Self Help Tapes: A Gender Swap Story

“Hello, Stacy.”

“Hi Robert.”

“How’s it going?”

“Fine thanks, you?”

“It’s alright. So, uh, look. A couple of us are going down to the bar after work. I thought maybe you and I could go together.” Robert felt as though he had swallowed a sea urchin or some other devilish creature that had the gall to be both spiny and slimy.

Stacy looked up from her work. She had kind eyes that Robert could not meet. “Oh, that’s sweet. But, I think I have plans with some of the other girls.”

“Oh sure, yeah, that’s cool.” It wasn’t. Robert felt as though she’d plunged a trowel into his chest and rooted around for a while before scooping out his innards and plopping them on the floor, not out of malice, but out of disinterest. “Maybe some other time then?” She smiled and turned back to her work. To Robert, this was the equivalent of finding a potato masher and turning his aforementioned innards to a gruesome pulp. Robert grew very aware of himself. Had other people seen his rejection? Were the other women listening? How could he have been so stupid? Stacy was beyond him in every possible way. Prettier, of course, sophisticated, she brought her own lunch which she seemed to make at home rather than grabbing a greasy log of meat and bread from a food truck each day, cultured, having a greater knowledge of film and literature than superhero movies and Star Wars novels — all the important qualities of being a modern woman. Robert had cast his fate with the line of “how’s it going”.

He smiled and backed away, as though he’d stumbled upon his own murdered body. When he was far enough away that his embarrassment would be indiscernible to the flock of hens who would soon gather around the offended lady, he broke into long, quick strides to get to the elevator as quickly as possible. He sighed with relief as the doors closed and the wires and gears whisked him down away from the scene. Robert used this time to consider where he’d gone wrong. He believed it started when he was nine years old. Marie Bolton had given him a daisy and asked to be his girlfriend. He’d replied by throwing sand in her face and running away laughing. That was the last time a girl had asked Robert for anything greater than office supplies.

Robert had tried several times throughout the years to date. It always ended poorly, usually with Robert becoming much more attached to his girlfriend than his girlfriend had been to him. His longest relationship had been during his final year of college, but it was actually Robert that ended it. After waking up one morning in the girl’s deplorable apartment to find her eating cereal out of a dirty soup pot, he reconsidered his level of desperation. In total, the relationship lasted four drunken hook ups and two contiguous weeks. Robert did not think himself poor in social skills or generally unattractive. He had mastered the ability of having a normal human conversation through his friends, but struggled when topics drifted from things he considered familiar. Mirrors did not break when he looked into them and children did not scream at the sight of him. He considered himself fairly average in looks other than his height, which he often lamented as taller than girls who wanted a tall man wanted. He had a pointed face with short-cut, brown hair sitting atop a pair of close shoulders. His body was narrow set and thin. Over his life, he’d instinctively restricted his lanky movements, mostly to not knock things off shelves or short people in the eye, but it wound up creating a bird like posture instead of the barrel chested gait of a more confident man.

The elevator dinged and he slipped out of the barely cracked doors. He towered over the cubicles of his coworkers in the IT department. They looked up at him and smiled as his head bobbed along. Robert was well liked among his own people. He thought he should perhaps consider finding someone more his equal, but only one woman worked on his floor, and she was married. As he settled back at his desk, he cursed vertical architecture for strangely aligning with social structure. Stacy worked several floors up with all the other young accountants. Robert worked on the second floor with the rest of the IT department and a small security office. The troglodytes representing janitorial and building maintenance departments occupied the basement level, presumably fearful of sunlight and the gaze of the top floor elite. Robert wondered if he could find an up and coming young woman in the building’s bowels that would accept him.

“How’d it go,” Dave asked from the opposite side of the cubical.

Robert shrugged, unsure of how much to share with his workmate. The two had been sharing a small level of privacy in a cubical for two years. They’d become friends and often shared tales of romantic disappointment, though both tended to hold the details close to their chests. “She had plans already.”

“Like, already had plans but you should try again later? Or, already had plans how is the plebe talking to me.”

Robert cracked a grin. Self deprecation provided them most of their solace. “I think she had a crisis of confidence wondering if she’d let herself go to the point that someone like me would have asked her out.”

Dave shook his head in commiseration. “We’re still on then, right?”

“For drinks? I’m not sure I’m in the mood.”

“Oh, that reminds me,” Dave said with a start. He pulled open the bottom drawer of his desk and fished out an old cassette player. “I got this for you.” He handed it over to Robert.

“The hell is it?”

“They’re self help tapes. They boost your confidence. They’re all about how to talk to women and stuff like that.”

“You’ve used this?”

“Sure. I mean they’re not perfect, but they have some good tips on them. It’s a lot about how you compose yourself and the way you think about things.”

“Why are they on cassette tapes? I haven’t even seen one of these in ten years.”

“This set came highly recommended, but they went out of print so I found these old ones on the internet. I need to get something to digitize them, but it’s one of those things that you put off.”

Robert turned the cassette player over in his hand. He held out the three tapes and read the title. “’How to Become the Person You Should Be, Volume I’ and the subsequent volumes. How long is each tape?”

“About two hours, front and back,” Dave answered. Robert noticed he was looking around nervously. “It’s like listening to a podcast, but like a hipster. And it all goes by really quickly.”

“Why’re you so fidgety about it?”

Dave gave a breathy laugh. “I mean, I don’t particularly want other people to know that we’re trading thirty year old self help cassette tapes. I’m pretty sure the tapes would tell you not to do that if they remade them today.”

“Alright,” Robert tucked the device into his desk drawer. “I’ll give it a shot. And sure, we can still go out for drinks. I have nothing better to do. I’ll go home and change after work and then meet you at Hanno’s.”

Robert swiveled back to face his computer and sighed as he spotted the flashing email icon. He glanced at the clock and resigned himself to several more hours of work.

Work finally ended for the day. After saying a few goodbyes, Robert headed to the elevator, but as it opened he saw Stacy already on it chatting and laughing with other women Robert thought too attractive to acknowledge his existence. He opted instead for the stairs. As the stairwell door slammed behind him, he fished around in his bag for the cassette player. He chose not to use the supplied gaudy headphones and instead plugged in his usual earbuds. He pressed play on the tape and heard the scratching sound of analog audio. With some difficulty, he managed to shove the player into his pocket so that he was at least not wandering around holding the outdated equipment.

“Welcome,” a pleasing female voice began. “In a few moments, we will begin our first lesson. I am happy you have decided to join me on this journey to becoming the you that you were always meant to be.” Her voice faded into a dated instrumental riff. Robert shrugged and started bounding down the stairs two at a time. His brain issued the general instruction to his legs and arms to get him home safely and then turned its attention to the woman’s voice. “Too often in these modern times, we struggle to identify our true selves. Look around you. All those other people that you see face the same problems you do. They have trouble keeping wrinkles out of their clothes. They’re hungry for things they know they should not eat. They’re lonely. They’re yearning to be left alone. We all struggle with our roles in this world. But there is a solution. Listen now to the calming tones. These will relax you and open your mind to ideas you might otherwise resist. Go for a walk, gaze at the stars, or even take a nap while you listen.” The woman’s voice faded and music returned to his ears.

At first, Robert was frustrated that he had to listen to more nonsensical music before actually learning anything. The music itself was quite unpleasant at first. Several atonal notes jarred through his skull before it smoothed out into a blissful melody. Robert guessed the strangely caustic start would repeat later for those who fell asleep. As the music continued, Robert relaxed. Without realizing it, his stride grew less rushed. He cut a swath through the other pedestrians as he languidly meandered towards his apartment. More than once someone griped at him, but Robert paid them no mind. His thoughts were adrift in the sea of sound echoing in his head. He knew music usually affected his mood, but this was unlike anything he’d ever experienced before. He was in the middle of the evening commute. He should have been feeling a growing sense of panic and claustrophobia from the crushing rat race surrounding him. Instead, he felt as though he had been set free at long last from a prison of his own thoughts.

The caustic notes sounded again as expected. “Now that we’re relaxed, it’s time to do some self reflection. I want you to concentrate on what you want most in this world. Picture it in your mind and hold it there. Whatever it might be — an item, the love of a specific person, or a desired moment of victory — cut away the shadows from the image in your mind. See not just the superficial, but the flaws and the practical designs. See not only what you desire, but what is real and tangible.”

As the voice spoke, Robert conjured up the image of Stacy. In his mind, he saw her smiling face. He searched for other details. He knew what her hair looked like and more or less the curve of her form, but he quickly realized he didn’t know her at all. Nevertheless, he filled in the gaps as best he could. He pictured pert breasts, a delightful ratio in her figure, and smooth, unblemished features. She grew taller and slightly broader of shoulder to match her chest. He imagined her first in a red close-fitting dress, but tossed it aside for a blue variety to match her eyes. He was not certain of their color, but he preferred blue. Continuing to explore, he tweaked the woman’s facial features, adding a few bits he’d liked from others in the office. After a while, he stripped the dress away entirely and saw in his mind’s eye a naked woman. He made the breasts slightly bigger and cleared away most of the pubic hair. He even paused to consider the shape of pussy that he would find most desirable. Then he imagined his hand moving down that body. Cupping the supple breasts and grazing over the flat tummy until it reached wet lips between thick thighs.

The door slammed behind him and snapped him out of the reverie. In disbelief, he pulled the player out of his pocket and hit stop. A shiver ran down his spine. He’d walked all the way home already? Had he been so focused in his thoughts to forget everything else on the walk? He checked his watch. The normal twenty minutes had passed from the time he left his office till the moment he closed his apartment door. It had flown by as though he’d been dreaming. For that matter, much like a dream, he couldn’t exactly recall what he’d been thinking about. It tugged at the corners of his mind, always just evading his comprehension. All he could be certain of was that he enjoyed the experience.

Putting aside the recording, he changed out of his work clothes for something more casual. He thought about taking a shower, but instead decided just to freshen up and shave. It was a tedious task for his wiry stubble and so he rarely bothered, but trying to be an optimist, he figured he should look his best on the off chance that a woman caught his eye. He put his slacks and button up in the laundry and grabbed a pair of jeans and a clean shirt before heading to the bathroom. He turned on the water and rummaged in a drawer for his razor before looking at himself in the mirror. The stubble was gone. Robert leaned close and ran his hands over his cheeks. They were smooth and soft, as though he’d just had a professional shave, or perhaps even better. His skin hadn’t felt that smooth since before puberty. Curious, he looked over the rest of himself. While his sparse chest hair remained, he was pleased to find that all of his blemishes had disappeared.

“Something I ate?” he murmured to himself. “Better to not look a gift horse in the mouth, Robert,” he added. He cleaned himself up and splashed some water on his face before getting dressed. He considered listening to the tapes on the way to the local bar, but decided it would be too awkward to carry around the player all night. With one last look in the mirror, he smoothed out his hair and once again admired his strangely bald face before heading out.

The only people at the bar were Dave and about two dozen other single men all of whom seemed to be in pairs. Some of them huddled around the bar having heated discussions about sports while occasionally cursing the televisions, while the others staked out the more comfortable spots in the bar. Dave had found a table of decent quality and was already halfway through a drink by the time Robert arrived. They exchanged greetings, and Robert went to the bar to order a vodka. Drink in hand, he headed back to the table only to pass Dave on the way as he went for a refill. Robert took his seat and hunched forward over the drink as he stirred it with the mixing straw. When Dave returned, he asked, “You in a hurry?” and pointed to the second drink.

“Happy hour ended right before you got here, but I had bought a round already so the bartender said to come back for a refill.” Dave took another long swig before continuing. “So, another week in the books.”

“Paycheck is a paycheck. I wanted to tell you, I started those tapes on the walk home.”

“Oh yeah?” Dave once again began to avoid eye contact.

“It was the damnedest thing. I started the first one right when I left work and the next thing I know, I’m in my apartment. Never had that happen with a podcast. I guess it happens sometimes when you’re driving, maybe?”

“Yeah, I’ve heard about that,” Dave quickly agreed. “Your brain focuses on something and shuts out the rest of the stuff going on. Well, maybe not shuts out because then you’d walk into traffic, but it gets written into super short term memory and dumped almost immediately. Happens all the time and you don’t even notice.”

“Such as?”

“Such as anything. What’s the bartender wearing? What was the score five minutes ago? You saw the bartender’s shirt and the score, but your brain didn’t think either thing was too important so you forgot it immediately.”

“Hmph, I guess you’ve got a point.”

“So, did you read that memo from Helen?” Dave changed the subject.

They stayed at the bar for an hour and a half. In that time, Dave slowed his drinking, but Robert managed to catch up. Their conversation drifted from office politics to entertainment news and a variety of others. Their most heated debate centered around the controversial casting of an actor in a role neither thought he was suited for. Throughout the evening, Robert watched the door hoping to see a pair of lonely women wander in, but none ever came. A few women arrived as part of a larger group, but the bar remained very male heavy through the night. Finally, Robert gave up hope and announced he was going home. Seeing Dave a little downcast about it, he invited his friend back to the apartment to have a beer and play some video games. Dave accepted.

On the walk, Robert fought back the urge to bring up maudlin topics as the alcohol started to take control of his emotions. They made it to the apartment without any type of outburst. Dave went to pee and Robert dropped onto the couch. Immediately, he noticed the cassette player. A strong desire to hear the music again compelled him to put the earbuds in and turn on the audio. At first, he heard nothing but incoherent noise. It was a series of screeches and moans that slowly coalesced into the woman’s sultry voice. Dave returned and sat down on the opposite end of the couch, but paid no attention to Robert. It was difficult to focus, but eventually Robert made out the words. “You love cock, don’t you? Picture in your mind the throbbing hard dick of someone you know. Imagine it pushing into your mouth or sliding against your aroused pussy.”

Something was wrong. Robert knew he’d just heard something out of the ordinary. The tape kept playing, but the words faded away again. He was once again picturing the imaginary woman he’d focused on earlier. He smiled dumbly to see her once again. The vision shimmered as a prickling feeling started to spread over his body. Once again his hands were massaging the imaginary beings breasts. He let her thighs rest on his shoulders as he lowered his tongue to her juicy snatch. He could hear her moaning in his ears, urging him onward, begging him to go deeper.

A tearing feeling snapped him out of the trance. His eyes fluttered open, and he was looking at Dave still sitting on the couch. The other man’s eyes were as wide as plates and his mouth half open in shock, but the truly alluring thing to Robert was the noticeable bulge in Dave’s pants. With a tug, the earbuds fell out and Robert sat up. A weight shifted on his chest, and he looked down to see his shirt bulging out, one of the buttons ripped off. “What the fuck?” he said softly. With no regard for privacy, he pulled at his shirt, popping the remaining buttons easily as two C cup breasts spilled into view. Robert gasped, and Dave stood up in pure astonishment.

“Oh fuck, it worked?!”

“What do you mean it worked? Why the fuck do I have tits?” Robert’s voice was not his own. He’d heard it before though. It was the same as the woman’s on the tape. He scrambled to his feet, but found he could barely move due to a tight pressure around his waist. His hips had widened and his jeans no longer sufficed to contain his newly bubbled butt. Again, not considering his audience, Robert tore at the confining garment managing to rip it at the already stretched seams to reveal wide set hips and a jiggling ass stretching the pair of boxers which were his final layer of privacy.

“I thought it was a joke or something. I didn’t think it would actually work.” Dave gestured to the tapes.

“Become who you should be,” Robert muttered. He walked down the hall to find a mirror. He looked at himself and saw a woman that had become familiar in the past few hours. Looking back from the mirror was the woman he’d imagined. Every inch of her exactly as he’d thought. His hands ran down to his breasts, feeling the supple curve and hefting the delightful globes. With some trepidation, Robert moved his hands down his flat stomach both dreading and excited about what he would encounter. His fingers managed to wiggled under the overstretched boxer’s waistband. Lower and lower he moved until his fingers slid against wet lips. Not Robert. Robbie.

Robbie stamped down the hallway to find Dave. Her friend was still standing in the living room, his face awash with shock. Robbie intended to rail and demand an explanation, but a new craving settled in her mind. Desire coursed through her body. She couldn’t believe how sexy she looked and felt. Every inch of her skin was like a divine blessing. She was the perfect woman as imagined by her male predecessor. Her body was not only designed to be the perfection of sexual desire, but it came with the drive and motivation to fulfill its purpose. Robbie smirked. The tapes had given her confidence and assertiveness after all.

“Is this what you had in mind, Dave? Did you want me to listen to the tapes and turn into your little bimbo? Don’t worry, I’m not angry. I can’t think of anything more wonderful that could have happened to me. Look at these tits. Go on, feel them.” She moved forward, jutting her chest out. Dave tentatively brought a hand up and stroked her breast. “Isn’t that amazing. They’re completely real, but that’s not all.” Turning around, she grabbed the waistband of the boxers and pulled down hard as she bent over. The apartment’s cool air rushed over her ass and freshly exposed pussy. She heard Dave’s involuntary groan as he saw her bald pussy. “Well, Dave, I’ve got this brand new, virgin pussy. It’s all hot and wet. I’d love to feel a nice thick cock pushing into me. If only there were a man available?”

She moved closer to him. As much as she wanted to toy with him and torture him gleefully for giving her such a remarkable gift, her desires were starting to overwhelm her games. She inhaled his scent and smelled something she never had before. She knew it to be the scent of a man, something Robert’s mind had instinctively ignored his whole life. It was intoxicating. Her body pressed into Dave’s and her hand moved between his legs to slide roughly against the bulge in his pants. “So, I think you owe me something for what you did. Don’t you agree, Dave?”

“Oh god, yes.”

Working quickly, Robbie stripped him until she had him sitting on the couch entirely naked. Her mouth watered at the sight of his surprisingly large cock. Dave did little other than wait as she positioned herself in front of him. The couch provided the perfect angle for her to sit on his cock. She pushed her legs together, giving him a full view of her big round ass and the puffy pussy lips as she wiggled at him. “Are you ready to put that fat cock inside your friend Robert’s pussy?” She looked over her should to see the bewildered look on Dave’s face. His conflict only excited her more. She lowered her hips and felt his cock pushing against her lips. “Isn’t it strange and a little fucked up, Dave? I sat beside you for all that time. Were you always thinking, wow, what if I could get Robert to have a pussy so that I could shove my cock into his slit?” She lowered herself further, and Dave groaned as his cock pushed inside of her with a pop.

Robbie’s stomach fluttered from the feeling of having a man inside her. The sensation was entirely foreign and mind bogglingly pleasurable. She kept going, amazed as inch after inch of cock slid easily inside her well lubricated pussy. She had both hands on her tits squeezing and kneading them. She had understood male sex and pitied Dave, even though he was probably having the most pleasurable experience of his life. The male mind could only focus on the penis and the few dull touches of groping. Robbie’s body was electric from head to toe. She was conscious of every inch of herself and all the right areas to touch and play with. She finally felt her ass touch Dave’s thighs as he bottomed out inside of her. She gasped as she felt his cock twitch inside her stretched walls. “Oh god, Dave, your cock feels so good in my tight little pussy. I bet you wanted to cum inside me? Don’t you want to cum inside my little pussy?”

Robbie bounced up and down faster and faster. It must have been the alcohol that gave Dave his stamina. His hands groped at her ass pushing her closer and closer to her climax. She could feel it building like the coiling of a spring and she was desperate for the release. She let go of her breasts and let them swing as she moved, using her hands as leverage to go faster. She moaned as she looked over her shoulder at Dave. He met her eyes and immediately started cumming. He groaned loudly and pulled her hard against him. The first burst inside of her made her whole body shake in excitement. The second shattered her world with pleasure. She began to quiver while sitting on his lap, his cock still buried inside of her to the hilt, pumping what felt like gallons of cum. Robbie felt each spurt splash inside of her and cause a new peak to the waves of orgasm.

The moment subsided. Robbie stood up, letting her friend’s cock slide out of her slowly. She felt the torrent of cum gush out of her and start to slide down the backs of her thighs. Dave watched her move with a mixture of hope and dread. Robbie put her hands on her hips and smiled. “I’m gonna go clean up and then we’re going to talk about this.”

By the time Robbie returned, Dave had passed out on the couch. She initially thought of waking him up, but then had a better idea. Dave had given her the perfect body, it seemed a shame not to do the same for her friend. Getting the old headphones from her bag, she gently placed them on Dave’s ears. She rewound the tape to its start and pressed play.