CHAPTER 5: All About Sex Toys For Men

Note: This chapter was written for the perspective of genders with a penis.

Let’s pass the mic for a minute. When it comes to sex and orgasms, a lot of the dialogue surrounds the issues that coincide with having a vagina. But what about men?

Gender roles expect men to be A+ performance, sex-hungry machines around the clock. Everyone takes one look at the orgasm gap (for every one orgasm a woman has, a man has three) and assumes that men’s sexuality is AJ squared away. “Men always get off,” we assume. “Men have it so easy.”

In this instance, assuming does make an ass out of you and me. Everyone was shocked when a Canadian study revealed 25% of men admitted to faking an orgasm. The world didn’t want to believe that men’s approach to sex was anything other than simple.  

While headlines and researchers stay busy studying the female orgasm, men face unacknowledged sexual insecurities and conflicts. Male sexuality is important, and deserves the same dedicated investigation and thorough understanding.

One area that doesn’t forget about male sexuality is the sex toy industry. (Should we start a list of why this industry is so lovable?)

How Many Men Are Using Sex Toys?

Women are given proverbial medals for their nightstands overflowing with vibrators. Resources encourage men to use sex toys in their relationship. Yet men with sex toys for single use are brushed off. People presume that a man with his own sex toy implies some rendition of Lars and the Real Girl.

Despite these dumb expectations, men are jumping on the bandwagon. According to FHM magazine, 51% of men own a sex toy. Cock rings are the most popular. Then it’s masturbators, prostate massagers, penis pumps, and erection rings.

Women worry that a sex toy would insult their male partner, yet 69% of men want their partner to use a toy on them.

Many men say that sex toys enhance a solo play session, and that they’re sick of being judged for it. In fact, 70% of men believe they should be able to buy a sex toy without feeling embarrassed.

They also want to involve toys in their sex lives. Women worry that a sex toy would insult their male partner, yet 69% of men want their partner to use a toy on them. A miscommunication between women and men? Never!

There are many sex toys for guys that help them learn more about their body, pleasure, and orgasms. Sex toys acquaint you with your specific preferences. They introduce you to stimulation you’ve never felt before.

Some toys elevate the standard masturbation routine, like masturbators and cock sleeves. Other toys introduce anal pleasure, something some straight men are afraid of. But toys make it easy and friendly to understand why anal pleasure is for everyone. If you haven’t taken advantage of your back door, you ought to start.

How The Male Ejaculation Process Works

Let’s put to bed the major myth that’s confusing men about their orgasms. The truth is, orgasm and ejaculation are two entirely separate things. There are two kinds of male orgasm: an orgasm with ejaculation, and an orgasm without ejaculation.

The journey towards your orgasm begins with arousal. As stimulation arouses your body, blood rushes south and fills the erectile tissue in the penis. This causes an erection, and the more aroused you are, the harder your erection.

Along with an erection you experience higher blood pressure and heart rate. Your scrotum tightens, signaling the testes to tighten and secrete pre-cum. As you near your intense climax, muscles throughout your body start to spasm, like your fingers and toes. Finally, as you orgasm, the tension in your body releases. Rhythmic contractions pulse in the base of your penis, causing the ejaculation of semen.

Afterwards, your penis returns to its normal state. Your body enters a refractory period due to a flux of prolactin. The refractory period is the rest time required before you can get another erection. It varies anywhere from five minutes to an hour.

Post ejaculation, it’s normal to feel a little bit high and tired. That’s thanks to the endorphins released during your orgasm. Your brain also released a flood of the hormone oxytocin, making you a little cuddly.

What Are Multiple Male Orgasms?

Men experience multiple orgasms when they learn how to control orgasms and ejaculation. Most men are surprised when they learn men can have multiple orgasms. You don’t have to ejaculate when you orgasm, but you do have to orgasm to ejaculate. It’s a skill worth learning— many men have insecurities about how long they last in bed. This gives you real control over that.

An orgasm without ejaculation, or a dry orgasm, involves the same anatomical process. But it takes practice of stopping the semen from traveling down your penis. During the climax, the contractions in your penis want to usher the semen along. Instead, you stop the movement of semen much like you would hold back a sneeze.

Stopping the semen comes from the strength of your pubococcygeus or PC muscle. It’s the same muscle you engage to stop urinating midstream. (Which is exactly how you would go about exercising this muscle.)

The thing is, once you have a orgasm without ejactulation, you go into a much shorter refractory period and your erection stays. What does this mean? You can bone for longer and have a real good time while you’re at it.

In case you didn’t pick up on it, learning how to have dry orgasms takes some serious sweat and maybe tears. It’s hard work. And the most efficient way to master the skills is masturbation. Enter: sex toys.

How To Have A Prostate Orgasm — And WTF Is That?

While overhearing all this talk about women’s G-spots, consider this: you have your own.

The prostate, or P-spot, is the G-spot of the male anatomy. It’s a gland the size of a walnut located in the middle of your pelvic bowl, sandwiched by the penis, bladder, and rectum.


You can locate it one of two ways. You can massage the prostate externally via the perineum — the patch between the scrotum and anus. Or, you can stimulate it through penetration. Guys find that playing with the prostate from the inside is more likely to lead to a prostate orgasm. Or multiple prostate orgasms.

To reach the prostate through penetration, insert a finger or toy into your anus. (A partner can do this for you too, of course.) About two inches inside the rectum, on the same side as your belly button, you’ll feel a little bump. Once you find it, you can find the touch that feels best.

Using a finger isn’t always the most effective strategy. Fingers usually aren’t long enough to reach the top of the gland. Using the best male prostate toy is how to achieve prostate orgasms that’ll redefine your concept of pleasure.

Men find that prostate orgasms can be more pleasurable than a “normal,” ejaculatory orgasm. Instead of the pleasure localizing around your penis, you feel it all over your body. Sometimes prostate orgasms last for much longer. And, because you were wondering, there is semen involved. But instead of squirting out due to penile contractions, the fluid flows out. This is why the process has been coined as “milking the prostate gland.”

Prostate orgasms feel awesome, but they’re also wicked healthy by keeping the pipes clean. Male milking prevents residue from congesting the gland. It may even decrease the risk of cancer.

Finding a prostate toy to help you and/or your partner do the job makes the hunt for your P-spot easier and more enjoyable. The best prostate massagers fit the shape of your rectum, so it’s more comfortable than fingers or a penis. Plus, many of them vibrate. Let these prostate toys take you to another world.

Beginner’s Guide: What Do Cock Rings Do?

All happy men have one thing in common: a cock ring collection.

Just kidding, but cock rings do make men really happy. In fact, cock rings are the most common sex toys used by men. They are small in size and simple to use, but give the orgasm experience a makeover during masturbation or intercourse.

What is a cock ring?

A cock ring (also called a dick ring or penis ring) is a sex toy that slides over your semi or fully erect penis. Most cock rings fit snugly at the base, although some nestle beneath the tip or around your balls. While you’re aroused, blood flows into your erection making you hard and extra sensitive to touch — as if I needed to remind you. A cock ring is used to keep the blood in your erection instead of letting flow back out.

As a result, you have a mega-erection. Not only are you harder and bigger than ever, the purpose of a cock ring is to hold off your ejaculation. When you do orgasm, it’s more intense. Cuming feels extraordinarily satisfying. If you’re with a partner, they’re thrilled because the rendezvous lasted longer than usual. Everyone wins.

How to Wear a Cock Ring

Method 1: Around the cock

This is the simplest way to sport a cock ring. If you choose a cock ring made out of stretchy material, it’s easiest to put it on once you’re already hard. Stretch the cock ring. Keeping it stretched, put it over the head of you penis and slide it down to the base. (Always a good idea to use lube.) Then slowly release the cock ring. If you choose a cock ring made out of inflexible material like a metal cockring, you have to put it on pre-erection. Slide the ring to the base of your cock and you’re good to go.

Method 2: Around the cock and balls

Choosing a cock ring for around your penis and balls is just a matter of personal preference. Some men like wearing one around their balls too because it feels more secure, sensational, or comfortable. You need to be flaccid before you put it on. Put one testicle through the ring, then the second. Once they’re both in the ring slide the head of your penis through the space left, and work your ring towards the base. Use lube to finagle this move.

How Do I Know If I’m Using A Cock Ring Safely?

Check to make sure the cock ring isn’t too tight. The point of the cock ring is to give your penis a tight little hug. It is normal for your penis to turn a little pink and swell in size. But if the cock ring is too tight, your penis will turn red or even a little blue. In that case, take it off immediately. If putting on the cock ring causes you any pain, discomfort, or numbing – ditch it.  

If putting on the cock ring causes you any pain, discomfort, or numbing – ditch it.

If it fits just right, go about your business. Don’t wear the cock ring for more than 20-30 minutes total to prevent bruising or affecting the tissue. After you have your awesome toy-gasm, your cock will return to its flaccid size and you can take the ring off the same way you put it on.

Different Types of Cock Rings

Cock rings are like penis jewelry, and there’s a style to rock for every occasion. You want a leather ring with spikes? Check. A hot pink rabbit cock ring? Definitely. Every type of cock ring highlights a unique purpose, but they all amplify sensation. Here are some basics to get the balls rolling.

A classic cock ring is designed to sit at the base of your erection. It is a bit elastic, making it easy to put on and remove. If you’re new to cock rings, the 3 Cock Ring Set by Lyps would be a good place to start. The set has different sized rings made of 100% medical-grade silicone.

If you’re dealing with nightmares of a cock ring getting stuck on your penis, you’re not alone. There’s a whole genre of adjustable cock rings to defeat your fears. Some cock rings, especially the leather ones, snap on and off. But I recommend cock rings that have a little adjustment mechanism to give you the exact squeeze you like. Check out this one by Fifty Shades of Grey.

A lot of the joy from a cock ring happens when the balls get in on the action.

Let’s step up to the intermediate level: metal cock rings (and other hard materials, like steel). Since these guys aren’t stretchy, you slide them on when you are flaccid. The pro about rigid rings is the restraint feels sexy. The con is that if you measure wrong and wind up with the wrong size, it will be worthless to you.

Sorry, I’ve been a little exclusive so far. A lot of the joy from a cock ring happens when the balls get in on the action. Cock and balls rings have one ring for your cock and another for your testicles. Dual rings help the apparatus stay in place, and give your balls a little embrace. Many cock rings have at least one vibrator that sits on top of the penis and/or behind your balls. Keep in mind that a vibrating double cock feels effin-fantastic. So it may not help you prolong ejaculation, if that’s what you’re going for.

In my opinion, attaching a vibrator to a cock ring is a no brainer. You’re already using a toy. Why not maximize the pleasure for you and your partner? Vibrating cock rings have a vibrator on the top of the ring that perches at the base of your penis. It sends vibrations down your shaft and to your partner when you thrust. You’re sold, right? Try the Tracey Cox Supersex Twin Silicone Vibrating Love Ring.

The most advanced cock ring out there is a cock ring and butt plug combination toy. While the cock ring fits the base of your cock, an attached butt plug goes in your ass. These toys intensify your erection while stimulating your prostate. Dual stimulation is intense, but deeply rewarding.

While you’re honing in on which cock ring to pick for sex, remember to keep an eye out for materials. Tons of cock rings are made out of shitty jelly, PVC, or rubber. These ingredients wear down to become toxic, and just don’t last as long.

Some vibrating cock rings are even considered disposable. The battery is irreplaceable, so you have to toss it when it’s dead. If this sounds as wasteful to you as it does to me, you might want to invest in a luxury cock ring. While they are more expensive, luxury cock rings consist of top materials. Their battery is rechargeable; you just have to plug it in. Couples are crazy about the Tor 2 by Lelo.

How to Measure for a Cock Ring

Some of you are thinking, “Nah, I don’t need to do this, I’ll just guess.” You have been blinded by lust for the cock ring! When you finally get a hold of the cock ring and it’s too big or small – I will be saying I told you so.

Measuring for a cock ring applies mostly to rigid rings (cock rings that don’t stretch or adjust). Elastic cock rings are usually one-size-fits-all erections. But even these toys suggest a maximum and minimum diameter for size. Besides, don’t you want to know what the diameter of your erection is, just for kicks?

It only takes five steps:

  1. You need a tape-measure with inches.
  2. Touch yourself until you get an erection. See? I can be fun.
  3. For a cock ring measure around the base of your penis to get the circumference.
  4. For a cock and balls ring wrap the measuring tape around your cock and beneath your balls. Get as close to your body as possible and measure the circumference.
  5. To get the diameter, divide the circumference by 3.14.

You have been blinded by lust for the cock ring!

If anyone asks where you’ve been just say you were practicing math. If you get a decimal, round to the closest .25 of an inch. (Ex: If you measure 1.38, your diameter is 1.50 inches. If you measure 2.14, your diameter is 2 inches.)

Now that you have your diameter, I’ll let you shop in peace. When you buy a rigid cock ring, buy a size .25 to .50 inches smaller than your diameter. This way you can ensure the restriction won’t be too tight or painful.

If you’ve never used a cock ring before, I recommend buying an elastic silicone ring instead of a rigid toy. If you get hard and realize you hate the sensation, you can’t just stretch or cut off a metal cock ring. Instead, familiarize yourself with the adjustable or stretchy rings before you level up.

The Best Cock Ring Materials

Welcome to the world of cock rings, where simple toys make for ultimate pleasure. I mentioned a couple different materials that cock rings could be made of, like silicone, steel, metal, jelly, and rubber. Unfortunately, some materials are safer than others.

If you want the simple version, here it is: buy a medical-grade silicone, metal, or steel cock ring. Any other material runs the risk of toxicity or a porous composition, either of which can lead to irritation, infections, or worse. If you want to the nitty-gritty on material safety, head to Chapter 2.

Frequently Asked Questions

Q: Will a cock ring make me last longer?

A: Yes, at least that’s the idea. When you have an erection, your penile tissue swells with blood. A cock ring constricts the blood from flowing back out, which results in a bigger and more sensitive erection. The constriction also inhibits the muscle contractions that would signal the ejaculatory process. So most men typically last for longer while wearing a cock ring.

Q: What do I do if my cock ring gets stuck?

A: First of all, relax. Take a couple deep breaths. The easiest way to get the cock ring off is for your erection to go down. Think unsexy thoughts. If that’s doesn’t work, take a cold shower and/or put an ice pack on your erection. Use heaps of lube to help you slide it off. If it’s an elastic ring and it still won’t budge, try to slide a pair of surgical scissors underneath and cut it off. Under no circumstances should you use regular scissors or a knife.

If it’s a rigid cock ring made of metal, steel, or the like, the E.R. is your next stop. The good news is you won’t be the first person they’ve seen with a sex toy injury. It happens all the time.

Q: Why can’t I wear my cock ring for longer than 30 minutes?

A: Because it traps the blood and keeps it from flowing out of your penis. This means that toxins and other particles in your blood can’t rinse out of the penile tissue, which puts it at serious risk. By keeping it on for longer than a half hour, you’re also risking coagulation, a painful condition that will land you in the emergency room.

Q: Are there any contraindications to using a cock ring?

A: If you have any conditions involving blood circulation, the nervous system, or diabetes, you should not use a cock ring.

Q: Do cock rings make you bigger?

A: Sadly, no. The effects of a cock ring are only temporary, and your penis will return to its normal size post-erection.

Q: How do I wear a cock ring with a condom?

A: It depends on how the cock ring fits. If it’s a rigid ring that you have to put on before you are hard, you’ll put the condom on after the cock ring. If your cock ring goes around your penis only, you can put the condom on before or after the ring.

Q: Does wearing a cock ring make me better in bed?

A: Nope. A cock ring can delay ejaculation, making you last longer, but that’s about it. Your skills in the sack are still in your hands.   

How To Stimulate The Prostate — A Beginner’s Guide

Prostate massagers are the new guys on the block. Word is starting to spread about how to have prostate orgasms. So it’s understandable that men are searching for the down low on what these prostate toys are all about.

For one, prostate massagers are about better and hands-free orgasms. Of course, this is where a lot of the hype comes from. If it’s done right, milking the prostate makes orgasms up to 33% more intense, according to research by LELO. Lots of guys even experience multiple orgasms through prostate massage.

Prostate massagers are for men of all sexual orientations. For a long time, men assumed anal play was strictly homosexual. Straight men reserved prostate massage for the doctor’s office, since “milking the prostate” is a process used to check for prostate cancer. If you’re wondering about this process, search for a prostate milking video online.

Prostate massagers are about better and hands-free orgasms.”

Prostate masturbation or partner play is only intimidating on the surface. Don’t worry; your lady friend won’t be scared. Based on the research by LELO, 80% of women would perform a prostate massage for their partner.

A tragic number of men were missing out on a fundamental side of their anatomical pleasure. Now, they embrace anal play as the key to the same face-numbing orgasms women gush about.

Plus, consider the health benefits of prostate massage. Doing it regularly may decrease the risk of prostatitis, prostate cancer, erectile dysfunctions, and frequent nighttime urination. I think that seals the deal.

What is a Prostate Massager?

Most prostate massagers look a lot like a dildo, but shorter. Though they vary in shape, size, in color, they are all curved with a narrow tip for direct stimulation of the prostate gland. The tapered design of a prostate massager also makes anal insertion pretty easy.

The prostate gland is located about two inches inside your rectum. It feels like a walnut shaped nub on the anal wall closest to your penis. The prostate gland stores semen and provides a dose when an ejaculatory orgasm calls for it. While you can find and feel the prostate with your fingers (and a lot of lube), prostate massagers enhance the process and make a prostate orgasm more achievable.

Different Types of Prostate Toys

All prostate massagers are similar in appearance and function. The main differences you’ll see between toys are minor or stylistic details. The shaft of some prostate massagers are swirly, or bumpy, while others are straight — that sort of thing. Every prostate toy has a shaft for anal penetration, which is really the most important part.

NOTE: Don’t get any ideas about a homemade prostate massager, this area of your body is incredibly sensitive and requires professional toys.

Currently, there are three main types of prostate massagers on the market that you should know about.

  1. Classic Prostate Massager

A classic prostate massager is a short, phallic shaped toy. It has a narrow tip specialized to stroke the P-spot (the prostate). Typically the shaft has curves or textures to better accommodate anal insertion. The Aneros Helix Prostate Massager has been in the game of prostate pleasure since the beginning. Its shaft is extra narrow, it has straightforward design, and there are tons of resources available online to help you figure if you’re using it right. The Aneros is an ideal starting point.

  1. Vibrating Prostate Massager

This toy is the same thing as a classic prostate massager but it vibrates. Some toys have a vibrator already built in. Others have a vibrating bullet that you stick in the toy if you so choose. Typically anything that vibrates is a fat bonus when it comes to sex toys. But not all guys like the feeling of vibration against their prostate. If you aren’t sure what you like yet, it’s a good idea to get a vibrating prostate massager anyways. That way, if you like the vibes, you’re set. If you don’t, keep the power off. The Lovehoney Ripple Rider 5 is a winner, with an extra narrow head to help you locate the P-spot if you haven’t yet.

  1. Cock Ring and Prostate Massager

Cock rings go around the base of the penis to make an erection harder while prolonging ejaculation. They also intensify any kind of penile stimulation. When you couple the cock ring with the pleasure of a prostate massager, you’re super-sizing the orgasm. The Erection Enhancing Cock Ring and Butt Plug by Lyps is made of the highest quality medical grade silicone, with an effective design that has wooed every single user. If you’re looking for the peak of pleasure, this is it.

How To Give Yourself A Prostate Orgasm

First of all, congratulate yourself on making a huge step forward in your sexuality. Using a prostate massager has the power to revolutionize your sexual capabilities and satisfaction. Just by treating yourself to a massager, you’ve already succeeded.

How To Finger Your Prostate

Any self prostate massage will work better if you know the vicinity of your prostate gland. There are many ways to do this, but the best way is to use your own fingers (or your partner’s). This way you can feel it for yourself. Note — if you’re uncomfortable or worried about mess, you may want to look into douching beforehand.

Cover your finger and anus in lube generously. Make sure your nails are clipped. Insert your pointer finger 2-3 inches. Gently press your finger pad against the front wall of your rectum, the one closest to your penis. The prostate gland will feel like a bump, about the size of a walnut. It can take time and practice to locate it.

Once you’ve located your prostate, trace your finger in light circles to experiment with stimulation. Now, try doing the same process with your prostate massager.

How To Do A Prostate Massage

If you’re by yourself, the best way to use your prostate massager is on your side, with your top knee hugged up towards your chest. I still recommend this position if your partner is providing the prostate massage, although all-fours is also a popular option.

Make sure to read the directions for your toy so that it’s fitting your anus the right way. (It does make a difference; there is a top and bottom on every toy.) Use tons of lube and insert your toy slowly. Take your time! The most important component in prostate pleasure is that you are as relaxed as possible.

For 10 minutes to a half hour, keep the toy inside you without moving it. Regulate your breathing. For beginners, it can take 20-30 minutes for your anal muscles to relax around the toy.

Once you feel at ease, start contracting your anal muscles. Breathe in when you squeeze, breath out when you release.

Important: Just the anal contractions alone are meant to stimulate the prostate. You or your partner should not move the toy in and out.

It’s up to you whether or not you touch your penis during a prostate massage. If you want a hands-free orgasm, of course, keep your hands out of it. But adding in the penile stimulation adds a different kind of pleasure. Plus it gives your partner something to do.

Keep going with the massage for as long as you want. If you’re new to this, keep in mind that it can take time to habituate the prostate to stimulation. Some have to “teach” the prostate to feel pleasure through routine prostate massages. No one ever said prostate orgasms were easy, but everyone said they were worth it.

Safe Prostate Massage Materials

Just like any other sex toy, you need to be wary of the materials your prostate massager is made out of. Most are made of silicone, rubber, ABS, hard plastic, or glass. To avoid risks that coincide with porous or toxic materials, do yourself a favor: opt for silicone or glass prostate massagers.

Hop to Chapter 2 to learn more about which materials are safe in your sex toy and which aren’t.   

Frequently Asked Questions

Q: I’ve heard that prostate massages can be painful, is prostate massage safe?

A: A prostate massage will only hurt if you aren’t gentle. When you are searching for your prostate gland with a finger or toy, be incredibly careful. The gland is made up of sensitive tissues, and if you’re rough you can cause serious damage.

Q: How often can I use my prostate massager?

A: Most industry leaders recommend using it 2-3 times a week to start adjusting to the feeling of prostate stimulation. Try putting a day or two between massages so that your body will arouse faster.

Q: Why can’t I orgasm when I use my prostate massager?

A: When you start using your prostate toy, the sensation will be subtle at first. Because you probably haven’t felt prostate stimulation before, it’s difficult to recognize the sensation. Allow yourself to get into a focused mindset to pick up on the feeling. As you get familiar with it, the sensation will increase in intensity until eventual orgasm. But it is a timely process. If you feel next to nothing in the beginning, that’s completely normal. Just keep putting in the time and you will see results.

Q: Can I use a prostate massager if I have a genital or prostate condition?

A: If you have any kind of diagnosed genital or prostate condition, do not use a prostate massager until a doctor has approved it.

Q: Should I touch my penis while I use a prostate massager?

A: There are strong opinions on the question, but it’s ultimately up to you. Some men say that stimulating the penis distracts you away from prostate sensation, making a prostate orgasm harder to achieve. Others just use a prostate massager as a way to amplify orgasms caused by penile stimulation. But if you want to achieve a true hands free orgasm, don’t touch your penis.

Q: Are there other ways and male anal sex toys that stimulate the prostate?

A: If you’re reading about prostate orgasms and can’t wait for the massager to arrive on your doorstep, you can try other ways to experience the pleasure. Anal sex, butt plugs, dildos, and gentle fingering work for some people, but not all. Experiment with different methods and see what feels best.

Q: What is a Super-O?

A: A Super-O is the name given to hands-free, prostate orgasms. It’s an over-the-moon intense, sometimes emotional, overwhelmingly pleasuring orgasm. Super-O’s are much longer than your standard orgasm, too. Guys who have had them rant and rave about the pure bliss of a Super-O, so you’ll know when you have one.

Now that you know all about sex toys for men and women, head on to the next chapter, Chapter 6: Guide to Sex Toys for Couples