by JT Holland
Smiling widely, Taylor starts to laugh. “Oh my god,” she says. “I can’t believe you’re taking this so well.”
“You’re surprised?”
“Hell yes!” she says. “I mean, you’re a cool guy and all—otherwise I wouldn’t be dating you—but I thought this would be beyond your comfort zone.”
“So did I,” I say. “But I have to admit, I’m kind of enjoying myself.”
Taylor shakes her head and laughs some more. “Well, don’t get too excited yet,” she says. “Because we still have the toughest part to come.”
“Yeah, I’m still not too sure about this part,” I say, although part of me actually is looking forward to it quite a bit, even though I know it is going to cause some discomfort.
“This will definitely be tougher to take than the rest,” Taylor said. “But you can do it.” She flashes me a dirty little smile. “I have faith in you.”
“That makes one of us,” I say.
“You’ll be fine,” Taylor replies. “You can handle it. Besides, I’ll take things slow and easy. At first. Now let’s stop playing around and get this show on the road.”
She smacks my cheek playfully then climbs off me. I start to get to my feet too but she shakes her head.
“On your hands and knees,” Taylor says. “Right there on the floor. You know the position. You put me in it all the time.”
I do as I told, turning over and getting up onto my hands and knees, doggy-style, my ass facing Taylor.
“Arch your back more,” she says, doing something behind me that I can’t see. From the sound of her voice she’s on the other side of the room. It sounds like she’s rummaging through a plastic bag. “I want to see your ass up in the air.”
So I do that too. At this point my ego has totally disappeared. The trepidation and awkwardness of the situation is complete gone by now too. I’m simply here to please Taylor, to do whatever she says without hesitation or shame. And I find that I’m loving the idea of being her little plaything.
“There you go,” she says. “That’s better.”
I look over my shoulder and see that she has a bottle of lube in her hand. I take a deep, relieved breath.
“Happy to see this, are you?” she says, squirting lube onto her fingers. Her dildo is still strapped to her and pointing straight at me.
“Very much so,” I say.
“Well, we don’t want you to be in any pain, no do we? Discomfort, yes, but pain? No,” Taylor says, dropping down to her knees behind me and sidling up to my ass. I want you to enjoy yourself so you’ll let me do this to you again sometime. You are enjoying yourself so far, right?”
“I sure am,” I say. And I mean it too. God help me, I truly do.
“Well let’s hope you continue to like it,” she says, rubbing the outside of my asshole with her fingertips, working the lube in. “Because the best part is still to come.”
And with that, she slips her finger inside my asshole.
I suck in a deep breath and let it out slowly as Taylor works my asshole with her finger, taking things slowly for me, loosening me up.
“Holy shit your asshole is so fucking tight!” she says. “Just relax, baby. You’ll enjoy it a lot more.”
I try to but it’s all but impossible. I’m excited, yes, but also nervous and more than a bit anxious. I’ve only had someone else’s finger in my ass once, and that was just a few days ago when Taylor surprised me. But that was at the tail-end of the evening, right before I was about to cum, and I was so wound up at that point that it didn’t have the same effect as it does this time.
“Maybe I need to take things a little slower,” Taylor says, slipping her finger out of my ass. “Get you a little more excited first.”
“I think that sounds like a great idea,” I say.
A few seconds later Taylor is lying down beneath me, her head between my legs and angled upwards so her mouth is right in front of my cock. She takes my cock in her mouth and starts to suck on it, slowly at first, but quickly picking up speed.
My cock has been hard for a while but hadn’t gotten much attention until now, and the pleasure is more intense than usual. Taylor realizes this too and only blows me for a short while before pulling her mouth off and sliding back out from beneath me.
I groan in disappointment.
Taylor laughs. “I think you liked that too much,” she says, climbing to her knees behind me once again. “I want to get you excited, but not too excited. You can’t cum until I’ve fucked you in the ass proper. Now let’s try something else.”
The next thing I know Taylor’s hand is around my cock and her tongue is in my ass. She’s jerking me off while licking my asshole, working them both gently. It feels so fucking good it’s all I can do not to scream. But she’s working my cock gently enough that while it’s exciting as hell, there’s no danger of me cumming.
“Now this seems much better,” Taylor says after half a minute. “No danger of getting you too excited, but certainly getting you where I want you. Another minute and you’ll be ready to go.”
She starts working my asshole more aggressively, bouncing her face against my ass, forcing her tongue deeper and deeper inside of me. She’s no longer working my cock; it’s unnecessary. I’m moaning and groaning in pleasure just from her tongue in my asshole.
Two minutes later she pulls away, slipping her tongue out of my asshole. She’s right, I can feel my asshole open wider than before thanks to the relaxation that comes with the pleasure.
“There we go,” Taylor says, lubing up her fingers once again. “Now come the fingers. And after that, my cock. How does that sound to you?”
“Great,” I say. And it does. At this point, I can’t wait to feel what it’s like to have the dildo up my ass.
“That’s what I like to hear,” Taylor says. I can hear the joy and excitement in her voice as she slips her finger into my asshole.
This time it’s much easier taking her finger. It’s not that I can’t feel it, but there’s not nearly as much pressure thanks to the foreplay from earlier.
“That’s much better,” Taylor says. “Not nearly as tight. Ready for another?”
“Yes,” I say.
And with that, she slips a second finger inside my asshole.
“Holy shit,” I say, taking a deep breath.
“You felt that one, didn’t you?” Taylor says.
“Yeah,” I say, slowing my breathing down in an attempt to relax.
“I’m not surprised,” Taylor says, her voice still full of joy as she worked her fingers around in my asshole, getting it more and more loose. “It’s not easy taking two fingers in your ass, is it?”
“No it’s not,” I say. I’m relaxed enough now that I’m not too uncomfortable. And even with the discomfort I can still feel a undercurrent of pleasure. Not as much as when Taylor was playing with my cock but more than when she had her finger inside me earlier.
“And just wait for the coup de grace,” Taylor says, laughing softly. “Which, I think you’re about ready for.”
She aggressively banged my asshole with her fingers for another ten seconds, then let them slip out.
I let out an involuntary groan as they exited.
“Oh, don’t worry baby,” she says, taking my groan as one of disappointment. “I’m going to replace them in just one second. Just let me lube up this fat cock of mine and then we’ll be ready to go.”
I turn my head back to see her squirt a good amount of lube onto the tip of the cock and then work it around with her hand. I must admit to feeling anticipation along with the trepidation. I’m excited as well as terrified.
Taylor finishes up working the dildo with the lube and looks at me as I’m watching her. “Are you ready for this?” she asks, smiling widely.
“Hell no,” I say. “But let’s do it anyway.”
“That’s the spirit,” Taylor replies, grabbing her cock and guiding the tip of it towards my asshole.
I take a deep breath and let it
out slowly as the tip of her dildo touches my sphincter. And then a low mewling groan escapes my throat as the tip of it pushes into my anus.
“Jesus fucking Christ,” I moan as Taylor forces her cock inside my asshole. My head is facing forward now and my eyes are staring at the carpet.
“Come on, baby,” Taylor says. I can tell from the sound of her voice that she’s smiling. “You can take it. I know you can. You’re a big boy.”
I grunt in assent as she begins to slowly work the dildo, pushing it deeper inside my asshole for a moment before relaxing for a beat and then pushing again.
“Relax and take it like a man,” Taylor says, working her hips a little more quickly now. “This is just the beginning. I’m barely even inside of you yet.”
I try to relax but it’s difficult. There is pleasure there, but it’s mostly hidden behind the discomfort, which is growing larger and larger as Taylor works her cock deeper and deeper inside of me.
My groans are growing louder and more animated but Taylor doesn’t let up, working the dildo ever deeper inside of me.
“That’s it, that’s it,” she says. “My cock looks so fucking good moving in and out of your asshole.” Her hands grab ahold of my asscheeks and she pushes them apart, opening me up even more to her, allowing her to penetrate me even more deeply. It feels like the entire dildo is up my ass now, even though I suspect not even half of it is in there yet.
Taylor lets out a whoop of joy and pumps my asshole deeper than ever. I let out a shocked little yelp followed my a low moan.
“Oh, poor baby,” Taylor says. “Is it getting a little too deep for you?”
I nod my head, unable to speak.
“Well, let’s see if I can help you out a bit,” Taylor says.
She releases my asscheeks and runs one of her hands down to my cock and starts jerking me off while continuing to fuck my ass.
“There, is that better?” she asks.
“Yes,” I manage to groan.
“What?” she says. “I couldn’t hear you.”
“Yes,” I say louder. The pleasure of her working my cock alleviates some of the discomfort of the dildo in my asshole but not all of it. But I have to admit, now that my asshole is getting more and more used to the cock inside it, the discomfort is lessening and the excitement is increasing.
“Tell me that you love it,” Taylor says, fucking me more aggressively now. She knows that by working my cock relaxes me, thus opening my asshole up even more, allowing her to fuck me harder. It’s a nice little feedback loop. “Tell me how much you love it when I fuck your asshole.”
“I love it,” I say.
Taylor slaps me on the ass with her free hand. “Louder,” she says.
“I fucking love it!” I scream.
“That’s better,” Taylor says, her enjoyment showing in her every word. “But it’s still not good enough. Talk to me, baby. Tell me how much you love having my cock on your ass.”
“I love it having your cock in my ass!” I say. “I love how it feels when you fuck my ass with that giant cock of yours.”
“Yes, yes, yes!” Taylor says. She releases my cock and slaps my ass with both hands a few times. “That’s what I love to hear! It turns me on to hear you talk to me like that. Keep it going, baby. Keep talking to me. I’m not going to stop fucking your ass until you cum, and I’m not going to let you cum until I cum. And since I’m not going to cum until you make me happy, you’d better make me happy!”
Since I want to cum badly and I also wouldn’t mind getting Taylor’s huge dildo out of my asshole, I decide to go all out trying to make her happy.
“Fuck my ass with your huge cock,” I say. “Hammer me with it! Stretch my fucking asshole out!”
“That’s what I’m talking about,” Taylor says, her face glowing with pleasure as she fucks me harder than ever. She keeps slapping away at my asscheeks with both hands. “Keep it going, baby. Keep talking and I’ll let you cum!”
Grunting and groaning loudly now, I scream. “Fuck that ass, fuck that tight little asshole! Hammer me with your cock! Break me in fucking half!”
“Yes, YES, YES!” Taylor screams back at me. “Give me more, baby! More! You’re making my pussy so fucking wet! I love hearing you talk dirty!”
Tears are leaking out of my eyes and my ass is on fire but my cock is rock-hard. It feels as though it’s going to burst through my skin. Despite the pain, on some level, I’m obviously enjoying myself. But that doesn’t mean I don’t want it over with already. So I turn it up as notch.
No longer screaming, but begging in my most pleading voice, I turn back to look at her and say, “Please give it to me. Give it to me like never before. Slam my fucking asshole with your cock. Give it to me. I need it, I need it, baby, I need it so bad!”
This last part is what puts Taylor over the edge. She slips her hand between her legs and furiously rubs away at her clit while continuing to fuck my asshole, deeper and more aggressively than ever. She’s banging away on my asshole so intensely that I can barely breath, let alone talk anymore. So I face forward once again and drop my head towards the floor, biting down on a scream.
“Fuck, FUCK, FUCK!” Taylor groans, letting out a scream of her own as a monstrous orgasm flows through her. She shakes and shimmies and holds her cock deep inside my asshole until the orgasm passes through her. “Goddammit that feels so fucking good!” she says, pausing to catch her breath. “Great job, baby. I haven’t cum that hard in years!”
Her cock is planted so far in my ass I can’t even reply.
“I suppose you’re ready to cum now too,” Taylor says. I can hear the joy in her voice.
I nod my head.
“What?” she says, taunting me right up until the end. “I can’t hear you.”
“Yes please,” I manage to say.
Taylor laughs. “Okay,” she says. “I suppose we can finish you off once and for all.”
And with that she goes back to fucking my ass. Shortly after starting up again, she grabs ahold of my cock and pulls back on it, so it’s pointing straight down at the ground. I let out a groan of pleasure as she starts jerking off my swollen cock.
“But I’m not going to stop fucking your ass until you’re finished,” Taylor says. “I want you to cum with my cock up your ass.”
That’s fine with me. Based on how hard I came the night before with her finger in my asshole, I can only imagine how much harder I’m going to cum with a cock in there.
And luckily, I’m so excited that it doesn’t take long at all. Between Taylor jerking me off and fucking my asshole less aggressively now that she’s already cum, it doesn’t take more than half a minute before I’m ready to blow.
“Holy shit,” I groan as I creep right up to the edge of orgasm. “I’m gonna fucking explode!”
“Do it, baby,” Taylor says. “I want to see how big your load is!”
“Holy shit,” I say again as my body tenses up in the final seconds before cumming. “Holy shit, holy fucking shit!”
And with that, I release, my whole body spasming as my cock explodes, sending stream after stream after stream of cum out of me. Taylor continues jerking me of and fucking my ass until my cock is completely dry, then, thankfully, she slides the dildo out of my asshole.
I immediately collapse to the carpet, right atop my huge puddle of cum, but I don’t care in the least. I’m spent far beyond normal. Eventually I roll over onto my back and stare at the ceiling, trying in vain to ignore the throbbing pain in my asshole.
Taylor flops down next to me and lays her head on my chest. She’s still wearing the strap-on and the dildo is lying on my stomach.
“So,” Taylor says, smiling at me. “Was it everything you were expecting?”
“And then some,” I say in an exaggerated moan.
She laughs. “It wasn’t that bad, was it?”
“That depends,” I reply.
“On what?”
“On if my response has any bearing on whether or not we’re
ever going to do this again.”
“Oh, don’t worry, honey, we’re going to do this again no matter how you respond,” Taylor says. “So you might as well tell the truth.”
“It was . . . interesting,” I say. “Far more intense than I was expecting.”
“Is that a good thing or a bad thing?” she asks.
“Both,” I reply. “It was uncomfortable and degrading and fucked-up in more ways than one but it was exciting and crazy and perverted and incredible too. Not something I’m going to want to do all the time, but certainly something I’d do again.”
Taylor claps her hands and giggles like a little girl. “Oh, I’m so glad you didn’t hate it,” she says. “Because, as you can probably tell, I liked it quite a bit.”
“I know you did,” I say. “And I’m glad it made you happy.”
“More than happy,” she says. “Ecstatic. It was so much fucking fun. And because you were such a good sport, tomorrow night I’m going to let you do whatever you want to me.”
“Whatever I want?”
Taylor nodded emphatically. “Anything goes. Absolutely anything.”
“Anything, huh? Anything at all?”
“That’s right,” she says. “Under one condition.”
“What’s that?”
Taylor flashes me a nasty little smile. “You make me pay for what I did to you tonight.”
“Really?” I ask, already getting excited just thinking about it.
“Yep,” she says. “Tomorrow night I’m going to be your little fucktoy. So bring you’re A-game baby, because I’m expecting to get punished quite a bit for tonight. Deal?”
“Oh, I think that can be arranged,” I say, pulling her head towards me and planting a kiss on her lips. “Now, if you don’t mind, I need to get some ice. My ass is sore as hell.”
#####
COMING SOON
Punishing My Filthy Girlfriend: My Filthy Girlfriend – Volume Three
ALSO BY JT HOLLAND
MY FILTHY GIRLFRIEND
