Sissy Training

[Mistress Lilith]

Hi All

I am hoping that you all might be so kind to give some suggestions. I have assumed the roll of a dominant Mistress in order to train my husband to be a submissive sissy slut. I will be using a wide variety of toys and strap-on’s during his training.

What I would like are some suggestions on how best to train him! I would welcome any advice on dressing, teasing, cum feeding, scenes to employ, dildo training etc… Needless to say I will employ bondage also.

Regards
Mistress Lilith

 

[gingermango]

I'd be curious what kind of response this generates. My Goddess has been training me for years . . . . Most of what she's done she's pulled out of her own imagination and creativity so I'm interested to see if that's how other female dominants generally proceed, or if they actually solicit and receive detailed advice.

* sits back to watch the replies, munches popcorn expectantly . . . *

 

[catalina_francisco]

LOL, hope you enjoy the adventure. As to cum feeding, I just surprised him with the order after having him empty into a paper cup. He was obedient, but didn't like it much, so I guess he will have to learn to like it as much as some other things he hungers for.

Catalina

 

[catalina_francisco]

I'd be curious what kind of response this generates. My Goddess has been training me for years . . . . Most of what she's done she's pulled out of her own imagination and creativity so I'm interested to see if that's how other female dominants generally proceed, or if they actually solicit and receive detailed advice.

* sits back to watch the replies, munches popcorn expectantly . . . *

I love the opportunity to use my creativity and over active imagination...so far it has not let me down, and I have tons and tons of ideas to still try.

Catalina

 

[Netzach]

Cum feeding for the reluctant can often be achaieved by getting it on your gloved hands, then pinching the nose shut. The mouth will eventually open.

 

[gingermango]

Cum feeding for the reluctant can often be achaieved by getting it on your gloved hands, then pinching the nose shut. The mouth will eventually open.

Heh. I've been on the receiving end of that sort of thing a time or three. As a practical matter, if he objects to the taste and you're feeling charitable, make him drink a few glasses of pineapple juice throughout the day to sweeten it up. Alternately, you can use a few drops of a glycerin-based lube whatever you jerk him with or on his hand if he has to jerk for you. The lube will sweeten the taste a bit, too.

Goddess has gotten the pineapple juice thing down to somewhat of a domestic ritual, such that I know if she buys some at the grocery store, I know to expect to be swallowing my own juice within a day or two.

 

[Master Sensei]

Cum feeding for the reluctant can often be achaieved by getting it on your gloved hands, then pinching the nose shut. The mouth will eventually open.

I normally don't find much interest in male subs, but I just have to say that your post was really erotic.

 

[AAkasha]

Hi All

I am hoping that you all might be so kind to give some suggestions. I have assumed the roll of a dominant Mistress in order to train my husband to be a submissive sissy slut. I will be using a wide variety of toys and strap-on’s during his training.

What I would like are some suggestions on how best to train him! I would welcome any advice on dressing, teasing, cum feeding, scenes to employ, dildo training etc… Needless to say I will employ bondage also.

Regards
Mistress Lilith

Dress him up in tight pink panties and a pink bra, make him suck your strap on cock and then pour his cum all over it (you can take frozen cum from a milking session, thaw it out). Make him lick his cum off and suck it clean.

That's just a starter. There's much more, but that's all I have time to write at this moment!

Akasha

 

[MistressHelan]

Best of Luck

I really envy you starting out on this adventure. It is one of the most rewarding experiences for both a mistress and her play toy. I only wish I could start over again with my sissy.

Well some advice
Training is very important and you don’t want to rush it. Start out slowly at first and then pick up the pace. Be prepared to spend several months training youre sissy. Once you set a pace, keep to it.
If I was starting out again I think I would make use of a chastity device after all, all naughty girls like to play with their clitty. These are very common and can be found on most internet shops. The CB-3000 would be a good option that seems to be popular. Its worth denying her a organism for a period of time, and remember it is you who will be getting the pleasure in the long run.
As many of the posters already stated, be creative. Use youre imagination.
Remove all male under garments and replace with very girly panties, bras, etc… Make sure these are worn 24/7.
Get the basic female make up things right. Show how to apply lipstick, eye-shadow, makeup etc…
Find a strap on dildo you are confortable with, after all once you get into it you will be straping it on many times a day.
Use plenty of lube.

These are just some quick thoughts. In my case I spent almost 6 months teaching my girl her womanly ways. Now she craves for my strap on daily, loves her own cum and is the most loyal person you could ever met. When I switch her back to a male roll, I must say, she really out performs her previous efforts. It was ohhh so worth while all the time I invested. I wish all the best and will be checking back hoping for progress. If you wish you and send me a private message to discuss further

Have fun and enjoy
Helan

 

[Rrrosyn]

Interesting...

Now I never tried to turn j into a sissy, just feminize him a bit. Panties during the day but nude at night. He has long hair, that is not permitted to be longer than mine. He must shave, of course. A lot of it is just verbal. Calling him lovely instead of handsome and such.

Problems I have run into are usually due to the fact that I don't wear feminine clothing or makeup, etc. It is very hard to properly teach a sissy to apply makeup when you've never worn more than lipstick yourself! I couldn't even teach him how to wear a thong! I have always been au natural, and even make my shaving rituals, his job!

 

[Netzach]

Those secrets are out there for anyone who wants to learn them.

I certainly have to make an effort to be femme. It's not natural, no one is born with eyeliner in hand.

And what a good way to keep your sub occupied with a little research.

 

[Rrrosyn]

... no one is born with eyeliner in hand.

You're kidding!!

I make little effort. Would make more if I had a job. Otherwise, I just do my hair and add a little lip and nail color before going out to munches and other public events. Strangely though, I prefer skirts to pants. *shrug*

Anyway, love the idea or research. I remember a little booklet that you used to be able to get free from a tampon company. It had all sorts of stuff about being a girl and even a little Maybelline makeup guide. Really simple steps to follow. Also, any female teen magazine would probably have tips.

 

[BattyBattyBats]

Who's idea was it at first?

 

[Mistress Lilith]

Thanks to all of you who gave me some suggestions, I have looked at and purchased the CB-3000 it looks very interesting and can’t wait for it to arrive in the post.
To date my sissy has been wearing nice girly G-string panties, I’ve been getting her to clean herself daily so as she feels comfortable. So far I’ve just been teasing her either with toys or with my strap on, sometimes tying her up and using it on her. I still have not allowed her to cum…. reaction is quite an interesting thing to watch.

Helan, I’m quite interested in the comment you made “When I switch her back to a male roll, I must say, she really out performs her previous efforts.” Would you mind if you were to kindly elaborate a little.

Thanks again to you all, I will keep you posted with updates.

Mistress Lilith

 

[MistressHelan]

More to come

I was delighted to read that you had purchased the CB3000. This will add considerably to youre adventure. I don’t have much time at present, but here is the basics of what you asked.

What I was meaning with the switch is that when my sissy takes back on the roll of a male, that he out performs his previous efforts. What I have found is that he does not climax as quickly. I am accounting this to him being more in touch with his feminine side and the fact I kept him in a state of high sexual arousal. Denying climax while in sissy is key and also cum feeding him(her) when he(she) does climax. This is what I believe.

I will add more later. Remember have fun and enjoy.
Helan

 

[timberwolf05]

wellllllllll?

in MY experience ONLY.....

tie an old pair of nylons/pantyhose between and around his legs and teach him to take smaller steps as do MOST women..vs huge strides as a male.
take him to a parlor and have a pro do his makeup and make him learn to do it himself.
make him start sitting vs standing in the bathroom.
make him wear skirts vs pants. make him wear girls' jeans w/o the pockets in the back vs male jeans..
make him wear all girl clothes...period.
make him wear female pads in his panties..

there are all kinds of female training...use your imagination..and it will be Your delight.

woofie

 

[MistressHelan]

some more thoughts

At last I’ve had the chance to get back and add some more thoughts. First of all, have I answered youre question in my previous post? If not I can expand further.

The chastity device you have purchased is an excellent device and will help considerably in youre training adventure. Some advice I can offer in this respect, is that you should consider massaging the prostate. This can have one of two effects (a) when the device is removed, cause a much more intense climax, (b) if not removing the device, will drain youre sissy, without climax. It might also be an idea to purchase an Aneros Prostate Massager. The only problem with this is that it requires practice to get it to work but the aneros website does provide some information.

A benefit, however is if you do not have time some day to take care of some training, then you could order youre sissy to use this massager while being tied up and locked in the chastity device. Also you could leave her (sissy) tied up and remove the chastity device and let her cum (without touching herself) only to punish her latter! Could have some very interesting consequences (for her that is)

Just writing out the above has put an idea into my head I’d like to try out later on my sissy. I will post about it in the coming days, and maybe give some of the details.

Something that will become evident to you as you scan through some forums and discussion boards, is that there is some really extreme ideas out there. Personally I’m not into them and neither is my sissy. Some humiliation can be OK if you are comfortable with it, i.e. getting her to shop for makeup, lingerie, clothes, etc… Some times the sales assistances figure out what is going on, and this can be exciting. I am not into involving others in our play, but I do fantasies about her being taken by a real man. I don’t think I’d ever go to this level, however but see no harm in the fantasy, or her knowing about my fantasy. I often describe the fantasy to her while she is sucking me or taking me from behind, describing that it is a real man she is pleasing and that I am sitting watching it in the corner. Sometimes the reaction can be interesting! I know that she understands my boundaries, and this is something that you should also establish early in the adventure.

I will be most interested in hearing some of youre experiences and some of youre sissies experiences throughout her training. Will you be allowing her to post to this thread or another?

Have fun and enjoy youre adventure,
Helan

 

[experiment102]

This has always been a huge fantasy of mine. Are there any women out there who would like to take on a sissy??

 

[pantyslutx69]

How far do you plan on taking your sissy slut... any special activities you have in mind for her?

Sissy Slut Kt

 

[landcruisergal]

Those secrets are out there for anyone who wants to learn them.

I certainly have to make an effort to be femme. It's not natural, no one is born with eyeliner in hand.

.

but getting it tattooed on permanently comes close. No smudging, no mess and to wake up and step out of a shower with perfect lines is almost liberating. Sorry for the hijack....
A perfectly painted toenail 24/7,(choose a polish from your collection, and send him to find and buy one identical, this can be a challenge in itself) is a subtle reminder also, and good practise for when he attends to yours.

 

[AAkasha]

How far do you plan on taking your sissy slut... any special activities you have in mind for her?

Sissy Slut Kt

Humiliation in a place like Victoria's Secret is a sure way to put a man in his place when he wants to engage in "sissy play."

Also, humiliating men in front of female friends.

Akasha

 

[BattyBattyBats]

Make him do housework in a french maids outfit!

Strut around the house wearing the strap on and make him kiss it whenever you walk past.

Have him talk to his friends on the phone or watch his sports only if he's in panties, stockings and wearing a butt plug.

Get him to walk to the local store wearing feminine underthings and have him buy feminine products, condoms and 'suggestive' vegetables.

Make him earn any masculine time with degrading and/or feminine behaviour.

 

[lisa-CD]

Personally, I think your sissy is very lucky. I’d love to be in her place, being trained to take it like a real slut. While my master has made many attempts at doing something similar for me we have failed. The main reason is my lack of follow through, and his inability to maintain the dominate roll when I beg him to stop.

I would advice you, to always remain the dominate but be considerate also. If she wants you to stop, then do so. But maintain a high level of arousal maybe by telling all the things you will do to her. For me seeing my master naked and his cock standing to attention will often excit me to continue after a short break.

Make her suck your cock when she refuses to take it. Be naked around her doing simple things, reading, watching TV, hovering etc… Sometimes having a break for a day helps, but keep the arousal. I know from my experience that I simply become too tired and refuse. Deep down I have desires that I want explored but am unable to at that point. I feel that if my master was more forceful than caring then I would become conditioned to serve him.

These are some personal observations. I’m sure they might apply equally to your situation.

 

[domlinn]

Being a dom myself and having trained many male sluts, I guess I am eligable to make some sugestions her

Some very valid points on the thread thus far.

She must wear panties 24/7 7 days a week.

She must satisfy you when you want her! Accept no excuses

Its good practice to have her suck your cock (I assume a strap on) many times a day (you have to get her use to it)

Do use a chasity device as one poster suggested, this will help keep her excited and prevent her from creaming her panties while you have them pulled to one side showing her how to take it like a man (ha ha)

Do it in a public place

When she does cream her panties (maybe by rubbing her clitty while chastiy device is off), have her lick them clean or use them as a gag.

Take photos of her dressed up and servicing you. Show them to her when she refuses to service you!

Remember to be a bitch (after all you are the dom)

Do you intend traing her to service another man?

 

[lisa-CD]

Got a little side tracked on Akasha website and forum. You should check it out, some very good pointers in that forum!

Bring her shopping for smalls, ask assistant for help, and when she suggest something, tell her its not for you, that you caught your man wearing yours and decided to get some for him. Afterall you don't what yours stretched! This would be good humiliation.