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FETISH STORIES

A Night In Key West

A Night In Key West

by tosshhh_
20 min read
4.7 (12400 views)
adultfiction

Many of my stories I draw from personal experience. I embellish on little details and exaggerate to an almost comedic level. But most stories do have a modicum of truth to them. This story is a true tale of one of my favorite memories that still pops into my mind from time to time. Names and details are changed of course but I hope you enjoy.

I was on my way to Key West to join some friends for a wedding. I was in my mid twenties at the time and had just moved in with my girlfriend. She sadly couldn't make the wedding but that was alright as it was one of my rowdiest college friends weddings and the bachelor party was anticipated to be a bigger event than the wedding itself.

Now I had actually had something on my mind in the weeks leading up to this wedding. I knew a girl who lived in Key west from my single party days. She had moved to Key west years ago. She was by far the best fuck of my life. I used to attend swingers parties with her before she moved to key west. She was wild to say the least. When we dated she was a cam model and had even done some porn videos. 0lI had heard she was married now and I didnt expect to run into her anyway but I was extremely tempted to look her up.

She was purpose built for sex and the two of us were completely and hopelessly addicted to each other. I actually ended things with her because I was so hooked. She was blonde, Huge tits, a tiny petite little thing and skinny, which made her nice ass and huge tits quiet eye catching, and the tightest pussy I had ever fucked and she squirted with every orgasm. She had absolutely no limits sexually and was my kinky little sex slave that did whatever I said. I mean whatever I said no hesitation at all. To this day I have no idea why I ended it probably because I couldn't get anything done lol. I did know I couldn't settle down with such a wild little sex kitten or introduce her to my mom so there was that.

I have mentioned in some previous stories but I have a 11 inch dick. Its fat even for a dick that size and some girls struggle with something so big. Most girls get excited by it but cant take the whole thing, which isn't a deal breaker. A lot of times I find girls who are size queens and have a dildo to match me and can handle it. Kelly she was special, She had a unique combination of ability to take it all while being just the tightest addictive pussy I had ever used, It was like her pussy was a fuck machine, She could squeeze me in a way that felt like she was massaging my dick with some fancy sex toy.

She was a complete nympho. When she first saw my dick she told me. "From this moment on, I'm your sex slave, I will do whatever you say, you want me to suck your cock in public I will, You want to fuck me to death I don't care I'm your fuck toy until the end of time." Kelly said in a serious tone I had never heard before.

Man did I test that statement and I soon learned she meant every word of it. I once took her to dinner in a see threw dress, tits out and everything. I made her blow me in the uber to and from the dinner. I fucked her 10 times a day, everywhere I could think of. I fucked her in public constantly. I tied her up, and kept her in my room for a week naked and tied to the bed.

Before long I started filming her and posting our videos online. I took her to swingers clubs and she would blow husbands while I fucked their wives. I fucked so many girls that way. I really should tell more stories about her. It was like having a living breathing sex doll. I don't think I jerked off once in the year we were together she fulfilled my every sexual need. I could even have her visit me at work strictly to blow me and leave.

One time I was so cruel we were at her friends house having a little party. Most of the guys had left and it was just a couple of her close girl friends were left. The topic of sex came up. The girls giggled as clearly Kelly had told them all about our sex life. The girls even joked about the size of my dick. I figured if she was opened about it so could I. "Yeah Kelly is my sex slave, She will do whatever I say." I said.

"Well with a foot long Pringle can for a dick I am not surprised." Her friend said with a giggle.

"No seriously watch, take off your clothes." I said chuckling.

Kelly giggled nervously then looked at her friends and laughed. "I'm sorry guys, I have to do it." She said then got serious and whipped off her clothes right there in the kitchen.

Her friends watched in silence except for the occasional giggle fit as Kelly sucked my cock to completion in her friends kitchen. When she was done she got dressed and we carried on like it never happened. That was nothing for Kelly. I frequently asked her what if questions. What if I asked you to do this... Her answer was always the same. "Absolutely." She had asserted that if I told her to suck my cock in front of her parents she would do it. I still cant believe I broke things off with this women.

Now here I was in a happy healthy 2 year relationship with a beautiful women I saw a future with. But in a couple short hours I was going to be on the same island as Kelly and the temptation was so great. I had all her socials and could see she looked happy and in a long term committed relationship but I was still so tempted. Then all at once something amazing happened.

I had just checked into the hotel everyone is staying at. We all met up in the lobby and someone posted a group photo and tagged me in it. Then the most exciting thing happened. I looked down at my phone and I had a message. "Are you in Key West?" and it was from Kelly. I fully expected everything I said in this conversation to be scrutinized by my girlfriend back home so I decided to stay professional despite all of the thousands of marathon fuck sessions flooding back to my memory.

"Yeah I'm here for a wedding." I said simple and polite.

"Oh okay you should have told me you were coming, How long are you here, Maybe we can meet up?" She said.

"Just a few days but yeah hopefully I see ya." I said trying to keep it polite while still keeping the door opened.

"Do you want me to come meet you somewhere?" She asked.

"I'm not sure what our plans are yet but yeah maybe." I said wanting so bad to see her but wanting it to seem like I was just being polite.

"Just tell me where to be and Ill be there." She said.

"I mean I'm sure well end up at ricks eventually lol." I said.

"Do you want me to wait for you there?" She asked.

My mind was spinning I was so torn. I couldn't get myself to tell her I had a girlfriend who wouldn't like me talking to you. I also wanted so desperately to see her. I also was afraid to make definite plans with her because I was afraid of the temptation.

"Well I mean if you're not doing anything Id love to say hi." I said trying to sound casual.

"What time should I go?" She asked.

I was feeling the pressure. I wanted it to seem innocent and be innocent. "Well anytime is fine I'm not sure what time we will be there yet and I know were making it an early night tonight so if we run into each other great if not no big deal." I said trying to sound and innocent as possible so I could tell myself I wasn't trying to meet up with an ex girlfriend.

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"Alright I was supposed to have dinner with my husband but Ill cancel it, Ill head there now and wait for you that way I wont miss you, If you guys change your plans let me know. What should I wear?" She asked.

I felt guilt and panic I thought to my girlfriend back home, and worried about her marriage too, this was too messy I felt I had to call it off I didnt need this temptation.

"Oh don't do that just to say hi to an old friend, Enjoy your dinner and if we see each other great." I said.

"Okay." She said. "But I really want to see you :(" She said immediately after.

"Well I mean If your there great, if not no big deal, congrats on the marriage btw." I said feeling like I had done the right thing.

"Okay, If I'm there, do you want me to wear anything specific? I still have that green dress you like, and thank you Mike is great, and he is aware of you btw." She said.

"Oh Great." I said unsure of how to possibly respond to that in a way that sounded innocent.

Wouldn't you know within the hour we were on our way to Ricks bar. I got to the top of the stairs and immediately locked eyes with Kelly. She was wearing that sheer, barely there, tight, short green dress that left her looking practically naked. She clearly had no underwear underneath any of it and she was sitting at the bar drinking her patented white wine. I gulped hard and pretended not to notice her as myself and the wedding party got settled.

There was one more element to all this. The groom had gotten his dick sucked by Kelly once at my command while he was dating his current soon to be wife and had asked me. "No Kelly" on our way here. His wife wouldn't recognize her but he would. I decided to find a moment to casually say hello keep it friendly but distant go back to my party and pretend this whole thing never happened.

After everyone was in a groove I excused myself and went to the bar to get a drink. I saw Kelly still sitting alone. I went up right behind her and tapped her on the shoulder. "Hey Kelly how's it going its good to see you!" I said.

"Yeah you too, I was wondering if you were ever going to come over." She said and she stood from her chair.

My god did she look good. Her blonde almost white hair was up in a tight bun. Her face was done up with some expert smoky eye makeup. Her tits, OMG her huge perfect tits were painfully visible threw the sheer fabric of the plunging neckline. The sheer layers covered her lower half less transparently but it was still clear this dress and those heels were her only clothing that night.

"How have you been, Your married now so wild, What's the husband doing tonight.?" I asked trying not to stare at those massive perfect tits.

"Oh he just dropped me off, he is going to get some food and then he is going to hang out down the street in case I need a ride home, He wants to meet you actually if you're still around later." She said smiling up at me and pushing out her chest slightly.

"Oh yeah Id love to, So how's life?" I asked. We carried on some small talk over a couple drinks and genuinely were just two old friends catching up. Finally I broke my composure and lost my innocent tone for only a second of weakness. "We had some fun together didnt we, Man I wish I could relive some of that." I said.

"Okay sir, what would you like to relive." She said in a sexy serious whisper.

"Oh no obviously your married now, I'm just saying we had fun, but its in the past."

"No I told Mike about our relationship, He understands that what you say goes." She said casually taking a sip of her wine.

"Oh yeah right, I know it was like that before but I wont make you do any of that stuff again, fun as it was." I said still wrestling with my emotions.

"Well its up to you completely just know though, When I said I was yours, I meant it, You can still do whatever you want with me, That cock of yours in framed on my wall, If I was willing to let you almost drown me blowing you underwater, of course Ill let you use my married pussy all you want." She said casually sipping her wine.

I was in such shock I just sat there for a moment blinking. Then I realized I had been gone from my group for a while. I was pulled back in as Kelly stretched her arms over her head deliberately pushing those huge naturals out. I leaned a little closer to her as she wagged the big tits back and fourth for my eyes barely contained by the sheer fabric. She giggled as I drooled over those massive fun bags.

"Wow so out of all our shenanigans, that blow job underwater in the water park is still the most extreme to you." I said with a chuckle.

"Yeah you have no idea what its like having a foot long cock down your throat underwater, with people all around and not knowing which would happen first, you would cum, or I would drown." She said giggling.

"So you really were willing to die just to make me cum." I said with a laugh.

"Of course sir, you said don't come up until I cum, I'm your fuck toy remember." She said completely serious.

"Okay fine, We will have one drink but in an hour, because I gotta get back to my group." I said lost in her cleavage. "Do you have time to wait, maybe meet me in that cocktail bar next door" I asked.

"Okay sir, or maybe somewhere we can have a dance, like the club next door?" She said placing her hand on my thigh right beside my huge throbbing cock snaking its way down my leg. An image of my dutiful girlfriend kissing me good bye flashed to my mind but was quickly expelled as her thumb grazing my head threw my slacks.

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The rest of the outing I was lost in thought. Half of my mind was racing worried my girlfriend might find out about this little violation of trust, The other part of me was thinking back to all the countless sexual fulfillment with that sexy little slut that would be waiting for me next door. I was snapped from my day dream when one of my friends repeated the question. "You ready the ubers almost here?" He asked.

"Oh you go ahead, I'm gonna get one more drink Ill get my own ride back." I said.

"You sure?" He asked again. Though I wasn't sure at all I encouraged them to leave me. I still hadn't made up my mind if I was even going to meet her. I was leaning towards calling an uber and releasing myself of this temptation. Half of me wished she would just return here and remove the decision. That's when my phone buzzed.

"Are you still coming? I'm waiting for you, Hubby just wants to know how much longer you will keep me." It said.

"Hey look it was great running into you I just don't think we should, were both in relationships and it just seems too messy, I'm glad we caught up and all I just don't think I need this temptation in my life." I typed back feeling a weight lifted off of me.

"Okay sir, Its completely up to you, I wont tell anyone though, its just one drink, but if you want me to go home I will, If you want to chat a bit great, If you want to dance I'm for it, I'm flexible." She said being her typical accommodating polite self. I felt a little guilty for ditching her but I decided to stick with my guns and book the uber home. "Ill be waiting at the garden of Eden for you if you change your mind it closes at 4am hubby said he would wait, no pressure though." She said.

If any of you know Key west, Garden of Eden is a nudist bar. The image of her nude at the bar forced my thumb towards the cancel button on the ride share app. I didnt respond to her text I just started walking. The primitive part of my brain told myself if I didnt answer her its like I just ran into her on accident. I ascended the 3 flights up to the roof top bar and there at the bar practically surrounded by drooling men was Kelly naked.

Kelly was a sight with clothes on but a naked 24 year old sex kitten holy shit. Again she's all of 5'2" petite little pale thing. White blonde almost silver hair done up in a tight bun, sharp angular facial features like some high fashion model. Perfect figure, nice ass, tight waste but those fucking tits. These tits haunt my dreams to this day, must be at least an E cup, natural, bouncy, perfect tear drop they are just spectacular. I strode over to her. "Hey Kelly." I said almost feeling defeated. "Another white wine for the lady and get me a beer please." I said.

"I didnt think you were coming so I told hubby to join me, but Ill tell him to wait downstairs." She said texting away.

"So he doesn't mind you having a drink with me?" I asked in genuine curiosity.

"Well he loves me, and I was up front with him in the beginning that I'm already someone's sex slave." She said.

"Even after all these years you still consider yourself my sex slave huh?" I said placing my arm on her chair and staring down at her tits.

"Of course sir, I'm your plaything, that's how I like it." She said smiling and leaning against my arm.

"Well I have a girlfriend that I see a future with so its just going to be one drink." I said regaining my composure.

"Okay sir, Whatever you want, One drink then." She said putting on a pouty face.

We got our drinks and I watched mesmerized as the naked little sex pot led me by the hand to some seats in the back.

"You look exactly the same Ill admit you are a sexy little thing." I said leaning closer to her on the corner section of the couch.

"Thank you sir, I gained a little weight actually but it all went to my tits." She said cradling her huge boobs in her arm and bringing them closer to my face.

"Well yeah, No complaints here, You are something." I said placing my arm over her shoulder more on the couch than on her naked body.

"Well its all for you sir, By the way your monster cock must feel so stuffy all cooped up in those pants, I picked this place so you could let it breath a little bit if you need to." She said as we watched all the naked people dancing to the electronic music of the opened air bar. "Its just one innocent drink but no need to feel uncomfortable, I know how hard that thing can get to keep contained." She whispered as she leant into my arm further I felt her tits brushing my chest.

She was right my cock had been throbbing since the moment I landed here. I looked down and you could clearly see the huge outline extending down my leg almost to my knee of my giant fat throbbing member. Her huge boobs against my side caused my fat cock to lurch. Kelly giggled and stroked my other thigh right where my cock would be if it was down that leg. She traced her finger knowingly from my crotch down my leg to the exact parallel of my cock head. I could almost feel a phantom finger on my cock as she did it.

My cock had a life of its own and was flexing and lurching wanting so desperately for physical touch. My arm even flinched almost needing to reach down and grip my cock as Kelly continued stroking my other leg with her manicured nails giggling softly to herself. "My hubby is only this long." She said pointing to a spot on my leg about 3 inches from my balls. "Annnd the biggest I've had since you is about here." she said pointing to a spot a couple inches shy of my head. "Want me to take it out for you so it doesn't suffocate." She said not waiting for a response before gripping my zipper.

"Wait come on, I think that's a bit much even for here." I said despite a better protest being I have a girlfriend.

"That guy over there is hard and nobody cares." She said pointing at a fat old man with a little hard on down the couch.

"Yeah but come on, you know that this is different, It will cause a scene." I said.

"Oh don't worry your not the first monster cock to walk in here, They have seen it all." She said as she unzipped my pants and pulled out the huge organ. Finally in the free air my cock had the room to grow to its full size. My huge cock stood straight up and visibly throbbed in the dull light of the roof top bar. Kelly's head was only maybe 5 inches from the throbbing 11 inches of huge fat veiny cock. "All better, Now we can have our innocent drink in peace." She said taking a small sip of her pinot griot.

I mimicked her and took the smallest sip being more preoccupied with our bodies touching. With each breath we became closer. What started out as two people seated side by side quickly became her snuggled up into me my hand over her shoulder and fingers inching towards her chest. She had one hand beside the base of my cock and the other on my chest as close as she could get to my cock head.

Everyone walking by stared at the pair of us. a blonde busty slut naked snuggling up against a 11 inch cock creates quite a sight believe me. Even in a crowded bar, with bumping music we had a small crowd gathered around us discreetly staring. I shrugged my shoulders once and used it as an excuse to reach around and reposition my right hand on her giant jug. After only a moment of simply resting my hand on her tit I grabbed her boob trying my best to make it seem like it was just innocently resting.

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