Lost Bet-Part 5 By Pippa

"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.

"Just one last thing that you should know, Pippa." Said Master Jerry glibly. "The pub that we're going to is a Biker's Bar. I don't think that they'd be too impressed if they found out that you have a dick hidden between your legs. Let's go girls." He smirked at my patently obvious horror, as I was lead into the street.

Blushing visibly through my make-up, I considered running away and ending this horror but remembering the photos soon put paid to that idea. I couldn't believe that this was actually happening to me. My mind was racing with fright as I thought of the serious assault that would surely come my way, if and when I was discovered! I shuddered involuntarily at the scene in my mind!

"There it is." Signalled Master Jerry, as he pointed to the next corner on the street. "It looks like it’s pretty busy too, if you stop to consider the amount of bikes that are in the car park."

The place was loud and rough looking with large car parks both front and back. The rear car parks lead into a garden area that was dark and seemed woody, with trees surrounding the drinking area. My mind raced as my wife turned and said to us all:

"Looks like fun to be had by all! Pippa my darling, I shall make sure that you have a night to remember. In fact I shall make sure it's all on videotape so that you can't forget it… even if you want to!" She laughed mercilessly as a gleam shot through her eyes.

"We have to buy tickets at the door because there's a live band tonight. I think that we ought to let Pippa do that for us, don't you?" asked Mistress Jackie nonchalantly.

"What an excellent idea!" Replied Mistress Lisa immediately, grinning ear to ear.

She shoved the small of my back, propelling me toward the great ape of a man who was selling the tickets at the door. He looked me up and down, taking in my style of dress and said:

"Well, well, lookie here! What can I do for you little miss? Maybe later I'll ask you what you can do for me."

He guffawed at his own base humour then grabbed my arse.

"How many then?"

I showed him my five digits so that I wouldn't have to speak and, as I pulled the money from my tiny purse, my lipstick fell to the floor.

"Don't bend your knees Pippa, but pick that up immediately!" Ordered Mistress Helen, my wife.

I blushed profusely as I tried not to show my panties whilst having to bend, my arse toward the door attendants. I felt hands stroking my butt as I retrieved the lipstick, straightened up and hurried to take the tickets from the big guy’s hand.

"Maybe that will teach you to be more careful Pippa." I felt a tug on the leash attached to my collar. "Believe me when I tell you that even the smallest of errors will be used as a tool to humiliate and humble you." Instructed Mistress Jackie.

"Of course, we will also find it entertaining as we watch you squirm." Added Master Jerry.

"In fact, we'll be looking for any opportunity, darling." Said my wife.

"To be honest, we want to see how much we can make you squirm, Pippa" finished Mistress Lisa as she delivered a sharp stinging smack to my bottom cheeks. "You are, after all our humble plaything, servant and slave 'girl', aren't you dear?"

Surreptitiously, my wife pulled me close and whispered in my ear:

"I love you very much, Darling. I just want to thank you for being such a good girl for me. I'll never forget it. You've made me so proud and so happy."

This short sentence made me glow inside. I knew now that I was doing the right thing, no matter how difficult, painful or humiliating the things I was made to do had made me feel. As we entered the dance hall, the thudding of the base ran through me and I felt my nipples become erect. It was dark, busy and humming with intoxicated bikers, both male and female. I drew a good few looks, both for the sexiness of my appearance and for the collar and leash that I was being forced to wear. Thankfully, Master Jerry had been to the bar and bought us all drinks. My neck felt the tug on my collar as we made our way to the front of the crowd right up next to the stage.

"Excellent!" I heard Master Jerry exclaim, "I know this group. The lead guitarist and I are drinking buddies. Wait her a moment, will you. I just need a quiet word in his ear."

I thought nothing more of it as the ladies chatted amongst themselves, every so often stopping to pat my bum or, to stroke my breasts. They made it very obvious each time they did, attracting more attention from the guys in the crowd. Mistress Lisa spotted a coat hook screwed into the wall by the side of the stage and, after some whispers between herself and my wife, I was taken there and my leach tied to the hook.

"You will stay here until we fetch you, my love." Stated Mistress Helen. "You will allow yourself to receive any attention that you are given. No matter who by. We will be keeping an eye on you. We're only six feet away. Have fun, Pippa." At that, she walked away, leaving me feeling very vulnerable.

Less than a minute later, Mistress Jackie appeared with the rubber ball-gag that she had used on me earlier. As she attached it to me, forcing my lips and mouth open, she said conspiratorially:

"This will make sure you don't have to speak, so that you don't give yourself away. I'm being kind to you Pippa, really I am." With that, she strode off, back to the other girls.

It didn't take long for me to start getting attention. I felt hands stroking my bum, lifting up my skirt and grabbing my titties. A couple of the guys actually licked my lips round the ball-gag. It wasn't until someone started trying to strip me that Mistress' Lisa and Jackie came along to retrieve me. I was handed over to Master Jerry and I began to think that we might be on our way back to their house. I couldn't have been more mistaken.

"It seems that you're attracting the wrong sort of attention, Pippa. So, I've had a word with my friends in the band and they've agreed to let you be a little stage decoration for them."

I couldn't believe my ears but sure enough, I was being led backstage and up the stairs. As the band finished their set, Master Jerry led me through some curtains and on to the stage. He led me to a lighting rig, which had been situated centre stage and proceeded to handcuff my wrists. My arms were raised above my head and the cuffs placed over a bar holding me in place, in full view of the entire audience.

"Don't move about too much, Pippa. If this rig falls on you, it'll probably mean a trip to the hospital!" With that, Master Jerry left, returning to the ladies and to his drink.

To say I felt humiliated would have been the understatement of the year. I could see some of the bikers pointing at me and laughing, others were leering and I could hear wolf whistles and catcalls. The band returned and thus I stayed until the end of their next set. Mistress Jackie came and released me and I was led through the throng of hot, sweaty bodies to a fire exit where the rest of our group was waiting.

"You did very well, Pippa. As a reward, we've decided to let you eat out Mistress Lisa in the garden. I will video the whole thing for posterity, so make sure you do it well." Resounded Master Jerry's voice. "I shall lay out a blanket for you so that you don't dirty your clothes. I've asked the landlord to switch on the car park lights, so make sure you're quick and you might not be seen. The band's last set takes 30 minutes." He grinned wickedly as Mistress Lisa lay back on one of the tables and removed her panties.

"Get to it girl," She said: "I'm feeling good and randy!"

I knelt on the blanket and buried my face between her legs, working my tongue like a rabid animal, thrusting, probing and licking with a passion. She was soon bucking on my face as her cream covered my face in its sticky goo.

"Well done Pippa, you're becoming quite the expert. Now tidy yourself up. We've called that nice cab driver that brought us to Jackie and Jerry's earlier."

I knew what that meant and shuddered as I prepared myself for another mouthful of jism. Sure enough, the fare was paid in the same way, though this time Master Jerry caught it all on video. This time though, I managed to swallow the lot, even licking the residue from the drivers throbbing pink head. We arrived back at the house, I was led straight to the dungeon where I was cuffed to the wall, and left to ponder what was next.