Tag: crossdress

pleasantprincesscandy:

You were sitting on the bed, still in a daze from the fucking He had given you. You only rarely dressed and and got so horny that you felt the need to meet a guy, but today had been one of those days and as you sat there you could still feel his cock in your sissy pussy and your throat, taste His cum in your mouth.  Then your phone beeped and when you picked it up you suddenly saw a picture  of yourself, face filled with a huge cock, a needy submissive expression on your face – he’d taken pictures!  How???? There was a simple message.  ‘Don’t do anything silly and no-one needs to see these pictures. Be ready at the same time tomorrow evening. I’ll be bringing a friend”. Looks like your life is about to change:  better cancel whatever plans you had for the foreseeable future sissy!

Fancy a spot of Blackmail?

Ummm, oh no, this is…terrible. Yep. Just terrible. Just don’t gangbang me, please. That would be…um, awful.

Your little brother always seemed like such a kid. Even when you all were kids. Four years was forever back then. So even before you started dating her, Silvie and her little sis (by just a year) would fawn over your cute brother whenever he was around. They’d play silly kids games, dress him up in girls clothes and coo, and let him snuggle into their laps and nap. 

He never seemed to outgrow that, in his eyes or theirs. At an age when you’d already been trying to date, Iggie was content to let Silvie and her sis put makeup on him and have cutesy girl sleepovers. Not to mention crawl over them in a way you didn’t think was proper anymore. By then you were dating Silvie and told her not to treat him too much like a baby. He needed to mature, and frankly you wanted Silvie to spend time with you doing more adult sleepover things. It was perfect cover, but you could never convince her to slip away and be naughty.

“Oh I think he’s plenty mature,” Silvie said, giggling. “Don’t you, Cammy?”

“Gosh, I’d say he grows UP, fast enough alright, sis.”

You didn’t understand them at all. Why would they spend so much time being so childish? They just stayed up late telling dramatic bedtime stories, apparently, laughing and crying out. It almost sounded painful. You wanted to barge in at times, but Silvie locked the door. When you rattled the handle, she’d teased you that “no little boys” were allowed while laughing and sounding breathless. 

Years later, Cam and Sil are still very close with Iggie and treat him like one of the girls. They embrace and kiss and are generally touchy feely. They don’t get to see each other as often, but when they do they all hole up in Igg’s old bedroom and cause a commotion for old-times’ sake.  You still don’t understand but by now you just think it’s cute.

feminizationstation:

Crossdressing Caption – Persuasion

Of course when you got there you saw your frat brothers out on the lawn horsing around. Men sporting sundresses with chest hair sprouting where cleavage should have been. Big beards over slips, their junk tenting the smooth fabric and obviously not tucked thoroughly as you had. And certainly no one else had shaven their legs. They were parodies. No one came close to passing. Even though they’d all assured you there would be prizes for the most convincing getup. 

Freaking out, you asked your girlfriend to pull away immediately before anyone saw you. She just took the keys, got out and started striding away, greeting your roommate loudly. Shit! 

“Who’s your hot new frien-” your roomie started in, “Oh my god! Sam!?!? You’re smokin’! I can’t believe this worked- I mean, that your outfit is so good. The seniors need to see this!”

You were quickly ushered into the house – past many roving eyes, wolf whistles, and ass slaps – to the house elders. After much laughter and being made to twirl and bend over you were summarily declared the winner for the title “Queen Sissy”. Yay? Wait, the prize was to be the Party Hostess? You’d have to take everyone’s orders, drink and…otherwise. If everyone wasn’t pleased by the night’s end, you’d have to dress like this for a month!?

You looked to your girlfriend in panic. She just smirked and said in a sultry voice not to worry, that she’d teach you exactly how to please all the men. This was met with raucous approval.