Chapter 1 - Part 1


      OMG. There she was. Brandi Jones, the hottest girl in school. I remember she only just turned 18 but already she was a full blown woman, curves to put Christina Hendricks to shame and a rocking set of tits with long blonde hair. Beautiful, in a word. Her mere presences froze me where I stood like a spells was cast on me. She walked past me in the hallway, I sniffed the air after she passed, it smelt like flowers and sunshine, nothing to disappoint me. It was dumb, it was stupid, I knew I had no chance, but I was entranced by her beauty. I had to say something to her, anything to get her attention, get her to look into my eyes and realize that I’m the guy for her, a nice guy, I’d treat her well. Before I could stop myself I had walked right up behind her, my mouth talking with no brain to back it up.


      “B-Brandi?” I said, what the fuck was I doing, “Hey, uh… hi, it’s me Chet.”

      Brandi whirl around, her long blonde hair just missing my face, she looked me up and down, I was more aware of my pathetic physique than ever, I was a boy with a small frame with hardly a muscle on it, my face bore a weak jawline, I was practically the exact opposite of studly. At first a look of disgust began to curl up her face, but then, then she tweaked it into a smile.

      “Yaa…? What do you want?” her voice was laced with the sound of a typical ignorant airhead blonde, someone too good for anyone except herself, her mouth smacked together as she chewed her bubble gum. A smarter me might have recognized Brandi for what she was; An egotistical narcissist not worth my time. But I was young, dumb, and full of cum, and I was thinking with my dick.

      “Well, I was just thinking, you know, you’re cool, I’m… kinda cool…”

      Really Chet? I thought to myself, this is your best?

      “…I think you and me, we would be pretty awesome right? You’re popular, I’m smart…”

      I was not smart.

      “…I’m pretty… well off, if you know what I mean,” I added like an idiot motioning not so subtly to my groin. At best I was packing four inches. But my mouth apparently forgot all that.

      “We would make a pretty good team right?”

      “Are you seriously asking me out?” she responded, her tone a mix of incredulity and indifference.

      “Uh… yeah, of course,” I said, leaning against the nearby locker, only to absolutely misjudge the distance, almost loosing my balance, Nice.

      She looked me up and down again.

      “Turn around.”

      “What?”

      “Well, I want to see what I’m working with, right?” she said as if any idiot could have understood what she meant.

      “Oh. okay.”

      I gave her the tour, not sure exactly why, my face getting redder and redder.

      “You know what? Sure,” she said with a big wide smile.

      I almost couldn’t believe what I was hearing.

      “Wha…” I mumbled, the words escaping me like the wind was knocked out of me.

      “Why not? It’s been soo loong since somewhat had the balls to ask me out, here I’ll text you my address, come by tomorrow, say seven o’clock?”

      I was speechless. This had to be too good to be true.

      “Cool, see you then.”

      And she was gone, and it absolutely was too good to be true.



      The next day was Saturday, I had all day to prepare. I showered twice, and then a third time out of shear nerves. I fretted all day about what to wear, I had no idea what we’d be doing. Was I supposed to come up with the date idea? Was she? I constantly checked my phone but there were no new messages since yesterday, still the same, singular text reminding me of the time and her address. The only one in our text history. I knew I needed to text back asking for more details but somehow if felt like if I did it might break my reality that I was about to go on a dating with Brandi Fucking Jones!

      Even as seven 7pm approached I felt less and less ready for this, I was wearing my best, I was as clean as can be, I even went out and against my better judgement picked up a few condoms, the first time I ever purchased any, a part of me hoped…no dreamed I would get the chance to use them.

      Before I knew it I was standing outside Brandi Jones’ house and I was knocking on the door as the night sky above me turned to dusk. The door swung open, almost tantalizingly slowly, and there she was, in a short skirt and tank top, casual but sexy, exposing her lean and curvy midriff. I was immediately off put.

      “Hi Brandi,” I stumbled meekly, “I brought you some flowers.”

      “Oh, flowers, how original,” she said as genuinely as she could muster, “Now come on in. My parents are away for the weekend and I want to get started.”

      She grabbed my hand and pulled me inside closing the door behind me and dragging me up to her room.

      “Started!? Started with what?” I said, I was wondering if she had the same ideas in her mind that I did, I hoped she did, but oh god what if she did?! My heart pounded as my mind raced. Brandi let go once we were inside her room and she promptly locked the door with a key, odd for an interior door. Her room was your typical high school girls room, the walls were alight with shades of pink all over, posters of hot boybands and hunky athletes littered everywhere, her closet was large with the doors closed, no doubt all the room was necessary to house her many, many outfits and shoes. Her bed was large and fluffy with lots of pillows. There was a large dresser with lots of lights and mirrors on it, a necessity for anyone using large quantities of make up.The whole decorum was slightly off putting, having never been in a girls room before, being an only child.

      “Do you want me?” Brandi asked, turning around towards me after locking us in, she stared intently at me waiting for my answer.

      “Uh…uh?…” was the only noise that came out of my stupid mouth.

      “Do you want me? Do you want to take me like a woman?”

      Jesus Chris! Was I really going to loose my virginity to Brandi Jones!?!

      “Yeah! Sure! Whatever you want!” 

      “Mmm… music to my ears,” Brandi and I were face to face at each others eye level, being about the same height, suddenly she reached forward and stuck her hand down my pants but outside my briefs, getting real close with dick, which had been fully erect for some time now, “Ooh, you weren’t kidding, you’re really packing down there!”

      Did I read it wrong? Was four inches above average? Maybe Brandi was just as inexperienced as me? Either way Brandi was getting way more intimate than I ever expected.

      “Do you want me to get… do-do you want me to bring…” I stammered unable to finish my own sentences.

      “Listen to me Chet,” she started getting even closer and whispering into my ear, she smelled so beautiful, I couldn’t think at all, “I have a very specific kink, one that I think you can fulfill.”

      I stopped. Like my brain hit the reset button. I felt like I could think again.

      “Yeah!” I said, impossible to hide my excitement, an emotion that seemed equally matched by Brandi’s giddy smile. She reached her hand into my underwear now and caressed my cock, feeling all around it. I had to be careful that I didn’t jizz my pants, I couldn’t afford to blow it now.

      “It’s so hot, I know you’re going to love it!” She said leading me on further and further.

      “I’d be happy to do whatever gets you off!”

      “Totally awesome! It would be so hot if I could dress you up in girly clothes!”

      “Wait, what?!”

      “Yes! Please it makes me so wet just thinking about it, here!” she grabbed my hand pulled it to her and under her skirt, placing my fingers on her pussy. I was so surprised that it took me a moment to register that she was indeed dripping wet.

      “Whoa…”

      “Please, it has to be you, it has to be now!”

      “Why me?” almost hating myself for finding excuses to not be banging Brandi right now.

      “Are you kidding, you are so hairless, especially where it matters,” she said as her hand rubbed my smooth crotch. I had always been unusually hairless, “and you’ve got such cute pouty lips, they’d look great covered in lipstick. I already know the perfect colour for them.”

      I looked at Brandi, she was practically begging for me to do this. There was no way I could say no, whatever it took to get into that dripping wet pussy.

      “Alright, I’ll do it.”

      “That’s fabulous, now come over here I need to show you to your new outfit for the night.”

      She grabbed my shoulder and led me not to her closet but to the bed where I’d failed to notice that she already had laid out some of the pinkest and girliest clothes I’d ever seen. First was a pair of soft thigh high socks, some ultra frilly pink silk panties, a short pink skirt, a ruffled pink crop top with what looked like extra puffy shoulders, and to cap it off was a pair of black heels at the bottom of the bed.

      “I can’t wear that!” I said, girls clothes was one thing, this was downright humiliating.

      “I’ve waited all day to do this, you can’t flake out now. Just try them on, they’re surprisingly comfortable, you’ll see.”

      I don’t know why her words held so much sway over me, perhaps the prospect of fucking her after going through all this spurred me on.

      “Go on, strip, let’s see that bod.”

      I hesitated, I mean this is what I wanted right? yes, but not exactly like this. However I submitted and started to remove the clothes I’d so carefully picked for this date. First my shirt, then my pants, finally my briefs and socks. As I removed each article Brandi watched with rapt attention, give me the old up and down. I suppose it was flattering, but it was also slightly creepy.

      I grabbed the thigh-highs, the fabric was super soft like fresh cotton, and one after the other I slid my toes into them and pulled them high. They felt so god damn comfortable, they hugged my skin but not too tightly, Brandi was right. My trust in her, despite the bizarre request, heightened. I looked to her and she motioned for me to get on with it.
“The panties are the best part,” she said, “they’ll feel even better.”

      Before she even finished her sentence they were in my hand, I surprised myself, eager to see just how comfortable they really were. In a second I slid them up, the silky fabric practically massaging my thighs on their journey upwards, I pulled them around my ass and up into place. They were amazingly snug, cupping my cock and balls gently but firmly. Once I finished revelling in the feeling I noticed a slight chill around my backside. I reached back to discover that there was a hole right over the ass on these panties, and by design too, the edge of the hole was laced with white frills, the same kind as the top and around the legs.

      “Wait? What is this?!” I said feeling the hole that was exposing my ass.

      “Oh don’t worry about that, it’s just for flavour, beside you have a cute butt, you should flaunt it a bit more.”

      “You think my butt is cute?” I asked, blushing.

      “Totes,” she confirmed, laying down on the bed, not taking her eyes off of me, she certainly seemed to be really into this little dress-up game, I hoped it meant that I was at least doing something right. So I put on the skirt which fastened at the hips with just a couple buttons. I couldn’t help but appreciate the way the skirt swished and swayed with the movements of my hip, it was actually turning me on.

      Putting on the top was no real fan fare but once I did I couldn’t help but notice what the purpose was of the ruffles in front, they gave the illusion that I had tits, at least B-cups, when in reality the material, like all the others hugged my skin leaving little else to the imagination, and to top it all off the puffy material at the shoulders completed the innocent little girl look that Brandi was obviously going for.

      “You look so hot,” Brandi said, “but we have to put on the final touches.”

      She jumped off the bed and ran behind me to her dresser with all the mirrors on it and came back with a large purse. She started pulling out all sorts of make up accessories I could barely name, let alone understand their purpose.

      “Let’s see, bubblegum pink? No, ah, here it is, hot pink lipstick, just the right colour to show off those perfect pouty lips of yours, and it will match your outfit perfectly, now come closer.”

      I was hesitant to shuffle forwards know what she intended to do with the little tube of emasculating cosmetics.

      “Oh come one, please don’t ruin the fun, you won’t really look right without it!”

      Brandi looked at me with uncharacteristic puppy dog eyes and I fell for it hook, line, and sinker. Once I capitulated she grabbed me by the chin, forcing my lips into a nice pout and tracing over them two or three times in places before stepping back and admiring her work.

      “There we are, now who’s a little sissy?”

      “uh…” I stammered, “I am?”

      “Yes you are, and what little sissy would be complete without some nice blush and some pink eye shadow,” she said coming back to me with some brushes and more pink colours. She started rubbing it over my cheeks and eyelids, I don’t know why I let her, maybe because her enthusiasm was infectious.

      “And voila!” she cheered springing back to get a look at the final product, “We’re finished. You look so hot.”

      Throughout the ordeal I felt thoroughly humiliated, now that it was over I was relieved, my cock throbbed, both in Brandi’s presence and aided by the silky feel of my new tight underwear. I looked at her, she seemed so happy, so I took my chances and leaned in towards her, face first lips ready, I closed my eyes, anticipating my reward.

      Then I made contact, but it didn’t feel like lips, I opened my eyes to see Brandi at arms length from me, my lips stopped by a single index finger.

      “You are incredible,” she said, but it didn’t sound like a compliment, “you really thought this whole time that I was going to have sex with you?! You must be, like, literally retarded.”

      “Huh,” I was thoroughly confused.

      “Babe, come on out, your new toy is ready!” Brandi shouted out.

      Behind me the closet door opened and hiding in there the whole time, no doubt watching, was a goliath of a man. Naked from the waist up wearing only grey sweat pants, skin as dark as the night, the white’s of his eyes affixed to me. His form was extremely muscular, almost sporting an 8-pack abs. As he walked there was an unmistakeable python hidden in his pants, down to his knee, itching to come out and play.

      “Yeah, she sure look ready to me,” he said, his voice a booming low timbre freezing me in place, unable to look away at the sheer masculinity and testosterone before me.

      “This, my sissy little friend, is my boyfriend Jamar,” she said stepping forward and grabbing his hulking arms and caressing every muscular aspect of his torso, “He’s a college man, going to be a professional NFLer one day, making millions. A real man. Although I love him dearly, he’s a devout catholic which means my pussy doesn’t get to enjoy his gorgeous manhood, not that he can’t please me in other ways. Sometimes I just look at him and, like, wet myself. He’s so hot, isn’t he?”

      Brandi was looking all over Jamar’s body with absolute and genuine admiration, desire and lust.

      “And I ain’t allowed to masturbate neither seeing as it’s against god an’ all” Jamar said, still staring at me with what were clearly rape-eyes, “That means I got two options, the mouth and the butt.”

      The realization of my situation was dawning on me much more slowly than I’d like.

      “And as much as I love him I don’t, like, do anal, I’m not that kind of lady. But I figure, you’re, like, a nobody at school, so it doesn’t matter if you’re known as the anal queen or not. And you would have to be a queen to take this beast.”

      I couldn’t believe it, I had to get out of this nightmare. I slowly started stepping to the side, hoping they wouldn’t notice me eyeing the door on the other side of the room, but subtlety, especially now, was not my strong suite.

      “Hey now little filly, where do you think you’re going?” Brandi said also side stepping to keep her between me and the door. I panicked and bolted for it. But Jamar was quick, cause of course he was. He grabbed my shoulder and just held me there with one hand in a vice grip. I couldn’t move.

      “If it’s any consolation I wasn’t completely lying to you,” Brandi said a wicked lusty smile spreading wide on her face, “I do really get horny when I see little dumb sissies like you get destroyed by my boyfriends big black dick.”

      “Get on you knees,” Jamar ordered.

      I didn’t. Brandi showed no mercy.

      “You’re going to find out what happens when a pencil dicked white boy thinks he can have me!” She shouted and grabbed my balls and squeezed, the pain causing me to fall to my knees, “See, she does know her place, now take out your masters cock.”

      From the ground my face was less than a foot from Jamar’s legs where the giant anaconda in his pants was all the more alarming, but I found my will to resist broken, and my hands reached out to the top of his pants, reaching in I grasped the base of his huge cock and slowly pulled it out of his sweats, it took ages as I gradually revealed what would be the bane of my existence, but before long I had all of his monster cock before me. A true terror to behold.

      Brandi leaned forward towards me now, more intimidating than I ever imagined.

      “So, you want a kiss do you?”

      I nodded meekly, not really sure what I was agreeing to. Brandi took Jamar’s cock out of my hands and put the head to her mouth, she gave it one long drawn out kiss, slathering his head in saliva. She pulled her head back, a trail of saliva connected briefly before snapping, the head of Jamar’s cock had a faint imprint of Brandi’s maroon coloured lips. She pointed his cock back towards me and I stared at the head, almost going cross-eyed as it approached closer.

      “Go on, take your kiss.”

      I don’t know why, but seeing Brandi’s faint lip marks made it somehow easier and I closed my eyes and pressed my pursed lips to the very end of Jamar’s ebony pillar. It was so hot to the touch, pulsating and engorged.

      As I began to part my lips around the hot bulbous head Jamar grabbed my head with both of his large powerful hands. I opened my eyes, fearing what he was about to do, and looked up at him doing my best impression of sympathy. He grinned, wide, toothy and sadistic. And he pulled my head forward while thrusting his hips, impaling my head on his ebony phallus. Immediately his cock filled my mouth and pounded at the back of my throat. My eyes rolled up and I started gagging. He continued to press hard, desperate to worm his thick cock past the small of my throat, through my gagging and convulsions of stress and pain I could feel it squeak through inch by inch, my throat gripping his cock tight, no doubt offering endless waves of pleasure in only one direction.

      “Oooh! bitch has definitely got a virgin throat on her!” Jamar exclaimed as his mammoth prick continued it’s path of destruction, “Looking forward to making it a pro cock holster!”

      I moaned at the pain and humiliation, dressed like a little sissy and forced to suck some black guys big fat cock. The moaning accidentally did the trick and with a flash of pain his cock sunk deeper, my throat expanded significantly, maybe even permanently.

      I reached up to feel my throat, almost expecting to feel a rip or tear. It felt intact and healthy, but when Jamar pressed on deeper I felt a bulge in my throat snake deeper in time with his movements. I was horrified that my body could even accommodate such girth and I knew that even if there was no other evidence to the crime, my neck alone would tell the tale of major deepthroating action underway.

      When Jamar got about two thirds of his cock in my mouth he stopped going deeper and started fucking my mouth like a goddamn pussy. I had an excellent view of his hips pushing back and forth and his cock slide in and out of my mouth. My gag reflex began to subside gradually until it was gone and my convulsions stopped, my mouth went limp, letting him use it for his sexual benefit, one arm fell limp at my side, the other was still fascinated by my bulging throat, it caressed it as he moved in and out of my esophagus. I felt like a rag doll, lifeless, an object held aloft only by Jamar’s powerful hands and cock.

      In my haze I barely noticed when one of his usual thrusts that he started going in, but didn’t start going out, he kept going. I was too unaware to do anything to stop him as he simply pulled my head all the way to his crotch, almost zero resistance left in my throat. Next thing I knew is that my eyes wear pressed into his rippling abs, my lips touched the base of his cock and my chin was buried into his bulbous black balls.

      It was a throughly stressing position, no longer painful, just worrisome, like I should only feel this violated during a medical procedure or something.

      “Hehe,” Jamar chuckled as I flailed helplessly, fully impaled, “That’s one hole conquered. You really look like you belong there you know, you little girl you.”

      Jamar made sure to hump my face a few more times before finally letting go and I peeled off him, his cock sliding from my mouth almost endlessly until I fell back on my ass gasping for breath. His long dong dangling before me, multiple strands of spit and saliva hanging between both our heads. Staring at it now, glistening wet, the reality that I had just deep throated that thing hit me when I saw a bright hot pink ring clearly visible at the very base of his cock.

      “Oh totally!” I heard Brandi say just off to the side, one hand down her skirt the other holding her phone, and then I heard the snap, “This will, like, make for an awesome photo.” She admired the photo which no doubt left little to the imagination as to what exactly had just transpired recently.

      “Wait! No! You can’t!” I said rushing to grab the phone, but Jamar once again stopped me with but a single powerful hand, grabbing my wrist and holding me back.

      “Relax, I don’t plan on sharing this,” Brandi said, her voice feigning innocence, “well at least as long as you don’t do something to upset us. But we can talk about that later, Jamar baby, I’m sure you’re excited to get to the main event?”

      “Most def, but before that this sissy needs to learn to worship her gifts proper,” Jamar wrestled me back down to my knees effortlessly and lifted up his cock displaying his prodigious set of black balls. I never noticed before just how unusually large they seemed, “When a real man offers his load to you you make sure it’s a big one. Worship my balls.”

      “Cool, babe, well while you’re doing that I’m going to get the stream set up.”

      “Stream!” I exclaimed before Jamar popped one of his balls into my mouth, followed shortly by the other one, muffling my cries.

      “Well there’s no way I’m like, not going to take advantage of this opportunity, I mean Jamar will be making loads of money in a few years, but for now I need the money to go shopping, duh. Do you know how many people would pay to see a private screening of this. So Jamar, what do you think of this title: Virgin white sissy boy gets buttfucked by monster black cock?”

      Jamar meanwhile was giving me a thorough tea bagging, popping both balls out at once, a feat that great stretched my mouth even more than his cock, before dunking them back in.

      “Catchy,” he said simply, letting his cock fall onto my head so that my profile was outline with thick black meat as Brandi leaned down to face me.

      “Don’t worry, I’ll try not to get your face on camera, not that anyone would recognize you now anyway.”

      I whimpered, balls in my mouth, unable to disagree with her even if I could talk.

      “All set?” Jamar asked.

      “Yep,” Brandi respond from her laptop, a small GoPro camera in hand, “wow, it’s only been   two minutes and there are already over a hundred paying customers, so let’s give ‘em a show worth the money.”

      Jamar pulled his balls out of my mouth and grabbed me by the neck.

      “Alright sissy bitch, time to turn that ass out.”

      He pulled me over to the bed and bent me over the side, knees on the soft carpet, ass out. He grabbed both my arms and crossed them behind my back so that he could pin me down with one strong hand. Then I felt something enter my butt, though it was too small to be Jamar’s dick, I looked back, as best as I could in my restraint position. There was Brandi, looking at me, a hand behind my butt.

      “If nothing else, Chet, at least I’m not completely unmerciful.”

      And she squeezed. I felt a thick viscous liquid shoot up my ass coating the first few inches in lube, I felt slightly relieved, but that quickly vanished when Brandi got behind us all to get the best view.

      “Alright! We’re live!”

      Jamar, one hand on me, the other on his cock got into position and I felt him stick his cock into the open hole of my panties and rub his incredible cock head up and down my ass, getting it good and slick with lube.

      “Wait! You’re a christian,” I desperately tried to reason, “isn’t this against the bible or something?!?”

      Jamar leaned in close and whispered.

      “It ain’t gay if you the girl!”

      And he pushed. Hard.


To Be Continued...
