Beginner Strap On Guide: Everything First-Timers Need to Know

Exploring strap-on play opens new dimensions of intimacy, role reversal, and pleasure for couples of all genders and orientations. Whether you're curious about pegging, want to experience penetration from a new angle, or simply crave novelty, your first strap-on experience hinges on choosing the right equipment, communicating openly, and starting slowly.

This guide covers selecting beginner-friendly harnesses and dildos, essential prep steps, comfortable positions, and troubleshooting common challenges—so you can approach your first session with confidence instead of confusion.

Who Should Try Strap-On Play?

Strap-on experiences aren't limited to specific relationship dynamics or identities. They're for anyone curious about exploration and communication.

• Couples exploring role reversal where the receiving partner wants to experience being penetrated by their partner
• Partners with erectile challenges who want to maintain penetrative intimacy
• LGBTQ+ couples seeking varied penetration options beyond anatomy
• Pegging enthusiasts (when a partner with a vagina penetrates a partner anally)
• People with mobility limitations who benefit from hands-free penetration control
• Those craving novelty who want to break routine and try something adventurous

You don't need BDSM interest or dominance dynamics—strap-ons work in gentle, egalitarian contexts too.

How to Choose Your First Strap-On Setup

Strap-on systems have two main components: the harness (worn around hips/waist) and the dildo (insertable attachment). Beginners should prioritize comfort, adjustability, and ease of use over complexity or aesthetics.

Harness Types for Beginners

Recommendation for beginners: Start with a two-strap jock-style harness in nylon or leather. These offer maximum adjustability, stability during thrusting, and compatibility with various body sizes.

Dildo Selection for First-Timers

Size guidelines:

• Length: 5–6 inches insertable length (realistic average)
• Diameter: 1–1.25 inches (approximately finger-width to slightly thicker)
• Shape: Straight or gently curved—avoid extreme textures, ridges, or large heads

Material priorities:

• Body-safe silicone: Non-porous, easy to sterilize, flexible yet firm
• Dual-density silicone: Soft outer layer over firm core—mimics realistic texture
• Avoid jelly rubber or PVC: Porous materials harbor bacteria even after cleaning

O-ring compatibility: Most harnesses use O-rings (circular rubber rings) to hold dildos in place. Check that your dildo has a flared base that fits standard O-ring sizes (typically 1.5–2 inches diameter).

Tip: Choose a dildo with a suction cup base—it doubles as a hands-free solo toy if the harness doesn't work out immediately.

Complete Beginner Starter Kit Checklist

• Two-strap adjustable harness (nylon or vegan leather)
• 5–6 inch silicone dildo with flared base (1–1.25 inches diameter)
• Water-based lubricant (generous amounts—at least 4 oz bottle)
• Toy cleaner or antibacterial soap for post-session hygiene
• Towels or waterproof blanket to protect bedding
• Communication agreement on safewords and check-in phrases

Preparing for Your First Strap-On Session

Proper preparation reduces anxiety and increases the likelihood of a positive first experience.

Step 1: Communicate Boundaries and Desires

What to discuss:

• Who will wear the harness first (or if you'll alternate)
• What the receiving partner enjoys (slow, fast, shallow, deep)
• Hard limits (positions, depths, or activities that are off-limits)
• Safewords or check-in phrases ("yellow" for slow down, "red" for stop)

Why it matters: Strap-on play involves vulnerability for both partners. The wearer may feel awkward or uncoordinated; the receiver needs trust and reassurance. Clear communication prevents misunderstandings mid-session.

Step 2: Fit and Adjust the Harness (Before Getting Aroused)

How to do it:

1. Step into the harness like underwear while clothed or in comfortable attire.
2. Pull straps snug but not tight—you should fit two fingers under each strap.
3. Position the O-ring centered over your pubic bone (or slightly higher for leverage).
4. Walk around, squat, and test range of motion. Adjust if straps dig in or slip.

Why it matters: Fumbling with buckles during intimacy kills momentum. Pre-fitting eliminates surprises and ensures stability during thrusting.

Tip: Some wearers find underwear beneath the harness more comfortable; others prefer direct skin contact. Experiment to find your preference.

Step 3: Attach the Dildo Securely

How to do it:

1. Slide the dildo's flared base through the O-ring from behind (shaft pointing outward).
2. Pull the base fully through until it sits flush against the harness.
3. Tug gently on the dildo—it shouldn't slide or rotate easily.

Why it matters: A poorly secured dildo slips out mid-thrust or rotates awkwardly, frustrating both partners.

Troubleshooting: If the dildo wobbles, the O-ring may be too large. Most harnesses include multiple O-ring sizes—swap to a smaller one.

Step 4: Practice Solo Movements (Optional but Helpful)

What to do: The wearer stands in front of a mirror and practices hip thrusts, adjusting their stance and angle. This builds muscle memory for thrusting motions.

Why it matters: Strap-on thrusting requires different mechanics than penis-based penetration. The dildo sits higher on the body and doesn't have nerve feedback. Practicing solo reduces first-time clumsiness.

Step 5: Warm Up the Receiving Partner

What to do:

• Spend 10–15 minutes on foreplay: kissing, touching, oral stimulation, or using clitoral vibrators or prostate massagers.
• Use fingers or smaller toys to gently prepare the receiving partner's body.
• Apply generous water-based lube to both the dildo and the receiving partner's entrance.

Why it matters: Arousal relaxes muscles and increases natural lubrication (for vaginal play) or readiness (for anal play). Skipping warm-up causes discomfort or pain.

Tip: The receiving partner should feel relaxed and eager—not pressured or rushed—before penetration begins.

Beginner-Friendly Strap-On Positions

Not all positions suit first-timers. These four prioritize visibility, control, and comfort.

1. Missionary (Face-to-Face, Receiver on Back)

Setup: Receiver lies on their back with hips elevated by a pillow. Wearer kneels or lies between their legs.

Why it works: Maximum eye contact and communication. Wearer can watch their partner's face for discomfort cues. Receiver can guide depth and angle with their hands.

Tip: The wearer should start with shallow, slow thrusts—depth perception takes practice. Receiver can place hands on wearer's hips to control pace.

2. Doggy Style (Receiver on Hands and Knees)

Setup: Receiver kneels on all fours. Wearer kneels behind them, holding receiver's hips for stability.

Why it works: Natural angle for G-spot or prostate stimulation. Wearer has leverage for deeper, controlled thrusts. Less face-to-face pressure reduces performance anxiety.

Tip: Receiver can lower onto forearms (instead of hands) for a steeper angle if desired. Communicate constantly since you can't see each other's faces.

3. Spooning (Side-by-Side, Receiver in Front)

Setup: Both partners lie on their sides. Receiver's back presses against wearer's chest. Wearer enters from behind while holding receiver close.

Why it works: Intimate and low-effort. Ideal if either partner tires quickly. Allows wearer to reach around and stimulate receiver's genitals with hands or bullet vibrators.

Tip: Use a pillow under the receiver's top leg for better access and comfort.

4. Receiver on Top (Cowgirl/Reverse Cowgirl)

Setup: Wearer lies on their back. Receiver straddles and lowers onto the dildo, controlling depth and pace.

Why it works: Receiver has full control—they set speed, angle, and depth. Wearer can relax and focus on hip movements without worry about going too hard or fast.

Tip: The wearer should keep hips still initially, letting the receiver adjust. Once comfortable, the wearer can add gentle upward thrusts.

Common First-Time Challenges and Solutions

The Dildo Keeps Slipping Out

Why it happens: O-ring too large, dildo base too small, or thrusts are too vigorous without proper angle.

Solution: Swap to a smaller O-ring. Ensure the dildo has a flared base that fits snugly. Slow down thrusts and focus on angle rather than force.

The Wearer Can't Feel Anything

Why it happens: Unlike biological anatomy, strap-on dildos don't provide direct sensation to the wearer.

Solution: Choose harnesses with internal pockets for bullet vibrators or small vibes that stimulate the wearer during use. Alternatively, use strapless strap-ons (double-ended) for internal stimulation—but only after mastering basic harness use.

The Receiver Feels Discomfort or Pain

Why it happens: Insufficient lube, inadequate warm-up, thrusting too fast/deep, or tension from anxiety.

Solution: Stop immediately. Add more lube (you can't use too much). Slow down and return to foreplay. Check in verbally: "Does this feel okay?" "Should I go slower?" Never push through pain.

The Wearer Feels Clumsy or Uncoordinated

Why it happens: Strap-on thrusting requires different body mechanics than penis-based penetration. Lack of sensory feedback makes it harder to gauge depth and rhythm.

Solution: Practice makes perfect. Start with exaggerated slow motions. Watch your partner's body language. Use your hands to guide the dildo initially if needed. Consider positions where the receiver controls movement (like cowgirl).

The Harness Chafes or Feels Uncomfortable

Why it happens: Straps too tight, incorrect positioning, or sensitive skin.

Solution: Loosen straps slightly—they should be snug but not biting. Wear soft underwear beneath the harness. Apply a thin layer of coconut oil or body lotion to areas where straps rub (but avoid near the dildo insertion point).

Aftercare and Communication Post-Session

Strap-on play—especially first experiences—can be physically and emotionally intense. Aftercare strengthens connection.

Immediate Physical Care

1. Remove harness and dildo slowly: Don't rush. The wearer may feel stiff; the receiver may be sore.
2. Clean up together: Wash genitals with warm water and mild soap. Clean the dildo immediately with toy cleaner or antibacterial soap. Learn proper toy cleaning to prevent infections.
3. Hydrate and rest: Drink water. Cuddle, use the bathroom if needed, and rest together.

Emotional Check-In

Discuss:

• What felt good and what didn't
• Whether pace, depth, or positions worked
• Any surprises or discomfort that arose
• What to adjust for next time

Why it matters: Vulnerability during strap-on play can trigger unexpected emotions—excitement, awkwardness, or even emotional release. Talking through the experience normalizes feelings and improves future sessions.

Long-Term Maintenance

• Inspect the harness: Check for frayed straps, broken buckles, or stretched O-rings. Replace as needed.
• Store properly: Hang harnesses to air-dry completely. Store dildos in breathable pouches (not sealed plastic). Keep components separate to prevent material reactions.
• Recharge or replace vibes: If using vibrating inserts, recharge batteries or replace disposable ones monthly.

Lube and Material Compatibility

Strap-on play requires generous lubrication—more than you think.

Recommendation for beginners: Use water-based lube. It's universally safe, rinses clean, and won't damage your dildo. Reapply frequently—strap-on play requires more lube than typical penetration.

Frequently Asked Questions

What size dildo should I start with?

Aim for 5–6 inches in length and 1–1.25 inches in diameter. This approximates average anatomy and feels manageable for most receivers. You can always size up later.

Do I need a specific harness for pegging?

No. The same harnesses work for all strap-on scenarios—vaginal penetration, anal pegging, or any combination. Choose based on fit and comfort, not the specific activity.

Can the wearer feel pleasure during strap-on sex?

Not directly from the dildo, but many wearers enjoy:

• Psychological arousal from giving pleasure
• Physical stimulation if the harness base presses against their genitals
• Adding bullet vibrators in harness pockets for direct sensation

Is strap-on play only for certain relationship dynamics?

No. Strap-ons are used by couples of all genders and orientations—heterosexual, same-sex, non-binary, polyamorous. There's no "right" dynamic; only what feels good and consensual for you.

How do I avoid awkwardness the first time?

Expect some clumsiness—it's normal. Laugh together, communicate openly, and remember that coordination improves with practice. Start slowly, check in frequently, and prioritize comfort over performance.

Can I use a strap-on if I have mobility or flexibility limitations?

Yes. Choose positions that minimize strain—spooning, receiver-on-top, or seated positions. Consider harnesses with fewer buckles for easier dressing. Sex toys for couples include adaptive designs for diverse needs.

Conclusion

Your first strap-on experience doesn't need to be perfect—it needs to be communicative, curious, and comfortable. With the right equipment (adjustable harness, beginner-sized dildo), proper preparation (warm-up, lube, communication), and realistic expectations (coordination takes practice), you'll discover a new dimension of intimacy and pleasure.

Ready to explore? Browse our collection of body-safe sex toys designed for all experience levels, and start your strap-on journey with confidence.