How to help my boyfriend?

Sooo we are fast approaching the six month mark (well, nearly!) and my boyfriend and I are having a great time together, I think we're still in the honeymoon phase. We love each other and he has said he wants to spend the rest of his life with me (strong words I know!) and we plan to move in together by our one-year mark in the relationship if everything goes well. We both know we're both in it for the long haul and we are like best friends as well as each others soulmates.

He can make me laugh, happy, or sad, and we have been through seeing each other drunk and sad and up and down. He's seen me have a mental breakdown and didn't go running for the hills, he helped me through it. If squeamish look away now!! --> I even started bleeding during sex twice and instead of freaking out and being disgusted he was more concerned for me, making me book myself in at the doctors and cuddling me for hours. He's given me a massage and looked after me when I'm ill... He's the One.

ANYWAY, after my huge rambly paragraphs... The only thing I wish I could help him with is his self-esteem. He is concerned that he doesn't satisfy me sexually, he has a smallish penis (I'm guessing 4-5 inches) and sometimes doesn't believe me when I say I've orgasmed cause he cums pretty fast. I explained to him that orgasms aren't everything and I love making love to him regardless of whether I have one or not but he wants me to have them. He thinks I should orgasm every time! I love all of him and his penis size doesn't bother me at all, as he uses it well and we do positions that are easiest for us. After finding out missionary is a no-go (he's heavy and even with a pillow under my butt he can't get in very far and his thrusts always end up with him falling out) we mainly sticking to cowgirl, doggy or spooning. He likes doggy the most though!

What can I do to help him boost his self-esteem? I tell him during sex how good it feels, how wet he makes me, etc. How amazing it is to look in his eyes as he cums. He isn't happy with his body either and dislikes his wobbly bits. I have wobbly bits too but I have lots of self- confidence... How can I pass some of this to my OH, and help him love himself?

This is a hard situation because im on the reverse and always feel like i can never satisfy i guy.

Does he know you have an account because if so you can tell him that i personally enjoyed my average (5 inch) boyfriend's cock to my large (9inch) boyfriends cock...

Oh my god orgasms are not always the be all and end all i wish he could understand that but maybe just tell him to play with you and get you really close before he actually pentrates you.

Plus try and explain to him there is a huge difference between fucking/having sex and making love. Its about the connection. Doggy is good as it helps create depth. You could buy a karma sutra book and work though it to find stuff that suits you both.

And if he really CANT believe that hes making you happy then love honey so sell penis extenders and extra girth toys.

Make a list of reasons why you love him and why you like being with him...or get him to make a list of ways he feels he is not good enough (in detail) like i cum to quick...or im not big enough...etc...and then for everyone he gives you can give him a million reasons why what he thinks is not true.

I hope this helps. Good luck please ask me if you have any questions

It sounds to me as though you are doing everything you possibly can already. I'm sure as you continue to grow together in your relationship his confidence will grow too.

Not very helpful, sorry but I just wanted to say that I don't think you are doing anything wrong. I hope you live a very happy life together, it sounds as though you are off to a great start :)

If he feels that he wants to last longer is the problem have you considered a delay spray at all, as I suffered many of the same problems when I met my gf. One of the products i can highly recommend is this:

http://www.lovehoney.co.uk/product.cfm?p=27146

I used to be slightly lacking in self confidence not so much anymore.The most important thing for me was to make everything be completely genuine. No matter how good you may be at faking an orgasm, it is not worth it, your boyfriend can proably tell at least some of the time, as a rule don't say something if you have to think about what you're saying.

Don't necessarily worry about telling him how good everything feels, they do the same in porn and I doubt many people really believe that. Make sure that everything you sayis genuine, not everything has to be positive (don't be negative but the odd "I prefer it when you do x,y,z"). Most people aren't great in bed to begin with, and everyone can improve, if he sees that you are slowly starting to orgasm more the longer you date then he will believe you are actually orgasming.

if this makes sense: Ttry not to convince him that he is more than good enough if you can do it more passively, it will come accross more genuine and so will work better. My best example would be smiling everytime you see him rather than telling him he looks great immidiately after he compliments you. (I'm not saying don't complient him. If you compliment him and make him question it and you argue your case will make him feel really god about himself)

Most importantly give it time you're not going to improve his self esteem quickly, he's probably been thinking it for as long as he remembers, and so isn't going to change over night it could and probably will take years.

It sounds to me that you are doing a great job on his self-confidence already. It will just take time for him to actually start to believe it and to believe in himself. Please don't worry, I think things will turn out just fine, and I am so happy for you that you have found someone so special to share your life with :D xx

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OPJ, I don't think she is faking orgasms? I think what she's saying is that she does orgasm, but he doesn't believe she has? That's how I read it anyway.
My husband used to feel like this too, that sexually he wasn't good enough as he came too fast. But we just have really long, great foreplay, where I get to come, then it's his turn. This works great for us, he loves 'exploring' me with toys and so its pleasurable for us both. Hope that helps x

I wasn't sure whther or not she is so I thought I'd put it in just in case as it is pretty important to me at least.

mainly my point was just be as genuine as you can

As people have said, be genuine. Speaking as a man who used to suffer self esteem issues, the best way to make him believe that you like sex with him is to SHOW him you like sex with him.

Don't wait for him to initiate sex. If you feel horny, come on to him. Initiate it yourself. I personally love it when my OH tells me she wants me and is all over me.

I know people are recommending toys to use, but don't do that yet. It will probably make him feel worse going, "Hey, you know you dont last long during sex? This thing will help!" That's something you want to bring up when you are BOTH comfortable with each other.

Also remember, 6 months isn't THAT long a time. It took me and my OH a few years to get completely comfortable and begin being able to explore each other properly. Confidence will come in time.

My advice in a nutshell: Don't bring it up to him unless he mentions it first, don't mention any performance enhancing toys, that's likely to upset him, initiate sex more often, don't wait for him to come on to you and give it time. This isn't a case of sex life needing to be spiced up. It's a man who loves you wanting to give you as much pleasure as possible. Just keep showing him that you do, that you love him and his body and he'll get the message in time.

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Size isn't everything . Its how you use it that matters. Keep praising him expecially the parts that he doesn't like or feel confident about.

To boost his confidence tell him that his member is the right size for you and anything bigger will likely hurt you .

Keep communicatong with him and praising him and his confidence will grow. At that stage introduce a vibrating cock ring but tell him its for your benefit as well ie a couples toy. That will help him to keep to his max size longer and give him confidence.

Good luck

To OP, it sounds like you're doing everything right! I know it's not nice to hear when you just want him to be happy, but you can't make him feel secure in himself. Your current actions and time will certainly do so, but there's no quick fix I'm afraid. Just keep being as supportive and loving as you are, given enough time he will find comfort in your actions as much as your words :)

And regarding performance enhancing toys, definitely let him be the one to bring that up. You doing so could reinforce that he isn't good enough, whereas if he brings it up it's a case of 'I don't think you need them hun, but if it would make you feel better lets try them'.

You can get penis extenders that fit over the cock to give an extra few inches and feels really real my fiance thought he had a 5 inch cock for years until after 4 years of being with me i measured him and hes actually 7 re asure hi that you enjoy it and even if you dont orgasm try using sex toys together this will help both of you feel more comfortable in the bedroom

Have you tried having orgasms before penetration? If you give him a blowjob and really make him enjoy it, the sit and play with yourself, make yourself cum good and hard. This will give him time to recover and should delay his next orgasm. The opposition should work for you.

Once I have had one orgasm they come thick and fast.

So after having a bit of fun with him watching then try penetration and see how that goes. You will already be wet and very sensitive and a do think you will orgasm with him.

good luck

With bringing toys in (if you want them) bring it up in a way of "I'm getting this for myself for when you're not around" then it is less likely to come across as he's not good enough and more you've found something that you want and turns you on which seems to be something he want.

some guys like having toys in the bedroom some don't although my guess is that most would come around to the idea

Another agreement that it sounds like you guys are doing great already. And its only 6months, it can take a lot longer to feel fully comfortable and familiar.

If he s worried about his penis size or you not orgasming enough then its likely he has a somewhat unrealistic view of normal sex. Either porn, the bullshit people say to sound better than they are, or past experience has led to this. Lots of us have been there . He needs to adjust his views but it will take time. Maybe get him reading places like this as the forums do give a great, if slightly more open and often kinky, view of real sex

Other than that just time. And tell him that.

On the personal note,
I worried with partners when younger because I'd been with some that orgasmed very easily and later ones didn't. Took a while to realise not all women are the same in that regard.
My other half is 35 and we've been together 18months yet only this year month has she felt relaxed and comfortable enough with someone/me to be so much more sensitive and able to orgasm much more intensely.
It takes time

Thank you for such good feedback guys! Yes we are doing very well, we're open with each other and he knows I test sex toys and own them for personal use. He enjoys it when I wear lingerie and loves me being confident :)

MissBrownEyes92 - That is a great idea to emphasise the difference between making love and fucking, we connect so well on a sexual level and can never keep our hands off each other... Seeing as we only see each other two times a week (and I sleep over if we're lucky enough shift-wise) I think we do pretty well hehe. Maybe I could write a list... Or a love letter! That sounds a good idea, thanks hun for the inspiration!

OPJ - Yes Char99 is right, sometimes I do orgasm but he doesn't believe me when I tell him I did. Other times I won't and even though I tell him it felt amazing and so connecting he'll still feel bad that I didn't cum. That's a good idea to say I prefer x, y or z without being critical and it also gives feedback on his technique. Cheers! I will try that!

Lovebirds - Yeah I think I will let him bring up toys/sprays etc even though they are really good ideas. I wouldn't want him to think that he isn't good enough or needs help... He actually confessed that he wants to see "what he's replaced" cause I admitted to him that I haven't used my toys since new year now. He said he'd like to use them on me! He hasn't mentioned it since but I haven't brought them to playtime yet. If he asks again I was thinking of bringing along the LH silencer USB clitoral vibe as it's small and non-threatening, and we could use it during sex.

Fun Louise - Yes I've had little orgasms before from giving him oral, and told him so, he seemed really chuffed but disbelieving a bit... Maybe if I gave him more of a show, and made it clear I was masturbating myself whilst giving him oral, he'd get off on that and feel happier that I came when/before he did. Yes orgasming before actual sex, maybe during foreplay, would be a good idea so we could have sex without him feeling worried/guilty that I may not cum or I haven't cum yet.

Everyone else thank you so much for your time and supportive comments! If I could reply separately to you all I would but I don't really have the time now!
Thank you for the tips, advice and general helpfullness and keep it coming, I love your ideas!

Sounds like you got some great advice. Hope it all goes well for you both x

Well the foreplay advice is working and I am orgasming before penetration, but our main problem is now that he goes up and down a lot during foreplay and when it does come to penetration he is not aroused enough yet and/or has lost it cause foreplay took too long. He feels very embarrassed and has gone down on me in these situations, or started kissing me again and touching me when he realises that he's not erect anymore. He then gets erect and sex happens but I know it's getting him stressed/upset about losing his erection. Is there anything I can do to help him maintain a stiffie (haha that word) or stop him from losing his erection or is this totally normal?

Simple- Use the vibrating cock ring as I prescribed in my previous post. The type I use is a top quality one and was bought from another well known chain( the only toy that I have bought from else where. All the rest are LH) . You need to place it on him , with lube of course, before he gets big. Then with that on if you stroke him he will get big and he will be able to maintain it . Set the cockring to vibrate and then ride him cowgirl or reverse cowgirl . I will guarantee that he will orgasm inside you . It certainly works with me as I had a simlar problem.Just to add why not wear you sexiest lingerie when riding him .A lady clad in stockings might be a turn on for him as well .

Thank you for the advice mysteron, that sounds like a brill idea! I have news!! He produced a cock ring during our last session, and said "I've been on your lovehoney site and I found one of these whilst browsing - fancy using it today? It'll help me be harder for longer."
I was surprised but happy and thanked him for thinking of me, I said something along the lines of that I'm happy without him using it but let's give it a try, it may help both of us. We didn't use any lube (I must remember to bring that up one time!) but we did use the ring and it helped a little, mostly it boosted his esteem I think cause he felt harder, and maybe bigger too? Anyway he lasted a bit longer than usual and I masturbated myself during sex which he found incredibly hot, and he came pretty hard :) I think we've taken a good leap in our relationship considering we can now talk about sex and sex toys openly. My sex cheques from LH are being well received too, he's cashed two of four already! Thanks all for your advice!