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TransPhases - A Most Memorable Date

 
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It's been said that there are no better cocksuckers than men, and when you consider that men should know best how to work their own equipment, the reasoning is quite simple. I was once a professional cocksucker myself, so from my own experience, I know this to be true.If you met me for the first time, you'd never guess that I was born in a male body. I've already written a lengthy series about my transition nearly fifty years ago, so I won't go into much of that here. I'll just say that I know what I'm talking about when it comes to men being the better cocksuckers.I'll admit that percentage-wise, most of the men I've been with were bisexual cocksuckers like me. Then after I transitioned, I attracted heterosexual men looking for the unique sexual experiences that only t-girls can offer, and I was never shy about taking money for sex.To be fair, most of them were just as respectful of me as the bisexual men I usually had sex with. Some of them, though, were conceited assholes who thought they were in a higher class of their own.Sexually speaking, their bedroom prowess hardly ever matched their arrogance. I was far more experienced than most of them in that regard, so I easily had them wrapped around my little finger once I gave them a taste of my exquisite t-girl cocksucking skills.Trans girls, you see, know the male psyche better than the average woman, since we were born with the same equipment. We're also, in my opinion, better at working the equipment.To prove my point, I'll tell you about an experience I had back in the early nineteen-eighties, after I'd been taking hormones for about eight years. It involved a heterosexual man who regularly cheated on his wife because he thought no woman could resist his cock.~~~~~For those unfamiliar with my TRANSformation series, let me first explain that before we transitioned, my life-long soul mate Allie and I were already into cross-dressing and fucking guys for money. Our clientele often referred to us as escorts, but we always knew what we were.We were effeminate male prostitutes, and as we transitioned to female, we morphed into uninhibited, high-class transsexual whores. Trans girls were a rare commodity back in those days, and once we learned to take advantage of what we were, we used our unique sexual attributes to become rich.We mainly became rich because we were fortunate enough to get into prostitution through a secretive, invitation-only club the members simply called, 'The Club'. This secret society was made up exclusively of very successful business and professional men who had one thing in common, they were all very bisexual.Most of them, I should add, were obsessed with anal sex. Back then, ass fucking was considered so degenerate that hardly any woman would give her consent. But Allie and I were really into it, so we were always happy to let them fuck our tight young asses in exchange for their money.To make a long story short, when Allie and I found out we had a condition now known as gender dysphoria, we were already living full-time as girls. The Club was very supportive of our decision to transition to females, and for the better part of twenty years, we were the Club's exclusive whores. We made a fortune gang-banging the guys at their meetings twice a month, and we made even more money dating them individually two or three times a week.Out of all the men I've privately dated, Norm was my absolute favorite of all time. He was the first guy I met at the Club, and the first guy who ever paid me for sex. Over the years, he taught me almost everything I know about the business, and being thirty years older than me, I looked up to him like a father.Norm was one of those guys who loved his oral sex, and his wife was one of those women who despised it. Norm was so addicted to cocksucking that he always had a secret male lover on the side to give him what his wife couldn't, or wouldn't.After we fucked a few times at the Club, I became his secret male lover, and we dated often. He loved having a secret cocksucker who was also a cross-dresser, and when I transitioned to female, it got even better. We were so in tune on a sexual level, we were like husband and wife in bed.On a much higher intellectual level, he was my mentor, guiding me through my young adult years like a father would guide his daughter. I loved those times when after an hour or so of mutual fellatio, we'd snuggle up and just talk. I'd lay my head on his bare chest, and he'd teach me so many things about getting Artvin Escort ahead in life.The most valuable lesson he taught me was identifying a man's weakness and exploiting it to my advantage. We became so intellectually close that we could see into each other's soul, it seemed.~~~~So when I met Norm for a date one night, I immediately knew something was wrong. He'd always greet me in the hotel lobby with a hug and a kiss, then he'd brush his hand across my ass and tell me how anxious he was to fuck it. I'd always giggle back and say something like, "It's the best ass money can buy."Whenever something was bothering him, he'd always grab my ass instead of just brushing it. On this particular night, he grabbed me so tight I had to remind him we were in a public place before he finally let go.Later on, when we were having dinner, he was unusually quiet. He'd normally be all bubbly and always cracking jokes, but on that night, hardly a word."Anything wrong, baby?" I asked."I'm sorry, Jill. I don't mean to ignore you, it's just that I have a lot on my mind. I probably should have canceled our date.""Want to tell me about it?""Naw, it's my problem, not yours.""Problems at home? Or is something going on at work?""No, the wife is fine.""Then tell me what's going on at work.""You wouldn't be interested. It's pretty boring stuff.""Try me," I said with a wink. "Whatever it is, you can tell your girl about it. You know she won't tell a soul.""God dammit, Jill," he chuckled after I'd prodded him enough, "I've taught you too much about exploiting a man's weakness.""Your weakness," I said as I reached across the table to hold his hand, "is me! You know you're gonna tell me, so when's it gonna be? Now?? Or will I have to squeeze it out of you later, when I'm sucking your cock?""Damn?! You can be a pushy little bitch at times.""Well, didn't my mentor teach me to assert myself when I know I'm right?""Okay? okay," he finally gave in, "if you must know? one of our subsidiary companies has invented a new technology that could revolutionize the way farmers harvest their soybeans.""And that's a problem?""Well, it is and it isn't. We've received a decent offer to sell our interest in the company, but I think we can do a lot better if we buy out the other interest and develop it ourselves.""So why don't you?""It's not that simple. There's a fucking problem somewhere, and I'm not sure where it is. I think an insider in our company is trying to steal it before we can acquire full ownership of the subsidiary company.""How could they just steal something like that? It must be worth a fortune.""It could be worth billions, Jill. The problem is, we only control a small majority stake in the company. I think the offer is a hostile buyout attempt, but I don't know who's leading it. I have a couple of hunches, but I can't make a move without tipping them off.""That's all you know right now?" I asked as we finished eating."Yeah, unfortunately, I can't do shit until I know more, and then it might be too late.""Well, if you can't do shit about it right now, why don't we go up to our room and get comfy. You've always told me it's best to just relax and sleep on it when you don't know what to do."~~~~~I'd never seen Norm so nervous as we went up to our room. There wasn't anyone in the hallway when we got off the elevator, so I hung on him like the little whore I was back in those days. If there's one thing that gets a man's mind off his problems, it's knowing he's about to get a great blow job, and Norm knew I was the best in that department."You're really worried," I said as we closed the door to our room, "can you forget about it for a few hours and just let me take care of you?""Thanks, baby doll," he said as he lifted my dress and grabbed my shapely ass, "I don't know how good I'll be tonight.""You don't have to do a thing," I said as I unzipped his pants and grasped his soft cock. "You pay me to pleasure you, but I love you so much, I'd gladly do it for free.""We've kinda been in love for a while," he acknowledged as we stood by the bed."Yes, we have," I swooned. "You've been so good to me, how can I be anything else but in love with you?""How long have we been dating now?""Almost ten years," I told him, "and in that time, I've gotten to know you inside and out. In some ways, I know you better than your own wife. I know this problem at work is deeply troubling you, and I think it would help if you'd talk to me about it.""You shouldn't be bothered Artvin Escort Bayan with my problems," he said as I helped him out of his pants. "I've been a CEO for over twenty years, and I've handled problems like this before.""But I've never seen you this worried before," I said as I knelt on the floor to suck him.Looking up into his eyes as I licked his flaccid cock, I saw a worrisome look I'd never seen before in this normally confident man. I softly moaned the way he always liked me to as I kissed the head and took him into my mouth. He'd usually be leaking pre-cum at that point, but I wasn't tasting it that night."Your cock isn't even starting to get hard, baby," I stood up to confront him. "I'll be so disappointed if I can't swallow your load.""I'm sorry, Jill," he said with a dejected look, "I told you I probably wouldn't be good for sex tonight.""Then how about a back rub?" I asked as we hugged. "Maybe you'd like me to feed you my cock after I massage you?""Mmmmm? yeah, baby. I like that idea!"Luckily, I had a bottle of massage oil handy in my purse. An escort never knows when she'll need things like oils, lubes, and condoms on a date, so I always made sure I was well-supplied. Norm pulled the covers to the foot of the bed as I got the things I needed from my purse.I did a sexy strip-tease for him as he lay naked on the bed, but I couldn't get a rise out of him. His limp dick told me I wouldn't be getting fucked, so I joined him on the bed and gave him a massage. Like I said before, some of our best times together were when we just talked.Over the next hour, we talked about a lot of things. I was straddled over his shoulders, teasing my cock across his face, when I finally got him to open up about the problem he was facing at work. Apparently, he suspected the person behind this potential hostile takeover was a young executive named Jason, who joined the company about a year before.Norm lapped at my balls as he described Jason, an arrogant opportunist who made it known that he wanted to climb the corporate ladder all the way to the top. In other words, he wanted Norm's job. He was licking the velvety-soft skin of my hard feminine shaft when he told me that rumors were circulating around the company that Jason thought he was God's gift to women, and he cheated on his wife at every opportunity.That got the wheels turning inside my head as I began fucking his mouth. I swear, that man gave the best blow jobs of any man who's ever sucked me, and almost at the very moment he made me cum, I came up with what I thought was a brilliant plan."Hey, baby," I suggested, "Why don't you have a dinner meeting to discuss this new technology with all the company big shots? If you take me along, I can put on my best bimbo act and sniff this Jason guy out."Norm gulped at the idea. "You'd do that for me?""Yes, darling?" I whispered as my tongue dipped into his cummy-tasting mouth, "I'd do anything for you. If he thinks he's a ladies' man, I can probably seduce him and see what I can squeeze out of him. If women are his weakness, I know how to exploit it.""I'm not sure it'll work," Norm expressed some doubt, "but at this point, I'm not sure what else to do. It's at least worth a try."~~~~~About a week later, Norm picked me up at our house to take me as his date to the company dinner. He'd taken me to a few before, so I'm sure everyone knew the nature of our relationship. I took extra time with my makeup for that date, because if I was going undercover, so to speak, I needed to put on my best look.I wore a skimpy, spaghetti-strap mini dress that barely covered the tops of my nylon stockings. I never did like wearing high heels, but on this night, I wore my four-inch platforms. I hated corsets even more than heels, but for Norm, I wore one to make my waist appear thinner than it already was.I've been skinny all my life, so my body filled out real nice when I transitioned. The hormone treatments really set me free and gave me a great female figure. My breasts also developed so well that I never got implants like most t-girls do. My tits might be on the small side, but they're all-natural, and I think they fit my petite body just right. I wore a special strapless push-up bra that night to make them appear larger than they were, so all in all, I looked pretty hot."Damn, Jill," Norm said when he saw me, "you're dressed to kill!""If I'm going to sniff out a rat," I laughed, "I need to look my seductive best.""You look so seductive, Escort Artvin doll, I'm tempted to take you to a cheap motel and fuck your tight ass before we even get there.""You could if you wanted to," I said with a kiss, "but we'd probably be late. You'll have more fun fucking me after I've slain this asshole for you.""I sure hope this works," he nervously said. "I'm not even sure he's the one we're after.""I'll find out," I said with confidence, "you've taught me well? daddy!"On the way there, we talked about how he might introduce me to Jason, and how he'd arranged the seating so that Jason would be sitting at our table next to me, along with several members of the board. I'm telling you, the more Norm told me about him, the more excited I was getting. My tightly-tucked cock was starting to get hard at the thought of seducing this arrogant asshole and taking him out!~~~~~Always the perfect gentleman, Norm came around to open the car door for me when we arrived at the ritzy hotel. He had his arm around my waist as we walked into the lobby, then held my hand as we entered the banquet room where the dinner meeting was being held.We arrived an hour before dinner was to be served, and probably twenty people out of the thirty-five expected were already there. I always found it entertaining during cocktail hour at these corporate events to listen in on various conversations going on around the room.The talk ranged from common office gossip, to people trying to impress the others about how much 'insider information' they were privy to. This was corporate life, and everyone was kissing ass to promote their standing in the company. Seeing the rut most of them were in always made me feel good about being a whore, because I wasn't stuck in that rat race.There were always a few single secretaries at these events so the big executives would have some targets to hit on, and that's how I met Jason. Norm pointed him out to me across the room shortly after we walked in.On first impression, he was indeed very handsome, and seemed very confident as he talked with two attractive secretaries. They looked like they were impressed with whatever he was saying, or maybe they were too naive to realize they were only there as potential pieces of ass.Because Norm was the CEO, everyone wanted to kiss his ass to gain favor, so a crowd flocked around us as soon as we walked in. At that point, I was just ornamental eye candy myself, and I was anxious to start feeling out Jason.I nudged Norm to say I was thirsty and going over to the bar to get a drink. We gave each other a wink, knowing that the unsuspecting Jason was near the bar area, and this sting operation was getting underway.~~~~~Jason was still putting on his playboy act when I left Norm. One of the two young secretaries he was with had moved on, and he was standing closer to the one still there. I immediately caught his eye as I walked towards them, and when I smiled at him, he got a bit flustered. It was like he had a sudden impulse to move on me, but didn't want to blow his chances of getting a piece of ass off the young secretary.She seemed a bit annoyed when his eyes shifted towards me as I approached, so just to piss her off, I wiggled my ass as I pranced by them. She was quite attractive, and it gave me a thrill to capture his attention, even though he was still with her.I hung around the bar for a while, running my fingers through my long, black hair to keep his attention as I sipped on my tequila sunrise. I could tell by the way the young secretary was getting more annoyed every time he glanced at me, his time with her was growing short.It wasn't long before another executive joined them, and Jason backed out to come towards the bar. I didn't want to appear too easy, so I turned away as he approached me. I did arch my back so my ass stuck out, but other than that, I waited for him to make the next move.I could feel his eyes checking me out from behind, but I played shy, still not wanting to appear too easy. I waited a while for him to make a move, but not getting the response I expected, I quickly turned around to catch him staring at me."Hi," I said as our eyes met."Well, hell-oooo," he responded favorably with an arrogant smile. "Why haven't seen you before? Were you recently hired?""I'm not an employee, I'm here with a date.""And who, may I ask, is the lucky gent attached to such a beautiful woman?""I'm not that beautiful, compared to all the young ones around here. I'm here with Norm. He's the CEO.""Yes, Norm," he sneered. "The big C-E-O. How did he snag a hottie like you?""He didn't 'snag' me. We've known each other for years. I've been to a few of these before, but I don't remember seeing you. I'm Jill, by the way," I offered my hand, "Jill Cox."
09-02-2023, at 02:22 PM
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