Annie's Night Outbymeistere©
We were staying at the best hotel in the city for our third annual "braless weekend and summer getaway." It was our way for a middle-aged couple in their forties to put a little zest in their relationship. After an afternoon of indoor delights our appetites were sharp and it was time for supper and a night out on the town.
I went to the closet to find something appropriate for the occasion. I chose a pin stripe button down shirt, khaki slacks, tie and blue blazer. The hotel's restaurant was definitely on the upscale side. Annie straightened her clothes and went into the bathroom. She came back out in a few minutes, freshened up, wearing bright red lipstick and a hint of blue eye shadow. "Do you think it's too much?" she asked.
"Not at all," I replied, "very classy." My cock, amazingly, became hard again. Annie looked like a fantasy come to life. The combination of high heels, silk skirt and blouse, satin camisole and make-up gave her an incredible erotic appeal. She looked elegant with an understated sexiness. And I loved the idea of her going without a bra, displaying her large, firm, beautiful breasts in all their glory to strangers, knowing they would be looking at her wherever we went and, that I would be there to watch their reactions of amazement and pleasure.
"You're sure?" she asked again. "I don't want to go out looking like a streetwalker."
"Not to worry, my sweet," I reassured her. " Definitely not a streetwalker I thought to myself- maybe a movie star, fashion model or very expensive escort.
In the elevator I couldn't help myself. I kissed Annie and felt her up like a horny teen-ager. It was a game we often played: me trying to get her nipples hard, she trying to stop me. She slapped my hand playfully. "Don't do that!" But she was too late. She looked down at her blouse to assess the damage. Her nipples were puckered and hard, pushing through the layers of satin and silk like pencil erasers. "You naughty boy, look what you did. If you want everyone staring at my breasts, they will now."
I smiled. Annie knew what I had in mind and was becoming more and more comfortable with having men appreciate her. "Come on honey," I ventured, "you like the attention. You've got the most beautiful breasts a woman can ask for and you know it. If I had those tits, I'd be President by now. You've got tits to die for."
"Yeah, sure. You always say that."
"It's true. You're so pretty- nice face, lovely legs and those gorgeous breasts. If you got it, baby, flaunt it. Strut your stuff! Seriously, you should be proud you're so gorgeous."
"It just feels so risqué but I'm starting to like it... feeling more confident I guess. Feeling more comfortable about my body and as I do, feeling okay about other people liking it too."
"Well, I sure do," I said. I gave her another squeeze right before the elevator stopped. "Other men should get to enjoy those tits as much as I do. I mean, it's the right thing to do."
As we went through the main lobby to the restaurant Annie stood up straight instead of walking with her usual bent at the shoulders slouch. The effect was electrifying. The high heels gave her body a little wiggle, making her breasts bounce up and down with each step, and easily noticeable through the sheer blouse. You had to look close to see that she wasn't wearing a bra but I noticed that a number of the men we passed were indeed giving her a careful scrutiny, savoring the sight of a voluptuous young woman.
At the restaurant, the maitre'd led us to our table, a special one overlooking the river. As he held Annie's chair for her his eyes dropped momentarily to her chest. He gave us our menus and a warm smile.
Our waiter, a handsome young man in his thirties, kept on stealing glances too. As he took our orders, he tried to be professional but kept on looking over at Annie to enjoy the view. My cock became hard again as I caught him furtively checking out at my wife. During our meal he seemed more attentive than is usually called for and both Annie and I knew that he was feasting on the display she was giving him. Whenever he came over to our table I swore Annie's posture improved and that she was thrusting her chest forward to focus attention on her still erect nipples, trying to tease the lucky fellow.
The meal was delicious, made even more so with the sight of my wife's show for the pleasure of a stranger.
After desert, we left our waiter a big tip and went out for a stroll on the Promenade. "Sweetie," Annie asked, "did you realize that he was looking at my breasts?"
"I kind of thought he was giving us pretty good service."
"C'mon now, a woman can tell these things. He was trying not to be obvious but I could tell."
"Did it bother you?, I inquired.
"It was a little scary at first and then I started to get aroused- knowing you were there and watching you watch him watch me. I got that feeling of power again.... being the object of such desire. I know I couldn't dress like this unless you were there. It makes it feel safe and okay. In fact, makes it kind of sexy, like I have a freedom to experiment and act in ways I normally wouldn't- without getting nervous or too embarrassed. I guess I have to say that I liked it. The tricky part is when I get this horny my nipples get hard and stay hard. I'll bet he could see them too."
"I had a feeling that you liked it. You seemed to really relish giving that poor guy a special thrill."
"It didn't bother you?"
"Far from it," I replied. "Made me feel proud that he was enjoying those lovely tits of yours. It was getting me a little horny too."
"So my husband gets off on having his wife go around showing off her breasts to total strangers...."
"Yup! Doesn't every waiter like to get a big tit... ah, I mean tip... for good service?"
We walked and talked, holding hands, feeling the warm, romantic glow of a beautiful city. The path led us back to the park we had been at in the afternoon. "I feel brave," Annie said. "Why don't you go sit down on that bench over there and let me give you a show." She chose a bench directly opposite me, facing mine, with about eight feet of path between us. She sat down with her hands folded in her lap, looking prim and proper. The setting sun was at the right angle, shining through her blouse to highlight her camisole. It was if the filmy blouse had become invisible and she was sitting there with just the camisole on, every curve and contour of her breasts evident. The sun cast shadows on the tips of her protruding nipples against the taut satin, making them seem even more prominent. I captured the exquisite scene in my mind, knowing that I would play it over again and again in memory.
Looking at me with a mock, sultry smile, Annie reached into her purse, making believe she was trying to find something. She bent over, taking stuff out of the purse and then placed a foot on the bench, her leg bent at the knee, as if she was trying to get more comfortable. With her other foot on the ground she gradually spread her legs, giving me a progressive view of her black slip, nylons and garter belt. The final touch was a shot of her new panties, the satin a glowing silver in the warm sunlight. She looked over at me and grinned. I responded by putting my hand over my chest as if I was having a heart attack.
Caught up in our little game, we didn't hear the footsteps. A young couple strolled down the path between us. Annie froze, not knowing quite what to do. The man's eyes dropped to Annie and I saw him look briefly up her skirt. His girlfriend didn't notice a thing. After they passed us, he put his arm around her. I grinned at Annie and whispered across to her, "you are magic for romance."
We continued our early evening walk. "I have an idea. Annie," I said, "do you feel like dancing? There might be a club in the Old Quarter we could go to."
"Hmmmm, sounds good," she replied. "You know I love to dance. If I knew this outfit would inspire you, I'd have worn it a long time ago."
"Sounds like a tremendous loss of missed opportunities, my dear," I said in a mock serious tone of voice.
We made our way down the promenade, just the two of us in the fading twilight. Passing a small copse of trees set off from the path, Annie took my hand and guided me into the darkness. Hidden from anyone, she pulled her skirt up and drew me close for one of her famous French kisses. As we kissed I ran my hand over her slinky slip, stroking her wet, eager cunt. "Boy, you're getting bold," I said.
"Told you I was feeling brave." She reached into my slacks and stroked my cock. "I never thought I'd get off on showing myself off to strangers but it's such an incredible turn on. I've been walking around for the last few hours so horny I can barely stand it. If I wasn't so nervous about it, I'd have you fuck me right here."
I pulled up her slip and inserted a finger inside her. Annie was literally dripping. She took my hand and pressed it hard against her as we kissed. I felt the same way she did. Part of me wanted to take my cock out and fuck her standing up; the other part wanted to continue our adventure. "C'mon, my little cum bunny," I said, "Time to go dancing."
With some difficulty we ended our embrace and continued our early evening stroll. In the Old City we heard music and followed the sound until we came to a club. It was on the second floor of a large, very elegant eighteenth century loft like building. A man at the elevator took our money and wished us a good time.
When we got to the second floor and stepped out of the elevator a swing piece from the big band era of the forties was playing. "I think I'm going to like this place," Annie said enthusiastically.
The club was crowded with people of all ages- from young, twenty something trendies to middle aged couples. The women were dressed for a night out, most of them with skimpy tops, short miniskirts and revealing blouses. I noticed quite a few of them were fashionably braless. Annie fit right in.
I spied two empty seats at the bar and guided Annie through the mass of bodies. The bar stools were high and unless you were six feet tall you had to perch your feet on brass rungs. We sat down and ordered drinks.
Annie swiveled around to face me and get a better look at the dance floor. The way she was sitting, high heels on the top rung of the stool, elevated her legs, knees slightly higher than her waist, giving a perfect view up her skirt to the luscious valley between her thighs. Even with the uneven lighting I could make out her slip and panties. She was so excited with the idea of being out in a night club with some of her favorite music that she was unaware of her skirt gradually riding up her nylons. When she bent over to mention something to me the skirt rose even further. The clasps of her new garter belt holding her stocking tops appeared. I was in heaven.
The bartender came back and served us our drinks. His gazed openly at the front of Annie's blouse with her nipples, erect from the over active air conditioning, poking through the thin silk. Annie seemed blissfully ignorant of his interest and I sat back and watched him. After a while he looked over at me and gave me what seemed a sly smile. He knew that I was enjoying showing off my wife's lovely tits.
I slid off the seat and went to the men's room. On the way back I took my time and blended in with the crowd in front of the bar to enjoy my wife as others were enjoying her. Annie had turned around fully on the stool to face the dance floor. The DJ had turned up the lights for a fast jitterbug number. Without realizing what the effect would be, she had spread her legs wide to get more comfortable and leaned back to rest her upper body on the edge of the bar. The bottom of her shimmering black half slip lay draped over the edge of the seat. Annie's panties were fully exposed, almost to her waist. I caught the outline of the delicate lace trim of her garter belt under the tight satin.
Her panties were like a white, shining beacon under her skirt, attracting others' interest. A man standing in front of me turned to his companion and said, "look at the cute babe over there flashing the silk."
"Hmmmm," the other man murmured. "I love it when a sexy woman likes to show off her cunt. I'll bet that little hottie is one good fuck."
A shudder of excitement shot through my body. When I looked over at the erotic display Annie was so unwittingly and casually giving a roomful of strange men, my cock became a steel pole in my pants. I stayed with the crowd for a while to watch them watching. Finally I went over and stood in front of Annie. Her eyes were on the dance floor, mine were on the patch of sleek white satin, looking like a light at the end of a sensuous tunnel formed by her skirt, slip and black nylons. "Do you like the music, Sweetie?" she asked.
"I love the music- among other things."
Her eyes widened in shock as she realized what I was referring to. She looked down and quickly closed her legs. "Oh, my God!" she whispered, "could you see anything?" She tugged her green silk skirt down but it remained at mid thigh because of the seat. Her garters still peeked out from beneath the hem.
I leaned over, whispered in her ear, touching a knee as a signal for her for her to resume her visual gift, "just the silken sweetness of your lovely body."
Annie hesitated for a moment and then slowly parted her legs again. "I'm feeling so horny. Can you really see up my skirt?"
I looked down at . "Nah, can't see a thing my dear." I grinned. Her panties were damp from arousal.
"Oh, it feels so good to be naughty," Annie said in a low breathless voice. "I can't believe I'm letting a room full of strange men look up my skirt. Do you mind if they look at your wife's cunt, Bunny?"
"I love it," I replied. "I love the idea of these strange men looking up your sexy little skirt and what I really like is that you like it. I'm gonna bet that you're making a lot of men very happy tonight."
Annie smiled and seductively licked her lips with tongue. "How about a dance?"
"Sure," I said, helping her off the stool and getting another lovely upskirt view in the process.
The band was playing Glen Miller's theme song, "String of Pearls." We went out into the middle of the floor and started our own version of the Lindy. Annie closed her eyes as if in a trance and moved in time with the music. Her breasts swung back and forth under her blouse; her sweet nipples, easily visible and rock hard, rippled the almost see through silk with every motion of her body. It was joyfully apparent she wasn't wearing a bra and I feasted on the sight. I took her hand and twirled her around. As I had hoped her skirt flew out and up to give a view of her legs up to her nylons and garters. I twirled her around again, quicker this time. The light green silk ballooned out again, this time exposing her panties. I could see some of the men watching her, surprised and delighted with her little show. Annie, caught up in the music, was oblivious to the admiring stares.
We danced three or four numbers. I lost count. As the song from My Fair Lady put it, I could have danced all night... just watching the attention that the audience lavished on my wife's exuberant displays of swinging, bouncing breasts and the visual treats of the satin world under her swirling skirt. I caught men glancing our way, some staring intently as Annie did another jitterbug type spin.
We finally stopped. We were both hot and somewhat sweaty from the bright lights. "I'm going to the lady's room," Annie said. "I'm so hot I feel like i'm boiling. This blouse keeps in all the heat."
"Take it off then," I humorously suggested.
Annie smiled mischievously. "Oh? Would it bother you if I did?"
"What do you think?"
"You'd probably like it, you dirty old man... have me showing off my breasts to everyone."
"Well, you'd fit right in with this crowd. If you haven't noticed, bras aren't too popular here."
"Dirty old man."
"I'll be right back," she said and then turned and left the dance floor. I went back to the seat at the bar to wait. Annie was gone for about ten minutes when I spied her coming across the room, threading her way through the dense crowd. I'll be dipped, I thought to myself, she's done it! She had taken off the silk blouse and was wearing only the skin tight camisole. Even at a distance I could make out her breasts, jiggling and bouncing as if they had a life of their own.
She climbed back on the bars stool, her face flush with excitement. "What do you think, Sweetie?"
For once I was speechless. "Isn't this what you wanted?" she asked.
"Oh, yes," I replied in a soft voice. One of my biggest fantasies had come true.
Annie rested an arm on the surface of the bar and threw her chest back to exaggerate her chest. I could make out every ridge and pucker of her nipples through the clinging satin, even, very faintly, the pink circles of her aureoles. "Nice tits, huh, big boy?" she joked. "They're going to cost you another dance."
"Well worth it, my dear."
She turned around on the stool to get a sip from her drink and in the process inadvertently spread her legs wide. I stared up her skirt astounded. The bottom part of her panties were bunched at her cunt with her enlarged lips almost surrounding the narrow band of satin. Her entire pubic mound was in plain sight. Annie pulled her panties tight like this whenever she masturbated. Ah hah, I thought to myself, this was why she took so long in the lady's room. "Ah, Sweetie," I said, "looks like you have been busy, you naughty girl."
It took Annie a minute to figure out what I was referring too. When she did, she blushed and look horrified. "Oh, my God! Can you see my vagina?"
"Yup, and it looks lovely. I'll bet I know what you were doing."
She turned beet red. "I'm going to go back and fix myself."
I took her arm and held her to the stool. "It's all right. In fact, you look great. Might get you horny."
"It is getting me horny. The material keeps on rubbing against my clitoris. Gets me so horny I can barely stand it."
"Then keep it that way. Enjoy the sensation. C'mon let's have another dance. No one's going to see."
As Annie slid from the stool the satin tightened against her cunt. She closed her eyes for a second, awash in feelings of lust. "It does feel good," she said in a husky voice.
The band was playing a slow number and we held each other tight. I could feel her breasts pushing into me; the tips of her hard nipples raked my chest. "Hmm," I sighed. As we danced I moved my hand down her back until I felt the waistband of her panties through her skirt. I gathered the elastic in my fingers and slowly pulled it upwards to stretch the satin tighter over her clitoris. Annie's body twitched as passion consumed her and she pushed her pelvis between my legs, almost humping me on the dance floor. My hard cock prodded her cunt through the thin layers of silk and satin. She was breathing heavily, barely able to control herself.
The music stopped and and the band began a spirited version of "Don't Sit Under the Apple Tree." We separated and went back into our version of the jitterbug. Annie's big breasts rolled back and forth under the flimsy camisole that appeared molded to her body. And I couldn't keep my eyes off of those hard nipples pushing against the slinky satin, moving around lasciviously with every step. I doubt if other men could too.
When it came time for a twirl I spun Annie around quickly. The silk skirt flew up to her stocking tops. I tried again and spun her like a top. The skirt rose higher this time, exposing her panties and giving anyone watching a brief glimpse of her furry mound. My heart almost stopped in my chest. I twirled her around one more time to let everyone have another lovely view. The bunched satin had disappeared into the inner recesses of her body, enveloped by her puffy cunt lips. All you could see was my wife's sweet cunt, naked and available.