Bend That Gender


Shannon's Shocking Discovery

Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covered shoulder next to her. She knew when she visited this bar that she'd encounter gender bending possibilities. Her neighbor Casey mentioned the bar during one of their numerous conversations about love and lust.

Casey worked at Mitchell Brother's as an exotic dancer and knew a lot about the erotic scene in San Francisco. Shannon met Marilyn during her first visit and was relieved to run into her again. Shannon was intrigued by the possibility of making love with another woman but the butch women hitting on her that first visit were certainly not what she had in mind. It wasn't clear to her whether Marilyn was a lesbian or bisexual, but she was in this bar. Of course, there were straight men among the mix of patrons as well, so it was not impossible Marilyn was straight. All Shannon knew was that resting against a woman's breast, smelling a woman's perfume was comforting, regardless of whether it resulted in a sexual liason or not.

"Do you want to get some air?" Marilyn's familiar voice, at once husky and sultry, broke into her reverie.

"That might be a good idea." Her friend turned slowly and began guiding her toward the door leading to the parking lot. The fresh air was instantly reviving as they stepped into the dark evening. Shannon allowed herself to be drawn into Marilyn's embrace as they turned toward one another on the landing overlooking the parking area. The feel of firm breasts against hers, then warm thighs touching her own was surprisingly exciting. She slid her arms around her friend's slender torso and returned the gentle hug. It seemed natural to lift her face to meet Marilyn's gaze and then to accept the lips lightly touching her own, despite the fact they were a woman's lips. The kiss broke and Marilyn whispered.

"You're so lovely, I just couldn't resist." Shannon smiled, her tongue sliding forward instinctively to moisten her lips. Marilyn smiled and lowered her mouth again, apparently taking Shannon's move as an invitation. Her eyes closed as lips softened together. When the tongue touched her lower lip she instantly relaxed into the kiss, her lips parting to receive the sensual caress being offered by this gorgeous woman. It was the first time she'd kissed a woman with passion before.

The kiss broke as the door behind them cracked open. Shannon's breathing had become ragged with her growing excitement. Marilyn's fingers slid off her bottom and rested on her waist as the pair of guys left together arm in arm.

"Maybe we should find some place more private." One of Marilyn's hands slid up from her waist, the fingers turning to spread over her breast as the two men disappeared into the night. Shannon glanced down at red-tipped fingers gently squeezing her breast, marveling at the realization she was actually making love with another woman. The door opened again and Marilyn's fingers eased off her breast. Shannon was shocked to feel disappointment well up.

"We could go to my place."


Shannon heard her friend's heavy breathing behind her as she slid her key into the lock. Then hands were on her waist drawing her body back against Marilyn's lush curves. The hands slid up to caress her breasts as she pushed the door open. They literally stumbled into the dark foyer. The door slammed shut behind Marilyn as they dove into one another's arms, lips quickly finding each other. Their first two kisses were all the introduction these lovers needed. Lips and tongue quickly began their dance, mouths opening and sucking as they each lost themselves in the other. Fingers roamed over her back and bottom and Shannon felt compelled to reciprocate, her fingers forming over the high round cheeks of Marilyn's perfect bottom beneath the silk skirt. Her fingertips told her there were no tell-tale lines suggesting panties, only the straps of a garter belt. The knowledge added to her excitement as fully as did the lushness of breasts pressing into her own. Finally the kiss broke with a mutual sigh. Without words they turned and walked down the darkened corridor. Shannon pushed the door of her bedroom open and led her partner to this most private domain. She'd invited a couple of men into her inner sanctum but only after respectable courtships. Tonight she hesitated not a moment. She turned on the small lamp next to the bed before turning to face Marilyn.

"I've never done this with a woman before." Her words were breathless with her excitement but hinted at her fear.

"I'm honored to be the first, my dear." Marilyn stepped closer, lifting her hands to once again cup Shannon's remarkable breasts. As she grew up she wasn't certain whether her dramatic bosom was a blessing or a curse. She both appreciated and abhorred all the attention she got just because her breasts demanded a brassiere size generally unavailable in her small town stores. It was only when her mother got a copy of a Victoria's Secrets catalogue that she could find a brassiere that was more than utilitarian. Of course that created problems of a different sort because most were not only lovely but very sexy as well.

Whenever she took off her blouse or sweater in the locker room before gym class all eyes were drawn to the daringly low-cut brassiere she filled so dramatically. But this was the first time a woman was caressing her breasts, fingertips finding her nipples through the thin silk of her blouse and gently teasing them. Her breathing quickly became a series of sighs. She gazed down as the fingers began sliding the buttons running down the front of her blouse free. The garment fell open to reveal the deep cleavage between her breasts, then the beautiful brassiere holding the full mounds which came fully into view next. Marilyn pulled the blouse from her slacks and spread the panels wide to expose entirely her bosom.

"Breathtaking my love, absolutely breathtaking." The fingers returned to caress each mound for a moment before Marilyn pulled Shannon into an embrace and once again captured her mouth with those devilish lips and tongue. She was no doubt sober once again yet she was swooning with the excitement coursing through her body. Perhaps it was because she was doing something so forbidden, making love with another woman. Or maybe this lush creature who with such confidence played her increasingly willing body was simply the lover for whom she'd been waiting these many years. Then the thought crossed her mind about how much she loved a man's cock, whether in her mouth or pussy. That would be a loss no doubt but she'd heard about how women use dildos to satisfy that urge. She wondered whether Marilyn had a dildo.

Shannon felt the edge of the bed against the back of her legs and allowed herself to fall backward at Marilyn's urging. She gazed up at her beautiful seductress standing between her legs. The silk blouse she wore was buttoned to her neck but the fabric fell on her heavy breasts like a soft caress. Marilyn's eyes were caressing her body as well and Shannon loved the attention. Her lover leaned over and began undoing her slacks, quickly finding the button and drawing the zipper down before stripping the garment from her legs.

She felt so exposed, so vulnerable, yet at the same time so aroused. She groaned as Marilyn leaned over to press those wonderful lips between her breasts, watching the hungry mouth move from one breast to the other before beginning to slide down her flat belly. Shannon knew instinctively where those lips were heading and couldn't contain her hips as they shuddered off the bedspread. She gazed down the length of her body, between her breasts to the face now framed between her thighs. Marilyn's eyes held hers as her tongue extended, then lasciviously licked along the silk pouch covering her genitals. The pressure on her clitoris made her groan. Marilyn lifted her mouth and smiled before pressing her lips more firmly into the silk, increasing the contact with her genitals.

Then without warning Marilyn took hold of her panties and pulled the material to the side, exposing Shannon's naked flesh to the marauding lips and tongue. The kiss directly at the opening of her already wet pussy drove her over the edge of release, a sharp orgasm that lifted her hips off the mattress. Marilyn road the release, her tongue busily playing across the hard nub as a second orgasm rolled in behind the first. The mouth lifted again, offering Shannon a look at the moist lips and tongue that had ravaged her womanhood.

"Mm, you're as sweet as honey." Marilyn licked her lips and then pressed them once again between Shannon's spread thighs. Before she could speak her body began the inexorable journey toward another orgasm, slowly tightening as the tongue and lips played their magic game with her. She'd never experienced anything this delightful in her entire life! She lay back on the bedcovers and closed her eyes, giving herself completely to the sensations stirring in her loins.

She didn't know how long she'd slept. It was still dark outside and the lamp next to the table still cast its gentle light across the bed. Glancing to her right she saw Marilyn lying next to her, now dressed in a peignoir which likely came from Shannon's own closet. She turned toward her new lover, whose eyes were closed. Shyly she extended her hand to lift the shimmering silk from Marilyn's body, longing to see her lover's naked body. As the panels fell open she saw Marilyn still wore her brassiere and panties, as well as her garter belt and nylons. At that moment Marilyn's eyes opened to meet her gaze. Shannon felt her face flush with embarrassment at having been caught. She smiled sheepishly, grateful the dim light concealed her blush.

"So we're awake." Marilyn took the hand that had opened the peignoir and guided it toward her breasts. Shannon felt her embarrassment return but allowed her fingers to be pressed into the firm mound. The only breast she'd touched before was her own and this contact was exhilarating to say the least. She felt the juices flowing once again. She shyly squeezed the full mound as Marilyn's hand released hers and began its own journey between her thighs. Almost immediately slender fingers found her moist pussy and began stroking her, slowly easing the lips apart until a single digit slid into the heat of her body.

Marilyn leaned toward her and pressed her lips to Shannon's ear, the tongue slithering out to penetrate the opening as the finger penetrated deeper into her pussy. Then the tongue withdrew and Marilyn whispered in her ear.

"Do you want me to put my cock in your pussy?" The words sent shivers down her spine. For a moment she felt profound confusion but then she recalled her earlier musings about a woman having a dildo. Did Marilyn have a dildo with her? The thought made her groan, hips lifting toward the finger now sliding in and out of her body, mimicking the familiar feel of being fucked by a man's cock.

"Oh yes!" Her head turned until their lips met in a deep, passionate kiss. As their lips broke away with a gasp she moaned, "Give me your cock!"

"Lie back my love and close your eyes. Women like to keep their secrets after all." Shannon did as she was told, listening to the rustling of silk and feeling the shifting weight on the bed next to her. She really wanted to look, to see how the dildo was fastened to her lover's body, to see how realistic it looked in the dim light of her bedroom. All the thoughts coursing through her mind added to her excitement as she lay with her legs spread waiting to feel her lover's latex rubber organ penetrate her moist pussy.

"Now keep your eyes closed lover and enjoy the fuck of your life." Marilyn's lips spread over her genitals again, that devilish tongue sliding into her pussy to prepare the way. Then the mouth disappeared and she felt weight shifting on the bed. A moment later she felt the familiar pressure of a man's organ spreading the lips of her pussy. She couldn't contain the gasp that rose in her throat. The pressure continued as the bulging crown of the organ wedged into the opening, pausing for a moment before entering. Inch by inch the thick member penetrated her softness. It was exactly as she knew the feeling of being fucked, nothing was lost in translation.

She turned her pelvis toward the organ, offering herself completely to the rigid member which quickly slid to the bottom of her pussy, filling her completely. A moment later she felt breasts pressing into her own and then lips spread over her mouth. Her eyes opened for an instant to confirm it was Marilyn fucking her, then closed as Shannon gave herself to the kiss. The organ withdrew, then plunged forward, beginning the primordial act of fucking. She groaned into her lover's mouth, then reached around to cup the tight, round cheeks she'd appreciated earlier in the evening. She was surprised that she didn't encounter any tell-tale straps from the dildo, but then admitted she really knew nothing about those things. All she knew was that this creature was fucking her brains out and she was loving every minute of it!

Her earlier lovemaking had taken some of the edge off her excitement and she was able to ride the waves of arousal without driving past the point of no return. Her lover had raised onto her arms, her body between Shannon's wide spread thighs, rising and falling as the insatiable cock continued to pump in and out of her body. Shannon's eyes were open wide now, peering up at Marilyn's beautiful face which somehow mirrored her own excitement. It was as though the cock were fucking them both at the same time! She knew she was getting closer. Glancing down between their bodies she saw in the dim light the thick organ sliding in and out of her pussy. The instrument seemed to spring directly from Marilyn's loins in a remarkable simulation of a real cock. She felt an impulse to reach down to touch the realistic looking organ but hesitated, her eyes lifting to meet Marilyn's gaze. Her lover smiled.

"Touch it lover, feel my cock." Shannon lifted her hand from her side and extended her fingers. Marilyn's invitation shook her. It was almost as though her lover believed she actually had a cock! But the thought quickly slid from awareness as the organ drove her closer to release. Then her fingers made contact with the slippery instrument, grasping it for a moment as it reached the height of it's stroke. Marilyn paused to give her this moment which in truth only added to her dismay. The organ was so lifelike, at once hard and warm, almost with a pulse of its own.

Then it was buried in her once again and she fell back against the rumpled sheet and gave herself totally to the fucking she'd longed for through this night of debauchery. Suddenly her orgasm exploded, her body convulsing beneath the weight of her lover who continued to pump the organ in and out of her pussy. Then Marilyn was screaming her release, a voice that rode the register from high to low and then to high again. A moment later they were collapsed in one another's arms and to Shannon's amazement, the hard cock within her pussy began to wither and eventually slid from her body. Her mind spun with questions as her eyes closed and once again she slipped into a dreamless sleep.

Marilyn was gone when she wakened early the next morning. A note on the table promised a call later that day. Shannon rolled over and closed her eyes, this time returning to dreams of making love with a strange creature with both breasts and a penis, a creature that looked remarkably like Marilyn.

Mark stepped out of the shower and began toweling himself off. He could hear Daniel in the other room singing along with the radio. He really needed to get a place of his own. It was too complicated trying to share an apartment and to live the life he found himself living in his mid-twenties. Daniel was understanding of course, sharing a similar interest in cross-dressing. As Danielle he was quite stunning in fact with his dark coloring and tanned skin.

They'd been occasional lovers for a couple of years, though his natural bisexuality made Daniel nervous. His roommate's interests were exclusively with men. Women scared him, despite the fact he so spectacularly imitated them in his dress and manner. Daniel frankly admitted to being a queen, quite happy in the gay world, though willing to indulge those heterosexual men fascinated with cross-gendered transvestites and transsexuals. Mark dallied with men as well, and definitely enjoyed tempting them with his pseudo breasts and his real, very willing ass. He even enjoyed going down on a man when the opportunity presented itself. But never in his wildest imagination would he consider saying no to such a delicious female as Shannon.

It surprised him how willing she was to believe his substantial cock was a dildo. Although they hadn't talked explicitly about it, there could be no other explanation for her willingness to play with him like that. He expected once she touched him that she would know for certain. But such is the power of the mind that thoughts can override actual physical experience. He knew he had to tell her about it if he had any hope of creating a relationship with this gorgeous creature.

That had always been his fantasy, to find a beautiful woman willing to accept his bizarre interest in crossdressing and engage in a sexual relationship built around his delicious fantasies. He'd have to wait until they spoke to see whether she'd freak out or not. He pushed open the bathroom door, feeling the cool air from the bedroom wash over his naked body. To his surprise he discovered Daniel standing in the middle of the room completely naked, his quite dramatic cock in a state of full alert.

"What the fuck are you up to?" Both men had lithe bodies with practically no hair, which was essential if you were serious about passing. But in the all together, especially with a rampant erection, there was no avoiding the fact they were men. Mark gazed down at his onetime lover's familiar organ and couldn't help pondering the possibility of taking it in his mouth. One orgasm with Shannon was little more than the minimum daily requirement. He'd often required one orgasm every couple of hours of a waking day, though that was during his more decadent gay period where fucking and sucking is a way of life.

"I need a little tender loving." Daniel stepped in front of him and casually slid his fingers around Mark's damp organ, stirring an almost instantaneous response. Mark allowed himself to be drawn into an embrace, feeling his cock sliding against Daniel's rigid member. Their lips met in a kiss that immediately deepened. His roommate's hands were cupping his bottom, fingers sliding between the cheeks to tease the sensitive skin around his ass. Daniel knew of his anal fantasies, having indulged them on more occasions than either of them could recall. That thought brought Mark's organ to immediate attention. Their lips parted and Daniel smiled.

"Let me lick that little ass of yours." Not even waiting for an answer Daniel was on his knees, his lips quickly spreading over the tip of Mark's cock and without a moment's hesitation deep throating the long, thick member. This was one of the two pleasures men gave him which he'd been unable to resist. A woman may like to suck cock, but very few could take his entire organ in their mouth and throat. Most gay or bisexual men were adept at that wonderful service, using lips, tongue and throat to milk his cock dry. He gazed down at Daniel's lips spread around his cock, at the fingers cradling his scrotum. Then the lips withdrew, prepared for the next stop on this station of the homosexual cross.

Report Story

bygenderbender© 0 comments/ 66660 views/ 13 favorites

Share the love

Report a Bug

5 Pages:123

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: