‘What the fuck just happened?’ The thought echoes through me like a shockwave, making my skin tingle as if lightning had just struck a nearby tree. The memories of this night have me feeling raw and exposed.
I can sense her taste on my lips, and the subtle remains of her fragrance is lingering on my shirt. If not for these sensations, and the warm burn of her touch on my skin, I wouldn't believe any of it ever happened. Yet, I know it did.
This is a new and exciting feeling. I want to remember it vividly, recorded in my own voice. Looking at my phone, I see the soft, red light glowing steadily, telling me it's recording every word I say. With a deep sigh, I try to capture this feeling, knowing full well that words alone could never truly express what it was to actually live it.
***
I felt a rush in my veins when I woke this morning. There was an extra bounce in my step, as if I knew something special was about to happen. I didn't know what it would be, but I knew it would be big.
I was newly, happily single, and ready for my life to take a turn for the better. 'You've got the luck of the Irish with you today,' I told myself. 'You better do something worthy of it tonight, boyo. Life doesn't give this gift often, especially if a man lets it slip between his fingers.'
Of course, 'the luck of the Irish' is just a cliché, but as with most such phrases, there is a truth hiding behind the words. Another cliché', and one I'm particularly fond of is, 'lucky at cards, unlucky at love.' This one, especially, seems to define my life. So it was that after my last, failed relationship, I was again at the casino, ready to try my luck with ladies who have been far kinder to me than those of the flesh and blood variety.
I was in no hurry though, so I stopped in the Kensington's lounge for a drink. Playing cards for high stakes takes nerves of steel, and a bit of liquid courage before taking a seat at the tables often lets me relax, despite the stress of the games. I was sitting peacefully at the bar, enjoying my tumbler of Hennessy, when I saw her saunter through the door.
She was tall, with long legs and a figure that made my cock stir the moment I saw her. Her dark hair shimmered like black silk, flowing over her shoulders and perfectly matching the ebony coloring of her dress.
There was an almost regal grace to the way she moved, a confidence that had me hooked the moment I saw her. By the time she made her way to the bar, I'd completely forgotten about my date with the two-dimensional ladies of the deck.
Flagging the bar tender, I told him to bring her anything she desired. Perhaps it's another of those endless clichés, but buying a woman a drink is always a good way of breaking the ice. Sure enough, the magic worked, and her face lit up as I approached.
"Thank you for the drink, darling," she said with a volume that matched her confidence. "I'm glad to see a lady can still find a gentleman in a place like this."
"You're very welcome. I saw you come in, and I just knew I had to meet you."
"Really? And why is that?" A wide smile grew on her face as she brought the glass up and allowed some of the sparkling fluid to flow into her mouth.
Sitting as she was, with the champagne glass held close to her ruby-red lips, my eyes drifted from her partially obscured smile to the deep cleft of her impressive breasts.
"I suppose it's because you're so beautiful. Surely, there's no harm in a man being attracted to a pretty woman?"
"None at all," she said with wry smile. "I'm June."
Her eyes were bright and cheerful, and I could tell she was enjoying the moment. Her mirth was infectious, and we shared a quick giggle as I took her hand in mine. "I'm Sean."
"Nice to meet you, Sean. So, are you here to play?"
The way her eyes bored into mine felt like she was looking into my soul, and I stuttered as I tried to grasp her meaning. "Ah, what?" I finally managed to ask.
"Gamble, Sean. Why else would you come to a casino?"
My cheeks warmed at her teasing tone, and I smiled back, willingly taking the bait. "That depends on the game."
Nodding slightly, she smiled again. "So, I take it, your interest goes beyond having a drink with me?"
"You might say that..." I began until I realized with a start that she wasn't a woman! Oh, her transformation was amazing, but her shoulders were a bit too broad, and her features too strong. I was flirting with a transgendered woman, but while I felt deceived, somehow, my cock just didn't care.
"Ah, there it is."
"Excuse me?" I managed to choke out. My mind was whirling, but incredibly, I wasn't ready to walk away.
"That blank look of surprise. You've just realized that there's something a little different about me."
She was so unexpectedly direct that I almost spilled my drink, but as her smile grew, I chuckled at my own embarrassment. "Yeah, I have, but I have to admit, I'm intrigued."
"Intrigued? Really? Well, good for you, sweetie," she replied happily. "You haven't run away, so I'd say there's hope for you yet."
"Hope for what?" I honestly asked, but when her eyes bored into mine. I instantly knew where she was going.
"Ah, I love how men suddenly get shy when a woman turns the tables on him. Let's not kid ourselves, sweetie. I knew what you wanted the moment you bought me this drink, so if you are ready to try something new, I'm your girl."
***
By the time we got to the room, my body was tingling with anticipation. Whatever my pre-conceived notions of transgendered women might have been, being this close to June washed them from my mind. To me, she was all woman, and I took her into my arms and pinned her against the door, just as it closed.
One might have expected her to vie with me for the lead, but she was wonderfully, deliciously submissive to my advance. Willingly, she accepted my kiss as I pressed her against the hardwood of the door.
June felt soft and feminine as her arms encircled my neck. In the heat of our first kiss, my doubts and nervous hesitation were swept away. Her lips felt as warm as any woman’s I’d ever kissed, and she melted into me as our passions grew.
The sweet scent of her perfume enveloped me, filling me with an intoxicating need to explore her body. I no longer doubted or cared about her unusual nature. By the time my fingers began to lower the zipper of her dress, my thoughts were only on the taste of her skin, and the firm resilience of her breasts.
"Mmm, I love an aggressive man," she whispered excitedly as her dress slipped off her body.
"Good, thing," I replied as I cupped her breasts. "Because I'm not in a gentle mood tonight. You're as sexy as hell, and I can't wait have you."
June moaned and held my head to her breast as I took her smallish nipples into my mouth. I hadn't even begun to undress, and there she was, with only her tiny black panties hiding her most intimate secret.
Her breasts were magnificent, firm, upturned and beautifully full. Her nipples hardened and lengthened as I sucked, and June was cooing softly as my tongue flicked over them.
"That feels really good, Sean,” she murmured, and she gasped in surprise as I clamped my teeth down. I felt her body tense, and her breath caught in her throat as I sent stinging bolts of pain into her.
"Ah, fuck, yes. Bite me! Make me feel it, Sean!" she hissed inwardly as I held her to the door. When it became too much, she pulled me up and kissed me hard.
Stumbling frantically, we both worked to loosen my tie before she flicked open the buttons on my shirt. I was naked from the waist up by the time she sat on the bed. Reaching out, she gently squeezed me through my pants, tracing her fingers over my now fully erect shape.
"I'm dying to suck your cock," she told me as she fished my erection out of my pants. Kneeling at my feet, she tugged my slacks and boxers down with her. "Mmm, fuck, baby. That's a nice cock. It's big, but not too big. I can't wait to have you inside me."
There was an almost wistful longing in her voice that left no doubt of her desire in my mind. I watched in lurid fascination as her tongue glossed her lips before inhaling deeply around my cock as she took it into her mouth.
"Oh, shit, that's good, I gasped as her mouth closed around me. The quick rush of cool air sensitized me in a way I'd never felt before, and the sudden, wet heat of her mouth made my knees begin to tremble.
June quickly proved her skill at sucking cock, and as her lips and tongue played over my shaft, I began to fear I was going to explode down her throat. Sensing my excitement, she pulled off and gently massaged the underside of my shaft with her lips.
My cock was throbbing, but she managed to keep me on the edge, sucking my balls, and stroking me with her hand each time I thought I was going to lose it. I barely noticed as she turned us around and urged me down on the bed.
"I'm so torn," she mused as her hand slid up and down my glistening shaft. "I'm longing to taste your cum, but I don't want you to pop. You aren't going to run off on me the moment you come, are you?"
God, just seeing this beautiful creature kneeling between my thighs, all but begging me to come in her mouth, almost made me lose it. I shook my head, surprised at myself for being as aroused as I was.
Part of me was still nervous, and I wasn't sure if her transformation was complete, but I did know I no longer cared. Lifting her chin, I bent down and kissed her again. "I'm not going anywhere, June. I want to see what you're hiding under those panties, and I can't wait to fuck you, however you like being fucked."
"Mmm, good boy. I knew I could count on you." Her beautiful lips curled up in a smile and her eyes held mine as she slipped my cock back into her mouth.
This time, June gave me no chance to hold back. Her mouth was so deep that she had no trouble at all taking me down her throat. Her hands cupped my nuts, fondling them as the pressure on my glans grew. I could feel my thighs growing tight, and I lay back on the bed as her head bounced furiously over my lap. It was the best head I'd ever received, and June seemed to know exactly how to touch me. Just as my orgasm approached, she slid a wet finger into my ass, driving it deep with a single, hard thrust.
"Holy fuck!" I growled, but then a new sensation spread through me, and my whole body began to jerk in ecstasy.
June sucked and swallowed, taking my entire load down her throat as she fucked me with her finger. I must have shot the biggest load I had in years, but only the slightest but of cum leaked down my shaft as she finished me off.
Only then did she pull her finger out, and we shared a laugh as my heartbeat began to slow. "Holy shit, June. You could have warned me."
Licking the last bit of errant cum from my shaft, she grinned wickedly. "Not a chance, baby. I wanted to surprise you. It felt ready good, didn't it?"
"God, yes. I don't remember the last time I came that hard."
Sliding up on the bed, June glazed her lips over mine. Holding her tightly, I crushed my lips to hers, swirling my tongue in her mouth.
"There's a lot I can teach you about anal play," she mused as I fondled her breasts. "It can feel amazing if it's done right."
Running my fingers down her belly, I gently traced my fingertips over the growing bulge in her panties. "I'm sure it does, and I'm looking forward to it, but first, I really want to see your cock."
For the first time, June actually seemed to grow shy. Wordlessly, she hooked her thumbs on her panties and lifted her hips as she pushed them down her gorgeous thighs.
I'm not sure what I expected, porn sometimes gives the impression that transgendered women have small cocks, but the piece of meat that stood from her body was at least as big as mine. Nervously, with June watching intently, I took her in my hand.
“Mmm, God I love being touched," she moaned as I began stroking her. Her cock was firm and hard, and she was already leaking precum. Knowing what she wanted, I kissed my way down her body and took her into my mouth.
It was the first time I'd ever sucked a cock, and I was immediately surprised at how perfectly shaped it was for my mouth. Locking my lips over her shaft, I began sucking her as deeply as I could take her. I could feel her hips gently thrusting, and her breath began matching my pace.
The tangy flavor was surprisingly pleasant and I quickly learned to like the sweet taste of her precum. I wasn't nearly as skilled as she, but her deep sighs told me how much she was enjoying it. When I felt her delicate fingers in my hair, I smiled around her shaft, letting her know how much I wanted to please her.
As the minutes passed, I began to understand why she wanted me to come for her. I was frightened about taking her cum, but part of me longed to experience it. I'm sure I wouldn't have stopped until she shot in my mouth, but she finally pushed me away.
"I'm ready, Sean. I need you to fuck me."
"Yeah, me too," I replied and I gave her one, last, hard suck before wiping the saliva from my lips. This was the moment I'd been waiting for, and my stomach was churning as I remembered the one time I'd tried fucking a woman's ass.
It had been a clumsy and unenjoyable act. I was clueless, and she wasn't able to relax enough to let me get inside her. I desperately hoped this time would be different. Stoking my newly awakened erection, I looked at her, waiting for her to show me what she wanted.
Sensing my indecision, June smiled warmly. "Let me suck it a little, baby. I'll get it nice and wet and you'll get inside me easy. I'm really used to this kind of sex."
Once again, having her wet mouth on me had me groaning. My cock was wet with saliva and hard as steel by the time she pulled off. Afterward, she reclined on her back and parted her legs, giving me access to her dark passage.
"Come, on, Sean. Fuck me deep. I love having a hard cock in my ass."
Shit, just looking at her laying there had me panting. Her body was beautifully feminine, but her cock was lying on her pelvis, wet, hard and ready to be sucked. Licking my lips, I gave it a hard, deep suck before bringing my own cock to her aching hole.
I expected her body to resist, but when I pressed forward, I was surprised at how easily I slid into her. June's eyes widened as I slid inside, and a look of intense pleasure grew on her face as I began pumping into her. Holding her hips, I drew myself in, filling her completely.
"Yes, that's it, baby," she gasped as her muscles fully relaxed. Soon, I was plunging into her with long, deep strokes that made her breasts bounce erotically each time I hit bottom.
I had just hit my rhythm when she gripped her cock and started stroking it hard. Together, we match our pace, and I could tell we were both soon going to come. I'd never seen a man jerk his cock before, and seeing a woman do it was more than I could take. My body was covered in beaded perspiration, and my heart pounded in my chest as I watched her yank her shaft with unmerciful need. When she began to come, her body tightened around me.
"Should I pull out?" I managed to gasp, but she shook her head.
"No, come inside me! Fuck, I'm gonna come!"
With that, her cum erupted out of her, shooting in long ropes over her stomach and onto her breasts. In that moment, I lost it, and with a loud grunt, I filled her ass with my hot seed.
We lay there for a while. I wasn't yet ready to let her fuck me, but now, on my drive home; I look at the card she gave me with her number emblazoned on the front.
It was incredible, and I have no doubt that next time, it's going to be me lying there on my back with her cock shooting cum inside my ass. The luck of the Irish, indeed.