I've had a few experiences in real life. My ex and I played with a few sissy maids and had them clean our house. It was fun, but they seemed more interested in the trappings of dressing up and being feminine than the actual service/submission aspect. Of course, a blowjob's a blowjob, so once my dick was in their mouths, their attitude didn't matter; I just grabbed their ears and took care of biz.
In a cuckold fantasy situation:
I like it when the wife takes the more active role in the sissy's training while I sit back and watch in amusement. I think it's incredibly sexy when a woman shows a cruel streak to a wimp, only to turn to me and in the next sentence be sweet and flirtatious. The contrast drives me crazy.
I do have a cruel streak. I like to make a wimp stand in the corner while I'm making love to his wife. He has to stick one forefinger in his mouth and the other up his ass. Every ten seconds, he switches fingers. I call it "sissy ass-to-mouth."
Or else the missus and I will make love while the sissy stands at the foot of the bed holding up his skirt, exposing his chastity device. That's hot, knowing he hasn't been allowed to cum in a month. And we hold it over his head; if the shine on our shoes isn't perfect, or if there's lint on the carpet, the sissy knows both of us have no problem singing out, "that's another week." A few fuck-ups add up, and the next thing you know, the sissy has to wait a fiscal quarter to cum. Keeps the bitch on his toes.
I like to fuck with the sissy's head from time to time. I'll make shit up. I'll tell the wife, "I caught sissy smelling your dirty panties," and sissy will look so sad and confused, knowing it's a lie but knowing he can't say a damn thing. I give him a wink and say "poor sissy, that's gonna be another month at least," as his wife marches him to his punishment stool. She says, "that's two months," and the sissy starts bawling. I know it's mean...but fuck it!
I'm not really into doling out too much pain, but I like to watch her do it while I kick back on the bed toking a doob. She tans that sissy's ass until he's blubbering and promising everything under the sun. Then she throws down her cane, sashays over to me, takes the joint and hits it, tosses it in the ashtray and straddles me cowboy style. We kiss to the sounds of sissy's whimpering.
Although I'm not a sadist, I will slap the shit out of a sissy if he gets out of line, or even annoys me too much. For instance, I don't like my coffee too strong, so if a sissy brings me some of that bitter-ass shit first thing in the morning, I'll slap the taste out the bitch's mouth, while his wife giggles. She likes it when I take an active role in her sissy's punishment, and will often use me as an incentive to behave. Kind of like "Wait till your father gets home." Because even though I'm not really into flagellation, I hit a lot harder than the wifey, and once I get going, I've got to admit, I do start to get a boner watching the faggot squeal and squirm, which only makes me want to hit him harder. Okay, maybe I am into giving out pain! Especially when I see how hot it's making the lady of the house, who plays with herself and encourages, "hit him harder; blister that little sissy ass."
It's great to just lay around cuddling with a woman and watching TV while her sissy scurries around preparing a lavish, romantic dinner for two. We dine on lobster by candlelight, sipping wine while sissy stands at attention. I imagine it's got to be murder standing in those heels all day...but fuck it. The sissy needs to be standing nearby in case we need a refill or something, so who gives a shit about the sissy's comfort? Sissies don't need breaks; they're sissies!
I realize it must be tough for sissies. Sometimes a fag will be sucking my dick and I'll rip a nasty fart that could peel paint, and I chuckle watching the poor little thing continue to obediently bob his head up and down. That has to feel pretty degrading, not to mention the olfactory ramifications. But I don't give a shit; what am I going to do, interrupt my blowjob so I don't fart in the queer's face? The thought never crossed my mind. My credo when it comes to sissy is: "Deal with it."
It's good to have sissies around. I wish I had one with me right now; my toenails need clipping.