
Is there any manga that deals with being trans, not just cross dressing

http://www.mangago.zone/read-manga/kono_koi_ni_mirai_wa_nai/
Only one I know of

http://www.mangago.zone/read-manga/shimanami_tasogare/
This one has a bit of everything represented by different characters, being gay, cross dressing, and being transgender

http://www.mangago.zone/read-manga/paradise_kiss/
Not the main characters

What would you recommend to someone who is a yuri virgin?

Something light sweet for the first time. Citrus and Magan&Danai is an absolute must.
Then stuff that has sex scenes but not too graphic like
"My Girlfriend's Ex-boyfriend " "The Third Party" and "Prism"
Then eventually the good Yuri shit like "What Does the Fox say" There are so many good Yuri's out there it sucks they don't get the same recognition as yaoi.

http://www.mangago.zone/read-manga/girl_friends/
http://www.mangago.zone/read-manga/citrus_saburo_uta/
http://www.mangago.zone/read-manga/asagao_to_kase_san/
As for Citrus a character named Mei frustrates a lot of people at first. It takes until around ch16 for her to give Yuzu a break.
Two guys meet watching an outdoor concert, they get drunk and have sex in the seme's tent. The uke is bigger, has muscles and is a bit of an idiot. The uke is smaller and I think has a bit of a punk vibe. It was is a volume of shorts
http://www.mangago.zone/read-manga/sokuochi_yarichin_yankee/
This one. (▰˘◡˘▰)
It's chapter 5 from this manga! :
http://www.mangago.zone/read-manga/sokuochi_yarichin_yankee/