Shemale Beauty: 1st 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 dMolestationd 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 dMolestationd 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.I looked at the couple who were stunned by what they were witnessing.
I smiled casually, as if we three were admiring a cute Pekinese Rocky at my feet, “She is such a good pet.”
The man smiled (lecherously, I have to admit), while the woman gasped. The elevator paused at their floor and she quickly got out, while the husband reluctantly followed.
As soon as the door closed, I ordered, “Stick your head under my dress, my pet. Get a good look at what you’ve been craving.”
Again just the briefest of hesitations, before her submissive nature and her hunger for my cock resumed control.
I watched her disappear under my dress and heard her gasp. Either because of what she had just done or at the sight of my fully erect cock held tightly in check, perfectly visible behind the sheer pantyhose.
I asked the question I already knew the answer to. “You like?”
“God, yes,” she replied underneath my dress.
The elevator slowed as it neared our floor. I ordered, “Crawl to the room, my pet.”
She reluctantly moved away from under my dress just as the door opened. A teenage girl was waiting, and she watched in stunned silence as I left the elevator, my human pet crawling behind me, her head down, avoiding eye contact with the stranger.
I smiled as if nothing was out of the ordinary. “Hi, nice shoes.”
She stammered, “U-u-um, thanks. You too.”
I walked confidently to our room with my pet crawling behind me. Once we were locked securely in the room, I walked to the bed and said, “Come to me, my pet.”
She obeyed, slowly crawling to me and sitting Rocky-like at my feet.
“Slip off my heels, Ms. Pennington,” I ordered.
She obeyed again and I ordered, testing her obedience, “Lick my stocking soles, my pet.” As expected, I felt her tongue licking the bottoms of my feet. One of my fondest fantasies was to have my feet worshipped, and it was the first one I planned to make a reality. Once she had licked both soles thoroughly, I had her suck each of my toes through the sheer nylon… surprised by how pleasant and erotic it felt… my cock staying rock hard throughout.
Remember, I had never done any of this in real life before. I was flying by the seat of my pants so to speak, and a small detached part of me was continually amazed at the clarity and confidence of my instincts and decisions. Every step of the way I not only knew what I wished to do and what I wished to have happen to me, but more importantly, I knew exactly what Sandra was feeling and how she was responding as I pushed her boundaries. I wanted this night to be an experience we both would wish to remember for a long time, and for some unexplainable reason I knew I could carry it off. Even so, I was looking forward to experiencing several lifetime firsts of my own.
Guiding this kindergarten teacher, looking so sweet and innocent in her school picture on the website, a divorced mother of two young girls, secretly an inexperienced but eager submissive, was an amazing turn-on and I knew this was only the beginning.
Getting horny myself, I sat up, removed my dress and unclasped my bra. Now only in my pantyhose, I asked again, “You like?”
“Yes, Miss Kara,” she moaned, her mouth literally drooling with anticipation and hunger.
“You really are a hungry cock slut, aren’t you?” I asked.
“Yes, Miss Kara, I’m desperately craving your cock,” she admitted; now that we were alone in the room her inhibitions had faded away… I knew she hadn’t been with anyone since her divorce over a year ago… her only orgasms self-induced and often during online role play.
“Get undressed, my slut,” I ordered.
Standing up, she unbuttoned her blouse and tossed it aside. The plaid skirt joined the blouse on the carpet, followed by her lace bra. She began to lower her pantyhose but I ordered, “Keep those on for now, my pet.”
She obeyed again and stood in front of me, awaiting further instructions. I noticed her prior nervousness was completely gone. By now she had decided on a deep level that I was worthy of her trust, so she was standing there placidly, content to wait forever if necessary until I told her the next thing she was to do.
“So why me?” I asked, as I slowly ripped a hole in my pantyhose (I would learn later you could buy crotchless pantyhose) to release my rigid cock from its nylon prison.
“I don’t know,” she started, before adding, “no, actually I do. I’ve always been curious about women. I love the idea of soft breasts and soft kisses, but I never could get into the idea of licking pussy, and I also desperately miss cock. You were the best of both worlds and when we chatted online you seemed to understand what I needed, the balance between fantasy and reality, the safety of submission and the comfort of obedience. I never came harder than in our role play fantasies, and when the opportunity came to meet you I didn’t hesitate.”
“Not at all?” I asked, as I stroked my hard cock in front of her.
Staring at my impressive package, she answered, “Of course I had doubts. What if you weren’t who, or most importantly what you said you were, and being submissive online isn’t necessarily the same as in real life; yet once you suggested meeting for coffee first, the last of my reservations were gone. If I got uncomfortable, I could always leave.”
“Are you uncomfortable now, my pet?” I asked, smiling.
“No, Miss Kara, I’m completely at home with you,” she responded with such sincerity and gratitude that she was close to tears.
“Is my pet hungry?” I asked, the question rhetorical.
“Famished,” she responded, staring at my cock with a lust I had never seen before… but would witness hundreds of times from this moment on.
At my gesture she dropped down and knelt directly in front of me, her lips inches from my cock, and I asked, “Well, what are you waiting for my dear cocksucker? Get cock sucking.”
She didn’t need to be told twice. She opened her mouth and took my swollen, thick cock head between her lips. I had often imagined what having my cock sucked would feel like, but it didn’t come close to the real thing. The warmth of her mouth, like a moist oven, had me moaning in seconds and I knew my first load would arrive rather quickly.
For such an innocent looking teacher, she bobbed back and forth like a ravenous college slut.
In only a couple of minutes she had my balls bubbling and I ordered, “Swallow it all, my pet.” She didn’t slow down and seconds later I was coming in her mouth. The sensation was so much more intense than my many self-induced orgasms, as the pleasure of her mouth continued throughout my state of bliss.
Finally spent, I pulled out and congratulated her, “Fuck, are you a good little cocksucker!”
“Thanks,” she replied, as if I had just complimented her outfit.
“Can you imagine how your colleagues would feel if they knew what you were doing right now?” I probed, for some reason wanting to keep reminding her of her submission.
“I imagine they would shit,” she smiled, “most of the other teachers call me a prude.”
“That’s a shame,” I said, helping her up from her knees to stand in front of me, “Everyone should see you for the radiant sexual being you are.”
“Oh God, no,” she began.
I clarified, “I don’t mean a slut, or a lez, or a cocksucker, or a submissive; I just mean a sexual being. You are pretty, you have a nice body and a powerful sexuality, and you shouldn’t hide that,” I complimented. I added, “It’s not as if your colleagues are opposed to sex in general. When people criticize sex, they’re usually objecting to specifics which are none of their business. But very few people think it’s a crime simply to look beautiful and sexy.”
“But how would I do that?” she asked, her vulnerability so adorable.
“By being yourself. Dress with confidence, wear your hair down, wear sexy lingerie beneath your teacher clothes, and so forth,” I suggested. “You already shave your peach; that’s a wonderful first step.”
“I suppose,” she replied, clearly not convinced.
“Are you my pet, Sandra?” I asked, my finger sliding between her breasts.
“Yes, Miss Kara,” she replied without hesitation.
“And you will do what I say?” I continued.
“Of course, Miss Kara.”
“Good; even after I am gone after today, we’ll be in contact and I’ll help you become the person you want to be,” I promised.
“Ok,” she said, tentatively.
“Good; enough chat for now,” I smiled, “lie down on the bed.”
She quickly obeyed.
“Open those lovely legs,” I instructed.
Again utter, unhesitant compliance. Now although I was pretty confident for a virgin, I was somewhat nervous about her vagina. I had breasts, so I understood those, but other than recorded images in porn I had never really seen a vagina up close. I was excited, but slightly nervous at the thought of licking pussy, even though it was my most frequent fantasy.
I moved between her legs, hiding my insecurity and moved my hand to her pussy. It was covered by pantyhose, which clearly had a wet spot. For some reason that relaxed me, to know she was wet because of me, and I moved my hands to her prized possession. I purred, “Is my pet wet because of me?”
I traced her pussy through the sheer nylon as she whimpered, “Yes, Miiiiiss Kara.”
I lowered myself between my pet’s pantyhose covered legs and put my lips directly on her nylon-covered pussy.
“Ooooh yes,” my sexy MILF moaned instantly.
I responded back, my lips on her pussy, her scent strong and intoxicating, her taste just a tease, “Hmmmmmm,” I hummed, causing vibrations directly on her pussy.
Her legs twitched and she moaned loudly, “Oh that feeeeels so good.”
I used my strong hands and my long, manicured nails to tear her pantyhose at the crotch so I could get direct access to her pussy. I wanted to taste her, to get her off with my tongue, to taste her cum. For the moment I was no longer her Domme, I was just an eager teenaged girl about to taste her first pussy.
I heard her breathing stop as she waited in anticipation for my tongue. I felt so hungry for her slit, just like she’d been earlier for my cock, and I leaned forward, extended my tongue and licked.
Like receiving my first blow job earlier, my first taste of cunt was way better than one could ever imagine. As my tongue probed between her lips, making her wetter and wetter, I couldn’t get enough of her taste.
Her moans only enhanced my eagerness to get her off and taste her cum. I used my fingertips to part her pussy lips, trying to get my tongue deeper inside her.
“Oh yes, Miss, your tongue feels so gooooooood,” she moaned loudly.
I explored her pussy with a mixture of lust and wonder… wondering what it would be like if I had my own pussy. I was fascinated by the constant wetness (I had pre-cum on the tip of my dick sometimes… but never anything like this) and the variety of erogenous zones just on the outside… not even beginning to explore her insides.
“Oh God, Miss Kara, please don’t stop,” she begged, a couple of minutes later.
Sensing she was close to climax, about to come quickly like I had, I moved to her clit and started flicking it urgently and repeatedly.
Her body shivered and quaked with each concentrated flick and she got very animated. “Oh God, ooooooh, fuuuuuuuck, oh-oh-oh, yes, more, more, I’m so fucking close, Miiiiiiiss.”
I turned my hand so my palm was upwards, slid two fingers inside her wide open pussy, tapped upwards hoping for her g-spot and demanded, “Come for me, my pet, I want to taste you and your full flood of cum.”
“Yeeeeessss, Miss,” she moaned as if she had been holding back until she was given permission, as she lifted up her ass, trembling violently. Feeling her body shaking like that because of me was a major rush, and I was rewarded with my very first pussy juice facial. I was surprised by the first gush that exploded onto my mouth, tongue and face, while I continued fingering her.
Her heavy breathing continued even though her trembling gradually subsided and her muscles relaxed, and after a minute I rolled her onto her side, slid my cock easily into her flooding pussy and began fucking her.
She moaned, “Oh God yes, fuck your slut.”
Hearing her call herself my ‘slut’ was a major turn-on and I reached over, cupping her breasts as I thrusted into her.
“Your cock feels so good buried in my cunt, Miss,” she whimpered.
“Your cunt is so fucking tight, my heavenly slut,” I countered, in awe for the third time in half an hour, reaching my third first time experience in a very short amount of time.
And although I had no idea if I preferred oral sex to vaginal sex or the other way around, I definitely found them both enthralling and similar, yet paradoxically, completely different.
The similarities: they were both wet, both warm and each of them enveloped and caressed my cock.
The differences: pussy was wetter (which was surprising, because from the inside my mouth almost always felt very wet), and even though she was responsive to my every whim she was unmistakably in charge when she was sucking me off, but during fucking I was in charge (although in retrospect I suppose I could have face fucked her… and if she’d been on top I could have had her fuck me).
Thankfully, having already come in her mouth, in addition to jerking off at my grandparents’ earlier, I was able to last a long time.
I wanted to try as many positions as possible:
I bent her onto all fours and fucked her from behind… loving the powerful control I had in this position. I controlled the pace and the depth.
I started slow, wanting to enjoy the position… enjoying watching her body tremble and listening to her moans.
After a couple of minutes, I began going faster… equally enjoying watching her body bounce back and forth like a sexual Raggedy Ann doll as I slammed into her.
“Oh God, yes, fuck me hard,” she moaned.
I disengaged, lay down on my back and ordered, wanting to watch her fuck herself, “Lower yourself on my cock, bounce on it, fuck yourself, my teacher pet.”
“Yes, Miss,” she moaned, instantly obeying, sitting carefully down on my cock, then bouncing up and down hard… taking it as deep as it could possibly go.
After only a minute in this position, she begged desperately, “May I come again, Miss?”
“Tell me what you are,” I demanded.
She surprised me with her response. “I’m your slave, your cocksucker, your slut, your fuck-toy, your…” she went on and on, her descriptions flowing out like water between her moans as she fucked herself furiously.
“Fuck, are you a sexy slut,” I grunted, my own orgasm imminent.
“Your slut,” she replied, clearly holding back the rising tide.
“Hold back just a few more seconds, baby,” I said, my heavy breathing matching hers as I resumed being the one doing the fucking, using my abs to piston my tool powerfully upwards over and over into her streaming twat.
“Kkkkkkkkk,” she whimpered, clearly near apocalyptic bliss.
A few more deep hard thrusts and I felt my balls bubbling and I screamed just like a passionate woman, “Now, baby, RIGHT NOW, come with me!!”
In unison we both screamed as our orgasms erupted together and our cum collided in a desperate rush to leave our bodies.
My arms around her, her hips now resting on mine, I felt her body tremble as my cock remained lodged inside her. Our moment of equilibrium was frozen in time as we allowed ourselves just to enjoy the lingering afterglow of our shared euphoria.
Eventually I pulled out and collapsed onto the bed; she rolled onto her back too, turned her head to face me and said, “Wow!”
“Wow, indeed,” I returned, kissing her softly on the nose.
We spent the rest of the evening together: room service, a lavish leisurely 69 where we each swallowed another load of cum, a rented movie (Disney’s Snow White of all things for a complete change of pace), and one last lengthy fuck session where I finished by filling her pussy one last time. I wanted to stay the night, but that would have sent my grandparents into a frenzy.
We said goodbye, Sandra deciding to stay for the night and enjoy the luxury of having a hotel room to herself for once, and breakfast with no cooking necessary and no dishes to wash.
We promised to keep in touch and we have. We still get together a couple times a year, sometimes more. She has a special place in my heart and was shocked when I finally told her a couple of years later that I had begun that day as a complete virgin.
Her oldest daughter is now eighteen and I have to admit that although she is a complete sweetheart, she would be oodles of fun to seduce. She calls me Aunt Kara, completely unaware of her mother’s and my special relationship. Although I’m beginning to think she may know something is up, I doubt she knows what that something is.
After a rather romantic first time with a girl, I wanted my first encounter with a man to be very different. It would not be intimate or romantic, but strictly sex.
I would be in charge… I would completely control the situation… I felt this needed to be a test drive (pun intended) for when I decided to take my revenge on that no-good, girlfriend-dumping, unfeeling asshole quarterback. I had figured out that there was a major difference between totally dominating a man and leaving him grateful for the encounter, and doing the same but leaving him feeling like shit, so both adventures would be learning experiences, even though there would be similarities. My inexperienced but certain instincts had served me very well tonight with Sandra. I trusted they would remain reliable as I explored some very different versions of sex in the near future.
And that is a different story (actually it’s two different stories)…