Bottoming with My Mentor Pt. 02

Once again, this story is entirely fictional. Names are changed.

*****

It had been over a decade since I last saw Fred because of a falling out due to a miscommunication.

Not long after our intimate experience together, he had tried to contact me to hang out casually but I was indisposed and couldn't meet up. He took this as a slight, like I was blowing him off or something, and he never called me again...

...Until recently. Over a decade later, I'd been in some decent relationships with women, but then that need came creeping back to the forefront from deep within my subconscious; the need to bottom with a man who was superior to me in some way.

As I stated before, I had been dating women and having heterosexual sex, even anal sex with some of them and thus fulfilling that aspect of my anal fetish; the absolute joy in seeing and feeling my cock buried up a woman's ass. Knowing that she was willing to surrender that most intimate of places in herself to me, her submission of mind and body, and the simple visual beauty of her asshole wrapped around my shaft was absolutely heavenly. I attempted anal sex with all of them, and some of them relented. Of those that did, some liked it, some loved it, and some LEARNED to like it, but none of them hated it.

I could never tell them though, that I knew exactly how they were feeling at that moment when they had my cock buried in their rectums.

See, whenever I notice a big juicy ass on a woman, I immediately imagine what anal sex with her would be like. I'm ATTRACTED to women and especially their beautiful posteriors. It is a triumph of nature which consumes me in my desire for the opposite sex.

That being said, every so often...I need to bottom to a man. I have no attraction to men whatsoever, the male form doesn't arouse me, in fact, the very idea of sensual activity (kissing, oral pleasure) with another man repulses me,

FUCK, it just felt SO GOOD when Fred topped me though! Having that warm cock up my asshole and knowing that he was better than I was, mentally and physically, fulfilled this deep dark need in the very core of my being that I barely knew existed.

Such sweet SURRENDER! Such exquisite SUBMISSION...

So recently I noticed that my sexual needs kept going back to the last time Fred and I had sex and how attentive he was to prepping my mind and my asshole before penetrating it, so I decided to try my luck with reestablishing communication with him.

I was newly single due to my recent breakup with my last girlfriend, so I was free to visit the hospital during a week that I had taken off and I ran into him in the hallway.

It took him a second to recognize me, then he stood with his arms crossed and asked me what brought me back to Lewis Memorial. We were alone in the hallway so I just looked at him and told him that I had "pleasant memories" of my time spent there, and gave him a sideways glance.

He raised his eyebrows in surprise and asked me what I was hinting at, so I just shrugged and asked him if he wanted to catch up after he got out of work. He looked around to make sure nobody was around before quietly asking me if I remember where he lived. I nodded and then he just said "7 o'clock" and walked away.

I then went home and showered, then ate a quick dinner before heading across town to his apartment. I buzzed his door at exactly 7 because I knew how important punctuality and promptness were to him, but it took a minute before the door buzzed me in.

I was having flashbacks from the first time I visited him In addition to some nervous anticipation because I had no idea what he had in store for me. Then I got to his door and rang the bell and again I found myself waiting for a minute before the locks turned and he opened the door to his dark apartment. To my surprise, he pulled me in by my arm and closed the door behind me.

He pulled me into his livingroom and made me sit on his couch, and he asked me why he should even consider talking to me again after I blew him off all those years ago. I told him to sit down and relax, and then I calmly explained why I couldn't hang out with him that day and that I really was preoccupied and that he took it the wrong way. I said that I was sorry that I made him feel that way because the memories of our time spent together, both socially and intimately, were fond ones and I just wanted to clear the air with him and start over.

He sat there silently for a minute before nodding and saying "ok...ok" and then I stick out my hand which he shook and we both got up. Then he smiled and asked me with a sideways glance if I wanted to stay and hang out for a bit, to which I nodded and asked him if he had anything to drink. He then strode into the kitchen swaying his hips happily as he did, and returned with a couple of glasses and a bottle of scotch.

We toasted , sipped our drinks, and talked about old times at Lewis Memorial for a little while until he decided to get up and put some soft opera music on. Then he sat down right next to me, put his hand on my thigh, and asked me if I remembered anything else about him fondly.

I put my hand on his and told him that our little tryst had opened my mind to the fact that bottoming was extremely pleasurable, but only if the man was physically or intellectually superior to me. I went on to say that although I loved bottoming, I still didn't like kissing or oral sex because I just wasn't attracted to men.

Then I playfully wagged my finger at him and told him that it was all because of what he did to me that day over a decade ago. He smirked and rolled his eyes with embarrassment, but then stood up and held out his hand for me to stand up also.

He called me a flatterer while holding my hand and then I saw the bulge in his shorts. He caught me looking, then asked me if I was interested in getting reacquainted with what I was staring at, and that he was interested in seeing if we could recapture the magic of that first time together.

I smiled coyly and said "I thought you'd never ask..but I'm still not kissing you or sucking your dick!!" He just shrugged and nodded impatiently, then pulled me by my hand into his bedroom.

He closed the door and we were alone in that familiar room which was dimly lit and warm and smelled like clean laundry. My stomach was fluttering from that old familiar nervous anticipation and when he started pulling down his shorts, he revealed his wobbling erection, and I saw that he still had that nest of black pubic hair.

Then he stood nude and flexed his muscles in front of me and chuckled and asked me "is this what you mean by physically superior?" I told him he did look great for his age and then I began to take my clothes off.

Though because of my nerves, my penis was shrunken which made me blush with embarrassment, but he just chuckled again and shrugged his shoulders. Then stepped towards me and gently pinched the head with his warm fingers and tugged on it, stretching the shaft which lengthened it a bit.

He raised his eyebrows and said "there see? I knew it was just nerves.." then he ran his hand over my naked chest and belly and cupped my balls and penis in his hand for a moment before running his hand around my waist.

It was at that moment when I realized that I had to prep myself first, so I told him to hold on a second and he gave me a confused look and said "ookkkk..." Then I hurried into the bathroom and cleaned my ass out as best and as quickly as I could.

When I dried off and came back to the room, he was slowly pacing back and forth with his arms crossed and his erection had subsided. He said "thanks for cleaning up first, but now look what you did?!" Then with mock anger, he took my shoulder and roughly turned me around and spanked my ass like he did back in Lewis Memorial that day.

It made a loud cracking noise and I gasped and jumped because I didn't expect it, but then just as I was about to turn around indignantly, I felt his hand slide between my damp cheeks and he began rubbing up and down my crack.

Then he quietly told me to bend over and put my hands on the bed, and I felt the blood go to my ears as I assumed the position. The room got quiet and I waited for what was going to happen next.

I heard that little drawer open and I knew he was taking out the bottle of lube and a condom. Then I heard him pop open the lube, and a second later I felt his finger and thumb spreading my cheeks, followed by the cool gooey fluid running down my crack which made me gasp softly and clench my cheeks reflexively.

Then as he stood behind me, I felt his finger begin to smear the lube around my anus, massaging it into the soft wrinkled pucker. It felt really good and I moaned and began to arch my back and thrust out my hips, which naturally spread my cheeks a bit.

He took this as a sign that I wanted him to keep going, so reached back and spread my cheeks apart for him, and then I gasped softly as I felt him worm his lubed finger up my asshole. I knew how to relax myself by that point so it slid in easily, and he murmured "ohHo! So you learned how to relax, eh? Ok..."

He worked his finger in and out of my asshole and I just leaned my knees against the edge of the bed and kept my hands planted on the mattress, and I began breathing deeply in response to his probing finger. He muttered "hmmm there you go, can you take another finger?" I nodded and grunted as I felt my anus stretch around his second finger, and I stiffened a bit at first but he kept pushing in slowly and firmly.

I felt his knuckles pressing against the outside of my asshole and I knew he had his fingers as deep up my ass as he could get them. Then he began massaging the walls of my anal canal and worked it until I felt my sphincter get soft and I heard the moistness of his fingers churning inside my ass. He twisted his fingers and pressed down on my prostate and asked me how it felt to which I replied "oh my god so good..."

Then just like that, he pulled his fingers out of my ass with a wet slurp that made me grunt and jump slightly. He lightly slapped my ass again and urged me to climb on the bed, hand on my ass guiding me forward.

The bed creaked slightly as I climbed onto the bed, following his lead as he manually maneuvered my hips until we settled into position for mounting me. I was now in the middle of the bed on all fours with my knees splayed wide and my hands shoulder width apart, supporting my upper body. This had the effect of naturally tilting my hips up so that my anus was exposed and my balls and penis dangled between my thighs.

My ass was being offered and made available to him in this position and I felt very submissive and vulnerable at that moment, but I also felt my whole body tingling in the warm air of the bedroom in anticipation of the sodomy that we were about to commit.

I felt the bed shift as he crawled up behind me and settled his knees between mine, then I heard the condom wrapper rip open and after a second or two he squeezed a little bit more lube onto my waiting asshole. I breathed through my mouth and looked over my shoulder as I felt the lube run down around my balls. It made my butthole feel cold, gooey, and exposed for a moment until he got into position when I sensed the comforting warmth of his body against the back of my thighs and asscheeks.

He held my hip steady with one hand while with the other, he tapped my asshole with the head of his penis before dragging it up and down my spread open asscrack.

When he finally pressed the head into the pit of my anus, I immediately felt it's blunt warmth and found myself thrusting my hips out and arching my back in eagerness. I hung my head, opened my mouth and concentrated on relaxing my sphincter so as to let him inside me.

After only a couple of tense seconds, the elastic ring of my sphincter opened up around his burrowing head. I looked over my shoulder with my mouth hanging open and felt the stretching inside my asshole as it offered it's weak and futile resistance.

At last, it gave way and he slipped through and slid slowly and smoothly into my rectum. I gasped, jumped a tiny bit from the initial shock of penetration, then exhaled deeply as he entered and filled my ass, softly groaning " ohhhh yessssss..." until I felt his pubes bump against my cheeks.

"There you go...you've got it all now.." Fred muttered softly, then he moved his hands to my hips and began rocking my body gently back and forth as he slowly commenced sodomizing me.

I hooked my feet over his calves and let my body relax as much as I could, feeling my belly sagging and my balls swinging.

There was no pain at all.

With practice at home, (I was using some decent sized toys that were bigger than he was) I had gotten to the point where anal penetration wasn't uncomfortable for me anymore, it just felt REALLY good!

Physically, it was the slightly stretched open sensation in my anus, the dull fullness in my rectum, and the smooth sliding of his penis against the walls of my anal canal and my prostate.

Mentally, it was the surrender and submission to another man who was better than me in some way, letting him invade and take my body, giving him control over it.

I just kept groaning softly as we hit a slow rhythm and the bed creaked in time with his thrusts. My head hung between my shoulders and my jaw was slack, and at one point I looked off to the side for a second and noticed something that I didn't see the last time we had sex all those years ago; the full length mirror on the closet door that just happened to show a full side view of him fucking me in the ass!

It was a very arousing sight to see; there I was positioned like a woman in a porn scene with my back arched and belly sagging, my hips tilted upwards and his penis disappearing between my asscheeks only to re-emerge glistening with lube and my secretions.

My face had that expression of submissive open mouthed concentration that turned me on so much when it was on a woman's face, like Teagan Presley when Mark Ashley was pounding her asshole at the end of their scene in BUTT CREAM PIE 4 (one of my all time favorite porn scenes...SO HOT) except Fred wasn't plowing my ass hard and fast...yet.

Fred was watching too and when our eyes met, his lips were rounded as he blew out his breaths. I looked him in the eye and mouthed "fuck my ass...fuck my ass...yeah fuck my ass.." and

he responded by curling his lips into a sneer and softly muttering "yeah? You want more of this cock? You want it harder??"

I nodded, licked my lips lustfully, and gasped "YES...OH yeah...YES fuck my ass hard...FUCK IT!!" So he gripped my hips tightly and began to increase his pace, which made the bed squeak more rapidly as my ass slapped lightly against his bushy groin.

I tilted my head back, staring at the reflection and whimpering with a pained expression on my face as he sodomized my ass. It took my breath away and his cock felt SO good up my asshole, like pleasant pleasurable friction inside it's elastic walls.

We filled the room with the sounds of two men fucking, that deep panting and grunting, and the smell of men's sweat mixed with the odor of lube, latex, and that salty odor of rectal secretions.

Pure, raw, INTENSE anal sodomy.

The room itself was warm and comfortable, and the dimly lit atmosphere felt like our own private universe together with nobody else around to bother us in our moment of physical intimacy.

I enjoyed the pleasant sensation of his puffy pubes gently scratching the tops of my asscheeks and the occasional bump of his balls against mine, and I also felt drops of sweat falling onto my back from his chin.

We were both sweaty, him from the effort and me from the intensity of the anal sex that I was receiving, and at one point he slapped my ass which made a loud cracking sound. It made me yelp and groan, and I felt more submissively feminized than ever before.

His penis was sliding in and out of my asshole smoothly while creating little moist sounds due to all the secretions that my rectum was producing. My sphincter felt loose and relaxed, and he must have felt it too because he began pushing in deeply and pulling me towards him for maximum depth.

It felt amazing and I conveyed this by moaning "OOOO yeah that feels SO GOOD.. DEEP in my ass like that...ohhh!!...OOOHHH!!..." He responded "yeah you love it..you love it don't you.." and slapped my ass again.

We kept up the rapid pace for a couple of more minutes until he stopped for a second to catch his breath but we were both breathing heavily and sweating. He still had his dick up my ass though and never actually took it out since he first put it in.

Then he leaned forward which made me flop down on my belly with my knees splayed out on either side. My groin muscles were stretched to their limits, but once he planted his hands on the mattress on either side of my chest and started plunging in and out of my upturned ass, I forgot about the groin muscles and just concentrated on the alternating sensations of fullness and emptiness coming from deep within my bowels.

I gripped the sheets in front of me and stared down at the sheet pattern as he had his way with my ass. His pistoning hips slapped against my sweat covered asscheeks and drove my hips into the mattress each time he thrust in to the hilt, only to bounce back up each time he pulled back.

By now, he had been fucking me for at least twenty minutes, but his dick still felt good in my asshole and the usual ache that came from prolonged anal penetration just didn't seem to be happening, although he was breathing heavily and sweating profusely from the exertion.

I guessed that the condom was keeping him from cumming, so I turned my head to look back at him, trying to stimulate him by urging him on, "YEAH Fred TAKE my ass, fuck my ASS...YESSS fuck it! Fuck me UP MY ASS!!...it feels SOOO GOOD!!.."

He responded with breathless grunting, but I could tell that he was fading fast because he fell down to his elbows and I felt his hot, sweaty body on my back and his wet chin on my shoulder. He kept fucking me by undulating his body and thrusting his hips up and down, basically grinding against my ass. This kept his cock mostly buried in my rectum and it felt really good, so I pushed my hips up to meet his thrusting and we were locked together in intimate sodomy.

The pure lustful pleasure of being the receiver in this unnatural sexual union was so intense that I knew I had to jerk off after this was over!

Just at that moment he seemed to catch his second wind and raised himself up again, but this time he moved his legs around my legs so that they were pressing mine together. Just like that, he was now straddling my upturned ass.

I raised myself onto my elbows and tried to look over my shoulder again as he put his hands on my shoulders and began banging his hips into my ass which jolted me forward rhythmically.

I yeIped and grunted with each thrust, and I felt his shaft sliding past my cheeks as it punched in and out of my asshole. I clenched them together for a moment just to enjoy the sensation.

My head hung down between my sagging shoulders and my feet rubbed together reflexively, and all I could do was grunt, moan, and pant in time with his thrusts. Throughout it, I kept whispering "yes...uh uh uh ..uhn... oh...uh uh uh...fuck...yeah...uh uh..shit...yes..."

Finally, his pace began to slow down and I just knew that he was going to cum momentarily, so I laid down prone with my arms tucked into my body and my head resting on it's side, watching our union in the mirror as I was pushed back and forth on the bed.

From that angle, I could just make out his cock going in and out of my ass at a downward angle, and my asscheeks rippling just a bit as he bumped against them. I always loved watching a woman's fat ass rippling and wobbling as a guy banged against it, so it was fascinating to see mine doing the same thing, except that my ass wasn't very impressive to begin with so the effect was somewhat diminished. Oh well...it was still hot to watch anyway!