Help me humiliate a sissy boy (F/20)

[annodaM]

I have a sissy friend (M/25) who is much into feminisation as well as other kinks and he would like me to sort of dominate him for the holiday season. So I’ve decided to ask you guys on gD about what great fun we could have with him (he doesn’t know anything about this page so he’s up for a good ride).

He’s into:

• Anime
• Crossdressing
• Strict Bondage (he loves it)
• Sensory deprivation
• CBT
• Chastity
• Female Feet
• Private and public humiliation
• Femdom

He’ll be staying next to my place so I’ll use my own toys (listed in my sig) to torment him, but we’re willing to buy things if needed. Also he has the following clothing items:

• Maids outfit
• One piece swimsuit
• Red dress (long)
• Schoolgirl outfit
• Long socks
• Pantyhose

Also he has access to my wardrobe so if anything else is needed surely I’ll be able to provide
Do your worst ;)

[Spleen]

First of all:
- His asshole should be always filled with your buttplug
- You should tease him every day and let him cum only with your permission

[Subboyj]

Always filled seems a bit much if he’s new to anal but you should definitely start training his ass with plug
I’d say leave him with only 1 pair of male underwear for emergencies but other than that he should be wearing panties, if you’re feeling mean make him go out and buy them in person

[annodaM]

Originally Posted by Subboyj

Always filled seems a bit much if he’s new to anal but you should definitely start training his ass with plug
I’d say leave him with only 1 pair of male underwear for emergencies but other than that he should be wearing panties, if you’re feeling mean make him go out and buy them in person

First thing we’ll do when we meet is going out to buy some panties,

[Blue Griffin]

How much/far public humiliation is he willing to do?

[annodaM]

Originally Posted by Blue Griffin

How much/far public humiliation is he willing to do?

Very mild/hidden public, not much else I’m afraid, but he’s willing to crossdress in public tho

[Blue Griffin]

Ok. How about you both to a lingerie store and have him get measured for a bra? Not actually wear/buy one, but just get measured? Oh and have him in normal clothes, but some slight heels?

If that's too much, I understand. I'll work on some more private ones too.

[annodaM]

Originally Posted by Blue Griffin

Ok. How about you both to a lingerie store and have him get measured for a bra? Not actually wear/buy one, but just get measured? Oh and have him in normal clothes, but some slight heels?

I will check with him if that’s okay but it is certainly a great punishment

[NoPantsKayla]

So he has one pair of boy underwear... You should swap it out for a pair of christmas themed goofy men's underwear :3

Here's some possible inspiration: https://www.amazon.com/s?k=chictry+m...ref=nb_sb_noss

Red boxer shorts, snowflake print underwear, or even a little g string that looks like a reindeer! :P

Imagine, he thinks he's getting a break by being allowed to wear men's underwear, only to find out his underwear has been replaced with a goofy gift from Santa! xD

[Blue Griffin]

How about a nice bondage makeup session? Dress him up and tie him up in your favorite bondage position. The have him beg you to untie him. Of course if it's not to your liking or up to snuff, you get to pull out your makeup kit. Go wild and don't hold back. Go as slutty as you want. Keep having him beg and plead. Maybe act like how you have him dressed or try out a girly voice.

Once you are done you can choose what to do. Maybe you can drag him to a window or out on the back porch at night. (or just teasingly threaten him.)

[Mrr]

Something that may really to help set the mood, for both of you, would be to leave him moderately restrained while as feminized as possible while he sleeps. Of course, given what he enjoys, it seems only reasonable that he is also entirely blinded and deafened during that time.

That is, with only one possible exception: leave him with headphones on playing a playlist of sissy hypno/encouragement audios with him entirely unable to hear anything else while he tries to sleep. Even better, something like a VR headset showing a long series of something like pictures of massive cocks so that's all he can see as he listens to the audio might be a nice touch, as well. I'm sure the right punishment could be arranged if either the audio or video devices were to come loose before it's time for him to wake up!

[lowlysub]

All the time of your visit he should be locked in chastity with you controlling the key. Only released when you want.

Handcuff, or just secure, his hands in back. I would unlock him for a cbt session. Make sure it includes strong kicks to the nuts. Lock him back in chastity before releasing his hands.



ok, below would need modification as likely beyond his limits. Probably only 1st part.
For public humiliation make sure to go shopping for supplies for him. Make him try on assorted clothing. If his size fits, Victoria Secret for bra and pantie shopping is a must. You can also consider after bra/pantie shopping to have him put them on and go shopping for outer clothing shopping. For an even higher level wearing all that go macup shopping.

[Temeya]

Here's a simple idea just to tease him a little. Tell him that you're going to spend some time watching anime together. Make sure the audio is not in English (or any other language he knows) and then blindfold him while you watch. This will be especially effective if it's a new episode of a show he likes (even more so if he's like me and hates any sort of spoilers). You can further tease him by reacting to things as you watch such as by saying things like "Wow!" or "I can't believe he/she just did that!" but not actually telling him what happened.

Feel free to modify this according to your preferences. Obviously if you don't like anime you don't have to make yourself watch too or you can pick something else entirely. Feel free to add additional restraints or toys as well such as securing his wrists so that he can't take off the blindfold.

One additional suggestion: if there's an anime girl he especially likes and that show has a beach episode you can pick that one to watch specifically and then wait to put on the blindfold until right before she first appears in her swimsuit. I don't know how effective this would actually be to tease him; mostly I just thought it might be funny.