First Time Anal

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I do not claim to be a grammar expert and as such you will find some grammatical errors in this story.  The errors can be the switching of tense, spelling errors, or typos.  I ask if you find an error please send me an email so I can correct and make the story enjoyable for others.



This text file contains sexually explicit

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First time anal

Each person remembers their first time for the major events in their lives such as going to school, their first date, first kiss and when they lost their cherry.

Most people are conditioned to have normal sex. They are not willing to explore all the possibilities for sexual pleasure.  For the more adventurous anal sex can be enjoyable for both the person receiving (bottom) and giving (top).  The results of sex studies have reported only a few men have had experienced the pain and pleasure receiving anal intercourse.

One sex study reported eleven percent of men aged 20-24 said they took part in of sodomy.  The number declines in the next higher age bracket,  then steadily rises in succeeding brackets, leveling off at nine percent among men in their 40s and 50s.

I had my initial bisexual meeting when I was forty-three. My first anal intercourse happened in 2001 when I was fifty-one.  In my early days of being bisexual, I only met men to receive head.  After three years of one-way oral sex, I wished the experience of giving fellatio to a man. It took me eight years to go from the receiver of oral pleasure to the receiver of anal intercourse.  This happened by accident when I met a stranger named Carl.  We became friends, and he helped changed my life.

I met Carl online.   I would post messages to various Yahoo groups to find strangers to meet for anonymous sex. Carl responded with an X-rated picture of him and a statement of why he would like to meet me.  One reason I agreed to meet Carl was he lived close by, less than two miles.  Carl and I met a few times where I gave him oral.  He liked lying back and having his cock and balls sucked.  I like giving men oral pleasure.  We meet when Carl was horny about one a week.

The next time Carl called he said, “My girlfriend would like to watch two men go to it.  She will not share but wants to watch.  Are you interested?”

At first, I did not know what to say. Gathering my thought, I questioned Carl, “Go to it?”

Carl replies, “You know what we did a few days ago. She is hot to want to watch me and another man.”

“Sure, sounds exciting to me.  I love spectators.” I boasted.

Carl and I discussed the time to meet and found our schedule worked to meet the next night.  I parked in front of Carl’s apartment in the label visitor’s parking space. I am fresh out of the shower dressed in my work clothes, slacks and dress shirt.



Carl meets me at the door with a beer and welcomes me into his apartment.  As I entered a tall blond woman approached.  I shook her hand and say I am Roger at the same time she says she is Mary.  We smile as we sit on the couch.  We start conversing about our jobs, how we ended in this town and other polite topics. We chatted about how it was convenient to live near the beach, how we met Carl.  Mary stated, “Carl and I have been dating for a year.”

I replied “Oh that is great.” I was at a loss for words.

Mary continues with no sign of embarrassment in her voice, “Carl told me about you sucking his cock, and it got me so excited I had to see for me.  So I asked Carl if you could do that again.”

Flattered by her words and with a pride in my voice, I said, “I love to.”

Carl chimes in, “Let’s go to my bedroom where we will have more room.”

We walked to Carl’s bedroom, Carl leading Mary and Mary leading me by the hand.  Carl’s bedroom had a king-sized bed and plenty of room; I noticed the sheets turned down and there was a chair next to the bed.  Mary announced, “I want to watch so I will be sitting here,” as she waved over to the chair. She said, “I want to have a pleasant view as you two put an excellent show on for me.”

Carl removes his clothes. I started to take off my clothes while Mary sat in the chair watching. Carl and I jumped onto his bed naked.  Carl’s girlfriend remained fully clothed ready to watch two men go at it.  I lie down next to Carl, and because this is his show let him lead the way.  Side by side, Carl started to kiss my neck, then my ear and ended kissing my mouth.  In our past meetings, Carl and I did not make out, and his kissing caught me off guard.  I made out with one man in my past, now for the second time I was making out another man. Carl held my head in his hands; his lips firmly pressed to mine.  His tongue darted out, and I naturally open my mouth to accept.  Carl was passionately Frenching my mouth.

Carl’s moved one hand from my neck but keeps constant pressure as he continues to kiss my mouth.  Carl’s other hand moved to my breast as he fondles my nipple.  He played with one nipple then the other.  I never had anyone play with my nipples before.  My nipples responded to Carl’s touch by getting hard.  Carl continues to rub, pinch, squeeze, my nipple resulting in a stimulation sensation from my nipple to the tip of my cock.  Oh, what pleasure Carl was giving me.

With Carl kissing me and playing with my nipples, I was not sure was Carl trying to seduce me? I was not sure what Carl would do next. I decided to follow Carl’s lead, he was playing with my tits, and I would play his.  Both of my hands were available to explore Carl’s body.  My hands went to his hairy chest, finding his nipples. My fingertips applied the same pressure and motion to Carl’s tits as Carl was doing to my tits.  I wondered, were these as much a turn-on for Carl as it was for me?  My nipples were hard; I was hard, there is a different connection between my tits and my cock was adding to the passion.

I was on my back lying on the bed; Carl was on top of me, partially kneeling and bending over so he could kiss my lips passionately, then suck on my nipples.  Sitting in a chair, Mary watched.  Mary was quiet that I had forgotten that she was there.

Carl moved to sit on my chest allowing him to move forward placing his cock on my lips.  I know what Carl wants an open my mouth.  Carl slides forward as I curled my lips over my teeth allowing his cock to slide over my lips. Carl’s cock entered my warm, wet mouth as I am still fondling his tits with my hands.  Mary watches me licking, sucking, kissing, his cock while Carl starts fucking my mouth.

After a few minutes, Carl moved to the sixty-nine position.  With Carl on top, I could not see, but could feel his mouth sucking my cock.  Carl raised his hips moved from my face and lowered his cock into my waiting mouth.  Carl now can slide his cock deeper into my mouth, enjoying that more than half his cock was in my mouth.  I use my tongue to tickle the head of Carl’s cock; each time he pauses, gives me a second to tickle him in all the right places.

After a few minutes, Carl removes his cock from my mouth and moves his hips, so his ass is inches away from my mouth.  Carl had showered and was clean. I lift my head contacting his hole.    I did not mind rimming a clean man.  Mary stands leaning over to get a better view.  I felt her presence as Carl, and I played.

Carl moved again as if his actions were directed and the positions scripted. He rolled me over onto my stomach.  Carl now kneels at my head causing me to turn me head to face him.  I took his cock into my mouth allowing him to use his hips to fuck my mouth.  Carl reached down with his hands rubbing my cheeks.  As he rubbed my cheeks, a finger finds my crack then my hole.  I was tight, and he could not penetration deeper. Mary moved to the bedside table, pulls out a tube of lubricant.  I continue sucking Carl’s cock thinking I knew what was going to happen next.

Mary places some lubricate onto Carl’s hand then Carl’s spread the lubrication between my crack, putting lubricate on and in my hole.  Carl’s finger now could enter and probe deeper into my rectum.  I felt no pain, but his finger felt uncomfortable because I had had man’s finger in my ass. Except for doctor, this was the first time I had had man’s fingering my ass.  Carl seemed to enjoy fingering my ass after some probing Carl placed two fingers inside me reaching my prostate. Carl finger inside my rectum placed cad pressure at the correct location resulting in, I pre-cum leaking   from my peep hole. Mary was standing in a position where she can sees everything happening, me sucking Carl’s cock and Carla finger fucking my ass.  My pre-cum was dripping on the bed sheets.

I began to enjoy the prostate massage, but I realized what was coming next.  Was I ready for this? Carl applied more lubricant.  Am I ready to have a man enter my backside?  I read that anal sex is painful and that if not done right could do some damage.  I was committed, did not want to say no to Mary’s fantasy, watching two men.

Carl changed positions moving behind me.  I was still on my stomach as Carl spread my legs kneeling between them.  He pulls on my hips to position me for what is coming next.  Carl’s hands were on either side of my body supporting his weight.  I could feel Carl’s legs next to mine.  I wondered whether Carl planned to fuck me that first time we met.  Maybe he came too soon and now to meet me again he had used the excuse that his girlfriend wanted to watch. I am naked face down, butt up with my legs apart and my ass hole exposed for all to see.  In this position, I could not move. I wondered if it was turn-on for Carl knowing a man was surrounding to his will.  At this point, I could look back and see Mary lying on the bed, reaching out for Carl’s cock.  I realized that she was guiding his cock to line up with my hole; I was going to be fucked by a man.  I have read about anal sex, this was going to hurt, and my body tensed.

Carl’s cock head pushed against my hole and did not enter.  He tried again; I can feel his hardness against my hole, but I was tight, a virgin and not sure what I needed to do. Carl was in the top position, in command.

I heard Mary’s voice saying to me, “Relax,” I did.  She guided Carls’s cock again as Carl pushed forward.  I felt him now as he pushed past my anal Sphincter.  I felt some pain, or at least I thought it was a pain.  Mary continued to guide Carl’s cock and reminded me to relax.  Carl kept a constant pressure forward, and the sound of Mary’s voice was reassuring; the lubricate also helped.  It started to hurt now, I said so, and Carl stopped as he pulled out a little and stopped.  The pain subsided, being replaced with feeling of pleasure.  The same pleasure, as when Carl had his two fingers in my ass messaging my prostate.

I knew that Carl was larger than the average man.  My concern was I able to take all of him into my hole.  Carl was patient, between my cries about the pain then saying, “OK it is better now”, he inched his way in until he stopped.  He started to use his pelvic to thrust his cock far deep in me then so he can push far in again.

I could feel both Sphincter muscles grab Carl’s cock tightly and holding him firmly as his cock slid past my Sphincter muscles.  I knew that Carl felt me as tight and warm.   Carl’s hard cock penetrated my rectum caused me to be involuntary react by setting up rhythmic contractions, causing a “massaging” sensation along the shaft of the penis.

I could feel my climax building up; I was going to cum and could do nothing to stop it.  I was no longer in control of my body and resigned to let it happen.  I let out a cry or shout, “I am cumming.”  With that, my body contracted, I jerked uncontrollably.  My Sphincter muscles got tight, cum oozed out of my pee hole; I have a wave of extreme joy, of well-being. Carl plunged his cock deep into my bowel he grabbed my hips saying, “Oh shit I cumming.  I am going to cum in your ass.”

With that, I felt a flood of warmness in me; the jerking of his cock deep inside me, his moans of joy as man cums. His body falls on top of me.  He was heavy but not too heavy; his mouth was near my ear; I felt his breath, heard his exhaustion as Carl whispers, “Wow Roger; you have a tight ass, and was a hot fuck.”  Mary sat back in the chair; I looked at her; I had a smile on my face, and so did she.

My ass contrasted like having a bowel movement; Carl’s cock squeezed out, and I hope there is no mess.  I do not want to smell or see any crap.  I feel the wetness between my legs and figure it was Carl’s cum leaking from of my hole.

Carl rolled off of me, grab a towel, cleans his cock of cum, and lucky there was no brown stuff.  He gave me the towel as he heads to the shower.  I lay there trying to clean the creamy mess between my legs. I remembered feeling like being used, like a warm place for Carl to put his cock and cum.  Feeling his cum in me was a different feeling and not unpleasant.   I think I liked it; I like being on the bottom and having the man do the fucking.  I liked fucking while I was the passive participant.

Carl finished showering then I took a quick shower, got dressed and returned to the living room where, Mary and Carl were sitting on the couch.  I entered the living room with a smile on my face.  Mary asked, “How was that?  Did you enjoy Carl’s cock in you?”

I responded, “It was an experience.  It hurt at first.  However, with Mary’s help I relax. I would have never realized that all of Carl’s cock would fit.”  Sitting in the chair I could still feel Carl’s cock deep inside me cumming.  Mary and I were comparing notes about Carl’s cock and how it felt being fucked by him.  I think Carl was a little embarrassing about the conservation.

After that first time of having anal sex, I was addicted to being a submissive bottom.  I met Carl several more times, but he did not fuck me again.  What Carl did when we met is another story.

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