Wheel of Doom

Can't really say that I thought this would happen. If anything, it opened my eyes to a whole new world. And what's funny is it started as sort of a wager, a way of encouragement, something to boost morale. Never in my wildest dreams would I have thought that my life would change in the way that it did.

You see many years ago Brenda and I started a law firm. We were right out of law school and wanted to change the world as all young idealistic people want to do. Together we built our firm from just the two of us to where we are now. Today we have seventeen people on our payroll and we are highly successful in what we do. Case after case we walk out of the court rooms victorious. So, we decided as a group that if someone lost their case, they would have to spin the Wheel of Doom. A device we created to leave our fate up to chance and let it decide our "punishment." Not that it was really a punishment. More of a means to have some fun. Our career choice is a very serious one after all and we didn't want people getting burnt out due to stress.

Things on this wheel included dressing like a cowboy for a couple of months or wearing an inflatable dinosaur costume everywhere we went (when not in court of course) for two weeks. Nothing that would cause harm and was agreed upon by all to be in genuine fun. As I said we were good, we hadn't lost a case in a long while. No one could really remember when the last time we lost in fact. I knew that our record was roughly three years long and had every appearance of not ending anytime soon.

That was, at least, until yesterday when my client lied under oath. As they say, all good things must end so that is how I found myself standing in front of the Wheel of Doom. It was my case, and I wholeheartedly agreed to do this like everyone else when we created it.

Everyone standing behind me was joking and poking fun, taking guesses on what the wheel would land on. All the banter kept the atmosphere light and humorous. Giving everyone a sheepish grin, I stepped up to the wheel, grasped its edge and gave it a spin. A chant started up of 'cowboy.... Cowboy.... Cowboy!' Everyone knew of my dislike of country music. So, they thought it would be absolutely hilarious if I had to dress as one. I had a feeling it was Brenda who put that up there on the wheel. She liked to poke fun at me. Probably because I liked to poke fun at her. We pranked each other relentlessly. When the wheel stopped spinning and everyone saw what the arrow pointed at; laughter, squealing and cat calls erupted throughout the lobby. "Dress as the opposite sex until your next court appearance." After reading that I busted out laughing. I started to sashay around the lobby, and act like one of the people from a drag show a group of us had all went to a few weeks back. The performer had walked around the audience with exaggerated feminine flair in an outfit that resembled a peacock and what appeared to be not a care in the world for what anyone thought. We all laughed and joked for a few minutes with my coworkers prancing around with me arm-in-arm. It was not until I remembered that my next court appearance was not scheduled until three months from today that I started to panic. Oh shit!

'Alright everyone, let's get back to work' I said. And with a last round of applause directed towards me I retreated to my office. How in the hell am I going to pull this off? I am a guy. Someone who doesn't have a girlfriend or wife to turn to for advice, so I had no idea about what to do or how to do it. How does one go through with making themselves into a woman for a day much less three months? As good as a sport as I am and all, I had no idea what I was getting myself into. A knock at my door interrupted that line of thought.

'Come in' I said. Opening the door and poking their head in was Brenda. 'Got a minute?' Waving her in she approached my desk and took a seat. 'Are you going to go through with this?' she asked.

'Yup, not sure what I am doing but a deal is a deal. I agreed with this the same as everyone else did. I just didn't think I would be the first to have to do it!' I told her with a huge smile on my face hoping that it looked genuine. Deep down I was fighting off an anxiety attack!

'It's a good thing it's Friday, gives us the weekend to make you presentable' she said.

Now I would never have thought to ask for help with this to be honest. Brenda is a great person, very caring and has been the closest person to me than my own family ever was. She is my best friend. And I have had a crush on her since the day we met. We started this firm together. Consoled each other through losses and other challenging times. She is the one that I would turn to if I needed anything, and I hoped that she knew that I would give anything for her. She is also really, REALLY good looking with her long black hair, bright green eyes and a figure that screams "sexy". I like to watch her enter a room because of her confidence and how she just lights up the room but love to watch her leave for her ass. So, it took me a moment to register what she said.

'We?' I asked.

'Yes, we.' She replied. 'Wouldn't want you to make us look bad, besides with your build and face structure I bet I can make you snap some necks when you walk by! This is supposed to be fun. We all agreed on the Wheel of Doom to keep our crew having fun in a world that doesn't want us to. So, let's have some fun.'

I couldn't be more surprised at that moment if flying elephants zoomed past my window than by her words. She was right though; I am not a big guy. Standing at five foot, six inches; and tipping the scales at a hundred and ten pounds, I was often called an "Elf" in college because of my build. My face didn't help any either, I had been told by many people that my face was elfish, narrow jaw to a pointed chin, big eyes. Hence why I was nicknamed "Elf". Not like the guys who bullied me, who had the typical strong male face.

'Ok...let's make this fun then, what should be the first thing we do? I don't want to look over the top and I have no idea what I need. Do you really think I can pull this off?' I asked her.

'Well for starters let's hit some stores. You are going to need a lot of things to last you the three months you signed up for! But to answer your question, yes, I think you can pull this off. You have anything you need to take care of for the rest of the afternoon?'

'No, I'm free.' I replied.

'Well, no time like the present to get this started then huh! Let me get my jacket and let's get out of here' she said. 'Meet me at my car, I'll drive.'

During our shopping trip we talked about what all I would need to do to present myself as a woman. From ensuring that my legs were shaved when I wore dresses, skirts, and shorts, to masking my genitalia by tucking it in between my legs, to wearing padded bras to give the appearance of breasts. She said that I should watch all the woman around us on how they walk and try to mimic them. Listen to how their voices sounded and how they spoke. 'Guys talk, walk and present themselves in a manner that is not all that different from gals, but there are some subtle differences if you look and listen carefully.' What she was telling me and how she presented it gave me the distinct impression that she had done this before.

When I asked her how she knew what it would take to change a guy into a gal she said 'a very long time ago, before we met, I was friends with a guy who liked to cross-dress. And he asked me for help in getting the stuff he needed. He felt too embarrassed to go alone so I went with him. We learned a lot about how to transform him. He eventually had all the procedures needed to transition. Now she is very happily married and living in Europe. You probably won't remember her; you very briefly met her once; her name is Sabrina.'

I wracked my brain trying to remember ever meeting Sabrina and came up with nothing. 'No, I don't remember her. Were you there for the entire transition?' I asked.

'No, she moved to Europe before she had her reassignment surgery. I hear from her now and then. The time difference and distance makes getting together near impossible but she is still a close friend.'

After many stores and my hands full of shopping bags I found myself back at my car feeling a little overwhelmed. 'I'll be by your place around nine and we'll start transforming you,' Brenda said.

'Sounds great' I replied and after stuffing all the bags in the passenger seat I headed to my apartment. Getting through my door I deposited the bags on the couch and wandered into the kitchen to fix something to eat. I had not really paid attention to the time, so I was a bit surprised to find that it was almost nine and with Brenda being Brenda, I knew she was going to show up early. Sure enough, there was a knock at the door. Not bothering to wait for me to answer, Brenda comes bounding in with a gleeful look on her face and a few more bags.

'You're not having second thoughts, are you?' she asked.

'Nope, want a drink?'

'Got that covered' she replied rummaging in a bag and pulling out a bottle of wine. While she was opening the bottle, I retrieved a couple of glasses. After clinking our glasses together, she says to me 'Let's make you beautiful!' The excitement in her demeanor was palpable and contagious. I was starting to feel excited about doing this. 'Strip.' She told me. That one-word command...

I never thought of myself as a subservient type of person but the next thing I knew I was down to my boxers. 'Your turn' I said with a chuckle.

'Not me getting transformed so no!' she laughed. I was a little disappointed, she is a knockout. It also occurred to me that of all the years we have known each other we have never seen each other naked. Walking around me, mentally measuring me to the last ounce she stops in front of me, squats down and with one quick motion yanks my boxers down to the floor. With my parts dangling in front of her face I could not resist the thought of her lips wrapped around me and started to get an erection.

'Mmmmm' is all she said as she straightened back up to stand in front of me with a twinkle in her eye. 'Very nice. And that is going to pose a slight problem though' she said pointing to my growing penis. Now go shower.'

Doing as I was told I headed into my bathroom. Just as I step in the shower she hands me a new bottle of soap, shampoo, conditioner, and razor. She said if I were going to make myself up, I would need to use stuff that would make me smell like a woman and not musty like a guy. I also needed to make my body smooth and hair free. Shaving was easy. I didn't have much body hair to begin with but after I was done, I could barely keep my hands from running up and down my smooth legs. And the smell of my hair.... Divine! As I finish and towel myself dry, I open the curtain to see her sitting on the countertop looking at me up and down. 'Nice, and you smell delightful. Might have to pick up some of that shampoo and conditioner for myself.'

Like I said, Brenda and I are best friends. Yes, I have always wanted more but I never got the impression she wanted more. That look in her eyes though...I was starting to wonder if we both kept our deepest feelings for each other hidden from one another. It was a look I had seen from her when she thought I wasn't looking at her. The look of people admiring their significant other. Lord knows I had been mooned eyed over her. She is everything that I wanted in a girlfriend. She is wickedly smart, quick witted, funny, kind, and my goodness drop dead gorgeous. Now I don't think of myself as ugly by any means. I honestly thought that she liked more manly men because of who I had seen her date.

'Now, remember to use moisturizer,' she said hopping off the counter and squeezing some lotion onto her palm. Coating both hands she starts to rub it into my legs. The moment she slides her hands up my thighs my erection returns. I couldn't help it, she was taking her sweet, sweet time with long slow strokes working one leg then the other. Sliding her hand up between my thighs and back down, back up and back down. With each up stroke grazing my balls and with her lips so close to my penis... the feel of her warm breath flowing over it, I was loving every second. Looking down at her I can see that her lips are slightly parted, and she is breathing a bit faster than she normally does. Was she making it known now of all the times we have shared to let me know she wanted me and was taking this opportunity to show it? With a kiss to the head of my fully erect penis, she stood back up and led me by the hand to the bedroom.

That made my eyes pop. I nearly exploded when her lips touched my penis and I really wished she did not stop there! I swear that my balls changed from their normal color to blue at that moment. In the bedroom she had laid on the bed a pair of panties, a bra, blouse, and skirt. While she watched I started with the bra, it was padded a bit and as I put it on, oh my! The feel of the soft, silky fabric gliding over my nipples instantly made them hard. The feeling that elicited...oh my god! I knew my nipples were sensitive, but my goodness! Fastening the front closure, I felt a twitch in my penis. The panties came next. The panties were boy short style in their cut which I appreciated. Especially since after seeing the skirt on the bed. I did not want to pop out at the most inopportune moment. Sliding the panties up my legs had me about ready to explode again, the silky-smooth material against my freshly shaven, smooth legs, was making my penis twitch uncontrollably and I noticed that there was a lot of precum oozing from the tip. I left the panties down some so I didn't get any precum on them and I tried hard to concentrate on something mundane to get my erection to go away but I was failing miserably. There was no way I was going to be able to tuck with it being hard as a rock! She noticed my predicament too and scooped up my precum with her finger before it could reach the waist band of the panties. The touch of her finger produced more twitching and more precum and elicited a moan from my lips. She scooped up my precum with a finger and did something unexpected, she put her finger in my mouth.

"Surprised" is the word I would have chosen at that moment if it weren't for the fact that like some lost instinct resurfaced, I closed my lips around her finger, staring deeply into her eyes and sucked my juices off it. Surprised turned to shock as I realized what I did. She just smiled a knowing little smile, dropped down to her knees, and took my penis into her mouth. I must be dreaming. There is no way this is actually happening! I am going to wake up any minute. Of all the fantasies and dreams I had about Brenda...nothing compared to what was going on now!

She stroked me with her mouth and swirled my head with her tongue with great care. I was moaning in ecstasy with the first touch of her lips. I was so turned on that it didn't take long, and I told her I was about to cum. She doubled her efforts and in no time at all I flooded her mouth. She continued to suck, drawing her lips up and down my shaft making sure that I was completely empty. After ensuring she had every drop she stood and kissed me. Her full mouth depositing the cum into my own. We stayed kissing for quite some time, each of us savoring the taste as our tongues danced. I was still intensely hard and now I was even more turned on, which I did not understand. A bit dazed and wobbly from the intense orgasm I just had, and the intense kiss we shared, I plopped down on the bed when our lips finally parted. I looked up at her in bewilderment. There had only been a few times where I was able to get off from a blowjob and never ever had it been that quick. She smiled down at me in a wicked little manner and scooped up a bit of cum from the corner of my lower lip that had escaped our kiss. As she sucked it off her finger she started walking to the door.

'Finish getting dressed so I can help you apply your makeup; we are going out'.

Still a little dazed and in absolute shock I sat on the edge of the bed. Holy shit did that just happen? I must pinch myself because this really has to be a dream. And why is it that I just found out that I really enjoyed the taste of cum. Was it because of the way it was delivered? A lot of confusing thoughts were floating in the back of my mind. And I couldn't pick them apart. I tucked myself away when I was finally flaccid and regained my senses; and pulled the panties up the rest of the way. The skirt was next. It was a white pleated mini skirt; to better hide my male parts she explained to me when we bought it; that ended at mid thigh. There was a bit of a bulge that the tight boy short style panties just could not hide but the pleated skirt kept it fully and nicely disguised. Tucking everything down and back to make my groin as flat as possible was an odd sensation. It wasn't uncomfortable, just different than how I normally presented. The next to final item was the blouse. It was a silky tank top of a noticeably light pink color. A pair of heels that matched the shirt finished the look. Walking out of my bedroom Brenda looked at me and wolf whistled

'Come here so I can get a better look at you.' Spinning around in front of her, she appraised me and said 'wow, you have an amazing figure you know that? An hourglass figure that a lot of women wished they had. And a really cute butt! Nice and round, not to small and not huge! Just the way I like them!'

I gave her a curtsy and asked, 'now what?'

'Now I will teach you how to apply makeup! Have a seat.' For the next half hour we went through the basics. Once done she sat back admiring her handiwork. 'Ok, go look. These little mirrors don't give the full effect.'

Getting up from the table we were sitting at I started to head to the bedroom with Brenda following me. On the back of my bedroom door, I had a full-length mirror. Closing the door, I got to see the full effect of our efforts and I did not recognize myself one bit. I had curves and cute little titties thanks to the padding of the bra. I knew that my waist was a bit narrow, just hadn't realized just how feminine my figure was with the clothes I normally wore. We had not done anything to my hair yet but wow.

'Impressive huh? It is utterly amazing how a little makeup and a change in clothes can alter someone's appearance. Now let's do something with your hair. Tomorrow, we will get it styled but for now I think we can just put it in a ponytail with a couple stray wisps in front of your ears to complete your transformation. For now, anyways.'

During the entire process we joked and flirted with each other. I really wanted to return the favor and get her off by burying my face in her pussy but did not have the chance to even give her a peck on the lips. She fended my advances with skill while at the same time making it known that she wanted them, just not right now. I was still in shock that what happened did indeed happen. I was really expecting to wake up and find that I dreamed it. All finished with my hair I took another look in the mirror.

Following me into my room and putting her head on my shoulder, encircling my waist with her hands from behind me she smiled at our reflection and said, 'you ready?'

'Ready for what?' I asked.

'Ready to get a drink of course. Here, I already put your wallet, keys, and lipstick in here, let's see how many heads we can turn!' She said kissing me on the neck while handing me a small purse. I would have rather stayed in and fucked like rabbits but she was already out the door.

Down the street was a bar that I had only been to one other time. From what I remember it was a classy place. People who went there were obviously professionals of some field or other. And the best part about the place, it was well within walking distance. Only a block away! I thought I would have trouble walking in the heels but found that it was not as difficult as I expected, navigating the stairs was the only area that I really had to pay attention to. Brenda walked behind me for a bit and remarked how well I was doing, like I was a natural. Going as far as to say my walk was no different than any other woman and noted how my hips swayed slightly back and forth looking enticing and natural.