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Lost Bet By Pippa

It all began as a bit of a joke really. We'd all been out clubbing in some raunchy nightspots 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 eyeliner 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.

Continued...