Crossdresser to Sissy Whore
Jack had been cross dressing since he was a teenager. His sister’s thongs and bras were first, and they felt soo good on him. He’d jerk off and put the things back. Things escalated, stockings felt good on his legs, he spurted even stronger. Next was makeup, Jack was surprised how good he looked and at this point it would only take a couple of strokes to release the cock cream. He’d been doing this for a couple of years and at seventeen he was a horny guy and found something that really turned him on. He finally grabbed a tiny mini skirt (his sister liked looking slutty) and blouse, which he tied to leave his tummy exposed, he thought that he looked pretty good with the high heels, his ass looked nice. He had the house all to himself since Sis was out and his parents were on vacation for the summer. Then he heard, “Gee brother, my clothes look good on you,. I think you should wear them more often. I’m glad my date stood me up. This has possibilities”. He collapsed, crying, “Please, please don’t tell, please I’ll do anything, please”. Sister Joanie, “Make sure you mean what you say you little slut, cause I’ll hold you to it, I’ve already taken a lot of pictures of you getting dressed”.
Jack’s gut twisted, his sister had him and she had a kinky mind. She explained to him what would happen and she thought he would like it anyway. So that summer Jack learned how to be a slutty cross dresser from his sister. He learned how to shave, apply makeup, choose sexy outfits and how to be girly. She introduced him to lots of things, her dildos and a butt plug became frequent visitors to all his “fuck holes” as she called them. She blackmailed him at first and was a bitch, but then she softened after she saw he only wanted to please her truly. She had broken him into a cross dresser who loved being a completely submissive girl. He now loved his mouth cunt and ass cunt being used and referred to his cock as a clitty since she showed it was kind of small. She did this by having Jackie service her boyfriends at her lesbian lover. She even got him to lick her cunt and ass clean after she had been thoroughly fucked by her male friends. She introduced him to the joys of golden showers and hot nectar to drink a couple times also. She was kind of proud of what slut she had turned her brother into.
As summer was coming an end and Jackie was established as cock sucking slut in town Brother and sister sat down to talk. Jack was going off to college and Joanie had a job to start working at. Joanie promised never to tell, but, she told Jack, “Jackie will always be in there waiting to pounce on a cock. You’ll have to learn to control her or she’ll take over”. Jack nodded and thanked her for everything. He packed his alter-ego clothes in a box and put them in the attic. Everything was fine in college. He found the adult bookstore a great place to keep Jackie under control and his lips and mouth were welcome anytime at the glory holes. He went out with girls on dates and found he liked them as friends and never had any desire for sex with them.
Jack (and Jackie) graduated and started work in the same city as big Sister. Everything was fine until he was 25 and a friend was browsing the internet and asked him to come see this this crap. His friend was viewing aShemaleTube.com. This site had all sorts of videos with shemales doing everything you could think of. He looked at the video of a shemale getting fucked by two guys and instantly got hard. His clitty, err, cock was fully erect. He turned and told his friend he was a kinky guy. Jack called his sister in a panic after he got home. She talked with him and told him it’s time for him to let Jackie out. He asked about her life and she told her marriage to Dave, well Donna was great. Jack listened as his sister explained how she had turned her husband into a complete sissy slut and the both of them fucked guy after guy and loved it. She invited Jack over and met Donna. Donna was hot; she had a 38DD figure with a nice round ass and was dressed in a tiny micro skirt and mesh top that showed her pierced nipples. Joanie showed Jack a surprise, she had gotten the Jackie box from the attic the last time she visited their parents and gave it to Jack.
She made Jack an offer; she had a good job as a Senior Partner at a law firm. She had paid for all the changes Dave went through to become Donna. She had several Doctor Clients who were glad to barter services. She looked at Jack and told him, “you can come live with us Jack and become Jackie, I’ll pay for the treatments and changes you need. In return you’ll become my second sissy whore in the house. You get to fuck all the hot guys you want along with us and we’ll be together again.” Jack agreed immediately and his sister stood up and told him to rim her ass deep to seal the agreement. Jack giggled and asked if she used this method with her clients, she told him only a few of them, seriously, as she lifted her shirt and moaned as his tongue pushed deep into her ass. Donna watched her wife breathing hard as her brother pleasured her ass; she fell to her knees and crawled to service Joanie’s pussy. The evening ended with Jack servicing Donna’s large cock to a creamy conclusion followed by Jack having to drink his Sister’s and Donna’s hot piss. Jack quit and moved out of his apartment the next day. Joanie made all the arraignments with her doctor friends and filed the legal documents to change Jack to Jackie.
Jackie was coming along fine. All his male clothes were gone and he only had slutty girl clothes. Hormones had given him rounded hips and small tits, plus some of treatments had the effect of increasing his sex drive to nymphomaniac level. Joanie and Donna told him that was on purpose and were pleased with their slut in training. Jackie was being thoroughly trained on how to orally pleasure men and women. Jackie excelled at sucking cocks and pleasuring pussies for Joanie and Donna. Joanie was training Jackie’s ass cunt using dildos and plugs, but had not let a cock enter her pussy yet.
Jackie was looking forward to the end of the year when Joanie said he’d be ready to get his DD implants installed, plus piercings with some tattoos that would forever identify him as a Fucktoy and a Cocksucking cumdump whore. He couldn’t wait. Joanie told that was a small problem, HE wasn’t a full sissy whore yet and he had to become one. Yes, he dressed as a slutty girl all the time. Yes, he had swallowed enough cum to please all the sailors on navy carrier. Joanie told him, that he still said “he”, him” and “Guys” and it was time for him to fuck a guy as a girl. She told him it was time for Jack to go and she had arraigned his first client to fuck the Jack completely out of her and only leave Jackie.
Joanie told him you aren’t a real sissy whore when you start sucking dick or swallow your first cum. You need the moment of no return. The moment that first load of sperm spurts into your ass cunt, it starts. Jack, it takes a lot of courage for sissies to set up that first fuck date. Jack will have given up a lot to put on that make-up and lingerie, hose and high heels and start hormones. Jack has sucked cock, swallowed their loads. But this is different. You’ve fucked your ass cunt with toys and plugs, but never a real cock before. Jack knows when he takes that first cock in the ass cunt, a change begins. The deeper the cock goes the more the Jack persona is erased. You will be fucked like a gurl. Your smooth rounded cheeks spread wide for his thrusting cock. Jackie will hear her pussy making sounds now as his cock thrusts. From somewhere inside of her moans start.
Feminine moans for more and more.
Jack will be erased forever and only Jackie will remain. The male thoughts are gone for good and replaced with what you really are, your real self, a complete sissy whore.
He’ll continue to thrust and pound, working towards the end Jackie has been dreaming and fantasizing about. Please cum in me, you’ll be screaming!!” He’ll pound hard and then thrust once very deep as his cock fills your ass cunt with sperm. That will be your surrender of being male no more, you will have let a man cum in your pussy and it felt so right. This is the moment you become a sissy whore, what you were born to be.
So Jack, are you ready to become Jackie the sissy whore for your sister?
Jack looked at his sister and said yes, yes I’m ready. When does my first client arrive Mistress Joanie? I want to be ready to please him in all ways.