An Unforgettable Halloween

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Tessa gets tricked at a Halloween ball but it turns out to be an unforgettable treat.


This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This year all proceeds were designated to go to Hospice. The cause itself was good enough reason for me to attend. However, my decision to go was cemented when I saw pictures of the mansion where the party was being held. It looked like a spectacular place to spend Halloween. It also gave me an excuse to shop for a new dress and attend the party as my alter ego, Tessa.

I do not get many opportunities to go out dressed as Tessa so I decided to take full advantage of this one. I took the time to seek out a salon that would do my hair, makeup, and nails. I spent a day searching for a new dress and of course shoes too. I wish I had been able to shop for all of this as Tessa. That would have allowed me to try on different options instead of buying something and hoping and praying that it fit and looked hot.

I had a pretty good idea of the style of dress I wanted and I found a couple very nice choices at a dress boutique. The woman manager of the boutique was a great salesperson and talked me into earrings and other accessories to go with each dress. The dress I really wanted to wear and hoped would look the best was a shimmery, form fitting sleeveless sheath style that featured a low cut v-neckline designed to show some but not too much cleavage. I suspect the manager knew I was buying the dresses for myself but she did not show any apprehension about helping me. I think there are plenty of men who wish they could shop with a person like I was fortunate to have met.

As I mentioned I was going all out for this event so I treated myself to a new VS bra and panty set. I also bought some shapewear to help give me more of an hourglass figure and lift up my round ass. I am only five foot six and weigh one hundred and thirty pounds so I am on the small side for a man. When I am dressed I think I my body looks better than many women. Of course I keep my body shaved and smooth and that makes it look more feminine too. My legs are toned from running but still shapely and they look feminine in heels. I have let my hair grow past my shoulders, and I planned on having it cut and styled at the salon. I didn’t know anyone in this town who would recognize me dressed as Tessa so I decided to just go for it all and have fun. I was planning on showing up as a woman and enjoying the evening talking and mingling.

I took the purchases back to my hotel and found both dresses fit nicely. I decided on going with the blue shimmery dress that fell a few inches above me knees. With all my purchases taken care of all I had to do was wait one more day for the party which, after a sleepless night due to the excitement I felt about attending the pending party, finally arrived. After a light breakfast I set off for my salon appointment.

I entered the salon dressed in male clothes. I was trying to be incognito with sunglasses, hat, hoodie, and jeans. I was hoping no one would think much of the garment bag and small suitcase I had with me. I was glad to have found a parking spot in the back of the salon next to the door so I would not have to walk too far in my dress and heels after my appointment to get to my car. As I walked up to the receptionist counter there were three women hovering around. They all smiled brightly at me and seemed to be very interested and excited about my upcoming transformation. I had told the person whom I booked the appointment with that I was going to the costume party and it appeared that everyone in the salon now knew it too.

One of the women at the counter said, “The party is gets better every year. I went last year and it was great. You will have fun. Everyone that attends is very relaxed but it can get pretty wild.”

I was glad to hear I probably wouldn’t have to worry about hearing any derogatory comments that sometimes get directed at guys in dresses. Another woman introduced herself as Tara. She said she would be doing my makeup but Rachel was going to do my hair first. I was taken into the back of the salon. Rachel had me take off my clothes and put on a soft white robe. She then walked me to her chair and told me her plans for my hair as if she had been thinking about it for some time. She told me she was going to add some volume through layering. She also wanted to put in some extensions. My hair was already down to my shoulders but she said she wanted to have it cascading midway down my back. I figured if I was going all out then this would fall into that category so I agreed to let her do it.

Rachel did not let me see my new “do”. However, when she was finished I could alanya escort feel bangs on my forehead but also more volume on my head and neck through my robe. Rachel then walked me over to get my nails done. I got a pedi and a full set of nails on my hands. The nail tech painted both my toes and hands a bold blue that matched my dress quite well. While my nails dried I closed my eyes and tried to imagine what the night would bring. I was starting to drift off when Tara came to get me.

“Oh, wow! Your hair looks awesome! I am going to start on your makeup in a minute but first I want to shape those eyebrows a little.”

Tara waxed and shaped my brows. She took her time shaping and arching them and I knew the final result could only be deemed feminine. Tara then had me sit in her makeup chair and began working on my face.

“I am going to take a minute to even out your skin tone and then give you a flawless airbrushed complexion.”

I sat silently as she went to work.

“Then we will do a dramatic smoky eye with long lashes. I have something I am going to put on your lips to plump them up. I think that will really help your look. Everyone loves big, pouty lips. Don’t worry they won’t be over the top, just sexy.”

Tara continued to work on my face. I was impressed how fast and effortlessly she worked. She told me how she has worked on several film sets. I was very lucky to have basically stumbled upon this salon and was very fortunate to have an expert doing my makeup. When she coated my long fake lashes with mascara I could really feel the weight of them. I blinked a few times and Tara said I would get accustomed to them quickly. She then said they really made my eyes pop. As she stepped back to look at her work a sly smile came to her face.

“Yes. You look great. Quite pretty.”

Whatever Tara had put on my lips had really made them plump up. Even before she applied lipstick and a high gloss I could tell they were much fuller. I was getting excited to see how I looked. Tara brushed out my hair and said she was finished.

“Are you ready to see yourself, Hon?”


“Why don’t you get dressed first so you can see the full effect?”

Tara led me to a back room where the women had placed my dress and bag. Someone had covered up the only mirror in the room. Tara told me to get my dress on and then come out and model for her.

As I got dressed I was shaking with excitement. I loved the way the dress clung to me. The strappy platform sandals I bought were way too high but I did not care because they were so sexy and I loved the way they showed off my newly polished toes. I put on my earrings, bracelets and necklace and stepped out of the room so I could finally see myself.

Tara greeted me as I stepped out of the room.

“Holy shit!”

Her voice startled me.

“You look so damn good!”

I walked over to the hair cutting station so I could see myself in the mirrors. I had to bring my hand up to my mouth to know I was looking at myself in the reflection. I did look good… nothing short of pretty. I suppose anyone studying my arms would know there was a little too much definition there for them to belong to a female. However, there are plenty of women who work out that have arms as muscular as mine. On close inspection there were other clues that gave me away but without too much scrutiny most people would think they were looking at a woman when they saw me. I could not have been happier with the results. I looked quite pretty, like someone I would want to date. That brought about some concerns for me. As I pictured myself going to the costume party I knew I wanted everyone to think I looked great and the ultimate compliment would be to be mistaken for a woman but that could also mean a lot of trouble too. Then I thought what the hell, no one would know me and after all I would be attending a charity costume party. It’s not like I was going out to a bar to try and pass as a woman.

Tara looked at me from my head to my toes and said, “You know there are going to be people wondering why you did not wear a costume.”

“What do you mean?”

“I mean there will be plenty of people who will see a hot woman in a dress. They will think you came without a costume.”

“No way.”

“Oh, yes way. Wait and see.”

As I looked in the mirror it dawned on me that I could be mistaken for a woman. I had long real hair, a perfect makeup job that hid my masculine features enough to make me pretty, and I had a thin, hot looking body. I had a new, stylish dress with killer heels and I had the perfect accessories. I knew I was dressed better than many real women would for a formal party. I downplayed Tara’s comment and after thanking her for her tremendous help I walked out of the salon to my car.

I was glad it was unseasonably warm as I only had a shrug over my dress and no coat. I loved hearing the click of my heels on the pavement and feeling the air rush around my smooth legs. I had an incredible artvin escort amount of sexual energy streaming through my body.

I managed to get to the mansion without getting into an accident. Driving in heels is not an easy task. I pulled up to the valet parking area and let the valet park my car. The valet happened to be female and she politely handed me a ticket and took my keys without giving me a second look. She either didn’t care I was dressed as a woman or didn’t know I was a guy. I wasn’t sure but what did it matter? I walked away from the car, took a deep breath, and walked up to the entrance of the palatial house. The home was exquisitely decorated for Halloween with an interesting mix of ghoul and elegance. There were many people milling about. Most people were in actual costumes but some had chosen to wear formal attire with Mardi Gras type masks covering their eyes and forehead.

I headed straight to the bar and got a vodka on ice with lemon. I forced myself to be ladylike and sip it but I wanted to slam it down to help me relax. As I was taking the last sip of my drink three women walked up to me. It only took me one second to realize they had come together dressed as the female trio from the Big Lots holiday commercial. As they approached me I noticed they were in the same formation as the commercial. A woman in a black dress walked slightly ahead of two women, one on each side of her. These women had gold dresses that were an exact match of the dresses the ladies wore for the commercial. Their shoes matched perfectly too. I half expected them to break out in a song and dance from the commercial. I thought this was a great costume idea and I let them know it with a smile. One of the women noticed me smiling and stopped to strike up a conversation.

“Hi. How are you?”

“Hi. I’m good, thanks. I love your costumes.”

“Oh, so you know who we are?”

“Of course! You are the Big Lots women from the holiday commercial. Your outfits are perfect to the last detail. That dress looks exactly like the one in the commercial.”

“That’s because it is the same one I wore for the shoot.”

During our initial exchange, the other two girls of the trio moved to huddle around me. We all laughed at the last comment.

The women in the black dress gently touched my arm and asked, “Isn’t this a great party? It seems to get better every year.”

“It is a beautiful venue. It’s the first time I have been here.”

“We’ve been coming for the last four or five years.”

“So even before you were stars on television?… I just happened to notice an advertisement for the party so I decided to come. I am just visiting, well I am here for work actually.”

Damn. Now she was going to ask me about my job! I needed to think of something fast.

“Oh, well you made a good choice.”

Good, no questions about work.

The women in the black dress complimented me. “I love those shoes. They look great.”

“Thank you. I think you all look great.”

One of the gold dress girls said, “Your eye makeup is stunning.”

“I hope so. I spent a lot of time at the salon today.”

The other woman wearing a gold dress asked about my dress.

“Did you buy that dress at Lila’s Boutique?”

“Yes I did.”

“I saw it there the other day. I was going to try it on. It looks great on you.”

“Thanks. I would like to see how I look in gold. Maybe we can trade?”

I was half kidding but the woman said, “Okay. I am sure a little later we can find a room upstairs and swap, if I can fit into yours.”

I was a little surprised at her response but women always try on each other’s things so I simply agreed.

“Great. I would like to…I’m sorry I did not get any of your names.

The woman in the black dress said, “We are the Big Lot girls.”

I smiled and assumed they wanted to stay in character or simply did not want to give out their names so I played along.

“Oh, of course. I knew that. I am Tessa. Nice to meet all of you.”

All three women gave me a quick hug. The woman in the black dress gave me a little longer hug. As she stepped away from the hug I noticed her looking at my chest. I looked down to see if there was something wrong with my dress.

“Is there something on my dress?”

“No, I was just checking out your girls.”

I was shocked at her bluntness. I had chosen to wear a VS push up bra with little chicklet inserts that helped to give me a little something and a little cleavage. That combination in addition to pushing up my own pecs gave me the look of a small-breasted woman. I decided to respond to her comment with some sarcasm.

“Oh, these little things?”

“I think they are a perfect size for your body. Believe me having big ones isn’t always so great.”

As I looked at the woman I realized her breasts were on the larger size. She actually resembled the woman in the commercial. She not only looked like her but she had the same body type.

As burdur escort she eased further away she said, “It was nice to meet you, Tessa. We will catch up with you later.”

“Yes. Okay. Sure. It was nice meeting all of you too. Don’t forget about me!”

The women walked away to mingle with some other guests. I had enjoyed talking them. It was fun talking to them as a woman and I hoped we could talk later. I went to get a drink but before I could buy one a man dressed as Robin Hood asked if he could buy me a drink. Before I answered I smiled and reminded myself that free drinks were one perk of being a woman so I accepted.


Robin Hood bought me a drink and I thanked him for it. As he handed me the drink he seemed a little unsteady as if he had already had too much to drink. He tried to make conversation with me but something in the other room caught his attention.

“I am truly sorry but I have to check on something. I hope to talk to you later.”

He rushed off before I could reply. That was okay because it was nice to have a free drink without having to “pay” for it with conversation. I took my drink and walked to a less noisy part of the room. Then I continued to wander through the magnificent home. As I strolled around I noticed I was getting several looks from men as well as women. I loved the feeling of walking around dressed so beautifully. I was very glad I had decided to attend the party. I spent a little more time touring the house before settling on moving to a quieter room off the main room. I was just about to sit down in an open spot on a couch when a couple dressed as Luke Skywalker and Princess Leia sat down and occupied the seat. They started hugging and kissing. I could not help but think that their behavior was a little incestuous, and I wondered if anyone would get that joke if I pointed it out.

I turned to look for another spot to sit and as I did I nearly bumped right into a man dressed as a Union Civil War general. He carried two glasses of punch in his hands and he had to take a step back to avoid spilling the refreshments on him or me.

Making sure I kept my best female voice I apologized. “I am so sorry, sir. I hope you didn’t spill your drinks.”

He smiled and replied, “Not a drop. May I offer you a glass?”

“Oh, I wouldn’t want to take your date’s drink.”

“Oh, no. I was planning on offering it to you.”

“Why thank you. It’s nice to meet a gentleman. Are you on leave from the war?”

“Just a short break. But I am certainly lucky to have bumped into you.”

I played along assuming the general knew I was a guy and was just having some fun. However, the lustful look in his eye sent me some warning signals. Before I could respond an older gentleman dressed in formal wear and a Mardi Gras mask stepped in and interrupted.

“Excuse me but may I have a dance?”

The dude had just asked me to dance! I had not even considered anyone asking me to dance especially since the band was in another room. Oh, boy. The man did look attractive but I was not interested at all.

“I am sorry it would be rude of me to leave such an interesting conversation I am having with my General friend.”

The man bowed silently and walked away. As I watched the man walk away my eyes caught the Big Lots women. They were huddled together far across the room but I felt their eyes on me. I knew they were talking about me and by the look on their faces it was more bitch talk than the friendly exchange we had earlier. Could they be upset that two men were talking to me and there appeared to be no men interested in them? They were too nice for that sort of pettiness. Also, if they knew I was not interested in men they probably would have found the situation funny instead of whatever negative emotions it was generating in them. I glanced over at them hoping they would come rescue me from the general. As I turned back to the general I apologized.

“I am sorry.”

“There is nothing to be sorry for. A man found you attractive. You must be used that. And I would love to dance with you too.”

How was this happening? I needed to set this guy straight. I leaned in to him and whispered, “You do know that this is a costume. I have the same parts down here as you.”

“All I see in front of me is a beautiful woman. What do you say about a dance?”

On one hand I was flattered the man saw me as a woman but I had no intention of being with him or any man. I looked over to make eye contact with the Big Lot Girls but they were gone.

A second later over my shoulder I heard, “Hi, Tessa!”

The girls were here to help, I hoped.

“Ready to take that walk with us now?”

“Oh, yes.”

I turned to the general and excused myself.

“I am sorry but I promised my friends I would spend some time with them.”

The girls huddled around me like mother hens and walked me away from the general. I am sure he was disappointed but I could not have been more relieved and I thanked all of the girls.

As we walked away the dark haired woman in one of the gold dresses said to the general, “Does your wife know you a trying to pick up our friend?”

I had not noticed a ring on the man’s finger but apparently my new friend did.

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