I needed some cash bad but didn’t know how to get it. Then I thought of burgling someone. It seemed like the perfect solution: simple and low risk. But then I started thinking about it more. Who could I hit? I could try a house in some rich neighborhood, but what if there was an alarm? Someone with a gun? A noisy neighbor?
Then I thought of a woman I had seen in a friend’s apartment complex a few times. She was a hot brunette and she dressed like someone who was loaded. That seemed perfect. My friend would let me in, it seemed unlikely that she would have an alarm, and being seen by a neighbor seemed unlikely too.
So I found myself in front of her door the next day. To be safe I knocked on the door. I was ready for a cover story if she answered it. But when the door didn’t open and I didn’t hear anything from inside I jimmied the door and went inside.
I found myself in the kitchen which didn’t seem too promising. I really needed some cash or jewelry or electronics. Something small and valuable. So I stepped into the next room and…holy fuck! It was full of weird tables and benches. And the walls were covered with whips and paddles! I was getting a bad feeling about this…but I was here and I did need some green. So I looked around some more, trying to avoid looking at the implements on the walls. And then I heard a key turn in the front door…
Fuck! I thought of hiding and looked about, but there was nowhere. And then the door opened and she was there! It was clearly time to bail so I put my hands up and said as calmly as I could, “I haven’t taken anything so I’m going to leave now.” She gave me an incredulous look and said, “Were you tying to rob me?”
“Not any more…all I want to do is leave and never come back.”
She said, “I think I have something to say about that.” Then she stepped closer. And bam! She kicked me right in the balls…hard. I dropped to my knees, she pulled some handcuffs from her purse, and cuffed my hands behind my back.
After a minute I recovered and barked, “What the fuck is this?”
There’s a blur of movement and I feel the sting as she slaps my face hard. “Keep a civil tongue in your head or your balls will feel the point of my shoes again.” Then she smiles, “Most women would call the cops when they come across a man trying to rob them. But I’m going to give you a choice: either I call them and you go to prison or you agree to play with me.”
“But if you don’t play well I’ll call the police. And you know what will happen once you’re in prison. Before the week is out you’ll be some gorilla’s bitch and he’ll pimp you out everyday for a package of cigarettes. You’ll get more cock than a hooker in Thailand!”
Oh god. I could just see it. Some huge tattooed thug pushing me to my knees. Taking out an enormous cock and making me suck it. And fucking my ass. No way. No fucking way. But what could I do? I didn’t have a lot of options with my hands cuffed behind me. I could try and over power her. But I was on my knees and I didn’t like the odds. And if I lost I’d really be screwed. Assaulting a woman…the judge would bury me.
So I swallowed hard, looked up at her, and said “I’ll play with you.” She gave a little smile and bent forward a bit, “You’d better play well! If you don’t it’s off to prison with you!”. Goddamn. Did she have to say that while leaning forward like that? Fuck. She’s even hotter than I remembered. I so don’t need to think about being punked in prison while looking at her fabulous cleavage.
She tells me to be still and pulls my wallet out from my pants. She calls her girlfriend and gives her my name, address, and driver’s license. I lean forward and rest my head on the floor…now I am really screwed. There is no choice…I have to do what she wants…whatever she wants.
She has me stand and then slaps me again, “Are you going to be good?”
I blink away a few tears and mumble, “Yes Ma’am”.
She has me undress and then binds me securely..very securely to a device shaped like a large T. She gets close and whispers in my ear, “Do you know what’s going to happen now?”
“I’m going to whip you…hard. I’m going to whip you until you beg me to stop.”
I try to be brave. She did want me to play well after all. But I can’t help shivering. I’m sure it’s going to hurt. It will probably hurt a lot…but no matter what it has to be better than spending years in prison on my knees. It just can’t be worse than being a bitch in prison…
I wait and I wait…but nothing happens. Damn…she is going to whip me. Isn’t she? Isn’t she? Then she cracks the whip and I jump. “Are you ready sissy?” I can’t help trembling but I say yes. And she starts whipping me. Ohhhh. It hurts but it’s not so bad. I can’t help moaning a little bit, but I can take it.
Then there’s a pop and my back is on fire. And unlike before the pain stays. And again…pop…pop..pop. Damn, that hurts. It’s so much, I don’t know if I can take it. Without even thinking I start crying out, “Please…please…please”. Then I remember prison and her saying I need to play well. But damn it hurts! Haven’t I played well enough?
She says, “Try and take it like a man sissy.” And she strikes me again and again. It’s too much. Way too much. “Please stop…please stop…please.”
“Oh, I’ll stop sissy. All you have to do is beg to suck my strap-on”. Then she whispers in my ear, “But you’d better do a great job sucking cock. Because if you don’t I’ll fuck your tight little ass with it!”.
Then it’s back to the whipping. Oh god! I can’t suck cock! Pop…pop…pop. But…but…it’s not a real cock. It’s not going to cum in my mouth. And If I do it really well she won’t fuck my ass. Pop..pop. “Please…I’ll suck your cock! I’ll suck it like a high class hooker! Please let me suck your cock!”
“Wow! You really are a sissy! Maybe you’d enjoy prison.” I just hang my head. I can’t believe what I about to do. But I have no choice. I had no choice since I decided to rob her. All I can do is suck her cock as well as I can and pray that she doesn’t decide to fuck me.
When she turns me around I can’t look at her. So I stare at her feet. And she is wearing black stilettos. Shiny black stilettos with a really high heel. Shit! I start getting hard and of course she notices and laughs. “Like the idea of sucking cock sissy?”
She has me kneel facing the wall while she gets ready. Oh god. I’m going to suck cock. But it’s this or prison. And it’s not a real cock…it’s not a real cock. But I have to suck it really well. I have to do it just like a call girl would. I have to go to town on that cock. I probably even need to pretend to enjoy it. Oh god…
Then she has me turn around. And she is wearing a cock…a big black cock hanging between her legs. A much bigger cock than mine. I gulp and she crooks a finger to beckon me closer. On my knees I shuffle over. All the while my eyes are fixed on her cock…not her wonderful breasts, not her sexy heels, not her smile…on her cock.
And i get there. Still staring at that cock which is now inches away from my face. She takes it in her hand and slaps my face a few times with it. “Give it a big sloppy kiss sissy!” What can I do? I have to suck her cock. I just have to. So I do what she wants and give it a sloppy kiss right on the head. She pats my head, “There’s a good little cock sucker.”
Then before she says anything else I lick the shaft up and down and take the tip into my mouth. I wrap my lips tightly around the shaft and start to flick my tongue against the underside of the shaft. It kills me but I even moan a bit. It’s not real cock after all and if I do well enough…if I’m enthusiastic enough maybe she won’t call the cops. And this nightmare will end.
So I slowly take it deep into my mouth. I keep my lips pressed tightly against that cock and slowly work my head up and down, up and down. All the while tonguing the underside of the shaft and head. She gives a delighted little laugh and says, “That’s how you suck cock!”. I cringe a bit but then I feel my cock start to swell.
What the fuck? I’m not a cock sucker. I don’t like cock! But now it’s actually starting to get hard. I pray to god that she doesn’t notice, but then I feel the sole of her stiletto rub against my shaft. She doesn’t say anything but she knows…she knows. I got hard sucking cock. I flush with shame but keep sucking and she keeps rubbing. And she keeps rubbing. I’m getting excited, very excited, while I am sucking her huge cock. I can’t help thinking…maybe I do like sucking cock? I feel even more shamed, and even more excited. Too excited, but just before I am about to blow she…stops.
“Looks like you enjoyed that cock sucker. But I’m not here for you to get off while you suck dick!”
She points to a padded bench and says, “Go lay face down right there.”
My head is swimming and I just want this nightmare to end. Without even thinking I lie down on the bench and she quickly binds me into place. As she fastens the last of the bonds I realize how I am bound: with my head down, my ass up, and my legs apart…
This is not good. This is not good at all. She’s not really going to fuck me is she? I sucked her cock! I sucked it so well! She can’t be planning on sliding her huge cock deep into my ass! I struggle a bit but I am not going anywhere. Then I think, well maybe she is just going to do something like paddle or cane my ass and I calm down a bit.
But then I feel something cold probe my back door and she says, “Are you ready sissy?” I can’t help myself and start babbling, “Please…please…please no!”
She laughs a bit and says, “Oh yes sissy! I’m going to fuck your tight little ass long and hard!” Then I feel the tip of that big cock enter my ass as she leans forward to whisper in my ear, “And you’re going to enjoy it…I’ll see to that.” I let out a little moan and say, “No….” as she slides it in deeper and deeper.
God, she has her cock so far into me and it’s filling me up so much. My head swims…I really do have a cock all the way in my ass. Then she slowly pulls it out and it actually starts to feel good. My god! The only thing worse than getting fucked is liking it! I’m so ashamed that I bite down and try to remain as unrespsonsive as possible.
But then she starts working the tip in and out…in and out…in and out. It feels so good that I can’t help myself and I moan and she says, “I knew you’d love being my bitch.” Then she begins to fuck me…slowly and deeply. And it does feel good. There’s no denying it: she’s fucking me and it feels wonderful. I try to remain stoic and hide what I’m feeling and I think that maybe it’s working.
But then she says, “Tell me you love it sissy!”
“Tell me you love it…or I will stop”
Stop? She’ll stop? God it’s good. I don’t want her to stop. I really don’t want her to stop. And I have sucked her cock…and she is fucking my ass. It’s not like saying it would be more embarassing than that. So I do, “I love it…I love it!”
“See! I just knew you’d love cock in your ass just as much as you do in your mouth!”
I’m moaning for real now. With shame and with frustrated desire. And she fucks me and fucks me until I feel like my head will explode. Then she stops. And as I lay there limp as a dish rag she releases me from the restraints and cuffs my hands behind my back and my angles together. And I find myself helpless at her feet…feet shod in shiny black stilettos. My head is still spinning but I can’t help but stare at those so sexy shoes.
A Phone Call
Until I hear her take out a phone and make a call. I can’t believe it! After everything I did! After everything I’ve been through! She’s calling the cops! As I gaze upwards at her in disbelief she says, “What? Did you think I’d just let you break into my dungeon and try to rob me?”
“But don’t worry sissy. I’m sure you’ll adapt to prison in no time. I’m sure that before the first week is through someone will make you their bitch. If you’re lucky he may even pimp your mouth and your ass out to anyone with a pack of cigarettes!”
“If you’re smart you’ll practice tonight. Just offer to blow a guard. Maybe he will give you a candy bar as a reward!”
I can just picture it. In jail…in prison…on my knees sucking cock after cock. Being bent over and having to take a cock in my ass. Being someone’s bitch. Having to drop to my knees and suck whenever he snaps his fingers. I blush, my breathing becomes ragged and…my cock starts to swell…again.
She laughs and begins to play with it using the sole of her stiletto, “Oh yes…a slut like you will just do just fine in prison!”
Special Thanks to Glory Holes!