10 Best Pegging Positions: First Time Pegging Guide

Last Updated on February 15, 2024

If you're curious about the best pegging positions for first timers, you've come to the right place! My area of expertise is to help a happily married husband and wife or partners stuck in a sex rut to re-ignite their sensual passion & sexual pleasure in the bedroom to feel like a wild, exciting couple.

Repetitive sex is boring sex, so couples turn to different sexually adventurous activities to make lovemaking more exciting and feel brand new. If you're seeking to enhance your erotic enjoyment and are curious about anal pegging him, find out what is pegging sex first. Scan through the FAQ with your lover and see if it's something you'd like to try.

Pegging Him for the First Time

Being on the other side of the counter, we know how many couples engage in this style of adventurous erotic play. You wouldn't believe how many boyfriends and girlfriends search online for doggy style or sensual pegging positions before taking the plunge.

We're so accustomed to the man as the penetrator, so when gender roles are reversed and now the woman is the penetrator, the game changes entirely! Instead him giving her a vaginal orgasm, she gives him a pegging prostate orgasm, (that's the ultimate goal, anyway!)

What you'll need for first time pegging sex:

1. Pegging strap on harness
2. Toy for pegging
3. Lube for anal sex

If you've never had anal sex before, it's important to realize that it is somewhat trickier than vaginal intercourse. The butt cheeks like to get in the way, they close down and protect his butthole like a big, cushy clamp.

Think of it as a giant oyster and you're seeking the small pearl hidden within with a tiny probe. All joking aside, you'll need to pry open the butt cheeks to gain access to his anus.

This is the major difference between these two styles of intercourse, you can't just walk up to him and peg his butt. You'll need to get your hands involved to maneuver things in the right position before inserting the toy.

Once your bodies are in place however, your hands remain free to stroke his penis, pinch his nipples, do whatever you want to please him. Pegging sex is all about HIS pleasure while SHE is in full control.

An important tip is to get the right gear before you begin. Sure you can buy a strap-on penis, liquor him up and and have your way with him, so to speak, but if you choose something too large, he'll clam up and establish his rear as a permanent no-zone. Be cognizant of the size of your attempt and make sure you follow steps on proper techniques to assure a fun first time anal experience for him.

10 Best Pegging Positions

In the following list of best pegging positions for couples, there is a picture demonstrating how to do it and a rating system that helps to asses which one you'll like most. The suggestions range from beginner friendly, first time pegging sex to fully acrobatic, advanced contortionist like poses for a real wild night together.

Pegging position rating criteria:

1. Kink Factor – If you think awkward, acrobatic sex is fun and put the PLAY in sex play choose a position with a 10/10 kink factor. Couples that enjoy dominant/submissive encounters or hard sex will appreciate these.
2. Sensual Factor – If you like romance and put the LOVE in lovemaking, choose a position with a 10/10 sensual factor. These poses emphasize the emotional connection of such an intimate shared sex act.
3. Level of Difficulty – This rating factor is based solely on how easy or difficult it is to penetrate his anus. It does not pertain to physical strength requirement, it's all about quick anal insertion. Easiest is 1/10, most difficult is 10/10.
4. Prostate Orgasm Potential – Men who enjoy prostate massage like pegging sex even more when the prostate can be stimulated. It's a serious bonus for him. Minimal prostate stimulation, 1/10, maximim prostate stimulation 10/10.

1. Practical Pegging Posture

Doggie style is the first time pegging position that beginners like best. Why? For men who are unsure of the whole idea to begin with, they appreciate the impersonal doggy style. You're facing away from each other and there is a good amount of emotional separation so you don't share weirdness. It's the best position to try to determine if you like sexual pegging or not.

Body size does not matter with this sex positions like this as much since he can spread or close his knees to adjust the height of his butt in relation to her pelvis. There is high level of customization available to align your bodies together for penetration. He can put a pillow under his arms and lay his elbows down to level out his torso if needed.

She is in full control while holding his hips with her hands. Communication is extra important here as he will let the partner know how fast & deep to go (or not to go!) It's completely hands-off for him as he leans forward and lets the partner totally dominate the play.

If you have a short pegging dildo (less than 5 inches long, for example) it may be challenging to achieve full & consistent anal penetration since his butt cheeks tend to be held tighter in this position. The dildo can pop out when she retracts her pelvis during in & out thrusting. The longer the probe, the easier it will be to enter and stay in the rectum. Shop our category of dildos for guys that have a longer insertable shaft that works better with this position.

• Kink Factor: 1/10
• Sensual Factor: 1/10
• Level of Difficulty: 5/10
• Prostate Orgasm Potential: 1/10

2. Passionately Pegging

This is one of the easiest pegging positions for beginners with a small strap on dildo. He spreads his legs and wraps his feet around her waist. This naturally spreads his butt cheeks open so she can locate his anus quickly. It's also more interactive and passionate when the couple is face to face with eye contact.

The couple can kiss, be close and feel each other breathing, it's highly sensual being so connected. In fact, the couple is so close that his erection is squeezed between both of their torsos adding extra sensation for him. He can reach around her body and give a big bear hug engaging in a full romantic embrace.

If she is too short to reach him laying on the bed, try the sofa or a footstool to better align for penetration. The straight-on position limits poking inside his rectum, the probe goes straight in, straight out, seamless and easy for maximum comfort and pleasure.

• Kink Factor: 1/10
• Sensual Factor: 10/10
• Level of Difficulty: 1/10
• Prostate Orgasm Potential: 1/10

3. Prostate Perfection

This is a slight variance on the aforementioned position with your partner, but there is a huge difference to his p-spot stimulation experience. By having him lift up his hips by propping his arms on the bed (or sofa), it angles his pelvis higher which not only enables easier penetration, it encourages prostate stimulation with each thrust inwards.

He can control exactly how high to lift his pelvis to get the best angle for prostate massage. I like this position because she has no idea when she's hitting the P Spot, but he can customize the angle to make sure she reaches the mark every time. The possibility of pegging orgasms is very high with this position. It also leaves the body exposed so you can use adult toys on each other.

It's not just the wife in control, the husband has a part to play too. When he lifts up his legs and places them on the shoulders, it offers excellent access to his anus, it's easy for her to split the cheeks and plunge that toy nice and deep right away with minimal fumbling required.

If he has the strength to maintain his body position for the duration of intercourse, she can leave her hands completely free to masturbate him. Stroke that penis until he cums, but make sure to have a towel handy so he doesn't ejaculate all over himself!

• Kink Factor: 8/10
• Sensual Factor: 3/10
• Level of Difficulty: 3/10
• Prostate Orgasm Potential: 10/10

4. Good Ol' Missionary

A good, standard pegging position for the first time. It has minimal kink factor for your partner so it's the perfect choice for hesitant beginners or shy guys. He doesn't have his private parts splayed out in the open for her to see, it's more modest and subdued.

She is in full control with the strap-on dildo, he lays there waiting for it to happen, a great way to give her all the power and be completely submissive. Secretly, women find this very romantic & erotic at the same time the eye contact makes it lusty & sexy. She can control the depth and the speed of movement too.

The only disadvantage is she may hard a hard time finding his anus because he's laying on top of it! When he props his knees up as shown in the picture, it helps to lift up his butt so she can find it with minimal searching. You can practice first with anal toys or finger sleeves. Much more hygienic than searching your your bare finger!

A longer probe will serve you better here, choose something longer than 6 inches (yes we do have probes that are this long but still thin as a finger) and you'll have a better time getting everything into place. He is free to fondle her breasts, pinch her nipples or even finger the vagina if he can reach; mutual masturbation certainly makes play more fun!

• Kink Factor: 1/10
• Sensual Factor: 8/10
• Level of Difficulty: 8/10
• Prostate Orgasm Potential: 3/10

5. Pegging Paradise

A highly acrobatic angle like a reverse spooning position tailor made for extra deep insertion and proficient prostate stimulation. This may be challenge for really big guys, but slimmer boyfriends won't have a problem folding their body over in front of their girlfriends without pushing her over!

When he retracts his knees up to his chest, that exposes his butt nicely for her. He can rest his feet on her chest and use his arm to prop her pelvis upwards. The higher he goes, the easier it will be for her (and the deeper the dildo can thrust).

She is in a mighty controlling pose here, grab his ankles, push his hips back (as demonstrated in the picture) and control his body pose in any way she pleases. She can also thrust hard and let him take the brunt of her dominance. It's really not for the faint of heart!

He'll experience unrelenting prostate rubbing since the angle is correct for reaching the gland. Since she can go deep, this is a position that experts really like because she can enjoy full-on anal pleasures. Most attachments have a curve to reach the gland, but even a straight realistic dildo can touch the prostate from this direction.

Alternatively, he can place a pillow under his tailbone to angle the body upwards lessening the need to hold himself up. Now his hands are available to fondle her clit or vagina and add an edge of sexual sharing.

 
• Kink Factor: 10/10
• Sensual Factor: 1/10
• Level of Difficulty: 2/10
• Prostate Orgasm Potential: 10/10

6. Lovers Crabwalk

This is a highly sensual pegging position for lovers who like to snuggle and get right up close. The legs are overlapped on top of each other like a pretzel. With knees relaxed outwards, it leaves the privates exposed on both partners. (If she places her legs under his, he will be in a more upright pose to encourage easier anal entry.)

If he sits on her lap, there will be full & complete penetration as their bodies are intertwined like lock & key. The pegging session toy can rest in his anus like a butt plug, it doesn't even nee to be moved. This amplifies the sense of sharing & intimacy, movement is not required so now the lovers can relax in embrace with their bodies as close as possible, a true Ying & Yang connection.

Why not slather yourselves of flavored massage lotion and enjoy the slip & slide? Even though this position is very romantic, you can increase the kink factor by adding nipple toys and slippery massage oils to the mix.

Alternatively, he can sit on her lap, lean back slightly an leave just enough space for a hand job. If this is the case, this position should be done next to a wall so he can lean back on the wall while she jerks him off. If he leans back even 15 degrees, it will increase the chances of prostate contact.

• Kink Factor: 5/10
• Sensual Factor: 10/10
• Level of Difficulty: 2/10
• Prostate Orgasm Potential: 5/10

7. The Standing Plunge

This standing pegging position is best if the woman is tall. He rests on the edge of the bed and she stands infront of him. (If she is too short for anal penetration, improvise by getting him to sit on a chair, sofa, or something lower than a bed.)

When he lifts his legs up high to rest on her shoulders, it leaves the ass area more exposed which allows for easier penetration. He can either hold his legs as shown in the pegging position picture, or he can sit on his hands to prop his buttocks in place for insertion.

This stance allows for extra deep penetration. If the strap on attachment you choose is very short, you'll have great success doing it this way. Her groin will naturally sit close to his anus, you can go extra deep and have excellent control since both partners are fully interlocked like lock & key. He'll feel even the subtlest of movements.

Anal penetration is really easy here giving this option the highest kink & sensual ratio with the lowest difficulty level. With his head held high, the couple can kiss which adds a highly sensual and romantic aspect to pegging sex for lovers. You can hear each other breathe, it's a true up close & personal experience.

• Kink Factor: 8/10
• Sensual Factor: 8/10
• Level of Difficulty: 1/10
• Prostate Orgasm Potential: 3/10

8. Her Highness

This is one of those simple pegging positions where she is royalty and calls the shots! Not too many couples think of a pegging orgasm this way, but it's one of my favorite positions to try. Even first timers can do it effectively on the bed, a nice and safe location for beginners to try something new.

The secret is to place a large pillow under his lower back. You might even need to stack 2 pillows to raise his hips high enough. You'll know when you've reached the perfect angle because as you kneel over him, the strap on attachment will naturally rest near the anus. The likelihood of prostate massage is very good too.

His effort is only at the beginning - he needs to lift his legs high to let her gain access to the hidden sphincter, but once she's in, the legs can be lowered, but keep the knees slightly bent (this will be more ergonomic anyway with pillows under his pelvis).

This is an excellent position for adding in a hand job during while on top, her arms will naturally rest in the magic spot for fondling his penis. If you want to add more passion to play, learn forward and give him a kiss or a nibble on the ear. There is plenty of versatility for her to experiment and do whatever she pleases. Handcuff his arms behind his back to raise the kink factor.

• Kink Factor: 6/10
• Sensual Factor: 8/10
• Level of Difficulty: 1/10
• Prostate Orgasm Potential: 8/10

9. Reverse Cowboy

Many couples don't realize the reverse cowgirl also works as reverse cowboy! Super high on kink factor, she'll have a first person view of the dildo entering his anus. He controls the pace and how deep it goes while she provides the platform for him to sit on.

If he's a big guy, then sitting won't work, she'll be squished, so he'll have to squat or kneel over her body. I think that squatting works better anyway, he can rock back and forth while stabilizing himself with his hands on her knees, or even place his palms on the floor is he has a long enough reach.

The motion is quite similar to heterosexual intercourse, not much changes when using this pegging position so it's actually quite straightforward, assuming that you've done reverse cowgirl before, of course!

He sits facing her vagina, making this an excellent opportunity to buy a vibrator sex toy that he will use on her. By adding a female vibrator to the mix, it boosts kink factor and adds sexual pleasure for both partners, not just him. This is a surefire way for the husband and wife to experience orgasms together.

Normally, a wife pegging a husband puts the focus on him, but if he uses a vibrator on her, it changes the dynamic of the activity and creates an equal balance and a nice departure from regular girl on guy anal penetration.

• Kink Factor: 10/10
• Sensual Factor: 1/10
• Level of Difficulty: 1/10
• Prostate Orgasm Potential: 5/10

10. Cowboy

Last but certainly not least is the cowboy pegging position. The difficulty rating is somewhat higher than the previous because the anus is not visible, so you'll be navigating solely by feel. Once in place however, it's up to him to bounce as he pleases and control the pace, just as in the reverse.

Being more challenging, why would lover even assume this position? It's nice to be face to face, and if he is weary about exposing his ass to he face, it's more modest too. He can lean over and kiss her to add romance.

To add kink comes naturally because his erection is front and center the entire time, completely exposed for stimulation. Stroke his cock and play with his scrotum while he's up there.

There is a high chance of the strap on attachment slipping out just because the angle of entry is slightly awkward and not as ergonomic as some other positions, so a little more work is required on behalf of both partners. Still it's a good one to try on “Strap On Saturdays” when you want a different way to play, but perhaps not a good choice for the first time pegging him.

• Kink Factor: 10/10
• Sensual Factor: 4/10
• Level of Difficulty: 9/10
• Prostate Orgasm Potential: 3/10

Best Positions for Pegging Toys

Prostate stimulation is one of the best sensation for guys during anal play. The best positions for pegging using a toy include any that pushes the dildo or curved anal pegging toy to the front of the body. The prostate gland is located about 3 inches inside the anus facing the front (towards the belly button) so a sexual position that encourages the toy to point this direction will be more enjoyable for him.

Also be sure to use plenty of lubricant. You can use water based lube, or thick anal lube. Lubricate the top half of the toy, but also around his anal entry and about a half inch or so inside. You can use a lube shooter if you're not keen on sticking your finger in his butt. I advise against using silicone lube because it is more difficult to wash out, some guys even need to resort to an anal douche to clean the rectum completely. Silicone lube can also melt silicone toys so it's best to stick to a thick gel water based formula only.

Speaking of cleaning, make sure to wash the toy with sex toy cleaner after each use and let air dry before storing. The strap on harness can be hand washed with soap and water in your bathroom sink. Never share toys between anus and vagina, so his pegging toys should be kept separately from anything else.