Because I Deserve It - Redux

I carefully hooked my arms under David's knees and lifted and parted his legs a little more, also tilting his pelvis back, to give me better access to the area I was interested in. I moved slowly, trying not to wake him. I sprayed a little cream on to my first two fingers, very gingerly moved David's balls to one side and wiped my fingers on his asshole. I repeated this three times and nice amount of cream was now covering his anal opening. I took my little finger and even more cautiously pushed it through the cream and into David's ass. Looking up a movement crossed his face, but he gave no other sign. I moved my little finger in and out slowly, working the cream into his hole. Then I changed to my index finger, which slipped in easily enough. I also moved it in and out a few times. I paused and licked the cream off my fingers, spraying a little more onto David to lube him further.

OK, now make or break. Very carefully I positioned the nozzle of the can on David's anus. Thankfully the leading edge was rounded, not sharp, maybe the designers had this use in mind. It was thinner than my index finger and, with a little pressure, it slipped right in. I tentatively depressed my finger for a fraction of a second - no reaction. I held it down for two seconds. David half opened his eyes.

"What's going on Em?"

"Nothing. You must have had a bad dream go back to sleep."

He nestled into the pillows and closed his eyes.

Right. Phase 2. This was going to wake him alright, so how to approach things? Let's have the courage of our convictions shall we? David says I love forced anal penetration and that's true. I'm guessing he will love it too. I picked up the vibrator formerly known as Rob, which I had brought from my room. Holding it in front of my eyes, I squirted cream onto its tip and rubbed it down the shaft. I added an extra dollop of cream on the top for luck. I rested the tip against David's asshole as lightly as I could, adjusted the angle and thought it was now or never.

I pushed as hard and quickly as I could. I was expecting a lot or resistance, but it slipped in beautifully and was most of the way into David's ass as he jolted awake. The look on his face was precious and I couldn't help but laugh at my disoriented lover, filled with whipped cream and impaled on a dildo.

"What the fuck is happening Em? What are you doing to me?"

I continued to giggle.

"Oh David. Did you like your wake-up call? Was it a bit too loud for your David? Are you cross with your little girl David?"

"Cross? What have you got up my ass? It's Rob right. Fuck. Yes I'm really angry with you. You can't just do that to someone when they are asleep."

"Stop that laughing young lady. I'll work out what to do with you later. But for now, can you turn the motor on? And I think I can take another inch or so."

He smiled, grabbed the backs of his knees and opened himself to be fucked by me.

"OK, you really should punish me. But I can fuck your ass first if that's what you want. I'll try to be a more obedient girl. OK?"

"Let me lube you a bit more first."

I pulled the vibrator out. It was streaked with white foam.

"What the fuck did you use Em?"

I held up the can of whipped cream.

"Seriously? I thought I felt cold. Well give me some more. And can I eat some when you are done?"

Putting down the cream, I first licked the traces of it off the vibrator. I pushed it into my mouth and l fucked my face a few times to clean it thoroughly.

"Mmm. David's ass flavor. My favorite."

I put the nozzle back into his ass and squeezed for a good four seconds. David opened his mouth and stuck out his tongue. I sprayed some on to it and he ate it smiling. Finally I lubed the vibrator with fresh cream. There wasn't much left. I knelt in front or David and eased my toy back into him. This time I was more considerate and gave him an extra inch or so with each thrust before pulling almost out of his ass and pausing.

"Ready?"

"Ready angel. That's good angel. Mmm. Fuck my ass. Just like that. Now give me more. Oh that's good. Is that all of it? OK, let's try the vibrations."

I turned the dial on the base to 2 (1 was for wimps) and felt it start up. David clearly did as well as he opened his mouth and took a sharp breath.

"That's good Em. You bought a good toy. Can we try faster?"

I turned it up to 4 and David's eyes opened wider.

"Fuck yes Em! Oh God, it's right on my prostate. OK enough speed for now. I want you to fuck me."

"Whatever you desire. A dutiful girl's only purpose is to please her lover."

I started to pull and push my eight-inch vibrator in and out of him. Withdrawing two inches or so before pushing hard back into him.

"Would you like it if I did this as well?"

I gripped his cock with my other hand and started to jerk him off at the same pace and with the same two-inch strokes.

"Yes I like that a lot sweetness. Maybe I could take the next level. Turn it up, but maybe just one level."

I turned it up to 8 and David flinched.

"You disobedient girl. I'll make sure you regret that. But fuck it's good. Oh my God that's intense. Harder angel please. You are going to make me cum."

I upped the pace with both hands. Now I was pulling back by four inches and I jerked his cock with longer strokes and a faster rhythm. David closed his eyes and bit his lip. He moved his head from side to side and quietly repeated "no", "no, no, no".

Stopping jerking him momentarily, I turned the dial up to 11 and felt David's whole body tense. I grabbed his cock and jerked it furiously, while pulling out close to the full length of the dildo and shoving it in again hard. I leaned forward and took the tip of his cock in my mouth, sucking and rolling my tongue round it while still fucking his ass and jerking him off.

"No... No... No... No... No. No. No. No. NO'OOOOH!"

I put my whole meagre weight behind pushing the toy deep into David's anal cavity. He bucked upwards, driving his cock a couple of inches into my mouth. I pulled down on his shaft, using his upwards movement to stretch his foreskin back down. He bucked twice more, now silent and grimacing, eyes tightly shut before releasing a torrent of cum into my waiting mouth. I slowed the pace of fucking his ass right down, while maintaining the depth. I pushed my hand on his cock down hard reaching the root of his shaft and gripped hard there. I sucked avidly on his cock, looking to drain every last bit of cum from his spasming member. I moved my head up and down, my lips massaging his twitching shaft.

As his convulsions abated, I lifted my head and swallowed the warm sticky liquid filling my mouth. I released my grip on his cock and withdrew the vibrator. Sitting back a little away from David, I licked the remaining cream off of the still buzzing toy before starting to rub my clit and vaginal opening with the tip.

"Have you forgiven me David? Am I still your favorite fuck-buddy?"

"I only have one fuck-buddy, more's the pity, so that bar is set pretty low."

His voice was husky and his was out of breath.

"No I haven't forgiven you. You are in big trouble little lady. You have no idea."

"Oh dear, have I been a bad girl?"

I sucked on the vibrator and pushed it deep into my mouth before withdrawing it spluttering.

"Did you want to make your little girl gag again?"

I slid the dildo down my throat again and pinched my own nose, counting to ten slowly.

"I liked that game."

"Bad girls don't get what they like. They get what I say is good for them."

"Right now, you filled me up with cream. You had better clean me up."

He spread his butt-cheeks for me. I got on to all fours and obediently licked his anus clean, poking my tongue inside him for good measure.

"Did I do a good job? Are you less cross with me now?"

"It's a start, but I am still angry. Your next punishment is no fucking for a while. We are going out and I need a shower. You can come and wash me. Make sure you clean my cock and ass thoroughly. Oh and I am confiscating your vibrator."

I did as I was told. I had to use my mouth to make sure David's cock was clean and he told me that the best way to clean an ass is to insert fingers covered in shower gel into it and waggle them about. I did everything I was told to do. David wrapped a towel round his waist.

"You had better wash yourself now as you are such a dirty little girl."

"When you are done, come back to my room and we'll discuss this matter further."

--

PART III -- PUNISHMENT

With a towel wrapped round my body and another round my head, I opened the door to David's room nervously. He was dressed, which made my heart sink. Maybe he really was pissed at me.

"Come in."

As I entered the room, I saw some things on the bed. There was some shiny black material laid out, was it a dress? Next to it was a leather belt, no it was too small for a belt, a collar? It had a single metal ring dangling from it, an odd fashion choice. There was also a pair of the highest heeled stilettos I had ever seen. Finally I recognized the latest (and largest) butt-plug I had asked David to buy me, but which we had not yet gotten round to trying. It came complete with a remote control which David picked up and put in his pocket.

"As I say, we are going out. This is what you are going to wear. I'm going to teach you to respect your elders."

"But I can't wear that out. What if I meet someone I know? They will think I'm a total slut, or an escort."

"But you are a total slut Emily. Today your name is Emily the Slut. You won't meet anyone you know where we are going. Anyway, you need to show me you can obey me as a good girl should."

"Oh and you'd make a great escort. Perhaps you could start to pay me rent that way."

"David!"

"Don't have a tantrum, you'll only make things worse. Now you have thirty minutes to get ready. You can go get your make-up from your room before I start the timer."

"But what about panties?"

"No panties. Don't look at me like that, I said no panties."

--

So where to start? Butt plug I guess. I eyed it worriedly. The box said five inches insertable and a two-inch diameter. Time to stretch Emily. I rummaged through David's bedside drawer and found a bottle of anal lube. Removing my towels, I spread them on the bed beside the other objects and laid down naked on them. I propped myself up on some pillows and parted my legs, my knees bent. I flipped open the lube and poured some on to the tips of my first two fingers. I wiped these around my asshole and dipped one finger into it, pushing the lube inwards. I repeated the process, this time inserting first one then two fingers and probing myself more deeply. Mmm... that was nice. But looking at the clock, I didn't have time to pause for pleasure.

I withdrew my fingers and lubed the other two as well, scrunched them to make a point and pushed this into my tight ass, twisting to try to stretch my muscles. I couldn't penetrate myself very far with four fingers, but early days. I then lubed my two index fingers and inserted them together, pulling myself open in first one way and then another. I picked up the butt-plug, it felt heavy and large. It has a stiff stalk at the base ending in a circular base, complete with the mandatory cheesy fake jewel, amethyst in this case. I drizzled lube on to the top, making a small circle from which the lube trickled down. I smeared it around with my hand and then did the same again. I dripped some more onto the tip and was ready for try number one.

I held the tip of the toy against my asshole and pushed gently. It was tapered and my ass yielded to it fairly easily. But as it widened, I started to meet resistance. I twisted it and changed the angle, keeping up the pressure until two inches were inside me and... ow! That was uncomfortable. I eased back to one inch, dripped some more lube onto the portion of the toy that was outside me and turned it round to spread it. Then I pushed again, my ass opened to take the extra inch and then maybe half an inch more. OK, too much. I withdrew the butt-plug completely, my asshole was gaping ever so slightly. I poured lube directly into my hole, put my index fingers into it and stretched it again. I drizzled more lube on to the toy and spread it evenly. 25 minutes left and time for try number two.

I lifted both my legs up and placed the toy next to my ass. I was going to try the direct route. After working the tip back in, I placed both hands on the base of the butt-plug and pushed. I made it to the halfway mark again, conscious that the issue was width, not length. Again it became painful. I remembered what David told me when I had previously been trying to set a new personal best for butt-plug insertion. He had said that bearing down softened the anal muscles. So, as I pushed in with my hands, I counterintuitively tried to squeeze the intruding object out of my ass. I felt myself opening a fraction more. We were now at three inches inside me. I eased the pressure momentarily and bore down again. As I felt my internal squeezing pushing the plug out, I shoved it in harder with both hands. Four inches now, but I needed a break. I took the toy out. I was gaping quite a lot now. I ran my finger round the inside of my open, twitching ring sending electricity up my spine. I wished that David was there to lick round inside me. I poured more liquid into my opening and lubed the toy again, ready for try number three. Still 20 minutes to go, but I needed to dress and do my make-up. Better get a move on.

I decided a change in position might help. I knelt on the towels and lowered my face to the bed, turning my head to lie on my cheek. I tilted my pelvis up, reached back and pulled one butt cheek to the side, while sliding the tip of the toy into my gaping ass. Getting back to three inches was now easy. I let go of my backside, put my hand between my legs and started to rub my pussy as the other hand pushed and swiveled the plug, changing the angle of attack, working it deeper into my body. It was now virtually all in me, but the last half inch was the widest and so the toughest. I moved my hand from my pussy to my face and started to suck my thumb. Not for the first time, I thought about having a cock my mouth and another in my ass. I started to bear down once more, feeling the pressure of my inner muscles pushing the toy back against my hand. Come on Emily, you can do this. I sucked and slurped on my thumb and spread my knees further apart. Fuck that was tight. Suck, suck, suck. Squeeze, squeeze, squeeze. Push, wiggle, push. Suck, suck, suck. Squeeze, squeeze, squeeze. Push... oh my fucking God, shit! With a sharp stab of pain, my ring yielded just that little bit more, unwillingly accepted the final half inch and sulkily closed around the stalk, twitching slightly. The pain subsided and turned to an amazingly stimulating feeling of fullness and internal pressure. Go team Emily, new personal best, you have achieved total anal slut level! An inch of stalk was still outside me, but with my ring defeated, it was not too much work to ease the butt-plug further into my anal cavity so that the jeweled base nestled between my butt-cheeks.

I knelt up, the movement making me even more aware of the large foreign object deep inside me. I had made quite a mess. It was good I had put the towels down. I used one to wipe excess lube from my ass and thighs. 15 minutes to get dressed, dry my hair and do my make-up, that's doable.

I held up the dress, if dress you could call it. It was more a scrap of shiny black material. It was strapless, really just a rectangle made of three panels, designed to be closed to form a tube. The thinner outer panels, which would form the back, each had half a zipper down one side and were fixed to the wider front panel by black laced cords. It was short. It was very, very short. I held the front panel on to my back and wrapped the two other panels round my petite frame. I slotted the bottom of the zipper mechanism together and drew it upwards. Wow! that was so not going to work. Maybe I had eaten too much whipped cream and cum earlier. I held it up again and figured out that you could loosen the lacing. Let's try again. This time the zipper closed, the two joined back panels not quite reaching my breasts. I knew I would have to wriggle the whole thing a half turn round me, so I had left some slack in the lacing. With a little difficulty I span it round the right way, pulled it up slightly and smoothed it over my body.

I looked at myself in the mirror. I had been worried that there would be a void at the front that my meagre breasts would be unable to fill, but it fitted me snuggly, it even accentuated my modest curves a little. The twin circles of my nipples were fairly obvious to make out if you looked closely. Hopefully no one would. It wasn't sitting on me quite right, but when I tightened the side laces a bit, it clung to my shape more. The front was lowish, but not too low and I could carry it off, even with my lack of cleavage. I actually looked pretty good. Sure it was hooker good, but whatever, I had learnt to embrace my inner slut over the past few weeks. Turning slightly the laced sides exposed at least two inches of flesh all the way from my ribs to my thigh; David was right, no panties! Turning further and looking over my shoulder I realized that the base of my ass was showing, so I jiggled the dress down. The stretchy material clasped my butt tightly and stayed in place. There, I might be slightly less likely to be arrested now. However the skin-tight dress left very little to the imagination, it looked like I had spray-painted my butt. Could you even make out the base of the butt-plug in my ass? Maybe I was imagining it.

I realized that I had been assessing the look of the dress from a play wear perspective. With a jolt, I recalled that I was going out in public like this. I felt an empty pit open in my stomach. OK Em, focus. I sat on the bed (not an easy task given what I was wearing) strapped on the shoes and teetered back to the mirror. Their shiny black leather matched the dress. Turning to evaluate the view from the rear, they did make my legs look longer and my butt more pronounced. I dried and brushed my hair and pulled it back in a ponytail, held with a band, black of course. I quickly did my make-up, assuming David would expect the slutty end of the spectrum. Finally I strapped the black leather collar around my throat. I went for buckle at the back and metal ring at the front, I hoped that was right. Done and 5 minutes to spare.

Surveying the overall result, it wasn't too bad. I think at least a few guys might have stopped the car and rolled down their window to chat if they drove past a girl looking like I did. I smiled and then jumped, startled as a buzzing began suddenly in my ass. David was in the doorway looking at me, the remote control in hand. He pressed it again.

"Let's leave that for later. Emily, I wanted to say that you look like a girl that any guy would be proud to take out. Let's go."

"Where are we going?"

"You'll see. Walk in front of me to the car angel. I want to see that ass wiggle and your ponytail swing."

--

Thankfully David's car was in the drive, but I still wobbled to it as quickly as the unfamiliar high heels allowed, scanning around to see if anyone could see me. Between the stilettos and the dress, it was not easy getting into the car and I ended up flashing both my pussy and butt-plugged ass at David; he didn't seem to mind that much. Sitting self-consciously in the passenger seat as low down as I could manage, I asked a question that had been on my mind.

"So you just had a fetish dress and other gear lying around? And they just happen to fit me like a glove? What's with that?"

"Can't you work it out angel? I know you're not always the sharpest tool in the box."