All persons and depicted activities are between consenting adults over 18 years old at all times.
I love my life. I love my homies. Most of all, I love my skateboard. I am what you would call a skater-bater. When I was not boarding and hanging with my homeboys, I was jerking off. I have no job; I never even looked. I barely graduated from high school. I live with my dad in a big high-rise condo apartment in Toronto, Canada. My Parents divorced when I was 9, and my mom moved to another province.
My name is Tommy Wagner. I am 19 years old, with long, dirty, sandy blonde-brown ash hair. Some said I looked like a dishevelled cat-faced Jared Celma, but with more rugged and bad-boy looks. The homies and I are all a bit gothic and punkish. We are adorned with earrings, piercings, tongue studs, lip studs, bracelets, chains, belts, and goth tattoos (Boy, was Dad ever pissed about those!). We loved our ripped and torn half-shredded jeans with undies hanging out. Worn-out Rock T-shirts, bandanas…you get the picture.
I am not sure about my sexuality. I never really had a girlfriend. Kissed a few and felt them up this past year behind malls after we were all 18 (Of course), but I was finding myself these last few months fantasizing sometimes about me and my buds having sex. Most of all, I knew deep inside what got me super horny and raging hard was older college dudes and young men in their late 20s or 30s, even a few 40 or 50-year-olds. Perhaps it is because I need a Daddy, as mine was never there; even though he was right there, I was invisible to him since Mom left. The year after I turned 18, when dad was not around (Which was most of the time), I started playing with my virgin asshole. Holy Fuck! It felt so awesome, especially that hard, round walnut part, which was called something…When I pressed and rubbed it hard with a few fingers, I could squirt fantastic cum from that alone. Many older dudes played into my anal masturbation. I am a virgin to all genders; really, nothing with no one.
One professional in our building, Jordan Brown, was a notable Individual. I am not sure what he did for a living, but he drove a nice, orange-yellow, badass four-door Dodge Ram Pickup truck, complete with all the bells and whistles. The homies and I used to joke about stealing it, but we were all pussies. We harassed him regularly in the parking garage as we flew past him on our boards, always ensuring we almost knocked him over and then laughed and pointed, saying, “Sorry, Dude!” We got away with it because my dad is the Superintendent and complex manager.
If Jordan only knew, secretly I loved hitting him to feel his strong, muscular thirty-something body. He must be six feet four inches and in fitness model shape. I tried not to stare at him in the pool and fitness room, but many times, behind my black sunglasses, I couldn't keep my eyes off those ripped, lean, chiselled muscles; the warm, silky, dark brown, perfect medium hair; those blue eyes; and teeth like arctic white, with a Hollywood quality. Recently, late at night, he was my go-to fantasy jerk off; sometimes I almost thought I would get my entire hand up my ass as I pumped my cock and blasted cum all over the headboard and wall. I would lick it up and wish it were his.
Today, it all changed. I am here, shaking and sweating, unsure of what to do. You see, Dad has been on my case about being a useless twat…Well, I can’t dispute that now, can I? Today was the monthly Fire Alarm and sprinkler clearance testing throughout our twenty-story condo building; required by law under an act and compliance by the Office of the Solicitor General, If we (Dad) can’t prove that it was done, he could lose the job he has had in the condo building here for over ten years since Mom left. He was short-staffed and begged me to help with the unit inspections. I decided to accept his offer, as he had agreed to pay me, his unappreciative son, $200 for the day, so I leapt at it and agreed.
We started at 8:00 AM on the main floor, as notice of entry had been given to all residents three days prior.
The condo owners were accustomed to it monthly. Dad worked on the East side of the building, and I worked on the West. I was exhausted, with a clipboard in hand, as the alarm sounded, the lights flashed, and the dozen or so sprinkler heads in each unit were confirmed to be cleared of obstructions. By the time we reached the penthouse on the 20th, as each floor had 20 units, totalling over 400, 200 units each were assigned for checking and initialling by me. Some people were home, while others were not. If the solicitor's office were to audit, it would involve reviewing our paperwork and conducting direct contact with residents, or a mail survey. Each unit, as we entered with the master key, took about 3 minutes to check and verify, so 200 units would be a 10-hour job. We had three quick twenty-minute breaks and piss stops.
Finally, I was in the last unit corner of the penthouse floor. As soon as the door opened, I was taken aback by its luxury, beauty and super sexy décor. The residents were not home. The Black gloss walls and Red Leather Furniture, the light maple hardwood. Strange, the lag hooks in the walls about the sofa and the halls. Umpteen hoses in the vast spa-like shower. Then I entered the master bedroom with what I can only describe as a king-size bondage bed. I was skulking all around and spying as I checked the flashing lights, alarms and sprinkler heads. There were several chests, drawers, and a tarp-covered shelf unit—numerous books on human sexual behaviour… written by Jordan Brown, PhD.
Then I noticed the naked male erotica and sex pics on the walls. Holy Fuck! It was Jordan! I was in Jordan's unit. I wasn't paying attention to the names on the list, as I didn't have time for that. Since it was the last one on the list, I could not help but indulge my horniness. OMG, his cock is huge in these naked pics. It must be almost 10 inches and thick, with an awesome brown bush. I found my 6.5” cock swelling and starting to lube a boatload of precum. I couldn't help myself, so I decided to open the drawers in the bedroom. All I saw were things I had no idea what they were…Metal cage type cock like shapes and locks, and metal tubes and rubber this and that spaghetti type shit, handcuffs thing I never saw or could understand.
I pulled back the tarped shelf units and almost passed out. There were dozens of massive, giant dildo creatures cocks as big as my arms and some the size of my legs. How could anyone get these up their butt? I had no idea. Why is my cock getting so hard and dripping? I released my 6.5” cut boner and started to pump…I am going to cum just from the thought of these penetrating…penetrating my ass…Oh Fuck am I insane! Surely my insides would explode…but Jordan has these… so…Oh God. Looking at his nakedness pics and all the sex toys, I became dizzy and lightheaded. My cock has never been this erect ever!
Oh Fuck! What is that! I peered at the corner of the ceiling. Horror and complete utter mortification washed over me. The place is full of motion sensor recording cameras. The lights are Red and sometimes flashing. Jordan was watching and had recorded me…Oh Fuck!
I quickly zipped up my fly, damn near catching my cock in the zipper. My erection was still very evident; torn jeans cum soaked, so I ran out to the elevator after slamming the door and locking it.
The elevator opened, and there, lo and behold, was Jordan. Smiling at his phone. He glanced at me, smirked and exited. I ran in with my head down in shame and pressed the close button as if doing emergency Morse code; I dare not make eye contact! My heart was racing, and my head was exploding. My erection is still like titanium.
I texted Dad that I was done and that I left my results in the office. I ran to our unit and straight to the shower. I locked the door and turned on the water. I spit in my hand and jam my fingers up my hole. Two…then Three…then Four. I quivered them and cried out in great rapture as my semen exploded all over the grey tiles, dripping down. I licked and sucked up my cum, savouring its youth and fresh sweetness.
I pulled out my fingers, which were covered with feces. My mind turned to all those hoses Jordan had in his bathroom spa shower. I took the shower head and reduced the water pressure until I could unscrew the head from the hose. Slowly, I popped the hose end up my asshole and came again as the filling water was so pleasurable, having done this for the first time. After a few more small ejaculations, I was crystal clear and re-attached the head and continued to shower and wash my hole inside and out and rinse and repeat; all was sparkling clean and fresh!
Why did I have an inexplicable need to clean my hole? My cock was hard and dripping again. I collapsed to the floor as the water sprinkled over me. What was I going to do? Would Jordan file a complaint that I invaded his privacy? Well, I hadn't shared or told anyone… yet! I am sure he would be embarrassed if anyone found his…his…his…I was getting dizzy again. The thoughts of his unit. The toys, the instruments, the implements…what would it feel like? I loved my fingers and almost got my hand up my ass. I wondered, what does it feel like to have a hand or these massive toys in one’s ass…or his giant, beautiful penis in my ass? Well…maybe I am gay or bi at least. Now what do I do?
I recalled his books on Human Sexual behaviour. I speculated that, as he is noted as a PHD, he must be a professor at one of our universities. Surely the thought of that settled and calmed me. A big breath, and I now felt certain that I should put on clean clothes and go up and see him. Perhaps he or I could come in to apologize for what he saw and recorded me doing. This now percolated in my punk ass skater-bater horny 19-year-old uncertain sexuality anal enjoying penetrating brain.
I had some water and a small amount of food. Dad has left $300 on my bed as a thank you for the great help and a tip. He had gone to his curling club meeting with his buds. He would not be home until midnight or later, perhaps. It was 8 PM. I walk back to my bedroom and grease my asshole with some water-based pineapple-flavoured lube. God…I hope I know what I am doing. I have never had a boy’s or man's penis in me or sucked a boy's cock. All I have done is pathetically kiss a few girls and rub their tits…I didn't even get half a chub or wet at all…But I secretly loved playing with my hole till I came. Down deep, I had fantasized that my fingers were Jordan’s cock. Little did I know his cock was the size of my arm.
I gave myself one more look over and wet my hair with some gel. I put on some eyeliner and decided to embrace my femboy yearning. I went to the elevator and pressed the button for the twentieth floor. Jordan’s end corner unit on the southwest was # 2020. How appropriate, the perfect vision result. I felt my heart racing and sweat on my head and neck. I then realized that the 2/3rd cut off jeans I had on yet again had a tear and rip right on the ass crack seam…maybe that would be handy?
I reached his unit, breathless and shaking in my six-foot-tall frame, weighing 140 pounds, with a lean, moderate sculpting form (thanks to skateboarding).
“This was it. Fuck it, Tommy, come on, you pussy! Man up and knock already.” I said to myself. I was all ready to say “hi” in a sexy, seductive look. I practiced knocking for almost a minute. Then, by accident, one knuckle knocked on the door, so I was committed. I then jumped in and knocked forcefully, almost in anger, 5x! Fuck!
I knocked again; my heart raced, and I thought I was going to piss my pants. The door opened, and there stood Jordan, wearing nothing but a red net thong!!
He stared intensely at me, saying nothing. I stammered out, “HHHHHHHH ……. HHHHHHIIIIIII HHHHHIIIIIII! UUUUUMMMMM AAAAAAAHHHHH…HHHHHHHIIIIIIIIIIII!” Oh Fuck I felt so stupid, I almost began to run.
Finally, Jordan spoke, “Hello Thomas, I have been expecting you. Would you like to cum in?”
I nervously replied, “Yes, Mr. Brown, I would like to cum in.” He smiled, and I entered. The door shut forcefully and was immediately locked with three locks. I was so turned on that all he had on was a see-through thong. His huge cock was half hard and had a large drip at his glans tip.
I said, “I'd best take off my shoes, Mr. Brown.”
He replied, “No, Thomas. Please leave them on. You will need them for balance and support. You will always address me as Professor Brown. Is that clear?”
I said, “Yes, Professor Brown.” He slowly pushed my back against his foyer wall. He was just inches from my face and body. My penis was tented and visible in my jeans. He was a complete, perfect god and so fucking gorgeous. I swallowed hard, not knowing what to do. He rubbed his cheek against mine and then slid his tongue up and down my neck to my ear and around my jaw line.
He asked, “Thomas, have you ever touched a man’s penis before?”
Shaking and gasping, I answered, “No, Professor Brown.”
He continued, “Thomas, would you like to touch my penis?”
I swallowed and, with trembling anxiety, answered, “Very much so, Professor Brown.” Nodding and bobbing my head like a rock 'em sock 'em game. He led me to his area rug in his living room. Once there, he pulled me close and sucked my mouth, taking my tongue deep into his, swirling it around. I felt my cock ejaculate a semen cum squirt and knew immediately at that point that this was the sex that I had wanted my entire life. I melted like butter in his arms; his tongue and hands caressing me all over. I returned the moves as much as I could. I grabbed his hard package and fondled his huge cock and balls beneath his red net thong.
Professor Brown suddenly pushed me to the floor. I instinctively rubbed with both my hands his penis and testicles and began to suck and lick his thong, tasting his man cum juice for the first time. His precum tasted like honey and mangoes. I was dizzy again with excitement. When he was fully erect, I pulled down his thong. Just as I had hoped and feared, before my eyes bounced a cum dripping, beautiful, 10” raging man cock, the likes I had never seen in porn.
He grabbed the back of my head and slowly slapped and slid his big cock all over my begging lips and face. I grabbed it with both my hands and took him in my mouth. It tasted incredible. Salty and sweet. I wanted it down my throat and to feel his orgasm down my stomach. Fuck! He is so big.
Suddenly, he grabbed my long, shaggy hair and began to thrust his huge penis in my mouth and throat. This I was NOT ready for. I coughed some and had a little choke.
He said, “Do you want me to stop Thomas?” I froze, not knowing how to answer, as I sure did not want to fuck up sex with him.
I blurted out, “No, Professor Brown. Please do not stop as long as it is fine if I puke some on your rug…I have had very little to eat and drink, so face-fuck the hell out of me. I am a little begging virgin cock sucker wannabe!”
Oh Fuck! I can’t believe I just said this death sentence line! He smiled and forced his cock in my mouth hard and fast as I gasped and gagged. He kept my watering, tearing eyes on his as in some fucked up way I was really enjoying being hard and rough faced fuck like this from such a massive man cock, even though I could hardly breathe and was close to barfing. Still, I love it!!
Harder and deeper, he forced his great, long, thick penis down my mouth and throat, and released and repeated just before I was about to choke and puke. It went on for twenty minutes. I swallow a lot of precum, but not a blown ejaculation yet. My cheeks were soaked with tears and spit, and cum was dripping from my lips and mouth.
Suddenly, he lifted me and turned me around on his sectional sofa, placing me in a doggie position. He knelt behind me, and I felt his strong man's hands grab my split jeans and pull them apart. He tore my worn underwear in 1/2, and when my lubed, flavoured anus felt the cool air, it was quickly followed by the most heavenly sensation I have ever imagined. Professor Brown had his tongue licking and slurping up and down my ass crack and parting and circulating all around my little virgin, clean, pineapple-flavoured asshole. He sucked and ate my hole as I cried out in bliss, joy, and rapture.
“Yes, Professor Brown! Yes! Please eat my virgin Boy hole and turn me into a real man. Oh Fuck your tongue, it feels so good on my cunt! Yes, Eat My cunt, Professor Brown…OOOOOOHHHHH FFFFFFFFUUUUUCCCCKKKK!” It felt so good with his tongue going deep in my loosening, sparking sweet rectum> I wanted his cock so bad, and I hoped I would feel the pain…I wanted to feel the pain I knew would bring me to the ultimate anal pleasure ever!
Finally, after 10 minutes of devouring my boy-cunt, Professor brown stood up and grabbed my belt. The next thing I felt was his large penis tip pressing on my hole. He spat some and rubbed his fingers and twiddled; it felt glorious as my ass and hips rotated in the pleasure.
He said, “Just breathe, Thomas and relax your anal hole. I can tell you have been playing with it for some time. My cock is huge, and this will hurt. I'm going to breed you and promise you that by morning, you will have experienced orgasms and pleasure like you can’t possibly imagine. Now here is my man cock fucking and breeding your virgin boy-cunt!”
I felt the entry and pressure much more than my fingers. Suddenly, his big glans popped in, and I breathed a huge sigh of relief. He stayed still for a second and then started to thrust deeper and deeper. Each thrust and drilling penetration with his huge cock was much deeper than my fingers had been; each thrust had a burning pain and intense pressure, yet I wanted more and more. I winced and bit through the discomfort.
He stated, “Thomas, I am in you over six inches and now will penetrate through your sigmoid second hole. This will hurt at first, but in ten minutes you will be pounding back begging more and more.”
I answered, “Please, Professor Brown Breed my boy-cunt and give me your entire big cock balls deep!” What am I saying!!! I fucking out of my mind!!
Both his hands grabbed my belt, and suddenly I screamed with intense searing pain. I was sure he was coming out of my stomach like an alien creature. I screamed and yelled some more with gasps, grunts, groans, and moans. A few more thrusts and suddenly I felt his pubic hair on my crack!
I cracked a smile! I was alive, and he was balls deep. I turned my head and made eye contact. He leaned forward and kissed me hard and wet.
“Here we go, Thomas, welcome to man fuck heaven!” OMG! With one hand on my shoulder and the other on my belt, remember that he is fucking my ass with my jeans still on, my zipper and buckle done up. My raging cock is trapped in my tight undies. His penis and hips started thrusting like a train geared wheels starting up, gaining speed down the track.
He and all had said this would happen. In about ten minutes of his continued boy-cunt pounding balls deep, the pain faded more and more as my cunt opened like an alien pod, and I found myself in an anal slut fucking mode, starting to push back against his thrusts. The building pleasure and sensations…I never could even fathom the possibility. It was exponentially more incredible than my fingers could have imagined. I felt my little walnut cum button must be the size of a baseball by now. My orgasm was commencing; he knew it and went even deeper and faster, bruising my hips and ass bones…I wanted even more!
In another minute, I hollered, “Professor Brown, I am cumming! Oh Fuck! I have never cum like this! OOOOOOOOOOOHHHHHHHHHHHH FFFFFFFFFFFFUUUUUUUCCCCCCKKKKKKKKK YYYYYYYYEEEEEEEEESSSSSSSSSSS GGGGGGGGGGGGOOOOOOGGGGGGGGGG OOOOOOHHHHH YYYYYYEEEEEEEEEESSSSSSSSSS” I am not sure how many eruptions I had. Still, my semen was dripping and running out the back of my underwear down my torn jeans and down the inside of my jeans to my knees. I sure hope my poor little seven-inch cock gets released soon.
Then I felt it! Professor brown grunted and groaned and screamed, “I am cumming and breeding you, Thomas. The last will go down your throat. Get ready and be open.” Immediately, as he yelled in his orgasm, I felt a lovely hot wet pelting deep in my upper left side as he filled me repeatedly with at least eight torrential volleys of his man cum. He pulled out quickly and ran to the front of my open throat. He released another four massive semen squirts all into my mouth, throat, and covered my dripping face. His cum tasted lovely like a dessert parfait. I took his cock into my throat that had just been up my clean pussy and cleaned his semen entirely. He kissed me passionately, sharing his cum.
He said, “Thomas, take off all your clothes now, shoes too, and lick and suck up all your semen and boy-cum that you spilt in your pants and clothes. We have just finished page one in our sex training; this novel will be the length of “War & Peace!” Oh Fuck Yes!
