A New Workout

"Hey Jack!" Haley shouted as she walked through the door.

Jack came around the corner into the living room carrying two Rum and Coke's.

"Hey Haley, perfect timing! I just got the movie queued up, and a couple of drinks made. Captain Morgan alright?"

"Yep," Haley replied, sitting down on the couch "but I can't have too many. I'm trying to get back in shape, and booze and pop isn't going to make the process any easier!"

Haley had been working out recently to impress Jack, but it seemed that Jack only had eyes for the typical bleach blonde bimbos that hung around the bars he frequented. She was still a bit overweight, but she was making progress - her figure was getting curvier by the day, and her chest was starting to fill out her shirts better as well.

This fact did not escape Jack. He had always had a bit of a lustful attraction to Haley, but considered their friendship platonic. He always had considered her more of a little sister than anything, but at the same time couldn't help but feel a stirring in his stomach whenever she sat a little too close to him, or wore short shorts or knee high socks, a personal favorite of his.

"The effort is really paying off, you look fantastic!" Jack said as he slid the drink over to her. "What's your secret?"

"Lots of waking up early, and being in constant pain" Haley laughed as she took a sip.

"That sucks," Jack replied, "is there anything I can do to help? I have a couple advil if you want?"

Haley felt her stomach start to turn. She had been thinking about ways to get closer to Jack recently, and while she never thought that she would have the opportunity or the guts, she couldn't pass up such a perfect opportunity.

"Actually, would you mind rubbing my back? I went running, and my back is killing me!" Haley asked, hopefully.

To her relief, Jack immediately replied with "Sure! Here's a pillow, you can lay on the floor and I can start at your shoulders and work my way down".

Haley laid on her stomach on the floor, head under the pillow Jack gave her. Lustful thoughts began racing through her head as she anticipated Jack's hands over her body. She told herself to push the thoughts out of her head, but that just made her mind race even faster.

Jack straddled her hips, noting that his cock was mere inches away from Haley's pussy. He too told himself to push the thoughts out of his head, but too no avail. He felt his dick twitch as it began to grow in anticipation.

Haley felt him adjust his position, and couldn't help but wonder what he was thinking. She felt his hands touch her shoulders and rub deep into her muscles, through her shirt. It felt amazing, but she still felt that something was missing.

The two continued this for a bit, and save for the occasional happy moan from Haley, you would think that it was just a regular massage. However, as the massage continued, Jack's dick continued to grow as he gently moved his hips back and forth across her ass, while his hands worked her back.

"Jack" Haley suddenly looked up.

"Y-yes?" Jack replied, suddenly brought out of his reverie.

"I... I think this would work better if I lost my shirt. That's how they do it in real massage parlors, and while you're doing a great job, I think that the heat from your hands on my back would help the soreness a lot."

Jack could barely contain his excitement. His dick throbbed as the thought of Haley's tits ran through his mind.

"Yeah, I think you're right. If it would make you feel better, I could lose my shirt also? That way we both get a show!" He laughed, hoping he hadn't taken it too far.

"I think that's a fantastic idea" Haley replied.

Both of them took their shirts off, and Jack ran to grab a bottle of baby oil. He returned to Haley still facedown on the floor, but saw the sides of her breasts against the floor. He lowered himself against her ass again, and couldn't help but feel that Haley could feel his now full erection against her ass, but she didn't say anything, so he began to pour oil across her back.

When he had enough, he capped the bottle, and began to run his hands over her back to spread the oil out. A small moan escaped Haley's lips as she felt the heat of his hands sink into her skin, spurring Jack to be more courageous and begin to run his hands along her sides. His hands grazed along the sides of her breasts and Haley let out a quick gasp.

"Sorry, is that alright?" Jack asked, hoping he hadn't overstepped his boundaries.

"No, that felt fantastic," Haley replied, "In fact... if we're going for a real massage, why don't we go all the way with it?" Her stomach filled with butterflies as she readied herself to give her request. "Why don't I take off my bottoms as well? My legs are sore too, and they definitely need some attention".

Jack paused for a second, not wanting to seem to eager. "I think that's a great idea... but I should take off my shorts as well, just to make sure we're both as comfortable as possible".

Haley agreed, and soon they were in the same positions, but with Jack only in boxers, and Haley only in panties. The smell of sex filled the air and Jack noticed a wet spot develop on Haley's panties between her legs. Haley felt Jacks erection against her leg as he began rubbing her back again, much lower than he had been before.

Jacks hands wandered to the top of her panties and ran along the top and along her sides. His hands skipped down to the outside of her thighs and he gripped her legs tightly as he rubbed her sore muscles. He heard her breathing became more labored and faster, and as his hands roamed over the back of her thighs he saw the wet spot between her legs grow.

"Haley, my boxers are a bit confining at the moment... would you mind if I took them off?" Jack asked, knowing the answer and already moving to remove them.

"Only if I can take off my underwear too!" Haley giggled as she reached down to pull her panties off.

The two naked friends continued the massage, Jacks hands getting closer and closer to Haley's exposed pussy, but never touching her. He moved on down to her calves and began rubbing her legs again.

"Jack, can you rub my upper back again? It's still a bit sore." Haley asked, a plan hatching in her mind.

Jack obliged by moving up her body, his erect cock now nestled between her ass cheeks as he moved gently back and forth, his hands rubbing up and down Haley's shoulders and upper back.

Haley lifted her ass, and Jack's gliding dick slid inside her, with no resistance. Both gasped as Jack leaned forward, and his entire length entered Haley's pussy. Both of them sat there, feeling his throbbing dick pulse inside her.

"Jack, please fuck me" Haley begged

Jack wasted no time, and immediately pulled back as far as he could without the head of his dick leaving her pussy, and pushed all the way back in. His thrusting sped up as Haley began panting, moving her hips back to meet his thrusts.

He pulled Haley the rest of the way up onto her knees, and continued fucking her, pulling his cock out as far as he could and slamming back into her. His hands wrapped around her hips and brought her ass back into his thrusting, forcing his cock even deeper inside her.

Haley reached up and began rubbing her clit. "I'm so close Jack, don't stop!".

"Oh god, me too Haley. Cum with me!"

Jack leaned back and pulled Haley's ass back into him as he thrust forward, penetrating deeper into her than ever before. Feeling his cock throb, Haley began to orgasm, her pussy contracting and squeezing Jack's dick. Jack couldn't hold on anymore, and let loose a torrent of cum inside her. Both moaned and panted as they continued to cum, and Haley felt Jack's cum fill her up and begin to drip down her legs.

Jack pulled out and collapsed next to her. Haley rolled over and leaned against Jack's chest and said "You know, I think I'm going to be even more sore tomorrow morning. But I'm pretty sure I just found my new favorite workout!"