This year I discovered cross dressing. Granted, I’ve done it before. Slipping on a dress and panties and modeling this before a man before he fucks me. But this year I went all out. I had a young lady that helped me pull all of this off. Makeup, really nice fake tits, and clothes I bought off CL from a lady that was quite attractive herself. It added another layer to my bisexual experience. Unlike before, I went out in public dressed like this. I had a man take me out as his date and I sat in a booth at a restaurant in full female attire. Probably the single most erotic thing that I did this year. And mind you, I’m not a passable cross dresser. Think Billy Gibbons in a skirt. It’s not pretty! I enjoyed it. My date was very turned on by it. I think before we enter the dark depressing days of winter I’ll do it one more time.
Today I take it to a new level. I have a female that helps me get prepared. She assures me she can do a tuck (that stays fixed) and I'll look like I have a vagina while standing in front of my BBC lover totally nude.
I’m all dolled up. I will say that during the process of getting tucked I kept getting hard so the lady that helps me sucked me off. That was nice. Now I’m tucked and slightly super glued in a few spots but I appear to not have a penis. And it looks vagina-like. Lol. Time to go get laid.
I always look forward to Holloween. My wife loves to make me up as a woman, not a very prettty woman. I look more like one of the Monty Python guys as a woman. On the outside, I appear like a fat old house hag, but under my housecoat, she dresses me in a very sexy thong,stockings, bra, with wig and makeup. Its a turn on to be dressed like that. When the Trick or Treators are done, the housecoat comes off and I parade around in my sexy outfit. Since the first time she dressed me up, she has always fucked me with her big strapon. Holloween or not, when I dress up for her, its always funtime.
@parris001 That's amazing, I have friends that do this to me too, do all my make-up, dress me up, large fake breasts, wig, high heels, the full works, then take me out to bars and restaurants showing me off. It's so liberating isn't it! Did you go for the classy or tarty look? I enjoy variety and love being dressed up many different ways and being taken out.
I can't do much in the way of heels. I've always had weak knees and ankles. And I go for the classy look. This last outing I did, I did so with some clever taping and glueing. My cock was completely gone and my scrotum transformed into a vagina. My friend, Darlene really outdid herself this time. I even drove over to my lover's house this way and sitting and driving....... not uncomfortable. But as soon as I got some lube on me and started messing around and he was fingering my ass I started to feel it swell. It felt even hotter getting a swollen sensation down there. Like my labia was getting blood engorged. When he started fucking me, a few good poundings and my tape and glue came undone.
Good for you. You owe it to yourself. I know it’s hard to do but we might try to pay less attention to what other people think not only when we’re out en femme, but all the time. When I’m out, although I present myself well en femme, I am very vocal about the fact that I am not a woman, or a man who is trying to be a woman. I am simply a guy who loves wearing women’s clothing, both in private and when out in public.
I wear dresses all the time, especially during the cooler months, but I do not consider it "cross dressing", because dresses do not belong to women alone. I don't try to look feminine, but I do feel more sensual and less restricted than I do in jeans. My dresses are made of denim, plain cloth, or stretchy material. I like to have pockets to hold stuff. My outdoor work dresses are very practical. I really like my stretchy tee shirt dress when I'm indoors, and it's so comfortable, sometimes I fall asleep in it. Dresses just feel better. My girlfriend understands, and so does my boyfriend.
