Lost bet
- 4 years ago
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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.
"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.
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ReluctanceMy husband is the one who got me started. Though I would never admit to anyone other than my husband that I read these stories and that they excite me, I never dreamed that I would be writing one.Truthfully the only reason that this whole thing happened and I am now documenting it, is because of my loosing a bet with my husband.Without giving too much of myself away, I will tell you that I have been with my husband for 24 years, I am 48 years old, and we have 2 grown sons, 18 and 20 years...
The Bet Prologue The envelope was unexciting. At first glance, the plain white exterior looked like it might be from the bank, or a sales company. Most likely it was just a bill, demanding money as such things do. On a closer inspection, however, the multitude of stamps on the front would reveal that this envelope had flown across the Atlantic from England. It definitely wasn’t a bill. The young woman who picked it up from the mailbox casually flicked her hair out of her eyes as she glanced at...
"How about that guy?"My girlfriend was pointing at a guy walking up to the door of the rest area. I'd lost a bet, and she takes paying off bets very seriously. I'd bet her that she couldn't get me off by giving me a blowjob in less than 10 minutes. I was so sure I'd win. See...she'd given me lots of blowjobs. And don't get me wrong, they all felt great! But I'd never come from one unless I sort of 'helped'. That is, if I thought about certain extra-kinky fantasies, or if I talked dirty to her,...
The Bet By Cassandra Morgan Hers was the perfect face. The dancing eyes. The plump, but not obscene, lips. The way the bangs of her blonde hair danced on her forehead. The white teeth. The dimples. Above all else, that heart-capturing smile Lauren Howard stood in the living room of the Kempers, still as beautiful as the day we were married. When she was around, no one noticed the other women in the room. There was just Lauren. She was the star of the show, the one whose eyes you...
[Netzfund] Wieso liegt Abou in Mami's BettbyAmelung©Abouadi John Obote, oder Abou, wie er stets nur genannt wurde, war während eines dreiwöchigen Namibia-Urlaubs unser liebenswerter, lustiger und immer gutgelaunter Barkeeper im jugendlichen Alter. Der smarte Afrikaner aus Windhuk sollte jedoch einige Wochen später unser bislang so geordnetes Familienleben vollständig auf den Kopf stellen...Anmerken sollte ich vielleicht noch, dass diese Reise nach Namibia unsere erste Fernreise war, die wir als...
“You’re an idiot,” Karen said, shaking her head and looking away from her husband. “How in the hell is going to a horse race a date night?” “It’ll be great!” Greg said excitedly. “You can get dressed up, they have good food, it’s just like going out to dinner but with something extra!” “Yeah, something extra. You gambling away all our money. Again.” It stung but was true; Greg loved to gamble but was quite bad at it. Poker, slots, sports, any time money could be wagered Greg was there to do...
YOU BET by Throne and C.C. Cecil's wife Bette came home in a state of amused agitation. She looked down at him from her superior height, over the hills of her watermelon boobs, and said, "Ceece, you won't believe what happened with Dara and me. She made this crazy dare and I took her up on it. And then I got her back with one of my own. Here's what's going on." He was more interested in the slim chance of going to bed with her. It had been way too long, at least since she had...
Jasmine becomes a slave part 1 Chapter 1 The betRacheal was going to the B&D party at Shelia’s that Monday night and was picking out her outfit. She selected the black leather cat suit that hugged her body and while it covered her, it allowed everyone to know she had a hot body. Shelia was a fellow Domme and was the area’s leading supplier of fetish gear, from clothes to dungeon items and all of her parties were events not to be missed as she loved to demonstrate new items on her slaves. As...
She's sitting at her favorite table by the front window, her back to the wall, so she has a clear view of the room. She is carefully nibbling an almond croissant with her coffee, reading a book. She is probably around thirty, but presents herself as older. She has quite a pretty face made dour by the absence of any make-up. Her hair is a nice medium brown with some natural red toning, pulled tightly back in a workday bun. Her only jewelry is a thin gold chain around a first-class neck. Her...
Lesbian"It's time to wake up now."With just those six words, I regained the ability to open my eyes. Regained? I guess that's not the right word. I'd only just dozed off—nothing more."Well, how do you feel?" The hypnotist grinned at me. I didn't see why he was grinning, though. He was a friend of mine. His name was Kyle and he liked to think he was a master when it came to hypnosis. I guess in a sense he was. I did get into a trance, after all—well, I did if that's what you call falling asleep from...
Bikini Beach: The Bet By Julie Butch sat at the bar of his favorite club, looking around for any likely targets. He was a predator, although he didn't think of himself in that light. He stood 6'3" and weighed around 225. He thought of himself as being 'buff'. He worked out regularly because he liked the high he got off of the endorphins that the body produced during an extended workout. It was almost as good as sex. He never had any problems finding a sexual partner. One of...
At school, I was on the wrestling squad. I wasn’t exactly stocky, but well-built. Apart from wrestling, I also dabbled in martial arts and boxing. The latter was not my forte and didn’t come to me naturally, because my foot and hand speed were never quite up to scratch. But when it came to grappling, I was able to hold my own.I was also not the greatest student and settled for a trade after leaving high school. I chose the electrical route. Two years after school, I had completed my trade and I...
Gay MaleKalie was already pissed at David, they had argued earlier in the day about coming out tonight. The two had been dating since their sophomore year of high school and had been nearly inseparable since. It was now the start of their second semester at college, they had gone to the same school in Colorado. The two were from Nebraska and the school had been a compromise, Kalie wanted to get out away from home but David wanted to be near his parents. Now they were a short drive away but at least...
I was bored, watching a bad porn movie on cable TV when the phone rang. "Hello." "Whatcha doing, playing with yourself again," my step-daughter Teresa asked me. "Funny," I answered. "Isn't that what you do most of the day?" Teresa was 20, a cute, top-heavy bottle-blonde with several piercings and tattoos and one of those tongue studs, and she worked as a repair dispatcher for the cable TV company. Thanks to her connections I got great service and the fastest Internet service possible, and at a...
TabooSybian and Venus Racing –4 Couples and The Bet.I fancy a chance of fucking any of my mate’s wives. All six are sexy in different ways. So after a drunken night out we boys all agreed to find a way to swap partners for a night…….. but how?I told my wife about our drunken agreement while I was in the bath the following day. Not to my surprise she said that she was up for it. She moves close to the bath and places my hand on her pussy and as I slip a finger in its obvious that she’s highly...
It all started as a simply little bet. It was one of those bets where we were both 100% sure that we were right. Sound familiar? First the bet was for $5, then she upped it to $20 and I upped it to $50. That’s when things got interesting. She said “I know you’re wrong but if you win, I’ll do anything you want me to do, but if I win, you have to do anything I want you to do - anything at all!”This did not intimidate me in the slightest as I was so sure I was right. “OK, I’ll take that bet.”Less...
Kalie was already pissed at David, they had argued earlier in the day about coming out tonight. The two had been dating since their sophomore year of high school and had been nearly inseparable since. It was now the start of their second semester at college, they had gone to the same school in Colorado. The two were from Nebraska and the school had been a compromise, Kalie wanted to get out away from home but David wanted to be near his parents. Now they were a short drive away but at least...
Cherry was the perfect name for ripe innocence, at 18 and her last year in high school had taken a bet from several of the other girls. She had always done wild and crazy things and had always won every bet she had ever taken. Thinking this latest one would be no different! The bet was that she had to go to the Rusty Dyke a notorious lesbian bar that had a reputation for catering to the meanest Bull Dyke's that one could imagine. She was to act like she was a young lesbian bottom and kiss...
Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was on my way to meet my usual group of friends. The eight of us had been friends since high school, and we...
CrossdressingThe Bet by Laura Brooks I can pinpoint the day this all started. It was a chilly, Sunday afternoon in early December. A light rain was falling outside and Carol (my wife) and I had built a cozy fire in the fireplace. She was sitting on one of the couch, her legs curled up beneath her reading and sipping a glass of wine and I was sitting at the other watching the Giants begin to give away a 21 point lead to the Eagles. Carol stood up and stretched, heading toward the...