Boys will be Girlsbygenderbender©
Jack sat at the bar, his eyes moving about the dimly lit room as he sized up the possibilities. He was relatively new to town and had yet to draw a circle of friends around him. He was the sort of fellow that typically drew others toward him. He was handsome, athletic and wealthy, but it was his friendly manner that put people at ease. He really didn't have time for those hangers on who simply wanted to indulge themselves with his generosity.
He'd notice the blonde and brunette sitting together in a booth on the other side of the room. They were seated together on one side, which suggested either they were waiting for other friends to join them or they might be an item. They were stunning women and the thought they might be lesbians was the source of some disappointment to him. He knew San Francisco's reputation as a haven for gays, but he was hoping he'd find at least a few straight people with whom to enjoy life and a little passion. At that moment the blonde caught his eye and smiled. He nodded in her direction but she turned away, her attention once again focused on her seatmate.
He turned his attention toward the others occupying the rather intimate room. In the mirror behind the bartender he caught the eye of a very lovely woman seated at the other end of the bar. She smiled and tipped her glass in his direction. Jack called the bartender over and ordered another drink for the woman. As the bartender was delivering the drink with his compliments he eased off his chair and sauntered in her direction. Her long legs were turned toward him, crossed with a skirt riding at mid thigh, one high heeled shoe extended, the other resting on the barstool frame. Jack quickly took in the image. Long blonde hair swept back from a perfectly made-up face with deep-set eyes and full lips. The woman's silk blouse was buttoned to the neck, but the heavy forms of her breasts were visible in the softly caressing fabric. He slid onto the stool next to her as she spoke.
"You're a dear, thank you." Her voice was sultry and throaty. She lifted her glass in his direction before tipping it to her full, moist lips
"Ah yes, your pleasure is most important. In fact, I would venture the guess that your pleasure would be my pleasure." He was seated facing her, his feet still on the floor, his legs spread on either side of her knees. He saw the woman's eyes quite openly lower to assess the condition of the front of his jeans. He could feel himself responding to the frank appraisal.
"So what is your name? I don't believe I've seen you in here before." Her left hand lifted to push her hair back, the move causing her blouse to pull tightly across those oversized breasts. Jack allowed his eyes to stare at them a moment before responding.
"Jack Miller." The woman smiled before continuing, a smile that acknowledged their mutual appraisal.
"And was I right? Are you new in town, or just new to our lovely watering hole?"
"Both, to be exact. I moved from L.A. last week."
"How fortunate for you and how lucky for all of us girls." Jack couldn't help but wonder whether this creature was putting him on with her almost theatrical manner. The thought crossed his mind that she might be an actress.
"My name is Marilyn." She extended her long slender fingers, which he accepted in the palm of his hand.
"Nice to meet you Marilyn." The bartender had brought his second drink and he lifted the glass toward his new acquaintance.
"So have you found a place yet?" She had shifted slightly on the stool, a move that brought her nylon covered knee to within inches of the bulge which now was more than noticeable in the front of his jeans. Her foot was between his legs, the pointed shoe rocking slightly as her leg moved from time to time. Jack knew the move was no accident, that she was playing the sexual edge between them.
"I'm staying at a hotel for a few days until my furniture arrives. I expect I'll move in early next week."
"How lucky that you were able to find a place. Is your hotel near here?" The shoe touched the inside of his leg just below his knee.
"Yeah, I'm staying at the Fairmont."
"Oh my, you travel in style. I like that!" It was her ankle against his leg now. "I think you should invite me over for a brandy." Her smile sparkled, the tip of her tongue resting on her lower lip.
"That might be nice. Were you thinking of this evening perhaps?"
"Am I that transparent or are you just a very clever boy. Tonight would give me great pleasure."
They stood next to each other at the curb waiting for a taxi, Marilyn's hand resting on the inside of his elbow and her firm breast pressing against his arm. She was almost as tall as he was in those high heels. He held the door for her when the cab finally arrived, watching in appreciation as her skirt rode up along her thighs as she slid onto the seat. They continued to make small talk as the cab traveled up the hill toward the hotel. The man at the desk gave no notice to his companion as he handed Jack the key. Marilyn stood close to him as they rode up the elevator, almost inviting him to slide his arm around her waist, which he did without hesitation.
Things happened quickly when they entered his suite on the top floor. Marilyn stepped in front of him, pressing her body against his as their lips quickly found one another. If pleasure had been her goal, it was clear they would waste no time in finding it. He marveled at the firm breasts spread against his chest, at the hips grinding against his own. Then he felt fingers insinuating themselves between their bodies until he experienced the tight grip on his erection. They stepped apart, both partners staring down at Marilyn's fingers stroking him through the denim.
Jack appreciated a woman without inhibitions so Marilyn's obvious willingness to speed ahead wasn't a problem for him. He watched as she slid the zipper down his jeans and carefully extracted his throbbing member. Then she was on her knees, lips spreading over the bulging crown of his cock as her fingers released the top of his jeans and began pulling the tight garment off his hips. Her expertise was dazzling, lips and tongue playing together as more and more of his substantial organ disappeared in her wet mouth. Her fingers were now caressing his bare bottom, pulling his hips closer until those red, glistening lips were pressed into his pubic hair and her throat milked his rigid organ. He'd never experienced this before!
Someone was actually deep throating his long, thick cock. He braced his knees against the onslaught, aware of the tension building within his loins. Somehow he knew this creature wanted to drink his cum and he gave up any notion that he needed to give her pleasure in exchange for this incredible gift she was offering him at the moment. Suddenly he was cumming, his cock exploding into the upturned mouth, cum splattering against the roof of Marilyn's mouth. He grabbed her shoulders to keep from falling. The mouth continued its milking action and to his shock and delight profound new waves of sensation washed over him.
He kept cumming, his organ surging over and over again until at last he could do no more. Marilyn tilted her head back to give him a view of the long, pink tongue cupped to contain the thick, white liquid that had erupted from his cock only moments before. As their eyes held one another she slowly curled the tongue back and swallowed his cum. She kissed his shriveling cock one last time and licked her lips before slowly rising to her feet. Jack willingly accepted her lips and the deep, tongue swirling kiss that followed, aware that the tastes he experienced were from his own body.
"Now why don't you fix us that brandy and I'll make myself a bit more comfortable. Where's the bathroom sweetheart." Jack pointed toward the bedroom, then watched her swinging hips as she retreated, marveling at the tight skirt and the round curve of her perfect bottom so obviously on display. For some reason the thought occurred to him that it might be nice to fuck this incredible creature in the ass. He shook his head and carefully slid his organ back into his shorts and pulled up his jeans.
He opened four small bottles of cognac from the liquor cabinet and poured them into brandy glasses he found on the shelf above the cabinet. He sauntered toward the leather covered sofa in front of a fireplace that appeared to have a gas fired log awaiting a flick of a switch. He set the glasses on the table next to the sofa and attended to the fire. Just at the moment it burst into flame he heard Marilyn's voice behind him. Turning he found she'd taken off her blouse and skirt and had somehow found a silk peignoir that hung open down the front. She must have carried the diminutive gown in her purse he mused, his eyes taking in the exciting spectacle.
A triangle of red silk covered the mound where slender thighs came together. A red garter belt circled her narrow waist, long straps reaching down to hold the top of sheer, lace trimmed nylons. She was still wearing those dazzlingly high heels. Her brassiere fully covered those deliciously full breasts, but the translucent nylon cups permitted him to see erect nipples rising from darker circles at the center of each mound. Jack was surprised to feel his organ stirring within his jeans once again.
Marilyn walked slowly toward him, her hips swinging sensually from side to side. As she stepped to his side she casually pulled the peignoir closed before leaning close to kiss his lips. They quickly eased into one another's arms and once again he was treated to the pleasure of heavy breasts against his chest as well as fingers caressing his erection. His hands slid down her back until they spread over those round cheeks he'd so appreciated just a few moments before. Clearly Marilyn was wearing thong panties because her firm bottom was naked except for the soft silk. He lifted the peignoir until his fingers were caressing bare skin. Their lips parted and Marilyn tilted her head back until their eyes met.
"You want to play with my bottom, I can tell." Her hips thrust against his erection, then back toward his caressing hands. "Maybe you want to fuck my little ass. Is that it sweetheart?" His fingertips slid between the cheeks, slowly tracing the cord holding her panties in place that ran along the crevice. He smiled.
"Maybe." Marilyn's lips lifted into a broad smile, tongue darting out to caress her lower lip. Without comment she stepped back, slowly turning while she lifted her peignoir to show off her tight, round bottom.
Jack was the one on his knees now, lips moving over the firm cheeks, tongue sliding along the cord lying between them. He'd always enjoyed this erotic territory, though he seldom found women interested in playing along. He took hold of the cord with his free hand and pulled it to the side to give his tongue greater access to the delights awaiting his attention. He was aware of Marilyn's fingers playing between her thighs and guessed she was adding to the excitement by teasing herself as his tongue slithered across the tight opening she appeared to be offering for his pleasure. He could hear her groan as his tongue stiffened and simulated the act he hoped soon to be performing, thrusting toward the circle, then back again before lasciviously licking the sensitive flesh. He attempted to run his finger between Marilyn's thighs but found the way blocked by her hand. He withdrew and his newfound playmate rose from her bent over position. She turned and bent to kiss his lips, playing her tongue between his lips and along the tongue which had been pleasuring her with such abandon.
The next thing Jack knew he was once again receiving the most wonderful blowjob of his life. He watched those lips spread around the thickness of his organ as they rose and fell, gradually taking more and more of the substantial instrument. Then her lips lifted and she smiled up at him
"I think he's ready, don't you?" With that she rose and turned, glancing over her shoulder as she walked toward the full length mirror covering what appeared to be a closet next to the bar. Her long legs parted as she pushed the peignoir to one side, again offering her incredible bottom. Jack pushed himself off the sofa and walked toward her, his cock obscenely hard as it swung from side to side with each step. His eyes caressed her bottom. Marilyn's knees were locked and she'd bent over slightly at the waist, thrusting her cheeks toward him. One hand reached back to slide the cord from between the cheeks, offering him an unobstructed access to her ass.
"Give me that big, hard cock, lover!" Her other hand was between her thighs. He could see it reflected in the mirror. Her breasts were also reflected, the full mounds visible between the parted silk peignoir. He stepped behind her, his cock clutched in his fist, the tip easing between the round cheeks. He spit on his other hand and smeared the saliva over the bulging crown before guiding it toward the waiting circle. He gazed down at the tip wedging between the round cheeks as he eased his hips forward. He could feel the familiar resistance but continued slowly. The tension held for a moment, then eased slightly, allowing his organ to slide past the tight opening. He pressed forward, staring down at the thick shaft. His hands were now on her waist, gently pulling her willing body back against his rigid invader. He paused, then withdrew a bit before pressing forward again. This time his cock slid deeper, tightly held by the muscles buried between the cheeks. He withdrew again, then forward. His cock didn't stop with this stroke, sliding deeper until the round cheeks were nestled against his belly. Marilyn's groan announced her appreciation of his effort.
"Fuck me you stud, fuck my ass!" Marilyn thrust her bottom back, arms extending to brace herself against the mirror. Jack withdrew and began the familiar stroking motion of his hips, driving forward, pausing, then retreating before thrusting forward again. His cock was in the vice grip of Mairlyn's ass. It was unlike any other sensation he mused as he gave himself to the rhythm of fucking. He peered over Marilyn's shoulder and caught her eyes in the mirror.
She was on fire as well. He slid his hands up her side and reached around to cup those beautiful breasts, marveling at how firm they were. He longed to kiss them but knew it was impossible from this angle. Later he'd lick her nipples. She stood erect, leaning back into his embrace. He watched his fingers moving over the full mounds, then watched her fingers playing between her thighs. He was about to slide one hand down to join her when one of her hands withdrew from between her thighs, the fingers turning toward the mirror as they appeared. His hips thrust forward, then back. He knew he was getting close to cumming. He closed his eyes for a moment, then opened them again, focusing on Marilyn's fingers.
Something in the image didn't compute. For a moment he let it go, his loins on fire with excitement. He'd never fucked a tighter ass! Then it suddenly dawned on him what he was looking at! The fingers lifted higher, the silk triangle sliding fully to one side. Marilyn was stroking a cock, a man's cock! Jack's hips suddenly froze but the sensations building in his loins simply could not be stopped. With a groan his cock erupted in the tight grip of this creature's ass. He clutched Marilyn's waist to steady himself, his eyes still fixed to the perfectly normal cock between Marilyn's pumping fingers. Suddenly that organ erupted as well, spewing white juices against the mirror. He watched the cum run down the glass, knowing his own juices were running past his slowly softening organ. Then his eyes met Marilyn's gaze in the mirror. She winked.
"Thanks for the memory lover boy." The tight ass clenched around his cock as she spoke. His eyes lowered to those breasts he'd been ogling all night, his mind still warped completely out of shape. He released her waist and stepped back, his cock popping free from the grip of that delightful ass. He staggered back to the sofa, falling onto the cushions, still staring toward Marilyn, who was slowly turning to face him. She stood obscenely still, the vision of feminine beauty but with a still substantial male organ thrusting from the side of her silk panties.
"Welcome to San Francisco, lover."