Location: North Dakota
I’m a widow and I am so sad. The fellow I’m going with, I really love him, but I can’t have an orgasm with him. I was able to have an orgasm with my husband who is passed away. And I can when I am playing with a toy by myself.
He has such pride and I don’t want to hurt his feelings, because it would take me about a half hour of foreplay to get there.
You say that your man is prideful and that you don’t want to hurt his feelings. But are you really willing to sacrifice your sexual wellbeing on that altar? I hope not. Even prideful men can learn something about pleasuring the woman they are with.
Let’s just say that this guy your dating knew how to pleasure all the women he has ever been with previous to you. That pedigree doesn’t make him an expert on pleasuring every other women he will meet, and that includes you.
Allow me to share with you the exchange I had with another woman in your situation. Perhaps my advice to her will be helpful to you. This is from…
I learned how to masturbate when I was 12. From that first time I’ve loved how it makes me feel. No matter how good my lovers are; they never come close to the pleasure I feel when I’m touching myself. I like the intimacy I have with my boyfriend, but he’s not very good in the sack. I’ve been trying to get him to watch me masturbate, or we could masturbate together, so that he’d know how to touch me and make the bells ring. Unfortunately, he’s really straight-laced and he thinks my suggestion is perverted. He resists every time I bring it up. Sometimes after we have sex, I wait for him to fall asleep then get myself off. Is this selfish?
You betcha it’s selfish, selfish as all get-out. Not you, Zoe, but the bonehead you’re fuckin’. This is a classic, “you can lead the horse to water, but you can’t make him drink” sorta deal. Only here we have a “you can lead the horse’s ass to the mysteries of pussy, but you can’t make him appreciate them.”
I gotta ask, what makes a sexually enlightened chick like you hook up with and stay with bozo like him? Do you actually think that he’s gonna magically come around one fine day and let you lead him to nirvana? I think not. You know why I think this? It’s because you’ve created a monster — an “all I need to worry about is me gettin’ off in my girlfriend’s snatch” kinda monster. And that’s one scary kinda monster.
I am of the mind that it’s fruitless to try to get an obstinate partner, like your guy to do something he doesn’t want to do. The nagging alone will harden his resolve to resist. This does not mean you’ll never get your way. It just means that you have to go about this in a completely different way than, “oh honey, won’t you please cum and watch me jill-off? In the numbskull’s defense, he may be missing the point completely. He may not understand why you want him to watch you pleasure yourself. So if your agenda is to get him to be a better lover, that’s how you’re gonna have to approach the big lug.
First off, he needs to be told, in no uncertain terms, that he’s not the Hercules in the boudoir he thinks he is. This is gonna sting his ego like crazy and it might very well be the end of him and you altogether. But I assure you, risking this is much better than maintaining the status quo. Because, with each passing fuck, he will be more convinced then the fuck before that he’s da man.
Once you burst his bubble, you’ll need to immediately inflate a new one for and with him. Us men folk can’t live very long with out our illusions. Begin this inflation process by taking some responsibility for this predicament. Own up to keeping him in the dark about his lack of sexual prowess. Then tell him that there’s a very easy and fun fix for the problem. Maybe if he understands that you want to jill-off for him as a tutorial, he’d be more compliant.
I’d be willing to guess that if you made this presentation more of a game or a role-play scenario then a seminar he’d be more receptive. Why not try something like this. Introduce a blindfold into your sex play. Have him strip down to his jock for you, then blindfold him. It’s gonna be his job to get you off without using the magic wand he has stuck in his jock. The blindfold will necessitate that he use his hands (and mouth) to find and pleasure you. While you tease his dick inside his jock guide his hands to your pussy. He’ll no doubt be fumbling around at first, so you’ll have to encourage him with some dirty talk, or actually use his hand to jill yourself off. Just remember keep it fun and playful and keep his dick safely tucked away.
You can see how this little exercise could be educational for him without being emasculating. Once he figures out that there’s more to sex than the old in and out, he might actually cum around, so to speak. Similarly, you might, on another occasion, submit to the blindfold yourself and have him use your hand to jack himself off. In time, you be able to do away with the blindfold altogether. But then, you might want to introduce restraints of some sort. While he’s buck naked and restrained put on a hot and horny show for him. Tease him with your self-pleasuring, but don’t let him touch you. Maybe rub yourself with his stiff cock. Since he’ll be unable to resist, it will be like masturbating with his pecker. Doesn’t that sound like a load of fun for all concerned?