The Challenge

by Thuglord

10 Jul 2020 2933 readers Score 9.0 (40 votes) PDF Mobi ePub Txt


In my first year at the University, I was caught fucking in an uncompleted building.

What had happened was that I had been chatting with a particular dude online for a while and he was passing through the state at which I schooled. I begged him to stop over and he did. But unfortunately, my cover up girlfriend appeared from nowhere like a ghost and refused to leave.

Myself and my guest had to look for an alternative because we were both extremely horny. He wanted to get a hotel room but because i needed the money (he was limited on cash), i suggested we go for an uncompleted building.

He vehemently refused but I insisted. Moreover, school was still on break and majority of the student had gone home so the environment was friendly.

He finally accepted and we found a secured corner among the rooms in the uncompleted building and swung into action. After i had sucked him to my satisfaction, I touched my toes for him to fuck the rubbish out of my man hole with his big juicy dick.

Few minutes into his hard pounding, someone whistled in surprise and another shouted "heeeyyyy!!!!! See homo". It was miracle i didn't faint on the spot. We never heard a single sound of anyone approach or else we would have quickly disengaged and pretended as If nothing happened.  But we were caught completely RED HANDED!!!

His penis was still inside my hole as i bent down.I recognized who the men were. They were the community vigilantes and among them was a man we (students) knew as "double cross". He was their leader and was so brutal that Even school cultists feared and dared him not.

Prior to that incident, i had met him one on on one over an allegation.  One guy in my hostel had accused his roommate of attempted rape and it was indeed a very funny and messy story. The guy claimed his room mate rubbed charm on his penis for it to stand and then commanded him to penetrate his ass hole. He said it was because he prayed seriously that the charm was broken but unfortunately, he had already released semen inside his roommates ass hole.  (You can imagine the nonsense).

How was I involved? His roommate is my friend.

The truth is that both guys have fucked several times and I was aware of it. My friend (his roommate) had told me that anytime they fucked, the guy will start praying to God for forgiveness even when he was the one who initiated the whole sex thing. My friend got fed up with his drama and stopped responding to his advances at night and perhaps that was what pissed him off.To save my neck, I denied i wasn't gay when asked by double cross. But even at that, I was asked to buy drinks for the vigilantes. Thankfully, my friend was acquitted because the stupid idiot who accused him, suddenly  went dumb when asked- "how he could allow another man rub charm on his penis and fuck him to the point of ejaculation without raising alarm or fighting him off in the process?".He was asked to pay a fine eventually and that was how the case ended.


Now, here i was. Touching my toes with another man's penis buried deep inside my anus. What excuse did I have?

Double cross immediately recognized me. As his men wanted to start beating us, he ordered them to stop. He pulled out a poorly made local pistol  and ordered we continue fucking so that he could watch. His men, (who were clearly irritated at seeing to men fuck) , were very confused at his consent and interest but they couldn't question him.

He insisted that he wouldn't let us go until my guest released (ejaculated). Infact, he told us to pretend that he and his men weren't around and watching us. They began smoking weed and ordering my guest to fuck me harder as he commenced. At some point, double cross asked my guest to bring out his penis so that he could see his dick size.  When he did, double cross whistled loudly and said women ought to fear me. After I was re-penetrated, he demanded I moan loudly and stop pretending like i wasn't enjoying it. And I did as I was told.

Miraculously, my guest released and they inspected my ass to be sure.After collecting all the money (physical cash) my guest had on him, they gave him until the count of 5 to get out of the building and he bolted out without hesitation. As he ran out, they smacked the back of his head.

As for me, I was told to come to their office the next day, same time- so that they would "treat my matter ".

As I got home, i was in complete panic. My girlfriend was still there like lots wife- a pillar of salt. As she started asking me silly questions about where I went, I called off the relationship instantly and screamed at her to GET OUT!!!!!. I was in total fear and the last thing I wanted was nagging.


The next day, i went to their so called office. It actually wasn't an office...it was more of a residence filled with all manners of shady scary looking criminals masking as vigilantes.

I had barely crossed the gate when a voice shouted - "homo boy". It was double cross. I almost fainted but I summoned up courage. Nothing happened during my visit. Instead of beating me up like I'd expected, i was told to "feel at home".

 I got himself and his boys alcoholic drinks and food from a nearby  restaurant.  I spent close to N20,000 that day. While I was there, double cross started asking me very embarrassing questions about my sexuality openly. He asked me to come the next day..and the next...and the next. That was how i became a regular visitor to his house.

Double cross became my protector in school. Anytime there was a situation, he was there. Even when my friends had kito situations, he tackled it effectively.  No school cultists dared cross my path or that of my friends.

Did I also mention that double cross took me to a whore house to experiment if I could fuck a prostitute? It was a total disaster. I struggled with erection and vomited in the process. He laughed at me all through. Also, he had once asked me to call my guest so that he could watch us fuck again but unfortunately, the man had blocked me on all platform the very day of that incident at the uncompleted building.

Double cross was an odd freak. He often told me he wanted to see how my ass hole receives big dicks once again. It seemed that incident had triggered a gay vouyer fetish in him. But for some unknown reason, it never happened.

I eventually graduated, served moved state and got a job.


Life went on and for over 5 years, I wouldnt hear from double cross until the day he called me out of the blue.

He had ran into one of my friends from the university and had gotten my number. He informed me he was getting married (the second time) and wanted my contribution as well as be part of his grooms men. I sent him a generous amount of cash and he was over the moon.

One day, during the course of our phone conversation, he started asking me if i still take dicks in my ass hole. I could hear a voice at the background and it seemed  there was an argument already taking place.

When I asked what was the matter, he told me that his friend was arguing with him that because women run away and complained about his dick size, no ass hole could comfortably take it.  As they argued, he started exaggerating to his friend how big the dick i had taken at the uncompleted building years ago was. His friend disbelieved and insisted that he was lying.

Double cross demanded that they placed a bet but his friend refused on the grounds that i was a guy and he wasn't homo. But double cross wouldn't hear of it. He accused his friend of being a coward and insisted that the deal was - "if i could take dick (or not)" and  not " if i was a guy or not".

 The argument was dragging and eventually, it seemed his friend was getting persuaded. He asked to see my photos and double cross hung up and called me back on video. I saw an older,  very ugly and ruggedly looking huge guy.

"Na clean guy o" (" He is a clean guy") he said as he looked at me.

He asked of my name and told me i should not mind his friend's gimmick. But in response, I told him outrightly that he would loose the bet to double cross. Clearly, he felt challenged.

"E be like u want die" ("it seems you wsnt to die") He said in defense as he tried to protect his pride and ego. His friend (Double cross) wasn't helping matters. He kept making mocekry of him and clearly, it made him upset. "I go tear your nyash o" ("I will tear your ass")he warned.But myself and double cross called him bluff

He promised I will be the one to run away when he handles me. Double cross was not ready to hear him.  He insisted that it was he- his friend ; who will run. This was evidently a "dare" situation.

Two days to the wedding, I took a trip to Asaba (where the wedding was to be held) and I had lodged in the hotel which also, was the wedding reception venue.

Double cross showed up to my room with 3 dodgy looking guys. They openly discussed  their 'operations" as they all drank and smoked. I asked him about his big dick friend and he told me he was on his way.Moments later, he took a call and gave the caller my room number.

"He's here" .

Turning to his friends, he informed them he had something he wished to discuss with me alone and dismissed them. As they made their way out, a very tall thickly built man dressed in baggy jeans, large jersey, big white snickers and wearing a base ballcap  that pulled all the way down to his nose like some 90s hip hop rap artist  was already at the door.  The men leaving greeted him in some weird language code and hand shake. They obviously "belonged" to the same "brotherhood".

"Boy!!!!...." the visitor said to me in a coarse voice that sounded like he had gravels a stuck in his throat. I instantly recognized the voice as the curious guy on the phone with the supposedly "big dick".

He looked much older in real  life than on video call.

"So you are the person who can collect penis more than woman right?" He asked- his voice heavy with arrogance as he starred at me as if i had absolutely no clue what I was up against. He started rolling a blunt and in the process, sprinkled something on it which smelt very awful as he smoked. He handed me his blunt and when I took few puffs, GOSH!!!! it felt like church bells exploded in my brain. The room was literally dancing and both men laughed at me as I struggled  to manage the high.

Double cross said something that sounded like their fraternal language which his friend responded.  They did this a couple of times and then,  Double cross said "go on".

To my surprise, his friend began to take off his clothes. Though his body looked shiny black, it was covered with scars and i saw what looked like bullet wound as well.  He pulled down his shorts to reveal a very thick and long flaccid penis.

"You aren't scared right?" He said menacingly.

Double cross on the other hand, was clearly excited.  He asked me to make his friends penis have an erection. I was shy and hesitant at first but it seemed both men weren't patient at all.

As i held the very fat dick in my hand, i saw how artiscally, the many network of veins travelled all over the penis even at a soft state. I rubbed his thick solid body and started to slowly kiss it along side. Maybe it was what they gave me to smoke because I was worshiping this man the way i would my lover.As my tongue found his tiny nipples, he moaned "fuck".

While mouth pleasuring his man nipples, i feathered caressed his ribs which made him stiffen to my touch. By the time my hand got to his penis, it had already multiplied in girth and length. He was nothing less than a 12.

FACT!!!!!

 HE WAS BIG!!!!!

HE WAS VERY BIG!!!!!

I led him to the edge of the  bed and grabbed my lubricant from my bag. As I knelt on the bed and stuffed my face with his over sized man meat , I started working my hole with my lubricated  fingers. I made sure i could comfortably put 4 of my fingers into my ass hole before turning around for him to penetrate my now opened hole.

Unfortunately, the penetration didn't go easy as I thought. His friend pushed hard into me and it hurt like MAD!!!!!!. Only bottoms will know and understand how excruciatingly painful this could be.

 Double cross had to quickly close my mouth to keep me quiet.

I felt my hole pulled and stretched so wide as my rectum was stabbed mercilessly. Never in all my life have i been fucked like that. As he fucked my hole, his extra large balls were hitting and smashing against my own balls and it really hurt. My body was shivering in agony and double cross, whose hand was still in my mouth, was whispering - "take it...yes take it" Into my ears. With his other hand, he patted my head in a comforting way .

As I reached my hands behind to urge his friend to slow his pounding, he slapped away my hand and intensified his thrust.

Even though I'd lost my erection, precum was still pouring out from my dick hole.

With one powerful move, i was flipped on my back and re-penetrated almost instantly.

Double cross was no longer holding my mouth. Instead, his friend was. All his body weight was on me as he grabbed me tight to himself from beneath my back while his other hand was over my mouth.

As he pounded me ,the noise coming  from my ass hole became so loud as if a full bucket of water was emptied inside. Though he was moaning , I could hear another voice moaning alongside at the background with a rapid slurping sound as if someone was wanking,I knew it was double cross.  But because his friend held my mouth firmly, it was impossible for me to turn my head to see what he was doing. From the sound of it, he was furiously masturbating himself as his friend fucked my brains out.  Because my dick was crushed in-between our stomachs and his movement was causing friction, i began to feel myself approaching climax.  Double cross also, was grunting and moaning like an animal and I knew for a certain he was cumming.

My dick could no longer endure the sensation as it erupted all over our stomachs. As i fought hard to contain the intense pleasure, he paused for couple of seconds and began to growl very loudly. I could feel several squirts inside my hole. To my amazement, his hands went off my mouth and we started kissing passionately.  We sucked each others tongue and lips as he fucked me very slowly as if he was savoring the sweet wetness of my hole.

"You try...you too much " he panted as he stood up and went to the bathroom.

Double cross was loud and happy as he praised his friend in languages I didn't understand. He even started spraying me money as I laid down on the bed.

It took me over 30 minutes before I could stand up. When I managed to get up, his friend said- "you get sweet toto shaa.." as he grabbed my soft ass hard and then put his fingers inside. 

In a husky etotic whisper, he asked - " did you enjoy it?"

"Yeah" I replied.

"Hmmmmm???  He whispered as he came very close to me and gave me a big kiss on my lips and he wriggled his finger in my ass which made very watery noises. 

Double Cross asked his friend how come he could stay so long during sex and he replied that he actually went two rounds and the second round took longer.No wonder the extreme wetness my hole was feeling. 

"This guy's ass is too sweet" he said to Double cross who couldn't stop talking about how much a " bad ass fucker " his friend was.

They both left shortly afterwards and funny enough, they never mentioned the bet. I counted the money thrown on me and it was N35k. The next day, i was full of pains. Double cross told me he'd given my number to his guy because he asked for it. 


His friend called me to let me know he had my number. Our discussion was brief...guess he isn't much of a talker.

On the day of the wedding, I realised he was the best man. 90% of the men in attendance were members of their fraternity because they all wore a certian color code. I guess double cross held a top rank position.

During the reception, he walked up to me like a bold lion and told me we should go to my suit. 

"I want to feel you " he said outrightly.

Automatically, my body began getting smoking hot. The pain I was feeling in my hole dissapeared. I didn't think twice. I followed him.  As i walked out of the hall, I turned back to see double cross smiling as he gave me a thumbs up. 

When we got to my room, we didn't remove our clothes. We just pulled down our pants and fucked. Surprisingly, my hole didnt struggle when he entered me.  It just opened easily. The sex was so sweet even though it was a quickie. I guess it waa because my man pussy wasn't fully recovered from the last serious pounding. 

After we both exploded our cum, we kissed passionately.  He asked me to suck his nipples briefly afterwhich we pulled up our trousers and went down to join the guest at the wedding.