Doing the Most He Can Pt. 01

Todd and Gary hung out the next weekend just playing video games and getting slightly wasted. As he was leaving late Saturday night Rebecca intercepted him at the front door. She grabbed his sleeve pulling him into the hall closet. Gary quietly closed the door while Rebecca went to her knees and pulled his sweats down. He had gone commando today and she moaned in approval as she was putting his growing penis in her mouth.

Gary had always loved the feeling of getting hard in a woman's mouth, loving the way her tongue circled the head. Rebecca soon stopped playing around and deepthroated him.

Coming up for air she gasped, "Face fuck me deep until you come."

It was very sensual to listen and feel her work his hard cock deep but not be able to see a thing in the dark closet. She had her nose against his pubic hair and was squeezing him in her throat when he pulled back to just the head before filling her mouth. She started humming as she kept sucking and soon had every drop in her mouth. She reached out and found his hand and held it to her throat so he could feel her throat work as she noisily swallowed everything in her mouth.

She took her mouth off him and kissed the head of his shrinking prick before helping him pull the sweats up. Helping her to her feet he gave her a long kiss that tasted of cum. She pushed him backward until she found the door and opened it. Closing the closet door, she opened the front door, gently pushing him out. When he was standing outside, she blew him a kiss and quietly closed the door. Gary stood there for a minute then let out a laugh and headed for his bike.

Gary was at work Monday morning when he got a call from a number he didn't recognize, he almost didn't answer but thought it might be a customer he had given his private number.

"I was about to hang up," Lisa said cheerfully. "You get to take a break for lunch, don't you?"

"Sure, it's supposed to be an hour but it usually turns into taking a bite of sandwich every time I walk by the workbench. It's a good thing I like greasy bread."

"Well I had a wicked thought. I have two study halls and lunch back to back so I could leave school from eleven to one any day I wanted. That give you any ideas mister?"

"It gives me a lot of ideas," he said. "All of them are rude, crude and socially unacceptable. Did you have today in mind?"

"Oh my god yes, I am so wet I slosh when I walk" Lisa told him giggling. Mom and Todd are working so meet me at my house. Tell me when."

"Let's say 11:30, that way we have plenty of time. If I am late Randy won't mind."

"I can hardly wait. I have to get to class, bye."

Randy was smiling at him as he hung up the phone. "So, what new pussy are you fucking now?"

"How do you know it's a new one?" Gary asked.

"Because you don't take a lunch break unless it's for a new gal."

"I suppose you're right about that. Yeah it is a new one, kind of special too."

"Well," Randy said dryly, "try to be back before closing."

Gary patiently worked and watched the clock until 11:15 then couldn't stand it and was out the door. He pulled into the Strom driveway five minutes later and used his key to get in the house. Calling out Lisa's name and not getting an answer he went to her room and found it empty. Wandering into the kitchen he looked out the sliding glass door and saw her sitting naked in the tire swing in the back yard.

He had two thoughts: why was she in a tire swing and thank god for California weather. He grinned and quickly stripped then boldly slid the door open and stepped onto the patio.

Lisa heard him open the door and called out, "Nice entrance, you should be the one in drama class."

"What are you doing out here?" he asked, "it's secluded but not exactly private."

"I thought it would be obvious, I wanted to swing."

"Smart ass," he replied as he reached her and gave her a kiss.

"Now that you're here I'm kind of embarrassed about why. Maybe this wasn't such a good idea after all."

"OK, I'll bite. What did you want to do that doesn't seem like such a great plan now?"

"I was like ah, watching a video, you know and uh, I uh, saw this couple doing something and I thought that I could, or we could, kind of do the same thing maybe."

"Wow, drama class has really helped with your articulation, maybe I should take a class," he teased. He saw that he had hurt her feelings, so he kissed her again and said, "I'm sorry, let me try over. You were watching a porno and saw a couple doing something and you want us to try it. What were they doing?"

"I'm not sure I forgive you for being mean to me, but here goes. The girl was bent double in a swing like this so her butt was sticking out in the back. The guy was standing behind her pushing her. When she swung back his thing went inside her."

"That sounds like that might be fun."

"Yeah it does," she said hesitantly, "except the thing is, he was not going into her vagina, he was going in her butt."

"Whoa, that is really hot," he asked her, "but are you sure you want to try anal?"

"When I watched it, I was wondering what the attraction was. I had never really thought about doing it that way before. I lubed up my dildo and put it in my rear and now I know what the attraction is. I really want to try it that way. We don't have to use the swing like the couple in the video, you can just stand behind me and use the swing to get a little movement."

Gary said, "You have thought about this a little, haven't you?"

Lisa nodded and told him, "I watched that video like twenty times and then I came out here and got in the swing like the girl did, to make sure I could do it. That was yesterday afternoon, I was up half the night rubbing myself raw thinking about us doing it. I was up a six and it took me until after second period this morning to get up enough courage to call you."

"I'm glad you did. I love doing butt stuff. We are going to need some lube you know, this won't work without being really slippery."

Lisa reached into the tire and pulled out a tube of K-Y. "I told you I thought about this a lot."

Laughing he asked, "You want me in your pussy for a while first? To kind of warm you up?"

"I wasn't kidding when I said I rubbed myself raw. I abused my poor pussy so much it will probably hurt to pee. In other words, lube me up, stretch me out and get that hot rod of yours up my butt."

Chuckling as he shook his head, he took the lube from her and ordered her to, "Assume the position."

Lisa jumped out of the tire and standing in front of it, bent over and sat in the tire wiggling until her butt was through and sticking out the other side.

Gary walked behind her and came to a stop as he admired the view. Bending nearly in half to get into the swing had pulled her ass cheeks apart so he had a perfect view of her pink sphincter and her very red pussy. He couldn't resist and got on his knees and starting using his tongue on her backside.

Lisa started squirming as soon as she felt the tongue touch her. She had never done anything that felt so good. It was hot and nasty and a little taboo. She couldn't believe her two holes were that close together yet felt completely different but at the same time the feelings were connected somehow.

"Fuck Gary that feels good. Get a finger in me, maybe two, please," she begged him.

He fumbled around, losing the cap from the tube in the grass but finally had two fingers coated with the slippery stuff. His middle finger slid into her very easily, so he added his forefinger.

This got a moan and, "That's enough with the fingers, I stretched it out pretty well with my dildo. Get that fat dick of yours in my butt please."

Gary stood and squeezed out a line of gel along his cock. He rubbed in on smoothly then put a glob on Lisa's protruding ass. He lined up and slowly started easing into her backside. Her orifice slowly and steadily opened up and soon the head popped inside. Lisa grunted and he stopped to let her adjust.

"My dildo is nearly as long as you are, but it's not as wide and it certainly doesn't have that plum-sized head like you do. Fuck that feels incredible. Please get the rest of it in me so you can start fucking my not quite virgin anymore ass."

Gary pulled on the tire to get his cock buried in her tight ass. When he was in all the way he held her against him then slowly let the tire fall away. When the only thing left inside her was the head, he moved closer so that when he let go of the swing it hung straight. To get the maximum stroke all he had to do was give the tire a little pull.

The first time he did it Lisa almost lost her mind. She let out a loud groan and said, "Definitely not an anal virgin anymore. That feels so freaking good. I have heard of women who could come from anal, but I didn't believe it. Fuck me harder and I will prove it's possible."

Gary kept up a steady rhythm and he was getting close to losing it.

"This is the best anal, maybe the best sex, I've ever had. Your ass is so tight, but my cock goes in you so far. Come for me Lisa. If you come for me, I'll coat your insides with my load. It is going to feel so good to unload in your butt."

"That did it you butt fucker, I'm coming. Yup here it is, I'm going to cover your thighs with my goo. Oh keep pumping me, I can hear our thighs slapping together. Paint my insides now," Lisa screamed.

She started to spasm and that was all he could handle. He let out a roar and held himself deep as he let loose. He stood there hanging on to the tire rope to keep from falling. Lisa was moaning and mumbled incoherently.

After a minute Gary thought Lisa must be getting uncomfortable after being bent double for so long. He eased his spent cock from her and a flood of cum rushed out of her gaping ass along with a generous amount of air. He staggered around to her front and told her to put her arms around his neck then holding her legs behind her knees extracted her from the tire.

Lisa locked her legs around his waist and he carried her into the house and right into the shower stall. They soaped and washed each other, sharing little kisses and touches then toweling each other dry.

Lisa went to her room to get dressed while Gary got dressed where he had left his clothes in the kitchen.

Lisa came out ready to go back to school and said, "I only have fifteen minutes to get back."

"Randy will be tapping his foot and pointing at the clock when I get back. I just want to say, it was totally worth it. You never cease to amaze me."

"You ain't so bad yourself, mister," she said kissing him. "Oh damnit, I forgot to have you take a picture of me in the tire."

"I didn't have my phone on me, no pockets in my birthday suit you know."

"You idiot," she giggled, "I stashed my phone in the swing and then forgot all about it. Would you run out and grab it, please?"

"OK, but you are going to owe me a big one."

"Ha, I think I just gave you a big one," she retorted.

"That you did," he replied as he opened the door.

When he got back to the shop Randy saw the satisfied look on Gary's face and shaking his head pointed to Gary's next repair.

Lisa got to school in time to get an apple and a juice from the cafeteria before her next class. Her best friend Jenna caught her at her locker and asked where she had disappeared to.

Lisa said, "I have a lot of things to tell you, come over after school so I can shock you."

*

A special thank you to Clyde A. for editing this. Thanks for reading and watch for chapter 2. As always, vote and leave a comment if you wish.