At first, I thought forcing him into bras might be to sissifying, but it makes an awesome punishment if he messes up. Force him to put a bra on and sleep in it [in chastity, of course].
In case he might actually enjoy that… Threaten to make him sunbathe in it. That would be a hard tan line to explain away in the gym lockeroom!
I love being feminized, love to shave down smooth. I also love the encasement feeling that quality hose or pantyhose provide. Especially with a full corset or body briefer. The body briefer provides the crotch flap, that I unfassen to either do myself with a vibrator, or get pegged by my Mistress. Usually we will play a number of TS or sissy videos, and I lube myself up and start to slide my vibe in and out while Mistress looks on, feeding me her pussy dipped fingers. She inserts two or three into her tasty pie, then holds her fingers oiut firmly, and instructs me to clean the pussy juice off her cock, and I am to engulf all her extended didgets, licking and sucking then clean as if they were a coxk. She person, that’s my good little faggot, suck my cock clean bitch. Yes Mistress I mutter as I give her fingers a mock blow job. She will then ask, you are planning on licking up every drop of your sissy bitch cum aren’t you bitch? Yes Mistress, of course I will eat all my cum, your hornet little cum slut hasn’t cum all week as instructed Mistress. That’s my good little cock sucking faggot. Now get your rubber dildo out and show me how good your cock sucking skills have gotten, I told you to practice this week remember. Yes Mistress, I did practice two nights this week. I would have practiced more, but I get so damn horny, and I was afraid I wouldn’t be able to not do myself and cum Mistress. Well let’s see you suck that cock bitch, you know you want a real juicy cum filled cock in your mouth and another in that bitch pussy that you fuck for hours at a time while day dreaming about a hot tranny cock filling your cum hungry mouth with huge loads of cum, ain’t that right faggot. Tell the truth bitch, you dream about sucking cock and gobbling cum all the time don’t you? Yes Mistress, it’s true I crave cock and cum everyday. I know you do, I see how hard that bitch cock clit gets when you watch those fags sucking those tranny cocks in your TS movies and sissy training videos. In fact, I bet your sucking dick behind my back, you shameless sisdy faggot. No Mistress, I would never cheat on you. I never have and never will Mistress. You better never let me catch you cheating bitch, I own you. Yes Mistress.Well okay, suck that dildo cock and fuck that bitch pussy harder faggot, and you better cum a huge load to lick up for your Mistress, or I will know you been cheating. Yes Mistress, do you want me to cum now then. Not yet, let me forward this tranny video to a good cock sucking scene so you crave that cum load even more. Turn your vibrator up and fuck your pussy deep cum slut. Oh yes Mistress, oh yes that feels so damn good. Thats right, look at that fag suck that huge tranny cock bitch, that’s who you wish you were. Here’s your cum cup bitch, you better not spill a drop either. Yes Mistress, oh fuck yes I need this cum Mistress, you’ve trained your sissy so good. Awwweweee ooooooh yeah, yeah, yeah here I cum Mistress, a huge thick load saved just for you. Ooooh yes, yes, yes mmmmnmm ooooh damn. See Mistress, a huge thick creamy load I saved for you. You saved it for you, ya cum guzzeling faggot, now swallow up every single drop sissy. Mmmmmmmmmm its so yummmmy Mistress, I wish I had more to eat up for you. And see, I’m licking every drop from the bottom of my cum cup. Very good, that’s my good girl, that’s my good little faggot girl. Thank you Mistress, it was so yummy. You have me loving my own.cum now, you’ve trained me well Mistress. Yes, I have. Now I just got to find you a couple other sissy’s bitches to fill both your holes at once. I’m going to video that, then you’ll be my full time cock sucking, cum swallowing, butt fucked sissy faggot for life. You will suck any cock I tell you on command. Yes Mistress, I’m your sissy cum slut for life.