Your Date

Marry for Money

Meeting His Roommate's Other Side

Marry for Money

I have a ton of shemale pictures that I haven't used yet and I've been wanting to make one for some time, so here it is! The story just sort of jumped at me when I saw the picture, but I couldn't figure out how to end it properly. I'm still not terribly happy with the conclusion, but it'll do I hope!

Transcript: Today is my wedding day. The ceremony starts in just a couple hours. So what are these two guys doing here with me you might ask? Allow me to explain. Though it may seem like it, I’m not just some cock crazed whore who can’t help but rip down the pants of every man she comes across. Far from being an impulsive act of passion, this is in fact a very carefully thought out step in an extremely intricate plan.

As you might’ve noticed, I’m not like most girls. One particular feature on my body tends to stand out in a very distinct way, my cock. You see, I’m not actually a girl. To get my hands on the Wilson fortune however, I had to pretend to be. With some practice, I got to be pretty good with a makeup brush. Add a well styled wig, life like breast forms, and some Oscar worthy acting, and Mia was born! Though the initial investment was extremely costly, the return will far outweigh the cost. As soon as today’s ceremony is over, I’ll have made it all back tenfold. As the new Mrs. Wilson, I’ll be entitled to at least half of Mr. Wilson’s estate, which is easily worth millions.

Now as for the two men servicing me, that’s Paolo and that’s Damien. I’ve paid them to help prepare me for tonight’s occasion in some very special ways. As old as Mr. Wilson is, there’s no doubt that he’ll want to fuck his new bride tonight, or at the very least, attempt to do so. He’s not marrying me for my wit or intelligence after all. Mr. Wilson believes he’s marrying a sultry, voluptuous brunette, and with a little help from an extraordinarily realistic faux pussy, he’ll have no reason to think otherwise.

To pull off the illusion however, my ‘pussy’ does need to be fully functional, which is why its opening has been made to lead to my ass. Though I am quite certain that Mr. Wilson’s member will be nowhere near the size of Paolo’s, I’m still having Paolo stretch it out for me now, such that my ass will be absolutely ready to provide the warm welcome of a woman’s flesh that Mr. Wilson is undoubtedly craving. Damien on the other hand is in the process of sucking me completely dry. I don’t want any mishaps tonight once things start to get hot and heavy. But with my exhausted cock tucked away behind a convincing façade, it’ll be utterly undetectable, and with my balls completely dry, there’ll be no surprising climaxes either. Mr. Wilson will never suspect that his gorgeous new bride, with whom he is sharing his bed, his life, and most importantly, his fortune, isn’t entirely the woman she appears to be!

Preparing for Your Date

I actually wrote this one out...maybe almost a year ago, but I just never got around to making a caption out of it, so today I decided to make it happens. I quite like this cap personally, it's only the second cap I've written in the second person voice (I think, the other being Caught in Purple which I wrote a long time ago!). Let me know what you guys think! Do you like second person voice caps?

Transcript: These were the moments that you lived for. Everyone was out of the house and no one was due back for days. You’d waited an hour after the last person had left the house, every minute seeming to take twice as long, just to make sure that no one had forgotten anything. As soon as the hour was up, you’d sprung out of your seat and into action, your whole body trembling with excitement. With three whole days to yourself, you would have plenty of time to transform yourself into Sabrina and savor it too.

Your first order of business was to completely exfoliate your entire body. A special cream could be applied to all but the most sensitive of areas and a good razor easily took care of the rest. Once done, you’d hopped into the shower for a quick wash and to lather yourself in a variety of moisturizers and other bath products, their fragrant scents lingering around you, even after rinsing off. You spread layers of cool moisturizing lotion upon your newly hairless body afterwards, to ensure that it would preserve its soft supple nature.

You’d then sat down at your sister’s vanity table, picked up a small brush, and began with the foundation. You’d wielded your brushes with expert skill, applying blush, eye shadow, and mascara, which helped to hold up your false eyelashes nicely. Retrieving your wig and breast forms from a place that only you knew about, you’d attached the wig to your head and watched as the familiar dark, auburn, locks tumbled down into place. The breast forms came next, the cool glue of your silicone falsies sending shivers down your spine. You cupped the two mounds carefully, being sure to press them firmly against your chest long enough to allow for proper adhesion.

Applying a few puffs of your favorite perfume, you’d stopped for a moment to take in your new feminine scent, the aroma giving you an instant hard on as your fantasies ran wild. Ah yes, you’d almost forgotten about that. Waiting until your naughty little clit had settled down a bit, you’d grasped it firmly and winced as you pulled it hard between your legs as far back as it would go. The bit of discomfort was regrettable, but there was no sense in letting a little pain get in the way of the perfect look. A generous amount of surgical tape was sufficient to secure it in place, ensuring that it would not make any further unexpected appearances; that would’ve been quite undesirable.

Then slipping into your sister’s bedroom, you’d flung wide the closet doors and paused for a moment before strolling into a world of all things feminine. This was when having a shopaholic twin sister paid off. With so many choices and possibilities, you’d been unsure of what to try first. Eventually you’d settled on a colorful summer dress and slipped into it with practiced ease, the stretch of soft clingy cotton giving you pleasurable sensations as the tight dress hugged your body.

As you pause to examine your handiwork, the sound of the doorbell announcing your date’s arrival interrupts your thoughts. Throwing on a pair of flirty platforms, you teeter over towards the door, take in a deep breath and mustering up the most seductively feminine voice you can imagine, open the door and greet your visitor, “Hello Mark, I’m Sabrina. I’ll just be a minute more. Won’t you come in?”

Seductress

Recently, I've started going over my caption document and trying to finish those that I've started but just never got around to finishing. This is one of them. I wrote this one way back at the end of summer last year I believe, but I was just never satisfied with it, so it never got published. I've made some changes to it once again and instead of letting it collect more dust, I've decided to set it free and see how it flies. Let me know what you guys think!

 Transcript: Her luxurious hips sway sensually as she slips out of her black mini-skirt, leaving her stripped down to just her little pink panties and tight fishnets. The scent of her provocative perfume emanates from her alluring presence, intoxicating the room with her feminine fragrance. She wears it because she knows its effects. She yearns to be desired, to be ravished, and to be submitted to. 

She bats her lashes and flashes her lover a salacious smile as she slowly slides her perfectly manicured hands down her undulating body and towards her sex. A long, lascivious moan arises from her lips as the two meet, shattering the silence that had existed between. Her lover’s outstandingly obvious arousal immensely turns her on, urging her to continue. With her flawlessly round bubble butt in his face, she begins to peel back the last physical barrier separating her from him. She only does so because she knows that her power over him is complete. He will do anything she asks of him now, even suck the long hard cock she’s been so desperately trying to hide in her panties.

Springing the Trap

When I started this caption, I had drawn my inspiration from another photo and it was meant to be a quickie...well, you can guess what happened. I started writing it as a monologue from Mr. Stevens a.k.a. Jake's point of view, but then decided to add in the little bits of thought processing in between and voila! 

Leave me some comments and let me know what you guys think of it!

Transcript: “Did you really think that nobody would find out Miss Winther? Or should I say Drew? Dressing up as a woman in order to improve your chances of getting a job here as a secretary?”

Mr. Stevens, or Jake as he preferred to be called, stood towering over me as my cherry coated lips worked his hard cock. My only response was to keep sucking. It was the only way to avoid the public humiliation he had so eloquently threatened me with.

Jake continued, “You thought you were so clever didn’t you, with your fake documents and equally fake silicone breast forms spilling out of that low-cut blouse? You thought you had me fooled didn’t you?”

Funny, he still couldn’t seem to keep his eyes off my ‘breasts’ and actually, I did. He only found out about me because I had a ‘slip-up’ and he ‘accidentally’ saw some things that he wasn’t supposed to see, but I’d just as well keep letting him think that he was simply too smart for me. Guys liked that sort of ego stroking, especially if they didn’t know that you were the one doing it.

“I must admit, you do look very pretty and if I didn’t know any better, I might actually mistake you for a real girl, but unfortunately for you, I do, which brings me back to the discussion of our little arrangement.”

If I was pretty drunk, I might’ve actually taken that as a compliment. As it was however, I needed no further confirmation of what he thought of me than the gargantuanly engorged member in my mouth. Very pretty indeed. I was a downright gorgeous sexy babe and both he and I knew it, even if he didn’t want to admit it. There was no hiding the fiery inferno of desire. He wanted me, badly.

“It’s only a matter of bureaucratic paperwork to have you transferred to a position as my personal assistant, a job requiring special talents for which I am finding you extremely qualified.”

Damn right I was. I hadn’t spent all that time practicing on those dildos for nothing.

“Now as long as you keep those lips nice and tight, no one will have to find out about your little escapades. So what do you say? Are we agreed?”

I thought he was never going to ask. I gave my response in nonverbal form, using my tongue to gently flick the underside of his shaft as I took him all the way in. Then suddenly producing a powerful vacuum sealed by my wet lips, I brought him to the edge of glory before letting him back down again. He moaned zealously. I was pretty sure he understood what I meant.

Now it was his turn to be cryptic. I felt him place a hand on the back of my head, pushing his cock down into my throat as I squirmed from the forcefulness of his grip. I had no problem understanding what that meant. Glancing in the direction of one of the many hidden cameras in the room, I knew that his wife wouldn’t either.

Cyber Girl Thrills

Transcript: It had started innocently enough for Alex. His only intention had been to see how well he could pass by presenting himself en femme on chatroulette. It was quite a thrill, never knowing who would come up next or how they might react, but nothing excited him more than being able to pass for a girl in front of a complete stranger. He worked hard to achieve his desired look, shaving himself smooth from head to toe, even though he knew they couldn’t see his legs, and investing in a high-quality wig and realistic breast forms, which further enhanced his passability. Going by Giselle, it didn’t take long before he found his new identity blossoming and attracting plenty of male attention.

It was on one such occasion that Giselle found herself engaged in a rather raunchy exchange when partway through, she was completely taken aback when the man she was chatting with discreetly implied that he would be willing to part with a generous sum should she be willing to go a little further. The proposition both frightened and delighted her at the same time. To be made such an offer was an enormous compliment, but the circumstances were hardly less than ideal. After some deliberation, Giselle politely declined, but the encounter had planted the idea in her mind.

Two weeks later, Giselle anxiously performed her first cam show to a meager crowd of less than twenty. Within a few weeks however, she was regularly pulling in thousands of dollars per night from her hundreds of fans, all of which had no idea about her not-so-little-secret hidden within her panties. In fact, some of them had even gotten in touch with her privately about a more…intimate experience. She was still contemplating their offers. With her latest acquisition, it was possible, and she had wanted to test her faux virgin pussy out, but would it be convincing enough? There was only one way to find out…

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…

Your Date

Preparing for Your Date

I actually wrote this one out...maybe almost a year ago, but I just never got around to making a caption out of it, so today I decided to make it happens. I quite like this cap personally, it's only the second cap I've written in the second person voice (I think, the other being Caught in Purple which I wrote a long time ago!). Let me know what you guys think! Do you like second person voice caps?

Springing the Trap

When I started this caption, I had drawn my inspiration from another photo and it was meant to be a quickie...well, you can guess what happened. I started writing it as a monologue from Mr. Stevens a.k.a. Jake's point of view, but then decided to add in the little bits of thought processing in between and voila! 

Leave me some comments and let me know what you guys think of it!