8 Reasons why you should start crossdressing

sexy crossdresser in red lingerie homemade selfie

Crossdressing means: wearing clothes of opposite sex. But as a sissy, crossdressing is something more than that. Biologically it may be dressing as the “opposite sex”, but you’re a sissy – you ARE a feminized girly slut, so crossdressing is not just dressing as something “opposite”, it’s an important expression of the femininity that already exists within you! Therefore it must be appreciated and embraced for a sissy girl to be truly happy! You should never doubt, or feel ashamed, for something that is an expression of your inner identity, and as a sissy it is time to learn why you should be a fabulous crossdresser and never be ashamed of it!


1. Crossdressing is a means of sissy training

As straightforward as this might sound, it cannot be ignored how crossdressing will prompt you to be in a feminized state regularly, allowing you to get in touch with your girly identity by actually being dressed in femme as often as possible! After all, doing is learning. Good practice of being femme outside of your sissy sexuality is invaluable, as you’ll find that you’ll be understanding yourself more and more as you dress up, learning how to look and act pretty, strutting your sexy body and figuring out more and more ways to make men cocks hard in a purely feminine essence!  Furthermore, when dressing thoughts of being a sissy girl are magnetized into your subconsciousness by the repeated affirmations of femininity that comes from dressing up. Soon enough you’ll find yourself able to transform into girl mode as soon as your blood is rushing down in your pants.


2.  Exercising creativity and developing your artistic prowess!

sissy in front of mirror learning to apply makeup

Crossdressing is often mistaken as just throwing on whatever you can find that is for women, then reveling in the excitement of wearing women’s clothes. However, crossdressing is simply so much more! It’s a very demanding hobby, and will take research and knowledge of fashion trends which you will then twist and turn into fabulous outfits that will downright swell up every cock in the room! Learning how to best pair a mini skirt with your crop top, how to fashion your wig to accentuate your boobs or walk in a pair of high heels with your fishnets. Body shaping to bring out the best of your curves whilst being able to match your colours in a way that expresses your sissy personality! Want to look lustrous and sophisticated? Wear neutral office colours. Want to look like a street whore? Colourful, revealing and tacky! Cute princess? Cosplay and babydoll dresses! You got to learn and pair! Of course, this is integral to makeup – which takes time, effort and dedication to learn how to apply. Skill will develop over time and practice, but the fun and creativity will be with you now and always!


3. Getting male attention!

A lot of sissies can vouch for that, after taking a girly photoshoot, picking out your favourite pics and uploading them sissy in slutty stockings making selfieonline is a process which is deeply enthralling and oh so satisfying. Likewise, with those girls who pose for men on Omegle, Chaturbate etc – the excitement derived from watching a real man cum simply from your girliness is unlike anything else!

Besides you’re a sissy girl aren’t you? You’re just an attention whore that seeks validation by serving men and making mistress proud. And guess what, you can do just that by exposing your beautiful sissy stature to the world that is hungry for sissy bimbos like you! So why dress up in average underwear or an old dress, and receive a few upvotes and nice messages – when you can instead dress like a proud girly slut and receive hundreds of upvotes, dozens of private messages of men aching to dominate your boy pussy and countless other stroking their fat cocks solely for you to perform on webcam!


4. Getting into shape!

Crossdressing is not always easy. And often, the biggest hindrance to your girly look is from your own body. Yes, some things we cannot help, like broad shoulders for example, but even these things don’t stop our favourite trans role models from looking simply gorgeous. No, the key to looking like a beautiful trap queen is entirely achievable by committing yourself towards getting that sexy sissy body! With exercise, you can eliminate fat % and develop an hourglass figure, get a bigger and plump ass, and striking legs that will make any man swoon for you! Of course, exercising is important for all aspects of your life, not only will you be getting a sexy body, but your health will improve drastically. You will feel more energetic, happy and calm. You will love yourself, reduce anxiety and develop your self-confidence. Who said being a sissy isn’t productive? So, crossdressing is a great way to motivate yourself into getting in shape. You will look sexier, feel sexier, and make yourself a happier and healthier sissy! Now let’s improve that squat game!


5. Building your girly wardrobe!

sissy in store looking for high heels

Guess what sissy, now that you like to dress up as a girl, you’ve opened yourself to a vast new world that is GIRL SHOPPING! Yay! A sissy loves to shop, apart from submitting to big huge cocks, this is her second favourite activity. Girly shopping is unlike male shopping in soooo many ways. Men have fewer options to choose from, and barely any accessories and different choices of clothing compared to women. Crossdressing will have you searching far and wide for that perfect crop top, that sexy pencil skirt, that insanely naughty bralette and of course the millions of cute pretty panties and sexy thongs. You will have so much fun building your own girly wardrobe, and each time you try on a new item the excitement and glee in doing so will be felt again each and every time.


6. Having a sense of purpose

Like all great hobbies, there is always a focus on something you can attain if you work for it. You can dress up in countless styles and explore a range of different girly personalities. Want to look like your favourite role model or a fictional character? Buy their outfits, adopt their makeup style! You can also enjoy being able to express your sissy secret in your day to day life; maybe wear panties during your daytime activities, painted toes and cute lingerie hidden under your day clothes. You can dress up and meet other crossdressers, and engage in a large and vibrant community!

7. Stress Relief

Outside of sissyhood, life can be stressful and exhausting. Responsibilities can always become tiresome and tedious. Fortunately for you, crossdressing is fabulous way to escape the boundaries of life in a fun and arousing way! Crossdressing is a deeply sexual form of expression for sissy girls. Playing with yourself while dressed in sexy lingerie is like a happiness drug that helps to forget daily problems. The thought of a juicy cock fucking your mouth or thrusting inside your boy pussy is liberating and exciting. This makes you feel stronger and more recharged than ever. Now you can get that happier and stress-free sissy glow! You only need to ensure yourself: There is nothing wrong with crossdressing


8. Acceptance

sissy daddys girl on floor taking selfie

A true and content sissy girl understands that there is absolutely no shame in crossdressing, but instead the opposite; pride. A femboy loves herself and

 understands that her femininity is as a part of her colourful and broad identity which does not change or overwhelm any other part of her life. She dresses like a slut because she wants to! She acts and moves like a princess because she feels like it, and she enjoys it. She doesn’t care what people may think, because she knows how to live on her own terms! A sissy crossdresser transcends everything we know about conventional sexuality, sissies experience sex throughout the broad spectrum of human sexuality and all the more happier for it!  She doesnt fall victim to boring, restrictive social norms, she’s too good for them! If you have problem with it, but you embrace being a sissy and want to crossdress full time. I suggest joining Sissylover Sissy Academy.


39 thoughts on “8 Reasons why you should start crossdressing

  1. Rose says:

    I’m so excited going fully into sissification yesterday I bought 2 cute short skirts with pink ribbon.
    I want to start taking breast enhancing pills

  2. Cumbunny says:

    I will be a good sweet cumbunny for you to use the same time as your friends need a little weak white willing wanting. Whoring lusting lover of the best beautiful blessed black balls and boss master slave swallowing stupid slut mark schrader Utica ny

  3. Jazmine says:

    I have been dress as woman since I graduated from high school and in the military I love been woman but I can’t be a sissy. I do love sucking cocks and I am good at both giving women a good lick make them cums I’m in charge not man

  4. julia-sophie says:

    I wear bras,panties and even silky,feminime blouses on a daily basis.It feels so right.Even my clit is shrinking to a satisfying 3cm.Sissy forever !

  5. steve says:

    I’ve cum to realize I was born to be sissy. I’m such a femboy now. My little sissy clit is so small. 3 inches hard. I know there isn’t a girl alive that would want me to even try to fuck her so I now understand my role in life. I’m to worship cock. Suck cock. Fuck cock. Swallow cum. I need a black master to own me and tell me what to do for him. I’m a slave to bbc. I fuck my sissy ass with an oversize dildo preparing it for a monster cock in the future.

    • Sissycandice says:

      I am a true Sissy, but I worship all cock and will serve my owner,mistress/master whom ever so tells me that I am their property.
      I will become the best SissyWhore for them and will gladly do ANYTHING, ANYBODY AND EVERYONE THAT I AM ASKED FOR THEM

  6. Shirley says:

    I have been crossdresser for most of my life and would like to take the next step to be totally feminized

  7. Tammi Love says:

    My breasts have started to grow. I crave cock all the time, especially BBC. After Sissy training, I may just go all the way, and get my pussy installed, and become a pornstar

    • Eddie Freeman says:

      I totally agree with you on that. I’ve been a cross-dressing for 15 years and I totally love black cock and if I can get a sex change I would do p**** movies just so I can do more black guys and get paid for it so I’d be doing something I love I’d be doing a lot of work

  8. Lynnzie says:

    I’m a lifelong C/D, and I’ve always been a sissy down deep. I’m dreaming of warm, fat cocks all the time now. I’m getting pounded daily with my 7″ dildo, but it’s time for the real thing. Can’t wait!

  9. Nixa says:

    Im soo excited finally i have become a sissy baby.Now i can enjoy monster cocks even a double anal feels good to me. Specially that embarssing punishments given by my owner infront of soo many male and females and that one on roads n streets are just love. Love u all sissy babies.Just transformed from a boy to sissy.

  10. Sissy Annette says:

    Sissy Annette secretly started wearing her mom’s silky panties,
    silky nylon and feminine lace trimmed half slips, and nylon stockings, and more, she fell in love with this lingerie.
    She enjoys and loves silky lingerie and it became part of her
    ever since then, and into her private closet adulthood life, and she doesn’t regret it at all.
    It keeps her calm and relaxed.
    She gets embarrassed when she buys her pretty and feminine lingerie in stores with women sales associates there,
    while she is in her boring drab male clothes.
    She can’t wait to get home to wear
    the new silky lingerie she bought
    that day .
    She is hetero, but she fantasizes about being crossdressed and being
    Bi with women and men 😉.
    Maybe 1 day 🤔.

  11. Katie says:

    Hi Ladies, I’ve been dressing in secret since I was very young. Having been raised with all sisters to me it always felt natural. But as you know reality stops you from doing what you love sometimes. But I’m so ready to just be my self and enjoy my life 😁👍😘

    • SissyFreya says:

      Hi everyone
      My wife found me dressing 2 yrs ago – her friend Debs saw me out and told her. They set a trap and found me one early evening- The you know what hit the fan and it wasn’t nice. I’ve always been effeminate (shaved legs arms and undercarriage ) shaped my nails and eyebrows- they checked my laptop, found sites I visited and gave me an ultimatum- dress 24/7 as a sissy maid – lose my Male clothes and go on hormones. Easy decision- I’m now SissyFreya the gay maid – I was locked in normal size chastity, then down to medium for six months, then small for another six months and now I’m locked in the “very small”. This has caused Atrophy- shrinking- I was 5” and now I’m 2” and my shaft has lost a lot of muscle and is like a girls little finger. My testes are like two Maltesers! In fact Helen (my wife) is having me go to a clinic in November to have my testes removed and I can’t wait. My bubble butt is loved by all men and I let them bareback me regularly at naughty places I frequent (Sauna Sauna Northwich England) my wife has a lover (Paul her boss) and he practically lives at our house now. I have given him my blessing and given him my wedding ring to wear when they go out together- the whole family knows I’m their sissy maid and I wait on at family gatherings. Debs is in charge of my sissygasms, she milks my prostate once per week and videos me with paying clients who fuck me. She sells the clips on line (Clips for sale). I’m to have large breast implants in he spring next year and really look forward to that – kisses – SissyFreya xxxx

  12. Penelope says:

    I dont know why I love to crossdress,
    I dont care why I love to crossdress.
    All I know is that it is a part of me, and it makes me a happier person.

    • Kevin Floyd says:

      I Love to crossdress it makes me feel so good. Now my wife love’s to dress me up and her friends too. Now they always fuck me like I’m the woman and there the men. But we are still ourselves but they always tell me oh your so femme anyway and they love being the men! It’s been wonderful since then them being like that! It just feels right! Bye!

  13. TinaRivaire says:

    I’ve been crossdressing since forever. I can remember locking myself in my moms room to use her shower and would somehow always find myself drawn into her walk in closet to explore her lingerie drawers.
    My mom was very attractive and had excellent taste in clothes and “unmentionables”.
    I would get all tramped up in her baby doll nighties, seamed nylons, full red haired wig and go thru the adult ads in the “Berkely Barb” finding m4t, m4m and BDSM ads that I would call fantasizing about what was going on and hoping to talk dirty while my pre-teen penis was rock hard in my moms bali or vassaret panties.

  14. Arissa says:

    I had been cross dressing or about 6 years before I told my girlfriend my secret. She was inexperienced so I had to teach her how to wear the lingerie. Her mind was blown when I walked in wearing 6″ Platform high heels with seamed stockings, a miniskirt garter with a school girl miniskirt on top and a lacy matching bra. My hair is chest length so I put it up in pigtails and last but not least I had put on eyeliner, eyeshadow, an lipstick. I walked in like a slut yearning for pussy and while shaking she immediately got naked and grabbed other lingerie I had laid out on the bed. Out of my collection she chose a similar outfit to me and promptly transformed into the sluttiest nympomaniac I’ve ever seen. She pulled my dick out and sucked it feverishly until I was about to cum I told her and she pulled out and jerked me off all inside her mouth, on her cheeks, neck, and titties. Before I could go soft she immediately shoved my dick inside her while she was lying on her belly so she could squeeze my dick as I lied on top of her. It felt like she could suck my dick with her pussy. It was the best sex I’ve ever had. I was able to completely be myself sexually with a woman I loved. We both quivered in orgasmic extacy while embracing in a copious lock. She kissed me and swapped cum into my mouth and told me to swallow it and in the heat of the moment it made me so fucking hard that we ended up fucking again.

  15. Terra says:

    I started wearing my mom’s panties and i felt like i was wearing the right clothes, but i had to put it back. But i needed that feeling do one day i visited my friend and when he was doing something I asked his sister for a pair and i came out to her and she agreed! Now i borrow clothes from her every now and then

  16. Kay says:

    I have started cd when i was young with my family members lingerie and have been turned on to it ever since now that I’m older especially when i smoke crack or meth and drink. I love to be feminine slutty cd and suck cock and get fucked slowly. Today i was at a store to buy lingerie but was nervous. I didnt buy it… Any advise?

    • Josie says:

      I started out similar to you would wear nylons and such started about 9! Then about 10-15 years ago I started to dress more especially when I smoked crack! Now I have several outfits, shoes, wigs, makeup, shave my legs chest face and armpits

  17. Maurice D Slaughter says:

    yeah im new to crossdressing but it make me feel alive. I consider myself half and half and I think I do them both well

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