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Tips for the First Time Sissy Cocksucker

Miss Rachel loves to encourage the sissy cocksucker in you! 1-800-356-6169Hello, Horny Readers! This blog post is a special shout-out to the sissy cocksucker. More specifically, it’s aimed at those gurls who have spent a long time working themselves up to sucking a real cock, and are ready, but maybe a little bit nervous. I’d like to offer some tips and reassurances that have been helpful many times in My tenure of training and encouraging the oral fixation common among the feminized.

How does a sissy cocksucker know s/he’s ready for the real thing?

In short, a sissy cocksucker will know that s/he’s ready for the real thing when s/he can’t stop thinking about it, and sucking he/r dildo is no longer enough. But there are more practical considerations as well:

  • Has s/he actually become proficient with he/r dildo? Can s/he lose he/rself in sucking it, and give a smooth, sensual blowjob as well as a more vigorous one?
  • Has s/he perfected he/r sissy look, so that s/he is able to present he/rself to he/r stud as he/r feminine best?
  • Is s/he in a position to protect he/r sexual health, and that of any prospective partners?

If s/he can say yes to the above, then s/he’s ready.

How should a sissy cocksucker go about choosing a cock to suck?

Many sissy cock sluts are content to visit gloryholes and adult bookstores, and I’ve given up on trying to dissuade them. Why would I dissuade them? Well, there’s a lot less you know about some random who sticks his cock through a hole in the wall, and although oral sex is one of the lower-risk sexual activities in terms of STDs, lower does not mean nil.

Also, although I realize not every sissy is a size queen, I always picture a certain kind of cock as worthy of being worshipped, and it’s not a little one. Heck, I do know plenty of sissies who don’t care how small a cock is, just that it can get hard and shoot, and frankly, god love ’em because impartial sissy cocksuckers may be the only action little cocks get.

I suppose a sissy size queen could simply wave away an inadequate cock at the glory hole, but that’s kind of awkward, isn’t it? I say, if you can, choose one or more cocks that you know will give you an unforgettable experience, rather than just accepting whatever you get.

Lastly, some sissies get an erotic charge just being in a place where they could service a cock, even if they wait around for hours and nothing pans out. But that seems like a waste of time to Me.

At the end of the day, I say “to each their own”. I’ll listen with relish and without judgment to a sissy’s cocksucking tales no matter where s/he found it, but if you’re asking, I say pick the cock, and pick it from someone who’s at least willing or able to chat a bit about expectations and safety. Popular sources would be Craigslist, Adult Friend Finder, and

Some final tips for the first time sissy cocksucker

Eat a light meal a couple of hours before your date with dick. Personally, I don’t care how Miss Rachel loves to encourage the sissy cocksucker in you! 1-800-356-6169messy a blowjob gets, including a little regurgitation (I’m perverted like that), but your stud cock might find it a bit indecorous to have his balls painted with your dinner. Besides, you’ll muss your dress! You can always take yourself out for a more substantial meal afterward and might want to if you’re an enthusiastic gurl who works up an appetite when s/he sucks cock.

Bring a small makeup kit with you if you’re going out for cock. Your face is liable to get messy. Some of you enjoy self-administered public humiliation and wear your smeared makeup (or even his cum) as a badge of honor as you make your way home. But if you would rather remain presentable, bring a bit of makeup with you, and a few other products so that you can touch yourself up: lipstick, mascara, maybe a little pressed powder in a compact, a bit of rouge, and a brush to apply it with.

Also indispensable is a small bottle of toner and a few cotton pads to clean up the smudged bits a little. This way, if you feel like taking yourself out for a post-suck cocktail to toast your experience, no one around you will be the wiser. I mean, they’ll obviously know you’re a girl-dressed guy, but not what you’ve been up to!

Lastly, bring a bottle of water. Nerves can dry your mouth up, and as Miss Rachel has counseled you before, your mouth should be as inviting as any pussy, and an inviting pussy is wet.

Okay gurls! You’re ready! Be sure to tell Me how it turns out!


Miss Rachel, the sissy cocksucker consierge!





16 comments to Tips for the First Time Sissy Cocksucker

  • princess

    Thanks for the tips Ms Rachel….i have decided that 2018 WILL be the year i progress from practice…. to real cock (Although i will always try to improve via practice) I personally can relate to the ‘bring a bottle of water’ tip….When practicing with a 10 inch thick toy cock, i often get a bit cotton mouthed….I know that wet BJ’s are the only except able ones, so water helps with that and with deep throat. I’ll definitely use your other tips too…..I am quite nervous, but more excited and READY!!!

  • A perfect post for a good New Year’s resolution of being the best sissy cocksucker ever. Very expert tips from Ms Rachel makes this doable in large doses. Oh yes, the messy blowjob is not my thing. A bottle of toner on hand and maybe some baby wipes can work well in a sissy purse before she steps out for that blowjob of a lifetime.

  • ollie


  • Ms Rachel, a very supportive and helpful blog post for would-be cock suckers. I think all guys should have the experience of being a cocksucker so as to destigmatize the practice…let’s face it, everybody loves a beautiful cock!

  • vanilla

    Cocksucking…yum! vanilla loves glory holes, there’s something so, well, dirty about it. Nothing makes a sissy gurl feel like a filthy, cock addicted slut like kneeling on a dirty floor sucking a cock poking through a hole in the wall, with no knowledge of who is on the other side. Makes you understand you are nothing, not even a person, to the man you’re servicing, just a wet mouth meant to please him. There are ways around the disease issue, keep a box of rubbers with you, before you think about doing the real deal in a glory hole, take your dildo and practice, practice, practice putting a rubber on it using your mouth. Put the rubber in your mouth and get to where you can seamlessly slide it on the dildo as you take it into your mouth.

    And, don’t look down your nose at a smaller cock, you’re not there to choose, you’re a dirty slut and whore, your desires don’t matter. Sooner or later the big ones will poke through, but it’s not your place to reject anyone. You are there for one purpose, to make real men happy.

    • Rachel

      I appreciate the condom tip, vanilla! I’m sure other gurls do too!

      Just the same, not everyone is into degradation as part of their sissy identity, and I want those who aren’t to know that there are other alternatives to get their cock fix.

      • vanilla

        That’s true Mistress Rachel, not everyone is into the degradation aspect. But, if they’re visiting a glory hole to satisfy their cock sucking desires, well, that pretty much isn’t the wine/dine/flowers kind of affair now is it?

        vanilla learned the condom thing early on, suspect you’ve not been around many actual whores as most seem to practice it. vanilla learned it when s/he started doing “outcall” massage services and “escorting.” If you do it well, your trick doesn’t even know you slipped one on him till after you’re through. Very good technique for dealing with those “I don’t wear rubbers” kind of men. Of course most of that business has dried up now that vanilla is no longer a “chick with a dick” but them’s the breaks.

        • Rachel

          Just because a gurl doesn’t necessarily need romance, or doesn’t expect it, it doesn’t mean s/he wants or expects degradation. Some gurls go to gloryholes because they’re convenient, or because they don’t have the confidence in their desires to make other choices and prefer the anonymity that the glory hole or booths at the adult bookstore provide. Some feel more comfortable going to a semi-public place for reasons of personal safety.

          And you’re right–I know some high-end escorts, and plenty of sluts, but not many street whores. Just the same, no matter where a gurl decides to get he/r cock, you’ve shared an excellent tip for the safety-conscious among My readers! I’m sure they’ll appreciate it.

          • vanilla

            Safety is critical. vanilla kind of envies people who were into this back in the day when whatever diseases you might catch weren’t fatal or antibiotic resistant. s/he can also understand the anonymity and semi-public aspect now that You mention them. Still and all, it’s got to provide a touch of dirtiness to the act, which can be exciting even if the gurl isn’t into true humiliation or degradation.

          • Rachel

            Oh, I’m sure it does!

  • missy laflamme

    As you told me b4, it is inevitable ! It is CUMMING…omg….funny how girls can tell that I do it…and they just tell me they know. I asked one girl out and she said ” I’m not going to date a GIRL, especially one like you ! I’m a good girl….

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