Shemale Beauty: 1st Female Conquest

Summary: 18-year-old discovers her powerful sexual persona.

Note 1: This is the first of potentially many shemale stories starring the beautiful seductress Kara...

Note 2: Thanks to... Tex Beethoven, Robert, and David for editing this story.

Shemale Beauty: 1^st Female Conquest

Everyone has hobbies. For most people, hobbies can be activities like travelling, fixing old cars, playing musical instruments or collecting coins.

An approach to sex that began as my hobby has blossomed into my career. It has brought me a lot of wealth, allowed me to travel all over the world, and has made me a sought after woman in a world that is still driven primarily by masculine principles and attitudes. At least it is when I'm not present.

I am a transwoman, although people often refer to me as a shemale, a chick with a dick, or whatever other label you want to use to describe me. I am a mixture of the best qualities, psychological and physical, of a man and a woman.

As a woman, I have long, natural flaming red hair, falling a few inches past my shoulders, I have emerald green eyes that most people find hypnotic; I have a dazzling warm smile that disarms men and woman into trusting me instantly. I have adorably cute dimples that make me look sweet and innocent, the perfect girl next door. I have long, tanned legs that I accentuate with dark colored hosiery, usually mocha or black, that have men turning their heads even when they're with their wives or girlfriends. I have firm 36D breasts that literally defy gravity and lastly, I have the JenLo bubble butt that all men drool over. I have used my feminine wiles to my advantage ever since I can remember, since I have a diverse set of weapons to disarm almost any man, regardless of his sexual quirk.

As a man, I have a 'take no prisoners' attitude and the confidence to go with it. I am determined and hate to lose...ever...and thus have grit that borders on psychotic, and an ego to match. Lastly, if the rest of my body is feminine perfection, my cock is the golden standard that sex toy manufacturers should use to mold the perfect plastic cock. Eight inches, not too big or small, seven inches in girth with just a slight upward curve that performs miracles in a girl's tight pussy, or more times than not in a man's virgin backdoor (his 'man pussy', as I call it).

As a person, I love the thrill of the chase, the final submission and conquest; I love taking a straight man and sending him to his knees so he can prepare my cock for his man pussy, or draping him over his expensive desk at work so I can fuck him while he whimpers like a little girl. I also enjoy taking a straight woman and drawing her into the world of lesbianism...and the delighted look on her face when she first discovers a cock where a cunt should be is priceless. Plus, when a hetero woman finds her self-image suffering when she finds herself unable to refuse the charms of an irresistible woman (me), but she's still struggling against the idea of becoming gay, her relief when she finally unveils the sole physical indication of my manhood is priceless. I may seduce her as a woman, but I can fuck her as a man. Problem solved!

Personally, it's all the same to me. Sex is sex and I am an equal opportunity fucker.

Which brings us to my career. The most succinct description of what I do is that I fuck for a living.

But without further explanation that description would be highly misleading. I'm not a call girl or a gigolo or whatever new label you might wish to invent for a transwoman selling her favours. I'm not hired to provide pleasure, even though I invariably do give and receive great pleasure, taking enormous pride in my craft.

A label that would be far more accurate is Assassin. Except that nobody dies, they just wish they had. I seduce people, men or women, and then deliver recorded proof of our assignation back to my client.

On rare occasions this encounter doesn't present the slightest difficulty to my target, most often because the person is part of the swinging lifestyle. If a person is comfortable admitting they're not sexually monogamous, an admission that many swingers are very comfortable with (especially with their partners), then the target and I discover we have enjoyed a lovely time together and my client has wasted his or her money. I've even been known to refund my fee when we've had a sufficiently lovely time, and in two memorable instances the target and I invited my client to join us for a threesome! Free of charge, of course.

Unfortunately (for themselves and for those who trust them), most licentious people are not particularly forthcoming about their practices. They make commitments (such as marriage vows or religious proclamations or campaign promises) in public, then ride completely roughshod over those commitments in private. People get hurt. So another succinct label for my occupation might be Karma. I bring people's pigeons home to roost.

It probably goes without saying, but I'm totally immune to blackmail. My life is an open book, and I freely admit to anything that I do. I'm telling you, am I not? Here's my card. My fees are posted online.

Most of my jobs boil down to rich, jilted wives wishing satisfaction from their cheating bastard husbands. Those jobs are the easiest; the husbands are already in the habit of cheating, so they naturally succumb to my beauty and charm, and once I have them in the hotel room, they're putty in my hands.

But I have also been hired by an opposition party to bring down a political leader; I have been hired by the female best friend of a bride-to-be to turn the bride gay so she will call off the wedding and marry her friend (I had to take great pains to finesse my cock so I could pull that one off); I have been hired to get revenge on a military father who was a little too enthusiastic with his son's corporal discipline; I have been hired to seduce the wife of the popular but corrupt mayor of a major city so that he wouldn't run in the next election; and I have been hired to bring down people in positions of power in a plethora of corporations, both men and women. Those are all fascinating stories I may tell one day, and since I travel a lot I have lots of time to write my memoirs...so who knows? Perhaps this story will lead to more revelations down the road. Giacomo Casanova was still engaged in memorable activities to write down when he was an old man!

My first straight conversion happened when I was eighteen and back then I was still very secretive about my condition, as I then called it. Only two friends knew I was a transwoman, and I had gone to great lengths to avoid being found out by anyone else, by never playing sports, providing written instructions from a doctor that I was never to participate in gym (my discrete doctor of course knowing full well that this restriction was for social reasons rather than physical impairment). I had even avoided the public school system completely until the start of eleventh grade by being home schooled.

But I craved friends, and thus my supportive and loving parents agreed to send me to high school for my last two years. I soon learned there was a very clear social hierarchy there, and being pretty and well-endowed in the chest department, I quickly climbed the invisible ladder. It did become tougher and tougher to hide my secret, especially when I was constantly hit on by the guys.

Yet, it was these same horny guys that finally led me into my passion...converting straight guys.

Wendy, a gorgeous friend of mine, had been dumped by the football quarterback, Jake, the day after prom when she hadn't put out, and a couple of days later Jake was fucking Tiffany, our school's sure thing.

I comforted Wendy, but got angrier and angrier at how guilty she felt about the break-up. I thought it was absurd for her to blame herself for being dumped, but shallow societies such as the ones that permeate high schools expect girls to have a certain cooperative approach to dating, and if we don't buy into it we get ridiculed.

Wendy was one of the two friends who knew I was a shemale, and accepted me unconditionally. I comforted her and said, "It isn't your fault he's a selfish bastard."

"But..." she began, but I cut her off.

"No, buts," I insisted, "he needs to be taught a lesson."

"How?" she asked, curious about my plan.

Although only eighteen, I already had a fair amount of experience with sex, even if it wasn't the hands-on variety. The Internet was a great way to learn that many others were like me (in numbers if not percentage) and many curious men liked the idea of a shemale; people like me made the act of sucking cock or becoming a bottom appear less gay.

My own sexuality was complicated. I liked both men and women, and yet had no up close and personal experience with either. Using the Internet, I explored my sexuality and feelings through many online chats, emails and some role playing. I quickly learned and came to accept that I loved the idea of dominance. I liked role playing where I would seduce a straight married man and make him my personal plaything; I loved being called Mistress, and I loved telling people what to do. I pondered whether the sexual thrill of online role play could transfer to real life, and thus I created an online account and bio for when I was going to be in Toronto for a week (my grandparents live there). I was inundated with offers by tons of men and a few women to meet, and I hadn't even posted a picture (not wanting my 'condition', which I still kept closely guarded in real life, to be accidentally found out).

I chatted with a few male and female candidates and narrowed them down to three. I hoped to meet up with one man and one woman to experience the best of both worlds, per se. I also had a back-up guy planned in case something fell through. I researched them online, had photos of each, and primarily through role playing, felt very comfortable with each of them.

I arrived in Toronto, excited and nervous about my sexual rendezvous. I was confident online and in real life, but I was still a virgin.

I had decided to meet Sandra first. She was a thirty-two year old mother of two and a kindergarten teacher. I researched her thoroughly, finding her school's website and her own class website, where I confirmed the pictures she'd sent me were really her. Believing I could trust her but still valuing an element of caution, I agreed to meet her for the first time for coffee at a café on Yonge Street just a couple of blocks from the hotel I had booked, even though she was generously paying for the room.

She was already waiting when I arrived, having chosen a secluded table in the corner; she was clearly nervous and kept looking at the door. I walked up to her table and said, "Hi, Sandra."

She was surprised by me, asking tentatively, "Are you Kara?"

"In the flesh," I joked.

"Wow," she said.

"I'll take that as a compliment," I replied playfully.

"You're beautiful," she said, clearly expecting someone less attractive.

"You're quite pretty yourself," I countered.

"Thanks," she replied, blushing.

"Give me a second while I go grab a mocha," I said.

I returned a couple minutes later and sat down so we could confirm our intentions and size each other up face to face.

"You are even prettier in person," I complimented, trying to get her comfortable with our unique plans.

"Thanks," she said, her tone revealing just how nervous she was.

"Don't be nervous, Sandra," I said, moving my hand on top of hers.

She seemed startled by the intimate contact but didn't move away. (You will notice that I was the one reassuring her, even though she was just four years shy of being twice my age. Even back then I was well on the road to becoming the take-charge person I am today.)

I continued, "I see you're wearing the outfit I requested." (I won't belabour the point; you get the idea.) I loved the idea of expanding people's horizons by pushing them out of their comfort zone, and had instructed her to wear a schoolgirl outfit: a white blouse, her hair in a ponytail, a plaid skirt and pantyhose (just because I love the feel of the silk).

She replied, "I felt awkward buying the plaid skirt."

"But you did it for me didn't you, my pet," I purred, perpetuating the term I had given her since our early online role plays.

"Yes, Miss Kara," she admitted, addressing me as she had done since we began chatting online and our domme-sub relationship had begun.

"Are you ready to be my good girl?" I asked, my hand slowly moving up her arm.

I could feel her shivering at my touch and nervousness exuded from her as she whispered, "Yes."

"Yes what, my pet?" I questioned softly, almost in a whisper, even while keeping the emotional intensity up and my expectations clear.

"Yes, Miss Kara," she rephrased.

"Good girl," I purred, before clarifying our timeframe and trying to make her submission even more humiliating. "How long does your ex have the kids?"

"All night, Miss Kara," she admitted, still not able to make eye contact with me.

"Oh my, you are one eager little pet," I commented playfully.

Her face was as red as Snow White's apple, but she didn't respond to my playful banter.

"Look at me, my pet," I ordered, even though my tone remained soft and sweet.

She obeyed, uncertainty showing in her eyes.

"If you're having second thoughts, we don't have to continue this," I pointed out.

Her eyes went big and she stammered, "N-n-no, I want to, it's just that I've never done this before."

"I need to be confident that you want this, Sandra," I stressed, "I need proof," moving my hand away and leaning back in my chair.

"I'll do anything," she said, a sudden panic in her voice.

"Go to the washroom, remove your panties, put your pantyhose back on and bring me the panties. Carry them draped over a single extended finger so it's obvious to anyone paying attention what you're carrying," I ordered. "If anyone asks about them, say you're bringing a present to your Mistress, and point me out. I'll smile and nod."

"Really?" she asked, surprised by my request.

"Now!" I said, my tone shifting to sternly dominant for the first time.

"Yes, Miss Kara, I'll be right back," she said, standing up and nervously rushing away.

I sipped my mocha as I awaited her return, the anticipation of what was to follow growing exponentially. My cock was hard, but well contained within my own pantyhose even though I was without any panties.

She returned, looking very awkward and nervous with her silken powder-blue panties draped in front of her like a delicate banner even though nobody seemed to notice. She sat down and handed me her panties, portions of which were wet. I surprised her by taking them and lifting them to my nose. "Hmmmmm, you have a sweet scent, my pet."

"T-t-thank you," she stammered, clearly embarrassed.

"Thank you what, my pet?" I questioned, her panties still openly displayed in my hand.

"Thank you, Miss Kara," she quickly rephrased.

"I'm beginning to think you want to get punished, my pet," I quipped.

"No, Miss Kara," she said, "I'm just very nervous." After a pause, she added, "Nervous and excited."

"I can tell," I agreed, "your panties are very, very wet, my pet."

Her ruby red cheeks returned, as I placed her fragrant panties in the center of the table, in clear view of any passers-by.

Pushing our encounter along, I shifted to a more frank conversation. "Are you ready for me to fuck you, Sandra Pennington?" I didn't know why I added her last name to the question other than because I could, but I did. Later I would learn that addressing a person by their full name when you're challenging their comfort level emphasizes the fact that they're not anonymous, and thus makes the challenge feel more personal and vivid to them. I didn't have all the theory at my fingertips that I do now, but my instincts were sound even then.

Her eyes again went big, she looked around to check that no one had heard my forthright question before answering, meek like a mouse, "Yes, Miss Kara."

Raising my voice a little, but still not loud enough for others to hear, I added, "And are you hungry to get my cock nice and ready with those pretty cock sucking lips of yours, Sandra Elizabeth Pennington?"

I didn't know a face could go that red, her humiliation at my questions causing her extreme discomfort, which for some reason turned me on. She again answered in the affirmative, "Yes, Miss Kara."

"Be descriptive, my pet; tell me exactly what you will do to my cock, my pretty cocksucker," I pushed.

Again she glanced around, and this time I scolded her, deliberately increasing her discomfort by raising my voice even further. "Slut, don't worry about what anybody else might hear, your only concern is pleasing me, is that understood?"

"Y-y-yes, Miss Kara, I am t-t-truly s-s-sorry," she stammered, clearly worried she had disappointed me.

Building on her insecurity, I added, "Good girl; please don't disappoint me again, my pet."

"I won't, Miss Kara," she replied, her nervousness about our surroundings gone and replaced with a focused eagerness to please.

"You will be a good pet, won't you?"

"Yes, Miss Kara. I will be a very obedient pet," she agreed.

"So back to what you plan to do with my cock once I've wickedly lured you to that hotel room," I said, returning us to our previous conversation.

The shift from insecure to eager complete, she never even glanced away, her eyes staring constantly into mine as she answered, "As I told you after you sent me that picture of your cock, I've been obsessed. I've fantasized about making love to your cock with my mouth, about having you face-fuck me until I swallow your cum."

Hearing the sweet kindergarten teacher describing my face-fucking her was hot, especially after how timid and insecure she'd been a few minutes ago. "Well, let's go make that fantasy come true, my pet," I suggested, standing up.

She stood up too, taking a glance at her wet panties on the table.

I smiled, "Leave them there my pet; you won't be needing them, and they might provoke some enjoyable speculation for whomever clears the table."

"Yes, Miss Kara, whatever you say," she submissively replied, making my cock flinch, desperate to be released.

She followed me out of the café and the couple of blocks to the hotel.

"Nice choice," she commented as we entered the lobby.

"Only the best for my pet," I replied smiling, both of us ignoring the fact that she had paid for the room. An important undercurrent to our upcoming interactions was the idea that she was entering my space, and we were both aware of that requirement.

We went to the front desk where the woman was professionally pleasant and had no idea of the debauchery I was planning to launch in just a few minutes.

Given our keys, we headed to the elevator where I took her hand in mine. We waited a couple of minutes for the elevator and another couple, in their fifties, waited with us. I looked at the couple and saw their surprised look at encountering two lesbians in person, or at least what appeared to be two lesbians.

I smiled at them just as the elevator door opened. Once all four of us were inside and the door was closed, I decided to shock the older couple and test my pet. "On your knees, my pet."

Sandra looked surprised but hesitated less than a second before falling to her knees.

"Good girl," I purred, like I was talking to a puppy.