All depicted activities and individuals are fully consenting adults, at least 18 years old at all times.
My name is Charlie Baxter. My life growing up has been very different from that of most boys. It has not been bad or anything. In many respects, it is relatively calm and super phenomenal!
You see, I do not have a known father. My mom, Ashley, at age 19, had cum out as gay and lesbian. She is very pretty and reminds me of the famous, gorgeous actor Charlize Theron. She had decided that she wanted to have a child, just not with a man's cock doing the impregnation deed, although she had been cock fucked several times; not wanting to know the father directly or have him know his child directly, so Artificial Insemination and here I am 18 years later.
She went to a local fertility sperm bank and sifted through profiles and pics. There are no names or dates of birth; just approximate ages, birth signs, IQ scores, current career areas, degrees held, and the field. She picked a hot, blond young man she thought resembled a mix of Travis Fimmel (Actor-model as he looked when he did Calvin Klein undies – fucking hot!) and Christopher Atkins (The Blue Lagoon – original, Actor-model). The donor is smart, with a master’s degree in business administration; apparently owns his own distribution business at 28—a Greek God at 6 Ft 4” and 170 ripped lbs.
So out I came 18 years ago in 2007, on Feb 14th. Yes…Fuck! Valentine’s Day birthday: well, I always got kisses! Some were unwanted, others I was dying for. Given my sperm-donor father's profile and my mom’s love of the movie and its “Charlie and the Chocolate Factory” repeats, I was so named.
Many said that, as I was growing up, I looked a lot like Charlie Plummer (actor, grandson of the famous Christopher Plummer, God rest his soul). So, at 18, I was not complaining. Similar bodies, six feet two inches tall, about 160 lbs, lean with nice, light definition, perfect teeth, deep blue, gorgeous eyes, and long platinum blonde hair past my shoulders in a messy wolf cut, with wild back strands and shoots down my back. My dick…a nice cut 7.5” with dark brown pubes and pits.
So, apart from my father being a sperm donor and my mom being a lesbian, hold on; it gets so much fucking better!! Mom is a fully certified PHD, local-renowned Sexologist, Gynecologist, Obstetrician, Urologist, Andrologist, and Proctologist, with a degree centred on sexual pleasure, psychology and sociology. Basically, she knows all there is to know about both genders, genitals, kidneys, bladder, anus, rectum, colon, and all the related orgasm climax glands and nerves and how they connect in the pleasure ecstasy centres of the brain. My life growing up with her was quite liberal and sexually very open-minded, especially considering that, in private, we are naturists and nudists. There was never any body, sex or pleasure question that was embarrassing. It is terrific!
Mom has had a few lesbian lovers and live-in girl friends over the years, although before settling in as mostly lesbian, she had had sex with young men before conceiving me. Over the years with her female lovers, we were all often fully naked. None of them ever once abused or touched me or suggested sexual activity at all in any inappropriate manner at any age or exposed me to any underage age sexual activity; I mean, apart from me hearing through the walls their wild sex; all kids hear their parents and their partners at some point.
I really do not understand what all the hubbub is about with some countries and parts of the world so uptight about our God-given nakedness and sex. It was so relaxing to cum home from school, strip down, shower, dry off and stay nude until we had to leave the condo for whatever. I often left my door mostly or partially open; there were no secrets, and I wasn't hiding anything or any fun activity. It was so relaxing and supportive; I can’t imagine how other people live so bound, restricted, secret, scared, and stressed. I loved the freedom and the lack of embarrassment about our nude activities and lifestyle.
Of course, back when I was 13, my mom taught me all about the birds and the bees, our body functions, and pleasure nerves, with a 2x4 ft laminated book of male and female anatomy. The only embarrassing thing about that was over the years in late grade school and high school, having to correct the teachers about sex, orgasm, ejaculation and making babies. Fuck me! I practically taught the classes. All the teen boys and girls thanked me for having and sharing so much important information and clarifying and correcting all the erroneous crap available on the internet. Yes, private teaching sessions occurred; not saying anything more on that!
Sleepovers with boyfriends until the age of 18, we all at least kept our underwear or Speedos on, and no real sexual activity at all; just the usual messing around that all teen Boys & Girls do as a regular part of healthy and natural curious experimenting growing up to become young adults. Mom never forced me into any orientation or gender, as we really hated the labels and segregations.
I mean, I was taught that people have sex and make love with people; there should be no attention to what body parts they had or what they psychologically felt inside they identified as; same as race and skin colour; we are all human and all sexual beings.
I started PREP at her clinic a few weeks ago. Until I was 18, I was in fact a virgin. My first 18+ night as a young man was unforgettable.
I guess I would be considered multi-sexual because at 18 now, I informed Mom as follows, given our very open, supportive, professional and non-judgemental family and home,
“Mom, in hours now, once I am 18, I do plan on being extremely sexually active with all people over 18 of all genders and orientations; I am certain you are okay with partners nude and engaging with me in various sex acts openly about the condo. I am also interested in trying some of the very big toys anally. But first, I have a bit of a bomb shocker to drop!”
She replied, “Of course, Charlie. I am so proud that for the major things, you have waited until you are a young man. As for big toys, I suspected so; just be patient and wait a few more hours for surprise BD gifts tonight! Now, what bomb do you think would possibly shock me?” She smiled so big as I blushed. I was so excited and anxious now!
I began, “Well, although now that I am 18 and will be having sex with Young men, Twinks, and maybe even experimenting with Girls and other Genders, what really turns me on is the thought of sex with… ah…ah…well, like an older man…like a much older daddy type guy to actually take my anal virginity? Is that fucked up, Mom?”
“Oh, Charlie, of course it is not fucked up. Many people in my therapy practice share that they have had consensual adult sex with their older adult family members and friends or even strangers. You are a young man now, and what is important to me is your absolute happiness, sexual pleasure and safe satisfaction. Do you have a much older man in mind?” She said, smiling from ear to ear.
I answered, “Well, in fact, I do. But I am unsure how to approach him. Mom, it is Danny who lives down the hall from us?”
“Oh, Charlie! He is fucking gorgeous and super sexy hot. I have only ever seen him holding hands with young men and Twinks, so I am sure he is open to it. I think he is in his late 40s, maybe 48. He looks fantastic, doesn’t he?” she beamed. I think she was anxious to see how big his cock was, too!
I continued, “Mom, so many times when I bump into him these years and decades in the halls, elevators and common areas, pool, sauna, steam and fitness, he is so friendly and respectful; always kept covered and never once flashing his cock in the changeroom or private showers; neither of us have any idea what our naked looks like; deep inside he makes me melt with those muscles, and piercings and hot queer tattoos, and my god that crotch bulge under his clothing is so fucking big. He has never once made a pass, asked, suggested, or talked about any sex. I guess I will be blunt and just cum out with it.”
“Well, I have fun plans for your birthday tonight and some incredible gifts; if you see him, invite him to cum knocking about 5 PM. I would just say, cum for my birthday party. Then I want you to fuck and breed my virgin twink asshole and share the other surprises that mom and Bailey have in store for me,” She giggled. I nodded and began to percolate my approach. Her current live-in lesbian partner, Bailey, has a hot look like actress Megan Fox, a different demeanour and character.
On Friday, February 14, 2025. I got gifts like no other 18-year-old boy ever had. Mom owned several of the local sexual health clinics and had privileges and demands at many regional hospitals, so I am sure she raked in millions each year, very blessed in that regard.
Our two-bedroom condo on the 30th floor of one of Toronto's most luxurious buildings was incredible. It was all open-concept: each bedroom had its own private, huge ensuite and a third full bathroom for guests, with in-suite laundry in the third bath as well.
I got dressed and ready for school. Looking at my watch, it was 7:47 am. I knew Danny would be at the elevators soon; we had nearly the same meeting schedule at 7:50 am every day as far back as I could remember. We are almost always alone in the elevator and often chat about sports, the weather, politics, economics, and stupid things. I dare say, Today’s chat would be life-changing.
I left our condo, and lo and behold, Danny was locking his up and heading down. As we met at the elevator, he greeted me.
“Good morning, Charlie, how are you this Valentine's Day? Is it your birthday, right? How old now?”
The doors opened, and we were alone. In my reply, “I am 18 today, Danny!”
“Oh wow, an adult, gorgeous young man, congrats. Any big plans?” He spoke.
I peered deep and seriously into his incredible hotness, blurting out, “I am praying you will cum fuck and breed my virgin ass and pound and plow me all night long with your very big cock, I am sure, while Mom and Bailey have other pleasure surprises waiting and watching!”
I swear I thought his eyes would explode, and he might collapse into some attack. He smiled and giggled, “Are you serious? Because I have mediocre plans, but this would be a million times more fun. Charlie, you are absolutely one of the most beautiful boys I have ever seen; if serious, it would be the honour of a lifetime to be with you and take your virgin hole. Just name the place and time.
I responded, smiling away, “100% legit, Danny. I have found you extremely attractive and want a Daddy to teach me all about boy-on-boy gay daddy sex and anal pleasure; we are nudists, so arrive at 5 PM and expect to stay the entire weekend. Just one request I need right now, show me your big cock, please?”
Danny giggled and continued, “Not here on the elevators and cameras; why don’t I drive you to school today as an early birthday present?”
So excited, I was bouncing and beaming, “Totally yes, dude!” We got into Danny’s big black, fully loaded Cadillac SUV with dark-tinted windows on the P3 parking level.
I said, “Wow! Bitching ride, man!”
“Yes, but it has always been missing the most important accessory,” he said. I fucked up my face looking around. He giggled and answered, “A super hot twink like you; now cum lick and suck my huge cock, you hot little fuck.”
OMG! He was not kidding. I mean, he is 6 Ft 4” and a 170lbs ripped and shredded, picturing him just like the daddy I never knew; when Danny reclined his seat back, and I got on my knees leaning over the centre console, when he unzipped his fly and pulled down his jeans, his hard, tented bulge was massive. I was gasping and dove straight for his dripping mammoth glans, the size of a large mushroom. I sucked his pre-cum through his tighty whites and tasted the sweetest semen I had ever imagined. After several glorious minutes of worshiping, sucking and pumping his huge kielbasa-like penis through his AC thong, I released it from his silky bondage. OMG! X2!
I stroked him to a full oozing erection in no time and sighed and gasped, “Holy Fuck, Danny, your cock is like the most gorgeous huge fucking dildos online, but Jesus Christ, you must be a fucking foot long and as thick as my Twink arm!”
“It is just the angle. I am 10.5” long, and the widest part along my shaft is 1.75” thick or 6” around in circumference. Unfortunately, no one has ever been able to deep throat me, so I doubt you can get more than 4” down your sweet Twink throat. Mostly take my pre-cum and your saliva and jerk me off with your pretty cool little fingers; nibble and lick me till I blow a gusher down your throat.”
“Fuck yeah! Give me all that hot white blasting Daddy cum down my Valentine's birthday tummy!” We both laughed, and I began my task. My cock was so hard in my jeans, and I felt my wet spot running like mad. I did not care as I was super horny, turned on about the thought of walking into school with an 18+ huge, tented cock in my jeans and a massive cum spot visible for all to see.
I licked and swirled all around Danny’s Cock as he held my blond locks powerfully in his big hands. I began a slow open bobbing motion with my jaw breaking open just to get 3 or 4 inches of his titanium-bursting cock in my mouth and throat. I knew my tongue had to do its best.
I was so excited and happy, babbling, moaning, and groaning, “Danny, your cock and cum taste so good and sweet. I am so glad I have waited for a real man to break me in. Now, please give me a full load down my Twink tummy.”
He nodded and forced my face faster and much firmer on his cock. I was starting to choke trying to get him further and deeper down my oral Tunnel. I was gagging and coughing up spit and snot, with tears running from my eyes; I doubled my efforts and just kept my best up as I thought if I died, it would still be the best birthday ever.
His cock was so fucking massive. My cock has never been this hard and wet ever; just the thought of him pounding my ass open had me terrified yet so anxious for the pressure and sensations to finally get ass fucked big time; I wondered if the rumors were true about he pain dissipating and a boy able to cum hands free from the sensations and prostate vesicle pressures bashing through all my silky sensitive routes and doorways. My nerves were like lightning bolts. My brain is going wild!
Suddenly, Danny cried out, “Oh, Charlie, yes, yes, I'm going to cum! Get ready. Oh, fuck it is a huge fucking load, oh Fuck YYYYYYEEEEEEEEWWWWWWWW FFFFFFFFFFFUUUUUUUCCCCCCCKKKKKK GGGGGGGGOOOOOOOODDDDDDDDDD YYYYYYEEEEESSSSSSSSSSSSS FFFFFFFFFFFFUUUUUUUUCCCCCCCCCKKKKKKK!”
Holy shit! I had to pull off to keep from choking as massive torrents of boiling, thick 48-year-old Danny cum squirted and pelted hard against my Twink throat. I pulled off for a second and just opened and let him squirt volley after volley after volley all in my mouth and down my gullet. I savoured and loved every drop. After ten minutes, he was finally done. My face, mouth and throat are drowning in Danny's cum! I was sold; totally gay I am! This was the best thing I ever tasted; I felt so complete and powerfully manly.
“Holy Fuck, Danny, that is like a quarter cup, I fucking swear. Best thing I ever tasted…Daddy.” I spoke.
“Cum kiss me, Charlie, and share my cum back to me, please, Valentine's Birthday boy,” he chuckled. I leapt at his face, and we shared his hot, lovely semen as he passionately twirled and swirled our tongues with spit and sucked our mouths and faces for another ten minutes, probing spots and sensations so dreamy, erotic and exciting! Thirty years apart, and I am so hot for him!
We finished with a cuddle and a little peck; Danny smirked, “I am going to make your cock hard all day now. Look at your tent and the wet spot. Sure, you are OK to go to school like this…oh, and you have some cum on the side of your face and hair.”
I answered, grinning from ear to ear, “Perfect for this hot Valentine’s Day birthday.” We did up our pants jackets, seat adjusted and belted up. I rubbed his crotch all the way to school, and he stroked and circled his fingers on my jeans' tented pocket with the wet spot the size of a large orange now.
He pulled into the school parking lot; most of my friends were in view, staring wide-eyed through the SUV windshield. I leaned over and gave Danny a super hot kiss, making sure all the 18+ boys and girls saw me with my crotch squeezing Daddy.
As I undid my seat belt and opened my door, I yelled so all could hear, “Danny, I can’t wait for you to breed my virgin hole with that massive footlong cock of yours…no jerking off now!” He shook his head affirmatively; my friends were like Medusa, stone-faced and tongue-tied on the ground. I walked over and just said, “Great morning, boys!” As I continued, I heard whispers about the cum on my face and hair…Finally, I had a medal of honour and wore it so proudly! I am a sexual Man!
All day, I had to field questions from all the LGBTQ2FS2+ students and friends. I had three close male besties; all of them had been to sleepovers before. In weeks, they would all be 18, and I was dying for real Twink orgies now, with us all finally naked around the house and Mom cheering us on.
I practically sprinted like the Flash home at 330PM. Mom and Bailey both took off work early for my Birthday and Valentine's Day. I was walking into the condo's main foyer when they pulled up in the entrance lobby circle, honking the horn of a brand-new, fully loaded 2025 Acura MDX in bright blue. I knew right away it was my first gift.
After enjoying an hour driving around with them in my new set of wheels, we got home. I parked in my new spot, a few cars down from Danny's SUV, on P3. Even at nearly 40, Mom and Bailey were super hot; the three of us were turning heads. This was so much fun, but all I could think about was super hot Danny and his huge, gorgeous Cock waiting for my starving, begging virgin hole.
Once we came off the Elevator, Danny, with perfect timing, walked up to us, “Hello Birthday Boy, was that your hot set of wheels I saw you beaming in?” My cock went to max trapped erection, and I squirted a massive pre-cum ejection just at the sight and anticipation of what was cumming.
I replied, smiling even bigger, “Yes, it sure was. What a great Mom I have, or what!”
“Oh, just wait, in a few hours, you will be screaming and doing backflips about your new Daddy,” He gushed.
Mom interjected as she unlocked our Bio-locking unit door, “Please do come in, Danny, and once the door is closed, I know that Charlie has informed you that it all cums off…everything!” He nodded with thumbs up.
The door closed and locked, and the four of us stripped. My cock was a solid 7.5”; I flung pre-cum webs everywhere. Danny was dripping and half hard at about 10”.
Bailey was speechless; Mom bugged out her eyes, saying, “Holy Fuck, Danny! Charlie was not kidding. That is the biggest cock I have ever seen, and you're not even fully hard yet, are you? I see why Charlie said he happily choked taking an oral load this morning on the way to school.”
“I would love to feed Charlie every day before he drives to school; I know you leave earlier for your medical work,” he said.
I answered, “We will work it out. I am so horny, guys, can we get on with it please?”
Bailey walked to the kitchen and said, “I will go get a case of cold water.”
Mom mumbling something about hydration being the key. She took me by the hand and walked me down to my bedroom, with my exploding, bouncing cum-webbed penis; my nice, hanging testicles bouncing about as usual, with my darker brown pubic hair that matched my pits, just like Danny’s. Danny was behind us hard as rock and fucking huge with a perfect, slight curve and big, dripping glans with cum strings to the floor now too, just like me!
There on the floor were three enormous 3ft square boxes with red ribbons. She must have had her other building orgy girls come over when we were out and get it all ready as a big 18th BD Surprise.
I will just cut right to it. One had the heavy-duty Cyclops XL Fuck Machine with a height-adjustable locking stand; the other had dozens of the most enormous dildos from Hankey, Topped Toys, Bad Dragon, and Square Peg. I gasped with excitement; I was flabbergasted…my penis…fully erect and bigger than ever; dripping precum wildly and proudly with no embarrassment –beautiful home and family life I have. Best Mom in the entire world forever!!!
Danny said, “Oh, wow! This is fantastic, Charlie. I wish you guys had told me. My company distributes most of these dildos and sex shop BDSM products; I could have gotten you wholesale with friends and family discount, saving you thousands!”
The third box was full of BDSM items like metal and silicone cock rings, metal and silicone Urethral sounds, metal steel and metal black cock chastity cages, leather collars, appendage cuffs, restraints, a few large Carmen Revera strap-on harnesses, floggers, crops, paddles…various anal rectal douching wands and hoses, Fuck water lube, X-lube and some oil-based shit too. It was fucking hilarious! I was over the galaxy with horny dripping excitement! Danny is beyond wet hard.
Mom said, “Charlie, my dear young man. Now that you are 18 today, I want to welcome you to all the pleasures your body is capable of. Tonight, we three will show you how to safely use all of these and reach the greatest anal orgasm your 18-year-old body can do, especially from massive deep anal penetrations with huge penis, dildos, and maybe even hands and fists. I can hardly wait to see how cute you are all cock caged up in chastity, my dear young man!?!”
“Oh, Fuck Mom! This is so awesome!!! I have been so horny, curious and anxious to try all of this stuff. Where do we begin, guys, so Danny can fuck and breed my virgin twink hole?” I asked.
“Well, let's grab this douche hose here and an 18” silicone anal wand; get it connected in your oversized open black and white tile shower. We will guide you on how to clean your anus, rectum and colon safely and no embarrassment about feces or smell…promise,” She answered.
I replied, “Well, you used to change my diaper, so it’s not like you have not seen or smelled my shit before!” She, Bailey and Danny giggled. We proceeded into my 10 ft x 10 ft ensuite with an open (Glassless barrier) shower and big floor drains. We hooked it all up in no time. She is so beautiful, with her Charlize Theron looks, and Bailey is so off-the-charts gorgeous, with her Megan Fox-like hotness. Their pussies were puffy and wet, staring at my oozing, raging, hard, near 8” cock; then they smirked, shaking their heads, staring at Danny’s massive missile that made mine look tiny.
I went to the toilet and took a quick dump first to make sure the bulk was out. My cock was so hard and running like a busted faucet. They directed me on lubricating the douche wand. I slowly inserted it into my anus and rectum. Very little came out; she and Danny guided me repeatedly until all were sure I was clean right to my transverse colon. Grinning beyond belief, it's evident they've all been doing this regularly as well. Several times, I squatted and fingered my hole with the lube and washed and cleansed all my bits down the centre large drains.
I dried and got back to the bedroom. Bailey was unpacking and assembling everything on the shelves and in the drawers in my room as my mom and Danny began guiding me through the toys.
We began with the urethral sounds. As Danny lubed and inserted an 18” long silicone one up his cock; when it hit his prostate, the gasps, moans and groaning facial expressions he exuded had me squirt a little hot white load. Now it was my turn! We all chugged several bottles of water; hydration is the key to cum and piss play.
OMG! Holy shit! I never imagined such sensations in the prostate. After I used the silicone and stainless-steel ones, I ejaculated incredibly hands-free all over my belly, chest, face and mouth.
I asked, “Guys, is it ok if I eat my cum and semen?”
“Sure, Sweety, it is quite healthy, so whatever turns you on is most important; piss is fine too, but be cautious with scat and shit play, not to ingest any. In the treasure box is even a 4ft clear tube with an open metal hollow urethral sound you can insert into your penis to your prostate or hook up with the cock cages; the other end is a dental-like brace device you can put in your mouth so your semen and cum ejaculations get sucked and swallowed through the clear tube. Is that not cool or what!”
Danny stated, “I have several of these as well. All my partners love them in conjunction with the cock cages; the anal penetration produces the most voluminous and powerful ejaculation you will soon see, and it is total shock, awe and fun to eat and slurp up all that hot, creamy boy-cum.”
I smiled and nodded as I used my fingers and hands to wipe the cum off my body and into my mouth with savouring sounds as they giggled and cheered me on. Fuck it is so awesome to have a mom, her lover, and a Daddy friend that recognizes an 18-year-old young man as a horny sexual being wanting nothing but the best orgasms and ejaculations possible. Fuck I love cum!!
“Mom, thanks for being so cool with me inviting Danny. Although you are the best doctor in all these areas, it is super reassuring to have a grown older man here who is also well-versed in all things for young men and Twinks.” They all giggled with thumbs up.
Mom said, “Charlie, Danny has given me permission to share and confess that Danny and I have several times had coffee and private sex chats over the years; also, he is in fact my patient.”
I jovially answered, “So cool & reassuring that we are all great friends here. Now more questions, when I am getting fucked and using the Fuck machine and dildos, could I cum on a plastic plate and lick it clean at anytime if I do not want to use the urethral tube to my mouth, even if I am cock caged?” I suggested. Bailey perked up her bright eyes, ran to the kitchen to get out the black plastic patio plates; we drank more bottles of water.
Mom continued, “Now, boys, remember all the king-size beds have the fully encased waterproof mattress cover and box spring covers too. The hardwood flooring is also super sealed; as long as it is wiped up in 24 hours, piss, water, cum and shit will not do any permanent damage, so no mess worries, just total pleasure for my gorgeous boy.
As you have been doing since age 11, you mop your room and clean your own sheets and clothes, and those of your partners as well. If the washer is in use, please put it in the Laundry or the guest bathtub with some of our health-app body-safe wash. Please do the same for the massive dildos and all the toys. Please never use harsh detergents, soaps, or chemicals.
“Got it, Mom! Danny, I am ready for fucking and breeding; cageless the first time, but later these sexy cages and huge dildos really turn me on,” I excitedly exclaimed.
“You bet, buddy. Get on your back first so I can suck your nice big cock,” he said.
“Big Cock…yeah right…look at you!” I sighed.
“Charlie, I have had some of the greatest orgasms and enjoyable sex with young men and Twinks between 5-7,” both as top and bottom. Size does not matter for anyone's orgasm or sexual pleasure and enjoyment of each other. You would be shocked at how much power and volume some Twinks and men ejaculate with penises that are 5” s. If you love and care about the person, that is the greatest turn-on of all. Wait until you get caged up with other 18+ boys and forget about your dicks and concentrate on your asshole and all its magnificent wet pink and red curves, nerves, bends, doorways and glands that will send your head exploding with pleasure beyond the stars!” Mom and Bailey nodded with thumbs up at Danny’s revelation.
I got on my back, and Danny dove for my cock. It was so incredible hearing Mom and Bailey cheer him on with loving approval and support, “Oh yeah, Danny, suck my boy's cock and eat his ass, teach him how to do it so good!”
OMG, could Danny ever suck cock! For my first time holding his long, blonde, wavy hair with grey bits brought me to my daddy fantasy so perfectly. His tongue and lips were exquisite beyond belief. The wet, sloppy slathering and sucking he did was unreal, taking me balls deep and chewing on my cock and nuts; pulling out my trimmed pubic hair actually turned me on incredibly. The chewing and biting were an unexpected drive to a wild, feral Twink cumming out! I like the pain!
I cried out as they continued stroking and encouraging Danny's cock eating, “Oh Fuck Danny, you better stop, or I am going to cum! You can eat me later, but please, I need my hole busted wide fucking open right fucking now!” Danny flipped me over effortlessly into a doggie position. I grabbed my headboard and held on for dear life! Suddenly, I felt Danny’s entire mouth and tongue going wild with rimming my Twink’s begging hole. This was a fantastic sensation, so different than even a wet finger or two or…whatever.
“Oh, Fuck Mom! Danny’s Tongue deep in my hole feels so heavenly! OH, Fuck Yes! Eat my hole, Danny suck and lick it all out, please, Daddy, please deeper, faster!” I was screaming and pushing my ass into his face, tongue and mouth.
Mom answered, “Oh, yeah, Danny! Eat my boy’s hole! Take him beyond this universe, show him the infinite male eroticism that lovers can do!” I was getting dizzy in pure pleasure, relaxing and just in an astonished state. That soon ended as I felt Danny pull off and thrust three fingers in my hole to the depth of his hand in one fell swoop. Bailey reached and squirted a good several ounces of fuck water all over his hand and fingers.
He began coaching, “Good boy, Charlie, just relax and I'll twist and massage you hole open; my cock is much bigger, so breathe and relax.”
Mom started in also, “Perfect, Charlie; Deep breath and relax; we know you want it all to max depth and pounding orgasmic widths, breath; relax, sweety, doing great, my love, so proud of you on your 18th!”
Danny pulled out his loosening fingers. Finally, I felt his big cock head tease my anxious, horny hole. I moaned and groaned with panted sighs in anticipation of that huge cock popping my Twink Cherry.
Mom sighed, “Danny, please go slow and gentle, that is a massive, hard, purple cock you are about to breed my boy with!”
He answered, “I promise, Ashley, he is in good hands; you and Bailey keep stroking his back and ass.”
I interjected, “Bailey, I will need to hold on to the headboard here. Can you point my hard penis, so I squirt my boy-cum load all on the black plastic plate, please?”
“Sure, Buddy, I would love to pump your big, beautiful cock; show us how much you can cum with max climax and orgasm ejaculations; you are both so fucking gorgeous and hot!” She obliged.
I breathed deep and nodded, turning back to Danny, giving him the “go-ahead” smile and nod. His thumbs massaged my hole as his mouth dripped hot man saliva. He began to rub his huge glans and cock head up and down my sensitive ass crack, often slapping my hanging nuts. I shuddered and sighed, letting out delightful whimpers and gasps. He placed one hand on my right shoulder and the other on my left hip as his ginormous penis began its entry to my begging outer hole. I whimpered and groaned more as it finally popped in.
“Holy Fuck, Danny, that is the widest stretch my hole has ever had. Lots of pressure and some pain, but please keep going; I want to feel your bush deep in my crack,” I begged.
“Ok, Charlie, here we go with thrusting deeper and deeper; Ashley and Bailey will caress and stroke you,” he announced. In seconds, Mom leaned in for a peck on the cheek and whispered to relax and enjoy, without inhibitions or worries about what they were doing. I blushed and smiled so big as now I felt both Mom and Bailey stroking my huge 8” dripping cock with a thick white cum pool on the plate, almost 3” wide. Their free hands intertwined with Danny, so it was like the three of them were one incredible pleasure machine. I was the finished product being bred and made a man.
I cried out louder as Danny began going deeper and faster; Mom and Bailey continued their encouragement. Now the pressure and pain were really building. At the same time, I was unexpectedly enjoying the pain and felt so safe with Mom, the doctor of everything, watching Danny’s thrusting, huge cock slide deeper and faster in and out of my devouring, hungry hole.
Bailey, God bless her, added more lube with a cheek peck, too. This is the best fucking birthday ever! Now I felt the depth and pain tremendously; Mom sensed and knew exactly where Danny was inside my anal love tunnel.
“Charlie, you are doing fantastic, my love. The cum dripping out of your beautiful penis is incredible. Danny’s dick is in your anal canal and rectum about 7” s. There will be more pain and pressure as he hits the sensitive curves, turns, and bends to the sigmoid in the next 4 inches. As he opens your sigmoid, I will be watching and guiding you, so do exactly as I say, and you will enter Elysium; no pink or bleeding, so you are ready, my dear. Danny, take his entire ass and go balls deep right fucking now! Charlie, I command you to push back and wince through the pressure and the pain… trust me, my love, trust me!”
Suddenly, Danny grabbed both my shoulders and forced his entire 11” cock balls and bush deep till I felt him scratching my crack with his hot pubes just as I was dying for. I raised my head and screamed as I pushed back with all my painful, wincing, tear-jerking might; I thought I would pass out from it all. Luckily, I was distracted as Mom started to jerk my cock with Bailey pulling hard on my strangled nuts. I was grunting and groaning; I felt so reassured as mom watched so intently with every thrust and plow. I heard Bailey exclaiming oh fucks and " So hot. After 5 minutes of slapping ass pounding, Jackhammering breeding, I felt a bit of relaxation and a big pop open. I saw pictures in my mind of my anatomy; I knew my sigmoid valve had just given way.
“Guys, it is suddenly incredible; my sigmoid just opened and popped. I feel like it will be unbelievable now; Danny, harder, faster, please, balls deep; oh, fuck Mom, it's so fucking good. I never imagined it feeling so intense and sensational, fuck me, Danny, Breed me, fucking breed me now!!” I hollered. I could not believe it. I was grabbing the headboard edge and actually pushing back against Danny’s huge balls deep pounding ass breaking 11” penis!
I screamed and yelled, “Harder! Deeper! Faster, Danny Breed me with your hot man cum fucking now, Oh Fuck Mom! I am going to cum! Holy Fuck! Never like this ever! Oh My God! Yes, Danny, yes, YYYYYYYYYEEEEEEEESSSSSSSSS OOOOOOOOOHHHHHHHHHHHH MMMMMMMOOOOOOOOMMMMMMMM YYYYYYYEEEEEEESSSSSSSSSSS FFFFFFFFFFFUUUUUUUCCCCCCCCCCCCCCKKKKKKKKKKKKKK YYYYYYYYYEEEEEEEESSSSSSSSSS GGGGGGGGGGGGGGOOOOOOOOOOOOOOODDDDDD YYYYYYYYYYYYYEEEEEEEEEEESSSSSSSSSSS AAAAAAHHHHHHHHHHHHHHHH FFFFFFFFFFUUUUUUUUCCCCCCCCCCCCCCCKKKKKKKK!”
My head was back, and my body shook and arched so contorted in the best climax ever! I was staring at the wall and ceiling. All I saw were stars and fireworks, I swear. Then I came back to earth, hearing and feeling Danny ejaculate deep into my rectum and sigmoid with thudding hot splashes as he screamed the same as I had; Mom and Bailey were beside themselves with apparently my impressive ejaculation volume. I then saw and noticed my splashed and ricocheted semen all over the plate, my cock and balls, belly and chest. This was hands down the greatest ejaculating orgasm of my entire life!
“Holy Shit, My Boy! I was hoping for a great anal hand-free orgasm and ejaculation for you, but Wow! This is fucking massive, Charlie! Check out all this hot boy-cum for you to eat up. Danny, pull out; feed all that man cum dripping cock from my boy's ass to his parched mouth and throat for his birthday supper!” Mom insisted; Danny did so.
I sucked and licked with so much fun pleasure, Danny’s cum dripping 11” cock. I was nice tasting my musk and clean hole on his penis. I felt so manly and powerful. Bailey brought the black plastic plate to my face and doused it all over my mouth and head like a bukkake contest. I shovelled every ounce and drop into my mouth and throat along with Danny’s dripping cum cock. I was drenched like white Carrie!
After twenty minutes, I had it all licked clean. My boy-cum tasted so good mixed with Danny’s. I could not believe the volume I blew. I collapsed back to the bed on my back, panting. Mom and Bailey gave me more birthday pecks and said the following parting words,
“That was stupendous, Charlie. We are so Happy for you. Bailey and I must go fuck our assholes with huge dildos and the Strap-Ons. I am ensuring the rest of the week is fun for Danny and you. We are right just feet away, so call if any needs.”
“Thanks, Mom! I love you all so much. That was the greatest orgasm ever. I am ready for some big dildos and fuck machining too. This is so much fucking fun!” They giggled, hugged, and went to their master bedroom after more birthday wishes and admiration.
Danny, can you help me get into position and choose a dildo and the right lube? I see that while I was eating all our sweet boy-cum up, Bailey has the XL Cyclops fuck machine assembled and locked in place at the end of my king-size bed. I am so horny; weirdly, my hole feels hungry and starving for even bigger than your huge cock, I am going to cum again from the thoughts alone,” I said.
“Yes, Charlie, that was planned next, but we should slip the secure straps like horse reins under your mattress first so you can hold on while the fuck machine pounds your Twink ass silly. You are going to have so much fun tonight and forever more!” He laughed.
“Danny, do I really have to anal douche for each penetration session, or can I try dirty riding?” I asked.
“Well, I do not want you douching daily, as really just a few times a week max is recommended to maintain a man's digestive biorhythm and healthy bacteria. I mean, take a shit and maybe stick a few lubed fingers up, and pull any excess out, but sure, lube up and plow your ass and do not be embarrassed about shit. Turn your bath fan on and open the window.”
I replied, “That is great. I love it so much and am so grateful to have such an open, supportive mom, man lover and all recognizing and encouraging my wild, feral pleasure and orgasm, as most important. What do the cock cages do apart from trapping the penis from erection?”
“It causes a twink like you or man to focus on the very deep and wide anal penetrative pleasure; later tonight, your sexual energy will all go straight to your plowed and pounded open gaping Twink hole. Your penis will soften, but you will have the most potent and voluminous orgasms and ejaculations you can’t possibly imagine or expect, even better than my cock did.” He spoke.
“That sounds like fun; my cock is softening some, so help me pick a cock cage,” I replied.
Danny came over with a heavy ventilated metal dragon-shaped short cock cage. He guided me to slip my lubed balls, cock through the base and squish my penis up with the 4” Urethral cum tube, just a few inches shy of my prostate. Once locked and latched, it felt so awesome, just like the silicone-and-metal sound did. I pranced around with the heavy stainless steel nice, ball and cock stretched cage, he stated,
“I suggest we start with the most famous XXL Seahorse dildo. The penetration will have incredible pressure and some pain; I will be right here beside you to ensure no injury or bleeding. Just as with my big cock, you must relax; you will likely piss and cum at the same time, which is just such a hot, horny, mind-boggling experience with the most cosmic screaming cum blow.”
I put on a tight black silicone cock and ball ring duo to strangle my stretched cock and nuts even more; then, I dressed up in the leather collars and cuffs. I was so fucking hot and adorable in my room full of mirrors. Danny grabbed the XXL Seahorse Dildo with all its incredible graduating bulges and ridges; Balls deep, it will be over 14” up my hole and nearly 5” wide. I was scared, but so horny and anxious for it.
He helped me fasten it into the fuck machine base holder with the Velcro straps and some extra-wide bungee cords; then showed me how to slather the X-lube all over the dildo and mix it up with some oil-based lube too to ensure continuous lubrication; Danny and I stuck a few handfuls of creamy oil lube up my hole as well.
My cock was puffed up in the small metal cage, and I had semen dripping out the cum tube spout; semen webs all over myself and the bed as I was assured of a healthy sexual big 18-year-old explosion. I got into doggie position on my king bed and scooted my hole back to the tip of the massive dildo. I started to hear Mom and Bailey in the throes of deep ass pounding in their bedroom (not the first time!). I was hot to try strap-on sex with Danny & 18+ school friends.
Danny continued, “Now, Charlie, once you have conquered a few safely, then the night and entire weekend are yours to pound your hole and cum away and ask me for anything. Have some more water and feel free to piss like mad.” (He brought the bottle and I gulped some). Now, slowly scoot your legs back until we have the big glans head of the dildo in your first few anal sphincters.”
I was so excited and horny for my first big anal penetration that made his cock pale in comparison. I grabbed the massive dildo head and slowly popped it into my hole. I squirted a small cum shot out of the penis tube all over the black plate below and whimpered and moaned. It was fucking huge and a real pressure stretch, even more than Danny’s stretching cock had been.
“Oh, Fuck Danny! This is so much fun, but this dildo is fucking huge. It already hurts a little bit, and the pressure stretch is so intense, I trust I will stretch just like you cock pounding,” I gasped and moaned.
“I know, Charlie, my dear boy. Trust me. Slowly push back; take the control knob, flick the switch, and slowly crank the dial to higher numbers. Yes, it will hurt at first, just as my cock had, but in hours or parts of days, you will be begging for the largest ones, balls-deep, at max speed, I promise. You will not believe the anal orgasms you are about to experience, just like your mom and Bailey are screaming about now on their G-Spots and clits through our own girl assholes. Bottom anal sex all the time, you learn that it is the main pleasure spot for all genders. Now suck it up and commence your hot Twink dildo ass deflowering,” He commanded, getting impatient with my timid trepidation.
I did as he instructed. Slowly, I pushed back and started the thrusting fuck machine on level 1. The pain and pressure were incredible, but I winced and bit my lips and tongue and pressed on. He pulled and stretched my balls and got underneath me to stretch and chew on my nuts and ream on my caged cock. He stroked and slapped my butt cheeks, periodically breaking, telling me to breathe and relax, breathe and relax. After about twenty minutes, I noticed the pain was easing, and it started to feel fantastic. I think I had about 2/3rd or about 9” of the beast in my anal canal and rectum.
I said, “Danny, it is starting to feel much better and fantastic just like before, with all the sensation I feel it plowing through my anal rectal curves and folds; good thing mom taught awesome boy anatomy. I want to turn up the speed to level 5, and go a few inches deeper, ok?”
“Sure, Charlie, all looks good back here; you are doing awesome coating my mouth and throat with lovely hot creamy white boy-cum. Your penis is running precum like a severed artery. Once you get to the huge dildo base, you will be well into your sigmoid. The 5” width will be pounding on your prostate and seminal vesicle. Then you will see what I am talking about, pissing,” he excitedly let out, all smiling away. Like a good boy, I did as I was told.
In minutes, the pleasure was impossible and off the charts as I felt the massive dildo bash in and out of my hole, folds, bends and fleshy curves. I could see in my bedroom, strategic mirrors that I was just inches away from the final massive ridge and bulge on the seahorse. Soon, the dildo glans would be in my Sigmoid, and the base would be balls deep in me.
I suddenly cried out in total bliss and rapturous joy like never before as I plowed balls deep, busting through and exploding all the nerves and sensations in my curves and sigmoid valve, my prostate in total nuclear overdrive explosions,
“Oh, Fuck Danny, Mom cum quick! Something is happening again, even bigger than Danny’s cock! (Bailey scooted in, carrying mom with a huge dildo missionary up her asshole -Slammed her against the wall so I could watch). I have never done it before! It is fucking huge! It feels so incredible! Oh, my God! Oh Fuck I am going to piss and cum, oh Yes Fuck! Holy Fuck! Yes! Oh, Fuck Oh GGGGGGGGGGOOOOOOOOOOOOOOODDDDDDDDDDDD FFFFFFFFFFFFFUUUUUUCCCCCCKKKKKKKKKKKK OOOOOOOOOHHHHHHHHHHHHH YYYYYYYYYEEEEEEEEESSSSSSSSSSSSS FFFFFFFFFFFUUUUUUCCCCCCCCCKKKKKKKKK OOOOOOOOOOOOHHHHHHHHHHHHHHHHHHHH!”
The pelting squirts of splashing piss and cum flying out of my caged dick spout and overflowing the black plastic plate, bouncing off and coating my thighs and belly several times bigger than before with Danny’s Virgin ass pounding 11” beast.
As mom was getting ass fucked hard by Bailey, she winced and yelled, “Oh, Charlie! Yes, my boy! Holy Shit! Good for you! That is the biggest boy cum and piss blow Bailey, and I have ever seen. We are so happy for you; this is what we were talking about. Keep going, sweetie,” she yelled. I turned up the dial to 7, faster and harder cumming and pissing everywhere. I felt so cosmic and euphoric, rapt with indescribable joy.
Bailey stated, “Wow, Charlie! That’s a fantastic Cum and piss for you! That must have felt amazing.” Danny handed me the plate to lick and slurp clean and dry, and returned it for me to fill again and again.
I answered as Mom started to squirt all over Bailey, the girl cum and piss too, “I can’t stop Mom! It feels so fucking good. I want to go even bigger, deeper, and wider soon, but oh Fuck! I am going to piss cum again, OOOOOOOOOOOHHHHHHHHHHHHH FFFFFFFFFFFFUUUUUUUUCCCCCCCCCKKKKKKKKKKK YYYYYYYYYEEEEEEESSSSSSSSS FFFFFFFFUUUUUCCCCCCCKKKKKKKKKKKK! YYYYYYEEEEEEEESSSSSSSSSSS GGGGGGGGGOOOOOOOOOOOOOOOODDDDD FFFFFFFFFFFUUUUUUUCCCCCKKKK!!”
It was so much fun to have zero inhibitions or embarrassment about sharing my sexuality and abilities with my mom, Bailey and hot Daddy Danny. It really excited me tremendously for them to watch me pound like mad back against the firing dildo and fuck machine as it ravaged my hole and still was only partway to max speed.
I ejaculated cum and piss, several dozen more times in the hours that followed, with lots of water. We switched to the 3XL Seahorse for an hour, then to the 3XL Dragon. We then switched me over to Crackers, Abyss and Chance, followed by Artemis, Mordax and Pegasus. My hole was so red and sore; yet I yearned for more to expand and stretch my hungry, starving hole. My sheets and pillows were soaked with cum and piss. Danny, several times, slid under and enjoyed my blasting cum and piss all over his face, mouth and down his throat. A few times, he jerked his cock in my mouth as I was screaming with the continuous cum piss blow. His daddy man's cum was so powerful and hot.
Mom and Bailey retired to their room for anal fisting orgasm fun. Danny & I took a small break at 4 AM and decided to take some of my dildo conquests to the bath and laundry for cleaning. I peeked in on Mom getting double-fisted by Bailey. It was beautiful watching her cunt squirt and explode as Bailey pounded her ass, elbows, and shoulder deep. I was glad she got me a few Carmen Revera strap-on harnesses as well; fisting, I was dying to try and soon.
Good thing that Monday was a statutory holiday in Canada called Family Day. We all got little sleep the next 72 hours as I tried every single one of the dildos and each of the urethral sounds, and all of the cock cages. So much Fucking fun. Danny helped eat so much cum and piss; then kissed it back so passionately, dumping it down my throat to my hungry tummy.
On holiday, Family Day Monday, I used the hollow metal sound and clear silicone tube to my mouth for direct cum feeding. It was so much fun cock caging and trapping my erection and then sucking my semen and ejaculation through the pipe with fresh hot clear boy-piss down my throat. Danny, Mom and Bailey are smiling away, so happy at my moans and groans and slurpy sounds like a kid at the fall fair. I think all I did for three days was drink water, eat cum and swallow my own piss. When you are well hydrated, swallowing boy piss is very erotic and tastes so good.
Days, weeks and a few months passed. Each night, Danny came down after his work and ran down to me after I got home from school; he ate my ass violently, sucked and chewed my cock and fucked and bred my hungry boy hole spilling ounce after ounce of his hot man cum, until I blew on the plates or down my throat if I had the cock cages and tubes and dental oral mouthpiece in me.
Then we shared hours of semen kissing. He confirmed he was 48! He could have easily passed for a hot older college dude. Then we started the dildos and fuck machines with more shared cummings. We were saving first-time fisting for group play with my boyfriends; Danny would guide and instruct.
It was so cool, though, when mom and Bailey came home each evening, and we were so relaxed, playing with Danny and all the awesome toys. Doors wide open, all naked and cum and piss flying everywhere up Twink assholes and down throats.
Many 18+ Twink BDSM orgies with Danny Breeding in tow ensued over the next few months to the end of the high school year. I had to get more douche hoses and splitter valves. It was so awesome to eat a boy's clean asshole for hours, suck cock and share each other's ounces and cups of hot white creamy boy-cum. All our cocks were close in size, about 6-8” s. They were all broken in by 48-year-old Danny with the Great 11” cut dick; we started to nickname him Big D.
As a graduation gift, Mom, Bailey and Danny installed a sling over my bed and got me a second XL Cyclops machine and two splitter dildo rods. I could now get in the sling with three other boys, and the four of us all get ass fucked with the massive dildos and the two fuck machines smoking on max speed and depth. We went for hours and hours, squirting cum and piss all over each other's mouths and faces and down our throats as our assholes got destroyed balls deep, often in Chastity.
In mid June 2025, just a few weeks before Canada Day Long weekend in July, Danny disclosed that he had a surprise for me. Mom and Bailey were there as well, all of us nude as usual.
Danny began, “Ash & Bail, as we all know, Charlie now has the ability, along with a few friends, to take most of the largest dildos base and balls deep. I am on summer vacation for 10 weeks until their college and Uni start back in September. I have a secret place, like a cabin, cottage, or summer home, and would like to take Charlie and three boy friends for an extended 10-week stay. I have all the toys and slings up there and can take mine and Charlie's stuff along so that all four can enjoy together at once. The sole goal would be training their holes for anal fisting to their transverse colons, shoulder, and armpit deep over the ten weeks. It is very private, and no one is around for miles, so all will be nude inside and out, with all the safe, clean amenities you can imagine. So, thoughts?”
Mom replied, slapping her hands, “Well, Charlie and his closest boy friends are all 18, so he is a young man, and I have no power or control over his life and decisions. Charlie, I fully support your plan and recommend going for it. I know we all trust Danny as if he were your father.”
I answered, “Well, so many times I sneak in a cry out to Daddy when he is pounding and breeding my hole, but it is so close to Danny you never noticed, did you?” They shook their heads, smiling and giggling.
I continued, “On one condition, the three boys I chose, this is to be like a medical ritual vacation where we are made to wear cock cages and cum tubes continuously for 6 out of seven days; maybe on Sunday, we get to suck and fuck each other as a cageless orgy day. All boy-cum from all must be swallowed or anally taken.
I want the day filled with fun recreation, but the 18 hours not asleep, I want a strict regimen of all sorts of ass, cock and ball BDSM orgasms; maybe a little flogging and spanking, but I have just the perfect three boys in mind who love the anal and urethral penetration cum and piss eating and group play. But I am serious, Big D. I want it structured like a medical clinic with continuous 18 hours daily of nothing but play, orgasm, cum, and piss eating; final goal is rosebuds for all of us and fisting to ballroom ability, I guess we say it will be an "Anal Twink Fisting Rosebud Retreat!”
Danny gave smiles and thumbs up; Mom said, “You lucky little fuck!”
To be continued… in the next hot story-chapter or book.
