Anal Sex Positions for Crossdresser, Transgender & Gay People

Anal sex is growing in popularity, and being a crossdresser this something you should not restrict yourself from doing, if you desire to experience the pleasure it offers.

Anal sex can provide a unique orgasmic experience when approached correctly, employing suitable positions stimulating pleasurable spots.

However, anal sex demands a lot of experience and safety. Learn more>>Anal Sex Safety: Everything You Need to Know

So, if you are someone who has never done it, there are a few things you should consider.

First and foremost, start slow by playing around with your fingers, gradually working your way up from small to big.

Get comfortable with the feeling by initiating with the rim of the butthole before inserting a penis, strap-on, or dildo.

Don’t forget to use a lot of lube for a smoother and wetter experience.

It’s crucial to have a conversation with your partner before proceeding.

If discomfort is felt during penetration, hold back, prepare your body and mind again, and restart.

There’s no shame in taking things slow and stopping in between because always remember, safety comes before pleasure.

Okay, now that you know everything about butt sex, let’s look at the 15 anal sex positions you can try for an ecstatic orgasm.

14 Anal Sex Positions to Try

Lap Dance

Lap dance is a perfect position for crossdressers who haven’t tried anal sex before, as it gives enough control to the person on the receiving end to pull out if required.

As the name suggests, this position resembles giving a lap dance to your partner. In this position, your partner needs to sit with their legs wide open, and you need to sit down on them and let them enter you.

You will do most of the work in the lap dance position, using your thigh muscles for up and down motions.

You can control how far you want to go.

To increase intimacy, reach your hands around the back and grab your partner.

You can also play with your penis for extra fun.

Piledriver Position

If you enjoy being controlled by your partner, you will enjoy this sex position, although you have to be a little flexible if you want to try it.

In this position, you need to lie on your back and allow your partner to grab your legs and push them right back so that your ankles are literally by your head.

You’ll love this position as it leaves you in a vulnerable spot with no control. Once in this position, your partner can squat on you and insert anally.

Laying Doggy

Again, trying the lying doggy position is a must if you enjoy being controlled. In this position, you lie on your stomach with your partner entirely on top of you in a dominating position, entering from behind.

You can lift your buttocks a little to enable extra penetration and thrusting.

Additionally, anal nerve endings are located two inches from the opening, so this is a great way to experience stimulation even if you’re new to anal sex.

You can also tell your partner not to hold back on spanking for extra fun.

Missionary Position

This position is a dream come true for many individuals who enjoy crossdressing, as it resembles vaginal sex involving anal penetration.

Being in the missionary position can genuinely evoke a feminine feeling.

To try this position, place a pillow beneath your buttocks to elevate your hips closer to your partner’s pelvis.

And don’t forget to make eye contact, kiss, talk, and moan during the experience.

These actions will enhance the intimacy of the moment.

Cowgirl Position

If you want to take control during anal sex, the cowgirl position is worth a try.

Simply straddle your partner and lower yourself onto their penis.

As you’re in control, you can determine the depth of penetration and the pace of the intercourse.

You can also move back and forth for additional stimulation.

Feel free to explore and enjoy playing with your penis for added pleasure and fun.

Reverse Cowgirl

While not as popular among anal sex enthusiasts, the reverse cowgirl position is worth a try if you haven’t experienced it before.

Similar to the cowgirl position, your partner will lie down, and you straddle them facing the opposite direction and slide down in your comfort.

You can incorporate penis play for additional stimulation, like in the cowgirl position.

Backsided Lotus

Wow, this is the most romantic position where you are incredibly close to your partner, sitting on their lap. Have your partner sit and cross their legs, and then you get on their lap and wrap your legs around their hips.

Since you and your partner are now face to face, close to each other, there is so much you can do, and the sky’s the limit.

Enjoy making out, maintaining eye contact, moaning, and more.

Doggy Style

This is the most dominant position among all the other positions for anal sex and also one of the most widely adopted positions.

In this position, your partner can penetrate you from behind, and you can push back onto your partner if you want.

You simply get down on your knees and hands while keeping your legs close together to get into the position.

Your partner will then squat above you and put their hands on your hips, waist, and shoulders or hold your hair.

They need to start thrusting into you from here, and you can push back against them.

Standing Doggy Style

This position is very similar to doggy style, but in this one, you and your partner are standing, and you, on the receiving end, are bending over at the waist.

Your partner can enter you from behind. Let them grip your wrists, holding them by your sides for balancing.

You can also grab your partner by their hips or let them grab and spank you to show domination.

The position is very sexy as your movements are restrained, and your partner controls the intercourse.

Pro tip: Try this while wearing breast forms to feel the extra weight on your chest and experience the jiggling effect.

Trust me; it will make you feel more feminine and give you an elusive sissygasm.

Bodyguard Position

This is the ultimate anal sex position where you are very close to your partner, enabling you to have kisses, talk, and engage in biting during sex.

In this position, you and your partner will stand upright and face in the same direction.

They will enter from behind, and you can lean back against your partner.

If you want to enhance the experience and make it more vigorous, do it in front of a wall so that you can thrust back against your partner.

You can also ask your partner for some hand play in this position.

Teaspooning

Teaspooning is a derivative of the bodyguard position but is slightly less vigorous and slower.

You and your partner are on your knees in this position, and the rest of the process is the same as the bodyguard position.

You can also easily incorporate doggy style by kneeling forward on your elbows.

Hold your partner from the hips area to increase the thrust and pressure from the backside.

You can also try this position in front of a wall or mirror for more vigorous sexual intercourse.

The Caboose

One of the cutest anal sex positions is the caboose.

In this position, your partner sits on the bed or a chair, and you back yourself into their lap and spoon each other while seated.

It’s a very intimate position where you’ll be attached to your partner from the torso to the legs, and you can kiss each other to enhance the romance even more.

See Saw Position

The see-saw position is challenging and playful, guaranteed to generate laughter as you engage with each other.

In this position, you and your partner face each other.

Your partner sits on the bed, using their hands behind them to support themselves upright.

You then sit down on their lap, allowing them to enter anally.

Use your hands to help balance yourself and lift your buttocks slightly to create space for thrusting motions.

Maintaining eye contact adds an extra level of intrigue to this position.

The Deep Impact

This position lives up to its intriguing name.

You lie on your back and lift your legs to get into the Deep Impact position.

Your partner then slides into position so your ankles rest on their shoulders.

If your partner kneels and positions their thighs beneath your buttocks, they will be closer to your anus for penetration.

You can also incorporate penis play and allow your partner to stimulate your breasts for excitement.

Conclusion

Anal sex is a great way to explore sexual fantasies and have extra fun in the bedroom.

It’s completely normal and even considered healthy sexual activity, backed by studies.

Just remember, safety should always come first. Make sure to follow the safety tips mentioned earlier before trying anal sex.

Sometimes, you may not experience pleasure, but that doesn’t mean anything is wrong with your sexual health.

Give different positions a go from the list above, and you will find one that brings you immense pleasure and satisfaction.

Enjoy the adventure!