Anonymous said: Hey Jenna, I'm an 18 guy and dressing up as a girl is such a turn on. I consider myself straight, but I'm still a virgin. Do you think I should get a chastity belt (cumming makes me not want to be a sissy anymore) and try to get fucked by a guy, or do you think I should reconsider after having sec with a girl?
That really depends on how important crossdressing is for you. But it seems to me that this might be a great opportunity, since many others discover their kinks at an older age. If I were you, I’d give chastity and anal sex a try and see where it leads to. But don’t try to run before you can walk. Buy some toys and explore anal masturbation. You really need to feel comfortable with it before you try getting fucked by a man. Take small steps in discovering your sissyness and have fun! And if you have any questions, feel free to ask anytime. Good luck! :) Kisses, Jenna