A wonderful night out.

I hope you are going to have a wonderful Halloween night.  Jules has provided a delightful reading of The Apartment for us. If you’ve no other plans perhaps settling down with a glass of wine just before midnight and enjoying this story would be the perfect way to end the night. You can see the video here.

As I am sure you are aware the start of November marks the end of the competitive eating season. Marjorie, my neighbour has excelled this year, surpassing her best in the highly coveted sausage eating division, a fact made even more surprising because she is in a lesbian relationship with my wife’s appalling friend Amanda.

Marjorie is often billed as ‘The Silo’ in these events. I am told this is an affectionate nickname.

In celebration of her successes Marjorie and Amanda decided to take Sebastian, Sylvester and I to dinner. After some discussion it was decided that we’d go to a very exclusive newly opened sushi restaurant.  To mark the occasion I am thrilled to say I found a lovely new skirt from my good friends at The Drag Queen Closet.

As you’ll notice this skirt has a stylish ruching effect.  Like all the Drag Queen Closet products this one has a high quality fabric which beautifully expresses the depth of the claret color I had selected. Fabric is very important. Many of us just look at the cut of the skirt, but to carry the color with depth a good quality fabric is required. The sheer nature of lanon is perfect for this.

What I most love about this skirt is it actually helps my deportment. I always wear a bit of a heel, which gives me the posture I am looking for, but the slight tapering inward of this skirt just reminds me to keep my knees together in a ladylike manner. This is a serious business for one who has a propensity to slut out at the slightest opportunity.

Sebastian has commented that I should probably be buried in a Y-shaped coffin, finding that final resting place in that most familiar of postures. He really can be most coarse.

We ended up at the sushi restaurant at about 7.30, enjoyed a lovely Japanese beer, and then settled down for a mixed platter of sushi. This particular restaurant had rather nice arrangement of private cubicles behind those lovely Japanese paper screens which afforded a level of discrete privacy. We sat at a low table and the food was served on the low table before us. All of this was most elegant and sophisticated.

I enjoy salmon particularly, though all the different sushi dishes were excellent. However, part way through the meal something did happen that left a rather strange mark on the evening.

I was sitting, my legs delicately folded beneath me looking quite lovely in the skirt and a plain black silk blouse, and stockings. Sebastian sat opposite, glancing from time to time at a screen which silently played the football game highlights. Sebastian is such a sports nut I really do find it irritating at times, but with my back to the screen I was able to ignore the screen easily.

Then, surprisingly at one point Sebastian murmured, “He really should go deep. One good pass and he’d be away.”

I understand this is a football comment. Having grown up in South Africa, where Rugby is a religion, this is all beyond me. However, from time to time Sebastian would look at Sylvester and say something like, “He should go deep, for heaven’s sake. Did you see that? I mean, really! Did you see that?”

I was enjoying the sushi and Amanda and Marjorie were enjoying each other, as far as I could see. There was a certain amount of touching going on beneath the table, I think. The privacy of these Japanese table arrangements is very discrete.

What happened next happened very swiftly. Sebastian had been putting away the Sake at a pretty good rate, as had Sylvester. I chose to stick to a very light lager while the boys and the two girls raced to the bottle of the nearest barrel. I was really enjoying myself when Sebastian became fixated on the screen and started saying quite loudly, “Go deeper!”

Suddenly an impressive young man was running with the ball and setting up a long pass and hurled the projectile down the pitch. Sebastian was suddenly on his feet shouting, “Deeper! Deeper!

At that very moment Sylvester started coughing wildly and a moment later his face went from it’s usuall ruddy red to a horrible shade of blue. It quite clashed with my skirt. In a heartbeat Amanda was on her massive feet, stepped behind Sylvester and said, “Don’t worry! I’m a trained professional.”

As Sylvester turned from blue to blue grey, Amanda started jerking Sylveter’s chest in a bear hug and I realised she was doing the heimlich maneuver. A moment later Sylvester coughed and a radish flew from his mouth across the tiny cubicle.

The manager, roused by the cries of “Deeper! Deeper!” came hurrying into the cubicle in time to see Sylvester go sprawling across the delicate low table, and the Sushi plater, only to be pinned under Amanda’s not inconsiderable weight.

“You are animals,” he cried in heavily accented English.

At that very moment Marjorie gave a loud belch, and grinned sheepishly. It’s apparently a common affliction of competitive eaters.

Moments later we were ejected from this exclusive establishment, to my disappointment. However, I suppose all things considered I should not be surprised. One way or another I’ve been thrown out of some of the nicest establishments in the country. Why should this evening have been any different.

If you’d like to buy a lovely skirt like the one I wore that night you can do so here: https://thedragqueencloset.com/products/skirt-miss-secretary-3-colors  I know you won’t be disappointed. Be sure to let the girls at The Drag Queen Closet know that Fiona sent you.



– http://FionaDobson.com

The Apartment – A Halloween ghost story

When Jeff returns to his old apartment he gets more than he bargains for. Enjoy this Halloween ghost story.

Be sure to comment if you feel like it.


Keeping it in the family.

When a partner decides they want to explore the gender fluid world of crossdressing it’s going to introduce some new strains on a relationship. But does it have to be the end?

Enjoy the Fiona Dobson playlist.

When I first started sending out the weekly messages I would often embed a music video. I don’t so often these days, as the messages are much more text heavy.

However, over the last few years the videos were very popular and were compiled into a playlist. It’s turned out to be a rather unusual and eclectic collection.

You may enjoy it.


She made me do it.

A walk home from school takes two young people on a diversion that will have far reaching consequences. A short story by Jules Sanderson.

I just can’t dress as femme as I want!

Many times I hear from members wishing to dress in a very feminine way, but they find that they simply can’t due to family or others that would never find their emergence as a CD or gender fluid person acceptable.

For many of us the answer is to move more gently into the centre of the gender spectrum.

Below are a few ideas of how you can do this. Be sure to follow me on Pinterest to get more ideas. If you do venture into this space the addition of a little makeup and some heels and you’re firmly in the Crossdressing arena, however in many cases without make up you’ll simply appear to be dressing in a more gentle manner.

A bit of luck and a nice package!

When I got an urgent call this morning asking me to stand in as Master of Ceremonies for a charity event, I was caught short completely. It was really quite tragic, their own MC having met with an unusual accident involving a hamster, a length of pipe and a lighter.  I’m told they should be out of hospital in a week or so, though the hamster was less fortunate. The situation was made doubly dramatic as I had just sent several of my favorite dresses to the dry cleaners as I have a string of events to attend in the coming weeks, and I had nothing to wear. However, as luck would have it I received a delivery when I got to work directly from my friends at Glamour Boutique.

What a stroke of fortune, a beautiful purple lace sleeve dress delivered in their usual discrete packaging.  Now, there’s a number of excellent reasons you should buy from a supplier like Glamour Boutique, rather than off the shelf.  I will go into that shortly, but first, let me tell you exactly how this evening played out.

I called Sylvester who, while he does look like a gorilla that has been strategically shaved when he wears a suit, can be quite fun at these events. He agreed to join me at home at Huckleberry Close and we would then go on from there.

He pulled into my drive right behind me as I arrived home from work, and then waited in the living room as I hurried upstairs to change. As I did so I called down, saying “You’ll have to give me a moment to slip into something.”

I pulled on some fishnets, slipped into a pair of patent leather black heels, and then stepped into the dress. A moment spent on make up, and then I descended the stairs.  Sylvester was gawping at me as I walked into the hallway.

I turned and inspected myself in the full length mirror, Sylvester looming behind me like a great henge.

I watched his reflection as I adjusted my hair, and saw how his gaze fell to my behind, framed nicely by the cut of this particular dress.

“Yes,” he muttered. “Slipping into that seems a good idea…”

“Sylvester,” I said sharply and he averted his gaze.  He really can be most coarse at times.

Moments later we were off to the event, Sylvester driving and I feeling quite excited. A new dress always makes me feel coquettish. Particularly this one. The lace sleeves are so perfect for crossdressers, as they hide a multitude of sins, such as unsightly arm hair. Additionally, the cut of this particular dress is perfect for so many of us. The Empire waist really is a good choice for those of us in the gender fluid space. Most of us don’t have a very pronounced waist, but this style really does lend us a little more shape.

I’ve said before that buying from a company like Glamour Boutique is a good idea. These dresses are synthetic and almost impossible to crease. This is important to me as there are times I have to fling something in a bag without much preparation, and I may not be able to hang it as precisely as a silk or cotton dress might need. Wearing creased clothing is always awkward and a sign of very poor taste. This comfortably sized synthetic dress fits easily to the curves of my body, while still giving a little in those areas I need it to. The fabric has enough stretch to work for a male body shape, and for those of us who occasionally like to add a few body form accessories.  After all, don’t we all have moments where adding a little extra presence to our bust measurement can be done to good effect?

Well made crossdressing dresses will work with or without such accessories, and stretch to accommodate either option. This is why I generally go with clothing from Glamour Boutique, rather than from local stores. I know I will get clothes specifically chosen to be good for a crossdresser, rather than something that might look great in the store but really doesn’t work so well in front of the mirror at home while Sylvester stares at my ass.

And on the subject of my ass, I have to tell you I love this empire waist.  It’s not usually my first choice of dress shape, but it really does work well. Coupled with a high heel the effect is to give just the right flare to the dress, as my ass is slightly exaggerated by the cut of the dress combined with a nice heel. The effect is a dress that has a nice swing to it, looks smooth and well fitted and is really comfortable to wear. So, you can see, I was pretty happy to get to the event, stand up in front of the crowd and enjoy a moment in the spotlight looking great.

I know you will have the same sense of satisfaction if you get in touch with my friends at Glamour Boutique.  Be sure to tell them I sent you.


Some people should be bloody well hung!

I have been hard at work with some of my corporate clients at the advertising agency recently, and as we move toward the closing months of the year some are organising their staff parties and corporate retreats.

Naturally I get to be invited to many of these, both as a part of the client’s team, but also as I am generally advising the organising committee. So it was that I happened to be asked to attend a costumed event recently, and was asked to bring one or two friends to add color and vibrancy to the situation.

Now, as you likely know, I am very introverted and shy at heart, however I decided to throw myself into the process.

After finding the perfect costume, I decided to go a little retro and go as Xena Warrior Princess. I have always liked that look, and like Xena consider myself something of a problem solver. It’s just the kind of gurl I am. As SylvesterAliMax and I prepared for the party and got into our costumes Max’s mother, Marjorie, came over to see what all the excitement was about.

“Hello, Marjorie,” I said as she wandered into my kitchen. “We’re almost ready.”

“So, I can see,” she replied eyeing my breast plate. “And Max is doing a wonderful job of buffing up the brass of that breast plate.”

“He’s been most helpful,” I replied. Max was rubbing away vigorously at the brass.

“Wouldn’t it have been easier if you’d taken it off first?” asked Marjorie.

“Oh, no,” I replied. “What with Max so hard at work…”

At that moment Ali, who you may remember looks after my garden, came in dressed in a set of Klan robes.

“Ali,” I said. “Are you sure that’s entirely appropriate?”

My Syrian friend replied, “I thought I looked very presidential.”

I could hardly fault that, and said so.

“Perhaps we should all go out and stand on the front lawn, Perhaps Marjorie could take a photograph of us from the landing upstairs? That window overlooks the garden and the picture will be lovely with the roses in the background.”

Marjorie agreed and went up the stairs. A moment later she called down to say she couldn’t get the window open, and that she needed a little help. The window seemed blocked by something from the outside.

“Don’t worry,” cried Ali. “I’ll get a ladder and clear it up.” With that, and a flurry of robes, Ali disappeared to get a ladder. Now the reason I explain all this is simple enough. You can imagine the scene when I was then standing on the front lawn, along with Sylvester dressed like a warrior from Middle Earth, about to go on a quest, Max as a Viking, and all of us staring up a ladder at Ali dressed as a KKK klansman, complete with hood, trying to open the upstairs window of my house on a sunny midweek afternoon.

As the sun glinted off my breastplate, we heard the silent hum of Amanda, my wife’s appalling friend, arriving visit with Marjorie, with whom you may remember she is in a torrid lesbian relationship. I will not go into detail.

With the unmistakable sound of tweed rustling Amanda stepped from her car, open mouthed, and said “What on earth is going on here?”

“Ali’s taking care of a blockage,” I said helpfully, and stared up the ladder. Amanda followed my gaze.

“That’s Ali? I thought you’d finally upset the wrong people,” murmured Amanda with her usual distaste for everyone around her.

Ali’s voice drifted down, “Marjorie’s  Areolas are coming out beautifully this year.  I’ve not seen her garden from this angle before.”

Sometimes I wonder about Ali’s English lessons. Being a Syrian refugee, who was welcomed to Canada in somewhat disadvantaged circumstances, one might forget that he was also a professor in Damascus University prior to the war.

“I thought something dreadful was happening, as I drove up. I could see this crazy Klansman trying to break in through the window. I thought maybe… Honestly, those people should be bloody well hung!”

Looking up Ali’s klan robe, I replied, “Amanda, from where I’m standing, I think Ali’s pretty well…”

“Oh my god,” said Amanda. “You people make me bloody sick. I just dropped by to see Marjorie. I can’t believe the stress on the newsdesk at Pig and Pig Farmer. Sometimes I fear I may be wasted there.”

“Oh,” I replied. “If you were to leave Pig and Pig Farmer it would be a tragic loss to the world of journalism.”

However, that is not the main reason I am writing to you. I wanted to encourage you to look at the details of our Mexico conference. We’re already taking deposits for the January event and we’d love to see you there.

Have a wonderful weekend,



Weighing up your options.

Hi there,

I’m often asked how I can help my members who want to come out and tell their families. It’s such a delicate subject, and often these feelings rise to the fore at a delicate time.

Recently a 24 year old from Cincinnati asked me the question on my online chat on the website, “Fiona, I wish so badly to become a girl but I can’t figure a way to tell my family. Can you help me?”

I chatted with my member while on my  tablet sitting in my garden and this is what transpired. First of all it became clear that my friend had told no one about this desire.  Not family, not girlfriends. Additionally they’d never been out to a drag bar, never been out crossdressed and have essentially just gone through life so far denying their feelings of gender confusion.

The first thing I had to suggest is that without having discussed this quietly and calmly with others who either understand or are on their own journey into the centre space of gender they would be moving without reference point or real information.  Being able to chat or talk with others in the same boat and hear their stories provides a little bit of a guide.  There are, after all, right ways and wrong ways to approach this. To simply go with some preconceptions, which may or may not be realistic was not likely to be a good idea.

As I pointed out to Ali, my Syrian gardener, while I chatted if you’ve never been exposed to a group of people who are familiar with this, you really don’t know what the options are. He helpfully pointed out that in Syria the options are being stoned to death.

“That’s only one option,” I said.

“Well, you could possibly choose large stones or smaller stones. But that’s about it.”

I made a note to mention that where you are in the world also makes a difference. I am not sure that Cincinnati is a very liberal place, but I suspect it’s marginally ahead of Damascas, or so I am told.

Continue reading “Weighing up your options.”