject whenever he brought it up but in reality, I have already decided that it was going to happen, but I wanted it to be a surprise.
One evening I was waiting for him at home, dressed in sexy black underwear and prepared to make his ass mine. I lined up all the toys I was preparing to use on him and sat on the bed, waiting for Kyle to arrive. I could hear the door open and him walking in. He called out for me, but I didn’t answer. When he walked inside the bedroom looking for me, his eyes went wide. He became even more surprised when he saw all the toys that I got ready for him.
“Is this what I think it is?” he asked, looking at them and then at me.
“It’s me telling you that your ass is going to be mine tonight. Are you ready for it?”
I got up, walking closer to him. I was ready to show him how dominant I can be. I looked him in the eyes and put my hand on the front of his pants, feeling his cock. He groaned, looking at me with desire and I knew that he was ready.
“Do you really want it? Do you want me to own your ass?” I asked, groping him harder.
“Yes, yes I do,” he nodded, looking a little nervous. I liked it a lot.
“Let’s get you undressed then”
I started taking his clothes off slowly, seeing how much Kyle was enjoying it. When he took off his underwear I could see that he was already getting hard. He didn’t know that it was only just the beginning for him and that soon he was going to be overwhelmed with desire.
“Get on the bed and get on your hands and knees,” I commanded him, standing at the foot of the bed. Before doing anything to him, I wanted to see how willing Kyle would be to go along with my commands. He took the position I told him to, perking his ass up and spreading his legs just a little.
“Good. Now take that bottle of lube and start fingering your asshole”
He looked back at me, unsure, but still followed my commands. I saw him taking the lube and putting some straight on his asshole. I could tell that he wasn’t used to being in this position once he laid his head on the pillow, and used one hand to spread his cheeks, and the other to push a finger in his asshole. I came closer, caressing his back, as I watched him lubing himself up. His finger was thrusting in and out of his tight ass, while he was whimpering and moaning.
“Come on, go harder,” I said, grabbing his hand and making him push the finger in deeper. “Yes, that’s right”
I took one of the smaller toys I had and pulled his hand away from his ass, instantly pushing it inside. Kyle moaned harder, feeling me fucking him slowly.
“Feels good, doesn’t it?” I asked with a smile.
“Yes,” he answered, sounding breathless.
I smacked his ass while pushing the toy deeper, seeing him enjoy it. I took his cock in my hand, stroking him slowly. Maybe he was ready for something bigger.
“Want this inside?” I asked, dangling the anal beads I had next to his face. “They’re going to stretch your ass so nicely”
“Do it. Use my ass any way you like,” he moaned again. I liked his obedience, it was turning me on.
I started slowly pushing beads inside of his tight ass, one by one, hearing Kyle whimper. He was taking it well, even though his asshole wasn’t trained for it. Once they all were inside, I started pulling them out, making him moan harder.
“You like it? When your ass is stuffed and fucked hard?” I asked with a laugh, smacking him again.
“Yes, yes,” he said, shaking. “Fuck me, please”
I smiled. I couldn’t even imagine that he would be so ready for it, that he would offer me his ass so willingly. I started to think that me taking his ass today would be just the first time of many.
“I think you’re ready for something bigger. Go and lay on your back”
While Kyle was changing his position, I went to put on a harness and adjust the strap. It wasn’t the biggest one I owned, but it was big and slick, enough to satisfy him for now.
He was looking at me, holding his legs, as I stood close to him, with the tip of the strap almost touching his asshole. I put lube on the length of the strap to make it easier for him. I smiled, looking Kyle in the eyes, as I started slowly pushing deep inside him. He was groaning and whimpering, while I was pushing deeper inside him. He was taking it well, and I was able to get halfway inside him before I started fucking him fast and rough. I put my hand on his cock as I did it, stroking him.
He looked at me with desire, his body was covered in sweat, while I was taking him faster and faster. My strap was going inside him deeper and deeper until it was fully in. He whimpered again, louder, and spilled on his stomach. He was breathing hard and I knew that I had just changed his life.
“Did you like it?” I asked him.
“Yes, I loved it,” he nodded.
“Good, because we’re going to do it much more often now because your ass is now mine”, I said smiling wickedly.
