Woman preparing for painless first time anal sex with dilation tips

 

I wonder if many Hong Kong girls often hear their boyfriends say: “How about we try anal?”

Or something like “Let’s clean it up and try putting it in the back.”

Originally, I never thought about trying anal play. I had no idea what anal sex felt like — I just assumed it would hurt a lot, so I always refused. And honestly, not many girls do anal, right?

But my boyfriend kept gently suggesting it, and recently I finally told him we could try.

He was absolutely thrilled 😂😂

Is First Time Anal Sex Comfortable?

 

After trying it once, I’d say anal sex didn’t hurt, but there was a strong foreign-body sensation. Still, it felt quite pleasurable. Have you tried anal? Was your first anal comfortable?

Below are essential steps for a woman’s first time anal sex: proper cleaning, anal training, lubrication, and how to maximize pleasure during anal penetration.

What to prepare before anal intercourse? Here are my personal tips for safe anal preparation and beginner anal play.

Related Reading: 6 Blowjob ultimate guide to Drive Him crazy

 

First Time Anal Tip 1: Prepare Proper Anal Cleaning Tools

The anus is where poop comes out — everyone knows it needs thorough cleaning before anal intercourse.

 

In the bathroom, I spread my legs while my boyfriend brought out the essential anal cleaning tool: an enema bulb or douche pump. Any reliable anal douche works — just fill it with water, insert, and squeeze.

 

He used warm water so it wasn’t cold — this makes first anal much more comfortable.

 

I thought the water would leak out immediately, but it doesn’t at first. You need several rinses before clear water flows out. Mine was transparent — probably because I’d pooped that morning and eat lots of fruit.

 

The feeling during first-time anal cleaning was strange: normally only solid things come out, but now it felt like peeing from my anus with a warm, slightly burning sensation — totally new!

 

Summary: Always clean thoroughly before anal sex. Use warm water. The water usually comes out clean (though it varies by person).

 

Step 1: Anal cleaning with enema douche bulb for safe first time anal sex

 

First Time Anal Tip 2: Use an Anal Plug to Relax and Train

After cleaning, we started the anal training phase.

(Tip: Lay a towel on the bed for peace of mind.)

 

We began with a basic anal plug — the kind with a flared base. Even a beginner-friendly one works perfectly.

 

Use plenty of lube or anal relaxing cream/spray to help the sphincter relax. At first, there was no pain — just a noticeable foreign sensation.

 

The anus has many nerve endings (source: Wikipedia), so feeling some pleasure during anal training is completely normal.

 

The goal: Let your sphincter relax and get used to having something inside.

 

Related Reading: 7 Benefits of Male Masturbation

 

Step 2: Anal training with beginner butt plug for relaxation before anal penetration

 

Anal Tip 3: Use Fingers Before the Penis

After preparation, start with the smallest finger. My first anal involved fingers only at first — I allowed just one.

 

He inserted very slowly, constantly asking if it hurt.

 

Fingers felt thinner than the plug, so I let him try two. The foreign sensation was intense, but no pain.

 

When he gently moved them, one spot felt surprisingly good — maybe that’s the famous anal pleasure spot?

 

Related Reading: Male Squirting Guide

 

Step 2.2: Using fingers for gentle anal preparation during first anal experience

 

“The #1 Rule for First Time Anal: Use Plenty of Lube!”

 

Worried about pain or tearing? 😱

With enough lubrication and relaxation products, pain can be minimized or eliminated.

 

Click below for recommended anal-safe products!

Perfect For

Fear of Pain Extra Wetness First Time Nerves Hygiene Concern 

 

 

 

Why Choose sFun HK?

🚀 Free Shipping: Over $200 anywhere in Hong Kong! Same-day delivery available.
🔒 Total Privacy: 100% discreet packaging.
🌟 Huge Selection: Over 10,000 authentic products from Europe, US & Japan
 😭 Crazy Deals: Monthly flash sales & mystery bags!
🎁 Member Perks: New members get $10 credit, spend $1000 get at least $88 credit!

Join Now 

Anal Tip 4: Apply Lots of Lube Before Penetration

I thought we’d stop at fingering, but my boyfriend playfully said he wanted to try his penis since I was already relaxed…

 

Two fingers and a penis are very different in size! He used silicone-based anal lube — Pjur med PREMIUM is long-lasting and highly recommended.

 

Apply lube on the penis, not just the anus. If it feels sticky or painful during insertion, add more — never force it.

 

Step 3: Applying silicone lubricant for comfortable anal sex

 

 

Anal Tip 5: My Actual First Anal Penetration — Go Slow!

 

Lie on your stomach with a pillow under your hips to raise your butt — this position makes entry easier for first time anal sex.

 

I expected him to go slowly like with fingers… but he suddenly thrust all the way in! My anus felt completely full. Thanks to lots of lube and prior stretching, it slid in smoothly — but I was shocked and yelped!

 

Advice: Insert the penis very gradually. Anal requires patience and technique to avoid injury.

 

Step 4: Slow anal penetration position for beginner anal sex

Anal Tip 6: The Sensation is Intense Heat…

 

Initial entry wasn’t painful — just a huge full, warm feeling. As he moved, it became hotter and more intense, like a burning pressure.

 

After a few minutes, my whole body went limp. The pleasure was different from vaginal — deep, overwhelming, and unique.

 

Next time, with more experience and better prep, I’ll be able to focus purely on the anal orgasm sensation.

 

Related Reading: Why Men Love Grabbing Breasts

 

Intense warming sensation during first time anal intercourse compared to flaming heat

 

Anal Tip 7: Stay Relaxed for Maximum Pleasure

 

Apart from the sudden full thrust, I stayed relaxed throughout — helped by my boyfriend being gentle and caring.

 

Mental relaxation leads to physical relaxation, making anal penetration easier and pleasure stronger.

 

Anal play is slow and gentle. Communicate constantly — ask if it feels good, if you can go deeper. That’s the key to an amazing first anal experience.

 

Hope my honest first time anal story helps you enjoy safe, pleasurable anal intercourse!

Funny cartoon reaction to surprising first anal experience

First Time Anal Sex FAQ (2025 Updated)

1. Does anal sex hurt? What preparation prevents pain?

Pain usually comes from insufficient preparation. Use thorough cleaning, anal training, relaxing products, and lots of silicone-based lube. Go very slowly. Individual tolerance varies — start solo if nervous.

2. Does liking anal make someone gay?

No. Sexual orientation isn’t defined by one act. Many straight men and women enjoy anal pleasure (especially prostate stimulation in men). Enjoying anal doesn’t change your orientation.

3. What does anal sex feel like?

A unique deep fullness, intense warmth, and different kind of orgasm compared to vaginal sex. Many describe it as overwhelming and highly pleasurable once relaxed.

4. What counts as anal intercourse?

Any object (finger, toy, penis) entering the anus qualifies as anal penetration.

5. How to make first time anal painless?

Clean thoroughly, train with plugs/fingers, use relaxing spray and thick lube, stay relaxed, communicate, and go extremely slow.

6. Can anal sex cause injury?

Yes, if rushed or without enough lube — possible tears or discomfort. Always prioritize safety and stop if painful.

7. Best position for first anal?

Doggy with hips raised (pillow under stomach) or spooning — both allow control and easier relaxation.

8. How long should anal preparation take?

30–60 minutes of cleaning, training, and foreplay is ideal for beginners.

sFun HK has everything you need for safe anal play — check our anal products section!

Various anal toys and butt plugs for backyard play and anal training in Hong Kong

 

Men's sex toys and masturbation devices in Hong Kong
Men's Toys
Women's vibrators and dildos sex toys in Hong Kong
Women's Toys
Men's libido enhancement supplements and products
Men's Libido Enhancement
Water-based and silicone personal lubricants for sex
Lubricants