Scarleteen

Hello, and thank you to whoever reads this. I'm writing to ask for help with anal.
I'm a twenty-something transwoman. My girlfriend is also a transwoman. Neither of us have gotten or wish for bottom surgery. I'm a strict bottom- I have never wanted to put my penis inside anything.
I'm somewhat scared of anal. The idea of thing going inside my butt in that way makes me feel a bit queasy- ive never known why. The few times I've attempted anal I bleed, and I'm too tight for anyone to fit in. My gf is... very well endowed and it scares me for the future. I've tried just using my fingers as a way to get myself used to it but it still always makes me feel queasy. My questions are, how can I help myself get over this fear? How can I become able to take it without bleeding and whike being able to fit it inside me?
Thank you very much for your time.

Welcome to the boards, wingsof-feather. Good to see you here

I think being anxious about insertive sex is completely understandable. After all, that involves someone else's body parts and/or items making contact and interlocking with our own body parts. Not to mention that usually, the person whose body is being entered tends to be more physically vulnerable too, not just from STIs and pregnancy (in some cases) but also from abrasions and other physical pain. And for a lot of people, literally inviting someone into our bodies is a form of emotional vulnerability and intimacy. So yeah, it's not weird at all that you're scared and worried. That said, sex shouldn't be painful for everyone involved. It is concerning to hear that you've bled from anal sex--were you able to get this checked to a medical professional?

It'd be great if you could let us know how you've been doing anal sex, solo (masturbation) and partnered. Some questions to consider:
- Were lube and condoms involved all throughout, since the anal doesn't lubricate itself?
- Did the two of you take it slow, including "warming up" with other activities that get you aroused and relaxed? This can be kissing/making out, manual sex, oral sex (in your case, since you prefer not to insert your penis into anything, analingus or "rim job"), and more, among other things.
- Did your partner take her time with inserting her penis? Was she gentle?
- This one's less physical and more psychological: just to be sure, is anal sex something you've consistently wanted throughout these moments, doing only for yourself, and feel ready and enthusiastically excited for? If you've had any doubts about it, it might be helpful to address said doubts.

I also believe these articles can answer some of your questions in more detail:
- Why does anal sex hurt?
- Let's Get Metaphysical: The Etiquette of Entry
- Pelvis Problems: Anodyspareunia (aka: Pain with Butt Stuff)