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Lost Bet

Gamble gone wrong

Lost Bet

By Pippa©


It all began as a bit of a joke really. We'd all been out clubbing in some raunchy night-stops and were still high on the atmosphere. As the night wore on and morning was quickly rearing its bright and beautiful head, the group began to dwindle until only three of us were left. My husband Phil, my best mate Lisa and of course me. My name is Helen and what follows is a story that we three will never forget.


Lisa lived far away so, we invited her to stay at our place. She readily agreed but pointed out that none of us could sleep yet, even though it was already nearly 9 AM!


"Why don't we play some cards?" Lisa suggested, a twinkle appearing in her eyes.


We agreed and were soon lying around the living room floor. The sounds of the Trance music in the background sounded sexy and rhythmic. I knew Lisa well and wondered what she had planned!


"Do you feel lucky tonight?" Lisa joked. "Why don't we make it interesting? You're not shy people are you? Neither am I so, let’s play for our clothing!"


My husband Phil and I like a challenge and, we still felt horny from the dove. We nodded to each other and Phil said:


"Okay." Adding slyly, "But, let's make it really interesting. Unless you're scared of a bit of a real gamble!" continued Phil. "Whoever loses must do a forfeit of the other two's choice. No backing out and, anything goes."


Lisa didn't bat an eyelid. She just smiled and nodded her assent. Phil looked at me. I was a little nervous but nodded too.


Phil really thought it was going his way to begin with. He'd not lost a hand and, both Lisa and I were in our undies already.


"I'm going to really enjoy being your Master when you lose." Phil said to Lisa cockily. Obviously feeling very sure of himself.


"You have to win first" Replied Lisa, looking equally confident.


As she said it, Phil's luck seemed to turn. He lost continuously until he was only wearing his boxer shorts. The next two hands saw Lisa and I both topless and now it really was 'Game-on'. The last hand was nerve wracking but to his amazement, Phil lost!


"Off, off, off…" She chanted.


I found myself joining in, egging him to lose them.


"Okay, Okay, here they come!"


Smiling, Phil dropped his shorts to the floor. He was semi-erect and, obviously thinking he had it made, either way.


"Go and get us some more drinks." Ordered Lisa. "And don't come back for 10 minutes. Helen and I need to discuss your forfeit!"


Phil left for the kitchen, closing the door behind him.


"Helen, what I am about to suggest may sound a little strange to you but hear me out I think I know a way to put a little dent in all that ego." Lisa smiled knowingly. "Have you ever wanted to be served on, hand and foot? By a French-maid, complete with tarty little uniform, sexy undies, the lot?"


I was a little taken aback but I did find the idea amusing.


"You want to make Phil into a French-maid?"


I giggled. I could almost picture his face when we told him what he had to do!


"Let's do it!" I cried.


That was the fateful moment that I discovered a new me and …a new Phil!


"Okay Phil, bring us our drinks!" I shouted to the kitchen. "We have a little surprise for you."


He swaggered into the room, a drink in each hand and, his prick sticking right out in front of him, as hard as rock.


"So, which one of you wants me first?" Sure, he knew what was to come.


"Neither just yet, we have to prepare you for your role" I told him firmly.


Lisa helped me get him into the bathroom where, I tied his hands to the rails, leaving him helpless. Next, I got out my Immac depilatory crème and, covered his entire body, right up to his neck in it. We left him alone like that for 20 minutes and, went out for our drinks. When we returned, I let him loose and made him shower it off. As the crème washed away, so did his hair, leaving him smooth as a baby's bottom! Phil was less sure now and, complained a little as I tied him up again, this time strapping his arms and legs to the chair by the mirror. I shaved his facial hair and then decided to pluck his eyebrows, thin and shapely. Next, a thick layer of foundation was applied to his face and neck; the canvas was ready. I handed control over to Lisa, who immediately started his make-up. Some mousse helped us change his longish hair into a more feminine looking style. Things were getting interesting!


A few years before all this took place, I'd been a much fuller figured woman and, I was now pleased I'd kept some of my clothes in the back of one of the cupboards. I sorted out what I had whilst Lisa finished the revamp and paint job on Phil. She was obviously taking the whole thing quite seriously. First, she covered his face in a light foundation, making sure to have covered Phil's facial hair areas quite liberally; next, she put on some kohl eye liner and a heavy dose of 'lash-lengthening' mascara. She applied an eye-catching effect on his lids; narrowing his eyes slightly and making them look stunning. She stood back to take in the effect and, followed up by applying blusher to his cheekbones. Now for his lips she thought carefully as she outlined his mouth, making it pout sexily and, filling it in with 2 different types of red and some 'high-gloss' over the top. The finished product was quite amazing, my husband really looked like a sexy woman!


I found my old waist-reducing corset; hold up stockings with a Cuban heel, panties and a sports bra. "Just what I was looking for." I whispered to myself, gloating at Phil's unexpected turn of events. Now for the top layer, I thought to myself. Digging deep, I found some of the sexy outfits that I'd bought to entertain Phil in those days.


"Yes!" I cried. "I knew it was still here somewhere." I'd found the 'Anne Summers' French Maid outfit that I'd bought some 5 years before. "This'll top it off perfectly!"


When I returned I was shocked at how well the transformation had gone. Lisa had completed the effect by varnishing Phil's nails – Hand and foot!


"Your forfeit will be as follows: You will dress as a French-Maid following which, you will serve the two of us, and however we deign to be correct. You will obey our every whim, to the letter. If you should fail to please us in any way, you will be disciplined. Whatever punishment you are to be given shall be agreed by us both. Do you understand?"


Phil looked shell-shocked and though still bound to the chair, began to protest. Lisa slapped his face hard, leaving her palm print on his cheek.


"Do you understand?" She repeated for me.


"Yes, okay. Whatever you say!" replied my husband, the beginnings of humility in his voice.


We untied him and made him put on the sexy silk hold-up stockings that we'd selected. We told him to make sure the line was straight up the middle of each leg. Phil found this a real challenge, having to bend and turn around at the same time. We each inspected one leg, pulling the Cuban heel into place.


"Very good for a first time" said Lisa aloud. "Now Helen, shall we help him… I mean 'her' into the corset you found?"


I found myself pulling the straps in tightly, pulling in Phil's waist by a good 12". The effect was stunning, pushing his flab up over the top of the corset into the little half-cups at the front. It made him look like he had real tits, small but pert with his nipples erect from all the extra blood flow. It made it difficult for him/her to bend so; I slipped a pair of black lacy tanga style panties over his rather excited manhood.


"We can't have you sticking out like this," I exclaimed, "open your legs a minute while I stick this under your balls and fix your panties to hold it in place."


Immediately Phil responded to my orders and, I tucked his dick between his legs quickly pulling the panties into place. Lisa was already standing beside our luckless slave 'girl' and ordered her into the sexy little French-maid's outfit that I had once worn for him, hoping to add some spice to our sex lives.


"We can't call her Phil anymore, how about Pippa?" Lisa asked me,


"That sounds domesticated enough for me." I replied, laughing. "Pippa, put on the apron and that silly hat that you like so much!"


The transformation was completed with some strap on sandals that just about fit Pippa's feet. A 4" heel shaped her legs nicely, though it took a while for our 'servant' to get used to walking in them. We marched 'her' over to the mirror and, you could have seen the shock on her face as the reflection showed a sexy young woman with an almost hourglass figure and pert little breasts.


"This can't be happening" Cried Pippa. "I really look like a woman. What will I do about work tomorrow? My eyebrows, my hair. Good God, even my toenails!"


Lisa slapped her bum hard, a sharp crack sounding as she did. "Ouch!" Cried out Pippa, as she struggled to keep balance on those heels.


"You will only speak if you are spoken to, do you understand that Pippa?" Ordered Lisa dominantly.


"Yes, and you will obey our commands without hesitation, or face the consequences!" I barked at him loudly, only inches from his face.


"Yes, yes, anything you say."


I slapped his face, hard on his left cheek, marking my palm print there and leaving it burning.


"Yes Mistress. You will address us both in that manner unless and until we say otherwise." I continued, almost at a yell. "Do you understand? Moreover, stand up straight, chest out in front of you. Be proud of your new titties . Oh, and make your hips sway when you walk!"


Phil started to protest but wearing the corset made moving quickly impossible and soon he/she was bent over Lisa's lap. I went and fetched my leather belt and, with no mercy, I strapped 'Pippa's' Bum until she was crying like a baby.


"Stop, please, stop" Cried Pippa. "I'll do as you say. Please just stop hurting me! Please, I beg of you…" She continued, sobbing.


"Very well, but you must realise that this was your own doing! You WILL obey us to the letter. Do you understand?" I replied sternly.


"Yes Mistress, as you wish, so shall it be done." She replied meekly.


I couldn't believe it; in just a few short hours, we'd broken Phil and, created Pippa. I was stunned and yet, very excited and getting more aroused every minute. A feeling of power began to surge through me and, I liked it! Lisa saw the state I was getting into and came over to hug me. Pippa was told to top up our drinks. While she was in the kitchen, Lisa began to rub my nipples gently through my bra. It felt like a million volts and I responded by kissing her full on the lips.


"Let’s make it uncomfortable for our new home-help, shall we?" Lisa whispered in my ear. "Pippa, stand very still right in the middle of the room and, watch as I bring your wife off on my face!"


Lisa went and opened all the curtains and the windows, leaving Pippa clearly visible from the road, should anyone look in as they passed. Then she turned her attentions to me, stripping me naked and laying me on the couch, which hid us from the windows.


She was an expert with her tongue and, soon had me writhing in ecstasy. I was moaning loudly, which would attract stares from the street. Pippa looked nervous and fidgety but remained rooted to the spot, transfixed by what was happening to me. At that moment, a parcel delivery van pulled up and the driver smiled as he saw Pippa standing there. He came to the door and rang the bell.


"Answer that Pippa!" I moaned, Lisa's tongue still deep inside my pussy.


"I can't go like this," Pippa exclaimed in fear, "He'll know I'm a man in drag!"


Lisa jumped up and smacked the other cheek, reddening it visibly.


"Go." Was all she said: broking no argument?


Not wanting a repetition of her punishment, Pippa obeyed and went to answer the door. The courier looked surprised at the sight that greeted him and, smiled at Pippa in a knowing way.


"Parcel for Helen." Was all the guy said.


"Invite the gentleman in." Lisa shouted from the lounge. "Helen will have to sign and, I have some other questions for him!"


Pippa blushed as she showed him in.


"The courier Ma'am." Was all she said, as they entered the room.


He was a fine specimen of the adult male specimen, about 20 years old and a well toned muscular body. Lisa and I both smiled at him. I signed for the parcel then said…


"What do you think of our maid, Pippa?"


He grinned broadly and said that he thought she was very sexy.


"Good," I replied, "She is very subservient, you know? How would you like it if I instructed her to do something for you? …As a tip, you understand?"


He was a little nervous, but agreed readily.


"Pippa, get on your knees in front of the young man. Do it now!" I was surprised that Pippa didn't object, immediately obeying my orders. "Undo his fly and get his lovely manhood out. You are to suck it until he comes in your mouth and, then you must swallow it all. Do you understand?"


"Yes, Miss" She replied already holding his growing dick in his hands.


Pippa had tears in her eyes as she began to lick the young stud's rapidly hardening pole. I watched fascinated as she began to swallow his now rampant member; her head bobbing up and down, like a piston head. Lisa and I began kissing, deeply turned on by the turn of events, our hands roaming freely over each other's bodies. The lad looked as if he was nearing his limit as he grabbed Pippa's head in both hands and, started pumping his rod deep into her throat. Nearly gagging, Pippa redoubled her efforts as he gushed wads of cum into her mouth. She tried valiantly to drink it all down but, try as she might trickles of it gushed out over her lips and onto her stockings below. As soon as he'd finished, the lad got nervous and muttering something about his job, he quickly dressed and flew out of the house.


"You didn't drink it all Pippa! Look at those stains on your legs. You know that we have to punish you now, don't you?" I said coldly.


Lisa looked at me and winked wickedly.


"Tidy yourself up Pippa. We're going to drive to a friend's house near here. They're a nice couple, they enjoy little surprises and, they're swingers, very open-minded people. This'll tickle them pink!" She looked at me for approval and, I just was carried away with it all.


Pippa was horrified and started to protest when; Lisa grabbed her and put her over her lap in one swift motion.


"Spank her Helen and, make sure she remembers it. Do it hard and fast."


I complied without thinking, slapping her arse with all my might. I gave her twelve before stopping and, by then she was crying openly.


"Make sure you redo your make-up Pippa. I want you looking your best for my friends. I'm going to lend you to them for a couple of hours, while your lovely wife and I make love to each other and watch what happens." Lisa slapped my bottom playfully and kissed my full on the lips.


I smiled broadly, as Pippa tottered off to redo her make-up and tidy her clothing. Lisa and I dressed in only our short dresses, leaving off all of underwear but, keeping the heels and called a cab to come and pick us up. We made Pippa sit next to the driver and, as we drove away, we began stroking each other openly. The driver kept staring at Pippa's legs and her exposed stocking tops. We decided to play a little so, I said:


"Driver, if Lisa and I put on a little show for you and, Pippa sucks you lovingly, do we get the fare for free?"


"You betcha girls! Just let me pull over for a while, eh?" He said excitedly.


Lisa and I pulled off our dresses and went at each other like hammer and tongs, licking each other all over and, kissing each other's sensitive bits. Pippa was obviously nervous of being asked to strip too so, her head went straight to the drivers lap for the second blowjob in less than an hour! I felt a real bitch, using him like this but I was also beginning to enjoy the feeling of power that we both had over him like this. I didn't doubt for a second that he'd comply fully with whatever we said, you see it was a matter of honour with him and, he always paid up, without fail. Not to do so would be too much for him to bear, his honour was sacrosanct to him, which meant that tonight, I could push it as far as I liked! The driver leant over his seat to watch, while holding the back of Pippa's head, as he rhythmically pumped his huge dick into her mouth. Lisa and I spun around as we 69'ed each other’s sopping pussy lips, stopping occasionally to nibble each other's throbbing little love buds. We couldn't see Pippa's head anymore as our faces were full of each other's sticky gashes but, we could hear the slurping and slopping of her working away at his cock and, the occasional gagging sound as the driver rammed it home into her throat. Before either of us could cum, the driver let out a deep moan and jerked his lower body, pumping his seed deep into Pippa's semi-willing mouth. Try as she might, she still couldn't swallow it in its entirety, letting little trickles fall out of the side of her mouth, slipping over her glossy red lips and finally dripping off her chin and onto the apron of her maid's outfit, leaving little tell tale marks there and, making it obvious what she'd been up to.


"Thanks girls," the driver said, obviously chuffed with what had happened, "it's only another couple of minutes till we get to your destination now so, you better get yourselves together." He laughed quietly to himself as he drove us away, watching as we scrambled back into our clothes.


As we pulled up in front of Lisa's friend's house, he leant over and kissed Pippa full on the mouth, slapping her thigh as she rushed to get out of the cab.


"I finish at 10 PM tonight, my call sign is 64, ask for me if you like and we'll do the same on the way back!" He grinned as he pulled away and gave us all a little wave.


It was time to go to stage two of this lovely situation that we'd unknowingly pulled off over 'Phil/Pippa'.


"Now Pippa, you must be on your best behaviour for us while we are here. I don't want you to do anything to embarrass us while we're visiting Lisa's friends. If you do, we will have no option but to embarrass you too so, beware that if you don't do exactly as you are told, you will be made to walk home!" I said gleaming.


My now feminize husband looked shocked at what I'd just told him. The only way home from here took him straight through the centre of town and, the only way around it would take him through the roughest estate in the county!


"Yes Mistress, I will obey your every command… I am your servant Miss, I am your slave." Pippa looked abashed by what had just come out of her mouth, almost unbelieving of how things had turned out and, of how cruel I was being.


"Not only will you obey Lisa and I Pippa but you will do exactly as you are told by anyone within the walls of this building. Do you understand that?"


I winked at Lisa who nodded back at me, pleased that I was getting so involved in the whole scenario. Looking straight into my eyes, she said:


"Helen, I've seen a different you today, one that I like very much and one that I'd like to see more often. Do you think that we might do this again from time to time?"


Pippa's face looked ashen as I replied:


"I must admit that this has really excited me, turning the tables on Phil's arrogant male ego and, having total control over him/her is something that I'm loathe to give up easily. We'll talk later, after we get home. Let's see how Pippa gets on with your friends, okay?"


We hugged lovingly, brushing our lips together sensually and ordered Pippa to straighten her dress and her stockings before making her ring the doorbell.


Jacky and Jerry was a lovely couple. They were very good looking, she being quite small but perfectly proportioned and stunningly beautiful, he being very well built and athletic. Lisa had told me a little about them. As far as most people knew, they were both upstanding and respectable members of the community. She was a professional singer with the voice of an angel, while he was a broker by day and, a professional drummer by night often working with his wife. What only a select few knew about them was that, when it came to their sex lives, they had a penchant for the unusual and the unexpected...


"Well hello there," were the first words out of Jackie's mouth, as she opened the door to see Pippa standing there, a French maid in all her glory... then she noticed Lisa and I standing behind her, "I should have known you'd be involved in this somehow Lisa. Come in and, let me call Jerry. He's still in bed, it is only 11:30 in the morning you know!" She giggled out loud, as she herded us into the living room. She shouted up the stairs, telling Jerry to pull on a robe and to come and see the surprise that Lisa had brought for them.


Jacky was even hornier looking than Lisa had described, standing there in an aerobics outfit made of Lycra that hugged the contours of her sexy torso and perfectly formed legs. She was about 5'1" tall with a gymnast's body and perfectly proportioned 34B-21-34 figure. She had long jet-black hair and bright emerald green eyes. Her high cheekbones formed the basis of a truly beautiful face, with perfectly trimmed eyebrows and long dark lashes, a cute little slightly upturned nose and lips that were to die for, full and moist with a definite pout to them. She wore no underwear beneath the Lycra outfit and the outline of her shaven Mons was clearly visible through her leggings, as were her pert hard little nipples poking through her top.


"Jacky meet Helen, a good friend of mine and Pippa, her maidservant and slave. Pippa is Helen's husband, Phil but he gambled for some serious stakes with us, in the belief that he'd be able to have us both in his bed, submissive to his every whim... and he lost! His transformation and enslavement was his forfeit. I must admit though, Pippa has surprised me so far by holding up her end of the bargain to the letter. Apparently, Phil has a bee in his bonnet about the honour of any 'gambling debt' he incurs. He always pays up in full, no matter what and, he has agreed to become Pippa and to obey any order that we give him. Which reminds me, Helen has instructed him to obey any order given in this house, no matter whom by?" Lisa grinned an evil grin at Jacky and winked naughtily at me.


"Yes, that's right," I agreed, "so, feel free to use her in any way you wish. By the way, allow me to say hello, Jacky. You look absolutely fantastic!" I leant over and gave her a friendly hug, brushing my erect nipples against hers in an openly sexual gesture.


"Why thank you Helen," said Jacky playfully, gently brushing her lips against mine, gently and tentatively stroking her tongue over them.


She looked directly at Pippa and said:


"Okay Pippa, you may begin by washing my feet. They're tired after my morning exercise routine." Pippa started to run the tap at the kitchen sink but Jacky stopped her. "No Pippa, get on all fours and clean them with your tongue. Don't forget to clean between the toes too and, don't stop until Lisa, your wife and I have finished getting to know one another a little better.”


Pippa looked shocked but obeyed without objection, kneeling down and beginning to lick Jackie's feet all over. Just then, Jerry walked into the room; he didn't bat an eyelid at the scene before him. He greeted us all and walked over to Pippa's backside, raising her skirt and slip and spanking her bum with three hard slaps.


"You'd better make sure you clean them properly." He said: "Or there'll be plenty more where that came from. Now will someone tell me what's going on here?"


Jacky and Lisa quickly explained the scenario while my eyes roamed over Jerry's hard lean body. He was about 5'10" tall, hard muscle from tip to toe and by the looks of the bulge that was forming in the front of his robe, he had a prick to match! He was a handsome man too with very dark hair and eyes to match; he complemented Jackie's looks really well making them a most enticing and sexy couple. I could hardly wait to see how this little episode panned out.


"Well that's a turn up for the books." Jerry commented, having had the whole thing put into perspective for him. "And so early in the day too. I do believe today is going to be an experience to remember. Pippa, you should know that I am a Dom Master on a regular basis, I have a lot of experience in the role and I will brook no refusal to any order I give. Jacky and I have a fully stocked and equipped 'Dungeon' area downstairs in the cellar and, if necessary, I will take you there for punishment. Is this clear?"


"Yes Sir, it is very clear." Replied Pippa, very nervous now.


Jerry slapped her face very hard, leaving a big red handprint on her cheek and, making her sob.


"You will address me as Master from now on, or I will punish you. You will address all of the ladies as Mistress and, should any other person enter these premises, you will wait until I instruct you how they should be addressed. Is this clear, slave?" Jerry said sternly.


"Yes Master, as you instruct so shall it be." Replied Pippa as submissively as she could be.


I was really enjoying having my husband in this predicament and, already I had plans vaguely forming in my mind as to how I might make this situation more permanent in our lives.


"How do you fancy brunch?" asked Jerry. "Pippa can make it and serve it, then while we're eating she will be ordered to service each of us from under the table."


I grinned joyfully and said:


"That sounds like fun, then after food, she can wash up while the rest of us get better acquainted."


We all agreed and Pippa was told to stop licking Jackie's feet and get on with the preparations. While she was preparing the food for us Lisa, Jacky, Jerry and I retired to the dungeon, where we decided how best to use Pippa to the advantage of all. Jacky and Jerry were fascinated by how we had managed to make Pippa so subservient. I admitted that even I was surprised by how malleable Phil had allowed himself to become in the guise of Pippa the maid. I explained carefully that Phil was extremely proud of never having reneged on a gambling debt and, that to him it would be as bad as him allowing harm to come to the family or, deliberately hitting a woman or child, a thing he would never do, under any circumstances. Jacky and Jerry smiled broadly at that information and asked:


"So you really don't mind us doing whatever we feel like with the little tramp then?" Nodding knowingly to each other.


I thought carefully before answering but decided to play along fully.


"No, you have my permission to do anything you feel like to him/her, just as long as I can be there to see it and maybe take part. Is that a deal?"


"Absolutely, you'll enjoy every last bit of it with us, we promise" Replied Jerry, with a nod from Jacky and a laugh from Lisa.


Therefore, the scene was set, little did I know what I'd just condemned my poor husband to!


The dungeon area was home built but very well equipped, with lots of different bits that would restrict the 'user' in bonds of various kinds. There were other pieces of equipment that I was totally unfamiliar with too, but they all looked very interesting.


"I think we ought to start her off gently." Said Jacky looking at Jerry and then smiling at Lisa and I. "Let's go and eat. We'll see how good a servant she makes, then we'll take things from there."


We all made our way upstairs and sat ourselves down at the kitchen table.


"You will serve us with our food now Pippa, then you will retire to our bathroom and redo your make-up. You look a state and, we all like our playthings to look pretty, wanton and sexy."


Pippa obeyed without so much as a mutter, things were going well, I thought. When she returned, she looked great, having tidied up her outfit and redone her make-up perfectly. We'd just about finished eating by then too and instructed Pippa to wash up and, then to follow us into the front lounge. Jacky asked me if I thought we should 'Dress' for the occasion, unsure of what she meant I asked her to show me what she had in mind. She showed me upstairs to the main bedroom and opened a large closet in the corner of the room. Before my eyes were a selection of leather and PVC outfits, most of them very revealing yet equally sexy!


"I think that there are some items here that'll fit you." Jacky stated. "Do you like the idea of dressing as a Mistress?" She asked.


"Will you help me find something? I've never tried anything on like this before and, I'd like to look really sexy and powerful."


My head was reeling at the thought of being dressed in all this sexy fetish gear.


"Will you ask Lisa to join us too, I'd like all 3 of us to make the impact, if you don't mind.”


Plus the fact that I'd love to feel your sexy bodies through it, I thought to myself, imagining the scene. The next thing I knew, the three of us were naked in the bedroom and, helping each other into various sexy bits of gear. The feel of Lisa and Jackie's hands over my body was almost too much to take and, I could feel my pussy juicing up rapidly. Jacky was the one to bring me back to earth, by unexpectedly saying:


"Helen. Lisa. I think were revved up enough by now and, we all look the part so, let's get started with our little toy downstairs. Jerry can get changed too that way, not having to keep an eye on the little vamp anymore."


Therefore, so it was, we tidied ourselves up a little and headed for the lounge looking absolutely stunning in our leather fetish gear. All three of us were sopping wet and horny as hell! We found Pippa in what was becoming an all too familiar position, kneeling in front of Jerry, with her glossy red lips firmly around his cock.


"Is she naturally this talented or has the little slut been practicing?" asked Jerry, the expression on his face showing how good the 'head' was that Pippa was attacking with gusto.


"We've introduced her to it a couple of times, so far. She seems to have a talent for it though it would seem." I replied, smiling broadly at the scene before me. Jerry continued controlling Pippa's head while all the time setting the pace and rhythm.


As the pace increased and his breathing became more erratic, Jerry started ramming his throbbing missile deep into Pippa's throat. A deep moan escaped from his taught neck, as he pumped seemingly endless gushes of sticky fluid into her face. We all watched fascinated by how hard Pippa was trying to swallow every last drop of it. She very nearly managed too, with only a few droplets escaping over her juicy red lips and, onto her top. Jerry released her head and looked down at her.


"Well done Pippa, if you continue like this, you might even enjoy yourself!" He said, licking his lips as he did so. "I'm off for a shower," he said to we three bitches on heat, "Why don't you get her 'properly' dressed love? In the full kit I think." He said to Jacky as he left the room.


"What did he mean by that?" I asked casually.


Jacky explained that her gear included a full M/F transformation kit, leaving the wearer as a completely submissive and very sexy looking TV slut. We decided to get Pippa to perform a little striptease for us; she did so awkwardly enhancing her humiliation. When she was fully naked Jacky had Lisa help her tie Pippa hand and foot, over what looked like a leather massage table. She nodded approvingly at how well we had done. She fetched some lubricating jelly and generously applied it to Pippa's arse , then she fetched a leather strap and as I realised what it was, she slipped a 4" butt plug all the way in there. She strapped a leather device over it and around her waist, securing it tightly in position. Next, she decided to stick silicon 'falsies' over her chest, making Pippa's breasts look almost real. The couch that she was secured to rose up vertically, allowing us to put a really tight leather corset on her, which narrowed her waist to a remarkable 22"! A harness was now attached to Pippa's penis, holding it up between her legs making it look like a closed up pussy. A leather studded bra held her new tits in place, it was time to release her and finish the job. Fishnet stockings attached to the corset, and led to 6" calf length boots that we were making Pippa wear. The French maid outfit slid over the top, giving Pippa a strangely futuristic look. We spent the next thirty minutes laughing, as we tormented Pippa into learning to walk in those heels, with her plug inside her. Jerry looked at the three girls fully equipped as the 'Dom' Mistress' they intended to play and said:


"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 hand grips, 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 weal's.


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, look-see 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.


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