Fantasy Fest – PART 1

The Air Hostess

Key West has always been a magical place to me, which is probably why I have always had a part-time residence there, at least for the last 20 years or so. One of the most enjoyable festivals on the planet has to be Fantasy Fest. Anybody with an open mind can appreciate the humor, the satire and the openness of the people and the festival. Yes, there is a sexual undertone throughout the days, but it’s all in good fun and yes, there are a great many sexual experiences people enjoy throughout. Key West has is more than just this festival to me but on this occasion, this was one of the more memorable years. My typical day on island consists of heading down to the beach, a block away from my home, and spending some time in the sun, swimming in the ocean and walking up and down the beach. This day, I noticed a young lady sitting by herself on her towel. She went through the usual paces of applying sunscreen to herself, drinking water, and enjoying the weather and the scenery. She was a strawberry blonde with light blue eyes and very fair skin which made her easy to spot and a bit out of place. More curiously, was her choice in bathing attire - a very conservative bikini. Not the usual eyepatches and anal floss, but rather a more covering style and design. It all screamed of someone who still was not comfortable with her body and her sexuality. Nonetheless, she was attractive woman with an athletic figure and perfectly rounded medium breasts. As happened from time to time a gust came off the Atlantic and sent her hat flying in my direction. I caught it mid-flight as I was sitting there enjoying a beer. My beer went airborne and spilled onto the sand. I looked over and saw her walking in my direction with a look of embarrassment and amusement at the same time. “That was a fine catch my good, sir”, she said in a British accent. “You saved my hat, and I am grateful”, “Well there fair maiden I believe I am now entitled to a ransom. I have not only saved your hat, but it has cost me my beer” I responded in an almost sarcastic British accent. Marcia was her name.

We’ve bantered back-and-forth for a few moments, her with her intoxicating accent and me with my dripping sarcasm and both found a great deal of laughter in the back-and-forth. She asked me how well I knew the island, and I told her that I was a local. She mentioned that she was an air hostess, who had an extended layover and drove down from Miami to explore Key West. She’d heard much about it and wanted to experience it for herself. I invited her to pull up her towel and join me as I reached into my cooler for another beer and offered her one as well. As we chatted, she finally summoned the courage to ask about Fantasy Fest, and what that was. I explained that the island has a healthy mix of pretty much every character under the sun. Straight people, gay people, many races’ people, Bahamian descendants, and people from pretty much all over the planet, all of which had come to Key West and adopted an open mindset about everything under the sun, including, and especially, sexuality. She blushed at the notion. “Totally uninhibited?” She asked. “There’s pretty much anything for anybody if you’re just willing to look and be patient on the island “, I responded as describing a place one would expect to find at the very end of the road. The day progressed, and it was now rounding four in the afternoon, and we were a few beers in, so the conversation became more lighthearted and, at times a bit provocative around the topic of Fantasy Fest costumes. Even with sunblock, she was already getting a little bit red, and I mentioned that it might be a good idea to get out of the sun. I mentioned to her that I only lived a block away and that I had a pool with a fair amount of shade as well as sun, depending on her preference. It was a private yard with a fence, and I mentioned to her that I frequently swim naked in the evening and sometimes late at night without the concern of anybody watching because of the high shrubbery and the fence. She thought for a moment and decided to come back to my place but wanted to walk across the street to her hotel first to grab a sundress and some sandals since she only had her bathing suit and did not want to walk through the streets uncovered. A short walk later we walked in to my place I grabbed her a bottle of water and out to the pool we went. I opened the sliding door, and she marveled at the pool and back yard. “What a lovely oasis you have here” she commented. It was not an expansive pool, but it was perfect for a small backyard, and it was set in a lush environment. I kicked off my sandals and pulled off my shirt and walked into the pool, the water temperature, perfect. She slipped out of the sundress and let it fall to the floor, kicked off her sandals and joined me in the water. She downed the water very quickly and looked in my direction. “Would you mind if I had some wine? “She asked. I pulled myself out of the water, walked into the house and retrieved a very nice, buttery Chardonnay from the fridge and poured us both a glass. Between the beers in the ocean, the glass of wine and our conversation, now felt more familiar and more comfortable.

The sun was now starting to hang low in the sky, and the hunger was starting to arrive. I suggested dinner at a local restaurant that served some of the best red snapper on the island. She seemed excited, having not had fresh fish right out of the ocean very often. I offered her the use of my guest shower and bathroom to freshen up to which she replied, “I was hoping there would be dinner involved, so I brought some things to change into, if you don’t mind”. I raised my arm, gesturing towards the bathroom for her, and off she went. I went into my own room, my private sanctuary and rinsed off, putting on a loose-fitting pair of shorts and a button down top. As I walked out of the room, I saw her standing in the kitchen, refilling her glass of wine in a bright flowery print sundress with spaghetti, straps and sandals. Her hair pulled back and her makeup and lips, perfect. “Is what I’m wearing all right? “She asked. “It’s lovely and perfect! “, I replied. We arrived at the restaurant and were seated right away. The wine list had an exquisite White Bordeaux, which I imagined would go well with any fish on the menu. I ordered a bottle and asked her permission to order for both of us. She was delighted that I took the lead and a bit excited at the surprise that would be our dinner. “We will take the large, whole red snapper, grilled with lemon butter and capers. I think that would go great on top of a bed of parsley and jasmine rice with warm honey sautéed carrots. Your house salad would be great to start the meal off and we’ll see about dessert after dinner but hold a slice of Key Lime Pie for us in reserve “, I ordered. She responded enthusiastically to my food order and was eager to sample the feast. In short order, our wine and our salads arrived, and we consumed the salad voraciously. She sat back in her chair and looked at me and smiled “You surprise me. The men in England can at times be not very well mannered. I am enjoying these moments because it’s clear that you are educated, refined, and worldly. I think that is very classy! I can also sense that there is a knowing about you, a sexuality that has me intrigued and aroused “, She confessed. “My girlfriends say I’m a prude and unimaginative when I tell them the things I’ve done with the few boyfriends that I’ve had. I have never enjoyed giving oral sex to a man and I’ve only ever experienced missionary”, she went on.

I was absorbing her confession and wondering how someone so beautiful and so exotic had never had the opportunity to have her sensuality repaid back to her by a lover. It was confusing to me and yes, it also made me wonder about some of her choices in men. Regardless, she was being vulnerable, and I was not going to break her stream of consciousness nor was I going to embarrass her. “I’m not a slut. In fact, I’m very inexperienced but I’ve always had fantasies. Oh, my goodness, I’ve probably said way more than I should. I’m so sorry. Just ignore me. The wine has me rambling on”, “You need not apologize. I totally understand and I’ve heard everything you have said. For now, let’s just enjoy dinner and let things go where they go. How do you feel about that?”, I said. “I think that’s perfect. It looks like the main course is on its way so let’s Enjoy and let the mood and the wine guide us”, she replied. The fish arrived soon afterward and was laying in the center of the table between us. I showed her with the tip of the fork how to pull the meat apart. “Now you can be formal and use your fork and your knife like stuffy British people do and take the fish away on your fork or, you can pull some of the meat away and pick it up with your fingers and eat it the way we islanders do”, I mused. “Oh no, I like the way the Islanders eat”. She immediately went about following my lead, using her fork to peel the meat away from the fish, and then picking it up with her fingers and dropping it into her mouth, delicately. After a few attempts at this, she discarded the fork and simply just used her fingers. The entire process was very erotic to me as I’m sure it was for her as well. The olive oil, the smell and taste of the herbs on our fingers and our lips seemed to heighten the arousal that was building between us. We continued consuming the fish until there was nothing left, but the head and the Boney skeleton. She took the small napkin under her wine glass and covered the head because she didn’t like the eye of the fish looking at her which immediately brought laughter to me. “You do know the fish is dead, right? “, I asked in amusement. “I know he is, but he’s still staring at me, and I don’t like it! “, she responded in her slightly cockney British accent. More laughter followed. “I think we will take a slice of Key Lime Pie, but could you make it to go? I have the same wine in the fridge at home and a very inviting pool, so I am thinking the Key Lime Pie and the wine in the pool will be our dessert “, I bantered. The waiter looked at me and smiled. “That sounds perfect and just lovely!”, she said that as she smiled at me and winked.

We walked up the street for a few minutes and arrived back at my home. She arrived at the open sliding glass door looked over to where her bathing suit was on the chair drying from our swim earlier, but before she could head in that direction, I said, “tonight’s swim is clothing optional “, she smiled at me but was clearly confused at what to do next. Thinking and conflicted between what she wanted to do and what she felt she should do. The conflict was visible. She walked towards the pool, where I was standing, bent down, grabbed the glass and took it down in one swig. “Another, please! “, she asked. I refilled her glass as she looked at me and took it down as well. Instantly, she slipped the spaghetti straps off her shoulders allowing the dress to fall to the ground, revealing that she was only wearing panties. It was clear to me throughout dinner that had been the case as there were several times throughout our dinner that her nipples revealed her mood. She bent down and removed the sheer panties and slipped out of her sandals. As if a continuation of her unplanned disenrollment, she jumped into the pool, sending water in every direction. She came up out of the water and pulled her hair back ringing out the water. She walked towards me with her arm outstretched for her glass of wine. This time, she took a more moderated sip and then wrapped her arms around my neck and pulled herself towards me, giving me along deep kiss. “Tonight, has been amazing. The first date I ever had with a gentleman who treated me like a complete lady. All night my mind has raced with thoughts of things I never found myself wondering about that I could do with you. I know I’ve had a few drinks and perhaps my inhibitions are quite low, but I just wanted you to know the effect our day, and our evening has had on me” she said. “I’m flattered by your words, and by your willingness to push your boundaries, but I must confess while I may be a gentleman there may be a point tonight when I stop being a gentleman and I hope you also stop being a lady.” I responded. “I want that all the time that I’m with you. After tonight, I have three more days and if that’s OK with you, I’d like to make the most of it but not really make any plans. For once in my life, I’d like to not be on a schedule and allow my life to surprise me”. “You are in the right place with the right person at the right time for all of that. Let’s make it happen”, I responded. At with that, we began along deep kiss.

As we kissed, I could feel her nipples becoming hard against my chest. I could feel her pushing into my chest, but reluctant to move her hips. Sensing the reluctance, I slipped my hand down from around her waist and onto her butt, pushing her hips against me. She could now feel my erect cock against her and her body reacted instantly. She moaned in both astonishment and arousal, tentative at first, but then pushing back to enjoy the sensation. I knew from her confession these moments would have to focus on her enjoyment and her pleasure first and allow her curiosity to take her to things that would pleasure her. We kissed more, endlessly. “Are you really this generous of a lover?”, she asked. “Kissing is where it all starts. Kissing is what opens the erogenous zones and the mind. Kissing is the beginning, the middle and the end of intimacy. I enjoy kissing and as luck would have it I am enjoying kissing you tremendously”, I responded to her. Her mood and her arousal only intensified hearing that. Our kiss continued for a bit longer, and then I slid both my hands under her arms, pulling her out of the water just a bit and began to trace her nipples with my tongue. She gasped, both at the sensation, and at the tenderness she was now experiencing. I lifted her and motioned her to lock her legs around my waist and to lean back, placing her arms around my neck. She did so, which allowed me the freedom of my hands to massage her breasts tracing the outline of her face with my fingers as I kissed her. Her legs around my waist, loosened a bit, and now my hard cock was pushing up against her, tickling the lips of her pussy. I could feel the heat and the wetness building inside her. Once reluctant earlier, she now pushed towards it as if to want more. I allowed that sensation to remain for the next little while because I knew she enjoyed it, and she wanted it. I wanted it too.

The time had now arrived to leave her world of vanilla and move into all the other pallets of sexual exploration. I moved towards the edge of the pool and lifted her up so that she could sit on the edge. I grabbed one of the floating cushions in the pool and slid it behind her and said, “Lay back and enjoy “. Her legs still dangled in the pool, and I moved between her knees and spread her legs apart. I began slowly kissing the inside of her thighs and using my tongue to tease the gentle flesh between her legs. I could sense her hesitation disappearing as her arousal intensified. I moved my hand up and with the very tip of my tongue, began to slide up between the very wet lips of her labia until I arrived at her clit. She wanted more, her body needed more. The sensation was both new and intense for her and it signaled crossing a boundary that was unfamiliar to her but now welcome. I slipped my arms under her legs to use my thumbs to spread her lips apart and allow better access. I was now rhythmically making small circles with a tip of my tongue around her clit. Her arousal intensified, exponentially, and at a pace that surprised her. It was an arousal that took her to a place she had only dreamed about. She was now actively pushing back against me to feel the sensation more entirely. It only took about five minutes, but she came, violently thrusting her hips and squeezing her legs around my head. Reaching down to grab my head and pull it closer into her. I used my tongue to retrieve every drop of her sweetness. I could taste her, all of her, and as her contractions began to loosen, I guided her back into the water and kissed her. The kiss was a compliment for her efforts, but also to share my reward with her. She relished it. She grabbed my head and held it tightly up against her so that every drop was shared between us.
“It’s been so long since I’ve had an orgasm. Well over a year. I’ve never felt anything so intense, not even when I play with myself, which is only just to relieve a momentary tension. Everything inside of me felt that. Thank you”, she confessed. “The night is still young, and there is more for you to feel.”, I whispered. As she regained her composure, I lifted her back to her previous pose on the edge of the pool and returned to the space between her knees this time using a finger to gently flick my way across her clit. Her arousal returned instantly. Her hips, pulsing, her breath in increasing. As she became more tense, I took that finger and inserted it inside her gently massaging the tissue inside her at the very top until I found the spot of most of her pleasure. Once there, I leaned in, and with my tongue began kissing, and then tracing those same small circles around her clit again. Her arousal became convulsive. In moments, she came and this time rather than stopping my free hand rose to her belly to keep her in place. I paused only for a moment to allow her to recover, and then began again slowly, then more intensely until she came again. Each touch inside her pussy with my finger and each caress with my tongue on her clit, elevated her orgasm as she came time and time again until there was no break between orgasms.

We continued for a bit in that manner until her breath could no longer keep up with her demand. She slid back in the water against me and began to kiss me. “I am a complete woman now. Before now, I hated when men did that to me because they never got me where you just did. I sensed they did it because they felt obligated so only did it for a little bit to indulge me which turned me off. I will never think that again and will simply discard anyone who can’t get me there again”, She confessed. “You should have your pleasure, you should demand your pleasure, and you should never settle for less”, I responded. “I want you inside me, I want you to fuck me.”, She begged. “Not yet my dear. There is something I want you to do for me first.”, I said. We kissed to celebrate her moment and, so she could yet again share in her sweetness with me. She enjoyed it, she wanted it. She used it as a sign that her body and her mind were in an evolution, and she welcomed it.

We both laid there, breathing and appreciating each other staring with a hunger into each other’s eyes. She know there would be more…