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Discovering the Deep Pleasures of Anal Sex

"Mary has multiple orgasms from anal sex, and subsequently demands it often!"

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When I was in university, my sexual experience blossomed with my girlfriend, as did hers, along with our sexual identities. My love for Mary was complete, and our very active sex life solidified our heterosexuality. Mary shared an off-campus apartment with Karen. My sexual landscape began to change, however, when Karen's boyfriend John entered my life, which confused my sexual identity. This true story tells how Mary and I became fans of anal sex.

Although I had a few encounters with John, I wasn't at ease with it. It still seemed taboo, but John was always comfortable! I let him make all the moves and was just a passive participant at first, but then became a willing actor after a couple of times with him. The only thing I did was to actively put myself in positions where John could make a move on me.

After the first encounter, I stayed away from John and tried not to be there with him at the girls' apartment. But after that one night at John's house (revealed in a separate story), I went out of my way to "make myself available." Also, after that night, I could not stop thinking about John's smooth, beefy, muscular butt. You may have seen this kind in the gym. Muscular glutes, smooth, and big. When romping at John's house, he got down on all fours and raised his ass in the air—a very erotic site. I should say I was always an ass man but never gave a dude's butt any notice. But after that night, I constantly checked out campus boy-butt. I replayed in my head over and over, rubbing my swollen cock into John's butt-crack, feeling his puckered anus on the underside of my cock, and ejaculating on the spot against my will.

Now, for one of the last encounters of my senior year. One thing of interest was pubic hair. As you may know, Mary, my athletic girlfriend, often trimmed or shaved her pussycat. I was hairy-chested with a big, thick, black bush, and Mary was always spitting out pubic hair while sucking my cock. One time, she suggested I trim. So after some thought, I did. I had an electric trimmer, which I sometimes used on my hair and beard. So I attached a quarter-inch guard and trimmed my pants. My cock was rock-hard during the entire time. My erect penis looked even bigger. I was so horny after trimming; I got in the shower and shaved my balls and the base of my cock completely. I could not wait to fuck Mary! Although I wanted to stroke off badly, I decided to save my huge load for her. All I could think of was Mary's tight butt and how I'd like to fuck her up the ass, something we hadn't done yet. After my erotic encounter with John's muscle butt, all I could think of was butts. I called Mary up and made a date to go bar-hopping. I threw some KY in my backpack. I wanted to get Mary drunk and fuck her butt.

I headed over to pick up Mary, and we hit the bars. We had a great time and ended up walking from the last bar to her and Karen's apartment, about a half mile. Neither of us should drive. When we got in, John and Karen were really going at it in her room. The constant groaning rhythm of the creaking bed, John's low, short grunts, and Karen's moaning told the story. Between hearing their loud sex play and knowing I was in for a long night of sex, I was already hard.

I could not wait to expose my cock and trimmed pubes to Mary. Off went my shirt, revealing my cut 6-pack. Off went Mary's shirt, immediately exposing her breasts, nipples hard and pointed. Off went my jeans, my penis bouncing out like sprung steel from going commando.

"Oh my God!" cried Mary when she saw my nearly bald cock.

"You trimmed! I LOVE IT!!!" she said enthusiastically.

Off when Mary's jeans and pants in a flash. Mary swiftly kneeled in front of me to worship my big, thick penis. I put my hands on my hips and swiveled them, knocking my cock across her face. She squealed in delight as she sniffed and tried to lick my swaying cock. Every time she tried to get her hungry lips around it, I moved it out of the way. I wanted to tease her good and long so that I might have my way with her ass. Mary reached between my legs and up to scratch my ass. Once again, she tried to get her lips over my cock, but I won again. Mary whined in frustration. She needed to suck some cock. I reached down and played with her nipples, her hungry moans now very frequent. One hand played with my big balls, while the other felt my ass. I teased her for minutes on end. She finally grabbed the base of my cock, holding it still so she could go down on it. I wrapped my hand around hers and rubbed my cockhead into her nostrils. My cock glided easily and wetly across her nostrils from my pre-fuck leaking from my slit. She gave me wanton girl-grunt.

"Whatcha need, baby?" I teased.

She whimpered in response. I again rubbed my cockhead into her nostrils; she inhaled deeply and rubbed her pussy.

"I need your cock, you fucker. Let me suck it."

"Maybe... whatcha need, baby?" I teased again.

"I need to eat your hot, thick juice!" Mary finally gave in. She was hot for my spunk. No doubt about it.

"OK, babe, eat it." I placed my fists on my hips, and she immediately began sucking my cock. She ate like she was starving! Slobbering, whimpering, and moaning all over my cock. This always gave me such a sexual high... to have a hot, horny lover in heat for my cockmeat.

I let Mary suck it for at least ten minutes. I could smell her wet pussy from where she was kneeling before me, worshiping my big one. What a little bad girl; man, I loved her! Her moaning was now just a constant string of vocalizations, all centered around her enjoyment of sucking my cock.

"Ahhh, grrunnng, mmm, ohhhggg," and all the wet sucking and licking sounds.

As you may know from other stories, we were both very vocal and very loud. We never cared who heard, and often our windows were open to let the neighbors masturbate to our fucking. Mary was very hot at this point.

I threw her on her bed, face down, her knees at the edge of the mattress. I kneeled down behind her, slid my hands under her taught belly to her tits, and played with her nipples. She instinctively spread her knees farther apart, showing me her swollen pussy lips and pink puckered hole. Waves of pleasure coursed through my cock, over and over again just from the sight of her pussycat and anus. I inhaled deeply her strong feminine scent. Grunting like a beast, I began rubbing my face into the crack between her tight athletic butt cheeks. My cock jumped involuntarily.

"Unnghhh, unnnghhh, unnghhh." Guttural noises escaped my throat in an automatic and animalistic way.

Our sexual drive was in high gear, and no longer were we thoughtful creatures. Just beasts in rut, our biology had taken over our reasoning. Both of us were oblivious to the world, and if we were in Times Square, we'd have continued, no matter the thousands of onlookers.

I rubbed my face into her wet pussy over and over and over and over, never getting my fill. The strong, heady, sweet wetness was something to feast upon. Grunting with each exhale, I wanted—no need—my face to smell like her. I must have rubbed my face there several minutes, my penis fully erect and now starting to throb. Mary's squeals, moans, and groans were loud and timed to which part of my face was rubbing which part of her female gems. Finally, I had, just had, to eat her out. I skipped over my usual cunt-kissing. I lived to kiss her pussycat and usually spent a half hour just kissing her lips, clitoral area, and vulva. Only after this ritual would I lick and eat her pussycat. But I was in a rut and needed to eat her now. Groaning in deep lust, I licked deep into her pussy, my tongue tasting her thick nectar. She moaned a high-pitched moan, which drove me crazy. I rapidly licked and ate her, never lingering on one spot for more than a moment.

Her moans became louder, and I could hear her breathing become shallow and rapid. I knew she was headed to orgasm. Not yet, I thought to myself. I reluctantly pulled my wet face away from her pussycat. My face was drenched with her scent; I loved it.

"DON'T STOP!" she yelled.

Of course I stopped and played with her very hard nipples. She begged me to continue to no avail and began rubbing her pussycat.

"Damn you, eat my pussy!" she cried.

"Relax, babe, relax," was my only reply.

I continued to stroke her tits, belly, thighs, and back until her breathing calmed down just a bit. Then I began to slowly lick her lips. Shortly, her arousal state was again high, with constant moans, groans, squeaks, and vocals. Now was the time. I planted a slow, wet kiss right on her puckered anus.

"Ooohhh," she cooed.

I had often eaten her ass but never fucked it. Mary thrust her ass back into my face. I wetly kissed it again and again. My cock was aching for attention, but it would have to wait. It throbbed with anticipation of what would happen. After kissing her anus, I began licking it—first with just my tongue tip. I rimmed it, outlining circles over and over. Her coos of delight told me she loved it, but they were not the pre-orgasmic sounds I was so used to. I licked and rimmed for several minutes, and then began licking with the flat of my tongue. Her coos changed pitch to lower vocals.

"Uuunnnh, unnnh," escaped her mouth with each breath she took.

I snaked a finger into her pussycat, and she gasped. I then probed my tongue just a bit into her anus, and she gasped again, only louder. I snaked another finger into her pussy and shoved my tongue deeper into her anus, and I felt her sphincter tighten reflexively. This made her grunt and push her ass back against my fingers and tongue. Her anal musk acted as an aphrodisiac as my nostrils flared and my cock spasmed.

"You fucking stud, give me your big cock now!" she demanded.

Fuck, she was ready, but I still need time for my plan to unfold. But once Mary was like this, it was hard to stop her from getting what she wanted. Usually once she demanded my cock, it was only seconds before it was buried and pumping into her. I needed to control the situation absolutely.

"Oh yeah?" I asked playfully.

"NOW!" she demanded, her breathing now rapid again.

"Just wait, babe," I responded.

With two fingers deep inside her, I began moving them in circles, and she bore down on them.

"Ooohhh.' She loved this.

I further rode my tongue into her butthole. It was clean-tasting, with just a musky taste and odor. Not nearly as strong as John's. This thought made me think of John forcing his 6'4", 240' frame down on me, forcing his spread muscular glutes to my face, and him rubbing his puckered anus on my nose and lips. My cock jumped again. Eating pussy got my cock in a highly aroused state... almost to the point of ejaculation. I always had to be careful not to shoot off right away in Mary after eating her.

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I could tell from Mary's new vocals that she was enjoying this new attention to her anus. With two fingers buried in her pussy, I sucked on a finger of my other hand and snaked one knuckle past her anus and wiggled it around.

"UNNHHHGGG," she gasped loudly and backed into my fingers once again.

Slowly I worked my whole index finger into her butthole while reaming her pussy with the other. By her sounds, I knew she was building to an orgasm. I could not let that happen. I rubbed on her clitoral area while reaming both her holes. She gasped, and her toes curled; her breathing became rapid.

"Fuck, do me NOW, fucker!" Mary was in heat. My cock needed attention too, but I did not want to blow my plan—or my load.

I knelt up, my cock impossibly hard, veins sticking out, Mary spread so wide, her pouting pussy lips big and spread, her anus relaxed and swollen from my fingering. I moved my hips forward and, inch by inch, eased my big cock into her tight, wet pussy. She at once backed herself into me, but I would have none of that and withdrew immediately, causing her to whimper in desire.

"Give me your cock NOW," she yelled, very loudly, I might add.

I entered again, she backed up, I withdrew, and she groaned in frustration. After four or five attempts, she stopped backing into me, controlling her urge to be filled with my big, hard, throbbing dick. I eased it in gently, not wanting to shoot and not wanting her to come too soon. After a couple of minutes, I was in balls deep. I pinned my hips to her butt to ensure no thrusting would happen, causing me to cum. I then sucked my thumb and began some butt-play. I eased my thumb in, triggering a slew of sex-noises from Mary. What a little cutie. After a few minutes of this, Mary began to squirm wildly while impaled on my penis. Again, she was nearing orgasm. I pulled my cock out, and she groaned again in disappointment and frustration.

"I'm not through playing with you yet, babe." I went to my backpack and got the KY.

"I need to be fucked, Tom," she pleaded loudly.

I showed her the KY, and she watched wide-eyed as I spread it on my fingers.

"No way. You'll split me in two! No way."

"Just relax," I said, my voice thick with lust.

I put her on her all fours and slipped two lubed fingers into her butt, easily. I began to fuck her butthole with my fingers. She winced but soon began to coo again. With my other hand, I played with her pussy lips and clitter. It was not long before her body showed me the telltale signs of her approaching orgasm. I pulled my fingers out.

"DON'T STOP!!!" she yelled. I knew my teasing had paid off. "FUCK ME NOW!"

I didn't say a word. My cock was begging for relief, and I knew Mary's body would not last much longer... she was going to orgasm soon, whether I liked it or not. I got the KY and squirted a lot on my big, very erect penis. It felt cool and smooth. I slowly spread it all over my cock, from head to balls, with my fingertips. Mary turned her head to try and see what I was doing. I squirted a second dose on her anus; I was going to put something pretty big into something pretty small.

I repositioned Mary on the bed so that we could both be on it. Her head faced the headboard. I pushed her shoulders to the bed and raised her hips up. I eased one slick finger into her butt and slowly added another.

"UNNGHH!" she gasped!

I pulled them out and pushed my flared, leaking cockhead to her anus. I gently thrust forward.

"No! it'll never fit!" Mary yelled.

"Just relax your sweet anus, babe, and at least try; I know you like it!"

I felt her anal sphincter relax, so I pushed again, and my well-lubed head entered Mary's bunghole, and she gasped an exhale with a deep, long breath. I began to push my hips further. The tightness was extraordinary. Her pussycat was very snug. But this was even tighter, and a different shape... her butthole gripped my cock in every spot with the same tightness. I pushed more. Unlike her pussy, there was constant pressure.

"Stop! Let me!" Mary panted. "Let me back onto you!" she said breathlessly. 

"OK, do it!" I said.

Mary, grunting, began to gently scoot back onto my raging cock, ever so slowly impaling herself. We were loud during sex, as you know, but tonight, everyone in the apartment complex had to be listening in. I didn't care.

I looked down, and what a view! The dim desk lamp provided enough light to see, but not enough to be garish. Fuck, my cock looked extra huge without the thick bush, and it was now half-buried in Mary's ass. Her anus sucking my meat in, spreading out widely around my thick penis. Mary's vocalizations became increasingly loud, incoherent, and rhythmic with her breathing. Every time she exhaled, she groaned, and every time she inhaled, she "ahhhed." I watched in sexual bliss as she slid her ass forward, exposing three or four inches of my cock, but not enough for my cockhead to pop out. She slowly slid herself back onto my cock, the KY making it slide easily. She did this several times. Luckily I had been drinking; otherwise I'd shot off by now, but I was very close! Now she was incoherently babbling and moaning non-stop. I looked down; she had backed herself up so much that she had only an inch or less to go until I was completely buried. Looking down at her trim athletic ass, my cock buried made me throb and leak, and when I say leak, I mean a stream of hot, thick semen—my usual pre-orgasmic flow.

"Gnnn... I... grunnn... feel...grunnn....your...grunn... hot...grunnn... seed...grunnn... filling...grunnn... my...grunnn... ass... grunnn..."

Mary's voice was choked with lust, barely getting out her words. I loved it. Once again, I was conquering pussycat, making it a slave to my cock.

I felt my own orgasm begin to well up. Fuck not yet! I held her hips steady to prevent my orgasm.

"Stop, don't move!" I barked, choking my words out, trying to refrain from ejaculating.

My cock throbbed once, twice, three times, and then a fourth, and I knew my thick semen was oozing deep into her butt.

"Ahhh," Mary gurgled as I spilled more seed into her butt.

I held her hips firm until I edged past the urge to shoot. I took a deep breath. I reached around to play with her box. I fingered her clitoral area, stroked her cunt lips, and ran my fingers in and out of her wet hole. Her reaction was immediate; each breath and moan was audibly louder than the last... her body tensing... she was building up to a big orgasm. I reached both hands down around her to the nipples. I stroked them, rolled them around my fingers, pulled them, and pinched them.

"Unnghh... fuck... Ahhggg... fuck... Aaaggg... fuck..." I'd never seen Mary in such a high state of arousal.

All during this time I was not thrusting, but Mary was squirming all over my rod now, firmly but wetly impaled in her ass.

"Ohhh,.... Ohhhh,.... OOhhh,....OOHHh,.... OOHHH," she was now writhing underneath me, and I don't think anything could stop what was coming (no pun intended).

I kneeled up, grabbed her hips, and slid my greasy cock all the way out until just my head was in. She gasped. Slowly, I pushed it back in. She shouted. Slowly, I pulled back out. Slowly I pushed it back in, this time all the way, burying it completely.

"AHHHGGGGHHH," she yelled.

I looked down. I was buried completely, my short, bristly pubes right against her anus. I ground my hips into her ass, my cock reaming her.

"I feel... your... prickly... pubes... on... my... ass.!" Mary eked out in staccato vocals... "AHHH... AHHH... AHHH," she started coming.

I stopped all motion as I felt my ejaculation welling up, trying to prevent it. Mary barked as she exhaled, her orgasmic spasms starting. I felt her powerful contractions as her anus squeezed my cock. Looking down, seeing her ass, I thought of John's muscular big butt. That was it. I felt my orgasm triggered from her own, fantasizing that John, not Mary, was down on all fours, my cock firmly buried and ejaculating deeply into his butt.

"UNNGHHH, I'm going to fill your ass... UNNGH." Still motionless, my cock spurted. My eyes are still closed. I pictured John's perfect ass; it's musky butt-scent, his thickly muscled body beneath mine, and his ass filling with my spunk.

"UNNNGHHH," I spurted again into Mary's butt, my cock pulsing with exquisite pleasure.

"UNNGH," I spurted again. Mary was squirming and panting, speared by my throbbing cock.

Mary's head was turned, her mouth wide open in a breathless shout, unable to get out words.

"UNNGH." I spurted again and again, grunting like a beast with each spurt, holding her hips tight against mine, as my cock spasmed in orgasm, my back arched, my hips pinned tightly to her ass, motionless.

"AHHH," I'm still coming!" Mary was in a constant state of orgasm at this point. To me, it was either one incredibly long orgasm or just several in a row.

Mary was flailing around, completely impaled on my spurting cock. Without thrusting, my orgasm went on and on. I was filling her ass with a big hot load. After what seemed like minutes, and it was at least three, Mary's shaking subsided. I did not want to remove my cock. It was still in a state of absolute pleasure, the constant echo of orgasm still present. Eventually, I pulled it out an inch or two, and Mary gasped. I thrust it back in. I did this a few times until I took it out all the way. I looked down at my cock. It was no longer flagpole hard but still swollen. It glistened with cum and KY in the dim lights.

"Unngh!" Mary cried when I pulled my cock out entirely.

She flopped down on the bed, her arms and legs spasming. I watched her, and she kept making noises, her arms and legs twitching. I'd never seen her like this. My cock felt so very good, although a bit sore. The tight pleasure of Mary's ass was a new experience—for the both of us.

"You OK?" I asked.

She gibbered in response. My cock was sticking straight out in its typical post-orgasmic fashion. As I was to find out, Mary had had it for the night, completely wiped out by her anal penetration orgasm. I had to stroke myself off a half hour later as she was stone cold out, and I was flush with sexual energy. Anyway, this opened up a new sexual avenue for us, and afterwards she needed a good butt-fucking regularly. Graduation was around the corner, so Mary and I had sex a few more times before we parted ways. She told me it triggered multiple orgasms, which she'd never had before!

 

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Written by swpmexec
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