A
male
age
36-40,
anonymous
writes:Hello All,I am a guy aged 23, single (in fact, never been on a date yet) and a virgin (no surprises). I am not really desperate to lose my virginity and I think I can wait till I find my true love or till I get married. But for the last two weeks or so, I was experiencing a tremendous surge in my sex desires and wanted to do something different from the usual masturbation which I have been doing all these years. But, visiting a prostitute was against my principles and I wanted a healthy and safe way of trying something new. So, I bought a sex toy that is supposed to provide an experience closest to real penetrative sex. And when I tried it out, I found that penetrative sex (with my sex toy) is a lot different than my regular masturbation. In fact, I had a tough time getting the full length of my penis into it (even though I used lots of water-based lube). My conventional masturbation technique involved the stimulation of my penis shaft more and it involved very little stimulation of the penis head. On the other hand, in penetrative sex (with my sex toy), my penis foreskin was pulled all the way back (I am an uncircumcised guy, by the way) and as the foreskin went all the way back, it was hurting me. In fact, I felt "stings" at the base of my penis head. I am aware of the fact that the ability of the foreskin to retract all the way is very essential and my foreskin is able to do that. But it hurts (the pain is not unbearable, but the pain caused prevents me from inserting the full length of my penis into the sex toy. Because, the more I try to insert, the more the foreskin has to retract and beyond a certain point I am not able to thrust in. That is the reason why I am able to insert like 60% of my length, and not the full length). Also the pain makes me wonder if penetrative sex is enjoyable at all..Moreover, my erection was not as hard as it used to be during my conventional masturbation.The following are my questions:1. Is a person required to make some adjustments during the transition from masturbation to penetrative sex? If yes, what are they?2.Will the "stings" in my penis head (when my foreskin retracts as far back as possible) reduce in course of time as I continue with this more realistic masturbation? In other words, will my penis get accustomed to this new method of masturbation? Please note that I tried this sex toy just today. So,...just a couple of attempts with this "realistic" masturbation.3. Will I be able to enjoy penetrative sex with my sex toy? (The toy's insertion passage is made of a material that is really soft and is said to be almost like a vagina. Also, it has many specially designed contours to increase the stimulation and pleasure). But presently, I am not even able to feel the softness, the feeling of being "engulfed", the contours and any special stimulation.)Any helpful tips, suggestions are most welcome.My heartfelt thanks for your time and effort in reading my post. I would be very grateful if you could help me out with my problem. Thank you very much and sorry for such a long post.
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erection, foreskin, my penis, prostitute, sex toy, vagina Reply to this Question
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reader, anonymous, writes (19 May 2010): This is verified as being by the original poster of the questionThank you TimmD. That was a nice answer to my question and definitely helped me. Thank you
A
male
reader, TimmD +, writes (19 May 2010):
 Male masturbation, this includes ALL forms of masturbation including fleshlights, etc... are not the same as sexual intercourse with a female. When you are a virgin (no matter what age you are) you just cannot understand until have have sex. The questions you are asking are quite common for someone who hasn't had sex yet. Other things you may experience include not being able to climax as easily with your penetrative toy as easily as using your hand, etc.
All I can tell you is when you do finally decide to have sex (and I commend you for waiting for the right time like you are doing) it'll be nothing like you have tried to duplicate through masturbation. Products like the Fleshlight may attempt to duplicate the feeling of inserting your penis into a vagina, but they do not duplicate a woman's vagina as a whole. There are things that happen to a women's body during sex as well as a man's that make it TOTALLY different than masturbating. I guarantee you will not be having the issues you are experiencing.
For now, do what works best for you. Your hand, this toy, etc. Do what doesn't hurt. Just know that whatever you do, it won't really prepare you for sexual intercourse with a woman.
Good luck.
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