Diaper Sissy Play: Training His Ass and Dressing Him Up

A little adult diaper sissy play for my sub!

Diaper sissy play is always so fun to torment my submissive boyfriend with! He LOVES wearing a diaper and dressing up like a cute sissy for me. So it’s a two-for-one whenever I get to doll him up and make him play along and be a good boy. Most of the time, though, he doesn’t want to be a boy at all. He loves when I give him the cute pink diapers with princesses and sparkles printed on them. And he absolutely loves when I put some bubblegum pink lipgloss on him. My little pet was born to be a sissy! So I even gave him a brand new name: Brittany. As soon as I say that, it’s showtime—he’s ready to be a good girl for me!

My sissy loves all the frills, bells, and whistles of diaper sissy play. So when it’s time to dress him up, I always go all out. It starts by having him strip down and take off all his ‘man’ clothes, all his adult clothes. They go right into the hamper, not to be seen again for the night. He lays back on the bed for me, and the process begins. “Aw, you’re being such a good little sissy for me, Brittany! Let’s get you a new diapy…” I coo, baby-talking my little sissy as I set him up with a diaper from his favorite set. Diaper sissy play gets him so excited that his little clitty perks up before I even get him dressed!

He gets so excited about his diaper.

A little sprinkle of baby powder and ta-da! I pull those tabs and attach the fresh new diaper. My little sissy is excited right off the bat, and he can’t help but wiggle around. His clitty makes a bump in the diaper, and I can’t help but giggle, knowing how he will cream those diapers in a second! The next round of our diaper sissy play is the makeup. I apply a little bit of that sexy, bubblegum pink lip-gloss. She pops her lips like a prima-donna to show off the cute new look. And sometimes, I even get her a sexy blonde wig with pigtails to really complete to look.

After that, I have to let out my rough side! My mean side comes out to play. First, I gave my sissy a little pink pacifier to suck on, what he calls his ‘baba.’ He sucks on it for a little bit, but then he knows it’s time to upgrade to the big toys! I whip out a nice, thick, pink strap-on as I go full-Mistress mode. I pull that on and harness it, bringing it to his lips. My sissy happily obliges, dropping the baba to suck on the head of that lovely pink sex toy. The diaper sissy play continues, and he knows what’s coming next! The wetter and sloppier that he gets that strap-on, the easier it’ll be to fuck him.

Diaper sissy play has him craving a good fuck!

After sucking on my toy to get it nice and juicy, he can’t wait any longer. So I baby-talk my little sissy and have him turn around. Brittany plays along, being such a good sissy girl for me! He turns right around, and I pull that diaper to the side. The diaper sissy play gets really fun here. My sissy gets to enjoy every bit of the bouncy, cushiony diaper as I finally slide my strap-on cock into her ass. Inch by inch, she stretches around that thick cock and moans for me. What a good sissy! She starts begging for more, bouncing her little ass back against me.

And I love giving her every inch of my toy, too. She got it so wet and juicy with her lip-gloss and saliva that I can now pound her tight ass mercilessly. And I even reach around and give Brittany her ‘baba’ back, so she gets to suck on something while getting fucked. Aren’t I such a kind Mistress? She loves the diaper sissy play so much that she always ends up creaming her diaper! And sometimes, I’ll even make her wear it for the rest of the day: a diaper filled with cum, and a sore little ass from such a hard fuck! Would you like to wear a diaper for me? Call me, let me dress you up too, honey.

Call Kali 1-888-317-3123