Tuesday, October 27, 2020

Many Halloweens Ago

By Carollyn Olson

Other Captain & Tennille Emulators 
Unlike many crossdressers, Halloween has never been one of my favorite “holidays.” 

It’s not that I don’t enjoy the children knocking on the front door for “trick or treat” candy because I like seeing the little ones in costume, especially when a boy is dressed as a girl. What I don’t like is when men dress as women once a year and flaunt themselves in an embarrassing way, which is negative to the crossdressing community and all we strive and stand for the other 364 days a year. Is this understandable?

About 30 years ago when I was basically a less experienced crossdresser, I had the opportunity to do a costume exchange with my loving wife for a good friend's combination Halloween and birthday party. 

A few months earlier, my spouse and I had dressed as the popular singing duo Captain & Tennille at a company convention/theme night. It was her idea to “blow our friends’ minds” by reversing roles for the Halloween/birthday dinner party.

When my wife asked me if I was interested in switching roles, I “manly” shrugged it off, but mentally embraced the opportunity. “Let me think about it,” I said, not sure if she was serious, but knowing I would be agreeable in a couple of days.

Going to a party en femme was exciting. I had been out-and-about many times, but this was different. In my mind I began to prepare for the “big night.” What would I wear, where would I buy shoes, makeup, finger nails, jewelry, etc? Remember, I had been crossdressing for about 10 years unbeknownst to my spouse. I had plenty of clothes in a storage locker, but I could never tell he, so I wasn’t going to wear any of my femme wardrobe. I would start from scratch.

After agreeing to make the Halloween switch, we first worked on her costume: a captain’s hat I had worn at the company outing, a striped blue and white shirt, blue blazer, white pants and tennis shoes. I wanted her outfit to be perfect and she looked great, especially when her flowing blonde hair was stuffed under the captain’s hat. Then we went to work on mine.

Since we wore the same size dresses, she asked me to try on her undergarments, hose, red sweater dress and shoulder-length blonde wig. Everything fit perfectly. All I needed was a pair of heels and I knew where to go – Payless Shoes. A few days after the fitting, I returned home with black Mary Jane heels to complement the dress. I also bought clip-on earrings and press-on French tip nails. I was all set to make my Halloween debut.

The night before the party, my spouse insisted I shave my legs, which I did without hesitation. She suggested that we do a costume “dry run” to which I had little objection. Within an hour she had applied my makeup, I had dressed and was parading around the house in heels. She was amazed how good I looked, my mannerisms and how well I walked in 2-1/2–inch heels. If she only knew!

The afternoon of the big day, I started preparing about four hours before we had to leave. I wanted to be perfect and really surprise our friends. After shaving and showering, my spouse did an extra special application of my makeup. I proceeded to dress, making sure I added a little padding for my hips and my bra. My spouse combed out her wig so it would fall precisely on my shoulders. She handed me a matching red purse packed with makeup and said, “You look amazing, but I don’t want you to make a habit of this.”

My 20-ish daughter was also preparing for a Halloween party and she was aware of our party plans. I knocked on her bedroom door and when she opened the door she screamed in amazement. 

“I can’t believe you are my father,” she said. “You look so good as a woman.” 

We shared a good laugh as she had me twirl around and observed me walking in heels across the family room. I picked up our white kitten, which was following me step-by-step and my daughter took a couple of pictures for our photo album.   

I was a bit nervous when I drove the 20 minutes to the party and faked even more nervousness (for the sake of my spouse) as we walked to the front door. I actually felt comfortable and anxious for my friends to meet “Brandi,” the name my wife had given me. We were welcomed by the son of the host, who was a perfect match for Eddie Munster. 

As we walked in, we were greeted by our friend John, who was dressed as a monk. He was shocked at how great I looked and immediately wanted to take photos. Being a dirty old priest, he attempted to grab my breast, but I slapped his hand and told him to act like a gentleman. We had a good laugh as the camera clicked.

I spotted Howard across the room. He had his back to me, so I walked quietly up to him and tapped him on his shoulder. He turned around and I placed a big, wet kiss right on his lips. When he realized the woman who kissed him was me, he yelled an obscenity and ran off to the bathroom to clean off his lips. Everybody laughed.

My appearance as Brandi was the hit of the party. Before the night was over, I had won the best legs contest and many of the men tried to walk in my heels. Drinking alcohol and trying to walk in heels for the first time is not the best idea and one could imagine the results. Anne, the classy, lovely-looking lady, who was the runner-up in the legs contest whispered to me:, “You deserved to win. Your legs are much nicer than mine.”

My spouse chided me throughout the night for being vain. And why not? I was constantly checking my makeup and reapplying my mascara and lipstick in the bathroom. I wanted to look the best I could. 

We departed for home some time after midnight. Since it was colder than usual for a late October evening, the car windows began to fog up. I safely stopped the car at the side of the road and retrieved the squeegee from the trunk. As I was leaning across the hood of the car to reach the windshield with my dress riding up my thighs, a police officer pulled up and rolled down his window. 

“Is everything OK, Miss?” he asked. 

I informed him my windows were fogging up and I wanted to make sure I could see where I was going. 

“Good idea,” he responded. “Drive safely.” 

He turned on his flashing lights and accelerated on to the thoroughfare. I would never know if he turned on the lights for me or had an emergency call.

When we returned home, I poured my wife into bed (too many Long Island iced teas). Still on a high and not wanting to change, I decided to try on a few of my wife’s other outfits. I felt so femme as I wore some of her fancy and casual longer and shorter dresses. 

Finally, exhausted after 12 hours in heels, I fell into bed at 4 AM completely satisfied and on Cloud 9 after a night I will never forget.

So, what’s your Halloween story? I’d love to read it and share it with my readers. And don’t forget to send along a photo or two from your holiday in heels. 

Boys too can cut a pretty figure in this beautiful dress from Eloquii.
Boys too can cut a pretty figure in this beautiful dress from Eloquii. 

Alex Saxon femulating on television’s Ray Donovan (2013 and 2015)
Alex Saxon femulating on television’s Ray Donovan (2013 and 2015)
Thank-you, Gina, for tipping me off about this femulation.


  1. Thanks for a GREAT Halloween story that turned out on a positive note.
    I hope you have other stories that you are willing to share.
    Halloween is most certainly our 'National Holiday'.
    October 29, is National Cat Day!

  2. Stana , has there ever been a Holloween Femulators Ball ?

    1. Not that I am aware of and I am sure that if it was called a "Femulators Ball," I would have been informed about it.

  3. despite the halloween tradition being around far longer than the USA itself, for some reason it has always been celebrated with much more fervour there than in the auld country. thanks to the ongoing americanisation of this green and pleasant land it seems a lot more popular today, but in my childhood it was a very much a low-key affair - where if we could be bothered, we went around knocking on a few doors of neighbours in home-made horror costumes to give them a "fright". but then again we had no reason to mental over it, as unlike americans we had "guy fawkes night" to look forward to the week after (another form of hegemony, which involved burning an effigy of someone who conspired to depose the monarchy on a bonfire whilst letting off fireworks to "celebrate" that).

    so there was no "trick or treat", no pumpkins, no mass-produced witch or skeleton outfits in shops, nor anything else along those lines to my recollection. even when i worked in an office in the 80's and 90's, there was no tradition of celebrating the event in fancy dress. therefore no convenient excuse for a closeted transvestite like myself to "hide in plain sight" (i suspect that phrase is another "americanism" that has recently become popular here btw).

    however, i am getting the impression from reading the femulate site that it has become almost commonplace for guys with secret feminine fantasies to turn up at the office on halloween in drag, as opposed to being dressed as dracula or something. if so, then i would probably have done exactly the same. in fact, i made use of a similar occasion in order to make my debut public appearance en femme without raising too many eyebrows - which was on a new year's eve, where it was tradition for the whole town to go out celebrating in fancy dress!

  4. btw, i thought i would point out that the pictured "captain" impersonator (he and ms tenille were never big in blighty, so transvestites couldn't have used them as an excuse to cross-dress with the missus) has (unless it's part of the "joke") seemingly never played or even looked at a piano keyboard in their life!

    that pic does makes me wonder: on the occasions i had a female partner in my life, were we to do similar with male/female pop duos popular in the UK, who could we have chosen from? the only examples that immediately spring to mind are travolta and livvy, or elton john and kiki dee! feel free to offer up other suggestions...

    1. Sonny & Cher, Travolta & Olivia Newton-John as in “Grease,” Karen & Richard Carpenter, Ike & Tina Turner, Simone & Garfunkel (LOL)

    2. Steve Lawrence and Eydie Gorme', Burns and Allen, "The Bickersons" for us old coots who remember radio shows and my personal favorites, Kiki and Herb https://www.facebook.com/kikiandherb/

  5. I am totally confused by your blog entry Carrollyn... you are offended by men who crossdress once per year, yet you then tell the story of how crossdressing on Halloween is how you found yourself..?

    Perhaps because I've tried to my open myself to the truly magnificent judgement-free attitude of those in their twenties and thirties, I have been able to gain their freedom to live life openly while fully committing myself to an open sex - and love -life. In my case my initial crossdressing began with the full support of an also-youngish woman friend leading to public dressing at Halloween. This was ten years ago and I was a very youthful 45 (indeed, I look back at those pictures an amazed I was that old -- feminizing made me even "younger"). My actual sexual liberation came - with full support from much younger friends - when I got divorced and started a new life that not only made my libido expand exponentially, but also led to my seeking rebirth as a full lifestyle crossdresser.

    I was experiencing an intense hetero love life despite those annual Halloween thrills and was in fact living with a much younger woman I admired for her fluid sexuality -- she was convinced she could enter a loving relationship with anyone straight or LGBTQ, a beautiful thing. All I knew was that we had sex constantly for more than a year and I did not feel like I was 24 again -- I felt better than that.

    It was while living with this woman at a University where we were both seeking advanced degrees that I was invited to a Halloween-like, conservative old-school hazing event --- an evening where the new graduate students were ordered to serve both the male professors and existing male grad students while dressed as Playboy Bunnies. It was a tradition that apparently had been occurring for more than thirty years. One of my young friends who was Gay had confessed not long before that he crossdressed; he and I therefore helped each other get ready for the "primer" which was a rehearsal of sorts in street clothes to make sure the newbies were in the spirit of things. When we were handed our bunny outfits for the actual evening of hazing service, I remember almost hyperventilating at the idea of serving men while fully committed to acting as a woman.

    As I stated, that fateful night, in addition to those many Halloweens before, fully changed my life for the better, and I have been living as a "bi-woman" ever since, presenting myself as such to both supportive friends and business clients. While I have aged a lot since then, I have never questioned those Halloween nights of "flaunting", or the Sad Cinderella next-days of reverting to my male self, because they all led me in this direction, a new life lived in a more open and freer world, without a single person needing to feel hurt or offended. And when I see men laughing or sneering at the idea of crossdressing, I know that deep down most of them are just a high-heel click away from joining me!

  6. Omg... ive been searching for community like this for decades... where were you guys all this time? 😂 Whenever i tried to communicate with any crossdressers n trans folks online... i always got repulsive self degrading shallow responses from the wierdest people. There is so much negativity in our culture, perpetuated by the people of our very own culture... It made me feel disgusted about myself for the longest time. Where are the decent self respecting n hopeless romantic crossdressers n trans folks ... i would ask myself. Im so happy i found this blog post... n this website... i dont know about others but ive never seen this much positivity on a crossdressing forum ... im crying... 😢literally... 😭 ... i feel like so nice to finally meet some genuine crossdressors i can relate to. <3 ... you guys are Amazing! Your blogpost gives me hope n dreams! Your pic looks fantastic... such a lovely couple... i wish i can achieve that someday... Thank you for sharing this with the world... kudos ! <3