Anal Cherry Popping

For the first time, Karin wasn't just hunting for her pleasure and selling sexual release: for the first time, she was enjoying giving pleasure as much as getting it. And yes, she was willing to experiment.

Her professional, efficient blowjobs became softer, longer and far more enjoyable, not only for me, but most of all for herself. Her taste for cuddling and caressing grew dramatically, transforming her into a real kitten, permanently ready to be touched into excitement and even into orgasm.

Toe-fucking her under the table at the restaurant became a must, something we never jumped when out for dinner. Sex on the drive also became a habit, and truck drivers really loved when, on the highway, we offered them the view of my sweet whore blowing me while I was passing them.

Karin quickly became a more hard cored exhibitionist than I was, as we started making out at the most inconvenient spots and times.

So I wasn't that surprised when, after lots of persuasion and teasing, she finally accepted to let me have my way with her gorgeous ass.

I wasn't an expert myself, and had no Literotica "How to's" to help me, so I wasn't so successful at the beginning.

Poor Karin was screaming out in agony as I tried to push into her with the only help of a body cream, and I was just slipping around her back entrance helplessly, until we were both sore.

Then, one day, it happened.

I loved massaging her. It was a wonderful way to have my hands on her supple body, enjoying all the sinuses of her lithe frame, and sensing the pleasure slowly growing into her.

It could easily be a long affair... I mean hours long. I would start from her shoulders just to relax her, to go down on her back like for a proper massage. I would then go on her head, to complete the relaxing and prepare her for the pleasure to come. Next, I would take her hands, one after the other, to slowly start climbing up along the arms, enlightening the first sparks of electricity under her permanently tanned skin. Climbing her arms, I would start alternating caresses with kisses, paying much attention to her inner elbows, up to reach the armpits.

Karin was a real blonde, like most Dutch and Flemish blood: her body hair was fair, short and thin to the point there was no shaving for her. The faint golden fur on her smooth skin made it just more velvet and appealing... So I ended up caressing, kissing and sipping her armpits for quite a while, until she shivered and moaned.

I would feel and caress her breast of course, but not kiss it, feeling her not ripe for that yet. Rather, I would jump to her feet, and start on her long legs the same proceeding I just accomplished on her arms.

Any woman is sensitive on her feet; many are along the whole legs. Karin wasn't aware, but she was actually hypersensitive on her inner thighs.

After fifteen minutes of work on her long limbs, she was hardly shacking with desire.

My cream-coated hands reached as far as the side hair of her lush golden bush, without actually reaching her pussy, teasing her mercilessly.

"Hmmm..." she would moan, like a sex-starved kitten.

Now, my hands were again on her slim, nerved back; from her sides they travelled to her incredibly long neck, to slip back down along the sides of her flexible spine... Down, down to the crack of her buttocks.

Time to smear more and more cream on her body, from the root of her blond mane, down to her muscled ballerina calves; then, I was ready to shift to phase two of the massage.

I slowly lay on her with my whole body, sinking my mouth in the full of her neck to kiss and bite her with harness, as to remark my ownership over that beautiful piece of female flesh.

I was by now rock-hard, and she could feel it: due to our different size, my cock slide just exactly in the smooth crack of her ass while I was kissing her behind the ear, and my knees were just behind hers. By holding on my elbows, I was now in the perfect position to rub the whole of Karin's body with mine, in what was just an attempt to a Thai full-body massage.

"Oohhh..." she purred, her eyes closed to better enjoy, "Oh yesss..."

It's a special training in the Army, to crawl very slowly making leverage only on your elbows and foot toes: I was doing it on Karin's frame, rubbing myself on her back, with a thin layer of body cream to lube the contact between our excited bodies.

"Hmmm... I love it!" she hissed underneath me. "It's sooo good..."

I loved the full contact with her body, and I loved rubbing against it. From my mouth lips to my knees, I was touching her with all of myself, but for my elbows and toes which worked as the leverage for our mutual motion.

My fully erected cock was sliding comfortably in the crack of her warm ass, in full accordance with my rubbing movement: up and down, up and down...

"Oohhh... So good..." Karin moaned in her blurred mode, by now hot like hell but still totally relaxed in all the fibres of her body.

Up and down, up and down...

"Oh yes, keep going please..."

Up and down, up and... IN!!!!!!!!!!"

"YEAAAGGHHHHH!!!" Karin yelled, arching her back at the sudden, totally unexpected intrusion.

I had felt just a slight resistance on my cockhead during my surge, and just pushed stronger to overcome it. Suddenly, I felt my cock slip into her like it had been ambushed, and I was into her ass.

I had not planned it. I didn't even realize immediately what happened. For a second, I thought I had smashed into her relaxed cunt.

But it wasn't. It was far too warm, almost burning, and TIGHT!

"Oh my GAWWDD..." Karin gasped in disbelief, feeling far too well what had happened, as I naturally finished sliding into her rectum up to the hilt.

She tossed her head to look at me, her eyes bulging in astonishment.

Boys she was relaxed! I'd never thought it was ever possible to relax THAT much... Her sphincter was more open and helpless than a sleeping duck in a pond, and offered little if any resistance as my bulge pushed into. Yamamoto had no clue what a surprise attack can be... In our case, ever the aggressor was so stunned by the event that for a second I froze, looking into Karin's bulging blue eyes as she lay still under me, unexpectedly stabbed.

I feared I hurt her badly; maybe I even damaged her... But no, there was no pain in her eyes: just surprise. Wonder. Shock.

Tentatively, I tried to slide back.

Karin's eyes bulged ever more, as I felt her anus contracting to keep me in.

As instinctively, I pushed back into her rectum.

"Oh my God..." Karin gasped again, shivering under me.

"I'm sorry," I uttered, still in amazement, "I didn't intend to..."

"Oh, shut up and fuck me!"

For the first time in many months, I couldn't read her expression: rage, pain, lust, surprise, excitement were all mixed up on her face while I slammed back into her asshole, consuming our unholy coupling.

"Aahhh..." she panted, feeling my greasy shaft sinking again into her bowels until my balls slapped against her hairy pussy lips.

When her face sank again into the pillow, I kissed her back behind the ear, and she purred with pleasure.

"Oh my God," she hissed face-down, "You busted me!"

I stood frozen for a second, recollecting my thoughts and enjoying the feeling of her muscles slowly chewing my deeply embedded cock.

"Did I hurt you?" I finally asked with a worried tone into her ear.

Karin shook her head: "N... No. Not at all. It's... Strange. Gosh, I feel so full! It... Burns. Just a little. But it's nice..."

I didn't need more.

I started moving inside her. Slowly at first, to avoid slipping out or to rip her rim.

I couldn't believe it: I was butt-fucking her! I was feeling her muscled buttocks contracting under my hips as I got into a fucking rhythm, and her sphincter was pulsing too, slowly adapting to the massive intrusion.

I rose on my knees, ending up sitting on her closed thighs, so that I could watch the evidence. There was no mistake: my cock was fully embedded into Karin's asshole. I opened her ass cheeks with my hands to better enjoy the sight. It was awesome: the shaft was pumping back and forth the overstretched anal opening, which rippled rim appeared smeared with cream and just slightly reddened. No blood or any sign of a bruise.

"What... What does it like?" Karin asked from under the pillow.

"No damage, honey," I grinned: "Get ready now, we go!"

"Ouch! Be careful, this is the first time... Oh my God! Oh my God, it burns... Oohhh!"

The first time... That was the point. It was the first time. I got engaged with prostitute, and besides she got countless men before me, I still got her cherry.

I deflowered my bride.

She was really and truly mine.

And since that was my first time too, I was hers as well.

It felt wonderful.

I slide on her back again, feeling once more the feeling of her skin all along my body, and grabbed her breasts from under her chest. I squeezed them hard, exacting a moan of pain from her contracted mouth, while I pushed her thighs together with my knees and forced myself on my feet to find leverage again.

I whispered, "I love you..." in her ears, and then I started fucking her.

"Aahhh..." she moaned "It burns... But it doesn't hurt. Fuck me. Fuck meee!"

And fuck her I did, deep into her ass, with all the eagerness of my long waited forbidden desire.

"Ah! Ah! Aahhh..." she was panting at each and every push, getting accustomed herself to the new practice.

I don't know how long I fucked her ass, that first day: maybe it was hours, maybe just a handful of thrilling minutes, but it worth all the sex I had before Karin, and maybe more.

It was so tight and hot that I was feeling really hard to resist. All the excitement of cornholing Karin for the first time, and of cornholing a woman at all for that sake, combined with the delicious sensations that our forbidden union was giving me, all made it look like as the final outburst was getting close.

Normally, I had a clear intent while I was doing Karin the normal way: having her climax before me. In this situation, I had no clue.

I raised the tempo of my thrusts into her, heading to my orgasm, when I felt Karin contracting and tensing under me, arching her back towards my chest and accelerating her already quite fast breathing.

Suddenly, she gasped in disbelief and shook all her body, pushing all herself against me.

"Oh my God I'm coming!" she yelled in shock. "I'm cumming... Oh... Oh... Oohhh!"

Karin climaxed under me, shaking and convulsing like when hit by her strongest vaginal orgasms.

I felt her rectum clench around my cock like a vice, literally milking my inner essence not only from my balls, but from my brain too.

"Uhnnngg..." I muttered as all my body contracted and arched in turn, and I instinctively pounded back into her bouncing ass, sinking as deep as I could reach into her bowels.

"Aaghhh!" Karin screamed, this time in pain for the violence of my last thrust, feeling stabbed and pierced through her belly like I had somehow reached bottom inside her belly.

I felt like a bomb exploding in my head, such was the violence of my release. I orgasmed into her own unnatural climax and a blast of sperm shoot violently into Karin's ass, washing her clenched rectum with powerful jets of cum.

"Oh my God, I feel it!" Karin panted painfully, "I can feel your cum filling my ass!"

Wave after wave, my climax seemed never ending, just as Karin's. I felt like I was passing out, as my arms got limb and I couldn't hold myself anymore.

I fell on her slippery back, grasping for air, loosing completely my hold on her, but her ass didn't loose its hold on my shaft, so we remained strictly entwined anyway.

For a moment, I thought, This is a good way to die, than I realised it had to be ever stranger and newer for Karin, since that one had been her very first anal orgasm.

"That was awesome!" Karin sobbed suddenly, still trying to retake control over her exhausted and used body.

I had no strength to reply. Her asshole was still holding me tight, so much I was starting wondering weather there was any risk we needed to go to the hospital to get separated...

Then I felt a couple of contractions, followed by a soft laughing from my beloved one, and I realised she was back in control of her body.

Slowly, her sphincter de-contracted, and my cock started finally deflating and softening, until it finally slipped out of her abused hole.

"Uuhhh!" Karin shrilled, as a rivulet of cum leaked out of her rippled anus.

I had no more strength than her to react to that, so we let it dribble along her ass crack and down her thighs, to make a puddle in the middle of our bed.

After a couple of minutes, I managed to rise unsafely on my side, and turned to admire my naked and dishevelled companion.

She looked lovely: her soft skin was all smeared by the mixture of body cream and sweat, her blond hair was a mess on the pillow, and her wonderful blue eyes were sparkling joy and satisfaction at me.

Somehow, I managed to reach her mouth and kissed her death-cold lips.

"I love you..." she hissed softly.

We lay on the bed for at least half an hour, striving to regain some composure while holding each other in the most caring of the embraces.

When we finally managed to rise from the bed, I checked on the puddle between Karin's thighs, and appreciated that what came out of her ass was just a mixture of sperm and cream, with no traces of blood.

While Karin stood to clean the sheet, I bended to inspect her hole.

"How does it look like?" she asked, half embarrassed and half intrigued.

"Hmmm..." I smiled, since the tissue wasn't yet closing back and the hole was gaping open, "It's most definitely not a virgin hole any more, my dear."

"Oh, it was so cute!" she complained in mocking sorrow.

"You've got a cherry popped today, my love..." I added, with open satisfaction.

"Yeah!" she agreed, "We have to celebrate!"

So we took a shower together, and she gave me a blowjob under the jets of warm water, and then she wore one of my favourite (very short!) dresses and we got out for dinner. In the restaurant, we went to the restroom to wash hands before eating, and there I got the chance to eat her out as an appetizer; when we went back to our table I kept her knickers in my pocket.

During the dinner, I toe-fingered her naked and sloppy pussy between the pizza and the ice cream, and after dinner we ended up in the courtyard of our apartment building.

It was well past midnight, and the place was empty and dark. We made up for a while on the small bench which lay in the corner, until Karin was moaning with desire.

I had no whish to go upstairs, so I just raised the hem of her dress, uncovering her more than willing pussy, and offered my desperate cock to her eager mouth.

Karin blew me stiff, and then I opened her legs and drove my erection into her hungry cunt.

It was fast fuck: we were both tired and excited, and my position wasn't the most comfortable. Besides, Karin yells might well weight up the whole neighbourhood, so I pounded heavy and fast, driving us both to a more than satisfactory climax.

She barely checked her shrill as her pussy contracted in orgasm and I shot my load against her cervix.

"Yes... Yes... Fill me up," Karin panted in my ear as I released myself deep into her steaming and spasming cunt: "Hmmm... So good! Oh, so good! Today you didn't cum in here yet... Gosh, I can well imagine my pussy will be quite jealous of her little brother hole from now on!"