“Very much so,” I said.
“Well, we don’t want you to be in any pain, no do we? Discomfort, yes, but pain? No,” Adriana said, 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 said. And I meant it too. God help me, I truly did.
“Well let’s hope you continue to like it,” she said, working the lube into the dildo by jerking herself off. “Because the best part is still to come.”
I must admit I felt anticipation along with the trepidation. I was excited as well as terrified.
And just like that, she grabbed her cock and guided the tip of it towards my asshole.
I took a deep breath and let it out slowly as the tip of her dildo touched my sphincter. And then a low mewling groan escaped my throat as the tip of it pushed into my anus.
“Jesus fucking Christ,” I moaned as Adriana forced her cock inside my asshole. My head was facing forward now and my eyes were staring at the carpet.
“Come on, baby,” Adriana said. I could tell from the sound of her voice that she was smiling. “You can take it. I know you can. You’re a big boy.”
I grunt in assent as she began 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,” Adriana said, working her hips a little more quickly now. “This is just the beginning. I’m barely even inside of you yet.”
I tried to relax but it was difficult. There was pleasure there, but it’s mostly hidden behind the discomfort, which was growing larger and larger as Adriana worked her cock deeper and deeper inside of me.
My groans were growing louder and more animated but Adriana didn’t let up, working the dildo ever deeper inside of me.
“That’s it, that’s it,” she said. “My cock looks so fucking good moving in and out of your asshole.” Her hands grabbed ahold of my asscheeks and she pushed them apart, opening me up even more to her, allowing her to penetrate me even more deeply. It felt like the entire dildo was up my ass now, even though I suspected not even half of it was in there yet.
Adriana let out a whoop of joy and pumped my asshole deeper than ever. I let out a shocked little yelp followed my a low moan.
“Oh, poor baby,” Adriana said. “Is it getting a little too deep for you?”
I nodded my head, unable to speak.
“Well, let’s see if I can help you out a bit,” Adriana said.
She released my asscheeks and ran one of her hands down to my cock and started jerking me off while continuing to fuck my ass.
“There, is that better?” she asked.
“Yes,” I managed to groan.
“What?” she said. “I couldn’t hear you.”
“Yes,” I said louder. The pleasure of her working my cock alleviated some of the discomfort of the dildo in my asshole but not all of it. But I had to admit, now that my asshole was getting more and more used to the cock inside it, the discomfort was lessening and the excitement was increasing.
“Tell me that you love it,” Adriana said, fucking me more aggressively now. She knew that working my cock relaxed me, thus opening my asshole up even more, allowing her to fuck me harder. It was a nice little feedback loop. “Tell me how much you love it when I fuck your asshole.”
“I love it,” I said.
Adriana slapped me on the ass with her free hand. “Louder,” she said.
“I fucking love it!” I screamed.
“That’s better,” Adriana said, 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 said. “I love how it feels when you fuck my ass with that giant cock of yours.”
“Yes, yes, yes!” Adriana said. She released my cock and slapped 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 wanted to cum badly and I also wanted to get Adriana’s huge dildo out of my asshole, I decided to go all out trying to make her happy.
“Fuck my ass with your huge cock,” I said. “Hammer me with it! Stretch my fucking asshole out!”
“That’s what I’m talking about,” Adriana said, her face glowing with pleasure as she fucked me harder than ever. She kept 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 screamed. “Fuck that ass, fuck that tight little asshole! Hammer me with your cock! Break me in fucking half!”
“Yes, YES, YES!” Adriana screamed back at me. “Give me more, baby! More! You’re making my pussy so fucking wet! I love hearing you talk dirty!”
Tears were leaking out of my eyes and my ass was on fire but my cock was rock-hard. It felt as though it was going to burst through my skin. Despite the pain, on some level, I was obviously enjoying myself. But that didn’t mean I didn’t want it over with already. So I turned it up a notch.
No longer screaming, but begging in my most pleading voice, I turned 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 was what put Adriana over the edge. She slipped her hand between her legs and furiously rubbed away at her clit while continuing to fuck my asshole, deeper and more aggressively than ever. She was banging away on my asshole so intensely that I could barely breath, let alone talk anymore. So I faced forward once again and dropped my head towards the floor, biting down on a scream.
“Fuck, FUCK, FUCK!” Adriana groaned, letting out a scream of her own as a monstrous orgasm flowed through her. She shook and shimmied and held her cock deep inside my asshole until the orgasm passed through her. “Goddammit that feels so fucking good!” she said, pausing to catch her breath. “Great job, baby. I haven’t cum that hard in years!”
Her cock was planted so far in my ass I couldn’t even reply.
“I suppose you’re ready to cum now too,” Adriana said. I could hear the joy in her voice.
I nodded my head.
“What?” she says, taunting me right up until the end. “I can’t hear you.”
“Yes please,” I managed to say.
Adriana laughs. “Okay,” she said. “I suppose I can finish you off once and for all.”
And with that she goes back to fucking my ass. Shortly after starting up again, she grabbed ahold of my cock and pulled back on it, so it was pointing straight down at the ground. I let out a groan of pleasure as she started jerking off my swollen cock.
“But I’m not going to stop fucking your ass until you’re finished,” Adriana said. “I want you to cum with my cock up your ass.”
That was fine with me. I was so excited that I wanted to see how hard I was going to cum with a cock in my asshole.
And luckily, I was so excited that it didn’t take long at all. Between Adriana jerking off my lubed-up cock and fucking my asshole less aggressively now that she’d already cum, it didn’t take more than a minute before I was ready to blow.
“Holy shit,” I groaned as I crept right up to the edge of orgasm. “I’m gonna fucking explode!”
“Do it, baby,” Adriana said. “I want to see how big your load is!”
“Holy shit,” I said again as my body tensed up in the final seconds before cumming. “Holy shit, holy fucking shit!”
And with that, I released, my whole body spasming as my cock exploded, sending stream after stream after stream of cum out of me. Adriana continued jerking me off and fu
cking my ass until my cock was completely dry, then, thankfully, she slid the dildo out of my asshole.
I immediately collapsed to the carpet, right atop my huge puddle of cum, but I didn’t care in the least. I was spent far beyond normal. Eventually I rolled over onto my back and stared at the ceiling, trying in vain to ignore the throbbing pain in my gaping asshole.
Adriana flopped down next to me and laid her head on my chest. She was still wearing the strap-on and the dildo was lying on my stomach.
“So,” Adriana said, smiling at me. “What did you think?”
“I think it was . . . interesting,” I said. “Far more intense than I was expecting. Not quite as bad. Kind of exciting, actually. But I have to admit, I’m glad it’s over.”
“Yeah, I’m sure you are,” she said. “Because now you get one last shot to punish me for what I just did to you.”
“That’s right,” I said, grinning. “Just give me a little while to get myself together and we’ll get going to round four.”
“I can’t wait,” Adriana said.
“Neither can I,” I replied. “I’m going to open another bottle of wine and you’re probably going to want to help me drink it, if you catch my drift.”
“Loud and clear,” Adriana said. “In fact, you’d better open two.”
“That’s probably a good idea.”
#
One hour and two more bottles of wine later and I was ready to go back at it again. I was drunk enough that I no longer felt the ache in my asshole but that didn’t mean I wasn’t going to punish Adriana for what she’d done to me. We were both sitting on the couch, watching TV, when I turned it off and stood up without saying a thing. As she smiled expectantly up at me, I picked her up, threw her over my shoulder, grabbed one of the half-full wine bottles with my free hand, and carried her into her bedroom.
Once there, I set the wine bottle on the nightstand then tossed Adriana down onto the bed, her back on the mattress and her legs up in the air. I grabbed ahold of her ankles and spread her legs wide, as far as they would go. They were sticking straight out, knees locked, leg muscles tight.
“Hold them there,” I said.
Adriana grabbed her ankles and held her legs in position, wide open and beckoning. “I guess round four is officially underway, huh?” she said.
“You’d better believe it,” I said.
Still standing, I looked down at her, taking in her whole body before proceeding. We still hadn’t put on any clothes all night but I never got tired of her nakedness.
I grabbed Adriana’s hips and slid them towards me until her lower half was right at the edge of the bed. From this angle, with me standing and her on the bed, my cock was hovering right over her pussy as if showing me where it wanted to go. For a moment I was tempted to just stick it in her, but the temptation quickly passed. I had some other things that I wanted to do is first.
With that in mind, I turned slightly to the side to give myself a better angle, then slid two fingers inside her.
I started off slowly, moving them back and forth with the purpose, rubbing the underside of her clit, something that I knew drove her crazy. I gradually picked up steam, moving my fingers faster and faster in and out of her. Adriana had told me before that she liked getting fingered just as much as she liked getting fucked, if not more, and it showed in her face. Especially when I curled the tip of my fingers upward and went to work on her G-spot.
I paused for a moment to slip a third finger inside her pussy then immediately picked up right where I’d left off, slamming my fingers into her hard enough that her legs started to buckle, bending at the knee.
I immediately pulled my fingers from her pussy. Adriana groaned in disappointment, a sound that turned into a yelp of surprise when I smacked her pussy with my open palm.
“What was that for?” she asked, her legs folding even further.
“Did I say you could relax your legs?” I asked.
She shook her head and pulled her legs taut once again.
“That’s better,” I said.
“Now will you stick your fingers back in me?” she asked.
“That depends,” I said. “Can you keep your legs tight no matter what I do to you?”
Adriana nodded.
I gave her another smack on the pussy. She yelped again and flinched but didn’t fold her legs this time.
“Are you sure?” I said. “You almost collapsed right there.”
“I’m sure,” she said, showing a hint of defiance.
I smacked her again, this time on the inner part of her thigh.
She held tight.
I smacked her other thigh, harder this time. The sound echoed about the bedroom.
She bit down on her bottom lip but still she didn’t fold her legs.
“Not bad,” I said. “I think you’ve earned my fingers again.”
So I gave them to her, sliding all three inside her pussy. They went in even easier than they had earlier. Apparently getting smacked around turned Adriana on just as much as a good finger-banging.
I put my left foot up on the bed and leaned forward, altering the angle of penetration and allowing me to slide my fingers even deeper inside her. I pushed them in until they were well past the knuckles and held them there as her pussy clenched tight.
“Holyfuckingshit,” Adriana said as I started sliding them back and forth deep inside her, exploring her insides. Her legs were quivering but she held on tight, not letting them falter.
I hammered my fingers into her, trying to get Adriana’s legs to cave, but still she held them to the side, her knees locked out and her thighs rock-hard. My head was right above hers and she stared up at me, her eyes laced with defiance even as the rest of her features gave in to the pleasure. She was intent on outlasting me, taking as much as I could give her without folding again.
There was no way that was going to happen, of course. I still had a couple tricks up my sleeve. It was time I broke one out.
While my right hand still pounding away at her pussy, I reached down with my left and began to grope one of her tits, then pinched the nipple. Adriana gasped but didn’t relax her legs. I gave her other breast the same treatment. She reacted the same way, still not even coming close to collapsing her legs.
“Not bad,” I said. “Not bad at all.”
Adriana didn’t reply. All her energy was being spent keeping her legs tight. But she did glare up at me with an evil look while her breath escaped from her mouth in shallow gasps.
“You do realize you can’t win,” I said. “You’re going to fold again eventually.”
“Not if I can help it,” she said, her voice a raspy, wheezing mess.
“Then I guess I’ll just have to make it so you can’t help it,” I said.
“Go ahead and try,” she said.
I laughed softly. Adriana certainly was quite the trooper. Most women would have folded long ago. But I didn’t tell her that, of course. To do so would ruin the mood.
“If you insist,” I said instead. Then I let my hand wander up her chest to her throat.
Adriana’s eyes widened slightly. Whether it was in surprise or pleasure I wasn’t sure. Not that it mattered at this point.
Still continuing to bang her pussy with my fingers, I gripped her throat between my thumb and forefinger and started to squeeze.
Adriana’s face turned red from the lack of oxygen, then started to go pale. But still she held on, keeping her legs tight by sheer willpower alone. But it was only a matter of time until her body gave in, even if her mind didn’t. Fifteen seconds later the time came.
Her eyelids fluttered and then started to close. She released her hold on her heels and her arms flopped down onto the bed, followed by her legs.
I released her throat but continued slamming my fingers inside of her pussy as she came back to the waking world. The transition must have been an intense one, as an orgasm rocked her body shortly after I let go of her throat.
She bucked against my hand a c
ouple of times, then tensed up, her pussy squeezing the blood from my fingers. She reached out and grabbed my arm with both of her hands and held it in place, deep inside of her.
“Don’t move,” she said desperately, still short of air. “Don’t you dare fucking move.”
I almost pulled my fingers out of her to pay her back for what she’d done to me earlier but ultimately decided that would be taking things too far. Besides, there was no doubt we were going to play this little game again one day, and I didn’t want to incur too much of her wrath.
Her body seemed to freeze in place for just a moment, then released just as quickly. A torrent of juices came pouring out of her pussy, drenching my hand and wrist. She moaned and cursed under her breath as her entire body quivered and shook.
“Holyfuckingshit,” Adriana said, turning it into one long word. She released my arm and tried to refill her body with air.
“I take it you liked that?” I said.
Eyes wide, she nodded vigorously.
Smiling, I pulled my fingers out of Adriana’s pussy. They were shining with her juices, glistening in the light. I admired them for a moment then said, “Open your mouth. I want you to taste yourself.”
She did so without comment. Smiling, in fact.
I slipped all three fingers into Adriana’s mouth and she licked them clean, staring right at me the entire time. After I’d pulled them back out I told her to grab ahold of her ankles once again.
“Like this?” Adriana asked, grabbing her ankles and spreading her legs wide and holding them tight. “Is this how you want me?”
I nodded and slipped my cock into her. It felt great, especially after so much foreplay leading up to this moment. I loved fucking her pussy, especially when her legs were spread wide like that. It heightened the sensation quite a bit.
After slamming my cock into Adriana for a good minute and a half, she released her hold on her ankles and brought her arms back towards her chest. I hadn’t told her she could but it didn’t bother me at this point. I was enjoying myself too much to care at the moment.
While I continued hammering my cock in and out of her, Adriana grabbed one of her tits in each hand and started to play with them. At first she groped and fondled them, but it wasn’t long before she was attacking her nipples, squeezing and rubbing them between her fingertips until they were hard, and then going after them even more aggressively.
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