We now switch to the Dad's POV.
You open the little pocket mirror in your purse, ensuring your makeup is applied perfectly. Your red wig is adjusted, and your clean-shaven face shows no signs of masculinity. You shift your dress slightly and adjust your fake breasts. You look like a woman now, elegant and feminine. No one would suspect you were a male if they saw you in public.
You take a deep breath before getting out of your car. You knock on the door to your client's house, and then...he opens the door. The man smiles as he pulls you into the house. He's tall, dark, and handsome. He is also your boss. He discovered your secret when you were in the bathroom of your workplace. You begged him to keep it a secret, in return for a couple of favors. He unzipped his pants and the rest is history.
"Well, hello, beautiful," he says with a slight grin. You blush before he pulls you into a deep and lustful kiss. You can feel the blood rushing to your cock but it doesn't get hard. As per your agreement with your boss, you are to keep your member caged when with him. Your clitty, as he calls it, remains trapped in its metal prison as he closes the door. "Now on your knees, sissy," he demands.
You look down on the floor as you get on your knees. He unzips his pants, letting them fall to the floor, his massive member hitting your feminized face. You close your eyes as he forces his cock into your mouth. He doesn't bother to let you take control, instead using you more as a pocket pussy. You were there to give him pleasure and nothing else. "Fuck yes...you were made to pleasure alpha men like me," he groans as he places his hands on your head, keeping you stable as he fucks your throat.
Minutes fly by before he finally releases his cock from your mouth and leans down, forcing another kiss on your lips. "Go to the couch and get on all fours, slut. I want that ass." You blush and obey his command. The buttplug he forced you to wear made your ass hole looser and more equipped to take his monster. He doesn't bother with foreplay, not when he wants to take you. "You're all clean-shaven like I told you to be. Good sissy." You blush and groan loudly as you feel his cock head meet your ass hole and he begins to go deeper.
Your boss moves your body like a puppet. Your face is down, biting a pillow as he rails you, your eyes flying to the back of your head. Each lingering thrust makes you more and more horny and submissive, just like he wants. You belonged to him and you didn't even bother to fight it. You wouldn't want to fight it either way. Not when it felt this good.
You lose track of time, failing to realize how many sissygasms you would've had if your clitty wasn't caged. The buttplug and dildos trained your ass well as you managed to take it as deep as possible, his grapefruit-sized testicles casting shame upon your less-than-average-sized ones. You feel a slight throbbing sensation in your ass before he quickly pulls his cock out. He grabs your head and begins furiously rubbing his cock, finally cumming all over your face. You swallow as much as you can before he lets go of you and tells you to clean up. Your makeup is ruined, smudged, and combined with cum. As you wipe off the last bits of makeup and cum from your face, you notice a note on the sink.
"Hey, sissy.
You're staying the night. Put on this makeup I got you. There's also a buttplug that you will keep on all night. You're not sleeping in my bed or on the couch. You will be kneeling next to the bed with my cock in your mouth all night. I'm already in bed and I'm still hard. See you there, slut."
You had no choice but to comply. You expertly applied the makeup and then inserted the plug into your ass, forcing you to moan softly. You then make your way to your boss' room. The light is already off and he is on his side. You walk over and his cock is sticking out of the blanket. You slowly get on your knees before taking his cock into your mouth. You take your time with sucking, milking him for all of his cum throughout the night.
This was your life...and your son didn't even know where you were. You wondered how he was doing as you sucked, entertaining the thought of being a sissy slut for him too. Or maybe he would join you in worshipping your boss.