This story has its basis in fact but, unlike my other two stories, has been embellished to add length to it. It is about 20% true.
My wife was a woman in a bit of an emotional or moral turmoil. On one hand she wanted to explore but on the other she was a complete prude. When we were at home she dressed in a very conservative manner seeming uptight all the time. The only exception was when we went on holidays when she would loosen up and wear bikinis and somewhat revealing clothes – not much mind you but certainly more than she did at home.
We had discussed going to Key West for Fantasy Fest a number of times and looked at the information on the web. Karen was interested in the pictures of the men and women walking around in broad daylight with very little else on other than body paint, but said there was no way she would do that. Personally I thought she would be a hit, she has a slender figure, not overly endowed on the top but certainly enough to enjoy – a full B cup. Her legs and ass were her best assets and could easily have belonged to a top lingerie model.
We finally booked the trip and left to see what it was all about. Our hotel was a couple of blocks off Duval Street where we knew the action was. We arrived there about 6:00 in the afternoon and got ready to start wandering around. In spite of the warm weather Karen wore a dress that would have looked good on her grandmother. We wandered from one bar to the next for a little while just watching the sights. Karen wasn't very good at holding her liquor so was starting to get high.
By the time it got dark we were starting to do more watching and walking than drinking as Karen had pretty well reached her limit and when we passed a very discreet looking store that seemed to sell lingerie and sex aids we decided to go in. The store was run by a very classy woman probably in her 60's with a name tag that said "Anne". She took Karen under her wing and started showing her all the different toys. Karen was blushing and trying not to look interested. Anne finally pointed to a dish on the counter with pills in it and said "You need one of those". Karen asked what they were and Anne told her they were pain killers called Percocet and said they would relax her, give her a sense of euphoria and let her enjoy Key West more. Before I could say anything Karen had taken one and quickly swallowed it.
As the sex toys didn't seem to be of much interest to Karen, Anne started showing her nightgowns and other lingerie. The obvious sex oriented outfits were quickly passed over but she did seem to be interested in the nightgowns. Finally Anne talked her into trying one on and, after a few minutes in the changing room Karen came out with knee length nightie that looked very nice but was about as transparent as a burlap sack. Even Karen seemed a little disappointed and much to my surprise said "You can't even see me through it; I could wear it to work". Anne went to the rack and pulled another one off and handed it to her saying "Try this". Karen was back in a few minutes wearing the new one. I could see her bra and panties through it reasonably clearly. She said "I like the way this one looks but it's very itchy". Anne never hesitated and pulled a third nightie off and handed it to her.
This time Karen was gone awhile longer and when she came back giggling it was obvious she had taken her bra off. In fact everything was obvious. She might as well have been standing there in her panties. The nightie just provided a slight blue tinge to her body. Her nipples were very erect and she was breathing a little hard. This was not a Karen I had seen before. She turned to Anne and asked "Do you think I would be safe wearing this out on the street? Its dark now and it won't be like it is here in the store will it?" Anne, bless her soul, said of course she would be safe but it would be better if she took her panties off as well. Anne stepped forward and crouched in front of Karen. "May I" she said. Karen just nodded and Anne reached up under the nightie, grasped the waist band of Karen's panties and pulled them gently down. When she had them down to the floor level she waited for Karen to step out of them her eyes locked on Karen's vagina which was only about a foot away from her nose. Karen placed her hand on Anne to keep her balance while she stepped out of the panties. She almost lost her balance anyway when she tried to shake the panties off her right leg and Anne quickly slid her hands up both sides of Karen's left leg somehow managing to get them under the nightie and steadied her. I noticed that the top of her right hand was right against Karen's vagina and her thumb looked like it was searching for her clitoris. Karen stood there for a moment and then stepped back giggling again as Anne let her hands drop.
As far as I knew Karen had never had a lesbian encounter and I had no idea how she felt about this latest experience but she certainly looked like she was ready for anything. Her breasts and nipples were on display and her vagina was clearly visible. She had never had very much pubic hair, just a sprinkling above her slit and the top of her vagina lips could be seen quite plainly through the nightgown.
I paid for the nightie and Anne said she would mention to friends to keep an eye out for us and make sure we didn't get into trouble. Taking Karen by the hand we walked out into the night. In the dark of the street Karen's nightie seemed a little less transparent. In fact you had to look closely to see she was naked under it.
The gown was full length and I guess she pretended she was fully covered. She actually got more attention than the women that were walking around naked with just body paint. Any time I got behind her I reached under her arm and cupped her breast. At first she objected but then seemed to get into the swing of things and didn't mind. In fact when we stopped to look in a window I stepped up behind her and reached around and cupped both breasts tweaking her nipples which were getting very hard.
A couple of times men stopped us and asked if they could take pictures of her. The first time she just stood there almost covering herself with her arms. But by the time the third man asked she grabbed the nightie at the sides and pulled it tight around her body. Her breasts, her by now very erect nipples and vagina were fully on display. He asked her if she would drop one shoulder strap which she did without hesitation and one breast was completely exposed; the nipple standing proudly erect. After her "photo shoot" we moved on.
At one point we were stuck in the middle of the street in a crowd that wasn't moving, we were just standing there watching a juggler. I was just to her right and behind her. A man who was directly behind her put his hand on her ass and I thought shit, she is going to kill him. She glanced at me and saw it wasn't my hand and turned to the front again. The crowd wasn't moving and the guy started to move his hand up over her hip and under her arm. She actually lifted her arm to accommodate him. He reached around and cupped her right breast. We stood there with him fondling her breast and playing with her nipple with his right hand. His left hand was now on her ass. I saw him trying to get it between her legs but she wouldn't move them apart to let him. The only other person who noticed was a woman on her other side. She was smiling as she watched the performance.
Finally, after a couple of minutes, he let go of her breast and moved closer behind her and reached around her other side with his left hand and, I guess, started playing with her vagina. I couldn't see what he was doing but the other woman turned towards Karen and reached out and started playing with Karen's other breast. Soon Karen started humping her hips forward in a jerky, uneven movement and finally spread her legs. At first she had her feet about a foot apart but then she moved again and her feet were about three feet apart and she was still humping her hips forward, now with a more even pumping action. It was obvious she was trying to fuck something. She started to crouch. It seemed she was trying to get her knees farther apart. I pushed ahead a little so I could see what the man was doing to her.
I guess he had "walked" her nightie up with his fingers and his middle finger was pushing slowly in and out of her cunt in time with her humping. The other woman was holding the nightie up for him and Karen's cunt was in plain view for anyone who cared to look. God, she was fucking his finger. The man reached down and under the nightie and back up to Karen's ass. He spread her cheeks and started rubbing her asshole. Her head was down and she started to wobble on her feet and I was afraid she was going to fall down. The other woman let go of her breast and put her hand on her shoulder to steady her. Karen looked at her and grabbed hold of the woman's jacket for balance. She started to moan and whimper and her breath was catching but she never lost eye contact with the other woman. It was almost like she was looking for approval for what she was doing. She grabbed the man's wrist and pumped his hand harder. She was staring into the other woman's eyes when she came and grunted "Uh ... Uh ... Uh", in time with the thrusts of the finger she was fucking. Nobody else seemed to notice and the woman just smiled and quietly clapped her hands.
The crowd started moving and so did we, me leading a rather dazed Karen. We soon stopped again. This time she was facing me. Another man was standing beside me also facing her. I saw him looking up and down her body. Then he reached in his pocket and pulled out his car keys which had a small flashlight attached. He held the light up, looked at me as if asking for permission. I nodded my head and shrugged. He turned the light on and played it across her breasts which were clearly in view in the light. I noticed Karen had her eyes closed and it appeared she was not paying any attention to the man. She was just standing there with arms down at her sides. The man just looked for a minute then slowly reached out with his other hand and touched her breast. He kneaded it gently and pulled on her nipple. He reached up and slid her left shoulder strap down and gently uncovered her breast. Bending over he took her nipple in his mouth and sucked gently as he bunched her breast up with both hands, his palms almost flat on her chest, the sides of his hands squeezing her breast up and out. When he took his mouth away after a while her nipple was standing up hard and red and her breast was squeezed between his thumbs and forefingers on both hands. He stared at his erotic display for about 15 seconds then let go of her breast and gently raised her shoulder strap. I was surprised when he turned to me, said "thank you" and as he moved on I noticed a stain spreading on the crotch of his pants.
Again the crowd started moving and we began walking again. Karen was starting to wobble on her feet and I was getting worried she was going to fall. All of a sudden there was another couple walking beside us. The man, a small fellow with glasses about fifty years old said that Anne was worried about Karen as she had allowed her to take the pill. His partner, a woman who looked in her forties, said that Anne had suggested they come and find us and take us back to Anne's apartment above the store.
At that moment Karen started to wobble and giggle more than before and I readily agreed as I didn't want to try to carry her all the way back to our hotel.
The man introduced himself as Michael and we each took one of Karen's arms. The woman introduced herself as Kathy and walked in front trying to clear a path as we led Karen back to where the store was.