Winners and Losers ( R )
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Chapter 1

I am happily married to a wonderful lady, Stephanie, who enjoys most of the same things I do. We are both enjoy outdoor sports, camping, and have a fairly active lifestyle. We both stand about 5-5 and have similar builds. She is fairly strong and energetic for a woman, and given her overall size is amply endowed. I, on the other hand, tend towards more of a runner/swimmer physique.

It all started over a friendly competition. I had been teasing her a bit during a tennis match. I was winning, (although not by that much), so I was urging her on in a slightly mocking way. All in fun, of course. However, I guess it got to her a little, because when we took a break after the first set - which I won - she told me she didn't appreciate it.

I appologised, of course, but it led to a brief discussion about relative assets and handicaps.

"I bet you'd have a lot more trouble if you had to deal with these 'issues'," she said, while cupping her C+ breasts. I laughed and said that shouldn't make any difference, as tennis at our level didn't require a man's power. As you might expect, that led to 'the bet'.

"I know you don't have a clue as to what you're saying, so how about this: If I win the match, for the next week you have to try to put up with my 'issues'. If you win, you get to take off for the week camping with the guys, no questions asked. Deal?"

I agreed, not really thinking through what was involved. Next week was a vacation week, and some friends had thought about a camping trip. All of a sudden I was looking forward to it.

That'll teach me. With my mind elsewhere, Steph took the next two sets and the match with relative ease. Afterwards, we sat having a cold drink to cool off. That's when she dropped the bombshell on me.

"When we get home, I'll get you ready for your week as a girl. I've got a few things to pick up on the way home, and then I'll meet you there. You know, it's probably a good thing you've taken the week's vacation already."

"What do you mean?" I asked.

"Why, in order for you to experience a week with the issues I have to deal with by having breasts, long nails, wearing dresses, etc. In short, being a girl! That's what you agreed to, and for that, I'll need to pick up a few things. Fortunately, many of my things should fit you."

I was shocked. This was NOT what I had planned. But I had made the bet, and, as Steph pointed out, if I had won I would have expected the prize.

What had I gotten into?

I went home and took a shower, and then sat there wondering what she could be doing. Stephanie made it home about three hours later, with several bags full of items which she wouldn't let me see. She smiled and told me that I'd find out soon enough.

"It's too bad you took a shower", she said, "As you'll just have to take another one. However, first I have something for you."

With that, she handed me a large container of hair remover. I balked at that, but she put her foot down. I didn't want to make her mad, and figured what the heck. I stripped and she helped me to cover my chest arms and legs. Fortunately I'm not to hairy, having light sandy colored hair. After about fifteen minutes of tingling, I washed away my hair, leaving only my pubic area.

Then, Steph told me to lay on the bed. She brought out one of the packages and set it next to me. She picked something up, applied some gel to it and then placed it on my chest. Then she repeated the process. You guessed it, she had two fake breasts that she had affixed to my chest.

"I got these from the medical supply place. They are designed for active women who have had mastectomies. They are as close to real as I could get. The glue is a surgical adhesive, and should last the week."

While telling me this, she had held them in place while the glue dried. Once done, she had me sit up. My chest felt huge, and they pulled on me almost painfully. When I complained, she laughed at me. You don't seem to complain about the size of mine. Now you know why I always wear a bra.

She got out one of her bras and helped me into it. It did relieve the weight, distributing it along my ribcage and shoulders. Just as I was dealing with that, she handed me the matching bikini panties.

"Why do I have to wear those?"

"First of all, it's a matched set. Secondly, that's what I normally wear and that's what you've agreed to. Thirdly, I don't expect you to complain or try to weasel out of everything I give you. Once and for all, you promised to do this for the whole week, and I call the shots. Now, if you're real good, I may let you try a double-or-nothing bet in a day or two."

I pullled on the panties.

"I think we may be able to have some fun with this," Stephanie commented. Her hand brushed against me, and I realized that I was fully erect, straining against the flimsy nylon of her panties. "It seems someone is secretly a Sissy!"

I protested, but she overrode me. "I don't want to hear it." She continued to stroke me gently. "It's obvious you are enjoying this!" Unfortunately, she stopped before things went any further.

I won't belabor the next couple of hours. I had fake nails attached and was dressed up in a dress of hers and given some low heels to wear. After initally making a fool of myself, I finally learned to walk. That's when I got my next shock. Steph handed me one of her purses, grabbed another one and headed to the door. "Come on, silly."

I was stunned. I hadn't thought this through at all! "You didn't think we were spending all week hiding inside, did you?"

I sputtered something, but Stephanie overrode me. I have made some plans, and that's it."

She took my hands, and assured me, "If you follow my plans, we'll make it so that nobody will laugh at you. But it's up to you. Either way, we're going out!"

What could I do? I hurried to the car, and hopped that nobody could see me. Steph got in, and soon we arrived at her destination -- the beauty parlor.

Chapter 2

This was not one I remember ever taking Stephanie to. But, it turns out she had made an appointment for me here. She told me, "I thought that this time it might be better for you to go somewhere where nobody knew us, and you wouldn't have to worry about seeing them again. Plus, I picked out a place that was small, and not in a busy area. So you really should be thankful!"

I was (I guess), but still...I realized that I had to get out of the car. I looked around, and it was fairly deserted. Yes there were cars going by, but no pedestrians, and nobody to stand and stare at me. The shop was a small private building, with no more than three of four operators in it. Of course, when I walked in they all looked up. But to my surprise, nobody really said anything. One of the women came to the front counter and asked if we had an appointment.

Stephanie responded, "Yes, I'm Stephanie. I made an appointment for a hair style and a makeover for my...." She looked at me and said with an evil smile, "My new girlfriend."

I'm not going to belabor the next hour or so. You can all imagine. The hairdresser was actually very nice. My hair was long for a guy, and kind of unkempt. She turned it into a flirty bob, that looked anything but manly! Then she plucked and trimmed my eyebrows into a delicate arch. She added some hair remover to my sideburns, until all that remained was a delicate little whisp in front of my ears. Now my face was totally denuded and no five o'clock shadow would be seen for a few days! (I could normally go several days without needing a shave anyway, but this made sure of it.)

Once all that was done, I had makeup put on me. Stephanie watched and told me to pay attention, as I wouldhave to do this at home. The beautician was actually very helpful, and coached me through each step. At the end, I looked up and was surprised. I looked like a normaly young woman. If I didn't know any better, I thougt I looked like the type of girl I might have tried talking to. The beauticians all congratulated me for 'coming out'. I didn't know what they were talking about initially, but then I understood -- they thought this was my idea! I was speachless, and Stephanie filled in for me.

"Yes, she's been thinking of this for some time. We appreciate all your help in getting her on the road, so to speak."

The beautician asked me if I had any immediate plans, and again Steph answered, "Well, we have a little shopping to do first. But tomorrow we are going to the beach. Plus we've got a tennis game rematch," she gave me an elbow in the ribs at that, "and we thought a golf game and maybe going horseback riding or some camping. We have a fun week planned!"

They all thoguth this was wonderful, but then 'my' beatician asked me if I had a swimsuit picked out yet. Steph said that she had a coupld that I would probably use. I could select either a one pice or a bikini.

"And are they, umm, High cut at all?" asked the beautician. "I mean, she's done a wonderful job so far, but perhaps a bikini wax might be in order?"

Stephanie thought this was a wonderful idea. I, of course, had no say. She immediatly pointed out, "What a good idea. I hadn't thought about it, but of course I get them regularly this time of year. It's just one of those things we girls put up with to look pretty!"

Everyone agreed with her, laughing in a friendly way. I was escorted into a back room, and sat down on a bench. Some wax was heated up, and soon I was told to lift my skirt up about my waist and spread my legs. I could keep my underwear on, I was told.

I hadn't gone into any detail on what I was given to wear before. Perhaps I should mention it now. I was wearing one of Stephanie's matched sets of lingerie. A Bra, Bikini and Garterbelt (suspenders) all of a pretty delicate rose print on nylon with lace trim. The panties barely covered my parts, and looking down I saw a lot of hair sticking out.

When the beautician came back in, after an initial chuckle at my expense, she proceeded to business. She took a wooden spatula and spread a patch of warm honey wax across my thigh area and up towards my privates. Then she lay a strip of cloth over this and pressed down on it, rubbing it in the direction of my hair growth. Then, without any warning, she took hold of one end of the strip and pulled it in the direction against the growth of my hair in one quick, firm pull. I think they heard my shriek three blocks away.

"Well, aren't you the big sissy," said the beautician with a smile and a laugh. You'd think you never had a waxing before the way you're carrying on!" She calmly continued to apply wax to the other side and repeated the process. Then she tugged my panties up and to the center, barely allowing me any coverage and repeated the process on either side again. She told me (actually, she was looking at Stephanie), "I'll step out for a moment and you can take a better look. THen let me know if that's good or if you need more done."

She walked out, and Stephanie immediately pulled down my panties to get a better view. I could see myself in the mirror, and I now had what is referred to as a landing strip. There was a neat little patch, sort of triangular in shape, over my privates, but no hair anywhere else. It no longer looked like an adult male's growth, and I felt more ashamed by this than anything so far. Stephanie laughed and said I looked quite girly now. However, when we got home she promised she would 'finish the trim' so I wouldn't have to go through any more here.

I pulled 'my' panties back up. How strange, I thought, as I was already thinking of them as my panties. I adjusted the garters and nylons so everything was neat, and replaced my dress.

When we got home, Stephane had me lay down on the bed and spread my legs apart (after removing my panties). She got out her tweezers and started plucking one hair at a time. Ouch, Ouch, Ouch. It seemed as if she were trying to remove anything I had left! However, once she was done, before I was allowed to look, she took my hand and made me feel between my legs, my scrotum. They were silky smooth. Then I was allowed to look. My triangular patch had been 'shaped' into a heart. Now my feminization was glaringly obvious to anyone, should they see. I just wondered how long it would take to grow back.

"Don't worry, honey," Stephanie said, as if reading my mind. "It will grow back in a month or two! With a giggle she continued, "But meanwhile, you've got to pick out what suit you want to wear tomorrow!

I could hardly wait...

Chapter 3

But tomorrow was still a long way off. First we had to have dinner.

Normally we both help out with meals. Lots of times I'll cook and Steph will set the table, or sometimes we both cook. Whichever, it's a team effort. Tonight, though, I had to learn how to cook all over again. OK, women, I'll admit it. While guys may drool over 'em, sometimes breasts can get in the way. And nails really require some getting used to. I was finding it difficult to use a knife on a cutting board, as I couldn't see what I was chopping easily. I couldn't pick up things easily with the nails. Finally, I was banished to set the table and Stephanie took over.

"Not as easy as you thought, is it?"

Over dinner, which strangly was only a light salad and a glass of white wine, we had a long conversation. I won't bore you with all the details of self discovery, but I did admit to her that she may have had a point.

Stephanie, however, quickly found a way to lighten the mood. "I bet the whole block heard you yelping when you got waxed!"

"Hey, I wasn't ready," I exclaimed. "I've never been waxed before."

"Personally, I think you're enjoying yourself. Perhaps a little too much. I've got an idea. How 'bout a little additional bet -- double or nothing?"

OK, I had learned. "Just what did you have in mind?" I was anxious to get out of this perdiciment, but what were the possible consequences?

"Oh, nothing much. Just that If I win, your week gets taken up a notch or two. Actually, just what I sort of had planned already, only a little more so. If you win, it's all done with."

"And what's the bet?"

"A simple one. We get ready for bed. I bet that you can't help responding to being dressed as a girly girl. That you are, in fact, a sissy."

Well, I knew I wasn't a sissy, and I couldn't let her get away with a statement like that, could I? "Your on!"

After dinner, we did the dishes. I was coached on using gloves to protect my nails, and being careful not to splash on my dress (yes, I was wearing an apron - OK? I just didn't want to admit it.)

Afterwards, Stephanie went into the bedroom. A little bit later, she called to me. It was time to get changed for the evening. I joined her and saw what she had laid out on the bed.

"Hmm," I thought. "I always liked her in that outfit."

She had put out her babydoll nighty and matching panty. All very filmy and sheer. I removed my daywear, and at Stephs instructions I was careful not to put a run in the stockings with my new nails. Then, I first put on the panties, then the top.

Stephanie turned the floor mirror to face me, and asked me, "So, are you an edible little sissy slut or what?"

I saw myself. I don't know if it was the sight, or the silky feel of the nighty and panties, but I was standing ther with a raging hard-on. The tip of my penis was peekingout of the waistband of the delicate panties.

Stephanie giggled, clapping her hands and chanted, "I win, I win, I win!!"

She reached over and stroked me, and said, "But don't forget, you're still my little sissy slut!" Then she changed into a similar nighty. We went to bed, and soon began fondling each other. As things progressed, however, I was not allowed to follow our usual course. Instead, I was told to switch around and start using my tounge.

Meanwhile, Stephanie was licking me. Without any extra hair in the way, she didn't mind and the areas were MUCH more sensitive.

"Mmph," Stephanie said, "your little clitty seems excited."

When all was done, Stephanie confided to me that she had always fantasized about lesbian sex. This was the next best thing.

I had too, of course, but not like this...

Chapter 4

The next morning, it took me a few moments to figure out what was what. I was sleeping on my back, but I felt strange...as soon as I sat upright, it all came back to me. I went into the bathroom to relieve myself and Stephanie's voice came from behind me. "That's something we'll have to fix."

"What?" I asked, flushing the toilet.

Just think what would happen if we were out in public, and another lady walked in to a restroom and saw you, and apparent girl, standing in front of a toilet? Women, after all, sit. Besides, you look silly standing there pretending to be a man while wearing a frilly little nighty."

That 'pretending' crack got me a little uneasy, but she did say it with a laugh; I guess she was just being funny. However, she did have a point about being seen in public. I was attempting to 'pass', and I would have to be careful.

Stephanie, however, had a way of 'helping' me. Once again she had me lay down on the bed. After first placing an ice bag over my privates to shrink everything down (Guys, you know what I'm talking about. Ice and certian parts of the body don't mix well!), she made me spread my legs apart. First she started prodding me about, untill she manuvered my testicals up into my body cavity. Then she pulled my penis down between my legs. This is the process generally referred to as "tucking". However, she had a different spin on it. Instead of securing things with a gaff or tight panty, she got out that surgical adhesive. She pulled the skin of my scrotum around either side of my penis and glued it together. This created, in effect, a sheath that surrounded all but the very tip of my penis. As things warmed up, she rubbed the tip which caused me to become enlarged, and she continued to glue the skin around it. When she was done, my penis was totally surrounded and held in place. When it shrank, nothing was visible. When it became fully erect, it was still tucked away and only the very tip was exposed.

"Remember, this adhesive should stay for at least a week, perhaps longer. So for at least that long, you'll have to pee sitting down. Also, you'll need to wipe yourself properly - no shaking anymore! And of course, any sex will have to be done like a woman as well. I did say you were going to learn what it was like, didn't I?

Now, before you get up, there's one more thing about being a woman that you certainly are aware of, but I'm sure you never gave it any thought. She reached into her bag by the bedside and pulled out something white. I looked up as she tore it open, and saw her holding one of her tampons.

"Yes," she said with a gleam in her eye, "you need to be aware of your time of the month. And, since we will be going to the beach, you can't wear a pad. So..."

Before I could begin to protest, she placed it between my cheeks and inserted it into my anus. She deftly pushed the plunger, forcing the tampon further up my passage, and then removed the applicator. She gave the string a gentle tug, which casued a unique feeling. In a few moments, the tampon had expanded enough to be secure. I was then allowed to get up.

The first thing I noticed was that the tampon was not really uncomfortable, but was certainly noticable. So, too, were my privates. They weren't painful, but it certainly felt different! I must have walked a little more gingerly, as Stephanie lauged and told me that I was walking with a bit more swish today, which was appropriate.

I also noticed that the panties of my nighty fit better, as did Steph. "No unsightly bulges, are there? This way you won't attract any stares at the beach. At least, not that kind. You might get some stares from some horney guys, though..." She trailed off, and then broke up in laughter at my expression.

"You should see your face! Face it, we're going to be two women on the beach, and if there are any guys there, they may be looking. Deal with it!"

Then she handed me a swimsuit to wear. "Here, I'll let you wear the once piece. I figured you might not be releaxed in a bikini."

Leaving me to pull it on, she got hers on as well. She was in a modest 2 piece bikini, and looked georgous. I stepped into the leg holes and pulled the suit up over my hips. Dropping my arms into the openings, I pulled it up over my breasts and about my shoulders. Stephanie showed me how to 'adjust' myself so that I was properly situated in the cups. Then I got a look in the mirror. First of all, it was a good thing I had shaved. Because it was a one piece and held up by the shoulder straps, the sides could be and were cut much higher than Stephanie's bikini. I would say that almost half of my groin was on display! And the top plunged down lower than hers could as well. The back was also scooped very low.

I'm not going to go into a lot of detail about our outing. It was the first day at the beach for us this season, and Stephanie wanted to work on her tan. We were both very pale, so once there we put on some suntan oil, put down towels and just relaxed. Stephane had brought some magazines for us to read, and I had the dubious pleaseure of looking at fashion magazines, and reading about how to please my man. I was told that anything else might look out of place...

The beach we went to was, fortuantely, pretty secluded. And since it was a weekday and early in the season, not very crowded. So we were well away from everyone. There were some families there with young kids, but everyone was in their own world and nobody paid us any special attention, which kind of worried me. I mean, shouldn't everyone be staring and pointing?

That night, when we got home and were getting changed, I noticed that we both had a little sunburn. However, When I took off my suit, it hit me -- I had a decidely feminine tan line; A glaringly obvious tan line. Where the suit had been was white, but everywhere else was bright red. And by tomorrow it would be worse.

"Don't worry, honey, the tan will fade. Nobody will notice it by next year..." With that she giggled her way into the other room, leaving me to wonder what I had gotten myself into.
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Mina Silverwind
I love what you have written thus far, keep up the fabulous work in the future chapters. amd you rock as a writer.
success is not how many times you win but is instead our ability to learn that we win by never giving up when times are tough.
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Baby Flo
Very nice. I can't wait for the next part. Thanks
Love everybody
and
everybody will Love you
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ty666
This story has a lot of potential great job
Ty666


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Sissy Wanda C
Good possible plot, well written, and common intrest.Keep adding to the story.
Bestest holiday wishes
Sissy Wanda C
xoxo
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BabyJackie
Hope U continue I am enjoying the story
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dj1ob1
Added Chapter 2
Hugs 'n Kisses to all the good ones, and get ready for spankings to the bad ones.
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lilykitten
Great story, I love the heart at the end alots^^
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