Lost Bet

It all began as a bit of a joke really. We'd all been out clubbing in some really raunchy nightspots and were still high on both the atmosphere and the 2 Love-doves that we'd swallowed a few hours before. 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, lets 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 really 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 of all 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 eyeliner and a heavy dose of 'lash-lengthening' mascara. She applied a really 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, 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? And 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. "Lets 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 got 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 others 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 2 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 feminised 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 were a really 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...