Jack and Diane’s relationship flourished after the ice was broken on that infamous afternoon in Jack’s room. Jack forgot all about Marcy, and Diane hadn’t been in a permanent thing with anybody. As their sophomore year ended, they found their relationship heating up to ever hotter levels. They stole all the time they could to spend together and spent as much of it as they could to continue their fun that started in Jack’s room that faithful day.
The thing they never seemed to accomplish is getting Jack across home plate. Diane was determined to make it happen this summer, and since Jack’s birthday was coming up soon, she wanted that to be her gift to him. He was being the perfect gentleman; she always knew he was by never trying to rush home plate. It just fed the love she was feeling for him, making it even deeper.
So, when Diane found out her parents were planning to take a trip in a few weeks, she put a plan in motion to surprise Jack. She cleverly looped in Jack’s best male friend to help with her plan. Coincidently he was also one of her closest male friends. They spent the next few weeks getting all the details set up and getting the plan in motion.
Of course, Jack knew about Diane’s parents’ trip. He spent as much time at her house as she did at his. Diane knew there was no hiding the trip, but she had to put Jack off on his hints to play house together that weekend. Besides, his parents knew about hers going away, and she was pretty sure they wouldn’t let Jack just disappear to her house to be alone with her.
So, about halfway through the week before her parents were leaving, she told Jack that she was going to her aunts for the weekend. He was disappointed but knew he could go with his friend for the weekend. He knew he’d miss Diane but knew he’d have fun all the same.
When it was all said and done, Diane patted herself on the back that the plan was working. Jack’s friend would pick him up Saturday, and then the plan was in motion. Know she only had to find the right things to wear for Jack. She was as excited for the weekend as much for herself as the gift she was giving Jack.
For Jack, the end of the week was a little depressing because Diane would be gone to her aunts. Also gone was their chance to be alone and his chance to hit a home run with her. Of course, he would never let her know he was disappointed but disappointed he was. He’d go hang out with his buddy for the weekend. At least then, he wouldn’t have his mind on how bad he was missing Diane or the lost opportunity.
Diane busied herself, getting as much ready for their weekend as she could and not be obvious to her parents or Jack. She bought some sexy lingerie in a couple of different styles. One of her girlfriends covered for her while she went shopping. The hardest part was the drain it had on her bank account. She would never have guessed clothing that covered so little would’ve cost so much. She suffered a harsh fashion lesson. She only hoped Jack liked what she had bought.
Friday came too quickly for both of them. Diane was down at Jack’s as usual. She kissed him goodbye and said she’d see him Sunday night. She left to go home to see her parents off, and as far as Jack knew, to pack to go to her aunt’s house. This left Jack feeling a bit down for the rest of the evening. Even hanging with his buddy, the next two days wasn’t cheering him up much.
Jack’s buddy called Saturday morning and told him they couldn’t leave until about one that afternoon. Well, all Jack could say was okay because he sure didn’t want to hang around home without Diane. So, he moped around until his friend showed up.
Piling into his buddy’s car, he said, “Whew, I didn’t think you’d ever show up.”
“Well, I did, but bad news, I have to stop at the mall on our way out,” his friend replied.
Jack just groaned at that news as they pulled away from the house.
Pulling into the mall parking lot, Jack’s buddy pulled over by the cinema that wasn’t open yet stopped. Jack was just about to ask him what the hell he was doing when there was a tap on his window. Jerking his around, he saw the smiling face of Diane looking at his startled one.
Jumping out of the car, he asked her, “What are you doing here?” over the laughter of his friend.
“I thought I’d surprise you with a little weekend of fun. You okay with that?” she said, smiling.
“Hell, yes, I am, but what about dingbat there,” indicating his buddy? “We were going to hang out until tomorrow,” he replied.
She leaned in and winked at him and said, “He has other plans until I bring you back here tomorrow at noon.”
Leaning over so he could look up through the passenger side of the car, he replied, “I sure do. I won’t be seen around here, so you are safe to hang with her. Have fun, buddy,” with that, Diane grabbed Jack’s bag from the back seat. She then closed the door, and he drove off, leaving them standing there.
“Okay, let’s get out of here before somebody sees us. My mom’s car is over there,” she pointed, indicating the other side of the cinema.
Jack, still playing catch up, started following her as he said, “Where are we going?”
Diane looked back over her shoulder and said, “My house, I only told you I was going to my aunts so I could surprise you. When we get back to the house, you’ll need to scrunch down until I pull in the garage, though.”
By this time, they had gotten to the car. They climbed in, and Diane headed towards her house. She made sure to come up the street the opposite way from Jack’s house just in case. Jack scrunched down as they rolled down the street and got in the garage.
After they got into the garage and got out, Jack came around and grabbed her before they made it in the house. Squeezing her hard, he asked, “So, what is the plan now.”
She wiggled in his grasp, trying to get away but gave up and said, “I have a few movies for us to enjoy, a nice dinner planned, and the rest you’ll just have wait to see,” finishing it with a peck on his nose.
The rest of the afternoon was spent watching a couple of movies and some heavy petting. Anytime Jack tried to stretch a single into a double, she shut him down. He got plenty of chances to feel her up and knew she had no bra on, but she would get off his advances as he tried to go deep.
After the second movie, she felt horny then hell herself, so she knew he had to be too. Yet she still avoided his advances on second base by getting him into a PlayStation game they both loved to play. As he settled into playing, she told him she was going to fix dinner. She also told him he needed to change into the clothes that were on her bed before dinner.
He’d been playing for a while when he heard her yell, “Go change and then come back out to the living room.”
He reluctantly saved the game and walked back to her room. When he walked in, he saw a pair of his slacks and one of his nice polos laid out. There was also a note lying on top of the clothes.
He picked up the note and read it,
Don’t worry about socks, shoes, or underwear. Go commando for me tonight.
His first reaction was to read the note a second time, and then he wondered to himself what she had planned. But doing as instructed, he got dressed sans socks, shoes, and underwear. As he moved back out to the living room, the slacks rubbed his cock and balls ever so softly. He thought it felt good.
A few minutes after he returned to the living room, Diane breezed through still in the shorts and t-shirt she had been. He heard her go into her room and then cross over to the bathroom. Listening, he could hear the shower come on and just as quickly go off. He was tempted to go back to the hall but thought better of it, not knowing what she had in mind. Yet his cock did give off all the signs of desire, knowing she probably was naked in the bathroom, and they were alone. He behaved though and stayed on the couch channel surfing the TV.
A short while later, Diane came back out into the living room wearing a small black dress, no shoes, and her blonde hair cascading down her shoulders. Jack sat there in shock. He took her in and thought, oh my god, she is beautiful, I’m so damn lucky!
After a full minute of Jack, just staring, she finally said, “Do you like?”
“Hell, yes, I like! You are freaking gorgeous, Diane,” he exploded out.
Twirling around before stopping and looking at him again, she said, “Thank you, Jack. You look pretty good yourself,” winking at him.
After another moment of them staring at each other, Diane finally said, “Let’s eat before it gets cold.” She offered Jack her hand.
He took it, and she gave him a little tug as he stood up. She led him to the dining room, where she had a beautiful meal laid out for them. She sat him at the end of the table, and she sat next to him on the side. The whole time they ate, she alternated, running her foot up the inside of his legs. She never quite got to his crouch each time, but by the time dinner was over, she could feel his hardness tenting his pants nicely.
After dinner, she left everything on the table and led him back to the living. She had him sit on the couch. He tried to pull her down with him, but she slipped away. She was now standing a few feet from him.
While looking at him, slipped one strap off her shoulders at a time until she was holding her dress up with one hand. She then let it slip to the floor around her feet, leaving her standing there in a sexy matching white bra and panty set.
After standing there a few moments showing herself off to Jack, she asked, “Do you like this better than the dress?”
Jack, who had gone slack-jawed and instantly hard, could only gape at her with his mouth open. He had never seen her in anything other than the simple bras and panties she wore. He had to admit she looked great in them, but this was a whole different level.
Finally, able to speak, he said, “Oh my god, Diane!” he just couldn’t get any more out.
“I’ll take that as a yes,” she said.
She walked over to Jack, swaying her hips from side to side until she was standing right in front of him. She could see his cock damn near tearing through his slacks; he was so hard. Seeing this, she knew she’d have to slow him down if the rest of the night was going to work out.
He reached for her, and she slapped his hands away and instead dropped down until she was straddling his lap. She could now feel his hard cock pushing up into her crotch as she wiggled over him. He brought his hands back up, and she let him hold her at the waist.
As he held her, she worked herself back and forth over his covered cock. He had started moaning the longer she did it. It was only with great will she wasn’t moaning as well, but she could feel the wetness on her skin from her own juices already leaking from her pussy.
Jack leaned forward, trying to move his hands up her back to unhook her bra. She leaned away from him, causing his hands to slip away before saying, “Enjoy lover, just enjoy.” Jack let out a moan that was part in frustration and part in desire.
Seeing she couldn’t tease him much more, she grabbed the bottom of his shirt and started pulling it up his body. As she pulled it up, covering his face, she leaned forward and sucked first one and then the other of his nipples. She had never done that to him, and he just about bounced her off his lap on surprise.
As soon as the shirt uncovered his face, he said, “Damn, girl, that was a surprise and felt great.” She just smiled, placing her hands on his shoulders before leaning forward and taking a nipple in her mouth again, giving it another long suck. Jack moaned out louder.
After releasing the nipple, she looked down and could see a wet spot on his slacks. She honestly couldn’t say if it were him or her creating it. It didn’t really matter after all. After teasing his nipples a little longer, she slid off his lap to the floor, kneeling between his legs.
She reached for the button on slacks and slipped it open. Then as he watched, she pulled the zipper down, releasing him from his cloth prison. His cock sprang out like a Jack-in-the-box or, in Jack’s case, a jack-in-the-slacks. She audibly moaned at the sight of his hardness. She thought he was harder than she had ever seen him.
Grabbing his slacks on each side, she tugged at them. Jack getting the hint, lifted his ass off the couch, and she was able to pull them down his legs until she had them removed. She just tossed them to the side before turning her attention back to the nicest cock she had ever seen.
She slipped her hand around Jack’s rigid cock. She knew from them playing around so much as hard as was; he wouldn’t last long. She was okay with this because she really wanted to get to the rest of the evening with a less excited Jack or at least a less excited jack-in-the-slacks.
She started slowly stroking his cock in small movements. Reaching under him, she also slipped a hand around his balls to fondle them. Jack moaned at her attention but let out an even louder moan as she dipped her head over the tip of his cock. She licked down the shaft until she got her hand. Letting go of his shaft, she took even more of his cock until it was right at the verge of slipping into her throat.
Jack moaned and pushed his hips up, but she slid her lips back up his shaft. She swallowed a few breaths and went back down on his cock. This time getting the tip of his cock into her throat before gagging a little. She retreated again, leaving Jack moaning loudly and thrusting his hips.
Now on her third attempt, she was able to get a good portion of his cock into her throat before needing to retreat again. She continued until she had her nose pushed against the base of Jack’s cock. Unfortunately, when she got him that deep, it pushed Jack over the edge. Jack erupted violently down her throat, gagging her. She quickly pulled back and tried to swallow, but Jack came so much she had his cum running back along his cock.
Jack moaned and thrashed as his orgasm shot through him. She had never taken him so deeply, and the pressure of her throat on his excited cock trigged his orgasm. He heard her gag, but there was nothing for him to do. He rode out his orgasm, gagging her and making a mess of himself.
Diane finally pulled herself off his cock. Cum coated her lips, cheeks, and his cock, pooling around his base. She jumped and ran back to the bathroom. Grabbing a towel, she returned to the living room, wiping her face before kneeling down, then wiping Jack clean. Jack just sat there recovering while she took care of him.
When she was finished, she looked into Jack’s face and asked, “Did you like that? I’ve been practicing deep throating a banana.”
Jack smiled and said, “A banana?”
She leaned back on her haunches and looked at him before saying, “Yes, a damn banana!”
“Well, that was one lucky bunch of bananas, and I’m one lucky guy,” he finished.
Diane stood up and reached for Jack, pulling him up from the couch, she said, “Now that you are calmer, let’s go to the bedroom and continue our night a bit more comfortable.”
Holding his hand, she led him back the hallway. He was thinking they’d be going to her room, but instead, she pulled him into her mom and dad’s room. Still holding his hand tightly, she stopped beside the bed and pulled him to her for a kiss. He needed no encouragement and wrapped his arms around her pulling her tighter as their tongues danced.
As they kissed, Jack started running his hands over Diane’s back. He slowly worked one hand to her panty covered ass and squeezed it. As he played with her ass, he slid the other to a breast. He could feel her hard nipple through the thin material of the bra. He pinched it through the material, causing Diane to moan as they kissed.
Maneuvering her to the bed, he started pushing her onto, but she stopped him by gently pushing back. As he watched, she slid the bra off one shoulder and then the other before finally unhooking it. She dropped it to the floor and then grasped her panties and pushed them down her hips until they fell to the floor also.
Looking at Jack, she said, “We won’t be needing those,” grabbing his as she climbed onto the bed with him following her.
She was getting ready to flip around on her back from her knees, but Jack stopped her. Her ass was facing him with her on her knees and her legs parted. It gave him the most perfect view of her pussy, and he couldn’t resist pushing his face into her pussy right there. She felt him and moaned at his touch.
He kissed her pussy and then ran his tongue along her slit, tasting her. She was already dripping wet with excitement, and he was now pushing her even further. Doing a first for him, he ran his tongue from her clit to the rosebud of her anus. This caused Diane to shake and moan loudly. She had never had anybody lick her anus either.
Feeling her shake, he knew she liked it. Taking advantage of this knowledge, he retraced the path of his tongue across her anus to her clit. She moaned even louder than the first time. Jack kept up running his tongue back forth every once in a while, pushing it between her lips. Diane was moaning continuously as he worked her over.
Finally, she twisted from his grasp and rolled over on her back. Scooting into the center of the bed, she parted her legs as an open invitation for him to continue on her pussy. An invitation Jack took. He had his tongue on her pussy and then as deeply as he could get it. He started stroking her clit with his fingers as she had taught him.
It wasn’t long before her orgasm rocked her body. As Jack lapped her pussy and teased her clit, as she shook through her first orgasm. Jack didn’t let up, and a second stronger one followed the first until she was pushing his head away. He reluctantly retreated from her now sopping wet pussy.
After she recovered a minute, she looked at Jack and said, “Come here, baby!”
Jack crawled up next to her, and they cuddled for a moment. Then Diane traced her hand down to his already stiff cock and stroked him lightly, hardening it even further. When she felt he was ready, she rolled to her back and said, “Make love to me, Jack.”
The look on his face was priceless, but he moved until he was between her widely spread legs. Looking down into her smiling face, a thought hit him, no condom!
Swallowing a little, he looked her sheepishly and said, “I don’t have a condom.”
She reached up and pulled him down on her before saying, “No need, I’m on the pill.”
“Oh!” was all he said.
“Now make love to me, you fool!” she said in reply.
It took a little effort, but with her help, his cock got lined up to her vagina. He started pressing forward, and she kept her hands on his waist. She wanted him to go slow and enjoy this first time. He let her pull him in at her pace, enjoying the feeling of her warmth and wetness surrounding him.
When he was finally all the way in with his pubic area smashed against hers, she moved her hands to his face and asked, “How does this feel?”
“You feel so warm, wet, and tight!”
“Relax a minute and enjoy this because then I want you to make love to me for as long as you can.”
Enjoy it he did until the urge to move inside her took over. With her still controlling the pace as much as she could, he started working back forth in her pussy. He felt so good to her. She wanted to enjoy their first time together as much as she wanted him to enjoy his first-time having sex.
They developed a natural rhythm together of him pushing into her as she pushed against him. Of course, nature caused that rhythm to pick up as she neared an orgasm for the first time with him. She encouraged him to go faster and harder until her orgasm hit.
She cried out, and this scared Jack. He stopped and started to ask if she was okay, but she interrupted him by saying, “Don’t stop,” in between the deep breaths she was sucking in.
He felt her tighten around his cock and realized she was having an orgasm. It felt wonderful to him as he kept slipping in and out of her now ever tight pussy. It wasn’t long before he felt his own orgasm build. It felt she was squeezing his balls. His cock got stiffer and was pulsing hard, but he kept going.
She felt the change in him as he slipped along her sensitive walls. She knew he was going to cum and wanted to cum with him if she could. She encouraged him and directed him to go faster, harder, and push into her as deep as he could. With this encouragement, she felt her second orgasm building as well
Jack moaned, “I’m going to cum!”
In the throws of her own orgasm starting, she didn’t answer him other than pulling tight against her by wrapping her legs around him. She held him to her as she felt his cock pulse, shooting jet after jet of his cum into her as her own pussy contracted and pulsed with her own orgasm.
As they both finished, Jack just collapsed on her panting. She rolled him to the side, so she was cradling him as they both caught their breath from their orgasms. Neither moved for the longest time until finally, Jack leaned up and kissed her. She kissed him back as they cuddled.
By the time the night was over, Jack was far from the virgin he was when he walked in the door that evening. The next day when Diane drove him back to meet his buddy, his buddy couldn’t do anything more than smile at him.
Yet as soon as Diane drove away, he looked at Jack and asked, “So, how was it?”
Jack just smiled and said, “Go,” pointing at the driveway. He wasn’t going to share what happened with anybody but Diane.
Copyright © 2020
All works published under the author’s name of Road_Runner are entirely of my own work. No part of this material may be reproduced or transmitted in any form or by any means, mechanical or electronic, or used in any other fashion without the express permission of the owner.