Braless.
I don't recall ever going out on a date braless before. A couple months ago, on the way back from dinner with him, in the car, I took off my bra, giving him a peek down my unbuttoned polo shirt. Out to dinner is different. There would be more people around to potentially see.
Here it is, the four year anniversary of the day we met. Yes, he still remembers the day, without prompting from me. Occasionally, I'll give a hint around the second of the month for a monthly reminder, but he does well on the anniversary. As part of the celebration, he asked if I would go braless.
We've talked about us going out, me in a button blouse, no bra, and discreetly having one too many buttons undone. For his eyes only though. There is one problem. I have only one button blouse. It doesn't blend with a lot of my wardrobe. A girl can't go out in just any outfit, it has to look good too. Have to have matching top, skirt, and shoes.
Knowing this, two weeks ago, he bought me three button down blouses. White, black and maroon. They all have pockets over both the left and right breast. The white and black ones have those already rolled up sleeves, to three quarter length. A dressy, casual style. The maroon one is full length sleeve. He also bought me two skirts. Short of course. One is stretching, clingy, form fitting, black. The other is knit, flaring, back a little longer that the front (still short), loose fitting, swaying, dark gray. I tried the blouses on and they fit. Nice to know after almost four years, he knows my size -- small.
A week ago, I tried on the skirts. He was downstairs at the computer. I came down first in the clingy black one. No stockings. It felt tight and I'm concerned panty lines will show through. I turn around to give him the 360 degree view. He likes it. It shows off my legs. I then sit on the couch. The skirt rides up a bit, and I pull it down. I cross my legs to see what happens. He says nice view of my dark blue panties. I'm not concerned about him looking up my skirt, but about others if I wear it out. That might be a problem, but from his reaction, it would at least turn him on if I only wore it inside the house.
I go change into the gray knit one. This one feels better, looser, more comfortable. A fun skirt. I twirled around in it for him, it does sway or , shall I say, sashay. I sit on the couch again. This one doesn't ride up and is much more demure. It covers the view, if I want it to. Initially I do, teasing him. Then, as I'm crossing my legs, I lift up the skirt, showing him my panties. What a tease I can be.
I get up and sit on his lap. He tells that he likes them both, short, and they can be revealing. I feel him getting hard. I sit back on the couch, facing him. I spread and unspread my legs while talking. Crossing my legs to give him a view. He pulls down his pants and starts stroking himself while I do this. I see him getting hard, harder. It is turning me on too, both the flashing and the reaction. He takes his pants all the way off and sits next to me. He starts to put his hand up my skirt. I stop him, tell him this is for him. I start stroking his now very hard cock.
Taking my hand, I keep going up and down, up and down his hard shaft. Concentrating on the tip, then back to the shaft. Up and down, up and down. I feel him starting to cum. The movement of the hips, the extra hardness, stroking, stroking, he leans back, my hand stroking his cock, picking up the pace, faster, faster, closer, closer, faster, now as a load of cum spurts out. A second spurt, as his hot cum flows down from the tip, down the shaft, over my hand. White, sticky, hot cum, all over my hand. It takes three napkins and a wet towelette to wipe it all up. Based upon the reaction and the quantity of cum, I would say he likes the skirt.
With that image vividly in my mind, I know what skirt to wear for the anniversary dinner.
We have the restaurant picked out. We've been there before. It is two restaurants, same kitchen. One is a sports bar, the other upscale. The upscale part also has a bar. Our plan is to sit at the end of the bar, where there are only three seats. He would sit on the side closest to the door, thus blocking any view of him putting his hand up my skirt. I am a little modest about providing others that view. I would unbutton the third button of my blouse in the car to give him a view, both coming and going to the restaurant, but be buttoned up inside. Maybe have two buttons undone.