Training the Femboy

So as luck would have it when I refreshed my calendar Mildred and Frank were thankfully not coming until this coming Friday. A week after our first meeting at the mall and Josh’s colossal vodka incident.

Today was Tuesday so we had a full three days to prepare clean and decide what to tour for them in the building and our unit or what was fair game to discuss and what was off limits.

I was having my coffee and Peanut butter toast, when suddenly I heard Josh frantically call from the Master Bath,

“Taylor come quick please, I am bleeding!”

I ran to the bathroom and Josh was holding some paper as he just had done his morning dump, and on it were a few pink streaks and a few heavier red blood marks.

I asked, “Do you have any pain or recall major pain from last night's 4 fists and arms?”

Josh replied, “ No in fact there was more pressure and pain the first night you deflowered and fisted me and I just had a tiny bit of pink then for  a few days as we kept playing, and really barely any since then, but this is the most ever, not  a lot I know but…”

Nicky and Logan both came into our bath, Nicky said,

“ I have some heavier pink also with some red streaks, but no pain and nothing dripping but first time ever this quantity and colour.”

I replied, “Well, you boys did the 4 fists and arms to our elbows last night for the first time, so you're not bleeding out, so let's have a relaxing breakfast and then we will check your bellies with the ultrasound machine and do a colonoscopy ok?”

Josh replied, “ Well we both better go douche then.”

Logan and I yelled in unison, “No!”

Logan continued, “It is likely just some micro nicks from over-stretching but if you do have a tear or fissure, the water pressure can make it much worse or hemorrhage it open!”

I replied, “Josh your log of shit here in the toilet looks very solid long and large and well-formed, and just a bit of pink in there so I don’t think we will encounter anything to stop us scoping deep up into the descending colon and transverse ok.”

Josh said, “Fuck and I guess no Vodka for this procedure.”

I replied, “That’s not funny!”

Nicky said, “My shit was almost identical to Josh’s….Fuck I can’t believe we are having this morning shit conference.”

Logan said, “Oh come on guys we have all seen and smelled our shits and we all are loving and respectful no matter what….and if you ask me I am really getting horny right now talking about our shit!”

I said, “Ok Ok back to the plan, let's relax and have some food and then we will get you both on the leather bed in the Play Palace and check you both out with the ultrasound and the colonoscope, and no worries about your shit, we must ensure we play safe and if we need to change gloves or lube or whatever…and..”

 

Josh interjected, “Well there is no way I am not talking 4 fists up my deep cunt again, that was the greatest cum last night since my first fisting night with my Love Taylor, and like fuck I want it soon again…like tonight!”

Nicky added, “Yeah I agree, I never imagined being able to stretch and I had no pain just pressure but fuck it felt so wonderful like spiritual and beautiful with someone else sharing the same together!”

Logan said, “You 2 fuckers are making Taylor and me jealous cause we have never had 3 and 4 fists and arms yet and have not been cuddle quadruple fisted yet so stop bragging!”

I answered….” Well, I once had a XXXlarge toy and a guy's hand so likely about the size of 3 hands and arms never an issue but fuck let's eat and get to the inspection to calm all down here…fuck you guys!”

We finally did just that all had a nice breakfast and meanwhile, I texted Markus and asked him about what they use in Germany for extreme fisting up to 4 arms past the elbow.

We all went to the play palace and all stripped down nude in order to keep this like an equal play session. Josh was first to get raging hard and the rest of us followed. We asked each of them to first get in the doggie position so Logan and I could inspect the anal opening, the anal canal, and their rosebud blooms.

I said, “Okay boys just relax and Logan and I will slowly insert our gloved lubed fingers and then very gently and as long as it takes as we are relaxing your hole, try to produce your bloom, we have some baby wipes and will check for any blood.”

After about 7 minutes Both Josh and Nicky were moaning and groaning and so turned on by this medical scene they beautifully bloomed and had good-sized ejaculations.

Logan and I at the same time took the wipes and saw nearly in close similar spots on their blooms that they had a micro scratch not even really a tear, but a tiny speck of oozing blood. Both of us agreed it was likely from the quick punch-fisting.

At that point Markus texted me back he said, “ Wow 4 holy shit...good for you boys….its quite common near the canal entrance of a bloom and also check deep at the end of your stroke around the sigmoid descending colon curve as this happens from the kinetic energy of the multi fists sort it all lands there with pressure and although the bottom boys love it as the most religious spot, this micro tear from this can be resolved by loading slowly with your hand a large cup of the triple organic mix gently deep into the descending colon at the transverse so it trickles down like a buffer airbag for the end of the hands so no need to panic. What we have found in the extreme clubs here in Germany is that for this very wide and deep punching play the coconut oil does not quite cut it, and many of the guys like going organic so they are not crazy about the hybrid lubes or the major commercial marketed ones and many have found their own private triple mix as I mentioned ….they take the coconut oil that gets slick and watery quick melt and in a blender put it with the good old Crisco sticks, and some guys like to add in a bit of unscented Cetaphil hypoallergenic hand cream featured by a lot of the women into the giant toys and fisting online…hope this helps  and even though trimmed nails and double gloves are best so this extreme depth and width are like an extra cushion but….assure the boys relax it will be fine and for fuck sake all of you keep doing it and cumming!”

I texted back, “Thanks Markus, will start the triple blend now and the double gloves all around …God Bless you Fist fucker Germans!”

Logan and I asked Josh and Nicky to get on their left sides and bring their right knee up to their chest. Logan grabbed the ultrasound machine and checked their rectum and anal canal sigmoid and the colon all the way to the transverse. Both boys laughed and quivered at the cold gel on their belly and sides and pubes, and both had a little ejaculation from the feelings as we ultra-sounded them..it was very cute!

Logan said, “ I see nothing no blood or tears or anything in either of them, and the organs look perfect.”

 I replied, “Yeah me neither.”

Josh excitedly said, “ OK OK now get the camera thingy our asses I want to see what we look like deep up there.”

I said, “Okay both of you stay in this position and I will put the HDMI cable into the large screen TV for the colonoscope, and I am hitting record.”

Josh said, “Fuck I thought our first porn posting would be a major fuck fist session not a medical scoping but ok!”

I did Josh first and Logan helped guide me into him with the scope…we all 4 gasped…it was beautiful, with the red and pink folds and valves and curves and accordion-like tube that explained how one can expand so deep and wide inside. Josh was in awe, and said,

“Guys I am cumming  here watching this knowing and understanding what is happening when we put the toys and fists up us, fuck this is beautiful like and tunnel coaster at the fair with all the ups and downs so fucking cool!”

I was about 21 inches in Josh when Logan said,

“Stop stop back up look to the outer left just past that nice piece of pooh”

Josh said, “Great fuck guys my shit is on TV the size of a Beer box!”

I said, “Yes yes I see it, it's exactly what Markus said is common, it's okay, you see there is just a micro scratch there with a bit of blood vessel but I don’t think it needs cauterization.”

Josh said, “That is for fucking sure, no way you are lighting a fire up my ass!”

We all laughed and agreed a few days break and all be fine and perhaps now was the time for Logan and I to get to 3 and 4 arms.

We did Nicky next after washing and sterilizing the colonoscope. Josh said, “Cool man what a nice asshole and rectum…Nicky that prostate still looks like it has a bit of congestion…oh wow there is a nice piece of Nicky pooh!”

Nicky said, “Well all is fair in Love and ass taping.” We proceeded past it and slightly further about 23 inches in Nicky had a similar little micro scratch on the outer wall, and all agreed just a few days rest and we would change the lube and glove routine and be cautious about the end of our strokes.

Josh rubbed Nicky’s ass cheeks and said, “It's beautiful Nicky an absolutely perfect pink love tunnel, I wish Logan and all of us could stick our heads deep in it and lick every inch so pretty!”

Logan said, “Okay 4 fists are enough we are not lubing out fucking heads up into one of our assholes we would suffocate you dick heads!”

We all roared and laughed and I said, “ But what we can enjoy is to think of a way to fist or attach the scope here to the toys with medical tape or something so we can see our penetrations on the TV from toys or fists.”

Josh quivered and shook and said, “ I just shot a load off the side of the bed guys!”

He really did, we all were so excited to see the wonders of the inner human body and this gave us a new appreciation of how and why we were having such ecstasy, pleasure, and orgasms.

Logan and I said we would work it out safely with some medical engineering. Seeing as Josh and Nicky had cum we cleaned up the machines and put them away and Logan and I felt cock blocked and really needed a cum.

Nicky asked, “Josh, how were you able to first deep throat Taylors Big 8.5” cut cock there ...I know you can do it now in any position, but it's taken you three years?”

Josh smiled, “I did it that first night we were together and only one position worked and it was directed all by the man I am madly in love with till death and then some more...My lover Taylor. After I blew (and blew I did boys) from my first fisting, Taylor laid me on my back on the leather table there and put my head over the edge, and then slowly came straight in from a standing position as his cock is pretty much 90 degrees straight and if anything with Logan, Nicky, you could work that anaconda cock curves down just a bit. What do you guys think?”

Logan began, “ Nicky I am crazy in love with you and I really do want you to deep throat me and I know you want to also and have been trying and getting about 50% there, but what if Taylor you deep throat into Nicky first and try to train him on your cock and Josh, I have been dying for you to deep throat me or try to please.”

Josh looked at me and of course, I nodded with approval as we had just discussed this while douching the other night.

Josh said,” Yes we agree let's try this and we can switch once your mouth and throat are relaxed enough, or keep trying another night so no pressure guys. Also, not today as Nicky and I need to heel our asses a bit, but how would you guys feel if later in the week, I pound Nicky's ass with my cock and Taylor I know would love to fuck you Logan….thoughts?

Nicky was laughing and Logan replied, “Fuck guys like do you have hidden microphones in our bedroom, Nicky and I have been begging each other for this exact scenario to happen so let's all be open and get our wants and needs on the table now.”

I said, Logan, Nicky, this is awesome, and I do want to fuck you both and want each of you to fuck Josh and me and flip who is doing who. We have done so much together, and we know who is in Love with who Let us all just enjoy the sex and cumming and toys and fists and cocks so we all agree were are all open to doing anything with any of the other 4 of us any positions, holes and acts …yes?

Nicky cried out, “Yes yes,” followed by Josh, “Well Fuck this is my dream guys.” Logan said,

“ I want to do it all with all of you too, but I and Nicky also have a special request as soon as the boys are well and healed and all and any of us can bottom…Nicky wants to be triple fucked like we did Josh, and I love watching Josh and Nicky face to face in close passionate kissing and breathing like they did when we fistfucked last night….it was beautiful… you two made Taylor and I mega blow on you!”

Josh said, “Look at you Nicky, you little anal slut, now let’s get the cock sucking under way yes?!”

With that, we moved 2 of the tables close to each other, and  Nicky and Josh laid ceremoniously down and put their heads over the edge, their hands between them fell to the side and their fingers lightly touched. Logan and I looked at each other seeing this and both grabbed the hands Logan said,

“Hold and squeeze each other's hand as we share and connect as 4 and Taylor and I will hold hands between us and each of us will hold your other free hands we are all as one!”

It was a gloriously ritualistic and lovingly beautiful circle of love.

I slowly instructed all, “Josh and Nicky are you ready?” They both replied, “Yes Masters.”

I recited “Both of you breathe through your nose and concentrate on relaxing your throats.”

They did just that with begging eyes wide open. Slowly I entered Nicky's mouth with my dripping cock and Logan entered Josh's mouth as I saw and heard Josh had to open even further to get the anaconda head in. Logan and I started a slow rhythmic thrust as I instructed the boys to relax their tongues and use them to slide over the glans of our penises. We continued and Logan and I started to really lubricate and precum and it flowed all over their faces and out the side of their beautiful mouths with youthful pink lips and perfect noses brushing out lower shafts. We all started squeezing each other’s hands over the next few minutes. Josh was starting to struggle with Logan's anaconda cock and Nicky similar to how Josh first did that night. I said,

Boys I know it hurts but open and relax your jaws like never before big like at the dentist and breathe deeper in your noze. We could see their chests and breathing quickly increase and feel the pulse in their throats and watch their beating chests. We were ¾ in and Josh and Nicky did perfectly after 5 more minutes I said we were getting close to cumming and the boys squeezed our hands and nodded lightly they were ready. I instructed,” Relax and deep breath and here we go, boys.”

 With that Logan and I plunged all the way balls deep down the boys’ throats and really started to face fuck them hard. I don’t know how Josh did it as that huge cock all the way down his throat should have blocked his airway but then I reminded them …” Lift your chest up now boys we are going to blow.”

Logan and I went full bore and pounded their sweet faces and offloaded huge, massive squirts down their throats. Tears came out of both their eyes and both boys sprayed me and Logan from their raging erections. Logan and I opened our mouths to catch as much of their sweet cum sprays and squirts as we could…we now realized hands-free cums just from the mental sexual emotional stimulation without any anal, rectal, colon, or penile prostate stimulation was also possible as massive cum poured out the sides of their mouths as Logan and I watched them swallow after swallow after swallow which almost causes them to not be able to breathe. Both Josh and Nicky continued to shower us with their beautiful cum as Logan and I tried our best to eat as much flying around without disrupting our thrusts. We both came deep down their throats for about another 4 minutes and they slowly exited and wiped our cocks all over their mouth nose cheeks mixing all our cums together. Both Boys gasped and gasped through their mouths now as if coming up from a near-death deep ocean dive. Logan and I panting like the marathon end game.

Josh gaspingly said, “Holy Fuck that is a massive cock, Logan, my throat hurts but fuck I can’t believe I did it, and Nicky you took Taylor, fucking good boy!”

Nicky said still panting away, “Yes, wow fuck yah my throat hurts a bit too but that cum squirting down my throat is so exciting and at the same time relaxing and surrendering, feeling all of us cum and knowing we were all cumming on and in each other and holding our hands ...fucking talk about male bonding, holy fuck guys! Logan my Love I know how to deep throat you now, but think I need to try Josh’s cock first as he is almost the same size as Taylor, so maybe tonight I’ll suck Josh and Logan are you game to take Taylors' big cock tonight?”

Logan replied, “Yes that sounds awesome guys.”

Josh said, “And what the fuck do you mean…almost as big as Taylor…do you know how hard I stretched this fucker from 7.5” when he first met me to 8.5” same as him now,”

As Josh was still rock hard as I was, I said,

“Okay lover, tape measure time.” I grabbed the tape measure and Josh pressed it to my pubic bone into my light-trimmed bush, then he extended it to the tip of my pink glans and read the number as Nicky and Logan looked on to judge, as we were all still cum dripping from head to toe, it was hilarious.

Josh said scowling, “8 & 5/8th…Fuck!” He then checked my glans circumference, “6.5” around your glans…and at your base you widen out to…7.5””

I said, “Ok Josh, let's check you now…8 & 3/8th” (Logan and Nicky conquered, which really pissed Josh off) and at your glans, 6 & 3/8th”, and at your base 7.25”

Josh proclaimed, “Fucking fine he has an extra ¼” all around on me…Fuck, Fuck, Fuck!”

Nicky said, “Check me check me.”

Josh grabbed the tape measure and began, “7.5” from your pubic bone to your glans tip (Which was leaking more pre-lube), 7” around your glans, and at your base 7.75”

Next up…anaconda cock, Logan get your ass over here, Josh snickered and commenced measuring, “10” exactly from your pubic bone to your cute uncovered glans, and 6.75” around your glans, and 8” around your base…holy Fuck Logan I have no idea how we just got that down my throat.”

I said, “Ok guys let's do a quick hose down here and clean up and then continue tonight after supper the cock sucking, but let's leave Logan and I getting 4 fists and you guys fisted again until Friday night after Frank and Mildred have gone.”

Josh replied, “Yes I think that is a great idea, as I am hoping they will be overly accepting of everything here guys as I plan to cum clean and show they everything including the play palace.

Logan replied, “Well you don’t need the life insurance money, but if you want them to go into cardiac arrest, at least Taylor and I can resuscitate them!” We all laughed so hard.

I said, “How about a 4 man piss shower guys and then we will hose down the room.”

Josh replied, “Yeah now that we have the drain trough we can do that in here too guys, Logan I want to taste and swallow your piss from that snake you just had down my throat.” Josh knelt and Logan squirted directly into Josh’s mouth a nice light colored 2 cups of piss and all over his face and chest and hair, fuck Josh looked so beautiful piss covered. I knelt for Nicky and said, “Choke me thicky Nicky with that sweet nectar.” Nicky came over and holy fuck now that we repaired his prostate, he damn near blew my head off from the powerful stream, even Josh was worried, but I managed…barely. It was a nice taste but not like my Joshua.

Next, we decided that I would piss into Logan and Josh into Nicky. Logan only did a bit of this before with us, but now was totally turned on and got rock hard and ejaculated some as I filled his mouth and he swallowed nicely and sucked the tip clean. Nicky went nuts and took half of Josh’s cock in his mouth and held his breath while he gulped and gulped every drop of Josh’s piss.

Nicky licked the tip clean and pantingly said, “Fuck Logan you have to taste Josh’s piss its just like pineapple juice…fuck how do you do it, man.”

Josh replied, “Sith Lord secret!” We all roared and started to clean the room, so much faster and easier with the hose and power washer and built-in dehumidifiers and heaters. God Bless Fritz and Gerhard…brilliant!

We had a light supper, a little wine, and cognac all showered together in the master bath. It was weird not anal douching but putting a relaxed spin on the next cock sucking session as we still washed and cleaned our outside assholes perfectly so we were all fresh to flip the deep throating on the tables.

We got into the play palace and decided to push the 2 tables even closer together. Logan and Nicky got up on them and moved as close together as they could so they were touching from their sides and all the way down to their feet. Logan Grabbed Nicky’s thick hard cock with his hand and Nicky grabbed Logan's anaconda cock and each proceeded a slow milking jerk. The boys recalled my instructions so pretty much easier. They slid their heads off the edge and opened very wide. Both Logan and Nicky were dying to suck and deep-throat us. Josh and I started to tongue dance kiss and we grabbed the boy's other outside free hands. Josh pulled away and opened his mouth, I produced a good gob of spit and spit into his mouth as he moaned and swished it around and then returned it to my open mouth. Both Logan and Nicky shot a little white cum squirt onto their chests as we did this very turned-on they were. Logan had been used to sucking Nicky so my width was no problem but the depth and extra few inches might be a challenge. Josh and I entered their mouth and throats looking into their eyes, we could see the deep desire and lust in each of them so excited for what was coming. We started thrusting slowly and all was going well. Nicky started moaning like crazy which really started all our juices flowing and each time Nicky pumped Logan’s cock a massive clear precum oozed out. Nicky was so excited he became engorged and so big like he did the previous night’s quadruple fisting I dare say approaching 8 inches and glans deep explosive red. Josh and I were now each 2/3rd of the way down their throats. I said,

“ Big breathe through your noses guys and arch you back and open your mouth and throat as Josh and I are now going balls deep.”

They both did very well and their cocks started shooting thicker white cum over our faces and all our chests. Both Josh and I again tried to catch in our mouths their creamy seeds. I noticed Josh really picking up the pace staring into Nicky’s blue eyes and long gorgeous blond hair hitting his inner thighs and sculpted legs. I was now balls deep in Logan's mouth and announced I was close to cumming, and he nodded ready, and moan, and groaned. Next, Josh stated the same to Nicky and started to pound and face fuck him like I could not believe.

I said, “Josh be careful you don’t want to injure him.” Josh backed off a minute and pulled out enough for Nicky to breathe.

Nicky said, “Okay I’m ready now Josh pound my face balls deep as hard and fast as you can please choke me with your big cock so I can do Logan easy please I want to get anaconda in my throat so rip me apart please.”

Josh said, “Ok buddy here we go.” Logan and Nicky were now pumping each other cocks furiously and Logan squeezing my outside hand and Nicky squeezing Josh’s outside hand.

I announced, “Logan I am cumming eat it, swallow,  eat it all you Scott stud jock, eat my cum take that cock all the way. Logan did just that and my pronouncement drove Josh crazy into some sort of superhuman ninja as he super fast-faced fucked Nicky’s mouth so deep and so violently Josh’s pubic triangle wedge was actually in Nicky’s mouth. Josh then proclaimed,

“ Oh fuck Nicky you asked for it this, it’s a really big famous Joshua cum, fuck I’ve wanted to do this to you since we met in the sex shop you fucking hot twink, eat my cum eat my cock Nicky deeper, deeper swallow you slut cunt swallow it now!” Josh shook the entire room and at that exact moment, Nicky and Logan blasted many fantastic loads of scalding hot creamy thick torrents of cum from their cocks all over Josh and me as we scrambled to catch their loads in our mouths. I pulled out of Logan as my cums were done as he had eaten a good 250mls ½ cup. He then leaned over and started to suck off Nicky like there was no tomorrow. Nicky started to squirt deep into Logan's devouring throat and then my Joshua, my Joshua cried out and cried out as he blasted into Nicky's throat another 500ml full cup of his sweet apple pie cum. It was too much and Nicky had to pull off as he coughed up ½ cup of the cum Josh had fire-hosed down his throat. Logan leaned over and started to slurp up all of Josh’s cum that Nicky coughed up.

 Josh said, “Oh Nicky buddy fuck are you OK?

Nicky replied, “ That was so awesome Josh, just what I wanted but I tried I am sorry but your beautiful sweet cum shoots so incredibly hard and strong, and fuck your volume…wonderful, unbelievable fantastic, where does it cum from how do you make so much!”

Josh replied, “Sith Lord Secret!” We all laughed and slurped around the surfaces of our bits of cum and kissed each other swapping taste and textures ….everybody loved Josh’s apple pie cum!

We got up and chatted about how much fun this was and cleaned what little cum was not already down our throats. We had some more water and snacks and crashed asleep looking forward to Friday’s Josh’s parental first visit!