It is quite daunting as a man when you know that most sexually active women are considerably more experienced than you and generally started out quite a bit younger.
I too used to consciously or subconsciously pass up on a lot of opportunities because I was worried about initially lack of experience and later, perceived lack of performance. Plus the porn & the wider media reinforce messages of women being creatures who demand multiple orgasms over a considerable period of time before you're allowed to come, otherwise the interaction is considered a failure. Women are often very wary of inexperienced men and it's not unheard of to be dumped if they feel they have to 'coach' a man. However, missing out on experience because you are short of experience is one of the most vicious circles out there. There's nothing worse than being horny but too scared to do anything about it in case you screw up somehow!
Some may find this morally questionable due to culture or upbringing but I think if you're losing out on women because you feel uncertain about the whole bedroom thing, it's not a bad idea to consider a decent escort. In many cultures it is seen as normal or even a rite of passage for inexperienced men to seek 'tuition' from a courtesan. If you browse the appropriate websites it's usually fairly obvious which ones genuinely enjoy what they do, offering a gentle, sympathetic service, and which are just out for mechanical rutting in exchange for cash. They won't be turned off if you explain the situation, in fact some actively specialise in 'initiations'.
Aside from any preconceptions about the morals, ethics and pride issues surrounding 'bought' sex, it's really a question of investing in yourself actually getting to a stage when you can easily get sex without having to pay. See it as being the same as paying a driving instructor - a means to an end rather than a last resort. The main downside is of course expense - driving tuition is cheap by comparison and hourly rates can rival a lawyer's - so it's not a bad idea to have a savings jar specifically for this purpose to soften the financial blow - just don't pay her in loose change, haha!
Once you've got naked with a few different chicks and got over the initial 'OMG I'm actually having sex' feelings it starts to seem a bit more normal and it becomes easier to escalate with women you meet and date.
I would say, however, if one does choose to follow this route, always use the internet to source this kind of help rather than street prostitutes as you're far more likely to come up against the usual negative stereotypes of drug addiction, human trafficking, angry pimps and so on by using the latter. So stick to websites where you can vet profiles and enter into some dialogue before putting yourself into positions where you have to part with anything.
