Things to Worry About

Two Caps!: Make Me Proud and Timid Adventures

Meeting His Roommate's Other Side

Sweet Candy (for realfield)

I knew from the moment that I saw this image, which was admittedly a long while back, that I would use it as a capback for realfield. The way she's looking up at him, her arched back, her position on all fours, it just screamed submission, the type of cap that realfield usually enjoys. Hopefully realfield will like this one!

Transcript: James couldn’t have planned the result any better. Few would believe that the servile bimbo writhing in front of him had once been Carl Jenkins, former Associate Vice President of Gasser Corp. and an ambitious young man who had gotten too aggressive for his own good. Not that he would blame them for failing to recognize Carl, with her marble skin, gorgeous features, and goddess-like figure, Candy, as he had come to nickname her, looked nothing like the man she had once been. No man, after all, had beautiful breasts as she did, or luscious cock sucking lips as she did, or a sweet juicy pussy as she did. Dr. Merkberg had really outdone himself this time. The facial reconstruction, tracheal shave, electrolysis, implants, final surgery and a few other highly experimental but effective procedures had all been his handiwork. The double doses of female hormones had been his idea too.

James was extremely pleased with how Candy had turned out. Dr. Merkberg had done such a good job that even her tight pussy felt indistinguishable from that of a real woman’s. Dr. Merkberg would be receiving an exceptionally generous bonus from him very soon.

“What have you got say for yourself now, Carl, or should I call you Candy? You look as sweet and feel as delicious as a piece now.”

Candy’s resigned whimpers and encouraging moans were indistinguishable from one another as James continued to fuck her newly constructed pussy, “Please Mr. Slade, call me whatever you like, but please don’t stop fucking me. I need to have your big fat cock shoved between my legs, please Mr. Slade!”

“Oh, you got it slut,” James answered as he intensified the pace. He would fuck this bitch over and over again until she could barely walk straight. Then, after he’d had his fun with her, he’d bring her with him to the office to service the other executives, ingeniously letting her serve as a reminder of what would happen to anyone who tried to cross James Slade.

A Process of Satisfaction (for Candy aka realfield)

"While most saw nothing more than another piece of exquisite arm-candy, James saw his masterpiece."

Transcript: Perfect. James Slade felt nothing but satisfaction as he gazed upon the yielding blonde in his bed. Tiffany James called her, though her legal name was something else. Her bleached blonde hair and shapely breasts were likewise no more real than her name. Even her tantalizingly sweet pussy was no more than an extremely well-crafted counterfeit. But no one except for James Slade would ever know. While most saw nothing more than another piece of exquisite arm-candy, James saw his masterpiece.

Tiffany had been a young man named Carl once. From the moment Carl had been introduced to James, he had begun following James around like a lost puppy. It was natural James supposed. James was everything that most men strived to be: handsome, wealthy, successful, and dominant. Much came from his inheritance, including the genes to his majestically sized body, among other things, and like many others, Carl had flocked to him for direction. In fact, Carl was so eager to please, that turning him into a sissy and had hardly taken any work at all. It had been somewhat disappointing actually; James quite enjoyed the gratification of crushing a man’s will before bending it to his own. Sure, Carl had tried to resist when James had had him injected with feminizing hormones and even cried the first time the James had pounded his tight virgin ass, but only the first time. Countless surgical procedures and untold hours of ‘instruction’ later, the finished product lay before him, awaiting its christening.

Adorned and painted in her very best, Tiffany had accompanied James to a company party earlier in the evening. Though it did not behoove her to stand as his equal, Tiffany had played the part of a well-groomed young lady marvelously well at James’ behest. Here in the privacy of a secluded room however, she could give in to her instincts; James was her master. She had hiked up her dress, removed her panties, and exposed her prize. Tiffany feverishly desired to feel her master’s enormously large cock within her once again, but she was his to do with as he pleased. Whatever James wanted from her, she would give. His pleasure became hers. Tiffany knew that she was her master’s sissy and nothing else could ever make her happier.

Final Inspection

Here's a one liner quickie for you guys today!

You Can't Hide It

Hey everyone! In case you were wondering, I am still alive! I really wish I had the time to write and post more captions, but as of late, I have been just so unbelievably busy that I just really haven't had the time. It took me nearly a week to make this one even though in total I probably spent only an hour on it! At any rate,  here it is! Hope you guys enjoy it.

Transcript: Oh, look at you, such a pretty little sissy. Who knew my step-brother could make such a sweet looking girl and all it took was just a touch of makeup and a few extra tricks! 

The purple teddy really suits you, you know. In fact, I think it looks even better on you than it does on me, especially with the way your ‘breasts’ fill out those cups. You can’t even tell that they’re fake, nothing more than artistically designed silicone forms glued to your chest. It’s only a temporary fix until you begin your hormones, but they’ll do for now to keep the boys interested. 

The blonde hair, I must say, is also quite an improvement, even if the coloring is as fake as your silicone lumps. Not that anyone will ever find out though, since I made you also bleach the carpet to match the drapes. Gentlemen prefer blondes after all, especially blue eyed ones, hence the contacts, and we wouldn’t want to disappoint them now would we? 

Why the long face? Isn’t this what you wanted? To be pretty, to be desirable, to be noticed? You certainly will be tonight. I invited Matt over, but I’ve also arranged to be suddenly called away, leaving you alone with him.

Aww, is someone suddenly feeling self conscious that their sissy clit might show through their sheer panties? You can use your hands to try and cover it all you want sissy, but it won’t do you any good, because once Matt pulls down your panties and bends you over for one long hard pounding, there won’t be anything you can do to hide the truth: that you are nothing more than a little sissy slut.

Sweet Sissy Temptation

Transcript: 

“So how’s living with your new roommate this year, Will? You guys getting along well?” Jack asked as he and Will walked through the front door of Will’s apartment.

Will hesitated before answering, “Well…I don’t know…it’s been difficult I guess you could say, he’s definitely…very different. It’s a bit problematic.”

“Oh yeah, how so?”

Before Will could answer, a topless brunette holding an oversized rainbow lollipop sauntered into the room. Jack eyed her up hungrily, “Why, hello there. Will didn’t tell me he had such beautiful company around,” then turning to Will, “aren’t you going to introduce us?”

Will shifted uncomfortably, “Umm, yeah. Jack, this is my roommate Eric. Eric, this is my friend Jack.”

“You mean she’s a…”

“Yeah.”

Although evidently surprised, Jack, to his credit, did not seize the first opportunity to bolt out the door and run away screaming. Instead, he extended his hand and smiled, “Nice to meet you, Eric.”

The brunette giggled and smiled back at him. “Likewise, but you can call me Emma,” her sultry feminine voice once again catching Jack off guard. There was also a hint of playfulness, as Emma began to gently trace expert circles along the length of her lollipop.

“That’s a pretty big lollipop you’ve got there, Emma. You seem like a sweet girl. How would you like to hang out some time?”

“That depends, have you got a tasty lollipop for me?” Emma asked, glancing downwards at the same time.

 “Oh I’ve got a very special lollipop for you. It’s big, thick, and unlike regular lollipops, it’ll actually get bigger the more you suck on it.”

“Mmm, I like the sound of that. I do hope there’ll be a sticky surprise at the end too. I just love it when it gets all over me.”

Jack had a grin the size of Texas on his face as he turned to Will, “I honestly can’t see where you think the problem is, but if it’s really bothering you all that much, I believe that it is my duty as your good friend to offer to let Emma move in with me for the remainder of the year. Consider it a selfless sacrifice for a friend.”

A Hard Time

Transcript: Allen had thought it wouldn’t be a problem. Sunbathing nude? It wasn’t his idea of a great time, but it was what his buddy Taylor wanted to do and it wasn’t that unbearable, so he’d agreed. The nude part had also been Taylor’s idea. He’d wanted to avoid getting any tan lines and it shouldn’t have been an issue, he had argued, since they were all guys anyway. Allen had agreed then, but he was beginning to have a real hard time with it now.    

He and Taylor had been best of friends ever since the sixth grade, when he beat up the bullies picking on Taylor for being a sissy. He remembered what he thought about it at the time: so what if Taylor wore his hair a little long or wore girly colored clothes? A lot of guys did that, that didn’t make him a sissy. 

But as the two of them grew older, the differences began to become unmistakable. Whilst other guys began to shave their beards, Taylor began shaving his entire body. Whilst other guys began to develop an interest in sports, cars, and girls, Taylor became fascinated by fashion, clothes, and beauty. And whilst other guys began using aftershave and cologne, Taylor began to use makeup and perfume. Even his physical characteristics became overtly distinguishable. Whilst other guys began to put on muscle, Taylor stayed slender and thin. Whilst other guys had their voices drop, Taylor’s stayed lyrical and high in pitch. And whilst other guys began to develop angular, Olympian physiques, Taylor developed goddess like curves. All throughout however, Allen had remained true and loyal to his friend, never giving him a hard time about it.

As Taylor began to peel off the last of his garments and beckoned for him to join him however, Allen couldn’t help but feel uneasy. Despite the logic of his mind, he could already feel himself embarrassingly beginning to stiffen down below. It didn’t matter what he knew about Taylor, his eyes only saw a girl and a ravishingly gorgeous one at that. He tried to use a towel to cover himself up, but his eight inch tent gave him away. Taylor just smiled as he beckoned him forth again. Allen gritted his teeth and took his place next to Taylor. He may have never given Taylor a hard time, but Taylor was certainly not returning the favor.

A Process of Satisfaction

While most saw nothing more than another piece of exquisite arm-candy, James saw his masterpiece.

Transcript: Perfect. James Slade felt nothing but satisfaction as he gazed upon the yielding blonde in his bed. Tiffany James called her, though her legal name was something else. Her bleached blonde hair and shapely breasts were likewise no more real than her name. Even her tantalizingly sweet pussy was no more than an extremely well-crafted counterfeit. But no one except for James Slade would ever know. While most saw nothing more than another piece of exquisite arm-candy, James saw his masterpiece.

Tiffany had been a young man named Carl once. From the moment Carl had been introduced to James, he had begun following James around like a lost puppy. It was natural James supposed. James was everything that most men strived to be: handsome, wealthy, successful, and dominant. Much came from his inheritance, including the genes to his majestically sized body, among other things, and like many others, Carl had flocked to him for direction. In fact, Carl was so eager to please, that turning him into a sissy and had hardly taken any work at all. It had been somewhat disappointing actually; James quite enjoyed the gratification of crushing a man’s will before bending it to his own. Sure, Carl had tried to resist when James had had him injected with feminizing hormones and even cried the first time the James had pounded his tight virgin ass, but only the first time. Countless surgical procedures and untold hours of ‘instruction’ later, the finished product lay before him, awaiting its christening.

Adorned and painted in her very best, Tiffany had accompanied James to a company party earlier in the evening. Though it did not behoove her to stand as his equal, Tiffany had played the part of a well-groomed young lady marvelously well at James’ behest. Here in the privacy of a secluded room however, she could give in to her instincts; James was her master. She had hiked up her dress, removed her panties, and exposed her prize. Tiffany feverishly desired to feel her master’s enormously large cock within her once again, but she was his to do with as he pleased. Whatever James wanted from her, she would give. His pleasure became hers. Tiffany knew that she was her master’s sissy and nothing else could ever make her happier.

Meeting His Roommate's Other Side

Transcript: 

Nicholas honestly hadn’t meant to spy, but as his gaze passed through the opening of his roommate’s cracked open door, the captivating brunette he saw made it impossible not to. Despite having never seen her before, he’d recognized who she was instantly by the tattoo on the bottom of her left ankle. ‘She’ wasn’t a ‘she’ at all, but a ‘he’, and none other than his roommate, Ryan. With the way Nicholas was staring, he was thankful that ‘she’ had been too preoccupied thus far to notice him yet.

Nicholas had known that Ryan had had a penchant for cross dressing, it was something the two of them had discussed after living together for some time, but he had never actually seen Ryan dressed as a girl before, a point he had gone to great lengths to maintain. He’d seen some stomach churning photos of men in dresses before and spontaneous hurling on his apartment’s fresh carpet was something he’d much rather avoid. Seeing Ryan however, he found himself experiencing a much different reaction altogether, an autonomic response that was localized a bit further south of the stomach.

Dressed in white short shorts and a brightly colored tank top, ‘she’ looked like something out of a raunchy magazine spread or a teenage boy’s wet dream. ‘She’ was striking provocative poses and examining ‘herself’ sensuously in the mirror, putting on quite the performance for ‘her’ unannounced audience. Nicholas couldn’t believe how good ‘she’ looked. Seeing ‘her’ as ‘she’ was now, he doubted anyone else would’ve been able to tell.

‘Her’ exhibition soon turned into a real show as ‘she’ put on a sultry melody and began to dance. Nicholas watched in a mixture of arousal and awe as ‘her’ lithe form swayed and seduced an imaginary crowd with fascinating expertise. Slowly, playfully, and meticulously, ‘she’ teased ‘her’ way out of ‘her’ garments until only a tight pair of cotton panties remained. Nicholas wasn’t so sure that he wanted to see the rest, but he felt certain that he didn’t want to miss it either.

As the song came to an end, ‘she’ leisurely slid ‘her’ panties halfway down, exposing a gorgeous bubble butt that Nicholas would’ve sworn only could’ve belonged to a woman, but then stopped. Looking over ‘her’ shoulder and straight through the semi-open doorway, ‘she’ appeared to be staring straight at him as ‘she’ cast a come-hither glance and then winked. Then slowly moving out of view, the last thing Nicholas saw was a perfectly manicured finger beckoning him inside. A few moments later, ‘her’ panties landed in the doorway in front of him. The ball was in his court now. He had little doubt what he would do with it…