Rocco,You both are relatively younger to begin with. What i mean by younger means not agewise but emotionaly you are not matured enough. And i have got confused reading a word 'engage'. At one point it appears that you tried to engage in physical act but did not suceed. Second' engage ' could be mean that you did everything in sex but actual penetration!
Then the third 'engage' where you want to get it on and hard with the commercial sex worker to be blunt or with an 'escort' to sugercoat it! (Which in itself is a bad thing which you know on your own and stll pondering upon it )
You began stating that you both have been in relation from last couple of years. Its clear that you both love each other and want to spend life together . But this thing of gettingrid of virginity is destroying your relation and life. But dear have you ever thought why she has been suffering this unbearable pain? It is natural that most of the females go through pains while having their first intercourse but once it is done they enjoy it fully and if one of us female members to be believed younger the age of getting rid of virginity longer are the days of them being active sexually (Not that it is true but question to this effect has been discussed in last couple of months). Reason for her experiencing such a pain could be that the hole of vagina could have been relatively narrow. To find it visit the gynac and she/ he will tell you the cause and if required give her a treatment.
If she could have been normal then you have to improve your technique . If you have been' engaging' in enough foreplay it will allow for her vagina to lubricate enough quantity of fluids that the penetration would be almost painless.
What i think is this could be an emotional issue on her part. She just is not able to overcome the emotional barrier of bearing the pain and the moment you approach her vagina her reactions starts coming in. It also could have been the reason that she does not want to loose her virginity before getting married. (If this being the case she is very much correct, not that i am against any premarital sex thing but then many girls prefer to stay that way for their very own reasons and justifications for which they are entitled to) So(1) you seek a medical help,(2) prepare her by having a lot of foreplay (3) find if she really wants to go all the way or not at this particular point of time and you will get an answer to your question.
If you decide to go for a complete sex then always remember to use condoms as we do not want you or her coming back to us asking questions like ' had unprotected sex, period dalayed , is she pregnant!'. Take an informed decision .Be prudent. Best luck.