The sissy whore experience

There is nothing more humiliating for most men to dress up as a woman. For sure by now you already have your partner wearing pretty panties and I'm sure you fuck him regularly with your strap-on. But why not spice things up a bit and prepare him slowly for a greater humiliation (and bigger thrill).

This multi-day scene idea is to prep your partner as the perfect little sissy cocksucker he craves to be (he doesn't know it yet but trust me, he'll love it ;-) ). I'll add many deviations on this scene idea for you to choose from but I suggest you go all out!

So as I said before the main idea is to humiliate your partner in a new way feeding his submissive needs. This will be an adventure that both of you will enjoy. We'll start simple and take it further one step at a time. 

week 1
On two separate days demand your partner to get out your favorite strap-on. Put on the strap-on and make him

strip naked apart from his panties (very important!). Sit down on the couch and tell him to be a 'good little cock sucker' and suck your penis. These sucking sessions should last around 10 minutes each after which you dismiss him and tell him to clean up. A small giggle followed by something like 'you are such a sissy boy' will do for now. While he is getting you off make sure to verbally encourage him and call him humiliating names such as sissy cock sucker, slut, little whore etc.

You can wear your strap-on over your normal pants/underwear or decide to be naked as well. A little bullet vibe might get you off for real while he sucks your big strong cock.

week 2
Repeat week 1 but now force him to deep throat your strap-on for the last 2 minutes of each session. Really force his head down on your cock and ignore the gagging noises he might make; they're part of it and pretty normal, any girl who ever sucked a real cock (not the useless thing your partner has) knows what I'm talking about ;-).

While he is sucking explain to him that he is your little sissy cock sucker and that you will teach him to be the a real sissy whore. Make sure he is blindfolded during these sessions; explain to him that's so he can imagine sucking off a real cock. Notice how rock hard his little peepee is while he's 'going down' on you.

week 3

Pretty much a repetition of week two with the exception that you will leave him a present on your bed. Send him upstairs to fetch the strap-on and explain you left him a present on the bed. Tell him to wear it and come back down. The present you will leave him are a pair of stockings. I suggest suspender stockings or something frilly with a bow tie or something. Either use a pair of your own or buy a pair for the occasion on ebay (2-3 usd). Make sure he is properly shaven or waxed as hairly legs in stockings are jukie. (Remember that the idea is to humiliate your partner, not to make him look like a sexy girl! He needs to look like a dressed up man, not like a real girl).

Once he gets down stairs exclaim how  much like a sissy he looks (you look like such a looser, o my god i cant believe what a sissy you are, you look like a real whore now etc etc)

While he is sucking you off this time tell him he's becoming such a good sissy whore / cock sucker. Tell him you always knew he wasn't a real man but that its even more clear to you now. 

Once you are done tell him to repeat after you: 'I am not a real man, I am a sissy cock sucker'

Additional task: One of my personal favorites! Ask him if he is a sissy, of course he will answer with yes (if not a good slap in the face and repeating the question might prop him to give the proper answer). Tell him every sissy has a pair of heels and give him 20-30 Euro's. Send him to town to go buy a pair of heels and give instructions on what he should come back with (minimum height, color etc). If he has a decently big shoe size there is no way to deny he is buying the shoes for him self a great way to humiliate him!

week 4
He should now do his sucking duties while wearing his new heels and stockings. But we'll add a new twist: lipstick! Men are very afraid of make up as it is something you can not simply take off in a second. Also it makes them look hilarious most of the time which should give you a good laugh and him a decent humiliation!

Remember that he should wear a blindfold while performing his duties! Before you let him start you now ask him the following questions; 'Are you a real man? (No)' 'What are you then? (A sissy cock sucker)' followed by: 'good girl'

Optional: Order a cheap wig at E-bay to make the humiliation complete! 

During the weekend you will plan an extra special session! Do his make-up the proper way including foundation, blush, lipstick, lip liner, mascara, eyeliner, loose face powder etc etc and dress him up in his stockings, panties and high heels. (Look up a drag queen makeup guide) Also do his eye brows (don't over do it just make them slightly more pointy and take out excess hairs). Make it so that its hardly noticeable for anyone else; it's just the idea that counts! Trust me you'll have so much fun together! 

Make him kneel and close his eyes (to bring out those nice smokey eyes of his). Make sure your phone is nearby. Tell him you want him to keep his eyes closed and take four deep breaths (time for you to grab your phone and turn on the camera function) and tell you what he is ('I am not a real man but a sissy cock sucker'). Record him sitting there and saying that sentence with your phone. Once he said it end the recording and replay it near his ear. Once the play back ends tell him 'good girl you are really mine now looser'.

Optional: leave him with his outfit and make up for the rest of the day for added humiliation.

week 5 and on wards
Same as week 4, no need for the full blown make up; just do the lipstick (or learn him how to apply his own).
If you have a corset laying around in his size you could add it at this point for the added effect. While he is sucking you play back the recording a few times and giggle. Tell him he is almost ready for his first real cock. He will either not reply or beg you not to but this doesn't matter. 

Place an advertisement stating your sissy boyfriend needs a cock to suck. Find a guy that seems suitable to you and explain the details to him. On a specific day of your choosing you will invite him over. You will make sure that your partner is in the bed room, blindfolded and dressed up with full makeup on. For added effects you can paint his nails etc as well (remember, he shouldn't look like a girl, he should look like a dressed up man / bimbo).


Explain the guy to not ring the doorbell; the idea is that both of you enter the bedroom silently. You will then ask your boyfriend again to tell you what he is (a sissy cock sucker). This should be a ritual by now. Tell him he is a good girl and should open his mouth. I suggest you record this all on camera. While he sits there with his mouth open the guy should take out his (hard?) cock and move towards your partner. watch as he puts his cock in your partners' mouth and tell him to suck it like the good little whore you trained him to be!

This will be an experience for both of you to enjoy and possibly to repeat but you should at least try it once!

Have fun!