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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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How To Turn Her On

Most of you reading this are probably hoping for some helpful “sexual” tips that might aid you in pleasing your female partner, more so, turning her on.

The truth is, the way to a woman’s heart isn’t through playing with her nipples, diddling her clit, or touching her in that place she likes. Sure those things help, but they’re not the the end all/be all of sexual arousal.

Most women need to be “in the mood” in order to reach an orgasm. i.e. relaxed, stress free, comfortable, and in a state of mind where they don’t have constant worries running through their head.

You can try all you want physically, but unless she feels that everything is taken care of, I can pretty much guarantee that you’re attempts at turning her on will be futile.

To help you understand why I say this I’m going to give you a brief glimpse of what runs through most women’s mind, even while your playing with that “special” spot…

*While you’re doing your best to get her in the mood:

Wow that feels good, a little higher, a little higher. He always knows right where to kiss me… don’t forget that the dishes need to get done. Why do I always have to do them? why can’t he do them for once?! Did he forget to buy toilet paper again? ugh, I hope the stores still open, these napkins are starting to rub me raw. That feels nice, a little lower, a little lower. Yeah right there. These sheets haven’t been washed in days. So gross. I’ll just put them in after we’re done. Perfect! I have to do the laundry I need that suit for work tomorrow anyways. What day was I supposed to pick up the dry cleaning? …

The best suggestion I can give when it comes to getting your lady in the mood is to help her feel like she’s not doing it all on her own: do the dishes, put your dirty clothes in the hamper instead of the floor, make her dinner, pick up the kids from school, bring her flowers, do some of the grocery shopping (without her), vacuum, dust, clean the shit stained toilet, or sweep. The more she sees you making the effort the more likely she’ll be able to let go and enjoy herself.

We women hate doing the house work just as much as most men do, which is why we appreciate it so much when you actually do make the effort!

Trust me, if your woman starts coming home to a clean house (one less thing she has to do) I can pretty much guarantee she’ll want to thank you for your hard work.

Don’t believe me? Give it a go for a full 2 weeks and see what happens…

*no I am not sexist in any way, nor do I believe in stereo typing, but I’ve heard it enough times from girls to know what makes the difference between him getting some or getting none.

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Having Sex On Your Period

Ever since I started making videos I’ve been consistently asked to cover having sex on your period. For as much as I wanted to, something internally fought me on it; the judgment, possible removal of the video, unnecessary flagging, trolls, wading through and deleting crappy/childish comments, dislikes etc.

With all the discouraged thoughts roaming in my head I put it off.

Truthfully, I just didn’t feel the need to invite any further negative attention, and assumed that a video on such a taboo subject would definitely bring that about.

Having said that, after much personal debate I finally decided that since these videos are for you – designed to educate, liberate, inform, and possibly help you engage in something you might enjoy – I would throw caution to the wind and make the video.

While having sex while on your period is nothing to be embarrassed about, ashamed of, or scared of, I do completely understand that for some of you it may be too “gross” to consider.  If you choose to have sex on your period, or not, that’s a completely personal decision that every person, and couple, has a right to.

If you want to do it, that’s okay.

If you don’t, well that’s okay too.

Just keep in mind that no actual harm can come from having sex on your period, nor can any damage be done. It’s just the body flushing out what’s no longer needed.

For those of you that want more information, here’s some links to sites that should be handy and helpful when it comes to learning about the ovulation cycle and menstruation in general.

Scarleteen, Clitical, Everyday Health, North by Northwestern – Carnal Knowledge

Regarding products mentioned in the video: Softcups, Diva Cup, Female/Internal Condom, and Diaphragm video.
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“Melon Balling” – a.k.a. titty f*cking

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Sex Ed 102 with Kara_Sutra: “Melon Balling”

For those of you not in the know,  “Melon Balling” is a term for an act you most likely know as titty f*cking, boobjob, titjob, coitus a mammalian, bangin the mams and pumpin the air bags…you should know what I mean by now.

The act itself is a low risk, non-penetrative form of outercourse that involves sandwiching a penis between a woman’s breasts and thrusting to create friction & visual stimulation for sexual gratification and arousal.

It can be used as a form of foreplay leading up to sex or in the place of sex itself,  without the worries of an unintended pregnancy or, if done safely, the risk of contracting an STD.

While it seems fairly standard, there are of course tips, tricks and techniques that can help make the experience a much more enjoyable one.

To learn more…watch the video 😉

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How to Choose a Sex Toy

Picking your first toy, or even buying your third, fifth, or tenth, can be an extremely frustrating, overwhelming, intimidating, annoying, and exciting experience. As someone who worked in a sex shop trust me I know, I’ve heard it a thousand times.

Fortunately I’ve crafted up this ‘quick beginners guide on choosing a sex toy that might just help you find something you’ll love.

Things to Keep In Mind

Before you go on the hunt for a sex toy, here’s a few things you might want to consider as they could help keep you from wasting money on something that’s far from what you really wanted.

Know Your Body

If you’re new to sexual exploration and/or don’t know your body very well, you might want to take some time to learn about your anatomy, as well as your personal likes and dislikes. Also, keep in mind that over 70% of ‘female’ bodied individuals require clitoral stimulation to achieve an orgasm. Sure, you could buy that cute little vibrator, but it probably won’t be that great if you don’t know what you like and what parts you’re trying to stimulate.

Know Your Needs

rabbit habitSpeaking of likes and dislikes, its best to not let appearances or things within the media deceive you. Sure the Rabbit Pearl seen on Sex In The City is a fantastic vibe (you can watch the scene here thanks to Dangerous Lilly), but that doesn’t mean that it will work for everyone or that it’s the end all be all when it comes to vibes. Figure out what you’re looking for personally (i.e. your needs) then go for the aesthetics.

How To Choose A Sex Toy: The Basics

Battery vs Rechargeable

no batteriesProducts that require batteries can be a major pain… especially when they die right before you climax. They’re also costly (over time), not that great for the environment, and can kill your product if they corrode inside the battery compartment. Rechargeable eco-friendly toys are often a tad more expensive but worth it in the long run. Do yourself the favor and shell out the extra cash.

hitachi magic wand

The Privacy Factory

Depending on where you live and whom you live with, you may need to choose something that’s discreet. If that’s the case items like personal massagers would be a good choice since they aren’t phallic and can be left out in the open without fear of being discovered. Although they are only good for external use, you can buy attachments that fit over the head for internal stimulation.



If it’s a gift for someone keep in mind that sex toys are a very personal thing. Some questions you might want to ask yourself before shopping; are they comfortable with toys, open to experimentation, have used them before and whether or not they have any specific likes in terms of color, shape or design. Any little personal details you can add will more often then not make a world of difference for the receiver.

Quality vs Quantity

cash-in-handFor most people spending over $50 on a toy seems a little unreasonable, but keep in mind that as it is in most industries, many sex toy manufacturers focus on creating high volume, lower priced products which unfortunately leads to poor quality, both in regard to the lifespan of the toy and the havoc it can create for your body. Personally, I believe it’s in your best interest to buy the highest quality sex toys you can afford, however I know that sometimes just isn’t an option. Fortunately there are lots of sex toys for around $20 that are pretty decent (the Pocket Rocket being one of them).

Shop Around & Read Reviews

Once you’ve got an idea of what you want look online for sex toy reviews to see if the product is good… or not. I can’t tell you the number of times I’ve saved myself from buying something crappy thanks to an honest review.

All Sex Toys Aren’t Built The Same

Don’t blame all sex toys just because one doesn’t do it for you. If there’s something that I’ve learned through my explorations with over 200 products it’s that some work, some sadly don’t. It’s fair and totally to be expected. Fortunately I’ve been able to learn through my experiences and narrow down the specifics of what I require to get off. Sometimes I’ll go astray and choose something even though my better judgment told me not to, but for the most part the ‘wasting money’ days are over.

Product Sizing

Vaginal_Dilator_Set1When it comes to size, the best suggestion I can give is to be realistic; if having a finger inserted hurts, it’s best to opt for something on the smaller side, then when you’re comfortable and ready to move to something larger, you’ll be able to do so with a minimal amount of discomfort. Choosing a vaginal or anal dilator set is a good way to get more bang for your buck while also getting a variety of sizes to work with.

Good vs Bad Materials

give_thanksFinally, pay attention to the materials. Unfortunately the sex toy industry isn’t regulated, allowing a plethora of crappy (read: potentially dangerous) sex toys to make their way into your bedroom drawers. When choosing a toy make sure to choose something make of 100% medical grade silicone (not a mixture), glass, ceramic, finished wood, metal, ABS plastic, and/or Thermoplastic Rubber (though I’d only opt for it as a last resort). Your best bet for choosing body safe sex toys is to shop with reputable sex toy retailers and manufacturers.

When All Else Fails

At the end of the day I know how hard choosing a sex toy can be, especially when you really don’t know what you want. When it comes to those situation, I’ve got a solution; rather than forking out a bunch of cash for one specific item, opt to buy yourself a few at lower prices so that you can experiment and see what works for you. Then, once you know what you like save up and splurge on a big ticket item that you know you’ll love.

Hopefully by following this list of suggestions you’ll not only be able to find a toy that’s right for you, but one that will last for years and offer many hours of enjoyment!

Now that you know all the basics, this ‘How To Choose A Sex Toy: The Specifics” has everything else you need to find something you’ll truly love!
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