How to Lose Your Virginity

Welcome to Part V of our "How to Lose Your Virginity" series.

In Part IV, we discussed the "dating" process and what to do on each and every date.

Most guys will lose their virginity after Date #5 or #6; they are comfortable by then and the girls are ready.

Let's discuss the period after you lose your V-Card and some other potential issues that you should be mindful of.


After You Lose Your Virginity

First off - congratulations. 

You did it.

So now what?

No matter how much potential you see/don't see in your first partner, I HIGHLY SUGGEST keeping her around BY ANY MEANS NECESSARY (scroll down).

Even if she's insecure and begging you to be her boyfriend.

Next Stop - Sexual Experience

If you lose your V-Card with this process (as opposed to banging some random drunk girl from a bar), she/you will have some degree of feelings for the other.

That's great.

That is the reason that she is going to come back for more.

She is your ticket to shedding your sexual anxiety and becoming confident in bed with EVERY WOMAN that you nail in the future.

You are playing catch-up with the rest of us and this girl is going to skyrocket you forward.

You don't need to sleep with a whole bunch of girls to beat sexual anxiety or become good in bed (although it certainly doesn't hurt) - you just need to DO EVERYTHING with one girl.

Everything - 

... and Whatever Turns You On.

I suggest doing WHATEVER it takes to keep her around.

Even if you have to be a "nice guy" or put up with some bullshit.

It's only temporary and it's totally worth it in the long run.

All the while - continue meeting other girls and try to get them in bed too.
(if you agree to a committed relationship - then don't do this)

Meeting women while you are already getting laid is significantly more fun and easier.

Although you have a ways to go, it's a bit of a mini "Golden Era" and it's much deserved after years of involuntary celibacy.

Enjoy it and make it productive as can be.

Here is our famous "Retention" guide for how to keep fuckbuddies around -

Use it, but be flexible and don't be afraid to get close with the girl.

Potential Issues and Roadblocks

Here are some concerns that you may have:

Lack of Options in a Small(er) Town

The most legitimate problem with online dating is that (just like approaching girls in-person) there are fewer options in smaller cities.

That shouldn't stop you from trying.

Sign up for the free sites - Plenty of Fish, OkCupid and Tinder.

Consider signing up for pay sites -, eHarmony (last resort), HotorNot, jDate, Adult Friend Finder (just try your best), etc...

Are you telling me that you can't go out with 2 or 3 girls if you hit up ALL those sites?

If that's the case -



Where the hell are you living?
(this is part of the problem with your entire life)

If you are against paying for an online dating site, look at it this way -

If I offered you one of my girls to lose your virginity to for $29.99 (or however much a pay dating site would cost), would you do it?

The correct answer is -


Growing Unrealistic/Low-Odds Standards

A lot of the guys that remain virgins into their mid/late 20's, consciously or otherwise, make the decision -

Well... I've waited this long, so I'm only willing to lose my virginity to a BEAUTIFUL WOMAN. 

You can probably see the problem with this.

Meeting and sleeping with that beautiful woman won't be easy (otherwise it would have already been done) and disqualifying 90%+ of the opposite gender is a recipe for your "slump" to extend into your mid-30's.

The main reason you don't Get Laid on a yearly basis is the same reason that other guys don't on a weekly basis - 

You are only open to meeting THE PERFECT GIRL and don't even give the rest a chance.

I'm not telling you to flat out 'lower your standards'.

But I am telling you to BE OPEN to more women if this is an issue.

There's an above-average looking nice girl with overgrown breasts that will fuck you after 5 dates and keep it real who will be a better first partner than the super hot girl that still goes to clubs for attention and has 10 guys chasing and jerking off to her.

You will have a hard time handling that "PERFECT GIRL" anyway.

You will be freaking out all the time and you know it.

Lose your V-Card to an attainable girl that turns you on but won't leave you in total despair if she walks.

Related -

I Want the First Time to Be Special

This is somewhat related to the prior concern.

While I generally think this 'I Want [Losing My Virginity] to Be Special' thing is a form of denial and avoidance, let's suppose your plight is authentic. 

The first time will be special.

It's the experience that is special, not the girl.

That is what you will remember.

You will be proud of yourself and you damn well should be.

In a few years, you won't even remember much about your first time other than you were nervous but you were successful.

You'll probably remember how happy you were the following day more than the actual sex.

After you have sex for the first time, you will be thinking "Damn... I want more pussy." and not "Wow, that she was so amazing and she's so perfect."

Stop thinking like a teenage girl and just go Get Laid.

Then do it again.

Online Dating is "Soft"

Some inexperienced guys will dismiss this guide because online dating is 'beneath' them.
(just like 90% of women are beneath them too)

They are "hardcore" players in the making.

That is an awful attitude to have and frankly the exact same attitude that has kept many of them sleeping alone for a lifetime.

Don't be that guy.

Say what you want about today's world of social media and declining social skills and physical fitness of our gender...


And I suggest that you take advantage of it.

Online dating is the EASIEST, MOST SELF-ESTEEM FRIENDLY WAY to lose your virginity.

I have a friend "Matt" who nails 25+ girls a year.

~ALL OF THEM he meets on Plenty of Fish or jDate.

He follows the exact same "dating" protocol that I have recommended to you - only he usually has them in bed on Date #2 or #3.

You can have a top 1% sex life JUST FROM ONLINE DATING.

I definitely think cold-approach and "party game" is worth getting into but don't think you can't tag 3 or 4 girls a month from the Internet.

What If She's a Virgin Too?

Although once you get a lot of experience under your belt, you probably won't mess with virgins (Brian and I don't) - if a girl shares with you that she's never had sex, I absolutely suggest that you take her virginity if she wants you to be her first.

You can even share your secret with her too.

She will like you even more but likely start looking at you as a long-term boyfriend.

With virgins, you will have to take the TOTAL LEAD but you will learn a lot.

There's nothing more amazing than teaching a young, inexperienced girl about her body.

The process is amazing and they stay around for months if you make them feel beautiful.

Inexperienced girls (virgins, especially) won't give you much feedback in the bedroom, but they are extremely loyal and you won't have to worry about them hooking up with another guy while you are dating. 

Their pussy is significantly more tight than the average girl, so you will have to gradually loosen her up.

Use 1 or 2 fingers at first and tell her to masturbate at home.

The first time experience for a female virgin can be a rough one.

I want you to reassure her and yourself that sex is not normally that way.

She will likely bleed, she may have tears in her eyes, she may be really nervous and confused as to what she should be doing during the process.

Just reassure her that she is doing a good job and is beautiful. 

Do not use your Bathmate to pump up your dick before sex. Your dick will not fit inside of her. Even if you aren't hung.

Will She Know That I'm a Virgin?

The answer is a very likely: 'No'.

If you simply follow this guide, you will appear more experienced/confident than most guys.

Even if you fall apart in the bedroom, so long as you undress the girl and eat her pussy - she won't think you are a virgin. 

She's seen erectile dysfunction (and premature ejaculation) before if she's had a boyfriend. It's not a huge deal unless it continues to happen.

If she hasn't seen it, then she isn't very experienced and you have even less to worry about.

If you are attractive enough for the girl to go out with, chances are - she thinks that you've been up with other girls that found you attractive too.

Even if she "finds out" you are a virgin, I see no reason why it would hurt you anyway.

If anything, she'll tell her friends and they will say that you are -


It's rare to find a male virgin. To girls - it's not a bad thing whatsoever. 

Beating Sexual Anxiety

If it's your first time (or your second time and the first time didn't go as planned) - you will probably have some sexual anxiety.

It's important to understand this about sex with a new partner for the first time - 

You can take some steps to make certain you get a good erection and perform adequately -

1. Take Cialis (go to your doctor for an Rx) 8-10 hours ahead of time. It works, that's why millions use it.

2. Practice jerking off in condoms (preferably to the girl you are going to sleep with). This will help you make sure you have the right size and get you used to being wrapped up.

3. Just go through the motions if you are nervous. If you take Cialis, your dick will be so sensitive that the slightest bit of pleasurable contact will cause an erection. Take your time, cuddle with the girl and try to keep your mind on HER and not you.

4. Remember - if worse comes to worst, you can always get the girl off with your hands and/or mouth. Some girls even prefer oral sex.

Go see your doctor for Cialis - do not buy it from an online pharmacy. 

Pour Conclure - Final Thoughts

That brings us to the end of our "How to Lose Your Virginity Guide".

I know many of you haven't known where to start, gotten highly discouraged from approaching women and will quietly follow this guide until it happens for you.

That is what I want.

I have a tremendous amount of sympathy for guys that are late-bloomers/adult virgins. 

Although I wasn't a virgin in my mid-20's, I consider myself a 'late bloomer'. 

Most of you guys have really beaten yourselves and may be living a total lie (appearing confident in front of friends, telling stories about getting laid, disqualifying girls that you like to avoid disappointment, etc.).

You haven't come to to become a "hardcore player", you have come in hopes of having a normal sex life and feeling decent about yourself.

I hear you. 

It's time that we start working toward that and get 'er done. 

If you follow my advice in this guide, in 6 months (likely sooner) you won't be a virgin anymore.

Come tell us your story, you should be proud.

Rooster's Program - How to Get Laid in 5 Weeks
(Even If You Are a Virgin)

Rooster aka Ross is one of our original members.

He is one of the only guys that I've have allowed to write blog posts that are published on

By now, he has more experience with online dating than I do.

I can actually learn from him at this point.

Recently, with my encouragement, he published his own guide specifically for inexperienced guys who may be looking to finally lose their V-Card.

It took him several months and he really put his heart into it.

I think it's very good and I've read every single page of it.

It incorporates (but in greater detail) what I have laid out and discusses other issues such as EXACTLY what to say, response rates, how to get your pictures rated, helpful mobile apps, tanning and additional anxiety issues that inexperienced guys tend to face with online dating.

He makes an effort to stay one step ahead of you and keep your mind right.

Furthermore, his guide contains a structured program that takes out the guesswork and tells you EXACTLY what you should be doing.

Like I said for Victor Pride's book, "30 Days of Discipline", if I made a "Lose Your Virginity" program - this is basically what it would look like.

Perhaps most importantly, he is providing support on "Rooster's Online Dating Forum" for those that join the program and additional help on Skype if you need it.

Whether you Get Laid in 5 weeks more/less depends on several factors, including: what city you are in, who you are willing to sleep with and your current physical appearance. Neither he nor I guarantee you will sleep with your first girl in 5 weeks.

But what I do guarantee is - YOU WILL EVENTUALLY LOSE YOUR VIRGINITY (or break out of your slump) if you don't quit.

In fact, although there may be some setbacks along the way, you will start to feel optimistic about your chances for finally getting laid.

For some guys - this will be the first time you have ever felt that way and the BEGINNING OF THE END of your life without sex.

I recommend his program and using him as a resource - 

Check out his other blog posts on -

If it matters to you -

I think I'm a decent judge of character.

Rooster is a good guy. He's not a piece of shit.

He genuinely wants to help people and will see that you won't get left behind so long as you put forth the effort.

Feel free to drop us a comment below, for specific questions about this guide or Rooster's program, please drop your message in our Online Dating forum.