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Amber Academy, Series IX: Utilizing A Wingwoman When Out En Femme

It doesn’t take alot to figure out that this current series of Amber Academy is all about getting out in the world to turn your fantasies to reality. I recently wrote a blog called ‘Time For Some Fresh Filth in 2016’, but what kind of Mistress would I be if I did not give you help with practical application? That’s what I’m doing now.

Establishing that there is a secret whore inside of you is never difficult. When you call me, some of you do your best to keep it together and play coy, but one mention of thick, juicy cock or pretty lacy dresses reveals your true self. Some of you are cocksluts or the ultimate girly girls and don’t you deny it! But what is going to get you off the couch, make you put down the remote and actually help you make your entrance into the wide world? This week, we’re going to talk about utilizing a wingwoman.

What is a wingwoman? Do you have one? Can you get one?

We all know what a wingman is. When two hot Alpha men are out in public, he’s the ‘bro’ that might connect you to the hot girl across the room. If you’re not super-Alpha but your buddy is, maybe he’s the pal that wants to see you happy and with Miss Right (or Miss Right Now!), and paves the way for a more sensitive you to meet a pretty girl at the bar/party/whatever. But a wingwoman is better than both of those. She’s a woman, so she’s automatically superior. But natural-born women are also often more comfortable in social situations. They can help instill confidence, give advice, boost your ego when you’re new to being out en femme, assist you in broadening your horizons and maybe even be the liasion to a hot guy or party or both. Maybe you just want to be girly and pretty, and you need someone to help ease you into public femininity. Need someone to actually stand with you in the makeup aisle, or take you bra shopping? A wingwoman eases the way.

Getting a wingwoman might require a leap from you….

Girly, slutty or both.....a wingwoman eases the way!

Girly, slutty or both…..a wingwoman eases the way!

Having a wingwoman in your corner might mean confiding in a female and admitting that you are a cockloving sissy slut or cross dresser looking to make an entrance. That strikes fear into some of you. But take a deep breath and consider this, thinking about the women you already know. Has it ever occurred to you that you might actually suck at keeping your true self under wraps? How about your best female friend or your ex-girlfriend or ex-wife from that time you were trying to walk the straight and incredibly narrow?

Let’s not discount just how perceptive women are. If an ex or a female friend has ever caught you trying on panties or playing with makeup, if you’ve ever been caught sucking a dildo, or enjoying secret solo anal play, if you visibly enjoyed being pegging by your ex and she made you beg for it, if you sucked a cock in front of her EVER, she knows. C’mon, she knows! And if she’s still in your life, still talking to you, and still friendly with you, it sounds like she accepts you and doesn’t judge you. Maybe she is your ex now because the two of you want different things, but if she is still your friend, she will not be shocked when you finally admit some things. Is it such a wild thought to ask if she wants to help you out sometime? Maybe she can give you a makeover, accompany you to a club or high class event and watch you play with a guy or socialize with other ladies? Boom. Wingwoman.

Maybe you’re sitting there like, nope. No way, no how, I don’t know anyone or I can’t talk to anyone, sorry Amber. Well, don’t close the book just yet. Read (or re-review) my last post, ‘Taking The Plunge To Make A Real Sex Connection’. There are sites online to connect, hook up, talk to and get to know people who can help you in real life. Want a friend to go shopping with? You can find that. It’s out there.

If you don’t have a wingwoman now, I would encourage you to get one. Yes, I’m awesome at guidance. We’ve established that a million times over, but a real flesh and blood woman to go out with and knock down some barriers so you can play for real? It can happen. How bad do you want it?

14 comments to Amber Academy, Series IX: Utilizing A Wingwoman When Out En Femme

  • Petey cream puff

    Id love to find women to do this with. To go shopping with would be great! Especially with her for girlish clothes/makeup!bras! I would go with her. I’m getting makeup application done to me next week and I’m going to wear leggings/ankle boots/boyshorts/bra under my sweater.I’m hoping she notices my bra and if she does I’ll confess that I always wanted women to do this to me.

    • Amber

      Many women are totally ready for makeovers and shopping, Petey. They love to be in charge of the transformation.

      • Petey cream puff

        I’m new to this and never had a girlfriend but I’ve found out women love to be in charge and in control. If I want to keep the friendship alive with girls I’ve got to do what they say and want.

  • SissyKrissyUK

    Mistress Amber,

    Utilizing A Wingwoman When Out En Femme.

    This sounds perfectly Amazing!

    Yes Please!


  • This is another great post, Ms Amber! your readers are lucky to have you, to guide them in the right direction and help along the way. A wing man always reminds me of the movie “Topgun”. But a wingwoman? Much more superior. No doubt.

  • Empress Rayne

    How awesome is the Amber Academy! Your readers must be loving the guidance they are receiving. I love this post. I often play wingwoman for femme friends and advise callers to make allies of coworkers, family members, or friends who they are terrified have seen pantylines or discovered their sissytime stash. They can make great girlfriends!

  • This would be so awesome to experience. I’d feel so embarrassed and humiliated yet so turned on. I don’t know where I would find a local woman willing to do this though. The reality is more complicated than the fantasy for us closeted sissies.

    • Amber

      If starting from the ground up, I don’t think it’s about setting out to find a wing woman, but rather making a friend that will be a wing woman.

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