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,
Hi Lover,
Don’t worry about socks, shoes, or underwear. Go commando for me tonight.
D
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.