Andy's Anal Adventures: Kelly

There are some mild BDSM elements in this story. If you don’t like a little rough play with your anal, this might not be for you.

By the time I ass-fucked Kelly I didn’t even like her anymore. And you know what? As sad as it sounds, that made it even better for me. I didn’t worry about her pleasure. I didn’t care if I hurt her a little. All my pent-up anger at what I perceived to be her transgressions were released through my cock as it rammed into her pliable anal ring. No doubt, I can be a bastard. And that night I didn’t care. That she got off on the rough treatment was secondary to me, a happy accident – for her, at least. I didn’t give a shit; I would’ve loved it regardless.

Kelly and I had an instant attraction. A redhead with the usual fair, freckled complexion, she also seemed to have the stereotypical Irish temper. I found out later that she was more psychotic than simply quick to anger. But I didn’t see that at first. All I noticed was her wide smile, quick wit and big breasts. I’m shallow like that. We were hot for each other from the first night, dry-humping on my couch with her shirt shoved up over her fleshy pale orbs, my tongue tracing a trail over the fine blue veins visible through her nearly translucent skin.

She turned me on with tales of her sexual independence and experience before we even screwed. “Nobody’s gonna call me a slut just because I’ve fucked a few guys,” she once told me. “I don’t need to apologize for loving sex.” Like I’d ask her to.

We quickly became a couple and fucking soon followed. But for all the pre-intercourse hype, the sex wasn’t great when we finally consummated. What a gyp. I’m not sure what happened, but we certainly didn’t set the sheets on fire.

I think what really turned me off was that I realized she was nuts. Not cute crazy like lots of us. No, I’m talking insane. She flipped out over the smallest things and her moods changed dramatically and with no notice. Alcohol just made it worse, and she loved to drink. She’d begin the evening a tantalizing angel, teasing me with proclamations she swore would send me to heaven. A few rum and Cokes later, though, and she’d have me in hell.

The crazier she got, the more I pulled away. I wasn’t into her enough to put up with the bullshit and, frankly, I just didn’t have the desire to match her intensity. We saw each other less and less, until I finally told her I didn’t want to “date” anymore. Strangely, she was okay with that and wanted to continue hanging out and hooking up. And then a really weird thing happened: The sex improved. It didn’t suddenly become all-time or anything that fantastic, but it definitely was more fun. And so was she. Her quick laugh returned, her moods leveled and she seemed to stabilize.

I’m no psychiatrist, so I didn’t try and delve too deeply into her transformation. All I did was enjoy it. She was even comfortable having sex without commitment – my favorite kind. She’d come over to the dingy basement studio I was renting for the summer and we’d have a couple drinks, maybe smoke a bowl and screw. Simple pleasures for a simple guy.

And then one night I was the one who snapped. I had my face between her legs, giving it to her good. She squeezed a boob with one hand and held my head in place with the other. Like I was going anywhere. I tongued her large clit and had two fingers from my right hand curled in her roomy pussy, rubbing that spot right behind her pubic bone.

“God that is sooo good,” she moaned, before whispering, “Maybe when you’re finished I’ll suck you off.” Now, number one, she said it like she was doing me some favor. And that alone irritated me. Number two, I knew she wasn’t gonna give me a great blowjob. She never had before, so why would she start on this night? For some reason it pissed me off. Here I was, giving her my best, and I knew she’d hardly reciprocate. Oh sure, she’d lay there when I was done, hold her thick thighs apart and groan with gusto as I speared her until I came. But there was to be no great sucking for me. There would likely be no position other than missionary. The sex would be perfunctory instead of just fun.

I felt myself getting angry, but I continued flicking the tip of my tongue over her little button, separating the hood from it gently and slowly bringing her to a huge crest. My right fingers still stroking the roof of her pussy, I pulled my left hand from around her thigh and wet my index finger in the generous juices her slit and my spit provided. I lowered my digit and made a few quick swipes over her anus, pressing persistently – but not penetrating – with each pass.

The area lubricated, Kelly loosened and relaxed and moaned louder as she neared climax, her hips jerking. I slowly-but-firmly worked my finger straight up her ass, the muscle spreading. “Ooooh!” her cries grew. The hand on my head pushed harder, and I responded by burying my finger in her tiny passage.

She peaked in a rush of breath, several quick gasps and a long, moaning exhale as I worked the fingers of both hands back and forth in her lower orifices. “Jesus Christ!” she exclaimed when she came off her high. “Jesus Christ that was awwwwesome. How can I get you off? Can I suck you?”

My face – resting in her pubes while I slipped my fingers from her holes – perked up. How indeed. “Kelly,” I said quietly, hopefully. “You’ve had anal sex before, right?”

“Yep, with one guy,” she answered immediately. “Why? Is that what you want?”

“Could we? Please?” I asked sincerely.

“Let me up,” she stated sternly. Uh-oh. Guess not, I thought, as I climbed off her body and gave her room to move. But all she did was roll over, then pushed herself up on her knees and turned her head to face me, smiling. “Yes we can. I want to. You’ll go easy, right?”

Grinning, I nodded my head and gave her thin lips a quick peck. The grin wasn’t for her. I couldn’t wait to shove my girth up her. And it wasn’t going to go easy. But once she assumed her position on all fours before me I was struck with two emotions. One was compassion. We had broken up, weren’t getting back together and yet she still was willing to take it in the ass. Her soft skin looked vulnerable and fragile and a part of me wanted to be gentle. The second emotion was lust and a desire to dominate. Guess which one I chose?

I smacked her right cheek and she yelped – I had never spanked her before – but didn’t move. Then I thought of the night she wigged out and left me at a bar, disappearing without a word after I apparently made her jealous by saying “hi” to an ex, and I hit her harder with my open palm, raising a rosy mark on her milky skin. I remembered her half-hearted head and slapped her ass again. Memories rushed to my brain: yelling at me for no reason, ten crazed voice mail messages in an hour, promising nasty fun but passing out instead. Spank, spank, spank.

“Oh, oh, oh!” came her staccato cry. Her chubby cheeks jiggled like Cosby’s jello with every blow as I beat them beet red. She shook her shit from side to side but didn’t try to escape and didn’t say stop. I’m not normally dominant, but I wanted to lord over her.

“You deserve this, you know,” I hissed, harshly kneading her bruised buns and leaning close to her flushed face. “You’ve had this coming.” As strident as her personality normally was, I considered the fact that she’d revolt, get up and go. Fine, whatever. If she did I’d just jack off to a juicier memory. Instead, though, she was cowed and submissive and kept her head bowed between her arms.

“I know I deserve this,” she cried. “I know I’ve been bad to you.”

Surprised by that admission, I nearly took pity on her. Nearly. Instead I pushed my luck. “Tell me you need to be taught a lesson,” I seethed, my fingers menacingly tapping her ass. She hesitated. Slap! I smacked her harder than before, raining five blows on her in quick succession.

“I do, I do,” she howled, squirming. “I do need a lesson. I’m sorry, I am so sorry.”

“You know sorry’s not gonna cut it, right?” I replied, my cock quickly growing rock hard again as I thought of the possibilities.

“Yes,” she answered in a small, little-girl voice I barely recognized as hers. “I know I need more.”

My anger read like a topography map upon her battered ass. Raised palm prints criss-crossed her delicate skin, which virtually glowed red in the room’s soft light. “Damn right you need more,” I told her. “And now you’re gonna get it.” She whimpered as I leaned down and spat on her asshole. I cupped her pussy and found it still dripping.

“What do you think I should do?” I asked her. “What do you think will help you get the message?” Taking some juice from her pussy, I scooped it up toward her tight pink ring and mixed it with my saliva.

“I think you should put your penis in my anus,” she quietly stammered, surprising me with her clinical language.

“I should do what?” I said, working more liquid around her puckered hole. “That sounds dirty, dirty girl. So say it in a dirty way.”

Confused for just a second, she caught on quickly. “You should put your, your…your cock in my ass,” she whispered.

“What?” I demanded loudly, surprising her with two more harsh smacks to her butt. “I can barely hear you. And ask nice.”

She paused just long enough for me to hit her again. “Please fuck my ass,” she moaned. Louder, yes, but not loud enough for my liking and I slapped her cheeks again. “Ow! Please, please fuck my ass. Come on, please fuck it.”

She spread her knees wider apart, leaned forward with her big tits pressing against the sheets and presented her asshole to me like it was a gift. I suppose it was, in a way, and I couldn’t wait to use my new toy.

I circled her tiny star and gently exerted enough pressure to allow my finger through the gripping muscle protecting her most intimate spot. Low moans escaped from both our throats at the feeling. Her warmth enveloped my digit, surrounding and pressing upon it. I withdrew, gathered more juice from her soaking snatch and returned to her nether hole. And this time I wasn’t gentle and careful.

I shoved my finger back into her ass and rooted around while she groaned. Mmm, hot and moist. I thought about adding a second finger, but I didn’t want to stretch her and make it easier for her to take my dick – I wanted resistance.

I moved my knees directly behind her and replaced my index finger at her ass’ entrance with the tip of my thick prick. I heard her suck in a deep breath and prepare for the invasion. I spread her red cheeks with one hand and guided my glans into her hole, which was open just slightly from my skinny finger. I grinned again, thinking about how the hole would soon be abused and gaping. The head of my cock slipped inside, her anal entrance attempting to close behind the crown of my circumcised prick. My progress stalled, I penetrated more forcefully.

I didn’t get far. While the head and a small part of my shaft reveled in the warmth, moisture and incredible tightness of her ass, the thickest part of my meat wouldn’t go in – I was stuck. I pulled her hips towards me while pushing. “Ohhhh. Oh god, oh god,” she yelped, before gasping, “Oh please, do you have any lubricant?”

I hesitated for a second, looking down at my six-inch-round dick trying to fit into her tiny dot. Hmm. Did I have any lubricant. Well, yes and no. Yes I did, but no, she wasn’t going to get any. “I’m sorry Kel, what’d you ask?” I sweetly replied, pretending I couldn’t hear her. I shoved forcefully and began making progress, drilling further into her soft chute.

“Do you have any lube--” she shrieked, cut off in mid-sentence as my thickness plunged through her barriers and plowed into her depths. “Ohhhh ne-ver-miiiind.” I smiled first in satisfaction and then with pleasure as my cock crashed into her cave and my pubic hair met the crack of her ass.

We both moaned long and loud as I kept my shaft sheathed to the balls in her gripping tunnel. “Jesus, Jesus,” she panted, her insides pressing hard from all angles on my invader. “God it feels so deep.”

That was sweet of her to say, because I’m only average length. Of course, shoved all up in her ass it probably did feel plenty deep. I slowly pulled out, feeling the cool basement air kissing my steaming cock. About two-thirds of the way out I pressed in again, but slowly and deliberately, savoring every second and each millimeter. When I was once again buried in her squeezing cavity I spread her cheeks wide and drove my hips in and up, changing the angle of the tip of my dick and driving it even further up her ass.

“Oh shit!” she cried. I pulled all the way out and admired her open hole. A minute ago her anal ring was tightly shut. Now it was stretched and red. In another few minutes it would be gaping. I let go of her cheeks and the elasticity of her muscle pulled the star mostly closed. I positioned the tip of my cock back at her entrance and leaned over her sweaty back.

“Ready?” I softly stated. “Want this back inside you?”

“Yes,” she immediately whispered. “Put it in me. Come on.”

I slipped just the head easily into her chute and she sucked in her breath, waiting for me to power it into her. I flexed my hips, making her think it was coming, and I felt her body tense, steeling herself for the thrust. “You deserve it hard, don’t you Kelly,” I said in a low, threatening voice. Kind of cheesy, yes, because I’m really not usually like that and I didn’t know if I could pull the whole dom thing off. But she had stirred something inside me. And I figured I had her in a very vulnerable position.

When she paused I smacked her ass hard, quickly reddening the already tender cheek. “Yes!” she yelped. “Yes, I deserve it hard.”

She braced a hand against the headboard and I firmly forced through her soft cylinder. My thick prick pushed her insides apart and my balls slapped her soaking pussy. “Fuck!” she moaned, her big tits swinging. I quickly pulled out and drove it home over and over. Hard. Unforgiving. She would whimper on each out-stroke and grunt every time I slammed it home again.

Her slick hole widened, her passage parted and it became easier to ram my thighs against the back of hers. Pounding away into her guts, I leaned over her and moved my hand around her hips to the wetness between her thighs. Separating her thick folds, juice was pouring from her pussy. I found her clit with the tip of my middle finger and strummed it while I sawed in and out.

To my surprise, she pulled my hand away. “Just fuck my ass, Andy,” she said. “Don’t worry about me. Just fuck my ass.”

Well, OK. Because I was already bending over her frame with my fingers underneath her, I simply moved my hands up and grabbed onto those big hanging breasts of hers. Using her oversized boobs for leverage, I changed my angle and increased the force of the thrusts into her clutching ass. Slamming into her smallest space repeatedly, my bone blurred with the speed of its invasion.

Her hot hole squished around my reaming spear as I roughly squeezed her cherry-tipped globes. The thick nipples grew hard and I caught them between my fingers, stretching gently. Her breath got ragged and she moaned and wheezed. I abandoned the short, quick pokes for longer, harder ones, my cock almost exiting her chute before shoving balls deep.

I pulled all the way out – her asshole audibly gulping – and thrust wildly, my dick desperate to return to her rectum. Instead of her ass, my prick plunged all the way up her still-wet snatch. She groaned sharply. “Wait, not in there, you don’t have a rubber on,” she whined while I involuntarily moved in her cunt. Her pussy was pleasant and sorta snug, but nothing like the vice grip of her ass.

I removed my rod, spread her flesh, leaned back and looked at my handiwork. Both of her lower openings were as crimson as her still rosy cheeks. While her spacious vagina’s entrance was only slightly parted, her anus was yawning wide. Red around the rim and pink just inside, it was a target I couldn’t resist. “Ready for me to cum?” I asked.

She nodded vigorously. “Yes! Yes, come on.” Holding her butt even further apart with my hands, I shoved forward and let my dick find its home. I didn’t stop until I hit bottom, grinding my groin against hers and rotating my hips while she groaned. I pulled out and did it again. Her outer ring was getting raw, chafing my pole. But she didn’t complain. And when I sped up, she encouraged me.

“Yes, oh, yes, oh, yes,” she chanted. Actually, her voice was so garbled that it might have been “Yes, ow, yes, ow.” I didn’t know for sure. And, as long as I heard “yes,” I didn’t care. Who am I kidding; I didn’t care either way.

Thinking about my thick cock reaming the tender insides of this headstrong, bossy babe brought me even closer to the edge. Not that I needed the added incentive. Her pulsing tunnel slid – and even scraped – along my cock until I knew it was time.

“I’m cumming Kelly!” I shouted. I sheathed fully inside her, clenched my cheeks and unloaded spurt after spurt into her butt. She cooed and sighed and gasped as I filled her. Finally I finished, my fingers still holding her hips. She collapsed on the bed, her abused, open hole leaking my thick white jizz.

“Oh god I can feel so much cum in me,” she said softly, gently rubbing her clit to spur more seed to spill out her asshole. “It feels so good.”

That it did. She was spent and I was exhausted – but so satisfied in so many ways. That was the only time we did anal. In fact, I don’t know if we ever even screwed again after that. It was like we knew we couldn’t match that night. I haven’t seen her since the mid-1990s, but I’ll never forget that ass.