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My Boy’s First Dildo

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1981virginia Specialist

1981virginia

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Hey guys. A new story for you. This'll be two chapters, and yes, the second chapter is already written. I'll post it soon. xxx

 

My Boy’s First Dildo

 

Chapter 1.

 

I’ll be the first to admit to having a solid thick six inches swinging between my legs. It’s not massive, but it is thick enough to stretch out a hole nicely. When my boy, Brian, and I started dating, I’d had a lot more experience than him. He’d had a few fuck buddies and a boyfriend or two, but he’d mostly just done oral. He confessed to me that he fantasized about taking POZ cum but wasn’t quite ready. I let him know that that didn’t freak me out and I might know a buddy who could help when he was ready.

 

In our first times together, I made it clear to Brian that I prefer to top. I can bottom in a pinch, but I much prefer to top, preferably raw, preferably in an opened-up hole that I can fuck for a long time. Brian and I had been casually dating for a few weeks and things got more serious. Our dates would end up at his place or mine, with us switching blowjobs and me eating his hole and loosening him up with a finger or two. Last month, he let me tease his hole with the tip of my cock, and then asked me to bag up to get the whole head inside. He said it felt so good that he needed to cum and shot a big load before I was more than two inches inside him. He wasn’t in the mood to get fucked after he’d cum, so it meant I needed to pull out and jerk off on his tight abs. We met up a few times a week until I was briefly balls deep, protected by a condom, inside him. It was like a switch. As soon as something went inside him, he’d cum, always without touching his own cock. I told him he needed to practice more so he’d let me fuck him longer.

 

I’d never been inside him raw and told him that as tight as he was, he’d make me cum immediately without the de-stimulation of the latex. I suggested we get him a dildo a bit bigger than my cock and we could properly train his hole to take my dick and eventually my cum. He thought hole training was a great idea and I told him we’d get him set up.

 

After work, we met up and I drove to a seedy sex shop. I called on the way over to make sure my good pal Kyle was working. I’d brought a boyfriend or two before to Kyle for his expert help opening up tight holes. I stayed close as we toured the shop, but let Kyle do the talking. I knew Brian was in good hands.

 

I introduced Brian to Kyle and we took a quick walk around of the shop, looking at some chastity cock cages, handcuffs and restraints, buttplugs, poppers, and some videos. I mentioned that Brian got off on POZ fantasies from time to time. He blushed but nodded. Kyle showed him a whole rack of bareback DVDs starring known POZ pornstars. Brian was practically panting and asked about different types of lube and toys.

 

Kyle explained the importance of good lube saying he’d never put his cock in drugstore lube again. Brian grinned and asked which was his favorite. Kyle smiled and showed Brian a tub of mineral oil-based cream lube. As he held up the jar, Kyle said, ‘this is my second favorite lube. Raw cum is my favorite.’ We all chuckled at that. He told Brian how silky smooth it felt, and how it was great for toys and even fisting, but not condom-safe. He explained that the lube might wear down latex causing it to break. Brian nodded and said that shouldn’t be a problem as he’d only be letting me fuck him raw. Kyle muttered, ‘we’ll see about that…’ and winked at me. I could feel myself getting hard.

 

Kyle showed Brian a selection of glossy black silicone dildos. He explained that these wouldn’t degrade with the oil-based lube. He went on about how easy they were to clean after play and asked Brian if he’d like to try it out. Brian gasped, ‘here?’ Kyle nodded and said the store had a strict policy of encouraging all customers to try out their toys before paying as returns couldn’t be accepted. Kyle asked me to whip my cock out, as if he hadn’t seen it before, so he could choose one a little bit bigger than me to get Brian nicely opened up. I unzipped my pants and Kyle took out a measuring tape. ‘Just over a solid six inches long,’ he said, licking his lips. I could see Brian blush, but I could also see him getting hard, and a nickel-sized dark spot of precum seeping through his jeans.

 

Kyle suggested that Brian get undressed and climb into the sling at the back of the shop. As Brian went into a fitting room to discretely change, Kyle locked the front door of the shop and hastily scrawled a note and taped it to the door.

 

My dick was still out when Brian came out, naked, and hard and drooling precum. Kyle and I helped him into the sling, and I gently placed his sneakered feet into the stirrups by my shoulders. I scooted his ass to the edge of the leather seat so his hole was hanging over the edge. Kyle suggested I get out of my clothes, so they didn’t get stained with the lube and I gladly obliged. Brian was grinning and staring at my dick, then directing his gaze to the toy in Kyle’s hand. Kyle’s other hand rested on his crotch, cupping what I knew to be a solid eight-inch uncut cock.

 

I knelt down and lapped at Brian’s hairy hole. He was so tight. I made sure he was having a good time and he eagerly nodded. I lubed up my finger and slowly worked it into his hole. His face alternated between a grimace of pain and a sigh of pleasure. He was really liking the lube and the anal stimulation. Kyle slapped the hefty dildo against Brian’s hole and I smeared some lube on it. Brian put his hands behind his head and told us he was ready. Kyle aligned the big-balled base to his crotch and pushed gently forward, using his body to keep Brian’s tight hole from pushing the dildo out.

 

Brian asked for more lube and I obliged, running my hands around the spot where the dildo was slowly slipping inside him. Brian looked at me and his eyes got big. ‘Hey, babe?’ ‘Yeah,’ I asked. ‘Do you think Kyle should take off his pants?’ ‘Why would he do that,’ I innocently asked. ‘We don’t want that lube splashing on his clothes, do we?’ I concurred and invited Kyle to disrobe.

 

Kyle gladly guided my hand to the dildo now partially embedded in my boy’s lubey hole and took a step back. He yanked his clothes off and his long cock tumbled into view. It was a good inch longer than the silicone dildo. Brian literally started drooling at the sight of that hole-stretcher.

 

Kyle stepped forward and reached to a cup mounted to the wall beside the sling. He got out a condom and opened it. Brian looked confused and Kyle pointed to his cock, now fully engorged, red, and a little angry-looking. Kyle’s cock was shiny and oozing precum. ‘I’m POZ, Brian. I should bag up, ya know, just to be safe.’ Brian looked a little dejected and I saw the beginnings of a pig born right there.

 

Brian nodded and Kyle slipped the condom on. It only went half-way down his shiny red shaft.

 

Kyle resumed his position, his body, naked except for a condom, lined up perfectly with my boy’s hole. He placed the base of the dildo to his pubes and gently eased his body forward. His sheathed POZ cock was inches away from my boy’s lubed-up hole and getting closer every second.

 

To be continued…

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1981virginia Specialist

1981virginia

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Chapter 2.

 

My boy moaned as Kyle fed more and more of that big dildo into his hole. He got it halfway inside Brian’s hole and Brian’s cock started to jerk. He shot three big volleys of cum straight into the air without even touching himself. Kyle kept his body where it was, solidly lodging the dildo inside Brian’s stretched-out hole, as he let Brian come down from his orgasm. ‘You like the oil-based lube, yeah?’ Brian nodded. ‘Well, feel how good it is mixed with cum. Brian gasped as Kyle pulled the dildo completely out of his quivering hole.

 

Kyle scooped up Brian’s fresh load and smeared it onto the dildo. He then took a swipe at my cock with his hand and grabbed a big pearl of my precum. He held it up for Brian to see and then eased it right back as far inside as it had been. Brian groaned and his cock jerked back to life. Brian’s whole body started quivering as he took more length inside him than he’d ever taken before. When Kyle slipped past a full six inches inside him, Brian came again, less this time, but still an impressive amount. He writhed in pleasure. As he moved around, the sling began to rock his body back and forth so he was fucking himself on the cummy lubey dildo.

 

Brian was moaning non-stop now and the scene was making Kyle hornier than I’d ever seen him. His long curved dick bounced up and down, slamming into the underside of the dildo. The tip of his sheathed cock was right at my boy’s hole. I could see Kyle’s copious POZ precum already starting to fill the reservoir.

 

Brian reached down and tried to grasp Kyle’s hips. In one thrust towards one another, Kyle got the dildo fully inside my boy’s hole, his own pubes and the base of his cock pressed against Brian’s ass.

 

Brian moaned as he came hands-free a third time. Kyle was relentless and sent him rocking further and further so the dildo plopped out momentarily before it was shoved all the way back inside. Kyle’s cock bounced up and down just as high as the tip of the dildo. ‘More,’ Brian exclaimed. ‘I need more!’ Kyle let the dildo fall out of Brian’s ass and he placed it on Brian’s belly. Brian looked up at him, then at me and said again, ‘more!’ Kyle looked at me and I nodded, as I’d done before, then he looked at Brian. Brian nodded too saying, ‘It’s ok. You’re safe! After all, you’ve got on a condom.’ Kyle shrugged knowing full well that that latex would not hold up long to oil-based lube. He said as much and Brian shrugged saying, ‘Just fuck me a little. You’ll have to pull out before it breaks!’ Kyle nodded and promised to do his best.

 

The weight of the precum-filled reservoir pulled the condom even further forward on Kyle’s shaft. I suspected that he’d lubed up his cock too before our arrival, which would help ease the condom off even if it didn’t break. Kyle asked for my help, and I grabbed the base of his big POZ cock, aiming it right at my boy’s quivering gaping lubed-up hole.

 

Kyle’s cock eased into Brian as he moaned and squirmed. Kyle slid so far forward that I needed to pull my hand back. ‘Poppers,’ Brian muttered. ‘I want to try poppers.’ I grabbed a fresh bottle and tore off the wrapper holding it up to my boy’s flared nostrils. He took a deep huff just as Kyle rammed his hips forward. He was balls deep in my boy, nothing separating them but a thin fragile sheath of latex. Kyle’s cock was so deep that Brian’s hole fully swallowed the base of the condom.

 

The two of them rutted. I knew Kyle’s big POZ cock was battering and bruising my boy’s insides, but he was loving it. He blurted out that this was his first time taking a POZ cock. Kyle oinked at him, and Brian oinked back. The scene got me so turned on that I knew I wanted to raw-fuck my boy’s open hole and fill him up. I stood beside Kyle and tapped his shoulder for him to back out. The condom was still on the tip of his cock, and still intact, but I’m sure some of his precum had sloshed into my boy’s guts. I said as much as I slid in, and Brian just groaned. Kyle got a fresh dollop of oil-based lube and jerked his barely-sheathed cock as I entered my boy raw for the first time ever.

 

He felt so good. Brian’s hole was more stretched-out than I’d ever felt it. He’d shot three loads and I smeared what I could and fingered it right into his lubed up freshly-opened-up hole. I told my boy I was going to cum and asked where he wanted my load, ‘Inside! Deep inside! I want you to fill me up! Breed me! Breed my pussy!’ He said that last part to me, but he was looking right at Kyle when he said it. I blasted my load six inches deep into his hole, more puffy than I’d ever seen it. My boy came again just as I was breeding him making his hole pulse on my cock.

 

Kyle scooped up my boy’s load and fingered it into his pussy. Brian looked up at him with pleading eyes, ‘Do it, fuck that cum into me. Shoot your load too!’ I knew he was purposefully tempting fate. I also knew that Kyle was glad to oblige. He slammed his cock fully into my boy and kept jackhammering his hips until his whole body was covered in a sheen of sweat. He shoved his hips forward and I watched his saggy butt flex as he shot his seed. Kyle leaned forward and kissed my boy hard on the mouth. I saw my boy’s cock bounce as Kyle pulled back. He pulled all the way back and his cummy raw cock plopped out of my boy followed by a torrent of fresh cum.

 

Kyle stepped aside and I knelt down. I lapped up that cum and inserted my fingers. Brian hadn’t seen that the condom had fallen off. I fished two fingers into his gaping ruined hole and felt the shredded condom. Brian’s cock bounced and danced as I swished my fingers around inside that sloppy hole. I slowly pulled the destroyed rubber out and held it up for Brian to see. As soon as he saw it, Brian shot his final load of the night. This time, Kyle knelt down and lapped up his seed. He brought his mouth to Brian’s and they shared a cummy kiss. As soon as Brian caught his breath he chuckled saying, ‘We’ll take the lube, and a dildo the same size as your cock, please.’ I was all too happy to pay and take them home. Brian promised he’d be back for more toys just as soon as his hole was ready.

 

THE END.

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