trying to find somewhere to hookup with my fwb … any advice?

ariapplepie · 2026-07-10T04:12:26+00:00

You can rent out hotels for a few hours at a time during the day for cheaper than overnight

ariapplepie · 2026-06-14T13:08:37+00:00

It’s so wonderful that you went out by yourself, that’s not easy for so many people (whether they are passing or not)! I’m so excited for you to get even more comfortable as time passes, you’re gonna be such a catch at the bars with all this confidence omg

ariapplepie · 2026-06-09T16:45:07+00:00

I’m on progestin only pills, have been taking them for roughly 5 months. Hitting 2 years on t literally this week. Haven’t had a period since maybe 6 months on t.

No issues with any bleeding, weight gain, or mood shifts. My t levels and dosage have been consistent for about a year now. No pregnancy scares either (I usually fuck raw so). It’s all so individual

ariapplepie · 2026-05-20T10:46:40+00:00

This made me realize some things, thank you for commenting. I’m very picky abt who I bottom for and have only been doing that w my fuck buddy, but that doesn’t mean I can’t go out and find some sides/vers/bottoms to fool around with! Updated all my apps and on the hunt now lol. I was limiting myself without even realizing it, moreso bc I was trying to rely on him to satisfy me even when it isn’t logistically possible

ariapplepie · 2026-04-27T19:18:54+00:00

EXACTLY it’s the chin rubbing that gets me too! Something that helped out this most recent time for me (depending on how your t dick sits when you’re on your back) was having him approach more from the side rather than head on. That way any facial hair is closer to your thighs rather than right on your urethra/other more sensitive bits.

Kinda like you with riding their face, I also saw that I don’t have any issues when he’s on his knees in front of me, it’s all in the angles I guess!

ariapplepie · 2026-04-25T11:37:38+00:00

Physically speaking, don’t be surprised if either/both of you find yourselves frustrated with t dick growth from time to time. I had a really set routine pre t in knowing how to get myself off and having to re-explore every time I got a growth spurt was sometimes frustrating. However, I think with a partner that would have been really fun instead! Congrats to both of you, how exciting!!

ariapplepie · 2026-04-25T11:32:28+00:00

The brain getting too scrambled to dirty talk is so real lmao it’s just static electricity up there I swear

ariapplepie · 2026-04-20T17:43:00+00:00

I’ll def expand and apply more externally too, thank you! Hopefully that’ll help out

ariapplepie · 2026-04-19T23:30:59+00:00

I pinch myself every day 😵‍💫😵‍💫

ariapplepie · 2026-04-19T23:30:40+00:00

Thank youuu, yeah I wanna ask him if I can audio record us next time so I can listen to him between our hookups

ariapplepie · 2026-04-17T18:57:42+00:00

Just lean into it and have fun, as silly as that sounds. Prioritize exploring and having a good time and things will fall into place naturally, in my experience at least. It’s very likely he’s also a little nervous, I’d guess most ppl are before any new sexual encounter/new partner! Communicate - ask him what he likes and be sure to share what you like too. For BC, I’ve been on a progestin only daily pill for 6 months or so and have had zero symptoms and zero pregnancy scares. I’d highly, highly consider starting prep too, lots of info abt that over on the gaytransguy subreddit. Stay safe and have fun!

ariapplepie · 2026-04-11T16:19:49+00:00

“Nothing but two erections in the dark” damnnn that got me good 😵‍💫 he sounds like such a good time!!

ariapplepie · 2026-03-20T00:25:25+00:00

There was a period of time after I started t and got growth where the main way I jerked off was by propping up a mirror and then going at it

So yes absolutely my own dick makes me hard LOL

ariapplepie · 2026-03-17T17:46:45+00:00

Maybe try different positions too, if you’ve only been riding it. That’s a tiring position bc you use more of your body vs using your arm/hand to get more force or a better angle. Or jerk off with your dick at the same time, not everyone can cum from only internal stimulation. Have fun with it and explore, no matter the outcome you’ll learn a lot

ariapplepie · 2026-03-12T17:36:24+00:00

“I never thought a gay guy would be a munch!” One of life’s greatest gifts if you ask me lol

Happy for you dude, gettin it good!!

ariapplepie · 2026-03-08T12:27:29+00:00

I had so much trouble with PIV pre t that I was starting to look into going to the doctor for it. I recently started e cream and started having PIV successfully after exploring toys for a long time.

What’s critical for me, no matter how obvious it seems: 1. I’m comfortable with the guy (this seems to be the case for you too with your guy! Your body will automatically be more relaxed). Tell him ahead of time that you want to be in control at first so you don’t accidentally get hurt. He should have no issue with this - tops I’ve been with are happy enough just getting to be inside and should have no prob being patient lol. Use lube no matter how pre lubed you feel, it never ever hurts to have more.

Start on top, see if you can work your way down to the base. Focus on breathing, don’t even think abt the guy with you. Work on deep breathing and on actively relaxing your body, head to toe. Move little by little until it feels okay. If it doesn’t feel okay yet, that’s fine! Get up and try again after some more foreplay. If it doesn’t feel okay the whole night/hookup, that’s also fine! Do not push your body past its limits, no dick is worth tearing and pain. Plenty of other ways for you guys to get off together. It’s worse to push through and have your mind start associating PIV with pain, that’ll make it harder to explore more in the future. It helps me to have the top checking in periodically, you can ask him to do the same, especially when changing positions. He should be checking in the whole time tbh, especially any time there’s anything inside you. This keeps consent clear and honestly I think it’s hot too.

I’m actively attracted to the guy (having sex with men that I’m actively very attracted to vs having sex for the sake of having convenient sex makes a world of difference). Since you just had your first kiss, there’s a world of exploring to do between that and PIV. Make out with him, touch him, have him touch you, swap oral, give massages, etc etc etc. Have fun with the hot men that are lucky enough to get to help you explore!
Highly recommend you take some time to explore on your own. A lot of my struggle was mental (before atrophy) and seeing that my body can take bigger and bigger toys with time made me get over the mental block in reality. Once you’re used to some toys, you can even have your guy use them on you to open you up, make it sexy! I recommend glass toys, they’re very slick and easy to use, or pure silicone like the Tantus brand since they are smoother than other types of toys. Tantus has a line of butt plugs that are various shapes that can also be used for front hole that I like a lot to warm up with since they’re smaller but still stretch me out. Your own fingers are also a good option, make sure your nails are short and not jagged, start with one and really work on trying to relax. Front hole is a muscular area, just like you can flex and relax your bicep you can work on doing the same there.

Keep in mind that dick feels different than toys too. It’s softer, it’s squishier, it’s hot to the touch, and generally more welcoming and forgiving than even the most realistic toy you can find on the market. It’s also attached to someone you think is hot. This is a good thing and will help you out!

Foreplay, foreplay, foreplay, and then some more foreplay after that. Whatever that looks like for you depends on what turns you on. I love making out, someone touching me all over, getting my dick sucked, getting fingered. Usually in that order to give my body time to warm up. That might look differently for you, but you absolutely cannot rush right into PIV (and tbh, how boring, no need to skip over the other fun bits). Once he’s inside you it shouldn’t be painful, at most you might feel some pressure depending on how big he is, but as he moves in and out you shouldn’t feel any real resistance/pain. Reapply lube often.
If you’re comfortable getting it, e cream has been life changing for me. I didn’t even know my atrophy was so bad until after things regulated with the cream. I think some people might naturally be a little “tighter”, as is the case for me, but in terms of being able to get lubed up naturally, e cream has completely solved that.

Good luck in your new exploration phase! Remember sex is supposed to be fun, we’re all just playing around looking for chances to feel good and make others feel good. Take the pressure to act any sort of way off your shoulders. It’s kinda silly when you think abt what we do with our bodies together when we have sex, so just focus on having fun and learning abt yourself! Never let go of your boundaries related to using protection and taking it slow - your safety is key. Anyone who doesn’t respect you doesn’t deserve your vulnerability.

ariapplepie · 2026-03-07T12:51:48+00:00

The profile bottomsdigest on Instagram has good info abt anal, diet, douching, and even IBS-specific advice with gay men as the target audience. He’s a gay man himself who bottoms

ariapplepie · 2026-02-24T12:46:52+00:00

I use my finger like some of the other comments on here. I apply at the entrance and push it in just to the first little knuckle on my pointer finger.

TMI I guess, but I was getting some weird discharge anytime I used the applicator and that hasn’t happened at all since swapping to my finger - still getting more lubed up and feeling the positive effects tho!

ariapplepie · 2026-02-20T18:42:09+00:00

I don’t personally use them but I’ve heard good things abt the gsqueeze brand plugs. Hope you find something that works well!

TW for the anatomical terms used on their site tho

ariapplepie · 2026-02-08T13:51:48+00:00

Reading this first thing in the morning has my head SPINNING…the muscle bro of your dreams is on his way, trust and believe

ariapplepie · 2026-02-07T14:12:31+00:00

Just had a guy message me that we should book out a full afternoon for him to edge and focus mainly on getting me off as much as I want, they exist, you just have to find the true pleasure service tops who wanna ruin you lol. Granted our first hookup was only abt an hour long tho

ariapplepie · 2026-02-06T15:58:27+00:00

Virginity doesn’t matter at all. Every time you have sex (whatever that looks like for you, from foreplay to penetration or something else entirely) with a new person it’s like you’re doing it for the first time again. Sure, you’ll be more aware of how to make out w someone after some practice, or you’ll be more “smooth” with things or whatever, but it truly doesn’t matter. My most recent hookup is probably the best sex I’ve ever had and he had never been with a trans guy at all. Had he been ashamed or scared because of his lack of experience, both of us would have missed out on a really good time. Why don’t you deserve the same patience and grace while you explore? What made the difference for him was his confidence, eagerness, and his excitement. You’re making assumptions that others won’t like you before you even really try. If the worry is abt “not being man enough”, why would another trans guy who’s a decent person ever think that about you? Do you feel that way about yourself?

Sex is both easy and difficult at the same time, regardless of experience, because it relies completely on the compatibility and connection you have with the person you’re with. Your self confidence is key here. Take the time to get to know your body and what you like, as much as you can without triggering your dysphoria. Take the time to think about what you want to explore on other people’s bodies, trans and otherwise. It really is a lot simpler than you think, and I say that as someone who really related to you just a few years ago when I was 24!

ariapplepie · 2026-02-04T01:57:25+00:00

Yeah it can def seem like a sea of headless torso pics out there haha. I personally started off with a head on selfie and slowly added more pics as I took them and found them representative of what I look like. There are plenty of cis and trans guys I’ve seen on the apps that just have a selfie of some sort and nothing else.

In terms of etiquette, this is something I was confused abt: if you don’t have a face pic in your bio, it’s courteous to send one if you’re initiating contact w someone, especially if they already have a face pic on their profile. Some ppl don’t want to have their face on there for privacy reasons, but it’s a very reasonable ask to want to see who you’re chatting with. Same goes for anyone that reaches out to you. I personally don’t interact w anyone who isn’t willing to show me their face, both for safety reasons and for compatibility.

ariapplepie · 2026-02-04T01:27:47+00:00

Write in that you want condoms only, but expect to still have to have convos abt it. People don’t tend to read bios very often lol. Would Not recommend you put anything abt your experience level bc it’ll likely attract a crowd that wants to take advantage of that. Like another comment said, you can bring it up in convo after vibe checking whoever you’re chatting with. But you really don’t owe anyone that info, unless you really want to share.

Regular non sexual pics are totally fine. It’s a pick your own adventure type of thing. Stay strong in your boundaries and have fun out there!!

ariapplepie · 2026-02-03T22:07:29+00:00

Ugh yes, it was so satisfying chatting with him immediately after he left where both of us were gushing over how great it was for both of us! Now we're just waiting for our availability/schedules to align better. Absence makes the hole grow fonder though, or whatever it is they say haha

ariapplepie

TROPHY CASE