Ellen
It was a late October evening, and I was feeling blue. Skinny, tall, shy and awkward with the girls, addicted to pain, at 19 I did not really had a girlfriend. With my shorts and my briefs around my ankles, I was massaging gently my ball sack and semi hard penis, wondering what the future will bring.
Mother was a big believer on corporal discipline, and as English descendent, a good canning on the bare buttocks was her answer to any rebellion. Her favorite position was the "diaper" position. The wide parted legs, held high in the air, exposing the genitals and butt hole added to the humiliation and offered a variety of places where the cane could land. The cane, held by an expert hand will strike the pale, unblemished skin, and almost immediately she will be rewarded with the appearance of these beautiful and unmistakably red tramlines, which will change color almost instantly when you look at them to angry red and then to angry reddish purple. For more minor offenses, a wooden spoon was used, still on the bare, but wrapped over her lap, leaving just red and purple blotches. But my obvious pubic hair started to make her uncomfortable to put me in those positions and she also could not be ignoring my big erections anymore.
As a teenager, our house was kept warm all summer and cold in winter to save money on electricity. During the summer time I enjoyed being naked when Mother was at work, sunbathing nude. When the winter came, when home alone I run outside butt naked and take snow on my hands, holding it against my inflamed dick. Also I took the big, thick icicles from the eaves and warming them a little I placed them between my buttocks cooling my asshole and testicles. Soon, shivering, I ran back in the house, jump in the warm bath I prepared beforehand. After 2 min warmouth I get out and furiously hit my wet ass and thighs with my doubled leather belt as a well deserved punishment for the blossoming perverted carnal desires. Wearing winter clothes covered my red and sometimes purple welts where the buckle made contact with my naked flesh. My grades fell, to Mother great disappointment. She searched for a year for someone who can tutor me whiteout breaking the bank.
Mother was so relieved when Mrs Duncan, who lived next door, suggested she and her daughter Clarisse are willing to help me improve my grades and get into a good college with the condition to be able to use their methods. Mother enthusiastically agreed, and gave her and Clarisse permission to use the cane on my bare ass when I did not do well on my work. Good God, both of them took every opportunity to enjoy themselves doing it.
The two of them explained to me that Clarisse reported weekly to Mother about my academic progress and when I got punished and why. The decision was, if I get any bad grades Mother will look for a new tutor. Because Mother also thinks an occasional motivational spanking with "just" the hairbrush helps with the focus, she paid Clarisse extra for helping her with that.
We always started the lessons with me kneeling, legs apart holding the cane on my mouth. Palms open, at shoulder level, waiting for the half dozen cane strikes on each palm. Clarisse thought those greatly improved my attention. Mrs Duncan, suggested that to Mother when I started tutoring and Mother gladly accepted
In the beginning Mrs Duncan supervised Clarisse, making sure she was not too lenient, but she stopped after she was happy with her daughter proficiency with the cane on both palms and buttocks.
Later Clarisse make me strip naked for the lessons, to help me focus (on my raging erection or embarrass me of the precum leaking in abundance? ) and always the cane was prominently displayed.
She also convinced both Mother and Mrs Duncan my unruly pubic hair was unsightly and gave me too much pride. Mother decided to let Clarisse use a sugar sticky paste to remove any trace of hair on my pubes and on my ass crack. The process was painful and humiliating, Clarisse gloved hand probing every crevice and skin fold, pulled the hair slowly just to torture me , and always "by mistake" will end with 2 fingers in my rectum when her other hand was squishing my testicles. That is the only part I didn't miss when Clarisse joined the Marines
Clarisse also offered me some learning "undisclosed incentives" without Mrs Duncan or Mother's knowledge, which no teenager boy will ever resist: she will show me her perky boobs, panty covered ass, naked ass, pussy, and as the ultimate perk was to let me lick her shaved slit if I was doing very well. The former will happen almost every day, after good academic performance, the latter, which involved licking clean of her juicy lady's parts, happened on Friday.
On Friday evenings, completely nude I climbed over the lap of the gorgeous teenager female, completely nude. Her lap was protected by a towel from my usual abundant precum when I got spanked. Clarisse arrange my position so my hardened dick would get in between her muscular tights, but safely separated by the thick towel, just in case of an "accident". When she was happy with my position, she pinned my right arm behind my back and methodically, without rushing, covered both my buttocks with hard hairbrush strokes. In no time, my entire rear end was blazing red with some purple bruises from Clarisse's motivational encounter with the oak hairbrush. After she was happy with her handiwork she will let me up, wipe my raging member clean with the towel, lay back with her legs open almost in a split and always asked: Are you ready for your treat tonight?"
Hungrily, I lapped at the virgin pussy with enthusiasm, savoring her freely flowing womanly juices. After her two orgasms, she will vigorously jerk my hopeless hard cock, and let me spurt on her wiggling back and buttocks. Once done, she make me clean her, eating my own spunk, and when I was done she parted her buttocks letting me lick her asshole for a new orgasm.
I was in heaven, my grades became excellent, and Mother gave Clarisse a nice Christmas gift until Clarisse went and joined the Marines, leaving an un-consoled 17 year old boy.
At 18 I left for college, Mother being very pleased I got full scholarship at a good college, and I got a small efficiency apartment in a nice apartment complex.
I found the girls my age immature trollops, behaving badly, drinking too much, dressing not to the standards of elegance Clarisse accustomed me to, showing crazy hairdos or tattoos. Also during those years I associate nudity and sex with pain in a wonderful whirlwind of sensations, but really I never put my dick inside any woman.
Hornier than usual, I remembered the complex have a private swimming pool, now closed for the winter. That would allow me to do some self spanking without fear of bring heard by any noisy neighbor. Just the thought of the further pleasures made my dick to start leaking!
I took the 3 foot length of 3/4 full grain leather I use to punish my tights and ass when masturbating and weighted in my hand, and stroke my left palm. Oh, yes! That would hurt soo good.
I have customize it by placing 6 3/8 inch round head rivets every 2 inches for a foot on one end and 1/2 inch rivets every 2.5 inch for a foot on the other end. That allowed me for painful hits without a lot of noise.
After putting some clean shorts and briefs I headed to the closed swimming pool of the complex. I looked and did not see or hear anybody, so I dropped my shorts, briefs and T-Shirt on the floor, with fond memories of times this act would gain me 6 of the best purple stripes on my ass. My dick was already rock hard, begging for attention. I carefully went on all fours, legs widely parted. Start swinging the strap end with the heavier rivets aiming at my naked buttocks. The pain feels so good, and I wish I could swing harder. But I am scared of the noise, so kept swinging and hope the pain will build. The issue was I did not have in that position a free hand to masturbate. I went to lie on my back. Eyes closed, with legs high in the air striking my thighs with the strap in my left hand and stroking my dick with my right. Felt good and took me like 10 minutes to squirt my seed on my stomach. Was not one of Clarisse sessions, but was all I had.
I opened my eyes and almost fainted: An older woman, blond hair tied in a ponytail, red yoga pants hugging a decent size firm ass, and sports bra holding her small tits, was sitting cross-legged in front of me. Her piercing ice blue eyes sparkled in the low light. She was close enough she could have grabbed the strap if she wanted and definitely did not miss any detail of the spectacle I was offering.
I was petrified! She got up effortlessly, dipped her fingers in the spilled cum on my stomach, wiped her fingers on my lips, and then bent over and kissed me, her tongue getting deep into my mouth.
Then she pulled a card from her pocket and put it in my open mouth, and said with a soft, sultry voice:
Tomorrow morning at 7 sharp. Don't be late; I don't like my breakfast cold.
Then, casually, she slapped my softened dick with her open hand and gracefully walked away. I was stunned. Got up and scooped the cum from my stomach and lick it. Look at the card: Was very simple, the name Ellen, a stylized whip and a address, in my apartment complex, but in the area next to the golf course where were 4 town houses.
Cleaned quick the cum left on my belly with my fingers, licking the spunk clean .Put my clothes on in a hurry and followed Ellen. She was enjoying her walk, stopping sometimes to listen to the birds. I did not want to get too close but I did not have any experience on covert investigations.
Ellen turned to me, with a big smile, and asked if I was sure I cannot wait until the morning.
I turned redder than her yoga pants, and starred at the camel toe I could clearly now see in top of her tight gap.
