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Play to lose By Denise This should be a story in Spanish because I'm Mexican, but I want comments from everybody so I did my best effort please forgive and correct my grammar mistakes. Denise 1. You bet your ass on this Bets are always an illusion whether you win or lose the risk is the reward, you risk to play because of the adrenalin, that rush you feel every time a challenge is issued and you know you want to be a part of it. It is widely known that you should only bet when you are sure you can pay your debt, play to lose is what I say. If you are not afraid to pay when you lose you'll feel great when you win, I know this by heart and betting has always been my doom. It happened last Friday night, I always hated soccer and never followed any of it a really big problem when you live in Mexico, but when you love to gamble you can't pass on an easy one like this one. Last July all my friends got together to watch the world cup final and I didn't want to be left out so with the promise of bonding, camaraderie and lots of alcohol I went to my friend Karla's house and sat with everybody to watch the awful game, everybody in there loves this game and as usual I was the only non sports person; I would much rather stay home and play video games, but that day I didn't want to be left alone. I had been feeling gloomy and even vindictive for some time and I always thought it was stress or work problems. Before we continue I'm going to introduce myself, my name is Antonio I live in Mexico city and I'm 28 years old I am an accountant and work as a manager in a savings and loan office. My work is really hard and the common idea of the Mexican leadership is that you work better the more time you stay in your cubicle, I find that to be abhorrent, but I comply with it 12 hours or more a day from Monday through Saturday of boredom and underpayment. I'm 1.7 meters tall that's average for Mexico, but I'm always hassled because my friends are taller, hell all my girl friends are almost my height or taller. I'm very slim a little more than 100 pounds and have slender features, green eyes and almost no facial hair so maybe you'll understand why all my friends want to stick me inside of a dress. So back with my story I was there mumbling around and even though I know eight beers are enough for me I was drinking the twelfth when my boredom got the best of me, so I stood up and made the stupid comment, "Holland is going to win..." and "Spain are a bunch of losers" I really don't know why I did that maybe I wanted attention, maybe I was too drunk; I just wanted a change, so like always everybody knew a lot more about soccer than me so everybody started screaming, so I did what every Mexican does in a situation like this I ignored them with all my heart; ... until someone said the magic words... "wanna bet?" so my face lit up and I was happy to make a proposal. So I told to my friend Melissa "If Holland wins I want to see you in a really small miniskirt for a whole day next time we are all together" You see as an architect she has a really butch dressing style, she always wears heavy work boots and jeans also flannel shirts and that kind of stuff, she's really pretty and has great legs or so I'm told because I have never seen them and of course I want to. The moment I dared her she stared at me in disbelief as if I were a pig because she would have to wax her legs and show them like she never had and all the girls just stood there in awe, the boys screamed and told me that it was a great idea so I felt powerful and expectant, she would fold to the pressure I was sure, it was just a matter of time; but then the other girls spurted the counter offer. "ok" said Irma, her best friend, "She'll do it, but your dare is the same!". "What?" I replied with a skeptical smug look, "you want me to use shorts all day?" "No, you'll use a miniskirt with waxed legs also", the boys just laughed and kept staring at the screen and the girls screamed loudly, I was so bored and felt in ease with my friends so I answered " I'll do it big deal, and I'll show you is just a silly piece of cloth" a little later I passed out from the alcohol, Spain won I was screwed. 2. Hot beer and cold legs I really wasn't worried I knew I had to pay up and I was even willing so I could show I never back on a challenge. The date was set in a going away party with close friends and it was the start of my vacations in a Friday night so if it got really embarrassing I could just drink a lot and pass out. Some days earlier Mellissa drove to my house and gave me the skirt, luckily it wasn't very small, she said it was because I would eventually forget about it and sit with my legs wide open, when I saw it I was kind of relived that it was longer than I thought, but I was also surprised to see that I kind of liked it. She also gave me some girl's underwear that were kind of big so I wouldn't be worried about my "package", completed the outfit with flat sandals (heels were not part of the deal) and a piece of paper. "That's the receipt, the girls and I paid for your waxing and for fixing your toes, we don't want to see your legs all hairy and ugly feet" I just laughed at this and assured her I would comply with all. Friday morning I was just a little scared, I was just too conscious of my hairless legs and painted toes under my work suit, I kept thinking that someone was going to find out and I would be embarrassed for life maybe even fired, but nothing happened. At 2:00 o' clock I was released from work, it was early because my vacations started that day, 2 weeks of nothing in my future and a lot of beer and a little silliness to start it. Just a little after 5:00 Melissa called me and told me the place of the party had changed and it was going to be in the place of somebody I didn't know and it was going to be bigger than expected, this of course struck some terror, but still I didn't back out so I packed the girly stuff and went to Melissa's were I was expected to change. We were going to carpool in Irma's car, I was even glad of this decision because I didn't know where the party was and also because I could get wasted and not be worried about driving afterwards. Instantly when I arrived I was asked to change, so I put on everything and of course I got whistled and harassed but as expected it passed quickly so we got ready and got on our way. I was going to be a pretty girl from the waist down and I completed the ensemble with my meanest Metallica T shirt, but I was really annoyed when I realized that my skirt had very small pockets so I had to take my money and car keys directly in them and leave my wallet and cell phone, because I wasn't allowed to have a bag with my male stuff, the conditions were very clear I shouldn't be able to change back in the night that would be only after the party was over. The party wasn't big, it was HUGE it was a way to embarrass me and to try and make me miserable. My strategy was simple I was going to sit, explain to every moron who asked the situation and drink a lot, the place I chose was a comfortable armchair near the bar and some of my friends sat there with me joking and helping me cope with the assholes who laughed at me and worse, the drunken people who wanted to hit on me. The house was the biggest I had ever seen so at one point in the evening I even ventured in exploring it because it was amazing, lots of rooms and great stuff the owner must have been loaded. I returned to my spot and continued with the task at hand: Free my legs of the surrounding cold with big doses of beer. 3. Bet to be Black, everything was utterly dark, I didn't know where I was or how I got there, but my head was spinning so fast I really didn't care I just laid down and expected that soon the world would stop circling around me. When I came to myself I had a killer headache, enough thirst to drink a lake and no clothes, I was in a bed in a tasteful but Spartan guest room, next to me a bath robe was laid and judging by the position of the sun it should be a little past noon, so I put on the robe and went outside to at least understand what had happened with me. I stepped out of the room and was again surprised by the enormity of the house and the efficiency of the cleaning crews who were just leaving a spotless building. I wandered for about 5 minutes when I found the owner of the house in the kitchen. I had seen him the night before I just didn't know who he was because frankly I didn't care, he was a lot taller than me and not heavy but built, he looked quite pleased and happy with the results of the party the day before. "Good afternoon" He said "I see you found the robe, your car keys are in it, I took the liberty to leave the robe there because your clothes were completely drenched in beer, puke and other things; if you don't mind I had them thrown away... or are you planning on use that cute skirt in another party?" he said with a smile. There wasn't sarcasm in the way he said it, he was smiling in a sincere way, and he knew the story like everybody else so I wasn't offended by his comments. "Sit, have lunch, or do you want to take a shower first'", "A shower would be great, but I have nothing to wear. I hate to ask, but could you borrow some clothes?" I replied. He sized me up and started laughing; I understood at once he was at least 30 centimeters taller and a few sizes bigger, so I just stood there and felt stupid for asking, but then he thought a little more and said " Not any of my clothes would fit you, ...but considering your ... ahem taste in yesterday's attire maybe I can help you" He stood up so I followed him into a room he showed me a closet and explained " My ex-girlfriend used to live here with me for a while, last year she had a work proposal overseas and she dumped me, but she left almost all her clothing and things here because it was too expensive to ship them with her, also because she knew I had bought almost everything. She was about your height, maybe just a little slimmer, but her clothing should do fine for the time being" I stood there for a moment and felt the breeze through my family jewels so I decided I could do it for just a little more time. Also I was here with a complete wardrobe so there should be some jeans or sweatpants around here. He looked at me and understood, showed me the bathroom and said he would be in the kitchen when I was ready. How come girls need so mucho clothing?! All the space was filled with dresses, formal, informal, short, long, cocktail, gowns; skirts, denim, penciled, bubbles; blouses, silk, satin, etc. and this was only what she left behind! There were also some jeans but the percentage of this was extremely low compared with the girly stuff! I must have tried every pair and all of them were very tight, so I looked for other options. After the jeans the shorts were the best choice so I tried some until I found some that weren't as tight or girly, but of course the cut in all of them is weird and whether you like it or not the shape of your hips and butt change entirely. When I found the shorts it was time for a T shirt and some underwear, so I opened the drawers and found all kinds of sexy lingerie some things I even didn't have names for, the weird part is there wasn't any in the "normal" range all were frilly and sexy so I accepted the bigger ones that were a low cut girl boxer that accentuated my but even more. For the top I chose a spaghetti strap t shirt and took a bath. When I finished I got dressed and couldn't believe that today I looked even more girly than yesterday, when I was about to go I looked for shoes and found out that this woman had hundreds of shoes but none of them were tennis shoes all of them were either high heels or very stylish flats, I chose a pair that had a little ribbon and no heel and went down stairs. When I entered the kitchen I was expecting laughter, but none came out; Robert (that was his name) looked at me in awe and said that I looked good, even beautiful, I blushed deeply and thanked the compliment. While we were eating he talked about his life. He was 36 years old, his parents had died when was 18 and became the sole proprietor of his father's business. Under his wing they had grown and became bored so he decided to sell everything and invested in stock and financial assets, his wealth has multiplied and is always looking for investment opportunities, as an accountant and advisor I knew a lot of capital ventures I had never the funds to invest in so I proposed some ideas and he was immediately interested. After lunch we chatted for a while and asked me what was I planning for the afternoon, I told him I was on vacations so there was not much I planned to do, also I couldn't do a lot without clothes or my cell phone, so he told me I was welcome to stay as much as I liked he was interested in my business proposals so he said I could stay all day and when night fell he could drive me to my car when nobody could see my female garments. I found this to be an acceptable idea so we talked for a few hours. Later on we got a little bored so he dared me to a Competitive match at "Modern Warfare" in the PS3, my eyes shone; it is one of my favorite games and I'm quite good at it so I agreed. We played for an hour or so friendly matches and like every gamer we sized each other, with more than 80% games won I decided I was a little better than him so I of course proposed a wager. You see I had checked his DVD and Blu Ray collection and couldn't miss various collectives that were almost impossible for me to find, don't get me wrong I earn good money I don't want to rip this guy off is only the availability of this stuff and that sometimes these are limited editions, so I said "If I win you are going to give me your special edition star wars blu ray box set" he said it could be interesting so I asked what were his conditions, he thought for a moment and said " I want you to change into a dress, you looked nice yesterday an you look nice today so that's what I'd like", I was surprised for a moment and measured the situation, but remembered I was already using girls clothes so I agreed, hell I spent all night with lots of strangers in a miniskirt so what?, I could manage that and I was far better than him so it was a profitable situation. We agreed to these conditions with the best of five games and started. With sadness in his face he accepted his loss, I knew it I was better and proved it, I saw his face and felt a little guilty, but a wager is a wager and I you have to honor your debts so I told him "that's it pay up", he hesitatingly stood up, turn at me and proposed "double or nothing what do you want?" " "ok, I kind of like your guts, how about your Full metal panic complete DVD set?" he agreed and the match started. Five games later he stood up picked the movies form the shelf and gave them to me, I was unstoppable and proposed another game, he hesitated but agreed, "What are the new conditions, let's go farther" he said "I agreed and asked for 2 more expensive sets" he thought about it and replied "Ok, but you'll have to use the dress I chose and heels" I wasn't worried I had won a lot and I couldn't lose, when we started something was weird I could clearly see that he was playing better I won the first game, but the margin was a lot smaller, I also won the second but he clearly dominated the other three, when we finished I had lost and my only stuttering idea was to say "Double or nothing, what do you want?" he considered this for a moment then excused himself, sent a text message and waited a little for the reply , when the reply got through he grinned and told me: "I have a friend who is a makeup artist, if I win he has agreed to make you over as pretty as possible, what is your answer?" . His winning streak was pure luck I would win and he would have to explain that to his friend who was on his way here, so I agreed and we started. Five games later I was devastated he won 6 to 4 and I had to pay up, so I followed him to the room and he rummaged through its contents, he was deciding which one did he preferred for my humiliation and a little later he made his pick, it was a black little cocktail dress with a little petty coating that could be seen in the lower part, he looked at me and felt good with the decision. It didn't have a low cut so I wouldn't have problems with the cleavage but he gave me a bra and said I should stuff it with something, he opened another drawer and produced the most perfect breast forms. His ex must have been very flat chested to use those things. After that I almost fainted when he gave a pair of 10 centimeter heels that to my horror fitted perfectly in my feet, But I put everything, I'm a man of my word then it hit me, we didn't agree on a time frame I could just use them wait for the makeup and just like that take everything off. 4. Dress for success His friend arrived really soon afterwards so I cursed the lack of traffic in a Saturday afternoon, he arrived and said his name was Alfredo, he oozed gayness, he even greeted Robert with a kiss in the cheek something I found very odd, he saw me and was like surprised because he wouldn't take his eyes of me, "OMG he is gorgeous, you weren't lying" he said and made me feel very uncomfortable. He made me sit and started working on my face, it wasn't as bad as I thought I almost fell asleep and what seemed like hours later he asked Robert for something; Robert went into the room and came back with a Black wig and some cheap jewelry including some clip on earrings, Alfredo bestowed this on me and told me to close my eyes. I was somewhat curious I knew that there was no makeup in the world that could make me look like a girl so I was expecting a freak when I was led to the mirror. I was surprised by what I saw, in the mirror there was a girl not a cheap street walker transvestite freak, it was a real beautiful girl, I even had to raise my hand to check it was really me. I felt something I had never felt, it was a mix of adrenalin, lust and feeling sexy. The feeling of being sexy is not the same as being sexy and is something men don't have the opportunity to feel, is an interesting thing and is something I was completely unprepared for. I stood there checking myself for what seemed ages until I heard laughter, Alfredo and Robert were also awed and saw me with curiosity, I saw later that Robert had a camera in his hand and before I knew it I was posing, first they told me to move like this or like that, later on I gave my own ideas and started doing what felt natural, they took like 50 pictures of me in my dress, later I became curious and Alfredo asked If I wanted to change in another pretty dress. I was surprised of myself when I said yes and ran into the closet. I understood that I was a beautiful girl, but also a lustful boy and this was my opportunity to see this girl dressed in ANY way I wanted so I tried everything that came into mind, some short skirts, stockings, boots, dresses, and sexy blouses. Also Robert's ex had a big wig collection that I tried; it was something that I thought was weird but accepted it nevertheless. Robert was enjoying this lot and to my surprise, me too. At nine in the evening I was very tired and it looked like I had tried like 50% of that closet, I was wearing a tight dress with high heeled boots the makeup was still flawless, Robert then said "Let's go for a bite..." I was starving and started to stand up when it hit me. I was dressed as girl! and terror filled me, "I can?t go like this" I stammered, "this is fun but I won't pass as a girl". "Sure you will", he took me by the arm and led me to the car, Alfredo followed us. 5. The big night rush We got into his Mercedes and I wasn't surprised to see a chauffeur diving us, of course I knew the house had a staff, but somehow it didn't register until now, also it was odd that there wasn't even a whisper about the boy in girl's clothing. If I had an adrenalin rush the first time I saw myself this time I was drowning in it the sole idea of being outside dressed like this, it was killing me, but also fed me and made me stronger; I can only say it was intoxicating, I started watching the faces of the people who looked at me and at first tried to see disgust or surprise, but I saw none a little later I started to admiration and sometimes even lust. We arrived at a big restaurant one that I always wanted to try but looked too expensive for me, when we pulled over, the valet opened the door for me and extended his hand, if he saw me as a guy or in any weird way he never showed it so I took his hand let him guide me. Another valet opened Robert's door and asked him if he was going to use his usual table, but more impressive he told him "Everything is fine today sir, we weren't expecting you so the manager is not ready with the reports" so I understood he was the owner of the place. We had a great meal, I didn't order mine first because the menu was so exclusive I didn't know what to order and because I really didn't want to talk and spoil "the illusion of female", every time Robert was asked "... And for the lady" I almost laughed. When we finished Alfredo excused himself and told us he wanted to see his boyfriend and it was kind of late, he approached me and gave me some pointers on how to maintain my makeup and gave me a little purse with everything I needed there, it was a great touch and I found myself listening with great interest. By this time I was relaxed we had drank some wine and felt confident in my appearance, it was very strange it was like somebody would have lifted a curse, it's great to escape your life once in a while to be who you are even though everybody thinks you are someone else, I was in that trance when Robert asked me if I wanted to dance, I told him I didn't know how and he eased me saying that he was a terrible dancer, but would show me everything he knew about it. We called it a night around 12. I felt like Cinderella and I had to go home before I turned into the ugly male accountant so I told him to take me home, I was so tired that I dozed off and he didn't wake me up until we arrived to his house, he told me it was late and he didn't know where I lived, but could take me there tomorrow I agreed and was led to a bed, where I found a beautiful pink satin nighty, I didn't make any fuzz put it on and fell asleep immediately. 6. Then the morning comes When I woke up on Sunday I felt what I was wearing and felt uneasy for a second, but remembered how much fun I had and realized it had been a great day, I stood up and was very surprise to feel my legs, ass and back extremely tired of so much heel use the day before, it felt also very bizarre in my calves not to have the extra support of my high heels, it was so weird I liked it. I washed my face and wasn't surprised to see that it had a lot of stains from the make up from the day before, I washed a little harder and was kind of disappointed to see my male face again, so I looked for the small purse and took the lipstick out when I found a note from Alfredo, it said: Hi Denise (yes I like that name for you), I knew you would want a new look for yourself in the morning so here are some instructions to make your own face, I know you will do a great job, if you need any help here's my number. Kisses Alfie. I was very happy after I read that and I did my best to make me up, of course it was a messy job, but I looked better, and promised me that it would be better the next time (I was planning a next time and didn't register as odd). When I finished I heard some noise and remembered Robert I climbed down the stairwell still in my nighty and saw Robert playing, he saw me and whistled loudly I blushed a deep red, but accepted the compliment, he looked at me and said "wann'a play?" "Sure I" said "what's the bet?" "easy" he said "if I lose I help you with that big erection, if you lose you do that for me" . It took me by surprise, but I can't say I didn't want it, until that time I had never fantasized having sex with another man, but at that moment I only wanted him to pull down my panties and to stick his big cock inside me so I played and had one of my worst performances. He understood this and kissed me, deeply in the mouth I responded and started to rub his pants in the crotch area, more arousal wasn't needed because he was already big, I went to my knees and used my teeth to open his fly I couldn't believe I was doing this, but I loved it my pulse was deafening in my eardrums and I couldn't stop so the fly gave away and his monster dick darted out, at that instant I was expecting it with my mouth, I of course was no expert, but knew what I liked so I reproduced that as faithfully as I could, it was outstanding and he enjoyed very much, when he inserted it in my mouth I wasn't prepared for the gag reflex and almost threw out, he understood this and inserted it gently until I had swallowed it almost completely, then throbbed it in and out until he was about to squirt in my mouth. Just a moment earlier hi took it out and laid me in my back at that moment his member was very wet of by saliva and also he had a lot of precum in his fingers so he pulled my panties expertly throbbed my cock, he inserted one finger in my ass and then two, it felt weird but interesting at the same time I was relaxing when inserted his big tool in my backside it was very painful but also enjoyable I couldn't believe I almost came at that moment, later on he started in and out and I was surprised it was so excruciatingly delicious, at the same time he continued masturbating me and the he stopped I knew he was about to cam and I started moving my own ass towards him so I could impale me even deeper. He exploded with quantities I didn't know were possible even for porn stars I was drenched in cum and a little later I came also in a way I never thought possible. We laid down for moment expecting the awkwardness to follow , but it didn't, at that moment I looked at his flaccid member and recognized my lipstick in it, I found out the most hilarious thing I had ever seen, but also I found very exciting that it was MY lipstick. That day we did it four or five times I never thought I could have so much sexual stamina. 7. Everything you ever thought you knew about life and you were wrong In the afternoon we were starving and he invited me to another upscale place so I took a shower and decided to use a black pencil skirt that went all the way to the knees. I needed a little padding, but found some padded panties in the drawer (just how flat was this girl?), a white silk halter top that didn't show boobs, because I had none; and the tallest heels I could find. It was weird that it was reassuring to use heels once again. I tried harder with my makeup and using the speaker I had a great class from Alfie. I finished completing the look with long clip-on earrings and a nice straight black wig. I was a stunner. When we arrived at the restaurant I wasn't even self conscious I checked my makeup in the vanity mirror and felt aroused by my sexy female self, even thought that maybe when we came back I could try sexier lingerie and have my cherry popped out again. We were led into a private lounge and when the doors opened I almost fainted, almost all of my friends were there, my face changed colors ten times my heart raced on and I could barely stay on my feet, I was caught by Robert as I fell on my back and could have died at that moment, my embarrassment was complete, what should I tell this people, they have known me for 20 years they know I'm not gay, They know the skirt was a bet, and here I was with the same person who fucked me multiple times just some hours ago, IN A DRESS, a dress and makeup I put on by myself, I could die just there and then... At that moment Melissa saw my face and ran to my side; "Honey, is okay we made this we put you to this" "whaaaat?" my face became red not with embarrassment, but with anger so she explained. "We have known you for many, many years and we have known for some time that your life is not going well you became darker and grimmer everyday it passed. So as you remember we have been leading you into female clothing for sometime because we see it in your face, you find it interesting so we took the chance. This bet was heaven sent and is not the first time we try it, we have tried it at least 5 times before and you never fell for it until this time; so we planned the chance for you to try it, to experiment and if you didn't like so be it we wouldn't force you, but you tried it you liked it and here we see a beautiful young girl, but more important a beautiful HAPPY young girl" "And Robert? What's the deal?" I asked "He is what you saw, but with a twist, his girlfriend the one who dumped him was a full time tranny who left and went to live in Europe, he also had a broken heart so we found a way for him to meet a new girlfriend, so when he saw you at the party he was struck by you and most important by what you could be" "But the bets, and games were my ideas I thought I only had become a victim of my game", "and you did" Robert answered "I really didn't know how I was going to be able to force you into something nicer to wear until you insisted on that game, you know giving away all those DVD's was a small prices to pay so I could see you like this" 8. Epilogue It's been two years now Robert and I got married in a civil ceremony in San Francisco of course I quit my job by not returning at it, I never even returned to my apartment or for my car. We started some businesses with my contacts and Robert's investment; most of them have been successful and I feel really happy to inform that I am rich on my own without my husband's wealth, my wardrobe has tripled and I now understand why we girls need so much clothing. Sometimes looking back I can't believe how much my life changed in so little time and were a little bet could take me, I just remember that when you make a wager you might lose, but be prepared for the consequences losing is relative and only time can tell what is the best or worst thing that can happen when you play to lose.