The Pimp and Her Ho

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Endless Opportunities

Just a Lollipop (For sarinedavis)

I made this cap for sarinedavis over on the Caption Trading area of the forums at Rachel's Haven. It was the first caption trading I've done so I was a bit nervous when I posted it, but it all turned out well!

Naughty or Nice

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Sooner than Later

Transcript: I’d known that getting caught whilst en femme was bound to happen sooner or later. I just hadn’t expected it to be this soon.
It’d been a quiet weekend in the house. My parents had left for the weekend and as had all three of my older sisters. I had volunteered to stay behind to watch the house and study for the SAT’s, or so I claimed. In actuality, I had no intention of studying. An entire weekend to myself however was the perfect opportunity to let my femme side run wild and go free.
Saturday morning started off without a hitch. I began by exploring into my sister’s wardrobes and selecting my first outfit of the weekend. Now, the great thing about having three older sisters is also having three older sisters worth of clothes, shoes, and accessories. I had access to just about anything a girl could want.  Eventually, I settled on a gorgeous green Jovani dress that my sister Ashley had worn to prom last year, along with some extra raunchy lingerie courtesy of my other sister, Vanessa. Then began the transformation process.
My first order of business was to prepare my skin. For total body exfoliation, a simple hair removal cream did the trick for the most part, while a good razor took care of the rest. A hot relaxing bath then followed, serving the dual purpose of softening my now silky smooth skin as well as putting me in the mood. I tried a variety of my sisters’ bath products, as well as their lotions and creams once I had dried off, leaving me smelling like a rich floral bouquet. Making my way to the vanity, I had just completed the long arduous process of attaching my hair extensions and applying my makeup when the unexpected happened. A voice called out and I could hear footsteps rapidly approaching down the hall.
I tried to hide, but it was too late. Standing at the doorway gaping was Edgar, Ashely’s boyfriend. Had I been fully dressed, I might’ve been able to convince him that I was a younger sister Ashley had never mentioned, but with my not so small cock still hanging free between my legs, I knew the jig was up. I could see it in his face, he knew exactly who I was and it was obvious what I was doing. I broke the silence first, pleading with him not to tell. Ashley would kill me if she found out that I had planned on wearing her Jovani dress without asking. Edgar, however, seemed pretty adamant to expose me. He informed me flat out that he would tell and there was not one thing I could do to change his mind. I stared at him in awkward silence for a few moments while my mind raced a thousand miles a minute to find a solution. It was then that I noticed his raging hard on. Slowly lowering myself onto my knees, I began to gingerly unwrap his package, first with my eyes and then my hands as I asked him one more time if there was really nothing I could do to change his mind. Nothing, I asked. Nothing, he said. Boy did I prove him wrong.

Demonstrating Talent and Initiative

"A few more hours later, I was pleased to see that I still had the touch. ‘Katie’ looked as ravishing as ever."

Transcript: Anyone that’s tried looking for a job recently knows that the job prospects are pretty terrible. First off, the chances that you’ll find a company or business that is hiring for a position in your field is small. But on the off chance that you do, you’ll also find that the competition is pretty stiff.

I know firsthand. Even though I had much experience in my field with numerous accomplishments and excellent references to show for it, I was being passed over in favor of younger, more obliging applicants, attractive females in particular. I remember one instance, in which I was lost out to a bewitching blonde, who admittedly, had one of the most voluptuous figures and stunning features I had ever seen, but couldn’t tell you the difference between a conditional variable and a semaphore. No one on the hiring committee seemed to care though, especially after she met with them privately, one at a time, in the corner office. I left my interview that day infuriated, but as resolute as ever. If that was the game they wanted to play, well, I could play at that game too.

It was a part of my past that no one really knew about me, save for a select few, but I had dabbled significantly into crossdressing and drag performances before giving it up after my college years. Finding my old cache of makeup, wigs, and clothes took only a couple hours of rummaging around the attic. A few more hours later, I was pleased to see that I still had the touch. ‘Katie’ looked as ravishing as ever.

A couple weeks later, I got hired. I barely had the time to say yes before my interviewer had me signing my papers. The special female pheromone laced perfume that I wore must’ve been a lot more potent than I thought. I swear he would have jumped on top of me and taken me right then and there had his office not had glass walls. It was a good thing he didn’t, or else, he would’ve found out about my tightly tucked away secret!

Since then, I’ve steadily moved up the corporate ladder. My looks may have gotten the job, but my skills get the pay. Exactly which skills am I referring to? Well, I’ll leave that up to you to decide.

A Different Sort of Roommate

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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.

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?”

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!

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?