Flat Chested Slut

Fake boobs were pretty expensive, so you were going for a different look. Not many guys were excited about ironing boards, but little Jake here had one saving grace. Sitting on his behind all day had given him a wonderfully doughy bubble butt. One you couldn't help but give a good smack when you'd been shaving him. You just needed to emphasize that.

You pull out all the pieces of Jacquelyn's new outfit, laying them on the table before you like the paints and brushes of an artist. You began with the easy part, picking up the bra you'd picked out for your sissy little pet. It was a hot pink number, frills around the edges, and an A cup. You clipped it on his chest, fumbling it around until he looked presentable enough. You followed it up with a loose top, the sort that was basically a t-shirt but a size or two large, big enough to hang off one shoulder and expose a bra strap. It wasn't anything too exciting, just a white shirt with SEXY spelled out in pink glittery letters.

That was the boring part done, now you could get to emphasizing what Jacquelyn should be showing off in the first place. You roll the **** boi over, giving his butt a quick spank. You quickly pulled a thong up his legs, wedging it between his cheeks and yanking it against his hidden away manhood. It matched the bra you'd given him and, while it would probably be ignored by his incoming guests, it felt like a nice touch. The thong was just the start though. The next part was what you were really excited about. You stretched them in your hands, taking a deep whiff of the rubbery material. PVC leggings...

This part took a good ten minutes, slowly working the leggings up, yanking and tugging once you got to his hips. At first you worried that you had underestimated just how thicc his sissy little ass was, but thankfully, after a lot of work, you yanked them up around his waist. You couldn't help but grin, knowing he wasn't getting those off without help...and his ass just looked perfect...even more so thanks to a little adjustment you'd made. A prominent hole was cut into the back of the leggings, showing off the pink ass floss that barely hide the boy's virgin rosebud.

"Alright...looks like I've got another hour and a half, lets get you looking pretty," You said to yourself, rolling Jacquelyn into a seated position. Her lips probably wouldn't see much action, but you still took the time to give them a quick pass with some plumping lip gloss, leaving them a lovely shade of pink. Foundation came next, followed by some light blush. You didn't bother with fake lashes, but made sure to go heavy on the mascara. It wasn't your most indepth makeover, but it would suit the purpose. His hair didn't need much work, it had grown out a bit and was a nice dirty blonde. You'd given it a good wash when you were shaving him and now just needed a few quick adjustments. First, a temporary dye...adding a bit of red to the tips. Next, you pulled his hair into two short pigtails, making sure to leave some bangs laying askew.

And with that, your masterpiece was done. But...like all great artwork, he longed to be displayed. You took another look at the apartment and then towards your bag. You could certainly set up a webcam in here and invite some lusty hunks over for the fun, but there were other places. You knew the red light district was just around the block.

(As usual feel free to comment on your preference)