Hi Sissies!! Happy Pride 🏳️🌈
If you’ve followed my blog, there’s a good chance you’re a sissy looking to have sex with men! I’m here to help you with that 😘
A little background on me first! 5 years ago during pride, I worked up the courage to hookup with a man for the first time! Since that night, I’ve hooked up with dozens of men dressed as Christina.
I’ve learned a lot in that time and wanted to pass on some of that knowledge to any sissies who might be taking their own leap into the world of gay sissy sex this pride month!
A picture of me right before I had my first hookup with a man.
Are You Ready for this Sissy??
The first step is to admit to yourself, “I’m a Sissy. And I want to have sex with men.”
For some it’s not hard, but some sissies still hang onto their heterosexuality. This won’t be a fun experience if you’re constantly second guessing yourself. You need to commit. You can tell yourself you’re just experimenting, but at the end of the day you need to accept you want to have gay sissy sex. Just enjoy it.
Now that you are going to finally let your sissy side have some fun, how do you get ready?
If you’re like me, I was dressing up well before I had sex. And nothing makes a sissy feel sexier and hornier than looking pretty. Never shaved your legs? It’s time. Do you only wear panties? Time to upgrade your wardrobe. Still learning makeup? Lock in sissy.
No shortcuts. No half measures. It’s time to bring out your inner woman. 💋
You’ve accepted this is happening. You are confident and looking your sissy best! Time to find your man.
Tell me sissy, what is your type? Ever thought about it before?
Personally, I love a tall, strong and dominant man. I love if he dresses nice, has a little facial hair, and if he has big muscles. While I won’t find exactly what I’m looking for, it’s important to set standards. With all this in mind, he has to be in good shape, 6ft, and clean up nicely.
Think about what kind of man you want to be pounding you sissy pussy and don’t settle. There’s plenty of men who want to fuck sissies and if you settle of a mediocre guy, you probably won’t have as much fun as you’d like.
Anyways Sissy! Where do you find your man? You’re probably not going to many coffee shops dressed as a sissy.
I have 3 places I find men.
1. Grindr - I find 90% of my hookups on Grindr. It’s full of guys looking to fuck asap. Don’t be shy when filling out your profile. Tell them what you want and post pictures. No one is going to find you and expose you. Especially if you’re in full makeup. The big downside is not every guy understands the sissy fetish on Grindr.
2. Fetlife - It’s less of a dating app but more of a kink website. The guys you meet will definitely understand the sissy kink. The big drawback is most men won’t be local or they are looking to sext. Good for online fun. Not so much for irl hookups.
3. Reddit - This one seems weird but I’ve met a couple guys off Reddit. There are subreddits like r/sissypersonals where you can put out personal ads looking for hookups. Kinda gives Craigslist vibes. I get tons of suitors messaging me here but again not all are serious!
On a side note I have the second most popular post on the sub. 🥰 insane to think 900,000 people have seen my sissy self!
Here’s some general advise in finding the right guy on these platforms.
No Profile Picture = Will Waste Your Time. I’ve never had anyone that anonymous be serious about meeting up.
“What all are you looking for on Grindr?”
“What are you into in the bedroom?”
“Are you clean and recently tested?”
Don’t assume he’s into everything you are. Personally I dislike having men touch my clitty. So if he’s really into that, I know it’s not a good match. Don’t let him get away with saying “i’m into everything” because that’s never true. But share what you enjoy and your limits!
Also for your safety make sure he’s tested and can show you a recent std test. You can also ask him to wear protection. Personally, im on PREP and recommend other sissies to take preventative action for peace of mind. 😇
Just make sure he makes you feel hot and horny but also safe!
So you found a stud who checks all your boxes. It’s time for the main event! If you feel extremely comfortable with him you can invite him to your place. But I personally love the first meetup to be a neutral third place like a hotel room. It’s a bit safer that he doesn’t know where you live. Just incase you don’t want to meetup again.
In my experience most of the time he will offer to split it, if not just pay for the room. For me it’s important I book it. Make sure it’s not a shady hotel and if I’m there first I can spend the afternoon in the room getting ready for him.
I usually send him a pic like this too. It lets him know what exactly he’s getting.
It also gives you an opportunity to make sure you’re shaven smooth, your makeup is perfect and your enema has cleaned you out. Additionally, I’d bring a dildo and some lube. Bouncing on your dildo before he arrives will both stretch you out and make sure the enema left you squeaky clean. You can also leave your butt plug in until he’s ready to fuck you.
It can be a little nerve-racking waiting for him! I like to dim the lights, have a couple glasses of wine and play some Ari or Sabrina to put me in the mood. Before you know it he’ll be knocking at your door!
You take him to the bed, get him a drink, now what?
Do what comes natural and let your feminine side take over. He expects you to be a girly little fairy. It’s okay! You can be who you truly are.
Makeout. Feel his abs. Let him grab your ass. Have fun! But sooner or later you’ll be on your knees looking up at your man. It’s time to suck his cock! 🫦
Sucking dick is a skill. If you’re good at sucking cock you should be proud! For me it took lots of practice to get to the point where guys will tell me it’s the best blowjob they’ve ever had.
Here’s a few tips for working those tips! 😘
Right around the head Is the most sensitive. Let your tongue work his head as you suck.
Lightly cup his balls while you blow him.
Careful to use no teeth. If you have trouble with this try covering your bottom row with your lip.
Don’t tell him you can deepthroat if you can’t! It looks easy in porn but it’s far from it! If you lie and say you can, you might throw up on his cock which kills the mood in a disgusting way.
I know you’ve probably never received a blowjob and never will, but keep in mind what he sees. I like to make eye contact, flutter my eyelashes and give him a nice view of my ass while I blow him.
At the end of the day, the more penis you have in your mouth the better cocksucker you’ll become.
He’s had your mouth. Now he wants that sissy pussy.
It’s a requirement if you want to make sure you feel good and won’t hurt yourself.
He’s the dominant one. He’s never walked a mile in your heels. He doesn’t know what it’s like taking dick. So if you’re inexperienced he could hurt you.
If you want to control the pace then you should start on top riding his cock. It’ll let you go at your own speed! Once you feel comfortable let him mount you doggy and go to town!
From there it’s easy! Bite down on that pillow and let him fuck you silly! When a stroke feels especially good let out a faggy little moan! That’ll tell him it felt good and he should keep fucking you like that.
If you’re anything like me you’ll love the submission just as much as the feeling of him hitting your sissy spot. Don’t just lay there stiff! Push back on is dick, moan all sorts of nasty stuff and enjoy your new sex life! 🥵
After he’s cum in your bum and left, you might feel that sissy shame. Before you purge your clothes and block his number, ask yourself “Did I have fun?”
If so text him the next day. If you enjoyed sex with a man, you might enjoy having a boyfriend!
I hope this post could help some anxious sissies who are exploring their sexuality during pride! I know it can be hard to be a sissy but you deserve to have a fulfilling sex life too! Love you girlies!
theartofmadeline
yousharknotpass
amandla
