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.
I'm wearing the aforementioned gray knit skirt. The maroon blouse. I don't see my nipples showing through. I put a small scarf on anyway, to be extra careful. My mind wanders a little, thinking because it has pockets, maybe he would like to put something in them? His hand touching my nipples? Hmm. I finish getting ready. Doing a mental check: skirt yes, blouse yes, bra no, pantyhose yes, high heels and jacket are by the front door. I'm ready, though still a little apprehensive and excited about going braless. The material of the blouse against my nipples also feels stimulating. I sense some wetness down there. I'm almost ready.
I'm upstairs putting on my lipstick. I hear the front door open. He has a key. I note he is on time. Usually he is 15 minutes late. Maybe he is excited too. He says hello to let me know he is here. I say I'll be down in a minute.
I come down the stairs. He looks up at me, and smiles. The wetness increases. At the bottom of the stairs, his arms go around me, and we kiss. Starting slowly, then getting harder. Our tongues dancing together. He says happy anniversary. I can feel his hands on me searching for a bra. I whisper in his ear telling him there is no bra. I can sense that he is pleased.
I sit down on the bottom step to put on the high heels. Oops, my legs spread giving a view not quite all the way up. How did that happen? After getting the shoes on, I stand up, he helps me put on the jacket, and we are off. He opens the car door for me. I get in, let my legs slowly go in, one at a time, flashing him once again. Teasing again. Plus, I know he likes it. He closes the door, gets in the drivers side. He reaches over for the seatbelt, his arm brushing against my breasts, sending a tinge of desire through my body. He clicks it in. leans over and we kiss again. He had starts up my skirt, stops, and moves to my chest. He feels my breasts through the blouse, finds the right side nipple and plays with it, all as we continue kissing. Luckily, no reservations are needed, because we would have been late. He starts the car. I unbutton the top button, then the second. He is watching me with great interest. I stop. He'll see more later, I tell him, let's go eat.
The restaurant is 10 minutes away. It is connected to a hotel, and the parking lot is fairly full. We find a spot, not too far away. He unbuckles my seatbelt, again brushing his arm against my breasts. I unbuttoned the third button to show him totaling braless. Then button up again. He comes around to open the door. Such a gentleman. As a reward, I spread my legs again for him. We walk to the entrance, holding hands, talking about our days. We get to the restaurant. Enter the bar area, there is someone sitting in our spot. Not only that, there is someone sitting just around the corner. And, they don't look like they are leaving anytime soon. We walk through the bar, checking for other possibilities. None. We walk through the restaurant to the sports bar. Nope, people on the end there too. What to do. All dressed up, no bra, no end of the bar, no hand up my skirt. What to do, what to do. It's our anniversary. Do we go somewhere else? Where is there a bar like that? What to do.
We improvise. The sports bar is too crowded. In looking at the dining room, which isn't crowded, he notices a table in the corner, near the window. We'll have to sit opposite each other, so no hand up the skirt. But the food is good, we're here. Improvise. The hostess seats us. My back is towards the rest of the dining room. There is a couple at the table next to it, (my left, his right) but they look like they are about done.
The server comes over. I order my wine, glass of ice (to put in the wine) and glass of water. He orders water. Our server informs us of the specials. The server takes the drink order, leaves us to read the menu. He comes back with the drinks, we place our order. I get up to use the restroom. As I walk, I feel the swaying of the gray knit skirt. I'm assuming he is watching, and my blouse is buttoned. After all, the restroom is in the sports bar where more people are.
I return to the table. The couple next to us has left. I take off the small scarf. I undo the top bottom. I undo the second button. Being careful because our food hasn't been served yet. I look across the table, we continue chatting, his eyes are going between my face, my open blouse and looking out for the food. Amazing what he can multitask on. Our food arrives. We start eating. I undo the third button, showing him cleavage, the curvature of breasts. I flap open the blouse, showing him more of my tits. I'm getting to like this, teasing him. Oh, the improvisation. It won't be a hand up the skirt, instead it will be some breast play. I offer him a taste. Of my food. I cut a piece of my parmesan chicken and lean over to put it on his plate. My blouse opens up some more, almost revealing my nipples. He likes the view, and the food. He shares some of his breaded veal cutlet. He puts a slice on my plate. Puts his fork down and reaches further to open my blouse more, revealing both of my nipples. He plays with each one, touching them, rolling them between his thumb and forefinger, all while watching for passersby. There are none. He removes his hand, but leaves the blouse open for his viewing pleasure. He sees the server approaching, informs me and I cover up. The server leaves. I button up and go to the restroom again. Too much water. When I come back, I angle my body so no one can see, unbutton my blouse, lean over to give him a view and kiss him. Kiss him hard, right there in the corner of the restaurant. Me, in my gray knit sexy skirt, braless, unbuttoned blouse giving him a view, our lips touching, kissing hard. Am I ever wet. Yes, I want to be fucked tonight and fucked hard/ Yes, I am really turned on.
We stop the embrace. I go to sit in my chair. I pull it out from the table. As I sit down, I flash him with a nice upskirt view. Blouse open showing cleavage, legs spread, it is getting hot in here, in more ways than one. Before anyone gets close, I sit back up at the table. Blouse still undone. He again reaches across the table to play with my nipples. Smiling as he plays. I enjoy it too. In a daring, for me, move, I leave the blouse undone, cross my arms to cover, when the server comes over. There was too much food, or was it too much playing and not eating the food, so we got to go containers. They were filled, as I'm sure I will be later. The check came and was paid. I buttoned up for the walk out of the restaurant. I needed to use the bathroom again. We went to the hotel lobby, found one down an empty hall. He held my purse and jacket. When done, I came out with two buttons undone. He helped me with my jacket. In doing so, he unbuttoned the third button. No one was around and I could wrap my jacket around if needed.
At the car, he once again held the door for me. I gave him a really good, long view up my skirt. He got in. Instead of reaching for the seat belt, he unbuttoned the fourth button, opened up my blouse, breasts totally exposed. He played with them, running his hand between them, under them. Playing with the nipples. So sensual. Will I cum in the car? He moves his body over and starts licking and sucking on my nipple. It is driving me crazy. In the crowded parking lot, dark, no one around, braless, blouse wide open, having my nipples sucked on. What an improvisation. I lean back and feel the sensations. My pussy is definitely wet and getting wetter with each lick. He continues sucking my right nipple, it has the best angle. Sucking on it, flicking it with his tongue, running the length of his tongue over it, my breath shortens, pulse quickens. I'm going to cum, and cum right there in the car, sucking, then flicking the tip while being sucked. More, more he does it, increasing the pressure of his tongue on my hard, sensitive nipple. Going a little faster, I feel it cumming, closer, closer. Oh I want him in me, want him to fuck me, but now, now, in the moment I want to cum. His tongue keeps up the pace, licking, sucking flicking. That does it, so hard, sensitive, braless at dinner, yes, yes, licking, now as I feel the orgasm release within me. He keeps licking, trying to bring another one, but I stop him. I'm breathless. I need to stop, temporarily. It is only ten minutes to home. He leaves my blouse open. I'm too tired to fix it. Besides, it has quite the effect on both of us. He starts the car, fastens the seat belts and we head for home. Happy Anniversary indeed.
On the ride home, I wonder what would happen if I was pantyless.