How to Ride a Guy for Gay Men: 12 Anal Master Tips!

how to ride a guy gay men
How to Ride a Guy

How to Ride a Guy for Maximum Pleasure and Avoid Pain

Learning how to bottom isn’t something that comes with a guide. The reality is that for many gay men, anal sex can be a real source of anxiety. It wasn’t that long ago that being gay was something that one had to hide because of understandable concerns about being judged.

In fact to some degree, there still exists anti-gay sentiment in many parts of the United States. With the legalization of same sex marriage however, it does appear societal views are changing.

And so the purpose of this page is to help you as a gay men understand the unique dynamics involved with anal intercourse with your man. We’ll walk you through some of the science of riding a guy and offer a set of 12 tips designed to make the experience as comfortable, pleasurable and pain free as possible.

Let’s jump right in!

Riding a Guy: Anal Anatomy

Before moving into the “How to ride a guy” tips, it is important to understand the anatomy of the anus. Similar to your penis, the anus is wired with tons of sensitive nerve endings. When properly executed, these nerve endings can make riding a guy very pleasurable.

At its core, the anus is the external opening of the rectum. Inside, it is controlled by two small rings of muscles referred to as external and internal sphincters. You have the ability to control your external sphincter. The internal sphincter, however, is involuntary in nature, meaning you don't have the ability to control.

What often happens is that when the two sphincters and too tight (tense), it challenging and painful for a penis to enter – particularly if it is large. If the sphincters are in a relaxed state however, they have the ability to stretch and expand, allowing you to ride a guy of any size.

Like your penis, your rectum is filled with super sensitive nerve endings. This is why riding a guy is so pleasurable for many gay and bi men – as well as women.

During anal intercourse, your prostate gland (a small, walnut-sized gland that is nestled between your bladder and penis) can be stimulated, which a lot of guys find enjoyable.

Some people call the prostate gland the male G-spot, which can amplify feelings of pleasure.

Ride a Guy Psychology
Ride a Guy Psychology

Riding a Guy: The Psychology

Most guys who ride other guys will tell you that half of the stimulation from the experience comes from the psychological aspects. Sitting on top of a man that you are very attracted to can be hot, erotic, intimate and romantic.

Some men have shared that the experience itself promotes strong feelings of wholeness. Others have even said there is a spiritual aspect involved.

Get to Know Your Anus

To experience pleasure when you ride a guy, it is vital that you get to know your anus. This means becoming comfortable with everything going on down there. Just like you got to know your penis earlier in life, the same holds true for your rectum.

If you experience strong feelings of shame about this, you might want to think about talking to a professional because your emotions can have a lot to do with how successful the riding a guy experience will be.

cowboy bathtub boots hat
Get to Know Rectum

One approach is to lay flat on your back on your bed or even in a warm tub. Once you feel relaxed, start to gently massage the area around your hole. As time goes on and you feel more comfortable, add a little lube to your middle finger.

With gentle care, gently press up against the surface of your anus. You will want to do this several times and increase pressure incrementally.

When you are ready, insert your finger into your hole, slowly and gently. The goal is to relax the external sphincter (the one mentioned earlier that you have control over).

As you wiggle around a bit inside, you may be able to feel your prostate gland. It will feel like a small walnut, around 2-3 inches inside of your rectum.

You may have to repeat the above several times over the course of several days in order to feel comfortable with something inside of your hole. As you continue to gain confidence and feel comfortable – and hopefully pleasure – you can then move on to experimenting with toys. The trick is to go super slow and use lots of lubricant.

Riding a Guy and Lube

Many men have reported that the best lube that provides the most pleasure are brands like Gun Oil Lube. The reason being is that Gun Oil is silicone based, which provides greater lubrication and more “slip” at the time of insertion.

Here is a tip that you likely won't hear elsewhere. It helps a lot before riding a guy (particularly a large one) to use a lube launcher. These devices are specifically designed to coat your anus with lubricant so that you're ready to rock. You can get your launcher directly from Amazon for a good deal.

gun oil lube
Excellent Lube for Beginners

This point can't be emphasized enough. The more you use the better. As time goes on, you may not need as much but don't worry about that right now. There's no shame in making sure you are properly slicked up.

FYI: Some guys find that using a desensitizing lubricant for anal works best – particularly for newbies or for men who have large partners.

12 Tips to Ride a Guy

Now that we have walked through the ins and outs (no pun intended) of the anus, it’s time to explore 25 tips to ride a guy. The following suggestions are designed to help you experience as much pleasure as possible while minimizing pain.

12 tips to ride a guy right
12 Tips to Ride a Guy Right

1. Ride a Guy Clean

The very first thing you will want to do is make sure you are clean down there. One of the most embarrassing things that can happen is when you are riding a guy and something unfortunate happens. That's why beginner bottoms needs carefully clean and wipe to avoid these kinds of accidents.

Related: Anal douche guide for men ultimate guide

There are many commercial products that you can buy on the market. Many gay men who ride guys report that OTTBA Enema Kit provides superior cleaning power while also coupling as a source for pleasure. It comes in a discrete box to your home and includes a small amount of lube. It's also FDA approved.

2. Ride a Guy Wrapped

The second suggestion that is to ride a guy with a condom. While it is true that we live in an age of PREP, there are still risks involved with the potential spread of various STIs.

The ultimate choice to ride it wrapped is obviously up to you. In committed, monogamous relationships, some guys who ride other guys opt not to wrap up. Some couples who invite in a third, which is factored into the wrap it up decision making process.

3. Ride a Guy Mindset

If you are going to ride a guy, it is important to be in the right mindset. This means being in a relaxed state of mind and not stressed out by the day’s events.

Some guys claim that riding a guy helps them to decompress and feel less stress. While this may be true, there is a difference between stress and anxiety.

Generally speaking, stress is the byproduct of cumulative events or responsibilities. Anxiety, on the other hand, is a function of mood. To help in both areas, consider listening to relaxing music or meditating may help bring about feelings of calmness.

4. Ride a Guy and Eating

One of the biggest turn offs for both the top and the bottom during ride a guy intercourse is the sound of bodily fluids and/or gas. This is why you don’t want to eat anything a good two to four hours before sitting on a guy.

If you are able to, reduce use of milk products and other belly bloating foods prior to intercourse. When you are gassy, it can act as a barrier to pleasure and potentially cause discomfort.

Brad Pitt Dressed Like a Cowboy
Brad Pitt Dressed Like a Cowboy – Thelma and Louise

5. Ride a Guy and Size

One of the biggest myths floating around is that in order to experience pleasure when you ride a guy, the man needs to be large. While it is true that a big (fill in the blank) can be fun to play with, it doesn’t have to be enormous when it comes to riding a guy.

Guys who have an average size penis often can provide loads of pleasure when it comes to rectal intercourse. In fact, sometimes larger sized guys can cause feeling of uncomfortableness.

6. Ride a Guy Control

Just because you are doing the bottoming doesn’t mean you aren’t in control. While some men who ride guys identify as total bottoms, this doesn’t mean they are all submissive.

When you first start your riding adventures, make it clear to your partner that he needs to be slow and that you will control the rate and speed of insertion. Don’t let him get all commando on you and pretend he is a power-drill. There will be plenty of time for that later when you gain experience and confidence.

7. Ride with Your Hands

Part of the control step as previously mentioned requires the use of your hands. If possible, wrap your palm around your guy’s pleasure stick and give it a few quick “pumps” so that it is firm.

Once it feels hard, use plenty of lube on the top and sides of his man-candy. There’s no such thing as too much lube so be generous. Also, take some of the excess lubricant with your finger and wet the outer and inner parts of your rectum.

ride a guys information
Squat Down

8. Ride a Guy Squat

If you are new to riding men, the easiest position to start out with is the squat. Here, you will lie your man flat on his back on the floor or on a bed.

Crouching over him and using the points mentioned above (particularly number 7), slowly and gently engulf his man-candy. Don’t try to rush this. Instead, do a little bit at a time, half inch by half inch. If you need to pause several times during the process, it is completely OK.

9. Ride a Guy Popper Free

Some guys who ride men suggest the use of a brown bottle to help create a more erotic experience.

As a general rule, anything that alters your awareness during riding has the ability to take-away from the experience. This includes other substances, such as alcohol or marijuana. Obviously, the choice is your but there’s something to be said about the natural experience.

10. Ride a Guy Breathing

When you first start riding a guy, it is important to control your breathing. You may be tempted to hold your breath during the insertion process. This is a bad idea because it causes your blood pressure to rise and heartbeat to increase.

Instead, take slow, deliberate breaths. Some men report that they are able to detach from their physical body through mindfulness based breathing techniques.

two hot cowboys
Ride a Guy Participation

11. Ride a Guy Participation

Another helpful tip when sliding up and down a piece of man-candy is to get your guy involved. The truth is, you don’t have to do all of the work.

When the time is right, ask him to do some gentle thrusting. Nothing rapid or anything like that. Again, the idea is slow and gentle. By having him participate, you conserve energy while allowing him to be more active.

12. Ride a Guy Positions

Once you have reached a place of comfortableness, it is completely OK to switch positions. This means moving out of the “crouch” position mentioned earlier and doing something different.

Practical examples include lying on your back, “mission style” and doing in on your side. Additionally, for ultimate pleasure, you may want to let him ride you and take turns. Doing so can maximize feelings of intimacy and pleasure. For extended play, it may help if both of you wear a quality penis ring.

Ride a Guy Book

Your decision to ride a guy could be one of the most pleasurable things you will ever experience. It is important however to not feel like you have to master this activity the first couple of go arounds.

One book that has helped many men is called: The Bigger Bang. Inside, you will find many practical tips such as the ones mentioned here. If you are looking to educate yourself on the riding experience, this read is for you!

Another great read for beginner anal tips is : How to Bottom without Pain or Stains. This one offers concrete advice on how to avoid discomfort while reducing the possibility of “an accident”.

Ride a Guy Poll

Just for fun, we are putting up a poll that asks questions about riding a guy. The results are unscientific but because of the nature of this page, you will likely see responses that show a preference towards bottoming.

Ride a Guy Myths

There are a number of myths “out there” when it comes to riding a guy. While we can’t list them all, here are several of the “biggies”.

  • Riding a guy means you are effeminate
  • Riding a guy is dangerous
  • Riding a guy is for women only
  • Riding a guy doesn’t happen with straight guys
  • Riding a guy is preferred by blue eyed men
  • Riding a guy can’t happen for tall men
  • Riding a black guy is best because they’re extra large
  • Riding a guy without lube doesn’t hurt
  • Riding a guy that is a wolf is best practice
ancient guy riding
Guy Riding History

Ride a Guy History

Many people think guy riding is a new phenomenon. The reality is that this pleasurable activity has been going on since the dawn of man. The historical literature suggests man riding started to crop up in ancient Greece.

Somewhere between 100AD and 800AD in the Northern part of Peru, the Moche culture revealed guy riding in pottery. Archaeologists have unearthed some 10,000 pots with various depictions of riders in various positions.

Final Thoughts

If you want to ride a guy, make sure you are in a physical, psychological and emotional place for it to happen. Never force yourself or feel forced to go through with the activity.

We hope these tips were helpful to you. Happy guy riding and be safe!

Other How To Guides:

About MJ Booth 122 Articles
Based in Los Angeles, MJ is a journalist and blogger who covers the LGBTQ community. Identifying as gender-queer, MJ focuses on topics that touch on a variety of life issues impacting men, women and non-binary individuals. Look for posts on science, dating, relationships, and culture.