cutting before a cycle? and detection times.

I was reading over other posts and saw that many people recomended that subject to start a cutting phase before he hit his cycle, just wondering why he would want to do that first, reason being, I have my gear for my 1st cycle, although after reading about that, my bf is around 30-35%, however, I am 6'2", 290, (o-line), 24 y. I want to play around 295 or 300, does that mean I should lose as much body ft as possible, then blast the weight on during cycle. Also, I need to start ASAP for this to be a true summer cycle, fb begins late august and they start random testing around the middle of sept. I thought I could hit 10 weeks and leave a little bit of time just in case. Here are my plans though:
wk 1-10 sust 500mg
wk 1-10 EQ 300 mg
wk 1-4 dbol 25mg/d
clomid 2 wks after

This is what I have available now, ready to start asap. I have nolvadex on the way just in case, this will be my first cycle. One more question, since I want to play at a wt. no higher than 300, 295 preferrably, should I add a cutting phase towards the end of this? This is my 1st cycle, besides a (hate to admit after reading here) a dbol only cycle last summer which didnt do anything but small strength gains, but that could just be coincidence. Thanks for all your help

It's always good to drop some bodyfat before a cycle but if your truely 30-35% I don't think you'll be able to drop much b/f without loseing alot of weight. And with the position you play I don't think loseing alot of weight will be benificial for you.
I wouldn't add a cutting phase at the end either. I'd either cut or bulk. I wouldn't advise trying to do both.
As far as detection times: Sus is detectable for 3 months and Eq 4-5 months so that's something to think about....

Mate drop the fat, eat clean then start and take prociniplad if your worried about testing, the prociniplad helps mask the agent and if you test pos to prociniplad tell them you have gonareah. as you were embarased.