A Date with a Riding Crop

When Walter came downstairs on Saturday morning his Nanny, Lisa, was already dressed for horseback riding. She was wearing a pair of tan riding pants, black calf-high boots and a blue pinstripe button-down shirt. Walter was sixteen and he admired the swell of Lisa's breasts under the button-down shirt.

After saying good morning to Lisa, Walter poured himself a cup of coffee from the pot Lisa had made. The newspaper was piled on the table where Lisa had left it and Walter sat down to read. He had finished his coffee and most of the paper when Lisa said "I was very disappointed in you last night. You did not work on your term paper and you lied to me. You told me you were working and I found you playing computer games".

Walter had been hoping that somehow Lisa had suffered a bout of amnesia during the night and had forgotten about this. He considered offering the explanation that he should be excused because he had been playing "Doom 3", a game he had been waiting over a year for. But he correctly guessed that this argument would carry little weight with Lisa.

"I'm sorry, Lisa. I'll finish the paper this weekend", Walter said, attempting to placate her.

"Yes, I expect the paper to be done this weekend. But that does not address the issue of your procrastination and lying to me. Now please go get the ruler paddle".

"Lisa, please..."

"The paddle, young man"

Walter turned and shuffled off to his bedroom. After retrieving the ruler paddle from where it hung at the back of his closet, Walter returned to the kitchen where Lisa was waiting.

"Come with me" she told him.

Lisa was 24 and had been paying her way through graduate school by working as Walter's Nanny for the last two years. Walter's parents traveled frequently and had an active social live. Walter, left largely to his own devices, had been barely passing most of his courses before High School. At the start of Walter's freshman year in High School his parents hired Lisa as his Nanny and tutor.

Everyone who met Lisa commented on how nice she was. At first Walter's parents were not sure they had made the right choice in hiring Lisa to deal with their recalcitrant teenager. Walter rarely managed to get Lisa to show even a sign of irritation and she rarely got angry. Walter quickly developed a crush on Lisa, who he thought was the most beautiful woman he had ever seen. He also rapidly discovered that there was steel beneath her velvet exterior. Lisa would not allow herself to be pushed around and she firmly believed in virtues of corporal punishment, at least in Walter's case. Under Lisa's new regime, the first time Walter neglected to turn in a school assignment he was shocked to find himself across Lisa's knee, crying out in pain as she paddled his bare bottom. The missed assignments rapidly disappeared into the past and Walter's grades improved. Although Lisa's methods did not conform to anything that parenting expert Dr. Spock had written about, they seemed to work with Walter and she had his parents full support.

As Walter followed Lisa into the living room he watching the muscles of her buttocks move beneath her riding pants. He could feel his cock starting to get hard. He tried to look at something else, but his eyes kept being drawn back to Lisa's figure. He loved her narrow waist and the swell of her hips under the skin tight pants. He wondered if she was wearing panties, since all he could see was the smooth curves of her bottom.

Lisa sat down in the middle of one of the couches in the large living room. Walter went to her right side and handed her the paddle. Lisa was tall, only half an inch under six feet and athletic. He knew that when it came to spankings, Lisa was like the Borg on Star Trek: resistance was futile. Walter's pants fell down around his ankles when he undid them. Lisa stopped him as he moved to lie across her lap.

"Panties down too", Lisa ordered

On occasion Lisa would would spank him over his briefs, but this was not one of those occasions. Walter pushed his bikini briefs down to the middle of his thighs. He had to stretch the front on his briefs over his hard cock, which embarrassingly sprung out pointing slightly upward. Walter hated the pain of Lisa's spankings and tried to avoid them, but to his dismay he also found the prospect of being punished by Lisa very erotic. Lisa ignored his hard cock and he quickly lay across her lap.

Lisa patted his bottom with the paddle. "I have a riding date with my friend Anne in half an hour, so I don't have time to punish you properly. But I'm going to give you a quick paddling now to give you something to think about while I'm gone."

Lisa brought the paddle down hard across Walter's bottom. Although it was a light paddle, it had a mean sting. Lisa played tennis and she had a strong right arm. Soon the crack of the paddle across Walter's bare bottom was echoed by his cries of pain. After Lisa had counted out forty strokes she told him he could get up.

"I'll be back at lunchtime" Lisa told Walter as he pulled up his pants. The pain of the spanking had deflated his cock. "We can have lunch and then take care of the rest of your spanking. In the mean time I want to see some progress on your term paper."

Lisa returned three hours later. Walter had added one page to the term paper, but when he heard Lisa's riding boots on the stairs he was day dreaming. When she came into the room Walter's eyes were immediately drawn to the black riding whip in Lisa's right hand.

"I'm glad to see you working on your paper" Lisa told him. She put the whip down on the bed. "Let's see what you've done so far".

Walter moved aside to let Lisa sit at the computer. She read through what he had written. "The is good, Walter. But it is only a start. You need to focus on your work and finish this. But we can discuss this more after lunch." Lisa stood up. "I don't know about you, but I'm hungry. Lets have lunch. I'll give you a spanking after lunch and then you can get back to your paper."

Lisa made them curried chicken sandwiches on sourdough rolls for lunch. Normally Walter would have wolfed his down, but the prospect of his upcoming punishment ruined his appetite and he ate only half of his sandwich. "I'll save it for later" he told Lisa.

"OK, honey" she told him. "Let's get your spanking over with. Now please come with me".

Walter liked it when Lisa called him "honey". The only problem was that this usually only happened when he was getting a spanking.

Walter followed her into the living room again. The paddle was on the coffee table where Lisa had left it in the morning. Without being told Walter bared his bottom and lay over Lisa's lap to take his punishment. Lisa gave him a short lecture about the importance of concentrating on his school work. She also told him that she was very disappointed that he had lied to her about how much work he had done on his paper. He answered "Yes, Lisa" and "I'm sorry Lisa" at the appropriate places. Walter felt guilty about not doing his work and especially bad about lying to Lisa. He knew he deserved a spanking and he wished that Lisa would just dispense with the lecture and start paddling him. Or so he thought until Lisa gave him the first stroke with the paddle. The paddle seemed to hurt even more than it had in the morning. Lisa concentrated many of the strokes just above his thighs and he was soon crying out with each stroke.

"I want you to go to your room, undress and lie over the pillows" Lisa told him after she had given him forty strokes.

Walter stood up. "I'll be up in a few minutes to give you a whipping" she told him as he pulled his pants up.

"Please don't whip me, Lisa. Can't you give me the cane instead? I'm sorry I've been procrastinating."

Lisa put two fingers to his lips, silencing him. "Shh. I'm sorry, honey. Now go to your room and get ready for me."

Walter went upstairs to his room. As he undressed he kept glancing at Lisa's riding whip, which she had left on the bed. The whip was about two and a half feet long, it's shaft sheathed in smooth black leather. The handle was built up from braided black leather and had a silver button on the end. The whip narrowed down to about a quarter inch and had a small stiff loop of leather at the tip. He picked up the whip, holding one end in each hand. It was stiff, bending only slightly as he applied pressure. The prospect of a whipping sounded scary and Walter guessed that the whip would hurt more than the rattan cane Lisa usually spanked him with. He was tempted to try the whip on his thigh but decided that he would know what it felt like soon enough.

Walter moved two pillows to the middle of the bed and lay naked over then, with the pillows under his hips, pushing his bottom up. It was about five minutes before he heard the sound of Lisa's riding boots coming down the hall, although it seemed much longer.

Lisa came into the room and shut the door. Walter thought she looked very beautiful as she crossed to the bed and picked up the riding whip, moving to to his left side.

Lisa tapped his bottom gently with the whip. "Do we need to have any more lectures about schoolwork and truthfulness?" Lisa asked.

"No, Ma'am", Walter answered.


Walter heard the whip slice the air and a line of pain burned across his buttocks. The pain seemed to spread after a few seconds. As the pain started to fade he felt the second stroke, lower down his buttocks this time. He cried out. Lisa whipped him slowly, one stroke every ten seconds or so, Walter's buttocks clenching slightly and then relaxing as the whip fell across them. When Lisa had given him twenty strokes she stopped to let him catch his breath. She caressed his bottom, feeling the heat and the raised lines of the welts left by the whip. After the pain of the whipping her hand felt very good. After a couple of minutes, Lisa moved to the right side of the bed and started whipping him again. After she gave him a stroke across the crease where buttocks and thighs met, he squirmed, pushing his hips into the bed, clenching his buttocks in pain, turning on his side.

"Lie still, honey" Lisa warned. "Or I'll have to give you extra strokes for moving out of position."

She continued whipping him. Walter's face was streaked with tears and he was crying softly. He was only thinking about how much the whipping hurt, not the consequences, when he moved out of position again, causing Lisa's next stroke to fall partly across his hip.

"That's two extra strokes, honey. Now please lie still." By the time Lisa finished administering the last eight strokes Walter had moved out of position one more time.

Lisa let him rest a moment, caressing him. "I'm going to have to give you four extra strokes for moving out of position twice." she told Walter.

"I'm sorry Lisa. Really I tried to stay still. But it hurt so much."

"I know it hurts honey, but spankings are supposed to hurt. And you know better than to move out of position.

Lisa moved back to Walter's left side and put her left hand on the small of his back, pushing him into the bed. "Please put your legs together. I'm going to give you your extra strokes across your thighs."

The whipping across his thighs hurt more than it had across his bottom and Walter sobbed as Lisa gave him the final four strokes.

"You can get up now, honey", Lisa told him. She stood beside Walter, cradling his face against her breasts and petting his hair as he sat on the edge of the bed. When Walter had stopped crying, his hope that his punishment was over was dashed when Lisa told him to get the round paddle.

Walter got the paddle from the closet. It was about the size of a ping-pong paddle, with an oval head, made out of half inch thick dark hard wood. Walter handed Lisa the paddle and she took him over her knee again. His bottom was crimson and lined with welts. As she caressed him she could feel the hot skin under her hand. She could see four red welts across the tops of his thighs.

"I'm going to give you forty strokes on each cheek, honey, and then your punishment will be over."

Lisa started spanking him hard with the paddle, alternating buttocks. Lisa spanked Walter in sets, giving him ten strokes on each cheek and letting him rest for a couple of minutes while she caressed him, telling him that it would all be over soon. As she punished him, she held him firmly with her left arm wrapped around his waist, pulling him close against her body. The paddling, over his sore, freshly whipped buttocks, was very painful and by the time it was half over he was sobbing. It was like being a little boy again, being spanked for being naughty and along with the pain Walter felt, at some deep core level, as safe and loved as he ever had been.

When Lisa finished punishing him, she held him for a few minutes, telling him that he had taken his spanking like a good boy. Then Lisa left the room to let Walter dress.

Walter sat on a pillow the rest of the weekend as he worked on his term paper. A sore bottom and the knowledge that Lisa would not hesitate to spank him again on that same sore bottom, greatly helped with his concentration. With Lisa acting as his editor and adviser Walter finished the paper and turned it in on time.

A week later his teacher handed the graded papers back to the students. Walter's paper had gotten an A, which he proudly showed Lisa when he got home.

"I knew you could do it, Walter" she told him. "I'm very proud of you"

Walter beamed at her praise. "Well, I had your help."

"That's what I'm here for. Why don't we celebrate and go out to dinner tonight."

"That would be great, Lisa"

Lisa picked a somewhat fancy Italian restaurant that specialized in what Lisa called Nouveau Italian.

Walter changed into a button down shirt and a pair of slacks. He was waiting for Lisa in the entryway when he heard her coming down the stairs. When he turned to look at her, she took his breath away. Lisa was wearing a black dress that hugged her upper body, flaring out at her hips and coming down to the middle of her thighs. Her long legs were encased in stockings and she was wearing a pair of black spike heels. Her honey blond hair was pulled up in a French braid, showing the shape of her neck. The dress was low cut in the front, showing the tops of her breasts.

Walter thought that anyone seeing them would assume that he was out with his older sister. But he did not care what anyone thought. He was with Lisa and she was beautiful. They had a wonderful evening. Lisa knew the owners of the restaurant and they looked the other way when Lisa ordered Walter a small glass of red wine with dinner.

"Thank you for a wonderful evening, Lisa" Walter said when they got home. "And thanks for the help on the paper. I really couldn't have done it without you."

"Well you did the work, all I did is help edit it"

"Yeah. But, well, I also mean the spanking too. It hurt a lot and I didn't like it much at the time, but I guess it got me going."

"You're welcome, honey. As I said, that's what I'm here for" She kissed him on the cheek and he watched her walk upstairs to her room.

September, 2004

Case Wintermute