Aunt Shakti's Guide for Male Virgins

Sixteen months ago I took a break from purely tantra postings to post an article aimed at helping women have a painless and more enjoyable introduction to sex.  Even though it's not about tantra, that article, "Aunt Shakti's Action Plan for Proactive Modern Virgins," has turned out to be one of the most popular landing spots on this blog for new visitors and I've also heard privately from several regular readers that they appreciate being able to give out the link to young friends who are on the verge.

Then last month I was asked to provide advice for a male virgin.  The background was a little different.  The young man was distressed that he didn't know what to do and would feel ignorant and embarrassed.  He said that all he knew about sex was what he had seen online, but that he wasn't sure it would really be okay to do many of the rough things he regularly saw in porn videos.

Unfortunately, that's all too common these days.  Even mainstream porn is now increasingly violent and extreme, and it's easy for people who have been in serious relationships to forget that young people have no way to tell what is pure fantasy and what isn't.

The guide seemed to fill a need, so I thought I would post it here as a companion to that earlier article.  Here's a slightly expanded version of what I wrote:

Shakti's Guide for Male Virgins

First times are frequently awkward for everyone.  If your girl is a virgin too, she will have her own worries, much greater than yours, and you'll need to read up on that (see the links below) so you can help her get through it with the least discomfort and most pleasure possible.  If at all possible, the two of you should be completely comfortable being naked together, giving each other handjobs and and doing oral before you rush into penetrative "penis-in-vagina" (PiV) sex.

If she is more experienced than you are, make sure she knows you're a virgin and she's okay with that.  MOST girls and women know quite well that first-time sex is often awkward and even funny, and they are very understanding and supportive and happy to coach you. They will not be expecting great sex, so you don't have to worry about living up to some impossible ideal.  Instead, they will expect it to be warm, charming, funny at times, and tender.

Don't worry about losing an opportunity if she knows you're a virgin.  You really, really don't want her to have expectations that are impossible for you to fulfill.  If you sign up for a tennis match and claim to be an expert when you've never played before, you won't fool anyone and your partner will have every reason to be disappointed.  

So don't try to fake it and don't surprise her.  But don't be embarrassed about it either. Everyone has a first time and this is yours.  Most experienced women will be happy to guide you and most virgins will be happy to bumble through it with you.  The few who decline are typically the impatient or demanding ones who would make it bad for you anyway.

Preparing for Your First Time

Buy condoms and practice putting them on correctly.  You should be able to do it in bad light and still get the condom oriented the right way every time.  Pinch the tip and fold it over to be sure you always end up with no air in the tip, so that there will be space for your semen.

Get an assortment of condoms and make sure you have the right size.  A condom should be snug enough so it won't slip, but not so tight that it hurts.  Buy lube that is clearly marked "Safe for use with condoms."  Practice masturbating with lube and a condom on so you get used to the feeling.

Study some pictures and drawings of the female genitals so you have a sense of where things are, but also of how much women vary down there.  (A lot!  There's tremendous diversity in the size, shape, and color of the various parts, so every vulva is unique!)  Learn the names for the different parts so you can understand these directions and have an intelligent conversation with your partner.  There are links below that can help.

If you have a stubble, grow it out into a soft beard or shave it off.  No one wants to make love to a Brillo pad.  Leaving raw abrasions on your partner's face, breasts, thighs, etc., is not a way to charm her.

Arrange your plans so you will have several hours for sex in a completely private place. You will have enough on your mind without subconsciously being worried about time or interruptions.

Trim your nails and remove any hangnails and rough spots.  BATHE.  Brush your teeth, scrape your tongue, and use mouthwash.  Wear clean underclothes.  Stick a travel pack of kleenex in your pocket or put a box of kleenex next to your bed if you know the sex is going to be at your place.

So... now that you're all set, what does "normal" sex actually look like?

A Basic Script for First-Time Sex With a New Partner

First, forget everything you've seen in porn that involves roughing women up, pulling their hair, choking or slapping them, or doing anything to the anus.  First-time "get to know you" sex should always be plain vanilla unless you know exactly what you're doing and the two of you have explicitly agreed to go outside those limits.

Okay, with that out of the way, there are hundreds of variations even on "plain vanilla," and different women respond to different things, so there is never going to be any one script you can follow and get perfect results.  But it's still not a bad idea to have a not-too-uncommon script in your head as a point of reference.  So here's ONE possible way things can go:

Step 1:  Make out.  Kiss passionately and rub your hands all over each other's bodies, maybe even do some dry humping.  Breast play is fine if she seems responsive, but don't maul her breasts. Backs and buttocks are important too.  Don't rush this phase.

Step 2:  Get rid of the clothing, in stages if necessary.  Continue Step 1 with one hand cupping her entire vulva region (crotch), pressing firmly and rubbing her outer labia up and down.

Step 3:  When she is moaning/squirming/breathing hard/pushing against your hand, cautiously introduce your (clean, closely trimmed) middle finger between her labia.  If it doesn't feel wet – meaning more than just damp – withdraw your hand, apply lube liberally to your 3 middle fingers, and transfer the lube to all of the smooth pink parts between her outer labia.

Step 4:  Locate her vaginal entrance and clitoral shaft by touch and make sure both are well-lubed.  Be gentle; don't poke.

Step 5:  With one or two fingers, slide the clitoral hood up and down, sideways, or in circles on top of the clitoral shaft, avoiding the head of the clitoris.  If she seems responsive, keep doing this until she has at least one orgasm – if she can.  (This can take a while for some women, so don't expect instant results.  On the other hand, some women don't like or don't respond to a lot of stimulation here, so be sensitive to her signals.  If you're unsure whether to move on, ask!)

Step 6:  Slide downward, kissing her breasts and belly, and – unless she stops you – slide further down and begin using your tongue and mouth to lick and suck her vulva and clit. Cunnilingus is an art with infinite variations, but here are a few moves you can try to start with.  Use a soft broad tongue to lick from the vaginal entrance up to the top of the vulva, like licking an ice cream cone.  Use the point of your tongue to lick in the gap to one side of the clit, between the clitoral hood and the labia.  Place your lips around the whole upper vulva area and suck, moving your head to gently tug her vulva in different directions.  For bonus points, curl your two middle fingers inside the entrance to her vagina, press the fingertips upward, and stroke outward.  Experiment and pay close attention to her responses.  Keep doing anything that seems to be desired and effective.

Step 7:  If she is able to have an orgasm from oral, she may want to stop after one, or she may want you to to continue.  Some women also like continued stimulation during an oral orgasm, but it's more likely that she will want you to pause and hold her tight until she's done.  Usually, her hands will tell you which.  If she doesn't push your head away, resume whatever you were doing as soon as she seems ready for it, and continue until she makes it clear she's had enough.

Step 8:  When she signals for you to move on, roll away, carefully open the condom wrapper, and put the condom on correctly.  (You did practice this, right?) While you're doing that, ask if she wants to be on top.

Step 9:  Either lie flat and help her to get on top and straddle your hips, or move on top of her with your knees between her legs and your hips over hers.

Step 10:  Liberally lube your penis and/or her vagina. Using one hand, guide your penis into her vagina, unless she does it for you. If she's on top, she'll control the pace. If you're on top, SLOWLY press inward, pausing if she seems uncomfortable, and adjusting your angle and position as necessary, until you are at full depth.

Step 11:  If she's on top, keep your motions *small* and match her rhythm.  If you're on top, start stroking in and out as slowly as you can.  It's not a race.  You may feel an overwhelming desire to pound hard and fast.  Don't!  Walk, do not run!  Finish each stroke with a little extra pressure and a slight pause.  Listen to her breathing.  As it speeds up and she gets more tense, allow yourself to slightly increase your tempo to match.

Step 12:  When your orgasm begins, keep stroking as long as you can and then press deep inside and remain there holding her tight for at least a minute while you ejaculate. (Surprisingly, the actual depth of penetration isn't what counts.  What matters instead is the pressure between your body and her vaginal opening, which creates the feeling that you have made a deep thrust and are extending it.)

Afterward:  Withdraw slowly, keeping a firm grip on the base of the condom.  Remove it carefully, twist it several times near the base, and tie an overhand knot in it.  Wrap it in a kleenex and discard it, or put it where you won't forget it later.  Offer her some kleenex too. Wipe your fingers and penis with kleenex and wipe up any stray fluids. STAY AWAKE, even if you suddenly feel sleepy! 

If she did not get an orgasm at any point in the process and/or she indicates that she wants more, return to Step 6 and do your best.  Otherwise, cuddle as long as she wants to cuddle. Say things she wants to hear.  Tell her it was amazing, tell her she's fantastic, etc. Emotional intimacy afterward is important!  Men who skip it are viewed as jerks.  Don't let that be you.

Final Thoughts

As I said, use this script as a point of departure. It won't go exactly like this, and it may take a sharp turn in the middle.  If that happens, improvise!  Talk to her, ask her what she likes, listen to what she's telling you about what turns her on, and pay attention if she seems uncomfortable with anything.  For example, some women are shy and feel uncomfortable with oral sex on a first encounter, so give your girl a chance to head you off before Step 6.

But the most important thing of all is your general attitude.  

Be relaxed and confident in your ability to improvise and figure things out, but not cocky – no amount of study makes you an expert without lots of practice.

Remember to breathe.  Keeping your breath slow, deep, and steady helps you maintain your pace and control.  Quick, shallow breathing often brings on an orgasm.  So will holding your breath.  So remember to breathe!

Pay attention to how tight your muscles are.  If you find that you are holding your back, leg, and pelvis muscles really tight, make a conscious effort to relax them.  It will help you be less tense and it will help keep your movements more fluid and rhythmic.

Be passionate and enthusiastic.  Make sure she knows how sexy and attractive you find her.  Many women have body issues and a lot of insecurity about getting naked with a new partner.  If you make it clear, in words and especially in non-verbal ways, that you are thrilled and excited to be with her and that she really turns you on, you will be forgiven for any number of beginner's mistakes!

Be patient.  Your conscious mind does not control your penis.  The parts of the brain that do control it are going to be working overtime figuring out this new situation, and they may not do everything the way you want them to.  That's okay.  If things go off plan, just go back to steps 3-6.  You've got all the time in the world.  It's very common for it to take several tries to get everything to work right.

Try not to be goal oriented and do not set any kind of performance standard for yourself. Whatever happens, happens.  Sure, you want to ditch your virginity, but your primary goal should be mutual pleasure.  It's really not going to matter that much whether it happens this time or the next time as long as the sex is good, loving, and passionate.  And if you focus on her pleasure first, instead of yourself, there's much more likely to BE a next time!

Several guides that can help:

Aunt Shakti's Action Plan for Proactive Modern Virgins – for general advice, particularly helpful if she's a virgin too.

You Can't POP Your Cherry! (HYMEN) – Almost everything you've heard about hymens and virginity is false.  Laci Green helps set the record straight.  Mandatory viewing if she's a virgin too.

Better Sex 101 – anatomy and tips that most virgins have to learn the hard way.

And this is a book every man should read many times: She Comes First: The Thinking Man's Guide to Pleasuring a Woman, by Dr. Ian Kerner – the best book for men who care about satisfying women.

Have fun!