Daniel,
In so many ways you have experienced and received everything you asked for from Jen (Jennifer). As this thread is named "Want Virgin Girl Friend (GF) To Date Others", stated back on October 2015, you introduced all of us to your fantasy along with a plausible plan to help Jen connect with a friend (Aaron) of your room-mates.
Since October of last year you have come a long way with successfully turning your fantasy of Jen losing her virginity to another guy to the documented reality of Jen connecting with Aaron with your creative assistance.
You indeed do have an issue with premature ejaculation based on your assorted post; while you say Jen teased you that Aaron would not have allowed it to happen, effectively leaving her unsatisfied with her sexual experience with you. You clearly do want to continued your relationship with Jenn as an effective cuckold with it comes to ablility to satisfy your girl friend through intercourse. You truly do need to leave to be much more proficient and effective with giving Jen oral; it should consider bringing her to orgasm via oral before even considering intercourse with her and as the cuck you have always desired to be, you should also give her oral following the less then spectacular intercourse.
So, you are not going to see Jen for another two (2) months? If this true, you will find just as she teased you, she will find she will on her own find another man or men to continue her sexual enlightenment and enjoyment respectively. Who knows, she may ever hook back up with Aaron if his situation with his girl-friend were to fall through.
You have received everything that you asked for, fantasy to reality.