Ron Ch. 05: Date with Courtney

Courtney at Home

Courtney Summers stood naked in her room admiring herself in the mirror. Looking back at her was an oval faced very young looking girl with large blue eyes, a small well shaped nose, and a wide smile with braces. Her 4 foot 10 frame and smoothly shaved pussy enhanced the illusion of youth but her slim waist, and modest breasts gave away her actual age of 18. She squeezed her breasts and rubbed her nipples into hardness as she turned to admire her firm, nicely shaped butt. Slapping it, she tried to see the double dimples that decorated her back but failed. She knew they were there because some guys would comment about them and kiss them. She could see them in dressing room mirrors designed to give back views. The whole youthful looking thing had been a powerful weapon in the dating and sex wars in high school. Her small size had also made her a key member of the cheer squad where she was always the one on the top of the pyramid and being tossed high into the air. Now that she had graduated she was wondering if she could use them to get out of her parent's house and on to her own.

She had just returned from a sex party which had been partially arranged by a former cheerleader friend, Sarah. She alternately tugged and pushed at the metal cherry ornament which hung from her clit hood while she reflected on the party. There had been some older guys there, including the father of her cheerleader buddy. He had a big cock and huge balls. She started to get off on her masturbation as she thought "I gotta get me more of that." She closed her eyes and recalled his cock driving inside her doggy style as his balls slapped against her clit. The thrill of orgasm pulsed through her body. She bent over to keep her balance and stifled her squeals so her mother wouldn't hear as she rubbed directly at her clit to increase the pleasure past the point of being bearable. She loved it when guys kept stimulating her while she orgasmed, though few of the younger guys she had sex with knew even how to do it. Sarah's dad sure did.

She took a few deep breaths and, resisting the urge to lay down on her bed, she pulled the bands off her youth enhancing, double pony tails, shook her hair free and headed down the hall to shower, half hoping her younger brother or maybe one of his friends would see him. She luxuriated in their stares when they saw her naked. She often considered whether to pull one of them into her bedroom for a few minutes of pleasure. She had done that with her older brother's friends when he was still at home, She still got calls from some of them for dates, usually when they were between girlfriends. Breakup sex was often really great as the guy would work out all his sexual aggression and anger and sense of loss.

In the shower she reflected on her upcoming date. She didn't know all the details but the sex party had been at the home of two cousins while their parents were away. One of them, Ron, was supposed to be a virgin but she doubted it because he sure knew his way around a girl's sex parts. He was real young looking like she was and he had been so cute. From the time she got there he was clearly taken with her. She was sure it was because she looked young like him. She could imagine that being young looking might make it harder for a guy to attract women but he didn't realize how being young looking made girls extra attractive to guys. Their experiences with the opposite sex were miles apart. He may have known about a girl's sex parts but was tongue tied when it came to conversation.

Ron had managed to ask her to stay the night with him and she had declined. Putting him off until today with a promise of doing something other than sex. She had hoped that he might forget, but he hadn't, even though he had spent the night with another girl at the party while Courtney had participated in an orgy with the other guests. She once again remembered Sarah's dad fucking her with his big cock and her fingers involuntarily penetrated her vagina. Ron had a pretty big one himself and big balls too. Tonight could be a lot of fun.

Her mom caught her as she returned to her room, Courtney! I've asked you to wear something out here. At least a towel."

"Oh mom, it's just a short walk."

"What if your brother or one of his friends see you."

Courtney looked at her and smiled with a twinkle in her eye.

"Was that a wink?" her mother thought, exasperated. Courtney's grades hadn't been good enough to get into college and she didn't seem interested in junior college, or any vocational school. When she and Courtney's father asked about what she wanted to do or told her to look for work somewhere, she'd say things like, "I understand there are legal brothels in Nevada. I need airfare." Her mother didn't know if she was serious or just trying to get a rise out of them.

"Too bad it was my mom and not Larson," she thought of one of her brother's friends. He had seen her naked once and she had stopped in front of him asking what he was looking at. She chuckled to herself as she remembered the outline of an apparently large organ making an increasingly larger bulge in his pants.

She had a couple of hours until her date so she threw on a pair of shorts and a tank top and went outside to sun herself and chat with some friends. The first thing she did was text out a picture she had taken of her cheerleader friend's dad's package with the caption, "look what I had last night."

She watched in satisfaction as the responses came back. One of her friends, Jennifer, had also been at the party and texted into the discussion, "I had some of the same. Nice inside."

Courtney had also taken a photo of Ron's parts and sent that out with, "Look what I get to play with tonight."

Courtney and Jennifer

Jennifer began a private conversation, "When you picking me up." Courtney was driving on the date and Jennifer had taken advantage to arrange some private time with David, Ron's cousin, while Courtney and Ron were out. Courtney suspected that Jennifer was hoping for some fuck time with Ron. Jennifer had also been a cheerleader and was a well built brunette. David had jumped at the chance to be alone with her. Courtney didn't realize something Jennifer knew: that David also "knew his way around a girl's sexual parts". Both David and Ron had been well tutored about this by Sally. Sally and David had been nerdy types at Courtney's high school, outside of Courtney's circle. At the party she barely recognized David and knew Sally only as as a girl who had gotten on stage and given a speech during graduation.

At the party they had "joked" about having a threesome with Ron but both knew they wanted it. So, a foursome with Ron and David could be in the cards for tonight. Ron was the prize but Courtney knew David would do just fine.

Courtney and Jennifer arrived at David's house around 5. Courtney had tied her hair into a single ponytail with a lace bow augmented with thin curled ribbons. She wore a pink cashmere top that was intended for girls without developed breasts and no bra. The shape of her bosom was clearly apparent as was a hint of nipple. She had a bare midriff below which she wore a pair of brief denim shorts, fashionably distressed, with the top button unbuttoned.

Jennifer always wore her hair brushed straight. She wore a white cotton, scoop neck, tank top. The top of a sky blue bra and substantial cleavage were on display. Loose fitting, floral print shorts completed her outfit.

David answered the door. "Hello girls." His mouth was dry from anticipation and the sight of the two wasn't helping his ability to talk. His voice got raspy, "Ron's still upstairs. He conked out from last night's fun and hasn't reappeared."

"I'll get him up," Courtney smiled, thinking that she'd now have an upper hand all night since he hadn't even been anxious enough to be awake for her.

Upstairs she found him asleep on his back, a flesh colored sausage draped over his left thigh and his wrinkled scrotum dangling between spread legs. The sausage showed the outline of a penis head through the foreskin that ended in a half inch long pursed tube. She knew exactly how she wanted to wake him, but, "which parts to begin with?" she thought and concluded, "I know! BOTH!" Gently sitting at his feet she cradled his balls in one hand and lifted the end of the sausage to her lips with the other. She flicked away at the dangling foreskin and the head moved upward, stretching it wide. As the head appeared, she engulfed the entire organ in her mouth while squeezing his balls up into his abdomen. The cock rapidly expanded and didn't fit all the way in her mouth for long.

Ron woke as she sucked his dick and quickly realized what was going on. He did his best to stay still and allow her to continue the action. But the constant movement of her tongue around the head of his penis caused him to gasp.

"I know you're awake." She pulled her head away and his cock audibly popped out. "You know it's pretty insulting for you to sleep through the time for our date."

"I was tired,' Was his weak response.

"Yeah, I know, it was that slut Kate. I could taste her pussy on your prick. I'm tempted to leave."

Ron protested with meaningless sounds, "uhh, no, bu.. no I, I'll."

"Go shower. get that slut's taste off. Be quick. Or I will leave," she chided playfully.

He rose and rushed out, but not fast enough to avoid her playful, but firm, slap on his bottom.

She took advantage of his time out of the room to look around in the dresser. Finding his underwear, she admired the collection of superhero briefs, though it wasn't anywhere near as extensive as her "My Little Pony" and "Care Bear" panty collection. She selected a blue pair with the Superman logo for him to wear.

Fun Castle

The two of them left for Fun Castle, a mini golf, go-kart, and arcade a few miles away that Courtney had suggested. They stopped at a local burger place on the way, "Fun Castle food is barely fit for dogs," she informed him.

Immediately on arrival Ron got a hint of why Courtney liked the place. Everyone there seemed to know her and he caught looks of jealousy from a couple of the guys. She had a tendency to play skee-ball in the most provocative manner possible. And Ron imagined that there would be a lot for the guys to see if she wore a short skirt instead of the shorts. Even with the denim she managed to show a nice, soft looking mound between her thighs. Her tight top, no bra and her iced drink rubbed against her chest, "I'm hot," brought hardened nipples into full display.

She was skilled on the mini-golf courses and knew exactly where the secluded areas were. She had this tendency to expertly flip the ball off the course to just the "right" spot. "Help me find that ball," she'd tell Ron and he'd follow her into an area where no one could see and she'd flash him or fondle his cock before picking up the ball and returning.

There were a few holes where she offered a bet on who would win, "loser does what winner asks." Ron had trouble hitting the ball straight and she never shot above par except when she intentionally went off the course. Those holes she bet on always had a very secluded spot or maybe a door into one of the decorative items. Ron never minded losing since she would ask Ron to lower his pants so she could suck him off or ask him to massage her tits or clit.

After soundly beating him on two of the courses, she suggested the go karts, "whoever wins decides what we do the rest of the evening." She let him have the lead car and zipped right past him on the first lap. "Best 2 of 3," she offered and this time he managed to hold her off for one full lap.

"Well, maybe that's not fair," she said, "since you aren't familiar with the track." She told him they'd forget about those two and do one more race for the night's winner. "This time I'll get the last car and you take the first."

There were eight other drivers so that put her well behind and he had learned enough to successfully hold off any other drivers simply by keeping to the inside of all turns and the accelerator floored, except in two spots he had learned were spin out spots. He was feeling good. Two guys had passed him, one by nudging through on a turn where he had let up on the accelerator and the other who had picked the fastest car went by on a straight section. But then he went ever so slightly wide on a turn and a ponytail tied with lace left him in the dust.

She was laughing as they got out of the cars. "I guess I get to call the shots," she laughed, grabbing his hand.

Ron let her lead him into the arcade where she went to the prize section and asked the guy behind the counter for an "adult grab bag."

"Gotta be 18, young lady."

"Gawd, Gordon, don't be a prick. You know I'm 18."

"Gotta have ID. Company rules. No ID, no adult prizes."

"Will these do?" To Ron's surprise, she lifted her shirt, exposing her breasts.

"Let's see." The clerk reached over the counter and fondled and massaged her. "Yeah, those feel like 18."

He brought out a large canvas bag and Courtney felt around inside. She pulled out a small box and dropped it back in. After feeling around again she pulled out a box she was satisfied with. "Two, Gordon?"

"Sure. two."

She felt around again and pulled out another, slightly larger box. "Nice. And I had enough for a couple from the yellow bag."

Gordon presented her with a smaller yellow bag and she extracted two condoms from it. She showed Ron, "Strawberry and Chocolate over your banana, yum!"

Gordon put her prizes in a small plastic bag, "You know a lot of girls under 18 have nice tits. I think next time you can't show your ID I'll have to probe your cute cunt to be sure you're 18."

"In Your dreams," Courtney smiled and turned away.

"With the big probe," Gordon said. And then to Ron, "Have fun, fella."

"What was that?" Ron asked as they walked to the car.

"Gordon and I like to kid around."

"But you let him touch you."

"Oh, so what. Part of the game. he's touched more than that."

"The big probe?"

"His cock? Yeah, not so big. He's been inside me, so have most of the guys that work there."

"Doesn't the owner object? How can you keep it hidden?"

"What makes you think the owner isn't one of the guys I was talking about? They are pretty careful about other customers seeing. 'Probing' with the big probe, or any of their ten smaller ones, is usually done in the back. The 'big probe' is good for special prizes." She smiled slyly.

In the car, Ron asked, apprehensively, "Going to the beach?" because Courtney had mentioned sex on the beach or in a public park as one of the things she might decide to do.

"No, maybe a cemetery. More private at night."

She laughed at Ron's expression, "Kidding you." She smiled. "Beds are much more comfortable. Don't you think?"

"Yeah," Ron said, relieved.

"And better for what I have in mind."

Ron wondered what that might be. He had limited sexual experience. With Sally who had introduced him to sex only a week ago. Then the party with eight beautiful women. The penile/vaginal action at the party had been more just stimulation than actual sex. Kate after the party had been real sex, more so than with Sally who was acting as an instructor. In a sense Courtney would be only his second real sexual activity. She was so much more experienced, he thought.

She drove carefully, even compulsively, hands on the wheel, eyes ahead at all times. Her friends often kidded her about it. At the first stop light she did squeeze Ron's privates and move his hand to her thigh at the hem of her shorts. Ron took the hint and caressed her thigh, occasionally slipping his hand inside her shorts to her crotch. She massaged his cock at the two red lights they encountered and he was ready for action when they pulled up in front of the house.

Back at Ron's aunt and uncles house, Courtney took a modest sized duffle out of the trunk. Ron thought it might contain a change of clothes except for the sound of hard objects hitting against each other.

No one was downstairs. "Probably upstairs fucking," Courtney proclaimed. The idea of anyone, let alone his cousin fucking the stacked Jennifer, further stiffened Ron. As if thinking about Courtney weren't plenty. Ron turned out the hallway lights and they peeked into the master bedroom. It was dark and quiet but there was a clear mound under the covers. "Must have worn themselves out already," Courtney whispered. "No staying power."

"It's been almost three hours." Ron wondered if she really did expect to keep up vigorous sexual activity for that long. Ron already felt so aroused that he wasn't sure he could go three minutes without shooting his load.

"No staying power," Courtney re-iterated mostly to needle Ron.

"You're pulling my leg," Ron surmised aloud.

In response, she flashed her braces in a wry and cryptic smile.

Courtney in charge

They went into the guest room where Ron was staying, "Get naked," she told him and he complied, though she stopped him so she could remove the Superman briefs herself, first kissing the tip of the hard staff that poked out of the waistband. Then she fondled it and the constrained balls. She eased the elastic down, kissing each inch as it was revealed. "You do have a fantastic set," she told him as his genitals were totally free. She sucked away at the cock and batted at the pendulous scrotum before pulling the briefs to his ankles and telling him to lie down on the bed, "On your back," she directed.

She pulled some velvet cuffs with attached rope from her bag. Ron was soon spread-eagle on the bed, his arms held by ropes attached to the headboard, his legs by ropes to the bed legs. "Only bondage," Courtney explained. "I'm not at all fond anything that hurts." A large, soft feather was next out of the bag and she gently tickled his entire body with it, paying special attention to the tip of the iron hard staff that extended vertically from his groin.

He moaned louder and louder in pleasure. She put the feather aside and knelt over his chest. Removing her top she presented her nipples to his mouth so he could kiss and suck at them. "Let's see what you can do with this," She exclaimed, standing on the bed and slipping off her jeans to show a pair of panties emblazoned with a teddy bear wearing a rainbow on its belly. "Cheer Bear," Courtney told him, "to cheer you up." With a smile she rubbed her soft cotton encased crotch in Ron's face.

Her panties got damp and then wet. She stood and removed them to show soft, fleshy major labia with a pair of triangular small labia protruding from the slit. "Time for my new toys." She jumped off the bed and returned wearing a rubber glove, carrying the vibrators she had pulled from the "grab bag", some K-Y and what looked like a tiny condom. She resumed her spot kneeling on his chest. He could feel the dampness leaking from her vagina. She put everything on his chest so he could watch. "Finger protector," she said of the small condom and tucked the tiny vibrator inside. She coated it with the jelly. Then, taking more jelly on her finger she turned around, lubricated his anus and shoved the vibrator all the way in. The rubber glove was turned inside out and placed on the end table. She turned the vibrator on and Ron gasped with the sudden shock of pleasure. "That works," she laughed.

Then she took the clit stimulator and strapped it in place. "Now," she said. "I think this'll work best with something hard and warm." Holding the stimulator out of the way she positioned herself over his cock and lowered herself. She loved the feel of a large, warm dick penetrating her. First the tip rubbing against her clit, and spreading her labia. Then the shaft sliding in, rubbing against her vaginal walls. The tip reached her cervix, slid to one side and began stretching her vagina to twice it's usual length. The whole shaft filled her and her clit rested against his pubes. He smiled and moaned in pleasure. "God, that feels good, doesn't it?" she asked him, leaning in and giving him a big kiss.