First Time Anal Sex? 8 Things I Wish I Knew

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This guide is for anyone about to bottom for the first time (or top for a first-timer) and wants the honest, unfiltered version — not a sanitized one. It's a personal story plus eight practical lessons, for any gender or orientation.
⏱ 11 min read

Quick Answer

A good first anal experience comes down to a handful of things: go slow, use way more lubricant than feels necessary, communicate constantly, and don't expect it to feel amazing right away. Some pressure or an urge-to-poop sensation is normal and doesn't mean anything's wrong; sharp pain does. Work up gradually with fingers before anything bigger, skip poppers if you're relying on them to tolerate size or pain, and only explore anal play with a partner who's genuinely on board — never as a surprise.

My First Time Bottoming — and What It Taught Me

My first time having anal sex was hell. Thank God, not literally, but emotionally and mentally, I was wrecked. I'd topped (been the penetrating partner) for men, women, and nonbinary people plenty of times. The bottoms (receiving partners) I'd been with were pros. They made it look effortless. They were clean — I could have eaten a meal off their asses. (Guess what? I did!) They didn't tell me to slow down or use more lube. They just took it like champs. So I thought bottoming was easy. Boy, was I wrong.
I bottomed for the first time at 22 with a guy I was dating and trusted. During sex, I kept asking, "Am I shitting on you?" He kept saying "no" until he finally snapped, "So what if you are? Stop asking!"
Let me be clear: I did not enjoy that experience. It hurt, I felt gassy, and I got none of the euphoria I thought anal and prostate stimulation was supposed to bring. After that, I decided bottoming wasn't for me. And I was cool with it! Until my next partner. She loved anal with men and told me my approach was all wrong. With her guidance, I tried anal again, and then... oh. Sexual epiphany. Now I'm an anal queen who loves all things butt play. I'll put anything up my ass given half a chance — as long as it's designed for it and I've checked it out first (more on that below).

8 Things I Wish I Knew Before Anal Sex

But it took a while to get here. I wish someone had sat me down before my first time bottoming. So, without further ado, here are eight things I wish I knew. This advice is mainly for bottoms but includes tips for first-time tops too.

1. Is It Normal to Feel Like You're Pooping During Anal Sex?

I touched on this earlier, but honestly, the entire time he was inside me, I thought I was shitting. Makes sense, right? Before then, the only sensation in my rectum was pushing out poop, so my brain linked that feeling with defecating. Just know: you aren't actively bearing down! Over time, you learn to separate the "poop feeling" from sexual pleasure.

2. Why Do I Feel Like I Need to Pee During Anal Sex?

So many new sensations, huh? If you have a prostate, stimulating it pushes against your bladder, making you feel like you need to pee. If you have a penis and prostate, you might also get "milked," where semen leaks out — totally normal, and means they're hitting the spot. Even without a prostate, anal sex can still make you feel like peeing; again, it's from unexpected pressure on your bladder.

3. What Happens If You Poop During Anal Sex?

I don't want to harp on poop, but I get tons of poop-related questions about anal, so it needs addressing. If poop happens, it's not a disaster — not even a little bit, and it's probably just a tiny bit. I've done anal sex hundreds of times as both top and bottom. I've pooped and been pooped on more times than I can count. It's part of the deal, baby. If you play in the mud, expect to get a little dirty. If a partner shames you for not being "clean," they're the asshole, not you — and chances are, nothing's ever been in their ass, or they'd know "shit happens" and wouldn't be so rude.
If you want to reduce the odds (not eliminate them — nothing does that completely), an empty rectum helps: some people find that having a bowel movement an hour or two beforehand, and skipping a heavy meal right before play, cuts down on the chances. A gentle external rinse is plenty of prep for most people; you don't need anything more intense than that.

4. How Much Lube Do You Actually Need for Anal Sex?

Remember that SNL sketch with Christopher Walken wanting "more cowbell"? Yeah, but for anal, it's "MORE LUBE!" Use as much as you can. A lube applicator (lube shooter) is great for getting lube inside your rectum. If you don't have one, coat your finger in lube and slide it in, then put more lube directly on the toy or penis.
Here's the part that's easy to get backwards, so pay attention: match the lube to what you're using, not the other way around. If you're using a silicone toy, you need water-based lube — silicone-based lube will degrade a silicone toy's surface over time. Water-based dries out faster, so you'll be reapplying often (remember, the anus isn't self-lubricating). If you're using a penis with no toy involved, a thicker silicone-based lube is a fine option too, since it lasts longer and there's no toy material to worry about damaging. So the actual takeaway isn't "always use silicone lube" — it's water-based for silicone toys, and either type works fine for penetration without a toy.

5. How Do You Prepare Your Body for Anal Sex as a Beginner?

Don't try shoving a thick 8-inch dildo up there first thing — that's aggressive. Start small, like a pinky finger, then slowly work up to a middle finger, then two fingers, then a toy, and so on. Practice by yourself before trying with a partner. It's even better if a partner helps with fingers first.
Whatever toy you eventually use, make sure it's actually designed for anal insertion — that means a flared base, a handle, or some other feature that stops it from being pulled all the way in. Skip anything without that, no matter how tempting it looks. 

6. How Long Should Anal Sex Take the First Time?

Sometimes it takes me a full five minutes — a long time during sex — to take a penis or dildo. I get the tip in, then my partner pulls out. We add more lube. I breathe. Maybe we try fingers again. Then back to the penis. Pull out. Breathe. Repeat.
Heads up: some people — especially men who've never been penetrated — can get pushy. Tell them to hold up. Don't just shove in. Take your time. Be gentle. Check in with your partner. Only go all the way when they say they're ready.

7. Are Poppers Safe to Use During Anal Sex?

Poppers (alkyl nitrites), often sold as VHS head cleaner, are found in sex shops and even some grocery stores. Commonly used for anal, especially in gay male communities, you inhale poppers. They relax smooth muscles, including your anal sphincter, and give you a brief head rush some find pleasurable during sex.
Many people use poppers to take a larger toy or penis than they otherwise could. This is a bad idea. If you need poppers to take it, that's a sign you're going too fast, not a green light to keep going. Poppers mask pain along with relaxing the muscle, which raises the risk of anal tears (fissures) — you might not feel the damage happening until it's already done. That's also why you should never combine poppers with a numbing agent for anal play: you won't feel pain or tearing until it's too late.
One more thing that's genuinely important, not just a caution label: if you take Viagra or another erectile dysfunction medication, you cannot safely use poppers. Mayo Clinic's drug information on amyl nitrite notes that combining sildenafil (Viagra) with amyl nitrite can cause a dangerous drop in blood pressure, dizziness, fainting — and in some cases, death. This combination has killed people. It's not worth the risk, ever.

8. Does Anal Sex Actually Feel Good?

Hopefully I haven't scared you off. Regardless of your gender or orientation, anal sex feels incredible for a lot of people. The physical pleasure is top-notch, it leads to more intense orgasms for many, and the intimacy of having someone (or something) inside you can be profound.
One thing worth being direct about: actually doing anal play should always be something your partner opts into ahead of time, with a real conversation — not something you spring on them mid-hookup. That said, if you're looking for a Valentine's Day gift idea, a well-chosen anal toy (flared base, body-safe material, the works) makes a genuinely fun surprise present — just introduce it afterward as something to explore together if they're interested, not an expectation.

One More Thing: What About STIs?

I didn't want to bury this in the middle of the list, because it matters on its own: anal sex carries a real STI transmission risk, arguably a higher one than vaginal sex for some infections, since the rectal lining is thinner and tears more easily.
The basics haven't changed just because it's anal: CDC guidance on condoms and HIV prevention confirms latex condoms, used correctly and with a compatible lubricant, meaningfully reduce STI and HIV transmission risk during anal sex specifically — not just vaginal sex. Use a new condom for each partner and each session, avoid oil-based lubricants with latex (they weaken it), and don't go straight from anal to vaginal penetration without changing the condom or thoroughly cleaning up first, since that moves bacteria somewhere it doesn't belong.
For toys, it's the same logic: Planned Parenthood's guide to safer sex recommends condoms on shared toys (changed between partners or body parts) alongside regular STI testing, especially with new or multiple partners.
None of this has to kill the mood — it's a five-second habit, not a whole conversation, once it's part of your routine.

Frequently Asked Questions

Is it normal to feel like I need to poop during anal sex?

Yes, very common — the sensation comes from pressure in the rectum, and your brain associates that pressure with needing to defecate. It doesn't mean you're actually about to.

What if I actually poop during anal sex?

It happens, and it's not a big deal or a hygiene failure. If you want to lower the odds, an empty rectum and a light meal beforehand can help, but nothing eliminates the possibility completely.

What lube should I use for anal sex?

Use plenty either way. If a silicone toy is involved, use water-based lube — silicone-based lube can damage silicone toys over time. If it's just penetration with no toy, a thicker silicone-based lube is a fine option too, since it lasts longer.

Is it safe to use poppers during anal sex?

Poppers relax the anal sphincter but also mask pain, which increases the risk of tearing if they're used to push past a size or intensity you couldn't otherwise handle. They should never be combined with a numbing agent, and never combined with Viagra or similar erectile dysfunction medication — that combination can be fatal.

How do I know if a toy is safe for anal use?

Look for a flared base, a handle, or another design feature that prevents it from being pulled entirely inside. Skip anything — including household objects — that doesn't have one.

How long does it usually take to get comfortable with anal sex?

It varies a lot. Some sessions take just a few minutes of gradual adjustment; for others, working up to full penetration takes multiple attempts over multiple sessions. Neither is wrong.

Do I need to worry about STIs with anal sex?

Yes — anal sex carries a real STI transmission risk, and for some infections it's a higher risk than vaginal sex, since rectal tissue is thinner and tears more easily. Latex condoms with a compatible lubricant meaningfully reduce that risk; use a new one per partner and per session, and avoid oil-based lubricants, which weaken latex.

Is an anal toy a good Valentine's Day gift

It can be a fun, playful surprise — just pick one with a flared base and body-safe material, and introduce it as something to explore together if your partner's interested, rather than an expectation. Actually trying anal play is a separate conversation your partner should genuinely opt into.

Medical Disclaimer

This article is a personal account plus general educational information, not medical advice. If you experience persistent pain, bleeding, or other concerning symptoms, or have questions about medication interactions (including poppers and erectile dysfunction medication), consult a qualified healthcare professional.

References

●    Mayo Clinic — Amyl Nitrite (Inhalation Route): Description and Brand Names
●    CDC — Preventing HIV with Condoms
●    Planned Parenthood — How Do I Make Sex Safer?

About the Author

Lin writes candidly about sex, pleasure, and body positivity, drawing on their own firsthand experience exploring anal play — including the awkward, unglamorous parts most guides skip. This article is a personal account, not clinical advice from a health professional. This article was reviewed by BEISAR Editorial Team for accuracy. 
Last Updated: [2026-08-03]