The Blackmailed Sissy

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did there was far too many women's clothes there to just be "left behind".

Peaking Jon's interest he returned to Eric's room and continued to snoop around and found several dresses and skirts hanging and organized by color in his closet. Jon also found silky panties and the like folded neatly in the dresser with a wooden scent bar having a strong lilac aroma freshening his panties, make-up discovered in another drawer, and a pink collar with a tag that reads 'Sissy Erika' hidden under his pillow along with a note on feminine scented stationary from Jon's girlfriend that read 'Erika, Maybe one day I will share your sissy persona with my boyfriend Jon. Love, Mistress Rose.'

With this last bit of evidence Jon now knows exactly what Eric is and it excited Jon he has wanted to own a real sissy for several years now. Rose also knew of Jon's deep desire to own a lowly sissy, so it slightly annoyed Jon that she would keep this from him but he had a plan. He started by taking pics of Eric's sissy clothing and sissy make-up in his drawers, the pink sissy collar, and his sissy note. Jon knew Eric wouldn't be home for awhile and Rose had a test the next day so she wasn't originally going to show up, he set to work changing Eric's room around he removed one small dresser out and replaced it with a vanity.

While Jon was out getting the vanity he also went to the store and picked up some feminine hygiene products, a tag with 'Rose' written on it, a matched set containing a pink frilly bed spread, comforter, and pillow covers to replace the gray ones currently there. As well as a few naughty sissy things from the sex shop next door to the department store he bought the pink frilly stuff at.

Jon then arranged Eric's make-up on the top of the vanity and replaced his bedding with the sissy pink stuff he picked out for Erika. Jon also took all of Eric's male clothes and boxed them up and hid them in his own bedroom. Eric was due home in about ten minutes so Jon went to the bathroom and placed feminine hygiene products around the tub like Christmas presents under the tree.

He then sent a pic of the note to Rose with a text attached 'What the hell is this?'

Rose replied "Oh my God! Where did you get that?'

'It doesn't matter just explain.' Jon texted back.

'It's a note I wrote for Eric to find I found him dressed and to keep me silent I decided to let him be my sissy. I am going to train him and was planning offering him to you as an anniversary present.' Rose texted back.

'Did you sleep with him?' Jon asked.

'He's eaten me out after I did his make up but I never let his cock anywhere near me.' Rose said.

'That's still cheating and unless you want me to dump you and tell your parent's and all of our friends about this I own both you and Eric now.' Jon stated.

'Yes sir.' was Roses only reply.

'I am going to blackmail Eric tonight be here at 11:00pm and enter the room after you hear me cum in his ass pussy.' Jon tells Rose. Jon set his phone on the table waited for Eric in the living room with the pink collar hidden in his sleeve.

Jon sat down just as Eric, (soon to be Erika) walked through the door. "Hello Erika. How was your day? I think we need to talk." Jon watched Eric for a reaction and got what he wanted Eric stopped in her tracks and all the color drained from his face. "I went into your room to get my charger back and found a lot of interesting stuff."

Eric started to stammer "Like..ah...like...ah..what did you find?"

"Well lots of women's clothes, make-up, and this." Jon drops the collar from his sleeve dangling it between his fingers. "As well as a note from my girlfriend."

Erica dropped to his knees and said, "Please don't be mad she made me do it, she blackmailed me."

Jon replied, "Well great minds think a like because I'm going to do the same."

"What? Why?" Eric said.

"Because I want to own a sissy slut. And you are going to be her," Jon said.

Eric asked, "How are you going to blackmail me?"

"I have photographic proof of all this stuff and unless you want it online and given out to everyone you know, I now own you. Understood?" Jon replied.

"I will not be your play thing. I am not gay." Replies Eric.

"Well you certainly aren't a man so it wouldn't be gay. I would be natural." Says Jon.

"What the hell do you mean I'm not a man? I have a penis I am a man." Says Eric.

"HA can't be much of one to fit in those panties." Jon retorted.

Eric is set back by the statement. "What ... You haven't seen it so how could you know?" Eric asked.

"I know because of the size of the panties. Now be my sissy slave or this all goes out I am done playing around." Jon says sternly.

Without thinking Eric said, "Yes Sir."

"Good now follow me." Jon lead Erika to the bathroom. "Draw yourself a bubble bath with these feminine oils." Eric hesitated for a second then Jon pulled out his phone. "One button press and it's all out there." With that Eric drew himself a bath, put the bubble bath in, and a few drops of the "feminine oils" which unbeknownst to him had high levels of estrogen in it. Then stripped and got in the tub.

"Good now from now on you will only take baths with these oils in them and only use feminine hygiene products to bathe with. You will also be clean shaven other than your head." Erika scrubbed herself clean and started shaving with the extra feminine scented shaving gel her master provided her until she was completely smooth as Jon talked, "Also from now on I will refer to you as Erika, your cock there will be your sissy clit, and your ass will be your sissy pussy."

"Yes, Sir. I am Erika from now on," Erika replied as she finished shaving and bathing.

"Good drain the tub, dry yourself, rub this cream into your breasts, and follow me." Erika does as instructed and then wrapped and fluffed the towel around her chest like a real woman.

"What is the cream for?" Erika asked.

"To grow your breasts of course." Jon stated matter of fact like without turning around. Erika opened her mouth then thought better about it and remained silent.

She then followed Jon to her bedroom. "What did you do to my room?"

"I made it better for your new identity Erika. Now open the top right drawer of the vanity and put on the pink stockings and garter belt." She walks over and opens the drawer seeing all her underwear put away neatly and does as instructed.

"Good now open the top left drawer put on the cock cage." Erika opened the drawer and saw a cock cage, breast forms, and butt plugs. Erika picks up the cage and just stares at it for a second before putting her two inch sissy clit inside, her clit barely fits this (what will happen when she gets hard or tries to she thinks). Then Jon hands Erika a small combo lock. "Now become mine completely." Erika hesitates for just a second before locking the cage in place and an evil smile crosses Jon's face.

"Good, now put on your black thong, matching bra, and also your cute sissy breast forms." Again Erika follows her instructions and notices with the breast forms brought her up to a full 34 DD cup.

"Good girl now sit down it's time for your make-up. We will start with your nails pink undercoats on fingers and toes." Erika carefully applies two coats of pink nail polish just as Rose taught the sissy to do last week, she awaits further instruction from her new Master Jon.

"Now write sissy on your left hand, Erika on your right hand, Jon's on your left foot, and sissy again on your right foot so that they look backwards to you since they will be viewed in public and people need to be able to read the cute sissy labels you have on your fingernails." Erika carefully does as instructed and writes the words slowly and deliberately.

"Very good now pink eye shadow, pink lipstick, and black eye-liner." After Erika applies all the other make-up Jon walks over to the closet and pulls out a low cut and short pink dress and hands it to her.

Erika puts it on "Now what Sir?"

"Now bend over the vanity pull the dress up and thong to the side." Jon grabs lube and a small but plug.

Erika begs, "Master please so not make me do this Sir, anything but this humiliation." In the end she does as she is told and prepares herself. Jon squirts lube on Erika's sissy pussy and starts to finger it getting the lube worked inside her before lubing the plug and pressing it slowly inside.

While it hurts at first it is not long before the sissy inside her comes out to play and Erika is now moaning the entire time and loving having her sissy pussy played with, though she feels so ashamed to have her manly roommate, now Master feeding her sissy needs with a big fat plug in her sissy pussy, as she thinks about it she is also ashamed at how rapidly her mind accepted new terms for her body parts.

When the plug is firmly in place Jon pushes the thong and dress back in place. "Now on your knees slut, careful not to snag or put a run in your sissy hosiery, you will be punished if you do sissy."

Erika kneels in front of Jon and could not miss seeing his huge bulge making a tent in his pants as it is only about three inches from her face (and mouth).

"Please sir may I see your cock?" She can not believe she heard her voice beg for Masters cock and then she thought, am I really becoming a sissy or am I just playing along trying to find some way out of this mess. As she gazes at Masters cock now one inch away so she feels the heat and smells his masculinity she notices a red light on a computer camera that is pointed at her and is obviously recording.

Again she begs master this time with, "Please do not share that video with anyone Sir! I will do anything you tell me to just do not let anyone else ever see the video you are making please!"

"You are such a slut. Yes take my cock out and kiss the tip." Erika reaches forward undoes Jon's belt and pants pulling his rock hard cock off and kisses the tip tasting some pre-cum droplets that have already collected at the tip, why do I like the flavor of my Masters cum drops, am I a sissy for real?

The taste drives Erika wild and brings out her true inner-slut. "Please Sir I want to suck your cock. You are a real man and I am just your sissy slut show me how a real man fucks a sissy sluts mouth Sir."

Jon grabs Erika by the hair and shoves her down on his six inch cock working her deeper with each thrust until she has the entire thing buried in her throat. Jon holds her there for just a second before letting her off.

Erika pants for a little bit before saying, "Thank you Sir I am yours to use as you see fit."

"Show me how much you love my cock and suck it like the whore you are." Again she hears a familiar voice saying such foreign words, a month ago she was just fiddling with women's clothes and now she is a full blown sissy, she can not stop the feelings that are coming over her like ocean waves and Erika grabs the base of Jon's cock with one hand, plays with his balls with the other hand, and starts licking his cock all along the shaft and head. Then taking the tip into her mouth swirling her tongue around it before bobbing up and down making slurping sounds and staring into Jon's eyes.

Jon moaning and enjoying the experience. The sissy in her is hoping she is pleasing her Master, though it is obvious she is, it is the nature of a true sissy to search for perfection and also feedback from her benefactor that in fact she is doing a superior job!

Her Master says, "You give head like a pro sweetie."

"Get up on the bed on all fours." Jon strips himself then climbs up behind Erika pushes her dress up and pulls her thong to the side. He then starts pushing the plug in and out of her ass as she moans.

"Oh god Sir please take the plug out and replace it with your hard cock I want you to cum in my sissy pussy." These words she said leave little doubt that she is already a sissy, somehow instead of running from her feelings of shame she experiences a new and warm and yummy feeling, that of pride that Master is enjoying her! Jon pulls the plug all the way out of Erika's sissy pussy and slams his cock in with one thrust.

"OH GOD thank you Sir. Your cock feels so damn good. Fuck me hard and rough make me feel like the sissy slut I am Master." Jon starts thrusting hard and fast inside Erika pulling her hair and slapping her ass all the while.

"You are my slut you will suck and fuck whoever I tell you to, the exact way I tell you to. Do you understand me sissy?"

"Yes Sir I will fuck anyone you want me to I am your whore to do with as you please." As Jon continues to fuck Erika she starts moaning more and more until she screams out and shoots her sissy juice into her thong.

"Oh god Sir your cock feels so damn good I just creamed my panties for you. Please give me your seed fill my sissy pussy with your cum. Can you please put the plug back in my sissy pussy after you fill me with your man cum, I want it in me all day Sir." Jon slams all the way into her and blast his cum deep inside her.

As soon as Jon starts cumming Rose walks in on Jon and Erika. "Hello Rose get over here and eat my cum from Erika's sissy pussy unless you want me to dump you," Jon says. So much for keeping my Masters cum in my pussy today she thinks!

"Mistress Rose what are you doing here?" Erika asks.

"I will explain as slave Rose eats my liquid treat from your sissy pussy," Jon replies, "Now get over here Rose." Rose did as commanded and knelt down behind Erika and as soon as Jon pulled out she moved her mouth in place and started lapping at the dripping cum.

"Now for the explanation slave Rose is here because she technically cheated on me with you, a sissy fagot, but more importantly knew I wanted to own a sissy and never told me about you. So for our relationship to continue I now own both of you. Rose will still be your Mistress though. Do you both understand?"

"Yes, Sir" both Rose and Erika chimed in.