How to get in my pants: a guide
Written by Mina SissyCD510
Found on Reddit
How to Have Sex With Me: A Complete Guide for Daddies to Meet Your Dream Sissy
nsfw
(Edit: thank you for all the kind words and awards!)
Recently, a daddy reached out to me asking for tips and tricks to connect with sissies. I realized that while there’s a ton of content on this sub for girls, we have plenty of great guys in our community that would love to own a sissy but aren’t sure how or haven’t had any luck. I figured this article would be a win-win to help both sides achieve their fantasies. While it’s written to men, I think sissies would benefit from the read as well.
ABOUT ME
I'm a mid 20’s CD that has been dressing for almost my entire life and sexually active in girl mode for the last 7 years. While I’m technically a switch, I have been topped and owned by a number of male lovers. Here are some pictures of myself that hopefully prove some amount of experience in the lifestyle.
Quick disclaimer: while I think this is generally good advice, these tips are based on my own preference. Every girl is different!
REALITY CHECK
Let’s begin by setting expectations about us girls. In my experience, the majority of sissies out there are both deeply in the closet and relatively inexperienced in dressing and sex en femme. This is NOT a dig on anyone at all, rather I think a lot of guys I’ve talked to have unrealistic expectations about your average sissy. The beautiful, smooth shaven, immaculately makeup’d girls that top r/sissies are rare. Those who also live near you and are open to sexual encounters are truly unicorn tier.
This isn’t to discourage you or make any girls feel bad, I’ve just noticed a lot of guys out there (mostly horny assholes) assume all sissies are totally put together and down to be in a gangbang at a moment's notice. This is just not true.
Here’s the good news! If you can empathize and understand where the majority of sissies are coming from, I guarantee you will start having more success making connections. Let’s start by painting a picture of the average sissy’s journey (this was me):
PORTRAIT OF A SISSY
Most of us started experimenting with girl’s clothing in c***dhood or puberty, likely from a mom, sister, or relative. This was almost certainly deeply in secret - I have personally never met a girl whose parents encouraged or made space for such behavior.
At some point, dressing becomes a sexual thing. This comes with a lot of confusing feelings, often causing girls to feel extreme shame and increasing the tendency to be secretive.
We begin accumulating our own clothes and toys, but very slowly. If you live with your parents or roommates, the simple act of buying girl things is an ordeal, let alone practicing makeup or taking pictures. I believe not having their own space is the #1 reason sissies aren’t able to engage in the lifestyle.
Taking all that into account, the average sissy might look something like this:
She is deeply in the closet and worries about her two “worlds” colliding
She does not live on her own or have a place to play (can’t host)
Her ability to fully dress is limited to maybe once a week
She only has a handful of girl things
She has limited experience in makeup and dressing and feels self conscious in comparison to the girls she sees on the internet
She likely hasn’t had sex with men yet
She goes through wild swings from desperately wanting to be more girly to feeling disgust or nothing for her girl side
On that note, while she loves the idea of being a bimbo fuckdoll, her fantasies and her actual limits are wildly different
If you’re able to empathize with this suddenly a lot of issues I hear from daddies I talk to start making more sense:
FAQ
Why does this girl respond to me then go silent for a month?
She’s likely experiencing swings between her boy and girl mode. Sometimes she’s super horny for cock, other times she might feel like a normal guy.
Why does this girl keep flaking on our plans?
Likely the same reason as above. Even if she desperately wants to, sex with men has likely only been a fantasy for her at this point. Confronting that reality is a massive step so large many girls will never do it.
Why can’t this girl make plans to meet within 24 hours?
There are a ton of logistics that have to be overcome depending on her living situation. Where will she get ready? How will she be able to leave the house if she lives with others? What if a neighbor sees her? Most of my hookups have taken at least 3 weeks to plan and wait for the stars to align.
Why won’t she show her face?
She’s terrified of getting outed and scared you might share her pics. She may also feel inadequate IRL compared to all the faceapp/unicorn pics guys have come to expect on reddit.
She agreed to let me dom her but she’s slacking on my commands. What gives?
Almost all sissies live a completely mundane male life 99% of the time. It’s impractical to stay locked up 24/7, dress up for you every night etc. Ownership must come with an understanding of the practical limitations of being a girl. Her desire may be there, the time/energy simply is not.
Like I said, simply understanding where the average sissy is in her life will go miles to helping you connect with one. Now that we’ve established that, here’s the step by step tips to seducing her.
1. STAND OUT
For the love of god, please, please do not begin a message with “hey,” a dick pic, or immediately ask to fuck. This is not an exaggeration - the last 17 out of 20 messages I’ve gotten on Grindr were one of those 3 things. Those types of messages don’t tell us who you are, what you’re into, or if you’ll be compatible. It’s also worth knowing that sissies who are willing to post decent pics with their face typically get bombarded by guys just like genetic girls on a dating apps.
Stand out by writing a longer, meaningful intro. At this point I’m so pleasantly surprised by anything more than a few sentences I will always read those messages no matter what. Unlike tindr hookups, don’t feel the need to come up with something clever or neg her - politeness ALWAYS wins for me. I would follow this format:
Compliment something specific about her. All sissies love affirmation. If she’s into degradation you can do that after you know that she likes it.
Honest statement of intent. It’s ok to be open about wanting to fuck, just make sure you make it clear you are willing to get to know her and take things at her pace.
Offer her something else that isn’t sex. Keep in mind you are competing with all the other horny guys out there that wants her attention. It’s a harsh reality but I think being aware of it will give you the highest chance of success. Below are some examples, all of which have gotten me to engage in a relationship:
If you can host, offer to give her a safe place to dress up with 0 expectation of sex. Most sissies absolutely crave freedom to express themselves and a safe haven would be a dream opportunity. It might even be enough to get her in the mood for more (it did for me).
Offer to be a safe place to mail stuff to. Again, just buying girl shit is such a hassle having an ally in that endeavor is a massive help.
Gifts. While I don’t suggest going full simp a physical reward can be a big motivator. Pro tip lingerie is my literal kryptonite and the idea of a guy buying things for me to wear for his pleasure is one of my biggest turn ons.
In terms of where to look, I’ve had the most success with Fetlife. People there seem more willing to communicate and stick around much longer than dating apps.
2. ENTICE HER
You’ve managed to get a few replies. Awesome! Unfortunately, the period that follows is where most interactions fizzle out in my experience. To avoid that, you need to continue to entice her to open up.
This part of the guide will vary wildly depending on the girl, but the general premise is to identify what she likes talking about and continually get her to open up in that area. Shocking stuff right? Here’s another way to think about it: the goal is to make it so she gets a rush when she sees you’ve messaged her, either on an emotional or sexual level. I feel like this all sounds idiotically obvious so let me give you some real examples:
Guy A: Learned that I like lingerie. He’d send me links and pics of outfits he thought I’d look good in and it was such a turn on to see what he was going to send next. Eventually I began taking pics in my underwear for him culminating in a very special “fashion show” at his place.
Guy B: Learned that I like public exhibitionism. We traded stories and I loved typing up my exploits for him and seeing how he responded. I have those emails saved and still pleasure myself to them from time to time. We eventually met in a parking lot for some outdoor fun.
Guy C: Early in my sissy years, a guy offered to help me keep me accountable for progressing as a girl. Not full on doming, but setting goals for buying clothes, learning makeup etc. It was an absolute pleasure to have someone genuinely try to help me improve while also taking the time to learn about me. I couldn’t wait to see what goal he had next.
See what I mean? Questions like “what’s up” or “how are you doing” will go absolutely nowhere. Find a specific common ground that you can both enjoy and stick with it.
3. MAKE HER COMFORTABLE
When it comes to actually meeting, your goal is to make her feel as safe as possible, because her biggest barrier will be probably be safety. This can mean a lot of things - safe that you won’t physically hurt her, safe that she won’t be outed, safe that she won’t get an std etc. You need to eliminate as many factors that might make her back out. Here are things a guy can do that make me feel at ease:
Pay for a hotel, at least the first time. Your place might be free, but a third party location offers more safety in her mind. An investment also increases her obligation to show.
Cool your dom side at first. While both of you have fantasies around domination, I personally think it’s too intimidating to relinquish all control to a complete stranger. Be patient. Let her set the time and place. Don’t make unreasonable demands. Be a total gentleman. Once she feels safe with you later on you’ll be able to do everything you want with her. I see waaaay too many guys message me demanding I submit to them out of the gate. It’s a huge turnoff.
Get tested. Regardless of transmission rates and how safe you promise you are, every sissy is afraid to do something that could impact the other areas of their life. I would literally be 10 times more willing and quick to action to sleep with a guy who has gotten tested than some random internet stranger. Sissies are looking for complete freedom in their feminine form and eliminating that risk can be huge. It may sound like a lot of effort but personally it’s a golden ticket to this sissy’s body.
Use a fucking condom and advocate it. It’s your life but I immediately form negative opinions about guys who brag about not using condoms or want me to go bareback on the first meet.
Send at least one clear picture of your face. If a guy won't do this I full stop end that conversation. While I understand discretion, it absolutely works both ways.
4. THE MEET
If you’ve managed to set up a meet congrats! Sex itself warrants a separate article but here are a few miscellaneous pieces of advice:
Bathe and brush your teeth. Do I need to say it? In light of a few of my hookups, apparently yes.
No matter how awkward it is, try a little small talk before the action. She will be self conscious about her voice - a guy once specifically reassured me and it honestly melted me.
Unless you have 100% established limits, HOLD BACK ON YOUR DOM SIDE AT FIRST. There will be time for all of that but she is going to be scared as fuck in the beginning.
Sissies like foreplay as much as any other girl, yet I've been with plenty of guys who think I want them to plow right into me right away. I personally enjoy having my bulge rubbed, my ass fondled, and my waist grabbed.
CONCLUSION
If you’ve read this far, thank you! I hope it helps you in your endeavors, and please let me know if you'd like me to write more. I’m always open to giving advice for sissies and daddies - you can find my kik in my other posts if you want to reach out directly. Cheers!
