Dressing with Debbie and Sue
By Ronnie (AKA) Anne
I’ve never written about the fact that I enjoy dressing as a woman. But it is a fact I get a great deal of pleasure out of cross dressing. This is a true story and all of the names have been changed.
This happened several years ago when I was going with a nice lady named Debbie. Debbie is a real woman not a cross dresser. She is the most uninhibited woman I have ever known. She is bi, loves anal and toys and anything else sexual that you could ever think of. Debbie has just recently separated from her third husband and she and I were at my place. She did as all women do she started to look in my closets while I was cooking dinner for her and I and her girl friend Sue.
“What the hell are you doing with all these women’s clothes in the closet in your office?”
“Well I happen to love dressing as a woman once in a while. You know how much I enjoy tweaking people. I hope that doesn’t bother you.”
“Hell no I love kinky stuff I’ve dressed as a guy before when Sue and I go out so what the fuck!”
At that exact moment Sue came into my apartment. Sue isn’t bi, she just likes women, but enjoys watching Debbie and I play as long as I don’t try and fuck her. I have given her oral more than once and she admits that I’m pretty good at it.
“What’s new guys?”
“Sue come here and see what I found in Ronnie’s closet.”
“Hey cool you dress?”
“Yes I do I even go out dressed once in a while. It turns me on.”
“Cool lets all three go to the mall after dinner and buy some sexy stuff for Ronnie at Victoria’s Secret! What do you call your self when you all dressed up?”
“Anne after my aunt who once told me that I’d be cute as a girl.”
“Cool do you wear make up? You must to cover your five o’clock shadow. What color wig do you wear?”
“I have a long black wig and a short one as well. They are also in the closet along with the shoes and my make up is in the desk in the office.”
“Well it’s a spare bedroom that I use as an office.”
“What’s for dinner I’m starved and I’m sure Debbie is as well.” Sue gave Debbie a long passionate kiss.
“For dinner we are having: a tossed salad, fresh bread, Salmon in puff pastry with a creamy dill sauce, and for desert Key Lime pie.”
“Good damn thing it Saturday or we’d be having hot dogs beans! Beans give me gas and Debbie kicks me out of bed and even you wouldn’t eat my pussy Ronnie or should I call you Anne?”
“I’m only Anne when I’m dressed. I would never serve you such a poor meal at that!”
We chatted as we ate and everyone was happy with my cooking.
After dinner Sue couldn’t wait to see me dressed as Anne Debbie was just as anxious to see me as a woman.
I stripped and the first thing I did was put on my make up. I explained that I got it from a web site that sells make up to transvestites. Then I put on my padded panties that give me an ass that is shaped more like a woman’s and then the artificial beasts (48DD!) and bra. Then I put on my black stockings and garter belt. I picked out a bright red silk looking top and a long black pleated skirt that came three inches below my knees. My long black wig and shoes were last.
“Fucking awesome Anne if I didn’t know you were a guy I’d try and pick you up! What do you think Deb?”
“I don’t know if I want him to fuck me or eat me! But then I never do. Lets go the mall this will be fun.”
Debbie drove, I almost never drive when I’m dressed, Sue sat next to me grinning like a kid in a candy shop.
We walked around the mall for a while Sue was having fun picking on me.
“I have to use the bathroom then maybe we can have a drink.”
“Well Anne, Sue said grinning, which one do you use?”
“The ladies, of course, I may be a slut but, I’m not going to the men’s room.”
“You know that there isn’t a urinal in the ladies!” Sue was enjoying herself to no end.
“I’ve been there before.” I said swinging my little black purse around like Debbie always does with hers.
“Cool I have to go to how about you Sue?”
“I wouldn’t miss it for anything.”
I went into the ladies room and went to a stall and could hear Sue laughing in the one next to me. The only thing I was afraid of was her letting it slip that I was a guy. When we all left the girls room Sue was laughing.
“You know you even sound like a woman when you shit!” She laughed so hard she brought tears to her eyes. Then she did something that she has never done before in the over twenty years that I have known her. She kissed me on the lips! She did it of course to shock everyone in the mall. Debbie was just grinning.
“You know Anne I’ve never seen Sue so happy!”
“I don’t know why but I just love Anne’s look!”
We went to Victoria’s Secret and to be honest I don’t know who was worse Sue or Debbie. I had to try on more stuff that night we were the last to leave the store before it closed.
“Hey were did you get a credit card with Anne on it?” Sue had been impressed with that.
“Simple I just told my credit card company that I wanted a card for my wife!”
Sue slapped my back and laughed. “I have to say it your one cool broad Anne. I have a thing for women with brains!”
We stopped at a bar on the way home and had a drink Three guys tried to pick us up but Sue told them that she and Debbie were lesbians but I was bi!
When we finally got back to my apartment it was almost midnight.
“I’ve can’t remember when I had more fun Anne. I mean in public! Lets all go to church tomorrow morning. You will have to be Anne then.”
“As long as you don’t kiss me like you did in the mall I’m game what about you Debbie?”
“I can hardly want but right now I need to get fucked so shut up and lets have some fun.”