Autumn in New York

by Whiff

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, Consensual, Romantic, TransGender, .

Desc: Sex Story: A man meets a unique woman on a fall day.

A Walk in the Park

It was one of those soft, cool New York days that make everyone want to be outside, since such weather is so rare. Dave had decided on a sweater, though it wasn't absolutely necessary, but the last few blocks of his walk home would be on the lee side of Central Park, and the breeze might come up. Anyway, he loved wearing sweaters in the fall.

The newspaper flew out of her hand just as he turned on forty ninth to walk over to fifth. It was almost a reflex action to take a quick step left, bend at the legs and waist, and scoop up the mass of newsprint as though it was a ground ball. As he leaned over there, trying to hold on and simultaneously re-fold the thing, he felt a hand brush his, and looked up to see the gorgeous redhead down on her hands and knees fumbling with the same twisting mass of paper. Her hair was blown toward him, framing huge eyes, heavily made up, dark tan lips on a full mouth, and a tiny, patrician sort of nose, all in all a refined yet sensuous face. He had a flashback of firm, twisting hips on a big woman just before the New York Daily News got away from her.

In a deep, sexy voice, she murmured "Thanks, thanks a lot. The wind kind of surprised me." Dave blushed, and stuttered "No problem. Damn high buildings, makes it windy even on the nicest days." His hands had stopped moving as he gazed at her, and he realized she had the paper neatly folded and tucked under her arm. She was staring at him. Naturally, people went walking by, ignoring them.

She had a strange look on her face. Sadness, he thought, but interest, and a little flush. They both stood slowly, and Dave felt it was almost a dance. She was only a couple of inches shorter than his six one, and held his eyes. He felt he wanted to just stand there. When the long pause got embarassing, she broke the silence by taking his arm, and pulling him, stumbling, down the block.In that low voice, she said "I'm heading for seventh avenue, to drop this for a friend. I don't usually read it." Then she laughed, a low, throaty guffaw. "Now why should I tell you that? Huh. Because I don't want you to think I'm the sort of person who reads the "Daily News." Isn't that funny? I've never thought of myself as a snob. Maybe it's you."

As she waited for him to continue the conversation, he kept staring at her. He thought she was younger than he was, but still over thirty, just a few wrinkles around the eyes, and all that makeup. High cheekbones. Such a sexy face, particularly for a big girl. Woman. Shit, he thought, she's waiting for me to say something. Okay, lemme see. "Uh, do you know you're a knockout?"

The minute he said it, he grinned, shook his head, and looked rueful. God, how dumb is that. He continued "Sorry. That just popped out. I mean, I knew you were waiting for me to say something, and all I could focus on was how pretty you are, so... Faux pax time. Sorry."

She gave him the throaty chuckle again. "I have to work at it, but thanks. Glad to see it's appreciated. Where are you going? Isn't it a lovely day?" As she spoke, he felt her grip on his arm firm up, and the soft mound of her breast gently caressed his arm. He felt his cock twitch, looked at her quickly, and she grinned at him. Then she pushed just a little more. "Look, my name's Jesse Moore. Here's an easy one. What's your name?"

By the time they had gotten across town, dropped off the paper, and started back uptown, Dave was in love, and really felt it was being reciprocated. At least a bit. By the time they had gotten to her building just off Park, they were talking about restaurants, and he impulsively asked "How 'bout tonight, Jesse? I know it's short notice, but I hate to say goodbye." He blushed as he said it, and the sadness came back to her face as she looked into his eyes. She seemed to be debating, and he wondered if maybe she had a prior date, or...

But she shook her head, as though to clear it, and answered "Sure, Dave. You're nice to be with. Come back about eight, we'll have a drink, and walk over to the french place. I've never been there, even though it's close. You paying? Good. Then it's a date. A real date." She glanced at the doorman lounging against the wall, then pecked him on the cheek lightly. Her perfume filled his mind, and he didn't remember getting home.

When he got to her apartment, feeling strange because of the way the doorman looked at him, even though polite, his mind emptied as she opened the door. The same lovely face, made up with slightly darker lipstick, and heavier mascara, giving her a more sensual look, atop the most spectacular figure he had ever seen. She was over six feet in high heels, with a black halter dress that showed off spectacular big tits. He had felt them, but he could see their fullness covered with a thin silk, nipples prominent, cleavage puffed up with some sort of bra, he supposed. Her wide shoulders and the figure hugging cloth showed off long legs, and full hips. There wasn't an ounce of fat, but she was still curvy and feminine. When she saw his reaction, she grinned, and pulled him inside.

She took the bottle of good port he had brought, and set it on the coffee table, the movement as she twisted around and down erotic as hell. The process of straightening up from her leaning over gave him a flash of nipple, and his cock jumped. She smiled and raised her hands to the side, sort of posing. "Not bad, huh baby. I'm glad to see you approve. Maybe we can have some port when we come back, but I have some chardonnay chilled and open. That okay?" He still hadn't been able to muster a word.

He floated through the evening, relaxed and intoxicated with her. There was a bit of a strange character toward the end, as he felt her attraction for him matching his, but he ignored the slight tension she seemed to feel. On the way home, she asked him about plays he'd seen recently. She apparently worked as an editor for a publishing house, and was very knowledgable about recent Broadway. After he reeled off several he had seen, she asked "M. Butterfly?" He told her he hadn't seen that one. She said she had the movie, and maybe they could watch it sometime.

Just before they turned the corner to her apartment, she stopped him. "Dave, look, I... can't ask you up. I know, we talked about port earlier, but... I have to think about this, okay. I had such a good time, it was so..." She leaned in to him, pushing her tits into his chest, and kissed him gently. He felt her trying to keep it soft, and reached up behind her head, and pulled her mouth to his hard, opening his mouth and sticking out his tongue. He felt her flinch, then move against him and give in to the kiss.

It was a wonderful, sensual, five minute thirsting for each other. She was strong, and between the two of them, their bodies heaved and writhed together, passion bubbling out. When they finally separated, he took a deep breath, and she started crying. He was shocked at her tears, and held her close as she sobbed. He muttered "Jesse, Jesse, my god,..."

She tore herself away from him, and pushed him away with one hand, gasping "Just stay here, go home, don't come to the door, okay?" He watched, shocked, as she hurried around the corner, her perfume still strong in his heart.

He started calling the next morning, and for three days got nothing but her answering machine. At first, his messages were cool, saying he had a great time, let's do it again, call me. By the third day, with no response, he felt hurt, depressed, and angry. He finally left a message in which he exploded, yelling how much he loved her, how could she treat him this way, pleading to hear from her. After slamming down the phone, he sat beside it, breathing hard, wondering if he had totally screwed up. As he rose to get another scotch, the phone rang, and he grabbed it before it even had a chance to ring a second time.

"Dave? It's Jesse. Look, I, I haven't been totally honest with you, and it's breaking my heart. I felt strongly too. I did. I don't know what to do. But I guess I owe you an explanation. Come over now." She didn't even give him a chance to respond.

He almost ran the five blocks, rushing past the same doorman, and when he burst into her apartment, she was standing in the door to her bedroom, wearing a black negligee that showed off her tits, and black thong panties under it. He started toward her, and she brought a gun from behind her back and pointed it at him. Shock jangled through his mind as she whispered "Just stay over there, Dave." He froze, then backed slowly a couple of steps.

She looked lovely, but tired. She closed her eyes, and said "Some of my friends warned me that guys like you get violent when they find out... my secret. I'm sorry Dave. Really sorry. In a few months, if we'd met then, it might have been... better. I guess the easiest thing is to show you. Stay there." With one hand she reached to the valley between her boobs, and loosened the negligee. It slithered to the floor, revealing her creamy white skin, slim, boyish hips, and lovely legs enhanced by the high heels.

Dave stared, and in spite of his confusion, felt himself harden, a combination of the memory of their one kiss, her body so sexily displayed, the obsessive need for her that had built up over the last days swirling madly around in his mind. As his hand went to adjust his cock, she watched him, and a tear ran down her cheek. She whispered "Oh baby, baby, I'm so sorry."

In a fumbling sort of onehanded movement, still holding the gun, she pushed down the panties, to her knees, then reached between her thighs, and pulled out her cock. It wasn't very big, maybe five inches, but he could see a ball sack too. His jaw worked, trying to take it in. She finished stripping off the panties. She was watching him carefully, but the red tool was twitching, and the gun was extended. "I'm sorry, Dave. I didn't mean to... it's just... oh god."

Dave collapsed to the deep armchair to his right. He couldn't take his eyes off her. It was still the lovely face, the gorgeous breasts, the big, wonderful body. His cock stayed hard. When he just sat there, still staring, she sighed. "I'm sorry about the gun, honey. I mean, I don't really know if I'd have used it, but everyone said... well, to be careful. I've been this way all my life. I wanted to be a girl. I felt like a girl. The doctors say it's a genetic thing, they actually have tests for it now, there are several kinds of, you know, sort of mixed up... people. I started dressing like a woman when I took this job three years ago, and had the surgery to my tits and hips. But, see, if you have the operation, and they give you the hormones, and... well, cut it off, you can never have an orgasm again. The way I am now, I have great cums. Really. But most herms, they can't. So I've been trying to decide what to do. I don't really like queers. Dykes don't like me. I..."

She collapsed to the floor, sobbing wildly. He heard snatches of gasping pleas. Don't hate me, Dave, Dave. Sorry, sorry. He kept trying to decide whether to bolt, get out of the suddenly stifling apartment, but felt a surge of feeling for the creature huddled across the room. She was still Jesse. Almost in a trance, he rose and walked slowly toward her. She looked up as he approached her, and he saw her grip tighten on the black metal in her hand. He knelt and put his hands gently on her shoulders. She stared at him. He leaned over and kissed her.

She threw herself at him, knocking him backward, and landing on top of him, as she ground her body into him. She kissed him wildly. He felt her cock at his belly, and she was still sobbing. He felt, and then tasted the salty tears. His own cock was suddenly poking at one of her legs. His mind was whirling. He felt her squeezing his spasming member with her thighs. She finally broke the kiss, and stared at his face. "Oh Dave, do you think... I mean, could you try it? I'll make it good for you, baby. You don't have to... just let me make love to you. We... oh I must look a mess."

She did. The heavy mascara was streaked, her lipstick smeared, the red hair tangled. She was watching him as they both gasped hard. She was damn heavy, he thought. He felt her hand grip his throbbing prick. He saw a big, crazy sort of grin. "Oh it's nice and big, darling. I'm just a little girl. Let me go clean up." She rolled over, sprang to her feet, and started through the bedrom door. Her ass looked lovely, twisting as she moved, and she stopped and looked over her shoulder at him. "Darling, either go, and break my heart, or stay. But if you stay, take off your clothes, get ready for me. I'm a hot piece of ass, baby. And I'm desperate for your cock."

Something very strange had happened to Dave's mind. It was as though the rational part was groggy, diffused, letting his carnal part, the part that had been longing for her almost constantly for three days plus, dominate his senses. Yet he undressed in the two minutes she was gone almost in a trance, still laying there on his back in the middle of her living room. He was pushing lazily at his boxer shorts when she reached around the corner, and flipped the light switch. The only source of illumination became the table lamp to his left beside the door, and she appeared in the bedroom doorway.

Jesse, the Jesse he knew and had dreamed of, appeared there with her thighs together, no sign of the male genitalia. She was posed, her chest pushed out, one knee turned in. He didn't think, try to figure it out, just let his cock stiffen again, gazing at her, wanting her. Her smile was luminous as she stared at him. She whispered "I've dreamed of this, darling. A handsome, nice man, wanting me as a woman, I want to be a woman, yours, darling. I want to be loved, desired, fucked. If only you could... accept me, let me keep it, I'd be your slave. Come in the bedroom with me, lover."

She pivoted, spreading her thighs as she did it, and in the dim light he saw only her butt, her jiggling boobs, the long red hair. He struggled to his feet and followed, into the large room with a king sized bed, candles burning in several places, and a nice incense smell. He looked around, briefly, and when he looked back, she was posed on her back, still no sign of the cock, legs together. He threw himself on top of her, one hand cupping the firm pillow of flesh on her chest, feeling the nipple harden. She breathed "Oh baby."

In his mind, she was still Jesse. He began sucking on the nipple of the breast he had first caressed, and his hand automatically started down her body toward her groin. She giggled and grabbed his wrist. His rigid cock was pressed against her hip. He heard her whisper "Come on baby. Fuck my ass. I want to feel you inside me. Get off whenever you want. Use me, baby, use me." She rotated to her side, and pulled his hand to her blinking asshole, which felt greasy already. "Put it in, darling. Put it in and fuck me good."

He arched slightly, finding the little hole, and let the head of his tool sink between her soft buttocks, and without hesitation it penetrated an inch or so. He heard her sigh "Oh god yes, oh darling, darling." Almost without any effort, he began to slide into her. One hand released her top ass cheek, and he realized as he started to pump slowly into the hot, tight intestine, that her hand was moving in her own groin. His mouth was near her ear, and as he stroked smoothly to his full eight inch depth, and heard her groaning in pleasure, he whispered "Let me do it, Jesse. God help me, let me do it."

Her head twisted around and their eyes met, her eyes smiling, her tongue licking her lips. She breathed "David, whatever, fuck me darling, fuck me." His hand reached to cover hers, and she groaned "Oh darling, are you sure, are you?" He wrapped his thumb and forefinger around the base of the prick, just below her hand, and forced his upwards, so hers let go. The tube was hard, but had not grown, and his hand covered it almost completely. He squeezed, and the whole feeling was so sexy he felt the early tingling of his cum. As his hips began humping more forcefully into her behind, his hand stroked.

"Jesse, hurry, hurry, I'm... uh, oh shit..." Her hand came down and made his squeeze harder, and as he started to gush into her ass, the cock in his hand started to spasm. She groaned "Aaaah darling, kiss me, yes, yes." Their hips were both writhing wildly, his member spitting into her, not fully buried as she twisted, and he felt spunk dribbling on his hand, as their mouths met. His mind was soaring. Jesse. Jesse.

They slowly eased their movement, both gasping. As the roaring eased in his ears, he heard her quietly crying, with little choking sounds she was trying to muffle. He asked her "What's wrong, Jesse?" She twisted around, for the first time letting her wet tool press against his stomach. It was still dribbling, and he realized it felt sexy, as she pulled his own half hard member between her thighs.

She choked "I feel so much like a woman, darling. You... no one's ever done that with me before. Even queers. I mean, I don't have much experience, honestly, I mostly jack off. But I've dreamed about a man, taking me, like a woman, yet... touching me... it. Oh god, you're still turned on, oh Dave, did you like it? Really? Oh darling." She flopped to her stomach, and pulled his prick into her mouth, sucking hard. His hand reached over to cup her ass.

As she sucked, and he felt his cock hardening, his mind was strangely at ease. Somehow, he had adjusted. There were questions nibbling at the fringes of his thoughts, am I queer, not much experience, what other things were possible? But his dominating feeling was satisfaction, and growing excitement as she cycled his now stiff dong in her mouth. She couldn't get it all down her throat, but he could feel her tongue licking the piss slit with each cycle. It rather quickly stiffened fully.

She let it out of her mouth and nuzzled it against her cheek, whispering to him "Want to get off in my mouth, Dave? I'd love to eat your spunk. Whatever you want darling. Fuck me again if you want. I'm yours, darling." Her eyes held his as she surrounded the head of his cock, licking gently.

He wanted insanely in his mind to fuck her femininity, her womanly charms. "Can I fuck your tits, Jesse? You know, between 'em?" She released his prick with a big smile, and pulled him on top of her abdomen, twisting so her hips were behind him. Tugging on his buttocks, she got his hard tool centered between the lush mounds, and her hands squeezed them together, as his pelvis began to thrust. She pulled on his ass a little more, then arched her neck and stuck out her tongue so when he was fully buried, she could lick the head.

After several strokes, she grinned up and breathed "I've never done this either, darling. It feels wonderful. Push harder, so I can suck it." He lost himself in the writhing together, his wet cock growing more and more excited, as he watched her avidly enclose his cockhead on each stroke. He started grunting, leaning back, and they went on and on. He felt climax approaching, his balls squeezed against the underside of the warm pillows of flesh.

Dave had always had an instinct to please his partners, and he felt the same urge grow, as his tension began to peak, his hand, almost of its own volition, reached back and surrounded the cock he couldn't see. It was hard, and he stroked it. Her eyes widened, she groaned, and he began to shoot.

She opened her mouth wide, her tongue flicking as the first burst hit under her chin. She grabbed his hips and pulled, and his second spasm happened with her mouth around the tip, and he felt the jism on her tongue. As his third, fiery yet weak dribble emptied into her mouth, her hips shot up, and she grunted hard. His hand was suddenly wet, and he felt several spastic movements of both the small rod, and her hips. Her eyes were closed as she sucked on the bright red head of his softening cock, arching her neck trying to keep it inside her mouth.

Their eyes were locked together as he stopped his movement, his hand still surrounding her cock. She was licking at his tool, smiling, savoring the taste of his spunk, soundlessly caressing his back. They stayed that way for several minutes, as their breathing slowed. Then he collapsed beside her, cuddling to her, and out of the corner of his eye he saw the little movement of her hand as she tucked her small prick between her thighs, so that the dark red pubic hair formed a triangle that appeared to be a normal, nicely trimmed cunt.

Finally, she whispered "Has any of my makeup smeared, darling? How about the lipstick? This brand usually holds up pretty well. You liked it, didn't you? I never dreamed you could handle it so well, David. You seem so... macho, in a subtle sort of way. I thought... I was afraid... that you'd just stomp out. Curse me. Hate me forever. I knew one girl who got murdered when this guy found out." She kissed him languidly, gently licking at his face, and he tasted his fluid. It all seemed uniquely lovely. "Why don't you borrow that black robe in the bathroom, and go open the port. I want to freshen up. A girl like me has to be very fastidious."

When Jesse joined him in the living room, David gasped at her beauty, now in a purple negligee with a white thong underneath, and very tall heels, prancing slowly across the room toward him. In spite of the confusion boiling in his mind, he felt nearly overwhelming lust for the fantastic big body she seemed willing to offer him in any way he asked. Instead of sitting down beside him on the couch, she twisted down to a leaning position at his feet, holding his eyes as she lifted the small glass of red, heavy wine to her lips. They sipped the liquid slowly for five minutes, wordlessly, and her smile got wider as he ogled her tits.

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Story tagged with:
Ma/Fa / Ma/Ma / Consensual / Romantic / TransGender /