SLUTTY CHEERLEADER WITH SURPRISE

You See a few options. You decide its a bad idea to upset your black mailer by picking the least Fem/Sissy outfit, but you don't want to go full sissy slut right off the bat (even if you have been enjoying this way more than you thought you would) So you decide on what appears to be something between the two, A Cheer outfit. It even has what looks like spanks to cover you in case the skirt rids up, which it will as the skirt is short enough it would show your underwear even when its at full length. The Top is more a glorified Sports bra, showing off your midriff, on the front where it would normally have team or school letters it instead reads Sissy. The socks are thigh high white they look like cotton and the shoes are black heels not suited for most activities but more reversed at 2in then most of the other options.

'In for penny, I guess'

"Ok SAM can I Have this one?" you ask.

" Yes you may, would you like me to put it on for you or would you like to do it yourself and put on a show for your partner?" Sam queries.

"I don't think I'm ready for that level of voyeurism just yet, can you do it for me?"

"Certainly, please spread your legs and lift your arms"

You feel Sam's robotic arms lift you up, you feel Sam start to move something up your legs and you look down. You see what look like spanks but there is an odd protrusion.

"Sam... what are those?"

"The undergarments you requested.'

"I know that, whats the weird shape in them" You ask again as they slide further up.

"That would be the buttplug, Good sissies need to be plugged when not in use. Now please try to relax."

Before you can respond you feel more arms touch you butt and pull your cheeks apart.

"Sam please stop, thats going to hurt" You feel another Arm touch your rim, you shiver alittle.

"Don't worry I will apply lube and aphrodisiac to ease the insertion, it is standard practice for all sissies until the are used to training."

You go to open your mouth to protest but lose your train of thought as you feel the robotic arm push a little into your rim and start to fill you with something, you amuse its the aforementioned lube and aphrodisiac, you start to feel really turned on. 'How far will this go, I was already a horny mess.'

As you are basking in the chemical starting to course through your body you feel the plug be inserted, Instead of pain or revulsion you feel full and completed. 'What is this vacation doing to me, what have these people and chemicals turned me into!?' you think to yourself, but there is a nagging though in the back of your head you can't quite shake (Maybe you were always this person, This Sissy,This SIssy SLUT, Just below the surface. Maybe you were just always too scared to show who you really were, had to be what others wanted you to be; but isn't that how sissies are submissive to others desires?)

You are so involved in your own head you don't notice you have been dressed. You now notice that this outfit feels a lot softer and smoother than you thought it would, more like fine silk than the cotton blend you assumed. Between the outfit, aphrodisiac, and plug you are getting so horny you can feel you self start to leak precum.

Before you can begin to process this you hear your black mailer say "My don't you look so cute horny and plugged for the first time sissy." You turn to look at her and see she is holding a remote, before you can ask she explains. "That cage and that plug are both remote controlled, Be good and get pleasure with your pain, be bad and just get the pain. Now beg me to let you suck my cock, I'm hard again watching you squirm."