I adore cross dressing men but there was a time when I was as close minded as some other women about men who love cross dressing. It seemed crazy, as though there was no possible way that would ever be fun or sexy. My friends all had boyfriends who went out and did things like fishing and hunting or the more upscale versions of those like polo or just sitting around being manly.
But I was just not attracted to those kind of guys. I wanted to be! I tried to be! You know that whole phase where you go out on lots of dates, certain that if you just meet the right guy everything will fall into place. That was me for years. I watched my friends get married and divorced or just date and have long relationships while I barely managed six months (and that was a long one), because the kind of guys I wanted, weren’t the kind I thought I should want.
Sounds confusing, doesn’t it? Imagine if you were me at the time! I was completely at a loss and I’ll admit to wasting most of my twenties and some of my thirties trying again and again. Then one day I decided to stop. I was almost thirty five years old and for some reason that number just woke me up.
Spending one more day not doing exactly what I wanted to do was senseless, so I went out with the first pretty guy I saw! That’s right, pretty. He was clean, smelled good, wore a pink sweater under his brown leather jacket, eyeliner and had the fullest lips I’d seen on a man. The fact that he was going to love cross dressing couldn’t have been more clear, but I didn’t care!
I don’t mean they like to jump on the bed and have girly pillow fights, though some might! What I mean about being more fun is that the men I love, that’s right guys, I’m talking to all you cross dressing men out there, are just more fun in general. They have a light hearted outlook on life, something that many serious manly men sorely lack.
They never want me to tell them how strong they are and don’t come home smelling like sweat. In fact, the man I’m seeing now, showers when he wakes up, presses his pants and shirts and my blouses too and then gets dressed smelling good. He showers after his work out and then again before we get in bed. I don’t care that he loves to wear a silky pajama top to bed with a pair of white silk panties, I just go topless and wear the pajama bottoms and we have all kinds of naughty fun!
There is that word again, fun! We have fun in bed, trying out new positions and our role play games are limitless, since he’s willing to be Marilyn Monroe and let me be the sailor picking her up at the bar, or let me be! We don’t have to spend time worrying about is he manly and acting manly, he doesn’t care.
I love helping him with his cross dressing, because that also means going shopping together and we both love that. We even had a…let’s say explosive. Time in a dressing room one day, trying on skirts and blouses. He wishes he had boobs like mine, so when he gets to look at and play with them, we get a little heated sometimes.
My current cross dressing boyfriend is about ten years younger than me and pretty enough to be a young woman. He has longish blonde hair and amazing blue eyes, loves pink and straight leg jeans, as well as kitten hoodies. When we go out together everyone stares, but he doesn’t care and neither do I.
We aren’t self-conscious about our age difference or his choice of clothing. Sometimes we both go out dressed in short sexy skirts and my only complaint is that he has better legs than I do! We are perfectly matched in so many ways that my friends are actually jealous.
They complain about men who go out without them, tell them what to do or criticize their choices of paint for the bedroom or dresses for a dinner party. My man never does that. He’s too busy helping me pick the paint or using his love of cross dressing to find us both amazing outfits for the party. So ladies, if you haven’t tried dating a man who loves cross dressing, I encourage you to give it a go!
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