Boots

With our short break out of the way and fully refreshed, I finally stripped to match the nakedness of the others. I’m nowhere as muscled as Dillon but I was without a doubt the man in the room.

I had the boys’ position themselves on the bed doggy with their arses facing me.

“Are you going to fuck us?” Asked Bill with a tone of excitement.

“Not yet, with virgin arses like yours you have to take it real slow, don’t want to tear or do any damage. Best to do a little stretching, take some time, make it fun”. I applied lube to their butt cracks and gently worked a finger into each. Bloody hell, these guys were super tight. They weren’t kidding when they said ‘nothing’ had been near their chutes.

I slowly and sensually worked their holes, gradually opening them up little by little. They were really getting into the attention I was lavishing their butts. When I had finally managed to get two fingers in and out with ease, I set about stretching them that little bit more. I inserted a butt plug in each and left them in place to continue the subtle expansion.

“On your backs”, I quipped as I playfully slapped each on the arse. They rolled over and as could have been predicted, were almost hard again. “There’s no limit to fuck positions but if you’re the one doing the fucking, this is the last one I want to show”, they nodded as they lay side by side, full attention. I glanced at Dillon confident he’d know what was expected from how the guys were laying. He scrambled up on the bed and, on his haunches took Ted’s meat and slid it into his pussy. The boy was enthralled. 

“This is good, it lets a ‘bottom’ like Dillon here accept the cock at his own speed. If he’s new or not used of the cock size it lets him make sure there’s no risk of going in too fast. Fuck’s pussy is well used of cock so he doesn’t have to be careful. Later when I’m fucking you, I’ll lay in the same position as you are now and let you take my meat as best you can.”

Dillon was now fully bouncing on Ted’s rod, driving the guy a little crazy. Just as the boy looked like he was getting ready to blow a third load, Dillon hopped off and sat on Bill. The surprise from both fuckers was great to watch, one of disappointment and one of delight. My toy was doing a fantastic job.

As he rose himself up and down his semi hard wood rhythmically struck the guys across their perfect abs, it was great to watch. At one point Ted reached out and took hold of the wayward meat springing up and down before him. I gently pushed his hand aside.

“Today it’s about making sure Dillon’s sending your cock crazy. Might be different if you’re with someone else, but here, don’t distract him from his job, here, his dick is just in the way, follow?”, Ted got it. Dillon didn’t miss a beat, never considered playing with himself. My collared boy had come so far, I was actually proud enough to scruff his millimetre length hair. I reflected that next week he was booked to get a sizable cock ring pierced into his piss slit. No more standing to urinate like real men, I smiled to myself.

Seven minutes later with excellent skill he had both absolutely on the edge of exploding. Holding eye contact I directed him to kneel on the floor beside the bed. The guys had no idea what to do.

“On your knees”, I directed to both. “Blow your loads on his head, face”, they were thrilled by the idea and immediately got to it. Being their third I hadn’t expected their nuts to have much left but I underestimated teen seed production considerably. They covered my fuck in thick creamy ropes, it clumped in his clipped hair and dripped, hanging down his brow and face. He knew not to wipe it, it would dry in place.

The three of us sat comfortably across the bed coming down, Dillon remained on his knees on the floor. We chatted, smiled and laughed about what they were learning and the exciting world of sex adventures opening their minds. Their innocence was effervescent.

In a conversation lull Bill reached out and stroked my mat of chest hair, I don’t have much body hair but I was by far the hairiest guy in the room.

“I don’t think I’m going to get much more hair”, the boy lamented. I agreed and told Ted I thought he was in the same boat. Bill’s hand slipped down to my junk, he took my rapidly hardening length in his grip.

“Are we going to fuck? I’m so horny, I want your cock bad”

“Maybe”, I replied, alarming both, “I fuck different to a lot of guys you might get with”, they looked at me quizzically, “How do you think I fuck?” I asked. They went into thought, but came up blank. I looked to jizz covered Dillon.

“It’s all about him”, was all he said, they both nodded smiling, getting it.

“So, we’re just gunna be like ‘little holes’ to you?”, Asked Ted, I agreed.

“That’s how I roll”, I confirmed with unflinching confidence.

“Cool!”, expressed Bill with Ted wildly in agreement beside him. “You gunna fuck us hard like you do him?”, meaning Dillon.

“Well, not so hard at the start, you’re new. Maybe in a later session” I added

“Fucken ace!, Can we go now?”, pleaded One “I’ve been thinking about it for months, ever since we met on the beach”

Without saying a word, I arranged myself to one side of the bed, flat on my back. I reached forward and pushed my rock hard meat vertical.

“You’d better sit on this then”, I grinned. ”Lube up, and take it easy, we’ve got all night”. Bill scrambled to get himself organised. He carefully pulled the plug from his arse and as he did I motioned Dillon to open his mouth to accept it. He did without batting an eyelid.

With the blockage out of the way he added lube. He was about to sit when I told him to slick me as well.

When he had himself in place I felt my cock head at his rose. The plug had done its job, his ring opened easily to at least let in the top third of my cut head. As he increased his downward pressure, I felt his arse expanding to cope, fuck he was tight. To his credit he didn’t rush. From time to time he paused to let himself catch up. Ten minutes later he was sweating, and about three quarters of the way home. He had dealt with girth, now it was all about length. With huffing and puffing he made it. His arse rested lightly on my balls.

“Holy fuck”, he declared, “wow, I fucken made it”

“What does it feel like?” asked Ted in anticipation.

“Feels fucken awesome man, I’m so fucken full. Been wanting this for so long, just thinking about it, all the time. Finally taken cock, a man cock! You won’t believe how good it feels”, he was beaming, thrilled.

He focused and raised himself a little, just quarter of the way up before retreating back down. His facial expressions were sensational. He picked up a little speed and was clearly having a fantastic first fuck. He worked his rod back and forth, I knew he was close to coming. I nodded to Dillon to get in place.

“Oh my god, oh my god”, he relayed “I can’t believe I had to wait so long for this”. I smiled to myself as Dillon rested his head on my abs, ten seconds later he was coated in his third fountain of youth for the afternoon.

Bill remained almost frozen in place. I suspected it could have been the best orgasm he’d ever had. I didn’t actually care, his brand new chute felt fucken amazing around my cock. I looked forward to really fucking him, now he’d been broken in.

Ted almost pushed him out of the way in his rush to gain access to my cock. Dillon had retreated with his fresh cum coat still dripping down his profile. He looked positively fuck slut, very hot.

With the way clear, Dillon ended up with a second plug in his mouth. Ted followed suit and aligned himself for entry. I knew instinctively he would rush, so I put my hands between his arse and my junk to deliberately slow him down, at least in the beginning. I wanted his hole later, there was no way I was going to let it be damaged now.

In time he worked himself lower and lower, he turned out to be much more vocal than his counterpart. His ring expansion seemed directly linked to his mouth. His freedom of expression was youthfully excellent, I really enjoyed his seven-inch journey into post virgin reality.

When he had reached bottom he knew he’d made it.

“You’re fucken right!”, he said looking directly to Bill, “totally fucken sick man! I knew it would be wicked, oh fuck, oh fuck”. He set about establishing an arse electrifying rhythm, the feeling up and down my shaft shifted to amazing.

It didn’t take him long to complain about how close he was. Of course, stimulation momentum wasn’t sacrificed because of it. His brain simply couldn’t surrender one for the other. Dillon didn’t need prompting and set about getting ready to receive another load. When it arrived I mused to myself how my fuck now had four inside and four on his head.

Ted almost fell off me, in afterglow heaven.

As they recovered and excitedly chatted on the bed I relieved myself in the bathroom and readied for my turn. I had yet to cum and fully intended to address the situation immediately. I fussed around in the cabinet and fished out the two items I cheekily bought along with the butt plugs when the boys’ first started texting me.

When I returned to the room I had each kneel on the bed. I clipped a small collar around each of their necks. It was less pronounced than Dillon’s, I didn’t want to destabilise him.

“Really?”, said Ted, “we’re holes?”

“Little holes, just for the day”, I added, laughing, “a bit of fun, not meant to be like Dillon’s. His is lifestyle, yours is about me fucking you properly, on top this time”

“Fucken Ace”, declared Bill as I manhandled him to all fours and where I wanted him. With him ready and waiting I lubed up and placed my cock at his opening. He held fast as I pressed into his now adequately stretched hole. I still took my time but when I was fully home I knew I could give him a solid go without damage. I moved to fuck master mode, and did.

Over ten to twelve minutes I pumped the boy soundly. His arse was sweet heaven. I pushed him to the bed top and drilled him to the mattress as if he was bolted there. I had a fucken great time and worried little about his ride. As I felt my balls lift I lent down close to his ear and let my full body weight rest along his length. With my ankles locking his knees wide, I whispered directly to his brain, one on one.

“Gunna make your arse mine forever boy”, I said quietly with utter fixed conviction, “seed your pussy boy hole”.

“Do it!”, he croaked, covered in sweat and almost beside himself in delirium, “do it, I want you to be the first”. I increased my tempo and filled his arse. It was excellent! I collapsed and let myself overwhelm any movement he may have wanted to make. I stayed in place until I felt him utterly surrender.

As I lifted myself my head started to clear.

“That was fucken amazing to watch”, declared Ted in awe. “Do you always do Hole like that?” he asked.

“Not that gentle”, I answered almost recovered and sitting up.

“You fucken won’t believe how good it is”, said Bill to Ted, lying where I’d nailed him. He hadn’t moved.

When I had re-hydrated and cooled down I immediately set about taking Ted’s real virginity with a vengeance. I had him lie on his back for something different but fully intended to finish up the same as I had ploughed Bill. I slowly worked my cock into his super warm hole. The vocal utterances of the first round continued to electrify the fuck. He was totally into it by the time I was all the way home.

With a full stretch achieved, I set about fucking him up down and middle, it was fantastic. I genuinely had a ball. As a second round cum he’d get a longer experience than Bill, I took my time to do him well.

As we progressed I set about rolling him towards having him fully face down. During his rotation I paused, to sit along his lower leg while holding his other one up my chest. I fucked him scissored as deep as I could. I blew their minds.

When I finally had him flat on his stomach I sawed his arse. Not as brutally as I regularly did Dillon, but rough enough for the guy’s second ever entry. By the time I felt the familiar nut tingle I was drenched in sweat and on fire. I pinned him to the bed and again went directly to his ear, the message between him and me.

“My cum is gunna fill your arse”, I murmured lowly to his mind, “as my seed soaks into your body I’m making your fuck hole mine, today, tomorrow and the rest of your pussy boy life”

“Oh god, that’s all I want, we want”, he cried heartfelt, tempting the edge of delirium, “all we’ve talked about since the beach, do it!”. I exploded as deep inside him as I could.

It took an age to get my breath back, I had worked hard. As before I used my body to hold him in place, until I had complete capitulation. Holy fuck it was fantastic, amazing fun. I rolled off and took a minute to fully enjoy the after effect. Every nerve in my body had been activated. I turned to Dillon and making sure I didn’t break the mood, asked him to turn on the shower, and order pizzas. It was time for a real break, we’d been at it for more than four hours.