Carolyn Makes Her Way

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After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity and applied my makeup carefully, I brushed my long red hair, no wig for me, and made certain that my purse was nicely stocked. I always carried five or six rubber just in case whoever was going to pound my ass had forgotten his. A girl has to be safe with strangers. Accessories are a must to complete any ensemble, rings on each hand, a necklace with a star shaped pendant, earrings of course, a gold ankle chain and three bracelets on one wrist. Finally I slipped on a pair of black stilettos, the five inch heel variety, and I was ready to go. With any luck at all I’d meet a man or two or more, get my tranny ass fucked hard and suck a nice fat cock. Gay, straight, bisexual, married or single, it didn’t matter to me. After all, I’d gone almost an entire week without anything except a dildo and my hand and I was super horny. As I drove to my favorite pick up bar, I thought about what they’d say about me at work if they only knew. As far as anyone knew my name was Carl, a very mild, milk toast man, never outspoken, and a very good worker. Tonight my name is Carolyn, a very sexy, always ready to party, sexily dressed, transvestite. My measurements, which I worked hard to maintain were pretty good, red hair, green eyes, five feet five inches tall, one hundred and twenty-two pounds, C cup boobs, which were store bought, very petite and dainty, and the biggest slut around. When I walked into the bar I saw that getting there early might have its drawbacks. There was me, the bartender, two men, obviously lover, or about to become so, sitting in a booth, a man at the bar with another girl like me hanging on his every word, as well as two tranny other girls I knew waiting for men like vultures waiting for road kill. “Hi, Carolyn,” Jerry the bartender smiled. “Hi, Jerry,” I smiled and waved. He and I were on a first name basis since he had face fucked me behind the bar a few times. “Ladies,” I said smiling as I approached their table. “May I join you?” “Sure, babe, pull up a chair,” Melanie replied. She had raven black hair and smoking hot eyes to go perfectly with her long, shapely legs. “Pretty dead in here,” I said, taking out a long, slim cigarette and placing it between my cherry red lips. “But it’s Friday and we’re early. It’ll pick up after the guys go home and clean up,” Sheila quipped and smiled. This week her hair was long and blonde, falling well past her shoulders and framing her face perfectly. Sheila was the wild one, even wilder than me. She had, on more than one occasion, given a table dance in here, stripping all the way down to her stockings and heels, then taken one in her ass and one in her mouth in the middle of the dance floor. “I’ve never been here this early, well once when I helped Jerry stock the bar and he paid me with a good ass pounding. You know, he’s got a dong on him that any horse would be proud to own and he knows how to use it,” I replied. “We look like a Neapolitan ice cream, a redhead, blonde and brunette,” Melanie observed and giggled. An hour later the place was more populated and then I saw the unthinkable. Mike, a man I worked closely with strutted into the bar like he owned it. At first I felt pure panic and then it dawned on me that he was in a gay bar and if he had anything nasty to say he was just as guilty as me, except I was there in women’s clothes. A few minutes later and one of the guys waiting on customers brought a round of drinks to our table. “Compliments of the gentleman at the far end of the bar,” he said, indicating Mike, who was now tipping his glass in our direction. “Gentleman? In here?” Melanie laughed. But Sheila said, “Ask him to join us.” Just a couple of minutes later Mike approached our table, “I couldn’t help but notice the three loveliest women in here all sitting together.” “Safety in numbers,” Melanie laughed. “I’m Melanie, this blonde cutie is Sheila, and that redhead sitting over there looking like someone just punched her is Carolyn.” “I’m Mike. Tell me something about yourselves,” he laughed, “and I’ll keep buying.” Sheila was the first to speak, “Nothing personal, Mike, but if you want some of me you better invite a friend or two. I like it rough, long and hard at both ends at once.” “Pity, I don’t think I have any friends here but I might make some real quick.” “I just like it anywhere you want to put it, Mike. I like one on one and twenty on one, if I’m the one,” Melanie giggled. Sighing I finally spoke and hoped he didn’t recognize my voice, “I’m just your average girl who works five days a week and likes to kick up her heels on weekends. In bed I’m a horny little slut who never, ever, says no.” “I like you already, uh, Carolyn,” he smiled and continued, “I’ve always had a thing for redheads.” “I’ve always been a redhead,” I answered quickly, “and if you’re lucky I’ll prove it.” “A natural born redhead, huh? You know, I work with a guy that’s got red hair. Maybe I’ll ask him out for a beer after work one of these days.” “Well if you’re looking for a man, honey, güvenilir bahis you’re at the wrong table,” I replied and met his eyes. “No, I think I’m at the right table. Three lovely ladies. Hard to beat three of a kind.” “But three kings just walked in, so if you’ll excuse me, I’d like to go talk with them.” Sheila said, standing to rise. Jerry and I continued our conversation, “So tell me about your red haired friend at work.” “He’s an alright fellow, kind of shy and reserved, but a nice enough guy.” “Do you think he’s the kind to take your interest?” “Probably not. But I’d like to think he’s a friend.” “You said he was shy, maybe he thinks of you as a friend but doesn’t know how to say it without sounding gay.” “I don’t think he’s gay, just shy,” Mike replied. “And if he was gay, maybe we could be really good friends,” he added with a grin. “So ask him out,” I said. “Then he’ll think I’m gay?” “Aren’t you at least bisexual?” “But he doesn’t know that,” Mike countered, “and letting the word get around work that I’m bi would be disastrous.” “Well, honey, you can be as bisexual as you want with me,” I told him bluntly. That was when Mike placed his hand on my thigh, just below the hem of my skirt. He moved it upward very slowly, gently rubbing my nylon clad skin. “Mmm, that feels good, baby,” I moaned just loud enough for him to hear me. When his hand came in contact with my panties I’m sure he could tell I was very turned on by the way they were bulging outward. Then his hand slipped inside my panties and he fondled my short dick and balls. “You’re getting me hot,” I whispered. “Very fucking hot.” “That’s the plan, sugar,” he grinned. “Plus I needed to make sure you weren’t a real woman. I’m not looking for a real woman. And you’re more passable than a hell of a lot of women I’ve met in here.” “If that’s meant to be a compliment, I’ll certainly take it,” I said demurely and let my hand find his crotch. His bulge was quite impressive, I thought to myself, and stroked him through his pants. “Oh goody, look at what I found, a lollipop,” I giggled. “Yep, you want a lick or two?” “Certainly, or three or four.” “You can have as many as it takes,” he grinned. “That’s what I like to hear, almost as much as I like to hear ‘I’m cumming’,” I replied with a huge grin. “Well now, this could be your lucky day, Carolyn,” he said, “I carry a heavy load in my repeater, the first one is like a hair trigger, the second takes a little longer, and the third one will wear your ass out. Quite literally.” “Three in a row? Damn! Most guys can do it a couple of times in a day. But three in one sitting? Wow!” “Interested?” “You better believe I am.” “Want to go some place with a little more privacy?” “Anywhere you want to go, honey, just lead the way,” I replied breathlessly. As Mike led us out of the bar, I could feel the excitement racing through my body. When we stepped outside into the cool darkness, I wanted to drop to my knees and suck his cock right then. I was so horny I felt like I might explode. He opened a car door for me and let me slide in before shutting it behind me. I waited patiently for him to get behind the wheel and asked, “Would you like a blow job?” “I thought you’d never ask,” he replied quickly and pushed his seat back to give me plenty of operating room. After fumbling with his zipper I finally got his long dick pulled out into the open and it didn’t waste any time getting rock hard. Leaning over to him I moved my head downward and my lips met the tip of his cock. Just a few minutes later my head was bobbing up and down on him. I know that the ridge and underside are the most sensitive but I’ve always liked taking the whole thing in my cock hungry mouth, and after some work, I managed to do so. Feeling a hard cock in my mouth is one of the most wonderful things I’ve ever felt, something I live for. He was right about at least two things, his first orgasm was almost like a hair trigger and he pumped a huge amount of cum, which I greedily took. I love the taste of cum, and I have loved the taste of cum since the first time I ever sucked a cock in his car several years ago. One time was all it had taken and I was hooked. His cum or my own, either one would satisfy me. “Mmm, babe, that was so damn excellent,” Mike groaned after shooting his load in my mouth. “I like to please my man,” I purred after swallowing most of his sperm. “Care to go to my place and get more comfortable?” “Is that the polite way to say get naked and fuck? Because if it is, let’s get moving!” “It is, and we’re off.” “Do you really think you can go again?” His response was to take my hand and place it on his naked cock. I was really surprised by how hard he had become in such a short amount of time. Quite pleasantly surprised. “I guess that answers that question,” I laughed. We pulled into his driveway and I saw that his house was huge, a lot bigger than I had thought for a single man and I commented on it. “Huge house you have here, Mike. You live by yourself?” “Just me. My wife ran off with some guy about four years ago, and I haven’t heard from her since. Hell, she was fucking around on me all the time.” “Sorry to hear that.” “Yea, I was too, at the time. I’ve gotten past her and I’m moving on.” He patted my leg and smiled, “If she only knew. If she only knew.” As soon as we walked though the door he pulled me to him and kissed me so hard he took my breath away. “Care for a drink?” “Only if you’re having one,” I smiled and let him decide. güvenilir bahis siteleri “Same as you were having at the bar?” “That’ll be fine.” “Make yourself comfortable and I’ll be right back, unless you’d care to join me.” “I’d like that,” I replied and followed him into his den. I say on an overstuffed sofa while he made our drinks. That was when I noticed a pair of locking wrist cuffs with fake fur padding. Then I saw a paddle that could only be used for spanking. “Are you planning on using these tonight?” “Huh? Oh. No, I make them in my spare time for a friend. Him and his wife like to get kinky every now and then, and he asked me if I could do any leather work besides make belts and wallets. I said I’d give it a try. Then he told a friend, and my hobby started growing by word of mouth. I make whips, paddles, wrist and ankle cuffs, full head gear. You name it and I can make it out of leather. I’ve made some that have a mark, or brand, of the Dominant, male and female.” “The workmanship on these items is excellent,” I said after examining them. “How long does it take to make them?” “Well, if I have everything on hand and there’s no special tooling needed, I can knock out a pair of cuffs, like those in a few hours?” “Can you make leather clothes?” “Yep. Takes a little longer to make a vest or a pair of leather pants and I have to have precise measurements.” I thought about some of the leather goods I’d scene in a shop a few years ago when I was in a bigger city and remembered the prices. This was exactly the type information I filed away for future reference. “Why? Do you want something?” “I was thinking about a pair of skin tight leather pants.” “I could let you have them at cost unless you want some kind of fancy design. I can make them so tight I could see the outline of your dick.” “Really?” “You want a pair?” “Yea, I believe I do.” “I’ll take your measurements after you have on a few less clothes,” he said and handed me a drink. “Are those your real tits?” “No, they’re just glued in place silicon boobs. I like the glue on kind so I can go without a bra and they stay in place.” “Good idea. Have you thought about growing your own?” “All the time but I think I might have a hard time at work.” “Hell, if that’s what makes you happy, find another job.” “I like what I’m doing and who I work with, but that could all change for the right situation,” I smiled. “Enough talking,” he said and moved closer to me, taking my glass and setting it on the table before moving in for another passionate kiss. Cupping my ass cheeks with both hands under my skirt, Mike pulled me closer to him. I could feel his bulging cock pressing into my tummy while his tongue explored my entire mouth and my slender arms went around his neck. All I could think about was having his hard cock buried deep in my ass and pumping me full of hot cum. “I want you,” I whispered. Before I even realized what he was doing my panties were around my ankles. I stepped out of them and returned to his kiss. Now his strong hands were kneading my bare ass and I was getting hornier by the second. He took me by the hand and lead me to the bedroom where he unbuttoned my blouse and pushed it off my shoulders while I began taking his shirt off. In short order we were both naked and I got to see his entire shaft, and it was very well worth seeing. Calculating quickly, I figured that Mike may be the biggest cock I’d ever had the pleasure of servicing. “Mmm, I like what I’m holding,” he said and kissed me again as we made our way to his bed. “You’ve got me too hot, baby,” I said, smiling at him. Mike played with my firm ass more and slipped a finger into me, making me moan with untold passion. We fell onto the bed and kissed and groped. Soon enough I was on my back and he was between my legs, tilting me upward toward his hard dick. With the help of a generous portion of lubricant and gentle use of four fingers, my ass pussy was hungry to accept hm. Placing the head of his cock against my puckered hole, he began pushing into me. The head of his dick gradually opened me, causing me to gasp and groan loudly. It had been a long time since a cock of this stature had been in me and feeling myself open so widely was amazing. “Damn, you’re tight,” he groaned, pressing steadily into me. “You’re just so fucking big!” I yelped as I pushed back against him. Then he slid completely into me and I’d never felt so full in my life. After a moment or two, he pulled my legs up over his shoulders and began to move slowly in and out. “Oooohhhh, baby, that’s so good!” I cried passionately. Mike picked up more and more speed until he was banging my ass pussy with long, hard, and fast strokes. “Yea, baby, yea! Oooohhhh yyyesss! Fuck my asshole with that big dick! Make me feel like a woman! Fuck me! Fuck me! Yyyesss! Yyyesss!” My mind was spinning with more passion than I’d felt in a long time as he slammed in and out of me. At least twenty minutes passed by and he showed no signs of letting up. I, on the other hand, was racing toward a tremendous orgasm even though I was a long way from being hard. “You’re gonna make me cum, Mike! Oh fuck, I’m gonna cum! Oooohhhh! Oooohhhh, I’m cumming! I’m cumming! “ I screamed as my entire body began to shake out of control. Wave after wave of glorious orgasm raced through my body and then started again. I was in my third wonderful orgasm, two of them where I had orgasms more like a woman than a man, one the other where I pumped my seed onto my iddaa siteleri belly, when he jerked, stuttered, and started pumping his hot seed deep inside me. I held onto him, riding his pulsing cock, my ankles locked together behind his neck while the heat of his seed spread throughout my very being. “Oh fuck, Carolyn, your ass pussy is so fucking hot! Mmm, baby, I love it!” Mike said and kissed me while remaining buried deep inside me. “Oh, baby, that was fantastic,” I panted, still holding him in me. “How about we go finish that drink and I’ll take your measurements while I’m at it,” he said as we both felt his cock beginning to shrink. “Sounds good to me,” I said as he slipped completely out. As soon as his cock unplugged my ass a flood of hot cum practically shot out of me. I liked feeling cum as it traveled down between my ass cheeks. After making us fresh drinks he pulled out a cloth measuring and asked, “How low do you want them to ride? Hip hugger? Lower?” “Lower. I like showing off.” “A one inch rise is the lowest I have,” he told me as he took the measurements and began writing them down. “Boot cut? Flare? Stovepipe? Skinny?” “Skinny, I guess. I just want to show off everything and look sexy. I’ll be wearing four or five inch heels with them.” “Got it. You want whatever makes you look the most like a slut.” “Yep, so use your own judgment.” “How would you like to go relax in the hot tub?” “Sounds divine.” The warm water felt glorious and so relaxing and invigorating and was made that much better when Mike sat next to me and let his hands roam over my nude body. We kissed and fondled one another until I could stand it no longer. “Mike, honey, you’re just gonna have to take me to bed again,” I moaned, breaking for air. “You sure you’re up to it?” “Mmm, yes, I need it! Please!” Once out of the hot tub and dry, I took his hand and lead him back to the bedroom. He was on me and deep inside my yearning ass pussy in short order and I was moaning loudly, this time we were using the doggie position. Mike took me with long, hard strokes, bumping my curved butt soundly with each down stroke. “Oooo, oooo, baby! Fuck me, Mike, fuck me hard!” I pleaded. “Oooohhhh, fuck yes! Oh damn, that feels so fucking good! Fuck me! Use me! I’m your cum dump!” “Damn, you’re so fucking tight and hot!” He groaned and slapped my ass sharply. The sting of his slap got me even hotter. “Oooohhhh, yyyesss, spank me, daddy!” And did he ever! With every third stroke he slapped my ass, one side and then the other. I’m sure my butt was becoming bright red since he was spanking me so often. “You’re such a naughty little girl,” he growled, “I should just put you over my knee and spank you’re sexy ass!” “Oooohhhh, yyyesss! Yyyesss! I’ve been so naughty, Daddy!” I don’t have any idea how long he fucked and spanked me, at least an hour. My orgasms were tremendous, crashing through me, one right after the other. When I looked back between my legs I could see my dick dripping cum onto the bed, but I couldn’t recall when my balls had released their creamy treasure, nor did I care. Suddenly, Mike held me tight and really fucked the hell out of me, and then started cumming in me, this load every bit as much as the first two. When he finished he pulled out of me and we lay together, his arm around me until we both fell asleep. We slept soundly through the night. The next day I was up and cooking breakfast when he walked into the kitchen. “Smells good!” “Hope you like it,” I said and poured him a cup of coffee. “I’m sure I will. Damn, fucks like a rabbit and cooks to boot. Clean house?” “Fanatically,” I laughed. “Married?” “Nope. Footloose and fancy free.” “Yea? One of these days you’ll make some man happy and be his bride,” Mike said with a grin. “I don’t know. Maybe. Maybe the right man hasn’t asked me,” I answered and placed his plate in front of him. “I’m curious. What would be the right situation for you to take hormones and grow your own titties. I mean, everything else is just perfect until you get to those silicon buddies.” “Oh, I don’t know, maybe a job where I could be a woman without being harassed by upper management. I mean, if I was being harassed because they wanted in my panties is one thing, but putting up with all the queer jokes and chides is something else. For instance, if I came out like this at the place I work now and got all the harassment I know I would, I’d be ready to walk out the door the first day.” “Understandable. I think if it got out that I like girls like you, or anything, that I’d be bombarded with that kind of shit. I wouldn’t quit but I’d probably get fired.” “So we stay in the closet, at least the workplace closet.” We chatted for a few hours until it was time for him to take me back to my car. “I’d like for you to come back to my house,” he said before I got out of his car. “I’d like that also but I need to get home and change clothes. You know what I mean.” “Any other plans? A date, maybe?” “No.” “Then come back to my place for the night. We can take a midnight swim if you’d like.” “Okay, I will,” I answered and wondered when he’d finally recognize me. He kissed me goodbye and I was soon driving back home, thinking about him the entire time. Once at home, I shaved my legs just to make sure there was no stubble, changed clothes, picked out a few things to take with me, and thought about what I was doing. I liked Mike, had always felt an attraction to him at work, and after last night I liked him even more. Sooner or later I’d have to tell him that we worked together and then he’d see why I couldn’t get on hormones, but in the back of my mind I was working on a plan that hadn’t quite formed. Three hours later I was sitting next to him while we watched a movie.

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