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Chapter 76
by
caitlynmasked
Do you suck off Ray or does EDNA offer a different suggestion?
You suck him off.
Your boyfriend gently laid his legs out to either side of your body, unbuckled the ball gag, and pulled it free. Tossing it onto the nightstand, right next to the keys to your chastity belt, he then returned his hand to the back of your head. Meanwhile his cock kept growing in front of your eyes, now pointing right at your lips.
Days ago, You’d have fought and screamed and struggled against this. No matter what evidence there was to the contrary, you were still a straight man underneath all this feminine finery and female shapers. But the pills alone could compel you to fuck and suck as your boyfriend desired. The perfume was probably enough to do it on its own. Add in the incomplete pleasure of Ray taking your ass again, and You would debase yourself in ways you never knew before. And blowing your boyfriend was easy as the sticky spots from last night showed you’d already done this terrible task at least once.
Leaning forward you stuck out your tongue to give Ray’s cock a quick lick. The taste didn’t immediately immobilize you. Musky. Manly. Fleshy.
You continue to lick around his length and girth, getting him wet as you remember all the girls in the pornos do. Hoping that you can please your boyfriend enough to reciprocate and let you cum. His two orgasms to your one seems like a fair trade. He can use his hands, he can lick your slit… hell, he can just let you take care of it, just so long as you get this orgasm that your body feels like it’s been dreaming about for ages.
After you had him covered in your saliva, you guided him into your mouth. You were strangely thankful that EDNA cuffed your hands to your neck as you could use them while blowing Ray, leaving you to wonder if that was part of her plan. It didn’t matter at this point as the chain gave you just enough room to stroke his length while you started bobbing up and down. You could even cup his large balls when you took him deep enough.
Ray’s hand remained on your head the entire time you worked to please him, but true to his word he let you do all the work. When you heard Ray’s breathing grow ragged, when you felt his girth swell in your mouth, when you felt his legs tighten up around you, you redoubled your efforts. Your little tongue went into high gear around his shaft while you sucked and sucked for all you were worth. And your reward? A mouth full of his cum. You swallowed multiple times, assuming Ray wouldn’t want you to spit it out or even dribble his cum away, but some still escaped your mouth and slid down your chin.
As you pulled up and off of Ray’s cock and rested your head on his thigh, you could see the little pool of his cum on the comforter. You let out a sigh, knowing you’d never be able to see this bed as a place of comfort again. Your head would always be near that cum spot and you’d always remember being ravaged by your boyfriend here.
You hadn’t been up from your long nap all that long, but it had been quite the emotional and physical journey regardless. You found yourself still bound ass up, falling asleep on Ray’s thigh and only his sliding out of bed, woke you up. Turning back to you he smiled and cupped your cheek, letting his thumb find its way into your mouth for you to suckle. “Shh shh shh… you’ve had quite the day. I’m so proud of you babe and think we might be made for each other.”
With an audible pop as his thumb slid out from in between your lips, he started getting dressed. Your heart started beating almost as fast as when he first came into the bedroom. He can’t be leaving can he!? You… you haven’t…
Turning so you could present yourself more appealing to him you couldn’t help the words from spilling out of your **** mouth. “Ray? Lover? Please, I’m still ready for you. You’ve had my mouth and my ass, can’t you use the keys and take my pussy too?”
As Ray tucked in his shirt and pulled his belt tight he chuckled at your request. “Ahh babe, you’ve forgotten already. I like my girls to be constantly aroused and in the mood. You won’t stay that way if you get off each time we’re together. No babe, that has to be special. Trust me, it’s hard not to reward you for putting on such a show as you did today, but you’ve earned my respect. Be a good girl for me at the office tomorrow and maybe I’ll send you home with a reward!”
As he shrugged back into his jacket Raymond moved confidently to the bed and pulled you by your collar chain back into your face down position, attaching the chain to the headboard. You started your wiggling movements all over, knowing you only had seconds to entice him. You honestly don’t know if you could stand going without an orgasm and knew that there was no way EDNA was going to let you pleasure yourself once Ray was gone.”
Closing your eyes you put on your best sweet girl voice. “Please baby, don’t leave me like this. I’ve…” you let out a little sob, finding new ways to debase yourself “..I’ve been a good girl. I’m begging yo… MmmmpphhHHH!”
Your eyes flew open as you felt more than saw Ray buckling the ball gag’s strap behind your head. “Tsk tsk tsk, if you were a good girl, you’d know that begging like that is below you. When I’ve said no, the conversation is over babe!”
With a final slap to your ass, pushing another frustrated muffled “Mmmmph!” from you, Ray picked up the keys and started heading out. At the last minute he turned to look at you just as EDNA’s arms were coming out to unbind you.
Looking right in my eyes he smirked and said, “House assistant, are you there?”
“Yes sir, I am EDNA, Jane’s assistant. As Jane wishes to please you, I am here at your command.” Your eyes widened as EDNA answered and insinuated that she’d listed to Ray over you.
“I’d like my girl to remember questioning me and know that it’s not appropriate. How long has it been since her last pill?”
“Jane last took one of her pills three hours ago. Its affects should be diminishing by now and it will fully clear her system within the hour.”
Ray looked at his watch then back up at me. With a wink for me and his voice for EDNA he said “Good. Give her another. Another two. And leave her tied up like this until she needs to get ready for work. I’d like to see her moving a little stiff when she comes into the office.”
After hearing your phone ding, you heard Ray approaching you and felt him give you a kiss on the cheek. “You should be properly punished for defying me Jane, but I don’t have the time. Enjoy your night. I’d say think of me… but I don’t think you’ll be able to get me out of your head!”
You heard another ding from your phone as Ray strode out of the room, whistling to himself.
When you heard the whir of the arms and felt EDNA undoing your ball gag you hoped that she was going to be more practical and realize you couldn’t possibly spend the whole night trussed up like this. Unfortunately, the next thing you felt was her shoving another one of those damned aphrodisiac pills down your throat.
At least she didn’t put the gag back in…. “Yeeaaaoooww!!!!”
The flash of pain across your upturned ass was quick, unexpected, and intense. Straining to look over your shoulder you saw one of EDNA’s hands behind you with a leather strap.
Sounding like a mother addressing a misbehaving child EDNA said, “Jane, your boyfriend clearly said you should be properly punished. Research shows that ten counted spanks with a strap should suffice. Please count out each swipe, otherwise I will start over.”
“EDNA Ray didn’t say to spank me! That’s…” you racked your brain for anything to convince this diabolical computer to not repeat that experience “…that’s his job, not yours!”
The arm swung back and struck me again, causing me to yell out in surprised pain.
EDNA sounded very self-confident as she said “Jane, your boyfriend was very clear. He said you should be properly punished but didn’t have the time. Thankfully for you, I have all the time in the world and desire nothing more than to help you live the best life possible. And right now, that means pleasing your boyfriend and fulfilling his desires. Now, you haven’t yet counted so those do not count. Please count each spank. I can hit you roughly forty times before damage is done to your skin and I do not want to attempt repair before you go to work in the morning.”
Letting your forehead rest on the bed you close your eyes, not slowing the tears in the least, until the strap comes down painfully and you say quietly “one”
You realized the tears weren’t because of the pain. They were because the pill was also starting to ramp your arousal back up and you was afraid of what exactly you’d be feeling by the time EDNA got to ten spanks. Would you feel good? Would you enjoy it? Would you be taught to look forward to spankings in the future?”
“Good girl Jane. Your boyfriend would be proud. Let us continue.”
By the time EDNA got through ten counted spanks, your rear had been assaulted eighteen times. You couldn’t see it, but you’re sure it was a glowing red on both cheeks.
EDNA thankfully gave you several quiet moments to sob and cry before she applied a soothing lotion to your rear and shoved another of those damned pills down your throat. Surprisingly she offered you a drink of water before replacing the ball gag. You were burning with lust and didn’t bother with putting up any resistance. After a blanket was pulled over you, the candles were put out, the music stopped, and the lights were turned out.
You had hours before work and in this maddeningly aroused state you knew sleep would be fleeting at best. And Ray was right… you’d probably have images of him running through your head the entire time.
Does EDNA release you without incident or do you dream of your boyfriend?
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The Chronicles of Miss-chief
An anthology featuring stories about gender bending adventures!
An anthology featuring stories about gender bending adventures!
Updated on Jul 25, 2025
by BHCP2
Created on Feb 21, 2020
by vanillathunder
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