I never talked a reluctant guy into sucking it... but I talked a reluctant guy into fucking me.
My college roommate Jim had the biggest cock I have ever seen- I mean Freakishly Large.
He also had the body of an olympic swimmer- was on swim team in high school and was in college on an athletic scholarship- altho that never went anywhere... maybe because that huge cock in his speedo was just too much drag in the water... it literally wrapped around so that the head was on his hip, and pulled the waistband away from his stomach.
Unfortunately, he had a face like a frog... but because there was nothing he could do to conceal his monster cock, he still ended up getting quite a few dates, because women were naturally curious about it.
But as the semester wore on he developed a definitive pattern... he would get a girl- date her a few times, and then she would dump him... He would find another new girl... and a few dates later she would dump him. Each time he got dumped he would get angry and want to go out and get seriously shitfaced. Being his friend and roommate, I would go along for the shitting of the faces.
SO- one night we're drinking a bucket of beer at a place half a mile from the off campus dorm we lived in; this was after he came back from a date early, freshly dumped, and really super pissed, and I make some comment that he should just be happy that his cock always gets him a new girl.... And he literally snarled at me, " you don't know anything about it!" I asked him to educate me and he practically broke down crying... "you think it's great having a huge dick, but it isn't. You know why they all dump me? Its because its too painful for them. They let me try and fuck them once, maybe twice- but it hurts too much and they just can't enjoy it. And Neither can I because if I get the slightest bit excited, I hurt them." he leaned closer to me and confessed, " I've never had it more than halfway in. And y'know what? I've never even CUM inside... they always stop me before I can shoot." He went on to tell me that its so big they couldn't even get more than just the head in their mouths... so he'd never even had a good blow job. For him, a big dick was a curse.
I suggested to him that he really needed to try and fuck one of them in the ass... I explained that, with practice, a person can take a much larger and longer cock up an ass than they ever could up a vagina. He sneered that if they were afraid of taking it in their cunt, there was no way he was gonna talk them into an assfucking. Besides, he asked, how would I know how big a thing an ass could take? I think he was expecting me to tell him some sordid story of using a baseball bat on my girlfriend or something... but instead, since he had confessed his deepest sexual secret to me, and he was a good friend, I told him about my own youthful experiences as a cum dump. He said he thought I had a girlfriend at some other school, and I told him that, sure, I preferred and felt emotional attachments to girls... but that the stuff with guys had just been raw, dirty sex for the sake of sex. He asked me all about the things I had done and I ended up telling him how much I had loved sucking cock, taking a load in my ass or my mouth, and even loved it when a guy fed me his piss. I confessed that even tho I didn't do things with guys anymore, that I still often wore a butt plug up my ass because I loved the feeling.
That seemed to be as much as he could handle and we drifted into other topics...
This was the first time I had told anyone of my homosexual experiences... and I wasn't sure if he would feel differently about me as a friend or not. Eventually we achieved peak shitface... and decided to stagger off home. The route we took went off the street and crossed a large empty field that had a copse of trees in the center... there in the little cluster of trees people had dumped a lot of junk... there was an old water heater, and a ratty old couch with no cushions, a few bald tires... and that's were Jim pulled up to a stop and announced that he simply HAD to take a fierce piss into one of those tires... And I said go right ahead...
He pulled out that monster in his pants and pointed it at the tire... but then he paused and wheeled toward me and said " UNLESS, you would Rather I piss in your mouth? "
I couldn't take my eyes off that cock of his as I sank to my knees and opened my mouth without saying anything.
He started pissing... and it came forth in a thick stream that first hit me in the center of my face... his unsteady hand wavered the stream all over my face, and then he pointedly sprayed his nasty piss all over my chest before bringing the current back up near my mouth and I drank my way up the stream of piss until I could wrap my lips around the head of his cock... even soft it was jaw stretching mouthful.... and I thirstily chugged his piss as fast as it flowed until I was sucking it dry.
As his bladder emptied... his cock swelled in my mouth and I segued into as much of a cocksucking motion as its enlarging girth would allow- my mouth was bigger than any of the girls he had dated- so I could get the full glans in my mouth before it just couldn't fit any further down my throat.
He moaned with pleasure as he grabbed my head and started short stroke face fucking me... but after a few minutes of this, he pulled his cock out of my mouth and grabbed me by the hair... he pulled me to my feet and turned me around to face the arm of the ratty couch, and growled in my ear about finding out if I was right about taking it in the ass... I dropped my pants and he shoved me over the couch arm... my ass high and my head and shoulders wedged down where the seat and the back of the couch met... He found the butt plug that I had inserted hours before... and yanked it out, causing me to gasp... and then he pressed the head of that huge cock against my still lubed hole and he shoved it relentlessly halfway in and I could not help but give out a little scream. Gawd it was huge. He just held it there halfway in while I panted with the pain...and then he started sliding it out, then in with a slow stroke... I tried to squirm myself over the couch arm to get my lower back at the angle I knew from experience I could take something longer... I could feel he was nervous about going more than halfway... and as he stroked a little faster I managed to gasp out, " all of it!". With a guttural growl he pulled nearly entirely out and then drove it deep in a steady push that made me cry out again... and I felt his hips grind against my ass, and then he ground it around in me hard before withdrawing to give it another full stroke balls deep.
With each slow and steady stroke I could feel him getting even harder and larger as he savored full penetration for the first time in his life... And with each deep thrust my cries devolved into a primitive grunting noise. He asked if that hurt and the most I could manage in reply was a breathy " hurt me". This made him start fucking in a faster tempo and I could feel the urgency of each thrust building... harder and harder.... 'oh, you like that pain, don't you bitch?" He snarled as he fucked me with increasing abandon. As my ass acclimated to his enormous size I found the strength to push back against the couch to meet the force of each ass slamming thrust of his hips until he was jackhammering me in a crescendo that ended in his cumming hard and deep... His final thrusts pounding into me and holding a second, then pulling put and pounding into me and holding as his jizz shot into me. Then he just kind of slumped over me a bit... and I could feel his cock begin to soften as he pulled out.
All he said, as he fumbled his cock back into his pants, was " fuuuck'. And then he left me there, bare gaping ass high over the couch arm, in the middle of a field under some trees, dripping wet with his piss.
I got myself back together and eventually made it back to our dorm room... I had to sneak in a back staircase to make it to the room without anyone seeing me soaked and smelling of beer piss. I found him there already passed out on his bed- I showered and went to bed and the next morning, he was holding his head and claiming he could not remember anything from the second bucket of beer on...
All I said was that was too bad because I remembered everything and we had a great time.
He never spoke of it nor admitted to it... but for the rest of the year, every time a girl dumped him, he would go get drunk, come back to our room, and just grab me by the hair and turn me ass up to jackhammer my ass in a fury. Our friendship pretty much ended- he didn't want to hang or drink with me anymore... He seemed to be angry at me all the time...but whenever he was particularly horny- he would drink heavily and then piss in my mouth and fuck me. And he always claimed having no memory the next day.
I think he was angry because he Wanted to fuck women... but couldn't. And he liked fucking me... but was resentful over his wanting to fuck a guy.
But I liked feeling used in that way. And so for me it was a great couple of semesters.