One Summer

Lilly had been gardening all morning and was finishing lunch when the phone rang. It was Mrs. Boswell, her nearest neighbor, whose voice she recognized from teas that her mother gave. Those teas were such a bore. And Mrs. Boswell could drone on so.

"Lilly, dear, is the Major free?", meaning Lilly's father.

"I'm sorry, Ma'am, but Daddy and Mummy are in France."

Lilly was almost eighteen, in her last year of Public School. She had use of one of the cars, a checking account and was a responsible girl, so her parents left her home, rather than drag her to France. It was a second honeymoon for them.

"Oh bother", said Mrs. Boswell. "I was going to ask the Major to give me a hand with Alfred. You know Alfred, don't you?"

Alfred was Mrs. Boswell's grandson. His parents died when he was young and he had been raised by Mrs. Boswell. Alfred and Lilly had grown up together, but since Lilly was two years older and went to a different school, they saw each other rarely. Although they were neighbors, the size of the old estates they lived on helped enforce isolation. Lilly remembered Alfred as a skinny, awkward boy.

"Yes, Ma'am, I saw Alfred at your Christmas party, the Christmas before last."

"Well he's been getting out of hand and needs to be taken down a peg or two. My arthritis is acting up terribly or I'd give his backside a good thrashing. But I can barely brush my hair, much less lay into the rapscallion with a cane, like he deserves. I was going to send Alfred over to the Major to get what he needs."

"Well... I could help you out there, Ma'am. I was head girl and a prefect last year. I was responsible for giving the cane to the lower form girls for things that were not serious enough for the Headmistress. And then I've certainly been on the receiving end of Daddy's discipline."

"Oh would you, dear? That would be wonderful. When shall I send Alfred over?"

Lilly looked at her watch. It was 11:45. "Why don't you have Alfred come by at 1:00."

"Thank you so much, dear. Now I want you to give him a good thrashing. He's been impossible the last two weeks. He needs a good hiding."

"Yes, Ma'am"

"And don't be soft on him!"

"No, Ma'am, I'll try not to be."

"If he gives you the least trouble, you can tell him that it will be off to the military academy for him if he does not toe the line. I'm at my wits end."

"Yes, Ma'am. Don't worry. I'll make sure that Alfred gets what he needs."

"All right then. Alfred will be by at 1:00 sharp. I shall tell him that you will give him extra if he's late. Thank you so much dear."

"I'm glad to help. I hope your arthritis gets better soon, Ma'am."

"Thank you dear. Bye bye."

"Goodbye, Ma'am".

Lilly finished lunch, washed the dishes and went upstairs to her bedroom to shower and change. She was ready when the doorbell rang at a little before 1:00. Apparently Alfred was taking no chances. She let him wait a few minutes before going to open the door.

When Lilly pulled open the old iron bound oak door she saw Alfred waiting, his bicycle proped to the side of the stone arched entryway. Alfred looked rather nervous, standing with his weight on one foot, as if he wanted to flee, which might well have been the case.

"Hello Alfred"

"Uh, Hi Lilly"

"Why don't you come in" she said, moving aside to allow him to enter and shutting the door behind him. He jumped when the heavy door shut with a thud. Knowing that you were in for a hard spanking does tend to make one nervious, Lilly through to herself, remembering the times she had waited outside the Headmistress' office.

"Gram told me to give you this", Alfred told her, handing her a cream colored envelope that was sealed with red sealing wax.

Alfred was not the boy Lilly remembered. He had grown since she had seen him a year and a half ago and was now about two inches taller than she was. Alfred was no longer the skinny boy she remembered. He was wearing a pair of light weight grey wool pants and a blue short sleeved polo shirt, which showed off his muscled upper body.

Lilly opened the envelope. Inside was a single sheet of paper, with the Boswell family crest on it. In Mrs. Boswell's shaky spidery script was written "Please give the bearer a good sound thrashing. If he gives you any trouble, please don't hesitate to call. With thanks, Amelia Boswell."

Lilly folded the letter and put it back in the envelope. She was suddenly nervous. The etiquette books said nothing about how to greet a guest who has been sent over by his grandmother for a hard spanking.

"How have you been, Alfred. I don't think that I've seen you since your Grandmother's Christmas party."

"I've been doing all right, I guess. Just school and studies. I've been studying for exams this fall. How have you been, Lilly".

"Oh, I'm fine. Mummy and Daddy are in France until late August. I'm going to King's College at Cambridge in the fall. Have you been doing sports at school?" Lilly looked at Alfred's angular upper body.

"I was on the rowing team last year."

Lilly decided that the small talk was getting ridiculous. "Do you know what the note from your grandmother said?"

"No. She just gave it to me and told me to give it to you."

"Well, do you know why she sent you over?"

Alfred looked down at the stone floor of the entryway, as if he wished it would suddenly open up and swallow him. "Yes", he answered.

"And that is..."

"Ah, you're to give me a spanking."

"Do you deserve it?"

"I guess that I do. I hate studying for exams and Gram has had to nag me constantly."

"Well then, I promised your grandmother that I would give you a good hiding. She told me that if you gave me any trouble it would be off to the military academy next school term. But you won't give me any trouble, will you."


"I think that we need to set the proper tone here. That's 'No Ma'am'"

"No, Ma'am. I will not give you any trouble".

"Right then. We might as well get this over with, don't you think?"

Lilly turned and lead the way toward the library, her high heels tapping on the stone floor. Alfred's eyes were drawn to the sound and Lilly's long bare legs, which were topped by a very short black leather skirt. He had been so nervous that he had not even noticed how she was dressed. Now his eyes were rivited to the curves of Lilly's bottom under the tight skirt. She was wearing a deep burgundy silk blouse, which hugged her upper body.

Lilly turned to Alfred, who remained rooted where he had been standing, staring at the most beautiful bottom he thought he had ever seen. "Well, come along then"

"Yes, Ma'am" he said, following her into the library.

The room was lined with bookshelves. There was a huge dark wood desk near one wall and chairs and a couple couches in the center. Lilly went to the desk and removed something from the drawer. When she turned back toward him, Alfred saw that it was a long thick ruler made from some honey-colored wood. Lilly crossed to one of the couches and sat down in the middle.

"Come here, please" she said, indicating a spot on the persian rug to her right side. When Alfred went to Lilly's side he saw that her blouse was cut low, the dark fabric tight over her breasts. Alfred could see the top of her black lace bra. The girls he had invited to school dances looked nothing like this.

Lilly unbuttoned and unzipped his pants, letting them fall around his ankles. His cock sprang out, hard and erect, when she pulled his briefs down to the middle of his thighs. She reached up and caressed his cock. "How nice. Is that for me? Well, maybe later. But we have some business to take care of first. Over my lap, naughty boy."

Lilly's skirt had hiked up as she sat, leaving her thighs bare. Alfred ginerly lay across her lap, his cock resting against the smooth skin of her thigh. Soon the smack of the ruler, hard across his bare bottom, distracted Alfred from any erotic thoughts about Lilly's bare thighs. At first Alfred tried to take his punishment quitely, but it hurt and soon he was crying out as Lilly spanked him with the ruler.

Lilly stopped spanking him for a moment. He really did have a nice bum, she thought to herself as she caressed him, feeling the rising heat from his buttocks. She tapped his bottom lightly with the ruler, allowing him to feel the smooth, cool wood, before bringing the ruler down sharply across his ass. When she had spanked his bottom to a light crimson, she stopped paddling him.

"All right then, up you go", Lilly told Alfred. "You can take off your pants and knickers. No sense in having them in the way."

Alfred stood up. His pants and briefs had fallen down around his ankles and he stepped out of them, embarrassed at being naked from the waist down in from of Lilly.

She crossed the room an umbrella stand beside the desk. It held several walking canes, some riding whips and some rattan canes. Lilly selected one of the rattan canes and swished it through the air, testing its flexibility. Then she slashed it into one of the over stuffed chairs. Alfred looked at the line cane left in the dark leather, thinking about how the cane would feel across his bottom. Lilly tried out another cane on the chair, before settling on a third cane and placing it on the desk. To Alfred's horror she then took out a smooth black leather riding whip and tested its flexibility on the chair. The crack of the leather whip against the leather chair echoed in the room. Satisified she carried the cane and the whip over to where Alfred was standing.

"Over the arm of the couch please, bottom up, good and tight" she told him, pointing to the arm of the couch. Alfred lay across the padded leather arm of the couch, his chest resting on the seat cushion, he toes resting on the floor. He was very conscious of how his bare bottom was pushed up, waiting for the cane, as Lilly put the whip down on the seat of the couch and moved behind him with the cane.

"A spanking is supposed to hurt and this will definitely hurt. I want you to stay in position, with your bottom up, no squirming. Or I'm going to give you extras. Is that understood?"

"Yes, Ma'am"

She brought the cane lightly across his bottom a couple of times, measuring her stroke, before bringing the cane whistling down across the center of Alfred's upraised bottom. He breathed in sharply but managed to avoid crying out. Lilly gave him another stroke, lower than the first. She aimed the third stroke at the lower curve of his bottom, near the top of his thighs, but the cane caught partially on the couch. She gave him several more storkes, but it was difficult to get the cane across both buttocks and not catch the couch. This would not do, Lilly thought.

"I'm sorry, I keep catching the cane on the couch. I just can't give it hard enough in that position. Daddy always spanked me bent over the desk, but that's so dreadfully uncomfortable. At school I make the girls pull their knickers down and bend over a chair, but that's no good for a long spanking." Lilly paused a moment, thinking.

Alfred was tempted to tell her that it was quite all right, don't worry about spanking him, he could just go home now, but he thought that silence was best.

"I have another idea" she told him. She picked up the whip. "Come with me, please." Alfred got up and followed her out of the library, into the entry way. His bottom was sore from the paddling she had given him and the cane strokes burned as he walked. His eyes were drawn again to her bottom and then to her right hand, where she carried the cane and the whip. Lilly started up the stairs, to the second floor. Alfred lagged several steps behind her, looking up as she climbed the stairs he could see the lower part of her bottom and her black panties underneath the short skirt. His cock started to get hard again.

Lilly turned, catching him looking. "Are you looking up my skirt, you naughty boy?"

Alfred tried to look down. "Yes, Ma'am. I could'n help it."

"I think that's very disrespectful. I'll punish you for that too. Now come on, follow me."

She lead him upstairs to her bedroom. The room had flowered wall paper and lace curtains, drawn open to windows that looked out on the back garden. Lilly's four poster bed had a eyelet spread, with a flower print that contrasted with the walls. At the end of the bed there was a brocade ottoman.

"Take off your shirt and bend over the end of the bed, please", Lilly ordered, indicating the ottoman. When he was naked, Alfred knelt on the ottoman, lying forward with his chest on the bed. The top of the bed was a little lower than the top of his legs, pushing his bottom up.

Alfred felt the cane again, light across his bottom as Lilly measured her stroke. "This is much better" she told him.

Lilly started caning him again, the strokes harder than before. Alfred quickly stopped trying to take his punishment in silence and was crying out. The strokes across his lower bottom and upper thighs were the worst. Lilly stopped caning him for a moment and moved to the other side, switching to a backhand stroke so that his buttocks would be punished evenly.

Lilly sat down on the bed next to Alfred and stroked his hair. "Now there is the matter of your being disrespectful and looking up my skirt. I don't suppose that you got to see much, so I'll just give you an extra three. But they'll be good and hard. Or I'll let you take off my skirt and really get a look, but you'll have to take six"

"I'll take six strokes, Ma'am"

Lilly stood up. "Come here" she told Alfred. He stood up and moved beside her. "Take off my skirt" she told him.

He moved behind her and unbuttoned the skirt at the waist and then unzipped it. Instead of letting it fall, he knelt and she stepped out of her skirt after he lowered it to the floor.

Lilly was wearing a pair of black string bikini panties, low across her full hips, leaving the top of the cleavage of her buttocks bare. Alfred could see the round curve of her bottom through the sheer material.

Lilly tied the tails of her blouse under her breasts and then pirouetted, letting alfred see both her front and back.

"All right, love. Over the bed again. You've got another six coming. I want you to count them out for me as I give them to you and thank me for each one."

Lilly gave the strokes very slowly and hard. Alfred cried out with each stroke as he counted and thanked her.

"Were those extra strokes worth the look?" Lilly asked as she caressed him again between his buttocks.

"Oh yes, Ma'am"

"Hmmm, you do know how to flatter a girl"

Lilly exchanged the cane for the riding whip. Alfred's buttocks and upper thighs were a deep crimson and lined with welts. He felt the caress of the cool leather as she ran the tip of the whip between his buttocks and down over his balls. The whip moved away and he felt a burning pain, even worse than the cane across his ass. He straighted up, in surprise at the pain, crying out.

"Stay in position, love", Lilly told him. "I'm going to have to give you extras for that. Now bend back over." He bent over the bed again, crying out as she whipped him, managing to stay in position for the next three strokes. Lilly whipped him across the tops of his thighs and he straightened up again.

"You're being a very naughty boy. You are just making your whipping longer."

"I'm sorry, Ma'am. I can't help it. It hurts so much."

"I can tie you if you can't stay still, but you will have to take extras."

"You'll have to tie me, Ma'am"

Lilly went to the dresser and took out a pair of padded cuffs. Alfred briefly wondered what these were doing in her bedroom.

"Come here and hold out your hands."

Alfred stood up and went to where Lilly was standing at the corner of the bed. She buckled the cuffs on his wrists.

"Raise your hands" she told him as she buckled a strap connecting the cuffs to the top of the bedpost. Lilly got another pair of cuffs for his ankles and attached them to the bottom of the bedpost. The bed frame was massive, made out of dark hard wood and Alfred felt no movement as he pulled against it.

Lilly thought that Alfred looked beautiful, his lean muscled body against the dark wood, his ass and thighs crimson and welted. He was hers and she could do what she wanted with him. She ran her hand down his back, over the hot welted skin of his buttocks, then down between the cheeks, caressing the base of his cock. He grew hard under her caresses. She kissed the back of his neck.

"All right then. You're going to get the fifteen strokes you still have coming, plus another ten for not staying in position and making me cuff you. Now push your bottom out for me, love"

Alfred bent over as much as the cuffs allowed, pushing his bottom out. Lilly brought the whip down hard across his ass. He cried out as she whipped him, straining against the cuffs, but he was held fast, the whip cracking across his bottom and thighs. After giving him fifteen strokes Lilly let him catch his breath, caressing him for a few minutes. His skin was lightly sheened with sweat.

"Your whipping would be over now if you had been a good boy. But you've got ten more I'm afraid."

She started whipping him again. He tried to count the strokes out to himself, but started to lose count as he cried out. Finally the strokes and his cries stopped. Lilly uncuffed his feet and then his hands. His cock was totally flacid now, any erotic thoughts banished by the pain of the whipping.

Lilly sat down on the side of the bed. "Go into the bathroom and get me the bath brush from the shower" she told him, pointing to the door across the room. She watched him walk out of the room. Some of the welts left by the whip where purpling across his muscular ass.

When he returned with the brush she held out her hand and he gave it to her. The use she planned for the bath brush did not occur to him until she ordered him over her lap and he felt the caress of its smooth wood on his bottom.

"Your spanking is almost over, love" she told him. "I'm going to spank you with the brush and then it will all be over. Please put your right arm behind you" she told him, holding his arm behind his back with her left hand. She brought the brush down hard on his right buttock, quickly following with another stroke on his left cheeks. His bottom was already exquisitly sore from the caning and the whipping. The pain of the brush filled his world, as she paddled him, giving the strokes hard and fast, alternating cheeks. The spanking seemed to go on for a long time. When she finally stopped paddling him he felt tears on his cheeks and was embarrassed to realize that he had been crying like a little boy being spanked over his mother's knee.

Lilly lay back on the bed, her blouse open showing her black lace bra. "Come here, love" she told Alfred holding her arms own. He got up and lay next to her. She could feel the wetness of his tears as he nuzzled her breasts as she held him.

"Have you learned your lesson?" Lilly asked Alfred after his breathing had slowed.

"Yes, Ma'am. Please don't spank me anymore"

"All right, love. That's good. Now we can move on to other things. You don't have to call me Ma'am any more"

Although she was not breathing fast, having Alfred naked and spanking him hard gave her that tight feeling in her chest that is the feeling burning lust. She was sure the crotch of her panties was soaked.

Lilly moved away slightly and unhooked the front of her bra. She cupped one of her breasts in her hand. "Bite, very gently"

Alfred took her nipple in his mouth, sucking on it and biting softly. Lilly could feel his cock hard against her leg. She let him remove her blouse and then her bra. Looking at her naked except for the lace triangle of her panties was the most beautiful sight that Alfred had ever seen.

"Have you ever been with a girl" Lilly said caressing his hair.

"Only a couple of times. You know, petting. But never..." Alfred's voice trailed off.

"You've never fucked a girl?"

"No" Normally Alfred would have been embarrassed to admit that he was a virgin, but the intimacy of the spanking Lilly had given him had somehow changed that.

Lilly rolled away from Alfred, toward the side of the bed. One side of her panties had moved into the cleft of her bottom, leaving her cheek bare. Lilly opened a drawer in the night stand and took out a box, from which she removed a condom.

When she had Alfred lie on his back, his cock stood up like a pole as she slipped the condom on. She guided him to her breasts again, to both of her nipples and them his hands, down to her panties, slipping them off. She showed him how to caress her vulva and how to gently caress her clit the way she liked. Lilly was on the edge of orgasm when she pulled Alfred on top of her and guided his cock inside her. Alfred's buttocks were hot under Lilly's palms as she guided him, first slowly, then faster, thrusting into her as she came, the image of his ass under the whip burning in her mind's eye.

Alfred always looked back on that summer as a point in his life where it took a new direction. Many people never learn the difference between lust and love. The difference is especially difficult to understand when you are young. Alfred fell head-over-heels in love with Lilly. With the carrot of Lilly's blazing sexuality and the stick, applied hard across his bare bottom, Alfred studied harder that summer than he ever had before. When he took his exams in the fall he did far better than he expected and was accepted at Oxford.

Lilly loved Alfred's muscled body and the tight curves of his ass. Alfred proved to be an eager student, both academically and sexually. When ever Alfred slacked off academically, she would punish him, covering his bottom and thighs with welts. When he studied hard and did the work she assigned she gave him long slow sexy spankings.

When the summer finally drew to a close and it was time for Lilly to leave for Cambridge, she broke up with Alfred. Women grow up faster than men and she knew that this was just a summer romance. For Alfred the pain of breaking up with Lilly eclipsed any whipping she had ever given him. As is usually the case with the young suffering from wounds of this kind, Alfred eventually recovered, but he never forgot Lilly.

September, 2004

Case Wintermute