sex advice column: He's set us a sex schedule and it's stressing me out

QUESTION: I never used to have problems reaching orgasm, but, aged 50 and after four years out of relationships following a bad break-up, I haven't yet managed to climax with my new man (of three months standing).

He's an assiduous lover and desperately wants to pleasure me. We're going to Spain in late August and he's set a target of making things happen there. But what if it doesn't? I fear he will lose patience and end things.

Rowan says the pair should look forward to holiday, and as soon as they learn to relax, the earth will move

ANSWER: The weight of expectation is stressing you to such a degree that, quite understandably, you're unable to release the tension - a situation made worse by the imposition of a deadline for your erotic compliance. How can anyone relax if they're expected to peak on schedule?
And it's not just your boyfriend putting you under pressure: you are placing yourself under enormous strain, too.
And no wonder. It's always difficult to come back to an erotic relationship after the last one ended badly, especially when there's been a gap of some years.
When people have been hurt, they tend to bury their most tender and open expression of feelings for fear they become vulnerable again.   
Most cases of anorgasmia have a psychological root, which is why it's proved so hard to develop a female Viagra.
You can't just treat physiological causes when there are so many complex emotional dimensions to the condition. The fact is that it's difficult to climax when you're not in your comfort zone.
You should also bear in mind that you're at an age where the menopause, or perimenopause, causes hormonal imbalances and depletes natural lubrication.
It's been four years since you had sex, so it's possible you have to adjust to this new stage of life, just as many women find their erotic wiring changes post-childbirth.
A large number report they find it more difficult to reach orgasm in their 40s and 50s and have to try new methods of stimulation. 
It's worth consulting a gynaecologist or sex therapist to see if there are simple remedies you could try, such as testosterone patches, oestrogen pessaries and even sex toys. (Coco de Mer stocks some very discreet vibrators.)
HRT helps restore libido for some women, but there are known (if statistically small) health risks involved, so talk through all the options with your GP first.
What's clear, however, is that if your partner stops being anxious about the orgasm issue, he will cease transmitting that anxiety to you. Tell him that he's a skilled and tender lover, that you adore making love to him, take pleasure from his pleasure and that it's difficult to experience a greater surfeit of passion than you do already.
It's pointless to measure a profound emotional, intellectual and physical connection in terms of numbers of climaxes banked.
Bear in mind your boyfriend believes he is being thoughtful and generous in striving so hard for your satisfaction. And, being a bloke, he's set a schedule, because that's how many men deal with emotional problems.
The main thing is that both of you look forward to this holiday as a blissful escape, rather than as erotic homework. My hunch is that as soon as the pair of you learn to relax, the earth will move.