Lessons Learned Ch. 03

"Let me help you," said his female companion slyly. She reached across him with her head buried in his neck. Gentle kisses made their way up from his shoulder to a tiny nibble on his earlobe. One of her arms stretched out over his lap and pushed a button on the far side of his console. "Lane assist," Felicity whispered in his ear. "That should help you relax a bit more." When bringing her hand back, she paused as his lap and pulled his engorged member free from it's still unzipped hole.

"Now that's more like it," Paul told his naughty passenger as she gave him a few light strokes. It pulsed in response to the stimulation.

"Oh baby," Felicity exclaimed playfully. "Have you been horny. Has this little slut not given you enough attention this week."

"What does that cock tell you," he replied as he took his rightmost free arm and reached over to her ass coming off the seat. She had her seat belt on, but all the straps were messed up, allowing a bit more freedom. Felicity's bare ass was now exposed her skirt had become a belt around her waist. It gave Paul a nice handful of cheek to squeeze and lightly slap. Butt cheeks jiggled in response, just the way he had grown fond of watching.

"It tells me you need so much needs attention," Felicity quipped as her index finger massaged the oozing mushroom-shaped tip. "Look at all that tasty pre-cum. Yummy!" Her fingers pulled away so she could lick the build-up off them.

"Fuck," he said as he watched her out of the corner of his eye. Casually, her hand began rubbing him in the ways she knew he liked. Each motion felt like pure bliss on his package. Paul attempted to get closer down from her ass to that hot little pussy, but it was just out of reach.

"No, Paul," she said, stimulating him a little faster. "This isn't about me, it about you. Adjust the seat a little back. Relax and just enjoy it."

"If you say so," he answered, then pulled his hand off her so he could fiddle with the electric seat motor. It moved back about three or four inches, and he could still reasonably touch pedals. The other lever let him tilt the back lower to a more relaxed place.

"Good boy! Now just enjoy," His sexy MILF told him. She swapped her hand to her mouth now that there was a bit more room. A wet, warm, knowing sensation enveloped Paul as he checked his mirrors while still speeding along.

Paul was happy that this part of the highway was reasonably sparse from traffic. The last thing he wanted was someone to see them and call the cops. According to the GPS on the dash, they had gone eight miles since they started this challenge. Cumming before they go to their destination didn't seem like it would be an issue. Felicity was making a tight sucking on the head of his cock, and the slurping sounds she made was making his toes curl. Subsequently, that made his foot press the accelerator a bit hard.

The car roared as Paul felt the pressure building and foot pressing. Felicity could give the best fucking blowjobs, but while he was driving was even wilder.

"I recommend setting cruise on," Felicity said, pausing the action. "The last thing we need is a cop to pull us over."

"On it," Paul groaned in pleasure as Felicity throated again, resuming her steady pace.

A little paranoia, Paul glanced around for the police. The sun was just beginning to hit the horizon, dimming the surroundings. Not a cop in sight, but a faint pair of headlights were coming up fast on his tail. It was a white pick up truck, and as it got closer, Paul could make out two people were in it.

"We got someone catching up to us," Paul warned. "It's a big pick up truck. They might be able to see you when they pass."

"Let'em watch," she mumbled back with her mouth still full.

Going twenty or thirty miles an hour over the speed limit, the large truck zipped past them like they were standing still. It was one of those super duty models with massive suspension that put it high off the ground. They weren't the first car to pass Paul as he drove, but they were the only ones that would get a clear view of the action when they did go by.

Paul kept his calm throughout the car, passing even though a rush of adrenaline flooded him. It was like an aphrodisiac as he felt himself almost blow. He fought it back and was very glad he did too.

A few seconds after the truck was off in the distance ahead, it's brake lights lit up. Abruptly, the truck got closer fast.

"Fel," Paul panicked.

"Relax," Felicity said as she looked up at him from his lap.

"No, Ummm. That truck is slowing down."

Felicity smacked his slightly dropping erection with a free hand. "Keep that baby hard for me," she explained as her head raised into view of the side window. "Let me handle this."

The white pick-up let them pass then sped up to match speed with their SUV. Two younger likely early twenties men in baseball caps were both staring at Felicity with her head sticking up just above the line of the window. The hand she was still using to fondle Paul's cock and balls came up and waved at the men. The driver beeped his horn in response, and the passenger grinned a goofy smile.

Doing his best to focus on the scene around him, Paul managed to stay hard despite all the various distractions, the hand still gripping him helped. Felicity, resuming to stroke him while watching their new voyeurs, both appeared to be watching.

"Roll down the window," Felicity asked Paul. "I have an idea."

"Uhhhhhhh," Paul said, squirming in his seat.

"Trust me," she told him with a wink.

Following her directions, Paul hit the auto down button for the driver's side window. A sound like a cracking seal hissed as a sixty miles an hour breeze roared in the cabin. The twenty-something passenger of the pick-up did the same.

"You're fucking hot!" The guy shouted as soon as his window was below his mouth.

"That's what they all say!" Felicity shouted back. *Enjoying the show!"

"We would love to join!" He called back.

"I only have fun with my man!" She told him. "We love being watched, though! Do you have girlfriends!"

Both men nodded entirely intoxicated by the sight before them. Felicity never stopped stimulating Paul as all this was going on. In fact, she was going faster now.

"Do they swallow?" Felicity asked them.

"No!" Both men cried.

"Then, keep watching!" She teased. "Paul, you feel ready to burst, think you can cum?" She asked him in a more normal voice.

"Not a problem," he said, smiling. "I have been holding back."

No hesitation, Felicity resumed her blowjob as they now had two gawkers. She was entirely in action as she was going faster than earlier. Paul felt himself swelling as he wasn't going to last much longer.

The driver passed something to his passenger, then the passenger's arm went out the window. In his hand was a smartphone, they were recording the display. Paul didn't have time to decide if he liked that idea as he came hard in Felicity's mouth. Five or six swaths of jizz fired against her throat. Paul was gasping for breath; it felt so good. That had been about a week worth the build-up, which had become unusual since meeting Felicity.

Cheers erupted from the men in the truck as Felicity lifted her head and stuck out her tongue. Paul only caught a glimpse of a few little bits of cum running out of the corner of her mouth. She gulped it down fast, then showed them her now empty mouth. It was amazing that she was still showing off for the camera they were waving at her.

"That's awesome!" Hollered, the driver barely in view.

"Want to see more!" Felicity hollered back.

Again they both nodded with enthusiasm of their youth. Paul tried not to chuckle as his imagination showed them as two drooling dogs out of Bugs Bunny cartoon.

Felicity told them her cam site address and screen name. She then hit the close window switch so Paul could focus on the road. The GPS announced that there was only half a mile away. That cued Felicity to lift up her top and flash them her fabulous tits. She shook them for the guys who were still filming, then waved as Paul without using a blinker took the next exit so they couldn't follow.

"Holy shit!" Paul said as Felicity adjusted her clothes and composed herself back in the passenger seat.

"You never cease to impress me," Felicity said as she pulled a tissue from the center console. "I was worried you might not cum."

"I can't believe we just did that," he said as he could still feel the adrenaline flowing.

"That definitely was fun," she agreed as she wiped up the mess still on her face. She began to touch up her smeared makeup using the mirror on the visor.

"At the next light, take a right," the GPS informed Paul. He looked down to see that they were about ten to fifteen minutes away. They were in the middle of nowhere now. Paul wasn't sure if they crossed state lines yet or were still in Massachusetts. It didn't really matter either because he was just having fun. Having this much fun was something he had probably never done before now, not even in college.

Felicity was now all put back together as she was done with her touch-ups. You could never tell that moment she had just taken a load, flashed some guys and swallowed on camera. This was a crazy, kinda woman, and Paul admired her lack of fear. He wished he was as fearless as she was in his eyes.

"So," Began his now grinning temptress. "Before we get to Kitty's place, I want to let you know a few things."

"Ok," Paul told her with some trepidation in his voice.

"Nothing bad, we are going to have plenty of fun," she followed up. "Just you need to know that this is not Kitty's usual type of thing. She hasn't had anyone else except her needle dick husband in over twenty years."

"I can understand that."

"Good," she explained with gently touch of his cheek. "This weekend is not about me. I want you to show her a good time. Along the way, if I have fun, that's a plus but not required. We can have fun back home."

"I can live with that as long as you can," Paul said, trying to be modest.

"Her husband has been running around on her for years," Felicity said with a bit of venom. "He is a huge executive for a pharmaceutical company. Last year she got a pile of proof he was cheating on her with a mistress in almost every city that he did business in regularly."

"Wow," Paul remarked.

"They have agreed not split for now as long as the kids are still college. I told her she needed some fun of her own and a few boy toys. Kitty isn't as outgoing as I am, and years of put downs have made her not think she is desirable as she once had been. Turning fifty-three put a damper on her too. Especially when the asshole is running around with about three women his daughter's age."

"She's fifty-three?" Paul asked, thinking back to the video of Kitty and Felicity fooling around he had now watched a dozen times. He could tell she was middle age, there were enough age marks, and she had a few extra pounds, but she was still really sexy. Her tits were at least a cup size or two bigger than Felicity, and that said something.

"Yeah," Felicity said with a wink. "I didn't tell you that, ok."

"Not a problem," Paul agreed with a head tilt of acknowledgment. "Anything else you want to spring on me," he joked.

"Nah, just take things slow," Felicity told him. "She is a bit nervous about all this, so we might take the fooling around slow. That's actually why I wanted to get you off before we got there. I know I have neglected you this week, so I thought I would take the pressure off."

Paul laughed, "Yeah, getting a blowjob at sixty miles an hour while two frat boys film you with their phone took off some pressure. Might have shaved some years off me too."

Felicity laughed, and the two of them continued to talk playfully as Paul follow the directions from the car. The last portion of the road was dirt for a mile or two but then turned to fresh asphalt that led up a steep hill. The hill went to a considerable home, Felicity had referenced this as a cottage or summer home, but this was ridiculous. The place was almost three or four times the size of his three-bedroom in the suburbs. Kitty must have some money if this is considered a summer home.

"It's big," Paul commented as he pulled the car into a spot in front of the four-car garage.

"Yeah," Felicity smirked. "That what most men say."

He couldn't help but laugh, his strawberry Milf knew precisely how to make him crack up. It took him a second to gather his composure before getting out of the car. It felt good to stretch his legs from the ride.

As he pulled both bags out of the back, Felicity squeezed his ass. "I wanted to make sure you know in your case, it's big should just be Oh My God."

"Thank you," he replied as he turned bright red on the walk up the driveway to the front door.

Felicity rang the doorbell as the sun was now almost gone. Paul could hear the peepers crying in the early start of the evening. The surroundings here were terrific, the house had lush forest all around it. It was darker, but Paul took note he thought he saw a hiking trail when they were over by the garage. He might ask about that in the morning. A good run was always great to get the blood flowing after a night's rest.

After a few seconds, they could hear the clip-clop of heels on the tile as someone came to the door. Felicity had warned Paul that Kitty might be timid, but the outfit she wore to the door was anything but that. A shorter dirty blonde woman answered the door in a leopard print bathing suit, black four-inch open-toed heels and silk black bathrobe fully open. Two chopsticks held her hair in a twist updo out of her face to expose a well-tanned neckline. The bathing suit was all one piece but was one of those plunged down the front almost to your belly button kind. It didn't take a keen observer to see how it split and lifted her rack very nicely. In her free hand, she carried an almost empty martini glass. Midway through opening the door, she gulped the last sip of her martini.

"Fel," the women said as Felicity stepped towards the doorway. The two embraced like the two old friends, Paul expected them to be. Focus changed to Paul, and Kitty turned a bit red as she greeted him. "You must be Paul," she said, extending her hand to him.

Paul took her hand, and instead of shaking it, he kissed the back of it. It felt slightly cheesy, but he figured an action like that might make the new woman feel a bit more at ease with him. He guessed it worked as he saw her shiver slightly with he did, and her face got more flush.

"Come in," Kitty said, gesturing inside with her now empty drink. "Make yourself at home. I have heard so much about you, Paul."

"All good I hope, Kitty," he replied as he brought in their two small duffle bags into the foyer of the house. Kitty only responded with a knowing smile and a wink.

Paul was taken aback, the foyer was small but immediately opened into a huge high ceiling living room. The room was as big if not bigger than Paul's house. The middle of the room was an open fireplace with several couches around it. Doors lead to other rooms off of the living area, and a stairway led up to a balcony that Paul assumed was the bedrooms. Over their heads, several skylights peered at the evening sky, now showing some stars.

"You got here just as I was going to jump in the hot tub," Kitty told them as she closed the door. "Put your things over there," she directed to a small side table in the foyer. "Drinks?" She asked and then followed up with, "Then maybe joining me in the hot tub?"

"We would love to," Felicity said, taking the bags from Paul. She placed them on the table then said. "I'll have a Martini."

"What do you have?" Paul asked, feeling a bit out of his element. He was a meager teacher, and Felicity seemed decent financially, but Kitty was in another ballpark altogether.

"We have a fully stocked bar," Kitty said, pointing to a full-size home bar in one corner of the room. Several shelves displayed dozens of various booze of types and flavors.

"He'll have a scotch," Felicity answered for him and kissed him on the cheek. "Neat. Give him some of Eddie's good stuff."

They all followed Kitty over to the bar, and she pulled a few glasses out from under the bar. Felicity was very much at home and had clearly been here several times before too. None of the spectacles around them fazed her. Paul wished he could feel that way also. Hell, if everything was supposed to go as planned, he was going to show this woman a good time in the bedroom. Paul was a little afraid now as he saw how outclassed he kinda felt. The drink might definitely help, he thought as he leaned against the bar.

"I'd love to join you in the hot tub, but I don't have my bathing suit," Paul admitted as he watched his new female companion make his drink. She pulled a very identifiable bottle of Johnnie Walker Blue off a shelf and poured him almost half a low-ball full.

"Oh, baby," Felicity told him. "You don't need shorts. I wouldn't let them stay on you very long."

He could hear Kitty, fight back a choke at the remark. Then Kitty pushed his drink across the bar to him. Paul knew Felicity long enough that he expected the response from her. Truth be told, he wasn't planning on wearing any swim trunks, to begin with, Kitty just didn't need to know that.

"You're the boss," he said as he picked up his drink and took a sip. It went down smooth and was the most excellent scotch he ever had. Back home, he liked similar but usually kept to Johnnie Walker Red or occasionally splurged on Black.

Kitty started making Felicity's drink as Felicity began to walk away. "I am going to put my suit on," she said casually. "Are Paul and I in the guest room at the top of the stairs?"

"Take your pick," Kitty said, shaking a metal shaker full of vodka. "Not like anyone else, but us is here."

"Ok, now you two play nice while I am gone," she answered, taking both duffle bags to go upstairs.

"It's not like I bite!" Paul shouted to her.

"Maybe I wasn't talking to you!" Her voice bellowed back just out of vision. A door closed, and Paul assumed that would be his and Felicity's room.

"Oh God," Kitty gasped. A slight look of panic shown on her cute little face. Her tiny little mouth and nose took up a pouty look. "That woman is encourageable."

"You're telling me," Paul said with a taste of his drink.

"Can I be honest with you, Paul?" The mature shorter woman said, pouring another martini, this one for herself.

"Of course," Paul said, giving her a look of understanding.

"I am very nervous. This sort of thing is not normal for me. I can't even be sure I really want to go through with this crazy idea."

Paul looked at her with empathy, he touched her hand gently. Her eyes were on the verge of watering, and he knew that need to stop something quick. It could ruin the night before it even began.

"Listen," he told her with assurance. "I am just here for fun and some beautiful female companionship. If you're not interested or think I am not your type, I won't be offended. Since we are staying honest, I have never done anything like this myself, so I have a few butterflies in my tummy."

Kitty looked Paul up and down. It was written all over her face that she thought he was reasonably attractive. "It is not that don't find you attractive, I just haven't been with any man but my husband Eddie in over twenty years. I have watched that video of you and Felicity on her site almost a dozen times. So many I ended up needing new batteries for my vibrator."

"I watched that video of you two just as many," Paul said then took another pull of his drink.

"I can't believe I did that on camera with her. We had a few drinks, she showed me that video of you guys. Next thing I know, I have her filling me with the biggest dildo I have ever seen," Kitty told him then followed up with a gulp of her fresh martini. "I pray my girls never see that!"