Hi Sissies!! Happy Pride š³ļøāš
If youāve followed my blog, thereās a good chance youāre a sissy looking to have sex with men! Iām here to help you with that š
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, Iāve hooked up with dozens of men dressed as Christina.
Iāve 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, āIām a Sissy. And I want to have sex with men.ā
For some itās not hard, but some sissies still hang onto their heterosexuality. This wonāt be a fun experience if youāre constantly second guessing yourself. You need to commit. You can tell yourself youāre 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 youāre 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? Itās time. Do you only wear panties? Time to upgrade your wardrobe. Still learning makeup? Lock in sissy.
No shortcuts. No half measures. Itās time to bring out your inner woman. š
Youāve 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 wonāt find exactly what Iām looking for, itās 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 donāt settle. Thereās plenty of men who want to fuck sissies and if you settle of a mediocre guy, you probably wonāt have as much fun as youād like.
Wow! Isnāt he sooo hot š„µ
Anyways Sissy! Where do you find your man? Youāre 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. Itās full of guys looking to fuck asap. Donāt 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 youāre in full makeup. The big downside is not every guy understands the sissy fetish on Grindr.
2. Fetlife - Itās 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 wonāt 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 Iāve 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. š„° insane to think 900,000 people have seen my sissy self!
Hereās some general advise in finding the right guy on these platforms.
No Profile Picture = Will Waste Your Time. Iāve never had anyone that anonymous be serious about meeting up.
āWhat all are you looking for on Grindr?ā
āWhat are you into in the bedroom?ā
āAre you clean and recently tested?ā
Donāt assume heās into everything you are. Personally I dislike having men touch my clitty. So if heās really into that, I know itās not a good match. Donāt let him get away with saying āiām into everythingā because thatās never true. But share what you enjoy and your limits!
Also for your safety make sure heās 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. š
Just make sure he makes you feel hot and horny but also safe!
So you found a stud who checks all your boxes. Itās 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. Itās a bit safer that he doesnāt know where you live. Just incase you donāt 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 itās important I book it. Make sure itās not a shady hotel and if Iām 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 heās getting.
It also gives you an opportunity to make sure youāre shaven smooth, your makeup is perfect and your enema has cleaned you out. Additionally, Iād 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 heās 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 heāll 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. Itās okay! You can be who you truly are.
Makeout. Feel his abs. Let him grab your ass. Have fun! But sooner or later youāll be on your knees looking up at your man. Itās time to suck his cock! š«¦
Sucking dick is a skill. If youāre 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 itās the best blowjob theyāve ever had.
Hereās a few tips for working those tips! š
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.
Donāt tell him you can deepthroat if you canāt! It looks easy in porn but itās 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 youāve 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 youāll become.
Heās had your mouth. Now he wants that sissy pussy.
Itās a requirement if you want to make sure you feel good and wonāt hurt yourself.
Heās the dominant one. Heās never walked a mile in your heels. He doesnāt know what itās like taking dick. So if youāre inexperienced he could hurt you.
If you want to control the pace then you should start on top riding his cock. Itāll let you go at your own speed! Once you feel comfortable let him mount you doggy and go to town!
From there itās easy! Bite down on that pillow and let him fuck you silly! When a stroke feels especially good let out a faggy little moan! Thatāll tell him it felt good and he should keep fucking you like that.
If youāre anything like me youāll love the submission just as much as the feeling of him hitting your sissy spot. Donāt just lay there stiff! Push back on is dick, moan all sorts of nasty stuff and enjoy your new sex life! š„µ
After heās cum in your bum and left, you might feel that sissy shame. Before you purge your clothes and block his number, ask yourself āDid I have fun?ā
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!
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