"Will it hurt?” This is one of the most common concerns I hear in my clinic, and it’s completely valid. Anal sex or anal play can feel intimidating, especially for first-timers.
Unlike the vagina, the anus doesn’t self-lubricate and is surrounded by muscles that instinctively tighten when we feel nervous or unprepared. But here’s what I always tell my clients: when emotional connection comes first, the body follows.
The First Step: Emotional Safety and Communication
Before anything physical happens, have an open conversation. Talk about anal sex, what are your concerns, what will make you feel safe. Go beyond the logistics and ask:
- What are your concerns?
- What would help you feel safe or relaxed
- What are you curious about?
Second Step: Don't Skip the Warm-Up
Jumping straight to the anus is a recipe for discomfort. Begin with full-body arousal:
- Deep kissing
- Sensual massage
- Gentle touch
- Meaningful eye contact
Arousal is both mental and physical. As you build it, the pelvic floor begins to relax—making anal play feel more natural, pleasurable, and far less daunting.
Third Step: External Anal Stimulation: Start Slow
When you're ready to explore the anal area, start externally:
- Use well-lubed fingers to trace around the anus.
- Try gentle tongue play or a soft vibrator.
- Stimulate surrounding erogenous zones to increase overall pleasure.
This part of the body is rich with nerve endings. For women, it can enhance the sensation of vaginal or clitoral stimulation. For men, it can heighten pleasure through indirect or direct prostate stimulation.
Last Step - Penetration: Lube, Pace, and Communication
If everything feels good so far, you can slowly explore penetration:
- Use lots of lube—always choose a high-quality water- or silicone-based option.
- Start with a clean, trimmed finger or a small anal plug.
- Let the receiving partner guide the pace.

Pause regularly to check in:
- “How does this feel?”
- “Would you like more or less pressure?”
- “Want to stop for a moment?”
These questions are not just courteous—they’re caring, and they build trust.
What If It Doesn’t Feel Good?
That’s perfectly okay. Your body always gives you honest feedback, and learning to listen to it without judgment is key. Not every new sensation will feel amazing right away—and that’s part of exploring intimacy with self-awareness and mutual care.
Real Anal Play Pleasure Comes from Connection
Anal sex doesn’t have to be goal-oriented. In fact, some of the most erotic, intimate moments come from non-penetrative touch, shared vulnerability, and mutual respect. Ultimately, anal play—like all sexual experiences—should center around comfort, communication, consent, and pleasure without pressure.
When you eventually move to the anal region, keep things external at first. Use your fingers, lips, or even a vibrator around the area to tease and awaken those sensitive nerve endings. The anus is rich in sensation for both women and men. Women may enjoy the added fullness when paired with clitoral or vaginal stimulation, while men may find it pleasurable through indirect or direct prostate touch. If it feels good, continue slowly.
Use lots of lube. Maybe introduce a finger or a small plug. Let the receiving partner guide the pace. And always check in, “How’s this feel?”, “Want more or less pressure?”, “Would you like to stop for a bit?” These are loving, respectful questions.
✨ Key Takeaways:
Pleasure isn’t about performance, it’s about connection. And sometimes, the most erotic moments happen not during penetration, but in the way you show care for each other’s body and boundaries. That, to me, is real intimacy. See what is essential below.
- Emotional connection and communication are essential.
- Always prioritize arousal and relaxation.
- Start slow and externally.
- Use plenty of lube.
- Check in often.
- It’s okay to stop at any point.
And if it doesn't feel good? That’s okay. The body gives honest feedback. Tuning into that feedback, without judgment, is part of building trust and intimacy.
Written by Dr. Angela Tan
Clinical Sexologist & Relationship Coach
Dr. Angela Tan is a certified clinical sexologist helping individuals and couples build deeper intimacy through trust, communication, and holistic sexual wellness. Her practice focuses on empowering people to embrace their pleasure confidently and without shame.