The Spirit of Halloween

I was not a fan of Halloween following a bad experience as a child which I never spoke about, but my wife was completely mad about it and I let her get on with it. We had grown up as childhood friends and just grew together, eventually becoming a couple, and then getting married while we were at college. We had a calm and loving relationship but were both still aggressively pursuing our careers and trying to make names for ourselves. I worked in information technology for a rapidly growing AI start-up and she was an architect in a small, but high-end practice. We worked hard, and I would like to say we played hard, but we did seem to be living to work, rather than working to live.

Having said that we did go out at least twice a month and enjoyed socializing, but we chose what we did carefully so that although we may not have been going out as much as our friends, what we did do was always really special. When my wife told me that we were invited to her boss' Halloween party that the company was putting on for their biggest clients I did not show that much enthusiasm. She knew I disliked Halloween even though I had never explained why and she pleaded with me a bit, explaining that it was important for her career that we were both there. I could see how much it meant to her which weakened my resolve, but my mind was made up when I saw that it was taking place in an old historic house downtown that I had always wanted to visit but was not open to the public.

The house was boarded up and had been empty for some time. It was to be redeveloped into a boutique hotel and my wife's company were shareholders in the development and so had agreed with the other partners that it would be a good venue for a Halloween event. We would have the chance to stay overnight and that was the clincher for me for one simple reason, the house was reputed to be home to several ghosts and I was fascinated by the supernatural. The only downside was that it was fancy dress which was not my thing, but I decided that it was a small price to pay and I had to exorcise my Halloween daemon.

My dislike for Halloween stemmed from the time my mom had dressed me as a witch for trick or treating. I had an older sister and all the other kids my age in the neighborhood were girls and they had made the decision that we all had to be witches. I was fine with that, in fact, I enjoyed getting dressed up and loved the feeling of the clothes even then. The girls thought I looked great and were really nice to me and I was having the greatest time ever when it all went wrong.

Unfortunately, in my excitement, I left my little besom brush at a house and had to go back to get it. A group of older boys had turned up and made fun of me in a nasty and intimidating way, one of them even lifted my little black skirt borrowed from my sister. I had never been so embarrassed. They kept hold of me and mocked me relentlessly, but one of them tried to touch me, and with a burst of energy I broke free and escaped their clutches. I ran back to my friends, mortified and brushing away my tears doing my best to hide my emotional state. Back with the girls I immediately felt better, but the psychological damage about Halloween was done.

My sister had no idea about my experience, but she could tell that I had enjoyed dressing up, so after that, I occasionally played with my sister who liked treating me as her doll and dressing me in different outfits. I really loved it, finding it really soothing and relaxing, but of course, we kept it secret from my parents. When she started dating it all stopped, and I missed it, so I managed to collect a small stash of her things that I could dress in when the opportunity arose. It always made me feel good, and as I got older it became quite erotic, but the very idea of being seen in public and tormented gave me horrible flashbacks.

I was still obsessed with femininity and especially women's clothes. That was my fetish. I loved going shopping with my wife as being surrounded by female fashion and lingerie excited me enormously. I still had a collection of panties and a few other items that I had hidden in the garage. I would sometimes wear them when alone and, because my build was quite slight and I had let my hair grow, they suited me.

You would have though that I would like fancy dress, but I was very self-conscious and dressing up was exclusively a private thing. When I was out I preferred to merge into the background rather than attract attention to myself. I was grateful that my wife was also shy and we shared a common thankfulness that we had not had to go through all that trauma of dating. A downside was that my wife was not interested in sex that much. We got on really well, but I had a much higher sex drive and that might have caused a problem for us if I hadn't been so busy and tired most of the time. When I did need relief I found it in wearing panties and lingerie.

***

We decided to hire costumes as they would be much better quality than internet fast fashion and it was far less damaging for the planet. There was a place out in the city limits that was renowned for its costumes and did hires for theaters and films, however, it was expensive and doubly so for Halloween. Although I gulped a bit when I saw the prices, if you took into account how good the party was probably going to be it was definitely worth it and making it a night to remember. My wife booked us an appointment to try on some costumes as we were warned they were going quickly.

Choosing a costume proved to be hard for me for three reasons. Firstly, as you know, I did not like fancy dress and all the men's outfits looked dumb. Secondly, I did not have much idea of men's fashion or what outfits looked good anyway. Lastly, there was not that much choice for men. The same was not true of the women's costumes most of which were very sexy and I found myself taking more interest in those, making plenty of suggestions about what my wife should wear.

My wife was quite patient with me until I went almost gaga over this one vampire costume. It was rather impressive with a black corset, black fishnet stockings, short pleated satin skirt, knee-length boots and an amazing black and red velvet cape. I was quite insistent it was the costume for her, but she felt it was far too revealing. When I tried to persuade her she put her hand up like a traffic cop and silenced me.

"If you like it so much, you wear it. It's Halloween after all, and, you know what, I think it would suit you."

"What?" I muttered. The assistant, who was a well-spoken and very attractive middle-aged lady, backed my wife up. She had been very attentive and patient despite our indecisiveness.

"Your wife's right sir, this one is quite popular with men, we have it in larger sizes as a result and can find a fabulous wig to go with it."

"There you go," my wife added triumphantly, "that's sorted then -- you'll get to wear something you like, and so will I."

I was a bit shocked and not sure what to say, but part of me was quite intrigued by the idea. I began to think that I was wrong about Halloween. It was not my enemy, it was potentially my friend.

"OK, I guess I can try it," I replied a little quietly, "like you say it's the sort of thing guys do this time of year."

"And what about you madam?" The assistant asked, seeming quite relieved that a choice might have finally been made and trying to close the deal.

"I'll take that one I saw earlier, the Vampire Queen costume, that was amazing and much more my thing!"

I looked at the rather impressive costume my wife was pointing at. It had a black camisole with a black lace top with lots of flourishes. There was a long sweeping, pleated, black skirt. There was gold embroidery and piping everywhere, especially on the long-tailed jacket. It was quite imposing and three times the cost of mine to hire, but I wasn't worried about that cost, I was more intrigued by how my costume would make me look and feel. I felt like I was a teenager and was extremely excited.

The assistant returned with two large boxes.

"Normally I would have another customer now, but there was a cancellation so if either of you need any help I'm available."

"Oh, that's wonderful! I suspect you'll need a bit of help dear!" My wife said a little acidly.

"Err, yes, probably," I muttered again.

The assistant was keen to move on. "Good, I'll just put some music on and get a few other things that might be useful. I'll be back in a moment. Madam, if there's anything you need just say."

***

The room had screens in the corners and my wife retreated behind one and I took my box behind the other and began to undress. The thought of wearing the outfit had made me quite hard, well, extremely hard, and I was not sure what to do. It wouldn't bend so I had to slide it along the waistband of my underpants. I pulled out the mini-skirt and put that on to hide my embarrassment before fumbling with the corset.

I heard the door open and close and, before I could say anything, the assistant was looking me up and down. She was carrying a pink bag and hair brush.

"No idea!" She said quietly, shaking her head. "Let me help."

I was frozen to the spot as she unzipped the skirt and let it fall to the floor. I could feel my face burning, it must have been as red as a beetroot!

"Oh dear, I can see there's a problem, but nothing we can't sort out." She said, crouching down and lifting my feet in turn to extract the skirt. Her head was right in front of my throbbing erection as she slipped my briefs down allowing my cock to spring out and brush against her cheek. My breathing was now ragged. My wife was just ten feet away and I had no idea what to do or say. The assistant looked up at me with a sweet smile while her hand took hold of my throbbing cock and she ran her tongue along the bottom of its purple head causing my legs to tremble.

The need to keep quiet added to the tension and seemed to magnify my excitement as she slowly wrapped her lips around it and I felt the warmth of her mouth slowly envelop me. My wife did not do oral sex, so this was a completely new experience for me, and I felt like I was melting. She squeezed the base of my cock with her hand and began to twist it one way and the other while she slowly rubbed her lips over its head, caressing the underside with flicks of her tongue.

She knew I was about to explode as she pulled back and looked up at me, her eyes shining with naughtiness under her dark lashes. That was enough to make me tremble convulsively as my cum spurted into her mouth covering her tongue in large creamy pools. I must have spasmed for thirty seconds or so while she sucked me dry. I was glad that the music had gotten a bit louder while I climaxed and wondered if that was a coincidence.

The assistant pulled my underwear down and I stepped out of it. She stood back up and kissed me, well I found out later that what she had actually done was snowballed me, as she pushed my cum into my mouth with her tongue. My heart was racing, my body was burning and I felt quite faint. But I also felt extremely happy.

"Are you OK madam?" She asked loudly, looking me in the eyes.

"Yes, fine thanks!" My wife replied.

"Now, let's get you dressed in the right order," she whispered.

She wrapped the corset around my waist and pulled it so tight that it felt a little hard to breathe. She asked if I was OK and I just nodded subserviently. She produced a pair of small black panties from her pink back and pulled them up my legs, sucking the remnants of my cum from my deflated cock before tucking it between my legs and sealing it in place with the lacy material. The corset has six large suspender straps and she attached these to some lace-topped stockings that she sexily rolled up my legs, rubbing them smooth to remove any creases which felt so heavenly I could feel my cock straining in its prison.

The skirt was next, then the boots. They were a good fit. The assistant pointed out that they only had a one-inch heel making them quite practical for the entire evening. She had made me sit down to put them on and the tightness of the corset made that quite hard until I got used to it. I liked the way it pushed my chest up and together, almost creating a cleavage. Finally, there was the velvet bolero jacket and cape, but before that, she put my hair in a tight-fitting wig cap and produced some makeup from her bag and spent a few minutes doing my face. She added false lashes to go with a smoky eye look and painted my lips with a dramatic crimson lip gloss.

I heard my wife moving around, her outfit rustled quite loudly as she moved. She asked if I was almost ready and the assistant invited her over to take a look as she was brushing out my wig. My wife appeared from around the screen and she looked amazing in the costume, just like a vampire queen, but she did pull a slightly puzzled expression when she looked at me.

"Well madam, that was an excellent choice," the assistant said, "if you would like I can quickly do your makeup too, and I have this vampiric jewelry that you can both borrow. Then I can take a few pictures so you can really get an idea of how good you both look."

"Do I look OK?" I asked, unsure what my wife's expression meant.

"Err, yes honey, you do, unbelievably so," she turned to the assistant, "and yes please, if you have time I'd love to see how I look with some moody makeup."

"Certainly madam, take a seat, and sir, you should have a look in the mirror by the door," the assistant said to me, adding with a laugh, "not that vampires can see themselves in a mirror of course."

I got up and strolled over to the door. I loved the way the clothes hugged me so tight and felt fantastic. When I looked in the mirror I was almost overcome. Maybe the assistant was right. I certainly could not see myself in the mirror. My cock strained against my panties again as I stared at this gorgeous femme fatale who was staring back at me. I put my hand to my mouth and smelt my breath confirming that earlier had not been a dream, then I put my hands on my hips and did a few triumphant body twists! I absolutely loved what I saw.

My wife joined me. She looked amazing too! The assistant certainly has fabulous makeup skills and smiled, offering us a collection of necklaces, rings and earrings. She had some clever clip adapters for my ears. Finally, she produced some vampire teeth which somehow stuck to your real teeth. She took a lot of photos of us, including some of our made-up faces, and then the sale was complete. She gave us a card and said if we needed any help getting ready then she could do that for a reasonable fee.

***

As we drove home my wife asked me a lot of questions about the outfit and whether I was really OK with it. I said that I did love it and that somehow it didn't feel like fancy dress. I guess that was an odd thing to say and she demanded an explanation. I just replied that it was more of a complete transformation, I was simply unrecognizable, and that made me feel more confident. She seemed to understand that, perhaps because women can hide behind their clothes, jewelry and makeup in a way men can't.

This implied that I wanted to take up the assistant on her makeup offer for the party and I confirmed that I definitely did. She said that her boss was going to be blown away by our outfits, and especially mine. It seemed I had definitely done something right as that night we hugged and kissed, and eventually she made me lie on my back and fucked me. That was her favourite way as she liked to stay in control. I came really hard, in part, I confess, because I was thinking of the assistant earlier in the day.

The days leading up to the party were strange for me. I was accompanied by a haunting image of another me that was stored on my phone and at which I looked frequently. For a couple of days I not only dressed up, but I also tried using some of my wife's makeup, but I realized I had a lot to learn, and returned to my new photographic images to relive the dream.

I contacted the assistant to book her for the session before the Halloween party, but I also asked if she could give me a makeup lesson before that. She was happy to, especially as her rates were not cheap, but I really wanted to look amazing again. She suggested I come to her apartment as all her stuff was there and that would give us more possibilities. I did wonder what that meant, but what I was really excited about was the makeover. I did tell my wife I was going and explained it was so I could fix my makeup if necessary during the evening. She thought that was a brilliant idea.

I arrived at 2:00 and she opened the door wearing a pristine white lab coat, just like a real professional cosmetic technician, which I assumed she was. She looked absolutely stunning with her thick blond hair down and well-made-up face. I guessed she was in her forties, but who could tell? Age does not define beauty. She was wearing nude pantyhose and white-heeled sandals.

She offered me tea or coffee, or a glass of chilled wine. I chose wine. We sat and talked about what she would do and I realized that this was going to be all-in. She took me to the bathroom and put on rubber gloves while I undressed. She covered me in hair removing cream and after waiting a short while I was relieved to get under the shower and remove it. I was not very hairy anyway, but it still felt amazing. She finished things off with a razor and showed me how to do an ultra-close shave on my face.

It was strange being naked with her in her white uniform and I told her so. She laughed and asked if I liked it. Then she reached out and rubbed my cock, asking why I was not as excited this time. Before I could answer she began unbuttoning her lab coat revealing a lacy white bra, garter belt and almost non-existent panties above her stocking tops, barely hiding a really sexy and voluptuous body.

"That's better," she said, as my cock began to respond, and she threw me a white fluffy dressing gown.

Next to the bathroom was her studio and I sat in this big comfortable chair as she got to work. Two hours later I had painted toenails in black polish, false black nails on my fingers and she had even persuaded me to let her pierce my ears and put in sleepers. I had learned the basics of how to make up my face and secure a wig. Once again I was amazed at the transformation, but this time it was much more complete and I felt I could, at a push, recreate the look.

"All done," she said, "and I can see you like the result."

My cock was poking through a gap in the dressing gown and was very hard.

"So we'll take some pictures of you, I've got some lingerie you can put on, then we'll mess up your makeup and see if you can fix it. OK?"

"Yes," I said, my cock throbbing as she handed me a black bra, panties, garter and stockings

Soon I was wrapped in the lingerie, some patent black court shoes on my feet and my cock sticking out neatly above the panties, so it went straight up my stomach.

She took a set of photographs and showed them to me. They were quite tasteful, even if I was showing off.

"There's nothing sexier than a hot girl with a big beautiful cock," she said when we had finished flicking through the pictures while sat on the sofa.

"Big?" I said questioningly. I had never thought that my cock was big.

"Yes," she said, taking it in her hand. "I can only just wrap my hand around it, but it's not just that, its shape and its shiny head, it's a very beautiful cock too. In fact, it's irresistible!" She leaned over and kissed the tip causing me to take a deep breath. I was expecting her to suck me, and she did slowly slide her mouth down over it until I felt her nose pressing against me, but after three or four deep throats, she sat back up and kissed me.