Meeting His Roommate's Other Side

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.”

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…