Ask Isabella Q&A: Sex Doesn’t Work For Me

Molly writes:

Hi Isabella,

I really would like to read posts from you more frequently. I enjoy learning about all things sex-related. I enjoy sex very much, however, I have a have never orgasmed from a man. I have no problem climaxing when I’m masturbating, but other people just don’t do it for me. Is there any advice you could give me? I derive very little pleasure from the act of sex. It actually hurts most of the time. I would love to be able to enjoy sex as much as men do. Any advice would be very much appreciated!

Thanks,
Molly

Molly—

I would agree with you by saying I prefer the orgasms I receive from masturbation to the ones I get from sex. Although sex orgasms are very possible to have, they’re a little more difficult to achieve and are not as stimulating as masturbation orgasms. During masturbation, we can customize everything to our liking by using our hands. During sex, though, we have the ability to physically and psychologically connect to a real person, making the entire experience much more meaningful than masturbating. In my opinion, the pro outweighs the con and over time you will learn what sexual techniques work best for you to achieve an orgasm despite this initial state of “not knowing.”

I’d like you to ask yourself how many men you have ever had sex with and how often with each one. The act of sex is something a girl needs to get used to, so if you’re not extremely sexually active, then you’re not going to learn much about your likes and dislikes regarding sexual pleasure. The more guys you get to experience, and the more often, the more you will realize what techniques better suit you. But size is also a fair concern. It is key that the dick inside of you is longer than 5 inches and has substantial girth (the average vagina is 5 inches deep and widely varies in width). If you’re dealing with a short dick, there is a chance that he won’t even be able to reach your g-spot. It’s also important that the guy knows what the hell he is doing. Otherwise, you have a lousy dick moving aimlessly inside of you, which is just plain frustrating on a physical level. And your mind starts to race about where you’d rather be.

In order for me to have an orgasm from my g-spot, I need a thick long dick to thrust into me really really hard and fast (for momentum). Overwhelmingly heavy pressure highly arouses me, but I did have to go through many sexual partners before realizing this about myself. Great dicks definitely take some time to find. Guys’ sexual skills take some time to peak, too. Just the other night, I was fucking this guy, who I now call Sex God, who I fuck every few months. He’s always been quite superb in the sack and thrusts very aggressively exactly how I like it. But this night, Sex God totally surpasses my expectations and enables me to orgasm from my clit and g-spot SIMULTAENOUSLY! I am sitting on top of his huge dick (long and thick), which is the deepest inside of me it has ever been. And he rocks me back and forth really hard without ever raising me off of his dick the slightest bit. Sex God is so deeply inside of me that the rocking back and forth enables my g-spot and his mushroom tip to constantly pump against each other. The rocking back and forth also enables the bottom of his dick outside my vagina to rub against my clit. The double sensation—unfuckingbelievable. To think, all this time I had thought working for a clitoral orgasm during sex was a waste of time and energy. Boy, was I wrong. I would never have learned this trick without experiencing it directly with the one and only Sex God.

The bottom line is that you need to just keep gaining more and more experience (with men you have chemistry with as opposed to losers) and just keep trying new things. The reason why I know my vagina so well is because I’ve had experience practicing with it and learning from more sexually advanced partners. The men who have more experience than you are who will make you learn more about your body than you ever knew before. Have sex often— and you’ll progress. Every girl’s vagina is different, so my tips about positions will only take you so far. You have to experience your vagina on your own and just keep using it! Of course I strongly advise you to have your boy ALWAYS WEAR PROTECTION. And the thinner and more-ultra sensitive the condom is, the more intense the sex will feel.

Molly, I wish there was a simple one-line answer I could give to clarify all of this for you, but there isn’t. Your body is simply YOUR body and the skills of being able to pleasure your body during sex are what you will acquire ONLY after steady practice.

—Isabella

The individual who asked this question wrote it anonymously from a noreply@learnlink address. I always take the time and write personal emails back to every single sincere email that comes into my inbox. Sometimes I respond with follow-up questions and then it becomes a message thread. I really do enjoy talking about these things and offering my perspective, so please don’t be too embarrassed to enable a reply. I published this question anyway because I thought it was a good one, but I really would prefer receiving an email from an address that I can actually respond to. Otherwise it feels like I’m talking to a wall :( Besides, I’m not exactly publishing every question.