I do love a good sissy so this article is about a very good sissy. If I were looking for a good sissy, and I’m not as I have one, then Dierdre from Dublin would be perfect.

I get a lot of correspondance through this blog and on the back of my novels. Most but not all is from sissies or wannabe sissies. I enjoy hearing from everyone but occassionally someone stands out and Deirdre’s email stood out for several reasons, one being she lives the lifestyle fulltime rather than playing at it or to get just sexual excitement.

Here’s Deirdre’s story.

I LOVE GOOD SISSIES

I prefer males as feminised sissies and in a submissive role. I do not like alpha males. It’s why I live in an FLR and I feminised my husband.

But enough about me and onto Dierdre. She first wrote to me from Dublin after reading my blog posts on the benefits of Female-Led Relationships and my books on forced feminisation, specifically the office feminisation stories I wrote in the Becoming Joanne series, A Very Dominant Woman and The New Assistant.

(This post contains affiliate links but you’ll pay no more by buying through them but the small commission helps me to write about forced feminisation)

However, after years of fantasising about being a submissive sissy and dreaming of working as a junior person in an office for strong assertive women, Dierdre put her deepest desires into practice.

SISSY DEIRDRE’S DREAMS

Like many men who love to be feminised and dominated, Deirdre went to see professional Dommes. She played out her fantasy roles involving feminisation, humiliation and submission. Over the years, she gradually became subsumed into a secret sissy lifestyle including sissy sex which she started to prefer to vanilla activities.

Because of this, her last long-term relationship with a real woman ended.

Some time later, due to pandemic, she returned to living with her parents. She was now bereft of any sissy outlet except for online. She created a Facebook identity to share her sissy photos and joined other online sissy sites.

At that time, her day job was teaching speech and drama; it didn’t pay well though and so she took on part-time jobs in the Dublin area. Once the pandemic finished, she went to live on her own again. This Lady Alexa blog and my novels motivated her to resume dressing en femme and to get back into the sissy lifestyle.

I was very happy to hear that as this was one of the reasons I started this blog a few years ago – to produce a real-life story, to meet others like Deirdre and and to encourage others to embrace FLRs and male feminisation.

The problem was that after her separation and because of her low-paid work, she could no longer afford professional Dommes. So she hit on a solution.

THE SISSY SOLUTION

Deirdre’s solution was simple but audacious and brave. She decided to apply for junior office jobs in her female persona.

She purhased an entirely new wardrobe of feminine office attire and started to make applications for jobs as Deirdre. At first, she applied for work in hair and beauty salons as a trainee, but she was considered too old and uncool.

Undeterred, she thought of other approaches, even more audacious. She decided to address the unfulfilled dreams of many sissies – she applied for junior secretarial opportunities.

This was a big deal and not for the faint-hearted sissy but she had come out as a sissy to a small number of women she knew and many were encouraging. The younger ones, who were largely her former students, were open-minded and supportive.

The few women she knew of her own age of early fifties accepted her but she feels they tolerate her rather than being supportive. She doesn’t mind this as in a perverse way, she enjoys the patronising way they talk down to her.

JOB INTERVIEWS AS A SISSY

Deirdre started doing interviews en femme. At first, she says it was mainly for the thrill of appearing out as Deirdre in real environments. She found she was grooving on the thrill of presenting as a girly and the challenge of not seeming incongruent as a feminine person.

Then things started to get real. A former student suggested she do an intern at her office where she works a solicitor. Deidre began her first real job in her feminine persona as an office assistant intern under the guidance of her former student’s PA.

Her former student, Bridget (not her real name), is a young woman in her late 20s and very progressive in her attitude. Bridget’s PA is a woman in her late forties named Fiona (not her real name) and who was very motherly.

Deirdre arrived on her first day in a black dress, jacket and matching tights with flat heels which is what Bridget suggested as appropriate wear for the office in a small legal firm.

SISSY SUPPORTED

While she found working in the office exciting at first, it was also terrifying. With the supportive atmosphere and the fact that it was mostly female and a small office, her confidence grew. In fact, she says she found it an orgasmic experience going to work each day as an intern from April through to May.

The teaching year had ended in early April and she was going to be without work until September. This was a big concern.

After about 6 weeks, Fiona told her about a vacancy for a receptionist at a bigger legal firm in a swankier part of town. Fiona thought Deirdre would be perfect for it as she’d knew the managing partner, a woman named Roisin (not her real name) who was in her late 30s, very successful and extremely sympathetic to transgender people.

With Fiona’s recommendation and Bridget’s reference plus the realtime experience, Roisin called Deirdre for an interview at end of June which she passed. Today, she’s now a front-desk receptionist at a law firm in Dublin.

Deirdre loves the work even when she gets publicly admonished in the office. Although it’s usually pretty minor, it helps her to embrace her servile role and help solidify a more submissive demeanor.

Being a junior office employee, en femme, in a female-led firm and reporting directly to a powerful alpha woman, nearly old enough to be Deirdre’s daughter, was the stuff pure sissy dreams are made of.

Deirdre admits that a number of her fetishes were being ticked off with this whole experience. her idea born out of desperation had worked. She’d adored working for Bridget and, as an former student, it was a massive power reversal. But when she presented for interview with Roisin, Deirdre realised she was in the presence of a true Domme.

SISSY CHALLENGES

However, Deirdre acknowledges it’s hard work to maintain her sissy identity at times. Maintaining the grooming standards, feminine movement and presentation, plus ensuring she uses a softened version of her normal voice at all times can be difficult. She says the the biggest challenge is remaining submissive.

Sometimes, Deirdre feels her natural male privilege rise when she least expects it, usually when she’s being ticked off mildly for something she may think she has not done wrong.

For example, when she was being trained, her immediate supervisor, Cara, the head receptionist, who is a good 22 years younger than her, would often use phrases like “Good girl, you take instruction well, but you just need to improve on…etc. etc.”

Another time Cara told her, “I was bit worried about you to begin with, but you have a lovely feminine style and presentation, all the girls here find you very feminine.” Deirdre finds these a backhanded compliments awkward to take and it’s at times like this her male side threatens to come out.

One day, she remembers stopping and looking at her reflection in the office plexiglass. She saw her pinned-up hair, crisp white top, pencil skirt, black sheer tights and black office heels. She was wearing red lipstick and a mix of dark and light eyeshadow and mascara.

She felt her body was smooth and plucked of hair and she was wearing gorgeous little g-string powder blue lace panties that kept her smallish peenie neatly tucked away. She wore a matching lacy bra with inserts that pushed up her soft chest giving the appearance of nice soft little boobies.

Thinking like a man, who was she kidding? She was presenting as an ultra femme fem-boi, a sissy. Not a complete real woman, of course, but certainly not a man.

She knew she had to change the way she thought.

SISSY LIFE AWAY FROM THE OFFICE

Deirdre would love to meet a dominant lady for an FLR relationship. But she also enjoys sissy sex which is what caused her previous relationship to end. Many dommes, such as me, would love their sissy partner to ‘play’ with other sissies albeit under certain parameters.

THE SUBMISSIVE TAKER

Sissy sex is non-penetrative by her but can result in being penetrated by whatever partner she’s with. She often ‘plays’ with other sissies, usually to amuse real men and/or Dommes which was the point I was making about parameters.

Under the instructions of the Mistress, the other sissy may penetrate her or simply the two of them will be told to kiss and play with each other’s clitties or suck each other off.

Deirdre has discovered that the most arousing kind of sex for her is totally feminised while sexually pleasing another sissy or an alpha male in a compliant and servile manner whilst being watched by a dominant female. And this, I believe, is totally correct behaviour for a sissy.

DOMINATED

In another strong echo of my personal beliefs, Deirdre says her most pleasing sexual experiences involve no orgasm for her and only for her ‘partner’. Sissies need to experience male cum so again, this is correct behaviour in my view.

Deirdre explains she was first became involved in this after being picked up by a dominant couple at a sissy event in a bar in Dublin. The couple both had sex with her and orgasmed but she didn’t and they never wanted her to.

Another experience she had was being out with some girls she’d once taught in college. She had outed herself as a sissy to some of the ones she admired. They insisted she go out with them for a night en femme.

They had dinner, drinks and nightclubbed. Deirdre explains it was a glorious rush of femme experience and she was completely engulfed by feminine feelings. One of her girlfriends had got off with a big rugby type who she had told of Deirdre’s background as her teacher as a male.

He was intrigued and invited Deirdre back to his appartment with the girl. Deirdre was encouraged to make the man hard and after he’d finished with the girl, to perform ‘clean up ‘ duties on his former student. She then had to fellate the man back to stiffness so his former student could enjoy more vanilla sex while she knelt and watched.

When a sissy finally embraces the humiliating and erotic feelings caused by homo-erotic activities, even if they never had homosexual leanings in male mode, they will get huge enjoyment and fulfillment in sissy mode. When an alpha woman watches a sissy being taken by a real man or sucked by a sissy, the bond is between superior and subordinate. The sissy is pleasing her with her submission and humiliation.

REAL LIFE SISSY

Deirdre has been working full-time en femme since late June. She’s the front-of-office receptionist and has to be groomed accordingly. She also does some junior secretarial duties and looks after coffee and hospitality for Roisin’s clients.

There are of course, dicfficulties. Deirdre’s tall and gets lots of looks, ranging from friendly to hostility or disgust. She lets the friendly ones contribute to the build up of her psychological body armour and she uses her sissy sensibilities to allow the hostile ones wash over her in a wave of erotic humiliation. A great way to use something meant as negative in a positive way.

However, when she has to get up at 6am each morning to have time to properly groom, take time with makeup, pick out an outfit and match tights and shoes, decide to wear hair up or down, the reality of what she’s done is powerful.

Then to take a deep breath and step outside the door of her little terraced house and into the area where she sometimes bumps into her neighbours leaving for work, the dream takes on the weight of daily reality.

Deidre can’t get over how much she’s revelling in being a real-time submissive in a professional role and how easily she’s adapted to living en femme at least five days of the week!

A VERY GOOD SISSY INDEED

Despite having sissy tendencies all her life and enjoying the thrill of going to  Dommes, and Dressing Services and then venturing out tentatively at first, then opening up to some former girlfriends, her general day to day life was very much as a middle-aged man who had been in a position of relative authority as a teacher.

To be actually living for a period 24/7 not just as a woman, but a woman in a servile role and in a female-run heirarchy is quite a culture jump. The good news is the thrill of it all stays at the core of it for Deirdre.

Now she knows she must act and respond as the submissive femme that she has chosen to be and to admit to her shortcomings by giving her female superiors the respect they deserve. Amen to that.

So, to all my sissy readers, do you wish this was you? To my Dominant lady readers, would you like to have a sissy like Deirdre? I know I would if I didn’t already have my sissy.

Let me know in the comments or by the contact form on this blog what you think.

And how about taking a look at one of the books Deirdre enjoyed? The New Assistant is just 99c from Amazon.com and available all other Amazon stores – click on the book cover below.