The Pimp and Her Ho

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Endless Opportunities

Home Early

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.

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.

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!