Sideways Anal (also called the anal side entry position) is the one almost every woman who loves anal says is her favorite. It’s gentle, relaxing, and gives you total control while still feeling incredibly full and pleasurable.
No awkward angles. No rushing. Just slow, deep pleasure that feels natural and exciting.
“We had talked about anal for months, but I was always scared it would hurt. One lazy Sunday afternoon my husband suggested we try it sideways while spooning. He went super slow and used tons of lube. The angle felt so natural that I actually relaxed and started pushing back against him. I had my first real anal orgasm that day — gentle waves that built and built until I was shaking. It didn’t hurt at all. Now it’s one of our go-to positions when we want something extra naughty but still super intimate.”
— Sarah, 34
What Is Sideways Anal?
You both lie on your sides in a spooning position. The receiving partner bends their top leg toward their chest while the giving partner enters from behind at a gentle, natural angle.
Why it works so well:
- Maximum comfort and control
- Zero pressure on the lower back
- Easy access for clitoral stimulation
- Very intimate with lots of skin contact
- Gentle enough for beginners, deep enough for experienced couples
How to Do Sideways Anal (Step-by-Step)
- Lie on your side with a pillow under your head.
- Bend your top leg and pull your knee toward your chest.
- Your partner lies behind you and matches your body curve.
- Use plenty of thick anal lube.
- Start with fingers or a small plug to relax the muscles.
- When ready, your partner slides in just the tip and pauses. You control how much more you take by rocking your hips back.
- Once fully inside, stay still for a moment and enjoy the feeling before starting slow, gentle thrusts.
Hot Hints & Pro Tips
- Run your fingers lightly down her back — it keeps her relaxed and connected.
- Place a small pillow between your knees for better hip alignment.
- Have your partner press gently on your lower belly (just above the pubic bone) — many women say this creates an intense “full” feeling.
- Keep a small bullet vibrator on her clit the whole time for blended orgasms.
- Try it in front of a mirror — watching yourselves from the side is incredibly erotic.
Pro Tips:
- Always start with 10–15 minutes of foreplay and lots of lube.
- Communicate constantly (“more”, “slower”, “right there”).
- Go slow the first few minutes — the best orgasms happen when you’re relaxed.
- Whisper something filthy in her ear (“You feel so good”) — it makes everything hotter.
Common Mistakes to Avoid
- Skipping the warm-up or lube (this is the #1 reason anal hurts)
- Thrusting too deep too fast — let her set the pace with her hips
- Tensing up — deep breathing is your best friend
- Forgetting aftercare — a gentle cuddle and some water afterward makes the whole experience better
Ready to try it tonight?
Grab the lube, set the mood, and give Sideways Anal a gentle go. You might be surprised how good it feels.
