Chapter 88 – Paris’s feminization fits finer while preparing to PrEP

Watching Ike the tech trying so hard to focus on his work and not me is way more amusing than it should be. I probably have Darnell and Trixie to thank for my humor and my teasing. That moment at the Barrell a few weeks back seemed to break me. Though while it certainly felt like I was breaking into tiny little bits at the time, it actually wasn’t that bad and my eventual reaction to it was… well, it was natural.

It’s not the blowjobs themselves as I really hate doing those. It’s demeaning and demoralizing and completely manically demasculating. I can’t imagine anything that would be less masculine than kneeling down, feeling my stocking clad knees land on the carpet, feel my short tight skirt tighten even further around my curvy ass, while running my long fingernails up and down the strong thick hairy thighs of a man and hearing him moan out his pleasure as I lean in and give the tip of his cock that first lipstick enhanced kiss.

No, it’s not the blowjobs that made me like this. It’s how I had to deal with them. It must have been that third time being led into the storage room by Darnell that I just gave up. Once the door closed, I let go of myself. Just let go. For the first time there was no Jamie present. Just Paris, the sexy, curvy, soft, bimbo secretary that loved going down on her tall dark strong very VERY masculine boy toy lover.

That didn’t make the blowjob good by any means, but being full-on Paris made it bearable. And the third or fourth time I did that I… it’s still embarrassing to say it, but I enjoyed it. I enjoyed teasing Darnell and knowing that my high-pitched giggle made his thick girth throb in my tiny hands. I think that night was the first time I used my smile.

I mean, I’ve smiled plenty as Paris. But when I got on the train, I was honestly tired. Mal let us go early that day, if you can call leaving at six thirty early, so the train was extra crowded. When it slid into motion, no one had moved to offer me their seat. I guess it was months of instinct that let me know the middle aged businessman pretending to read his phone while actually sneaking glances at me would be the easiest target. Two steps toward him, a smile with a little giggle, just a bit of a realistic ‘EEeep’ when the train jostled while acting like I almost fell over and voila. He got up and offered me his seat. Sure, he got the clear view down my blouse along with my crossed legs stretching my nude pantyhose, but being able to sit down for the rest of the train ride was worth a little girly play and a little showing off of the goods.

And the more I let Paris out, the more I realized just how easy I could make my life. Step into a store with a long line at the cashier? No problem. A dramatically loud sigh and a particularly exaggerated pout and I either get a new cashier to open for me or get invited to the front of the line. Missed the last head of lettuce at the little grocery store? No problem. Find some guy with a head of lettuce in his cart, fake a tear or two while letting out a sob that’s enough to shake my tits at him and boom, I have some lettuce and he gets a bit of a show. If he’s really nice and good looking, I might even give him a hug so he can remember the warmth of my tits against his chest.

And the more I use that side of myself, the easier it is to fall into it. In fact, more and more often I find myself just acting that way. Just being Paris instead of Jamie acting like Paris.

So yeah, as I grin down at Ike while he’s lying on his back under my desk, as I roll my chair a little too close to him, as I uncross and recross my legs for the fifth time and give him yet another peek at my hot pink panties, I can’t help but enjoy his squirming blush. Anybody with any tech sense at all would realize he’s unplugged and replugged in those four connections and that power plug at least a half dozen times… but it’s fun to watch him try to extend his time beneath my desk.

When the poor guy finally can’t fake his own incompetence any longer and finishes up, I make sure to give him a big hug and act super impressed that he fixed my computer. He doesn’t need to know that I’d crossed those plugs on purpose with the intent of getting him up here. And now that I have him fully worked up and barely able to hide the hardon in is cute khakis, it’s easy as pie to ask him to get me a new laptop for Mal. He simply nods and writes down the specs while starting at my cleavage as I lean forward to give him a better view, telling him I need an Intel Core Ultima 9 590HX Plus 34-Core processor with thirty-two gigs of RAM, a four-terabyte gen six NVME drive, and a 16-inch OLED 4K screen. He probably doesn’t even remember me mispronouncing USB and calling my mouse and keyboard the mousey thingy and the typey parts just a few minutes ago.

But hey, Mal will get the laptop he was told he couldn’t get for another three months. And if I were a betting woman, I’d bet he’ll have it tomorrow morning, fully configured, with all his files already moved over.

Once Ike is finished, I double check the travel arrangements as all the trips are coming up quickly. The Dallas security conference went off without a hitch and the guys all sent me flowers and candies as a thank you. Now all the attention was on me to see if I can reproduce those same results for Mr. Zeller’s vacation, Mr. Stirling’s symposium, Frank and Thomas’ conference in San Francisco, Grace’s trip to Miami and of course Mal and Darnell’s meeting in the Maldives.

When I see that everything is looking good, happy that I changed the flights at the last minute to avoid flying over the mid-east conflicts, I double check Mal’s email and voicemail and then log off my computer. Grabbing my purse out of the locked filing cabinet, I flash Mal a wide smile and a cute wave as I head out. I barely see his little pinky finger waving back while he’s on the phone, but I do see it and know that he’s aware that I’m heading out to my doctor’s appointment.

When I get to Sculpted Dream, I’m just on time for my appointment and am escorted directly back to Stephen’s office. I barely rest my backside in the comfy chair when Stephen walks in. In another sign that he sees me as Paris now instead of Jamie, Stephen strides over and instead of giving me that firm handshake where we fight to squeeze each other’s hands off, he gently grips my fingers and brings them up to his lips for a soft kiss in hello.

Even knowing Stephen all those years as buddies doesn’t stop me from blushing a bit. He is, after all, a famous plastic surgeon that’s very handsome, well built, rich, and currently looking at me as if I were the center of his entire world.

After a few minutes chatting about the weather, the Cubbies, and the new Taylor Swift album, Stephen finally gets down to business and starts asking about my healing. I answer all his questions as honestly as possible, letting him know that even I sometimes find it difficult to find the surgical scars. All except for the one under my right breast. That one just hadn’t reacted to the lotions and creams and hadn’t healed completely perfectly. It was still barely noticeable, but that made it far more blatant than any of my other multiple scars. I admitted that my back was bothering me and just nodded at his suggestion of getting more supportive bras. That was easy for him to say, but more supportive bras didn’t match my work uniforms at all, so I’d just have to deal with the sore back.

Stephen finally brings up Suzy’s regimen, and I lean forward with more interest than is probably warranted. But after thinking about how this could go, I was in fact very interested, “Yeah, about that. Look, she’s really good at cornering me into conversations where I have to admit to doing certain femmy things or even make up doing femmy things in order to keep her convinced that I want all of this femininization. Last week we got to talking about sex. I told her I was having sex with two men on a regular basis but was looking into maybe finding a different lover and trying a single monogamous relationship.”

It takes me a minute to realize I probably hadn’t told Stephen about actually having sex as a woman, which easily explains his eyes opening wider and wider. Trying to spin another version of my convoluted life I clear my throat and move back a step in my story, “I mean, of course you know I have to fake that stuff with her, right? I just watch some rom-coms and regurgitate that stuff to her. Anyway, she kept at me for having unprotected sex and said that I’d have to be responsible as I couldn’t expect men to take on that role for me. So now she wants me on some kind of HIV pill. Worse, she wants me on some kind of cleaning regimen to... well… prep me for anal sex.”

I don’t bother telling Stephen that I’ve been wearing her stretching butt plugs for weeks now and had just moved up to the third size earlier this week. I also didn’t bother telling my old buddy that I was currently wearing my ‘work plug’ that would occasionally buzz my rear whenever Mal thought I’d need a bit of pleasure. After clearing my throat again, I go on, “So, what I was thinking is that you prescribe the stuff she mentioned and I pick it up the pharmacy but then just not use it. That way she’ll see it’s been prescribed and filled but will have no idea that I’m not really using it. You can help me out in that, right?”

I sit back and lay my hands over my crossed knees. Stephen seems to consider what I’ve said deeply while looking down. I take it as a good sign as he’s not looking at my ample cleavage but it only takes me a moment to realize I’ve subconsciously let my strappy stiletto slip off my heel and was letting it dangle from my toes. While I can put my heel back on easily enough when I put my foot down, I can’t do much with it in the air. Since uncrossing and recrossing my legs will show off a little more than I want while Stephen is staring at that part of my body, I just stop tapping my foot and let the shoe dangle.

This time its Stephen’s turn to clear his throat before talking, “Look, Paris, I read Ms. Gardner’s recommendations as she sent them over to my private email box. The exact product she’d like you on is a daily PrEP or pre-exposure prophylaxis pill called Truvada. It’s a drug that can prevent HIV infection if taken regularly. She in fact asked for Truvada in a very particular dosage packaging to make you more comfortable in your transition.”

I can’t help but roll my eyes as Stephen shows me the Truvada medication dispenser. It only gets worse when Stephen starts talking about the anal sex preparation medicine and procedures. After he finishes telling me about the specific drugs and procedures, Stephen leans in closer to me and even takes my hand in between his, “Here’s the rub though. She was very particular in the brands she selected. There are plenty of legitimate reasons she could have picked these or any other versions of these drugs, but these ones in particular show up on inexpensive lab work. In other words, I can certainly prescribe them, but she’ll know if you take them or not.”

Twenty minutes later I’m walking down the sidewalk with the little bag from the Sculpted Dream’s in-house pharmacy, marveling at the messes I find myself in. While the PrEP is annoying it gets worse when adding the fact that they pack it in a birth control style dispenser. To anybody that sees it, it will look like I’m actively trying to prevent getting pregnant. And of course, why would a woman be doing that? Why, when she’s having promiscuous sex, of course.

The Truvada itself is public humiliation. With minimal side effects though it won’t be anything more than adding another pill to my morning regimen. The anal sex prep though will be a personal humiliating procedure. When Suzy talked about it at our last session, I thought it was just another pill. Maybe an injection or patch like my other meds. But no, this one is a direct application product. During three showers a week I have to prepare this little bottle with its long thin applicator, lube it up, slide it up my rear, and squirt it up into my rectum. Inserting the applicator shouldn’t be too difficult with all the butt plugs they have me using, though clenching my sphincter muscles enough to keep it in for the required five minutes will be an exercise all itself.

Just before the stairs up to the train station, I stop dead in my tracks. Ever so slowly I close my eyes and reach up to pinch the bridge of my nose in frustration. The butt plugs are working to stretch me to better accommodate something up my rear. The drug in this application is designed to make it easier to take something large up my rear without tearing or pain. But it just hit me that one other purpose of this application process is to have me exercising my own muscles in squeezing down.

Put them all together, and they’re literal exercise and salves to make me a better anal sex lover, able to not only accommodate a large cock but also to squeeze down on it.

Fuck my life.