Austin and I had already been anally opened this entire week from playing with the dildos, fucking, and fisting. The other three boys are partially now open from the fucking and light fisting from Ashton.
“Oh, Fuck me! This head and dildo are bigger than I thought; I'm not saying it hurts, but I can feel a huge stretch bigger than Ashton’s cock and fist, that is for sure.” Said Caleb.
“Well, tomorrow, Caleb, I will make sure to get both my little hands and arms up your starving cunt as far as I can, maybe my cock with them; we will see what you think then,” Ashton said, smiling away at his step-brother. We all giggled and proceeded slowly.
Ashton seemed to be doing quite well with the 2XL Seahorse. Caleb winced and struggled with 3XL Minotaur, and Matty was progressing not too severely on XL Horny Rhino.
Austin said, “OK, Boys, I know the first time is quite a stretch. When I had the dildo that Ashton is riding now, the 2XL Seahorse mounted in the Fuck Machine; I thought I was going to split open, not from pain, but pressure and pleasure. The latter arrived, and I had one of the best cums of my life, save for Jake Fisting me. Let us go slow and talk it through to each other, so speak about what you feel and want to do.”
Caleb answered, “I am at the broadest part of the glans just before it tapers. I am worried and scared to push down more to have it pop in.”
Matty said, “That is where I am also; the rhino head is at the widest, and I am fearing what will happen when this beast slides in from the most considerable part, passing and sucking in my hole.”
Ashton said, “Mine gradually increases wider and broader with each ¼ inch. I am okay now, down about 4 inches and stretched, but I feel some resistance yet want to go much deeper.”
I got off Dana’s grip, which I enjoyed, and had been down about 1/3. I went to the Great Room and grabbed the extra-large colored laminated pages of the picture book Male Anatomy. Austin knew what I was up to, so they smiled for the ass assistance. I opened the book to 2 large side-by-side laminated pages. One had the side profile of the penis, testicles, prostate, anal canal, rectum, bladder, Cowper’s-gland, seminal vesicle, and all the connecting ducts, tubes, and pipes. The other showed a front open profile with hollow cut-out bits of the path of the anus, anal canal, rectum, sigmoid, descending colon, transverse, and ascending, with the other abdominal organs.
Austin said, “Fantastic idea, Jake. Now we can teach the boys male anatomy. Ok, boys, you can see you all have the heads of your dildos nearly in. When it passes the exterior anal sphincter or rings, it will get sucked into the anal canal and strike the seminal vesicle and prostate, causing a preliminary ejaculation. You can see all the beautiful curves and twists in the rectum in the zoomed-in section—the multi-valve-like structure of the ampulla and then deep up to the sigmoid.
As we slowly venture deeper and further into the far rectum and sigmoid, the girth of the dildos creates massive pressure and massage as we ride on the seminal vesicle, prostate, and bulbourethral (Cowper’s-gland). Not only will the pounding and riding produce an incredible ejaculation, but the nerve ending in the entire structure and pelvic floor will have you going nuts with sensations in our huge pussy’s. You will feel pleasure that you never knew existed, even from your first penis pounding or adolescent ejaculation.”
I said, “Austin, you have memorized the book!”
He answered, “Well, when you were at work, I sat down and read and took photographs (in my mind) of the entire resource. Our bodies are magnificent creations, and these structures here on us, boys, will have you all very soon screaming at the tops of your lungs! Now get ready, guys. On the count of three, you will all push down, relax, and not fear the glory and rapture you are about to experience. One, Two, Three Push!” Holy shit! You have never heard or seen the look on three Twinks like the first time doing this was almost reminiscent of their first cum ever! The look of absolute blissful joy, words, moans, groans, gasps, and sighs was astronomical!
The 5 of us blew several ounces of cum, hitting each other's legs, genitals, chest, and stomach, and much on the book pages. Thank God for lamination!
Caleb said, “Holy Fuck! I can’t believe how fantastic this feels! The sensations and cum are incredible pleasure. Fuck boys. I want to go deeper now; it is like my ass is begging and pleading for it.”
Mattys answered, “Me too! Fuck I am sliding further down; holy shit, I can not fucking believe the feeling; oh, fuck I am going to cum again! OOOOOHHHHHHH FFFFFFFFUUUUCCCKKK GGGGGGGOOOODDDDDDD YYYYYEEEEEESSSSSSSS!” Matty shot four large ropes of cum all over the picture laminate book.
Ashton stated, “OK, I think I am about halfway down, and that was an unbelievable first cum doing this; now watch me, please, going further down. Here goes everything, boys.” He pushed down, and Austin and I knew the sensations he was feeling as that 2XL Seahorse plowed through the remaining anal valves. Judging from bottoming out on the base, he was well through his sigmoid 3rd hole. The bulging eyes looking on that little Twink with the massive, nearly 11” raging cock was just euphoric. He had done it and was balls deep on that base. Now Ashton started to ride and pound so hard and fast that even I was shocked.
Ashton screamed, and I mean screamed, “Holy Fucking Christ! It feels so fucking fantastic! Fuck me! I can’t believe I am fucking this giant massive dildo, and there is no pain, just pleasure fuck guys, I am going to cum; please, let's hold hands and all bottom cum together!
Austin replied, “That is precisely what is supposed to happen once you open the lower canal; the other twisting curved ampulla valves have now all opened as well, wanting us all to complete the mission. We are all going balls deep to the base now, so keep riding and breeding your dildos. Enjoy this and just let go; we are boys here, anally masturbating to group orgasms. Now go wild, guys, and fuck these beasts like it is the end of the fucking world!”
God, my Austin is so off-the-charts beautiful and such a sex beast. As Ashton suggested, we held hands and slowly pounded our beast's balls deep. Caleb and Matty also screamed ridiculously and violently loud.
Caleb stated, “Fuck man, I am past this massive ring on this cock, and I am sliding down; fuck guys, holy shit, it is going in me right to the balls…. fuck God, the sensations, fuck I am going to shoot fuck, Oh My God YES GGGGGGGGGGOOOOOOODDDDDD FFFFFFFFFFFUUUCCCKKKK, OOOOOOOHHHHHHHH FFFFFFFFUUUUCCCCKKKKK GGGGGGGOOOOOOODDDDDDD!”
Caleb had more than done it; his semen streams pelted over 6 feet and landed on Ashton, Austin, and me with five thick white snake ropes dripping from our faces and mouths. Austin and Ashton leaned to each other’s face and mouth slobber kissed. They shared in the volleyed cum gifts from Caleb. Austin and I rode balls deep to our dildos and screamed (not as loud, but loud enough). I covered Matty, Caleb, and Ashton in my six streaming ropes, and Austin covered Caleb, Matty, and Ashton in his five powerful swirling blasts. The 5 of us kissed each other beside us and shared all our semen treats. As we rode, our cocks flanged and swung every which way causing more semen to fly about.
Caleb said, “Holy Fuck Jake! You and Austin cum an incredible amount; like, that must be part of a fucking cup!”
I answered, “It really has to do with sexual health and doing this daily to keep the prostate and all the glands happy and freely flowing. Equally important are tonnes of water and a great clean diet, with few animal products, limited booze, and other unhealthy things kept at bay. Finally is exercise and resistance training.” The boys all nodded as we slowly pulled off our current dildo.
Ashton was so horny now for the 3XL Seahorse, but it is massive and 15” long, and the base would widen him out to 15” in circumference. I was sure that was not impossible, but it was unlikely based on his current size and frame. This would be Austin’s first time trying 3XL Dana’s grip. I knew he would love the knuckles, and cock sensation was just unbelievable. It was so fucking massive. I would get 2XL Horny Rhino which had brought me to great cums hundreds of times, being my second favorite after 3XL Seahorse. Matty was in for a real treat now, having to ride the 3XL Minotaur. Caleb would also enjoy tremendously the 2XL Seahorse.
It was 5:00 AM. We were about to rotate and mount our next dildos when I heard my phone buzzing and text messages. Bruce said there was a noise complaint from the unit beside us. He was required to come up and check. A minute or so later, we five had on our tight Andrew Christian open-ass thongs they borrowed from Austin’s boudoir purchase. It was pretty evident we all had hard, raging marble cocks.
Just as I was disarming the alarm, a knock at the door came. I opened it expecting Bruce, but with him was an extremely handsome young man dressed in the building security uniform. The four boys stood behind me in a very pissed-off, sexy pose and smirking grin.
Bruce said, “Oh, Good morning, Jake. I am so sorry, but we must check when these complaints happen. Michael had told me that Austin asked to borrow the freight elevator fob and passcode, so from what I see, you guys were just getting carried away by your boy-party gang bang.”
Before I had a chance to answer, the thing we all noted beyond a doubt was the security guard had a major hard cock in his pants and was glued to Matty’s face, and Matty was glued back to his. It was more than Cupid’s arrows. It was like a lightning bolt of attraction between them as they smiled ear to ear. Even Bruce started to laugh.
Bruce said, “Oh, let me introduce our newest young security guard, Lucas. Lucas is 18 and has just enrolled in the local Law and Security program at George Brown College. As you can see, he is handsome and put together like a lean JTF2 Operator.” I knew that Bruce was retired, ex-military, and gay. He often claimed to have been in JTF2 (our CAD equivalent of Green Beret/Navy Seal/Delta Force, etc.).
I laughed and said, “Lucas, welcome to the building. Sorry guys, if we were getting too loud; it was just a great group orgasmic climax.”
Lucas replied, “Wow! That sounds like fun. I am done at 7 AM and think I best come back here and ensure you are all quieted down at the end of my shift.” Bruce was giggling and shaking his head.
Matty said in a sultry Femboy sweet voice, “Yes, please! Lucas, do cum back and check my loudness at shift end! We will head to bed then for a rest, but please promise you will return to check on me.” Matty took several fingers and stuck them in his mouth, and the other hand rubbed his throbbing hard dripping cock.
Lucas said, “Oh, I definitely will!” We all laughed and shook hands with the visiting boys, sharing their names. I closed and locked the door. Lucas was about 6 ft 1” tall, perhaps about 160 pounds, with blondish brown flaxen hair past his jawline, parted at the right side and combed over with a bulky messy drop. He had aqua eyes very close to mine. He was a very nice-looking, hot young man, not as God-like gorgeous as Austin, but on par for sure with Caleb, Ashton, Matty, and me.
As soon as the door was closed, Matty said in a very Fem-boy demeanor and voice, “Oh My God! He’s an incredible complete dish; I am in love!” We giggled.
I noticed that Ashton grabbed Caleb’s hand in a couples-defining gesture. They looked into each other’s eyes and could no longer deny the love that had existed for a decade between them. They nibbled and kissed, holding each other close. We were all excited about this. Of course, we were all going to have sex with each other, but every boy and young man needs that special lover that they are in love with, so it seemed we would be a group of 3 couples who would have incredible group sex and BDSM with each other.
Austin said, “Ok, Love birds, we still each have four dildos to rotate through, and my cunt is painfully starving again, so can we get back to our group ride, please!”
Ashton asked and answered at the same time, “Well, is that because we have expanded our cunts I guess; it will now keep wanting that extraordinary full pleasurable expansion all the time.”
Caleb replied, “I sure fucking hope so!” We all returned to the master bedroom and play space. We re-greased our next planned dildos and started our plunge. As expected, each one of us experienced the sensation of what the other previous rider had. Knowing this deep in one's psyche, we felt a very animalistic, feral, and wild connection. The fact that we shared in each other’s cunt juice and lube was also very erotic and releasing.
Matty cried out first as he slid over the perpetual rings of the Minotaur, “Oh Lucas, get both your hands deep in my cunt, please!” We laughed. “Sorry guys- just practicing for when he is here!” We roared.
Caleb was now on the 2XL Seahorse that his stepbrother had just cum off of. He stated,
“Holy Fuck, man! This feels so different with all these wonderful ribs and ridges. Feeling it plunging through those folds and curving valves…Oh Fuck I am going to cum soon again, guys!”
Austin said, “Try to wait for the rest of us. This Dana’s grip is fucking incredible – Fuck Jake, these knuckles are so intense! I will push down and try to bottom on her here.”
Ashton Said, “Caleb, if you love the ribs and ridges, wait until you try this size-up 3XL Seahorse. The sensations are five times more intense. Jake and Austin, I am not sure I can get balls deep without injury.”
I replied, “No, I do not think you should try. If you are soon down about 80%, I think stop there and just enjoy the cum; give it weeks or months, and you will get there.”
Austin said, “Boys, I know I told balls deep; Jake and I can do it because he has been using these for years, and this past week constantly broke my pussy wide open. It will take time, days, or weeks; there is no rush, and none of us are going anywhere. But now I am going to ride this fucker. You guys ready for the second Cumming!” We nodded and laughed. Away we went, pounding down as far as we could on these magnificent creations. In another 3 minutes, we all erupted geysers of cum all over each other and the laminated anatomy book in the middle. A large cum pool was forming as it was liquifying together. The group's animal-like wildness was so electric. We continued to rotate through each dildo and came together, each time almost in unison. Our ejaculations seemed nearly to build and build to volcanic firings.
Finally, we had finished. We pulled off, and Austin started to slurp at the semen lake on the two laminated book sheets. Like horses, we were there with him in seconds, finding a cum semen oasis in the desert. This was an incredible boy-bonding experience. By the time we were finished, the book was crystal clean. We all kissed each other wildly as we shared our group's sweet semen.
It was 6:45 AM. I told them to leave the dildos and that we would clean up later tomorrow, after fisting the day away. We each got a large drink of water or Gatorade and headed to different parts of the condo with our primary lover. Austin crawled to our bed with his gorgeous body and face on display. God, he was a sight to behold! All of us looked at him with disbelief at his beauty. It would take weeks and months to get the other boys to his level of physicality and stature.
In just a week, he gained about 8 lbs and more muscle. His wiry frame now had hydrated fibers, tendons, and ligaments that popped perfectly, with God-like definitions everywhere. His body always had this muscle, fibers, and magnificence, but it was hidden from his street life effects. His skin was now perfectly tanned from our balcony sunning and sex. His cleaned-up mop-top was growing to past his shoulders; best of all were those eyes! His lashes and darker brows, like his darker pubic hair triangle, were like ornate frames for works at the Louvre. His gorgeous head was on the pillow; he motioned for me to join him.
Ashton grabbed his step-bro’s hand. He and Caleb headed for the other bedroom with the queen bed. I was not sure how much sleep they would get. It was now 6:55 AM. There was a knock at the door. Matty ran naked and rock hard erect, dripping, to answer it. How many of us were still able, even at our age, to get hard again was beyond me; just so fucking turned on teen hormones, I guess.
At the same time, I lay down beside Austin. We watched out our master room's double wide doors to the Great Room. I was closest to the door, and Austin was behind me, spooning me. His pillows were higher, so we could both watch. Austin whispered,
“I am so in Love with you, Jake! It is your turn to be made love to all night long.” I turned around, and we kissed deeply. I felt Austin spread my well-greased cheeks and slide his 9” cock deep in my ass, rubbing directly on my prostate. This resulted in my first of what would be dozens of ejaculations to cum till morning.
The front hall mirror beside the kitchen/dining area, which had a perfect reflective view of the second bedroom beside the fitness den, showed us exactly what Caleb and Ashton were up to. Ashton was getting rimmed wildly by Step-bro Caleb. We were both pretty sure that Ashton was now going to get fucked wildly by Caleb’s over 8” + cock.
I turned on the bourbon blues music with the remote and all speakers throughout the unit. We saw in the mirror two thumbs up from Ashton and Caleb.
Feeling Austin's fantastic penis slide in and up my anal canal and curves, hitting the glands precisely, had me squirting semen all over and off the bed. What was incredibly impressive was our entire view of Matty and Lucas. The unleashed passion and physicality were beautiful between boys who had love at first sight and were strangers just an hour ago.
Matty had opened, closed, and locked the door so fast you could see and feel the wind gush. The two boys went into a wild, deep, passionate, wet kiss as they both peeled Lucas's clothes off. Both are giggling and losing their balance several times. Austin and I snickered. From what we could tell, Lucas had a nice 8.5” cut cock, a bit smaller than Austin but about the same thickness. They continued to kiss wildly as we saw the pre-cum lines dripping from Lucas. In a sudden yet eloquent and smooth motion, Lucas lifted Matty in the air while Matty wrapped his Femboy twink legs around the ripped washboard abs and back of Lucas. Slowly he lowered Matty onto his titanium hard cock, and we saw it disappear into Matty’s welcoming, steaming, hungry pussy. Matty threw his head back and let out the most beautiful Femboy cry, moan, and gasp we have ever heard; a tear dripped from his face as they continued to kiss wildly. Lucas gently pressed Matty’s back to the kitchen tiled wall while Matty rode his fantastic dripping cock.
Matty’s cock was now sandwiched between their abs and chest. The look of complete bliss was mesmerizing. Austin whispered again,
“Fuck me! Look at them go, Jake. We are doing that position very soon, lover!” I shook yes as Austin continued to tap out one ejaculation after another from me as he continued to moan each time. I could feel his boiling semen fill my pussy like a spraying twirling sprinkler. At the same time, we could see in the mirror to the other bedroom Caleb was slowly fucking step-bro Ashton missionary style as the boys passionately kissed and slowly rode with Ashton's legs around Caleb's Torso.
The moans and groans and fucking wild sounds, from not only the bedroom but from the kitchen area, got louder and louder. Matty and Lucas were both approaching a massive mutual ejaculation. As we heard Matty scream and yell that he was cumming crazy, it caused Caleb fucking Ashton to also cum. Austin and I had had several ejaculations, but we both felt the big one cumming on now as well. The 6 of us, in our 3-couple configuration, all cried out in orgasmic rapture and euphoria as our major ejaculations occurred nearly simultaneously. It was such a wonderful experience hearing and seeing each other from a distance; so erotic and such a fucking turn-on!
My cum struck the wall behind us from my colossal, pointed cock as I lay on my side, taking Austin’s slow bunny fuck. The hot and wet pelting sensation in my boy-pussy was tremendous as he filled me with ounces and ounces of his white lava-gushing, spraying boy-cum.
Lucas continued to thrust deep and high into Matty. We saw a waterfall of thick white cum fall out between his thrusts from Matty's cunt. Between their stomachs and chests was dripping Matty’s ounces and ounces of liquefying boy-cum semen. Lucas carried him over to the sectional corner and gently laid him down. He knelt and parted Matty’s ass and legs. Lucas ate and sucked Matty’s boy-pussy, removing any cum and lube that had been left in him from the last 12 hours marathon.
He then took Matty’s 7.5” cock right down to his shaved mound and sucked the boy dry; Matty grabbed his head and face fucked him pounding his head hard so that his entire femboy cock was down Lucas’s throat. Holding him firmly with both hands at the side of Lucas’s head, the sounds and look on Matty’s face were incredible. As he came incredibly down Lucas’s throat, we heard and saw gulping and swallowing sounds while the blues still played on low; the rest of us continued our incredible fucking.
Back to Ashton & Caleb, they were cleaning each other pussies and cocks in a breathtaking sixty-nine alternating between eating their cocks or rimming their holes. The sun was rising, and we had been awake for 24 hours. Austin kept thrusting and superbly continued to slowly fuck me over and over. We both kept cumming.
Just before we dozed off, we saw Matty take Lucas to the bathroom and engage in what sounded like a giddy boy douching session, followed by the tub running. It was a fantastic first play day!
Austin whispered again as he bit my neck and earlobe, “We are going to have the wildest six boys fisting session all day tomorrow after we all cock-cage up and flog their asses and balls. I will not stop until there is so much cum all over that we can’t see the hardwood!” I giggled just as we both came yet again. I had never been so happy in my entire life!
“I am so in love with you and have never been so happy as I am with you; you are my savior, my night, my everything,” said Austin. We passionately kissed as his penis continued its unfathomable perfect symphony-like humping. The bed was soaking as waves or orgasms continued to wash over both of us, nibbling, kissing, and loving the sleepless morning away.
