I have, and still do, face this issue in my relationship. Even if the sex is fantastic, knowing that I didn't orgasm really upsets my guy. It kills me, because it's not a problem with him, it's just me, being a woman. I don't orgasm easily from penetration. I love penetration, but I NEED clitoral stimulation in most circumstances. Even when I squirt, it's because I have either external stimulation, or internal and external simultaneously. I can never do it on penetration alone.

What's worse is sometimes adding sex toys to the mix can bring about a feeling of inadequacy in the relationship. I agree with Lauren. What I've found works is guiding him with my own hands, or telling him exactly what I want when I want it. If you do choose to introduce toys into the equation, make him feel needed. Give him a role to play. Have him use a toy on you, or finger you while you pleasure yourself as well. Let him know that this isn't just for you, make it about him. Let him be a voyeur. He may even get off on it. Crazy as it sounds, sometimes my sweetheart and I will have what I refer to as "mutual masturbation sessions". We won't even touch each other. Just do our own thing, eyes hungrily tracing the movements of the other. It's a very intimate experience.

It makes me feel better that other people experience this too, hah. The pressure does make it harder because I know he's disappointed. One night I just found myself sooooo close, and then he finished and I was really frustrated. When I get that close and it doesn't happen, it's almost like all my nerves down there are live wires and I'm left squirming. That was the night when he started this persistence, and while it's sweet, I just feel like I'm disappointing him when he doesn't hit the jackpot.

I'm the same way. While I love penetration, I usually need both penetration and clitoral stimulation to get there. That's why I usually prefer positions that keep him close to me, so I get stimulated even when he doesn't know it sometimes. But I know he likes to play around more and different things get him off and I love new and I love doing things for him. I've never pleasured myself at all in front of a boyfriend, let alone my current boy, but perhaps that's something the he/I/we could try

We used to have this problem a lot, but in our case it was his oral skills that were lacking. You know the drill: "I know what must work from watching porn! I'll just keep doing this one thing for a while, and you'll orgasm so hard and be so proud of me for figuring this out!"

After often getting bored and faking it so we could get on with having sex, I eventually told him, and he actually came up with a wonderful idea. I had no experience with blowjobs, and didn't know where to start; he didn't know what the heck to do when going down on me. His plan: I'd lay back, and he'd start experimenting with as many different things as he could think of. He'd try each one for about 30 seconds, and I had to tell him if I liked it or not, or if it was closer to working. If it worked, he'd give me another minute (reward us, and so he'd remember), then move on. If it didn't work, he'd just move on. The next night, the table would turn and I'd experiment on him.

It wasn't the most amazing foreplay, and was a bit frustrating that one night, but it meant that all of a sudden, the next time he tried he was SO much better.

Giving feedback during sex can be really hard. You worry that it'll be a mood killer, or hurt someone's feelings, or you get impatient because damn it, you want that orgasm! When you change the expectations (this is a learning session, we're not immediately trying to have sex; we're learning each others' bodies so that next time is better), it becomes easier. You're expected to give feedback. You're not expecting it to be amazing. You're expecting false starts. It takes a lot of the performance pressure off, especially if you decide before hand that it's ok whether or not you move on to sex and orgasms after.

But after all that experimenting (with fingers, with a mouth, or with toys), we were usually ready to jump each other.

I like that suggestion, Luscious Lily...that may be something I pose to him. :] Thanks!

I think I understand what you mean by getting bored. Sometimes I felt like my man was trying his best to stimulate me with his hand and it would work but it wasnt just right so the pleasure of the stimulation didnt last long since it wasnt right and I would always be left focusing really hard on feeling him work me but would get distracted by my breathing.

So one night I showed him how I liked it. At first he had a bit of a hard time remembering what I liked, it was as if he was programmed in the other things he used to do. I had to remind him a few times but now he does it well. He gets me very wet.

So now if ever he isnt doing something right either with his hands or orally I tell him as we are doing it so he knows and changes his tactics to more productive ones. I know I will not orgasm from oral, it just hasnt ever happenned to me, the pressure of the tongue is not enough to get me over the edge,but I'm ok with that and so is my partner.