Installment number Nine of what was probably the best party weekend of my extensive "career" - back in 2006 in Provincetown. My hubby was in New Hampshire at a 4 day business convention and during those 4 days he was happy for me to do my partying in Ptown ,  with him joining me after his convention for his much more vanilla style non-enhanced sex. Thursday night my buddy Jimmy hosted a hot orgy for me but had to change Friday's plans for a personal emergency, as did Lou the local candy-man, who had an emergency leaving his assistant "Vice" a straight but hot Portuguese local guy to spend the day pnping with me - with Boston frat boy type Kieran (also staying at the guesthouse with his revealed to be former partyboi husband Charlie),  Karl and the other Houseboys and the skinhead Manager Zar. Then an old friend – an Episcopal Priest no less – shows up in time for the party.  This amazing weekend took an entire notebook to cover (I've kept sex diaries since I was a teenager) and never before or since has ONE weekend taken up an entire book. So along with me - at the time a 43 year old jock muscle leather guy - Caucasian, blond/blue - we pick up the story during the storm-caused power failure, and our str8 boy gets booty-bumped one too many times and pulls me back to my room because he needs to be fucked NOW...

 

We were in the midst of thanking each other profusely – me for offering me his cherry, he for me waiting for him to want it then doing so well – when a key turned in the lock and Lou peeked around the doorframe.

“Finally.” He commented. “Thank you, J-man, you are impressive.”

“Daddy-J is a master of his art” (which he pronounced ‘ahhhT’) replied Vice to Lou, “now shut up, get in here and fuck me!”

 

SATURDAY, 2AM and BEYOND: IN THE WEE SMALL HOURS OF THE MORNIN’

I laughed hearing the deflowered stud in my bed demanding more cock in his ass. Lou looked really, really pleased and fished in his pouch for a big rock to drop in the waterpipe. Sparking the torch, he melted the rock as Vice and I looked on, then took a big rip off the pipe and smiled.

“So,” he began as he blew out his cloud. “You liked it then?”

“It’s wickie hot,” was Vice’s reply as Lou took what looked like another massive hit. He then handed me the pipe and torch and pulled Vice in for a shotgun that turned into a major tongue-wrestle between them. As I took a big hit myself, Lou and Vice finally disengaged, their cloud dissipating between them.

“Feel any less like a man?” Lou continued his line of questioning. Vice shook his head several times then said: “Nah, it’s just like J-man here said, you can get fucked and still be all man… I totally get that now, J,” he looked to me as he finished. “And damn it feels hot as fuck too. Just like me fucking ass, I gotta try out a few more samples. For instance, I just had some amazing white meat, isn’t it time for some dark meat now?”

We all laughed. After passing the pipe and sharing shotguns between the three of us, Vice looked at Lou and said, “You been wanting a piece of this for a while, ain’t cha’ bro? Been jonesing for some fine straight-boy hole?”

With a big smirk, Lou replied “you don’t know the half of it homie… Been jonesing for that super ‘fine’ tail for a while – givin’ and takin’ now? Dat’s fly… jus’ wha’ I need for a real wingman, yo.” I was chuckling to myself as both of their speech patterns went totally street urban all of a sudden while they teased each other. I mean, Vice always had the Bahstan-Capecadd drawl to a degree, but he was unconsciously laying it on thicker now while Lou seemed to be able to turn on and off his “Official Only African American Dealer In The Town But Customers Expect It” Urban Patois that he obviously got a kick out of using when it was fun for him or when he wanted a customer or any possible threat to think that’s all he was… and hey, it certainly comes across strong, confident and badass… smart dude that Lou.

Seeing the rabid looks they were giving each other, I hopped off the bed and quickly removed almost all of my leather, grabbed a towel and my bath kit and my key and said “Sounds like I should give you guys a few… gonna go piss, shower and wander. How long should I stay gone?” “Only 15 or 20,” Vice replied, “I wanna’ try out that ‘Lucky Philippe’ thing you talk about.”

“Lucky Pierre” I corrected, and you’ll love it, see you in a few…” I saw Lou lining his chocolate cock up with Vice’s hole as I closed the door and headed to the shared bathroom. Just as I was heading in, a guy stopped me in the hall. This was an older gent, probably the oldest guest in the place that night – he’d been one of the gladiator movie fans from this afternoon and had to be 75 if he was a day, lean and wiry, his white skin tanned like well worn leather, about 5’6” and a few tatts that looked genuine Navy like the vintage white sailor cap he was sporting over his silver buzz cut, white canvas deck shoes and a military surplus jock completed his attire. “You needing to empty the tap, sir? Why waste it on the porcelain?”

Pleased with his nonchalant request, I figured, why not? “Sure thing Sailor, but you better know that this is definitely high-octane and very much not plain unleaded. That okay?” He nodded, “damn sir, that’s a bonus!”

“Okay Sea-dawg, front or back?” The armband on his thin right bicep was black so that wasn’t an issue. His face lit up as he answered “Back, back please. Much better bump from your fuel that way… don’t worry, sir all clean.” With the caverject shot still in full force I was hard again almost immediately. He wasn’t really my type, but he’d kept trim and the grin on his face and the twinkle in his eye were enough for me to recognize a fellow player who enjoyed the game as much as I did and probably didn’t get to play as much anymore… and yeah, this would be me someday too, so l gave this Korean War Vet/New Chembuddy as good a quickie as I could, I remember hoping karma would come back to me someday in the future!

I started to bring him into the restroom, but he asked quietly “out here?”. Which made me grin, and made my cock a bit harder, as I turned him and made him do a perp stance facing the wall in the hall, arms up and legs spread. He was lubed but freshly so, and I still had plenty on my tool that a bit of spit got us wet enough for me to slide right in… warm velvet I have to admit. We were near the edge of the now slightly dimmer emergency lighting and seemed like a few guys were watching from the shadows, so rather than give him my chempiss right away, I gave him a nice steady firm mid-pace fuck for a couple of minutes – he had nice muscle control I must admit. “Damn” I said out loud to please him as I pumped him while reaching around to tweak his pierced nips, “you may look like a salty dog, but you’re still an able-bodied seaman where it counts sailor.” (My several times playing Lt. Cable in “South Pacific” were serving me well here…)

“Oh yeah, Cap’n, you like that Squid Hole?” he groaned back. (How do I always wind up an officer?). I switched to a slow screw that I knew couldn’t last more than a few minutes as I seriously had to piss by this time, and I wanted to end with the piss so we didn’t mess up the hallway – which would happen if I continued a fuck on a piss-filled hole.

That was when I felt a fat warm cock slide into MY hole while a soft hairy belly from someone rather large covered my back and two hairy arms slid around me and started seriously tweaking MY nips, and both felt great. A grumbly voice spoke in my ear “You like filling my man’s sweet ass? You’re making him so happy I had to find some way to repay you.” I figured this must be the Bear from the afternoon’s Gladiator group who was sitting at the time with the Vet I was pumping now – seemed to remember thinking he could play Santa Claus at Macy’s without any false hair, false beard or false belly… hell, it worked for the moment.

“His ass is like velvet, man, and you feel great back there too, BUT I was just supposed to be emptying my chempiss in your salty dog here except when I slid in I just couldn’t resist a little bit of a fuck before I empty out. And I have to empty out SOON. Seriously, almost bursting here.”

“Okay, just let me have a minute or two more, I’ll pound you, you pound him – he can take it – then piss away!” Which is what we did. Maybe another 20-25 hard pounding strokes and I felt Santa shudder and jerk as he dropped a load in me while my battered bladder finally let go and filled his partner with a good amount of high octane chem piss. The naval dude just sighed and said, “Thanks Cap’n, anytime you need a snug harbor…”

“Thanks for that, both of you” I said to the pair as I finished pissing and quickly popped out of the now squishy hole, “but now I have to do a quick shower and run…” Santa wiggled his eyebrows at me, asking “Your straight boytoy waiting to fuck you some more?”

I couldn’t resist.

“No man,” I replied with a smirk. “My pet straight boy begged me to de-virginize his straight hairy ass, and he’s waiting for me to fuck him again – our dusky friend is filling the void for me right now, and I want to get back…” Okay, okay, I was actually bragging… wouldn’t you?

The look on their faces was priceless – and Santa’s cock jerked up a couple of times on its own and dribbled out a bit more jizz. I swiped my finger through it, licked it off my finger and gave a quick but proper salute then sauntered into the bathroom. In unison behind me I heard two male voices whimper “Fuuuuuuck…”

Within a few minutes, I had dumped lube and load out of my butt, did a spot clean, showered the outer layer of sweat and lube off, gargled some mouthwash and headed back to “my boys”. Entering the hall from the shower I realized the power had gone back on while I was in there – the red lighting from the beginning of the evening was back, looking around I noticed that there were less doors open and a few more “do not disturb” signs out as some guys, especially those not enhanced, got tuckered out and finished up their play for the night. I took a quick detour back to the stairs to the third floor and went part way up – the door to room 38 was only barely cracked, but it was evident that there was still a good bit of activity going on in there – as I tried to get a better handle on how things were going in there, the door creaked a bit more open and Sebastian popped his head out. “Just checking – we are going to need another fifteen minutes or so,” I whispered, “do you want the three of us to come back up?” Nodding his head with great emphasis, Sebastian replied “Oh very much so yes, things should go on for at least another two hours… oui, yes, come… come soon!” Promising we would, I headed back downstairs and slipped into the room. “Ready for me?” I asked as I came in.

One of the room lights was now on, and I saw that Vice was fumbling around – gently -by my laptop while Lou was pulling drinks out of my cooler with one hand and holding his monster water pipe with the other.

“Sweet, hand me one of those gatorades, man,” Lou tossed me a lemon-lime, my favorite and I feel like I emptied half of it down my gullet in 30 seconds or less, “thanks, I needed that. You boys enjoying your new activity!”

“Mmm-hmm-hmm” was all I could get out of a smirking, grinning Lou, while Vice replied, “Indeed we are, but I’m glad you are back, I need to examine these two styles side by side. Mind blown, J, mind blown!” He chuckled to himself a bit then looked down at what he was doing. “Oh, but first, when the power went back on, your machine booted itself back up but it seems to be freaking out a bit. I tried to calm it down, but you’d better… and maybe put on some more hot stuff now that it’s not on battery anymore?” He couldn’t have looked more like a little boy in that moment if he tried. The problem was easy – the dvd drive kept trying to engage, but no one was pressing “play”. I put in Hot Desert Knights with a leather theme and took the offered bong and shared a few rips with the boys.

I let them know the gang upstairs would be happy to have us return if they both wanted to AFTER we schooled Vice on “Lucky Pierre”. Since he’d spent the last little while being dicked by his bud’s weapon, it was time for him to fuck Lou while I sandwiched Vice from behind. Lou lay on the bed and raised his legs to the sky while Vice and I spent a minute or five tonguing that hole and Frenching each other with a few more clouds, then Vice got to his knees and grabbed Lou by the ankles and pushed in. “Ooh, hold a minute” asked Lou. “Seriously? You been fucked all night man,” I kidded, “not enough lube?” “No, dammit,” he replied, “freakin’ CHARLIE HORSE”, which made all of us, even him laugh out loud. I took those few minutes while he and Vice kneaded Lou’s calf muscle (with Vice still fully inserted) to rim Vice’s magnificent no-longer-virgin ass, getting it a bit more ready. “Done!” Lou said, “now get that daddy dick in the boy here…”

On my knees I entered Vice from behind while Lou held poppers under his pal’s nose – I slid right in like Brett Gardner stealing Third in Post Season… damn life is good sometimes, right? Both my boys were moaning and talking nasty and seemed to be in heaven, myself likewise. Vice commented finally – “this is the most amazing sensation my body has ever had, no wonder this is your fav, J Daddy!” A minute or two later, he called ‘switch’.

I stood at the edge of the bed sitting on a pillow, rolled onto my back with knees to my chest, then pulled myself back to the edge so that my ass was partly off with the pillow wedging it up, then I reached over pulled the other pillow behind my neck got my knees behind my elbows and said, “Ready boys.” Like I did before, Vice and Lou attacked my hole for a bit with tongues and clouds, then with a huff of Max Impact off a sweat sock, Vice once again sank his thick linguica into the guy who took his virgin hole. He was getting REALLY good working a man’s hole, and when his eyes widened a bit and then slowly closed in a blissful expression, I knew that Lou’s chocolate delight was re-finding its new home.

“Fuuhuuhgh, so wickie hawt, yeah, yeah – how do you dudes ever STOP doing this?” Lou and I both chortled a bit about that, and I answered, “that’s why I try to do it so often, right?” The expression on Vice’s face was one of sheer bliss. Lou caught my eye over his shoulder and murmured “get ready to do that muscle contraction thing you do with yo ass J-man, we’re going to send him to orbit from both sides…” I nodded and Lou raised his voice to a growl in Vice’s ear “Welcome to Nirvana man – there ain’t not going back to boring ass vanilla sex now!” Vice’s eyes shot open as Lou began a wild rough triple beat pound on this now ravenous hole of Vice’s while I worked my muscle magic on that hot cock of his at the same time… the poor kid looked like he

was about to hyperventilate.

“Fuck, fuck, fuck, yeah, Yeah, YEAH… FUCKIN HEAVEN BROS!!!” Vice bucked and heaved, then stuck both arms straight out to both sides and bellowed “STOP! … MUST BREATHE!” All movement came to a halt as the Dealer stud and I smiled at each other with the newly initiated stud muffin between us collapsed on my chest, tears streaming down his face as he laughed, giggled, panted and moaned “so good, so wickie good, so fuckin good…” and then laughed and cried some more hugging my chest, then kissing me and smiling “Oh daddy, so so so good… but I gotta have five to pull my soul back inta my body man… and then we go upstairs.”

“Excellent,” I responded. “That’s my wingman,” said Lou. As his chest slowed down from it’s heaving, Vice was laughing again “Nothing came out of my dick, but it felt like the most powerful cum I ever had… as good as when you fucked me to jizz without touching myself, J-daddy- not better cause it couldn’t be but LONGER. The two of you might kill me but I wouldn’t care.”  His breathing slowed some more, then he smirked at us “I realize I have two professional level players here with me, but I’m new, we’re all high as fuck and they are out there wanting us to join in… can we?”

“Hell yeah,” I said, “But do something for me. Enjoy getting more cock and more ass, but trust me if you want to take on Marcel, leave him for last and let us get you ready – everyone else should be fine.” I went to the closet and pulled a few things out; “let me set you both up so they think the whole master and his boys things is real since it seems to turn them on – AND it also allows me to protect our newbie here since they all seem to hop to my commands even Marcel, so… first of all, a subtle change…” pulling most of the leather off of Vice, I pulled the second black ribbon out of the wrist band and wrapped it around his right arm so he had two like Lou and I did, “don’t say a word, see who figures it out first.”

“Devious, J-man, even I could take lessons…” Lou quipped. I put them both in black cloth baseball caps not exactly matching but close, same with two white jock-codpieces (the waistband stays on but you can unsnap the pouch so your cock is free and it still has straps in the back to frame your ass perfectly, each with thick rubber cock rings, leather thongs tied around their biceps on both sides right under the ribbons, white sweat socks, and leather and cloth wrist wraps that could be locked together so one’s right wrist was connected to his buddy’s left and they’d need to walk in tandem. My master’s cap, my full metal harness, leather vest and a black leather jock-codpiece also with removable pouch, chrome taint tickler thick cockring, my engineer boots and we were ready.

“What, no leash and collars for us?” Lou joked. I took his hand, showed him my pale hand by turning it back and forth right over his, then took his dark hand and flipped it back and forth, then put them together showing the contrast.

“Hell no,” I said seriously, “if you ever want me to do that in private fine, because to me it doesn’t matter whose got more melanin and whose got less - and is fucking jealous!!” which made him laugh in that grave moment, which was good, “but with these guys? Some of whom may have the issues we talked about and joked about earlier? No way will I denigrate you that way or have them think that just cause you’re “my boys” that I think of you as anything less than me or that you are in a servant position to me, no. I just won’t do it. There’s too much real shit out there without having to add to it for a fantasy or for show. Hope that’s cool, but not me.”

Lou just grabbed me and planted a huge kiss on me, his eyes looked a bit wet. “That. That… damn man, look what you did to me you righteous fuck you! Respect man,” he touched his heart and looked down for a bit. “Respect” Vice just goggled at us during this whole exchange.

“Well then,” Lou announced. “Since Daddy J will NOT be Masta J, for which I thank him, then let’s go up there with heads held high, cocks half hard and asses primed and SHOW THEM MOTHERFUCKERS HOW ITS DONE!”.

Laughing our asses off we made it to Room 38, were welcomed heartily with clouds and booty bumps and kisses and gropes and rimming and more clouds, and Zar being the first to notice Vice’s “change of status” to versatile and so claiming “DIBS!” while the rest swarmed Vice like frat boys getting free pizza, so I stepped in front of my newbie, and got into my Daddy/Boy role play persona while holding out my hand, between the Tina, the fog of long pnp play and the hot situation, I was really chewing the scenery as we say, even getting bombastic but man it was fun.

“Just understand something here. This boy of mine is special, and he asked me to take his cherry tonight – and I did, then his brother there added his skills too. And my boy liked it – he liked it a lot, and he’s gonna be an amazing switch hitter, but on this special occasion, he wants to try a few more… and I gave my permission, I WANT him to enjoy this and so far he’s had remarkably little pain and let me be clear, it will STAY that way. Get it? Now he’s a real man and so I’m not saying you can’t fuck hard or get a bit rough or wrestle it up some, but this is his first damn time and I promise you he will enjoy it or you will answer to me. So no games with not enough lube, or scratching him up, or pushing too much in too fast or making him bleed, or any shit like that. Understand? I want him to WANT to do this again, so don’t fuck this up. Right?”

Head nods all around and it was all I could do not to crack up – they all took me at my word and only the brief smile of gratitude from Vice and the furtive look of merriment on Lou and to be honest, Zar’s faces let me know I had a few appreciating my over the top performance. But I was being honest, I wanted the kid to like this, not wind up bleeding and in pain and never repeating his experiences. Zar would get his wish from this afternoon as Vice wanted him to go first, which seemed to immensely please the hot skinhead guest house manager.

As a final note before sex, I pulled Vice and Marcel aside and whispered low to Marcel “Dude, I know you’re an alpha, you don’t get fucked only fisted and you are a master cocksman with that battering ram of yours and I can attest to how amazing that feels opening a guy up. But I’m asking you to let him decide if wants to finally have a go at that masterpiece, and I’m asking you to wait for a few smaller guys to go first, then go easy at first – and use some boybutter on that piercing of yours, not just spit, okay? You can do all that to me or my other boy Lou over there. Show your amazing skills to Vice by making him love it. If he says stop, DO, or he and I will double fuck you until you scream… that a deal – it’s a fine just cherry-picked hole and it will be worth your while. Deal?”

Marcel kissed us both on both cheeks and said “Agreed. You protect your boys, good. Like me with Sebastian. Now let’s all fuck – since our house manager gets him first, I’ll substitute his Daddy’s hole instead.” Overhearing that Zar tossed me Max Impact, a jock, and then held a pipe to my lips to get me started for Marcel’s monster.

And that’s how within 10 minutes from leaving my room the three of us wound up side by side fucking and rimming a hot dude in front of us with three studs behind us pounding our holes. Lou had Sebastian to fuck and rim, with Ed topping him, Vice was enjoying Rachman “Rocky”’s beautiful butt, with Zar blissfully pounding him out expertly, while I rimmed and fucked Gary while Marcel attempted to create a new lane of the Lincoln Tunnel in my ass… amazing, BUT… still amazing…

And so it went, the three of us got to be “Lucky Pierre’s” much of the time with the occasional bonus of either a cock or hot hole for our mouths and tongues along with our cocks in an ass and cocks in us. Much swapping of threes and fours, and Vice not only enjoyed Zar as a top, but had Tom and Ed and Gary fuck him too – Rachman and Sebastian leaning heavily bottom for the evening passed on a turn but asked for “rain checks”. There were times when Vice and I, or Lou and Vice, or Zar and me would be 69ing sucking the others cocks while each of us was being fucked too.

Finally, Vice decided it was time he tried the “Double Diamond Dick” before he chickened out. Wanting to concentrate fully on what was happening, he opted out of being a Lucky Pierre this time and got on his back for the penetration, pillows propping up his butt and neck as Marcel stood bedside like Vice had done to me down in my room. I knelt on one side of him on the bed with pipe, torch, poppers and Max Impact with Lou on the other side ready with several lubes but first while I was shot-gunning Vice a hit, tied off his bud’s arm and the hot dealer administered Vice a small pick-up slam while Sebastian, standing, did the same for his hubby Marcel.

Two snaps as tourniquets were popped off, two guys coughing and then Vice moaning, “okay man, give me that monster” with Marcel simply nodding and growling sexily as his fat head and piercing – covered with cream lube slowly stretched open a hole that until just a few hours ago had been “exit only” and that 48 hours prior would never have conceived of being where it was and WANTING this. I saw a bit of fear, and whispered, ‘Relax, you’ve got this, and trust me the way he’s doing it – you are going to love it real soon!” Vice nodded and the panic eased off his face and he was smiling again, allowing the big head to pop through and making him gasp and moan “fuck that’s big… but fuck that’s good.”

With popper hits, a couple of shared clouds and encouragement from everyone in the room, slowly but surely that beautiful beast went balls deep on our former str8 sex only convert. When those bull balls swinging beneath their leather ball stretcher slapped down against Vice’s sss skin he got a look of hungry triumph on his face saying “Oh fuck this is awesome… fuck me man, please.”

The rest of the room while still stroking other guys or with their cock in an ass or one in their own hole, slowed to watch this newbie take a cock many more experienced holes would balk at. And while he was huffing and puffing a lot, he was definitely enjoying it!

Marcel was true to his word, and so he kept his strokes long and slow but he did make them HARD and Vice seemed to like that as it must have been hitting his prostate just right. We all knew this couldn’t last long but it wasn’t Vice who had to tap out, it was Marcel! Vice started that blissed out laugh/cry thing he did the last two times he let go, and the laughing huffs must have made his hole contract each time because Marcel started shaking his head rapidly back and forth growling, “so tight, merde, can’t hold it…” and then roared incoherently while he blew a load up into Vice who immediately started that shaking anal orgasm thing again that left him smiling and giggling while Marcel looked out for the count!

That seemed the right time to call a close and as the three of us got ourselves and our gear back together, I pulled out 3 butt plugs I’d put in Lou’s canvas ditty when I knew we were on our way up, giving the fattest one to Vice whose hole was currently the one most stretched to hold everything in on our way downstairs. Stopping in the common bathroom, we all did a little cleaning rinsed off in the shower together, and retired to my room to collapse naked with each other, lightly playing while we relaxed and watched porn each catching a bit of nap here and there and enjoying each other’s bodies and company.

Vice was popping grapes and having a bit of Yogurt around 5:30AM when he looked at me, and with all sincerity asked, “So, Daddy J, is EVERY weekend like this for you?”

Lou couldn’t even control his laughter as I sputtered, “sadly no, Vice, even I cannot claim to have a weekend like THIS very often at all.” We laughed and I added “and hell, its still not even dawn on Saturday morning!!”