tagTranssexuals & CrossdressersThe Neighbour Who Had It All

The Neighbour Who Had It All


Not my usual fare, if I have enough stories to be considered usual.

Shemale, transsexual, chick with a dick, whatever you want to call it, it's here, so fair warning.

I'd also consider it a bit of a romance story, though not a straightforward one. There's also some master/slave, not very much, it's more a hint of where their relationship will probably go in the future.

* * *

Alan had been watching his new neighbour for months now, picturing her naked every time he saw her. She'd moved in a while back, and he'd been immediately struck by her beauty. His first glimpse had been while she helped the removalists by hefting some of the smaller boxes inside alone. She had a Mediterranean look, with a dark olive complexion, dressed in a pair of loose beige slacks and a country style red shirt, knotted together at the bottom with rolled up sleeves. Her copper coloured hair hung halfway down her back. He couldn't guess her age, it could be anywhere from 25 to 40. She was beautiful, and Alan's dick had immediately hardened. She looked very busty, and the slacks were tight around her arse, with a nice, big booty packed inside, and so began his campaign of voyeurism.

Alan was 25, of average build with pale skin and blond hair he kept short. He worked from home, running his own, moderately successful website. This meant he had plenty of opportunities to stay 'on watch' for his sexy neighbour. The house she'd bought had been a little run-down, nothing too serious, but the yard needed a lot of work. She'd get out there in a pair of cut off jean shorts and a red bikini top, and get stuck in to the gardening, her beautiful, sexy, round arse just popping out of her shorts. Alan would again be beating off to another big spurt.

He'd noticed that she didn't seem to leave the house during office hours. He kept a pretty close eye out, and she did seem to leave the house semi-regularly, but not until after about eight, and not with much regularity. Maybe she was on call or casual or something. When she did leave though, she was always dressed to the nines. Sometimes it was in a tight skirt, often there were tight, figure-hugging jeans, but even an evening gown or two made an appearance. It was clear her favourite colour was red, as he rarely saw her without a piece of red clothing.

* * *

He finally managed to learn her name and introduce himself a couple of months after she moved in. The postman had delivered a piece of mail for Elise Carver to the wrong address, which he knew had not been the old residents. He spent an hour that day getting dressed, changing outfits, styling his hair, choosing aftershave and building up his nerve. He'd never been the most suave guy, but she made him extra nervous. He considered liquid courage, but didn't want her to smell it on his breath at eleven in the morning and figure he was a deadbeat. Finally he'd plucked up the courage, walked up her footpath and pressed her doorbell. He waited what felt like ages, but he checked his watch and knew it had only been about fifteen seconds, but that was pretty long considering he couldn't hear any movement or reply. He'd been certain she was home, and her car was in the drive. He rang again and finally heard a muffled yell, "I'm coming, please wait a minute," in a delicious Spanish accent. Alan felt his stomach flutter.

When she opened the door if felt like he froze to stone. She was wearing a bright red track suit, and the zip on her top was only about halfway up, exposing a lot of cleavage. She didn't look to be wearing a bra either, as her nipples were sticking way out, clearly visible beneath her top, and her boobs seemed to sway and shimmy in that way that unbound titties do. She was almost a foot or so taller than him, placing his face right at tit-sucking height he thought before he caught himself. He couldn't afford to sport a woody while standing in front of her. She smiled brightly, before slowly lifting her hand to the zip and raising it up just a bit. Alan, embarrassed and frightened looked up into her startling blue eyes, but she was smiling, apparently not offended by him staring at her boobs. "Can I help you?"

As he started to speak his voice broke and he stopped speaking, dying of embarrassment. He closed his eyes for a moment, trying to centre himself. He opened them, a little calmer than he was before. She was now looking at him through her lashes, tilting her head forward slightly, still smiling, but much softer now. "Hi, my name is Alan Stevens, and I live next door," he held out the envelope to her, "I think I got your mail today?"

She looked down and took the envelope. "Thank you, yes, I'm Elise. That's very kind of you. Would you like to come in for a moment?"

Oh my god, she's inviting me in. For a split second his mind started to think of the possible outcomes of that, but before getting carried away he reigned himself in, knowing they'd never eventuate with a woman as hot as this. "O... Ok," he nervously replied. She stepped back to allow him past, but as he walked past her she stepped forward, brushing her breasts against him. They softly flowed around his upper arm, before he skittishly moved past her, his breathing hastened.

She led him to her kitchen, "Would you like something to drink, a cup of coffee? I was about to have one myself."

"Uh, sure, thanks, that would be great." He watched her bustle around the kitchen, surreptitiously checking her out as much as possible, while they made small talk.

They talked about how long he had lived there, what he did for a living, his family, where he was from. She dodged a few of the return questions, such as what she did for a living, and where she was from. He was starting to relax, and having a good time. He was also increasingly sure she caught his furtive glances at her body, but wasn't making an issue out of it, perhaps even enjoying his attention. Eventually though, Elise told him, "Well this has been great Alan, it's been lovely to meet you, but I really must get back to it."

She didn't mention what she had to get back to, but he knew that was a polite invitation for him to leave that he couldn't ignore, "No problem, maybe we can do this again some time?" He shocked himself with how forward that was, it was testament to how relaxed he'd become, as usually even thinking a statement like that would have turned him into the bag of nerves he was now becoming, waiting for her reply.

"Sure, why not, it's been fun."

Alan had lost the nerve to take the opportunity he'd now been given, "Okay, great, well I'll see you later then." He quickly left, and in so doing, failing to seal the deal on what had probably been a sure thing.

* * *

Alan was pretty angry with himself. It had been a couple of weeks since he'd shared a cup of coffee with Elise, but he'd not had the nerve to do anything about it. He'd almost gone over to her house a couple of times, but always chickened out before opening his own front door.

He left his home office and went to his bedroom, on the second floor, with the window that overlooked her backyard and pool area. He'd spent a lot of time looking out that window since she moved in. Now he spotted her out in her yard again, tending to her roses, wearing her customary jean shorts and red bikini top again. His dick hardened up and he dropped his slacks for another good stroke. He was working himself pretty hard by the time Elise stood up, turned and looked up at him, offering him a wave. He shot his load against the window sill, a small amount splashing against the glass. He gave a weak wave back to Elise, hoping and praying she hadn't seen what he was doing, and definitely that she hadn't seen him spray on the window.

He moved out of sight, depressed and angry at himself. There was no way he'd even be able to face her again now, let alone set up a date.

* * *

The very next day, he headed back to the window, cautiously trying to stay out of sight, while still being able to see her himself. To his surprise, she wasn't gardening, no, to his delight, she was sunbathing. She was lying face down on a towel beside her pool, with a tiny little red thong bikini on, not the one she usually wore. She was glistening in the sun, perfect. Her booty was even more beautiful than he'd imagined, and it was pretty much all out there for him to see. As he watched, Elise turned and looked up at his window, but he was confident she couldn't see him. Nevertheless, she gave a little wave, maybe hoping he was watching?

He was confused, he'd never seen her sunbathing before, and was it just a coincidence that she'd started the day after she'd possibly caught him jacking off? Was this her offering more fuel for him to jerk it? He cautiously moved towards the window, waiting for her to react, ready to pretend he just happened to be walking past the window. He didn't have to wait long before she looked up again. She smiled at him and waved enthusiastically, and then beckoned him down; at least that's what it looked like. He didn't know what to do at first, until his hand dropped down to his crotch, where his cock was straining to break free. That was the final straw, if she really was beckoning him down then there was somewhere better for his hard cock, if she wasn't, all she could do really was send him home, or scream or something, but she did look to be beckoning him. He quickly changed into a T-shirt and shorts, and bolted down stairs to his backyard. The moment of truth, "Hey Elise," he called over the fence.

"Hi Alan, do you want to come and join me by the pool?" It was true, she had been beckoning him.

"I'll be right over," he said before he scaled the fence. "Great pool you've got, I've often admired it and wondered if I should get one."

"Grab a towel and lay down by me," she indicated a stack of beach towels by her back door. Her pool was in-ground, so he lay the towel down on the grass as she had. He took a moment to admire the way her tits flowed out to either side of her chest, the thin red string being put to its limit. "You should take off your shirt and soak up some vitamin D."

"Really?" he'd never taken off his shirt like that with a girl before. He wasn't a virgin, but his limited experiences were very fumbling, amateur affairs within his own bedroom with girls who'd soon dumped him. "Okay." He took off his T-shirt and made to lay face down like Elise, but she stopped him.

"You should lie on your back, I think your chest could use some sun." Alan wasn't going to argue. Here he was in a goddess's backyard, with his shirt off, and her next-to-naked. He'd been so focussed on her that he hadn't noticed how obvious his boner was, especially now that he lay on his back. She apparently noticed straight away though, "Is that because of me Alan honey?"

"I don't... what... is what because of you?"

She pushed up her torso, like she was doing Yoga or something, and Alan got a good, close look at her tits within the skimpy bikini for the first time. They might be fake, but he was no expert, and they were big, enormous, and he was surprised he'd never realised just how big, E cup he thought probably. She looked into Alan's eyes, before moving her gaze down to his crotch and the enormous tent his cock made. "I like it you know? I like you too. But you ran off so scared, and didn't even grab my number before you left. I've been waiting for you. But look at you; you're so nervous, like a little mouse, it's adorable. But I knew I'd catch you sooner or later little mouse. Do you want me to take out your little mousy dick and stroke it Alan?"

Alan knew for a fact that his eight inch cock was far from mousy, but somehow, this goddess degrading it turned him on even more, "Oh god yes Elise, please?"

"Good boy Alan, that's a good boy. You should always use manners when you talk to me Alan." She reached down and pulled the waistband of his shorts down, freeing his cock to slap against his stomach before standing straight up, hard as a rock. "Ooh, you look positively bursting. Are you ready to cum already Alan? Are you about to shoot your jizz all over yourself due to little old me and my tiny little thong bikini?"

"Oh, Elise, yes, I'm going to cum."

She reached down and ran one finger along the shaft's underside, and Alan lost control. He'd never cum harder in his life. He bucked his hips while spurt after spurt fired out of his hard-on, some even landing on his chin. Elise just watched him shoot, amused that he'd cum from just one touch.

When he'd finished, he stayed hard, something that hadn't happened for a few years, but he hadn't been this turned on for a long time. "Alan, there's something you should see. Close your eyes." He was so in her power now that he immediately, unquestioningly obeyed. He could hear her moving around, until she told him, her voice coming from above him, "Okay, you can open your eyes now." She was standing above his head, naked, looking down at him. Her hands covered her crotch, leaving his eyes to devour the underside of her massive tits, sticking out from her chest, huge areolas and inch-long, thick nipples hard at attention. "Are you ready Alan?" He wasn't sure what she was talking about, but he was willing to do whatever she asked.

She didn't ask him to do anything, she just took her hands away from her crotch, releasing the biggest slab of cock Alan had ever seen in his life, including the few cocks he'd seen in pornos. Alan froze in shock. Elise was a transsexual? A shemale? How come he hadn't noticed she had a cock before? She didn't look like a man at all, how could she possibly have a man's cock? Didn't transsexuals all look a little bit male, weren't there tell-tale signs? He didn't really know if he was honest, but he was shocked to learn that Elise had a cock. And what a cock it was. It was enormous. Completely soft as it was, it had to be about ten inches long. She softly lifted it up and lowered herself to her knees. Alan didn't move, didn't know if he could move, was he breathing? He gasped for air all of a sudden. Elise picked up her slab of cock meat and dropped it right on Alan's face with a large slap, covering one eye and running down beside his nose, over his lips. "Alan baby, you have no idea how much this is turning me on. I think we're going to be very good friends you and I. Why don't you give it a little lick huh? For me? Don't you want us to be such very good friends Alan?"

Alan was in turmoil. He wasn't gay; at least, he'd never thought he was before now. He'd never looked at gay porn, never looked at other guys in gym showers or anything. He might have stumbled across a few shemale porn videos on the internet, but he certainly didn't seek it out. Did it turn him on? Now that he thought about it, sometimes it did. Why? There was something about a chick with huge tits, paired up with a huge cock that just did it for him. Most importantly, was he turned on now, with Elise? Yes, yes, a thousand times yes he was.

His tongue shot out of his mouth, slurping Elise's cock meat, licking it like a lollipop, with little technique, but overflowing with enthusiasm. "Ooh I think my little mousy boy likes my big cock." Alan continued to lick her cock as best as he could, which wasn't saying a whole lot, but it seemed to be working. Elise started sliding her cock back and forth across his face, giving him good access to all areas, "Good boy Alan, lick my dick good. You like that don't you? Well if you're a good boy, and lick it good, you're going to get all of it Alan. Now, why don't you open up and give it a little suck?" Suck her cock? Did he want to suck her cock? Yes, again, yes. Her dick had started to fill with blood, and harden up. He opened his mouth, inviting her to enter it. "Oh Alan, you really are a good boy, eager to please, aren't you? Don't worry; I'll take good care of you." She slid the tip all around his mouth and lips, while he continued to lathe it with his tongue. Alan had no idea how he was going to get his mouth around her fat dick, but apparently it was time to try.

Elise slowed her thrusts, placing the tip against his lips, allowing him to slowly admit it to his mouth, stretching around it. Once the tip was in, Elise, who'd been slowly losing patience, took control. Her cock was now fully hard. "I'm sorry Alan baby, but I have to do this," she grabbed hold of Alan's head, and thrust her cock in as far she could. This was Alan's first cock sucking experience on the giving end, and Elise had shoved her way past his tonsils and into his throat, and she was thick. Alan panicked. He couldn't move, couldn't breathe, and even trying to cough didn't seem to be helping. Elise seemed to be going wild though, she pulled back before shoving forward again, never leaving his throat though, so Alan couldn't catch his breath. Just as he thought he was going to pass out, Elise withdrew completely. Alan gasped for breath, feeling as if his life had just been saved. Elise stood up and walked towards her back door, before looking back at Alan and asking, "So, are you coming Alan honey?"

She'd nearly killed him with her enormous slab of cock meat, shoving it down his throat and making him her bitch. He shot to his feet, about to give her a piece of his mind. She stood with one leg cocked, and a hand on her hip. Her fuck stick stood at full attention sticking out from her crotch at a forty-five degree angle, visible in profile. Her copper hair glinted in the sun. Her massive, enormous E cup udders hung low, but still proud. Her naked, glorious booty stuck out, suspended above her heels. "Yes, I'm coming goddess."

"Goddess, I like that, I think you should call me that from now on. Now, come on inside mousy boy, I think it's time to have some real fun."

* * *

It wasn't long before Alan found himself face down on a heart-shaped bed, with red, satin sheets, having his most intimate area greased-up with lube. He was frightened, more frightened than he'd ever been before in his life, and there were two things he was frightened of. The first thing that scared him was the size of the cock which was being prepared to pop his arse cherry. The second thing that scared him was disappointing his new Goddess. In the space of an hour he'd gone from fantasising about the hottest female he'd ever seen in his life, to completely submitting and devoting himself to the hottest shemale he'd never even begun to imagine.

As rough as Goddess had been on his mouth, was as soft and gentle she was on his arse. She slowly, gently, but insistently, worked the tip of her dick in past his sphincter, and he felt relieved once that flared ridge was in. He knew it wasn't over however. Sweat was pouring from him, and his cock, which had been at its hardest only a short while ago, seemed to be setting new records for sheer solidarity.

Alan felt the pressure when Goddess started pushing forward again. Her hard-on flared out only a little after the ridged head, so though he felt pain, it was more discomfort than anything else. Soon he had the whole thing inside him, "Oh Goddess, I love it, please, fuck me Goddess."

"Oh yes baby, it's all for you now, all for you." She pulled back, and after a few thrusts, Alan realised the pain was gone, leaving only pressure behind. Goddess, sensing his growing arousal, grabbed hold of his hips, and began to really work her enormous organ in and out of his tight arse. He looked back over his shoulder, to see her big, heavy E cup milkers shuddering in time with her thrusts. The sight caused him to begin to buck back against Goddess, wanting to feel her really pounding him. "Oh good boy Alan," she gripped his hips in a vice-grip, and began to really slam into him now.

"I'm so worked up Alan baby, I'm going to cum really soon. I'm going to shoot all my cream, and I have a lot of cream Alan. Where do you want my cream? Do you want me to spray it all over that cute little face of yours? Or how about I paint your back with it, maybe a few strokes across your pretty little butt? Maybe you'd prefer to feel my milky goodness inside you, should I just spurt it up inside you now?" Before Alan had even had a chance to give it a thought, Goddess was pulling out of him and pumping her huge erection in her hand, apparently intending to paint his back with her batter. "OH YES ALAN! FUCK I'M CUMMING! FUCK I'M CUMMING!" It was like someone was squeezing out sauce from a squeeze bottle in huge, long arcs, all over his back, except the sauce was coming from his Goddess's cock, and it was molten hot. He felt more than a dozen splatters on his back, and then a last few on his arse.

Report Story

byTheTitLover© 15 comments/ 196804 views/ 218 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: