Being ridden and horse whipped by Clarissa

In the last year of my education mother decided that it would be good idea for me to take horse riding lessons, I cannot for the life of me remember why.  She purchased the riding kit and every Sunday for four months or so she drove me to a local riding school.  I was not particularly keen on the idea but I changed my mind on that first day when I set eyes on Clarissa, a girl several years older who was in our group.  What actually attracted me to her aside from her pretty but stern features was her gorgeous ass.  The way her tight fitting jodhpurs cut into her ass dividing her buttocks had me salivating.  She had long slender legs and a petite waist; her hair was done in a bun, which added to the severity of her looks.

On the following Sunday’s lesson I managed to position my horse behind hers as we rode around the barn going through various horsey tasks, my eyes rarely strayed from her ass.  At lesson end after the horses had been led back to the stables we found ourselves waiting silently side by side for our mothers to pick us up, hers in a large range rover, mine in our small car.  I was too shy to engage her in conversation.

The next two Sundays followed the same pattern of events.  I would manage to be behind her throughout the days lesson enjoying the sight of her buttocks rising and falling during the trot and canter.  Then on the fourth Sunday whilst waiting for our parents to pick us up she came over to me pinned me against the fence and quite openly said, “Are you fascinated by my horse’s ass or is it my ass you keep ogling at?” I was taken aback by her forthrightness.  I stammered something to the effect that her horse had a fine rear but I much preferred hers: my quip failed to amuse her.  Her mother having arrived just then came over and glancing towards me asked Clarissa had she made a new friend and to introduce me.  Clarissa wryly said yes, ‘this boy’ (humiliating me) is in our group and he is besotted with my rear.  Well then you must invite him over to tea next Sunday was her mothers smiling reply as she surveyed me from head to foot.

The following Sunday mother dropped me off, I having told her not to collect me, as I’ll be given a lift home after the tea. (She too was pleased I had made a friend).  That day Clarissa had driven to the school in her mother’s mini; and after the lesson was to drive me to her parent’s house, which she did, but not unbeknownst to me before she took a detour.  The detour took us to a woodland reserve where she parked the mini in a small lay by car park.  Having two or so hours to kill before teatime it transpired she had planned a ramble through her favourite woodland, and only now told me.  It sounded a good idea and I was more than happy to go along with it.  She removed a canvass rucksack from the mini and to my puzzlement her horsewhip.  The sight of that raised my curiosity but I said nothing, and she offered no reason.  

We followed a well-trodden path in silence for some time passing a few other ramblers along the way before turning off to a narrower path.  This too we followed for a short distance before again turning off onto a barely visible track brushing aside low branches as we went.  Then a short distance along the track she stopped turned abruptly around slapped the whip across her palm and ordered me to strip.  I was taken aback, intimidated by her stern expression I complied without objection (and hidden joy at the prospect of things to come).  When I was completely naked she ordered me to put all my clothes into a black cellophane bag that she had produced from her rucksack.  Having done that she then hid the bag under the branches of a fir tree.

She then took out two lengths of rope and having spun me around tied my wrists behind my back with one. Then knelt before me her fingers curled around my sack between my cock and balls she began squeezing and pulling down on my sack. It was painful, my body jerked in response and I let out an anguished cry.  “Shut up boy,” was her response.  Having stretched my balls she looped the second rope around my sack and pulled to tighten the hold.  Thus roped and now led by my balls we continued on.  I was in a dizzy state of excitement and trepidation as I was compelled to helplessly follow, my cock now erect like a water divining rod.  Occasionally she would glance back enjoying my captive sight and tug on the rope when I failed to keep up with her.  She was still dressed in her jodhpurs and brown leather-riding boots. Her jacket she had left in the car and now as we walked she removed her top briefly revealing a fine pair of well-developed breasts.  

After some time we came across an old fallen tree in a clearing, its trunk lay horizontal on the ground and its only two remaining branches either side were raised skyward as if in prayer; it looked quite ghostly.  I was made to lie face down along the trunk, its bark was coarse and grated against my chest and stomach; my erect cock sandwiched between it and my belly.  Using the rope by which she had led me she tied it to one ankle, looping it under the trunk pulling it tight and tying it to my other ankle.  My wrists were untied and the received the same treatment.  I was now tied hugging the trunk.

She straddled me facing my buttocks; the bark grated my stiff cock even more as she repeatedly and slowly raised and lowered her self on my lower back. I must have remonstrated for again I heard her say, “Shut up boy”.  I then felt her warm hand caressing my buttocks then a moment later heard the swishing sound of the whip and then a cracking sound followed by a burning sensation on my cheeks as she gave each cheek at least ten strokes.   My buttocks were burning and I know I cried out half way through as the pain increased. Unbeknownst to me at the time was that afterwards I realised that I had cum.

In the silence that followed I heard her say, “I too enjoy looking at naked buttocks of boys especially of those that have nice red whelps on them.  I don’t want you riding behind me again do you understand”.  I said I did and after a while she dismounted me.  I was expecting to be untied, but she took something out of her sack and seemed to fumble around for a short while before putting whatever it was back.

She then untied me, told me to lie on my back on the trunk (I dutifully complied) and retied me in the same manner.  My buttocks still burned and I was expecting that (wishfully hoping) she would remove her jodhpurs mount and fuck me, for my cock was stiffening.   Instead, placing her sack on my stomach she took out a pair off scissors a thin ribbon and a tape measure.  And standing by my side with a smile on her face said, “ Now I’m going to scalp you,” and before I could utter a word she had grabbed a solid clump of my pubic hair pulled it upwards stretching my skin and cut a clump clean with two to three cuts, holding it up to her eyes in satisfaction.  She then proceeded to tie the ribbon around to secure the clump of hair before putting it into the sack.  Then, sack discarded onto ground she sat on my stomach with her back to me and proceeded to clip away at my pubic hair.  My cock rose to full erection at the feel of the cold scissors and her hand periodically bending my cock forward out of the way of the scissors until she had me cropped.

Having finished me she grabbed my stiff shaft and I felt her fingers doing something and realised she was measuring my cock with the tape. Having finished she proceeded to give me a vigorous and rather painful wanking until I spurted uncontrollably.  She then dismounted went to her sack and took out a Polaroid instant camera and standing on top of the trunk facing me took a photo of me.  Satisfied with the photo she exclaimed in a business like tone “all done” put the camera back and untied me saying, “Teatime, mother will be waiting”.  We made our way back in hurried silence with me occasionally catching glimpses of her bouncing breasts whilst I carried her sack slung over my shoulder, ropes and crop in my hands: we were both dressed by the time we got into the mini and drove on to her home. It was a large detached property, father it turned out was a company director, they were well off.

Mother indeed was waiting, asking what had kept us.  Clarissa’s simple reply was that I had been slow in coming as she dashed upstairs to change.  Her mother led me into the lounge sat me down and poured me a cup of tea (which I badly needed as I was really thirsty by now) and placed a plate of biscuits in front of me.  I spent an awkward 20 minutes or so making small talk waiting for Clarissa to come down. Finally she did, and brought with her what looked like a photo album.  Handing it to her mother she smiled at me as she walked past and sat down.  Her mother opened the album and turned the few pages before exclaiming I see you have added another page before silently studying it whilst periodically glancing at me.  An uneasy feeling came over me and I hid my discomfort by pretending to drink from my now empty teacup.

Would you care to see Clarissa’s handiwork she asked handing me the closed album.  I opened to the first page.  Each page had four pockets to accommodate the Polaroid prints and there in the top two was a naked guy bound to a trunk of a tree - I recognised it instantly, in the first pocket a picture of him face down just as I had been his buttocks bore the signature of a dozen or so whelp marks. The second pocket contained a picture showing him on his back bound, and his pubic hair cropped. The bottom left pocket contained a clump of that cropped hair secured by a ribbon.  And the fourth pocket contained scoring notes indicating cock size and girth, whether he had cried out and whether or not he had cum, and an overall score out of five.  He apparently scored three.

In dumb silence I turned to the next page and again there was another guy, same two pictures, pubic hair memento and score.   The third was yet another and on the fourth page there was I.  As I stared at my photos and score - I achieved a four; I felt two sets of eyes intently looking on.  Given the surreal circumstances I found myself in and browsing through the pages my cock had stiffened.  Then I felt the mother’s hand resting on my crotch and proudly telling me with a smile it’s Clarissa’s new hobby that she had recently taken up, while giving my cock a gentle squeeze.  I think I just smiled muttered something that I no longer recall, and embarrassed asked if I could have another cup of tea (my throat had gone dry again).  Clarissa came over took the album from my hand and cradling it to her chest asked her mother if she would take me home, as she had to get ready for her date, she was already heading towards the door.

And so a short while later without having been able to say goodbye to Clarissa her mother drove me home.  I thanked her for the tea and Just as I had one leg out of the door she lent over placed her hand between my parted legs, fingers clasped around my balls saying I must come and have tea again sometime soon before releasing me, and with that we both departed.

Needless to say the invite never came.  As for the remaining riding lessons I made sure that I was either at the very back   

of the group or as near as.  Clarissa would glance at me occasionally with the faintest of smiles across her lips whilst we waited to be picked up, but we never spoke to each other again.  Her mother would smile and wave to me from inside the car before driving off.  I had another eight lessons or so before I gave up my horse riding altogether.