This is a little story about love discovered between Jack and Diane. They grew up as neighbors; only a few houses separated them from each other. Jack was the typical neighborhood boy, all rough, tumbled, and getting in trouble with his friends. Diane, on the other hand, wasn’t your typical girl. She was right out there with the boys getting in trouble with the boys, much to her mom’s chagrin.
As they matured, Jack grew into a high school sports star. All hard-bodied and handsome, attracting the girls around school like bees to honey. Diane filled out as well. She developed into a very beautiful young lady with full breasts and a trim figure. The problem was as all of her girlfriends were going out for cheerleading, Diane just didn’t have that urge. Instead, she played sports and carried on her tomboy ways.
Jack and Diane hung out all the time. They ran together, exercised together, played basketball together but never found that spark that ignited their relationship beyond the close friendship they had. That was until the day Diane showed up Jack’s to find him crying his eyes out.
Diane walked over and sat on the bed next to him and asked, “What’s wrong, Jack?”
Jack sniffing back tears, said, “Marcy broke up with me. She wanted to go out with Troy instead.”
Diane kept her thoughts to herself but couldn’t help thinking, That figures that dumb slut would dump Jack for that neanderthal! Although Diane was into sports and a tomboy, she was also one of the smartest people in her grade, so she earned money on the side tutoring. One of her best clients was the neanderthal.
Diane reached out and caught Jack’s chin and lifted it until she was staring into his eyes. She realized she had never noticed how bright his blue eyes were. They were deeply intoxicating to stare in to. Without thinking about it, she leaned forward and kissed Jack while staring into those tear-filled eyes. Jack, caught completely off guard, tried to pull back, but Diane held onto his chin a little harder.
She brought her lips to his again, but this time pressing them harder to his. Jack responded without even thinking by opening his mouth and letting his tongue trace her lips. Diane parted her lips and let Jack’s tongue slip in until their tongues were dancing back forth. By this time, Diane had let go of Jack’s chin and instead had wrapped her arms around him, pulling him to her.
Jack wrapped one arm around Diane, pulling her closer as well, but it was the hand on the other arm that was about to set them down a path that would forever change their lives. His natural reaction with Marcy when making out was to cup her breast and rub her nipple through her shirt. This would always cause her to moan with pleasure and if he was lucky, get him rounding second and maybe heading for a triple.
Although he and Marcy had never crossed home plate together, they had progressed to exchanging oral pleasures. He always enjoyed it when Marcy would suck him off but enjoyed it, even more when he got to nuzzle his face in her hairy pussy. He wasn’t sure why but teasing her had always been more fun for him.
So, Diane’s first moan didn’t surprise him as much as the voice that emitted it did. It brought him back to it was Diane’s breast and nipple he was massaging. Her breast felt so soft, and her nipple was getting harder by the second. He also realized that he wasn’t feeling a bra either. Diane was sitting here braless, making out with him. The shocks just kept coming.
The next shock was Diane placing her hand on his crotch and flexing her fingers over his already semi-hard cock. She traced the bugle that was forming in the shorts he had on. This caused him to let out his very own moans. She applied slightly more pressure each time she traced his shape, and each time it got just that much harder.
All thoughts of Marcy were truly gone one he moved a hand to the crotch of her shorts. He cupped his hand against her mound, rubbed lightly. Diane let a protracted moan escape at the same time she pulled back from the kiss.
Jack, thinking he may have crossed the line, started to pull his hand away, but Diane caught it in hers and pushed it back against her cloth-covered pussy before saying, “Don’t stop!”
Well, Jack didn’t need any more of an invitation. He shifted around to give himself better access to her. In doing so, he also pushed Diane back on the bed, so her bare legs were hanging over the edge. She was still half sitting on the bed as he ran his fingers along her covered pussy. She opened her legs wider for him.
He leaned closer and gave her another tongue dancing kiss as he slipped a hand under the leg of her shorts. As they kissed, he slid it into her crotch until he was toying with her pussy through the thin material of her panties. He could feel how wet she was becoming as he slid and pushed his fingers against her.
He let his fingers catch the edge of her panties and pulled them to the side as his fingers slid across her now bare pussy. She gasped and then moaned into him as they continued to kiss. Taking this as approval, Jack ran his fingers along the full length of her bare pussy. He could feel the stickiness of her juices on them.
Slipping a finger into her, she let loose of a loud moan and threw her head back, breaking their kiss. He could see and feel she was enjoying what he was doing but at the same time. Yet he was afraid she would stop him at any moment. Watching her face, he kept sliding that single finger in and out of her. The look of pleasure and need on her face left him to hope she wouldn’t stop him.
Feeling more confident, he slid off the bed and knelt between her legs. He had pulled his hand out of her shorts and now reached up, catching the bottom hem of her short’s legs. Starting with a little tug, he started pulling her shorts off. He was hoping he wasn’t going too far, but she eased that fear by lifting her ass up so the shorts would slide out from under her. Surprised and delighted, he pulled them all the way down her legs slipping them off over her bare feet after she kicked her sandals off.
After dropping Diane’s shorts to the side, he turned back to see her in a pair of light blue cotton panties with a huge wet spot spreading over them. He couldn’t resist leaning down and running his tongue over the wet spot causing her to moan even louder. He licked back and forth, feeling her swelling lips of her pussy under the cloth.
Diane had given up on trying to propped up and had laid back on Jack’s bed. As he licked her panties, she let out ever louder moans and had balled her hands up in his blanket. She had only had one guy go down her before, and he was clumsy and crud in his efforts. Jack was proving to be much better skilled so far.
Wanting to taste her flesh, Jack grasped Diane’s panties and pulled them down. He slid them off, but before dropping them on the floor, he took a big whiff of them as Diane watched. He smiled as he dropped them to the floor and bent his head to her pussy.
He ran his tongue over her smoothly, shaving mound marveling at the difference of it compared to Marcy’s hairy one. He decided he much preferred this as his tongue traced the smooth out lips of her vagina before darting between them, quickly tasting her nectar.
Diane rolled her hips up to meet his tongue and cried out for more. She moaned uncontrollably as he darted his tongue from her depths to her clit and back. She had a death grip on his blanket each time he twirled his tongue on her clit. She thought, sweet Jesus, this feels fucking great!
All Diane’s actions did was encourage Jack to tease and pleasure her pussy more. He had moved his mouth over clit that had become swollen and jutted out from under its little hood. He sucked it gently before licking it roughly, keeping up the varying pressure and sensations. As he teased her clit, he slipped two fingers into her pussy, pumping them deep and hard.
Oh my god, I’m going to cum soon, raced through Diane’s mind just as Jack sucked greedily on her clit and pushed a third finger into her pussy. She was crying out in pleasure and asking him to let her cum. He wasn’t listening until she screamed out, “I need to cum, damn it!”
Jack upped his efforts to make her cum and was rewarded with a howl from her that had to be heard all the way down the street. He had her clit between his lips when her orgasm started, and she closed her thighs around his head, crushing him. She also threw her legs over his back, holding him to her as her orgasm rocked her from the tips of her toes to the ends of her blond hair. He thought, damn, Marcy never reacted like this on her wildest nights!
Diane finally started to relax, and Jack was able to pull away. He just scooted back, still kneeling on the floor watching her recover from what he thought was a very intense orgasm. Little did he know that was the strongest orgasm she had ever had in any way, shape, or form. She was still panting, trying to catch her breath.
When she finally recovered, she sat up and scooted to the edge of the bed. Jack had already stood up, and she reached for him. His bulging cock was obvious in his shorts. She caught the waistband of his shorts and tugged him closer. As he got closer, she could see just the smallest dark spot on his shorts.
As he came to stand right in front of her, she slid off the bed to her knees. Once on her knees still, with the waistband of Jack’s shorts in her hands, she pulled them down swiftly, taking his underwear along too. His cock sprang out in front of her, and she let an audible moan escape from her.
She had only been with a few boys, but she knew a nice cock when she saw one. In her opinion, Jack’s was the nicest she had seen so far in her young life. She wrapped her fingers around the shaft and felt how hard he was. He moaned out at the feel of her touch.
As he watched, she stroked her hand back and forth along the length of his cock. Taking her other hand, she palmed his balls, fondling them. Jack thought, Jesus Christ, don’t let me cum too quick! He didn’t need to worry about that; Diane was going to enjoy him before she let him cum. Where was the only question mark for her?
Looking up at him, she said, “Sit down in the bean bag, so your ass is on the high part.”
She let go of him, and he turned around, sat on the big bean bag he had in his room. He did as he was told and sat backward on it to keep his ass higher than his head. As settled onto, he watched Diane crawl over to him. As she got closer, she moved between his legs and pushed them apart before grasping his cock in her hand again, causing him to let loose with a low moan.
She scooted close to the bean bag, so she was partly lying on it as well. She started stroking his cock again with gentle strokes, feeling him harden even more in her fingers. Laying the way, he was able to watch her. In no time, his cock was rigid in her hand. She could feel the pulse of his blood filling it.
It wasn’t long before Jack could do nothing but moan with each stroke. It was then that Diane bent down and took his head between her lips, sucking it gently. This sent Jack moaning even louder. Diane just kept working her lips further over his cock with each gentle suck she made until Jack was three-quarters of the way in.
Diane had moved her hand to the base of his cock. She was still stroking him softly as she started working up and down his cock with her lips. As she moved up, she would snake her tongue along the shaft. As she went back down, she would let her lips glide the length of his shaft, taking him as deep as she could. She hadn’t learned about deep throating yet, but she had him touching it each time.
Jack moaned and thrust his hips up to meet her each time. He could feel his orgasm building the longer she went. He had never had Marcy give him such an amazing blow job. She was always quick and never let him cum in her mouth. He moaned; he was close. He didn’t want to just explode in Diane’s mouth and make her mad.
Diane heard him and worked his cock even harder. She even gripped his balls in her other hand, rolling them around the best she could. They had gotten so tight in his excitement. She felt the pulse of his impending orgasm in the base of his cock and decided then she would let him cum in her mouth. It would be a treat for him and her.
“Oh god, I’m cumming,” Jack moaned out loudly just as the first spurt of cum coated the inside of Diane’s mouth.
Diane held him in her mouth tightly but had let him slip most of the way out so she could hold his cum. He filled her mouth until she looked like a squirrel hoarding nuts in her cheeks. When he had finished, she pulled her mouth off of his cock. Looking down at Jack, she opened her mouth so he could see his cum filling it fully before closing it and visibly swallowing his cum down.
Jack just stared at her, astonished that she had done that. Marcy would’ve been spitting it all over him. In fact, the one time he hadn’t warned her that he was close, that is precisely what she did. He thought, what a difference between these two.
After a moment’s rest, Diane stood up and offered Jack her hand. She gave him a tug until they were standing facing each other. Him with her dried cum on his lips and her with his fresh cum still on hers. Without a moment’s hesitation, he leaned forward and kissed her. She kissed him back and then opened her mouth for his tongue as he opened his for hers.
They were both contemplating where this was going next when they heard a shout call, “Jack, where are you? I need help with the groceries.”
They both jumped at the sound of his mom’s voice from downstairs and quickly scrambled for their shorts. He was able to slip his on, underwear and all. Diane had to settle for just getting her shorts on because she couldn’t find her panties. Jack would find them later under his bed.
By the time they made it downstairs, they were both flushed from hurrying, so their post-sex faces weren’t as noticeable.
Jack’s mom looked at Diane as she came bouncing in with Jack and said, “Hey there, Diane, you and Jack having fun with something?”
Jack about died on the spot, and Diane just coyly replied, “He was helping me with biology.”
