Summer of My First Time Pt. 02

Literotic asexstories – Summer of My First Time Pt. 02 by SummerSammy,SummerSammy
This series is complete! I’ll be uploading a chapter every few days.

All characters are above the age of 18. Sam is 18, almost 19, and Matt is 20.

PART 2

I had been at Matt’s place for a few days now. There was a free concert being held by the boardwalk with carnival rides and stuff like that. I put on a cute flowery yellow dress that hugged my curves but realized I didn’t have any clean underwear left. I quietly found Matt’s mom and told her. She said there wasn’t enough time before I had to leave for the concert to do laundry and since my dress was form fitting, I should just go commando. That sounded like something my mom would say! No wonder they had been friends all these years. She also said she and her husband were meeting up with my parents and would be home late.

Matt, a group of his friends, and I had a blast at the boardwalk that night. Matt drove as usual. I sat in the back with some of the other girls. We ate and went on rides. The sun went down and I wanted to go to the concert. No one else wanted to, so Matt went with me. We were towards the front in the big crowd of people that seemed to get more and more crowded. People kept bumping into each other and I was getting jostled around. Matt came up behind me and put his hands on my waist to steady me, which helped. I kept dancing but was bumping into the guy in front of me. Even if it was a little too close, I thought it’s better to be too close to Matt rather than someone I don’t know, so I backed up more.

Matt saw I couldn’t really move forward anymore because of the crowd. He leaned in and said, “At least don’t dance anymore.” I said he’s ridiculous and continued. After a bit, a song I wasn’t as into started, and I realized Matt’s erection was pressed against my butt. As I danced, I’d totally been grinding against him, too lost in the moment. I froze, and Matt groaned, “Keep dancing.” So I did. His hands roamed my stomach and my shoulder, going under my dress strap. He asked, “Are you not wearing a bra?”

“No, my dress has built-in cups.”

“Hmmm.” Everywhere he touched me felt like it was leaving a wake of fire. His touch was strong but cherishing. I was burning up.

His hands roamed down my sides and his left hand skimmed up my leg, bringing my dress with it. He didn’t get very high, but I panicked since that was when I remembered I wasn’t wearing any panties either! I also felt some of my wetness start to drip down my inner thighs.

I abruptly announced, “We should go back and catch up with your friends!”

“You go on. I’m going to need a minute.”

We ate yummy, greasy snacks with the group and went on some rides. Then, everyone wanted to go on a version of the ferris wheel without the platform underneath the feet. It was just like hanging in the air. I said I would sit out on this one.

Matt was trying to be encouraging saying he’d be there with me the whole time. “I know you’re somewhat afraid of heights, but this ride is way less scary than all the ones we’ve been on so far.”

He kept pushing and practically started dragging me to the ride, when I finally whisper-yelled at him as quietly as I could, “I can’t go on the ride, because I’m not wearing any underwear!”

“Why not?”

“I ran out of clean ones and your mom told me to go commando!”

His eyes grew wide, “You know both our moms are crazy and we shouldn’t listen to them about things like this!”

I thought he was going to continue on to chastise me for going on all the other rides or for dancing with him without anything on, but no. He ran his hand on the side of my hip where there would usually be an underwear line but of course it was smooth. He groaned, pulled me closer to him, and said, “You’re not wearing any underwear and you rode in my car.” Boys and their cars…

We sat that ride out together and had a good rest of the night. It was getting late and after swimming the whole day, we got tired faster than everyone else, so left early.

There was a shortcut we would take to his house from the beach but it was a bumpy ride, which caused my dress to ride up as I sat in the passenger seat. I’d pull it back down then in a few minutes it would creep back up. I got tired and lost in the conversation so stopped noticing or caring, since it only went up so far.

Turned out Matt did notice. He kept looking over, and I could feel his gaze on my legs. A part of me thought I was making up his attention, so I spread my legs a tiny bit, which caused my dress to ride up more, and his grip on the steering wheel tightened. He then reached over and pulled my dress back down my legs. The bumps rode the dress up, and he pulled it back down, then kept his hand there, securing the edge of the dress.

My naive inexperienced teenage self asked, “Why are you getting so worked up? No one’s even around anymore and you didn’t care on the way over here.”

“You were in the back seat, so I couldn’t see before.”

“Okay, whatever.”

As we talked about the night, his hand on my leg seemed to sear into me. I didn’t know how to communicate that, so I told him the pressure of his hand was uncomfortable. He apologized and shifted his hand so it spread wider and now was gripping more of my inner thigh, which did the opposite of helping my situation. And was it just me or was his hand higher up now? I squirmed and clamped my legs together, which caused my dress to slip from under his palm and definitely shifted his hand up even higher.

“Sam?”

“Just don’t get closer.”

“So this is okay?”

“Yeah, I think so.”

He started caressing up and down. “You sure?”

“Mhm hmm.” My head fell back on the headrest. He was definitely getting closer.

“Your skin is so soft. Uh, you’re wet.” He was so close, millimeters away. “I’m not going to go any higher, promise.” That was sort of gentlemanly and also very frustrating. Was I so wet it had dripped down again? I was embarrassed but mostly I was going slowly insane.

His hand stayed there and teased me for who knows how long. It could have been seconds or minutes or hours.

Then we hit a big bump in the road that jostled the car and his hand bumped against me.

“Oh fuck!” Matt said when his fingers pressed against me. Yesss, I squeezed my legs together, trying to keep him there. The perfect driver Matt swerved, he was losing focus.

I was already completely lost to the feeling and grabbed his forearm when he tried to withdraw.

“Sam, you’ll hate me later for this.”

“I’ll hate you now if, if you, stop. But stop the car. You’re going to kill us,” I panted out.

He started drumming my clit and I shouted. He parked on the side of the road. Benefits to the backroad shortcut- no lights and no other cars. He unbuckled and leaned over me as his experienced hand continued to rub in all the right places. Teasing along my labia and flicking my clit over and over. He circled my entrance. My breaths seemed loud. It was too dark to see him clearly but his other hand was rubbing himself through his pants. He kissed my cheek then my lips just as he slipped a finger in me and pressed on my clit. I exploded and he swallowed my moans. My orgasm seemed to go on and on and he kept rubbing through it which prolonged it, until I was oversensitive and pushed his hand away. He kissed me again, long and hard. Then he pulled my dress back down my legs.

As we got closer to his home, street lights started going by. I was awaking from my orgasm haze when I spotted a wet spot on his jeans. I softly poked it. “Is that… did you…?”

“Yeah, you made me come in my pants.” I laughed and blushed. I hadn’t even thought of helping him.

Maybe I should next time.