Unexpected DP while on vacation

Our first full day with Pablo included lots of hours lying at the beach, lots of drinking, and lots of oral and anal sex. Day two would kick things up a notch.

Sir Jace woke up when the sunlight hit us through the hotel room drapes. His hard morning wood pushed against my naked butt cheek. It felt hard and seared against my skin. I only woke up when I felt it poking through my sphincter. Sir Jace must’ve lubed up his hardon very quietly. My eyes popped open and I grabbed onto the pillow and shouted “oh fuck”. He caught me completely by surprise. Sir placed his hand over my mouth and I bit down while he finished pushing his inches inside of me. He began thrusting at a slow pace, slowly moving his lovestick through me.

Then he pushed me down onto my stomach and pressed my head into the mattress, all his weight and strength bearing down on me, leaving me practically immobilized as he continued impaling me from crown to base. “Ooofff oooffff” I muttered with each stroke. Sir Jace began to bellow what started as a low groan and built into a loud roar as his balls exploded it’s very first load of his precious seed deep inside me; marking his territory. My hole his personal receptacle, happy swallowing up his discharge. Thinking his breeding was complete I attempted to move, “I’m not done with you, boy, don’t move”. Shortly thereafter I felt a warm sensation and slight bloating slowly growing  inside of me. When Sir completed his morning piss, he rolled over and smiled. “That was nice, boy. Get cleaned up and bring me some coffee”, and he rubbed my back in an affectionate way.

Of course I went to relieve myself, made Sir some coffee how he likes it and brought it to him before being excused to shower and shave. When I finished, I laid out a fresh towel for Sir, dressed, and waited for him so we could eat together.

As we approached the outdoor restaurant, Pablo was sitting at a table wearing a tank top and board shorts enjoying breakfast overlooking the beach. He saw us and flagged us over to join him. “So what’s on the agenda today?” He asked. Sir Jace suggested after breakfast perhaps a walk around the resort before hitting the pool. So that’s what we did. Wearing my next to nothing blue speedo bikini and his collar around my neck left nothing to the imagination. There were many stares, especially to my crotch as the Cellblock protruded. Sir just held his arm around my shoulder as if everything was completely normal, while I felt a tinge of embarrassment and humiliation.

Sir could sense I was becoming a little agitated. “Come on, boy, I think we’ve wandered around enough, let’s go to the pool”. So we did. There was fun and frolic. With each daiquiri we drank, Sir became more assertive, pushing me against the pool wall and making out with me heavily. It was clear Sir Jace was a man of considerable confidence. He doesn’t care what anybody thinks. I respect and admire him for that, and at the same time, I’m humbled by it. Pablo watched the show off to the side. When Sir slid his hand under my bikini to squeeze my ass Pablo interrupted, “maybe we should take this upstairs?” Sir nodded, “yes, let’s”. Sir smacked my ass and barked, “move it, boy. Wanna get into that ass”.

Pablo followed us assuming he’d be participating in our sexual perversion. As we walked into the room, Sir went to take a leak with the bathroom door open and said, “hey, you wanna try sliding your fist up his ass? I’m gonna give him my fist and stretch that hole wide open.” Pablo said, “I’ve never done it. It’s ok?” Sir assured Pablo that he’d walk him through it, and even told Pablo about our new friend Tyler back home who just fisted me for the first time a few weeks ago.

As he spoke, he laid out towels on the bed, poppers, and a tub of elbow grease lube. “First we’re gonna fuck him and fill him up good, then we’ll open him up.” Sir loved to show off and take charge, especially when he has an audience. “Boy, get over here and show our guest some respect. Get that cock of his nice and wet”. Sir stripped and sat on a chair watching me bob my head on Pablo’s raging boner and when I could sense he was going to blow, I quickly turned around, jumped onto the bed, on my back, legs spread and presented him with my aching hole. Pablo walked over quickly, jerked himself a few times before he pushed inside me, ejaculating that warm load into my guts. He just inseminated me with the first coating of lube needed for a successful fisting.

Sir Jace pointed over to me with instruction to clean Pablo’s cock, which I did sucking off its deliciousness. Sir mounted me from behind and because he’d been jacking off while watching me service our friend it wasn’t long before I’d had his load swimming inside me. Damn, within 15 minutes of returning to our room I’d been bred twice!

Sir Jace said “now I’m gonna start working that hole open”. Sir had me inhale some poppers as he’d began to coat  his fingers with elbow grease. I let out a deep sigh and relaxed feeling Sir’s fingers slip inside me and begin to circle and swirl. Oh how I loved this part. The slow working over of my hole, building to a most thrilling adventure. We were just getting started. Sir rotated and played in my hole, working 4 fingers inside. Pablo was now kneeling in front of me. We kissed, I blew him, he stimulated my nipples, I was having fun with him as Sir watched us enjoy each other.

I did notice that Sir didn’t seem to go further than 4 fingers, when he finally spoke up, “boy, you’re a little tight today. I think I know what we can do to fix that since we didn’t bring any of your toys”. Seeing Pablo’s hard dick, he said, “get on your back so he can mount you”. Once a straddled Pablo, Sir pushed on my back slightly. I was so slick and wet, his hard cock slipped inside and now I had another unexpected double dicking. I could feel my hole loosening as Sir used his hard cock as an instrument to pry my walls open, moving his pelvis round and round so the head of his cock brushed against my anal walls, pushing them out. This was brilliant, and with the added sensation of poppers I was on cloud nine.

I think all of the contact of Sir Jace’s cock was just too much stimulation for Pablo. He pulled my face to his and we kissed passionately as his breathing intensified and his body shook. He’d erupted once again inside of me. When Sir Jace began to drill my hole, Pablo slipped out. Now I was full of cum slime, full of elbow grease, and Sir’s 9” felt small, if that’s even possible. My hole just swallowed him up. He made quite a mess smashing inside me until he gave me his load.

I hungrily ate all of the cum dangling off his cock and balls, even if the elbow grease interfered with the taste. I was wild and completely uninhibited at this point. I spun around and presented my ass to Sir Jace. This time I was really hungry and really wanted to feel that big fist punching my ass out. Sir reapplied a generous coating of grease to his right hand and brought it towards my hole. “On 3 boy, I’m going in”. I was much looser by now thanks to the double dicking, I took another hit and pushed out when Sir counted down, and with a loud splash, Sir had buried his hand into me. Pablo now watched on, I could see his eyes watching me and watching Sir. He was definitely enjoying the show.

Sir said, “why don’t you have the honors of breaking his second hole open. Get your hand nice and greasy and come over here”. Sir slid his hand out, and he showed Pablo how to form his hand into duckbill position. I hoped he’d have a collapsible hand for easy entry. His hand being smaller than Sir’s, he fit inside easily. Sir said, “ok, now I’m gonna grab his torso so he doesn’t move and you’re gonna push hard up inside so you get up in that second hole. You ready?” Pablo nodded and the two studs coordinated their efforts to breach my second sphincter. Pablo’s hand was truly miraculous, sending waves of pleasure as he he pushed deeper inside of me. I may have even pissed myself!

Sir Jace worked with Pablo to guide him into balling his hand into a fist and moving his forearm back and forth, Sir adding lube up Pablo’s hairy forearm. Pablo’s forearm widens toward the elbow, so now I was stretching like rubber to fit him inside. He seemed to really enjoy it, and then Sir coated Pablo’s other fist up liberally and before you know it, this novice was body punching me, like he’d been an experienced fister all his life! I was out of control. Sir had to add towels below me because I was pissing like a racehorse, and it was truly fucking incredible to be on the receiving end. Delight? Jubilation? Bliss? Ecstasy? All those words and more to describe it! Once you’ve hit that high in your life, you always want it back again and again.

Pablo seemed to be tiring out. Sir began to lube up his right forearm. He had Pablo leave his forearm inside me, and lined up his hand over and to the side of Pablo’s and began to push in. With Sir’s much larger frame, this was an even larger stretching but my hole was completely wrecked and had no give at this point. Sir grasped Pablo’s hand inside me and they formed a larger fist, and when that first punch hit me, I almost cried from the pleasure and the agony. A real fuck puppet I’d become.

Sir and Pablo continued to play inside my wrecked hole for quite some time, I could see the sun begin to set and I’d become a complete incomprehensible idiot, poppered up and useless. With all of the physical effort of the fisting, the two men had worked up such a sweat and Sir became horny as fuck. “Well, that hole ain’t gonna do us no good now, I think we wrecked it”. He flipped me over like a piece of meat, hung my head over the edge of the bed and skull fucked a load into my throat, I was so slack I hadn’t a gag reflex. Pablo took his place only he shot all over my head and face.

We all fell asleep exhausted from the activity. I honestly thought my cunt would prolapse and be wrecked for life after that session (that didn’t happen). It was now pushing 10pm and we’d almost missed dinner. After dinner we exchanged contact information with Pablo, kissed him good bye, thanked him, and wished him well.

Sir and I still had 2 more days…but my hole was worn out. That never stopped him before and it wouldn’t now.