The Roommate Pt. 04

'Now,' she said, her voice dripping with malice. 'You do exactly what I want, or I swear to god I'll send that video to James and everyone else you know, understand?'

I nodded. She smiled.

'Good, so just nod your agreement when I ask you the questions, okay?'

I nodded once more and flinched back slightly as the light from the phone turned on, dazzling me.

'Hello Ruby, are you enjoying yourself?' I nodded. 'Have you been a bad girl?' I nodded once more. 'Have you been fucking your best friend behind my brother's back?' Again, I nodded. 'And now you want me to fuck you, don't you?' This question was the easiest so far to agree to. I may not have wanted her in my arse, but the feeling in my crotch was certainly suggesting that I wanted her somewhere.

She tapped the phone again and looked at me instead.

'Seriously Ruby, I meant it. Don't fight it, it'll only hurt more. Just relax.'

She said this with such tenderness, such sincerity, that I did exactly that. Muscles all around my body that I hadn't even realised had been tensed, relaxed. I inclined my head slightly, indicating that I was ready. She beamed, tapped the phone again, and tilted it downwards so that it was pointing at the enormous dick sticking out from her waist. With her other hand, she lifted my hips slightly, but I took the lead and raised them higher, aiming my rosebud towards her.

I braced for the pain that I knew was about to come.

'We can stop any time you want,' Emily said. Again, the tenderness in her voice caused me to look at her, wondering what exactly was happening here.

I gasped, or at least, I tried to gasp, as the head began to separate my cheeks. Emily entered me slowly, carefully. My body tensed up once more, and I could feel my nails digging into my own hands where I was clenching my fists so tightly. She paused, just the head of the dick inside me.

'Breathe,' she said. I did so. As I did, my body began to relax once more, getting used to the intruder inside of it. 'Are you ready for more?' I indicated my affirmation, and she thrust her hips forwards slightly more.

It was at maximum an extra inch that she got inside of me, but my body seized up once more as though she'd slammed twelve inches inside. Pain was radiating through my insides, and I squeezed my eyes shut. Remembering Emily's advice however, I breathed deeply, and began to relax. We stayed in that position for several seconds, but Emily didn't say anything. Eventually, when I had become accustomed to the sensation, I looked her in the eyes, trying to convey that I was ready for more.

We continued in this manner for some time. Emily inching her way in, me tensing, breathing, then letting her know that I could take more. Eventually, and to my own surprise, I felt Emily's thighs against me. I looked down, once more letting the pain wash over me until it disappeared. My eyes bulged at the sight of Emily inside me, right to the hilt. She smiled down at me.

'I'll go slow, okay?'

And that's exactly what she did. Slowly, she removed almost the entirety of the cock from me, leaving just the head in, and even slower, she slid it back in. Every now and then, she would pause, letting me become used to the feeling, until eventually she was able to slide in the whole way with no breaks.

Slowly, methodically, she began to thrust her hips into me. I was surprised to find that the sensation was actually very enjoyable now that I had gotten used to it. I found myself pushing my hips back into her on occasion, as though trying to meet her halfway. Gradually, she increased the pace, moaning loudly as she did so. It was only at this point that I remembered that she had penetrated herself as well. Every time her thighs made contact with me, that dildo pushed further into her. The pleasure that she must have been receiving caused her to throw her head back as she picked up her speed.

She never let go of the phone, but I noticed that the light was bouncing wildly around the faster we moved. She had lost any semblance of control that she had over it's aim as she became lost in her building orgasm. Her tits bounced, and her hair was tossed violently as her pace built. I had long ago realised that I was enjoying it too. My own boobs bounced as I tried to moan my pleasure. It was completely different to vaginal sex, perhaps not as enjoyable, but different. And it was a different that I liked.

Suddenly, Emily cried out and thrust hard into me, causing me to whimper with pain and pleasure. She held herself in that position, as she rode her orgasm. Her eyes, which had been closed tight, opened slowly as she came down, and she looked at me, a slight smile on her face. She leaned forward and put her palm on my cheek. I pressed my face into her hand, but cried out as she found the edge of the tape, and ripped it off. Laughing, she then reached inside my mouth and pulled out her underwear, tossing them aside. I was about to say something, to shout at her for the pain I was in, when she collapsed herself fully causing my legs and hips to ruse uncomfortably, and kissed me.

Her lips were soft and tasted of raspberry. Her tongue delicately probed my mouth until it found my own, and they melded together in a passionate, loving dance. Her breasts rubbed against mine, causing a sensation of fire inside as my nipples, already more tender than ever thanks to the clips, responded to the touch of Emily's. Gradually, she pulled away, sliding the silicone cock out of my arse, leaving me with a strange sensation in my bum as the breeze entered my widened hole.

'Enjoy it?' Emily asked, as she clambered off the bed. She gasped slightly as she pulled the other dildos from inside her.

'I did, actually,' I admitted. 'Far more than I thought I would.'

'Good,' she replied, kicking the now useless toy away from with her feet. 'Now the real punishment can begin.'

'The... what? I thought the punishment was the anal?'

Emily laughed at this.

'No, that was just for me to fulfil a fantasy.'

With that, she left the room. I could hear her heels hitting the stairs as she went down them. It was at this point that I took stock of my situation. All I could fathom was utter confusion. Emily had found out, and her explanation made sense. She wanted to make me regret my actions, which I presumed had been what losing my anal virginity had been about. Yet she had switched. From revelling in my terror at the prospect of being fucked in the arse, she had instantaneously become tender. She had told me that we could stop whenever I wanted, and yet I had lifted my hips. I had presented myself to her willingly. What the fuck was going on? It had actually been quite enjoyable, but now I was lying, still bound, waiting for the real punishment. My crotch tingled at this thought. I became aware once more that my clit was being clamped, as were my nipples. I dreaded to think what would happen if they were touched.

I was brought back from my rambling thoughts by the sound of Emily climbing the stairs once more. I craned my neck once more as the door swung open, filled with a sudden desire to see Emily wearing another strap on, only this time to fuck me properly. Instead, she had a large, pink wand in her hand.

'Sorry, just had to make sure it was fully charged,' she said with a grin as she walked towards me. 'You'll like this, to start with at least.'

Before I could process what she had said, she had clambered over the foot of the bed and positioned herself between my legs. Without any further preamble, she leant forward and licked slowly from my arse to just below my clit, spreading my lips as she did so. I let out an involuntary moan, which became more intense the closer she got to my swollen clit. She dove back down and began to lick around the hole that she had only recently stretched. I had never been rimmed; I had never seen the appeal of anything being done to my butt. But I realised then and there what I had been missing out on. It was a strange sensation, but my moans became louder as she continued to circle me. My hips began to buck as I tried pushing her deeper, but Emily stayed resolute, teasing me.

After a few minutes, she stopped, and I looked down to see a wicked grin on her face again. As I opened my mouth to speak, she lowered her head quickly, and clamped her mouth around my protruding clit.

To say the feeling was intense would be an understatement. It wasn't so much an explosion that happened inside me, but rather a supernova. I had thought that my clit was becoming more and more sensitive, but never in my life had I dreamed I could ever feel like it did in that moment. I can't say that I enjoyed it either, nor did I dislike it. Instead, I merely experienced the feeling. But within seconds, it was becoming too much. My hips thrashed wildly. My hands pulled violently against their bindings. My legs desperately clawed at Emily's back, simultaneously trying to force her inside me, and get her as far away from me as possible.

Eventually though, Emily removed her lips from me. Wiping them, she let out a soft laugh at my expression. I dreaded to think what I looked like, I hadn't been in any sort of state to sort myself out before bed, and I'd woken up to find myself strapped naked to my bed, before being fucked in my arse. I can't imagine I looked attractive, more like a woman who had been found wandering the woods somewhere after going missing several days earlier.

My thoughts were brought back to the present by my ankle being bound back to its original position. Emily had taken advantage of the crazed swirl of thoughts moving chaotically through my head, and before I knew what was happening, one leg was tied back up. I began to protest and kick my other leg but found this to be a difficult task without the use of any of my other limbs. My feeble attempts lasted mere seconds, before Emily caught my free leg and began to bind it. A few seconds later, I was back to being spreadeagled.

'What the f-' I began, before Emily cut me off with a shushing noise.

She reached down, finding the tape from earlier, and placed the wand on the inside of my thigh. The bulbous head was brushing my clit, and the intense sensations began coursing through me once more. These feelings rendered me helpless, as I watched Emily use the tape to keep the wand in place, wrapping it once, twice round my thigh, before doing the same at the bottom of the wand.

'Em,' I just about managed to get out. 'Please.'

She didn't respond, merely smiling at me, before leaning down and pressing her body against mine. Once more I felt her breasts push into mine, my nipples responding instantly to the touch by spreading electricity through my chest. She kissed me again, slowly, passionately. Our tongues circled each other, until a pain in my breasts caused me to cry out.

The sudden removal of the bobby pins on my nipples had hurt far more than when they had been put on. I had been too lost in the kiss to realise that Emily had snaked her hands onto my breasts, distracting me so that she could remove them without much care. The pain was still radiating through me, leaving me unable to form words. I watched helplessly as she slid down my body towards my pussy. I felt the tears begin prick my eyes at the knowledge of what was about to come. I had been right to be scared. The pain of the pin being removed from my clit was excruciating, but somewhere, hidden deep down, was a subtle hint of enjoyment. I stored that information for later, choosing instead to focus on not crying again. Breathing through the pain as it slowly subsided.

Emily seemed to be happy to wait. She just sat there, watching me get through the pain. When I finally did, she gave me one more coy smile.

'Ready?' She asked, and without waiting for an answer, pressed a button on the wand. My pussy was now so sensitive that any slight touch was enough to set it on fire, so the vibrations were causing a raging inferno. I barely heard or felt Emily climb off the bed, and it was only as she reached the door that I heard her call to me. 'I'm going to go and run a bath; I'll be back when I'm done.'

And with that, the door clicked shut, leaving me helpless as I was fucked by a vibrating wand.

***

I was never really sure how much time elapsed between Emily leaving me there and her returning. Nor was I sure how many orgasms I had had. All I was certain of were two facts. Number one was that my pussy was beyond sore. Number two was that I was beyond tired. I was actually so shattered that I didn't hear her come back in. I only knew she was there when the vibrating suddenly stopped.

I lifted my head, using all the energy I had left available to me to do so. I just about registered the fact that she hadn't been lying, she had taken a bath. Her hair was wrapped in a towel, and she smelled of cherries. She had clearly taken time to redo her makeup, however, as her eyes still had eye shadow on, and her lips were bright red. I did not have the energy to wonder why this was the case.

She settled on the foot of the bed and gave one long kiss to my cunt. She then began to slowly undo the bonds tying my legs and arms to the bed. She remained silent the entire time, but as she was about to start undoing my arms, she was sure to make sure that she straddled my head. I took my cue and began to lick her dark lips. It took all the strength I had remaining, but I didn't let up, and became aware of her taste. It was only after a few seconds that I realised that a large part of the reason she tasted of cherries was probably because of the soap she had used to clean herself.

Even in my exhaustion, I managed to register Emily's moans becoming louder and louder, until they became actual screams of euphoria. I could feel her hand movements begin to lose control as she struggled to untie me, but her hips began grinding wildly on my face. She was trying to force me deeper and I was only too happy to oblige. I had only just penetrated her with my tongue when I felt her close around me as Emily's screams became the loudest yet. It hadn't taken long, probably only half a minute at maximum, but she was already cumming as she rode my face.

As she began to come down from her high, Emily's hands began working on my bonds again, and within a few more seconds, I was free. She climbed off me and the bed before walking over to her phone which had ended up on the floor and picking it up.

'Right,' she said, in a brisk manner. 'I've got two more jobs for you, and then your punishment is complete.'

'Em, what the actual fuck?' I said, sitting upright for the first time. 'Don't you think you've done enough?'

'Oh, don't worry,' she smiled. 'This time I won't be doing anything. It'll be all down to you and my dear brother.'

I gave her a perplexed look as she walked over to her coat. She bent down, being sure to give me another view of her bum, and put it on as she stood up. Reaching inside the pockets, she took out two more items, showing them to me.

'You'll need both of these,' she said, waving them at me. And then, she told me my mission.

'That's disgusting,' I said. 'I'm not doing that.'

'You are if you don't want me to send James the video of me fucking you, as well as the one of you fucking Erin.'

I did not respond to this.

'Well,' she said, throwing me the items which I spectacularly failed to catch. 'Here you go, good luck.'

***

Emily left the house shortly after setting me the task. She made me walk her to the door whilst I was naked, then pushed me against the wall and kissed me passionately just after she had opened the front door, letting anyone passing see that we were making out and that I was very much in my birthday suit.

One of the rules was that I was not allowed to shower beforehand. Emily had been quite insistent that I show her proof of that. When I had looked confused, she took me to my full-length mirror and sat me down in front of it. Spreading my legs, she showed me the bright red lipstick stain she had left on my pussy when she kissed it. I now had her own lips on mine, which made my task infinitely harder. How the fuck was James meant to not notice that?

And so, once she left, I stood in front of my mirror, and stepped into the first item she had given me. They were pearl panties. Essentially a g-string but with pearls that Emily assured me would get me nice and wet as I wore them. Before pulling them up completely, I bent over and, using copious amounts of lube, I inserted the second item that Emily had given me. I let out a low moan as the plug entered my bum, perhaps I could get used to this after all. Once the pearly panties were on, I threw on some leggings, a top, and some old trainers. Emily was right. The pearls felt exquisite as they slid through my lips, separating them and gliding smoothly along.

I headed downstairs, getting used to the sensation of the pearls and occasionally letting out a small moan. Once at the bottom, I grabbed my car keys, left the house and begun the drive to work.

I wasn't on shift today, and I had made sure to miss Erin, who had been working in my place. If I timed this right, she would be on the way home as I arrived at the centre. I knew James would be there, we usually hit the gym together after my early shift, and I knew he would go still, even though I wasn't working.

Sure enough, as I pulled into the car park, I saw his car. As soon as I had parked, I whipped out my phone and began to text him.

There were several changing rooms in the centre, and James and I had had sex in nearly all of them. The best one though was the disabled one. It was massive, which meant plenty of room to move about in. The downside of course, was that you could potentially be interrupted by someone who needed to use them, and who was likely to be able to put 2 and 2 together quite easily.

I rushed through reception, not acknowledging the greetings that came my way from colleagues. I was in no mood to talk. The pearls were sliding smoothly along my slit, and I could feel the wet patch spreading across my crotch. For now, I had only one thing on my mind.

He was already there waiting for me. I closed the door to the changing room behind me, and locked it. Without a word, I threw down my bag and turned to face him.

'Rubes, what-'

He got no further. Within seconds, I had crossed the room, and began pulling down his shorts and underwear. His cock sprung free as my knees touched the floor. Flaccid was no good to me, and so I took him and guided him into my mouth. I worked ferociously, bobbing my head forward and back, swirling my tongue around his head. The response was immediate. I could feel him getting harder as I worked his dick like I never had before. Within no more than ten seconds, he was fully hard, and I was gagging as he hit the back of my throat.

James managed to keep his moans quiet, aware that people were walking past us as I fucked him with my mouth. I continued for a minute or two, then stopped, gave him a few pumps with my hands, and turned around. I shimmied my leggings down so that they were round my knees. I heard him gasp as he saw the plug, which I pulled out slowly, letting out a soft, low moan as I did.

'Ruby, seriously, what the fuck is -'

'James, stop talking and fuck me,' I said, cutting him off. I was far too aroused for any kind of conversation right now. 'But first, go into my bag and get out the lube.'

Bless him, without question, he did exactly that. I say bless him, as though he was a well-behaved puppy, in reality he didn't question me because I'd just given him the blow job of his life and was now asking to be fucked in the bum. What man would question that?

'Ruby, are you sure?' He asked, as he began to massage the lube onto his shaft.

'James, do you want to fuck my arse or not?'