Sissy Magazine: 8 Tips For Losing Your Anal Virginity as a Sissy

I still remember the time I lost my anal, as well as my vaginal, virginity. In both cases, I was nervous, scared, and self-conscious. I wasn't ready at all—but I also was completely ready. I wanted it to happen. I wasn't afraid that I wouldn't like it. I was scared that I would look silly, that I would make a fool of myself in front of my boyfriend. I wanted it to be special for him. I only have one anal cherry, after all. I knew that sex was something that normal women do all the time, every day, perhaps even several times a day. I was doing it because being a virgin made me feel childish and I wanted to be a woman.

First, I need to say that I cry tears of joy every time a guy tells me he tried receiving anal sex and that he loved it, because I love it, too. I'm so happy that you accepted your role as a girl. And I can promise you that it's all going to be lovely from here on out. You can enjoy sex the way God intended you to—as a bottom, a sissy, as the girl in the relationship. Welcome to the club!

Full disclaimer: I am a hotwife active in the cuckolding lifestyle. I have guided my cuckold husband in his feminization and transition to life as a woman. At first it was mostly forced. Like a lot of cuckolding couples, I denied him sex after I found a new boyfriend. As time went on, we began to play with strap-on dildos, chastity, and crossdressing. He wasn't always a pretty or a very cooperative girl, but after a while he started to warm up to his new role very nicely.

Naturally, one of the biggest turning points in his transformation was the loss of his anal virginity to a man. Now, as a sissy, my husband didn't have a vagina, at least not at the time he started to see his first boyfriend. So, this was kind of like two big events in one. It was his first time being penetrated by another man as well as his anal deflowering. I know that when I lost my vaginal cherry, I considered myself grown up, a real woman. When I started having anal sex, I began to consider myself a slut. My husband got to experience both of these events in one night. When I started to let guys in my ass, I was pleasantly surprised by how comfortable and intimate it was. I told my husband he had nothing to worry about. Guys are awesome and they'll try their hardest to make sex fun for you, whether you are a girl or a sissy. If you are curious about anal sex, I have just one thing to say to you: dildos and vibrators are no replacement for a real man with a real penis. If you want to really feel like a sissy, you need to become one of us. Go find a man and let him break you in. I promise, it will change your life—for the better!