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.

The Girlhood Experience

Apologies for my recent absence, but being that it's spring, there's tons to do and lots of things to keep me busy! I'm afraid my captioning output will be lower than normal for awhile, but I'll still do my best to put my ideas to paper!

Transcript: “You want me to do what with that!?”

Kelly giggled as she watched her step-brother Brian, now fully made over into Brianna, gape at the size of the dildo she had selected. It was just too cute how nervous he looked. In fact, he looked pretty cute as a girl period. The hair extensions she’d put in looked completely natural, even when wet, and she had done a marvelous job with ‘Brianna’s’ makeup, if she did say so herself. Coupled with the unbelievably genuine looking breast forms that ‘Brianna’ was wearing, ‘Brianna’ looked completely passable as Kelly’s little sister. “Just start by playing with it. Give it a little lick and then, well, you know what girls do with these…”

“Yeah, but, but—“

“Oh hush! You were the one who admitted to me that you wanted to experience life as a girl after I caught you going through my things weren’t you or perhaps you’d like to see the pictures again? Maybe that would refresh your memory?”

‘Brianna’ looked at Kelly with an unamused expression as ‘she’ began, “You’re really enjoying this aren’t you?”

“Nonsense! I’m only trying to give you the experience you’ve always wanted!” Kelly tried to keep a straight face as she spoke, but she couldn’t. She was enjoying this immensely.

“Now just take your pretty little manicured hands and start stroking it. Use both hands, firmly, but sensuously. Just think of it as all just part of the girlhood experience, besides, it’ll be good practice for your date tonight.”

“What do you mean my date tonight, I—!?”

“Put those gorgeous lips of yours to good use now and shush! Now let it go all the way in, all the way to the back of your throat, there we go!” Kelly watched with pride as ‘Brianna’ performed masterfully under her instruction, even though ‘she’ was having some trouble with not gagging. But that was to be expected, it was a rather gargantuanly sized member and this was ‘her’ first time, as far as she knew anyway, after all.

“Did I not tell you? It must’ve slipped my mind. Fred asked me out to dinner yesterday and I told him I’d go only if I could bring my ‘little sister’ along and make it a double date, so he found Matt to go with you.”

The disbelief was blatantly obvious on ‘Brianna’s’ face, “You’re kidding right? I mean, letting you dress me up at home is one thing, but going out, and with a guy!?”

“Relax Brianna, if you do everything I’ve taught you, I’m absolutely certain that no one, not even for a second, will doubt that you’re my little sister. Besides, don’t you think it’s time to let the world meet my beautiful little sister?”

‘Brianna’ blushed, “You really think I look beautiful?”

“Absolutely. One-hundred percent.”

‘Brianna’ thought for a moment, “Alright then, I’ll do it, but I am not sucking his dick tonight, no matter how many times you make me practice!”

Kelly laughed, “Of course not! A real lady never gives a blowjob on the first date. That comes on the third!”

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.

Tricks of the Lips

Every now and then I get struck with sudden inspiration and today, I decided that despite my lack of time I absolutely had to write this one out. Let me know what you guys think! What do you think will happen at prom?

 Transcript: It was spring of my last year in high school and the weekend of senior prom. My parents had left a few days prior and my sister had gone off to college the year before.

Although I was old enough to stay at home alone, I had also recently been grounded, so my parents had insisted that Matt, an old family friend, stay over to watch me while they were gone. While Matt and I weren’t particularly close, I’d known Matt for years and he’d only recently graduated from college, which made him still relatively cool by my standards.

Still, I wasn’t particularly pleased. The plans I had made for prom had been formed around the assumption that I would have the house to myself and not being afforded that luxury would make things much more difficult.

You see, I had planned on going to prom as a girl. Despite how average or normal I seemed, if a teenage boy could be considered normal that is, I wasn’t. For years I’d secretly pretended to be a member of the fairer sex whenever I could, safe behind the privacy of drawn blinds and locked doors, but after I’d returned home from my first public foray, I’d known I’d wanted more.

Prom would be the culmination of all I had worked towards and dreamed of. It would be my female alter ego, Lexi’s, first real debut and I wasn’t about to let anything or anyone stop me.

When prom day finally arrived, I was giddy with excitement. Convincing Matt that I was upstairs busy studying for a major exam, I made sure to distract him with old reruns of Happy Days before I went to work.

Believe me when I say that it was not easy. You wouldn’t believe how much work it took to make beauty look this effortless. Most girls get their hair and makeup done professionally, but I had to do mine all by myself, as well as a few other things that the other girls didn’t have to worry about. Securing the perfect tuck required nearly twenty minutes and waiting for the glue on my breast forms to dry so that they would adhere to my chest took an entire hour. It took me nearly all day to complete my transformation, but the results were well worth it; I looked spectacular.

Now that the hard work was done, all I had to do was to sneak out of the house, which was easier said than done. I’d almost made it to the door when Matt nearly gave me a heart attack, causing me to put even the most foul-mouthed sailor to shame.

Despite my current appearance, Matt recognized me nearly right away. Like I said, he’d graduated college. He was a pretty smart guy and my unladylike outburst hadn’t helped matters much. He immediately began to question me, what I was doing, where I was going, and why I was dressed as I was. There was no point in lying. I told him the truth. 

Matt surprised me by first complimenting me, saying that it took guts to do what I had planned on doing and he admired that, but it didn’t change the fact that I was grounded. Using his large frame to bar the door, Matt flatly informed me that despite the circumstances, the rules were still the rules and he was going to enforce them. 

At six foot two, Matt towered over me, even in the four inch shimmering heels I was wearing. There was no way I was forcing my way out and I wasn’t about to try, there was no sense in messing up my hair, but I also wasn’t about to give up that easily. You know the old saying the best way to settle an argument is not with your fists, but with your mouth? Well, I decided to take that little bit of wisdom to heart. 

When I finished my oral persuasion several minutes later, the only thing he had left to say to me was, “So do you need a date?”

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.”

How You're Making It Up to Me

As usual, this one turned out to be a lot longer than I originally intended. When I saw the picture, the idea for this story immediately began forming in my head, so I began to write. What started out as a one liner turned into a paragraph and then two and the next thing you know, it's turned into a pretty dense three panel caption. 

At any rate, this is probably one of the few magical transformations you'll see from me for awhile as magic is usually not really my thing, but I really quite enjoyed writing this one. Who knows, maybe inspiration will strike again! 

As usual, comments are always welcome!

Transcript: “Oh dear,” Tim muttered as he stopped short, noticing the open book in Ron’s hand.

Two months ago, Tim had discovered a mysterious book of spells in the attic, but it hadn’t been until three weeks ago that he and Ron had finally mustered up the courage to try it. Acting impetuously, Tim had cast the first spell that caught his eye. Unfortunately, a few mispronunciations had altered the effects from helping him get a gorgeous girl to turning his roommate, Ron, into a gorgeous girl. To make matters worse, their efforts to find a way to reverse the spell had come failed. Luckily however, according to the spell book, the magic would last for only thirty days, after which the spell would be broken. Left with no choice, there was little they could do but to wait it out.

Unknown to Ron however, a few days after the mishap, Tim had actually discovered a counter to undo the spell, but the revelation was kept secret. Upon finding the reversal spell, Tim realized that over the course of the past few days, he had come to quite enjoy having Ron around as a girl. Even though he knew that the sultry brunette strutting around the house was his roommate Ron, that didn’t change the fact that Ron still had the body of a total sexpot. And since the change had been an accident, there was no harm in letting the spell take its due course was there? Ron had seemed to adjust quite well, accepting the fact that he would be stuck as a girl for thirty days, even seeming happier for it. In fact, he had even obtained a whole new wardrobe and had recently taken to parading around in nylon encased legs and revealing lingerie, a habit that Tim did not mind at all. And thus, Tim had reasoned that what Ron didn’t know couldn’t hurt him, and so Ron wouldn’t know. Unfortunately, it looked like all that was  about to change.

“Well hello there, I’ve been waiting for you to get home,” Ron paused for a moment, then continued as Tim stayed silent.

“I’ve been doing some reading. It’s amazing what you can find out when you open a good book. In fact, I may have even found the very reversal spell we had so much trouble finding when this all started. You’ll never guess where I found it: on a torn out page hidden in this book. Odd isn’t it, that it would be hidden in such a place? But you already knew that didn’t you?”

“Ron, I’m so sorry, please let me explain—“

“Save it, Tim. I don’t want to hear it. You held out on me, but you know what? I’m not mad. I’m not mad at all and do you know why?”

Tim began to think, but Ron cut him off before he could answer, “Because you’re going to make it up to me…in a very special way…”

Tim smiled nervously, “Of course Ron, I’ll make it up to you, just name it.”

Resting confidently in the rustic seat as if it were a throne, Ron spread wide her now long slender legs, offering Tim an uninhibited view of her sweet slit.

“Do you like what you see? I know you do. I’ve seen the awkward walk you do around me to hide your arousal. You’d love to play with a pussy like mine wouldn’t you? To fondle these breasts and caress this body? Well guess what? I found the spell. Oh yes, the very same one that started this whole mess in the first place. I even discovered some of the finer details that we failed to notice the first time. For instance, did you know that there is a way to make the spell permanent?”

“I’m sorry, I’m afraid I don’t I understand what you want,” Tim stammered. He really hoped that he hadn’t already done something to accidentally turn Ron into a woman permanently, thereby incurring greater wrath, or worse, that Ron wanted to turn him into a woman permanently, or both!   

Ron held him in a seductive gaze, powerful enough to melt metal, “I want nothing more than what you already want. Over the course of the past couple of weeks, I have come to truly find myself and as a result, I have decided that I wish to remain as I am, as a woman, forever. However, in order to accomplish that, I need something of you.”

A wave of relief washed over Tim, “Oh thank goodness, so you’re not going to punish me by turning me into a woman as well?”

“Heavens no! I have a very different use in mind for you. You see, in order to seal the magic of the spell, I require a very special ingredient to be applied within me, the seed of a man. Now the wine glass on the table, do you see it? I want you to—“

“Whoa, whoa, whoa,” Tim interrupted Ron as he deduced what Ron wanted him to do, “you want me to masturbate into a wine glass so that you can use my cum to seal the spell!?”

“Would you let me finish? On the table you’ll also find a bottle of vintage port. I want you to pour yourself a glass. White port wine is said to be a potent aphrodisiac and you’ll need all the help you can get.”

Tim was at a loss once again, “Are you saying…um asking me to…so you want me to do what?”

“Fuck me. I want you to fuck me. Long, hard, and deep. I want you to part my ready lips and impale me with your eager shaft. I want you to make me scream for more as I reach the throes of ecstasy, urging you to cum inside of me, but not just once, but multiple times, over and over again, all night long, until you are completely spent. Although once should be sufficient to seal the spell, it is better to be safe than sorry, hence why at sunset the next day, we will begin again, and each night after that until my thirty days have passed. So what are you waiting for Tim? I can see your cock struggling to burst free and if my pussy were any wetter, it would drip, so come over here and slide that cock within me already!”

Hot 'N Heavy Workout

Here's a quickie!

 Transcript: Since being transformed by a vengeful ex-girlfriend that also happened to be a witch-in-training, Andy has since begun to take an increased interest in exercise, particularly cardio. Not only is cardio great for maintaining a flawless figure, but also for increasing heart health.

These days, Andy usually hits the gym in her favorite white fitness catsuit several times a week, much to the delight of the male regulars. She typically plays coy, but always makes sure to give them a show as she strains and gets out of breath. Then, when she finds that she’s become too hot—or too horny—for her clothes, she’ll pick the first muscular hunk that catches her eye where it counts and take him somewhere else where they can both do something that’ll give their hearts a special workout.

Fringe Benefits

Transcript: Spectre could get used to this. It was barely noon, he had barely lifted a finger, was currently soaking up the summer sun, and he had already achieved almost half of his mission objectives. Meet and gain the confidence of Mario Valencia, an influential underworld figure, check. Board his secure private yacht, check. Remain undetected, check.

Spectre knew that it was all thanks to his latest disguise. He was currently posing as Rachel Novelli, an absolute bombshell bikini babe that also happened to be the free-spirited daughter of a fairly wealthy businessman. It hadn’t been hard attracting Mario Valenica’s attention. That wasn’t to say that he hadn’t done any work though. Struggling to fit himself into the restrictive mask and bodysuit had been work enough. Sure, it had made him look gorgeous and gave him the figure of a goddess, but it also had to squeeze down on some areas pretty hard to achieve that effect. The crotch surprisingly, was more comfortable than expected; it sure beat the hell out of duct tape and superglue and it was just as effective!

The rest had been admittedly light. Intelligence had already given him the dossier on Valencia, so he knew which hotel Valencia was staying at and what his activity patterns were. Spectre also knew that Valencia frequented the hotel pool and that he often invited women aboard his yacht to spend the day…and sometimes the night. All that had been left to do was to put out the honey and wait for the fly. It hadn’t taken long.

Now, Spectre found himself lounging on a luxury yacht, cruising welcoming tropical waters, being waited on hand and foot by the yacht’s staff, and with nothing to do except to drive Valenica mad with a potent combination of teasing and denial. His next objective required access to Valencia’s private quarters and the cover of darkness would be preferred to cover his escape. As such, Spectre would have to provoke enough interest as Rachel to be invited to spend the night, hardly a challenge given the way Valencia was already eyeing ‘her’ lascivious curves. Since achieving his primary objective was only a waiting game now, Spectre decided to entertain himself by working towards a bonus objective: how blue could ‘Rachel’ make Valencia’s balls? Since she had at least several hours until nightfall, she hoped that she could make them at least as blue as the waters around them.