Fantasy Island contest entry – F/M spanking stories

After Douglas’ death my sexual desires were becoming an obsession.  I loved my husband but he was gone and I had desires that needed to fulfill.  One of Douglas’ employees was a 26 year old man who I would have fallen for when I was 26 years old.  Jonathan was a classical bad boy.  He was 5’5″ tall and not very athletic.  He was more pretty than handsome.  He had risen to a position of power in one of Douglas’ companies and commanded a very high salary.  

Alexis is a lawyer who specializes in sexual harassment cases and she was representing on a contingency basis some of my employees.  These employees complained about Jonathan’s unwanted sexual advances and his crude remarks.  She arranged a meeting with me and presented her case.  There was no doubt that our corporation could be liable for his behavior and that litigating the case would be futile so we agreed to a settlement.  

Alexis is a 29 year old blond bombshell.  She was over 6′ tall and had the firm body of an athlete.  She was involved in a relationship with her 25 year old roommate Megan.  Alexis didn’t like men and felt that most were pigs who would benefit from the firm hand of a woman.  When I assured h. er that Jonathan would be terminated Alexis had a better idea.  Jonathan would be given the choice of being terminated or going over my knee for a sound no nonsense spanking followed by a severe caning from her.  

I confided to Alexis that I was never spanked and have never spanked; but, I had seen my mother spank my younger brother who was 10 years younger than me and that I always went out of my way to witness his spankings and found them exciting.  Alexis told me that she was an expert spanker and that she had promised her young roommate a well deserved spanking when she returned home.  Alexis insisted that I accompany her home to witness the paddling.  

When we arrived at Alexis’ home her roommate, Megan, greeted us at the door.  She was dressed in tight jeans and a loose t-shirt which showed off her lovely figure.  Megan was 5’4″ tall with dark brown hair down to her shoulders and dark brown eyes.   She looked more like a college coed than a 25 year old.  Alexis ordered Megan to put the straight back chair in the middle of the room and to bring the paddle.  Alexis took off her suit jacket leaving her dressed in a pencil skirt with a white silk blouse, black stockings,  and 6″ heels.  She sit in the chair and smoothed her skirt which had risen to expose the tops of her black nylon stockings being stretched by her garters.  

When Megan returned she was in tears carrying a wicked looking oval paddle about 1/4″ thick with holes drilled in the business end.  As she handed the paddle to Alexis she begged not to be spanked too hard or long and promised to never again use Alexis’ charge card without permission.  Alexis told her that she was going to give her a good no nonsense spanking and that when she was finished that Megan would be a well spanked unhappy little girl and that she deserved the spanking she was going to get.  

Megan was ordered to Alexis’ right side and Alexis unbuckled and lowered Megan’s jeans exposing Megan’s white nylon panties.  As she placed her over her stocking clad knees Alexis adjusted her to her liking so that her bottom was directly across her lap.  Alexis proceeded to paddle the kicking girl over her panties as her t-shirt draped over her head and her jeans were kicked off her legs.  Alexis paused to remove the t-shirt and then resumed the paddling.  Megan’s screaming started in earnest as Alexis lowered her panties down to her knees and told her, “I haven’t ever really started yet”. Another series of spanks landed now alternating cheeks hard and fast.  Megan was gasping, squirming, and tears were running down her face as her spanking continued.  She was pleading for mercy.  Her bottom was bright red and her sobbing was harder, her makeup was streaked and her shoulder length hair was in disarray as she squirmed kicked and howled.  When Megan was finally   left off of Alexis’ lap she danced and skipped around the room holding her well spanked bottom while wearing only her bra with her panties around her knees.  

I was excited at the sight of Megan’s paddling when to my surprise Alexis told me that if I was to give Jonathan a good paddling that I would need to know exactly what a good spanking felt like.  I’m 47 years old and this 29 year old beauty was proposing to put me across her lap and paddle me like a 10 year old.  I knew that the paddling would be painful but the excitement of going over Alexis’ lap was alluring as I obediently draped myself over her knees and she raised my skirt exposing my stocking tops and lovely tush outlined by my garter belt.  I took my spanking no better than Megan but this convinced me that Jonathan needed to learn the same lesson over my knee.   

Our plan was to propose to Jonathan that we would go on a business retreat to my island off of the coast of Tahiti and that our attire would be from different decades of the past.  When we arrived at my island home Alexis was dressed in a stunning skin tight black dress with a pencil skirt, black nylon stockings, and 6″ heels.  I had a green satin gown out of the 30’s skin tight and below my knees with black stockings and heels.  Jonathan was dressed in a double breasted pin striped suit out of the 40’s.

When we arrived at the island Alexis did all of the talking and explained to Jonathan his options in her best legal language.  He would be paddled by me and be given a severe caning from her with a bamboo walking stick or be terminated.  He agreed to be disciplined and signed a waver that she had prepared.  

I went first and remembered how painful Alexis’ paddling had been and was determined that Jonathan’s experience across my satin clad lap would be just as painful.  He was stripped naked and draped across my green satin clad lap.  I told him that naughty boys sometimes need a firm female hand to keep them in line and that the little boy inside you needs a good spanking.  I am much stronger than Jonathan and had no trouble turning him over my lap for a good spanking.  I spaced about one second between spanks and could hear his squeals and promises to be good, kicking and sobbing,  after the first couple of spanks.  I felt a strange pleasure and release as I used Alexis’ paddle on his naked bottom.  He squirmed over my knee as I watched the red outline of her paddle with the holes in it appear on his bottom.  His bottom turned pink and then red and he was kicking like a 10 year old.  When I finally left him off of my silken lap he hopped around the room holding his bottom and continuing to cry just as Megan had done.   It was the first spanking I had ever given; but, he was as well spanked as Megan had been.  

Before he gained his composure Alexis secured his wrists and ankles in leather cuffs and placed a pillow over the back of the straight backed chair that I set on while spanking him.  He was then forced over the pillow and his wrist cuffs were fastened to the front legs of the chair and his ankles to the back legs.  He was helpless yet comfortable.  Alexis and I enjoyed a glass of wine while he gained his composure. Alexis explained to him that she paddled her roommate as hard as he was just paddled for much less serious offensives and that he was now going to be caned the same way lawbreakers are in Singapore.  Alexis in her pencil black dress, black stockings, and 6″ heels was stunning as she switched the bamboo cane through the air.  He was to receive 6 strokes and after each stroke Alexis waited over a minute for him to calm down before the next stroke was delivered.  It took almost 20 minutes to complete his caning.  Alexis proved a master.  Not one stripe on his bottom crisscrossed another.  There was a perfect stair step of stripes covering his bottom.  Alexis rubbed ointment on his welts and left him over the chair while we enjoyed another glass of wine.  

During the remainder of our week on the island Alexis and I dressed in gorgeous sexual costumes from decades past.  Corsets from the turn of the century under our long skirts and dresses, pointed bras under our tight sweaters from the 50’s, and short flapper dresses from the 20’s while Jonathan was allowed no clothing until we were ready to leave.  Alexis and I rubbed ointments on his bottom daily and warned him that  if there were any more problems at work that he would be brought back here for a severe horsewhipping that he wouldn’t forget.  

To my surprise when we returned to the states Jonathan asked me out and we have been dating.  I’m not sure if he realizes that since my experiences with Alexis, Megan, and him that the idea of spanking him is exciting and after all I am old enough to be his mother.   Its only a matter of time!