Maybe long term Jordyn was right, but I wasn't really ready to leave her apartment yet. But she made me, holding on to my hand, but thank God that we weren't leaving the building. In Unit 1 there was a woman waiting for us who put a tattoo on my bare shoulder, marking me the “property” of the Boss, whose initials were apparently a stylized R inside a circular C. Nobody knew his real name and he wanted to keep it that way.
What I didn't expect was the shot she gave me in my butt, my first session of HRT. Nor didn't I see the corrections coming that she applied to my lips, making them much fuller and much more female. And I would have to come back the next morning for my first laser hair removal section. If I had any idea that maybe I could become myself again one day, the reality of my situation hit me full on in that office. Within two weeks I was scheduled for breast implants, a vocal cord shortening, and they would scrape off part of my adam's apple.
I got the code for the lock of my own apartment, or Unit, as they called it, next to Jordyn. And she explained how to operate the camera system, as more and more clients wanted a “souvenir” of their sexual encounter. And even if they didn't want it, there was always one camera active, essentially to protect us, in case a client became violent.
And suddenly the boss was back. He complimented Jordyn for doing a good job on me, and somehow I felt proud about that. He didn't waste any time as he dropped his pants, like before. And, showing him that I was committed, I wasted no time either and was on my knees right in front of him.
Things were slightly different than a few hours before. Obviously, I was dressed now, my skater skirt giving me enough room to spread my legs a bit still, as I sat on my knees on a much thicker carpet. The weight on my chest pulled me down a bit, so my face was much closer to his crotch. And I had to wipe my hair out of my face to make sure it didn't get in my mouth or wrap around his dick. Then, my fingers around the base of his dick had now red hot killer nails, which looked incredibly sexy, even in my own eyes.
But, the biggest difference was my lips. They felt like I was numbed at the dentist, so thick they were, yet I had all the feeling in them. They were cock sucker lips, no way around it.
Since they were mine now, I put them to good use, and soon the Boss was moaning, my lips and tongue soft cushions wrapped around his member. I knew more or less what to expect now, so I wasn't panicking, but I still put the picture in my mind that I was blowing a shemale, which funnily enough did not feel gay. Unfortunately the egg inside me was not vibrating, my second shemale not present.
I can only guess that Jordyn could read my mind and wanted to fix it, as my skirt was pulled up onto my hips. And then the egg was pulled out… No!!
I must have stopped paying attention to the dick I was working on, as I heard a voice above me saying “Suck it, bitch!”
That's when suddenly I felt two hands on my hips, and something new was pushed into my gaping hole. I gasped, which made my Boss moan again, as I inhaled his dick. Then my rear was filled with something that was much longer, much thicker than the egg. And it was warm and slippery.
I heard Jordyn behind me now moan as well, as the voice above me said “Fuck her hard!”
Is this what a strap-on feels like?
The good thing about this was that my fantasy of being spitroasted by two shemales was intact again, and I started sucking and squeezing like my life depended on it, as well as pushing back onto whatever it was in my rear.
I knew this situation wouldn't last long. I could feel my own orgasm coming up as the thing inside me started swelling up, touching a nice spot inside me. But I knew that the Boss had to cum first, so I pumped him hard, taking him practically in my throat. And he was swelling as well as I tickled the thick balls in his scrotum.
When he came finally it triggered my own high, as I could hear my own moan louder now than either the Boss's and Jordyn's who somehow shot her load in my rear at the same time. It was hot and hit my insides hard, just like I had fantasized about in my previous life.
As we all came down, the dick slipped from my mouth, as did what had to be a dick from my rear as well, and the Boss said “Plug her up!”
Something cold was pushed back into my hole, which in a wicked way felt comforting. It prevented the fluids that were clearly inside me from sloshing out. At the same time the Boss grabbed me under my arms and lifted me from the ground, seemingly without effort.
After he laid me on my back on the bed, with my skirt still on my hips, I could feel him pull my panties down, and he said “Ah.. I knew it! There's a puddle in her panties, yet she's still completely soft.” That made me think a bit. The leather panties had given my own dick no chance to grow, yet I had still shot my own load. That had never happened before.
I could feel the Boss touch my limp dick, and I tried not to wince from the feeling of a man touching me there. He was wrapping something cool around it, all the way around my scrotum, and then there was a click. I couldn't look down past my breasts, but I knew he had wrapped something around my manhood.
“Exactly what I thought”, I heard him say. “She's no shemale like you, Jordyn. She's a sissy. She's gonna make us some good money, as I've had to decline hundreds of requests for a sissy already. I want you to train her hard, until she begs to be fucked from behind. I want her to be proud to be a sissy. By the time she has her own breasts the money will roll in.”
Then he talked to me. “Good girl! Your name will be Baby. Tomorrow we'll make it official. Already you give the perfect blow job, and people are going to love seeing how you came from a dick in your ass.”
Then he warned me. “Don't mess with the cage, or it could burst your balls. I want to find out first if your clients prefer you being castrated or not.” And just like that he was gone again.
Finally I saw Jordyn, her skirt gone, with a huge dick between her legs, even limp much bigger than mine had ever been. And I realized that my wish had come true, from the moment I met her I had hoped she had a dick, but for some reason I had concluded she had to have a pussy, because of her breasts producing so much milk. Because of her twin sister, that had made sense. But if she was originally male, then her twin sister would not have had that effect on her, right?
It was like she could read my mind. “Sorry Baby”, she said, "I know you liked to suck my breasts, but I can finally stop with the milk pills now. They have messed me up for days, although I truly enjoyed you draining me. We'll try those pills on you, once you have your own breasts, I bet your clients will love draining them.”
I was shocked now. She had taken pills so her breasts would produce milk? “Why?”
“Well. We had our eyes on you for a while already. You'd left a few comments on some of the pictures on my profile. How you'd suck me, and how you'd take me up your ass. The Boss bet you were a sissy. I thought you were more like me. So we set up a little plan to trap you, and now you made me lose a hundred dollars. Since I was wrong, I'm looking forward to training you. You will beg me for my dick, I promise you, and any dick we can provide you with once the training is over.”
She wasn't wrong, even though I felt she had betrayed me. Over the next couple of days she still had milk in her breasts and I couldn't stop wanting it, two or three times a day. But, she'd only give it to me if I sat on her lap, my legs around her, and her pole in my rear. Then she'd slowly sink backwards until her back was on the bed, and as I kept trying to suck her breasts, I was in the most awkward position with no chance to move even, as her pole hit new depths inside me. The little bit of control I had was in how I sucked her breasts, and it made her bounce up and down, taking me with her like a rag doll.
Somehow it wired my brain so that the pleasure of drinking her milk became the pleasure of being fucked. I would cum at first when she'd shoot her load inside me, while squeezing her breast, giving me a huge squirt in my mouth. This changed slowly into me coming first, triggering her own release. In all this my own dick, with no chance to grow in its cage, shut down completely, to prevent the pain from growing hard.
But, when her breasts stopped producing milk, no matter how hard I sucked, nothing came out anymore, and she gave me a dildo to suck on instead. If I sucked hard enough it would release a liquid that tasted very much like her milk, at which I automatically came from her pounding my ass. The dildo was soon replaced by a very realistic dick, and she taught me all the tricks to pleasure it, and only if I did everything right would it shoot its load, which tasted more and more like the Boss's cum. And only then could I cum from Jordyn's dick in my ass.
I was aware that I became addicted, and maybe it was from the daily shots that I got as well, that I couldn't fight the addiction. By the end of the week I didn't need Jordyn anymore. The dick was mounted at crotch level on my full length mirror through a strong suction cup, and I used a huge dildo in my rear, as I sat on all fours. Each time I had to fill the “mirror dick” with a cum cartridge, and more and more my mind wanted the real thing. Not forced like before, but an unexplained desire to be throat fucked.
Again Jordyn was my savior, and with her monster pole my throat was a welcomed receptor. There was a prize though… I had to mentally acknowledge that I was now a sissy and submissive to whomever had the dick. And I learned that once you're addicted, you pretty much do anything.
I had to call her Mistress and beg each time for her cock. I had to accept that pink was now my favorite color, which I actually found rather easy. And she had me wear more and more latex. Which became a problem as my cage was very visible through my tight latex skirts. And by the end of the second week, when my surgeries came up, she had me begging for the removal of my scrotum.
A few days later I was recovering from much more severe surgeries than initially thought. My tiny penis, I don't even dare to call it a dick anymore, was not much bigger than an engorged clit, surrounded by smooth hairless skin where once my scrotum was, and looked now like a sexy camel toe when covered by latex.
I no longer needed a corset, other than for dress-up games, as my own skin was now pulled together on my back with pink leather laces, that could only be tightened more, but never released again. Before they took me under they removed my fake breasts, and already my own had started growing, thanks to the shots of hormones and apparently something was mixed also in my cum cartridges.
When the bandages came off, my new breasts had increased by a full size, much heavier than the fakes. And little silver bars had pierced my permanently swollen nipples. My heels no longer needed to be locked, but I had to wear at least four inches of heels at all times, or the pain in my legs would be unbearable.
I only found out later that a new egg, controlled through Bluetooth, so there was no need for an antenna anymore, was surgically sewed deep inside my rear. It would give remote clients a chance to pleasure or punish me. And both the Boss and Jordyn had full control over it as well.
So yes, my vocal cords were tighter now, giving me a bubbly voice that would never be mistaken for a guy. My lips were slightly thicker again and tattooed in bright red. My adamsapple was gone, and they did something to my eyes, nose and cheeks. Besides that, my skin was super smooth all over my body.
In the two weeks it took to fully recover, I fell in love. With Jordyn. Again!
I know. She tricked me, right? But she was also doing what the Boss told her. I mean, I now know that you simply do what he says.
And Jordyn was so gentle with me, teaching me how to be a woman, all the way. We soon slept together each night, she would spoon me, with her monster often buried deep inside me, her arms around me, her hands caressing my new oh so sensitive breasts.
In that time I got to know everyone else in the building, as they acted as clients with different desires, while Jordyn suggested how to handle each case. And finally, I was “ready” and apparently there was a waiting list already thanks to my spitroast video going viral. All wounds were healed, all pain was gone, I was used to the heels, the boobs, the lips and my new voice. And I was nervous like hell, despite all the practicing.
Let me real quickly explain the procedure. A client makes an appointment through the CSR supporting staff in Unit 1, either by phone, or through the app, or straight on our website, or as a walk-in and stay anonymous, like the good old days. The client will request a date, provide the amount of time needed and any special desires, with an option to pick a particular girl, or boy for that matter.
If no particular staff member was selected, the CSR's will match the best available resource, based on skills and availability, considering working hours, vacation schedule and monthly periods. The agenda for the selected member is updated for the desired day and best available time slot.
If there is a preference for a certain person, then the agenda is checked for the requested date, and if there is room, a slot will be reserved. Otherwise a new date will be suggested for when that person is available. Hence my own calendar being full for the next three weeks.
There is a tablet in my unit, hanging on the wall, showing my agenda for the day. Each time slot shows the preferences of the client and any details I may need to make the appointment as efficient and remarkable for the client. Luckily I don't have to deal with the financial side, that's all taken care of before the appointment starts.
And so, my first day on the job showed a fifty-some male with an interest in sexy clothing, but no preference for any speciality. Yet, he had specifically requested me. I was nervous about having to figure out how to give this man the satisfaction that he'd paid for.
I was ready for him, in a full-body fishnet style body stocking that left nothing to the imagination, yet covered every bodypart, except my head, my crotch and my rear. I had added a simple latex wrap-around skirt, that could easily be removed when needed. My makeup was perfect, my heels exquisite, my breasts standing out proudly. When I opened the door after he knocked I faced my father.
I was stunned. My first thought was, why would my father need the services from someone like me? Cheating on my mother?
Then I just hoped that he wouldn't recognize me, as that would be so embarrassing. I saw a shock on his face as well, but then he said, “Can I come in?”
Oh my god! Rule number one. Get the client inside and make him comfortable. So I apologized and ushered him in. I had him sit on the side of the bed. Then he said, “You have changed so much, I had to see it for myself. They gave me your very first appointment. You go by Baby now?”
So he knew. They told him. And in a way it was comforting that he wasn't yelling at me. “Yes. That is official now. I guess you didn't expect this from your one son, right?”
“Well. We knew you were browsing about transgenders. We just weren't sure what part of that you liked. Now we know.”
They knew about my fetish? Oh god, this is getting worse by the minute! It was clearly not easy to talk about for him either. He was not comfortable, and my training kicked in.
“Listen dad. Since you're here it is my duty to give you a good time, and get you relaxed. Why don't I take these pants off of you?” He started protesting when I opened his fly and pulled his pants down from him, but I told him, “Remember when I was a kid, having all these wet dreams, and messing up my bed? You taught me how to masturbate. I saw your dick when you demonstrated it. Why don't you give me a chance to teach you something?”
Maybe he contemplated my words, but I gave him no chance to back out. The moment his pants were down I was on my knees between his legs, and I had his dick out and in my mouth. I didn't plan on having sex with him, but I was going to give him a blow job he would never forget.
In the past weeks Jordyn taught me everything she knew, and she was an expert on the topic. Plus I could practice on her many times. And with these new lips I could make my grandfather alive again.
Already he was growing in my mouth and I heard him gasp a few times, trying to suppress his moans. I had to smile, as I knew he had no chance. I relied purely on my hand around his base and my tongue and lips around his member. Didn't try anything that could turn him off, like tickling his scrotum or around his anus. But cumming he did!
As I sucked him dry, swallowing every drop, he looked at me with curious interest now. “I didn't expect that, but thanks. You're a real girl now, right?”
“Almost”, I said, and dropped my wrap skirt, where my tiny leftover was still popping out. “At some point I will have a pussy, but this little thing will never masturbate again.”
“They took your balls”, he gasped. But I corrected him, "I gave up on my balls as I had no use for it anymore.”
He nodded, I think he understood. “What am I going to tell your mother?”
“That I still love you both, that has never changed. And if she wants to come here as well, I will eat her cunt, I promise you that. I have quite some talents now.”
He laughed at my joke, then choked, thinking that maybe I was serious. He got up, his half hour almost done. When he was about to leave, he turned around and asked, “Will we still see you for Thanksgiving?”
I laughed and said, “Of course. If you guys still want me. But, I will bring my girlfriend, if you don't mind.”
“That would be nice”, and he came back to me and kissed me on my forehead. “Bye Baby! Be safe please.”
And the remaining five minutes after he left I sat on the bed, dazed, yet somehow happy about what just happened.
Everything went fine for the remainder of the day. My hours, roughly noon to nine, with an hour for dinner, spent with Jordyn, were completely booked, and they would be for weeks to come. Not one bad word I heard. Well, a few should not be used in a school class, but you get the idea. Everyone seemed to enjoy the new me, and most importantly, I enjoyed it too. No stressing about work anymore, no tough problems to solve. Just how to give my client the most value for his money. Yes, so far I had only dealt with men.
My last client for the night, or clients I should say, wanted to spitroast me, so it showed on my tablet. And that happens to be one of my favorite positions. Until I opened the door to my two best friends.
Apparently they were invited as well, just like my dad this morning, but the shock was still intense for all three of us. Except, they saw that their friend was now a dripping sexy girl, and I could see their hard-ons appear in their pants. No training needed for that.
So, without talking things over, I took the lead, got them out of their pants, took one dick in my mouth and told my other friend to fuck me hard from behind. How simple things can suddenly be if you stop worrying about it.
And we have talked about fucking so often in the past, boasting even, but I had no idea their dicks were that big. And boy, did it feel good. For all of us!
Only afterwards they started talking, like “Dude. Why did you never tell us?”, and “God, you're a good fuck!” and “When can we do this again?” But, the best part was when they left and asked if I would still come to our get-togethers and parties. As far as they were concerned I was still me, no matter what I looked like. And I guess that's what friends are for.
That night, in bed, I told Jordyn all about my day. And about my dad. My friends. She told me I was lucky, her own parents dropped her like a rock, years ago. And yes, she loved to come with me for Thanksgiving and meet my family. And she'd come with me to see my friends as well, if the schedule allowed for it.
She started giving me a pill now, every morning, with breakfast. I knew better than to question it, I was the golden egg in the business for now, so I was sure the pill would only improve me. And indeed, after a week or so, my breasts felt full. And if I squeezed them, little squirts of milk would come from my nipples.
It was an unexpected bonus for my clients, only adding more to the waiting list. But at night it was for Jordyn. It had all started when she offered her milk breasts to me. My new life, perhaps forced on me, but already I knew I would do it again, given the opportunity. But now that it was me, on the other side, the feeling was so incredibly erotic when someone sucked on my nipples, especially Jordyn, I didn't think I would ever stop taking those pills.