Hailey s Secret
- 4 years ago
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Hailey Tries Anal free porn video
I sat at my desk doing homework and staring out my bedroom window hoping my boyfriend Mr. Chapman would get home soon. He’d been working a lot lately and as a result, we had seen little of each other. As a police officer, I knew his schedule was weird and I didn’t want to smother him or anything, but as his girlfriend, I worried about the late nights and wanted him to be safe and snuggling with me every night. Living with my parents threw a wrench in that particular fantasy, but I wanted it all the same. It was almost two in the morning when his car pulled into the driveway to his house. I finished writing my notes and packed up my school work for the night to text him.
I texted. I saw his face light up in his car as he pulled out his phone to check the text.
He texted back getting out of the car and heading into the house. It wasn’t exactly the response I had hoped for.
I asked, not wanting to be too pushy.
Uh-oh. Was I being too clingy? I was still kinda new to the whole ‘dating’ thing, I hoped I wasn’t encroaching on his space. Or maybe it was about the recent additions to our sex life. Both my and his friends had become involved, maybe that crossed a line for him. He seemed okay with it at the time. Had he changed his mind? Was he just going along with it because I said I wanted to? A knot formed in the pit of my stomach, and as much as I didn’t want to have this conversation, I knew I could never sleep if we didn’t. I texted.
I was wearing shorts and a tank top, but I threw on sweatpants and a sweater before I went over. Since so much of our relationship revolved around sex, I didn’t want him to think I was trying to distract him by showing up with anything even mildly provocative. I took him and our relationship seriously, and he needed to know that. My dog Rufus wagged his tail as I crept down the stairs as silently as possible so as not to wake my parents. It’s not like they’d care if I left, I’m an adult and can more or less do as I please, I just didn’t want to be rude and wake them.
The door closed behind me and I walked through the cool, misty night next door to Mr. Chapman’s house. I knocked on his door, and he let me in. “Hey, beautiful,” he said, leaning down to kiss my cheek.
“Hey handsome,” I said back, stepping into his home and making my way over to his big, leather couch.
“Anything to drink? I know it’s late, but…”
“No, I’m fine,” I said, pushing some loose strands of hair behind my ears. “What is it you wanted to talk about?”
“Right,” he said, sitting down next to me and staring at me with his bright blue eyes. I always got lost in those. It was hard not to.
This time, the knot in my stomach was enough to keep me from falling under his spell and though I admired him and his rugged beauty, I couldn’t truly get lost this time. “I wanted to talk about the other night. Y’know, with Dion,” he said and a surge of panic overtook me.
“I’m so sorry if that made you uncomfortable, he just seemed so sad and upset, like, I just wanted to help him somehow and when he got turned on I couldn’t help but be flattered, but I promise it meant nothing, I only did it because I thought you were okay with it and if you weren’t I’m really, really, sorry, I’d never do anything like that again if-”
“Woah, woah, woah, calm down! That’s not what this is about at all,” he said, putting my scared stammering to an abrupt halt.
“It’s not?”
“No, not at all. Baby, that was freaky, no doubt, but in a good way. We all had a great time and I don’t regret a thing. Do you regret it?”
I blinked at him, confused as to where this conversation could be going. “No, I don’t regret it.”
“So you had a good time?”
“Yeah. It was super fun,” I said, noticing now how hot my face felt. I wiped my sleeve on my forehead and there was a wet spot where my sweat had come off.
“Then where is this coming from?” he asked, putting his hand on my knee.
“I-I don’t know. You said you ‘wanted to talk’ and that’s always kind of a scary phrase and then you said it was about Dion and I don’t know how many girls let their boyfriend’s best friend cum inside them, but I did and I just didn’t-”
“Baby, baby, baby, caaalm down,” he said, putting both hands gently on my shoulders and looking me square in the eyes. That piercing blue took hold of me, despite my discomfort. “I’m sorry if I worried you, this isn’t about that at all.”
“What is it about then?”
“I just wanted to say… well, I noticed Dion was able to… well, he could go to town on you in a way that I can’t because of my size,” he said, looking suddenly self-conscious.
“You are hung like a racehorse, this is true,” I said. It was an honest response from me, but it made both of us laugh.
“Well, I was thinking about it, and since I’m too long to really give you the business from the front, I was wondering…” he paused and looked away, like he was embarrassed.
“Wondering if you could give me ‘the business’ from the back?” I asked.
“Yeah. Kind of.”
“We’ve done it that way before. Our first time, you had me belly down on this couch and showed me the meaning of the universe,” I laughed.
“No, no, not like that. I mean, like, through the back door,” he said, still averting eye contact.
“You mean… anal?”
“Yeah.” Ho boy. When I met Mr. Chapman, I was basically a virgin. Every sexual experience I had was because of him, and we’d been through some doozies in our few months together. The concept of anal wasn’t upsetting to me, I wasn’t grossed out or anything, but it wasn’t something I ever considered. And knowing just how large his cock is, and how difficult it was to get in my vagina the first time, my first thought was that I’d be walking funny for a week if we even tried to do anal. “Y’know what, it was a dumb idea, never mind,” he said, shaking his head.
“No, hold on,” I said, not wanting him to be embarrassed. “What makes you want to try anal? And what does it have to do with Dion?”
He sighed. “Well, uh… okay, all cards on the table. If we did anal, there’s a much better chance that I can get deeper inside you. The, uh, end of the rainbow, so to speak, is much farther so a guy like me can get a little more bang for my buck. If you know what I mean.” My eyes widened. I was trying to wrap my head around it. “Not that I don’t get enough bang for my buck with you normally. I mean our sex life is great, I just mean like… well, I can get all the way in if we practice a little and who knows, you might like it?”
“I see,” I said, still processing the idea. “Have you done anal before? Are you able to get deeper that way?”
“Yes, I have. And yes, I can. It’s totally cool if you’re not into it though, I just wanted to open up a dialog and see where your head’s at is all. Not like we have to answer now.”
“Let’s do it,” I said. I had never done it before, and honestly, the idea intimidated me. Both because of his size and because there are obvious inherent risks with butt stuff. It can’t be avoided. But my first experience with him was amazing. He was patient and kind, always checking in on my comfort because he knew how large he was. He gave me the time and the instruction to get used to him so we could both enjoy ourselves. Since then, my body had grown accustomed to his size and he never once tried to push his boundaries in a way that would cause me harm. There was always an element of restraint to our sex-life, one that I didn’t want him to feel boxed in by.
“You serious?” he asked.
“Sure, why not? You just have to go slow and help me out, like you always do.”
“Of course, I wouldn’t dream of it any other way,” he said, his regular confidence back. I could tell it was something that was bothering him for a while, and my openness to try it took a weight off his shoulders. I was glad to have given him that relief. “All right, well I don’t wanna keep you up too late if you have classes tomorrow.”
“Then we better get crackin’,” I said with a smile. He gave me a look.
“You wanna do it now?”
“Why not?”
“It’s pretty late, I’d hate for you to be tired tomorrow.”
“I always sleep better when you’ve given me ‘the business’,” I said with a coy smirk. He laughed and shook his head.
“How did I find you?”
“I showed up naked in your pool one night, remember?”
“Best night of my life.”
“So far…” I winked at him. He laughed again and took my hand, leading me to his bedroom where we could get more comfortable. I made him take my layers of clothes off to help get him in the mood, then did the same for him when I was fully naked. Like always, he palmed my enormous E cups and played with them for a bit before we settled on to the bed to relax. I always enjoyed the attention he gave my boobs, and rarely ever discouraged it. Several minutes into sucking on my nipples, I was forced to get his attention. “You gonna put it in my butt, or what?”
“Sorry, I got distracted,” he said, flicking his tongue over my nipples one last time before leaving them alone. He was probably just trying to help me relax and get into the mood, which was fine by me. His dresser drawer creaked open, and he pulled a bottle of lube from inside. I leaned back onto his pillows and lifted my knees, which spread my booty for him. My breasts fell to either side of my chest and I used one arm to keep them together and plump them up for his viewing pleasure. It was sort of a reflex at this point, I know how much he loves them.
He squirted some lube onto the tips of his fingers and lowered his hand between my legs. I always loved looking at the contrast between our skin tones. Something about the way his dark skin clashed with my pale skin never failed to excite me. He rubbed the tips of his fingers over my back door and massaged. It was a new sensation, one I was definitely not familiar with, but not entirely unwelcome either. “How we doin’?” he asked.
“Feels good so far,” I smiled back. I wanted him to know I trusted him, he had my full confidence. His gentle massaging gradually became more firm. He wasn’t actually pushing inside yet, but I could tell he was working toward it. I’m not ashamed to admit it felt kinda nice, like any other type of massage. It was relaxing, if a little foreign. With another squeeze of his bottle, he dripped some extra lube onto his fingers and the friction lessened. Then he pushed a finger inside. My breath caught in a short gasp. It wasn’t painful, just new.
He held his finger there for a moment, letting my body get used to it before he slowly pushed it deeper. It’s hard to describe if you’ve only ever had things going out as opposed to in. It was as invasive as you’d expect, but the naughtiness of it, and the fact that I was sharing the experience with someone I truly cared for, made it an exhilarating sensation. Like, there’s a man inside me where no man has gone before. Those captivating blue eyes gazed at me, gauging my reaction. I smiled down at him and nodded.
With that assurance, he moved his finger in and out. Slowly but steadily, I grew used to it. Maybe I was just out of my element, but my booty felt tighter than my vagina. Even if only by a little bit. It felt reluctant to let anything in, whereas when I wanted something inside my vagina it wasn’t much trouble. At the same time, it felt tantalizing, good even. It was a strange mixture of sensations I was glad to be sharing with my man. He worked his finger in and out for a while, letting my body get used to it before he pushed it as far as it would go.
A little squeak came out of my mouth that neither of us expected. He looked up at me, concerned, but relaxed as I started to giggle. The giggle caused my body to constrict around his finger and send a new and different sensation through me. It almost felt like things were more sensitive than my vagina, I could distinguish small movements and variations in pressure more. Once he saw I was okay, he continued to work his finger in and out at its full length, reapplying lube as needed. Eventually, he worked up to two fingers, and as my body got used to it he applied additional pressure, easing my body into everything at a snail's pace.
“We still doin’ good?” he asked.
“Yeah. Feels funny,” I replied.
“Good funny or bad funny?”
“Good funny,” I said, smiling at him and considering how odd it would look if anyone else were in the room. With my knees up and his fingers three knuckles deep in my back door, talking and laughing with each other like we were having milk and cookies.
“Think you’re ready for me?” he asked, already lifting his hips and stroking his cock to life.
“I’m always ready for you,” I teased. He smiled and kept working his fingers inside me while he tried to get himself hard. I loudly cleared my throat to get his attention, then opened my mouth and wiggled my tongue at him. He took the hint and brought his hips to my face so I could suck him to life. It didn’t take long. I think the excitement of having access to forbidden fruit had him rearing to go. Once he was nice and hard, he pulled his giant cock from my mouth and positioned himself between my legs. I smiled up at him, jiggling my breasts with one arm to give him some eye candy while I rubbed an extra layer of lube onto his already glistening cock.
He gripped his shaft and lined up in front of me, pushing his swollen cock head between my cheeks and slowly squeezing it between them. My booty resisted. He pressed forward, moving it back and forth to try to coax me open but had difficulty doing so. I took a deep breath and let it out, relaxing every muscle in my body to the best of my ability as I spread my knees farther apart to try to help him. After a bit more effort, he slipped in. “Hoof!” I said. My booty was so tight it felt like he was shoving a Coke can inside me.
“You okay?” he asked.
“Yup, just getting used to how much man you are,” I smiled. He waited patiently with just his tip inside me for a while. I gave him a nod, and he slowly inched his way inside me, deeper and deeper. Once I got used to the size of his swollen head, the additional depth wasn’t as jarring. I looked down and watched as his black cock disappeared inside me, inch by inch until he got about two-thirds of the way in and I felt him push against something. He slowly pulled back till only his tip was inside me, reapplied a generous helping of lube, and then pushed in again.
This entire process was fairly mechanical, but I still enjoyed it. He was so attentive to my needs, so careful to make sure he didn’t hurt me, it was endearing really. I knew this was all for him, a necessary warm up so he could really give me everything he had, but I enjoyed the feeling of him inside me and loved that I could do it for him. As my booty got used to his size, it was feeling better and better. He kept lubing up and pushing about two-thirds of the way in, approximately the same depth as he could in my vagina.
I wondered what was impeding his progress, or if he knew something I didn’t about those last few inches. Either way, I was more than happy to let him take his time and get my body used to his size. It became easier and easier, and after a big, deep breath, my body relaxed enough that I felt him push passed that previous wall and fit the last few inches of his mammoth cock inside me. I expected it to be uncomfortable, but it wasn’t. It was, however, strange to have that much man inside me. I had felt nothing that deep before, and it was a thrill to hit that milestone.
Once fully inside me, he smiled. “We did it,” he said, shifting his hips to wiggle his cock inside me like a victory dance.
“Go us!” I laughed, holding up my hand for a high five. His cock flexed inside me as he laughed back and gave me a high five. He stayed there, balls deep, for a while. He was giving me more time to get used to him, because phase two of this plan was gonna be the fun part. After a bit, he reached up and started playing with my breasts, kneading them gently and rubbing my nipples. At first, I thought it was kind of cute that he couldn’t keep his hands off them, but as I felt him start to swell up, I realized he was doing it to keep himself hard.
I figured a little dirty talk might help in that regard. “You ready to show my booty who’s boss?” I asked him.
“Am I the boss of that booty?” he smiled.
“You’re the boss of anything you want when I’m around,” I winked. His cock flexed as I said that. He adjusted his hips and started to pump. His long, thick cock felt amazing even at this slow pace. Everything was so sensitive and new it was like discovering a new favorite food, a barrage of unfamiliar sensations that you regretted not discovering sooner and certainly knew you couldn’t live without it. His hands stayed busy on my breasts, squeezing them and giving my nipples some love which only heightened my sensations.
His cock head was so swollen that it actually gave me a point of reference to focus on while he was inside me, something my vagina could never distinguish. Mostly I just felt warmth and pleasure, but this was like a laser focus of feeling. The whole experience was heightened, for me at least, because I was on my back looking up at my man and watching his facial expressions as he explored this unfamiliar area of my body like he never had before. He was staring at my chest, but I still watched his eyes and the subtle movements of his lips and brows as he focused on getting as much of his shaft inside me as humanly possible.
I loved it.
“Does that feel good, baby? Are you gonna cum nice and deep inside me?” I purred, trying to rev his engines more if I could.
“I’m gonna cum so deep, baby,” he huffed, working the last few inches of his shaft inside me over and over, arms and abs flexing deliciously as he held himself up without putting too much pressure on me.
“You better. I want you to cum so bad,” I teased, reaching up to feel his muscles. My teasing worked, and his hips sped up. He was enjoying his freedom, but I could tell he wasn’t taking full advantage of it. An element of restraint was still in play. I loved that about him. He knew his size and stayed vigilant with his responsibility to never hurt me. But I wanted him to cut loose, to take my body and use it to empty his balls in a way he’d never been allowed before. I wanted him to unleash that inner beast that was clawing its way to the surface. He deserved it.
“C’mon, baby, give it to me,” I moaned, licking my lips seductively and giving him a playful spank.
“I’m gonna, baby, I’m gonna-” his voice caught in his throat and his cock swelled even harder. I knew exactly what that meant. I reached up and cupped his face, forcing him to look me in the eyes as his enormous cock flexed and shot a giant load of his sperm deep inside me. Sweat dripped from his forehead and onto my left nipple. I felt a rush of warmth and a new slickness inside me, his cock gliding almost effortlessly with his massive load acting as lube. “Ohhhh my god,” he groaned out, staring into my green eyes while he finished his orgasm into my booty.
He pumped his hips a few more times, then pushed in as deep as he could. I felt his cock throbbing hard. I stared up at him as he caught his breath, smiling that I could give him something new. “That was incredible,” he sighed.
“You’re not done,” I replied. He raised an eyebrow. “I could tell you were holding back.”
“I mean, only a little. It felt amazing.”
“Take me again, and don’t hold back,” I said, staring him in the eyes.
“Right now?”
“I know you’ve got another round in you. You always do.” He smiled and shook his head.
“I think I’m in love,” he smiled.
“Good booty will do that,” I laughed. He pulled his massive shaft out of me and I felt some of his sperm drop out in the process.
“Flip over,” he instructed. I did. He gripped my hips with both hands and lifted me into a doggy-style position, then lined himself back up and entered me again. With his a fresh load of his sperm inside me and our previous warm-up, it was simple and fast. He took a moment to give some warm-up pumps, adjusting his position and making sure he was fully hard again. From this angle, he felt bigger and I wondered if maybe he was even more turned on than before. Good. I wanted tonight to be burned into his memory for the rest of his life.
Once he got his rhythm figured out, he started to really go for it. Both hands squeezed my hips tight, holding me in place so that his hips could speed up. His heavy balls swung underneath me and rubbed against my vagina in the most satisfying way. My hands and knees dug into his bed as I struggled to keep myself stable. At first, he only pumped the last few inches of his cock inside me, but once we had established our angles he worked his hips far enough back so I felt almost his entire length sliding in and out of me, from base to tip, over and over.
He gave my booty a smack and sped up, working his rock hard shaft into me harder and faster than he’d ever been able to before. His huffing and puffing turned to low grunts, like he was tired but unwilling to slow down and catch his breath. Each time his entire length buried inside me and his balls slapped against my vagina it sent a burst of additional pleasure through my body that I could tell was culminating to something significant, like stacking bricks on a Jenga tower. “Oh god, yes, don’t stop,” I moaned, lowering my face to the pillow in front of me to give my arms a rest.
Doing so changed angles in the best way. His impressive length filled me in ways I had never experienced and the whole situation was bringing me to places I had never been. My words of encouragement made him speed up again to a pace that can only be described as pounding. I felt his sweat drip on my back and heard him huffing and puffing for air but still unwilling to slow down. Little explosions of sensory bliss popped through my brain like firecrackers. A familiar tingling heat reached out from between my legs and took hold of the rest of my body. Am I really about to cum right now?
On all fours, getting pounded by my studly man who was deeper inside me than anything had ever been before, my jaw dropped and my thighs shuddered. I let out a hoarse squeak and clenched my fists around his silk sheets. He knew what that meant. A switch flipped and any restraint he may have had gone out the window. He reached forward and grabbed my shoulders with both hands, ensuring I could not go far as he slammed his enormous cock inside me. My orgasm hit me like a hurricane. I let out a wail of ecstasy, and my entire body began to convulse.
With his hands holding my shoulders, I couldn’t escape, so I instinctively tried to flatten myself out and get a break from the unrelenting waves of pleasure but he thrust his hips forward and kept me still while he worked his shaft inside me. My breath came in such fast, ragged gasps that I thought I would hyperventilate, maybe even pass out. Each of his thrusts forced a new squeal of delight from me and right when I thought my brain would shut off from over stimulation I heard him let out a groan that was closer to a roar than anything else.
His hips fired like a piston for roughly five seconds and his cock got harder than titanium as he finished his second load inside me. He released his grip on my shoulders and gave me the space to collapse onto the bed. He collapsed on top of me, huffing and puffing like he’d just climbed all the stairs of the Empire State Building. I felt his heart throbbing on my back and through his cock, which still hadn’t left me. He panted on top of me for a while and I basked in post-coital bliss.
“So apparently, anal orgasms are a thing,” I said.
“Yeah, I had two.”
“I meant me, smartass.”
“You’re welcome.”
We laid like that for a while. I might have even fallen asleep for a bit. Eventually, he groaned and lifted himself up, pulling his tired yet happy cock out of me. My booty throbbed and kind of missed him. I stayed belly down, relaxing while my body recovered.
“Wanna take a shower?” he asked. I prepared to get up and clean off, but my muscles vetoed that quick.
“Can’t get up. Too tired.”
“I got you,” he said, gently lifting me off the bed with his powerful arms and bringing me to his spacious waterfall shower. We relaxed in the steamy heat for I don’t even know how long. We cleaned each other off and massaged each other’s bodies. Sunlight peeked through the window as morning came. Worth it. We finished up our steamy shower, and I got dressed. I don’t know what it was about this man that got me so riled up. He could convince me to do anything, and I mean anything. If he wanted to be the next Bonnie and Clyde, I’d ask which bank he wanted to hit first. How did he have so much power over me?
I gave him a kiss goodbye, and he walked with me to the door. “I meant it, you know,” he said as I stepped out into the cool morning air.
“Meant what?”
“I think I’m falling in love.”
I smiled. “Good booty will do that to you.”
“It ain’t just about the booty,” he said.
I chewed on my lower lip, trying to hold back a smile. “I might be too,” I said, blowing him a kiss and walking back home to catch a couple of hours of sleep before school.
Libbie
- 13.09.2021
- 50
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- Category:
- Anal
