Ask for it!

Once a week Mommy spanked her boy. After taking his morning shower the boy put on a pair of sheer string bikini briefs. Wearing the sheer briefs reminded him the hard spanking Mommy would give him.

Although he was always punished on spanking day, the time depended on Mommy's "to do" list. Usually it was an item on the mental list of things she needed to do, but if it was a particularly busy day, she would write the list down. On those days the boy would apprehensively watch her check items off the list until she came to "administer spanking".

They had been out shopping earlier that day. After Mommy had put things away she told him to go to his room and get ready for his spanking.

"I'll be up in a little while and I want you to think about how naughty you've been this week while you're waiting for me." Mommy told him.

He went up stairs to his room and undressed, leaving on the sheer string bikini briefs.

After laying out the ruler paddle and the rattan cane, he piled two pillows in the middle of the bed.

The boy hated having to wait for his spanking, looking at the paddle and the cane, thinking about how much they would hurt when Mommy used them to punish his bare bottom.

The boy felt relieved when Mommy finally came into the room, glad that he could stop dreading his punishment and get it over with. Or he felt that way until Mommy put him over her knee for his paddling, his briefs pulled down to his knees.

Mommy paddled the boy's bare bottom with the ruler paddle bringing it down hard across his buttocks until his bottom was red and each stroke made the boy cry out.

When Mommy finished paddling him, she told the boy to get up and lie over the pillows. The boy's briefs had worked their way down to his ankles as he kicked his legs while she paddled him and he stepped out of them, putting them on the night stand. He lay across the pillows, his bottom pushed up, presented for the cane.

Mommy tapped his bottom with the cane and the boy arched his bottom up, offering the lower part of his buttocks for punishment. She gave him a few soft strokes making him wait a moment for the first stroke, which burned across his buttocks. She gave the cane strokes hard, using the full swing of her arm, waiting four or five seconds between strokes to allow the boy to feel each one.

Mommy laid the cane strokes hard across the boy's bottom and upper thighs. He was crying like a spanked little boy when she finished giving him the first set of fifteen strokes, switching sides to administer another fifteen so that his buttocks and upper thighs would be punished evenly.

"I'm going to give you the last ten extra hard. Get you bottom up for me, honey", she ordered the crying boy.

He arched his back, pushing his bottom up. Mommy laid the cane lightly across his offered buttocks twice before whipping the cane down hard across his cheeks. She gave the strokes slowly and, as she promised, very hard, allowing each cane welt to bloom across his buttocks before giving him the next stroke. The boy tried to keep his bottom up and presented for punishment, but a few times he pressed into the pillows when the cane welted his bare cheeks. Then Mommy would wait for him to arch and offer his buttocks before giving him the next stroke.

The boy was sobbing when she gave him the last stroke, the welt rising across his buttocks, just above his thighs. His bottom remained arched, presented for another stroke.

Mommy put the cane down and caressed the boy's welted bottom. "Your caning is over, honey."

Mommy lay down next to him, taking the crying boy in her arms, cradling his head against her breasts, stroking his hair. She held him until he stopped crying.

"I'm going paddle you now, darling", she told the boy. He pressed his face into her breasts. The caning had been very painful and he dreaded getting paddled over the cane welts.

Mommy got up and went to the dresser and took out the punishment paddle. The boy got up and went to stand on her right side. He could see the tops of her breasts, bared by her low cut blouse. He wished that he could nuzzle them again, burying his face in her cleavage.

"Over my knee, honey" Mommy told him, as she hiked up her skirt, exposing her thighs. He could see that she was wearing sheer black panties. The boy lay across her left knee, his feet braced against the floor, his upper body supported by the bed.

Mommy caressed his bottom, running her hand over the hot skin, trailing her fingers over the red lines of the cane welts that covered his buttocks and upper thighs.

Her hand felt cool on his hot punished skin as she caressed him. The boy's bottom was very sore and he knew that the pleasure of Mommy's caresses would soon be replaced by the smack of the paddle on his welted buttocks.

Mommy picked up the punishment paddle, wrapping her left arm firmly around his waist. She brought the paddle down hard on his left buttock, alternating cheeks as she spanked him and he cried out with each stroke. After giving him ten strokes on each cheek Mommy gave him a chance to catch his breath as she caressed him. After a few minutes the crack of the paddle and his cries were again filling the room. After giving him another ten strokes on each side she put the paddle down.

Mommy let go of the boy and told him that he could get up. She took the pillows from the middle of the bed and placed them on the end of the bed.

"Bend over the end of the bed please, darling", she ordered.

When the boy was bent over the end of the bed, Mommy replaced the punishment paddle in the dresser and took out a whip, a dildo, a dildo harness and a bottle of lube. After placing the items on the bed, she undressed to her bra and panties.

She sat down next to the boy and caressed his bottom, running her index finger between his cheeks. "Whose bottom is this?", she asked him.

"It's yours, Mommy" he told her.

"That's right honey. You're mine. I want you to ask Mommy to give you a good hard ass fucking to finish your punishment"

"No, please don't make me ask for it Mommy."

"OK darling, I'll give you a choice. You can take forty lashes across your bottom with the spanking whip or you can ask me to fuck you hard in the ass".

The boy looked over at the dildo lying on the bed. Mommy had laid out the punishment dildo. He knew that it would hurt when she first penetrated him.

"I'll take my whipping", the boy said softly.

Mommy picked up the single tailed spanking whip and moved behind him. She let the braided black lash trail across his cheeks. He pushed his bottom up.

"I'll give your punishment in sets of ten, my love", Mommy told him. "After each set I'll give you a chance to ask me to fuck you in the ass before I give you the next ten.

Mommy brought the whip down hard across the boy's ass. He was crying again as she gave him the first ten strokes.

"Is there something that you want to ask me for, honey?", Mommy asked the crying boy.

"Please whip me, Ma'am", the boy replied softly.

Mommy gave the boy another ten lashes. Between sobs he asked her to whip him when she asked again.

As Mommy brought the lash of the spanking whip down across the boy's buttocks he sobbed and begged her to stop spanking him, promising to be a good boy if only she would stop.

When she finished giving the boy his third set of lashes, he lay limp over the bed sobbing.

"Now is there something that you want to ask me for, darling?", Mommy asked. "Do you want to ask me to whip you?"

"Please don't whip me, Mommy. I'll be a good boy", he said as he cried.

"If you don't want me give you a whipping, you know what you have to ask for", Mommy said.

"Please don't whip me Mommy. I can't take any more", the boy repeated. Then more softly "Please give me a hard fucking in my ass".

She patted his bottom. "Good boy. Now I want you to spread your cheeks for me", she told him.

The boy reached back and spread his buttocks. His bottom was very sore and hot under had hands.

While he waited, bent over the end of the bed, his cheeks spread and his anus exposed, he watched as Mommy slipped her panties off. She put on the dildo harness and put in the dildo. As he watched her get ready, he thought about how she would soon be giving him a punishment fucking in his ass. The dildo looked very thick. But it would be better to take the pain of penetration with the punishment dildo than another ten lashes with the spanking whip across his bottom.

She moved behind him and he heard the squish of lube as she prepared the punishment dildo. She pressed the tip of the dildo against his anus. The dildo hurt as she pressed into him.

"Relax, honey, and take your punishment", Mommy told him as she pressed the tip of the dildo into his anus.

"It hurts, Mommy. It's too big"

"Relax and take your fucking, darling. Or I will have to whip you"

The boy concentrated on relaxing his sphincter, pressing out as she pressed the dildo into him. He cried out as she penetrated him, pushing the dildo all the way inside him.

The boy moved his hands forward, gripping the bed spread, bracing himself as she started to move against him, thrusting hard, slamming into his sore bottom. She came as she fucked him, the dildo pressing against her clit.

September, 2004

Case Wintermute