by Zoe Brown
“NNnnnn—MMMMppphhhh!” The beautiful, sexy redheaded woman – and she definitely was a woman, biological-sex-wise at any rate, as far as I could tell – and I had a pretty significant amount of experience to draw upon in making my assessment – groaned and then whimpered as she impaled her warm, wet, welcoming vagina down upon my shaft, and I cried out in unison with her as I felt my cock penetrating up inside of her yielding, grasping, squeezing womanhood as I entered her, having to focus all of my self-control on not just blowing my massive, long-denied load the moment we came together. We both groaned and moaned (and in her case) whimpered for a moment longer as our bodies got used to one another’s, her new womanhood flexing and expanding and adapting to the presence of my cock inside of her, my own cock quivering with anticipation and throbbing with the need to fill her with my seed. Once she could focus again, Brianna blinked her eyes and shook her head to clear it, panting again with renewed arousal, licked her lips and fixed me with a look. I saw the lustful hunger in her eyes, and knew that I radiated it back at her out of my own. We held each other’s gaze then, both panting and slowly nodding to one another, encouraging each other to begin. This was where we both wanted to be; this was the moment our whole sexy, flirty dance had been building up towards, and neither of us wanted to pussy-foot around any longer.
Grabbing a hold of my lady lover’s hips in both of my hands while she gripped my shoulders in her own, I locked onto Brianna’s bright, brilliant green eyes as – in unison – both of our hips began moving at once. Mine ground up, into her, forcing my cock deeper up within her wet, willing womanhood. Hers ground down, onto my own, riding my cock deeper and inside of her depths. We both grunted and groaned, whimpering, crying, and moaning as we skipped right through the slow, gentle build up phase and right into full-blown cock-pumping, hip-gyrating thrusts within a couple of seconds – she was far too wet and eager and I was much too close to losing control.
We didn’t last very long that first time. Her head dropped back and she let out some deeply sensual, ruttingly-sexy moans not long after we first began, and my whole world quickly narrowed until it included only her, her alone, bouncing up and down on my cock, riding me with everything she had while I returned her energy with frantic, frenzied thrusts of my own, just trying to hold on a few minutes, a couple seconds longer, just long enough to let her cum, to make sure she got the pleasure she deserved before I … let… go…
“AhhhHHHHHHH—AHHHHHH!!!!—AHHHHHHHHHHHSTON!”
And then she did. And I did. I abandoned what little control I still possessed, fucking finally, and we came together like a fountain of orgasmic release. It was fucking glorious.
Chapter Seven
“Oh… my … god…” Brianna whimpered some ninety-minutes later, amidst her breathy pants, “…How… did you… do that…?”
“Do… what?” I panted back at her, a smug smile on my face. I knew exactly what she was asking about, but I lived for these little moments of stunned disbelief and amazement from the women I slept with. It was part of what made these encounters so thrilling for me – or had done, until recently, and to my delight, now did so again in the company of the Werewoman Brianna – knowing just how thoroughly I’d surprised and pleasured them.
“That … thing…” the redhead rolled onto her side with a tired little groan of protest and made a disbelieving face at me, “that thing you did… with your cock…” she tried to demonstrate the ‘thing’ with her hands, but she couldn’t quite get it right and finally just broke down into disbelieving laughter. “… I’ve had one of those for the better part of almost thirty years – I had no idea they could do… anything like that!!”
“Oh, well…” I rolled over onto my side beside her, grinning at the fetching expression of amazement on her beautiful face and leaning in for a quick, pleasantly moan-filled kiss, “… I’ve had rather a lot of practice.”
She laughed again, rolling her eyes and collapsing back against the bed again, legs splayed wide open and her pussy, on full display, positively pungent with the fragrant bloom of a soppingly-wet, well-fucked woman. “You can say that again. Balls… I don’t think I’ve ever had sex this good before.” Brianna smirked over at me, “and you can bet I’ve had as much as I could manage to have, just so that I could maximize the amount of time I could stay like this.”
“Well, I am flattered, my dear,” I responded formally, lifting the beautiful woman’s hand and kissing her knuckles softly. “But why so interested in what I can do with my cock?” I teased her back, laughingly, tracing the fingers of my right hand slowly and tenderly over her soft, flat feminine belly, marveling yet again just how deliciously beautiful Werewoman had made her, “Thinking you want to go back, try it again from the other side?”
“Ohhhhh hell no,” Brianna intoned, with intense surety. She shook her head, then glanced over at me and gave me a wicked, wanton smile, sliding the fingers of one hand slowly and teasingly over the full curve of her hips, across the flat emptiness of her pelvis, and then up between her big, beautiful breasts, “I’m quite happy exactly as I am.” She winked at me. “I’ve had sex plenty of times, from both perspectives, and I can promise you, when you’re with someone who knows how to do it right, like you, Mister Sexy Old Spice, being a girl is wayyyyy better.” She laughed, and then arched an eyebrow at me, her smile turning slightly teasing. “Why, did you want a shot at being the girl for a change?” She batted her eyelashes playfully at me.
And it was right then, right there, that the seed of an idea was planted.
She hadn’t meant it as a serious question – I saw that right away in her eyes. And no, I hadn’t been thinking that at all. Well, not really. But when she asked me, the idea and all of its implications shot through me, and to my complete and utter surprise, the implications felt … sexy… to me. Very sexy. The image of my hard, masculine male body shifting and softening and changing into a smaller, delicate, curvaceous female one like Brianna’s suddenly filled my mind, and I felt a sudden thrill of intense yearning, and my cock went as hard as a rock.
But just as quickly as the idea turned me on, it also filed me with shame, and defensiveness. I quickly shoved the notion away, masking the half-second pause with a smile, a dismissive hand wave, and a half-vault off of the bed to reach for the pizza that was sitting on one of the nightstands to either side of my glorious, luxurious California-King-sized bed. “No, of course not,” I replied, as nonchalantly as I could.
But I was still a half-second too late with my denial. I saw that when I rolled back onto the bed, with the pizza box in my hands, and handed it to my date. Her eyes had gotten just a little bit too wide while she was waiting for me – me, the paragon of male sex and masculinity, the billionaire playboy renowned across the world for his thrill-seeking exploits and pursuit of pleasure and pleasant company – to dismiss the notion of turning myself into a sexy young woman as a ridiculous fancy. That half-second’s delay had cost me all of my credibility.
“Fuck me, you actually just considered it, didn’t you?” Brianna whispered, gazing at me with amazement for the second time in under five minutes. “And I don’t think you entirely hated the idea.”
I pretended ignorance and chewed on a piece of pizza, pouring myself a glass of wine while I ate it and trying to come up with a casual way to change the subject. “What, what idea?” Meanwhile, in the back of my mind, a question began to grow: Why don’t I completely hate it?
Unfortunately, my date seemed to have found a bone that she wanted to gnaw on. The fascination in her eyes was growing brighter by the moment. “You turning into a girl, trying sex out as one of us – uh, erm – as a Werewoman, I mean.” She snagged a piece of pizza and a wineglass for herself and held the drinking receptacle out, waiting for me to pour her some of the old vintage. “I asked you, and you thought about it for a second. And you didn’t totally hate the idea.”
I topped up Brianna’s glass and blew out a slightly annoyed breath. Discomfort and shame were surging th
rough me all of a sudden. So I hadn’t completely hated the idea. So what? I wasn’t going to go through with it. We were having a nice time. What did I have to say to get her to let this go? “I said ‘no, of course not.’”
“Yeah…” The redhead sipped some of her wine, then started munching on the pizza in her hands, taking some delicately miniature bites that made me smile in spite of myself. She really was quite adorable as a woman. Totally wasted as a man. Thank god for Werewoman, eh?
“Yeah,” she repeated herself a moment later, eyes starting to narrow, “but it took you a little bit. You kinda did this… half-freeze thing for a moment. Like the idea had never occurred to you before, but then it did, and … you didn’t hate it.”
I sighed again, rolling my eyes and shrugging my shoulder. The conversation was starting to make me uncomfortable. “Brianna—”
She interrupted me, holding up a hand and sitting up. A lock of her delicious, dark-red hair dropped into her face as she looked at me, thinking. An idea had just occurred to her. “Wait, this is the first time you’ve ever slept with a Werewoman before, right? That’s what you said.”
“Yeah,” I nodded, shrugging again. That didn’t prove anything. “So?”
“Where’d you get the pills?”
“Oh, them?” I smiled again, feeling more confident. Here I felt I was on safer ground. “One of the bargirls down at Eden’s Lounge in the Marina district sold them to me for two thousand dollars in cash a couple of weeks ago. She was beautiful, just like you…” I grinned teasingly and brushed the lock of errant red hair out of Brianna’s face, making her blush a little in response, “… and she was a Werewoman. When she told me, I was … very surprised. I had never met a Werewoman before, as far as I knew. She sold me the pills.”
“Why did she sell them to you?” Brianna frowned, still looking thoughtful. I sighed, ran a hand through my silver hair, and sat back against the headboard, feeling increasingly frustrated by the conversation. I don’t really want to talk about this, I thought to myself, though I refrained from saying that out loud. The more Brianna asked me about the Werewoman, the more defensive I felt myself starting to become. And of course, I wasn’t an entire idiot: recognizing my defensiveness was making me even more uncomfortable. Could she be on to something? I mean, I had enjoyed the idea – if only for a moment.
No, I felt the larger, more conscious portion of my mind reply, flatly rejecting the idea, No way. I’m a guy – I’ve only ever wanted to be the hottest, most successful guy around, successful with ladies, at extreme sports, and in the boardroom. I’ve achieved all that – I don’t need or want anything more.
Outwardly, I shrugged. “I was complaining to her about how boring everything in my life had become. All the thrill-seeking, the adventuring, riding rocket ships and illegal street racing…” I shook my head. “It hasn’t been very satisfying lately. Same with picking up random beautiful women in bars and clubs and taking them home for the night. It’s been losing its appeal for a while now – the whole ‘dating scene.’” Brianna’s eyes narrowed quickly, and she prepared to seize upon that, but I held up a hand to forestall her, “And before you say anything – I still love women,” I gestured to her beautiful body, “as you can attest. I’ve just kind of run out of energy for the same old boring scene.”
“Hmmm.” Brianna made a noise that sounded unconvinced, and then went back to munching on her pizza again. When she didn’t say anything else for a couple of minutes, I glanced over at her, trying for a smile.
“Now, do you think we can get back to the pleasures of the evening…?”
The pretty girl smiled back at me, but she held up a hand again, having a quick sip of her wine to wash the pizza down, then spoke again, “Hang on. I wanna clarify something first.”
I sighed and rolled my eyes again. “Alright, go for it.”
“You get tired of the dating world. You go to a bar, complain about it to a bartender. She tells you she’s a Werewoman and offers to sell you some pills. You suddenly get supercharged about the idea of sleeping with a Werewoman, chat me up, and ask me to hook up with you tonight—” She leaned over and planted a soft, placating kiss on my lips mid-sentence, then leaned back again, “—which I am very glad you did, by the way, don’t be confused about that—but then after all of that, you claim that you have no interest in trying out one of the pills and becoming a woman yourself?” She gave me a skeptical look.
I shrugged and made a face again, not sure where she was drawing the connection. “Yes, I do, without reservation. I don’t see where you’re going with this.” It was a lie, but… I didn’t want to deal with the implications of what she was suggesting.
“I’m just saying…” the pretty girl picked up the pizza box, set it on the bedside table on her side of the bed, and then reached for my empty wine glass, setting it aside along with her own. She started crawling across the bed towards me again, and I could see from the nipples on the tips of her breast, dangling beneath her as she approached, that she was starting to get turned on again, “You getting all fired up about sleeping with a Werewoman while standing in a bar filled with beautiful women – any of whom would have dropped their panties for five minutes alone in a corner with you, believe me, handsome – is a bit suspicious.”
Brianna grinned at me, pushing me down into the mattress again, and crawled over me, setting one of her knees on either side of my hips and sitting on my semi-erect cock with her full, plump, round bubble butt. I groaned again, feeling my cock starting to get hard again underneath her, and smiled back up at her. Oh, what the hell. If she wants to have another go, she can ask me all the questions she wants first.
“So, what – exactly – did the bartender say to you?” the redhead asked me, in a sensual, seductive tone, lifting her hips and rolling them over my middle so that her slick, wet womanhood rolled down over the semi-erect, swiftly stiffening shaft of my manhood, eliciting another, louder groan.
“NNnnggggg…” I panted slightly, reached into the open drawer of my bedside table for another condom wrapper, which I tossed at Brianna. She caught it and tore it open. “She told me that being a Werewoman had been great for her tips, and that, um—Nnnnnnggg, Ohhh, Brianna—that, um, she got to go home with whomever she wanted to when she was a girl, which she seemed to enjoy. That’s when I got really turned on, I think—Ohhhhhh!—mmmm…” Brianna’s slick, wet, warm pussy was riding back and forth upon my increasingly hard, sensitive shaft as she waited to hear my full answer, which was making it hard to think, but was also giving me plenty of incentive to get it all out: “And she said that if I wanted to add some thrill back into my life, if I wanted the best fucking sex of my life, that Werewoman was the ticket.”
Brianna laughed then, throwing her head back and laughing a pure, gay, happy laughter as she lifted her wet, warm, inviting pussy off of my cock and rolled the eighth condom of the evening down my shaft. “Oh, you silly, silly man,” she mocked me, playfully, moaning a little and whimpering as she began to position the head of my erect cock between her wet, warm pussy lips again, “She didn’t sell you a baggie full of Werewoman pills so that you could sleep with a Werewoman. She was offering you a chance to take a chance… and become one… yourself—AHHHHHHH!!—”
And then once more she impaled her hot, sexy vagina on my straining cock, and we didn’t speak any more about the subject for another fifteen or twenty minutes.
✽✽✽
We had sex a grand total of eleven times that night, before the both of us were finally spent. The subject of me taking a Werewoman pill and becoming a sexy young woman myself did come back up a few times, on account of Brianna’s persistence, and I finally had to ask her to just drop the subject so that we could enjoy the evening at hand. But even after she agreed to let it go, the buxom and beautiful redhead curled up in my bed privately confided in me that she was glad I didn’t want to take one – with her, that evening, at any rate. Apparently, she’d had that experience with a couple of her lovers befor
e, and both of them had been disappointed to find out that as a girl, Brianna didn’t much fancy women. However, she did extract a promise from me before she finally let the subject drop: ‘If you do decide to take one, one day,’ she told me, ‘you have to promise to let me meet her – the girl you, that is. I can’t imagine what a hot, sexy, lady version of you would even be like, but I’m dying to find out.’
At the end of the night we’d collapsed, panting with exhaustion, into each other’s arms, and we slept curled up together until I rose for work the next dawn. I was a little bit sad to leave her, truth be told. Brianna looked absolutely adorable with sex-mussed hair, lying cute and sleeping and quite thoroughly ravished, in my bed. I made a mental note to arrange our next date as soon as possible. I knew that I’d have to find a suitably magnificent venue for the occasion. It wasn’t that I was hoping for something romantic with her, or anything – we had both been pretty open with one another about our hook-up just being a sexual thing for the two of us, and I hadn’t sensed any indication coming from her that she had romantic notions towards me; she just really enjoyed fucking me – but as with any woman, Brianna deserved to be treated like a princess, or a queen, and yet I had the suspicion that life had never been quite so decent to her. I resolved to knock her socks off next week with an evening that she would never forget.
✽✽✽
When I slipped out of the apartment that morning, I left a note behind on the bedside table closest to where Brianna was sleeping. The note told her what a wonderful time I’d had with her the previous evening, thanked her for her company, encouraged her to take her time and enjoy herself in my extremely fancy shower before she headed out for the day, and asked her if she’d be free to see me again the following week – for a fancy-schmancy special occasion date. I also went out and got her some fresh orange juice and a couple of donuts, which I left on a serving tray beside the bed.
