Forced Feminization Training

Hey sweeties,

Trainer Frida here, I want to tell you about a chat with a friend of mine, Head Mistress Alyssa, that turned into this amazingly hot feminization journey. Alyssa used to work professionally full time, but is now running her own business. One day I sort of brought up sissification, or as we often like to fantasize about it, forced feminization.

Now get me right here. We are both all about full consent. If there is not consent in BDSM then it is abuse, or worse. None of us gets off thinking about abuse like that. We find it wrong and it is clear to us that the BDSM community is much more evolved in this regard than the rest of society.

However, there is a silver lining here that we love to discuss mostly as a fantasy, which is this idea if it is possible to “convert” a well selected subject and get them into something they would claim to dislike or disapprove of.

You probably know my stance on sissification, I think it is only truly possible to feminize boys that already have a deep down desire to explore their feminine side. That those that one could possible get to “full-time” and 100% conversion basically already had it coming inside of them. They were basically girls, maybe lesbian, maybe a bit tomboyish, but they were girls and the more they explore girl-life the more then just find it right. I believe, in a lot of these cases that we are just letting out the inner girl that are trapped inside because of societal stigma and cultural pressures.

However Mistress Alyssa also 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 are both quite sure that would not be possible to feminize a normally straight alpha male. Especially not take it all the way into getting them to sexual encounters with other men. Would it not request a submissive inner desire that we can fuel?

We often say that no one is 100% dominant or submissive. If someone that says that it tends to be more of a sign that the person lacks experience or maturity. What does that even mean? And anyone that says they are 100% something are often just carrying this fear about whatever they see the “other side” to be. Fear like this almost always appear as black and white thinking.

Taking a strong stance is a sign one is afraid to admit the world is more complicated, and that there is more than meets the eye. For a straight man to admit they had a sexual thought about another man they would have to be quite confident about their sexuality. Of course every man has had such thoughts at times, but of course it is the fearful ones that take the extreme stance.

We wanted to first see if we could take a submissive boy, that lacked a bit in the sexual experience department and see what would be possible.

So we posted an add 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 requirement.

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 not to 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 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, 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 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 practicing 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 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 few 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 the 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 were 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 giving 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 not to 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 is this stocks?”

The attendant smiles 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 that was 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 special 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 this 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 attraction 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 to 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 talk 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 not to 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 have 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 gay porn 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 at home
    • Get 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 feminized, 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 get 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 more healthy. More vegetables and healthy fats from nuts, fish, avocado and so forth. Don’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 suction 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 to moan 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 did wonder a bit if we had been too 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 were consistent and multiple times per day. On her own accord, she had added her porn watching sessions, what she watched, what hypnosis she listened to. 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 was 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 “transgender” girl. 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 transgirl, 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 hotel 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 maximized 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:

“Strip off all your clothes. On the 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 on 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 transgirl entered the room and told Jill 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 transgirl helped her into a position with her ass in the air, and then she undid the blindfold.

The transgirl 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 addicted, 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 are 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 trans of desire and moldability.

Jill was looking at the door as the transgirl started warming her up. Then the transgirl 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 transgirl 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 transgirl went around her and asked her to suck her off. Jill seemed not to think and just slurped and cleaned up the cock. Then the transgirl 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 colored 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 transgirl 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 your cock sir”.

And soon the big man opened his pants to reveal a sizable erect cock. The transgirl 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.

53 thoughts on “Forced Feminization Training

  1. Sissy marki dunlap says:

    I would love to be in that situation . I’m sure that I am a sissy foggot looking for a complete and total fiminization were the only thing I can do is make sure that I can get them to cum filling me full of the cum I crave .

  2. Alyss says:

    I dream of situations like this…if this or something like this were to be done again, I would be first in line…

  3. Destiny says:

    This is a hot fantasy but would not be something that I would enjoy because I enjoy my masculinity and male identity but I also enjoy play time where a scenario like this would be fun and the hottest experience I would have ever had you see I have had this fetish since I was 13 but still at age 36 have not been able to find a way to truly explore or satisfy it besides playing alone in front of a camera so that it kinda feels like I’m being watched . Do you ever train or have sessions with members that aren’t the equivalent of changing my identity completely or exposing my fetish to friends or family?? I have been reaching out more to people in my local community more aggressively but it is very frustrating and disappointing that I can’t seem to find anything f that is what I crave also I am 38 now but was married twice from 19-35 and neither wife knew about my desires because I did r feel like they would accept it or me if I tried so I guess it’s been 3 years of trying to explore but a lifetime of wanting and self training

    • Marcia says:

      Hi Destiny,
      I get that, I have been wearing for a decade or so, just panties until a couple years ago. I would like to wear more often but we take care of my wife’s mom here, and she is here 24×7, they both are. My wife knows I like panties and has seen part of my collection, with her mom here it’s too hard to get into it.
      But back to the masculinity part, I have been struggling to understand the humiliation aspect of this training, and I like to say I get it, but I know I don’t really. I have grown up a similar sexual fantasy, but it doesn’t include being tied up and force fucked like a little bitch by three or more big cocked studs.
      Essentially a cum dumpster. Now before I get knocked down by anyone… Please, I understand that IS the ROLE that person wants to be in, and I defend that because I know in most cases it is concentual and agreements are usually made ahead of time for such things as a “Safe” word or gesture… etc…
      So it’s all good for the people who want it like that. I think something in my personality prevents me from seeing that as erotic, it feels like abuse to me, I stress ME here because I know the people who like it do not see it that way. And I do ge that part of it, I just can’t quite figure out why they see it the way they do, it’s not apparent to me is all I am saying. I can handle giving up control and be submissive too, I have, but I know I’d have an issue with just the verbal part. It’s difficult being part way there too, it’s probably why I dislike labels… Not sure which one to use..? Anyway, I get what you are saying.

  4. ShaniaCay says:

    I really liked the organization of events that occured in the plot of this erotic story. After thoroughly reading all of it. I couldn’t help myself.. but to imagine if this were to happen to me realistically.. But, I would have to add 3 very specific things to my version of forced feminization.
    1. A tall bulky “Amazon” Head Mistress. Being either a (Female) or (Transexual)
    2. Start working full-time at an adult sex store. Dressed as a Sissy Slut. And working part-time on the (weekends) as a webcam Sissy/TS online model.
    3. Forcefully fed estrogen/hormones.

    • Tony Epperson says:

      Kind of scary..but definitely very
      Took a lot to get the “subject “there
      I don’t like the idea of the Alpha male being there, but that was the desired goal.hmmmmm

  5. Dj says:

    A typo can be seen

    ” felt good, but he admitted it had been quit arousing to do that and that he had cummed”
    Quit should be quite

  6. Sissy Kelly says:

    I need this .. I need more from this site. I dont live alone I live with family I need to move with someone who can teach me everything and I can work and y

  7. Sara says:

    I have a fantasy and strong desire to be force feminized.
    One day I am out and about and a dominant woman sees me and thinks I have potential to be a good submissive girl. Whatever she had planned for the day she gives up on and follows me home. She makes a call to an alpha male and tells him to bring another guy for a kidnapping and to bring rope, chloroform and rag, cloth gag and blindfold. The men wait a couple hours after the lights in my place go out and enter my place quietly and find me asleep. One man doses the rag with the chloroform and presses it against my mouth and nose, and the other man holds my legs down. I am quickly bound, blindfolded and gagged. They pick me up and carry me out to a van thats in the alley behind my place, and I’m put in the back on top a mattress and my hands are chained over my head to a metal wall that separates the front of the van from the back.
    Hours later I am barely semiconscious and pull against the hospital restraints, and as I become more aware of my surroundings I realise I am in a room made to look like a mental health ward. Then I notice a tube running from an I.V. bag to my arm.
    “Hello, is anybody there?” I call out, but no sponse. Again, I call out louder this time, “Hello, is anybody there!? Let me outta here!”
    I hear a “click” and a door swings open, and a woman dressed as a doctor and two men dressed as orderlies come into the room, “Who are you? What do you want from me? Why am I in these restraints?”, I ask. They remain silent as she motions for an orderly to pick up a chair and put it next to my bed. She sits down and the orderlies stand slightly behind her one on either side.
    She is finely dressed. Her hair is neatly done in a high bun and she is wearing black frame glasses, a string of white pearl necklace and matching earrings, a tight white button up satin blouse, black leather gloves, pencil skirt, tan beige or nude pantyhose or stockings with a black garter belt and matching bra and panties and side zip mid calf high heel boots.
    “Hello Sara” she starts, I look at her with confusion and disgust and I interrupt her, “Sara? My names not Sara, I’m a guy you crazy fu…” she quickly covers my mouth with her gloved hand. “You DO NOT TALK WHILE I’M TALKING, UNDERSTAND?” She states and asks with authority, she slightly looks back and says, “Gag her, I do not want to be interrupted again” an orderly steps forth with a ball gag in hand, she moves her hand to my throat with one hand and with the other pinches my nose gently squeezing and orders me to open my mouth, but I refuse for a few seconds and finally open mouth and the gag is promptly and firmly put into my mouth and buckled behind my head.
    “As I was saying, My name is Dr. Elizabeth Trent, and I am here to help rid you of your delusion that you are a guy. You are in these restraints so you don’t rip out your I.V. of female hormones and chemical castration. You’ll be released from your restraints when you accept that you are a girl. In the meantime I have this blindfold you’ll wear and these headphones on a repeating loop of hypnosis and girl affirmations.”
    Meal time rolls around, and an orderly comes in with a smoothie cocktail of fruits and vegetables laced with more female hormones. He sets it down and sits on the bed and removes the gag and picks up the smoothie cocktail and puts a straw to my mouth and tells me to drink it down.
    A couple hours pass and the orderlies come in and release me from my restraints and take me to the bathroom and force me to sit on the toilet like a girl and tell me to handle my business as they watch. When I’m done they tell me we’re going to a different room. In the middle of the room is a gyno table with leather straps at the forehead, neck, above and below the chest, waist, biceps and wrists, thighs and above the knees and at the ankles. Next to the table is a enemas IV bag with luke warm water. I try to turn around and leave the room, but they block my escape and grab me under my arms and lift me off my feet and carry me over to the table and put me down on top of it and strap me in. A couple minutes later Dr. Trent walks in washes her hands and puts on some latex gloves and grabs the enemas nozzle and lubes it up then applies lube to to my rectum and starts to insert the nozzle in. I jerk and whimper in pain as it starts to go in. “Shhh, it’s almost in sweetheart, you’re doing good” she states as she pushes it in further. When its in as far as it’ll go, she opens the flow valve and my hole starts to fill with water in seconds. After my enemas, she removes her lab coat, blouse and skirt, and walks over to a drawer then pulls out a strapon and steps into it pulls it up and tightens it around her waist. She grabs for the lube and applies it to the cock and rubs the tip around my anus for a minute then finally pushing it. I jerk and let out another cry of pain as she slowly slides it in all the way and just slowly back out, but not all the way. She pushes it in again a bit faster this time and back out. She picks up speed every time she pulls out and pushes back in. After she finishes, she lets the orderlies have a turn using my anus. They take turns filling me up with their cum over and over as Dr. Trent watches. “You love having two men fill you up with cum don’t you you little slut?” She asks, I reply “No, Dr. Trent, I don’t.” “Well give it time and you will sweety.” “Go and get ‘The machine'” she orders. The orderlies come back with and place a fucking machine between my legs and lubes it up and slides the machine forward til just the tip is in and turns it on and says, “have fun”
    A daily routine of training and disciplines for monthes has me acting feminine and feeling girly and accepting of my new role a submissive bi or lesbian girlfriend.

  8. Violet says:

    Omg that would be so hot to be transformed into a COCK sucking Bitch cum slut slave girl completely feminization is done and funded by my gf new lover who wants to pimp a SISSY especially his new wife’s ex bf turning his COCK into her new dildo to fuck sissy while making sissy give her hubby head and yells how much more you turn me on as our sissy COCK slave than as a jealous bf.

  9. SissyKendra says:

    How can I make this a reality? Would truly LOVE to live my life, fully feminized, and in complete service to my Mistress.

    • sissydiane says:

      I have thought about becoming a full time sissy for many years and have cross-dressed in one way or another since childhood. It has only progressed over time and now it is all I think about. I need advice and training as I still have worries about losing friends and family. Looking for guidance!!
      sissy diane

      • Stephanie says:

        It’s already happening to me since starting isolation back in March. I’m right there with you honey. I’ve been this way forever too but after dressing this long it’s hard to think of changing back to male full time now. It’s become ingrained as who I am now.

  10. kerry higgins says:

    i would luv to wake up one nite only to find out i had been transformed into a real sexy woman from a real stud muffin into his dream girl one nite after pleasing bunch of guys one nite only yo find out i am a girl inside and out head to toe would make me realy happy


  11. Kristal Satin says:

    I love it! Great experiment!
    Before I accepted myself as a comeplete Sissy, the thought of being forced somehow made it ok, or, simply said, that would be the only way that I would fulfill my fantasy of slurping away on a hot slippery cock until it exploded with sweet juicy cum.
    I bet there are lots of straight guys that would be in at one level or another. I love “forcing” guys to suck my stiff sissy cock. When they show up all shy and withdrawn and end up slurping away like a pro until my pretty big cum load ends up down their throat and all over dripping from thier lips – I love it! Of course I get to finish them off, mmmm yummy. It always baffles me how quick they want to leave after they shoot unusually huge loads of cum due to all the excitement. Now I refuse to untie them right away. I’ll tickle them with my satin scarves and their cocks get so hard again – and they beg for more – politely of course

  12. Victoria swallows says:

    This was amazing you should do this again to see if it’s what she wanted or if it can work on anyone. And maybe it’s what she grew to want

  13. sissycheraice says:

    I would love to have someone force me to become a sissy but you know what they say you can’t force the willing hehe I am such a little sissy slut

  14. Michele says:

    God I can’t resist or even control my sissy faggot desires and my incredible lust for juicy hard cock. I want to worship every beautiful cock in front of the whole world because there is nothing wrong with being a dirty cock obsessed sissy.

  15. ylyg123 says:

    This is such a great situation and only thing I would complaint about and next time you should probably adjust is the 5min sissygasm. It isn’t an easy things to do, and forcing oneself to make it within a timeframe could takes away the fun and enjoyment, possibly made them very stressed. There is no wrong in not coming climax at 5 mins, and punishing one for that isn’t very ideal. It is better if you set the goal to be a longer time or just to switch it to a different goal instead.

  16. Cumbunny says:

    Mark Schrader is a good sweet submissive person who is a great person who is willing to be used as a whore for the pleasure of having a black mans cock and I will never complain about the way I am used to pleasure beautiful men and women who a little worthless willing wanting whore who is a good guy and gets a lot better as well with loads and cock slapped on my face like a little slave who deserve to be used for

  17. slutCindy says:

    mmm, what a delicious story. i am sooo jealous of Jill and always have had fantasies of being seduced into a situation where i suddenly found myself not being able to back out (images of my slutty nylons being ripped, my panties being shredded, my little clit being teased mercilessly, my little anus being violated, all in front of the camera, oh my… that had me gasping…). i can’t wait to start my real training!

  18. Jizzellslut4ownership says:

    adam konkle gorrie ontario canada. 22 820 2550. take me away, keep me hi and turn me out into the biggest cum dumpster cock slut gangbang doll ever.

    • Sabrina says:

      I did love the story and wondering if there is really a sissy school like this, I don’t have that kind of time but I do have permission from my wife to attend a sissy school for at least 10 days to learn the fundamentals like dress n makeup, I would love to go in public without embarrassing my wife👗👗 any nice men I can get would be a bonus😈 thanks Sabrina 💋💋💋💋

  19. Salvatore says:

    I see that many people who have commented really want to be turned into a sissy girl.

    I am a sissy for my Mistress/girlfriend..we try on clothes together at home..go out as girlfriends, yes she treats me like a sissy girl during sex most of the time.

    Here are my recommendations
    1. Start by getting clothes, and dressing up at home either openly or discretely
    2. Wear women’s underwear, bras, panties, socks, etc under your regular clothes
    3. Be OPEN with your partner. If you dont have a partner, be open with men and women you meet. My experience is that over 90% of both women and gay/bisexual men think it’s cool, and get into it.
    4. Use dildos, butt plugs, etc. With yourself.
    5. Find an LGBTQ area (I found midtown Sacramento) where its totally cool to dress however you want. Its extremely liberating.

    It’s highly likely in those areas, clubs, bars, etc. You’ll meet people like you/us.

    6. Read and join blogs and online discussions, etc. It will make you feel part of a community and feel accepted.
    7. Go for it. And “Just do it.”


  20. debbie says:

    Dear trainer Frida,
    i just luv this story. i would luv to live that story over andover again. thank u
    your submissive sissy, debbie

  21. Louise says:

    Wow this story is soooo hot! It made me so wet just reading it. I love how they took their time and gradually worked on the subject with the toys, especially the cockring to determine the size and used it later for arousal purposes. This story makes me fantasize about being feminised even more. I’m just starting on this journey but could totally see myself getting lost in a program like this.

  22. John/Jenny(Sissy) says:

    Oh my! I’ve been a CD for a whole bunch and just about 5 months ago found sissydom!!!
    I started reading on xnxx and read until I figured I needed more info and came to this wonderful site. I just got my first plug 3 days and enjoy it .
    Any time I went to a store that had shopping carts I would walk with my feet stepping a bit closer and that gives me a fem walk, just a bit. With the plug , I don’t even think about it, it just happens. I do like my plug.
    Some of those videos had hypnosis on them and I listened
    to all of them multiple times.
    Even before I told a friend about those he always referred to my cock as my clit. He laughed and said “yeah you’re a sissy” Why…Yes I am .
    I’ve even been invited to join a cross dressers club here in town. I look forward to that and all of the possibilities and probabilities. Oh Gosh!!! Thank You so much!!!

  23. Cathy (trainee) says:

    I wonder if it is possible to have it both: live an open life as a married guy and, at the same time, be a secret sissy. I still like to have sex with girls, but on the other hand, I feel like a girl myself and I want to please a man. Not as a passive boy, but as a sissy girl. Living a double life doesn’t allow to get through with all the attributes of a sissy, though. Like chastity, for example. But I do have an urge to be a sissy, to dress like one and to please men

  24. MrBarbieDoll says:

    So, it kinda seems unrealistic?? That would definitely be amazing and all. Definitely a great story, just seems in real? I love forced Feminization and prefer the name over sissification. There needs to both be the will to serve submit obey an yea even feminine curiousness. As well as an almost equally same urge to Dom feminize and continue forward with the fetish as well as the sessions/progression.

  25. [email protected] says:

    I am in an unfortunate situation where there are no open crossdresser or any LGBT groups in my city. Everybody is closeted and repressed. I’ll admit it is a bit difficult to rely solely on online support.

  26. Stephi says:

    Some points would be to hard for me…. locking myself in a hotel room and waiting for someone I don’t know.
    Sorry that would be to much for me.

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