Training the Femboy

The next day Josh and I woke at 10 am, dressed just in H strings underneath summer shorts, so all of us barechested no socks or shoes, and had breakfast. Nicholas, around 11 am sauntered out looking totally stoned. He had to be at work for 1 pm so was still walking funny and sat down and ate also, but he was just in one of Josh’s White H Strings with his open hot ass.

Strangely, there was a knock at the door, Josh and I knew that everyone on this floor needed a pass key to get up and off the elevator and stairwells or be with someone who had a passkey. I peered through the security viewer, and it was Logan the 19 YO Scottish kid from across the hall (It was his Birthday a few weeks back and he was celebrating how he was finally Legal to buy booze). Logan was a total hot Jock, and Josh and I saw him taking some girls in and out of his suite, but once in a while another hot college dude, so we were not sure what his playing field was, but fuck he was hot with his slight reddish/strawberry blonde high-top curls and faded shaved sides.

 “Hey Logan, what up” I asked.

“Sorry, am I interrupting,” he asked.

I replied, “No No…come on in grab a coffee and some toasted bagels and whatever else you want.”

Nicholas Blurted out, “Me included!” with a giant half-stoned smile.

Logan looked straight at Nicholas, and Nicholas back at Logan…Josh and I looked at each other and literally saw fireworks between them as they big grinned and smiled at each other, like love at first sight!

Nicholas said, “Hi I’m Nicholas, a good old work friend of Josh’s” with total love beams eyes.

They shook hands reminiscent of Josh and I meeting at the BBQ buy over 2 years ago.

We both grinned at each other. Logan was 6ft 2, and about 180 lbs, a really gorgeous jock with a great Scottish accent often wearing half shirts and shorts showing off his washboard abs pecs, and biceps. They were both checking each other out!

I broke the staring silence as they both were drooling at each other, “So, Logan what brings you over?”

Logan replied…” huh”,

Still staring at Nicholas and all smirking, Josh put his hand over his mouth to stop from loosing his shit in laughter.

Finally, Logan responded, “Oh well, you know I am in pre-surgery med at the university, and I am struggling with the textbooks and online tutorials use of all the surgical instruments, and I just blew a test on some poor cadaver...it was terrible they said I butchered him. My Dad the UK Bank executive is threatening to cut me off support if I do not get my shit together and get straight A’s.”

Logan Continues, “I recalled you had mentioned that your company makes all those instruments so I figured you must have knowledge of how they are used and best articulated and manipulated, so I was wondering if I could come over some night and you bring some stuff home here and maybe…you have one of those dummies with all the organs and parts that can be played with …so to speak?”

 Josh blurted out, “Oh yes, he is very good at playing with all the body parts.”

Then Nicholas said, “I can vouch they are both top-notch body part guys…maybe the best!” with a huge grin on his face.

I was just beside myself. Logan laughed and had a puzzled strange look on his face.

I said, “Sure, let's see today is Monday, so how about Thursday night at about 6 pm, and come for supper OK?

Logan replied, “Perfect, I have no classes this Friday and nothing to do but study and learn the entire weekend, and supper would be awesome.”

Nicholas beamingly said, “I’m getting off, I mean off on Friday also and the entire weekend…I will be here working out with Josh and maybe we will help you study, like you could reach into our organs and practice!”

Now Josh had to put his head down on the high counter table and covered his face with his arms as the entire piece shook with his uncontrollable laughter!

 Logan laughed and said, “Sounds like fun, I will see you all then.”

Nicholas stood up to show him to the door revealing a major hard cock in his H String undies and dripping wet spot,…Logan could not take his bulging eyes off of it in shock and amazement.

Shaking Nicholas’s hand, Logan’s hand brushed over Nicholas’s package, and finger slid up the side of his bare ass. Nicholas shuddered and giggled, “See yah Later Logan” Nicholas said.

Logan replied, “Yes Nicholas, I am looking forward to seeing you too!”

 “Well I better get dressed and off to work,” Nicholas said as he left for the bedrooms.

Josh looks at me and speaks. “What the fuck just happened…that little cunt slut, did you see how hard and wet he just was with Logan here, sex should be far from his head this am…fuck Taylor what have we created here” Josh exclaimed!

I replied, “ Well now that we fixed his prostate and back pain he will be hornier than ever, so we are both going to enjoy these 2 now aren’t we!”

The next Wednesday night Nicholas said he felt ready for more training, so we all striped, douched and this time locked him up in the inverted cock cage. Nicholas pranced around in a replay of exactly what Josh had done a few years back.

Josh inquisitively said…” Looks familiar eh!”

 “Yup,” I replied smirking.

Same thing …he was amazed at how his cock was all squished inside him and how stretched his balls felt but no pain, in fact, he commented the pressure made him crazy horny.

Nicholas chose the XXL Seahorse dildo this time, and Josh took on Kathulu XXL. I just wanted to monitor Nicholas and ensure he did not overdo it, as his prostate should still be in recovery from the other night's blow-out cleaning. He had mentioned again that today he had another super strong piss like a fire hose, and that his pussy felt amazing and crazy hungry. Both boys got lined up and lubed and turned on their respective fuck machines. I toggled between the 2 of them putting my cock in their mouths to each delight. Nicholas was learning from Josh how not to gag and choke so he was working hard at being able to please a big cock. The night was proceeding well and then I decided to switch it up a notch, so I switched their fuck machine controllers!

“ Oh Taylor you cunt” Josh laughed, and suddenly Kathula cranked up to max depth and power and plowed into Josh’s pussy as he hollered, “Oh fuck, fuck…Oh, Fuck me Kathulu, harder faster Nicholas!”

Josh then grabbed the controller that he had and did the same to Nicholas sending that XXL seahorse balls deep in the novice’s ass. Nicholas cried out at first but breathed and really got into it again and sprayed a nice cum ½ cup all over the table as Josh did the same having toped up on vitamins and water so as not to have Nicholas win the cum competition again happening between them. After an hour of cumming for the boys, we all slurped the rivers up and swapped in our mouths. Josh invited Nicholas into our master bath shower, and we all had a nice piss splash drink all around and sat on the benches covered in cum and piss. I was in heaven! We invited Nicholas to sleep nude with us again, with Josh in the middle, we all really liked that.

Thursday was finally here. I went to work and returned with the anatomy dummy in a big box and a bin full of packaged instruments. We invited Logan to come early and join us for supper. We all laughed and shared stories. Nicholas shared the horrors about his ex-Jessica and all about the pegging and dildos Logan shared he broke up with Lisa, and sort of smirked and said, “I asked for ass play too and she dumped me.”

All excited Nicholas replied, “See we have so much in common, Logan.”

“Well, we will see, I have not really thought much about which way I swing, but I am really always super horny.” Logan disclosed.

Josh replied, “Well quadruple that here buddy 4 Horned up guys here right now!”

 I said, “Ok, You 2 hooligans go do your workout and keep it down, I don’t want any screams of overstretched muscles especially with me not there to spot.”

Josh and Nicholas ran hand in hand into the Burgundy bath which was closest to the Great room, as Nicholas looked back at Logan and they both licked their lips in an intense stare.

I got out the anatomy dummy and the instruments and started to ask Logan what he understood and what he did not. Immediately I was able to clarify what to use to lift and move the colon and sigmoid and best safest approaches in and out as he seemed very interested in the anus, rectum, and prostate and the nerves and veins connecting it all.

I said, “Do you know that in some prostate surgeries, the doctor will proceed with his hands through the anus and rectum and repair the prostate via a small incision in the rectum to expose the gland.”

 I explained what an amazing gland it was and how it all tied into the penis and testicles and was really the powerhouse of a man’s orgasm.

“Now what else did you want to learn,” I asked.

“Wow you can actually get your hands into a man’s rectum and deep up in him”, Logan asked.

I replied, “Yes, in fact, Joshua and I do it many times a week and have the best orgasms from it alone.” “Wow that sounds really interesting and hot” Logan replied.

Just then he heard moans and groans coming from the burgundy bath and the 2 boys ran out with just H strings laughing and smiling at Logan as they saunter down the hall to the playroom.

“Taylor, I thought most of your exercise and fitness stuff was out on the balcony, so why are they going down to the bedrooms” Logan asked.

“Well, there is other stuff down there too, don’t worry… let’s get back to learning anatomy so you can navigate the abdomen and thoracic blindfolded,” I replied.

We chatted and got serious and talked about other instruments and organs and used a few examples and procedures.

Logan said, “So you and Josh are a Gay couple Obviously, right?”

I answered, “Well pretty much if we put our hands up each other's ass, I would say…I think so. I started fucking girls and women in my mid to late teens and then after Dad passed had my first experience with a man….it was fantastic, and the best cum of my life at that  time!”

“So a guy's urge for anal rectal play is totally natural because of the prostate right, Logan asked. “

“Yes, Logan it really is, and it has nothing to do with orientation and all to do with how we are built,” I responded.

 Suddenly I hear motors turning on and moans and groans ridiculously loud coming from the closed playroom door. I looked down at Logan’s crotch and noticed a huge, formed wood running down his leg, which he started to rub. Based on the outline I thought he might even have me beat…he was so hot and cute!

I asked, “Logan, have you explored your anus and rectum with anything and anally masturbated?”

Logan replied, with his great Scottish accent, “Yes, I did buy a large dildo bigger than my own cock, which is pretty big and getting bigger as we speak about this.(He Giggled) … Boy, it does feel good when I jerk off with it in my arse and deep in my rectum, but after a few weeks I want more, and I have fooled around with a few guys a bit, but nothing major in the ass, but I am really wanting more exploring and not sure how to proceed?”

More crazy moans and groans came down the hall through the door.

Logan asked, “Taylor what are they really doing in there, please tell me the truth, I want to know, it sounds like a major fuck fest, and it is really turning me on to think about Nicholas in there?”

“Ok, Josh bumped into Nicholas a few weeks ago at the sex shop we were in. As he mentioned and explained he asked us to help him with anal training and to achieve anal prostate orgasms and after we had a mind-boggling session with that a few times, he now wants to get a rosebud and be fisted and double-fisted, etc., so the boys are down there riding Giant Dildos working their assholes to giant deep glorious prostate cum’s …OK!”

Logans' bulge twitched, and I saw that huge cock squirt through his tight crotch pants. Logan looked me yearningly in the eye.

I asked, “Did you want to go watch and maybe Join in?”

Logan rubbed his huge cock on his leg and said, “Yes I sure would love that, they sound so fucking hot and Nicholas is quite the catch, I ‘ve been jack off the entire time since I laid eyes on him, he is so fucking gorgeous!”

“If you want anal play do you need to also douche, I asked. “

“Logan replied, “No I actually did this afternoon when back from class before I rode my dildo.” He is giggling revealed. “I always suspected you and Josh were Gay, and he is a real hottie, you are very lucky.”

“Yes I am, so sounds like you have blown a load or to thinking about us also…Josh always said you were a real stud muffin and imagined with your stature that you must have a huge cock, so come follow me so we can all find out” I stated.

 I could hear Logan's heart pounding and his breathing triple as we got closer to the playroom door. I opened the door and both boys moaning got crazy loud almost on purpose it seemed, but they were riding crazy heavy killing those dildos.

I said, “Guys, Logan has heard you and wanted to watch and maybe join in.”

Josh said, “Awesome but you both must be nude to come in here, and we have been dying to see that Scottish snake there Logan.”

He was pounding his ass heavy on the XXXL Seahorse and Nicholas dripping with XXXL Minotaur balls deep up his ass yelled, “Let me see that raging Scottish Slong Logan!”

Logan obliged and stripped down revealing an incredible 10” uncut anaconda cock with Giant Walnut sized balls shaved clean with just a wisp of Redish strawberry blond hair above his massive meat and creamy white skin all over him. He was ripped and gorgeous. He grabbed his ragging-covered hard-on and pulled back revealing beautiful pink glans the size of a medium plum. We all gasped, Josh squirted and Nicholas said, “Holy Fuck it's gorgeous and massive!

I said, “Fuck Logan, your even bigger than me.”

Josh was like “Wow Nicky, what do you think of that?”

“Well, It’s a masterpiece, and I am sure it is meant to go up my sloppy pussy tonight for my first live man cock,” as he panted and cried on the XXL Seahorse dripping cum from his cage.

Logan answered “I would love to fuck you, or any of you hot guys for that matter, but I like it in the ass too, so Nicholas I want to reach the same goals you have set for yourself that Taylor just told of,… so Taylor and Josh, will you train us both up and maybe Nicky and I can become lovers like you guys…I find him really just so really so fucking hot and gorgeous!”

 Logan’s cock was fully erect and exposed dripping large precum.

Josh said, “We would love to do a double class…Taylor maybe we should hang a sign down in the lobby offering our prostate cum fisting and toys pavilion up here.”

I Laughed, “Yah funny boy you are ha ha…not!”

With that, Nicholas turned off his fuck machine and said, “Please unhook me Logan, I’ve wanted you since the moment you walked through the door a few days ago.”

Logan did so and Nicholas hopped down and planted a huge kiss on him and then got down to lick his massive cock. Josh and I soon joined in as there was no way in any position anyone could deep throat this boy. Nicholas tried and coughed and gaged almost barfed.

Nicholas said, “OK I do not care what I have to do, but if I can get this cock in my ass, I am sure as hell getting it balls deep down my throat, even if I have to have surgery from the future surgeon!”

We all laughed…OK OK, we will work out and try positions and you keep practicing on the big dildos.

“Let’s Fuck, Guys,” I said.

 Josh assumed the doggy position on one side of the Bed and Nicholas hopped up on the other. Logan said in his wonderful Scottish accent, “Don’t worry Nicky, I’ll be gentle as I know you are not like the farm animals I have had…” Josh Giggled so hard he pissed.

Logan said, “That’s hot!”

He was a great fit. It had been days since Josh, and I had had anal sex, and I was boiling for his juicy hole and so was he. I lubed my cock and plunged in with no problem as he was still full of coco lube. He cried out, “Oh Fuck Taylor it’s so nice”.

Nicholas took off his cock cage and revealed his thick almost 7” cut cock to Logan.

Nicholas commanded, “Common Big Boy, break my pussy with that Scottish Monster!”

Logan replied,” That’s a really nice thick cock you have Nicky…so come on it's going to be Nicky from me from now on OK!”

Nicky replied, I don’t fucking care, just fuck me until you fill my pussy with your creamy seed, please I beg you!”

 With that, I started fucking Josh, hard and fast, and Logan started fucking Nicky like he had not cum in years absolutely assaulting Nicky’s ass, and seeing as we now had Nicky stretched good and his prostate really healthy and relieved, it turned Josh and I both on like crazy to watch his friend bottom for the first time in absolute bliss with an equally hot gorgeous stud.

Logan was sweating and pounding Nicky’s ass like his life depended on it, for several minutes!

 I said, “I’m going to cum,” and Josh replied, “Fill me, lover, breed my pussy you Stud!”

Both Logan and Nicky both started screaming, “Oh Fuck, Oh Fuck” in unison, it was like a Gregorian Chant choir between a Westerner and a Scotsman…Beautiful!

Logan offloaded just about bucking Nicky into the wallboard and Nicky held his hand against the wall, screaming “Do it fuck, yes fuck, breed my ass fucking pound as hard as you can you anaconda Scott cock, I’m cumming, oh fuck me Logan Breed my cunt!”

With that, we could tell they both blew together and Nicky’s cum was all over the bed and wallboard, an impressive load.

Nicky got up and licked Logan's huge cock clean of his spunk and lube moaning and moaning.

Next, Nicholas hopped up into the sling, and said “Fist fuck me, Logan.”

I said, Fuck where do I find these fun boys and a great lover like my Josh, I do not know but thank you lord you are the savior of man!

Logan asked, “Have you been fisted before Nicky?”

Josh replied on his behalf, “Oh yah just last weekend we relieved his poor prostate and I was in him with my left hand up to my elbow and then I slid my right hand in on the other side…it was a colossal prostate blow and almost a ½ litre of cum.”

 Logan said, “Oh Bullshit!”

I said,” No, I thought both Josh and I came like a lot, but little Nicky here, unfucking real… like a ½ liter everywhere…took us part of an hour to slurp it all up!

Nicky said, “Well now that my prostate had its 2 decades clean out probably I won't do a 1/2litre, but I have been doing at least 300 mls with Josh the last few nights training. So come on guys talk him through it.”

Josh got on his back on the bed and removed his cage, then attached 2 leg hooks from the wall so that he and Nicky could be in the same position so that Logan could copy and mimic the moves getting his hand deep into Nicky.

I broke out a fresh lube bottle for each of us and gave Logan a pair of fisting gloves. He slapped them on, and we both grabbed a cushion and got comfortable.

I said to Logan, “Watch what I do and I will instruct,…ask questions if not sure ok?

“Got it Chief”, Logan answered.

We both slowly entered our boys as Logan copied perfectly, he even started to anticipate the rectosigmoid junction and maneuvered to get through it.

 I said, “See, you know anatomy there Mr. Surgeon.”

 Nicky gasped and said, “It feels perfect.”

Josh said,” It’s the very best every single time, the absolute ultimate!”

Logan's elbow disappeared into Nicky’s hole with a great cry and moan. He had gotten past the sigmoid and was at the start of the descending colon.

I was playing catch up to the med student as I said, “Ballroom time.”

 With that I went straight up and over the transverse colon and could feel Josh's heart racing just inches away …it was beautiful. I pumped in and out in that hook curve position and Josh went completely nuts as streams of cum flew out of his hard cock all over his face chest the bed and even the wall, he was always such a huge cummer! Of course, I caught in my mouth what I could as he tasted like vanilla ice cream with his supper healthy diet, fuck I love him so much he is so beautiful!

Logan said, “Wow I am a bit scared to go that far!”

Nicky commanded, “Do it Logan your fucking doctor, get into my ballroom fucking now!

Logan felt around and then found the curve to the Transverse, he hooked and pushed and went armpit deep just like I was doing to Josh. Tears streamed from Nicky’s face as he shuddered and Logan panicked and said, “Oh my God, are you ok?”

Nicky cried out ...” more fucking more it so incredible fuck put your other hand in me also fuck please deeper please just like Josh did the other night, more fuck deeper hard Logan FFFFuuuucccckkkkkk….!”

 Shaking his head Logan did as requested, while still thrusting his curved arm in and out about six inches each time and then navigating back to the transverse and also sticking his other hand in Nicky’s ass to part way up his arm. Nicky started grunting and groans and riding Logans' arms and then arched in the sling and cum flew out of the blond boy’s beautiful thick cock and almost …almost rivaled Josh’s first blow in that sling, but he did not hit the ceiling but was close in power and in volume to a few nights ago.

I pulled my arm out of Josh and we both clapped and whistled, “Blow Nicky Blow!”

And he sure fucking did! Fantastic!

Logan said, “Holy fuck man, that is so much fucking cum, where did that come from?

I said,” Logan, that is the work of the prostate, the seminal vesical and the Cowper's gland, and all the nerve ending in the anus, rectum, and colon.”

“Wow, Holy shit…I fucking want that like yesterday, Logan exclaimed!”

 

I announced, “OK, guys, here is the plan. Every single night we play no matter what. We alternate every other night who uses the dildos and fuck machines and gets fisted and fucked, so One night Logan and I bottom at the workings of Josh on me and Nicky on you, and the next night Josh bottoms for me and Nicky for you.

I suspect in a couple weeks or months both of you, ( As Nicky is already there in just less than a week which is unreal, …of course his swollen prostate took up most of his ass and abdominal cavity) Logan you will be fisted and doubled up into the ballroom, and 5” Rosebud sometime in the next few weeks, and the rosebud for each of you between 8 and 12 months but you must be patient, go slow and listen to the Josh and I…the pressure in your ass and do not overdo it… do you and Nicky Understand, I asked.”

“Absofuckinglutely” Logan said in a high-pitched Scottish roar, and Nicky said, “x2,” grinning from ear to ear!

 

With that, we all dumped our leather and headed to our master bed bath with the dual showers. We pissed all over and in each other and enjoyed every drop, and then washed and dried.

I said,” Logan and Nicky, you guys can permanently have the Safari Bedroom with the African carved king bed, and if you wanted, we would love for you to both move in with us” Josh jumped up clapping,

“Yes, yes awesome Taylor, fucking party time!”

They both accepted and were quite relieved as each was struggling with where they lived and the situations with their parents.

Logan said, “Although I am in this crazy expensive building I am just renting, and my Dad …that prick of a  UK Banker…with his threats, well Fuckem!! This really relieves the pressure Taylor how will I ever thank you.”

 I replied, “I can also offer each of you a part-time position and work from the condo here for the company with a salary of $72K annually...Logan, I could really use someone learning the freshest techniques in the surgery school and a liaison with the profs and surgeons to see if instruments can be perfected, and new equipment designed. And Nicky, I could really use help in customer orders to expedite faster and more accurately their needs.”

Nicky cried, ”You mean I can quit that fucking hell store and work for you from here?” 

“Yes”, I answered!

Much hugs and celebrations we did for a few more hours and I decided it all called to crack open the Remy Martin extra XO 16th century cognac…fuck… it's only a $3k bottle and this was the start of a life-changing journey for all of us….4 Horny Assholes!

Logan said, “Just I want 1 thing right now before bed.”

“Ok, what?” we all said.

He answered, “Please all 3 of you get on the sofa out here in the great room, bend over and bloom your buds for me please?”

Nicky just had a little gape but coming along nicely with a 2.5” tiny bloom.

Josh and I bore down with five hard thrusts each time getting bigger and bigger and we both were finally at 5”’s.

Logan gasped….” That’s the most beautiful sight I have ever witnessed, Thanks Guys, I can hardly wait for Nicky and I to both be a 5!”

But that is yet another chapter….