Chapter 43 – Damien Goes in the Back

Damien’s eyes snapped over in my direction as soon as I made my presence known to him. The big burly man tossed my panties aside and launched himself from the bed at me in a flash of movement. I barely had time to react and shut the door before he was upon me, kissing and groping my body like an animal in heat.

Sniffing my panties had really gotten Damien worked up, as I could already feel his hard, thick cock twitching and throbbing as it pressed up against me. His desire was as clear as day, raging within him, and I was eating it all up, practically putty in his hands, his strong, firm hands. One of which had slid down my body and begun to finger my pussy.

While I was indulging in the pleasure of his hands and lips upon my body, Damien was more focused on the task at hand, and I soon found the vial of lube and dildo taken from me. From there, I was led back to the bed, which I was immediately pushed down onto.

The big burly man wasted not even a second before joining me on the bed, but where I was laying face down on the bed, he was sitting upright between my legs. His hands caressed and massaged my supple butt, sinking his fingers into my ample cheeks, but he didn’t go right for the main event. No, instead he reached up over me and grabbed one of his pillows, which he then positioned under my hips to afford himself some leverage during what was to come.

Only then did Damien spread my butt cheeks and give himself a nice view of my tight little asshole and pussy. A pussy that was still quite wet from our earlier fun and still had remnants of his cum within it. Positioned as I was laying on my chest, I was unable to see what the man was doing when the attention he was giving paused for a few seconds, but I was immediately made aware of what it was he was up to when I felt a lubed up finger slide across my asshole.

"Ah, hold up for a second," I called out as I reached around there myself. It wasn’t like I didn’t want this, but if we were to continue, there was something I needed to do first. Something that was easily accomplished with a wave of one of my fingers over my asshole and a quick application of freshen up. "There you go, all clean."

Once I gave him the all-clear, Damien resumed his efforts, sliding his finger over my asshole and spreading the lube about. In time, he even began to ease his finger into my ass and I couldn’t help but let out a moan or two from the sensation. I had fucked myself in the ass with more than a few toys back on Earth, and I had even had anal sex once before in this new life of mine, but that was during a foursome where I was also getting my pussy fucked and blowing a guy at the same time so I wasn’t really able to focus on the feeling of having my ass played with. However, as it turned out, having someone finger my ass like this, preparing me for what was to come, was a whole other sensation. One that I thoroughly enjoyed.

That enjoyment shot up a notch as Damien slowly eased a second finger into my asshole. As more and more moans began to escape my throat, I lightly bit my lips and my eyes rolled back slightly. As it turned out, he knew exactly what he was doing back there, and before long, he was not only fingering my ass, but also my pussy. With one of his hands knuckle deep in my ass and the other knuckle deep in my pussy, my pleasure was reaching greater and greater heights.

However, before I came close to reaching any sort of climatic conclusion, the man slid his fingers out of me. I was a little disappointed to feel those thick, strong fingers leave me, but that feeling quickly faded when Damien shifted positions, getting ready for what came next.

"Fuck, you’re so damned big, Damien!" I moaned as he eased the head of his cock into my tight, little asshole.

I could barely believe just how much he was stretching me and it was just the head of his cock. If not for my blessed by an angel trait, I would have had serious concerns about letting him fuck my ass with such a big cock, but thankfully I didn’t have to worry about those kinds of things and could just indulge in the pleasure without worrying about any repercussions of taking such a big cock in my ass.

Thankfully, Damien was aware that although no lasting damage could be done to me, I could still feel pain and get uncomfortable when things were taken too fast too soon. As such, he took his time easing his cock deeper and deeper into me. With every slow thrust, a bit more of his cock pushed into my ass, stretching me wider and wider until finally, I was taking him all the way in. Which, unlike my pussy, was something my ass could actually do.

"I was right," Damien grunted as he thrust into me with so much force that his hips were audibly slapping against my supple butt. "Your ass is just as tight as your pussy, if not more.

"Damn right it is!" I giggled in between moans as I shifted my focus towards tensing my muscles as best I could to press down on his cock a couple of times as he fucked me. This, of course, made the man let out a couple more enthusiastic moans.

Again and again, Damien pounded away at my ass, driving the pleasure the both of us were indulging in ever forward. It took all my mental strength to remember to use my skills and apply them whenever I could remember, but I was getting there and it was slowly becoming second nature for me to use them.

After a few moments of intense ass fucking, the man spoke up. "Are you forgetting something, Eve?"

A look of confusion crossed my mind as I had no idea what he was talking about. It was only when he shifted us into a new position so that we were laying on our sides as he fucked me from behind, and put the dildo in front of me that I realised what he was getting at.

In this new position, Damien could no longer roughly thrust away at my ass. Instead, he was just slowly grinding his cock in my ass, but the reason for the change was clear as day. Between the fact that this position gave me better access to my pussy and that he had just put the dildo in front of me, it was obvious that he wanted me to put it to use.

As such, I wasted no time sliding the thick, wooden toy into my tight, wet pussy. The feeling of having two of such things fill me entirely, even if one wasn’t as real as I would have wanted, was just too good. My moaning soon reached an all-time high as I worked myself further and further towards my climax. However, Damien had different ideas and had not forgotten the true purpose of our fun. After all, we weren’t just having sex, we were training.

"Don’t cum until the last possible moment, Eve." The man whispered into my ear, but despite his words, he didn’t at all slow down in his grinding away in my ass with his cock, nor did his groping of my breasts slow down in the least.

Having no reason to deny him his wishes, I immediately let go of the dildo I was using to fuck my pussy and focused my mind on trying to delay the orgasm that I was getting dangerously close to. However, this was apparently the wrong move, and Damien scolded me for it with a slight pinch of my nipples, which obviously did not at all help with staving off my orgasm.

"No, continue to use the toy." He demanded before going on to explain himself a little. "If you really want to become an escort, and a good one at that, you will need to be able to continue to please your partner even despite everything else you are feeling. Your partner’s pleasure is all that matters. Don’t let yourself cum for as long as you can, and when you do eventually cum, don’t let your orgasm hinder your efforts to pleasure yourself until I cum."

I obeyed Damien immediately and resumed pushing the toy deep into my pussy over and over again, even as the toy got wetter and wetter, to the point it was literally dripping with my pussy juices. However, despite my willingness to obey, I couldn’t help but be a little confused by what and why he was making me do this.

The pleasure of a sex worker being secondary to that of their partners was an obvious thing to me, but what I couldn’t immediately see was how that was applicable here. Damien was my partner and he was just constantly fucking my ass. I wasn’t really paying any extra attention to him. I wasn’t focusing on his pleasure over mine.

Wait, no… Maybe Damien doesn’t intend for me to think of him as the partner in this situation. After all, I’m playing with myself more than with him, so maybe I am both the escort and partner in this theoretical situation.

Once that little revelation clicked inside my head, it made a whole lot more sense of what the man was getting at. By fighting back my need to cum and focusing only on the task of making my partner, myself, in this case, feel as much pleasure as possible, I was entering into a sort of feedback loop. The better a job I did at making myself feel pleasure, the more challenging my task of not cumming would be, which would in turn result in more efficient training.

Furthermore, not only was this helping me develop a talent that I would use if I chose to pursue this line of work, but it was also helping me train up my sex toy skill. Damien, fucking my ass was just a distraction. Well, not just a distraction as it was highly pleasurable for both him and me, but the main reason he was continuing to do it was to distract me and make my job harder.

Once I had realised all of that, I set myself entirely to the task at hand. No, not just the task at hand, because I wanted to take it a step further. Instead of just focusing on pleasuring myself with the dildo, I wanted to focus on using my ass as best I could to pleasure Damien’s cock as well. After all, it was the least I could do to thank him for all the help and support he had shown me since I showed up out of the blue.

To that end, I squeezed down with my ass, using my muscles to massage the cock deep inside me as best I could. Meanwhile, not only was I going to town on my pussy with the dildo, but I was also timing my thrust so that all three of us, the dildo, Damien, and myself, were in sync. By the time things lined up just right, I could push my hips back just in time to give a little extra push down on the big burly man’s cock whenever he ground into me, bringing both of us a little extra pleasure as this managed to allow his cock to reach deeper inside my ass.

Not to brag, but my efforts were a huge success. Both Damien and I were moaning and gasping like never before. The pleasure was rolling over us as the bedroom was filled with the unholy orchestra of our moaning. Unfortunately, doing a better job at those tasks also meant I was having a harder time delaying my orgasm. Sheer mental effort alone could only hold off the inevitable for so long, and before too long, I was cumming.

I had ridden the edge of that climax for as long as possible, which only made it all the more powerful when it did come. Still, I did my best to adhere to what Damien wanted me to do and remained focused on fucking myself with the dildo and his cock in my ass despite the immense wave of pleasure that was rolling over me.

Somehow my orgasm seemed to last forever, as each wave of pleasure that faded was accompanied by another high, not quite as potent as the last but equally pleasurable. It was a great relief when, before my climax had faded entirely, Damien reached his own climax and came inside my ass.

The moment Damien came inside me, I fell into a sweaty, gasping heap on the bed, stopping all other tasks as I savoured what was left of my orgasm. Now that he was done, I no longer needed to hold off and push through the overwhelming pleasure.

The two of us just lay there for more than a few moments after everything was said and done, catching our breaths as his cock slid out of my ass along with the dildo out of my pussy. Both holes were thoroughly flushed from their fucking and leaked copious amounts of liquids. However, where my pussy was gushing with my plentiful arousal, my ass was leaking the man's seed, which pooled on the bed sheets under us. Bed sheets, which were thoroughly stained with sweat and sexual fluids by this point.

"That was something else…" Damien gasped something, which I took pride in as I assumed it was a hard thing to make a man as high a level as him this out of breath. "You’re certain a quick learner, Eve."

"It helps that I have a great teacher." I said as I rolled over on the bed to face him. I would have crawled up onto him and kissed him too, but my arms and legs were jelly, so this would have had to suffice.

"Honestly…" Damien paused as he slid an arm around and pulled me tight into his embrace. "I know very little about what would be required of you in the kind of work you want to do. Having sex for the fun of it and as a job are two very different things, and I’ve never done the latter before. I was just kind of guessing with the advice I gave you."

"I don’t think your advice was wrong even if you were just guessing, but regardless of that, every little bit helps me grow my skills," I responded as I nestled my head against his burly chest. "Speaking of which, I wonder how they are going after everything we did. I turned off the notifications so they wouldn’t interrupt, but I’m really curious to see what gains I have achieved."

Fascinate has reached Rank 5

Stimulate has reached Rank 5

Tight Fit has reached Rank 4

Kissing has reached Rank 8

Sex Toys has reached Rank 8

Vaginal Intercourse has reached Rank 6

You have reached [Pervert], Level 10+1 Vitality+1 Charm+3 Stat points

"Oh, I hit level 10." I cheered aloud because I was actually a little surprised by this. I had levelled up twice not that long ago, so I wasn’t expecting another level all that soon. However, given that the sex with Damien lasted quite a bit longer than normal, almost as long as several bouts with Vel, it made more and more sense the more I thought about it.

"Of course you have," Damien chuckled, shaking his head, still unable to wrap his head around my quick levelling pace.