Training My Sissy Body

His profile was pretty straightforward on the site. He didn't seem to want anything for himself, although I'm sure he'd enjoy the process immensely. I'd come across the advert during one of my many late night online sessions. You know the ones, you have a little wine and start looking at who is local, and maybe going into the chat rooms. I'm not new to this, I've been dressing since I was very young. I used to suck one of my friend's cocks after school most days, and that had grown into meeting guys and other TVs through university. My dressing had got to the point I was pretty cute when dressed, and guys certainly approved. Of course I was hairless. I used a depilator to stay as smooth as possible, along with waxing the more intimate parts. I'd gotten into chastity through the various "sissy hypno" porn videos I'd seen, and it was a huge turn on, although I'd always been in charge of the key and would always free myself and jerk off in the end.

What drew me to Benn's profile was that he wasn't offering keyholding or denial. He was offering to train a sissy. Even better, he had a fucking machine, I'd always wanted to try one but on my wages it was simply out of reach. Benn seemed to be pretty well off and lived in the nice part of town. He said he lived alone and was happy for a sissy to move in so she could spend more time with the training. My own room, use of a fucking machine, free food, it sounded great. He'd get to use me for blowjobs and anal, but I wanted that anyway especially looking at the pictures of his perfect 8" cock on his profile. After my third glass of rosé, I messaged him to say hi and asked about the machine. One thing led to another and I agreed to go over that night. I was a bit drunk, but I wanted this. I figured I'd spend the night and see how we got on.

I messaged him by phone as I approached and the porch light came on. I preferred this to knocking just to make sure I was at the right house. He answered the door wearing some smart suit trousers and a shirt. He'd been working while messaging, he said he worked a lot and that it would be nice to have some company as well as some release through the day. He smelled wonderful; I think it was an Armani scent. Everything about him said success, although that success had clearly cost him as he lived alone and was working at 10pm. I walked into the impressive home, a little nervous but feeling more at ease since seeing him.

"You can dress through there" he said, pointing to a bedroom off to one side. The house was all on one level, and an impressive size. The corridor had several rooms, all of which looked neatly presented. I walked into the bedroom and saw that he'd been preparing for his fantasy. The closet was full of outfits all designed to show off a sissy nicely. These were not ordinary girl outfits, and I don't think he planned to turn me into a presentable girl. No, these were designed to make people horny. While I was in "boy mode" for arrival, I did have underwear on and discreet makeup as well as my breast forms in a bra. As I walked I pulled on my wig too. "We can start tonight if that works for you?" I wasn't sure what he meant, I had expected to come over and suck his cock straight away. "I have some work to finish off, but no reason you can't get started with the training". This was an interesting turn, I was used to guys getting off and kicking me out. "There's a cage on the bed, put that on and we'll get started". The cage was small. Much smaller than I'd ever seen before.

"That looks a little small compared to what I usually wear" I said meekly, hoping not to disappoint him on the first night.

"Well, we're not trying to deny orgasms here, we're training you to be a good sissy with a little limp cock and a loose pussy. The smaller cage will mean you can't get even a little hard. You'll wear it most of the day but we'll take you out and get you off every day too, it's part of the training".

This sounded like an interesting approach so I figured why not? I could always back out if necessary. I picked up the shiny metal cage and looked at it properly. It had the standard ring which would go behind my balls, and a solid metal dome an inch long. The dome had a urethral tube for pee, which would also make it more secure. There was lube on the bed next to it, so I picked up the lube ready to apply it to the tube before inserting it. I was hard as a rock, so this was going to be a challenge. Thankfully my panties were containing my erection for now, but I'd have to remove them to put it on. I undid my jeans and pulled them down, then took off my top to reveal my fake tits and sexy bra. With the number of meetups I'd had I was fine with undressing in front of strangers, especially when I intended to suck them off!

"Looks like you have a little problem, we'll train that out of you soon enough, and then you won't even need the chastity. Your panties will be enough once you stop getting erections, and you won't even be able to fuck anything if you try." he said this like it was the most natural thing in the world.

Did I want to go through with that? "Surely without chastity I'll always be able to get hard" I thought. It was such an exciting thought though, the only sex possible being anal or oral. Voluntary, permanent impotence. Never being the top in a situation seemed like the ultimate submission.

"Let's sort that out. Here, stand up straight." he went to the dresser and returned with a tiny pink vibrator and some leather wrist restraints. "Don't worry, the restraint is just to make sure you don't lose interest after you cum" he said as he approached me.

"I don't really like to cum during meets, I prefer to focus on you" I responded, knowing that when I cum I definitely do lose interest. Although he clearly heard me, he carried on silently and pulled my wrists behind my back, securing them with the restraints. I didn't even try to fight as I wasn't sure what his plan was. The tiny pink vibrator was only about 3" long. Probably just big enough for one AA battery, and certainly not designed for penetration. While this was happening my erection had gone down, so by the time he finished with the restraints I was getting soft.

"Ah good, we can start immediately." he said, as he started the vibrator and held it against the underside of the head of my little cock. "We need to train your clitty not to bother getting hard. You'll only cum when soft from now on, but I will let you cum. This isn't about abstinence or denial, it's about helping you to be the horniest little fucktoy you can be. You'll learn to get pleasure from sex as a sissy as you lose the will to have sex as a man." As he said this I could feel the vibrations in my cock, and it started to get hard again both from the sensation and from his words. The idea of becoming a limp fucktoy really got me hot, but as I started to get hard he pulled away the vibrator.

"No." I whimpered as he pulled away. I needed to cum, I was hot and horny and this felt like torture.

"Only when you're soft. We have to stick to the training and be consistent. You don't need to be hard to cum, and you shouldn't want to be. I want you to say it and think it over and over again. Make no mistake, this is brainwashing to achieve your goals, and we need you to internally brainwash yourself as it happens."

As he said this I thought "he's right, I don't want to fuck anything. Why would a sissy like me need to be hard anyway? I don't need to be hard". As I thought this, my erection went down and he resumed the vibrations.

"Keep repeating it in your head" he said, and so I concentrated on the words.

"I don't need to be hard, sissies don't need a cock" and things like that. It took only a couple of minutes for me to cum, during which time I got hard twice more, and each time we waited for it to go down. As I came he caught my cum in his hand from my very soft cock. It felt weird to cum with a soft cock, it was still unmistakably an orgasm, and release, but less powerful like I could manage more of these. I did get that feeling of clarity, though I was still pretty horny, and I did want to stop.

Before I could say so though, he held his hand up to my mouth "lick that up, sissies need the taste of cum, they love the taste of cum". He was right of course. The reason I'm here is because I love being a sissy and want to be better.

As I licked my cum from his hand I said it in my head. "I love cum, I love the taste of cum. I should enjoy it all of the time, not just when I'm horny". It helped, although I wasn't feeling it I finished the task and felt grateful that he was helping me.

When I had cleaned the cum from his hand, he pulled my balls through the ring of the cage. It was cold at first but quickly warmed against my body. He lubed the pee tube and slid it carefully into my cock then pushed until the metal dome covered my cock entirely. This pushed it back into my body a bit but it did fit and he quickly pushed the lock in sideways and removed the key. "There, now you can't even start to get hard. The secure feeling will grow on you and will help you not want to be hard." as he placed the keys on the bedside table he said "These will stay here. You're not trapped, this is a training device to stop you getting hard. You want this so I expect you to only take it off for cleaning and cumming. You can cum as often as you like, as long as you're soft and use the vibrator. It might be better if you keep yourself horny at first, though. I'll test you occasionally by making you cum at the start of play time."

As I considered this unusual approach to chastity, he pulled me through to a side room where I could see the fucking machine next to a leather padded bench. My heart skipped a beat, I'd never seen one in person before and this was very exciting. I'd finally get to play with a real fucking machine. The machine said "Willy Wanka" on the side and it had a wheel with a spiral of holes which attached to the shaft which would hold the dildo. I had researched these and fantasized for years. I knew that the holes allowed me to set the length of stroke to match a dildo, or to achieve a particular feeling.

"Of course, for the moment you won't be in charge of the settings. I have a training program set out for you for proper stretching. It's like at the gym, if you have a goal you need to use specific training to achieve that. We're going to start you off with the B7 Tango dildo, it has three bulbs like butt plugs, each slightly bigger than the last. I'm starting you today on the first and it'll move slowly in and out to stretch your hole. Because it goes in and out hundreds of times, you'll learn not to resist and your pussy will get nice and relaxed for anal. Eventually you'll take all three bulbs and move on the to the bigger B10 Tango, but that could take months."

My cock felt like it wanted to get hard but the cage stopped it. I started the mantra "I don't need a hard cock as a sissy" in my head to reinforce my training. It helped.

As I was doing this Benn lowered me forwards onto the soft bench in front of the machine. With my arms still secured behind my back he had to help me down. Once down, he did up some straps around my thighs and back, and released my arms moving them to the front of the bench before strapping them securely to the front legs of the bench. I wasn't going anywhere, but I was certainly comfortable. He set up the B7 dildo on the machine and set the thrust length so that only the first bulb would enter. This meant my hole would go from closed, to maybe 1.5" then down to 1" as the bulb was all the way in, then back out so I closed up. He applied some lube and placed the end of the dildo against my hole. When he turned it on I was surprised to find it quite slow. It gently pressed forwards with unrelenting force until the head popped in, then reversed. A total stroke of maybe 2" so it wasn't deep but I felt the stretch.

He left the machine running then set up the screen in front of me to play a sissy hypno playlist on loop. This began showing me sexual images of BBC, anal, chastity, with slogans and messages on the screen reminding me I was a sissy with a limp cock. All the while the machine was pumping slowly in and out. Not quite the image I'd had of a fucking machine but it was pleasant enough, and I love sissy porn. "I'll be back in ten minutes, don't forget to read the words and say them in your head, it'll reinforce the messaging better". And with that, he was gone.

Alone, I couldn't do anything but watch porn, think about the messages, and accept the dildo once a second or so. This was probably the most relaxing experience I've ever had, there's no room for new thoughts or for day to day stress to intrude, your mind only has sissy captions and anal play to worry about. I started to relax, knowing I was in Benn's hands. "Maybe I am better off with a limp sissy cock and letting men fuck me" I thought. At least it's easy, although I could do with a bit more penetration than 2" to get me off. Even the girth of that first knob had become a little too easy, my ass was open and stretched and no longer even closing up between thrusts. Why would it, it would only be forced open again a second later.

Just then, I saw Benn return out of the corner of my eye. "Well how is it going? Hopefully you've worked out who is the sex toy and who is the machine now." he said. I hadn't thought about it, but he was right, I am the sex toy in this scenario. The machine is just training my body to be a better sex toy for a man. The more I thought about it the more it made sense.

"I'll just stop this and adjust" he said, as he expertly slowed and stopped it at full thrust inside me. A few seconds later he'd moved the bolt and was ready to start it up again. I assume he must have marked the correct holes as it was perfectly set up now for two knobs.

The shaft first pulled the bulb out and then turned and thrust forwards. This time I felt the first bulb enter me but then the second, slightly larger, began pushing. I felt a stretching sensation before it popped in and began to withdraw. As it pulled out I felt the stretch again, followed by the first easier bulb. It was relentless and thrust in and out repeatedly, and I soon got used to the new stretch.

"There, now you're set up for the next hour or so." Benn said as he moved the screen in front of me. I hadn't noticed the padded seat before, as it was under the screen. He sat down, no longer wearing his trousers or underwear, but still wearing that sexy shirt. Clearly he was still busy at work. "I need to de-stress before I go back in. I've a meeting with Tokyo, hence the late night, but thinking of you starting your training has me worked up."

All I could think about was his cock in front of my face. "A sissy doesn't need to know about business, she just needs cum" I thought, reinforcing the messaging as much as I could. I believed it as well. I didn't need to know that stuff, I just wanted to pleasure my man and swallow his cum. He shifted forwards and put his hard member in my mouth. I eagerly sucked and tongued his head for several minutes, while the machine stretched my ass and it returned to a rest state allowing the bulbs to come and go without resistance.

He placed a hand on the back of my head but was very gentle, allowing me to pleasure him. When he came I felt him pulse several times and my mouth filled with cum. He'd obviously been horny as my mouth was almost overflowing. I swallowed a couple of times and gently cleaned him off before he pulled away. He reset the screen after standing back up.

"Very good girl, I thought you'd get into this quickly after our messages. You were clearly made to be a sex toy. You're looking very comfortable with the second bulb already, I guess you've stretched yourself before with dildos."

He was right, I regularly hammered away with a 10" realistic black cock at home so although this was stretching me it was far from uncomfortable. He stopped the machine again and set it to thrust all the way in, with the third and largest bulb. As he started it, he also turned up the speed and restarted the porn. "Back in an hour, enjoy" he said as he walked away to his meeting.

With the thrust speed increased, my pussy was almost vibrating with the speed the dildo moved and dilated me. There was no way to resist, I felt myself expand and contract three times on the way in then three times again on the way out. I couldn't even sense the changing sizes this time, it was just one endless sensation. At least the thrusts were now a full 7" long so I was being penetrated properly. My cock had started to leak precum through the cage but was no longer trying to get hard.

"A sissy doesn't need a cock, why would I get hard" I said to myself as I watched a tranny on screen get fucked by a very large black cock. She was in ecstasy, and I could see why. I wanted a cock in me, but Benn would be gone for another hour so all I could do was watch. After some time I began to feel a bit distant and paid less attention to the details on the screen or to the pounding in my ass. I just felt right and wanted this to carry on forever. This must be the sissy state people talk about, just accepting myself as a fuck toy. I relaxed and let it all happen.

Eventually Benn returned and turned off the machine. It was well after midnight at this point and I felt ready for bed but extremely horny. He also turned off the porn in front of me, which brought me back to my senses a bit.

"You must be very horny after all of that. I'm going to give you some relief so you'll be able to sleep tonight." At this I was kind of glad the night would be over, but a little disappointed he wasn't going to use me some more. Benn unlocked my chastity and removed the cage, and brought out the tiny pink vibrator again. This time I didn't get hard at all, and came within 30 seconds. Since the wine had worn off long ago, and I'd cum again my clarity returned and all desire for playtime was gone.

Benn had other ideas though, he presented me with a little dish of my own cum. I hadn't seen him put this under me since I was still secured to the bench. I knew what I had to do so licked up my cum and swallowed. I wasn't really enjoying it, but made a point of mentally repeating "sissies love cum" anyway as it was starting to feel natural to brainwash myself during these activities. While I lapped at the plate full of semen, he reattached the cage and locked it in place. I didn't really mind as I was spent, and the keys were next to my new bed anyway so if I woke in the night with a painful erection, I could remove it.

"I guess you're ready for bed now, but I'm super horny after that so before we get to sleep I need some relief". I assumed he meant another blowjob, and I figured he'd earned it but I would rather get some rest. "I want you to be aware of what we're doing, so I'll leave the porn off. I gave you an orgasm first so you would be completely aware and up for this too. I'm going to fuck you now and I want you to understand that you want this. You might not think that just after cumming, but remember why you came here. You love cock, you love anal, and this is the real you."

As he said this he turned on a camera which showed me myself in the room with him behind me. I still looked quite pretty, but a little dishevelled. "I want you to look straight into the camera and tell yourself what you want".

I considered my situation and knew he was right, I did want this. Or at least I wanted to want this. Not just now, I wanted to be like this all day every day. I never wanted to lose that feeling of wanting a cock, it was always there even when I had just cum but for some reason I talked myself out of it. "Let's change that" I thought, as I looked into the camera.

"I want you to fuck me. I want to give you relief before bed, and I want to want cock all day every day. I don't need to get hard as I'm just a sex toy for real men who will fuck my face and my ass whenever they want." It felt good to say it, and as I said it I realised I meant it.