Cronic masturbator gets caught and punished

Posted in: S & M

Stripped ,Stroked, and Spanked, By Zack Smyth
SYNOPSIS: While I was growing up, I used to haunt the riding stables and ogle girls in their tall boots and firm fitting riding pants as they moved their hips with the motion of their horse, Then I’d go home, don my black rubber hip boots & raincoat and masturbate. Later, when I got a summer job as a wrangler at a riding academy , I watched them from the bunk house window and beat off regularly till one day the riding instructor (female) caught me with my pants down and had the ladies punish me by being stripped and stroked and spanked….

Most guys go for anything in skirts. I go for anything (female) in boots. That’s why I used to haunt the local riding stables and ogle the girls carrying crops and wearing form fitting riding pants, tall black riding boots and spurs. After watching them for a while, I’d go home, sneak down to the cellar to masturbate furiously in my black rubber hip boots, raincoat and hat while whipping myself with a riding whip. When done, I wiped everything off with a damp sponge and hung them up to dry.
When in college I got an offer to be a wrangler for the summer at a women’s riding academy .
In exchange for tacking up the ladies horses, feeding them and cleaning out the stalls I would get free room & board, plus my own horse to ride and $100 per month plus tips. I eagerly accepted, packed my raincoat, boots and whips in the bottom of a trunk filled with other things, and drove up to the academy as soon as school was out. After meeting the manager, who was affectionately called the “Boss Lady”, I went down to the stables where the riding instructor, Miss Sadie, showed me around. I was very pleased with the lay out, and especially the bunk house which had windows looking out on the riding ring. When she left, I unpacked my things, being careful; to hang up my long black rubber coat, boots and whips in the very back of the closet where nobody would see them.
When the girls came down for their riding lesson the next day I had all the horses fed, groomed and saddled so that Miss Sadie was pleased with me. I held their stirrups and helped some of the girls mount while secretly staring at their highly polished boots and spurs. When they were mounted, I handed them their crop, which I had been examining and testing by whacking it against my boots.
While Miss Sadie put them through their paces, I went to the bunk house, dropped my pants, got out my fetish hip boots, pulled them on and slipped into my long black rubber rain coat and snapped the hat tightly under my chin. Then, getting my riding whip from its hiding place, I put my hand in the wrist loop and started to tickle my cock and balls with the whip lash while ogling the women in the riding ring right outside my window. I particularly liked the one in black leather riding pants and above the knee black leather boots who had a long black finely tapered dressage whip in her gloved hands. The whip had a “cute” little red lash, or popper, on the business end and I found out later name was Daisy. She sure knew how to use that whip! I gasped as I watched her hips undulating as her tits bounced when she whipped and spurred her mount around the course, wishing it were me she was riding and whipping,
Staring at her, I wrapped the skirts of my long black rubber raincoat around my rampant cock and masturbated happily till I came in great gushes of white, creamy jism that shone wetly against my black rubber coat.
When done, I cleaned everything up with a damp sponge, hung my gear up in the back of the closet, got dressed and was ready to go out and help them dismount.
Saturday night I went in town and drank beer at the local pub and purchased the latest copy of Playboy or Hustler or Playgirl Anything I could get my hands on that had a naked girl in its centerfold . When I got back to the bunk house, I laid the centerfold out on my bed, undressed, put on my fetish rubber outfit and kneeled over the display , pulling out my cock from the front fly of my rubber coat and masturbated to the slap-slap tune of my rubber coated sleeve smacking with each stroke against the tops of my rubber hip boots that stuck out a bit because I was kneeling in them. Usually it took only a few strokes till I started to ejaculate, and I tried to aim it at the model’s tits. However, I sometimes overshot a bit and it landed on her throat or face .Then I passed out and slept right there , wrapped up in my rubber coat like a cocoon. Sometimes later at night, I got up, tossed my rubber coat over the back of a chair, went to the bathroom and then sat on my bed to pull off my hip boots which I left in a heap along with the soiled magazine and got back under the blankets
The ladies didn’t ride on Sunday so I took my horse for a trail ride up into the mountains after getting a box lunch from the kitchen. I particularly enjoyed this outing on rainy days because I then wore my riding slicker and black rubber riding boots.
Thus I was thoroughly enjoying my summer job immensely. All too soon, though, I got a sore prick even though I used the skirts of my rubber coat as a sleeve when I wanked. Eventually, I got some medicated Vaseline and lubricated condoms to jerk off into. I smeared the Vaseline on the sore spots and, much to my surprise, I found the slippery rubber condoms actually helped me shoot my load faster . I had to be sure to put the used rubbers in the trash bin afterwards so the Boss Lady or Miss Sadie wouldn’t find them and think I’d been fucking one of her students, which was a nono.
It all came to an end one day when the Boss Lady came down to the stables to look for me. I was so preoccupied at the time with my wanking that I didn’t hear her entering the bunk house so I was surprised to hear husky voice saying, “Hey, what the hell do you think you’re doing young man? You naughty stable boy! I’ll see what Miss Sadie has in mind for your punishment”
With that pronouncement, she yelled at Miss Sadie to “Come in here and see what this naughty stable boy is doing”
I felt like going though a hole in the floor, but had no means of escape so just stood there, whip in hand, dressed in my black rubber outfit, with my cock poking out between the snaps in the fly front of the coat
“WHAT THE HELL DO YOU THINK YOU’RE DOING?”, barked Miss Sadie in her best ringmaster’s voice. “Masturbating in that outfit? You will be punished. Give me that whip right now”
Then she sent for her students and told them to”come in here and bring your crops with you”
Much to my embarrassment, in they came and ,pointing their crops at me, said things like “Now I know why he was staring at me so much”.”That’s why he fondled my crop all the time” etc.
When they were all assembled, the Boss took up my riding whip, made me take off my rubber coat and boots and indicated that I should undress and climb into the nearest bunk, “get down on all fours, then down on your elbows and stick your butt up in the air. Way up!”
When I was thus positioned, she gave me a sharp whack with the whip and, seeing a copy of Playboy beside the bunk bed, said “All right, now you are going to be punished for your naughty behavior. ”
So saying, she told one of the riders to get an empty tin can from the pantry and set it down on the bed infront of my erect penis. Then she stood by my left side facing my behind, put her left hand on my right shoulder and held me down to keep me on my elbows as she reached between my legs with her right hand and started to stroke my cock. As the girls gathered around to watch, the Boss stood next to Miss Sadie, and, facing my behind, placed one hand on my butt and started to poke my ass with the index finger of her other hand,
Then she told Daisy to “Go stand behind him and grab his balls. Squeeze them hard when I give the signal and try to dig your long fingernails into his scrotum”.
As she cupped my balls in her hand, the others all crowded around to get a better look.
“Watch closely now, ” she said,. He’s gonna squirt. His cock is TWITCHING!”
Indeed, as Miss Sadie stroked my cock harder and faster, I started to ejaculate. as she yelled “Squeeze!”
When Daisy squeezed my balls, I gasped and lunged forward as my cock spurted gobs of spunk
“Aim it at the tin can!” ordered the Boss Lady as I shot my load.
Alas, I missed and my gooy spunk gushed out all over the mattress.”All of it, Zack!” said the Boss Lady as she continued to milk my penis
“Now see what you’ve done”, said Miss Sadie giving me a hard swat with her whip.”You’ve messed up this nice clean bunk with your dirty sperm. You will be whipped for that.”
She then told the equestriennes to go ahead and “beat his butt with your crops till he’s good and red”
They took up positions on either side of the bunk bed with alacrity and plied their whips and corps on my poor behind. Daisy’s long flexible dressage whip hurt the most, and she applied it not only to my butt, but also my back and upper thighs till I couldn’t hold back my tears any more, and started to cry.
“Crybaby! Voyeur! Fetish slut! Naughty boy, Freakin’ masturbator, Bad! Bad! Bad naughty boy!”, yelled the Boss Lady as they whaled away at my butt.
WHACK WHACK WHACK
When they finally finished, I was made to get dressed. pack my things and leave immediately. All, that is, except my rubber hip boots, raincoat and whip, which Miss Sadie confiscated.
Then she went over and picked up the nearly empty tin can from the bunk bed’
Hmm, not much in there”, she said with a smirk as I fled out the door dragging my trunk behind me as fast as I could.

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