Story: Mistress Alyssa’s Sissification

Hey sweeties,

Trainer Frida here, and I’m eager to share a conversation I had with my friend, Head Mistress Alyssa, which led us down an incredibly thrilling path of feminization exploration. Alyssa used to work professionally full time, but is now running her own business. One day the topic of forced feminization came up.

How can many desire to be “forced” when it essentially implies experiencing something unwanted?

In fact, this phenomenon is quite prevalent in BDSM, with many women fantasizing about it. It involves playing with power dynamics and the subject’s loss of control. However, this doesn’t mean anything goes. We are cautious when selecting and planning, researching, and understanding our subject thoroughly.

The concept of “converting” a carefully chosen subject and getting them involved in something they would seemingly dislike or disapprove of can be an intriguing way to witness genuine submission.

Maybe it is only possible to feminise boys that already have a deep down desire to explore their feminine side? Or… maybe not?

Perhaps those who can be fully “converted” to embrace a feminine identity already had that inclination within them. They might have been girls, possibly lesbians or tomboys, but as they delve deeper into living as a girl, it feels increasingly right. In many cases, we might just be liberating the inner girl who has been suppressed due to societal expectations and cultural pressures.

Or maybe they get so submissive and let things play along, until their conflicted mind gives in and up? 

Mistress Alyssa believes that with the proper motivation, tools and that it might actually be possible to do this with more or less *any* submissive man. 

On the other hand, we both doubt that a typical straight alpha male could be feminized, especially to the point of engaging in sexual encounters with other men. Wouldn’t that require a submissive inner desire we could ignite?

We often argue that nobody is entirely dominant or submissive. Claiming to be 100% one way or the other often indicates a lack of experience or maturity. What does that even mean? And those who assert such an extreme position are usually driven by fear of the “other side,” which often manifests as black-and-white thinking.

Adopting a rigid stance indicates a reluctance to accept the complexity of the world and the fact that there’s more beneath the surface. For a straight man to admit having a sexual thought about another man, they’d need to be quite secure in their sexuality. Although every man has had such thoughts occasionally, it’s the fearful ones who adopt an extreme stance. We aimed to first experiment with a sexually inexperienced submissive boy to see what might be possible.

So we posted an ad on a BDSM place for this purpose, it read something like:

“Seeking an inexperienced straight male slave for five months of video training”

The photo showed me but with my face in shadows and the blonde hair to the side.

We had a list of requirements.

Of course we got massive amounts of replies to that.

So we had a few submissives and students of ours that helped to sort through all applications.

The one we picked seemed to be a nice and honest guy, instead of just crazy focus on sex, he explained how he had been more and more curious about being dominated after his last ex had tried that on him. 

So I had a video chat with him. I was quite casually dressed up and said before that the interview was just to be a normal everyday conversation and not revolve around kinks, BDSM, the training, just a first ‘get to know each other’ time.

He was not into sissification as far as I could tell. I tried hard to not ask direct questions about this and he did not seem gay. A quite normal straight guy. I would say a bit nerdy and computer oriented but quite capable of a normal conversation. He was of course super nervous but that was to be expected and a great sign that he was taking this seriously.

After talking to Alyssa we agreed our subject was confident enough for our experiment, and a quite good candidate overall.

I did not want to spend hours on a video camera with this guy, so we found an online dom to help us out, and we negotiated a weekly price for her to do the training.

I had another video call with our subject, let us call him Johnny. This time he got to answer long questionnaires about various kinks, and experience with them plus how he felt about the training program. He still did not really know what it was about but I made sure there was nothing in our plans that was a hard limit for him. We also discussed a bit how he would feel about having his limits pushed a bit, and he seemed a bit unsure but also admitted to it sounding quite hot. We then mapped out his life. I wanted to make sure that our “conversion training” would not cause problems with his living situation, work, relationships, family and so forth.

This guy was into bondage, submission, latex and feet worship, but not into anal, feminization, chastity, edging & denial, bi-curious exploration, and cocks. 

Our secret training plan was to open his eyes to these things and see how far we could go.

The rules were simple. He of course had to pay for the online mistress we hired, for any toys he would be ordered to buy, and every week submit an honesty questionnaire about how he felt about the training. If he missed a single meeting with the assigned mistress, or to submit the questionnaire then he would be out, and we would accept no further communication with him whatsoever.

The first week we got a report from the online Mistress Lucy that we hired to do the training for us. We asked her to have a revealing top and a key dangling there. This would play an important role a bit later on.

He had done well and had been obedient. While following orders from Miss Lucy to touch himself he was ordered to make moaning female sounds. This was to associate submission with acting like a female. Over that week he could only cum with permission and this was to associate desire to someone else having control over him. And he had to buy a tiny lipstick vibrator online, and a few different sized cock-rings out of metal.

The 2nd week Mistress Lucy used more language that connected being a submissive to being a female, and he was called Jona, a neutral but more feminine version of his name. This week most sessions were about edging and practising how close they could make it. He was also trained to learn to punish himself by spanking himself and squeezing his balls. This was so we could start to associate some mild pain and punishment to pleasure and domination. She also used the cock rings to determine his size, and he was ordered to have them on for a few hours before and after each session.

And at the end of the 2nd week he was ordered to buy a very small dildo.

As the 3rd week started he had a video call with me in person. In this call we opened the vibrator together and I asked him a bit of questions about his training. He seemed quite ecstatic and super excited about the training and asked me a lot of questions about what was coming. I dodged all those questions and was very strict about that if he misses out one single time we will end all contact, and that he is free to do so at any time. Otherwise he will continue to have an experience of his life, but that it would require dedication, a lot of training on his own to stick with the orders he is given through ups and downs. 

The 3rd week they started anal training with the vibrator. And more of the sort of humiliation that he had rated highest desire for connected to acting like a female, and the anal sex. Plus he had become so comfortable with one of the rings that he was ordered to wear it whenever he was home and to sleep with it on, and this had worked well.

At the start of the 4th week I was with him to unpack the dildo. He was never allowed to unpack things on his own. He did mention he was not into cocks or anal sex, so I asked him if the last week had not felt good, but he admitted it had been quit arousing to do that and that he had cummed several times after some sessions. I explained to him that this will just be better if you continue but you need to trust the program. Again I gave him the choice to back out with no hard feelings, but he decided to continue the program.

The 4th week included him licking the small dildo and teasing his butt, and the end of the week he had so much associated pleasure with the dildo that when Lucy asked if he wanted to fuck himself on camera that he agreed without hesitation. He now had also been trained to use and sleep with a cockring one size smaller, and outside being a bit annoyed of having almost constant erections during night and when home, this seemed to have worked out fine.

At the start of the 5th week he did not get a video chat with me. Instead he just received an email with instructions. The instructions was to go to a local sex store and be ready to pay for toys there for a specific amount of money. We had already contacted the store and prepared for this. He was to print a list that contained “A medium sized dildo, a large sized dildo, a pair of breast forms, and a black lingerie outfit with open crotch and pull ups, a pair of net pull up socks, matching net gloves and a bra that fit the breast forms, a cute pink collar that said “Jina”, a female wig of fair quality, a short skirt, a simple enema kit, a small butt plug, and some makeup. At the bottom it said:

“Ask the staff in the store to help you collect these things, and then pay for it plus a secret package to Jill. That is your new name from now on, and if they ask you what your name is then you must say your name is Sissy Jill. After payment is done then ask them if you can try to stocks while they help you on with the secret packet. You must take a shower and be properly clean all over before you go there.“

We made it out to be the “next level” and so it was again all okay, even understandable, if he wanted to back out at this point. He was warned that it would probably be very embarrassing and humiliating what was going to happen in that sex store but that it was all between us, the people working there and Lucy.

If he were to commit to this, then he would have to commit to give up more control than he had so far to the program. And that he would agree to 24/7 carry something locked onto him as a sign of his submission. He would not know what it was, but it would be something that no one else would notice, so maybe something around the ankle, or wrist. The most important thing was that it would be locked on and there would be no way to take it off except with the single key that comes with. And that he was to post the key to Lucy. And of course we attached a picture of a key dangling in front of her breasts.

I had talked to the local sex store staff to arrange a few things. I was a bit nervous if all the energy we had spent would matter or if he would back out now. 

I got a call from the sex store and one of the staff talked to me about what was happening while the other one welcomed Jona, well Jill rather.

Jill was apparently quite red all the time in the store. The girl that helped him had apparently gone to the same school, and she was making a lot of comments about the shopping lists. Of course normally the staff in stores like these are very kind and understanding, but of course they had gotten a few instructions by us to spice things up.

Some humiliation like this was important for what was coming. Humiliation in a safe environment, with kind people, can create a sense that it is not as bad as it feels. This was important because this was a quite small step for what was coming.

If was so adorable to hear Jill struggling to stutter the words while trying to ask for that last request. The attendant helping him had whispered back to him if he would prefer a man instead of her to do it. Apparently then he had turned red and silent.

The attendant then said:
“The secret package is paid for, so it is yours to take if you want. The instructions we got says it should only be given if you chose to have it put on in the store. Since you have already paid for it, it is up to you to follow those instructions. We do not care if you would prefer to take it with you home instead.”

The reply from Jill was something stuttering like “Eh eh maybe… better to have.. what is it?”

The attendant giggled and replied with a calming voice “We promised to not open it before you were locked up in the stocks, but do you want to open it yourself then you may?” and she gave Jill this wrapped box in black.

Jill held it for a moment and then asked “We.. where are these stocks?”

The attendant smiled and said “It is backstage. It is all up to you.”

Since I was listening on the phone and having the events described to me I asked the girl I was talking to if I could talk to Jill in person.

The girl talking to me in the staff area then came down to the front desk of the store with the remote phone and said to Jill, “Here someone wants to talk to you”.

We talked for a bit and I just explained that we had this secret gift specially made and custom fitted, that it would not be visible to anyone with clothes on. I explained that the stocks, which are those big wooden boards that you put both hands and your neck through, was just a fun way to have it put on so that she would not be able to see it until she got home. It would be attached around the cock, and I explained that his is why you have trained to be wearing that cock ring for the last weeks. Jill was super worried that she would be erect in public, and I promised that this one they were going to put would ensure she could not get erect. She did not seem to understand how that would be possible but I just ensured her that it would.

Eventually she went with the attendant to the backstage room and got into the stocks. Apparently there was no issue to put it on since Jill was super embarrassed.

It was obviously a chastity device, but the design was a bit different compared to the normal ones. Normal chastity devices usually create a bulge, and in-addition they are quite easy to get out of. We had this new design that had the penis inserted into a small semi-flexible tube that was then attached to a g-string-like attraption that left the bum and “pussy” open for access. It was not made out of a hard material like steel, but of a softer woven one more similar to kevlar. It is probably impossible to cut with normal tools and cannot be ripped off with force. Since it is a bit soft it follows with the movements of the body and causes no pain or itching. Also it is also coated to be non-absorbent and skin safe, and so it is meant to be taken into the shower.

These devices are something we are still working on, and we have not yet found a way to manufacture them in a factory, and we have not found a way to make them from cheaper materials. So what Jill did not know was that this was a very very expensive handcrafted device – the price Jill paid was just a small tip to have the shop attendant put it on.

Then the attendant pulled up her jeans, unlocked her from the stocks and gave her a silver key along with an unopened letter that said “Open when you are outside and close to the train station”.

The letter inside said:

“This is the key to your new chastity belt. You will no longer be able to stimulate yourself unless you use the key to open the device. I want you to post the key to me. If you do so then we will continue your training. Otherwise it will end right here. It is entirely up to you. If you need some time to think then take a walk around the city. Treat yourself to some nice food at a restaurant. You have to make a decision before you get on your train home. If you decide to continue then post the key to this address <Address to a post box we rented in that city> xoxo”

Later that night Jill had a planned session with Lucy. Jill had posted the key and was in. Lucy reported how Jill had been so conflicted and also super horny about this whole thing. They continued the training, and after this point Jill was ordered to not touch herself down there. Not that she could anyway. Instead she was taught to massage her fake breasts and inner thighs. She was also trained in how to clean the device in the shower. 

The 5th week escalated quickly with her having two sessions with Lucy every day. She was dressed like a whore in lingerie at all time when home, and was asked to do more and more frequent anal sex. After a few days she was so horny that her cage was leaking and dripping wet, and her anal training schedule had her fuck herself anally to sissy and gayporn more and more often. In a session later that week she managed her first anal orgasm after fucking for about an hour. Lucy told me it was one of the hottest things she had ever seen. That the horniness that Jill showed was outmatched by anything she had seen. Lucy was quite surprised that Jill already seemed like such a different person.

The 6th week Jill got a letter that said she had to get her anal orgasm time down to five minutes. That she would have to train on her own. No Lucy sessions until this goal was reached, no talks with me or any further instructions. She would write down her anal orgasm times in her online training book, and only contact me once she thought she could consistently get an orgasm in about five minutes.

Then we just ghosted her. She sent a lot of messages to both me and Lucy but we never replied.

2 weeks later, at the start of the 8th week, she still had not managed to get down to less than 15 minutes. She was begging for release. I felt it was time to step in so I sent her a letter with a list of tips to get her time down.

• Prepare before you start the timer and start to fuck yourself
  • Put yourself in your submissive mindset
  • Learn to arouse yourself with oral dildo stimulation
  • Learn deep throating the dildo
  • Do tutorials on how to pleasure men & cocks so you can learn how to do a proper tease orally & anally as a warm-up
• Daily take care of your body and soul for being the best sissy you can be
  • Always wear your whore outfit when you are home
  • Go up the same time every day and start the day by reciting for 5 minutes how happy you are to be a girl, to be feminised, to take cock in all your holes
  • Keep improving and adding to your morning mantra
  • Get shaving essentials and shave all your body hair each morning
  • Mark three days a week and treat yourself to a pink bubble bath
  • Meditate for 5 minutes before you go to work and when you come home
  • Lie on your bed and listen to a sissy hypnosis audio for 1h before dinner
  • Go to sleep same time every night and make sure to get at minimum 8h of sleep
  • Watch sissy, stright-anal or transporn with cocks & cum 15 min after you go up and 15 min before you go to bed every day. Imagine you are the one receiving cock, and match your anal fucking to what is happening in the video.
  • Put on your best female makeup when you come home from work
  • Increase the time that you wear your butt plug, mark times you train daily and the duration in your training book
  • Get panties to wear daily & start adding to your female wardrobe to wear at home
• Change habits
  • Mark two days a week in your calendar and take a jog, note down the distance and time it took you in your training book. Increase the distance you run with about 10% each time without dropping in speed
  • Eat healthier. More vegetables and healthy fats from nuts, fish, avocado and so forth. It Doesn’t matter what you like or not. You are a sissy and need to switch your diet to be more appropriate, it will feel good to submit to a better diet
  • Learn to fuck with the dildo’s sucktion cup in all kinds of positions, research ways to take cock and initiate porn stars for inspiration
  • Learn to massage your body like a horny girl, and train moaning like a slut

Then we ghosted her again.

It was so hot to see the updates in the online training book with all the progress. She started to send more and more emails about begging for release. It was quite pathetic but after 4 weeks she said she made the time.

She was then ordered to have a session with Lucy to show this.

Of course she did not make it. Lucy shut off the feed at the 5 minute mark.

For five days after that she made no entries into the training book. I wondered a bit if we had been to tough and lost her. 

Then the entries started again.

Another four weeks passed and this time she was really getting into the lifestyle. The updates in her training book was consistent and multiple times per day. On her own accord she had added her porn watching sessions, what she watched, what hypnosis she listened too. And the time to sissy orgasm was consistently coming down the more she seemed to accept this as her life. On her own she had added a list of items in the training book, like a bigger butt plug, yet another dildo, more makeup, girly beauty and skincare products, more feminine clothes. 

Me and Alyssa were starting to grow more excited about our subject reaching the final stage.

At week 17, a bit more than 4 months of intense sissy training and 7 weeks without release.

Her time was down to 8 minutes at best. We never really expected her to get to 5 minutes, we just wanted her to embrace the lifestyle 100%.

I sent her an email that she would need to pick a tgirl. She would then have to have sex with her at a hotel. And if she went there and got fucked to anal-orgasm by her, that she would then get the key.

Of course for the safety of the beautiful tgirl, Jill would have to wear handcuffs behind her back at all time. Also this was going to be streamed for our enjoyment and she had to go to the hotell all dressed up full femme. So this meant going out to buy a pair of tight female jeans, a cute top fitting the breast forms, and send the wig to have it styled and touched up at a wig-styling place.

It took about one more week until she replied to accept the terms and with pictures of her with the new outfit and the items she bought. She looked surprisingly good. She really looked like she could have been born a girl all along. It was so hot to know how far we had gotten her.

The weekly questionnaires showed her desire for men, cocks, bi-exploration, cum, anal sex had been maximised to a 10 each, from a 0 to begin with.

The night at the hotel was spectacular. She went there, of course all cleaned up before in all holes and body all shaved, and we had a girl waiting in the lobby to show her to the room. She was given a letter with instructions in her hand, and then left in the room by herself. The bed was quite big and had pink soft velvet bed wear. The room was very girly and pink, the lights softly faded. 

The letter said:

“Dress off all your clothes. On the bed in front of the bed is what you are going to wear. Get into that outfit and kneel on the bed facing the door, put the tiny vibrator on and put it in your panties, put the pink blindfold over your eyes, and then lock your hands with the metal cuffs behind your back. Then just wait patiently for what is to come. We can see you in the camera right now. If you try anything then it is up to you to figure out a way to get your chastity device off. Prepare for what is to come darling, xoxo”

She took on the pink outfit that was provided for her, with a way too short skirt, pink net socks, a pink bow for her hair. She looked like something of a kinky-sexy version of a pink ballerina.

She sat there for probably 15 minutes.

Then the girl entered the room and told Jill in a very feminine voice to be silent, she then asked if Jill was ready and wanted some cock in her ass. Jill nodded like an anticipating girl. She was then asked to bend over and the girl helped her into a position with Jill’s ass up in the air, and then she undid the blindfold. 

Our sexy girl teased Jill with her finger, and talked about them soon having a visitor. Jill seemed a bit nervous but you could almost sense the horniness from her, and the willingness to just be fucked. She said in many of her letters that we ignored that this process had made her so horny and sex crazy, and it was almost like the only thing she could think of was sex. The latter weeks this had changed to anal, cocks, and men. 

Of course we knew it would all go away if she came, but the beauty of anal orgasm is that while they are much stronger than normal ones, they do not leave you in a state where all arousal goes away. Instead it is more like multiple orgasms that girls can learn to enjoy, that just makes you want more and more until you are sort of exhausted of energy, but then you wake up horny again the next day. Men are so sweet like that. Their strong sexual drive is so powerful that when you bend it and get them to continually trigger this growing sexual tension then they eventually learn to go into a sort of sexual daily hypnosis of desire and moldability. 

Jill was looking at the door as the tgirl started warming her up. Then the girl asked Jill to suck off her tiny girly cock. And Jill first hesitated and struggled against the cuffs a bit but then gave in and started giving an impressive blowjob. We could see she had trained a lot. Then the tgirl went around back again and started fucking her from behind with a strapon, of course Jill did not know that it was a strapon. Jill started automatically go into some sort of fuck trance and started moaning quite convincingly like a girl. It was all so hot.

And it was not that long until Jill started spasming from a powerful anal orgasm. And the girl went around her and asked her to suck her off. Jill seemed to not think and just slurped and cleaned up the cock. Then the girl went up and sat on Jill’s back and said. Now look at the door.

In came a guy, quite big and muscular. Around the neck the man had a key… It was the key to the chastity device. He was dressed in what looked like an expensive suit with hair cut short at both sides and with sides coloured blonde. A golden pin in the left chest pocket said “Daddy”.

Jill had watched enough sissy hypno porn at this point to know what was going on. 

The man said that he heard that there was this super horny girl here that had a love for cocks. The girl said that she loves cocks, but that she had not seen anyone cumming anally like Jill. 

Jill looked shocked for a while and then said something. The daddy moved close and lifted Jill’s chin up and asked what she said. Jill then said “May I have cock sir”. 

And soon the big man opened his pants to reveal a sizable erect cock. The girl hugged Jill from behind and whispered into her ear “Is this your first time?”.

Jill nodded and tried to reach for the cock in front, but the daddy pulled it away teasingly and asked “Just how much would you like this?”

Jill said “Eh ah, I am so horny, anything, please. I need cock. Please fuck me, let me suck you”.

Then that night continued as you would have guessed.

The daddy and Jill happily went home together. Jill is not “free” from the program but never went back. As far as we know Jill is still with this daddy, and this is two years ago, she is living as a fulltime girl and has transitioned at work as well.

Sometimes we wonder if Jill had it in him all along, or if we made it happen. I guess we won’t really know for sure. Though he.. I mean she claims to be perfectly happy, and that life has never been better. 

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