Feeling inadequate

[Beebearjo]

I wonder if anyone can offer any thoughts.

I’m a 49 year old woman, and after separating from a 17 year, sexually dull, relationship 5 years ago, I have been back dating for the last couple of years. This has comprised of many polite first dates, one relationship of a few months which was fun and passionate, and I have now been with my current partner for 6 months.

This partner is really sexually experienced, and has spent the last couple of years, since his divorce, in relationships with women who enjoyed going to sex clubs. He is also bisexual and clearly is not a man who would be content with vanilla. However, as a 50 year old man, he has some degree of erectile dysfunction, and some lack of sensitivity and difficulty reaching orgasm at times, due in part at least to him taking citaopram for depression. Oddly, he says he has never had an orgasm at a sex club. He seems to get most turned on when talking about me having sex with another man, and likes cuckold porn. I think he would genuinely like me to do this in a sex club environment if I was happy to.

I have always felt that my sexual skills are lacking. I absolutely adore sex but was a single mum quite young, so never gained experience in the ways that others may have done in their twenties. To put in bluntly, I have never masturbated a man, not really , And whereas I have brought past partners to orgasm orally, this was at a time when the men were younger and prone to being sensitive and orgasming very quickly/ easily.

Im so embarrassed about my lack of skills that I haven’t said anything to my current partner. Yesterday he walked in the door after not seeing each other for a couple of days, and a kiss quickly led to passionate sex. Lots of PIV then I orgasmed twice, from oral and then again from his fingers on my g zone.
He didn’t orgasm at all. This is common. I really want to make him orgasm in this situation but not sure how. There was lots of oral on him and PIV, but clearly it wasn’t enough for him in some way. Later, still naked, we got horny again and he masturbated then I put my mouth on him to finish him off. But I couldn’t get him there, my rhythm could not match that of his hand , and things petered out again.
I feel so humiliated, and although he says this is how it has been for him since he has got a bit older, he must be so frustrated. I actually feel a bit nervous of his penis, which I know is a weird thing to say.

I’m left feeling like the worst lover ever. I’m embarrassed to fully say how inadequate I feel to him, partly because I think it may make matters worse rather than better.

This relationship seems serious with a good chance of a future. He is very very loving and adores me. I want a passionate, loving, adventurous sex life with him, but feeling so inadequate and out of my depth like this isn’t healthy.

Any thoughts most welcome.

I can really sympathise because I have these problems of my partner not being able to orgasm, no matter how much PiV, oral or hand help he gets from me. It has left me feeling useless and that my body isn't good enough, similar to you. I have never had problems "getting them there" with any previous partner.

Mine is 40 rather than 50, but I have discovered he is somewhat of a porn addict. Normal, real life sex doesn't seem to do it for him because he's addicted to the extremes of porn and to the death grip of his hand, which my mouth or vagina are never going to replicate. If he gives wanking a rest for a couple of days before we see each other then he's more likely to have success having sex with me. If he doesn't get there, then I can't enjoy myself because I know it's because he's prioritised porn over me.

Your partner may want to see if a different SSRI might help, but you might also want to ask him about his porn use.

I think you sound so unhappy with this guy that after just a short relationship of 3.5 months, you should leave. There’s better out there. You don’t owe him anything. This is not going to get better. Do you want to be here five years in?

No, but after looking for 3 years and having absolutely no luck my self esteem is on the floor anyway. It isn't all bad with him by a long shot, but this aspect of the relationship could be a lot better, I agree.

@jubs15 I don’t think staying with this guy is going to be good for your self esteem either. This should be the honeymoon of your sex right now. Unless he can stop the porn and retrain himself which sounds not very likely :(

@Beebearjo i think my biggest concern for you would be would you be happy to have sex while your boyfriend watched? Your relationship sounds quite passionate apart from fact he cannot climax.

when I haven’t had sex for 4 years so was worried that I’d forgot, I read up on sexual techniques to make me more confident. It was called something like “the bad girls bible” and there are podcasts too; you might find them useful x

Doesthislookgoodonme
-thanks for that, I’ll look into it xx

Being masturbated by a woman is one of the best things ever and beats doing it yourself completely.

I suggest next time you are going to have sex that you start with foreplay, and spend time getting to know his cock. Combine oral sex with masterbating him....or both together. The grip of a hand is a lot tighter than a mouth or vagina.....and you can loosen or tighten that grip depending on what he likes. Also you can tease him by speeding up & slowing down.

I always think that being wanked off by a women is the most basic sexual act for a man. Always takes me back to being a teenager and the "making out" sessions with girlfriends.

Finally.....he is less likely to lose an erection this way.

I don't see why you think it's all about your 'lack of skills'. This is an older man with erectile dysfunction, and with - from the sound of it - a porn addition (which will desensitise him further). It's not you, it's him.

Also, - old bloke who goes to 'sex clubs' isn't exactly adorable. You can have a healthy and adventurous sex life without fulfilling these 'cuckold porn' (?!) fantasies he has. Fine if that's what turns you on, but it doesn't sound like it does and you're just desperately wanting to please him.

Big Gay bear-
This is the exact point. I never did any of this teen bedroom stuff when I was young. And I’ve got to this age without ever doing it. I know that’s difficult to believe. I now have a man in who doesn’t have the sensitivity he used to, needs a helping hand, and I’m too underconfident to properly give it.
There’s nothing I would like more than to be able to do that for him and for him to be responsive to it.
I’m increasingly nervous of his penis, which is ridiculous I know.
I kind of jokingly wish I had practised on all the younger, easily responsive men when I was younger.

Well, so much the better. For him it could feel like being with a virgin. Again I would suggest going back a stage or two. Kiss & cuddle on the sofa and start touching him with his clothes on. If he gets hard just stroke/rub the outline of his hard on. Maybe take jeans/trousers off but keep underwear on. Nothing better than foreplay through boxers. You can slip you hand in & just start playing with his cock. Surely you've done that before?

@Beebearjo look up Jenny Keane (via Instagram or her website). Every so often she does workshops that relate to sex skills for women & men. You have to pay but they get great reviews. She covers topics like blow, women on top & other things.

I feel for you and I hope it either improves or you find someone better. I know how hard it is to find decent (or even half decent!) men after 40, so I completely understand you wanting to see how things go.