Anal Seduction Redux

Story Info
A young man discovers anal intercourse.
5.5k words
4.6
83.1k
110

Part 1 of the 4 part series

Updated 06/08/2023
Created 10/26/2016
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wiley4377
wiley4377
184 Followers

WARNING: This adventure takes place in the late 60's and before HIV epidemic. Do not fuck without a condom.

*****

It was a cool autumn day. I soaked in an old fashioned tub for a long time. The bathroom was still steamy when I stepped out of the hot soapy water. I wiped the fog from the mirror with a towel in order to shave. Staring back at me I could see a twenty-one year old boyish-looking face with blond hair and blue eyes.

In the big mirror, I could see a sheepish cock with large balls that hung down after soaking in hot water. They were swollen from lack of pussy. Madeline, my girlfriend, had run off to California two weeks earlier. Hope she has fun with the cash that she took from my stash.

I'm so horny, I thought, as I looked at my naked body in the full length mirror. My boyish cock when hard looked like a fireplug; it was three inches thick and six inches long.

I had a nice shaped ass. My hips were narrow and butt cheeks were nicely shaped and protruded not flat at all and smooth.

I got dressed in jeans (no under-shorts) and t-shirt and flannel shirt and walked down Highland toward Ponce. I liked the feel of soft jeans rubbing against my cock.

I was on my way to the diner when I decided to check out the adult book store down the street.

After entering the store I passed the chubby clerk to the back where the video booths were. I could see closet like doors. Some were closed and some cracked open. I decided to examine the infamous booths. Each booth had a preview picture of the movie within. The layouts were closet size with one or two larger.

I strolled nonchalantly by the booths, I glanced inside one and saw a man masturbating while watching a small window that cast a movie light. I could hear the movie actors groaning and moaning in passion. The man did not see me. I was chagrined and quickly moved on.

I stopped to look at the marquee pictures that demonstrated the movies. One movie in Booth 3 showed a man with a nice size cock protruding from a woman's ass hole while she smiled.

A tall dark-haired man walked up and asked me if I wanted to watch the movie together. He seemed very nice; maybe he was a salesman around 30 years old. I figured he just wanted to jerk off together.

I said yes and before I knew it, we were inside a 5X5 booth. He put several quarters in the money box and the movie started. The booth had a solitary wooden chair and a full length mirror on one wall.

We had to stand and look inside a glass window at the movie. The action was exciting as the young busty woman sucked a large cock while spit leaked out from her distended lips and drooled on her tits. Both actors moaned in sexual bliss.

We made some small talk and he said his name was Bill. My new companion was older and taller than I. His face was a little scarred from acme. He smelled nice like expensive cologne. I discovered that my new viewing companion was well endowed.

I was red faced and my cock was instantly hard while watching the movie. I noticed Bill unzipped his pants, pulled out his member and milk it slowly. I was too timid to acknowledge the act and pretended not to notice.

I was a little surprised to feel my new companion's fingers lightly stroking the outline of my very stiff cock through my jeans. The fingers outlined my penis and gently squeezed the shaft. However, I did not protest his touching; while in Rome. When I didn't object, the fingers got bolder with the squeezing.

"Why don't you take your cock out?" Bill asked.

"Hmm, Ugh yea OK," I stammered. I pulled on my belt and unbuttoned, unzipped my jeans and allowed my hard cock to feel the cool air. I noticed that my cock was harder than I expected. My cock sprang straight out at attention. He made a clucking sound and moaned in appreciation of what he saw. My nuts were real tight.

Bill turned toward me and his left hand grasped my member and started lightly squeezing and stroking. He continued working on his own prick with his right. We were both glued to the activities of the movie screen.

With his right hand, Bill took my left wrist and guided it to his semi flaccid member. It felt odd holding another man's cock but I reciprocated by squeezing and stroking. I could feel it swell and grow. I was amazed that Bill's member was so thick and long. He was a lot longer than me and much thicker too.

My finger tips did not touch its girth. Soon it was jutting straight out like a child's arm. It was at least nine or ten inches long and so very thick.

Bill reached into his pants pocket and retrieved a tube of lubricant. He squeezed some lubricant onto his right middle fingers. His slick fingers pushed between my ass cheeks and found my puckered anus. He poked and prodded at my tight nether hole. I leaned forward against the wall. The feeling was exquisite. I let out an audible moan of enjoyment.

Bill seemed happy at what he discovered was my virgin anus. He knelt down and pulled my jeans down to my ankles.

Before I could object, his mouth quickly encompassed my cock and I could feel his wet hot mouth gingerly sucking the head. He sucked expertly on my cock while my eyes viewed the woman being fucked in the ass.

He took all six inches in his mouth and throat effortlessly. His right hand pulled on my tight nut sack and coaxed the balls to loosen. He gently tugged on both balls pulling them downward. Then just as quick, he released my cock from his hot wet mouth.

After he released my aching cock, he slightly turned me so my ass was in line with his face. He spread open my ass cheeks with his thumbs and fingers. I could feel his fingers gripping each cheek so as to hold them far apart. He patiently examined my crack and its contents. He seemed to enjoy the treat that was in store.

I heard him moan in appreciation for what he saw there. I was a little apprehensive when his finger tips stroked and massaged my virgin ass hole. My hole was slick from the lube applied earlier. While pulling my left cheek apart, he began to rub my little brown hole with his slick fingers.

He helped me pull my pants off and slung them over the chair.

My cock throbbed while his slippery fingers were prodding at my little hole.

I wasn't sure I wanted him to do that but when one of his fingers managed to squeeze inside me, it felt so good that I let out a soft involuntary moan.

"Mmm, Ugh, mmm," I heard myself in total disbelief that I was actually enjoying this.

Soon he had his long fat middle finger deep inside my nether hole. His finger began a wriggling motion that massaged my prostate and caused my cock to spasm like it was cumming.

"Oh, Hmm—mm—Ugh huh ooo," I moaned.

"Here, hold your ass apart," he commanded. I used both hands to spread my ass cheeks to his close examination. He grinned approvingly at the sight of my little wrinkled rosebud stretched around his long fat finger.

"Oh, that's nice-Wow, that is tight. You got a nice tight little pussy hole," he commented.

Oh geez, did he just say pussy-hole? Oh my, I was so red faced but the feeling was so good.

I was powerless to stop him. I was on the verge of cumming. Bill wasn't satisfied with just one finger. He withdrew the digit to spit on two fingers that quickly entered my slick aching hole. His fingers stretched my tight hole but it felt so good. He began stretching the small brown orifice with two of his fat fingers.

He alternated squeezing my cock and prodding my ass with his fingers not allowing me to cum yet. I could feel the cool air on my spit drenched cock. His fingers moved inside caressing and stroking my inner rectum. Each stroke brought a spasm to my cock. He added a third digit to the campaign. Although it really stretched my nether hole, I surely did not object.

The intruding fingers in my ass caused such new sensations. I impulsively pushed my ass back onto the intrusion.

"Hmmm--Ugh—Oh, Yeah—Ugh Huh," I groaned out.

(I happened to glance at the movie to see the actor mount behind the actress and his long dangling cock directed at her brown wrinkly nether hole. Oh, I thought it was impossible for such a huge cock to ass fuck anyone. But he managed to push it through with little resistance.)

Bill didn't remove his fingers and continued to finger fuck my hot hole. It was such a great sensation. My cock felt like electricity was running through it. His face seemed pleased and fascinated as he watched closely as his long fingers snugly imbedded in my little orifice.

Each time he thrust his fingers in my hole, my cock jumped up noticeably. It was a spasm delight that felt like I was cumming.

He continued to finger fuck me for several minutes. It felt like I was about to cumm and I was concerned with where to put it.

Suddenly, Bill pulled his fingers from my achy hole. I felt him wipe his fingers on inner my ass cheek. He stood up beside his long member jutting straight out.

"Did you enjoy that?" he inquired.

"Yea, that felt good," I cried out.

Imagine how much better it's gonna' feel with my cock inside you," he smirked.

He stood behind me and reached both hands around in front under my shirt and found my nipples. He began pinching and pulling them. They were so hard and pointy. The pinching sent waves of pleasure to my hard cock. I could feel his huge member between my cheeks up to the small of my back.

Oh, I ached to feel his fingers return to my new found pussy-hole.

Then he asked me again if I had ever been fucked before and I stammered n-n-no.

I could feel Bill's enormous member on my naked thigh.

"That feel good?" Bill asked.

"Um, yea, Ugh Huh," I grunted. I assumed he meant the nipple pinching but in fact the finger fucking had felt great too.

Again he asked me. "You've never been fucked before have you," inquired Bill.

"Ugh, n-n-no," I stammered. The thought suddenly shocked my senses. My entire body was hot like a sauna.

I had wondered what it would feel like to be fucked in the ass. I had never before experienced such feelings of ecstasy with fingers up my ass.

Bill again guided my hand to his hard cock and encouraged me to stroke it. I looked closer at his extended member and was intrigued at how splendid it appeared with the slight upward curve and the purple plum-sized head.

"You want to suck my cock," Bill asked.

"Hmm, umm," and without answering, I knelt down and guided his huge member to my mouth. My lips were stretched to their fullest. I was amazed at the texture of the head and the excitement of having a cock in my mouth. My face felt flushed with the rush of blood.

He guided both my hands to grasp the shaft and stroke while he held my head. Bill's cock was more than two hands long by at least one hand. He was so thick that my finger tips did not touch.

His cock was noticeably thicker just past the head at the shoulder and thicker still at the base. I noticed two sizeable hairy balls that hung several inches below. He held my head and began a thrusting motion back and forth in my extended mouth.

"Use your tongue and try to swallow it," he instructed.

At first I gagged several times when Bill urged his member past my tongue. Several strange minutes passed until the heart shaped bulb pushed past my tongue and he pushed and pulled on my head. I was able to take several inches down my throat. The loss of air and gagging was a new sensual awakening.

My cock ached with passion. It strained at attention like never before. My nuts were blue in anticipation.

Bill pulled his spit drenched cock from my mouth. I was helped up and slightly turned so that my ass was in direct contact with his dripping wet member. Bill used his left hand to separate my ass cheeks and used the right to guide his long cock to my puckered brown hole.

He seemed impatient with the effort. I guess he wanted to fuck me before I changed my mind. I felt his soft cock-head at my nether entrance. Bill pushed the head attempting to penetrate my tight little hole.

"Spread your legs apart a little, now bend over a little-hold it there-here hold your ass open like this," Bill said as he instructed me again to pull apart my own ass cheeks with both hands.

He said he would go slow and stop if it hurt. I only nodded my approval. I felt some assurance that he would stop if it was painful.

He grabbed his cock again. It was so long and thick. I was just a little apprehensive about the work at hand but my curiosity was stronger.

His cock was wet from my spit. I watched as he applied more lube to the head of his cock.

I looked over in the mirror and there I was slightly bent over holding the cheeks of my ass open for his pleasure. I spread my feet apart and bend over my ass facing him. I could see him in the mirror holding his enormous member like the arm of a large child

He held his cock with his right hand as it nudged inside my cheeks and his left finger guided the head to my tight hole. It was then I feared because his member was so big.

My bung hole was itchy and really wanted more of his fingers inside me. I anticipated a painful entry but his soft cock-head massaged my anus as it prodded and it felt good when it finally popped inside. He repeated the entry many times. The prodding in and out was maddening for my hungry nether hole.

Finally the large bulbous head aligned with my puckered anus. After a brief struggle the head again suddenly popped inside the slick entrance with no resistance. My anal lips opened and snapped securely around the head. There was some full discomfort but no real pain. I guessed that his fingers loosened the entrance.

"Aww—Bill moaned. That's good isn't it," he inquired.

"Umm-Hmm," I moaned in agreement.

He reached around with his left hand squeezed my hard cock once. With just the head snugly lodged in my ass ring, my ass began to pump back against his cock. With his left hand he gently slapped my nuts twice. There was an instant inner pain reaction.

"Ughh, oh shit," I replied in some discomfort.

I was so hungry to engulf the rest of his hard cock. I wanted to satisfy my new found hunger for anal pleasure.

All of a sudden, his cock popped inside my sphincter stretching my virgin hole. The sudden penetration of the shoulder of his cock ripped through me like a knife.

"Ouch, Owie, Humph," I cried. "It's too big," I complained.

"No it isn't. Just breath and relax. You like it," encouraged Bill.

I cried out again but he had already pulled back in anticipation and with just the soft head of his cock still lodged inside the entrance to my aching hole. My legs quivered and my cock was still raging hard.

The biting pain ebbed and soon I was pumping back onto his cock again eager to fill my hungry hole.

We repeated this action several more times until finally I was pushing back on his cock when two inches of hard fat cock entered my rectum.

This time it didn't hurt and my rectum had an unusual full feeling that I could tell it was pleasant. My body felt really hot. Tears rolled down my cheeks as I experienced the first of many ass fuckings.

My cock throbbed with a new incredible feeling. It felt like cum was spewing from my cock but not ejaculating. I bent slightly at the waist and saw my cock ooze with pre cum in a long dangling string.

Bill slowly pulled his cock back and forth like a piston drilling a little deeper each time. His thick member gained more depth. My rectum felt totally stuffed and my anal lips were stretched completely. Gradually more of his huge cock gained entrance into my nether hole. I could feel his huge cock in my innards.

Oh but he was right. His hard cock felt so much better than his fingers. I could feel the tingling in my cock and my rectum that was stretched sore to its fullest.

"You got half my cock in your ass—it's good isn't it," he stated.

I reached back in disbelief and grasped his cock and then I knew that at least half his cock was inside me.

"Oh, wow, it's so big. Oh go slowly it feels good now," I groaned.

I continued to hold his cock directing it in my ass; pumping my ass against it. Each time his cock poked a little deeper inside my rectum, my cock would spasm in delight.

I glanced at the side wall mirror aghast at the sight. Bill's huge cock was half way up my ass. Seeing the vision of myself slightly bent over with my small ass jutting out while that monster slowly plowed in and out was delicious.

"Oh, ugh, my gawd, o my, yea, hmmm," I uttered gibberish as Bill fucked me deeper.

I pushed back in unison as he labored to fuck my ass. I could hear him grunt and moan so it must have felt good. He fucked me for a good while and I couldn't take my eyes off the reflection in the mirror, the union of cock and ass. His huge white cock was so deep inside my rectum.

He began very slowly plowing a little bit at a time in and out of my ass deeper and deeper. It felt like he was moving one inch back and forth sort of teasing my rectum.

As my new friend slowly fucked me with his big cock, my ass met his strokes.

Suddenly he grabbed my hips and urged his long cock for more penetration. I was standing on my tip toes as his cock pushed against my inner bowels.

Gradually, I felt my bowel give way and his entire huge cock was buried to the balls against my ass cheeks. I could feel his soft pubic hairs tickle my cheeks.

He released my hips and rubbed my nipples through my t-shirt then reached underneath and pinched my nipples hard and pulled on them. I glanced down thinking my cock was cumming but only saw a long string of pre-cum dangling. It was the beginning of a blissful journey of orgasmic delight.

I could feel my prostate pulsing and my colon spasm and milk his cock. We stood there for what seemed a long time. My butt rubbed his pelvis with my rectum totally stuffed with cock.

I let out a loud oomph and breath. It hurt a little but I was powerless to stop the onslaught of battering my innards with his hard cock.

His left hand released my left nipple and grasped my cock slick from the oozing pre-cumm. I was gyrating in blissful pleasure oblivious of the sights and sounds around me.

He released my other nipple from the delicious pinching, grabbed my hips and began to slowly pound his massive cock in and out of my stretched anus. Again, I heard the plopping noise his hips made when contacting my ass but I was lost to the oblivion of orgasmic delight. The fucking lasted maybe four or five minutes.

I was about ready to explode. The feeling of his hard cock in my ass, my ass pumping back and forth on his cock put me in orbit.

He started pounding my ass-slap, slap, slap-over and over-pulling almost all the way out and re-entering deep in my rectum. The pounding lasted less than a minute more and my cock launched into orbit.

"Oh Gawd YES I AM CUM—MING," I cried out in such passion. Each stroke caused my cock to spurt a jet of cumm. I was suspended in anal orgasm. My nuts felt like they were in a squeezed in a vice.

I began to want him to stop when after a few more strokes of hard pounding inside me and my cock was dry spurting, when he started to grunt and I could feel him cum deep inside me.

"Oh Oh, Yea yea mmff mmff," he exclaimed loudly as he came voraciously deep inside my bowels.

I could feel his cock throb as he came inside me. He pushed all the way as deep as possible and I could feel his warm cum squirting and filling my bowels.

We just stood there for several minutes with his hard cock still buried deep in my ass and my cock still hard and my nuts sore from spurting so much. I could feel my ass spasm trying to push his tool from my now aching rectum.

The booth had some paper towels like in the gas station bathrooms. He snatched some. His cock eased out with a plop. Bill then wiped his still erect cock. Then he applied the used towel between my ass cheeks just in time as the hot cum farted out.

wiley4377
wiley4377
184 Followers
12