Training the Femboy

So a few more months had passed and we were all enjoying our anal explorations and ejaculations. We started with our nice group lunch, as the boys had all been doing a great job helping with our household and doing chores and sharing in the upkeep responsibilities along with me. Our wild sex does result in a lot of cleaning and cleanup!

The company was doing well, and Logan was getting A’s at the top of his Med-Surgery classes liaising with the professors and doctors we actually made a few modifications that they attributed to saving lives with equipment and instruments, and Nicky got our customer service always to 5-star reviews on multiple sites.

Logan started to bottom regularly to Nicky’s cock and used a few of the smaller toys, with what he said were some of the best ejaculations he has ever had, but we all knew he had not hit near the “Peak Cum” yet!

Soon within days or weeks, he had agreed he wanted to upsize to the large Seahorse on the fucking machine while he would watch Josh fist fuck Nicky again, or so that was the plan. We were all very open sexually with each other and understood it was like playing hockey and, who was coupled with whom, so it was just sex and pleasure when we mixed between our betrothed or dedications. Nicky kept wishing that Logan would try his fist, but I emphasized patience, as I sensed Logan felt pressured.

Over the last few months though we all (including myself especially) noticed a change in my Joshua.

Josh started to wear his hair a bit longer and really did perfectly his eyeliner and shadowing but in a more masculine attractive way, with a very hot cat-like predator look about him. But the biggest change was his body. It was perfect, to begin with, but he started to hit the gym daily and really watched the booze and ensured maximum water hydration vitamins and supplements, and plant proteins. I was amazed and thought that he had peaked sexually with vitality and virility, but I was so wrong. My Joshua was just starting to be tapped into something none of us could believe!

Although in November here in Canada and cold below 0c many days, we all often in disbelief starred at Josh as he worked out with dumbbells and barbells out on the balcony in shorts and ½ T-shirt and tuque. He went from 150 lbs to about 165 lbs and was a lean ripped and beautifully sculpted young man, who filled out to perfection and seemed about an inch taller at 5”11” just shy of my height. During our anal sex and fisting and massive dildo riding, I was in awe as I could see all his ass and thigh and entire muscular system reach full body orgasms, every bulging line and fiber was perfect not overdone but just absolutely perfect…Fuck I was the luckiest guy on the entire planet to have him as my lover.

Having pierced his nipples with mini barbells, along with his tongue and his scrotum and perineum he was becoming so much more aggressive sexually, and we all loved it, me especially! He was perfect and gorgeous. He had also been going hard at the penis pumping, sounds, and rosebud anal pumps.  During last night's group fuck I noticed his gorgeous cut cock was now the same size as mine at 8.5”

 Earlier today I joined the boys down in the complex gym. I was amazed at the strength my Joshua had built and the perfect form he was in…. not only was he turning heads, but they were also spinning, and eyes on him were like lasers making him Swiss cheese from the women and the men! Although I, Nicky & Logan were all really great looking and in great shape, we all knew Josh was now a God! Nicky and Logan had mentioned after most workouts they would hit the male clothing optional pool, and of course, many guys half hard, but Nicky and Logan could not believe how relaxed Josh was walking around and swimming with his massive hardon of rock-solid iron. There was no way to tell the straight guys from the not, as they all drooled over my Joshua.

We were heading to the showers and hard cock Josh said,

“Let's all go to the mixed clothing optional pool!”

Logan replied first, “Why are all the guys staring at your gorgeousness not enough anymore, now you need the other team too.”

Josh stated, “Fuck off Logan, I just thought it would be a bit more fun and daring rather than the same old cock and lock we usually do.”

Nicky replied, “Hey I am game if you guys are?”

I said, “Ok sure we will all go to the mixed pool.”

I walked in first with a towel around my neck sporting my half-hard 8.5” member with a little moan from the 20 men and about 10 women, followed by Nicky who was also at the partial mast with moans, and then anaconda cock Logan with a bigger gasp and moan from all….but …but when Josh walked in…when Josh walked in ...oh my God… with towel in hand sporting his now-massive fully erect 8.5” cock there was a much, much bigger gasp! We preceding three might as well have disappeared as every eye male and female was glued to Joshua!

We swam around for about 20 mins with Josh doing much backstroke so his cock was well seen sticking up like a schooner mast!

We sat down at a table and Josh got out last and sat on his towel, still sporting his rock wood! I spotted out of the corner of my eye the 35 yo very attractive with big tits and shaved pussy and nice shape Mrs. Harrington approaching. Her husband was often in Europe on business, and she was well known as the building easy lay with no strings. She approached and said,

“Well, well gentlemen welcome, what a lovely surprise and treat for us for you all to join us tonight.”

She looked at all our bodies and packages but could not get her eyes off of Josh. She continues,

“Now you young man, …wow….(She pants and sighs)  you are spectacular! I suspect you play on the other team here with your hot friends, but if you ever want to switch, I take it in all 3 holes, but especially love it up my loose ass.”

Josh replied, “Oh really… I doubt your ass is as loose as mine.”

Mrs. Harrington replies, “ Oh it is trust me!”

Josh gets this devilish daring look on his face and says, “Can you do this!” as he lifts his legs up and does a massive rosebud bloom much to Mrs. Harringtons' bug-eyed gasp, she says…” Oh my God!” She yells, “Are you hurt… do you need an ambulance!”

Josh de-blooms and puts it away and says, “ No I am fine really!” Still panting and very flushed She says,

“Wow…holy shit! Um…Um…can I touch and suck your penis please?” She begs. Josh answers,

“No, I think enough excitement for one night we best be going.” Suddenly she plunges to her knees and grabs Josh’s cock and starts furiously sucking it. We are all amazed Josh is in shock not sure what to do, when we spy running down the poolside Jefferey, the building manager.

“Mrs. Harrington, how many times have I told not to accost the young men!” Jefferey exclaims. We all pulled her off of Josh’s cock as he grinned from ear to ear.

She says, “But look at him he is so gorgeous!” Jefferey being very very flamboyant and very very gay, also says, “

“Yes, we all know that, but you can’t assault the bathers like that, and you all know the rules, no sex in the pool area!”

Jefferey was the wife of my high school buddy, Gerhard. I had yet to tell Josh that Gehard was the man (18 yo teen boy at the time) that I had my first bottom anal sex. Jefferey smiled and waved and winked to us boys as he escorted Mrs. Harrington out of the pool.

Logan says, “Ok Boys I think that's a wrap, now let's get the fuck out of here!”

We all followed Logan, but you could see all the other bathers staring at my Joshua with tongues rolled out like dying dogs as he pranced past with the iron-hard cock and perfect body!

Once back at our penthouse unit as Josh was changing, Nicholas and Logan insisted I chat with Josh and see if all was ok upstairs, as his demeanor the last few months was so risky, daring, and aggressive along with the piercings, body and look transformation into a God, it made us all anxious and worried!

Josh came down to the Kitchen Island, and Logan and Nicky headed to their bedroom.

I opened a bottle of wine and Josh said, “I would prefer some water please?” I open the fridge and hand him a bottle of his favorite spring water. I begin.

“Joshua are you OK…is everything OK, are you happy here are you still in love with me and our life?”

Josh tears up, “Fucking yes, God I love you more than life itself Fuck why would you think otherwise?”

“Josh, I have always loved you just the way you are, but fuck this ripped sculpting and the gym and the piercings…are you competing with the other boys and risky behavior and aggressiveness it worries me and them?”

Josh replies.

“Yes, I am still and always will be very Gay and yes I am a Fem… It's not Nicky or Logan or you and yes, we both know they are very attractive and both in great shape. I am madly in love with you and love you so much I would give my life and die for you Taylor…and eat your shit! I love our group sex, but as I keep building my orgasms seem to be firing my testosterone off the charts, and I am really loving it. I am almost hard 24/7, and in the last few months, I have felt there is this 40% dark masculine side of me that needs to break out and mature and grow, so I ask you, my life, my lover, my everything Taylor,  that you and the guys please support this little split personality Jekyll and hyde in me needs to come out. I seem to be yearning for more and more pain as I love the pain from working out and sore muscles and hence the piercings, but I am missing the deflowering pain I endured the nights you took my anal virginity. I seem to have an unfulfilled need to keep re-experiencing the euphoric feeling as pain turns to exquisite pure pleasure.

I also seem to have a secret need to be the champ, so I need the heavy-weight cum title back!

I smiled and said, “Oh my Joshua…l... Love you so much you are so incredible, and fuck you have taken your look to a 20 /10 God!

Josh replied, “I love you too Taylor, but If I ask you and the boys to do something to me you know will be painful, as long as there will be no permanent serious damage I want you to do it without question. I trust that with your medical degree and Logan here you will make sure I don’t end up permanently injured or dead!”

I let out a big sigh, …” so my little Femboy has a deep dark bad boy masochistic side that needs to come out….so what things did you have in mind?...wait is it ok If I get the boys and we chat together about this.”

Josh replies, “Yes Taylor go give them the short version and bring them up to speed as to where I am in my head space and what is behind with my “God transformation.”

I go down and tell Nicky and Logan what going on. Nicky blurts out, “Well I am game to punish that hot ass Sith Lord and see if a lightsaber up his ass will give him the cum title back!

Logan replies.

“I understand and we learned a lot about this Taylor in the most recent human sexuality and Psych courses that we now have to do at the med school, so yes let's hear him out, and I think we will try our best to get him to where he wants and needs to be. We love you guys and want us all to be happy here!”

We all go down smiling and Josh is sitting there with a much different look on his face drinking Vodka. I said, “OK Josh we are ready and all willing to support you, so what did you have in Mind?” The boys and I all gather around the island on our chairs.

Josh takes another shot and starts off with a big sigh.

“Well, hot wax plays all over my nipples and cock and ass, hair pulling and pubic pulling out, more nipple, penile and scrotal piercings and scrotal inflation with saline, electro play all over my body and up my ass. I really want anal, rectal, and colon stretching to the point of pain and a bit of blood but not rupture or fissures. Flogging, caning, and whipping including my cock balls, and ass. Penile stretching with pumps and sounds, 2 of the largest toys up my ass on the fuck machines on max power and depth at once, and eventually 3 or maybe even 4 fists in me at once!

Forced to eat cups of cum, piss, and multi cocks choking my throat, group pisses down my throat and up my ass. Spank my ass, secure me on a leash tie-up, and gag multiple cocks in my ass at once and pounding hard as they possibly can. I am in fantastic shape I can take it. Suspension and whole body stretching….uh spanking till I am really red and pink….maybe more but that's all the cums to mind right now.

Logan says, “Well if you are serious, I am willing to try, but let's do it safely as possible yes!”

Josh replied, “Yes that is the support that I need, and I will also be more aggressive with you guys’ Taylor especially, but I want us to have more hard pounding ass breaking sex.

Nicky replies,

“This is music to my ears, and I am raging hard cock right now thinking about this, but first….”

I answered, “First we have to get you Logan to a first peak cum, tonight you will be anally broken in much wider and deeper than Nicky’s cock, and tonight you will take Nicky’s fist in your ass. At the same time, I will start to do some of Joshua's wish list, as he is my lover, my responsibility. So, if anyone is to hurt him as we start this, it is going to be me!”

Josh with a teary smile says, “Thanks Taylor, now fucking do me, lover! I’ll say stop or no or clench and open my fists as a signal to stop if I can’t speak, so all make sure you don’t tie me up and gag me or I will die!” Josh laughs.

I said, “OK boys let’s go wash up!”

Nicky & Logan headed to the ruby bath and Josh and I to our master bath.

Josh was rock hard with thick cum oozing from his perfect glans. We held each other for a few minutes as he kissed me deeply. As soon as he pulled off, I grabbed his nipple bars and twisted them, he screamed in shock and shot a small load of cum, then I lightly slapped his ass and spanked his cock causing more more whimpers and groans and more cum flow. He smiled and said, “Thank you master, I love you so much.”

I replied, “Bend over you bitch.” He did and I inserted the douche nozzle up his ass blowing some light brown water and solid shit chunks out of him. Once he was totally clean I said,  “Bend over on the bench.”

Josh was expecting my cock, instead, I started to spank his ass as hard as I could, and fuck he was solid muscle, and he screamed, “Yes Yes harder Master Taylor, harder, spank my bad boy ass!”

I did exactly as he asked, and just when he was going to cum, I pinched his cock head closed tight forbidding his orgasm. I kissed him hard and scraped his tough with my teeth. Josh replied,

“Thank you, Master.”

I put a leash and collar around his neck and pulled him into the playroom. Nicky was jamming Logan's huge cock into a cage and they had the large Seahorse connected to the fucking machine. Once Logan was all locked up with a 4-inch cage and 6” cum tube he got up on the leather bench. Nicky slid the Seahorse into place and slathered more than enough lube up his ass and all over the toy. Logan was excited to be finally deflowered by the traditional start dildo. A puddle of cum had formed similar to all the boy's starts but not as big as Josh's or Nicky’s.

I put on the locking cuff and angle shackles onto Josh and told him to kneel on the bed. Meanwhile, Nicky started Logan’s dildo breaking his cherry much to his Scottish moans and groans. Nicky started to mount the XXL Centaur horse cock in the other fuck machine.

I came back with a tube of toothpaste and slather coco lube and it all over the largest and deepest butt plug we had. As I inserted it into Josh’s anus and rectum a moan escaped him and then some whimpers….and then some

“Oh fuck, fuck that burns, fuck yes Master Thank you” Josh cried out. These words totally had us all dripping. I dragged him over to the St. Andrews cross and faced him forward. Then I inserted into his penis the 15” silicone sound that was 3/8th thick again with just a bit of toothpaste and jelly lube. His cock was so engorged he was rivalling Logan and the other boys stared in disbelief at how big and hard Josh's cock had become from all this ….just starting his wish list.

Logan and Nicky could not keep their eyes off what I was doing to Josh and how he was loving it. Josh moaned and groaned at the sound as it burned in his cock. Then I latched a parachute ball stretcher with spikes around his balls and hung weight totaling about 2 pounds. A tear streamed from Josh but he gave a nod. I asked, “Proceed?”

Josh replied, “Yes Master more please”. Now I lit a candle and started to drip the hot wax all over Josh’s nipples and cock and little triangle pubic hair. He looked so angelic. I had to piss so I pissed in a bottle and then told Josh to open and he did. He swallowed most of it but the bottle rush is much bigger than a cock stream so he started to cough and gag getting piss all over his face, chest, and cock.

Nicky was not caged, and I do not think I have ever seen him this hard and big and was dropping a good stream of cum as he rode Centaur hard to its base on his fuck machine.

Logan our virgin, was moaning guys It's too big, there is a lot of pressure and it burns.

Josh yelled out, “Take it you fucking cunt pussy, push down now and you will see, now Logan ride that cock to its base!”

Logan pushed back with great winces of pain, and then Nicky hit max power and depth and drove it in him. Suddenly Logan's head reared up and he cried out in his great Scott accent,

“Holy Fuck, Holy Fuck yes, oh my God yes, oh fuck more please Nicky hard and faster!”

Nicky replied, “It's on Max warp speed already dip shit, fucking ride it and enjoy it.”

Logan said, “Oh shot you bastards why did you not tell me it was this good, fuck the sensations, holy shit it's fantastic its in my sigmoid holy fuck it's like heaven!”

Josh was smiling but then I turned around with the flogger swinging across his chest, cock, and the spiked weighted parachute hitting his front from his nipples to his knees. He cried out in pain, and yelled,

“Harder Master Please, Harder!” When Nicky saw the look on Josh’s face of pain and euphoria, he cried out,

“Oh fuck, fuck I am going to cum, oh fuck it’s a great one.” With that Nicky pointed his raging cock toward Logan's face about 5 feet away, and his famous cum shots covered Logan's face, mouth, and hair. Logan kept moaning and riding the Seahorse balls deep.

“Fuck I can’t believe I am doing this, and fuck you guys I knew from watching you all that it was pleasurable but fuck this is fucking incredible.”

Nicky finished Cumming and pulled off XXL Centaur. He grabbed a pair of fisting gloves and a bottle of lube. Logan moaning and groaning said,

“Nicky, what are you doing?” Nicky did not reply he just dumped the Lube all over Logan's ass and Seahorse milking his prostate which has a 4-inch puddle of cum dripping from Logan's caged cock.

Logan started screaming as Nicky slowly slid his hand underneath Seahorse so that his knuckles were striking Logan's Prostate. Logan started to cry and whimper, it's too much Nicky wait!

Nicky said, “Breath Logan big breath relax, and breathe it ok.”

Logan replied, “I’m trying,  give me a few…oh Fuck Fuck holy shit oh Fuck Nicky is that your entire hand in me?”

Nicky replied, “Yes, it is lover, now fucking ride it and cum for us.”

Logan cried out, “Oh my God it's so good holy shit Fuck Fuck it sucked it right in like my ass has been starving for it...here it comes, Fuck it so big Fuck!”

With that Logan sprayed out of his cum tube a great 5 large squirts of thick white cum hitting the table with a loud spray of about 150mls or 5 ozs. He continued to moan and groan as Nicky kept working his prostate Logan started to push back even more and unexpectedly said,

“Oh shit fuck there’s more I am going to cum again of Fuck Fuck Holy Shit this is unbelievable.” Another 3 squirts and the sweat cover Jock collapsed, and Nicky pulled his hand out and slowed the Seahorse and pulled out the dildo.

Finally, Logan's cherry and sigmoid had been broken in and he was one of us.

Nicky helped him down off the table and they kissed deeply and then shared Logan's cum in a slurp fest.

Josh was rock hard and I unclamped the spiked parachute balls cage no blood but his balls and scrotum looked raging red and sore and pulled the huge plug dildo out of his ass. Then I removed the urethral sound and was kneeling as once out Josh had a massive hands-free cum so I opened my mouth and collected all of it as his huge cock pulsed and pumped out all his seed. God, he tasted like vanilla ice cream!

I went up to his mouth and he opened, and I returned all his 1/2 cup of cum to his mouth as he swallowed eagerly. Logan was wobbly done kissing and slurping with Nicky, so the 3 of us decided it was time for all 3 of us to fuck Joshua.

I laid down on the bed with my legs over the edge and instructed Josh to mount my cock with his ass near the edge of the bed so that Logan and Nicky could fuck him doggy style, with all 3 cocks ravaging his gaping hole. Still covered in wax and cum and piss he brushed up against my chest and face. He was so beautiful we kissed deeply, and he bit my lip and tongue which shocked me but no blood. I almost came.

Josh lowers his pussy onto my cock and started to ride it with many groans. Then he slowed and said, “Logan, cum get in me.”

Logan had removed his cage and was massively hard with his huge 10” uncut anaconda, he lubed his raging cock and entered Josh’s ass from the left of him. Then Thicky Nicky did the same from the right. My Femboy had 3 huge cocks up his pussy and started to ride like crazy!

Josh yelled, “Harder Boys Fuck me as hard as you can please, breed my cunt with your seeds, Taylor Hug me tight and hold me hard while you all gang bang me, harder faster come on you fuckers fuck me as hard as you can!”

Logan and Nicky were panting and pounding Josh’s ass and the feeling of our cocks hitting one another’s was just incredible, none of us had ever done anything like this! I cried out first.

“Oh Fuck I am Cumming, I Cumming,”

 Then Logan said, “Yeah me too here it comes boys Fuck Fuck it's so good.”

 Then Nicky yelled, “Oh guys yes holy shit Fuck I’m blowing a huge one Josh Fck you are awesome!” The 3 of us came and bred my Joshua.

Josh grabbed my shoulders and said, “OK Boys watch this now!” Josh started riding our cocks and he clenched down so hard none of the 3 of us could pull our cocks out of his ass. His muscles were fucking incredible, he had become an absolute powerhouse who could probably kick the shit out of all of us, as he sat up some, just about tearing our cocks from our bodies he started to scream and writhe to and from right to left and bucked like a wild horse and the 3 of us were in pleasure and pain having our cocks vice gripped and milked to death! Josh yelled as loud as I have ever heard him,

“Boys I am Cumming Fuck I am Cumming, Taylor Open your mouth ...holy Fuck here it comes Fuck so good!”

We could feel Josh’s prostate pump with each beat of his heart it was the size of a grapefruit just like Nicky had had. I sat up a bit and opened my mouth getting ready for my lover's seed, and oh my fucking God, he actually had the new cum title… my face hair and mouth, and throat were covered in over a full cup or about 500 mls of Joshua cum…he came for a least 3 mins of blasting squirts and did not stop until Logan Cried out.

“Please Josh release us you going to break our cocks!”

Josh collapsed on my chest and released our three swollen cocks from his vice-gripping pussy.

Logan and Nicky fell to the floor panting like we had all just swam 50 laps nonstop. Josh lifted his head and started to lick all his cum from my face, mouth, and lips and kissed me deeply sharing in his massive load. Logan and Nicky got to their feet and came over to see my face chest and hair.

Nicky said, “Wow Josh you have the record back… like where and how can you make so much cum. Although you tried to rip our cocks from our bodies this was the second greatest sexual experience of my entire life and the only thing that topped it was the night you guys drained my prostate….Fuck I love doing this with you guys its so much fun for me and my Love Logan.”

Logan said, ‘Here here… this was the greatest sexual pleasure I have ever ever ever had and I know you guys enjoyed these deep giant toys up your ass with your fists, and now I understand…fuck it's so much more than I ever imagined, I have never cum and had such pleasure in my ass.”

 We all kissed and headed to the Master Bath shower. The wax peeled from Josh’s bare chest perfectly and when he was not expecting I saw he had a huge chunk in his triangle pubic hair. I distracted him grabbed it and ripped as hard and fast as I could. Josh cried out and slapped me!

“Fuck Taylor, I was not ready for that!

I replied,” Well that is what you wanted yes!”

Logan and Nicky started to laugh hysterically as they looked down and Josh had a reverse Mohawk pubic bush…Very cute. We had some food & drink. Cleaned the room & crashed into bed.

Josh said, “Taylor thank you for loving me enough to do that to me…. It was all a great start to what I need and want.”

I answered, “I love you so much and the greatest pleasure I have is seeing you cum and scream in ecstasy tonight just like you did over 2 years ago. You understand your body and you understand your mind and mental emotions and entire physiological structure and central nervous system. Joshua we are just beginning to tap your full potential. When you peak climax soon as the 4 of us continue down this path with you, we will witness the greatest explosive climax orgasm ever in the history of humankind!”  

We kissed and passed out asleep holding each other.