My Pal's Second Cherry

[Tailgunner]

Craig and I had been friends since high school, class of 1980. We discovered gay sex our first year in college and quickly discovered our roles.

 

From the start, I was strictly a top, whereas Craig was versatile. Since high school I gained just a little weight, upgrading from 170 to 200.  I had also grown a good beard. I liked to masturbate a lot so I had also taken to keeping my nails bitten to the nubs. My cut dick was somewhere between seven and eight inches, with corresponding thickness. I liked to fuck tight asses as well as face-fuck the cocksuckers. I had tried using condoms but just couldn't get the feeling I needed in order to get my rocks off.  Over the decade Craig went from about 200 to almost 300 pounds.  He had a small, cut dick which measured about five inches, but he also got super hard, so he really enjoyed breaking anal cherries, as well as getting sucked off.

 

I was pretty much an exclusive barebacker, and in fact, the only time I nutted wearing a condom was when I fucked one asshole using Bengay for lube, which, I found caused his ass to flex around my dick while I fucked him as he tried to escape the abject pain. Looking back it may have been one of the fucks I most enjoyed, maybe ranking with my all-time favorite fuck, which was the time I took Craig's anal cherry.

 

Back in 1990 I was working in a small factory, but Craig, who I still occasionally fucked, had taken vocational courses in college and then went to trade school, and several jobs later was working in a junkyard.   I was pozzed about this time when, having gone on a month-long vacation, during which time I went to visit family out west, and ended-up at a bar which led to my attending a sex party. When I awoke the next morning I had a hangover and a sore ass. I remembered someone handing me a beer, which I had only partially consumed, but honestly I don't remember much more of that night.  Even so, life went on for a few weeks until I found myself feeling as if I had lost a fight with a gorilla. I went to see my doctor who ran a few tests, and eventually told me I was poz.

 

I called Craig, who I hadn't seen, and, of course, with whom I hadn't fucked since the week before going on vacation and told him the bad news. "Looks like our sex life is over unless you want to get pozzed."

 

"Things will be okay," he replied, and suggested I take things easy. I also called my boss who seemed understanding, probably because he himself was bi.  I spent the next two months recovering from the fuck flu, and eventually, after a long hiatus, I finally felt like masturbating.  It had been perhaps two months since I had last cum, and I readily shot my first poz load off into a bathroom sink.  It felt good to get my rocks off, and I found myself thinking of the first blow job I had ever received, which, as it was, had been given by Craig, who had also been my first piece of ass.  I found myself remembering the pleasure I experienced when my dick broke his anal cherry, even as he writhed in pain. Fair was fair, however:  he had fucked me first so he had been obligated to let me fuck him. 

 

A couple of weeks later I persuaded him to let me fuck him again and that time he came from getting fucked, so he was hooked.  Our sex life became a rich mixture of getting my rocks off in his ass and mouth, me jacking him off and us putting our meat and cum to others.

 

After I fully recovered from the fuck flu, I returned to work, and I could see I had been missed.  Although my boss had hired a couple of temp guys, none of them could match my performance.

 

A couple of weeks later Craig and I got together, and he confided he longed to fool around with me.  Sure enough, he ended-up giving me a blow job, and I jacked him off.  It felt good to use his talented mouth, get my rocks off in it and feel him swallow my cum with my cock in his mouth. I was on the crude drug cocktails and pondered if, by blowing me, Craig would likely end-up converting, especially since back in the mid-80s Craig had told me that if he ever got pozzed he'd want me to do it.

 

I should explain that back then Craig and I were more or less monogamous.  My dick was usually the only one up his ass, save for the dicks of a couple of friends of mine when we were still college where Craig occasionally played around with other guys, usually sucking them off, and I occasionally fucked other guys or had them suck me off.  Craig and I also occasionally had oral sex, and I tried once or twice fucking him with a condom, but that didn't work for either of us.

 

After I converted I looked into the dangers of each type of sex, top vs. bottom, oral vs. anal, and that the safest sex with a poz man of all was getting jacked off by one who kept his nails bitten or clipped to the nubs which prevented accidental cuts to the dick. As for penetration, getting sucked off by a poz cocksucker was safest and the most dangerous was getting fucked in the ass by a poz man.   So when Craig and I resumed having sex after I converted, initially we had more oral sex and one time, after he had swallowed my poz cum and kissed my poz dick, we had a short discussion and decided that it was time for me to inject my HIV-laden cum into him up his fat ass. My dick hardened as we discussed how I'd take care of him when he caught the HIV flu and he assured me his medical coverage would pay for his treatments as mine was doing.

 

The next afternoon he told me he had chosen to go on vacation in a month or so, which means if things worked out correctly, he would be hit with the fuck flu about the time he was scheduled to be off work.  With that, we both stripped, hugged and french kissed, then he spat in my hand and I jacked him off. He shot-off his last load of neg cum in my hand. He sucked my dick to full hardness, left it wet with his spit and lay on his stomach on the bed while I smeared his cum onto my dick. My dick was rock hard and throbbing as I mounted my buddy and lined-up my shot. I put my weapon to his hole and drove it home with a quick thrust to instantly hilt it up his ass as he squealed in pain. My dick felt really nice in his snug hole. I flexed it and felt my masculine power as it expanded in him. He felt it too. He hadn't been fucked since the day before I started my vacation so his hole was tight and very easily abraded by my dick, which encouraged the opening of more fissures to facilitate passage of my toxic virus into his body.

 

I began fucking him, and felt a sense of power over him, somewhat similar to how conquering I felt when I broke his cherry. Now I was breaking his HIV cherry and enjoying his hole which had tightened over the several weeks since I had last fucked him.  

 

This time, as I made it a point to pull out almost all the way, and to slam myself home as roughly as possible, just to make sure I tore-up his insides before my pre-cum began to provide too much lube. He felt the pain and asked what I was doing. "I'm preparing your ass to take my virus easier," I replied and rammed it home a few more times.

 

I knew it hurt him but putting pain to holes provided more pleasure to my prick and usually resulted in better feeling more intense orgasms when I ejaculated. I pulled my dick out of him to check for blood and found some along with the usual other stuff from fucking ass. I rammed it back into him with a snap of my hips and fucked him, piston-thrusting in, intensely enjoying fucking him and thinking how great I would feel when I pumped my dirty cum into him and how my prick would pulse with pleasure with each spurt of my HIV-laden cum into him and how he horrible he'd feel three weeks later when he suffered the flu.

 

I was so turned on I fucked him faster, harder, grinning in anticipation of my soon to come ultimate good feeling. I began breathing hard and working up a sweat as I fucked him good while he lay patiently under me accepting my self-serving thrusts in him. I knew he had trepidation about getting pozzed but then again he knew he'd get pozzed sooner or later and by someone else had I not fucked him soon enough.

 

My thrusts became jerky as I got closer and I slowed my thrusts just a little, knowing that a slower speed near orgasm would result in a longer, better feeling orgasm, ejaculating more cum into him which would slightly increase my chances of infecting him.

 

I had had mixed feelings about infecting my long time friend with such a life altering virus but as we'd discussed before, it would be better if I infected him instead of some Joe Blow. I varied my speed, got close and fucked him good, and then my dick exploded in one of my all-time best-feeling orgasms.  I enjoyed the knowledge that my mighty meat was pumping spurt after spurt of HIV-laden cum into his ass, my virus-laden sperm forcing its way into his ravaged anal walls.

 

After my initial eight or nine powerful spurts I repeatedly rammed it home to keep up that good feeling in my penis and to pump as much of my dirty virus into him as possible. I felt on top of the world conquering my friend a second and even more significant time. My hips took over thrusting my meat in him for another minute or two before i felt completely satiated. I rested on his back with my dick buried in his fat ass, feeling manly powerful like the studly mountain man who had conquered the fat asshole in the movie Deliverance.

 

I had read the book as well as seen the movie and each time got a precum-slimey boner. Now thinking of the mountain stud having the virus and pumping it into the fat ass turned me on even more. I thrust every few seconds in Craig's ass while laying on his back and he massaged my still mostly hard dick with his ass muscles. "How's your ass?" I asked him.

 

"Not too bad.  About like the second time you fucked me.  Oh, and I came," he replied.

 

"Good. I'm going to leave it in and fuck you again when I reload," I told him.

 

He felt a bit of pain but he agreed and I took a nap laying on his back, my dick still inside his ass.  I also figured he might cum from getting fucked again. About forty five minutes later I awoke and felt my dick was still semi hard in his hole so I began taking short strokes in him while thinking of how he would suffer from the flu and my dick hardened in less than a minute. I began fucking him and enjoying how my hard stiff penis was forcing my virus from my first load into his bloodstream with each thrust in him.

 

I had ass twice in a row before withdrawing many times as well a having someone suck me off for my second load and sometimes got the blowjob first and then fucked the guy's ass for my second piece. I sawed away in his ass and enjoyed the fuck, my first load of cum also providing additional lube but not too much, just what I needed to pleasure my penis and still further abrade his inner rectal tissues. It took about five minutes longer than my first fuck to nut in him. It was a great fuck with my dick feeling just as good pumping my second load up his ass as it had with my first. Again I brutally thrust and slammed it home while enjoying how great I felt pumping more virus up his ass and into his body. I also corkscrewed my hips and pinned him with my prick.

 

Spent, I lay on his back and asked him if he had cum again. He said he hadn't but it felt good even with the pain from being fucked brutally.

 

My dick, lodged in his hot ass, was in seventh heaven, and I found it quite comfortable to rest on his back, somewhat similar to laying on my good air mattress, so I remained in that position, on Craig's back, for another hour before my dick completely deflated and came out of his ass.

 

I dismounted and lay beside him. He got up and sucked my dick clean, doing a thorough job in swallowing all his and my fluids.  Then he lovingly kissed both my cock and each of my balls.

 

Over the next several days I fucked him daily, and occasionally I let him blow me.  Sure enough, right on time Craig came down with the fuck flu.  Of course I honored my promise to care for him until he recovered, checking in on him before and after work.  I showed him my hard dick a few times but he wasn't bitter. He knew the consequences of letting a man infect him and reasoned that it was better I had converted him than an otherwise unknown guy.  In addition, we both knew how much I enjoyed injecting my diseased cum up his ass.

 

He started feeling better after nearly another month and returned to work. He slowly built his strength back up and diligently took his drug cocktail just as I had been doing. He began losing weight, maybe a pound a month. He had lamented his decade-long weight gain and I had told him that catching the AIDS would result in weight loss. Craig and I fucked a poz guy or let one suck us off once in a while but Craig was still my main piece of ass and I was his stud. We continued our sex as we had before the pozzing. We also discussed various punks and assholes we could enjoy pozzing. Craig was curious about how good pozzing an asshole would feel compared to fucking someone of the same status. He did enjoy better orgasms when he broke ass cherries, feeling his manly power when the virgin hole suffered from the pain he put to him with his small but mighty prick, much the way I had felt when I broke his HIV cherry.

[MackyJay]

Nice and hot for sure.

[Tailgunner]

It had been five or six months since I'd pumped my pozz jizz up Craig's ass. I was fucking him regularly and my orgasms seemed better than when we were both neg, mainly because my dick seemed to "remember" the fantastic feeling when I pumped my life-changing spunk up his ass. I was also enjoying the great blowjobs he gave me and how he kissed my dick and balls after swallowing my cum and drinking my piss and especially when he sucked my dick clean and kissed it and my balls thanking me for the fuck I put to his ass. 

He was also getting his rocks off, either by me jacking him off to use his cum for lube to fuck him or by fucking and getting sucked by a couple of poz guys, one of whom I had pozzed.

 

I had just finished fucking him one afternoon and was laying on his back with my dick still up his ass enjoying the afterfuck, 

 

"Another nice piece of ass." I said and thrust in him. 

He told me he had cummed and then said, "I need to pozz a neg. I want to see how much better my dick feels shooting my dirty load in one. I heard some other guys say that pumping their pozz jizz up a neg ass and infecting him is a huge turnon."

 

"That's true. And I'd sure love to see you enjoy pozzing one." I replied and thrust in him again.

He then said he would love to pop a total cherry asshole or fist someone to cut the asshole's rectum up inside with his thick nails and then fuck and infect him.  He also wanted to see me pozz another asshole too. I thrust again and told him how sexy he was and how glad we stayed friends since high school and became lovers. He replied much the same. He had fallen in love with me soon after I had broken his mouth and ass cherries and then more in love after recovering from the flu I'd given him by shooting my infected cum in him.

 

A few minutes later I pulled out of his ass, dismounted and stood by the bed so he could get up and suck my dick clean. He did so and I then urinated while he drank it. Once the last of my piss joined what he'd sucked off of my dick and swallowed he sucked off of it and kissed it and my balls.

 

"Let's look for a piece of ass for you" I said after he hugged me.

 

We got dressed, had a snack and headed out to one of the bars where chasers cruised. 

There were no total virgins but one twink who said he was 21 said he was still neg. I asked him how tight he was and when he was last fucked. He said he was decently tight and had been fucked a couple of nights before, with a condom on the man's dick. I asked him about his last HIV test. He said he never was tested. Craig and I both wanted to be sure he was neg so Craig could truly experience the thrill of pozzing him.

We "interviewed" a few others who said they were chasers. We also needed to weed-out the infected ones who said they were chasers. I had run across some punks who had been freshly pozzed and either hadnt had the flu or had "completely" recovered from it and appeared neg. 

 

Over the next week we checked out more chasers and picked three who we'd have tested. One by one we took them to the clinic for testing. One was poz and the other two tested neg. The problem was that once a stud ejaculated in an ass it took over a week for any markers to show up in the chaser's blood. 

We settled on a homeless twenty-two year old who agreed to get tested, stay a couple of weeks, get tested again and get fucked. Either Craig or I would be keeping an eye on him 24/7 to make sure he didnt cheat on us. We allowed the punk to masturbate, fuck a masturbation cunt and dildo himself since his 'first cherry' was already history.

 

We headed to the clinic for the testing. Once the results came back as neg we moved the punk in and got him some new clothes from a discount store and gave him room and board. In addition to one of us with him at home he was always accompanied by one of us when leaving the apartment including going to a restroom and anywhere else. The two weeks seemed to drag and we had to put up with his somewhat mild drug habit but at least he was only popping and inhaling but not shooting anything so there was no contaminated needles to worry about. 

 

It was finally time to test him again. The punk tested neg so it was time for my asshole buddy to have his fun pozzing him.

 

Once we got home we all stripped as Craig grinned. All our dicks started hardening and the punk knelt and kissed and then sucked on Craig's dick. A few seconds later the man's dick was rock-hard.

 

"On your stomach on that bed." I said, gesturing to the rubber sheet covered mattress on the floor.

 

The chaser lay on the bed and Craig knelt, shoved his unlubed finger up his ass and thrust and twisted as the punk endured the pain. Craig pulled out his finger and smiled to see an adequate amount of blood on it. He told the punk to suck it clean. The punk made a disgusted face but opened his mouth, let Craig put his finger in, sealed his lips around it and sucked it clean. 

 

Craig's dick was still rock hard so he added just a little bit of grease on his dick, just enough for his own comfort and to facilitate easier penetration, spat on the punk's hole, mounted him and put his dick to the hole. He the let his weight drive it home as the punk yelped and shook from the pain as the man drove it all the way home and pinned him to the bed. He lay on the punk's back a minute and then began a series of brutal fat-shaking thrusts to further rip-up his rectum inside. His fat rippled with each snap of his hips as the punk begged him to take it easy. Our hero ignored the bitching and fucked the way he wanted. Craig held the punk's upper arms and threatened to drive his thick dirty nails into his skin if he didnt shut up. The punk, beside himself with the pain the stud was enjoying putting to him, quieted down and sobbed and suffered, knowing his fate. Craig worked up a sweat pistoning his dick in the now ravaged hole. He began breathing hard but didnt let up. I was proud of my buddy as I admired him working to pass my virus on to that punk. My own dick was hard, throbbing and oozing precum as Craig's potent penis pumped pain into the punk. Craig fucked that punk for a good ten minutes, let is hips go wild and then grunted and grinned wide as he hilted himself and pumped his deadly virus-laden spunk into the punk, his penis pulsing with pleasure with each spurt he shot into him. He then resumed his manly thrusts pumping more virus into the sore asshole who now sobbed feeling sorry for himself trapped under the big fat sex-hero and pinned by his mighty prick. Each additional thrust forced more deadly virus through the ripped and fissured anal walls into the punk's bloodstream, the stud's virus on its one-way mission to wreck the punk's health and lead to his eventual death because he would later take too many drug holidays. 

 

The punk was feeling miserable under the big fat stud, his hole feeling almost as bad as when he first got his cherry popped by a man who was wearing a condom. Craig was in hog heaven enjoying how great he and his dick felt after injecting the asshole with his dangerous jizz. Craig thrust and slammed several more brutal hip-snapping fat-shaking thrusts into the sore hole, rested and withdrew slowly in order to keep as much cum inside it as possible. 

 

Craig dismounted and stood up. I had to tell the punk to get his lazy ass up and suck his hero-stud's dick clean. He cussed us out and Craig grabbed his arm, yanked him up and threatened to punch his face if he didnt obey. The punk, afraid, obeyed and sucked my buddy's dirty cock clean and kissed it as ordered. The punk then massaged his arm which was bleeding slightly from Craig's nails when he'd yanked him up. The punk then cussed us out and threatened us but I told him that he would be a Bubba's bitch in jail if we told the police that he had let men fuck him. Back then the laws of the state there prohibited a man from sucking cocks or allowing anyone to fuck him but there were no laws prohibiting a man from penetrating the partner of his choice. The rape laws back then only applied to men raping women or someone having any kind of sex with minors and animals. Effeminacy was considered as soliciting to suck cock or take it up the ass. Drag queens and effeminate men were often picked up for soliciting to get penetrated. The punk wasnt a fem-queen but compared to us men he could be perceived as effeminate by the police. Geeks and nerds were considered masculine compared to many young guys on that era.

 

He clammed-up. We told him we'd take care of him through his flu if he caught it. That meant another two months but he would partially pay his way by being Craig's and my bitch until he was too sick with the flu to put out. I let Craig have the punk's ass but I did let him suck my cock a few times. I also got him to rim us a few times. Craig would suck my cock while the punk rimmed my sweaty ass when I got off work.

The punk caught the flu just about on schedule and suffered. Craig was ecstatic that he had caused it by fucking him. Pleasure for the penis = pain to the punk. The punk was bitchy going through the flu and we ended up kicking him out once he felt better and I'd finally had my piece of his ass.

 

During the two and a half months we dealt with the punk we were looking for a full anal virgin for Craig to break. Fucking the punk had fed Craig's ego but he still wanted to rip and infect a full virgin who was both neg and never had anything but maybe a finger up his ass. I myself wanted to poz a total virgin but I wanted Craig to have first go at one and I'd fuck the next one we'd find.

[Tailgunner]

It took us a couple of months to find a young man over eighteen who still had his anal cherry. The bars, baths, sex clubs, smut shops, dirty movie theaters, etc. were obviously poor places to find total virgins. I had a friend at work who said his "faggot nephew" had just turned eighteen. He never liked his nephew but not because he was gay. He liked our idea of giving him to Craig to pozz his double-virgin ass. He even said he'd have some friends help Craig get his piece of him,  mainly to hold him down in case he tried to throw Craig off and evade his diseased dick.

The guy had the typical long hair, even longer than Craig's. He seemed nice enough and was naive enough to know little about HIV/AIDS. He did indicate he's prefer a guy more like himself to break his anal cherry but his uncle had better plans in order to punish him.

 

The fuck took place in a basement sex room. A rubber-sheet-covered mattress on the floor with chains bolted to the floor by each corner was the main venue. A fuck-horse stood by one wall. The man in charge asked Craig what position he preferred and Craig said he'd like the punk on his stomach, legs spread and a pillow under his crotch. 

 

The punk was brought in and told to strip in front of a handsome guy his age. This gave him the idea that the young guy would likely take his cherry. Once he'd stripped he smiled at the guy who told him to lay on the bed. He obeyed and we held his arms and legs to put leather cuffs on them and secured them to the chains at each corner. He seemed to suddenly realize his predicament. Craig then knelt in front of his face and fondled his dick.

 

"This is your real stud. You should be glad he's small,  it'll be a little less painful when he fucks you than if I fucked you. Be glad it's only him and not all of us." I informed him while showing him my much bigger dick.

 

The punk was outraged but was as helpless as a new punk in prison about to get turned-out by a team of horny jockers.

Craig greased up his weapon, stood up, stepped to the foot of the mattress, knelt and positioned himself between the punk's legs. He then got on all fours, one hand on the punk's back, the other holding his dick which he rubbed on the asshole who tried to shake and move but he was also strapped to the bed as well as secured by his wrists and ankles. Craig put his dickhead to the asshole and forced his way in as the punk screamed in abject pain. He pulled out a bit, rammed it in further, pulled back an inch again and rammed it home as the punk screamed so loud we thought anyone in the next house over which was a good 1/10th mile away could hear him although the basement and ceiling overhead provided excellent muffling. Fortunately someone grabbed Craig's undershorts, wadded them up and forced them into the punk's mouth to gag him. Craig grinned as we cheered him on.

 

The punk was sobbing, his cherry broken and filled with pain and meat. Craig fucked that asshole good, enjoying the tightness around his small but mighty meat. Every man in the room sported wood and one man and a little bottom got together with the bottom bending-over while the man stood tall and proud fucking him. Both admired Craig as he heroically fucked his virgin conquest who was now resigned to taking it. Craig then pulled out and the punk looked like he thought it was over. We saw a little blood on Craig's dick.

 

You're doing good stud." I said.

 

Craig thanked me, stuck his dick right back up the asshole who winced and sobbed anew as the stud resumed fucking him.

Craig said he felt good in that tight virgin ass as he fucked him. The look of joy on his face turned us on as he fucked with gay abandon. He didnt need to cut up the asshole's insides with a fingernail nor pound him into the bed as he had the previous asshole he pozzed. His dick had done a great job all by itself splitting the virgin anal walls as it barreled its way up the hole, his first few thrusts doing all the damage necessary to allow easy passage of his virus into the bloodstream.

 

The stud began breathing heavy and just started working up a little sweat when he said he was getting close. He poured it on fucking faster and harder, grinning as he neared his orgasm.  His precum had already put a good amount of virus into the hole. He raised his head and then hilted himself, then pulled almost out and slammed it home, again and again as the punk shook from each manly thrust of our hero's hips driving his dick into the cunt ass pumping in more toxic virus with each stroke. 

 

"Man that feels so GOOD!" Craig announced as he finished ejaculating in the punk's hole.

 

He thrust a few more times and lay his weight on the punk's back. The punk could barely take the man's weight but the man liked resting and lazily thrusting from time to time to force his poz sperms through the asshole's anal walls into his bloodstream. I had shown Craig how to maximize the chances of infecting assholes by fucking him several times the way I had when I pozzed him, having learned from other gift givers who told me the best ways to facilitate passage of virus into the chaser's system. 

 

A few minutes later our hero pulled out, stood up and put a foot on the pink's back as we all cheered him and I held up his hand like a fight referee holding up the winning boxer's gloved hand.

 

"The winner, Craig!" I announced and hugged and kissed him amid more cheers. I also announced the loser's name.

 

Craig thrust his still semi-hard dick for all to admire as it peeked out from under his beer gut. It had some cum and trace of blood on it, the signs of successfully pozzing the punk who lay defeated under the stud's thick wide foot.

I was proud of my buddy and his conquest and turned on that everyone present hailed him as a hero for conquering the loser under his foot.

 

Craig stepped down from the mattress and some little guy knelt and sucked his dick clean and kissed it and his balls.

 

The punk was released. Once the gag came out he cussed a blue streak and tried to free himself from the men holding him so he could take a swing at someone. The leather cuffs were removed as two men restrained him. The punk looked defeated, the fight just about gone. 

 

 

The punk got dressed and one man said he'd take him home. The man gave us his number and said he was going to keep an eye on him.  The man would also keep in touch with the punk's uncle.

 

We were kept up to date and informed of his health. He caught the AIDS flu and was bedridden. The man who took him in didnt put his dick to him nor let anyone else get so much as a blowjob while waiting for the flu to kick in. he was sick for about a month. A month later the man taking care of him was ready to kick him out. He was taken in by a few of his uncle's friends and stayed at each place for a month or two. He eventually wore out his welcome at all of them and ended up on the street whoring for a living until he was no longer presentable. About a decade and a half later someone said he was found dead in an alley, most likely of the disease. During that interim Craig and I had fucked quite a few guys including bareback pozzing almost one a year and breaking two or three more total cherries.