Lost bet

"I think the time has come for us to take the lovely 'Pippa' downstairs, Ladies. Any objections?"

The three sexy girls looked knowingly from one to the other, finally looking to Helen my wife for her blessing.

"Let's do it. I really think I'm going to enjoy this and, who knows? Phil, I mean Pippa might too!"

I couldn't believe that I'd actually heard these words come out of Helen's mouth but secretly I was thrilled to know I would soon be totally helpless. Obedient to these people's every whim!

"Follow Mistress Jackie down the stairs, Pippa." Jerry ordered sternly. "Be careful not to trip up either, remember your new heels."

Gingerly and with my head bowed slightly, I began the journey that would forever change me and, the role I played in the bedroom with my wife Helen. Mistress Lisa followed close behind me, Master Jerry was next and closing up the rear was my lovely wife Helen. As we entered the dimly lit basement, I felt a surge of adrenaline pump through me, it was thrilling yet frightening all in one.

"Do you have any preferences, Ladies?" Jerry asked nonchalantly.

"Please Jerry," replied Mistress Lisa; "I'd like her over the spanking horse first, if you don't mind."

"Of course, a good starting place if I do say so myself." He replied.

In the middle of the floor was what looked like a shortened vaulting horse, the type of thing used by gymnasts. Instead of the two handgrips, though there was a kind of saddle built into the middle of it. It was wide enough for a person's waist and, lower ribcage to be comfortably placed over it. Underneath it, there was leather harnesses fixed firmly to a metal floor-pan fairly close together at the front and quite widely spaced at the back.

"Bend over the centre of the spanking saddle and, stretch your arms out in front of you." Ordered Mistress Lisa, who had obviously used the apparatus before now.

I complied immediately, a frisson moving down my spine.

"Helen, would you be as kind as to fasten his wrists in the cuffs? Jackie, do his ankles too, would you?" I heard Mistress Lisa instruct.

Before I knew it, I was securely fastened and unable to move from my supine position. Bent double and fastened, legs akimbo, holding my bum cheeks taut apart.

"Have you any birch twigs, Jerry?" asked Mistress Lisa innocently? "The sting is always preferable in a novice I find."

"We certainly do, Lisa," came a reply from Mistress Jackie. "I'll just fetch a couple. Would you like them long or short? Oh, and would you like them to be ones with lots of heads?" she asked knowingly.

"Long, I think I'd prefer and yes, the bushier the better. Young and springy, if you have any available."

Though I couldn't see her face, I could hear the anticipation in her voice. She was really looking forward to reddening my backside and thighs. Though I was now trembling a little with fright, my insides were tingling with expectation. I was going to be thrashed by a friend of my wife's whilst two strangers and she were going to watch and, all with her blessing!

"I think I'll leave her underwear on to begin with." Commented my tormentor. "Just so she knows what to expect."

"Would you gag her with that ball gag you showed me earlier?" I heard my wife ask Mistress Jackie.

I was stunned as I felt the hard rubber ball go into my mouth and be strapped tightly behind my neck.

"Thank-you" was all Mistress Helen said as it was done.

Within seconds, Mistress Jackie had handed two long birch twigs to Mistress Lisa and the scene was set to begin.

"You will now experience your first birching, Pippa." Explained Mistress Jackie as Mistress Lisa familiarised herself with the birch twig canes that she now had in her possession.

Though impossible for me to see, it was evident that she was practising her caning movements by the loud swishing noises through the air. Mistress Jackie continued to taunt me by saying;

"You can expect to learn the feel of this and several other instruments of punishment before we have finished your training, my girl. The slightest sign of disobedience or error will see you get a varied level of correction. Therefore, it is your best interest to do as you're told promptly and to the letter! Remember that slave, it will serve you well to do so."

With the ball gag still firmly in place, I was unable to respond, let alone plead for mercy. Suddenly and with no warning, I felt my thighs explode with pain and heat as the first blow hit home. I felt tears come to my eyes and panic rise inside of me. Thhhwwwackk! The air hissed as another hit its target.

"I think six will do to start with." I heard the voice of Master Jerry intone. "We want her compliant not unable to move."

The three Dominants nodded their agreement as another blow landed, right in between my arse cheeks. I wriggled as much as I could but was held fast by my bindings. A gurgle escaped from my throat as I tried to scream as loudly as I could, fighting the rubber ball in my mouth. The fourth, fifth and sixth landed in quick succession. My back fighting to arch as my wrists and ankles held it back, keeping me poised. Then all four left the room, letting me stew and ponder what had just occurred. Some twenty minutes later I heard steps and my true Mistress, Helen, my wife released me from my bonds.

"You're doing well, Pippa." Was all she said as she began rubbing cool moist cream into my wheals.

Just as I began to think that my ordeal might be over and that they'd had their fun with me, I felt the cold hard steel of a pair of handcuffs fasten themselves to my right wrist. Too shocked to struggle, I allowed her to cuff the other wrist to a second set. Both cuffs were attached to steel chains and I realised that a pulley was raising me. Though I hadn't realised, Mistress Jackie had returned and was hoisting me up until my arms were straight above me and my feet were just high enough to make my heels leave the floor, leaving me ever so slightly on tip toe.

"Now for a change of position we feel," uttered Master Jerry, as I felt the silky hands of two of the Dominatrix release the cock harness, adjusting it to make my semi hard member protrude from the front. "The ladies want to tease you a while so, I'm going to watch TV upstairs. Be good Pippa!"

Still gagged and helplessly hung from the ceiling winch, I shuddered as I saw my wife approach my dick holding some stinging nettles in her gloved hands. My butt plug was removed and a larger one inserted in its place.

"My darling husband, I'm enjoying this so much that I think we'll stay the whole week-end. Be a good girl and you might even get to enjoy it!" she laughed mercilessly as her two companions giggled menacingly.

I felt the nettles brush, ever so gently over my glands, almost tickling me. Then came the heat, the burning sting that those plants impart, swelling my cock to full hardness.

"Don't worry Darling, they'll do you no permanent harm," lulled my Mistress wife soothingly, "but they will enhance every little thing that we girls are going to do with you… And to you!"

I could feel my aching cock growing as it stung, throbbing as it grew in girth. My strength to keep my masculinity was rapidly diminishing and, I began to allow myself to enjoy my degradation. I felt the butt-plug being removed and shivered with relief.

"Move the 'chair' into position would you Lisa," said Mistress Jackie, "it's time for the next stage to begin."

I heard something heavy being dragged into position behind me then pushed into place under me, spreading my legs and lifting me off the floor. Looking down, I saw a large piece of furniture, somewhat similar to a chair or a stool but positioned in the middle of the seat there was a huge solid dildo, pointing straight up. To my horror and dismay, I then felt the backside of my harness being adjusted, giving free access to my bum hole. A pair of hands then held my cheeks apart as another liberally greased my anus with KY jelly, finishing by inserting a digit far into my hole.

"Lower away, slowly so that I can position her properly to receive her present." I heard Mistress Jackie say.

My body was lowered until I felt the cold hard tip of the dildo position itself at my rim. Gravity and my own body weight took over from there; as I felt the penis shaped object insert itself deep inside me, until I was sitting with it filling my insides.

"Are you beginning to get used to it yet, slave?" asked Mistress Lisa. "I hope you are, as it's something that will be happening to you regularly, I feel. Your loving Mistress, Helen seems to be enjoying herself." Mistress Jackie promptly replied to Lisa's comment saying, "Immensely if I'm the judge of anything!"

All three Dominatrices now began to play with each other in front of me, kissing, touching and licking each other's bodies. Instinctively, my cock started pumping and jerking. My arms still firmly held above me by the chains though, I was completely unable to touch my throbbing member, having instead to become more and more frustrated.

"Look girls, he's ready for us to play with!" I heard Mistress Jackie exclaim in glee. "Pippa, you must not, under any circumstances cum until you are told, is that clear?" she instructed me firmly. "We want to have some fun with you now and you must remain hard for the duration. If you fail in this, we will punish you severely!"

For the next forty minutes, I was teased mercilessly as all three of my captors lavished my straining dick with a variety of strokes, caresses, licks and kisses. Finally, the torment and wonder overcame my ability to restrain myself and I pumped my sticky seed over the lips and face of Mistress Jackie. Bereft of all logic, I felt awe at the power of my orgasm and yet a loathing at my inability to comply with my instructions. Mistress Jackie slapped my face suddenly and viciously. It stung terribly and brought me out of my orgasmic pleasure at once.

"How dare you? Did we tell you it was time? You'll pay for this! Lick this cum off my face at once!"

I had never tasted my own seed in this way and trembled as I fought to comply.

"Untie him girls. I have a suitably humiliating punishment for this pompous little slut!" She said as I finished cleaning her face with my tongue. "Bring the studded dog collar and leash too and, let's get Jerry. I think it's time he rejoined us. I believe that this will hurt our Pippa more than any physical torment we might inflict on her!"

She laughed raucously as she finished her sentence and looked at me with a glint of glee as she began to envisage my next stage of torment, terror and humiliation…

The Biker's Bar.

I was lead upstairs and ordered, in no uncertain terms, to get into the bathroom and freshen myself up.

"You'd better be sure that you look as feminine as you possibly can, Pippa. If you don't manage to pass as a real female slut, then this next task will surely be your undoing!" Remarked Master Jerry as he rejoined our little group.

As rapidly as I could, I entered the bathroom. I stripped off my clothing and showered, dried myself off and set about the task of becoming Pippa once again. The outfit that I had been given this time consisted entirely of leather and lace. My wife and Mistress Lisa insisted on tying me into the waist reducing corset. It managed to bring my waist down to an incredible 24" and, as it had all the lace ties at the rear, once they'd bound me into it, there was no way it could be removed without their help. It had the added effect of pushing my body fat upwards, forming small but very realistic boobs that just filled the three-quarter cups. It had its own suspenders which, I connected to the Cuban heeled silk stockings I was given. I very carefully made sure that the line was straight up the back of my legs. A leather cock harness hid my manhood between my legs and some lacy silk French knickers were put over it to hide the contraption. Thigh high boots with 5" heels were next, followed by a very short leather skirt. A sheer black halter covered my top and strong tarty make-up finished the effect. On with my wig! The transformation was complete. As soon as I'd finished my dressing and my making-up again, I stared into the mirror. My transformation was superb. Even I had difficulty believing it was a male standing there! Exiting the bathroom, I saw all four of my superiors waiting for me, Master Jerry let out a slow whistle and, my lovely wife complemented me on how well I had succeeded in my task.

"She looks just perfect," she said: "the perfect feminine slut!" Everybody else nodded knowingly as she stepped forward and put a collar around my neck, attaching a thin silver chain to a hook on the front of it. "Now for your surprise punishment." She said: "We're going out for a drink at the local pub."

I couldn't believe my ears, they had to be joking, and they were winding me up and trying to scare me. They were succeeding too.

"You will obey our instructions to the letter, slut. Don't for a moment think that we might hesitate to punish you, just because we're in a public place. We would and we will, should you falter in your obeisance. Should you outright refuse us anything, we may be forced to let slip a little something regarding your true gender!"

The trap was complete; nothing could make me disobey them now.

"Before we go, I think we need a little keepsake of how pretty you look." Said Mistress Lisa as she pulled out her camera and snapped off a couple of pictures of my female persona.

"Don't forget the video camera, Jerry." Slipped in Mistress Jackie as she pulled open the front door.