Disclaimer: This story is entirely fictional. All characters in this fictional work are over the age of 18. This work is intended to be consumed by adults, 18 or 21 years of age, depending on your location.
Note: This story contains elements of femdom including pegging, chastity and cbt. If these elements do not appeal to you, please do not read.
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It was late in the evening and I hummed a tune as I hurried up the stairs leading to Ann's flat. Punctuality was something I was known for and today was no exception. I had all the more reason to be on time to meet Ann though because I had a feeling she wouldn't take too kindly to me being late. As hot as it was to be punished by her, at the end of they day her punishments were measured but harsh and not things I looked forward to.
I rang the doorbell and smiled widely when Ann opened the door for me. She was wearing yoga pants and a long black shirt which reached her upper thighs and had the logo of The Strokes on it. She gestured at me to come on in as she was speaking on the phone.
I walked in as she walked around the house distractedly and began to undress. By the time Ann was done with her call and walking over to me, I was naked and on my knees in the "present" position (kneeling with my hands on my head and legs spread).
Her face lit up when she saw me presenting and she laughed.
"At least buy me a drink first." She said with a wide smile.
I smiled back but remained in the same position. "Just trying to be a good toy for you, Goddess."
"Well you might have just earned some brownie points with me for that little touch. Would you have stayed that way if I was on a call for the next two hours or so?" she asked me curiously.
"I assumed you were almost done with the call because we were supposed to meet." I replied. "I hope I wasn't keeping you from anything."
"No no that was just...you'll see later." She said mysteriously.
I wondered what she meant but her expression was inscrutable. I'd planned to meet Ann for a light meal and a catchup but had ended up having my cock locked up, my ass fucked and turned into her toy the last time we'd met. I obviously couldn't predict what she had planned for me.
"Come on then, I thought we'd just talk for a while but you obviously want to get right to the point." She said, her eyes flashing with mirth as she helped me up to my feet. "Now we'll have to multi-task. Go over to the wall and bend over."
I walked over to the wall she was directing me to and bent over, wondering what she meant by 'multi-tasking'. I assumed she was going to flog me or something but the pain never came.
"How was your week? How's your course going?" She asked me casually as I stood against the wall, wondering what she had planned.
"My week wasn't too bad, we just had a few fun guest lectures and a couple of painful assignments. Could have been worse but I'm glad that it's Friday. The next week is the one whi-OH FUCK"
I'd abruptly stopped and moaned because Ann had grabbed the plug buried in my ass before she thrust it back inside me.
"Continue." she said calmly, not responding to my sudden moan.
I knew the drill.
"The one which might get a little hectic. I'm on track to make sure it goes well but we sh-AHH."
This time she'd grabbed onto my balls and given them a quick but hard squeeze.
"We shall see." I ended and felt Ann pull my hair gently. I turned around and she took my hand and walked me over to the bed where she instructed me to lie down.
She sat on my chest and faced my locked up penis before she started to inspect it closely.
"No problems with the cage huh? You went a week in it."
"No I didn't have any problems with it really. Morning wood was pretty bad but I got a bit more used to it as the days went by." I replied.
"No one caught you either? No rumours about you being in chastity in your college group huh?"
I shuddered thinking about the potential consequences. There had been one situation where I thought the imprint of the cage on my pants could be seen but thankfully no one noticed.
"That's a pity, I can imagine you stuttering in that cute way of yours as you try and explain yourself out of that one."
I shuddered once more wondering how one could even explain one's way out of being locked up in chastity.
"Turn around. Let's get your poor little cock out of its cage."
I obeyed her and she casually handled my cock, unlocking the cage and pulling it off. Immediately I began getting hard. The lightest touch sent shockwaves of pleasure coursing through my body. After a week of being caged, I was incredibly sensitive.
She grabbed me by the cock and started walking towards her bedroom. I followed quickly, occasionally having to tiptoe because she'd pull my penis up a bit while walking. Ann was very casual with how she'd dole out amounts of pain and humiliation. Casual about it even.
She guided me to the bed and lightly spanked my ass, gesturing at me to lie down on the bed.
I lay down and let myself relax. Ann pulled out a a pair of handcuffs and some ropes. With that she deftly began to tie me up. I closed my eyes and let her guide me. My hands went behind my head and were cuffed before they were tied to the headboard. My legs too were spread and tied to the different corners of the bed.
I tested my restraints and it was clear that I was well and truly restrained and completely at her mercy.
"Close your eyes and relax. You're going to be begging and pleading by the end of this anyway." she whispered, giving me a kiss to the cheek before moving away to admire her handiwork.
Wanting to be a bit of a brat, I thought I'd mess around. It was clear that she was the boss but I wanted to play with her as well.
"Begging you to stop boring me?" I quipped while looking straight at her.
Looking at me with a surprised but amused look, Ann laughed before getting onto the bed and sitting on my stomach, looking me in the eyes. "Where was this bravado when your balls were in my hand and you were babbling away? Well it's good that you have some fight in you at least. I like my toys to squeak a little before I break them."
With that she lightly slapped my face once, which I responded to by staring at her defiantly and rolling my eyes.
Ann smiled and slapped my face again, using her right hand to slap my left cheek. She slowly began to slap me repeatedly, increasing the force. While I wasn't in any sort of pain initially, I began to feel it and it turned into a feeling of sharp pain.
I refused to beg her or apologise. I could take the pain because it wasn't that bad. My eyes began to water slightly and eventually she slapped me one final time before rubbing my cheek.
She smiled at me, her sweet smile betraying none of the pain she'd dealt me. Leaning lower she kissed me, slipping her tongue into my mouth gently before breaking apart from me.
With that same smile, she spat on my face. I instinctively attempted to wipe it off but my bindings prevented me from doing anything more than struggling a little. I felt it on me and I felt my false sense of bravado disappearing. The message was clear.
"Now close your eyes before I slap you again. You keep them open again and I'll redirect my slaps to your balls. I'm being nice and not blindfolding you but I can do that too."
I grudgingly closed my eyes at her words and waited. Ann was happy to keep me waiting. I could hear her moving around the room and occasionally humming what sounded suspiciously like S&M by Rihanna.
I found myself drifting away, not exactly going to sleep but just this sense of calm. I didn't know what Ann had planned for me but I also knew that she was in control. I was allowed to relinquish control and not worry about anything.
I realised I couldn't hear Ann anymore since I'd stopped focusing on what was happening around me but I figured she'd gone out of the room. All of a sudden I felt what was unmistakably a very warm, wet mouth enveloping my incredibly sensitive penis.
I let out what must have only been described as a cross between a moan and a squeal which caused a muffled sort of laugh and I looked to see a sight which caused my penis to get harder than I thought it was possible to ever get.
Ann was lying down on her front and had cutely lifted her feet up and was swinging them around playfully. She'd taken off her shirt and tights and was clad in only black panties which accentuated her ass. My cock was in her mouth and she was watching me as she suckled on it.
"You can watch if you want to but that means a punishment after this." she said, her mouth making a pop sound as she stopped sucking my cock to talk to me.
I was left with a conundrum. One one hand I could close my eyes and avoid whatever cruel punishment Ann had planned for me but I could watch an absolute goddess go down on me.
On the other hand a punishment by Ann was no joking matter. I decided to just focus on the here and now and I nodded to Ann with wide open eyes. She smiled in a way which almost seemed....proud? That I'd make that choice?
I watched as Ann's head bobbed up and down. She was definitely skilled because she seemed to know exactly what she was doing. She kept an eye on me to make sure she was paying attention to what I liked.
My cock was average to slightly below average in size so she had no problem taking in most of me every now and then. I wondered if she had a gag reflex or if she was just used to bigger cocks.
She also didn't just stick to one thing. She'd take in my whole length with ease before letting go and then she'd lick at the very tip of my penis. She'd play with my balls every now and then.
Suddenly I felt one of her hands go lower than my balls and I felt her press at my butt plug. She pulled it out causing me to gasp and immediately slipped in a finger into my well lubed and slightly stretched ass.
