Fellow femboy in need.
I have a fear of meeting men for sexual stuff, I struggle with it a lot, and haven't dared to meet anyone like that for 4 years. Any tips on how I can overcome this fear?
Love your content, I wish I could be as beautiful and courageous as you!
I think I can give some practical advice on this particular subject. I lost my virginity at 19 thanks to Craigslist, lol, and I think I’ve come a long way and learned a lot about myself and the process since then. I think I can break this down into a few concrete sections: knowing yourself, knowing what you want, how to communicate this online, and how to be safe about it. I’m also going to add a bit about consent at the end, because I find myself having to teach people about it sometimes; given how even I’ve learned more about proper consent recently, I’m sure you or others may find it useful and empowering as well.
I’m not sure if I have advice on how to psych yourself up for it. But I’m hoping that my advice can help you be more confident by making the process of hooking up online more transparent. This advice only really applies to meeting people online for sex.
Know yourself
By this, I mean you should know your body and what your limits are. This section mostly applies to bottoms, since it’s more complicated than topping.
If I see personal ads online for virgin bottoms, I’m usually very hesitant or not interested, since I don’t know how much they actually know about being prepared as a bottom. Do they know how to prepare? Or that they’re supposed to? Do they know their limits? Do they know how to properly clean themselves? Early on, I was fine with teaching my potential hookups these things because I wanted to fuck; I lost patience for it later. It’s still hilarious to see ads like, “Looking for BBC to ravage my virgin ass.” Like, do they have any idea what they’re in for?
Knowing what you’re physically capable of doing should give you a degree of confidence when it comes to the down to the actual hookup. Learn to warm up, if you need to. Different things work for different people, so find what works for you. Some like to stretch with plugs; I find that pumping my fingers in and out rapidly do a better job at stimulating my nerves to signal my anus to start relaxing a bit. Buy a dildo, and get used to it; if you don’t have one, I’d suggest one that is average penis size or less (5.5 inches or below.) Find a lube that works for you; If you don’t know much about water-based vs silicone vs oil or about various brands and stuff, start with a water-based lube. Astroglide Gel is a decent cheap option, and is my go-to actually. Know how thick you can comfortably handle. Know how deep you can comfortably go. It’s not universally a good idea to just wing it with such things on the fly unless you’re already experienced.
A lot of that seems like common sense. But if any of it is new to you, you should look into it more, as it will go a long way in bolstering your confidence.
Know What You Want
By this, I mean two things: know what kind of encounter you want to have, and know what kind of partner you want. It’s important because you’ll need to be able to communicate this effectively.
Knowing what kind of encounter you want to have goes beyond just what kind of sex you’re looking for. Knowing that is important, too, though. Do you want to bottom, or top, or both in the same session? Do you want to give oral, or just receive it, or 69, or skip it altogether? Are you ok with nipple play, or eating ass, or dirty talk? Knowing what you want to do and what you don’t want to do can help things proceed smoothly in the moment. Even with just common sex acts taken into consideration, the course that sex can take has a lot of permutations. If you’re nervous about hooking up, limiting your initial encounters to things you’re prepared for can make things easier by removing a lot of uncertainty.
There’s more to an encounter besides the kind of sex you want to have though. There are some basic things like where and when, travel, materials and supplies; logistics determine what is physically on the table, and people who don’t fit the plans can be dropped for consideration. For example, if you can’t host and you’re looking to go to their place, but they can’t host either, it’s pointless to try to get to know them or send face photos.
At the heart of what I wanted to talk about in this section, there’s the leadup to the sex and the time period after the sex. Think about it: what are you going to do when you finally meet? How are you going to act? Do you want a cum-n-go situation without a bunch of talking? Or do you want to converse for a while first to feel out the vibe? I often like talking about my geeky interests to break the ice. It’s also a good opportunity to set some expectations and boundaries if you haven’t done so yet. Do you like to kiss, or is that uncomfortable for you? Do you want to have an intimate cuddle, or are you just meeting for the sex?
This leads into the part a lot of people have trouble with. Who do you want to have sex with? How do you effectively communicate this to find a partner you’re comfortable with? A little honesty will go a long way here. And yeah, you’re gonna need some pics.
Communication and Honesty
When I say honesty, I mean about yourself and your situation. You definitely want to be upfront with your body type, even if you’re not comfortable with it: list your height, weight, dick size, ethnicity, pronouns, i.e. your stats. It’s also ok, or even a good idea, to admit your inexperience or nervousness. It’s ok to state up front that you’re looking for a very vanilla encounter. It’s ok to state that you’re really shy. You don’t need to worry so much about being good at sex or afraid that your partner will not enjoy themselves. Being a bit honest like this will ease some of the pressure you might be feeling. It also helps filter out people who aren’t interested in your body type or are too impatient to have consideration for your situation.
It’s ok to have a preference in what kind of partner you’re looking for, even if your criteria seems kind of narrow. This is especially true if you’re looking for a first time or you’re really nervous about it. Maybe you want someone around your age or younger, so you can relate to them more. Maybe you want someone just as inexperienced or shy for some empathy right off the bat. Maybe you specifically want a kind, experienced, older daddy to take the lead and guide you. It’s ok to write these things out, but I would try to keep it as concise as you can.
In my early days, I stated I was a curious student looking for other curious students looking to experiment. I wanted someone who was close to my height and weight, who was between the ages of 18 and 22, who was not really hairy, who was not a jock or very athletic and toned, and who had an average or below dick. For my first time, I shared that I was a virgin, and that I actually was looking to top. I didn’t share that my real interest was in bottoming; but that seemed more complicated than topping, and I wasn’t used to it yet. I gave priority to students at my school, to geeks, and to quick cummers, but made it clear that if they were not any of these things, that it was not a dealbreaker.
As far as your photos go, I understand the paranoia surrounding privacy. I think it’s a healthy attitude to maintain on the web. You should have a variety of photos available, but the ones you share publicly don’t need to have your face if you don’t want them to. Take a bunch of photos and then choose which ones you’re ok with posting. You’ll need at least one public photo to get more replies, regardless of what platform you’re using. But try to have at least one accurate photo of your body, your dick, your butt, and your face ready to share while you’re talking online.
I really liked Craigslist in the early days because it gave me the space to describe what I was looking for. Doublelist is the replacement, but it’s not as good since it has less powerful filtering. I’m not a fan of some apps like Grindr, because it has a pretty small character limit. Also, most profile pics there tend to be face-first oriented; I like the idea of getting fucked more than I am attracted to men’s looks, so it’s not my preferred app. But find whatever works for you.
Safety
Use anonymous accounts to communicate, or accounts you don’t mind abandoning if it were to come to it. Ignore replies that ignore specific requirements and deal breakers in your ad, profile, or post; unless they acknowledge they read my writing before asking about it, I don’t have time for people who don’t respect me enough to read about my preferences. Think hard before you give out your real phone number; I never do, preferring instead to use Kik, or whatever built-in communication the platform I’m using has (emails, chatbox, inbox, whatever.) If possible, tell a friend where you’re going and when, and then let your sex partner know that someone knows where you are. Keep in touch with your friend before and after; I check in with them during as well, when a preset timer for 20 minutes goes off. Don’t leave your phone, wallet, and keys unattended. Get full-panel STD testing regularly; if you’re active, it’s recommended to do so every 3 months, but with how slutty I’ve been recently, I’m considering doing it sooner or as needed. Get on PrEP if you can; it’s a daily medication that hardens your cells against HIV. Insist on safe sex practices and condoms; I have a ton on hand in case they don’t, so they have no excuse. Remember, using spit for lube, eating out an ass, or giving a blowjob unprotected are not safe sex practices. If you ignore that, you do so at your own risk.
Consent
I was not explicitly taught consent growing up. I mean, I sort of got it, but I didn’t really get it. Like, if we both agree to have sex and then we do, that’s consent, right? That’s correct, but it’s also very incomplete. It wasn’t until I met my current lover that I realized how far it goes. He was respecting boundaries I didn’t even know I was supposed to have. I have found myself reminding or teaching some of my hookups about consent, and it’s made my interactions noticeably smoother.
To be clear, you should understand that consent can be revoked at any time, for any reason. Full stop. You or your partner has the right to bail at any time, including during your communication online, after your initial meeting, or even partway through the act of sex, even if the reason is “I don’t feel like it anymore.” This power is available to you at any time, and if it helps, you can say so to your partner beforehand. I’ve told it to people who wanted to fuck me but were too nervous, and it helped put them at ease. I have also told it to people who I merely discussed logistics with rather than conversing in any meaningful way, to put my own self at ease.
Don’t be afraid to ask for consent for things during sex, as well. It doesn’t kill the mood or the flow or whatever. If you don’t know how to initiate sex, it’s fine to ask, “Can I kiss you?” While you’re sucking their dick, it’s ok to pause for literally two seconds to ask, “Can I suck your balls?” If they do something without asking first and it makes you uncomfortable, it’s ok to take a second to say, “I’m not really into that. Can you not?” I usually say that if they start aggressively playing with my nipples.
In Conclusion
That sums up my response to your question. Some people might think that this level of consideration is overkill, but I know what it’s like to be super nervous about hooking up; I’ve only been sexually active again since like, November 2021. Before that, I hadn’t been naked in front of another human for some years due to stress from work, anxiety, and depression. So I get where people might be coming from. Look at me now! I’m basically a huge slut. But only when I feel like it.
If you also have anxiety and depression or something and it’s really messing with your sex drive or ability to meet people online for sex, I actually suggest getting that treated first. I have sex when I’m happy. I don’t have sex to make myself happy, even though it does fulfill me in a lot of ways.
If you have questions about some part of the process that was glossed over or not covered, feel free to DM me or send a message to my inbox. I probably won't be compelled to do a full write-up like this though, lol.
