Whether He's Ready or Not...

Whether He's Ready or Not...

Randolph was just sitting by himself as usual. The young boy was on a bench near the garden, reading a paperback. He enjoyed the clean air and privacy, knowing that no one would come out to disturb him in this secluded area. Privacy was the main reason he chose to do his silent reading here, at a place where he can expect to be left alone. Little did the 18 years old know how wrong he was about all of that.

After he was able to read only 11 pages, Randolph heard someone clear her throat in front of him. He looked up. Standing there on her fancy high heels was the voluptuous figure of a tall, very popular girl from their school. Sarah just gave him a bright smile before sitting down next to the befuddled nerd. Most people never come to this part of the school where he was currently sitting, and the cool kids, which Sarah was definitely a part of, would never deign to grace him with their acknowledgement, much less to sit down next to him like this. Sarah is an exception though. She was well known for her sharp jawlines, fierce eyes and glossy long hair that frames her perfect face, large round breasts that seem to define gravity and a tight, muscular body from countless hours of cardio. The popular girl is also nice and treats everyone well.

Randolph, meanwhile, was underweight and had a very plain, ordinary face. He did however smile back at her politely, despite being noticeably confused by her presence and decision to sit down next to him. "H Hi!. H How a are you?" he managed to stutter, mentally yelling at himself to be more articulate, delivering self criticism of his failure to speak confidently and make some friends. The boy also berated himself for already getting a boner just from this beautiful girl looking and smiling at him. It's her perfume as well, the teenager tried to make himself better by reasoning so. As it getting turned on by how she smells is any better.

"I'm good, thanks! Can you please help me with something, Randolph?" Sarah replied. She gave him her million dollars smile, inwardly chuckling at how easy it was to get his petite boy flustered. He really was cute when embarrassed, the athletic girl thought to herself as she glanced down at the tent pitched in his pants by his erection. 

Randolph realized that she spotted his hard on and felt all the blood rush up to his cheeks. At least there won't be more flowing down to engorge his already rigid cock, he thought. He has already swelled enough and for his arousal to become clearer would be bad. Really bad. "Uh, o okay! Sure. I'll b be happy t to help you!" Stupid. Why did he have to say that right away, without asking what she wanted help with first? Never mind. She is one of the nice, popular people. Sarah wouldn't set him up or do anything to humiliate him, right?

"Well, I've been struggling a lot lately with physics. You seem to do okay enough in class. Would you please come over to my house today and help me study for the exam next week?" she asked, biting her lower lip. Swallowing, Randolph thought for a bit. He has never been to a classmate's house before, so this could be a new experience. Plus, he's always liked helping others, even those he doesn't know very well. Sarah respects him enough to ask for his help and that shows a degree of trust and good faith, so he should not disappoint her. 

He nodded. "I can do that," he muttered slowly, giving her a reassuring smile, before looking down at his feet coquettishly, feeling coy all of a sudden. The way her eyes pored deep into his, staring as though she could peer at the depth of his heart and see exactly what secret desires he harbours inside. He really hopes she can't.There are a lot of fetishes he has hidden beneath the innocent boy facade that Randolph would feel ashamed of, if they ever leaked out. Sarah squealed happily and gave him a hug, kissing him on his cheek, making the poor boy squeak. He shyly squirmed in her arms, only half-heartedly struggling, secretly wanting to feel her strong arms remain wrapped around him. Eventually, she let go.

"Come to this address at 4 PM, okay?" she said, leaving a piece of paper in his lap. Randolph just nodded, still in a haze after what just happened as she giggled, walking off and waving back at him. The boy remained seated where he was, looking down at her neat handwriting. He smiled briefly to himself, glad that he might be able to interact with another human being. She is a very sweet, nice person and he likes her. In a romantic sense? Maybe. They haven't been close friends although the two have worked on school assignments before, but perhaps something more could happen between them.

Later that afternoon, he gathered his textbooks and notes, and biked over to her place. The boy knocked on her door and waited patiently. She opened it. Standing there, she was clad in a form fitting T-shirt and booty shorts that cover quite less than half of the thighs, revealing her muscular legs that lead up to a firm ass. The girl smiled at him, beaming as she grabbed his wrist and led him inside her arm. "W Wait! Sarah, I c c can't k keep up with you!" His protestations were unheeded as she dragged him to her bedroom. He barely had time to take notice of all the plush, expensive looking furniture arranged on fur carpets as Sarah reached a door. She opened it, pushed him inside.

Three pairs of hands took hold of him and then forced him towards a king-sized bed. He was flung onto the mattress and two people grabbed each of his legs, pinning them down onto the bed and quickly looping ropes around the ankles, tying the knot tightly. The third tied his left wrist to one of the bed posts. They stepped back and as Randolph stopped thrashing around, he could finally see who was responsible for his predicament. "W W What do you want?!" he sputtered indignantly at the trio before him.

Morrigan, Betty and Melissa were all close friends of Sarah's. They shared a look and burst out laughing. "I can't believe it's this easy!" Morrigan said, struggling to catch a breath as she continued to laugh at the sight of the boy's despair-ridden face. "You really are a weakling aren't you?" the girl questioned.

"Shut up, Morrigan. He might be weak, but he is my weak little cutie," came a familiar voice as Sarah entered the room, heading for the bound boy. "Shh, it's okay baby boy. I'm sorry we had to be so aggressive with you. I know you're painfully shy but there's no need to be embarrassed. I'm just going to get rid of your clothes for you, okay?" Without bothering to wait for his reply, she took a knife on the bedside table next to her and began to cut through his shirt first. Removing the shreds, she salivated at the sight of the boy's thin frame. She began to lick one of his nipples, placing her lips around it, biting it lightly, making him moan in surprise and alarm. "Hmmm, that's it. I want you to moan for me." She rubbed the other one, squeezing gently at first, pinching. As much as it embarrassed him, the beautiful brunette's attention was making his manhood twitch into position, stiffening against his pants. Her friends were bent over with laughter, only silenced by Sarah's glare. She unbuckled his belt slowly, sliding his pants down his bony legs towards his feet. Grinning with lust, the girl used her teeth to bite the waistband of his boxers, dragging them along the length of his legs the same path where they ended just above his ankles. 

"You know, Randolph, I've wanted to fuck you for the longest time. It's your own fault you are so adorable I can't help but have to rape you. You have no one to blame but yourself for being such a cutie" the horny teenage girl declared, before swiftly yanking her top up over her head, revealing her really big, bare breasts. She didn't bother wearing a bra, not wanting to waste time taking it off when she finally gets to this. To fucking the only boy she wants. 

"Y Y You c could h have asked me out, you know? I I mean that y you're so s smart and n nice, and f funny... I would never turn you down!" he said, pouting looking aside. "C C Can you untie me first though? I d don't th think I I'm ready to l lose my virginity before a first d date, even if it's someone perfect and really nice like you... I'd really like to get to know you as a person before we, you know, get intimate." the boy coyly muttered, completely forgetting that he was tied up against his will.

"Hmmm, nope honey. You're so romantic saying all that to me but I'd rather fuck you first and then discuss our first date later. And don't worry, I've started taking the pill since I began planning to fuck you a month ago. I'm going to fuck you now whether you want it or not" With that said, she removed her short shorts and stripped off her panties as well. The lightly muscular yet still curvy girl walked towards the helpless Randolph, straddling his hips. She brushed her molten pussy lips over his groin, her labia fluttering against the underside of his rock hard dick. The girl smirked mischievously as she rubbed his swollen tool with her big, strong hand. She poured some lubricant onto her palm before starting to jerk him off. Sarah caressed his tool with love, squeezing him, rubbing the underside with her thumb as he started gasping from her touch. The boy was gripping the bedsheets very tightly.

His mouth was open as the girl started pumping up and down his solid penis harder. She used the other hand to cup his balls, massaging his scrotum gently. The fit girl was sliding her slick hand along the length of his dick, twisting her wrist as she went, making sure to coat every last bit of his short dick with lube as she beat him off. He was soon bucking his hips upwards involuntarily, trying to thrust and meet her hand, but she used her free hand to hold him down. She was the one fucking him with her strong hand.

The girl continued to pump slowly at a measured pace, alternating between squeezing and stroking him, rubbing along the entire length, sometimes focusing on the sensitive glans, driving him wild with pleasure, before focusing her attention elsewhere, not wanting him to cum too soon. 

Sarah kissed the glans gently, startling him. "D Don't. It's d dirty down th there," he shyly protested, completely ignored as she swirled her tongue around his cockhead, swallowing the spongy tip into her mouth, sucking on his dick, letting her lips slide down the length towards the base. "Y Y You sh should l let me wash it f first s so it w won't taste or smell bad to you."

"I won't allow you to be modest with me, baby. I love you and your body belongs to me. I can do whatever I want with it. Your dick isn't yours anymore, it's mine now and I want to suck it, so just shut up and enjoy the blowjob." The girl then continued to lewdly swallow his cock back into her warm mouth noisily. Her head bobbed up and down on his stick, moving at a faster pace as she sucks hard, humming as well, driving him wild before slowing down to tease him. She does this again several times. He is so small it's very easy for her to deepthroat him. Her hands were kneading his buttcheeks as she squeezed his ass while taking him in her mouth, completely overloading his nevers with sexual pleasure he never felt before. She wanted to make him completely addicted to her, so that he would never leave her, and will always belong to her.

Sarah paused for a moment before grabbing the bottle of lubricant and coating her left forefinger with a generous amount. She mischievously massaged his sphincter causing her to look at her in confusion and then alarm as she began to gently push her way inside, carefully adding more pressure. The lube allowed her to put her digit all the way inside his ass after half a minute of struggled and she curled her finger towards herself, tapping against a small gland inside of the boy which made him release a cute moan. Having found his prostate, she pressed on the spot while continueing to blow him. The dual sensation was too much and almost immediately his dick became rock hard and fired massive loads of semen into her mouth, which she greedily swallowed.

The girl removed her finger from his anus and stopped sucking his dick, but gently caressed his penis with softer strokes, knowing how sensitive his skin down there could be after that wrecking orgasm crashed through him only seconds ago. "How was that, baby? Did you like it?"

"Y Y Yes. I l loved it," he admitted, cheeks bright red with embarassment.

The teenage girl adoringly caressed his tiny balls, before eventually deciding to stop with the handjob and then guide his by now well lubed dick through her nether lips, making him enter her vagina. The walls of her cunt wrapped around his short tool as she slowly penetrated herself with him, always maintaining control. She buried him to the hilt within her, his dick balls deep inside her pussy.

The warmth and tightness of her sex engulfed him and sent him into sensual overload. Sarah immediately began to rock back and forth, sliding up and down on top of him, bouncing on his dick. She rode him, enjoying the feeling of being filled by his lovely little dick, as her vaginal walls slid along his cock. The girl clenched her kegel muscles, fluttering her pussy, making herself much tighter around him. His eyes opened in shock as the pleasure level increased even further in him.

Sarah was overjoyed by how her beloved moaned so adorably, making her pound him even harder, placing her hands on either side of the bed, almost breaking the bed in half with how fast and hard she was thrusting down onto him. Her body violently crashed down on to his, battering him as her pussy gripped the entirety of his cock, abusing his tender flesh, causing him to scream in pleasure. The girl bounced up and down on top of her little nerd with abandon, smashing her lips aggressively against his. 

"Harder! Please fuck me harder!" Randolph begged desperately. Sarah was only too eager to comply. She fucked him fast and soon he felt his balls tense up. The pleasure was indescribable. He has never experienced anything like this before. The way the walls of her pussy caressed his cock as she stroked him was amazing. His dick spasmed inside her channel, firing off loads of semen inside her womb. 

"Good boy, Randolph. Rest for a bit. When your boner comes back, I want you to cum again, but this time you will be masturbating while looking at me. You'll cum all over yourself for our amusements," she said, as her friends chortled behind her. The boy blushed madly, ashamed to find himself getting hard again quickly at her description. The girl smirked. She got off of it.

Standing at the edge of the bed, she watches as her boyfriend wraps his one free hand around his warm, slick penis, gently pumping up and down. Sarah eyed him lewdly as the shy boy breaths through his open mouth, using her pussy juice as lube to masturbate, jerking off slowly. He caressed his dick, stroking faster, looking straight at her with love, his fist beginning to fly quickly up and down the length of his tool, his hard, needy cock throbbing in his hand. The boy stares at her perfect round boobs and her flat stomach as he kept jerking off before closing his eyes at the pleasure. Suddenly, he began to feel a stream of hot liquid landing on his dick. Opening his eyes, he was shocked to see Sarah standing next to his groin, pissing directly onto his hard cock. The sight of the flow of her urine from her cunt to his dick, the smell that is bitter but not unpleasant and the sheer naughtiness of what was happening, along with the warmth which came from her piss on his cock drove him over the edge as he violently climaxed again, feeling the eruption in his cock as he unloaded massive amounts of cum, emptying out his balls as semen flew from the top of his dick, even as she continues to urinate on his throbbing dick.

"Wow! You came so hard when I peed on your cock! I can't believe it. You're perfect for me, darling. I'm never letting you go. Sweet dreams for now. You need some rest for what I plan to do to you later tonight." Sarah said all this before bending down to gently kiss Randolph on his eyebrows and exiting the room, allowing him to get some sleep.

When he eventually proposed to her four years later, Randolph was astonished when Sarah laughed and told him that she and her friends already planned a large part of their wedding that will take place in the fall of the same year back in the day they had sex for the very first time. Then he laughed along with them. Sarah and her cute Randolph lived together happily ever after.