Key West Adventures

Key West Adventures

This was Caroline's and her husbands first visit to Key West. Her husband Jim was an internet porn hound and seen all sorts of erotic behavior during Fantasy Fest, a weeklong town festival that bordered on naughty illicit sexual teasing and flashing. He always fantasized of watching his lovely wife lose control and succumb to her lustful desires that he knew she had buried deep into her subconscious.

Caroline was shocked and maybe a little turned on by the carefree lewd behavior that seemed to be the norm here for women of all ages. It seemed to be an expectation to push the legal boundaries and see how outrageous each could act out in public. Caroline was a conservative Midwest wife that couldn't imagine what she was seeing on the streets and in the bars. Public nudity, flashing and bawdy behavior seemed to be everywhere. She did not participate that first year until the very last evening when she consented to go braless under a flowery transparent shirt loosely tied under her breasts, all to please her persistent husband that desired to show off his lovely wife's charms. She thought since it was past sunset and they would be pretty much outside that the flowery pattern would hide her breasts and nipples.

Jim had hounded Caroline all week long to loosen up and join in the flashing that seemed to be the rule for all females in Key West during Fantasy Fest. He wore down her resistance and she decided to please and tease her man just a little bit. What Caroline did not know that with every camera flash she might have well been totally topless. Her shirt became non existent under the constant camera flashes that showed her entire breast, beaded aureole, and extended nipples. Soon Caroline was the center of attention and she reveled in it as she was stopped every couple of feet for another picture totally unaware that she might as well of been naked from the waist up. Men were posing with her, wrapping their hands around her waist and drifting over her buttocks as she was handed off from one man to another. As the evening progressed Caroline tired of pushing hands away from her ass just went with the flow and ignored the men's hands as they wandered all over and under her short thin miniskirt. As it became more crowded, she was jostled and pushed around on the street. The picture takers were now encouraging her to get in to it and untie her shirt. Baiting her with beads she slowly untied her shirt and let it hang open barely covering her nipples which were at least an inch long.

Caroline could feel her pussy moisten and her husbands looks pushed her to remove her shirt altogether. Caroline was now topless in public for the first time! No one except her husband had ever seen her naked breasts, and here she was topless on the streets of Key West with her breasts bare for all to see. Camera flashes intensified with Caroline's naked breasts and nipples on display as she pushed and rubbed her rock hard nipples against the hairy chests of her fellow photo subjects. Her nipples were a direct route to her clitoris, as her nipples were teased and caressed she was getting more and more turned on.

Jim was in seventh heaven watching his wife's wanton behavior and state of undress. Many of the men became more and more bold, frequently using one hand to caress and squeeze her ass while the other cupped and lifted her bare breasts continuously stroking her hard nipples. A pair of young men sandwiched her between them, the one behind rolling up her miniskirt and grinding his obvious boner into her nearly naked ass while the one in front bent down and took her bare nipple into his mouth. This opened the floodgates and soon every picture taken involved her nipples pulled and sucked on while bare ass was fondled by complete strangers. She was posed in all types of compromising positions.

Caroline was down to a sheer thong and short miniskirt that was a mere band of cloth bunched around her waist. Her thong hung loosely on her hips as it was pulled and stretched and no longer covered or protected her wet pussy. By the end of the evening her breasts and nipples were red and swollen with bite marks and hand prints covering them. Never had Caroline been the center of attention like this, it was making her legs weak as she was continually teased with no relief provided. They just continued to stoke her fire. Her pussy became a furnace with her juices overflowing and beginning to run down her thighs. Her husband was busy documenting her every move on camera without any hindrance or acknowledgement that it was his wife being manhandled.

When they got back to their hotel room Caroline stripped out of her skirt and thong to reveal her dripping wet puffy pussy lips and slowly turned to show Jim her marked and reddened ass. The guys obviously had been taking advantage of going under her short skirt moving her thong aside while fingering her ass and pussy. She pushed her husband back on the bed and sank her wet pussy down on his cock while fantasizing about those hard cocks that were pressed against her earlier were now fucking her. The memories would have to last for the next year. Jim had Caroline describe her lustful behavior over and over and over. He was never more turned on than watching her play to the crowd of men and he had it all documented. He would be reliving this night for years to come!

As for Caroline, she was already imagining what kind of situations and costumes she could plan for next year now that she wanted to explore expanding her sexual horizons. She loved the lustful hungry looks she got from all the males and a few females in the crowd. Caroline wanted more!

Second Year:

Planning for next year's trip to Key West began in January, a mere two months after Caroline and Jim returned from the last Fantasy Fest. This year they would be in Key West from Monday to Sunday and would be sharing a house with friends that they had made the previous year. The 5 bedroom house had a private pool and small hot tub. Three couples and two single males made up the house guests. Jim privately hoped that sharing a house would put Caroline in some compromising situations over the course of the week.

Their sex life had never been better. Caroline would spin endless tales of the antics she would get up to in Key West. Jim got her to agree that she would not be allowed to wear or bring along any underwear. She was a little worried just how much she would be on display. Her costumes that they jointly developed and put together were brief on their own and without a bra and panties she would have to be careful to limit how much of her would be seen. Both Caroline and Jim were excited about their vacation and soon it was time to go. Bags were packed, Jim secretly procured a large supply of condoms and a few sex toys. He also bought a few Wicked Weasel swimsuits that he packed in his own luggage and removed Caroline's conservative one piece swimsuit as he checked to make sure she hadn't packed any underwear. He did find a few sheer and a couple of crotchless thongs and decided they were too sexy to leave at home so he left them in her luggage.

Monday night was fetish night, so anything leather and bondage was in order. Caroline's costume consisted of a set of chains attached to three strips of leather, one strip on each side and in between her breasts, the strips connected to a leather collar, a split black leather mini skirt with a Velcro clasp, thigh high black leather boots and a chiffon like covering over her chain top. Her breasts and nipples were clearly visible through the transparent veil covering her chest. One of the male roommates started on Caroline early in the bar and soon he removed her outer covering revealing her bare breasts and rock hard nipples to everyone on the dance floor at Captain Tony's. He said she could get it back from him in the pool later that night.

After a few drinks and catching up with friends from the previous year it was time to head over to Kelly's as they were hosting the Kelly's Kinky Carnival. Fetish ware was required or you had the option of stripping naked at the door to gain entry. No exceptions! There were several naked men inside who thought they could sneak in without a costume. These men were standing around completely naked displaying their hard cocks with pride! As Caroline, Jim and a few house guests were walking through the bar and patio area she casually brushed against some of those hard cocks and she couldn't resist caressing and stroking a few as they made small talk. Everything was so casual! Nothing seemed out of line!

Caroline was again on the dance floor, not dancing with anyone in particular, more of a group dancing together. While Caroline was not the only woman with their breasts on display, her rock hard nipples garnered plenty of attention. Dance partners would just lean down for a little suck and pull that made sure to keep her motor running and her nipples at peak hardness, a few would cup and tease her nipples from behind as they ground their hard cocks into her supple ass, all under the pretense of dancing.

It was time for a break and as Jim and Caroline stood waiting at the bar for some drinks one of her admirers brought a drink for her and they started a conversation about life and work outside of Key West. Soon they were on the edge of the crowd continuing their chatting, Jim kept a casual eye on things enjoying watching his wife's casual nature and discussion while her hard nipples were openly displayed. Jim thought he would have had a difficult time carrying on a conversation with Caroline's hard nips starring at him! He had a feeling more was going to happen it was just a matter of time. A few drinks later, Ralph (her attentive dance partner) had Caroline leaning back against a wall as they started making out. They were kissing deeply while his hands were all over her tits, soon his mouth moved from one tit to the other, back and forth, her nipples glistening from his saliva. Caroline held his head and continued to guide her nipples to his mouth. Ralph's hands were not idle, he took advantage and grasped her ass under her short skirt discovering that she was commando and brought their pelvis together so she could feel his hard cock as he realized this was going somewhere. They were like two long lost lovers that couldn't get enough of each other.

As the couple came up for air, Ralph's cock was tenting his boxer shorts and Caroline was flushed and disheveled, her wet rock hard nipples led the way as she looked for Jim. Jim thought she was getting cold feet and looking for escape. Jim nodded toward the bar and Caroline met him while Jim ordered another drink. Caroline leaned over and whispered into Jim's ear "you don't mind if I leave for a little bit do you?" As she said this she inserted her tongue into his ear and her hand dropped to squeeze Jim's obvious hard cock through his leather pants. "I promise to tell you all about it!" With that Caroline spun on her heel and made a beeline for the door where Ralph stood waiting, his cock still tenting his boxer shorts.

Jim thought "what am I doing! She is leaving with a complete stranger and she is willing going to get fucked! She had met Ralph about an hour earlier and that is all the time it took for him to close the sale.

It was around 10:30PM and Jim had a few more drinks, watched the heavy flirtation going on around him, but could not get his mind off of what he knew his wife was doing right now! He imagined as soon as Ralph got her inside his place, he ripped off her skirt left her boots and chains on and plunged his rock hard cock into her dripping pussy. After all they had over an hour of heavy petting and foreplay before they got there. But that was a few hours ago so where was she? Did Ralph have roommates too? Was she being gang banged by more men that she did not know? This only made Jim's cock ache even more so he decided to head back to the house, he knew the roommates should be there as it was approaching 1:30AM. Hopefully it would take his mind off Caroline for a while.

Returning to the house all of the house guests were in the pool partying away, no one was feeling any pain. Perfect for Jim to relax, no one questioned where Caroline was, as a few of the roommates watched and knew what happened at Kelly's. With everyone still in the pool, Caroline appeared in the doorway dressed in only her miniskirt holding her boots and chain top. Cheers and clapping erupted all around, it was 3:30 in the morning! Caroline had been gone for 5 hours! She took a bow, dropped what she was carrying, shimmied out of her skirt and posed so all could take in her abused naked body! Her face and upper chest were deeply flushed, her lips red and swollen, her breasts and engorged nipples were covered with red bite marks, as she rotated her ass it was just as red with bite marks covering all of her buttocks and upper thighs, but the best as she continued to spin while bending over was her shaved pussy! Her pussy was a sodden mess, lip's open and distended displaying her inner lips and liquid center, her clitoris red and standing proud, and her inner thighs a bright red that would certainly display bruising tomorrow. With that she did a little curtsy and went to her room.

The pool erupted again with hoots and hollers as she disappeared. They told Jim it was time to reclaim his wife's pussy and kicked him out of the pool.

Well, Jim was a little too slow as Caroline was passed out on top of the covers, her legs splayed open as Jim took in all of the evidence of his wife's infidelity. "Wow! She actually did it!" Her dripping open pussy made it clear that she did not use protection! Jim was rock hard and quickly masturbated and shot his load all over Caroline's bare ass and pussy. Tomorrow he would get the story in her words and find out how true his imagination ran.