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.

No 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.

Relax

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.

Communicate

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.

Expect 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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