CHALLENGES OF SISSY HOOKUPS
Do sissy hookups – fantasizing about them, watching videos of them, talking about them – make you incredibly excited yet terrified at the same time? As I poured over the many amazing submissions for this year’s Sissy Pageant, I recognized a lot of repeating patterns that I am familiar with from being a Mistress to many sissies in varying stages of evolution. Today I thought I’d write about the challenges of sissy hookups.
CAN’T PULL THE TRIGGER
There are a few reasons why you might be procrastinating when it comes to sissy hookups. Fantasizing is one thing, but somehow you can’t actually pull the trigger. You love to scroll through the dick pics on the apps, watch porn, talk to your Mistress about sucking cock, but as much as you want to do it, for some reason, you just can’t.
PROCRASTINATION TO HOOK UP AND DATE
There’s nothing like the idea of sissy hookups to create ongoing conflicts with many of those who I chat with here. Why the hesitation when it’s something that you are constantly fantasizing about? What is making you put the brakes on when deep down it’s your most secret desire?
AFRAID YOU MIGHT GET CAUGHT
Many sissies find themselves hesitating because there is a slim chance they might get caught by friends or family. I am here to tell you that if you are careful, this will probably never happen. I have many callers who have been dressing for decades and have never been caught. It takes a little extra planning, but it can be done and I’m happy to discuss some helpful tips and tricks with you for not getting caught during your session.
WORRIED YOU CAN’T PASS
Worried that with your broad shoulders. muscles, and six-foot-plus build that you’ll never pass as a sissy? This barrier to taking action deservers a post of its own, but for now I’ll just leave at this: when it comes to sissy hookups, passing is not an issue. Who in their right mind is going to turn down a blow job from a sissy in pink panties?!
YOU’LL LOVE IT TOO MUCH
This reason is more stealth. In other words, it’s probably not even a conscious train of thought. Maybe it’s a can’t-put-your-finger-on-it warning feeling. You start thinking about a potential sissy hookup, really leaning into the fantasy about how good that cock will feel in your mouth, how much you want to be treated like a little sissy slut and handled by a big daddy in a way that humiliates and thrills you. Deep down you know you’ll love it, maybe too much! So much so that maybe you’ll be tempted to break up your relationship or out yourself.
DOING NOTHING IS SAFER
Maybe the rush of just thinking about a sissy hookup spins you out, to the point where you start feeling that you might not be able to stop once you start. You go to the worst case scenario that you’ll blow your life up to the point of no return. And maybe on some level you want to do that. So to keep things safe, you do nothing.
TRUST YOURSELF
Most likely, you will never blow your life up. You probably have much more self-control than you give yourself credit for. Not to mention, procrastinating only hinders your exploration of a part of yourself that can be so fun to enjoy!
Here is an excerpt that I really loved from this year’s Sissy Pageant entries. I think they got it just right:
In all seriousness though, the biggest challenge has been learning to trust myself. Allowing myself to express this side has been transformative. Trusting myself opened doors to self-discovery and self-love. This journey has taught me that femininity is about embracing every part of who I am with grace, humor, and trust.
WHAT DO YOU THINK?
Let me know in the comments or book a call or texting session with me so we can chat about it in person.
HOW TO CONTACT ME
Stroker boys, make sure to check the CockControl page to see if I’m available or email me directly at  Audrey@enchantrixempire.com with any further questions. Texting sessions are via skype and need to be booked with dispatch or online and SexyTexting.com before we begin. Make sure to contact me via email as I may not see your request on skype and need to accept an invitation to chat with you on Skype before we can connect there.
If you’re interested in a particular fetish, make sure to let me know as soon as you can we talk. Crossdressing Sissies and Transgender Transformation, Cuckolding, Cocksucking, Bi-Curious, Humiliation, Tease and Denial and Humiliation are some of my main interests, but there are many more.
Please send all gift cards to audrey@enchantrixempire.com * View my wishlist here
Looking forward to chatting with you soon!
Wow, Thanks for the awesome post Ms Audrey, i think you have nailed down all of my reasons for not doing the hookup thing, but i have at least tried it a few times and loved it so much, i think along with the reasons you mentioned my other big hang up would be worrying about all the crazy diseases etc out there , I guess ill get my nerve up again someday to do again lol, Thanks for the awesome post xoxos
Thanks Vinny for stopping by. I’m glad you’re enjoying my posts. I think you should try again if you get the nerve 😉
viola , Thanks Ms Audrey lol xoxos
I’ve gone through a few stages of sissy training. I first started out finding cocks to suck.
Then sucking cocks in panties, which was an absolute rush, especially when he commented on how hot my ass was. It got me so horny, I sucked that cock until he exploded in my mouth.
I didn’t think, I just swallowed like such a good boy.
Then one day I was convinced to try something a little different… I was told to jerk off right before hooking up, cum by myself and lose that urge. Then go suck cock right after it.
After doing this, I felt like such a loser and I absolutely loved it deep down. At this point I trusted the guy and we understood eachother on a good level, so he would call me worthless. I LOVED it.
Then the hardest thing I’ve ever done was jerk off, cum… then take his cock in my ass.
I did it, he fucked my ass as my dead limp dick flipped around. I knew then, I am a complete sissy and my role is to please.
I now think my stud gets turned on by the punishment of me not fully enjoying it. He fucks me so much harder but I love seeing how much it turns him on!
I need some encouragement from a mistress tonight before I go see him, possibly call, cum and go get fucked.
I hope we can connect sometime soon!
x. A.