Humiliating a Sissy

[RacyWilde]

How about having a dominatrix be his "babysitter" while you go out on a date? Give him strict orders to obey her as he would you while you're away, and have her make a list of his transgressions (real or imagined) for him to be punished for upon your return. "Mistress Babysitter" could supervise his dressing up and make him prance around to show her what a good little girl you've made him.

Upon your return, you could tell him about your date and punish him after Mistress Babysitter checks off the list of his transgressions. You could also apply a tassled butt-plug to his sissy ass and have him prance around for your Ladyships' amusement. His reward for being a good girl would be a good pegging from both of you. Just a thought for your consideration...

I do plan on bringing in a rigger (who is actually a Dom too). Maybe I can let the rigger have some fun with my sissy girl... create some art for me for when I return. And then all sorts of naughty things can ensue.

Cheers

 

[timeagain93]

serendipity

it's odd but im writing a note to a prospective mistress and im detailing my past experiences with this

 

[timeagain93]

a mistress would have me buy beige pantyhose and jack off in them. Then I’d put them on and wear them for 24 hours. She’d sending teasing emails asking if I liked wearing my cum.

 

[Quint12]

My mistress loves using her strapon on me, she likes putting me in front of a hotel window for the world to see just how much I like it.

 

[midwestdude]

I do plan on bringing in a rigger (who is actually a Dom too). Maybe I can let the rigger have some fun with my sissy girl... create some art for me for when I return. And then all sorts of naughty things can ensue.

Cheers

That sounds hot!! I'd love to be a sissy sub to a domme in the bedroom

 

[theCARS1979]

I want to be in that position

Thank you so much!

For at least one play session, I do plan to take him to a dungeon or play space. I'm in contact with a rigger (as I don't have the skills as yet to suspend him) and I plan for this male rigger to tie him up facing down spread eagle. I'll wrap him leaving his balls and cock to hang and to have easy access between his legs. I was also thinking of making him deep throat my strap-on and then forced ejaculation to collect for a fake cock. Then I'd peg his ass ejaculating his own cum into it.

Id love to be in that position to take it in the ass with your strap on nice and rough and hard and watch myself in the mirror submitting to you

 

[theCARS1979]

My mistress loves using her strapon on me, she likes putting me in front of a hotel window for the world to see just how much I like it.

wow thats awesome as long as you dont mind it
to get caught wow

 

[jradek75]

*

I need to expand my repertoire in humiliating a sissy. I'm looking for creative and innovative ideas to use in my real life sessions.

I am aware that everyone is humiliated by different things - I'm just looking for examples to get ideas flowing :-

My wife's absolute favorite way to make me cum is to put me in a pair of her panties, lay me down, flip my legs above my head, pull the panties down just a bit, and jerk me off onto my face and mouth. This makes the verbal part easy too; "Do you want to cum? You know it's going to be all in your mouth.... You better get every drop, you dirty slut.... You don't want to miss any and have somebody see you with cum on your face... Tell me that you want it.... Tell me EXACTLY what's going to happen if I keep going..... Maybe I'll take a picture in case you start acting up... You know you've eaten way, way, way more cum than I ever have... Probably more than anyone else I know... Did you taste good?.... If your friends only knew how much of a slut you are.... Let me know if you get hungry again later... etc."

The lines practically write themselves. None of it requires her to be "fake cruel or mean", just playful. That makes it even more humiliating because it's not faked. I know it's going to be a humiliating way to cum but she'll have me so turned that I can't help it. I'll agree to, say, and admit to anything at that point. Then when she knows I've reached the point of no return, she'll be smiling ear to ear with the cutest, sexiest, little giggle. Humiliating? YES. Hot as fuck? YES.

 

[yukonnights]

My wife's absolute favorite way to make me cum is to put me in a pair of her panties, lay me down, flip my legs above my head, pull the panties down just a bit, and jerk me off onto my face and mouth. This makes the verbal part easy too; "Do you want to cum? You know it's going to be all in your mouth.... You better get every drop, you dirty slut.... You don't want to miss any and have somebody see you with cum on your face... Tell me that you want it.... Tell me EXACTLY what's going to happen if I keep going..... Maybe I'll take a picture in case you start acting up... You know you've eaten way, way, way more cum than I ever have... Probably more than anyone else I know... Did you taste good?.... If your friends only knew how much of a slut you are.... Let me know if you get hungry again later... etc."

The lines practically write themselves. None of it requires her to be "fake cruel or mean", just playful. That makes it even more humiliating because it's not faked. I know it's going to be a humiliating way to cum but she'll have me so turned that I can't help it. I'll agree to, say, and admit to anything at that point. Then when she knows I've reached the point of no return, she'll be smiling ear to ear with the cutest, sexiest, little giggle. Humiliating? YES. Hot as fuck? YES.

Well, you convinced me

 

[yukonnights]

That sounds hot!! I'd love to be a sissy sub to a domme in the bedroom

I've just been wanting to say; That's about the coolest/funniest avatar pic I've seen

 

[Paintingwithautumncolours]

Defecate on the sissy. If its a first time experiment, consume a lot of fresh fruit and liquids to maximize the occurance of diarrhoea. It makes for the best spray.

 

[pensivepoet]

Shopping day
First to Target
The sissy must wear panties that can be seen. Panties high, jeans low, very short T-shirt.
Make him bend and squat often
Shop for bras, panties, dresses, and keep him playfully involved.
Perhaps even make him try on a dress, maybe even step out of the dressing room for your approval.
And make she he is perfumed before going shopping
Buy lipstick, make up, pink baretts, etc...
When the cart is complete, you choose the most embarrassing line and cashier
He is to go through alone
You follow a couple customers back with a small item and he is not allowed to acknowledge that he knows you.
Next, the adult store
He is to tag along silently
You make him try on wigs
You look at lingerie, ask the clerk if he/she thinks your sissy needs the s-m or m-l
Ask the clerk to recommend a good butt plug, etc...
Next, stop for a drink
You order a bourbon for you and a Shirley Temple for him etc...
Finally, the hair salon for women
He must wear flip-flops with his toe nails painted
He is not allowed to speak
You tell the salonist you're not sure how you want his hair, ask if she has any thoughts
If she says, "well, what does he want?"
You say, what he wants doesn't matter.
When you leave, you drive
He must sit in the back with no pants, only panties
You drive through a high traffic areas, lots of lights and trucks
Believe me, by the end of this day, he'll be humiliated.

 

[sterculius]

I'm not sure if this applies, but as it pertains to me, I'm a fan of what I like to describe as situational humiliation. I'm a Cocksucker, and I like being addressed as such. I don't consider it to be an insult, simply a statement of fact. I don't want to be insulted for being a cocksucker, that would be cruel. It offends me that someone might derive satisfaction from intentionally causing me pain or discomfort, but it thrills me to consider that it's irrelevant to them if, in the course of "using" me for their sexual gratification, that by chance, they do. I like being objectified, to be treated as a thing to be impersonally used. For my mouth and throat to be seen as little more than a tool whose sole purpose is to serve as a tight, wet and warm hole for them to fuck, and as a convenient receptacle for their cum Some of the men I blow have "passed me around" to their friends. It excites me to be on my knees, sucking cock after cock as the others stand around with their cocks out, laughing and talking about me while waiting to take their turn fucking my mouth.

 

[diaperedtiffany]

As a newly discovered submissive sissy, I figured this would be the best thread for my first post. The ideas and descriptions in this thread are phenomenal!

 

[cripple92996]

dfdf

43 dom love to online explore

 

[eroticspank]

*

I need to expand my repertoire in humiliating a sissy. I'm looking for creative and innovative ideas to use in my real life sessions.

I am aware that everyone is humiliated by different things - I'm just looking for examples to get ideas flowing :-

Physically
He loves wearing pretty girlie clothes such as school girl outfits - but that's the thing... he loves it. What are some outfits that humiliate? Or should I do stuff like smear his pretty make-up or draw a cock on his face and show him in the mirror?

Verbally - this is my weakness. I'm not a verbal person and I get lost for words. Do you have any harsh and unforgiving words or phrases (I'll try to memorise them for quick use)? But is it more about how you say the words than the actual words themselves? I know how to get heavily mean with my voice but I want to make sure that what I say will turn him on rather than destroy him.

Also, how do you humiliate him via his cock when his cock is actually pretty groovy?


Any advice is much appreciated.

Great thread and suggestions so far.

Regarding wearing pretty things and outfits, just because he loves it does not mean you can't still humiliate him while he is wearing those things. Tease him about what he is wearing and how he looks in the outfits. Tease him about looking like a sissy and a very horny slutty one. You will need to experiment and find out his triggers or things that cause him embarrassment or humiliation. Things like being seen by people he knows, or seen in a hotel window as mentioned above are possibilities.

Verbal is easy if you just think about describing what you see. Talk about how he looks in the outfit, how pretty his dick is in the panties, tease him about getting hard, embarrassed or humiliated. Talk about things you are thinking about doing to him. Having him fucked by a friend, forced to serve a bunch of ladies at Tea time, made to watch while you fuck your bf or play with yourself. Describe each scene in detail. When he starts to get more turned on, you know that scene is something you can use.

If you like his cock, talk about that you like how it looks in lingerie. Talk about it as an object, not as part of him. Talk about how you are going to make it yours, make him tell you it is yours to do with as you please. Get into a position so it looks like his cock is yours and not his.

ES

 

[timmyid2]

I second the "take him out in public for his first time." I did something similar with a guy that I hooked up with at a bath house. We'd hit it off so he suggested a picnic the next day. We met at a park, sat in his car in the back corner of the parking lot making out. No biggie, I'm Bi and no one was around. Then he got out, grabbed a basket and blanket from the trunk and led me by the hand to the top of a little rise. I felt like a little boy next to this tall, string guy.

When we reached the crest of the little hill we laid down and "had lunch" in full view of everyone. The excitement of being watched as he kissed and fondled me was amazing. I knew everyone was scandalized, but it was sexually exciting and scary at the same time.

So if he's never been "out" in public, drive him to a nearby town and show him off somewhere that is NOT part of the scene. A bar, a clothing store, even a shoe store will get him plenty excited.

As for the cuck part of the game... It seems like the most humiliating cuck relationships are where the husband has to serve his wife and her bull. He does not have to get queer about it, but little things like bathing her lover's with warm cloth and soap can be quite embarrassing.

Dressing the wife for her play date can also be exciting and humiliating at the same time. I was very turned on and embarrassed when my ex wife asked me if her bustier was too noticeable under her sheer blouse. As she slipped into the tight black mini skirt she explained that she wanted to show off for her new boss. As I stared at her slightly visible nipples I lied and said it was fine. Then I thought about it all day.

Begging is something I like from my sub. Give him a list of things that he must beg the bull's permission for. Promise that he'll be rewarded if he does a good job of begging. No need to let the bull know that sissy is begging to bring him a beer because it's on the list.

Sissies come in two forms... Homo / bi and hetero. If hubby is not too weirded out you can instruct him to "fluff" your lover. Does not matter if he's homo or not as long as it embarrasses him without driving him off.

Good luck and let us know how it goes.

timmy

 

[tfrah]

My husband has long confessed fantasies about being humiliated publicly but this is an area he has always strongly insisted would be a line he would never want to cross - but the more me have played the more he has been willing to risk posting photos and stories online and has increasingly been coming up with ideas and ways that we could expose his sissy side publicly online, just as long as he feels safe that no one we know would see it!

We've gone as far as creating a little tumblr blog and posting to reddit's femdomgonewil, but I know he likes the idea of going further - using skype or snap chat or whatever and inviting some dirty girl to watch and, well I'm sure you can imagine the rest!

 

[SissySalina]

sissy normally does not get embarrassed or humiliated and has not for a long-long time.
Saturday sissy was requested to wash the vehicles. She was sitting in a lounge chair sipping a drink under a tree. As normal sissy got the bucket, hose and mitten ready for the washing and pulled Her car up and started to wet it down.
She then requested that sissy remove the top of the bikini that sissy was wearing. For the first time in a long time this made sissy feel funny, like something natural was missing. As sissy washed the cars sissy was constantly feeling like something was wrong.
sissy would not really call this embarrassment or humiliation but sissy just felt something was not right.

 

[tristantrotsky]

Pleasure Or Pain?

I'm not sure if this applies, but as it pertains to me, I'm a fan of what I like to describe as situational humiliation. I'm a Cocksucker, and I like being addressed as such. I don't consider it to be an insult, simply a statement of fact. I don't want to be insulted for being a cocksucker, that would be cruel. It offends me that someone might derive satisfaction from intentionally causing me pain or discomfort, but it thrills me to consider that it's irrelevant to them if, in the course of "using" me for their sexual gratification, that by chance, they do. I like being objectified, to be treated as a thing to be impersonally used. For my mouth and throat to be seen as little more than a tool whose sole purpose is to serve as a tight, wet and warm hole for them to fuck, and as a convenient receptacle for their cum Some of the men I blow have "passed me around" to their friends. It excites me to be on my knees, sucking cock after cock as the others stand around with their cocks out, laughing and talking about me while waiting to take their turn fucking my mouth.

This is such a mutual delight, both for you enjoying the attention of their cocks, and for the Gentlemen that you are sucking off, that I'm not sure it really qualifies as 'humiliation' at all. For humiliation, shouldn't there be an element of reluctance or shame or embarrassment involved?
The original question here was 'How To Humiliate A Sissy' - and the obvious answer is right here. Dress up your Sissy in her most tarty cum-slut lingerie and take her to a sex party, but once there have her sit and watch as the wonderful Sterculius, or maybe another with a similar talent, sucks all the cocks and swallows all the cum. This will go against the Sissy's every natural instinct and desire to be the centre of attention, to be the object of all the guy's sexual focus, and to suck lots of cock. This will result in the poor Sissy being both frustrated and humiliated...