Courtney's Fist Time

Alex sat on his bed, flipping through his Instagram, only pausing for a few seconds whenever a busty model popped up on his feed. He was in a loose-fitting shirt and boxers with his legs spread apart, trying to release the the faint throbbing in his testicles caused by his encounter with Mrs. Brost earlier that night. 





“Whatcha doing?”





Alex quickly clicked out of the app as his eyes darted up to see Courtney standing in the doorframe looking like one of the models he was just ogling. She had on a skimpy black lace lingerie set that barely contained her enormous breasts. The black lace bra was a stark contrast against her smooth milky skin. It pushed her breasts together to create an incredible view of her cleavage with her tiny pink nipples just becoming visible along the lace trim. She had on a pair of tiny Panties that hugged her toned ass. To complete her outfit she had on black thigh-high stockings which were held up by a garter belt that was cinched around her tiny waist drawing Alex’s eyes to her flat stomach. The stockings themselves hugged her long legs tightly cutting into her soft thighs.





“Nothing just scrolling.”





“My Mom just left. She said she had lots of fun tonight and wants to get together soon.” 





Courtney took a playful step into the room, her heels clicking against the hardwood floor echoing in the quiet space. She had a knowing smile on her lips as she approached Alex, swaying her hips with each step.





“Well, I’m glad she had a good night. I knew it was important to you that your mom liked me.”





Courtney smiled as she stopped at the edge of the bed. 





“Come closer.” 





Alex scooted towards the edge of his bed so his legs hung off.





“I made a promise to you earlier didn’t I.”





Alex only nodded so he didn’t jinx anything by speaking the words aloud.





“Well, my mom loved you so you fulfilled your end of the deal. So it looks like it's my turn to fulfill mine. Are you ready to take my Virginity?”





Alex's eyes almost bulged out of his head as he gulped audibly. She had never been so direct before. He had thought that his day would never come. Since they had been living together every day Courtney had been an unintentional tease as she flaunted her perfect body around the house. Every time he had tried to find some privacy to release his aching balls Courtney would somehow walk in on him. Alex had now been living months with the worst blue balls of his life, but now she was actually willing to go through with it, it was almost too much for him to bear. He could feel his cock growing in his boxers at the thought of finally feeling her tight pussy around it. 





Courtney noticed his reaction as her smile grew wider. She placed a hand on his cheek and leaned in to whisper in his ear as her warm breath tickled his skin.





"I know you've been waiting for this," she murmured, her hand trailing down to grip his hardening shaft through the fabric. "You will have to tell me what to do.”





Courtney knelt so she was between Alex’s legs so her massive, soft breasts rested heavily on his thighs. Her warmth and softness made his cock throb even more. She looked up at him with her big blue eyes, full of curiosity and excitement. Alex felt his heart racing as Courtney playfully tugged at the waistband of his boxers.  He watched as she pulled the elastic down with a giggle, freeing his erection. It sprung up slapping her between her breasts as the swollen tip brushed a bit of pre-cum against the lace of her bra. Courtney let out a little yelp of surprise as she let go of the elastic band of his boxers. The band snapped back striking him in his already red and swollen balls. Alex lurched causing his penis to bounce back and forth like a bobblehead. Courtney’s eyes were bright with curiosity and excitement as they followed his penis





“Your penis is so funny.  It’s like it has a mind of its own!” Courtney giggled softly.  





She pulled down on his dick as she watched it spring back to attention. Her fingertips glided over the smooth skin of his shaft before flicking it causing Alex to shiver. Courtney’s eyes darted down as she saw his testicles hanging over the edge of his boxers. Without warning she reached down gripping his balls with a surprisingly firm grasp for such delicate hands. Her nails dug in slightly as she played with the sensitive skin. Her eyes were wide with wonder as she felt the weight of his testicles roll around in her hand. She looked like a kitten who had just gotten ahold of a new toy.





“Those are very sensitive.”





"Really? But they're so squishy!" Courtney exclaimed with a grin, continuing to squeeze and tug on them playfully. Alex couldn’t help but flinch, as she giggled at his reaction. “It’s like playing with stress balls but only better because they’re attached to you!”





Alex winced, trying to hide his pain with a forced chuckle. He knew Courtney didn’t mean any harm, she was just so clueless when it came to male anatomy making her innocence both charming and infuriating at the same time. 





“Courtney, please, that really hurts.”





"Like does it tickle?" Courtney asked not registering his discomfort. She gave his right testicle a little poke as Alex jerked back, his hand shooting down to protect his sensitive area. 





As he went to speak she gave his nuts a sharp tug catching his words in his throat. Her laughter filled the room, it was a sweet sound that was unfortunately paired with the pain she had just inflicted. He tried to sit up, but she playfully pushed him back down onto the bed, her breasts jiggling slightly with the movement. Her eyes were wide with excitement as began to gently tug on his testicles watching them stretch and retract as she played with them. Alex's face contorted in pain with each pull as Her laughter grew louder.  She continued her exploration, completely oblivious to the agony she was causing him. Alex’s hands clenched the bedsheets as his teeth gritted in an attempt to maintain a stoic facade. 





“It’s like a little water balloon. I wonder if I could pop one?”





Alex’s eyes went wide with horror, his breath catching in his throat. He didn’t know if she was joking or not, but the thought of such a thing happening was more than he could bear. He knew Courtney meant well, but her innocent curiosity might be the end of him and his manhood. He knew he needed to act fast and redirect her playful energy to something less painful.  Alex took a deep breath trying to speak through the pain as his words came out as a high-pitched squeak. 





“No!” He saw the look of shock on her face as he snapped at her. He quickly mustered a smile so she didn’t think he was mad at her. The last thing he wanted was for her to leave before finishing her promise. “It’s just that would be incredibly painful for me. I know you are just curious about it,  but  there are other ways to have fun with it. Let’s just go gently.”





 Alex took a deep breath and placed his hand over hers as he guided her hand away from his balls and to his cock, showing her how to stroke it gently. Courtney's touch became soft as it sent a shiver of pleasure through Alex. Her curiosity grew as she watched Alex’s face contort in pleasure with each different movement. She smiled to herself as she began to move faster causing Alex to let out a moan. As her hand glided faster along the length of his cock her hand slipped smacking her palm against his sensitive testicles. The sudden sting caught Alex off guard as his eyes shot open and a surprised grunt escaped his lips.





Courtney looked up at him with a puzzled expression, her hand suddenly stopping and letting go of his cock, not quite understanding why his reaction changed so abruptly. The sudden stopping of her strokes caused his balls to lurch with an aching pain as they released a tiny dribble of pre-cum  from his penis.





“Gross! What’s that?” Courtney said as another dribble came from his cock.





“That’s pre-cum.  It's like... a little taste of what's to come.” Alex was trying to keep his cool, but it was proving difficult her breasts pressing against his legs and penis.





“Oh, does it taste good?” Courtney leaned closer to inspect the clear liquid that clung to the tip of Alex’s dick. She stuck out her tongue and gently licked it off, her eyes never leaving Alex’s. He watched her as her tongue swirled around the sensitive head savoring the salty flavor. “Is like a warm popsicle!” 





Courtney excitedly opened her mouth as she caught his dick in her mouth with an innocent enthusiasm. Alex’s eyes opened wide as he felt the wetness of her mouth enveloping him. Her bright blue eyes looked back at him waiting for confirmation that she was doing a good job. Alex tried to form words but the way her tongue darted around the head of his penis rendered him speechless. Courtney took Alex’s moan as a positive reassurance as she licked his penis collecting the salty pre-cum.  She pulled back with a pop as a trail of saliva connected her mouth to the tip of his dick. She wiped her mouth with the back of her hand, a mischievous smile playing on her lips.





“Keep going, you’re doing great.” The words came out just above a whisper as Alex tried to hide the anticipation and pleasure he was feeling at this moment. Courtney’s eyes sparkled with excitement as she leaned back in going deeper this time. Her eyes would close with pure bliss, savoring the taste and the sensation of his cock filling her mouth as she reached the base.





As she bobbed her head up and down causing her breasts to sway in a rhythmic pattern. Alex couldn’t take his eyes off her as she worked his cock with surprising skill for a first-timer. Courtney's hand had found its way to her chest, and she began to squeeze her own nipple through the lace. Her eyes never left him, she seemed to be lost in the thrill of the new sensations. As she pulled up her teeth grazed the tip of him lightly making Alex’s body tighten as he gripped the bedsheets trying not to blow his load instantly.





“Mmm, your cock feels so good in my mouth, Alex,” Courtney murmured, her voice muffled around his dick.  Alex felt his orgasm building and knew it wouldn’t be long before he would erupt. He reached down and gently grabbed a fistful of her blonde hair, guiding her movements slightly to match his pace. He could feel his balls tightening and knew he was close. 





“I’m going to cum!" moaned Alex.





"Oh no, I'll stop then" Courtney pulled off his cock with a pout. Her eyes were wide with concern as she stood up. 





Alex’s eyes went wide with panic as he felt his orgasm slip away.





“No, it's a good thing.”





Alex grabbed her tiny waist and pulled her onto him. Her legs straddled him as he felt her plump ass rub against his erection. 





“I want this to be special for you. I want it to feel good for you too.” Alex said as he unclasped her bra with his hand. Her breasts bounced free as they pressed against his face.





With his other hand, he pushed her panties to one side and slid his penis into her. She let out a little gasp as she felt him enter her. He grabbed her hips moving them to give her the correct motion. She began to pump her hips faster. Grabbing Alex’s arms and pinning them against the bed as she began to take the lead. Her breasts bounced smacking Alex in the face. Courtney bit her lip as she felt a warming sensation growing in her pussy and thighs.





Alex could feel the tightness of her pussy around him as it felt unlike anything he had ever felt. He knew he couldn’t last much longer but he was determined to make sure Courtney enjoyed her first time. He reached down and began to rub her clit in slow circles as he felt her hips buck against his hand. Courtney’s eyes rolled back in her head as she moaned louder and faster. Her breathing was coming in short gasps. Alex knew she was close and so was he. He closed his eyes as he let the sensations wash over him.





Just about as he was going to cum he felt her soft hand grab onto his testicles. With a final push, he felt her pussy tighten around his cock as she climaxed as well as feeling of her hand grabbing his balls. He nails dug into his scrotum as she screamed out his name. She continued  ride out her orgasm on his dick while she kept his balls in a vice-like grip. He tried to call out but she could not hear him over her own screams. The pain was too much for him to cum as he watched longingly as her body collapsed onto him. Her breasts smothering his face.





“Oh my god, Alex. That was amazing!” she exclaimed as she got off his penis.





"But Courtney I ….."





Courtney's phone let out the ring of an obnoxious pop song interrupting Alex's words. She leaned over with excitement to grab it as her knee connected with Alex's balls with a sickening thud. Alex's eyes watered in pain as the weight shifted to her knee squishing his manhood underneath it.





"It's Amber!"  Said Courtney cheerily. "Say Hi."





Courtney shoved the phone into Alex's face. He could feel the ache in his balls spreading to his stomach as he tried to form words.





"Hello," His voice quivered before Courtney took the phone back. 





"One second Amber, Alex was saying something." Courtney pressed the phone to her breast, looking down at Alex with a waiting expression.





"I didn't cum." 





Alex’s voice was weak, his body trembling from the intense pain of Courtney’s knee still on his balls. Courtney looked down at him with confusion before realizing what she needed to do.





"Ok but I'll make it quick," Courtney whispered as she scooted back and off his legs to grab his penis in her hand. Alex looked up with shock as she picked back up her phone and started chatting with Amber as she beginning to stroke it.





“What were you saying, Amber?" Courtney’s voice was filled with glee as she babbled. Alex lay there, his body still recovering from the mix of pleasure and pain. He watched in disbelief as Courtney’s hand worked him with surprising enthusiasm, her attention split between her friend on the phone and the task at hand. He wanted the feeling to be nice but it felt rough from the lack of lubrication and the pain was still present in his balls.





“Hay Courtney I think I might need a bit of Lube.” He called up to Courtney.





She rolled her eyes and leaned over to her bedside table as she once again sending a knee into Alex’s balls. She leaned back with a smile as she squirted the white liquid out of a tube rubbing it all over his dick and balls before she began stroking his penis again. Alex closed his eyes as her hand easily glided over his shaft before she would play with the head. Alex soon felt a warm sensation on his penis and balls beginning to grow. He knew the feeling of an incoming orgasm and this wasn’t it. The heat began to grow hotter. Alex let out a yelp as his penis began to sting and feel like it was on fire.  His balls instantly shriveled up like dried dates as they tried to escape the burning pain. His hands quickly shot down trying to protect his junk but the feeling was unavoidable.





“Ow, it feels really hot.” He said as he tried to get his penis in a soothing position. 







“Oh My God! I’m so sorry that happened to you!” Courtney exclaimed with genuine concern. 





Alex smiled through the pain seeing she cared about his inflamed manhood, but soon the smile was wiped from his face as he realized Courtney was still engrossed in the conversation with amber. She looked down at him seeing him looking at here with his puppy dog eyes.





“I bet that feels really nice. I used some Heating Gel to relax your muscles.” Courtney said to Alex as she paused  her conversation.





“It really burns.”





“You're overreacting that stuff feels so nice. I put it on myself all the time after yoga.”  



Courtney just continued to stroke his penis with the same enthusiasm she had before as the gel turned into a burning inferno on his sensitive testicles. Each stroke was like a hot knife sliding across his skin. Alex’s hips bucked as he tried to escape the pain, but Courtney’s grip remained firm, mistaking his squirms for pleasure.



The burning sensation grew more intense with each passing moment, radiating from his balls up to the base of his cock. He felt like the gel was sizzling against his skin as if someone was holding a lighter to his most sensitive bits. The room felt spun around him as he tried to focus on Courtney, her words a distant echo through the haze of agony. She was once again chattering away to Amber, completely oblivious to the torture she was inflicting on him. The skin of his scrotum was tight and red as the pain grew to a crescendo. Alex had finally had enough as he grabbed Courtney's hand throwing it off of him as he went into the fetal position unable to stop the intense feeling. He looked at Courtney pleadingly just hoping she would realize the gravity of the situation this time. He moved his hands to show her his penis and balls but Courtney only giggled at the sight of his throbbing shriveled red junk. 





“It seems like you don’t even want to cum.” Said Courtney as she stood up frustrated turning around and storming out. "Yay, Sorry Amber. Alex is just being weird again.”





Alex watched in despair as Courtney’s perfect ass swayed away from him, her panties clinging to her teasing him with the promise of pleasure that had been snatched away once again.