Monday morning arrived with the sound of Cheryl’s alarm, summoning her from bed. I stirred and was embarrassed by how quickly my thoughts went from her to Liam. That reminded me of my recently shaved cock and balls, reminding me to be a bit discreet with nudity, as that wasn’t a conversation I was ready for yet. 

While she was in the shower, I pulled on some clothes and headed downstairs to start the day. It was normal for me to make her breakfast and coffee, but I felt mercenary about it this time, as though I was helping to rush her out the door.

Cheryl didn’t think a thing of it, of course, and was happy to see me helping her out as she got herself ready. The clock edged forward, minute by minute, until it reached the time for her to depart and she did so with a smile and a kiss. I don’t think her car was even out of the driveway before I was upstairs, showering and touching up the job I had done shaving. 

I dressed in panties and stockings and as I looked down at myself in them, I had to admit that being shaved made me look like even less of a man in them. I made my way back downstairs, wondering if Liam would make me wait today, and wondering how my mind would take that, after the teasing and anticipation of the weekend. 

I needn’t have worried, as I had barely poured myself a coffee when he texted me. 

“Put on your wrist and ankle cuffs, and your collar. Wear nothing over your panties and stockings. Plug your ass, cage your clit, and fetch your dildo and gag. Wait for me on your knees in your living room. Curtains open.”

He seemed to know how to torment me, even when I thought I knew what was coming. I quickly fetched everything and went to my office to strip down to just the lingerie. I then buckled on the cuffs around my ankles and then my wrists. I felt a tremor in my breathing with the close of each lock, knowing that he alone held the keys. I lubricated the plug and my ass, and then wriggled and pushed it inside. My body reacted to the sensations, and I had to hurry to get the cage on before my growing erection made it even more difficult. Lastly, I placed and locked the collar around my neck. 

It made my heart pound with nerves, to walk out into the living room dressed like that and pull the curtains open. It was only a week before that the sight of me through one of these windows had gotten me into this situation in the first place. 

Hesitation or negotiation wasn’t an option for me anymore, so I knelt down on the floor in the middle of the room and waited. 

I didn’t have to wait long, thankfully, before I heard his key turn in the front door of my house. He strolled in as casually as if he owned it, and took in my obedience with a quick glance. 

“Good sissy. Now, another quick lesson. Spread your knees wide, and lay your hands on the tops of your thighs, palms up. Focus your eyes on the floor in front of you.”

I moved my body as he said, feeling the submission expressed in not only obeying him in such exact detail, but also in how that specific posture made me feel: on display and subservient. 

“Good slut. This is called ‘nadu’ and it is another position for you to learn and take upon command.”

“Yes, Master,” was all I could think of to say.

“The next position is similar. Place your hands behind your neck, extend your elbows out to your sides, and lift your eyes.”

I lifted my arms up to the required position and looked up to him, seeing a satisfied smile across his face. 

“This position is called ‘collar’ and like the others, I’ll expect you to memorise it, and  assume the position upon command.”

“Yes, Master.”

“Tell me, sissy, did you enjoy meeting my wife?”

I reminded myself of how I needed to answer in his presence. 

“Yes, Master. Sissy Crissy enjoyed meeting your wife very much. She was very friendly and fun to talk with. Cheryl really enjoyed her as well.”

“That’s good. We had a wonderful time as well. It confirmed in my mind just how much I’m going to enjoy us all being friends. It was very fun to meet your wife in person – to see her smile and hear her laugh. She is very pretty, and very sexy. You must miss being able to fuck her.”

“Yes, Master. Sissy Crissy misses being able to fuck his wife, Master.”

“You may call yourself just Crissy, pet. I think that the sissy part is going to be assumed more and more as we move forward.”

“Thank you, Master,” I responded. 

“I saw you looking at my wife too, I’m quite sure. You probably liked what you saw. Lydia has a wonderful body, and she knows how to dress to show it off. Which reminds me. I have a special treat for you.”

“Yes, Master?” I asked.

He just stood there in front of me and started opening his pants. 

“I fucked Lydia this morning, just before she went to work. As I was pounding into her, I thought about my desperate and denied little sissy slut, and how much you might like to taste some pussy. So, just for you, I was sure not to shower afterwards. You may thank me, and then taste her on me, slut.”

I blushed, feeling humiliated and somehow excited as well. 

“Thank you, Master. Thank you for letting Crissy taste her like this.”

I leaned in, keeping my hands where they were, until I reached his half-hard cock with my lips. I parted my lips and extended my tongue and took him inside my mouth. He was telling the truth, and I could taste her on him, at least at first, until his taste and presence of his own precum took over. 

He moaned as I took him in deeper, and I felt him harden inside my mouth. He pushed with his hips and reached down around the back of my head to force my mouth forward. He kept thrusting and driving, pushing deeper and deeper into my mouth and throat, making me moan and gasp and drool around him. Knowing he’d had sex already at least once this morning, it didn’t surprise me that it took him some time before I felt the tightening and spasming of his cock in my mouth. The taste of his salty load came right after, as he grunted and pushed his full length into me, balls deep. He slid out, finished, and wiped his cock against my cheek, as I swallowed down the slippery puddle of warm cum.

“Thank you, Master,” I panted as he tucked himself away. 

He laughed. 

“Look at you, thanking a man for fucking your mouth, without even being asked to. You are learning your new role very well.”

I felt my cheeks burn hotly. I just felt the truth of it, as I continued to kneel before him, holding the commanded position. My cock ached in its cage, and the plug teased my ass constantly.

“We have work to get to, so it can’t be all cock-sucking for you today, slut, no matter how much you might like it to be. I was very pleased to hear about the proposed basement renovation you and Cheryl had planned, so I have decided that we should get that planning and work started immediately. My crew will be here in just a few minutes, to measure everything up, so that I can have plans drawn up. You’re not really dressed to accept guests, so I will direct them. We’ll just tuck you out of the way, so that they don’t ask questions you aren’t ready to answer.”

“Yes, Master,” I answered, already feeling the rise of panic in my chest at the thought of the house filled with men while I was dressed like this.

“Follow me to your office,” he said and started walking.

I began to stand and he corrected me.

“Like a pet, slut. On all fours.”

I obeyed, working to keep up with him as I crawled behind him. Once inside the office, he allowed me to sit in my desk chair and watch as he started up my computer. Without comment, he logged himself in, using my user ID and password. I was too shocked to say a word about it. He opened up the cam site, and soon there was the trans woman Brooke again, on the screen and just beginning to tease herself and her viewers. 

He interviewed me about the plans and hopes that Cheryl and I had for the basement, speaking to me for a moment like he was just another contractor, and like I wasn’t dressed only in lingerie and sex toys. He took notes in a small notebook, and asked excellent questions. I told him about how we wanted a finished family room, a proper washroom, perhaps a kind of recreation room or home gym, and perhaps even a nanny suite. He asked me about the nanny suite, and why we might want it, and I answered honestly and without thinking. Now that we’d moved to a new city, we thought it might come in handy if and when we had kids. It wasn’t until the words left my mouth that I realised how much I had said. 

“Well well well… is my little sissy slut thinking about getting our pretty Cheryl pregnant?”

“Crissy and Cheryl had talked about it, yes, Master, now that we were getting settled and had a new house.”

My heart was pounding. We hadn’t talked to anyone about these plans, and even I hadn’t really thought about how recent developments may complicate those plans.

“It will be an interesting challenge to see how you’re going to impregnate that sexy little wife of yours, when you have to rely on the permission of your Master to even fuck her, isn’t it?”

“Y.. yes, Master.”

He looked me right in the eyes, his gaze burrowing its way into my soul. 

“Crissy, is your wife on any birth control?”

I felt my heart pound as a moment or two of silence lingered before my answer.

“No, Master. She isn’t anymore.”

He just smiled at me with a new and even more sinister glint in his eye. 

“I shall be thinking about this more, to be sure, but for now we have men arriving soon.  Best get you prepared. Remove your plug, and replace it with your dildo.”

My heart was pounding, my mind racing, but I obeyed. The plug had stretched me some, but the dildo was still larger and longer, so I felt it invade me with a fresh intensity. 

“Sit down, so you can see the computer.”

I obeyed, seeing Brooke continue to please herself and torment her viewers, her wide smile only growing. 

He guided my wrists behind me and used a lock to link the cuffs together. He knelt down and guided my ankles back behind the post of my swivel chair, and similarly locked my ankle cuffs together. Lastly, he brought up the gag and had me open my mouth to accept it. The ring forced my jaw open wide and he pulled on the strap to make sure it was snug before buckling it behind my head. He placed my headset on me next, so that I could hear her words and sounds, without having to play them out loud. 

“Be good, slut. Feel free to bounce on that toy cock in your ass all you want. I’m quite sure the cage will keep you under control. In time you’ll be able to orgasm from just that stimulation, but I’m not convinced you’re desperate enough yet.”

There was a heavy knock on the front door, and he left me to answer it. As he left me alone to this torment, he shut off the light and closed the office door behind him, but not all the way. A sliver of light fell into my office, and I was sure that anyone who walked by would see my humiliation illuminated by the light of the computer screen.

I heard Liam’s voice, welcoming in the men. There seemed to be a crew of at least two or three of them, with gruff voices and heavy footsteps as they made their way into the house and downstairs. It was harder to hear them then, and my focus was taken by Brook and her low, sexy voice. She had stripped down to a bra and panties now, and her stiff cock was in her hand as she stroked herself with a slow, steady pace. 

I stared at her, entranced and aroused. My caged cock was denied its ability to harden, and I wasn’t even allowed the sensation of the panties against it. All I felt was the dildo in my ass, and the way it felt when I tightened my muscles around it. There was something about her that was so sexy, so entrancing, and it just drew me in. There were times I could imagine her thick, smooth cock in my mouth, as Master’s had just been. In other moments, I imagined myself as her, somehow transformed to be as feminine and sexy as she was, with my own former self all but completely lost. 

It was exquisitely agonising, watching her without being able to move or touch myself at all. My cock ached and leaked, and I squeezed and rode the toy inside me as best I could, even though it only tormented me more. With the gag holding my mouth open, I was soon drooling, with a trail of saliva constantly slipping from my lower lip down over my chest. 

It all went on for hours… Brooke’s show and my teased agony, and the work of these strangers down in the basement below me. More of Liam’s plans were taking shape in my house once again. I was also becoming amazed by Brooke’s ability to stroke herself and keep her cock this hard for this long without exploding in orgasm. She seemed to be able to last forever, waiting until her viewers chipped in enough cash to earn her total arousal. 

I moaned softly in agony, and even more so when I heard Brooke speak my name. 

“I understand we have a viewer who can’t speak or type, thanks to how her Master has left her… so I just wanted to say hello Crissy! You’re a good sissy slut, and your Master Liam wants us all to know that he’s enjoying having you as his very own plaything!”

There came a time when I was convinced that Brooke was moments from orgasm. She was finding it harder to speak more than a few words at a time, and she was moaning more than she was speaking. Her cock raged and she was gripping it so tight. I began bouncing as much as I could in my chair, riding the cock inside me and feeling every bit of my own agony. 

She was on the edge, I could feel it, and I felt right on the edge with her. I squeezed the dildo with my ass, and I moaned softly, feeling like I was right with her. Hearing the men come trampling back upstairs at that moment left me close to tears. 

I heard Liam thank them, and give them brief instructions on how to move forward, and with that, the sound of them faded away and the door closed behind them. I heard him approach and as he pushed the door open, I felt like he saw my every thought. 

“I trust you had a good time,” he said with a smile, and proceeded to unlock my restraints and remove the cuffs at my wrists and ankles. 

I did my best to gather and stead myself but there was an obvious stain of precum leaking at the front of my panties. Still gagged, I was also still drooling and unable to respond to him. 

“You may remove the dildo from your ass, slut, but put the plug back in. I’m sure you don’t want to feel too empty. Then put on some pants and a shirt. We have an errand to run.”

My eyes widened and my fear rose again. His eyes on me expectantly ensured my helpless obedience. I replaced the toy in my ass with the plug, feeling its presence smaller but still a teasing one. I then pulled jeans over my stockings and panties, and pulled on a shirt. He simply nodded at me and started towards the front door. My eyes darted around, hoping desperately that no one was around, as anyone giving any more than the quickest glance would surely notice not only the gag but also the collar still locked around my neck. 

Apparently oblivious, Liam walked to his driveway and to his truck where he opened the door for me. I stepped up and in, and he closed the door. I stared out the windshield in disbelief as he walked around to the driver’s side and got in.

He started to chat as he pulled away. 

“You’ve had a lot to think about, I’m sure, so you may have forgotten our discussion about your fitness program. To start, you’ll be limited to about 1800 calories a day. You won’t have to achieve all our goals with just willpower, however. In addition to a personalised exercise program, I’ve also set you up with a doctor friend of mine who has prescribed some vitamin supplements, appetite suppressants, things like that.

I nodded, wiping drool away from my lower lip. 

Thankfully, when we parked outside the doctor’s office, he removed both the gag and the collar. 

“I’ll be here when you’re done,” was all he said as he handed me a business card.

I took a deep breath and slipped out, gazing at the card as I made my way to the entrance. I was looking for a Dr. Pim, it seemed.

Inside, the place looked clean and professional and even boring, just like any other doctor’s office might. I found the apparent normalcy of it all reassuring. I approached the distracted receptionist.

“Hi. I’m here to pick up a prescription from Dr. Pim.”

“Take a seat,” she said. “The doctor will call you in a minute.”

“Oh no, that’s okay. I’m pretty sure I’m just supposed to pick the prescription up.”

“All new patients have to be seen by the doctor. It will be just a minute.”

“Uhm, well, okay,” I stammered and took a seat. 

I paged through a couple old magazines as I waited, feeling incredibly aware of the plug inside me, the cage locked onto me, and the lingerie covering it all. 

“Chris, Dr. Pim will see you now,” called the voice of the receptionist. 

I stood and headed down the hall that led me past the reception desk. The doctor was waiting for me at the door of a small exam room, and ushered me in as I approached. She was tall and thin, with straight blond hair. She was shorter than me, even wearing high-heeled leather boots as she was.

She was reading from a clipboard and spoke without looking at me. 

“Remove your shirt and pants, and you can put on the gown if you’d like,” she said.

“I’m sorry, doctor. I thought I was just picking up a prescription that Liam had arranged…”

“Yes, I’m familiar with who you are and what you’re looking for. In order for me to prescribe what we’re talking about, I am obligated to do at least a basic evaluation and interview, and go over the possible side effects. Trust me, we’ll have you out of here in no time.”

“It’s just that, well, I wasn’t expecting this today.”

How would I explain to her that I was in panties and stockings, never mind the rest of it.

“Don’t worry, Chris. I’m familiar with the kinds of patients that Liam tends to refer to me. I’ve seen everything.”

My face was burning, but I admitted defeat and began to remove my clothes. Once I was down to panties and stockings, putting on the paper gown seemed silly, and I didn’t bother. 

She was businesslike, giving me a thorough look over, taking my weight and basic body measurements, blood pressure and pulse. At her instruction, I lowered my panties as well, so that she could inspect my cock and balls, as much as they were available. I also had to bend forward and spread my ass cheeks, so that she could inspect me from behind as well. She gave the base of the plug a few taps and tugs, as though she was testing its tightness within me.

“You’re not using a very big plug yet, though that may change,” she said. “As much as you can, try to increase the size gradually, so your body has time to keep pace. I’ll remind Liam of this as well, as I imagine you will have his guidance in making these decisions.”

“Yes, Doctor, that is safe to say.” I blushed.

“So, let’s talk about your meds. I’m prescribing three different pills that you are to take daily. One is a fairly standard multivitamin. The other two are a little more than that. The second pill acts primarily as an appetite suppressant, and the third is most accurately described as a kind of hormone treatment. It is not hormone replacement therapy, but it does include some estrogen in the mix. The treatment changes the way your body processes the fat in foods, which will really help you shed weight, as your body will naturally just pass the kinds of fats that you might otherwise hold on to. While there are some side effects, I believe they are outweighed by the positives. Your whole body will thank you for losing weight, from your heart to your joints, and the earlier you start, the easier it is. Do you have any questions so far?”

“Well, can  you tell me more about the possible side effects?”

“Of course. Some people experience a bit of nausea at first, but that is rare. As a man on these treatments, you may notice some change in how often you need to shave, though other physical symptoms of that kind are very rare. Most likely in that category is possible nipple sensitivity. The medications may also reduce fertility and cause some ED, or erectile dysfunction. Given the current state of your genitals, however, I don’t imagine that will be much of a concern.”

My mind raced with those words, spoken so casually. 

“Do you mean that I’ll be impotent… or that I won’t be able to get hard at all?” I asked, trying not to stammer.

“Reduced fertility is more common, but there is a chance that both might occur. If you do experience these side effects, don’t worry, they should only last as long as you’re on the medication. I mentioned this all to Liam. I take it that he didn’t pass that information along yet?”

“No, he didn’t. It is just that, well, my wife and I had talked about starting to think about trying… trying for her to get pregnant.”

“Yes, Liam did mention that. I wouldn’t worry about that. Liam arranged to be tested, and he will have no problem stepping in for you in that regard. He made it clear that you weren’t likely to have permission to have sex with… with Cheryl, isn’t it?”

My face burned red and I felt like I would melt right into the floor. This doctor, this woman I’d never met, was talking so matter-of-factly about how another man was talking about impregnating my wife. 

“Well, that’s about all the information I have to give you. I’ve given you a six-month supply for now, and you can call for a renewal after that. You can get dressed now. Good luck. I think that you’ll feel a lot better once you see the weight coming off. You’ll look even better in panties.”

I dressed in a daze and wandered out of the office. There was Liam, waiting, a smile plastered across his face. My cock, trapped in its cage, twitched and tingled.

What in the world was happening to my life?