A drawing by the wonderful
Daniel was kneeling on a leather ottoman, that was pushed up against the end of his bed. He was bent over the end of the bed, with a pillow under his hips. Except for a pair of silk bikini briefs, streched tight over his upraised buttocks, he was naked. A rattan spanking cane, a paddle and a wooden bath brush lay on the bed next to him. Daniel knew that in the bedroom next door his sister Ann was also bent over her bed, wearing only panties, lying next to the same implements. Ann and Daniel were waiting for their Nanny to come upstairs and punish them.
Daniel was sixteen and Ann was a year younger. They had both gotten into a lot of trouble earlier that day. Nanny had told them that they were both going to be spanked, but she did not send them to their rooms for punishment then. They spent the rest of the day dreading their promised spanking.
"Do you think that Nanny will whip us", Ann asked Daniel in a whisper. "I hate it when she whips me. I'd rather have twice the number of strokes with the cane."
"Well, we're probaly going to get the cane too" Daniel said glumly.
Daniel knew that Ann had recently become more familiar with Nanny's riding whip that she might have wished. Ann was going through a rebellious phase. Most of that rebellion ended up being directed at Nanny, as their surrogate mother. In the last few months it seemed that almost every week Ann pushed Nanny too far and Daniel heard Ann crying in the next room as Nanny whipped her, bent over the end of the bed, her panties pulled down to her knees.
As bedtime approached they remained unpunished, silently hoping that Nanny had somehow forgotten about the spanking they had coming, although such a miraculous event had never happened before. They were trying to study in the library when Nanny come in and told them it was time for bed. As they left the room she added "Please get ready to take your spankings as well".
The walk upstairs felt especially long as they thought about their upcoming punishment. Ann and Daniel took turns in their shared bathroom. Getting ready for a spanking meant laying out the cane, paddle and bath brush, undressing to their underpants and getting into position over the end of the bed. The doors to their rooms was left open. Nanny had not spanked Daniel and Ann in the same room since they were ten, but she insisted on leaving their bedroom doors open.
Bent over the end of the bed with his hips pushed up by the pillow, his bottom protected only by his thin briefs, it was hard for Daniel to think about anything else but the spanking he had coming. Finally he heard Nanny's heels on the wooden stairs. Since Ann was younger and a girl, Nanny always spanked her first. Listening while Nanny spanked Ann, while he was bent over the end of the bed awaiting his turn seemed like getting two spankings.
Daniel heard Nanny go into Ann's room.
"I'm sorry I was a bad girl, Nanny. I'll never do it again. Please don't spank me" Ann pleaded, although they both knew that once Nanny had decided that a spanking was needed, nothing short of ironclad proof of innocence would sway her from administering punishment.
"I know you're sorry, honey. But I also know that you need a good hard spanking." Nanny told her.
"Please don't whip me, Nanny. I'll learn my lesson if you cane me, but please don't whip me."
Daniel knew then that Nanny must have been carrying the black riding whip that she used to spank them when they were especially naughty.
"Shhhh. No more of that honey. It's time for you to take your spanking."
In Daniel's mind's eye he imagined that he saw Nanny go over to the bed and exchange the whip she was carrying for the rattan spanking cane. He imagined that she would be standing to Ann's left side, as she lectured Ann in a calm tone, reminding her of the reasons she was going to get a spanking. Ann would be wearing only a pair of silk string bikini panties. Her panties would feel very thin as Nanny tapped her across the bottom with the cane, reminding her of what a bad girl she had been. Daniel heard the swish of the cane, followed by Ann's cry as Nanny gave her the first stroke. His buttocks clenched unconciously as he listened to Ann crying out after each stroke. After he had counted out twenty strokes, Nanny ordered Ann to pull her panties down. He imagined Ann reaching behind her and slipping her panties down to the middle of her thighs.
Daniel had never seen his sister naked, but he had seen pictures of naked girls in magazines. His favorites were poses where they were bent over, as if they were waiting to be spanked. Rather than his sister, Daniel imagined one of these pin-up girls, her panties around her knees, her shaved vulva showing between her thighs, her bottom pink, feint lines across her cheeks from the caning over her panties.
His cock grew hard as he listened to Ann cry out again as Nanny caned her across her bare bottom. He counted out another twenty strokes. Ann was crying now. When her cries got louder he knew that Nanny was caning her across the tops of her thighs. He knew how much the cane burned across the tender skin of the thighs.
There was a break as Nanny let Ann rest, Nanny's calm voice lecturing again, Ann's voice answering, promising to be a good girl. Soon Ann was crying again as Nanny continued caning her. Daniel knew that the second part of the caning would mirror the first: the strokes would first be across the bottom, then the thighs. Ann was sobbing by the time Nanny administered another twenty strokes across her bottom and ten across her thighs. Nanny gave Ann another break. Daniel imagined Nanny stroking Ann's hair and her back, Ann's face streaked with tears, as Nanny told her that she loved her and that Ann needed this spanking.
After a few minutes, when Ann had stopped crying, he heard Ann's voice, loud and pleading, "Please Nanny, don't whip me. I'll be a good girl. Please don't whip me." Daniel imagined Nanny standing to Ann's left side, holding the riding whip. As Ann begged Nanny not to whip her, her buttocks would be clenching, as she squirmed and pushing into the mattress, as if somehow she could burrow into it and escape the lash of the whip.
He heard Nanny's voice, also louder. "Get that bottom up, young lady, or I'll have to give you extras". Ann would be resigned now, knowing that no amount of pleading would allow her to escape her whipping. Daniel saw his imaginary magazine girl, her thights slightly spread showing her pussy, arched up and offered her bottom to the riding whip. He heard the smack of the braided leather across Ann's bottom, followed by her cries, which turned to sobs as the whipping continued. Like the caning he knew that Nanny would give the whipping first across her buttocks and then across the thighs. When the whipping was finally over Daniel knew that Ann's bottom and thighs would be crimson and lined with welts.
Daniel heard Nanny's voice, soft, almost crooning to Ann. Nanny always held them, comforting them after the pain of the whipping. After about five minutes her voice sharper and he heard Nanny say "Over my knee, honey".
He imagined Ann, her panties fallen from her knees to the floor, lying naked over Nanny's knee. As Ann lay like a naughty little girl over Nanny's lap, Nanny reminded her again of why she was being punished. Nanny then told her that she would get twenty strokes on each buttock with the paddle and then twenty on each buttock with the bath brush. As she would with a little girl, Nanny would pin Ann's right arm behind her, holding her firmly so she could not squirm out of the way as Nanny paddled her. The paddling had a one-two beat as Nanny spanked first one buttock, then the other. Ann was soon crying again, as Nanny paddled her sore welted bottom.
Nanny let Ann catch her breath, comforting her again. When the paddling started again, the smacks had more of a thud. Daniel knew that Ann was being spanked with the bath brush and that this was the last part of Ann's spanking. This was the part of Nanny's spankings that hurt the most. Where Ann might have struggled as she was spanked with the paddle, Daniel imaged that Ann lay limply over Nanny lap, resigned to her punishment, sobbing and crying out with each stroke.
When the paddling was over Nanny held Ann, crooning, telling her she was a good girl for talking a much needed spanking. Finally Ann stopped crying. Nanny made her bend over the bed again as she had for her caning and whipping. She would have to remain in this position while she listened to Daniel get his spanking.
Then Daniel heard Nanny's heels on the hard wood of the hallway, coming toward his room. When she came into the room the first thing he noticed was the black riding whip in her right hand.