Let's Do Anal Anonymous TwiFic Contest
Title: Uncharted Territory
Pen name: addicted-to-romione-bedward
Summary: Lady Isabella decides to punish her naughty boy, but instead of pain they both get pleasure from exploring his back door. Entry to LDA Anonymous Contest.
Word count: 3,217
Warnings: Consensual anal sex. Pegging
Inspirational picture: 24 .media .tumblr dot com tumblr_lbb73r1bGL1qbm163o1_500 .jpg (remove the spaces)
I've been Lady Isabella's pet for five full years.
I started at the ripe age of eighteen when I discovered what a relief it brought to me giving up control. Not once in my life before I had her, had I felt so…liberated.
For one year, Lady Isabella trained me in my spare time. She was supportive of me getting a degree—even hiring me as her personal assistant. At first, I didn't like being scolded in public for messing her files or bringing her the wrong coffee, especially when she was in one of her moods.
That entire first year, she didn't once show me her true nature. She taught me how to be obedient, how to never raise my head or meet her eyes, how to cook for her, how to clean, how to please her. In return, I got my release, unless I messed up somehow at one of my tasks.
To celebrate one year of submitting to her, she allowed me to do whatever I wanted to her for a day. She was extremely pleased by the time she went to bed. I'm sure I never—after or before—have I given her so many orgasms.
I've learned a lot over the years and rarely messed up. Lady Isabella is very intelligent and inventive. She'd time me and if I was one second too late, I'd get punished. She'd ask for her blue bra only to change her mind that she wants the red one when I bring the blue one.
But I am not complaining. I get off on the slight pain she gives me, because she is never brutal unless I truly do something awfully wrong. Like that time when I shredded the wrong papers. My ass was sore for a whole week.
Speaking of ass—that reminds me of why I'm kneeling in the hallway, waiting for her to arrive home.
Last night, I accidentally offered her peanuts. She didn't realize it right away…only when she couldn't breathe. I was such a fucking idiot. Taking care of my Lady was my top priority.
And what did I do?
I gave her peanuts. She's freaking allergic to them.
So that ended up with me sleeping on the floor.
It resulted in a fitful sleep and sore muscles. I haven't slept on the hardwood in years.
To add more punishment to my list, I was late with her coffee because some stupid chick kept changing her mind—while my eyes kept watching the clock's hands moving and moving and moving.
What's another punishment, right?
I'm sure she'll send me away for what I've done next.
First, I was late with the coffee.
Second, I interrupted her meeting with important people.
Three, my toe caught in a chair's leg and I spilled the coffee on her favorite fuchsia dress. Lady Isabella doesn't usually like that color—only on this dress.
I am so fucked.
The look in her eyes… I felt like I've been handed fifty lashes of her whip just by that one brief, angry look she gave me.
She politely excused herself to the businessmen who were understanding and gracefully allowed her to leave the conference room to change her spoiled dress.
I followed suit, head tucked in my chest, tears brimming in my eyes.
The second the door of her office closed behind me, a hard rezoning slap landed on my right cheek. Then she went to change her dress. I didn't move from my spot.
When she returned, looking fresh in a navy knee length dress, she pushed me away from her path making me stumble into the couch.
"Your ass in mine tonight, slut!"
The door slamming shut pulled me out of my shock.
She never touched me there.
True, I never said it was off-limits, but we never…
Fear gripped me.
I wasn't ready.
I tried going back to my duties, doing my best to keep my head clear and not get in deeper.
On lunch break, Lady Isabella took me to her private bathroom where I had to drop my pants. A cock ring and chastity belt locked on me then she made me bend over—my hands resting on my knees as she worked on loosening my back door.
Instinctively, I shifted away when her finger traced my hole. Her other hand brutally dug her nails in my hip making me stay still. Slowly, excruciatingly slowly she worked a finger then two into my ass. She kept dripping lube and scissoring her fingers inside me until the tip of one finger touched a spot that made me moan so loud I feared we'd alert people on the floor.
"Such a slut," she murmured, inserting another finger then pumped all three of them.
My dick ached not being allowed to swell to its natural length, but I was so close to coming. What a paradox. While I was wondering if it was possible for me to come while not erect, I heard drops of something on her bathroom's tile.
To my surprise it was cum. Mine.
In that moment something foreign was inserted in my ass making me shout in pain, but more in fear of the unknown.
"Disgusting. Clean that mess, then I want the conference room ready for my next meeting!" Lady Isabella snapped at me.
For the rest of day, I suffered.
The plug in my ass shifted with every step I took which resulted in a constant state of arousal.
When I left work, she instructed for me to wait in position.
All I hope is that she's going to be the one taking me up the ass. I'll probably want out of our relationship if she brought a man along.
We've experienced with others—a lot. I even shared her with another man, but she never shared me. She always said that I was only hers.
The door unlocking pulls out of my mind.
"Beautiful, pet." Her heels click on the tile as she approaches me.
Thank Baby Jesus.
One finger lifts my chin, but I don't make eye contact. Her other hand pets my hair.
"Why must you disobey me?"
I gulp, feeling horrible for everything I've done in the past twenty-four hours.
"I truly hope you are ready for this, my beautiful slut. I've wanted to claim your ass for too long."
I shiver violently at her words—it's all pleasure.
I trust her completely.
"Does it hurt? Is it too much already? Talk to me."
"Your pet loves the feeling of the plug, My Lady."
"Greedy little pet." Lady Isabella bends so her lips press against my forehead. "All mine."
"Always yours," I promise. "I'm sorry I talked without permission," I add quickly.
"Don't apologize for such beautiful words. Now, follow me to the bedroom."
I immediately obey, crawling after her.
We don't have a Playroom, but we don't need one.
Everything she owns is stowed away in a special dresser.
I stop at the foot of the bed—my hands linked behind me, my head down, waiting for my punishment.
Is she going to simply take me, or I'll have a proper punishment before she fucks me?
When I hear the squeaky drawer being pulled open I know that the fucking will have to wait.
"Lean forward, arms stretched in front of your body, ass up in the air."
I immediately move in the desired position.
"You have to count for me, slut. Fifteen for your unforgivable mistake from last night. Five for being late. Another five for interrupting. And if you're still awake, ten for ruining my dress and embarrassing me."
I can feel my blood racing through my veins as adrenaline takes over my body.
I've never gotten so many in one go. We're setting new records tonight—if I'm conscious by the time she decides to do the anal part.
"We'll work on five rounds then a little respire time."
I nod, tensing up at the sound of the whip swishing through the air.
I'm not sure what I despise most—the whip or the flogger.
"One!" I say loudly, clearly.
All too soon I'll be a blubbering mess. Might as well do it nicely while I can.
The back of my thighs is on fire.
"Four, five," I blurt out, pressing my forehead on my arms.
"Tsk, tsk. I didn't allow you to rest your head," she hisses in my ear, pulling my head up by my hair. "Don't make me repeat myself."
Her hand soothes somehow the ache on my ass before she goes back to administrating my punishment.
This round, her smacks are tapping the plug, making my eyes cross—the sensation it's between please and pain, leaning more toward pain.
By the end of the third round I'm breathing hard and there are tears rolling down my cheeks.
I doubt I can take four more rounds, but if I say my safe word, she'll stop. I don't want to stop. I just want to get over this disciplining thing.
"Three," I sob on my fourth round. "My Lady!" I wail loudly, my fingernails scarping uselessly at the floor under me.
"Am I too rough?" she asks worried.
I nod, not even stopping to think that she has never before been this concerned about me. Of course, she made sure to never break my skin and for me to be in proper mind shape, but never so worried.
Her knees thud next to my head, which found its way back to my arms.
Her long nails scratch against my scalp.
"Get on the bed, on your fours. I'm going to soothe the ache," she promises, standing and walking to the bathroom.
I crawl on the bed, quickly brushing my tears away. I don't want her to see me weak.
Lady Isabella returns with cream and rubs it on my flaming ass cheeks and the back of my thighs.
"Tsk, pet. Why didn't you stop me sooner? Now I ruined the best part of the night."
"No!" I shout, turning around, begging her. "Please, don't stop."
"Don't get an attitude now," she chides me lightly, stroking my ass. "Don't move."
She goes to the dresser and I see her pulling out a double dildo. She's only used that one when I had to share her with a woman.
Ah, that's a nice memory now.
To my surprise she puts it pack, shaking her head. Well, maybe we're not doing this after all. But then she takes out a strap on that will bring both of us pleasure.
When her eyes meet mine I realize I shouldn't be looking and I quickly drop my head, tensing up when she approaches me.
Why do I have to be so stupid?
After so many years I can't even listen to a simple order.
Lady Isabella touches my head. "Sweet pet, please I want you to be as vocal as you want tonight. Talk to me all the time. If I hurt you in the slightest, please tell me."
"Yes, My Lady," I answer.
"How about you call me just Isabella? Or Bella?"
I gasp, turning my head to stare at her in shock. I don't even care if I'm being disrespectful.
She cups my cheek, stroking her thumb over my lips. "It's just us, baby."
I swallow, finally understanding it's not part of the game.
It will be just us—Edward and Bella.
We got the lines blurred a couple years ago, and we couldn't go back to what we had before. Of course, our sessions are focused fully on my discipline or her personal needs—just like in the very beginning.
Though lately, more often than not we end up being just us.
This is the first time she'll use her special toys in our off time.
"Edward, are you okay with this? Do you still need to be in your submissive mind set?"
I shake my head. "It will be okay. Don't worry," I promise.
"Alright. I trust you, honey. Now, sit up so I can unlock you then I'll take care of your lovely ass." She kisses my shoulder as I shift in the desired position.
My ass cheeks hurt a little when they come in contact with my soles, but it's bearable.
Bella works on my chastity, freeing my poor dick. She strokes it a few times once it's free then puts aside the chastity. The ring is still around the base of my cock—it's not going anywhere any time soon.
"Okay, honey. Lean forward. You can rest your head on the pillow." A hand runs down my spine, over my heated ass then she taps the plug a few times.
I shiver, letting out a low moan.
"Fuck," I groan into the pillow, fisting the bedding.
Bella works on extracting the plug creating all kinds of delicious feelings inside me. She even fucks me with it for a few moments but when I get too close, she simply pulls it out, jumping off the bed to take the toy to the bathroom.
I can feel my hole fluttering, probably trying to close again.
My ass is surprisingly empty. I want something to fill me, make me feel good.
When she returns to me, I hear shifting and a few soft gasps of pleasure from her. Curious of what she's doing, I peek around my shoulder and groan at the sight in front of me. Bella's pushing one end of the strap-on inside her pussy before she fastens the belt around her hips.
She gives me a wink, coming to stand next to my head.
Fuck, the sight of her!
"Bella!" I moan, touching her thigh. "Please."
"Oh, my greedy little pet is back." She giggles, bending to peck my forehead. "Kiss my cock, honey."
My eyebrows shoot up as I meet her eyes to see how serious she is about this. She's dead serious.
"Edward, don't upset me or we're playing again and you'll be denied release!"
Keeping my hand on her thigh, I lean closer and kiss the tip of the silicone. She pushed in my mouth making me rip away, sputtering. It tastes horrible.
Suddenly, she's in charge again, my head pressed into the pillow—actually, my cheek is pressed to the pillow. My mouth is opened forcedly and the silicone is filling it roughly, her angry gaze penetrating my soul.
"Can you ever listen to me?" she hisses.
I beg her with my eyes, promising I'll be good.
She pulls out, taking my face between two fingers, glaring at me. It looks she'd like to spit on me, but she doesn't, shuffling around me to position my ass how she wants it.
One finger slides into my stretched hole, quickly followed by another. My ass feels slick with the amounts of lube she's using. The sounds coming from her pumping into me can rival the times I'm pumping into her—when she's extra horny.
"I truly hope you're ready. I truly wanted this to be our experience not just mine."
I disappointed her.
Then I feel the tip of the silicone at my ass and my muscles lock up.
"Relax, Edward." Her hand rubs the small of my back.
That—the use of my name shows me we're not actually in a role.
"I'm trying," I whisper, taking a deep breath. It feels good, remember? I try to will my muscles to relax.
Slowly, Bella opens me and slides a few inches inside me.
"FUCK!" I yell, bucking my hips.
"Hurt?" she asks concerned.
"More! Go deeper," I beg in a whiny voice.
She chuckles, holding my hips still as she inches further. The burning sensation dulls with every inch she penetrates me. All too soon she's seated deep inside me.
When she just rocks her hips, both of us moan loudly.
I can only imagine how good this must feel for her. She's in charge—one thing she loves—and she's getting her own pleasure by doing this to me. I'm getting pleasure too.
After a few pushes and pulls, Bella slips out of me and lies on her back next to me. "Come on, honey. Ride me—your back to my chest."
"I don't want to crush you."
"You won't. Trust me."
I listen to her and move to straddle her hips, lowering myself on the strap-on. It's a wonderful feeling to be filled like this.
I never thought having something in my ass could be so pleasurable.
We might have found my new addiction, though it will be hard to say goodbye to that vibrating cock ring she gave me for my birthday last year. That's my reward for being a good boy. Of course, I try to be good every day.
Try being the key word.
Once seated on the dildo, I start moving, fucking myself.
One of Bella's hands wraps in my hair, pulling my head back so she can kiss my neck. Her other hand finds my aching, purple dick.
"That's it, sweetheart. Fuck yourself. Make me come. Yes, just rub your ass on me like that. Ah, I'm so close."
Already? I think surprised.
I keep rounding my hips in small eight movements until Bella bites down on my shoulder, straining under me. I keep moving, the angle having change during her orgasm and now the head of the dildo hits my prostate gland.
"FUCK!" I yell when pleasure ricochets in every nerve ending of my body.
"Don't stop!" she begs in a mewling voice. I know she's about to have another one—much stronger one.
Not like I'm going to stop any time soon.
The way the dildo hits my glad is too much and the way her thumb smears precum over my purple head…My muscles lock, my back arches as I yell her name at the top of my lungs as long ribbons of cum shoot from my dick. Bella finds her second release under me, now holding me tightly to her chest.
"Whew! We need to do this more often," she murmurs in my ear, moving my wet hair away from my forehead. "Still alive?"
"Give me a few minutes and I'll show you how grateful I am for this experience."
I take the dildo out of my ass then take the strap-on from her hips, before covering her body with mine, hugging her tightly.
I love our time after every session.
She loves to cuddle, just like me.
"I'd like nothing more than to have you thanking me—but later. I'm tired."
I kiss her cheek, resting my head on her chest.
If disobeying brought me to that amazing orgasm, I'll do it more often.
I try to imagine how it will feel to have her plastic dick in my ass and the vibrating cock ring around my dick.
"I just told you I'm tired. I don't care if your solider is up for round two," Bella mumbles sleepily.
"Can I have the vibrating cock ring on next time we try this?"
"You're extremely naughty lately, my dear pet. I can't say no to you."
I just smile against her breast, closing my eyes.
I didn't win anything, but it was a wonderful experience to be part of this.
The other entries are these (some already posted on ffn):
All I Have to Give by LyricalKris
AP 101 by LovinRob
Everything by Marlea Pie
Hidden Desires by Siobhan Masen
I Never Knew by robownsme
Let My Love Open the Door by fbbroughtustogether
Show Me Something More by karenec & Discordia
Smorgasbord by julie_durden & Cris
Turnabout by coldplaywhore
Uncharted Territory by addicted-to-romione-bedward (me)
What's Good for the Goose by eternallyedward
Or you can read them here: letsdoanal .blogspot .ro/ p/entries .html