I love making him my little bitch.
Strap-on pegging was filling my boyfriend’s porn history to the brim. I remember when most of it was regular POV porn or even breeding whore kinks, but that slowly whittled away. The last time I stumbled across his porn searches, all I found was sissy play, pegging, or strap-on play. And honestly? It was exciting! It was fun to discover his never-ending streak of curiosity. Even I’m like that sometimes — I start off with a favorite, but end up far down the rabbit hole looking at something I’ve never heard of before. But this time I knew he was into it much more than that, it wasn’t the “flavor of the day,” it was a month’s worth of porn!
So I decided to try bringing it into our sex life. I always love teasing him with all his little curiosities and kinks. Sometimes, he’s intimidated by the thought of asking for it. I guess he didn’t want to be labeled as a sissy or a little sissy bitch, even though he loves it all in our kinky roleplay sessions. But I noticed some of my favorite little lacy panties had gone missing. And where did I find them? In his hamper, waiting his next wash day for when he could sneakily return them to my apartment. Sneaky little sissy. I was going to love exploring this strap-on pegging kink he had. So the first thing I did was to run off and buy a few toys for us to enjoy: a good lube, a series of butt plug sizes, and a big, vibrating strap-on. For the panties and sissy play, I’d let him keep using mine.
I didn’t know he’d love strap-on pegging so much!
But once I had all the toys, it was showtime. I even sent him a picture of my newest lacy pink panty. He texted about how hot it was, but I knew what he was thinking. He was daydreaming about how it might feel to wear it, and what a cute sissy he’d look like. So when he came over that night, that’s the first thing I did. “I bought it for you.” First, he looked bewildered, grinning, and confused about why I was saying this. “I know you’re a little sissy, and I’ve seen your strap-on pegging porn…it’s okay to admit it. Try these on.” He continued looking at me like a deer in headlights, rapidly blushing. But curiosity won him over, and he took the panties from me. “Are you serious?” he asked, and that’s when I showed him the little bag from the sex store.
“Mhmm… and I bought a few things for us to play with too. After you put those on. So, put them on, sissy.” I ordered him around and he swiftly got with the program. My new sissy pet stripped down eagerly, leaving all his regular clothes neatly on the chair. And then he cautiously took those lacy pink panties and slid them on. It was everything he had dreamed about from his kinky roleplay videos. I watched and giggled, and told him he was such a sexy little sissy bitch. Now it was time for the good stuff! I poured out the little bag of toys onto the bed. He looked over the butt plugs, but I knew what his favorite was. He was looking forward to that strap-on pegging and he couldn’t take his eyes off the big dildo I’d bought for him.
Strap-on pegging made him cum so much!
I made him spread his cheeks and put his little pink panty aside. First, we played with the butt plugs. It was such a fun little treat to have his girlfriend play with his ass… I didn’t know he’d love it so much, but his little sissy clit was excited even without me touching it. In fact, all I did was peg his ass with my butt plugs first! But once that tight little ass was stretched and relaxed enough, it was time for the real strap-on pegging. First, I had him lay on his back for it. It added to the immersive experience as hel looked up at me, with his cute little lacy pink panties on and pulled to the side. His legs were up and he was playing with himself as I lubed up that strap-on head and rubbed it against him.
And then I slowly worked it in. Inch by inch, my big cock slowly disappeared into his ass. He let out a gasp as the head rubbed past his prostate, his secret little g-spot that he’d been playing with for months. I started sliding it in and out of him, working the strap-on pegging into a little prostate massage too. His legs started shaking as he was cumming for me, but it was far from over. In fact, I was about to flip him over and fuck him doggy style too! My little sissy was not going to tap out after just one fuck!
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