Road Trip

*This is sort of a re-imagination of a story I read a long time ago. All characters are over the age of 18.

ROAD TRIP

My name is Bryan. This story takes place after my senior year in high school. It started off with my mom, Kasey (43 years old, pretty, dirty blonde hair), accidentally barging in on me as I was masturbating. Yeah, we've all been there at some point. Very embarrassing. Later in the day she pulled me aside and said "Look, all boys do it. It's ok, and nothing to be ashamed of. I want you to feel like that's something you can do, without judgement from me, alright?"

It was a liberating feeling. I stopped locking the bathroom door. I stopped waiting until the house was empty, etc. Once she caught me beating it on my bed. She walked in, saw what was happening, smiled, and turned around and left without saying a word.

Fast forward to June. I had graduated a few weeks earlier and we were taking a road trip across part of the country. We were packing up at our first hotel before hitting the road again, and mom went downstairs to check out. I had a few quiet moments to myself, so I pulled out my phone, loaded up some porn, and got to business. The door opened.

"Honey I forgot.... oh," she said, as she saw me on the bed with my hard cock in my hand. "I'll just be a minute," she said, evidently looking for something in the room.

"Mom! I'm sort of busy here!" I said, covering myself up.

"It's ok. Nothing I haven't seen before. Like I told you, it's nothing to be ashamed of."

She eventually found whatever it was and went back downstairs, so I resumed stroking. I finished quickly, still pretty worked up about having been caught like that. Or rather having been seen with my hard cock in my hand. It was exciting, and it gave me some ideas for the rest of the trip.

We were on the road shortly, and had a long day ahead of us. After lunch I lowered my seat back to take a nap. Being so young, I was fully recovered from the morning's "session", and was ready for round two. I sneakily began to rub myself over my shorts, until I was hard. Really hoping she wouldn't notice. But her eyes were on the road, so I continued rubbing my cock through the material of my shorts.

"Honey," she said. "Do you really think I can't see that?"

"Oh god, sorry mom," I spit out, covering myself with my hands.

"I know I said to not be embarrassed about that, but maybe don't do it when I'm sitting right next to you? Look, I'll stop up ahead at a gas station. I'll go inside and you can finish in the car."

She pulled over after a few miles and went inside. I made sure there weren't any people around, and then took my shorts down and resumed stroking myself to visions of Jennifer Lawrence. I had already cum earlier in the morning, so I had staying power. It was taking longer than I expected, and mom would be back any moment. I heard the car door open.

"Oh," she said, seeing what was happening in the passenger seat. "I thought I gave you enough time, I'm sorry. How about you move to the back seat and finish up?" she said, as she sat down in the driver's seat.

I crawled into the back and laid down, with my pants around my ankles. My head was behind the driver's side seat, so she couldn't see anything. The only sounds in the car were made by my hand pumping my cock. I then had a weird idea. I turned myself around, so that now I was laying the opposite direction. If she were to turn around, or look in the rear view mirror, she would have a direct line of sight to me abusing my hard cock.

"Almost done?" she asked, briefly turning around. She got a full look, and quickly turned back around facing the front. "If it's taking you too long, think about something that makes you.... you know."

"I am, mom," I replied, between pumps up and down my cock.

"What is it," she asked. Did my mom just ask me what I was fantasizing about?

"A teacher from last year. She was a MILF."

"Ok, that's good. Think about that."

"I'm kissing her and taking off her clothes."

"Great. Too much information, honey."

"I've got her bent over," I said, feeling the surge of cum coming now. Saying it out loud was just too hot. Seconds later I had blasted off all over my chest. I reached for the wet naps under the seat.

"All done?" she asked, before I hopped back in the front seat and we resumed our trip. This new policy on masturbation was fantastic. I loved it. Mom smiled and patted my leg. "Glad we got that out of the way. That's twice today, so I'm assuming you're all done until tomorrow?". No I was not, as she would be finding out later in the evening.

We reached our hotel at about 8 pm. We ordered room service and watched a movie. The room had one king size bed, and we were both laying on it at opposite ends. I was in just boxer shorts, and mom had changed into a robe, with her nightgown on underneath. It had been about 10 hours since my last ejaculation, so I was fully ready to go. I started rubbing myself through the fabric of my boxers.

"Mom?" I asked, leaning to my right towards where she was laying on the bed. "I'm starting to get super excited, and I want to jerk off again."

"Again?" she said, laughing. "That's okay honey, I'll just go into the bathroom and let you do your business."

"No you don't have to. You can stay right there. I won't be long." I slipped my throbbing cock through the hole in my shorts, and held it upright, slowly moving my hand up and down. Mom was trying to watch the movie still, but out of the corner of her eye she could see what I was doing. Finally she turned over on her side and faced me. "Almost done?".

"Getting there," I replied.

"What are you thinking about."

"The same teacher from before."

"And what are you doing to her."

"Kissing her, running my hands up her shirt and touching her tits, pulling off her panties..."

Mom watched me stroke my cock as I described what I was thinking. Being watched was electrifying. I scooted closer, and closer. I was now in the middle of the bed, with her right next to me. I too turned over on my side, facing her, and kept stroking. With my left hand I reached up and began to play with the belt loop on mom's robe. I scooted closer and closed the distance to almost nothing. I had to angle my cock to prevent it from poking her in the side.

Mom looked down and watched me play with the belt tying her robe together. I began to pull on it. The tie became undone. I pulled some more, as my stroking slowed down. The intimacy of what was happening was getting me close, but I didn't want her to know that.

"Almost done?" she whispered, as I continued pulling on her belt loop. It finally came free. She looked down as her robe opened down the middle. Her little satin negligee was partially visible to me now. I think that's why she was wearing a robe: It was very small, and somewhat transparent. I was mimicking stroking my cock but at this point my fingers weren't even making contact. I would have cum already. I wanted to make this last.

"Lay down mom," I said, angling her down on her back with her head on a pillow. Her cotton robe was still open down the middle. "Let me tell you more about what I'm doing in my head to my teacher. It will make me cum faster."

"Whatever you need, honey. It's ok, remember? Don't be ashamed. It's natural."

"OK." Here goes. "I'm in bed with her, and I'm trying to get her undressed. I'm dying to see what's underneath her clothes," I said, as my left hand began playing with one of the sides of her open robe. She looked at me. "That sounds exciting. Think about that, and tell me about it, if it will make you finish faster."

She looked down her body as I took one side of her robe and pushed it aside. I then did the same with the other. I leaned over her now and looked, with only her small satin nightie covering her. She picked up the edges of the robe, as if to re-tie them. I took her hands and placed them back down on the bed, leaving her robe open. I looked at her sheepishly. "I want to keep it open while I do this."

She said "Honey, it's ok. I know you're just playing around. Keep talking about what you're thinking about so you can finish."

"Then I start kissing my teacher," I said, while pushing the robe off one shoulder. "On the neck, and down her chest," I continued, as I pushed the other side off as well.

I re-positioned myself, so that my cock was almost eye level with her. I resumed stroking, very very gently. Right next to her face. I moved again, and was practically on top of her, as she was still laying on her back. My raging hard on, which would go off any minute, was now aimed at my mom's chest.

"And then I grab my teacher's shirt, and yank it off of her, exposing her naked breasts to me." As I was saying this, I took my index finger and drug it down her chest. It picked up the top of her night dress along the way, and was pulled down. I pulled it down as far as it would go, and then it snapped back into place.

Mom watched as I stroked my cock and talked about my teacher. She was being very patient. With one hand I took one of the straps of her nightie and began rolling it between my fingers. I gently pulled on it, until it had fallen down off her shoulder. She watched it fall. I then repeated with the other one. "Honey.... what are you doing?"

"Just trying to cum faster, like you said." I pulled both straps further down, until the portion covering her chest also started lowering down. I was getting very close. This was very dirty. As was my next thought. Where was I going to cum? I figured I'd ask.

"Mom," I whispered, "Where do you want me to cum?" I pushed the little nightgown further.

"Wherever you'd like," she said, watching her slim piece of covering travel further south. I can get a towel for you...." She started to move.

"No I mean, where would you like me to cum.... on you. I don't want to cum in a towel, I want to cum on you."

Her stunned silence said it all. I was very close now. I had just told my mom I was going to cum on her, somewhere. I knew where I wanted to cum. I positioned myself to where I was now leaning over her. Her top was now barely covering her tits. I took it in my hand, and bunched it into a little ball inside of my fist. She looked down, confused. "I'm going to cum on your tits."

I began to pull the bunched up nightie down more. "Oh.... honey, wait, you can't see my....," she stammered.

The swell of her breasts came into view. Feeling more confident, I said "I'm going to take this little nightdress of yours, and pull it down until I can see all of your tits. Then I'm going to cum all over them."

She said softly with the last of her strength, "Baby just leave it where it is. Cum on it there."

"I don't want to cum there."

She clinched the bed sheet with her hands, and closed her eyes.

I pulled down some more, and heard a soft moan as the pink of her aeriolas came into view. I was frantically pumping my cock now, just inches away from my mom's chest. I reached down and touched a nipple through the fabric. I began to bring the garment down completely off her chest, and then I stopped. I had managed to hold off my orgasm. I had more time. I let go of her nightie, and left it where it was: Just above her nipples.

I continued stroking myself, as my left hand now went to the bottom of her nightie. I began to slowly pull it up. I was watching carefully as it made its way up her legs, past her upper thighs, and then past her panties. I pushed it up further, to where it was bunched up just under her tits. The little nightgown now only covered some of her upper torso. I looked down at her white panties, and continued stroking my cock.

I moved on top of her. She was still clinching the sheet with her hands, and softly moaning. I positioned my cock right next to her panties. Then I pushed. I laid my entire body down on top of her now, and began to grind into her panties. I wouldn't last much longer now. The grinding caused her top to move all over the place. I took a moment to stop, grab the right side with my right hand, and pull it down. Mom watched as I tugged on it until the nipple poked out the top, and then I pulled the rest down completely.

We both took a moment and stared at her revealed chest. Her little nipples were so hard. I flicked one with my tongue, and she yelped. "Are you going to cum on my tits now?" she asked.

As an answer, I immediately pressed again into her panties, and felt her lips against my cock, with only a thin piece of material separating them. I reached down and grabbed the front of her panties, and pushed the material together, until it was barely covering her pussy. I took a chance, and removed the barrier. I pushed it to the side. I was looking down at her exposed vagina.

Now my cock was throbbing, about half an inch from her lips. I thought, "Should I?" I looked at her, and then back down at her pussy. It was right there. It looked ready.

I reached my hand out to touch it. Her hand caught mine. I then took her fingers, and placed them at her entrance. She moaned, as two of her fingers slipped inside of her. Now, I was watching her masturbate. I removed her fingers from her vagina, and brought them up to my lips. I tasted them. Her entire body shook.

I brought my attention back to my cock, aimed squarely at her lips. She was moaning, and so wet. I made the decision, and started to slowly press forward. As the tip of my cock went in, she cried out. I pushed in more.

END OF PART 1