Sissy Magazine: The Top 8 Best Sissy Vacation Ideas!

Who doesn't like going on vacation? Especially if you are a hotwife like me, vacations offer extra special opportunities for sexy and kinky lovemaking with your boyfriends. During the first year when I was cuckolding my husband, I would go off and have fun while he stayed at home cleaning the house and playing with his butt plugs. He was locked in chastity, of course, so I didn't mind if he played with his ass. And as we worked on his forced feminization, eventually I decided it would be a good idea if he tagged along on my next vacation, so he could crossdress in public without embarrassing me in front of our neighbors. As much of a sissy cuck as he was, he hadn't had his sexual reassignment surgery yet and he wasn't totally passable as a girl. We didn't have any trouble finding a hook-up for him though, so it was fine. At the end of the day, guys know that an ass is an ass, and that's usually all they're looking for.

I know a lot of husbands and wives who are facing difficulties in their marriage talk about taking a second honeymoon to reignite their passion. The truth is, if you really want to save your marriage, you should let your wife cuckold you and arrange for her to go on a romantic vacation with one of her boyfriends. As much as I love cuckolding now, I have to admit that I was nervous at first. A vacation is an invitation to step out of your normal life and to try something new. I know a lot of women who take sort of mini-vacations to cuck their husbands. Maybe they only meet guy across town and stay at their houses all weekend. Maybe they only hook up with guys while away on business trips. When an ex-boyfriend comes to town for a visit, she might stay at his hotel with him. As much as I still love my husband and I want to stay married to him, sometimes I just need a break—a little vacation.

A weekend with a bull does have one thing in common with a real honeymoon though. It's all about sex. Yeah, we'll go out to dinner, we'll take a stroll on the beach, and we might even go shopping. But all of this is basically foreplay. Being in a hotel is an excuse to get laid three, maybe four times a day. I have spent times at a hotel where we were just in the room all day and he was basically inside one of my holes the entire time. I actually didn't want to leave the bed, since my ass was so sore. So, we just took a bath together, and he tried to be more gentle as he entered me.

If you're a sissy, you can expect the same kind of treatment. When I first started setting up my cuckold husband with local sadists, all of them Alpha-male doms, I let him spend the weekend with them, so he could enjoy the full bottoming experience. I have to say, this kind of training really helped him accept his role in our marriage as a cuckold and a sissy. No matter how devoted a hotwife is, I think you really need a man to give a cuckold his anal training. I don't have a real penis, after all!

A vacation is your chance to feel free, to explore, to let yourself go. At the very least, if you don't have to clean the sheets yourself, it's an excuse to make a real mess of the bed with all your love juices.