Not A Member Yet?

Your Email is safe | Cancel Anytime Lost Password

First Time Sex + Hymen Questions (Mailbag)

First Time Sex + Hymen Questions (Mailbag)

Devon may have the opportunity to be part of a young woman’s first time at sex and take her virginity. He has questions about the hymen.


Hello Susan,

I’m doing what a lot of people do —coming to you for advice!

I am on a dating site looking either for casual sex or possibly a longer-term relationship if things worked out.

For the most part, I get messages and photos from ladies/women between 35 and 65 (I’m 66 myself), but occasionally I get messages from MUCH younger girls from 19 – 25.

These generally tell me they are looking for, or just fancy, an older man; not an unknown phenomenon.

It is one of these girls, a 19-year-old, who is causing me to write to you.

She has specifically informed me, “I’ve been holding out with sex for the perfect guy and I regret that now. I was so young and naive to think to lose my virginity would play out like some fairy tale. I said no to several opportunities for my first time at sex and I need a man who knows what he’s doing and you’ve been around for a while.” 

We have exchanged several texts relating to this and more general ones. Now, I’m not so naive as to not be aware that this might be some ‘come on’ but at the same time she has given me no indication that she isn’t for real.

That all said, it has nonetheless brought me to a point where I’m thinking – If this does come about, I’m really not certain how to go about the task! Probably like a lot of other men, I’ve never had the privilege of having intercourse where it has been the first time at sex for the girl – not even with my wife-to-be! 😣

I have told her that it wouldn’t happen the first time we met and I would want to know there could be a connection between us and to be able to tell that she would be completely comfortable with me being the one. I’ve also told her that she need to trust me absolutely to take care of her well-being. So, setting up the first meeting, even with a friend present, will be key to that.

I’m quite well-versed in the female anatomy and am aware that the hymen can be broken in more ways than the use of a penis—tampons, horse-riding, cycling, gymnastics, toys, etc. At this juncture, I don’t know (because I haven’t asked) whether any of the above possibilities have occurred and thus it’s just the penis into vagina bit that’s lacking.

If we take it that the hymen is intact I’m wondering what will be the best procedure?

My thoughts are that I will have to consider the setting, from the whole ambiance to having towels available, that there would have to be a lot of foreplay to make sure she is sexually aroused with a lot of attention paid to the whole vulva area using both hands and tongue.

I presume – and here you can correct me – that becoming aroused will cause her to become ‘wet’ even though she’s not had intercourse at this stage. I would obviously be trying to monitor her emotional and physical changes and make a judgment that she was in such a state that the time was now ‘right’.

It is the next step that I’m not certain about.

I know that the hymen can be set up in different ways -a central opening, one more to the base, split, several perforations, even one big opening large enough to make it almost non-existent. Should I explore the vaginal entrance to see what type it is with my fingers first for her to get used to something entering her a bit or should I just ease my way in with my penis? (psychologically she’s going to want to have my penis in her).

From what I know, since the hymen is at the very entrance of the vagina there’s not going to be any advancing bit by bit as when entering the anus, so it’s all going to happen straight away. Any tear-producing blood could be traumatic or otherwise. The tear could/will bring pain? Will a girl expect full penetration once her hymen breaks? If she has been self-lubricating up to this point, would the breaking of the hymen cause her to dry up and thus make penetration difficult (use of lube?)

That’s as far as I’m going! My guesswork might be near the mark; it could be way off. Hence I would now like to hear what you have to say about the whole process. I really want to know the best approach. This event will be the one and only time it will happen and thus I would want to make it the best experience possible for this girl for who it will be her first time at sex. I’d feel very privileged too at the end of the day that someone would place such confidence in me to “do a good job”!

Kind Regards,

Hi Devon,

You’re a well-informed and thoughtful man.

Thank you for taking such care with her virginity. When a tender lover makes the first time at sex special, it nourishes a person for a lifetime.

Don’t worry about her hymen. The chances of it being an issue at all are very, very, slim. You can penetrate her with your finger first to make sure the hymen is not blocking her vaginal opening. But 99% of the time, there is either no or very little tissue.

Penetration might stretch the vaginal opening and create a slight amount of bleeding. But if you use lubricant and go very slowly, she will be fine.

You might enjoy watching my video, “Losing Your Virginity.” It will put you in her frame of mind further. Your compassion is notable.

Click This Link ⇒ Watch My Video “Losing Your Virginity ” And Get Special Ideas for Your First Time At Sex


Next, please be careful that she is not “playing” you for money.

That is the BIGGEST issue about these online relationships with younger women. They often take advantage of men and the girls don’t even get the money… they are working for men who keep 95% of whatever she can get out of you.

KEEP AN EYE OUT FOR TROUBLE ⇐ 5 Ways You Get Scammed By Women Online


When you emotionally connect to her, it’s hard to have a clear mind… just be very cautious.

Guys write to me all the time that they have been ripped off.

It happens so much I wrote a book about the five ways they scam guys.

Please read the free ebook. It’s short and my friend Mark Edward Davis, who has helped many guys find the love of their life after they got ripped off, narrated it to me.

And let me know how things go!

her first time at sex

One Comment

  1. It’s exquisite not just fabulous!

Leave a Comment

Your email address will not be published. Required fields are marked *