Anal Peep Show

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Young man discovers anal sex for the first time.
10.2k words
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wiley4377
wiley4377
184 Followers

PEEP SHOW XXX

***It is not recommended to have unprotected sex with first time partners. I was first fascinated at a book with a variety of pictures of men fucking men and women. The anal intercourse was especially arousing.***

It started when I was 19 and for the next five years, I enjoyed anal intercourse with several men. Two men were regular visitors to my apartment over the garage of my parent's home. I measured Bill's cock at 11 inches long and 3 ½ inched wide. George was 10 inches and slightly thicker than Bill's.

Both parents worked until eight or nine each night except weekends. Bill and George visited almost daily between four and six. I had a part time job on weekends.

I liked the sex so much that I installed several large mirrors on the walls so I could enhance the experience.

Here is my story.

Chapter 1

Oh Bill, the Anal Training.

I had no idea that this was the day that my sexual world and desires would be so altered and perverted. Although the male to male anal sex is considered taboo, the intense attraction and satisfaction is undeniably satisfying.

It was a cool autumn day. I soaked in an old fashioned bath tub filled with hot steamy water. The bathroom was still steamy when I stepped out.

I wiped the fog from the mirror with a towel in order to shave. Staring back at me I could see a 19 year-old boyish 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.

I'm so horny, I thought, as I looked at my naked body in the full length mirror. My 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.

My cock was semi hard. I took a hand mirror and examined between my legs. I studied that crinkly shaped anus. With a little Vaseline, I poked until my middle finger squeezed inside. I experimented frequently with poking my ass.

The feeling was electric. Oh, this feels good. I heard other guys giggle about corn-holing but I was too shy to try it myself.

I got dressed in jeans (no under-shorts) and t-shirt and flannel shirt and walked down the street. My cock stirred at 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 saw books and videos and a glass counter where a chubby clerk was reading a book. The counter contained what appeared to be plastic dildoes of various sizes.

I walked past the 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 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 dimly lit 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 the far 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 soon 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. I was mesmerized at his hanging member.

I stared at it in fascination. The site of his flaccid member thrilled me as much as the first time I saw a pussy.

Even flaccid, it was at least seven or eight inches and very fat.

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 swollen and tight.

Bill turned toward me and his left hand grasped my member and started lightly squeezing and stroking. I could feel his flaccid cock bump and rub against my left hip. We were both glued to the activities of the movie screen

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 at the size of Bill's enormous cock. His member was so thick and long. It was twice as long as mine and a much thicker too. My finger tips did not touch as I squeezed and frigged his cock. It was at least 3 inches thick.

His cock skin worked effortlessly over the large plum-sized head. I was awed at its thickness and weight. There was an excitement brewing in my groin as I frigged this huge penis.

Soon it was jutting straight out like a child's arm. It was at least ten or eleven inches long and oh-my, it was so very thick.

I noticed my palm was oily from his pre cumm so I incorporated the greasy substance with my palm.

We just stood there side by side frigging each other watching the screen.

I frigged his member paying careful attention to the very large plum sized head. My grip was firm and oily as I frigged over the shaft and head.

The frigging caused my host some considerable pleasure as he moaned out loud. The moaning caused me some concern of being over-heard. But it did not seem to bother him and he showed his appreciation with his right hand between my ass cheeks.

Bill spit on his fingers. His long fat fingers pushed between my ass cheeks and found my puckered anus. I leaned against the wall as my ass pushed up for easier access to my anus.

I let his cock go and it swung like a pendulum.

I was mesmerized watching it dangle.

Bill poked and prodded at my tight nether hole. The feeling was exquisite. I let out an audible moan of enjoyment.

"Oh, awe, umm," I moaned.

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.

"Awwwwgh, hmm," I gasped out in sheer pleasure.

"Hmm," 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 thick inches 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. I could feel the cool air on my spit soaked cock.

After he released my aching cock, he slightly turned me so my ass was in line with his face.

He spread my ass cheeks with his thumbs and fingers. I could feel his fingers gripping each cheek to spread them far apart.

There was a full length mirror on the wall. I watched as he examined my ass crack and its content in the dim light. In the mirror, his face showed passion that he enjoyed the treat that was in store.

What Bill saw was a small virgin ass hole. He must have been ecstatic because what happened next was never on my menu of planned sex.

I heard him moan in appreciation. I was a little apprehensive when suddenly his face was between my ass cheeks. I could feel his five o'clock whiskers on my soft inner butt cheeks.

Bill used his tongue like a small penis to slightly penetrate my anus lips. He licked and probed with his tongue causing a shudder in my groin and erect penis.

"Oh my gawd, Hmmm, Ugh huh," I groaned out not caring who heard it.

Then suddenly he pushed his finger tips at my virgin ass hole. My hole was slick from his spit. While pulling my left cheek apart, he began to dig his long fat middle finger up my rectum.

I could feel a jolt of pleasure as my prostate responded by a noticeable spasm of my cock.

"Oooo, yeah, awwgh," I moaned.

He helped me pull my pants off and slung them over the chair. Now my ass was fully exposed to his invading fingers.

I glanced in the mirror and saw myself slightly bent over with one arm for support against the wall. My cock throbbed as his slippery fingers were prodding at my little hole.

"Mmm, Ugh, awww," I heard myself moan. I was actually enjoying this. The feeling was exquisite.

Soon he had two long fat fingers up to the knuckle inside my ass. 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 oh," I moaned out loud continuously.

I could not help myself. I pushed my ass back and forth involuntarily.

"Here, hold your ass apart," he commanded. I was slightly bent over at the waist and my ass was proudly protruding at Bill's face. With my left shoulder against the wall,

I used both hands to spread my ass cheeks to his close examination.

In the mirror I could see that 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?

I was extremely red faced but the feeling was so good that I did not object.

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. The intrusion was strange but not painful.

His fingers stretched my tight hole but it felt so good. He began stretching the small brown orifice with his long fat fingers.

He alternated frigging my cock, pulling on my nut sack 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 inside of me 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.

With one or two pushes, his fingers were in up to his knuckles. The intruding fingers in my ass caused such new sensations.

I impulsively pushed my ass back onto the intrusion. He pumped his fingers in rapidly filling my cock with a steady stream of nerve pulses.

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

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.

He stood-up behind me and reached both hands around in front under my shirt and found my nipples. He began pinching and pulling them with his greasy fingers. They were so hard and pointy.

I could feel his hard erect cock between my legs poking at my nut sack.

The nipple pinching sent waves of pleasure to my hard cock.

I closed my legs grasping his huge member with my inner thighs as his cock poked between my legs at my balls

He pulled his cock up and I could feel his huge member between my ass-crack up to the small of my back.

Imagine how much better it's gonna' feel with my cock inside you," he smirked as he pushed his cock between my clinched ass cheeks.

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 between butt cheeks. I was somewhat apprehensive as to the outcome of being fucked in the ass by such a huge cock.

"Um, yea, Ugh Huh," I agreed.

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

"Ugh, n-no," I stammered again. 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.

He moved to my side with that enormous member against my left thigh.

As we stood there I held that enormous monster with my left hand.

Bill confided that it would hurt a little at first until I got used to it.

"It will take some getting used to but when I am inside you will love it," he said. The words were of some comfort to expect the reward of a pleasurable experience that I never knew about.

Bill again guided my left hand to his hard cock and encouraged me to stroke it.

I looked close 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 soft subtle texture of the head and the excitement of having a cock in my mouth. My face felt flushed with the rush of blood.

My jaw was extended as far as possible. My lips were stretched around the shaft. My jaw was stretched to the limit.

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.

My nostrils flared as I tongued the huge cock head.

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.

When the cock head opened my throat and cut off my ability to breath.

"Gawk-gawk-gawk," as his cock face fucked my throat. My throat was suddenly choked and stretched by the invading monster.

I was able to take several inches down my throat. The loss of air and gagging was a new sensual awakening.

"Cawk-gock-gock-gock," was the sound of my throat being fucked.

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

Suddenly, Bill pulled his spit drenched cock from my mouth.

I took a deep breath and felt a little feint.

I was helped up and slightly turned so that my ass was in direct contact with his dripping wet member.

From his pants pocket, he retrieved a tube of some type of lubricant. He squeezed a generous portion on his finger and applied to my nether hole and rubbed it inside my anal lips.

Bill used his left hand to separate my ass cheeks and used the right to guide his long cock to my puckered brown hole.

I instinctly bent slightly offering my ass to his member.

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-now-hold your ass open like before," Bill said as he instructed me again to pull apart my own ass cheeks with both hands.

My face and chest were pressed against the wall. I could see our bodies in the wall mirror just adjacent.

What a sight, my naked body leaning against the wall with both hands holding my ass cheeks apart. My pussy hole was eager.

My ass was pushed outward and slightly up. My face and chest were pressed against the wall close to the viewing window.

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 admit that I was afraid at first and apprehensive about the work at hand but my curiosity was stronger.

His cock was spit lubricated. I watched as he applied some more lube to my asshole and slipped a finger inside.

"Hmmm, yes," I moaned.

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 bent 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 was afraid because his member was so big. The plum sixed head abutted my puckered orifice.

When the head connected and pushed, my whole anus was pushed in a little.

My bung hole was itchy and really wanted more of his fingers inside me. Finally the large bulbous head aligned with the porch of my puckered anus.

I anticipated a painful entry but his soft cock-head massaged my anus as it prodded and stretched.

After a brief struggle the head suddenly popped inside the slick entrance with no resistance. My buttery smooth anus engulfed it.

"Oh shit that's so big," I exclaimed.

My anal lips snapped securely around the head. There was some full discomfort but no real pain. I guessed that his fingers loosened the entrance. He repeated the entry many times.

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

"Umm-Hmm," I moaned in agreement.

"Take a deep breath, it will hurt a little," he warned.

He reached around with his left hand squeezed my hard cock. 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 ball sack. There was an instant inner groin pain reaction.

"Ughh, oh shit, oh fuck, it hurts" I replied in some discomfort. My inner balls were enflamed.

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

wiley4377
wiley4377
184 Followers