I am contacted occasionally by women who want to discuss losing their virginity with a straight male escort.

I am always happy to talk about this topic and to pass on what I know, even if you just want someone to talk to about it and aren’t considering booking a date with me. This issue is important enough that I am happy to give you my time if it helps make your first experience of sex a joyous, memorable one (like mine was).

If you are interested in losing your virginity with me then I will guarantee that your experience will be one to treasure.

I wrote an article on this subject that you may find useful, along with comments from readers: losing your virginity with a straight male escort.

I have also added another page about the practical physical aspects of losing your virginity and what you can do in preparation to make it a better experience: Advanced issue for virgins

So, how does a date with me work if it is your first time?

Firstly I have a rule now to make it an overnight date.  I have found that you will have the best experience if we have enough time to relax and get to know each other and still have enough time to slowly introduce you to sex and then explore it further.

I like to start in the afternoon, possibly with a late lunch or coffee, then retiring to a hotel, or wherever you would be comfortable. Then perhaps some long slow sensual massage, with music, kissing and cuddling …

From there I would suggest lots of physical exploration of each other. I think that losing your virginity should also be an opportunity to explore a man’s body, and learn about things like giving oral sex, putting on condoms, how to touch and please.

Then when we are both ready we lay you back (most women prefer missionary position for first time sex, but that’s entirely up to you of course) and taking it nice and slow we have sex for your first time. My focus is always on you and making it as comfortable and enjoyable as possible.

There will always be a little pain from first penetration (whether from a penis, or a sex toy) as you vagina learns to relax and accommodate something as big as a penis. Usually it comes from firstly the tip entering you which can be a small sharpish pain, then a deeper ache when I am fully inside you as the muscles deep inside are stretched.

Depending on how comfortable you are, I will just go very slow, perhaps thrusting just enough to keep me hard and let you experience that sensation of having me inside you. Eventually I will orgasm, which although it’s not my aim, most women seem to enjoy.

After the first time we can relax for a while, talk about the experience, play more, give you an orgasm and so on.

We can have dinner in there too somewhere of course!

Usually I would like to give you the chance to have sex at least three or four times. After the second time you are usually relaxed enough to really start enjoying the sex and have fun with it. Then you can explore different positions and techniques if you want to.

With an overnight date, you have the chance for some more sex in the morning too if you like.

Well, I hope that explanation is helpful.  If you have any questions, then please don’t hesitate to post a comment, or ask me via email.

John.