The special time known as our first time.We all here can relate.Do know,that fantasizing and reality are so different.Once the fantasy is fulfilled,new ones seem to emerge.Should you stretch it all out and try topping later or accepting semen on your first trip? Depends.  Maybe its best to stretch thngs out for later to enjoy one pleasure at a time.Maybe again, you see this as a one time fling.If you see this as a one time fling,then go all out and explore everyhing.If not, by all means stretch out the levels you attain.Being topped is usually the most intense sensation we can enjoy.Some like it hard and fast,some like it slow and easy.I tend to like being bent over and ravaged.Literally to hurt! But this is me.My first time was well searched out by recommendations from those in the know.I took the advice of many transies and focused on one certaain provider that all guaranteed would fuck the hell out of me.And yes, she did.Once the fantasy becomes reality,you may feel some emotions coming out.I did.I can remember looking up into her beautiful eyes as she deflowered me.The memory locked in me forever.I at first wanted a one time thing,but something got me addicted real quick.I then searched for more and more.Eventually I got to know all worth knowing in the tightknit TS community.Everyone knows everyone.Time has brought many a great experience and some total wastes.But I explore anyways.Always searching for the 'ultimate fuck'.As time has passed, I took bigger steps on what I wish to do and willing to do.The boundaries always seem to flex.In finishing,I have no regrets.I wish you well and hope you enjoy yourself.  Live your dreams,face your fears.

Yea, couldn't agree more tglover.  My first experience was terrible, in part due to my expectations, nervousnous, and shitty research.  My second experience was worlds better.

Admit to yourself:
a)You are pretty sure you are going to enjoy it, otherwise, you wouldn't bother. Imagine sucking cock and enjoying it as vividly as you can. Buy a dildo and practice. I would wait until you practiced with one before any of the anal stuff. Take it slow.
b)You've already decided that you are going to do it. Chickening out makes you feel weak and gutless, and you'll only keep wondering what you're missing.
c)What you are doing isn't hurting anyone, so to hell with them - it's all about you, and what you come away with from the experience. It's your dime.
d)Make an effort to relax and take it all in, even if you need a couple of shots of booze to loosen you up beforehand.
e)If you think being topped makes you gay, say to yourself, "So what? I'm GAY and I don't give a fuck what anybody thinks". There's more to being a man than vaginal exclusivity. Taking what you want in life is what makes you a man.
f)If it's not your thing, you will know - but be polite about it if it isn't. Offer her something for her time.
g) If you already have a pic of her, beat off to it until you are practically sick of it (don't worry - you'll be turned on enough to perform when you see her in person).
Good luck, and HAVE FUN!