Thanks SO much for the responses guys.

I took her out again today for a quick 30 minute ride, with no briefs on underneath my shorts just to see if that was the problem.
Alas, it wasn't. Still felt HORRIBLE in my "pereium" area. I even adjusted the saddle backwards and forwards to try and see if it was the position of the saddle but it wasn't that either. :/

I'm just going to take her in to the local bike shop and have them take a look, or possibly invest in a bib or some new shorts. Thanks again guys!

There is no substitute for saddle time to acclimate your butt on the saddle. You haven't ridden enough, period! Any adjustment to the saddle is not going to suddenly give you great comfort if you are not putting in saddle time. Now, what are you going to do once the LBS experts properly dial you in to your saddle, applied chamois butter and the best pair of bibs that money can buy and you still have pain? Are you just going to give it up and take up knitting?

Put in some saddle time.

Just scoot your ass back a few inches and enjoy.

I've rode 4x as much as you have this past week in cargo shorts and my taint doesn't hurt. Yours sounds like it needs some conditioning.

The condition is called "road chode." Like others have said:
Don't wear underwear under your bike shorts and find a saddle that is the right width to support your sit bones and is firm enough not to compress down to where there is pressure on your vitals.
Specialized's Body Geometry line of products for example has a very large selection of saddles in all shapes, sizes and firmness levels. I'm sure others do as well.

Its not a matter of new bibs or shorts. Its about finding a saddle that works go your geometry.
Nearly every response here was the same which concentrated on you looking into adjusting your saddle or finding a new. Out of all the replys here, you gathred you need new shorts? Come on dude. Take your bike in and we what they can do to help you.

I have found from my own experience that there is a major break in time for the saddle and your own body. That sensitive area of your body will toughen up. Secondly shed the briefs under the bicycle shorts, they will rub you raw and 3rd Chamois Butter(I think most bike shops sell it) helped me immensely, rub it generously into the chamois inside your bike shorts and on the appropriate area of your booty.

Like a lot of people already said: nothing under your bike shorts. I used to wear briefs too and they caused me major pain.

If it's a saddle/positioning issue it's not going to go away until you change saddles or move it in the right direction.

I only got back into riding this summer, too. My saddle was causing the same problem, pain in the taint area. I read a bunch and decided to try adjusting my seat. I planned on making small, incremental moves only, then ride and move again. My first adjustment solved the issue. I moved the seat back about 6-7mm, maybe 1/4 inch. Perhaps more importantly, I tilted the nose down, like someone else suggested, about one or two notches. Maybe a couple of degrees, max. I think the tilt probably did more to stop the pain, and moving it back was as much for balance as anything. I have no pain any more.
Good luck!

You didn't mention if you wear clipless pedals. If so, and you also feel penile numbness it may be your saddle is too high. Happened to me 4 years ago, after I switched to a new bike. Wanted to get more leg extension as I felt additional power, but it wasn't worth it. Lowering the saddle a half inch did the trick for me, I had to reach that after 2-3 adjustments, each lower than the previous. Hope this helps.

I'd like to add that one problem with soft saddles is that foam padding likes to fill voids. So even if your pelvic bones are softly ensconced on the wide part of the saddle, the foam in all the other places is putting pressure where you don't want it.

Get a well-made firm saddle that works with your anatomy and riding posture.

And right you are about the saddle too high, pecos. 39 years ago I went the route you describe and it hurt my crotch and bunged up my knees so badly I thought I'd never again ride more than 20 miles at a time. Then I fell in with a racing club, got some coaching, lowered the saddle, and learned how to turn the cranks around. Now, every once in a while I need to fiddle with my position, like when I buy new shoes or footbeds, and if my crotch hurts or gets numb, it's telling me to lower the saddle a half-centimeter or so.

I was having the same problem. Bought a new saddle and that did not help. Called the saddle manufacturer and they suggested lowering the saddle and using the fit chart that came with the saddle (read the instructions!). The manufacturers fit chart indicated I needed to lower the saddle over one inch from what the lbs had set up. Next ride was a thing of joy. I did get a bit of numbness after over an hour riding, but it went away after a short time standing on the pedals. I also got better shorts with a bit less padding and I can now ride for two hours or more with no numbness. You can also tilt your seat nose down and that will help the perineum but will put more weight on your hands.

U need a new saddle with a cut, that will relief the problem, like a specialized toupe or something maybe like a prologo that comes with diferential padding (hard in the back and soft in the front) that does the samething than a cut out.

Ask the lbs if they have a old one used one moving around for cheap, sadly for saddles u have to get used cheap stuff at the begining until you find the right one.

Another factor are the shorts, a lot of difference between a 25 bucks or a 80 bucks from performance than a nice 100 bucks castelli for example.

Good luck and hope the saddle is leveled.