Partner-Assisted Training
Here's an approach many couples find helpful: he can wear a strap-on with a smaller dildo to help train you before using his own anatomy. This offers several advantages:
Positions & Play
Best positions for comfort and pleasure, tips for your first time, and guidance for during the act.
Your First Time
The first time can be wonderful if you approach it right. Here's how to set yourself up for success.
Don't Rush
Pick a time when you have no pressure. Weekends or evenings when you're relaxed work best.
Communicate
Agree on a system: "slower," "stop," "more lube." You're in control at all times.
Get Aroused First
Foreplay, oral, or whatever gets you going. Arousal naturally relaxes your muscles.
Lube Generously
Apply to yourself, your partner, and have more ready. Reapply frequently throughout.
It's Okay If It Doesn't Happen
Sometimes your body says "not today," and that's perfectly fine. There's always next time. Never force it.
Best Positions
Different positions offer different benefits. Start with ones that give you more control.
You On Top
Best for: Beginners & control
You control the depth and speed completely. Face toward or away from your partner.
Spooning
Best for: Intimacy & gentleness
Lying on your sides, him behind you. Allows for shallow, gentle penetration with lots of closeness.
Doggy Style
Best for: Depth & access
Classic position allowing good angle and depth. Use a pillow under your hips for comfort.
Modified Missionary
Best for: Eye contact & intimacy
On your back with hips elevated on a pillow. Allows face-to-face connection.
During the Act
- Start incredibly slowly — Even slower than you think necessary
- Pause at the entrance — Let the muscle adjust before going deeper
- Keep breathing — Deep breaths help you stay relaxed
- Add clitoral stimulation — Use a vibrator or fingers simultaneously
- Reapply lube often — Every few minutes if needed
- Communicate constantly — Tell your partner what feels good or needs adjusting
If You Feel Pain
Stop, breathe, add more lube, and try again slowly. If pain persists, stop completely. Pain is your body's signal that something isn't right.
Better Control
A strap-on allows more precise control of angle and depth than his penis, which responds to arousal.
Size Progression
Start with a slim dildo (smaller than him), then progress to larger sizes over multiple sessions.
No Performance Anxiety
Many men lose hardness from nervousness during first-time anal. A dildo stays firm no matter what, removing that pressure entirely.
Room to Be Gentle
Without the urgency of maintaining an erection, he can take all the time you need—going slowly, pausing, and being truly patient.
Why This Approach Works
When his arousal isn't a factor, he can dedicate 100% of his attention to you—reading your body language, adjusting his technique, and taking breaks without frustration. This removes the common scenario where he rushes because he's worried about losing his erection. The result is a more relaxed, enjoyable experience for both of you.
How to Progress
Start with a dildo about 1 inch in diameter. Once that's comfortable over 2-3 sessions, move up to one close to his size. When that feels natural, you're ready for him. This gradual approach makes the transition smooth and pleasurable.
Enhancing Pleasure
Combine Stimulation
Clitoral stimulation during anal can lead to incredibly intense orgasms. Use a vibrator or fingers.
Explore Fantasies
The psychological aspect matters. Talk about what turns you on, set a mood, make it special.
Vary the Rhythm
Alternate between shallow and deep, fast and slow. Find what rhythms feel best for you.
Let's Talk About Accidents
We're adults here—sometimes things happen. Here's the truth: with proper preparation, accidents are rare. But if they do occur, it's not a big deal.
Reality Check
Minor incidents are a possibility with any anal activity. A mature partner will handle it gracefully— clean up, maybe take a shower together, and move on. If someone makes you feel ashamed, that's their problem, not yours.
Prevention Tips
Avoid anal play if you're feeling digestive discomfort. Time it 1-2 hours after a bowel movement. A quick external wash or light douche before play gives most people complete confidence.
Aftercare
What you do after matters too. Take care of yourself.
- Clean up gently—a warm shower or bath feels wonderful
- Urinate soon after to prevent any bacterial issues
- Some mild soreness is normal; it should fade within a day
- Cuddle, connect, and talk about what felt good
- Drink water and maybe have a light snack
When to See a Doctor
If you experience significant bleeding, persistent pain lasting more than a day or two, or any unusual symptoms, see a healthcare provider.