Third Encounter, Post Marriage

Everyone in this story is 18 or older, as are all my stories. This story occurred after I separated from my wife and realized she and I will never make it. We had already filed for divorce, but it was not yet finalized. The following story is based on a true event. Admittedly, there may be some sensationalism and embellishment for your sexual arousal.

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I was feeling pretty upset about my transgression against my wife. How could I have been so stupid? Well, the decision to divorce had been made and, though I regretted the way it happened, I was happy to be out of that relationship. now I was left alone wallowing in my misery and self loathing and it was uncomfortable. So, being the sex addict I was, I searched for something or someone to distract me. Sex always released endorphins allowing me to feel good for a time, though it was always too brief.

I returned to craigslist once again in search for a random encounter. I wasn't looking for a meaningful connection, just sexual satisfaction and experimentation. At this point I still hadn't experienced anal sex, from either side, and I had a very urgent desire to do so. I searched and searched looking for someone who fit the bill. I don't remember how long it took, but eventually I found someone interested in the things I wanted. Just like my first encounter, I didn't know much about this guy, not even his name, but I was eager and horny. We agreed we would meet at his house while his family wasn't home. Since I lived with my parents, I couldn't host, so I couldn't be picky about the places I met people.

I showed up at the agreed time, around 3 pm. I was nervous. I knew this guy was Asian and chubby, beyond that it was a mystery. He ushered me into his home. Upon first greeting, he led me to his living room and began to try and kiss me. At this point in my adventures, I hadn't kissed a man. To be honest, I didn't want to. It felt too personal and uncomfortable. The scruff of another man's beard against my cheek was a turn off. I turned to him and let him know I didn't want to kiss, but anything else was fine. I know, it's silly. Kissing, to me, was just too intimate, while having a dick in my ass I could try casually and not be bothered.

In my host's living room, we sat and I figured we'd talk a little bit. That is not at all what happened. He had no interest in conversing to ease the tension. For him, there was only the sexual tension he felt in his pants and he was eager to relieve it. He began to remove my clothing, revealing my average body of 165 lbs. Not excessively fit, but still in decent shape. I had shaved my crotch for this encounter so my 6" cock with my loose sack of testicles was clean and smooth. I began to remove his clothing mechanically. What I saw was very satisfying. He had lightly tanned skin, a chubby stomach and chest which gave him a nice full belly. Nothing like a pot belly, just a nice layer of fat all over. I put my hand on his stomach to move down to his shorts, his skin was soft, that was a turn on. I bent down as I removed his shorts realizing he didn't have underwear on. His hard, uncut cock sprang to life as his shorts fell to the floor. He hadn't returned the favor of trimming his pubes, but that was ok. I breathed in to catch his scent. He was clean, I was grateful for that.

His body was what I wanted. Chubby, plump in all the right places. His ass was nice and bubbly, just enough to be full and encourage my arousal. His cock, while uncircumcised, was a perfect size. It was approaching the same size as mine, maybe a little shorter. This was exactly what I wanted. Somewhere along the line I had decided I wanted to be bottom to all the small cocked chubs out there. An ass that the big boys could play with and enjoy without judgement.

My host got down on his knees and began sucking my dick. He was uncerimonious about it. He took my hard cock in his mouth and began sucking with fervor, but not much skill. I had no room to judge, at this point I hadn't touched another man's penis to test my skills in fellatio. Despite little skill, he was doing well. I was enjoying myself. After maybe a minute or so, he stood up and asked me to do the same to him. I obliged. I got to my knees to take him in my mouth. I wasn't excited about his uncut cock. To me, it was unattractive. I had never seen one up close. But, as he got harder, his tip revealed itself most of the way. With a gentle stroke I revealed what remained. To my pleasure, his cock was pretty. He had a pleasant scent, that encouraged me to go on. His head had a mushroom shape to it with a shaft that started slightly slimmer just after his glans and got thicker to match the thickness of his tip at the base. All in all, a nice member.

I opened my mouth, letting my host slide along my tongue and was introduced to my first taste of asian dick. It wasn't a good or a bad taste. I was again happy he was clean. My cock began to throb as my lips were gliding along his shaft, trying to take it all, but being subject to a sensitive gag reflex. I stopped at about 4 inches and worked my way to the beginning to make my glorious, and indecent descent along his pulsating rod once again. I was still very nervous. Was I pleasuring him or hurting him? I couldn't be sure and I was kicking myself for not paying attention to what the last guy had done to me. His mouth had felt very good. I assume it was because of his very chubby cheeks that made for a more cushioned cavity to fill. Either way, I did my best and hoped he enjoyed it.

My cock was still aching to be touched again so I was ecstatic when my host suggested we 69. With my sensitive gag reflex, I opted to remain on top to allow me more control. I straddled his head then leaned forward laying atop his ample body. Making skin to skin contact like this gave my penis a new reason to be alive. With his warmth radiating, I felt comfort. I looked down at his groin and admired his thick thighs that led to his soft fat pad. I kissed the base of his cock where it met his pad and trailed more kisses along his shaft. At the same time, he had fully swallowed me to the hilt. The feeling of my swollen tip being engulfed by his throat was surprising and all encompassing. Now that I knew of his talent, it was all I wanted. I had to take my previous judgement back, this guy was good. He reached around my waist getting a firm grip on my ass and pulled me down on his face allowing him to rest his head on the floor as he encouraged me to thrust into his mouth.

I continued to administer my treatment to his cock, though heavily distracted. While my tip was being inundated with attention, I slobbered all over his furry ball sack. I sucked on each testical separately, licked from the tip of his dick, between his two nuts, ending at his taint. He said he really enjoyed that so I did it a couple more times as I massaged his ass cheeks.

As if qued by my actions, my host began to massage my ass cheeks as well. As he massaged them, he would spread them and I hoped he was getting a good view of my shaved asshole. I got my answer as I felt a finger rub against my eager hole.

"Fuck, your asshole is sexy," he said breathlessly. "It looks really tight. Are you a virgin?" he asked.

I was embarrassed to admit this fact. Being a virgin had a negative stigma throughout my life so my initial reaction was quite negative. Though I was hesitant to admit it, I did in the end.

"Um, yeah!" I replied.

"That's so fucking hot!" he exclaimed.

I was glad for his positive response. Feeling more relaxed, I returned my focus to his stiff schlong, which felt harder than before, and to his gentle proding at my forbidden fruit. In hind sight, pun intended, I wish I had focused more on the thought of being penetrated by a real penis for the first time. It certainly would have increased the arousal for me. But, now you can enjoy the fact that I was going to have my first-ever, hard dick slide into my virgin ass. What was it gonna feel like? Was I going to enjoy it? Well, there was only one way to find out.

Unfortunately, my host felt impatient and prodded at my hole only briefly. It felt great having his finger rub against the soft, sensitive skin of my anus. Without lubrication, he tried to push his finger into my rectum. This was somewhat painful, so I asked for some lube. He declined to grab some and decided to stop pushing in and opted to move to another position. I knelt in doggy style while he placed his face between my ass cheeks. His tongue began exploring my exposed crevace, seeking out the sink hole hidden within. I could feel his tongue stiffen and relax with his efforts to tongue fuck my ass. At this point, you can imagine that my ass was fairly tight having never been fucked before. That being the case, try as he might, he couldnt get very deep. He spent maybe a minute or two continuously exploring me before his patience once again waned. His desire to fuck me was waxing strong and persistent. So he led me to his bedroom where he had his stash of lube and condoms.

As he began pulling out the sexual aides, he layed down on his back and motioned for me to straddle him. This was it! I was going to let this young, chubby, asian man slide inside of me. I took a condom from him and slid it onto his cock. I jerked him off as I storked the condom into place. he squirted some lube on the tip as I stood up to find the right angle for balance and penetration. I stood above him on the bed, facing him and began to squat down. As I reached his cock, I found that I wasn't flexible enough for this position and almost lost my balance. So I stood again and reset to a kneeling positon with my legs on either side of him. This time, I reached back and found his cock and my balance. I slid up and down his shaft, letting the lube get everywhere. I shifted and felt the tip of his dick press eagerly against my nervous hole.

As I pressed backward, I felt his tip begin to split me open. I hadnt prepared enough for this. As he began to enter I had to pull off because I hadn't quite mastered the art of relaxing my sphincter. he wasn't able to get in vey much. So, in his impatience, he decided to swap places.

I grabbed another condom and placed it on myself. He assumed a doggy postional and reached behind him, spreading his sexy ass cheeks. I was so nervous now that I found it difficult to perform. as I pressed my cock against his opening, it gave way just for me to go flaccid due to low friction and my own hesitancy. He was kind, though.

"Would you like to try without the condom?" he asked me.

"Are you sure that's ok?" I asked incredulously.

"You're clean, right?" he double checked.

"I am," I replied.

"Then it's ok with me as long as you're wanting to get inside me." he could tell what I wanted.

I quickly removed the condom and began my assault again. I slid in è further into his asshole. This felt great. I was finally popping my anal cherry. I was getting to stuff another man's ass with my throbbing member as he moaned with joy at every invasion.

It wasn't long before I was feeling ready to spill my seed.

"I'm gonna cum," I moaned. "where do you want it?"

"Inside me!" was all he said and all I needed to hear.

I felt my prostate tighten and begin to pulse as I shot rope after rope of cum inside my host's ass. I kept thrusting until I felt the last aftershock of my orgasm.

Shame and guilt hit me like a wall. What was I doing? Why did I just have sex with another man? Why didn't I enjoy it like I thought I would?

My host wasn't quite done with me. we made another attempt in doggy to get his condom covered and heavily lubed dick up my ass to no avail. He did manage to get a finger inside me, but he couldn't maintain an erection long enough to make any meaningful penetration.

So, we opted to have me sit on his chest as he strocked himself to completion. I had checked out and didn't want to be there anymore. I watched as he came all over his stomach and groin. Finished, I got up and began to get dressed. He did the same and showed me to the door.

"I think next time this will go much smoother." he said.

I turned to him and very coldly stated, "this will never happen again." and made my way to my car and never saw him again. I remembered his pubes. so thick and wiry. I decided I wanted smooth shaven chubs from then on.

After the feelings of guilt and shame subsided, I reflected on the experience. I had enjoyed filling his asshole with my cum and was now envious of that experience. Though reluctant to try it, I made a mental note of at least thinking about letting it happen some time. Little did I know I would come to love it.

The End