A Tale of Two Paramours Ch. 34

"If you were saying goodbye to me, I wanted to fuck you one last time. But I was quite sure there would not be any goodbyes once we did fuck. So far, looks like I was right. Oh, and I'm on to you now. You're trying to avoid the whole ass fucking issue."

"Because you do not have to do that, regardless of whether this a goodbye or not."

"I know. I want to. Or rather, I want you to do what you want. And who knows, in the right circumstance, I might love it. So, you just need to get over your fear of making me do it and, well, make me do it so I can get over my fear."

"What if you hate me afterward?" I asked her.

Jessi's eyes softened, and she leaned in to kiss me.

"I'm not going to hate you, Mark. I didn't after you fucked Amara when you said you wouldn't, although I was pissed. I didn't after watching you lick an almost stranger's pussy inches from my face. Hell, I didn't hate you earlier tonight when I knew you were trying to break up with me. I won't after this either."

"Jessi..."

"Mark, don't overthink this."

I took a breath and considered the possibilities. I knew I should not proceed. I knew I should do what I had come over to do. But as was usual with Jessi, I also knew that at some point I would no longer care about what I should do, at least not enough to stop myself at the moment. It was later that I would worry about the consequences of what we had done.

"Turn over on your belly," I snapped at my young lover, realizing I had already reached the point of ignoring what I should do.

"Yes, Master," Jessi grinned, kissing me again before complying.

"But we are not going to use the gag."

"Whatever Master wants."

"And do not call me 'Master'."

"Whatever Master wants."

***

"Are you ready?" I asked, and the blonde looked back at me over her shoulder and nodded. I pulled her wrists together behind her back, the handcuffs ready. For a moment I thought of Jessika in a similar situation just the night before, and in that moment doubt flooded into my mind. Jessika had wanted to do what we did, had set up the scenario then adapted when I needed to change it. But Jessi was different. She would lose herself in the scenario and drag me along with her, just like at the cabin. I tossed the cuffs aside and let go of her wrists.

"What are you doing?" Jessi asked, again looking at me over her shoulder.

"We do not need those any more than we need the gag. You will not resist."

"Are you ordering me not to resist, as my Master?"

"Something like that," I shrugged, willing to play along if it meant not having to restrain her and gag her. Doing so would have been too much like actually forcing her. It had been different with Jessika—she had wanted me to tie her up and do what we both wanted. I could handle that without being led down a dark path. With Jessi, it was better to just avoid the path she had laid out. And if she was willing to go along with the idea of not resisting under her 'Master's' orders rather than having to be restrained, I was all for it.

"Then your little slut must obey, Master," she grinned before turning her face away from me.

A flood of doubts washed through my mind, but I let them flow right on by. I grabbed the tube of lube, spread her butt cheeks apart, and rubbed some onto Jessi's anus. I then lubed the probe and gently placed it against her rear opening. The blonde's body tensed, so I used my free hand to rub her bottom and back.

"Here it goes," I cautioned her as I pushed the first half inch of the rod into her. A shiver spread along her still tense body while she buried her head in her pillow and screamed. I made myself ignore that as I slid another inch, and the first bulbous shape, inside of her.

"You okay?" I asked, pausing.

The young woman nodded again but did not look back at me.

"I'm going to push more in," I said before sinking another inch, and another bulb, inside of her.

The slender blonde's body trembled again, but afterward, I noticed that some of the tenseness was gone. And although I thought I had heard a muffled whimper, she did not scream. Taking these as positive signs, I grew bolder, pushing two more bulbs inside of her before stopping again.

"How is that?" I asked her. "Should I keep going."

Jessi turned to look at me over her shoulder, and I saw what I thought was frustration in her eyes.

"Mark, just shove it in," she told me, shaking her head. "This is torture. Just make me take it, pump it in and out a few times to get me ready, then fuck my ass."

"Saying shit like that is not going to make me want to keep doing this," I snapped, not understanding why she would not accept that I did not want to be as extreme as she wanted me to be, despite the fact I had told her that over and over again.

"Is your cock hard?" Jessi asked, jarring me out of my thoughts.

I was not sure how to respond. My penis was erect, but I thought she might take the wrong message if I confirmed that. On the other hand, I did not want to lie to her.

"From your silence, I assume it is," Jessi sighed. "So, you're turned on. You want to fuck my ass. So, do it. I'm giving you my full consent. And trust me, this half-assed gentle shit is worse for me then you just doing it."

I reached down and pulled the probe from Jessi's ass in one swift motion. The blonde's mouth fell open, then she shrieked.

"Why did you do that?" she asked, tears in the corner of her eyes. "It hurt like hell."

"Shut up," I snapped, and something shifted in my brain. I had grown tired of the games, tired of having to maintain boundaries for both of us. The darkness she wanted was right there, ready for me to enter it with her. And finally, I was ready.

Grabbing the previously discarded ball gag, I pushed it into her mouth and tightened the straps. Jessi's eyes sparkled, then she turned away from me, head against the bed. I smeared more lube on her anus and the probe, then shoved it halfway inside of her. The blonde's body jerked while she screamed and whimpered through the gag. I knew I should stop, but I pushed again, this time until all but an inch of the probe above the handle was up her anus. This brought one scream, but her thrashing lasted longer.

Since the probe was about six inches in length above the handle, I knew I had to get it all in to better simulate my own length. So, I applied more pressure to the handle. Slowly, the last inch sunk in. Jessi's body shuddered several times, but there were no more screams.

Leaving her for a moment, I retrieved the handcuffs from where they had landed on the floor. And after I climbed back on the bed, I yanked Jessi's arms behind her and fastened the cuffs to her wrists. Then, careful not to hit the probe, I smacked both her butt cheeks several times, the blows hard enough o jiggle her rear end and leave red marks. Jessi's body jerked with each impact, and several times she screamed through the gag.

After my hand started stinging, I moved to the next step and began working the probe out of her, until only an inch remained inside. Giving her no time to relax, I plunged it back in, this time in a single thrust. Jessi's hips bucked, and I heard another muffled scream before she relaxed. Then I repeated the process several times until her body no longer jumped at each intrusion. At that point, I withdrew the probe.

During all of this, my erection had lessened some. So, I moved around in front of Jessi intending for her to use her mouth to renew my arousal. I paused when I saw her tear-streaked face, then I took out the gag and moved her head to the side so her mouth was accessible.

"Get me hard so I can fuck your ass," I growled.

"Yes, Master," the blonde grinned, wrapping her lips around my shaft as I pushed it into her face.

After only a few seconds, I was fully erect again, but I let Jessi continue a bit longer. When I was sure I was ready, I grabbed her hair, pulled her mouth off me, shoved the gag in, and tightened it. Jessi whimpered but otherwise did not protest.

Moving behind her, I grabbed the lube and spread it over my penis. I next put a large dollop on my index finger and shoved it up her anus, moving it around inside of her. I was amazed at the grip her anus had on the invading digit, and I wondered what it would feel like around my erection.

When I was certain she was well lubed, I pulled my finger free. After giving her bottom a few more smacks, I knelt between her spread legs and slid my shaft between her butt cheeks until the tip was pressing against her anus. But just as I gripped her hips and started pushing forward, a series of frantic head movements drew my attention. Jessi was staring over her shoulder at me, eyes pleading. I moved back a few inches, then leaned forward and took off the gag.

"Do you need me to stop?"

"No, you can go ahead now," Jessi said. "I just wanted the gag out."

"So, how did the probe feel?," I inquired as I again placed the head of my penis against her anus.

"It hurt, but far less than I expected."

"And you want my cock in your ass now?"

"I want you to fuck my ass," she replied, and I was sure she had chosen her words with care.

"Okay," I replied, thrusting forward as my grip on her hips held her in place.

I managed to get a third of my length inside her as the blonde shrieked into her pillow. For a moment I rested there, trying to adjust to the unbelievable tightness. A few seconds later, I tried to push forward again, but I only moved maybe half an inch.

"Fuck, that hurts," Jessi whined.

"I should put more lube on my penis," I told her, starting to withdraw.

"NO!" the blonde said, looking back at me. "Just ram it in. I can take it. I have before."

"But the lube would help," I argued, pulling against the grasp her sphincter had on me.

"Getting it all in me will help because then the worst will be over. Please, trust me."

I weighed my concern with hurting her against her words, not sure how to proceed. But as I thought about it, I felt Jessi move forward, then ram herself backward. Now almost two-thirds of my shaft was inside the whimpering young woman.

"Is that it?" she asked, her breathing coming in short, quick gasps.

"About two thirds."

"Fuck! Well, one more should do it."

"Are you sure?"

"Just fucking make me, Mark. I don't want to go through this agony if you aren't going to take advantage of it."

Part of my mind screamed at me, the part that used to warn me about the things I did with Jessi. That part was telling me to stop. But it was as if the screaming came from a long way away. Another voice, a stronger voice, not only understood what Jessi was saying—that she did not want to go through the pain and then not have either of us enjoy it—but also did not want to stop. Focusing on that aspect of myself, I grabbed the young blonde's hips even tighter than before and shoved myself forward with as much force as I could bring.

As the last remaining third of my shaft drove into her anus, Jessi again buried her face in a pillow and shrieked several times. While she did so, I marveled at the sight of my entire length buried inside her bottom. I also marveled at the sensation of that tightness around me, squeezing me.

"I am going to fuck your ass now," I told her, giving her bottom a smack before I pulled myself all the way back out.

"Mark, what are you..." Jessi started to ask, but her words turned to a howl as I rammed the tip back inside her anus, driving forward until I was again buried as deep in as I could go.

"Fuck it hurts," the blonde sobbed, pulling me back to the reality of what I was doing to her, driving away the darkness that had enveloped me.

"Do you want me to stop?"

"What I want doesn't matter, Master," Jessi replied.

"Yes, it does, Jessi. And I told you, I am not your master."

"But I need you to be for this. Please."

"Jessi..."

"Mark, please just do it. I don't want this pain to be for nothing."

"I cannot do this to you."

"The worst is over. Trust me."

"I do not..."

"Trust me, Mark. Please. I want this."

"You want the pain?"

"I want you to do this to me. Feel my pussy. It's soaked."

My curiosity got the better of my doubts. I reached under her, my fingers finding her dripping labia before they slid into her. She was right.

"This turns you on? The pain turns you on?"

"You turn me on, Mark," the blonde breathed. "You mastering me, making me yours, making me do what you want. Nothing turns me on more."

"Fuck," I groaned, telling myself I had to stop this for both our sakes even as my hand sought out and found her protruding clitoris.

"Yeah, fuck is right," Jessi moaned, her hips moving back against me as I masturbated her. "Fuck my ass. Just don't stop doing what you're doing with your fingers."

Bracing myself with a hand on her slender hip, I pulled about halfway out of her tight anus. A whimper escaped Jessi's lips between her moans, and I gave her a moment to relax. When I thought she was ready, I pushed myself all the way inside her again. I heard another whimper followed by even louder moans.

After a few slow thrusts, I began to pick up the tempo. When sounds of pain started to become more prominent than the sounds of the young woman's arousal, I slowed down. When her moans again overtook her whimpers, I sped back up. All the while, I massaged her most sensitive spot with my fingers.

"Shit, I'm coming," Jessi grunted after several minutes. "Fuck my ass hard while I come, then fill me with your cum."

"Are you sure?" I asked, trying to temper my desire to do what she asked against the fear I should not do so.

"Yes, Master," she gasped as her muscles went rigid.

Moving my hand from between her legs, I straightened my torso, grasped both of her hips, and rammed all the inside of her anus. The slender blonde rocked forward as she grunted into her pillow, her body relaxing then tensing, and I suspected she had climaxed again. Encouraged by this, I began to pound in and out of her tightness, feeling her cling to me as I did so, exquisite friction bringing me closer and closer to my own release.

"I am going to fill your ass, slut," I growled seconds later, that sought after release coming sooner than I had expected.

"Yes please, Master," Jessi whined. "Claim your little slave."

With one last thrust, I buried myself inside of her and held there as I ejaculated. And while I did so, Jessi shuddered beneath me a few times before her muscles tightened once more.

"Did you come again?" I asked her as we both relaxed.

"Fuck yes, Master."

Almost entirely soft, I pulled out of her and lay back on the bed. Jessi turned over on her back beside me, and for several seconds neither of us spoke. I think I might have even fallen asleep, and Jessi's voice brought me back to wakefulness.

"You want me to clean that off for you?" she asked, sitting beside me and pointing at my groin. I lifted my head and saw that my penis was stained with smeared blood, at the least.

"Shit, Jessi! Are you bleeding?"

"A little. It stained my comforter too. I'll need to soak it good, maybe even use the spray stuff on it."

"I am so sorry, Jessi," I told her, sitting up so I could put my arm around her.

"Why? That's what happens after anal. I was just so, um, relaxed that I didn't think about it at first."

"I do not mean the comforter, although I am sorry about that too. I mean that I am sorry that I hurt you."

"You know you hurt me. I told you."

"Yes, I knew it hurt. What I mean was that I am sorry that you were injured."

"It's just a little bleeding. Like I said, it comes with butt fucking."

I almost told her that in my experience, anal sex did always result in bleeding, but I decided that would be a mistake. Well, an even larger mistake than everything leading up to this had been.

"Can I do anything to help?"

"Nah. I'll likely be sore a couple days. Plus, it hurts a lot less than the other two times I did it, so that's good. Now, you didn't answer my question. Do you want me to clean you up?"

"I can do it," I replied.

"Probably not the way I was meaning, but it'd be fun to watch you try."

"What did you mean?"

"Licking and sucking."

I had no words. Even with everything Jessi and I had done together, I would never have anticipated she was offering what she seemed to be offering. And Jessi must have read my shock on my face.

"Okay, I guess that's a 'no'."

"Did you... um, have you... with the guy who..."

"No. And I would have told him to fuck off if he had suggested it."

"Then why now?"

"You're you. And I want to show you I'm willing to do anything for you, at least once. Plus, I've been watching a shit ton of anal porn since I found out she takes it up the ass, and I've now seen a bunch of girls do ATM."

"Why have you been watching, um, that?"

"To learn what to do. I also read a lot online. I think overall it went well. I only cried a little bit. The first time I did it I cried the whole time. The second I time I cried most the time until my anger took over. This time it was just at first, then it felt better. You making me come with your fingers certainly didn't hurt that, because afterward, I was able to relax and almost enjoy it by the end."

"You climaxed twice more after my fingers."

"Yeah, I know. I was there."

"I mean, you must have enjoyed it more than 'almost'."

"I liked the end. As I said, I relaxed, and you really pounded me, and that gave me a small, quick one. Then you said you're going to fill my ass with cum, and that brought on another small one. I think they were as much from the situation as from the ass fucking itself. And you never really answered my question about cleaning you up."

"No, I do not want you to do that," I said, shaking my head as I spoke.

"Ah, so she doesn't do that for you, or you'd have me do it too. Shit, that makes me actually want to do it. Of course, it'd probably be like licking cum off the carpet—something I'm only going to try once—but at least you'd get that 'once'."

"I do not need you, or anyone else, to do it even once."

"Well, that's probably for the best. I'm sure it fucking disgusting, and I doubt even you'd kiss me afterward."

With that, Jessi hopped out of bed and disappeared into her small bathroom. For a moment the blood stain on her comforter caught my eye, and feelings of guilt started to make their way back into my mind. The blonde's grinning return a couple of minutes later, complete with washcloth and towel, helped me suppress that guilt.

***

We were sitting at Jessi's small table eating sandwiches and chips. Jessi, who was dressed in a loose t-shirt and knit shorts, had put a pillow on her seat, and even with the extra cushion, she was still wiggling around as we ate. It reminded me of a recent time when regular sex had hurt her more than she let on, and I started to worry that she was in quite a bit of pain.

"We still need to talk," I told her once it looked like she was finally comfortable.

"Why? I can give you everything she can now, expect a bunch of extra fat to squeeze. Dump her."

"It's not just about the sex," I said, trying not to show my frustration.

"Oh, I know. If it was, you wouldn't need to be with her. That makes this shit so much harder, and that's why it's easier for me to pretend it's about the butt sex than admit to myself that you have feelings for her."

"Jessi..."

"Not that I ever really believed it was just about the sex. That was just me rationalizing. I knew after I gave you that fucking threesome with Amara that you were in love with Big Tits too. I mean, she won't do it—I've tried twice to get her to—so it must be something else. So, I gave you another one, bringing Sheri in, and that was better for me. I'd even do it again if you had the balls to tell me I had to. Shit, I'd lick cum off carpet again if you made me. And you know that, but you keep her too. So, it must be about something other than fucking."