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First Time Sex Tips: For The Guys

Since most of the questions I’m commonly asked tend to be from those not yet sexually active, coming in the form of messages stating personal fears, worries, anxieties and misconceptions regarding the subject, I thought I’d write a series of articles to help guide my readers and viewers through their “first time”.

In the first article of this series I touched on the basics, including the decision about what type of contraception you’ll be using, getting products like a good lubes to help make the experience more pleasurable, the motivation behind the choice to be sexually active and making sure to have a person you can speak with, both before and after, who might be able to help and offer guidance should you need it.

For those of you jumping into the series, I highly suggest you go back and read the first article as it will possibly give you the insight you need to decide if having sex is something you’re really ready for.

As for this article, I’m going to be covering tips and suggestions I think every male should know before engaging in sexual activity, hopefully making the experience the best it can be for both of the parties involved.

*I’ll be covering first time suggestions for females next.

Getting Ready

No matter if you’re male, female or transgendered, I highly suggest masturbation before sexual activity. While this may seem like an attempt to keep you from having sex, nothing could be farther from the truth. To me, the act of masturbation can play an vital role in preparing you for your first sexual experience; helping you to learn about your likes and dislikes, giving you insight to how long you can “last” before ejaculating or having an orgasm (since they’re not the same thing), teach you about the type of stimulation you need to become aroused and maintain and erection (firm, soft, gentle, rough etc) and get you in touch with your body so that you can clearly relay everything you’ve learned to your partner. That said, if there is one thing I can’t stress enough it’s that communication is key to a good sexual experience – especially for the first time, but I’ll get to that in a bit.

tumblr_mpnkz1H5kv1rrlpmpo1_500No Glove, No Love!

While I brought up the issue of contraception and STD/STI protection in the first article, I want to touch on it again just to make sure you’ve got the bases covered and are well prepared to avoid any costly mistakes you may live to regret.

For Sex With Females: there are quite a few options when it comes to hetero sex; condoms, the female condom, birth control pill, diaphragm, IUD, the patch, contraceptive foam/spermicide and the sponge to name a few. Unfortunately when it comes to products females have to take/apply you don’t have much control over the proper application, but that doesn’t mean you don’t have the right to ask about them. After all, you need to take your safety and well being into consideration too.

On that note, the best advice I can give is to make sure you’re personally prepared by carrying a condom at all times, learn to apply it properly, find a size that fits comfortably by a brand you trust and never second guess your best judgment. If you’re about to engage in a sexual activity and don’t have a method of protection available, just don’t do it. Trust me, this is advice you might be thanking me for later.

For Sex with Males: unfortunately the number of available products for male on male sex is limited with the condom and spermicide (not recommended) being the only options. While you may not have to worry about a possible pregnancy, you should always assume the person your with has an STD/STI until you know otherwise. Better safe than sorry.

tip: if you’re unsure about what size condom you should be buying, I created a condom size chart which might help.

Tips & Suggestions

Some of the most common worries I hear from males are that they won’t last long enough, aren’t “big enough”, that they’ll do it “wrong” and finally that they’ll somehow accidentally hurt their partner(s) while in the process of trying to bring pleasure. If you can relate to any of the above, don’t worry, what you’re experiencing is normal, natural and definitely to be expected.

In an attempt to help I’ve listed some tips and suggestions that I hope will build your level of confidence as well, give you some insight regarding what to expect your first time around.


For as simple as it may sound, being relaxed is probably one of the best pieces of advice I can give. When you’re relaxed your heart rate is lower, stress levels decrease, the mind becomes still, you have a better chance of becoming aroused and any anxiety you may be feeling will usually drift away. Sure, it doesn’t seem like that big of a deal but maintaining a sense of calm will go a long way for helping you achieve an erection, as well as maintaining one.

My suggestion: When trying to stay relaxed you may think of the old standby techniques like breathing, maintaining a sense of calm and going with the flow will have the best effect, and to a certain extent, you’re right. However, I personally think being prepared in every aspect will make the biggest difference when it comes to the big day/night or otherwise. If you know how to put on a condom, what your likes and dislikes are, what type of stimulation you and your partner prefer, what type of lube you’ll be using and have talked about all your fears or anxieties with someone you trust, that will go a long way for helping you stay calm in the heat of the moment as you’ll already know what to expect and not be so caught off guard.


As I said early in this article, communication is key. Not only can it make a big difference when it comes to easing tension, calming nerves, learning about each others preferences and erasing fears, but it also gives you the chance to talk about everything before it happens so that you know, each step of the way, whether what you’re doing is okay or if it’s going too far too fast.

My Suggestion: The suggestion here is actually very simple – talk to your partner about what your feeling/thinking and listen to their fears, concerns, questions and suggestions. While that part is very straight forward, being a good communicator also requires the ability to listen and hear what your partner is saying. If they tell you (in the moment) that what you’re doing hurts, is too fast, slow, deep, hard, soft, shallow, or otherwise – stop, listen to what they’re saying and ask what you could do differently. I know it doesn’t seem like that big of a deal, but listening to your partner can be the difference between pleasure and pain.

tip: if you’re partner says that they don’t want to do it anymore – even if it’s right in the middle – listen to them and stop. It’s the respectful thing to do. More than that, if you don’t it will more than likely classify as rape and place you in a situation you’ll likely live to regret.

Be Gentle

Rough, passionate sex is great, but pushing too far too fast is a whole other thing. In fact, most people would probably be surprised by the amount of messages I get from viewers saying they don’t like sex with their partner because “he just shoves it in”, or that their partner won’t have sex with them because they accidentally hurt them once. It’s a common mistake, one that can very easily be avoided.

My suggestion: I don’t know how else to say this other than – don’t just ram it in there! Yes, I do know how funny that may sound but it sadly happens far more often than I care to admit. To help make insertion easier I suggest helping to get your partner ready by using lots of lube, making sure there is enough foreplay for them to be aroused, and inserting something small first (with their permission) like a little dildo, vibrator, finger or other object that’s safe for use (if it’s for anal use make sure it has a base so it doesn’t get “lost”).

Once inserted don’t start thrusting it about, don’t poke or prod at them, and don’t act like your a doctor giving your partner an examination unless your role playing. Instead, just let the item your using sit in place so that your partner can get used to the feeling of having something inside, while also allowing the muscles to relax and possibly “stretch out” a bit. When your partner is ready you can remove the device and slowly try to insert yourself. If it doesn’t happen the first time you try don’t worry, it’s common, normal and happens to even the most sexually experienced folks. Time and patience are your friends here, not a forceful jamming. It’s like the old saying goes – “if at first you don’t succeed, try, try again”.

tip: for those of you engaging in first time anal sex I wrote an article and created a video specifically covering the topic which you might find helpful.

Go Slow

Contrary to what most people think going fast and hard isn’t a requirement for “great sex”. In fact, it’s usually the exact opposite, especially if the person on the receiving end is a virgin as well. By going slow you give the person you’re having sex with the chance to get used to the feeling, without tensing up because they feel like their having sex with a jack rabbit on speed. While it may not seem like a very big deal, going slow can cause their muscles to relax and make penetration easier for both of you. not to mention possibly even bringing them to a heightened level of arousal in the process.

My suggestion: If you can, do your best to keep a steady rhythm going, one that is comfortable for both of you and feels good. If it’s too slow and not offering any stimulation slowly speed up, remembering to ask your partner every so often if it’s okay for them. Keep going until you find a speed that you both like and stick with it. Lastly, try to remember that you’re having sex with someone, not running a race. No one is going to clock you for the fastest time and it’s probably better if you don’t come first.

tumblr_mdta80tK9r1rol1w1Expect the Worst

While this might not seem that helpful I can guarantee that it is, especially considering that the worst thing you can think of may very well occur – what’s more, it’s normal, natural, common and for the most part happens to everyone. To help make my point let me just state that for every great “first time” story I’ve ever heard, there were at least anther 20 that were horrible, embarrassing or ended in a way that left one or both parties feeling like they “failed”. I know, it sucks.

My Suggestion: Be gentle with yourself, don’t take it too seriously and remember it’s your first time, not you’re hundredth. Just like riding a bike, learning to roller blade or playing a sport, being “good in bed” is something that comes with time, experience, learning, being open to change and willing to explore your opportunities. No matter how “perfect” you try to make it, I can almost guarantee something will go wrong. The more you expect that, the more able you’ll be in the moment to let it go, laugh it off, move on and not let it affect the moment.

Final Thoughts

No matter who you are your first time will most likely be scary, overwhelming, nerve wracking, exciting, intense and memorable. It’s supposed to be that way, it always has been.

Will you’re first time be what you expected? Probably not, but that doesn’t mean you can’t have a good time.

Will it be fantastic? Hopefully, though it seems first times rarely are.

Will it be something you always remember? I’d think so, which is why I suggest doing everything in your power to make it good, rather than something that left you wondering where you went wrong.

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Clitoral Stimulation Techniques


clitoris diagramFor those of you curious about clitoral stimulation techniques, including tips in regard to stimulating it during intercourse, as well as a few other facts that you may not know, this video should fill you in and hopefully help you find out what will work best for you.

Clitoris Facts

  • The clitoris serves no other purpose than providing sexual pleasure. In fact it is the only organ in the human body that exists solely for pleasure.
  • There are around eight thousand nerve endings within the clitoris, which is part of what makes it so sensitive.
  • Contrary to popular belief, the clitoris is much larger then people assume. Like a miniature penis, the clitoris consists of a rounded tip (the glans, think of the head of the penis), attached to a longer part (the shaft). The shaft has two “arms” that stretch backwards into the woman’s body, under the skin on either side above the vaginal opening. This picture shows the similarities between the clitoris and penis quite well.
  • Nerves controlling clitoral muscle contractions travel alongside the walls of the vagina, the bladder and urethra, passing along the sensations produced from orgasm or stimulation.  Which is why when a female experiences an orgasm during sex, the guy having sex with her will feel a throbbing or pulsing sensation inside her vagina.
  • When a person becomes sexually aroused, the clitoris fills with blood and increases in size just like a penis. After orgasm, the clitoris will return to its normal size. If the person doesn’t have an orgasm, the blood may remain there for a few hours and cause discomfort. This is pretty much the equivalent of “blue balls”.

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Male Sexual Response Cycle

Today’s video is going to cover the Male Sexual Response Cycle. For those that haven’t seen it, I created another video for the ladies to help them learn about their bodies and they way it reacts when a female goes through the phases. If you haven’t seen it yet, I suggest you check it out.

I’m hoping that through watching this video all of my viewers will not only become better educated in regard to their own body, but also will have a better sexual experience because of it.

The Phases Of The Male Sexual Response Cycle:

Male Sexual Response Cycle1.) Arousal / Excitement: This phase begins when your body first begins to respond to sexual stimulation.

Physical reactions like the following can be expected:

  • an increase in heart rate
  • flushing of the face and/or neck
  • nipples becoming hard
  • partial raising of the testicles
  • erection of the penis

2.) Plateau: This is the stage where your body is highly aroused and on the verge of orgasm.

Physical reactions like the following can be expected:

  • everything that happens during the first stage continues and increases
  • testicles will enlarge and be fully raised
  • a few drops of pre-cum will be secreted by the Cowpers glands. (This precum is meant to lubricate the urethra, as well as clean out any bacteria that may have been left behind)

3.) Orgasm / Climax:

This phase tends to be slightly different between men and women, with the men experiencing it in two parts; the first tends to be a moment of inevitability characterized by sensations that mark the point of no return with contractions occurring in the testicles, prostate and seminal vesicles. The in second part is the ejaculation of sperm due to contractions in the urethra and penis. Typically the actual orgasm lasts less than one minute for most males.

4.) Resolution: the body slowly returns to normal:

Unlike the female, who can be responsive to stimulation even after orgasm and even have multiple orgasms, the male typically goes through a period of unresponsiveness or a refractory period where he is no longer able to be aroused and needs some time before he can get another erection and orgasm. Tho this is true for most males, its not true for every one.

I do highly suggest that you take the time to learn about your body, either during masturbation or intercourse and see if you can identify the phases as you are going through them, which will in turn help you to become a better lover.

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Cut vs. Uncut

A lot of you have sent me questions and concerns about either your body or your partners body, especially in regard to foreskin. Unfortunately, those questions aren’t going to be answered in this video. Instead, I’m going to make a separate video at a later date that addresses everything you’ve messaged about.

Screen shot 2014-03-29 at 12.25.41 PMThis video is going to focus on making you a better lover and helping you understand – from a females perspective – whether or not being circumcised makes a difference when it comes to intercourse. Having said that, I’m basing the info and point of view within the video on the messages I’ve received from my female viewers – not just my own opinion and experiences.

To answer the question as simply as possible (again, I’m basing this on the number of emails I received from female viewers I polled about the topic)…  Yes, some women love cut dicks, others don’t prefer them, some don’t give a rats ass either way.

Whether you’re circumcised or not, great sex has less to do with your dick and more to do with how you use it, how well you stimulate your partner (in the way that they need), how open you are to feedback and honest communication, and how willing you are to make adjustments so that they can have a great time.

Key points to remember :

  • 70% of women require clitoral stimulation to achieve an orgasm. Your penis, as wonderful as it may be, cannot provide the necessary stimulation to her clitoris to get her to orgasm.
  • when it comes to sex and pleasure, not everyone is the same. The most important factor in being good in bed is learning what your partners likes and dislikes are and providing them.
  • Whether you’re cut or uncut, I highly suggest the use of protection to keep you safe from STI’s and unwanted pregnancy.

As always, if you are like me and understand the importance of inclusive sex education and want to help support what I am doing, please link, forward, or embed my videos to anyone that you think might benefit from them.

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Beginners Guide to Penis Extensions

After two years of questions from my viewers about their penis, its size, and how to make it larger, I thought I would offer a couple product reviews that might potentially help.

Before we move on, I just want to emphasize there is nothing wrong with having a penis that’s not the reported ‘average’. There are many people that prefer something not so big, and considering over 70% of women require clitoral stimulation to achieve an orgasm (something PIV can’t provide), having a smaller cock may just come in handy (it’s better at stimulating the g-spot!).

Having said that, I realize there is nothing I can say to make you feel better about your size, so instead I’m choosing to offer help the only other way I know how… by educating you on some of the options available. Hopefully it’ll make you feel more secure and confident in your body.

Like I’ve said time and time again, you’ve gotta learn to work with what you’ve got.  And when you can’t, sometimes accessorizing it might just be the way to go.

Beginners Guide to Penis Extensions

penis extensionWhat are penis extensions?

Penis Extensions are accessories that can be used for a variety of reasons, the most common are to increase the length or girth of your penis, to sustain an erection, or increase the pleasure your partner experiences.

They are often found in 3 basic forms; Realistic, Latex Roll On, and Strap-On Extensions.


The first are hollow tube like structures that are placed over the end of the penis and slid down until the penis fills the space (pictured left). Most are crafted out of ‘skin like’ materials, be it UR3, Cyberskin, Real Feel, or otherwise. You’ll also find them made of silicone, PVC, and plastic (though the last two aren’t suggested as they’re not body safe). Skin like versions tend to be a tad pricier, aren’t very discrete, require cornstarch or renew powder to maintain their texture, can be difficult to clean since they’re porous, may slide off during use, and are more prone to tearing over time.

For those that have issues with keeping them on, you might want to try the Tommy Gunn version or a Traz Rhino as they use a ‘suction’ action to stay in place. Here’s a link to my video review of the Traz Rhino.

latex penis extensionLatex Roll On

The second type of penis extension is made of latex (pictured right) and is designed to be placed on the head of the penis and rolled down like a condom. These tend to be a little less bulky than the ‘realistic’ versions, are easier to apply, are far more discrete, and a lot cheaper. On the down side they tend not to last very long and are only good with condoms if large amounts of lube are used.

strap on penis extensionStrap On Extension

Finally, you’ll find strap on extensions. Like the others they’re hollow to accommodate a penis, however they are held in place by a large strap of elastic or other adjustable material that either fits around the waist, or a combination of waist and between the thighs. Although they are the most ‘sturdy’, easiest to care for, clean, and use, they tend to be made of sub-par materials (pvc, etc) and not the most comfortable since there is limited squish or give to them.

When looking for an extension it’s suggested that you think about what type of experience you wish to have, how long you want the product to last, if you are doing this for yourself or your partner, the size you’re looking for (they usually vary from 1 inch to 4 inches in length), how much you’re willing to spend, and whether or not discretion is of importance.

As seen in the video:

latex penis extension in beigeLatex Penis Extension ($5.40 – $17.44)

The extension consists of latex and provides a comfortable feel for the man and an enjoyable, natural sensation for the woman (or other man). The extension is flexible enough to fit over a range of penis circumferences so you dont have to worry about finding one that is exactly right. Just make sure that the extension is not too tight to be uncomfortable or too loose to fall off while inside your partner. If this is a concern, you may want to use a condom over the extension and the penis to help hold everything in place.
penis extension cyberskin

Transformer Cyberskin Penis Extension ($9.92 – $33.07)

Designed for wear during intercourse, the transformer extends the penis up to a full 4″ and enlarges the entire girth. Made of Virtual Touch CyberSkin texture for a realistic feel with Dual Density material in the tip for soft, yet firm penetration. The custom comfort design allows maximum satisfaction and fit during use. One size fits all; however, you can cut the sheath to desired length if necessary. Virtual Touch CyberSkin texture provides the ultimate experience in sexual pleasure and stimulation.

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