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
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
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
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
"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.
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