Ruby...
What a wonderful and powerful 'connection' you have to your Guide/HigherSelf/OverSoul hon! Many who doubt the existance of theirs and who have not yet made that conscious connection would be most envious!
Indeed the male voice is that of your Guide! (Yang aspect)
Time and space are non existant on the level from where that dream comes... so the vastness is understandable! The swing is like your vantage point... it forms a structure of sorts - balancing you far above the 'time track' of 3D reality...
Soul is a unit of consciousness that has a 360 degree viewpoint!
I feel the dream places you at a Soul prespective - between dimensions, overlooking creation! You go there in dreams to swing (rock back and forth, or comfort Self) during times of stress... to check in with OverSoul and recieve Guidance! You have gone there so many times during your lifetime as you stated! The reason your Guide repeats this 'dream experience' is to get your attention and make you aware of the fact that you are never alone!
I feel the shapes you see in the dark may be Astral entities... they frighten you because you have not yet faced your fears of the unknown (darkness)! Meditate more... ask for direction and it will be given you! There is nothing to fear except the fear itself!
I hope these impressions help you understand these powerful, attention getting experiences! Thank you for sharing... it was a pleasure to read them!
Namaste...
~eerie