@Daniel97 you have a real conundrum then. Both Cuckolding and other kink related activities are different. So of course enjoy the attention of both ladies, but do realize from a female standpoint you are living on borrowed time, unless both girls are poly-oriented, but that brings other twists.
As others point out, looks fade, things that you find interesting and quaint over time can turn into irritating. So honesty is the most important thing you can have. You can't turn off the cuckolding desire if you are truly a submissive. I can understand that if you state you are a switch, but I think you haven't been on the "earth" long enough to evolve into those areas.
What I can infer from your writing is that Kendra is really into you, and Jen does love you from experience and time; however, it is probably due to comfort and time ********. When you are young and your first relationships are the most intense and long lived, while later in life you will need to learn to love others. There is no right or wrong aspect of it.
As an example, I had a close jock friend in college who was alternative and we talked since he knew I wasn't going to rat him out to the other guys, state his favorite thing was taking a heavier/less attractive woman and whipping them into shape. If he felt they were submissive enough he would let them go and find another, and when he would find an alpha he would submit. He had alot of three-ways in his life, but he was a switch like me.
My point is know your kinks, know what you like, and realize that you are dealing with another human beings with needs. Don't use or abuse, unless they desire it. Most importantly make sure both partners know of each other, who knows maybe Kendra likes women also and maybe you can get some other interesting twists to happen ... you locked up in chastity, while you are cuckolded by a woman with a strap-on on your Jen who then helps out on "disciplining you" .... Days like this I wish I was younger and could be in this with the knowledge I have now ...
someone like you would be locked up and edged by Jen and then sent to Kendra to be disciplined. I would then implement a 4.0 and a six-pack with weight training on you so you would be strong physically and intellectually, but your ability to cum would be very very limited ....