tagTranssexuals & CrossdressersShemale Milf Next Door

Shemale Milf Next Door

byLara_Longstaff©

Craig grunted and tossed the box onto the small, springy little cot that would serve as his new bed, at least for the time being. He wiped the sweat from his brow and looked around. He'd rented a tiny studio above a garage in a nice suburban neighborhood. The room was small, but neat, with hardwood floors, a small kitchenette complete with a little fridge, and just enough room for a writing desk and his thirty-two inch TV. "Home sweet home," he said with a smile.

"I'm glad you like it, young man," the matronly woman said from behind him. She grinned up at him from under her neat helmet of blue-white curls. The short old woman was as wide as she was tall, and reminded him of his grandmother.

"Oh it's just great, Mrs. Johnson!" he beamed, making her blush and start to fuss over him. He was a tall young man, with short but unruly dark hair and warm brown eyes. While not the hunkiest guy alive, the twenty-two year old had a boyish smile that never seemed to fail with women of a certain age. He only wished it had worked so well on the girls at college!

"Now you go ahead get everything situated just the way you like! Frank is about to put some wieners on the grill and I'm sure there will be too much for us. We don't eat much now, you see. It's one of the things you lose as you get older," she sighed, her massive bosom heaving.

"I'd really appreciate that, Mrs. Johnson. Tell Mr. Johnson thank you for me, will you?" He hard a hard time believing that the round woman had lost even a scrap of appetite with old age, but he wasn't about to tell her that. Not when she and her husband were letting him rent the room above their garage for next to nothing!

"You're such a lovely boy!" she patted his cheek affetcionately and made her way slowly down the stairs. "Oh, I almost forgot! I'm making a lemon cake too! I bet a growing young man like yourself would love a big slice of that!"

"Don't tell Mr. Johnson, but I think I'm falling in love!" he leaned against the door, smiling down at the old woman. She giggled like a schoolgirl and tottered off down the stairs. He watched her cross the back yard and return to her big house before closing the door and sitting back on the little bed. The garage was tucked away behind the house, with a narrow drive leading along side the two story dwelling. He'd have plenty of privacy there, and if Mrs. Johnson kept giving him food, as some older women seemed delighted to do, he'd be living there practically free! It was just as well. He'd only just graduated from college, and had yet to find himself a real job. Working three days at the local electronics shop wasn't going to last him very long. He needed to finish the polish on his resume, but he'd have to clear some space first!

Humming happily to himself, he rose from the bed and started organizing his meager belongings. It wasn't long before he heard a faint splash through his open window, and he glanced outside. Probably just the neighbors having a dip. He did a double take and moved to the window, peering out over the neighbor's fence.

"Better to be lucky than good," he grinned to himself as he spied. Who knew that the Johnson's had a curvaceous female neighbor? He watched, rapt, as she made several quick laps back and forth in the in-ground pool. With her splashing and at that distance, it was hard to get a good look at her. He tried not to get his hopes up, but he couldn't help but fantasize about a nubile young hottie living next door! It had been weeks since he'd had any action, with a girl he'd casually dated on and off. No chance of hooking back up with her now, though, as she had a year left to go at school and had probably found another guy to play with.

"That's it, come to daddy," Craig chuckled as the neighbor woman finally pulled herself from her pool. She had long dark hair that fell to the small of her back. It was hard to tell from across her yard, but she seemed rather tall and leggy. She had fairly broad shoulders, a tiny waist, and wide, curvy hips. All in all quite an erotic hourglass. She wore a little blue string bikini that barely covered her plump bottom. She turned as she emerged from the water, stretching her arms wide. She had breasts to match that ass, it looked like! She glanced his way.

"Oh, hello!" she called, grinning and waving in his direction. Craig nearly leaped back so she couldn't see him, but of course it was too late for that.

"Hi! I was just admiring your pool, Miss!" he called cheerfully, putting on his best smile.

"I had it put in last year. It's so nice to be able to swim any time I want!" she replied. Her voice carried well over the distance, a mature contralto. Not a young hottie then, but from what he could see, hot nonetheless. "Did you just move in?" she asked him as she grabbed a towel and began to pat her lush body dry.

"I'm renting a room from the Johnsons," he nodded, his eyes fixed like laser pointers to the top of her bikini. He was glad the window hid him from below the waist. The way she was jiggling as she dried herself was positively indecent!

"Oh, great!" she nodded. "Well, I'm sure I'll be seeing you around then!" she wrapped her towel around her waist, gave him a little wave, and in moments, was gone.

"Crap!" he kicked himself. He hadn't even gotten her name! No worry, the Johnsons would know, of course! He'd just ask them over dinner! He stripped off the dirty tee he'd worn during the move and put on a fresh, snowy white button down shirt. It always paid to look good for the landlord, he reasoned. His stomach growled, but as he made his way down the steps, he had two goals in mind. Feed his belly, and find out more about that sexy neighbor!

***

Craig knocked on the door, trying not to feel nervous as he waited. Silence. He checked his watch. It was after nine. Maybe his neighbor, a Delana Winter, as he'd learned, had already gone to bed? He wasn't sure what had compelled him to show up unannounced, only that Mrs. Johnson had encouraged him to send her over some of her delicious lemon cake.

He'd found out a little about her, over dinner and a long, torturous game of Spades. Miss Winter was forty, single, and apparently a woman of some independent means. She didn't work, the Johnson's had confided, but lived off some annuity or another. Craig sighed, about to turn around. The woman was nearly twice his age. No doubt she looked it up close, too.

"Yes?" came the husky, silky voice as the door opened wide. The bright porch light illuminated her nicely. She was indeed tall, Craig realized, at least two inches taller than his six feet in her sexy open-toed heels. Her hair, brown with golden highlights, fell in rich curls around her slim, bare shoulders. She wore a tight navy dress on her curvy body, black stockings on her toned, shapely legs, and a smirk on her beautiful face.

"Oh, hello, Miss Winter!" he grinned wide, trying his best to be charming and disarming. "Mrs. Johnson thought you might like some of her lemon cake!" He offered her the plate covered in a dome of crinkly aluminum foil.

"Oh did she now?" the graceful woman arched a delicate black eyebrow. She had fine lines around her eyes and mouth. Her jawline was a bit square and strong, and her nose a bit bold, but her big blue eyes were nothing less than electrifying. She stepped further out on

"She sure did, Miss. It's pretty good too."

"So, you're the boy who moved in over the garage," she lay a slim hand on his chest and frowned down at him. "Did you enjoy leering at me while I had my afternoon swim?"

"Well, I wouldn't say I was leering exactly," he gulped. Shit! She didn't seem incredibly angry, however. "All right, you caught me. But how could I resist looking at such a beautiful woman?" he smiled innocently.

"Ha! You're a sweet talker, aren't you? What's your name?"

"Craig Allen, Miss Winter."

"Oh don't call me that, makes me feel old. I'm Delana." she pouted, then stepped back into her home. She looked over her shoulder at him. "Are you going to bring me my cake, Craig, or make me carry it myself?"

"Sure, you got it, Delana!" he said cheerfully as he followed the woman inside. She swayed her womanly hips in the most delightful way, and he found his jeans growing tighter around his growing bulge.

"Right here would be fine, Craig." She took a seat at the kitchen table, gesturing to the countertop. She crossed her legs slowly, letting her open-toed heel dangle from one foot.

"Great!" he said as he set the plate down, suddenly at a loss for words.

"So did you like what you saw, when I was swimming?" she smiled at him coyly.

"Now your'e just toying with me!" he protested dramatically. "But sure, you're very beautiful, you know!"

"I would think that a boy your age would only be interested in bubbly little flip skirts. Cheerleaders and what not," she said as she lit a long cigarette.

"Those silly girls?" he scoffed. He didn't have the heart to tell her he'd wished she'd been a hot girl his own age at first. A little flattery never went astray. "I never know what to talk about with girls my age. They can be so boring," he said instead.

"So you like older women for the conversation? Pity."

"I did't mean-" he stuttered, not sure what she meant by that.

"Oh have a seat, Craig, and tell me about yourself," she chuckled in the marvelously sexy throat voice of hers. He pulled out a chair and sat across from her. She looked dressed up for an evening on the town.

"Say, I'm not interrupting something am I?" he wondered.

"Hmm?" she looked puzzled for a moment. "Oh, you mean my dress? I had a dinner date earlier. With a man my own age, more or less. I don't think he could have handled me, so I came home after dinner."

"He really should have tried harder," Craig chuckled. "You may be a lot to handle, but totally worth he effort!"

"Oh you're a charmer!" she threw her head back and laughed. She stabbed out her cigarette and the interrogation began. She asked him about his family, his schooling, his plans for the future. She seemed quite pleased that he had a marketing degree and was ambitious in his goals.

"Thanks, but this feels like a job interview!" he chuckled.

"Who says it isn't? Tell me, Craig. Young men can be a bit inhibited. Do you have any hang ups, in bed I mean!"

"Miss Winter!" he gasped, a little surprised at her boldness, but not displeased. Maybe there really was something to dating older women!

"Delana, remember?" she shook her head. "Really, if you can't remember such a simple instruction I might have to look elsewhere for my new boy toy!"

"Boy toy?" he felt a little degraded by that term, but turned on nonetheless.

"Yes, boy toy," she repeated, and lit up another smoke. "How do you feel about homosexuality, Craig. I like a man who is open-minded."

"Doesn't bother me a bit," he shrugged.

"Good. But have you ever experimented?" she wondered, leaning over to look into his eyes.

"No, but not because I hate gays. I've just never found men attractive at all."

"And if you did find a man attractive, would you ever consider it?" she pressed.

"I don't know," he said, leaning back a bit defensively. Was she questioning his sexuality?

"Don't be evasive, Craig, it doesn't suit you. Now think, imagine yourself as attracted to a man as much are attracted to a woman, myself for example," she explained.

"He'd have to be one handsome guy!" Craig chuckled.

"But would you?"

"Sure, why not? You only live once," he leaned forward again, catching her hand. Her skin was soft and her fingers long, but she seemed surprisingly strong. "Hell if I was half attracted to this mystery man as I am to you I'd jump right into his bed, no questions asked!"

"Oh Craig," she laughed. "You're delightful!"

"Yes, and sweet as honey too!" he rolled his eyes playfully. "But this boy toy thing. Sounds a bit S&M for me."

"Oh its nothing like that!" she patted his hand.

"Well, what's it like then? You have to know that I'm eating out of your hand right now!"

"Just where I like a man!" she said with a mysterious smile. "I date men my age from time to time, but find them, inflexible," she licked her lips before continuing. "Staid. Stuck in their ways. I'll admit to being a selfish woman. I like a young, adventerous man who isn't afraid to go the extra mile to please me!"

"Well, I'm your man then!" Craig said heartily.

"Oh?" she looked at him slyly. "Just remember what I asked you before, Craig."

"Sure, I'm not uptight!" he confirmed.

"Then why don't you get on the floor, and take off my shoes for me? These heels are sexy, but they can get a bit uncomfortable."

"Uh, all right!" he said gamely. He knelt before her, grunting a bit at the cold tile beneath his knees. She held out a foot for him, and he slowly pulled it off. Her foot was graceful, if rather large, though he supposed since she was so tall it fit. He couldn't resist sliding his hand up her shapely calf. The silky nylon felt so good beneath his fingers. Why did girls his age never wear them?

"Nice, but don't forget the other!" she admonished him and uncrossed her legs before recrossing them again with the other leg on top. She gently kicked her heel in his direction.

"Of course, Delana!" he repeated the process, and she let out such a long, low groan of relief he took her foot in hand and began to massage her soft sole.

"Oh you have good hands, Craig!" she cooed in delight. He moved his thumbs in firm little circles before taking her other slim ankle and giving the same treatment to her other foot.

"Is this the kind of thing in store for your boy toy?" he asked. "Because if so, I think I could get used to it!"

"Yes, and so much more!" she purred as she pulled her dress up her legs slowly. His eyes followed that rising hemline, taking in her long perfectly shaped legs inch by inch. She wore thigh high stockings, the wide lace band at the top a dark contrast to the hint of pale, creamy thigh above. She left her dress bunched up between her legs as she spread them slightly. "Keep moving up, Craig, you're doing great!"

"Thanks Miss-" he cleared his throat and corrected himself. "Delana!" He glided his hands up her legs. They were definitely the longest he'd ever had the pleasure of touching. He massaged her toned calves, then her tickled her behind her knees, making her squirm and laugh in delight. That laugh was starting to get to him, so deep for a woman, and sultry.

"It's time, Craig. Brace yourself, and remember what you told me about being open-minded!" she said as she pulled her slinky dress up, pulling it over her head. She shook out her long hair, and Craig feasted his eyes on her big, pale breasts as they wobbled in her flimsy black bra. Her body was tight all right, she really took care of herself! His gaze wandered lower, and she spread her legs even wider, and that's when he saw it.

"What the hell is that?" he yelped and pointed. Her black satin panties strained over a rather large and unfeminine bulge.

"What do you think?" she asked huskily. She stood, and he fell back on his bottom, looking up as she straddled his legs. The huge bulge was inches from his face. "I'm transgendered, Craig. I was born a male but twenty years ago decided to live my life as a woman. It suits me don't you think?" She cocked her hip to the side, accentuating her womanly figure.

"Well, I'm kind of surprised," he managed at last. She was still hot as hell, but just how hard up for sex was he?

"I can see that!" she chuckled, and unceremoniously pulled her panties to the floor. She straightened, and when she stepped out of them her cock swayed from side to side heavily. Her cock. She had a cock! And it was a big one too! Still soft but already a little longer and thicker than his biggest, best hard on, it hung between her slim thighs in front of a big pair of smooth balls. She'd shaved herself smooth, and there wasn't a hint of hair anywhere near the fat, pink organ.

"Don't you think I have a nice cock, Craig?" she slid a hand down her body, wrapping her hand around the shaft and holding it up. The pink tip drooped from her fist inches from his face. It all made sense now, the height, the hands and feet, the voice, that strong jaw.

"I should have seen this coming," he said. It was harder than he thought to look away from her big prick, but he did, meeting her gaze as she looked down at him.

"You should have, but I can forgive a rookie mistake when it comes to a cute young guy like you!" she laughed and let her cock dangle. He looked back down at it, watching it jiggle with her every move. He didn't notice she'd taken off her bra until the flimsy garment fell right on his face.

"Hey!" he pulled the bra off his head and looked back up at her. "I think, wow, I don't know what to say," he muttered. He scooted back and pushed himself to his feet. In her stocking feet, she was just an inch shorter than him.

"Say that you weren't lying about having an open mind. Say that you meant it when you said that if you found a man half as attractive as me, you'd jump into his bed," she said the words softly, her voice as rich as velvet. She crossed her arms under her bust, and he glanced down. They seemed awfully firm for a woman her age, round and pale with big pink nipples.

"Well, you're kind of putting me on the spot here! I need to think about this." he said quickly. She cupped the firm bulge in his jeans, massaging him to full hardness in an instant.

"What's to think about, Craig?" she asked as she fondled him. "You're hard, I'm horny. Don't think. I want you, and you want me. So be a good boy and sit down," she pulled him toward a chair, and he plopped down on it.

"All right," he looked up at her. She was still hot as living fuck, but could he? His eyes kept returning to her swaying manhood. Shit, she was well hung! He blushed. Great, a woman had a bigger dick than he did!

She pushed his knees together and straddled his legs, her feet planted on the floor and her body close to him. "So, since we're both into each other, just forget about everything else and suck my cock, please, Craig?"

He stared at her for a full minute, the longest minute of his life, before he made up his mind. Delana Winter seemed all woman, and if she had been, he no doubt would have loved to lick her pussy right about then. He inspected her cock closer. It was really quite handsome, straight, with smooth, lightly tan skin and a pink head shaped like a heart. Up close he could smell her perfume, sweet flowers mingling with a hint of masculine musk. No one would know what he was contemplating doing. Everyone would think he'd simply scored the hottest milf in town.

"Whatever you say, Delana," he mumbled before taking her in his hands. Her cock was so warm and soft! He gave it a squeeze, and it didn't stay soft long!

"I had a feeling you'd come around!" the older woman smirked, pushing her womanly hips closer. Her rod stiffened at his touch, growing inch by inch so that soon it not only was bigger than his own, it would put a lot of porn stars to shame.

"Wow, you're really well hung!" he gulped and looked up at her bashfully.

"Yes, I know," she shrugged, but her smile said it all. She was proud of her cock, and who wouldn't be?

"Uh, I hope you don't expect me to, um, outdo you when it's my turn!" he added, suddenly shy. He looked away, and found her steel-hard cock pointing right at his face. He gave her a quick little peck at the tip, just to test what it was like. Her skin was hot and rubbery against his lips, and not bad at all.

"Who said you'll even get a turn? You're my toy remember?" She laughed, her big breasts quaking. "Don't worry though, I have a feeling you'll be quite satisfied, in your own way!"

"That's oddly kind of a relief," he sighed, and laughed when he looked up at her. "One less competition in life suits me!"

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byLara_Longstaff© 28 comments/ 153766 views/ 305 favorites

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