The good news is that even though he's only climaxed twice via penetration and intercourse, you know he's able to do it. That's a positive. Think back on those two times and try to remember specifics about what positions you were in and other circumstances of the encounter.
But, also consider this: He might have a sexual or emotional issue that he's too embarrassed to talk about. He may feel some shame or guilt that is preventing him from having orgasms during sex. Or, he might actually just like to have an orgasm via his hand instead of intercourse.
In tantra, some men train themselves to last longer during intercourse by learning to orgasm via masturbation more. It's possible that he's doing that. It's common that the first way a person (man or woman) learns to have an orgasm is the method they like the most because it's comfortable and familiar. Most guys have their first orgasm at a young age by using their hand, so perhaps it's just his preference. The thing is, you don't know why this is happening because you haven't asked him. The first step here is to talk to him about it.
Now, talking to him about it probably scares you, right? Some sex therapists say it's not a good idea to talk about sexual issues in bed. I disagree wholeheartedly. Bring it up in a playful, sexy way during foreplay when he's nice and relaxed. Set up a sex date that's all about him. Focus on learning about his body and pleasing him.
You can set a sexy scene in your bedroom with candles and music and give him a sensual full body and lingam massage with coconut oil. Since we know he likes to come during hand jobs, let me first teach you how to be the Hand Job Queen so that you can participate in his orgasm on this level.
Lingam is the Sanskrit word for "penis." Unlike your average hand job, the lingam massage involves not only massaging and stroking the penis but can also incorporate more advanced techniques, including the testicles, perineum, and the sacred spot (the prostate) as well.
Start the massage by rubbing coconut oil on his chest, penis, balls, and legs. Start by sliding your hands up and down his thighs before getting to the good stuff. This will also make him feel more relaxed. Compliment him on something you like about what you're seeing and touching.
From there, move on to the testicles. Gently, slowly massage them. Once you've teased the areas around the penis and he's clearly wanting more, move to the shaft of the penis. Vary your grip from harder to lighter. Vary your stroke sequences between straight up and down and a twisting motion. Vary the action from one hand to two hands. When using just one hand, alternate between using the right hand and the left hand. Vary the speed from slow to fast.
As you are massaging him, ask him in a soft, sweet, and sexy way what he likes. Ask, "Do you like when I stroke you like this?" Touch his chest and nipples and see what other erogenous zones he reacts to the most. Encourage him to guide you and tell you what he likes.
You can say, "I really want to please you. Tell me what you like." Or ask him directly in a nonconfrontational way as you are massaging his penis, "I notice that you come with your hand more; what can I do to help you come inside me?" Or, "I want to learn how to make you come during sex. What can we do to make that happen?" Ask him what his favorite positions are, what turns him on, and to teach you how to better please him.
After you give him the lingam massage, ask him to give you a yoni massage. This will help you explore your clitoris and G-spot more so you can find out what works for you. For women who haven't had an orgasm like yourself, it's sometimes easier to learn how to orgasm through clitoral or G-spot stimulation first, either through solo masturbation or having your partner stimulate you. From there, you can take what you've learned into your next sexual intercourse session and play around with different positions that help stimulate those spots.
Yoni is the Sanskrit word for "vagina." There are five yoni massage techniques that you and your boyfriend can play around with. Circling, for instance, is where you circle the tip of the clitoris with the tip of your finger to stimulate arousal, varying from smaller circles to larger ones. Alternate the pressure from light to heavy.
Another is pushing and pulling, in which you push down on the clitoris and make small push and pull strokes, and then slide your finger down the shaft of the clitoris. Do this on both sides of the shaft, keeping in mind that some women are more sensitive on one part of the clitoris than another.
During the massage, let him know what feels good and what doesn't. Encourage him to explore your body so you can learn together what turns you on the most.
If you really want to go deep, you can try my Tantra 101 course, in which I have more details on the lingam and yoni massages and how to let go of shame, as well as tips on orgasms for women, sacred masturbation, multiple orgasms, and more.
Look at the positive here. Imagine all of the untapped potential you're only beginning to explore. This is a great moment of time in your life when you're starting to actually tap into pleasure you've never experienced. Instead of thinking you're broken or something is wrong, I want you to think it's the start of an amazing journey in your life and be excited about it. You are beginning a journey of sexual awakening.