Story time!
Today, my boy came over with the intention of tending to me because I had a very difficult calculus exam this morning. He and I played around for a little while, but for some reason, I wanted to take care of him, not the other way around. I left him sitting in the little room off of mine, and returned a moment later with something behind my back. I stood behind him and held out a pair of frilly pink panties in front of him (I have multiple pairs of those 😃 )
"Do you recognize these?"
"...no."
"You don't?"
"No. Are they yours?"
"Close," I said, as I ran them around his back and neck.
"What do you mean?"
"Well, I bought them, but they're not for me."
"Who are they for?"
"You. Now what do you say when someone gives you a gift?" I demand angrily, as I pull his hair.
“Th-thank you.”
“Very good, sweetheart. Now don’t you want to try them on?”
“…no.”
“Too bad. Get up. Drop your pants, and your shorts too.” As he lowered his shorts, I burst out laughing. (He’s not actually small; I just wanted to hurt his dignity.)
I knelt down and asked him to pick up one foot at a time so I could get the panties on him. I slid them slowly up his legs and stretched them over his excited member. I then retrieved my hairbrush and started brushing his hair very slowly. “Do you know what this is for, pumpkin?”
“…brushing hair?”
“Yes, but it also serves another purpose. I love when things are versatile, don’t you?”
“Yes,” he said uneasily. I caressed his ass with the back of my brush and enjoyed hearing him whimper. I wound up and spanked him as hard as I could, and he let out a pathetic little yelp. “Okay. You have two options: I give you ten swats and you get one treat. I give you twenty and you get two. What do you want?”
“T-two.”
“Are you sure, honey? That’s twice as many spankings!”
“Yes, I know. I deserve it,” he said, ashamed.
His willing reply surprised the hell out of me, but I’ll take it. I spanked him hard ten times and said, “You’re at ten now. You can quit if you want. Do you still want ten more?” He nodded and repeated several times that he deserved it. With that, I spanked him ten more times. His ass was bright red and covered in rectangular marks. By then, he was trying desperately not to cry. I didn’t want to deal with any sniveling sissies, so to get him to stop crying, I shoved a pacifier in his mouth. I handed him my silly pink shorts with white polka dots (that have been featured in another story) and told him to put them on. I was pretty annoyed because he looks better in them than I do.
I led him on weak legs over to my bed and gently laid him down. “Good job, honey. Your spanking is all over, and I won’t spank you again unless you piss me off. Now I want you to just keep sucking on your binky and I’ll go get your treat.”
I went downstairs to prepare a quick treat for him, and I also grabbed a pink Hello Kitty sheet. I returned to him and unfolded the sheet and said, “Okay, sweetie. It’s too hot for a blanket, but I think you’ll feel better if you have something over you.” With some maneuvering, I got the sheet over him and he clung to it like a little boy.. or a little sissy. Whatever. I then took his treat (chocolate milk) and put it in a sippy cup. I sat down next to him, removed his pacifier, and handed him the cup. He started sucking on it right away and didn’t stop until he was finished.
After commending him for being such a good little sissy bitch and drinking his milk all gone, I said that it was time for his second treat. I took the sheet and pulled it over his head temporarily so I could prepare. When I removed the sheet, he was faced with my bare chest. I sat him up a little bit and told him to suck, which he did. Feeling his tongue all around my bare nipple felt pretty awesome.
After a few minutes, I gave him his binky back and cuddled him. I said, “Now, honey. You’re very lucky. A lot of sissies don’t have someone to look after them, but you do. I think it’s very important for sissies to be looked after because they can’t help themselves. I think that sissies should always wear proper attire and be kept extremely sexually frustrated so they’re always suffering slightly. It reminds them of their station and that they will rarely, if ever, feel the pleasure that other people do. In my opinion, sissies don’t deserve sexuality and all the wonderful feelings it brings.” (This is not my opinion at all—it’s just part of the role play.)
“Yes, Mommy,” he said, meekly.
“There you go, pumpkin. I can’t wait to start treating you like even more of a little bitch soon.”
“What do you mean?”
“Well I think that in the near future, I’m going to make you wear really girly babyish clothes, makeup and nail polish, and play with dolls, and of course, you’ll be wearing diapers very soon.”
“Why?”
“Honey, you can never trust a sissy. I need to know that you won’t be wetting your pants, or more accurately, your cute little frilly panties, all the time.” I then got out of bed and rummaged through my laundry basket filled with clothes that I was too lazy to put away. I found my frilliest pair of pale pink panties with two bows on the front and soft white lace around the leg openings. “I think that until I can buy you some proper sissy plastic panties, you’ll just wear these over your thick diapers.” I said this slowly and sensually, and I could feel him squirming. “When people look at you and see this poking out from your dress or skirt, do you know what they’re going to think? They’re going to look at those panties and think about what a little bitch you are. And then they’re going to look a little closer and see that these panties are bulging, and you’re actually wearing bulky diapers. Then not only will you be a little bitch, but a sniveling, panty-wetting little baby.”
I knew that my mean monologue wasn’t going to upset him. He was rather intrigued by the whole idea and remained excited for a decent amount of time. After I was done berating him for something that didn’t even happen (yet), I cuddled him and ran my fingers through his hair. Unfortunately, just as both of us were starting to relax, he had to leave. I asked him to get dressed, but still leave his binky in, which he did. What a well-behaved lad!