Halloween Gone Wrong!

Halloween! Every crossdresser's favorite holiday! After this year, I may never dress for Halloween again.

It was Ken's fault. I never, ever, never should have listened to him. I loved him dearly; he was a great friend and we had unbelievable mind-blowing sex together, but he sure liked to take it to the edge. This time it would be only me taking that walk.

"Hey Luke!" (Luke is Maria's male persona. Luke is in a more-or-less loveless marriage and has a son. His wife usually takes their son to see her parents almost every weekend. It's more than a three-hour drive away so Maria has plenty of play time!) I was sitting in the company break room having coffee when Ken sat down.

"Yeah, Ken, what's up?" I could tell by the tone in his voice I wasn't sure I was going to like this.

"Have you seen the flyer about the company's Halloween party? There's a costume competition and Mr. Ross (the company owner) is offering a total of $30,000 in prizes for the best costumes. There are three categories, single, couple, and group costume. Each category will win $10,000 of the prize money!"

"Yeah, so...."

"I thought we could go for the couple's costume. That would be $5,000 apiece."

I just looked at him quizzically. "What couple's costume could Ken and Luke possibly wear that would win the prize?"

"They couldn't." He just smiled his most mischievous smile.

It dawned on me what he was about to suggest, and I cut him off. "No way, no fucking way! This is my fucking job, Ken, you asshole! No way am I dressing up and bringing Maria to the company's Halloween party. No fucking way! The women will take one look at me and know immediately I'm not just wearing a costume. They'll be able to figure out almost immediately Maria dresses on more than a regular basis! NO FUCKING WAY!" I was practically yelling at the end.

"I thought of that too." he said smugly. "Remember how you went to that transformation service in Vegas? You can go to one here, we'll say you did it for the contest, and that should satisfy even the nosiest busybodies at the company."

"You're fucking crazy, man. You're fucking crazy."

"Just tell me you'll think about. Just don't say no without thinking about it."

I should have said no right then and there. The more I thought about it, I had to admit Ken's plan wasn't bad. Before I left for the day, I popped into his office. "What's your costume idea?"

Ken got this huge grin on his face. "Hugh Hefner and a Playboy Bunny. My costume will be a lot easier, but I know you can pull this off. You'll look so fucking hot as a Playboy Bunny! I'm getting hard just thinking about Maria dressed like that."

"I know I'm going to regret this but you're on. I'll do it!"

Two weeks later, we pulled up to the company's lavish Halloween party. The company photographer was taking pictures on a red carpet leading up to the building. Ken had hired a limousine to pick me up directly from the transformation service and bring us to the party. The driver came around to let us out and opened the door.

Ken got out first. He looked like a classic Hugh Hefner. He had even dyed his blonde hair black. He was wearing a red satin smoking jacket and white silk ascot with black silk pants and black velvet bedroom slippers. He had the nautical captain's hat on his head and a pipe in one hand. He easily imitated Hugh's confident, loose smile.

I gulped. There was no turning back. I worked with all of these folks. In my wildest dreams (or nightmares should I say) I had never, ever thought about dressing up in front of my co-workers.

Maria's long stockinged leg ending in a black satin, open-toe 5" stiletto heel pump came first. The other leg followed suit. My sheer to the waist jet-black pantyhose covered my legs completely, including my ass cheeks which were half exposed. I eased out and stood next to Ken. I was wearing the classic bunny costume which consisted of a black satin corset teddy, complete with matching black satin bunny ears, white satin tuxedo cuffs on my wrists, and a white satin choker with black satin bow tie. I even had the satin ribbon on one hip with my name on it. My makeup was centered around candy apple red lipstick and matching nail polish on my fingers and toes.

I was slightly shorter than Ken's 6' 2" frame in my heels, but it didn't faze him. Then again, he wasn't the one standing in front of everyone he worked with wearing clothes of the opposite sex!

We stopped on the red carpet for the obligatory company party pictures. I hammed it up for the camera with all the standard bunny poses. Face-to-face with our arms around one another, me with one heel high in the air. Side-by-side with our arms around each other's waist, me with one hand on my hip, pouting sexily. There was the slightest chill in the air, so I asked Ken to get us inside.

We were immediately surrounded by many of our co-workers. "Ken, Luke! Holy shit, that's just amazing. You guys should win first place hands down."

Ken laughed a belly laugh; all I could manage was a nervous giggle. "You can call me Hugh for the rest of the night. This is Bunny Maria." I pinched him, hard, in the middle of his back so no one could see. He just looked at me and smiled, pulled me close to him, and gave me a kiss on the cheek.

Pretty soon the novelty wore off and we were just two more co-workers in costume at a company Halloween party. We even got separated sometimes. My co-workers were curious but complimentary when I explained about the transformation service. That is, until Theresa, one of the executive secretaries approached me when I was standing all alone.

Theresa had a thing for Ken. Then again, all of the single and half of the married women at the company did. Ken was that hot. Gorgeous, confident, successful; Ken was everything a woman could ask for and more. "You're not fooling me, 'Maria'," she said with anger in her voice.

"I have no idea what you're talking about, Theresa." I tried to respond as pleasantly and placatingly as I could. I knew where Theresa was about to take this.

"Transformation service, my ass! They may have done the cosmetic work on you for tonight but you're way too comfortable, way too confident in that outfit for this to be your first time. Just how long have you been dressing, 'Maria'?" she asked scornfully.

"Theresa, I have no idea what you're implying."

"You know exactly what I'm saying, you bitch!"

"Theresa," I continued to talk to her calmly. "Damn near everyone in this company knows you have it bad for Ken. It would be a shame if unfounded, vicious rumors began to circulate about tonight. About what was supposed to be a fun-filled evening for all of the company's employees. I'd hate to have to go to Human Resources about rumors like that. They're very good at what they do, and I have no doubt they'd be able to trace those rumors back to their source." I smiled sweetly at her as I said this.

Theresa stalked off. "Well, at least one person in this company knows." I said to myself.

I felt the need to go find Ken to let him know about my conversation with Theresa, but I didn't see him anywhere. It was a big company and a big party. Thirty minutes later, I still hadn't found him but there was a tap on my shoulder. I turned around and it was Mr. Williamson, Mr. Ross's executive assistant. "Excuse me, Luke. Mr. Ross would like to see you in Ken's office." Of course, Mr. Williamson would call me Luke when I was dressed like this. He had no sense of humor, didn't have a costume on, and was a straightforward, no-nonsense kind of guy.

My mind was racing a mile-a-minute, but I was somewhat comforted by the fact that I was going to see Ken in his office shortly, even if Mr. Ross was also there.

I didn't bother to knock; I'd been in Ken's office so many times as Luke it just felt natural. As I entered and looked around, I could see there was only one person in the room, sitting behind Ken's desk and it wasn't Ken.

"Good evening, Luke. Or should I say Maria? I have to admit, you look even more amazing than I'd heard."

"G-g-good evening, Mr. Ross." I stammered. I was starting to get a sinking feeling in the pit of my stomach. "Um, where's Ken? I thought he would be here too."

"Ken's gone for the evening, Maria. He had an urgent business assignment on the West Coast. Something I told him only he could handle. I assured him we'd make sure you got home safely in your limousine."

"O-o-okay, Mr. Ross. I guess I'll be going home now."

"Maria, the night is still young, the party's just getting started. You know, Theresa and I just had the most interesting conversation. I'm guessing she's right. I'm guessing this isn't the first time you've ever dressed up as Maria. As a matter of fact, I'm going to make an assumption of my own. Ken was overly concerned about being sent on this assignment immediately. He didn't calm down until I assured him you would be taken care of. That wasn't just friendly concern on Ken's part. You're lovers. You've slept with him before. And looking at you dressed like that, not only am I not surprised but I don't blame him."

"Um, Mr. Ross, that's a pretty serious accusation. Ken is one of your top managers and I've always gotten really good performance reviews in my time here at the company."

Mr. Ross stood up. He was completely naked from the waist down. "Maria, I'd like to give you a performance review of my own. I want you to come over here and sit down on my lap. I want to cuddle with you and see if I can tell you're not everything you appear to be. And please, call me Oliver. All my friends do. I think I want to be really GOOD friends with you, Maria!"

"Mr. Ross! I can't believe this; I can't believe what you're saying. That's sexual harassment!"

"It won't be harassment if you agree to it voluntarily, Maria. And I told you to call me, Oliver. I'm not asking you; I'm telling you to call me Oliver."

"Ol-ol-oliver, please. Please don't do this. Maria has never been coerced into anything before. She has always been upfront with her lovers before any relationship and there has always been mutual understanding and respect. I'd feel.... violated."

"Your choice completely, Maria. Of course, there probably wouldn't be anything I could do when your performance reviews begin to slip until you get fired. And of course, if your wife should happen to receive pictures of you dressed as Maria, I'm sure she'd be less than happy. Why, she'd probably be able to use them in the divorce proceedings and take most of the money and property."

"Oliver, no." I began to sob.

"Maria, I've had to be fairly ruthless to build up my business. I have private detectives occasionally following all my top executives, like Ken, and top performers like you. I could never allow you to bring scandal to my company. How do you think Ken's wife would feel about all this?" He allowed this to sink in and just stood there, half naked, staring at me.

I nodded, he knew I meant in agreement and not just understanding. I walked over behind Ken's desk where Mr. Ross, I mean Oliver, had sat back down in Ken's chair. "Maria, please sit with me. I want to feel that gorgeous satin ass and those luscious nylon thighs in my lap." I sat down gingerly but Oliver pulled me to him.

"Maria, my wife would never dress like this for me. She's turned out to be nothing more than arm candy. A blood-sucking bitch who only married me for my money. I've dreamed over and over of being with a woman like you, a woman confident in her beauty and sexuality. My wife is here tonight; that's why I had you meet me in Ken's office. We don't have time to make love, but I wanted to know what if felt like to be with you. Reach underneath us and stroke me while we kiss."

I turned my face towards Oliver and reluctantly moved my lips towards his. I reached underneath us and grabbed his throbbing shaft in my hand. He kissed me hard and began to buck his hips in my grasp. He suddenly stood upright causing me to stand up as well. I lost my grip on his cock. "Ol-oliver, what's wrong? I'm sorry, what did I do wrong?"

"Nothing, nothing at all. You're even hotter than I imagined. I'm just not going to cum like some lovestruck teenager getting his first hand-job. I need to get back to the party; I've been gone too long." He said this as he was pulling his pants back up.

"Mr. Williamson is going to give you the number of a private throwaway cell phone I have. My wife is flying to Florida tomorrow. I want you to text me telling me where to meet you tomorrow night. The place should be relatively discreet. I want you to dress up for me; hot, sexy, something we both know my wife would never wear."

"You're more than welcome to stay at the party. Ken's excuse for having to leave early is solid and no one will suspect. Who knows? If you stay, you might win the singles costume competition!" He smiled at me and walked out the door. Mr. Williamson came in shortly after and handed me a plain, white business card. There was a phone number written on it. Then he too turned and walked out the door.

I sat there devastated for what seemed like forever. I decided I HAD to rejoin the party. Ken's absence could be easily explained, mine would not. I slowly walked to the door, opened it, and moved back into the cacophony of noise and revelry. The only thing I remember was this sinking feeling in the pit of my stomach as if my heart had fallen that low.

Occasionally, I could see Theresa in the background of my vision, smirking triumphantly. Once, Mr. Ross was in my line of sight. He was looking over his wife's shoulder and winked at me. I ran to the bathroom; I was afraid I was going to throw up.

I have no memory of any conversations I might have had for the rest of the night. Apparently, I even won the singles costume competition for the evening. Shortly after, I thought it wouldn't be too obvious if I left. The limousine was taking me home.

I called Ken, sobbing unconsolably. I was too heartbroken even to berate him for getting us, for getting ME into this mess in the first place. Ken was furious as I told him all the details of what happened after he left the party. "Maria, do you trust me?"

"After tonight, I'm not sure I should!"

"Maria, will you trust me? I NEED you to trust me, baby. I can fix this, but I have to have your complete trust."

"I must be crazy, but OK, Ken. What do I do?"

"Meet Mr. Ross tomorrow night. Dress in the craziest, sexiest outfit you have. Meet him in the hotel bar where you hang out. I'll take care of the rest."

"Ken, baby, I'm scared. I'm REALLY scared. This could completely change my life; this could completely change both our lives forever."

"Maria, I PROMISE that is not going to happen. Trust me baby."

We hung up and I agreed to do as he asked. Ken was more than a little bit wild, more than a little bit crazy, but he was also brilliant and caring. I didn't have any other options as I thought about it.

I showed up at the hotel bar the next afternoon. I had gotten a room to make it easier to prepare and change. I was wearing the hooker outfit from my last outing with Daniel before he got called to the Middle East unexpectedly.

I was wearing a strapless black leather dress that zipped all the way down the front. Underneath, I had already glued on my silicone breasts and vagina. The dress was cut low in the front and showed ample cleavage. I was wearing 23" black leather opera gloves that came well above my biceps. The gloves alone cost a small fortune!

Underneath, I was wearing a black leather corset with eight garter straps. The straps were holding up the sheerest, midnight black stockings. They had Cuban heels, back seams, and a keyhole welt. I had a Barbie-blonde wig on my head that cascaded all the way down my back to just above my ass cheeks. I wore ruby-red lipstick and made sure to match the rest of my makeup around that. My outfit was completed with gray pearl jewelry. I had dangle earrings, matching choker necklace and choker bracelets and was wearing six rings.

There was one notable addition. Unlike last time, this time I was wearing black over-the-knee, 4" high-heel boots. They weren't thigh high but came about 3" above my knees. They were the softest leather, skintight, and molded to my sexy toned legs. I had purchased them with the money Daniel had 'paid' Maria during his fantasy. He had given Maria $1,500 for her 'services.' The intent was for me to return his money the next day. The payment was part of the roleplay.

I had texted Daniel and insisted on sending his money back to him. He refused and wouldn't give me his overseas address. He told me to keep the money and spend it on Maria. The boots I bought to accentuate his outfit cost close to $1,000. They were incredibly sexy but nothing that I could have afforded to buy on my own. And here I was, wearing them for the first time for the owner of my company who had sexually harassed me yesterday and was getting away with it.

I didn't dare tell Harold about Mr. Ross. Harold was the bartender at the hotel and my confidante. I had cried on his shoulder more times than I could count. Even though he was 100% heterosexual (I know, I tried to seduce him on more than one occasion!), Harold was very protective of me. I did NOT need Harold threatening the owner of the company where I worked.

I was sipping on my usual brandy when I felt a gentle hand on my shoulder. It was Mr. Ross. He was dressed to the nines in a Giorgio Armani suit and Luis Vuitton shoes. The rings on his fingers probably cost more than my entire outfit.

He looked very sheepish when he handed me an unsealed envelope. "Maria, before either of us say anything else, please read this."

I opened the envelope, inside there was a letter that read:

"To whom it may concern,

My name is Oliver Ross. I am a well-known and successful businessman. Yesterday at my company's Halloween Party, which I threw for my employees' enjoyment, I crossed a line and sexually harassed one of my most valued employees. I am writing this letter for this employee to give to our Human Resources Department if this employee chooses to do so. The witness to this incident is my Chief Operations Officer, Ken Johnson. It was an incredibly clumsy and awkward thing for me to do. I know I have caused this employee untold pain and anguish. This letter is some small attempt on my part to begin to rectify my mistake.

Sincerely,

Oliver Ross"

"Ol-ol-oliver? Is this for real? Is this some kind of joke?"

"No Maria, it's real. It took Ken to make me see I needed to write this and give it to you, but it's real."

"What the hell did Ken say to you?"

"You mean after he got done calling me a flaming asshole?" Oliver laughed. "Ken told me he would quit the company and take you with him. He said I might be able to ruin your personal lives, but he would do everything in his power to ruin my business life. He threatened to go to my biggest competitor. He also told me I didn't need to be Jacob Marley or Ebeneezer Scrooge to be successful."

"While I would hate to lose Ken, or you, to a competitor, I would hate to lose myself even more, by treating people badly who have helped make me successful."

I just sat there, stunned. Whatever else I thought might happen tonight, this was not it. I leaned in, hugged Oliver to me, kissed him on the cheek and said, "Thank you. You have no idea how grateful I am for your change of heart."

I invited Oliver to sit down. I signaled Harold and he got Oliver a drink. Oliver asked for a Nolet Reserve Dry Gin and tonic. Harold's eyebrows rose but he raised his hand in salute to Oliver's good taste.

Oliver and I just chatted. It was the first time we had ever talked about anything other than business. It was casual and relaxing. Lounge music was playing in the background. 'Corazon Espinado' by Santana came on. I couldn't help but sway in my seat. Oliver smiled and said, "Would the lady like to dance?"