A strap-on punishment and cuckold pegging.

Cuckold pegging is my favorite punishment to give. My little sissy cuckold started as a very regular fuck buddy. I never thought he’d be into anything of that sort, honestly. After all, the guy was very normal looking and macho. It took me a while to realize that he was actually overcompensating for all his sissy insecurities. Whenever we’d go to the mall, he took me around to all the stores I wanted to go to. I didn’t realize that he was actually guiding me to the stores he wanted to shop at mentally.

He guided me all over the mall at first. We ended up at Victoria’s Secret at one of our first store stops. Can you imagine him trying to act tough, pretending like he wanted to stay outside of the store? He knew that I’d make him come inside the shop with me so that I had more time actually to look around. I also wanted him inside the shop to ask him for his opinion on certain things and tease him with them. I made his jaw drop a few times from the little frilly thongs I would pick out. There was this one thing that had sparkles and crystals on the straps that go over your hips.

I didn’t realize he was dying to wear it himself.

He can get so naughty sometimes. After we actually got home with some of my lingerie, I started noticing that some of it would go missing. I would leave my little thong out on the bed since I planned to wear it out later that night, invite him over, and it would go missing for days. One time, I was going to approach him about it. However, I walked past the bathroom and saw him wearing it and playing with his cock. He wasn’t jerking off, though. He was playing with himself like he would rub his clit if he had one.

I didn’t know he could be so naughty. When I caught him, he instantly confessed everything. He said that he knew when I was going to go out and fuck a different fuckbuddy. After all, we weren’t exclusive. The thought of it excited him. I was so giddy that I didn’t have to keep any of it a secret anymore. It was fun, so I started coming back home after all my dates and telling him all the stories… Honestly, I didn’t realize I was enabling a much naughtier kink in him! I didn’t know he was into cuckold pegging at the time.

It was another dirty little secret.

I really didn’t know he was into anal. One kink came out after the other; I thought he’d even go as far as wearing sissy lingerie. At first, he just wanted me to come back after fucking someone else so that he could taste the creampie. He was such a cuckold submissive slut for me. Then, he wanted to hear the juicy details about the guy that I fucked. The real fantasy didn’t come out until much later. I was re-organizing my room and sorting out some of the lingerie. I’d taken my toys out of the drawer so that I could sort them and put them away in a little container instead. He paused at the door to stare at them, and I thought he was judging me until he spoke up.

He asked about the buttplug specifically at first. I told him it always felt a little fun and naughty to add that one while I played with myself. Immediately after he asked about it, he asked about pegging. Of course, I wasn’t going to use my own toys on him. I wanted to start him off with something smaller. He was still super-greedy, so he wanted to try a bigger toy for his first time doing cuckold pegging. So I ran off to the local sex toy shop to buy him a little something.

His first toy was a smooth dildo.

But I knew he wanted something bigger. So, I added a few more toys to the list. I picked up some juicy, mango-flavored lube, a thicker butt plug, and a nice twelve-inch strap-on, and we were all set to go. I packaged it all in a nice little black velvet bag and saved it for the next time he came over. Of course, he waited until I was done fucking another guy before he stopped by. He’s all about that cuckold phone sex, so he came over to eat me out and hear all the stories. As soon as he walked in, he got his surprise.

I guess he didn’t think I would really go out of my way to get some toys for him. Of course, I did! I love exploring all kinds of kinks, and that one is one of my favorites. He was a little uneasy about it, but I eased him into it. At first, I lubed up the butt plug and let him feel as every inch stretched him out. Slowly, I made his ass all mine. And as soon as he was used to the size, I jumped to the smooth dildo, making sure to stroke his cock a little. I kissed his neck as I let him feel the vibrations move slowly down his body until it was right in position to give him the cuckold pegging of his dreams.

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