Shemale Beauty: 1st Female Conquest

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 dog 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 dog-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)...

Coming in future months if enough people want to read more of this seductive shemale beauty:

Shemale Beauty: 1^st Male Bottom

Shemale Beauty: 1^st Straight Turn

Are there other stories you would like to read about... ones mentioned in the story or otherwise???

Jasmine June 2017