Tracy's Key West Adventure

by Tracy Love

 

I don't think that I've ever been to a place, quite like Key West, Florida. I had been driving for 4 hours and really needed a pee break. I finally pulled onto the island of Key West, roughly 150 miles south of Miami, and continued to mile marker zero, at Eaton and Whitehead Street. I continued on Whitehead Street, took a left on Caroline Street (made famous by Jimmy Buffett in his song, "There's a woman going crazy on Caroline Street") and then a right onto Front Street to the Key West Hilton Resort and Marina. As I pulled into the parking lot I see the huge banner strung ove the entrance, "Welcome to Key West, Gay and Lesbian Pride Week " (which for any of you dear readers, is during mid June). I check in under the name of Tracy Lanford ("Love" is my nom deplume), and the deskman doesn't even give me a second look. I guess that during this particular week, it's not uncommon to see feminine names attached to masculine personas. I can not wait to get to my room and begin the transformation to Tracy.

Once in my room, I draw a hot bath, pouring a libral amount of lavender scented bath oil into the water. I immerse myself in the steamy liquid, thinking to myself, "Calgon, take me away". After thoughroughy washing and shaving every square in of my body, I apply some breast cream to my now developing titties and put on my sexy black lace bra. I am so thrilled that I no longer need to insert breast prothesis to achieve a feminine bustline. I hook my matching garter belt in front and then rotate it to the back, and pull on my 15 denier full fashion black stockings and attach them to the garter tabs. Then I pull on my panties, a mixture of black satin and lace, over my garter belt, so I won't have to undo my stockings when I need to pee (or get laid). I then put on my full length slip, letting it float down my body, what a sensual feel it has! Then I slip into sheer silk blouse and a knee length skirt. I kneel down to hook the ankle straps on my sandals, selecting the 1 inch heels, knowing that I'll be doing a lot of walking, and my four inch "fuck me pumps" would be podiatristic suicide. I put on my Eve Arden 100% natural human hair wig, thinking that a thousand dollars was a lot of money for a wig, but "HEY", I'm darned well worth it! Next, I stand in front of the mirror, and begin to apply a little make up. I don't normally wear a lot of make up, I'm told that I'm quite pretty without it. I put on a little eye shadow and mascara, just a hint of blush and some Avon Pink Pearl lipstick. As I look in the mirror, I see a living doll peering back at me. What a twist of nature that someone as beautiful as this had to be born with a penis. I put on my gold necklace that has a fancy symbol hanging from it, it looks like chinese letters, but if you look close, it actually says "SLUT". I put on my Lady Bulova wrist watch and some dangly ear rings. I then sit down and apply several coats of Pink Pearl nail polish, waving my hands in the air to encourage faster drying. I put on my C.Z. ring, which leads people to think that I'm engaged to Donald Trump. I grab my purse and check it's contents, hanky, perfume, lipstick, condoms, money....yup, I think that I'm all set.

I walk down Caroline Street to the infamous Duval Street, jokingly known as the street of a thousand bars. There are quite a few, but I doubt that there are a thousand. You see all kinds of folks here, the young, the old, the straight, the gay...during this particular week, you most definately see quite a few in the gay catagory! I do not stand out as a member of this catagory however, I appear, for all intents and purposes, to be an attractive young lady, enjoying the sights and sounds of Key West. I stop at a booth, set up on Duval, hawking tourist attraction tickets to just about anything that you could imagine. I purchase a ticket to ride the "Conch Train" (It's a neat little history lesson, where everyone boards a seat among the 5 or so "railroad" cars, which is pulled about Key West by a locomotive looking engine.A local relates the sights and history of the area as you go). I put the ticket in my purse for use later. I then spy a cute little cafe called the Poinciana Lounge and decide to pop in and have something cool to drink. As I entered, I felt the icy cool air on my skin, and the droan of a slow blues type of melody playing in the background. I sauntered up to the bar, and a really cute bar tender asked what I like. I told him that what I'd like and what I'm going to order are two different things. He smiled and suggested that I try a "sex on the beach", I giggled and said I'd love to, but for now bring me a chardonay. We continued to flirt for the next 20 or so minutes, when he asked what I was doing for dinner. I told him that I had no plans, but before he got in too deep there was something he should know. When he said "That you're a guy, right?" I almost gagged....."how...how...did you know?" I queried. He said that he could barely make out an Adams apple. I told him that he had a very talented eye for detail. I gave him my room number and told him to stop by around seven. I leaned over the bar and gave him a kiss on the cheek. I then continued my stroll up Duval Street. I stopped to see why a crowd of people had gathered outside of the Bourbon Street Pub. As I got closer, I could see there was a fashion show of sorts, going on. All of the participants however were male, girly boys. They were each in some sort of lingerie, parading back and forth on a make-shift stage. The success of their performance was apparently gauged by the decibel level of the applause that they received from the crowd. I watched the show until one of the contestants came onto the stage wearing totally transparent panties, thru which you could plainly see his erect cock. I guess that's when Key Wests finest decided enough was enough. They told everyone to disburse and they escorted our well endowed contestant to a waiting squad car. Only in Key West, I thought to myself. I entered an establishment called The Hog's Breath Saloon to use the ladies room. I lifted my skirt and dropped my panties and sat on the toilet when out of the corner of my eye, I sense movement. As I turn my head, I see a huge hard cock poking thru a hole that someone has made in the wall. Well, I'll be God damned, it's a glory hole! A fucking glory hole! I figured, what the hell, I could use a little protein. I opened my mouth and engulfed the head of this monster, noisily sucking and slurping. I laughed to myself thinking this guy thinks he's getting his knob polished by some sexy gal, when actually it's by a sexy girly boy. I continued sucking on the head of this beauty until I felt it stiffen, I knew he was about to cum, so I deep throat him until I can feel his pubes against my nose. He cums down my throat, literally, in buckets. This guy hasn't cum in weeksI think to myself. As he withdraws his softening dick from my mouth, a little sperm runs down my chin, I catch it with my finger and push it back inside my mouth, swallowing it, along with the rest. I place my mouth against the hole and say "Thankyou". I finish up my business, and exit the restroom, just as young man exits the men's room next door, I figure he's the one I just sucked off. I smile at him, and lip the words "Thank you." He smiles and heads to the bar. I just head back onto Duval Street. I head all the way to the end of Duval, to the docks and am admiring the lovely boats there. I am brought out of my daze by a voice, "Want to take a ride and earn some money?" I look towards the direction that the voice is coming and see a 40ish or so gentleman, standing on the deck of an impressive boat, no, yatch is more appropriate a term. He and another fellow, I say in his late 20's early 30's, come over to where I am and introduce themselves. The younger fellow is Tony, the older fellow says he is known as Captain Stabbin. He tells me that he takes pretty young girls out to sea on his boat, and video tapes he and his partner sodemizes them, then posts the pics on his pay website, and would I be interested. It will take about 2 or 3 hours and we'll pay you $500, cash. I take the Captains hand and put it under my skirt so he can feel my hardening clitty and ask him if he still wants to make the offer. As he feels my panty encase dick, his eyes light up, and he says"More than ever!" He tells Tony to fire up the engines, that we're going to have fuck party.

We go out about a mile or so, we can still see the coastline, but anyone onshore would be hard pressed to see us. Tony drops anchor and starts setting up the videocam on a tripod. Captain Stabbin asks me to remove my skirt and blouse, so I'm standing there in my bra, gartered hose, panties and heels. Tony zooms in and tells me to freshen my lipstick, so I pull out the tube and apply some, being as sexy as I can. Then they start interviewing me. "This is Tracy, she is a he, and is in town for Gay and Lesbian Pride Week" Tracy has agreed to come with us and perform before the camerea, for your viewing pleasure, isn't that right Tracy?" I smile at the camera and say "what ever is your pleasure." The Captain asks what I have stuffed in my bra, that gives such a feminine line, I tell him that the only thing in my bra, are my titties. He says that he doesn't believe it, and to remove my bra. So I reach around and unclasp it and let it fall to the floor. They both gasp and remark what cute titties I have. Tony comes into camera view and sucks on my right titty, slightly biting my puffy nipple as he does so. I moan for my adoring audience. The Captain tells Tony to remove my panties so he can get an unobstructed view of my clitty for the camera. Then he tells Tony to suck on my clitty, but Tony says "No fuckin' way". I tell Tony not to get upset, if there is any cock sucking going on, it will be by me. I get on my knees before Tony, and undo his trousers and let them fall. I then take his beautiful hairless cock into my mouth and swirl my tounge around the tip. I look up into Tony's eyes while I suck him, then look longingly into the camera, I'm really getting into this. The Captain tells me to get on my hands and knees, and to stroke my penis while I continue sucking Tony. I can see that the Captain is applying K-Y jelly to his now exposed man meat. The thing was huge, I've seen a lot of cocks in my life, but never have I seen anything as big as this. I swear, he could make a horse feel inferior! He walked into camera view, and knelt behind me, placing the tip at my opening. "Oh shit" I thought to myself, "He is going to rip me open". Then I felt a slow steady pressure at my opening, and then to my surprise, he slipped right in. He and Tony got into a rhythm, theCaptain fucking my ass, and Tony fucking my face, and I'm stroking my shaft. I was in fuck-heaven. Just then the Captain starts grunting that he going to cum. He grabs my hips and starts slamming his meat into me. Then I feel Tony take my head in his hands, and pushes his shaft all the way down my throat and he holds me there, I start to get faint and think that I'm going to pass out, when suddenly, both men cum, simultaneously, filling my poor abused body with their sticky seed. Just then, I begin to deposit my own seed on the deck. The Captain withdraws his dick from my discended asshole and goes over to the camera and zooms in on the puddle of cum that I just squirted. "Lick up that cum, off of my deck", the Captain ordered. I did as I was told. Then the Captain zoomed in on my face and asked me all sorts of questions that he said his viewers would enjoy. "Did you like the taste of my cum?", "Is my cock the biggest you've ever had in your ass?" Stuff like that. Then Tony told me to get dressed, that we were heading back to shore. The Captain had me step into his Cabin to sign some model release forms and he paid me $500 in crisp brand new hundred dollar bills.

When we got back to the docks, I headed back to my hotel, so I could shower and freshen up for my dinner date. I chose my virginal white and pink lingerie for my date, I wanted to give a more innocent look, than the slut that I was this afternoon on camera. I put on my 34B Hanes her way satin and lace white/pink bra, and my matching garter belt. I attached the garter tabs to my white seamed stockings, and slipped on a pair of white satin panties adorned with little pink ribbons. I slipped into a set of strappy 4 inch heeled sandals (I'm going for the look tonight, rather than comfort) I slipped into a cream colored satin camisole with spaghetti straps and put on a sheer white blouse, with a high lacey collar, so my adam's apple would not show at all! I pinned a cameo to it. I wiggled into a knee length pencil skirt, and checked myself out in the mirror. I was pleased with the result. I reapplied my make up and glanced at the clock. I didn't realize how time had flown, just then there was a knock at the door. I spritzed some perfume on my neck, and went to answer the door. It was Steve, from the bar. He looked hunky as ever. He asked if I was ready for dinner, and I told him, almost. I have one tiny favor to ask of you before we leave. "What's that hon?" he asked. I asked him if he would pleeeeeeeeze put on a pair of my panties under his Dockers. He sort of snickered, and said "Aren't you the kooky cunt" I handed him a pair of light blue satin ones with rows of lace on the back and a darling little satin bow on the front. He removed his boxers, and put on the panties, without saying another thing. I knew it would turn me on all night, just knowing what he had on under his clothes. We left the hotel and walked up Duval, stopping every once in a while to watch some of the performing street people. We headed over to Boba Lu Southern Cafe for dinner. They had a Ricky Ricardo look-alike as entertainment. We dined on black beans and rice, Cuban Style, I slid real close to Steve and thanked him for a terrific supper, then I kissed him. Not a peck or a quicky, but a deep wet soul touching kiss. My hand fell to his lap where I could feel a serious hardness forming. I suggested that we pay our bill and head back to the hotel, but Steve said he wanted me right there. He told me to get under the table and to suck him off, right there in the crowded restaurant. That's exactly what I did, I got under the table, unzipped his Dockers, and kissed his cock thru his satin panties. Then I pulled the leg aside and freed his cock, only to entrap it again, with my lips. He kept whispering things like "He was in Lust with me" and "He loved my mouth pussy". I continued sucking him and fondling his balls thru the sensual fabric of his panties. He let out a rather load groan when he came and I was fearful that the entire restaurant knew what was happening. I swallowed most of what he deposited in my mouth. There were some rivelets of cum on my chin, which I didn't know were there, until I looked in my mirror to check my lipstick. As I got up from beneath the table, I could sense all eyes in the restaurant were upon me. My face felt hot as flames, was I ever embarassed. Steve reached over and scooped the cum trails from my chin and deposited them in my mouth, he did as everyone watched. How absolutely degradingly delightful. I told Steve that if he was a good boy, he could come back to my room and take me anally, he seemed to like the sounds of that.

 

When we got to my room, I removed my outer wear, and Steve said that I was a vision of loveliness standing there in my white lingerie. I put on a little more lipstick, and donned a pretty white and pink penoir set. Steve told me to suck him back to hardness, and then put some vasaline petrolium jelly on his dick, then get on all fours and spread my ass cheeks for him. I complied with his requests and was rewarded with a good stiff 8 inches. He told me to jack off while he fucked me. I stroked my cock thru the sexy penoir panties that I had on. Steve pinched and pulled on my tender titties while he fucked me, proper! I came at the same time as he did. He stayed inside me, until he was totally soft, then he withdrew and went to the bathroom to clean up. When he came back into the room, he asked me if I had any short skirts. I told him that I did, and he said that he wanted me to wear one, the shorter, the better. I told him I would have to change into some panty hose in order to wear a short skirt. He told me, no, you're not getting it, are you? I want you to leave on your garters and stockings AND wear a short skirt, oh, and no panties either. I was flabberghasted! But I did ask he instructed, Then we went out, back to Duval Street for some serious bar hopping. At first I was mortified, every move that I made seemed to expose my stocking tops and sometimes my clitty. But after a while, I guess I got numb to it. When we got to the Hogs Breath Saloon, Steve said he had a surprise for me. He knocked on the ladies room door, and when he got no answer, he pulled me inside and had me sit in the last stall. He pointed to a hole in the wall and told me that in a few minutes there would be a series of cocks appearing thru that hole, and he expected me to suck each and every one. I didn't tell him, I was already acquainted with this particular oddity. I spent the next couple of hours sucking cocks, big ones, little ones, fat ones, skinny ones, white ones, black ones, you name it, I sucked it that night. I was so full of semen that I had a belly ache. I didn't realize it, but Steve was getting ten bucks a head (no pun intended) for my services. Well, he did spring for dinner, afterall.

The next morning I had a hell of a case of diarhea, I guess that excessive quantities of sperm have a laxative effect. Anyway, I packed up and got in my car and headed back up to West Palm. I pulled my skirt up so that my garter tabs were plainly visible. I was going to have some fun with the truckers on my way home. I guess I take the Conch Train tour, on my next visit to the Island.

 

If you enjoy reading of my adventures please drop me a note at Tracy_LoveWPB@hotmail.com

The more detailed and naughty, the better.

  

  

  

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