A friend asked me to help with a BDSM scene. A long-time associate of hers, Jimmy, enjoyed wearing diapers, liked humiliation, anal penetration, and age play. My friend would take the role of “Mommy,” but she needed someone to be the big sister. Since I had the schoolgirl skirt and Mary Janes, I figured why the hell not? The idea of being someone’s kinky fairy godmother and making their fantasy come true appealed to me, even if I was slightly nervous about what that would entail exactly.
I wore my short plaid skirt, ruffled white shirt, and pulled my hair into pigtails. I grabbed a long coat that hid my costume so I wouldn’t alarm the neighbors, and I set out for Mommy’s play space. I always get a case of the butterflies before a scene, even when I’m not the focus of the action, and I wondered what Jimmy would be like. I didn’t have much experience with age play outside of my own D/s relationship, and I worried that I wouldn’t know how to play “correctly,” as if there even was such a thing.
The stereotype of Dominant women was that they wore latex or black leather all the time, and strode around in heels with a whip in hand. I had never seen my friend wearing any of that, and when I arrived, she was dressed in black skinny jeans, a scarlet red top, and heels. She didn’t need head-to-toe leather to appear dominant. It was in the way she moved, her energy, and the instructions she gave me. She assured me that I’d be fine and should follow her lead. I nodded and crossed my fingers that she would be right.
Jimmy was a man in his fifties with graying hair and casual clothes. He was shorter than me with a compact frame and quiet disposition. He smiled at me like we were meeting for the first time at a coffee shop and not in a room with multi-colored sex toys and large bottles of lube residing along one wall. He shook my hand and didn’t appear nervous at all when Mommy introduced me as Heather, his big sister. She then turned to me to explain that Jimmy was my new adopted baby brother. I smiled at him and welcomed him to our happy family, and then Mommy got down to the business of taking care of baby.
Mommy told him to take his clothes off, and then we all traipsed to the bathroom so that he could “get clean.” I twirled my hair and lounged against the door frame as Mommy cleaned Jimmy’s penis and balls with wet wipes. She explained to me that dirty boys needed to be cleaned, especially naughty boys who liked to play with themselves. Mommy asked him if he had saved himself for her, and he nodded. Then she snapped her latex glove and told him to bend over, so she could inspect her efforts. Jimmy obligingly parted his ass cheeks, and Mommy stuck a finger into his anus. He gave a soft moan as she slowly moved in and out of the tight hole. I watched his cock harden with her attentions, and she gave Jimmy permission to stroke himself.
My posture may have been casual, but I found their interactions fascinating. It was the first time that I’d participated in a scene with a male submissive where I could observe and absorb the dynamic. Usually I was the receiver of the dominance and sadism, but in this particular situation, I had a front row seat.
“You’re not allowed to come,” she warned him. “If you come close to orgasm before I give you permission, you may beg me for mercy.”
“Yes, Mommy,” he replied in a breathless voice.
With the inspection finished, Mommy withdrew her finger and tossed her gloves into the trash. “Let’s get you into your diaper, baby.”
We walked back into the other room, and Mommy laid out all the items she would need for Jimmy’s change. Talcum powder and a large adult-sized diaper with blue sail boats sat beside the massage table. She instructed him to lie down with his bottom on the diaper and his legs spread, and then she turned to me. My task was to sit between his legs and powder him. I nervously grabbed the baby powder and eyed Jimmy’s penis. In retrospect I should have focused more on the sensual feeling of powder on skin, but all I could think about was making the powder go where I wanted. I squeezed too hard, and a giant plume of white powder puffed into the air. I suddenly got a case of the giggles.
Mommy made clucking noises with her tongue and shooed me off the table. She neatly fastened Jimmy’s diaper. Then she handed me a coloring book and crayons.
“You two can color, while I get a few things from downstairs. Look after your brother, Heather, and be a good girl.”
“Yes, Mommy,” I said and put the coloring book on the floor. “We can color here, Jimmy.”
We shared the crayons and began coloring a Ninja Turtle. Spread out on our stomachs with our legs in the air, I felt exactly like the little girl I was supposed to be playing.
“You’re pretty,” Jimmy said.
“Thanks, little brother.” I could feel a slow grin tug at my lips, a plan forming in my mind. “So tell me, Jimmy, are you a good boy or a bad boy?
Jimmy heaved a loud sigh and furiously colored a turtle’s mask orange. “I try to be good, but I always seem to get into trouble somehow. How about you, Heather? Are you a good girl?”
“Oh Jimmy, I am most definitely not a good girl.” And to prove my point, I broke my purple crayon in half and threw it across the room.
Jimmy gasped, so I did it again. This time with a green crayon. “Let’s see if Mommy notices.”
There was the click of the doorknob turning, and the door swung open. Part of me felt very naughty, and I couldn’t look up to meet Mommy’s eyes. I watched her heels cross the carpet, a flush stealing over my cheeks.
“Have you two been good?” she asked.
“Mommy, Heather broke two crayons!” Jimmy yelled.
I had marked Jimmy as a goody-two-shoes from the beginning, and he had played his part perfectly. It took all my control not to burst into giggles again. Mommy frowned at me.
“Heather, that is very bad. I’m going to have to punish you.”
I tried to stifle my grin. “Oh no, Mommy. That would be terrible.”
She shook her head at my obvious glee and motioned for Jimmy to get back up on the table. “I’m going to spank Heather, and since you’ve been a good boy, you may pleasure yourself while you watch.”
As Jimmy settled himself, she unfastened his diaper and handed him a Hitachi. She warned him again that he had to announce if he was close to orgasm. The Hitachi buzzed to life, and Mommy pulled me over to a bench against the wall. I went over her lap, my ass sticking prominently into the air. With a few tugs, she had my white cotton panties around my knees, and I felt the first sting of her palm on my buttocks.
I adored a good spanking, and I hadn’t had one for a long time. Mommy found a rhythm, and I closed my eyes to relish the feeling of stimulation and helplessness. Her fingers landed tantalizingly close to my pussy, and it was no stretch for my imagination to envision something even more personal happening. She switched to a closed fist when her hand tired, and the firm impact of her fist on the meat of my ass pushed me even closer to orgasm.
“I think she’s enjoying her punishment a lot, Mommy,” Jimmy commented.
“I think so too, baby, and your sister has such a nice ass to punish.”
I squirmed on her lap and looked over to see Jimmy fully erect as he smoothed the Hitachi along the length of his shaft.
“Let’s switch,” Mommy said and helped me stand up. Then it was Jimmy’s turn to receive Mommy’s attention, and she made him lie down on a medical pad she had spread on the floor. His diaper was discarded, and Mommy donned another pair of latex gloves.
“Stand over his head, Heather, and let him see you.”
I blushed and did as I was told, gratified when I heard Jimmy’s breathing increase. Mommy lubed up her fingers and pushed two into his anus as she worked the Hitachi up and down his cock. The effect was immediate, and Jimmy moaned his pleasure. I let one of my fingers skim the edge of my short skirt to find the thicket of hair at the junction of my thighs. I didn’t have to see his face below to know that Jimmy was watching.
“See, little brother? I love being naughty,” I murmured, stroking my labia with a finger.
Jimmy writhed against the floor, breathing hard. “I’m close, Mommy!”
“Good baby. Good Jimmy. Come for Mommy.”
And he did.
