Time For a Road Trip Ch. 03

Chris and Jess locked hands as soon as they were out of sight of their spouses. They walked to Chris's car like a couple enjoying a date. Once at the car Chris spun her around and kissed her passionately. Anyone walking by would never have known that this man and woman were not a couple.

Chris broke the kiss and hit the unlock button on the key fob. He opened the door for Jess and only closed it once she was situated in the passenger's seat. He went around and got into the driver's side and started the car. "Man, this place is more packed than I thought. It's going to take forever to get out of here," he said as he surveyed all of the cars moving towards the parking lot exit.

Jess reached over and took his hand. "It's OK. We're not on a schedule. We have as long as we want tonight."

Eventually Chris was able to navigate the traffic and get them out of the parking lot and on the road. Jess had been looking at her phone as he was trying to find the best route out of the parking lot. Once they exited the venue she looked at him. There was excitement in her eyes.

"Can we make a quick stop? I need to pick something up," Jess asked sweetly.

Chris's next comment came out like a high school teen on prom night, "I've got condoms in my bag at the hotel."

Jess laughed. "That's so sweet that you thought of that, but I need something else. It's a surprise. But you're going to love it."

Jess read the directions from her phone that took them to an all night pharmacy. Once Chris parked she opened the door and went in. She was only gone for maybe 10 minutes. When she returned she was carrying a small white bag with the store's logo emblazoned across the front. She got back into the car and shoved the white bag into her purse.

"Ok let's go have some fun!" Jess said as she was buckling her seatbelt.

Once inside the hotel elevator, Jess pounced on Chris. They were kissing and running their hands over each other. They only broke contact when the doors opened. They made their way down the hallway to Chris and Shelby's room. Chris's hand was shaking with excitement as he slid the key card into the lock.

He opened the door and let Jess in. He stepped in and before the door even closed, Jess was on him again. She kissed him and untucked his shirt. She walked both of them to the edge of the bed as she removed the buttons of Chris's shirt. He let it fall from his shoulders to the floor just before the back of his legs met the bed.

He reached to undress Jess. She broke their kiss, pulled away to undress herself, and said, "Let's just get naked. I want you so bad right now."

Quickly they were both nude and sliding under the sheets of the bed. Jess reached down to grab Chris's rod, finding it already hard. She moaned and dropped under the covers and swallowed it whole.

Now it was Chris that was moaning. Jess was giving him an amazing blow job and he lifted the sheet to watch as her head bobbed up and down his rigid shaft. She would drop her head and let him slide as deep into her throat as he could. Then she would apply a deep suction as she moved her mouth back up.

Jess had been performing her oral talents on Chris for almost five minutes when she raised her head and asked in a breathy voice, "how fast can you get hard again if you cum?" She was still stroking Chris as she asked.

"It won't take long if I'm really turned on," he replied quickly.

"Are you turned on?" Jess asked with a smirk.

Chris put his hands on Jess's head and slowly guided her back to his erection. She resumed the actions she was performing before she stopped to ask the question. This time she intended to make Chris cum. She reached down and started stroking his balls in time with the motion of her head.

Chris was enjoying everything Jess was giving. His head fell to the pillow and he laid there enjoying her masterful talents. It was then he noticed Jess's finger sliding between his ass cheeks. He looked down. His face must have shown the shock he was feeling.

"Shhhhhh, just relax. It will make you cum harder than you ever have in your life," she whispered as she made small circles around his ass. Chris didn't know why, but he completely trusted Jess when it came to sex. He relaxed and felt the tip of her finger entering him as she sucked and swallowed him.

Jess slowly worked her finger in, inch by inch until it was completely inside of Chris. Once there she held it still and let his sphincter relax. Once it loosened up she slid it in and out at a slow methodical pace. Once she could tell Chris was completely at ease, she pressed the tip of her finger against his prostate and moved it in small circles.

Chris was laying there receiving the best blowjob he had ever had in his life. His mind started to begin to formulate a plan to get Shelby to do exactly what Jess was doing. He shook the thoughts away and once again lifted the cover to watch Jess.

Jess felt Chris grow in her mouth when she applied pressure to his prostate. She slowly worked a second finger inside of him, causing him to drive his hips upward, forcing more of his cock down her throat. She moaned around it, sending a shiver up Chris's spine. Her fingers pressed harder into him, massaging him towards a massive eruption.

It wasn't long before Chris said through clenched teeth, "Oh fuck I'm going to cum!"

Jess released him from her mouth and started jerking him with her free hand. "Yes. That's it. Cum for me. I'm feeling nasty. I want you to cum on my face, Chris," Jess said in that same breathy voice she had used before.

Chris's hands reached down and gripped the sheets below him. His back arched. His sack pulled tight and he shot what felt like a gallon of cum from them directly at Jess's pretty face. Jess was rubbing his ass faster, coaxing more cum from deep inside of him. She aimed each shot directly at her face and soon it was coated with the shiny white fluid.

Jess removed her hands from Chris and sat up on her knees. She used her fingers to scoop up his load and licked them clean as he watched. She put on a little show trying to keep his excitement piqued. She would moan as she slid her coated fingers into her mouth. She slowly extended her tongue and licked each digit.

As Chris lay there recovering, Jess got up and went to the bathroom. He heard the sink running. She returned shortly, her face completely clean. She handed him a glass of water. As he drank it down Jess started playing with his already retreating erection.

"Did you like cumming on my face Chris?" Jess asked in a sultry tone as she coaxed him back to attention. He nodded as he continued to drink. "I loved it. Now let's get you ready for round two. I want you inside me," she added.

Chris set the glass down and pulled Jess in for another kiss. She continued working his shaft as they made out. He lowered his head and took one of her nipples in his mouth. Jess emitted a low growl and pulled his head in closer to her chest with her free hand.

Chris rolled Jess to her back causing her hand to lose contact with his growing hardon. He ran a hand over her stomach ending between her legs. He slowly stroked her swollen lips as he nibbled the hardened nipple in his mouth. Slowly he parted her lips and lightly traced her inner folds.

Jess was enjoying the way Chris was taking his time with her. He was exploring her body with his mouth as his finger teased her, not just content to plunge into her and pound a way. This is what she was craving. Someone to take their time and use their hands and mouth finding her sensitive spots. The spots that put her libidio into overdrive.

WIth every sigh or moan from Jess's lips Chris inched closer to slipping his finger inside of her. Once he felt her body twitch and roll, trying to get his finger inside of her he slowly pushed it into her. "Yesssssss," she moaned.

Chris was kissing her neck and lightly biting her skin. Jess was on fire as his finger started working in and out of her. She felt his thumb start to apply pressure to her swollen clit, making small circles in time with the finger moving within her. She gripped Chris's shoulders and held his upper body in place as his hand sent her pussy onward towards an orgasm.

Chris sensed Jess's orgasm beginning to build so he focused on the actions of his digits. He then whispered into her ear, "I want you to cum for me." Jess sighed deeply and pulled him even tighter.

"You look so sexy right now. I can't wait to see you when your body explodes on my hand," Chris continued with his verbal stimulation.

Jess was so close. She tilted her pelvis downward forcing his thumb into more direct contact with her swollen button. This caused the most stimulation she could get in this position. It wasn't long and she gave Chris what he wanted.

Jess's mouth opened but no sound came out. Her body went rigid and slowly shook. It wasn't an earth shattering orgasm, but it was big enough that she wanted more. She wanted to cum hard. She wanted to explode in a way she had never cum before.

Once her body calmed, Jess rolled to her side and started kissing Chris all over his face. She reached down and felt his stiffness brush her hand. She gripped it and gave it a couple strokes. "I need this inside of me," she said in a demanding voice.

Quickly she moved to the other side of the bed and positioned herself on all fours. She grabbed Chris's hand and pulled him towards her. He quickly moved behind her and took himself in one hand. He slid the head of his dick up and down the swollen labia in front of him.

"Don't tease me, fuck me,"Jess hissed through clenched teeth.

Chris drove himself in slowly. Inch by inch he pushed into her until he was fully inside of her. Once there he gripped her hips and started moving in and out in a slow but fluid motion. Jess rocked her hips back and forth until they formed a compatible tempo.

They had been in this position for a few minutes when Jess pushed back hard and held herself there. At first Chris thought she may be having another orgasm until Jess disengaged and turned to look at him.

She was sitting on her knees staring straight at him. She had this soft look on her face and she spoke in an equally soft voice. "Chris. This has been amazing so far, but there is something I want you to do for me."

Chris was puzzled as to what it could be, "What else would you like me to do?"

"So I guess you've heard Josh is um well, he's big," Jess returned.

Chris was starting to feel deflated like he wasn't pleasing Jess. "Yeah, I've heard something like that," he said with a beaten down voice.

"No, honey it's nothing bad. I'm having a great time but I want you to do something I could never do with him because of that," Jess said, sensing the dejection in his voice.

Chris looked at her with a confused look, "What is it he can't do?"

"Chris, would you please fuck my ass? I've never done that before, I really want to try it and I trust you to be my first."

Chris was torn. He had this beautiful woman in front of him asking him to take her anal virginity, but he had promised his wife this was something he would only ever do with her. He was searching for the words to softly tell Jess he couldn't but at the same time not ruin the rest of their time together.

Jess spoke before he could answer, "I also would need you to promise to never tell anyone, even Shelby. Josh has tried many times, but he would be upset if I did it with anyone else before him."

Chris was weighing his options, but ultimately gave in. "Yes. If that's what you want. I promise I'll be gentle, but you have to tell me if it hurts you so I can stop," he said.

Jess smiled big and hopped from the bed to find her purse. She reached in and retrieved the bag she got from the pharmacy. She opened it to reveal a brand new package of lube. She quickly rejoined Chris in the bed and handed him the bottle.

Chris smiled and told Jess to turn around and to get back on all fours. He flipped open the bottle with one hand as he spread her ass cheeks with the other. He started to drip the slippery liquid onto her puckered hole. She squealed at the chilly liquid coming in contact with her sensitive ring.

"We can't just pop it in. We have to get it loosened up," Chris said as he started massaging his finger around her tight backdoor.

Jess moaned at his touch. Her face was looking back watching him knead and lightly probe her. His finger would push in ever so lightly then make a circular motion before sliding back out. He would occasionally add more lube, and his finger would slide in deeper while making larger circles.

Jess was in a constant moan it seemed. This man was working her backdoor and it felt amazing. He was taking his time stretching her out making it ready for the ultimate act that was to come. Soon she felt even more pressure as Chris added a second finger. With both fingers he repeated the probing and stretching until his fingers were all the way inside of her tightest of holes. Once there he started moving them in and out of her.

Jess buried her face in the pillow to keep from screaming out. She felt a burning in her ass, but immense pleasure at the same time. She started to wonder how much longer before Chris pushed his rod into her. That question was answered shortly after.

Chris withdrew his fingers and liberally applied the lube to his hardon. He stroked it up and down. Fully coating it. Once he knew his cock was fully lubed up, he dripped more back onto Jess's asshole. He placed the head of his dick against it and started to slowly push.

"We're going to go real slow. I'm going to work my cock into this tiny little ass of yours," Chris said to Jess.

Jess wasn't prepared for what was going to happen. Once she got through the initial pain of his fingers everything else was pleasure. Once Chris started pushing his head into her, it felt as though the dick she had been experiencing all night had grown ten fold. The stretching and burning it was causing was almost all pain initially.

Chris felt Jess's body tense as he pushed. "Relax baby. The head is the worst part. Once it gets in, it's all pleasure from there. Breathe," he said as he applied more pressure feeding himself into her tight hole.

Jess tried to relax as much as possible. Soon she felt her ass clamping down. The pain was starting to subside. She let out a deep breath. She realized that Chris had pushed the head in and was now slowly feeding her inch after inch of his shaft.

Chris felt her sphincter slam closed, swallowing the head of his dick. The hardest part was over. Now all he had to do was work all seven inches of himself deep inside her rectum. He pushed slowly. "Oh fuck you're tight. Your ass feels so good around my cock Jess," Chris said, trying to encourage her.

Chris's hips met Jess's firm ass cheeks. He was completely inside of her. He held her hips and allowed her to get used to him being there. He felt the heat encasing his shaft and he twitched slightly.

Jess felt full. She was loving the feeling of this man deep inside her bowels. She slowly started to rock her hips moving him in and out ever so slightly. Chris took the hint and moved in slow strokes. He would remove half of himself before slowly pushing back in. He waited for Jess's signal to go faster or harder.

"Oh fuck that feels amazing," Jess said. She felt Chris slowly working into a faster tempo. She lowered her head into the pillow and started swearing uncontrollably. She was finally getting her ass fucked, and she now knew she would be doing this anytime she could find the right man to do it.

Chris soon was moving in and out at a steady pace. Occasionally he would squirt some more lube along his shaft to keep the friction from building and hurting Jess. He sensed he was going to be cumming inside of her ass soon and he wanted her to cum first. He dropped one of his hands from her hip and located her clit.

He rolled and rubbed it with his hand as he pumped in and out. Jess was shrieking non stop into the pillow. He asked if she was Ok and she just nodded as she continued to scream into the pillow. The motion from him pumping in and out of her tiny backdoor and his hand working her sensitive clit soon pushed her over the edge.

Jess's legs collapsed and she fell flat. Chris fell on top of her. Her rectum spasmed over and over. Her body pulsed and hummed with the massive orgasm rolling through her body. This was too much for Chris to take and he grunted as he unloaded a huge load deep inside of her.

They both lay there panting and Jess started to try and push Chris off of her. "Wait. We have to go slow or it will hurt you," he said through his ragged breaths. Slowly he removed himself and Jess shuddered as another tiny orgasmic wave hit her.

Once Jess caught her breath she kissed Chris hard. "That was fucking amazing. I mean I'm going to be sore as hell tomorrow, but it was worth it!" she said between kisses.

They lay there catching their breath when Jess heard her phone chirp. She got up and found it. She looked at the text message and said, "Well looks like the fun's over. Shelby is ready to come back."

Chris told her he would drive her back to her hotel and collect Shelby when he got there. Jess was getting ready to send the text when Chris said, "We should probably clean up first." They moved to the shower and Jess put on the cheap shower cap she found in the bathroom. They stepped in the shower and started soaping each other up.

Jess had her back to Chris and she felt his cock was once again erect and poking into her back. She looked over her shoulder and smiled. "Damn. That thing must really like me," she said with a giggle. She bent at the waist and braced her arms against the shower wall. Chris didn't waist any time as he drove it deep inside her pussy.

They fucked until they both came one more time. They then rinsed off. Jess quickly texted Shelby and told her Chris would pick her up when he dropped her off. They dressed and headed to the car.

Chris pulled up to Jess and Josh's hotel. Jess texted Shelby and told her they arrived. She turned to kiss Chris one last time. "Tonight was wonderful. Thank you," she said before opening the door and getting out.

Jess and Shleby met each other in the lobby. Chris watched as they had a short conversation and shared a hug. Shelby then walked towards the car. He noticed her hair was damp. She opened the door and got into the car. The interior lights revealed she no longer had any make up on.

"You look like you had fun," Chris said with a smirk.

"We can talk about it tomorrow. Right now I just want to get back to the room and sleep until we have to leave," Shelby said in a very hoarse and raspy voice.