How to Know if Your Ready For The Big Time

Squirt From The Hose

Image: terwilliger911 (Flickr)

Some of you out there may have, at one time or another (or always), dreamed about meeting that perfect girl crossdresser. You know, she show up beautifully made up, slinky dress, expensive pantyhose and heels and smells like a flower blooming after a rainy day in Italy. Then maybe after a little wining and dining, she takes you into your bedroom and proceeds to spank and pound your ass flat and tender.

Mind that this is only after you first get a taste slurping her girl cock until she tells you when. If you’re lucky enough, maybe leaving a generous tip in your mouth and down your throat.

If you unfortunately find this absolutely disgusting or appalling, cover your eyes, find your mommy and I’ll give you the opportunity to leave now.

Great, still here?

Have you ever had an attraction to other crossdressers whether it be in admiration, willing to go the distance with a passionate foray or been there, done that? Well, for those “bi-curious” waiting for the experience no different than a teeny-bopper anxiously anticipating getting her cherry popped, I believe I came upon (quite literally) a foolproof way to determine if you’re ready or not.


Next time you are in your dress up routine (helps to make yourself look extra sexy here), wank it as usual dreaming you’re inching your way up your sissy lover’s ass. Then when you are ready to shoot your load, have a shotglass or small cup handy. Even your non-wanking hand will work.

Happily come into your choice of vessel, then without delay, and while still nice and hot, gulp it into your mouth. Savor it in there for a little bit, getting use to the taste, then swallow. If you prefer, spit it out. Of course we have to simulate a real situation and your options, don’t we now?

How was it, dear?

Typically, post-orgasm is the one instance where all those lustful, perverted crossdressing desires disappear, for a short while anyway. If you’re able to take down that hot, sticky milkshake without a flinch, wince or vomit then, congratulations, you’re ready for the big time. Bonus points if you actually enjoyed it.

If it wasn’t quite your thing, don’t worry, it may take a few times to get use to. Warm come is an acquired taste much like your very first beer or girly lover to be.

If this is something that gets your pantyhose wet, however, here’s an even sexier variation. Instead of swallowing (or spitting), fill your love honey into a squirting dildo and either suck on it or use it penetrate your ass and release the load after a few passes. If only a non-squirting dildo is available, no problem, just lube it down with your love gunk and get to work up there or down there. Again, doing this post-orgasm may not have the same kinky pleasure but the key is to learn to enjoy it and eventually you may crave it.

When all is said and done, more than likely you can decide whether you are ready to go down on (or into) that future toy of a crossdresser. Sure, you can test out your fantasies on the first CD that winks at you. Yet deciding you’re not game in the middle of having a cock going in and out of your mouth might just get a little weird, you know.

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Posted in Fantasies
8 comments on “How to Know if Your Ready For The Big Time
  1. Pantyhose n Poppers Queen says:

    That actually sounds like alot of erotic fun, though I’m also a watersports-loving gal too :-)))

  2. Lisa T says:

    That ejaculating dildo does sound interesting. P N P Queen, I’m a watersports lover too and would love to chat with you about it sometime. I’ve never brought it up I any of my posts here as I thought it might be too kinky and since this is Sheery’s site, I try to limit my comments to subjects that she has brought up.

  3. Sheery says:

    @PnP I wouldn’t expect anything less from you girl and such a great way to put it.

    @LisaT you’re such a nice girl (peck on the cheek to you). Considering our lifestyle, though, does the kinky line really get drawn? 😉

    I’m having a glass of wine right now and dedicating a toast to our new watersport club.

  4. Lisa T says:

    Hi Sheery, I’m not at all surprised that you’re open to discussions of just about anything that adds to the pleasure and excitement of our pantyhose fetish activities. You’ve demonstrated your wonderful imagination and willingness to push the envelope of kinky in so many of the articles you’re shared with us here. I think these kind of discussions are of great value because even if we’re convinced we’re ready for the “big time” the reality is that, for a multitude of reasons, most of us are going to be enjoying our fetish delights solo. Rather than lamenting the lack of that magical, fantasy fulfilling partner, why not do everything and anything we can to increase the pleasure, stimulation, and ultimate satisfaction of our own enjoyment of the pantyhose fetish experience. Rather than getting into a discussion of the pleasures of watersports and pantyhose here, maybe you could start another “kinky” thread to kick off another round of stimulating things to do in pantyhose.

  5. Sheery says:

    @Lisa Idea well taken my dear… stay tuned!

  6. Candi says:

    Such a fun read!!! Loved it!!! I have to tell you that I have lubed up my dildo with my own cum and then inserted it into my ass, OMG! the best feeling lube EVER!!!! So silky smooth and warm -mmmmmm- my dildo never glided so smoothly and slippery before, it was such a great experience! I’ve also raised my legs in the air (while lying on my bed) and put them over my head so that when I wanked I felt the wonderful feeling of my warm cum being plastered all over my face!!!! I love how that feels and looks. I just love how I look with cum all over my face especially when I’m wearing bright red lipstick!!!! i love looking at myself in the mirror seeing it all over -mmmmmmmm- licking my lips thinking about, and yes I did lick my lips to get some of the delicious cum into my wanting mouth -mmmmm- so good!

  7. Kim Cummings says:

    Ohhh, so naughty and exciting. I’m sure that I am available for the opening of the sensuous feeling of being a good little Bitch for your pleasure! I love the idea of what could happen to be able to make sure that my ” pussy ” gets a chance to try and get a good little girly cock in my mouth and ass. I like the idea of what could happen to know if it is a very erotic sensuously sexy fun and exciting time for me. I have a nice collection of lingerie and the vast array of my own attire. We are into the kinky sexual fun and exciting times in the future.

  8. Bobby says:

    Years ago I wanted to know what cum tasted like and tried to follow your advice about quickly slipping my fresh load into my mouth but I just couldn’t bring myself to do it. I also tried the legs over my head shoot into my own mouth but my aim was never good enough…although I did develop a desire for facials from trying it so it was worthwhile lol. What did work for me though was the cum ice cube. I shot a big load into a shot glass then poured into an ice tray and froze it. Next time I got dressed up and got very excited I popped it in my mouth and let it melt mmmm yum!!!

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