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Chapter 16 by Schmugelflugel

What are you waiting for?

Time flies by! [Skip two weeks]

From that moment on, the next weeks become a blur. Looking back on it, there were times where the speed of your progress felt unreal as the two of you continued on the road towards fulfilling all of your new fwtishes and goals as a couple.

Going to the mall, you not only were at Christys beck and call to pay for anything she and you tried out, you also witnessed her shamelessly flirt with other men right in front of you. One particular incident that day stands out as she was dressed in provocative lingerie and just walked out of the dressing room in plain sight of the entire store, giving a few men quite a show in the process. She also made sure to include many girly undergarments for you, and trying them on felt so thrilling and right. It was a no-brainer for you to buy a whole drawers worth as well as many more racy pieces for Christy.

Later that week, she continued on the path of feminizing you, as she took more and more control in your relationship (which was approved by you, of course). Trying on make-up was incredibly eye-opening and apart from your flat chest and miniscule bulge, as you were dolled up and dressed in lingerie, there was little separating you from a sexy woman. Meanwhile, during times where Christy wasn't continuing your femboy-transformation, you decided to take some matters into your own hands and set up a Tinder-profile for your girlfriend (with her approval as well, of course). Taking control in this aspect felt so naughty, posing as your own girlfriend to find men she might be interested in fucking instead of you. A few loads were spilled during these days as you alternated between trying on female clothing or having make-up and nail polish applied and browsing the male offerings of your city until the whole eroticism got to you and you shamefully masturbated on the toilet.

During one of these jerk-off-sessions, Christy caught you and proceeded with a new punishment, since the spanking had been more enjoyable for you than anticipated (and it also had become part of your nightly bedtime routine, as well as you fucking her with her dildos and/or eating her out). She had secretly ordered a pink chastity cage and as she held it in front of you, it only felt natural to submit and present your genitals to her for their new cage. As an alternative to jerking off, she had also ordered a prostate stimulator and an enema kit so you could start experiencing a new passive role in sex. All of these items of course were charged to your credit card and with these past days, the thought of giving up more and more control in that financial regard became a newfound kink that joined the others in your new repertoire of perversions. You explicitly gave Christy permission to use your considerable financial resources to her hearts content.

That became a point of contention, as Christy started to have doubts about the quickness with which the two of you delved so deep in unknown territory. You reassured her and you both promised to each other that you'd be mindful of each others boundaries and you also established the safe word "Kiwi". After that soul-searching conversation, Christy proceeded to flush your ass and bring you to a mind-blowing hands-free-orgasm using the prostate stimulator. You returned the favor by bringing her to a few oral and manual orgasms while she used her new Tinder account to sext with a few prospective bulls, sending revealing fotos of herself and as one man, James seemed interested, she also divulged your situation. He seemed to be receptive and as her fifth orgasm trembled through her body, Christy agreed to meet him for a date during the following week. During her cooldown, you looked at their conversation and as you scrolled through their exchange of flirty innuendos and revealing pictures, you stopped at a pic of his tanned, erect dick. The discomfort was immediate as your limp dick tried to grow into a miniscule erection at the sight, but restrained in its cage, this effort was to no avail.

After Christy taking pity on you and bringing you to yet another mind-melting buttgasm, you more and more fell in love with your new, kinky way of getting off. The following three days were unfortunately mostly occupied by your respective daily routines, but still you tried to use any opportunity for you and Christy to play. After setting up account-sharing, the two of you expanded activities on your girlfriends Tinder profile, slowly growing a stable of prospective bulls while getting horned up non-stop about your lewd sexting with a bunch of hung and fit men. Noticing Christys apparent preference for black men in her matches and chats, you decided to lean into that a bit more as well, and after an extensive google search, you set up a profile for Christy on a snowbunny website. The thrill of posting face-blurred nude pics or even masturbation photos that displayed her sexy body and naughty attitude in all its glory inspired you to many a ride on your new favourite toy. A nice secondary effect of your new way of masturbation was the minimized refractory period, allowing you to get off so many times that your dick seemed to be almost constantly leaking. As you took to wear female lingerie around the house, this meant that you often times exyposed yourself to neighbors or passersby, first accidentally and later on purpose. Christy meanwhile went on another shopping haul it seemed like, as your credit card showed expenses of several hundreds of dollars. The times where the two of you were intimate together became test runs of sharing another man in your bed, often times revolving around her many realistic dildos which the two of you worshipped in submissive role play scenarios before guiding them into her, fucking her with them and of course enjoying a thorough clean-up afterward. Due to her purchases, a dildo with a cum-pump joined your repertoire, adding to the naughtiness of the simulated blowjobs and clean-up-duty.

The following week brought a first date between Christy and James but due to her nervousness, they didn't go too far. In the end, they were only making out on your front porch, in plain view of yourself as well as your neighbors while you stood in the living-room and fucked yourself with a dildo and watched them get hot and heavy. They promised to continue right where they left off next week on a follow-up and you took the time to search a nice, romantic restaurant for them, pre-booking a table and services for your girlfriends date. Your submissive pleasure spiked as she presented you the check for their first date, spending 300$ of your hard-earned cash on luxury meals and wine. A little tipsy from the fine wine, Christy is just as horny as you are, with her still hot from the make-out and you from the anal pleasure. Taking things to the bedroom, the two of you engaged in an extensive role-play session with a dildo that the two of you christened James. Taking him in your butt as Christy spanked you, fucking her with him as you rimmed her, worshipping him by hotdogging him between her cheeks as you licked him were only a few of your constellations before finally collapsing in a fucked-out heap on your bed.

During the next days, you continued your respective routines, flirting on Tinder, shopping for naughty outfits and toys for the two of you and of course still working and studying, which admittedly had been sorely neglected over the last few days.

The first day of the weekend held a new, special surprise in store: Christy took you to a clothing-optional beach. And not only that, but she brought a unisex swimming speedo for you, that unmistakeably would display the form of your chatitiy cage. Holding the key for you, Christy of course refused to unlock you as the two of you dressed in the revealing clothing: You in the red speedo and Christy in a white thong. Going topless to the beach for what seems to be the first time judging by her tanlines, Christy seemed a bit out of her comfort zone at first, but slowly she grew more confident. At one point, she went as far as to call a man over to the two of you and chatting him up in front of you. Her hard nipples betrayed her arousal, as she "innocently" asked him to put lotion on her back. Taken aback, the man just looked at you and seeing your approval, you noticed a growing bulge in his pants.

Your restrained dick raged against its confines as you watched the stranger lotion up your girlfriends back, but soon after that, he excused himself hurriedly with a red face. Laughing about the awkwardness of his departure, the two of you resumed tanning, exchanging flirty remarks with and about several of the beach-goers, mostly men of course. Your new-found sexuality grew more and more on you and you realized that you were attracted to men almost as much as you were to Christy. Finishing up the day on the beach, your evening went as uneventful as one might expect: You eating Christy out while she watched porn on your big screen in the living-room and sexted with one of her matches on Tinder.

Your Sunday brought another surprise, this time for Christy as you had researched and found an adult store in your town, that not only had opening hours for the entire week, but sported a vast array of features with a gloryhole in the basement and voyeur cabins to boot. The two of you went to check it out, but after trying on and buying several lingerie sets for her and you, buying a new tube of fake cum and flirting with the burly store-keeper, the two of you chickened out on checking out the glory-hole, but promised to come back at a later date and commit to exploring the gloryhole that time.

As Monday and the new date night with James came around, you spent the daytime working while trying to to get distracted too much until the evening and finally, ready to be prepared for her date, Christy arrived on your doorstep.

How much will you indulge in preparing her? Or do you chicken out?

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