Penny In Harness

by Penny Birch

  Over the course of the week I increasingly came to want her at my feet in return. Ginny had told me the key to Amber’s submissive side, but the chance didn’t come; by the end of the week, I was beginning to consider abandoning the subtleties and just telling her to fetch the cane and get over the table. I know she’d have done it, but I also know she wouldn’t have taken full pleasure in it and so held back.

  What she did do was offer me the chance to be mistress to a pony-girl tack customer who had arranged to come up on the Sunday. The bulk of her customers were men, which she accepted with moderate grace as long as they kept buying tack. Oddly enough, it was the dominant males that she preferred; submissive male sexuality irritated her. Her closer male friends, like Anderson, were all men who were happy either way, the important thing being that they accepted that her interest in them was limited.

  She was explaining this to me on the Saturday evening as we lay together on her bed. I’d been spanked earlier, and was lying face down, fantasising about turning Amber’s bottom the same cheerful pink as mine was. She was very gently massaging my back and telling me about Sunday. The man coming the next day, apparently, was young, claimed to be good-looking and worked in the city. His fantasy was to be made over as a pony-boy and driven until he couldn’t go on, which Amber honestly admitted she couldn’t be bothered to do. I could see what she was hinting at and volunteered my services without hesitation. I felt I had watched her enough to make a passable job of it and was eager to try my hand at being mistress to a pony-boy. As far as he was concerned, then, I would be the fearsome Mistress Amber and she would just be the woman who did the leatherwork.

  The only difficulty, Amber explained, was that she had another customer coming in the afternoon. This was a woman called Anna Vale, who sounded absolutely terrifying, like Amber only without the softness. Amber had never met her, but they knew each other by reputation, both being lesbian and experts on old-fashioned clothing. So when Anna Vale — or Miss Vale, as she would expect me to call her — had decided to try a pony-girl fantasy with her girlfriend, Poppy, she had contacted Amber. Unlike Amber and me, Anna Vale’s relationship with Poppy never left the realms of fantasy. She wore styles from the 1930s and behaved accordingly, with Poppy as her maid. How she squared this in her mind with wanting Poppy as a pony-girl was beyond me, but Amber seemed keen to impress and wanted me to be her maid while Anna Vale was there. Anna Vale also despised men, unequivocally.

  I was perfectly happy with this, as long as I had Amber near me, but it would mean that we had to get the pony-boy, Chris Ford, out of the way and me changed before Anna Vale arrived at noon. I sleepily assured Amber that we’d manage, only to get a sharp smack on my unprepared bottom. Inevitably, this started the whole cycle of punishment and sex off again and it was another hour before we got to sleep.

  In the morning Amber had me getting into role the moment breakfast was finished. The first problem was that very little of her clothing fitted me. She had an impressive range of stern-looking dresses, also leather and rubber outfits and even a full set of studded body armour. In the end, we had to settle for riding gear, of which Amber had plenty of stock in the shop. We went to town, with corduroy jodhpurs and shiny black leather boots, a white blouse with a turquoise silk cravat, the traditional coat in hunting pink, a whip and hard hat. When Amber had applied a few carefully considered touches of make-up and I went to admire myself in the dining-room mirrors, I had to admit that I looked about as fierce as it is possible for a woman of my size and build to do.

  Chris Ford seemed to be impressed anyway, although he was so grovellingly subservient to us from the start that I suspect he’d have been impressed if I’d been wearing a gorilla costume. When he arrived, he was in the sort of expensive casuals rich young men affect nowadays. He looked every inch the confident, successful man-about-town: six foot odd; sharp, intelligent features; neat sandy hair and a Mercedes.

  I dare say he lived up to his looks in everyday life, but his attitude to me was positively worshipful. It gave me an immediate, and wonderful, feeling of power. The fact that all of a sudden I was no longer the little new playmate added to this; after all, for all he knew, I’d been doing it for years.

  He started by asking to call me ‘mistress’, but I refused him permission. Instead, I ordered him to address me as Miss Oakley, a bitchy touch I was sure Amber would appreciate. That seemed to cow him considerably, so I asked if he thought he was dressed properly to be a pony-boy. He obviously wasn’t and quickly admitted it, leaving me with the wonderful prospect of deciding what a handsome young man should have on. Amber may have been bored by the thought of controlling him; I wasn’t. I decided to have him strip, which appealed as I was already keen to see what his cock was like.

  ‘Then you had better strip, hadn’t you?’ I ordered, standing with my fists on my hips but sparing a glance for the workroom door, through which Amber had just gone. I knew full well that, in due course, I would be punished and humiliated in turn. Once he had left, I’d be lucky to keep my jodhpurs up for five minutes. When the time came, I would submit as meekly as ever. For now, I was in charge, and what Amber didn’t see, she couldn’t punish me for. Not unless I decided to tell her, anyway.

  Chris Ford, naked, certainly lived up to my expectations. He was lean and well muscled; his body was obviously toned by regular visits to a gym, not to mention a sunbed. He had nothing like the brute muscularity of Matthew Linslade, but then he didn’t work a farm. I was impressed, but kept my expression deliberately disdainful as my eyes travelled down his body, letting it turn to amusement at the sight of his genitals. Actually, they were quite impressive and my immediate instinct was to get down on my knees and suck his cock. Instead, I turned away, marching swiftly across the yard and snapping my fingers to indicate that he should follow.

  Amber had already made a harness for him, a straightforward affair that had actually been run up as a prototype for Mr Novak’s design. The leather was thick and hard, with a curious semi-gloss finish, not at all what I would have chosen for myself. He made no complaint. In fact, he simply watched dumbly as I examined the harness with a critical eye. I’d done some of the cutting myself and had made one or two tiny slips with the knife. I pointed these out to Amber, who bowed her head and apologised, although I caught a dangerous glint in her eye as she did it.

  ‘Harness him,’ I ordered Amber. This hadn’t been agreed on, but I was intent on working up a really good punishment for myself in the evening.

  ‘What’s your name, boy?’ I demanded as Amber fixed the waist belt around him.

  ‘Chris, Miss Oakley,’ he answered, looking nonplussed.

  ‘Your pony-boy name, idiot!’ I snapped back. ‘I know your real name. Do you think I’d forgotten? Do you think I’m an idiot?’

  ‘No, Miss Oakley,’ he stammered.

  ‘We’ll call you Flabby, then,’ I stated, choosing the name on the grounds that such an obvious fitness fanatic would certainly hate it. I was enjoying myself hugely and had never realised I could be such a bitch.

  ‘Yes, Miss Oakley,’ he answered, looking crestfallen.

  I immediately wanted to stroke his cheek and apologise. At the end of the day I’m not actually a very good sadist, but that didn’t mean I couldn’t act the part. Amber had fastened the waist belt in place and was getting the bridle ready. I watched as she pulled it over his head and began to tighten the buckles, the bit slipping between his teeth.

  ‘Well, Flabby,’ I continued, ‘I believe that you are to take me for a ride?’

  ‘Yes, Miss Oakley,’ he mumbled through the bit.

  I turned on him sharply. I had caught him with the oldest trick in the book. Well, not a trick really, because there’s no way around it. If he’d not answered I’d have had him for insufficient respect. He had answered and so I had him for talking after the bit was in his mouth. Amber constantly played it on me, and I knew how frustrating it is to have to do something but know that whatever you do leads to punishme
nt.

  ‘You spoke,’ I snapped. ‘Are you completely stupid?’

  He didn’t answer, of course, and I could see the expression of consternation on his face.

  ‘Well?’ I demanded.

  He still didn’t answer. Amber was fixing the last bridle strap, a short piece of leather that ran down the back of his head in place of hair rings. For a moment I thought she was going to start laughing and spoil it, but she managed to contain herself.

  ‘Right,’ I continued. ‘You will be punished for talking. You will be punished for insolence. You will be punished for stupidity. I suspect the whip will do little good, so I intend to drive you until you collapse.’

  Pretty neat, I thought, giving him his fantasy as a punishment, especially when I had thought the idea up on the spur of the moment.

  ‘Prepare the cart,’ I ordered Amber.

  ‘Yes,’ she replied, ‘of course.’

  ‘Yes, what?’ I snapped back at her.

  ‘Yes, Miss Oakley,’ she answered meekly, but again the look in her eye told a different story.

  ‘That’s better,’ I said. ‘Fetch a suitable whip as well, and you failed to lay out my gloves this morning.’

  ‘Yes, Miss Oakley,’ she answered.

  ‘Silly little girl,’ I remarked, not really addressing anybody. ‘I must whip her more often.’

  Amber went to fetch our cart, which we had got ready earlier. I threw Chris’s reins, or rather Flabby’s, over the hitching ring. There was a bit of a problem. We were more or less honour-bound to run Chris into the ground. He had, after all, bought his tack and we’d agreed to realise his fantasy. Unfortunately, he looked like the sort of man who ran up mountains for fun, while I weighed next to nothing. It was approaching ten o’clock, which meant I had two hours to wear him into submission before Anna Vale turned up. On the other hand, the men’s marathon record was just over two hours and he couldn’t be that good. Also, marathon runners don’t have to do it pulling girls in pony-carts, which is a pity really.

  We only had the paddock to drive in. It was enough for ordinary pony-girl games, but I could see myself getting bored just going round and round. Obviously something was needed to spice the event up and I was turning my imagination to the task as Amber brought the cart up. I accepted the pair of black leather gloves and the riding whip she had chosen for me, swishing it experimentally through the air as she attached his wrist cuffs to the cart.

  There was one obvious option; take him out cross-country. Not locally, of course, but there were some big areas of public woodland within twenty minutes’ drive, and if I put him in a pair of leather shorts we wouldn’t actually be breaking the law. I took Amber aside and explained my idea to her. She was uncertain at first, but agreed as long as I wore a veil and stuck to the loneliest section of the woods.

  Half an hour later, I was backing the horsebox into a lay-by and nervously checking around for watchers. Chris was in the back, invisible; to any casual observer, I just looked like a woman out for a morning’s ride. Over-dressed, perhaps, but quite innocent of any suggestion of sexual misbehaviour. A broad footpath led into the woods, apparently deserted. Working fast, I let the ramp down, ordered Flabby and the cart out and slammed it shut. I mounted the cart immediately, cracking the whip across his tight backside and setting him off at a run.

  I drove into the centre of the woods, my heart in my mouth but hugely enjoying the risk of being seen. Not that I could be recognised, as I now had a top hat and a black veil that completely hid my features. Actually, I quite wanted someone to see us, only not the sort of person who’d make a nuisance of themselves over it.

  It was also my first experience in the seat of a pony-cart, and it felt great to be on the giving end for a change. I could sit back as he pulled, watching the muscles in his back, bottom and legs work as he took the strain. A flick of my crop and a sharp word and he sped up, despite the fact that we were going up a shallow incline, pulling at a pace I doubt I could have managed myself.

  If the experience of being a pony-girl had been unexpectedly strong and had turned me on immediately, then the experience of being a driver was very different. I liked the feelings of power and control, even though they had been gifted to me. It was relaxing in a way, and certainly erotic, but with a far slower effect. Not that slow, though, and by the time we reached the centre of the woods I had begun to toy with the idea of taking my pleasure of my pony-boy in much the way Matthew Linslade had taken his pleasure with me on my first trip as a pony-girl.

  Flabby had worked up a good sweat on the slope and was beginning to breathe heavily. I estimated that we had done over a mile, mostly uphill and on fairly rough ground. I felt cool and relaxed, although the first bump we’d hit had punctured my composure. A dose of the whip and a few sharp words had ensured that it didn’t happen again.

  There was an area of large trees with open leaf-strewn ground between them to my left, and I turned him on to it. I was still undecided as to whether I should have him or not. There were condoms in my coat pocket and I knew he’d be delighted, so it was simply a question of whether I wanted it. It was wonderful to simply have that choice and, given that I could take it or leave it, I decided I might well take it. I hadn’t seen anybody at all, and so felt pretty secure as I drew the cart to a stop in the lee of a good-sized holly and dismounted.

  It actually takes a lot less courage to have sex with a man in the countryside than it does to strip and masturbate. After all, as a girl, you know that anybody who does see you will just think you’ve been persuaded into it by the rude and pushy male. OK, so maybe not when you’re dressed in riding gear and mounting a pony-boy, but I was probably going to do it anyway.

  I walked around the cart, admiring my mount. He was flushed from the exertion and breathing with deep, even draughts. The shorts, which were Amber’s, hung loosely around his buttocks but were tight on his waist and thighs — very tight over his cock. I remembered how good the same shorts looked filled with Amber’s more generous bottom and thighs and how it felt to kiss the taut seat. That decided me. I was definitely going to have him.

  Amber knew I had the option, she had even put the condoms in the coat pocket. The penalty for going ahead was being fucked myself, with her strap-on, another powerful inducement to go ahead.

  How to do it was a different matter. It’s easy to fuck a pony-girl. You order her to kneel and stick her bottom up and there pussy is, wet and ready to be filled. You don’t even have to unhitch her from the cart. With a pony-boy, it’s not so easy. I wanted to keep him in role and maintain my dignity, so I couldn’t just unhitch him and lie on the ground with my legs apart. I considered the problem for a moment and then ordered him to sit with his legs stuck out and his back propped up against the cart. That way I would be able to get on top, even though he’d be less than comfortable.

  He obeyed without hesitation and I came to stand over him, rubbing the tip of my whip against the bulge in the front of the shorts. His cock stirred inside the tight leather and I found my excitement rising fast. I leant down, popping open the button and easing the zip down. His cock sprang out, swelling quickly as it was released from restraint. To touch it would be to break my role, so I used the whip to stroke him. It stiffened quickly, rolling upright as it became engorged with blood, hardening into a rigid bar of flesh just suitable for my pussy.

  There is no dignified way to take a man’s cock in when you’re wearing jodhpurs. They have to come down and that’s it. I was going to have to squat over him with my knees up as if I was having a pee as well, an even less dignified prospect. I didn’t even want him to see my pussy, so I simply took off my hat and pulled it down over his face, leaving me with a nice cock to sit on and no disturbance from its owner.

  I pulled my jodhpurs down to the tops of my boots, listened for a final moment and then dropped my panties too. A testing finger found my pussy every bit as damp as it felt and so I squatted down on his thighs, his cock rearing in front of me, ready and waiting.
As an extra treat I decided to use my panties to give him a little wank. They were stretched tight between my knees, his cock lying against the part that normally covers my bum. He shuddered when I folded his shaft in the soft cotton and, for a moment, I thought he was going to come. Fortunately he didn’t and I began to jerk him into my panties while I slipped my other hand back between my legs and began to play with myself.

  Knowing he really would come if I wasn’t careful, I stopped after only a couple of dozen pulls and put the condom on him. I then took his shaft and raised myself, rubbing it against my pussy and then putting the head to my vagina. I had my eyes shut in bliss as I lowered myself on to him, my vagina filling with lovely hard cock until I was sitting on his thighs. My fingers found my clit and I began to frig, bouncing up and down on him to keep his cock moving in my pussy.

  I took my time, working myself to the edge of orgasm several times, never allowing him enough movement to come in me. I was delighting in not just the cock in my pussy and the fingers on my clit, but the whole atmosphere of the place. The smell of the woods, the warm sun on my bare buttocks, the helpless ecstasy of my mount. Only when I could feel the entrance to my vagina start to get sore did I focus my mind for my climax. I pictured what I was doing, controlling and mounting a strong young man; his body my plaything. I’d had him pull me through public woods, used a whip on his buttocks, given him a humiliating name and now wouldn’t even let him see my body as I used his cock to slide my pussy up and down on. It felt wonderfully powerful, me in total control. Of course when I’d used him, my lovely Amber would haul down my pants and spank me, then fuck me, maybe in front of him; yes, that would be the final humiliation. I’d be fucked over the kitchen table while he watched, with my bum up and a thick black strap-on dildo in my pussy.

  My orgasm hit me on that thought, making me shiver and cry out in the warm half-light of the wood. Even as I was coming, I was thinking that in the end I’d come over a submissive, lesbian fantasy for all my enjoyment in being in control of a man. He didn’t know, though, and that was what mattered. Even if he was my plaything, it seemed only fair to let him come, so I sat up straight on his cock and told him he could. He began to buck immediately, bouncing me up and down on his cock as if I weighed nothing at all. I had to grip the shafts of the cart to stay on as he got faster, then finally rammed himself right up me as he came.