Born to Ride
A riding girl needs more than riding lessons
Born to Ride
I don't consider myself a bad girl, but I will let you judge for yourself. After reading my story, you might come to a different conclusion.
My name is Babette, but my friends just call me Babe. I am 25 years old and very aware of my sexy body. I sometimes wonder how many men have secretly jerked off with my picture in mind. I like to play and consider myself an expert at teasing. But I am not a slut, not at all. The truth is that I only had 2 (two!) real lovers in my life so far, one in college a few years ago, and one current lover. I will tell you more about my current affair later.
I better admit up front that I masturbate quite a lot. Sex fantasies really turn me on and touching myself is one of my favorite activities. I am very fond of horses and love to go riding. When I think it's safe I ride naked, like Lady Chatterley, one of my heroes. Should I get caught like this, I will get a good spanking or might even earn myself a trip to the barn for a whipping. But let me start at the beginning.
Luckily my parents are kind of wealthy, so I grew up on an estate complete with private horse stable. Once I got older I discovered the pleasure of grinding my pussy in the leather saddle and I began taking long rides by myself. But I had to be careful. My mom always insisted that I wear proper riding pants, you know, the tight beige ones that fit like a second skin over a girl's behind.
One day, I had a really wet orgasm and the stain showed on the front of my pants, between my legs. For some reason my mom saw it and I received my first whipping. She made me pull my pants down and I had to bend over a sawhorse. I got twenty lashes with a riding crop on my bare bottom. Each one made me scream out loud, believe me. But later that night, in my room, I looked at the welts on my ass in the mirror and masturbated until I had another orgasm. I discovered that the "afterglow" of a whipping was a real turn-on.
To prevent getting caught with stained riding pants, I began riding naked, taking off my pants once I was by myself in the woods. Besides grinding my pussy, I began using my fingers, leaning forward and reaching behind with one arm. For some reason I liked touching myself from behind, although that was more difficult. Sometimes I already had one orgasm by the time I reached my special, secret place in the woods; a little clearing with a big tree in the middle for shade.
I always had a blanket with me and sometimes I just took a nap there. But mostly I indulged in my sexual fantasies. For example, I used a leather strap to spank myself. It took some practice to land the smacks on my ass so that there would be some welts. Even though it hurt like hell I seemed to be unable to stop. The only thing that could relieve me was another orgasm. Afterwards I often thought myself stupid, looking at my bruised behind. But the glowing heat that lingered on my bottom was a pleasant feeling.
And then one day the unspeakable happened: I got caught. I hadn't noticed the man on the horse because I was so absorbed spanking myself with the strap. It was Mr. Darrell who owned a large estate close to ours. I had met him only twice before. My face turned red with shame and I didn't know what to say. He didn't seem shocked at all and asked about my name. I stammered "Babette" as good as I could and watched him dismounting his horse. The next thing he said I will never forget:
"Well, Babette, I know a thing or two about naughty girls. I consider it my duty to do you a favor. Hand me the strap. I will teach you what a real whipping is like."
He took me to a recently felled tree, and threw the blanket over it. I had to put myself face down over it, with my naked bottom displayed on the very top. I was afraid and nervous, but also kind of excited. Then the first smack exploded on my ass with unbelievable force! From the corner of my eye I saw Mr. Darrel raising the leather strap high over his head and lashing it across my bottom as hard as he could. The pain made me scream and after ten lashes my tears were blinding my eyes.
He whipped me methodically, not saying a word, sometimes left, sometimes right, sometimes squarely across my ass. I lost count after twenty, but I think he administered a full one hundred lashes this way. Then he helped me up, handed me a tissue so I could wipe away my tears, and gave me back my leather strap. He said good bye and rode off.
For a while I was afraid he would tell. But Mr. Darrell kept it for himself. It was our secret. From then on he watched me masturbating from a distance, through his binoculars. I only talked to him a few times after the initial whipping. On one occasion, I handed him my riding crop and bent over for him. I learned quickly that Mr. Darrell did not have a playful attitude when it came to punishment. He whipped my ass methodically, without saying a word. There were a few subsequent encounters where I got over his lap and he spanked me with his hand. Even that hurt like hell initially, but the rewarding afterglow was worth it all.
When I was in college I could hardly wait for the summer breaks. I missed riding my horse. And to some extent I missed my secret encounters with Mr. Darrell. Because my parents were often out of town during summers, I was able to ride naked even at home during my breaks. Yes, I did have a boyfriend in college at the time, my first lover. A sweet boy named Robert. Unfortunately he was not very experienced. He spanked me when I asked him to, but he thought that was weird. And then he usually came within two minutes and it was over with. I had to use my hand anyway.
More and more I fantasized about Mr. Darrell making love to me. In one of my fantasies, I see myself bending over the sawhorse in the stable and Mr. Darrell fucks me from behind, spanking my ass at the same time. At the moment I reach orgasm, he withdraws and sprays his cum on my flaming bottom cheeks. He spreads it evenly across my ass and then he picks up the leather strap. After a sound whipping of no less than fifty cracking lashes he takes me again from behind...and again.
One day I couldn't stand it any longer and decided to visit Mr. Darrell. I called him first and he was surprised to hear from me. I guess he thought that I was happy with a same age boyfriend. Mr. Darrell is about twenty years older than I am and he probably thought I wasn't interested. I found out that he was by himself, how lucky! When I got there he showed me his place and we talked. His first name is Henri and to my surprise he was a little nervous at first. To get things going I asked him to help me improve my riding posture. I made sure he got a good view of my ass before I mounted the horse. Henri, an expert equestrian, knew all the right training methods to improve my posture.
He held the reigns of the horse by a rope about fifteen feet in length. In the other hand he held a long dressage whip the same length. I rode in a circle, very much like in a circus show, except that my naked ass was bouncing in the leather saddle. First he taught me to sit straight, with the small of my back arched inward. That gave my riding a very elegant and at the same time a slightly arrogant look. I liked it. The second pose he taught me was much more unconventional. I had to stand up in the stirrups and lean forward.
Keeping my legs straight he asked me to arch my back like a cat, so that I presented my naked ass in the most lewd manner possible. A cracking smack rang out and the pain made me wince. I recovered quickly though and lifted my ass with pride. He continued using the dressage whip to print countless stripes across my bottom. By the time my lesson was over I was exhausted and my body was covered with sweat.
Henri gave me a few minutes to catch my breath. Then he touched me for the first time. He ran his hand over my breasts, squeezing them lightly, then pinching them until my nipples were stiff. I kept my eyes closed and I was moaning rather shamelessly I have to admit. He pushed his finger into my pussy and I spread my legs for him. I moved my hips in rhythm with his finger and had an immediate orgasm. In a sense I still behaved like a girl.
I opened my eyes: "I need to be fucked," I told him.
Henri asked me to turn around and to get on my hands and knees. He pushed his cock into me from behind, so deep that I was gasping for air. With one hand he gripped me by my shoulder, I felt like an animal in his claws. Then he spanked my ass while he fucked me, just like in my fantasies! Henri told me how pretty the whip-welts looked on my bottom and that a girl like me ought to get whipped all the time. He made me come three times in a row, something I thought impossible before.
But Henri didn't whip me again until the stripes on my ass had completely faded. He put soothing Aloe Vera gel on my behind every day. Every time he nursed my backside I got face down over his lap and enjoyed him squeezing my bottom cheeks and stroking my pussy. Although he wouldn't whip me he had no problem spanking me with his hand. And after each spanking Henri made love to me. I felt like I was in heaven.
Once my bottom was smooth Henri suggested to document my next whipping. First he took a "before" picture of my backside. Standing up with my legs slightly spread, I arched the small off my back to make my bottom cheeks swell proud. Henri thought that was very arrogant of me and that he would punish me extra for that. Oh well!
The second picture shows me bending over a padded saw horse. My arms and legs are tied so that I won't move. My bulging ass cheeks are spread in all their youthful glory, waiting to be whipped. My pussy looks glistening wet and wide open because Henri just got done fucking me. Sticky cum was oozing down on the insides of my upper thighs.
The next pictures chronicle my punishment in stages. First, ten horizontal, blazing stripes. Printed across my ass with a riding crop. Twenty diagonal lashes, ten from each side, created a criss-cross pattern of red welts with white spots in between where my bottom wasn't touched. Next I got the strap, to take care of the white spots. My bottom was already sore and I was screaming after each cracking smack.
In the next picture my whole bottom looks crimson, a kind of glowing red. Ignoring my protests, Henri picked up the dressage whip. He put a wind-up clock on the floor in front of me so that I could see it. For the next half hour, every time the second hand passed another minute I got a lash with the dressage whip across my glowing behind! The final picture shows thirty vicious welts from the dressage whip criss-crossing my crimson ass and thighs. There is cum dripping out of my pussy again. Yes, Henri fucked me immediately after he was done punishing me.
It took two weeks and a lot of Aloe Vera gel for my bottom to recover after that whipping. The pictures, enlarged and nicely framed, are hanging in Henri's bedroom. I kind of live at Henri's place most of the time now. I didn't really move in, but I spend many nights there, in his bedroom.
Sometimes I look at the pictures and wonder what it is in me that makes me submit to such an ordeal. Henri never whipped me like that again. But every night I get spanked over his lap. Since he has a hand made of iron, I am quite content with that. Only once in a while I hand him a leather strap and then Henri knows what to do. And it turned out that there was something I could teach Henri. I showed him how to eat my pussy properly, with his mouth wide open so that his tongue can reach deep inside me. Hour after hour...
Now I can ride my horse naked all the time. I can masturbate during the day knowing that I do Henri a favor. We even talked about marriage, but decided against that. It wouldn't work, my parents are not that liberal and I don't want to loose their love. We shall see what happens. Right now I'm just happy and content. Maybe one day a man my age comes along who will strike my fancy. But I'm not desperate or actively looking. Henri, besides pleasing me sexually, is teaching me a lot about the world.
And we have frequent adventures, going on trips out of the country. I have climaxed on an airplane (don't ask) and while driving a convertible car, sitting with my bare bottom on the leather seat. My favorite leather strap always travels with us. Sometimes I get it before we go out, sometimes after. When he takes me out to a fancy restaurant I never wear any panties under my skirt. And I always wear skirts. They are easy to flip up when I sit down.