Feels Like the First TIme – Chapter 3

True story: Feels Like the First TIme – Chapter 3

by melanieatplay

I observed him tear open the little foil package and pull out the condom. He then rolled it down the length of his cock. I continued to watch as he opened the jar of Vaseline scooped out a large dollop and rubbed it over his condom encased penis.

He got back into the bed and moved between my legs which I hesitantly opened wide for him while ensuring that my bottom was still centered on the towel. He scooped out another large glob of Vaseline and rubbed it over my aperture.

“I’m going to go really slow, but it still might hurt. If there’s too much pain, just tell me, and I’ll stop, okay?”

“Okay.”

He reached down and rubbed the head up and down my vagina before positioning himself at my opening. I felt him splitting my lips and then push forward slightly until his progress was halted. He took a deep breath and I felt a sharp surge of pain as he pushed forward again and I could tell he had worked himself inside of me. There was some discomfort as he continued to slowly push inside of me, but nothing like the sharp pain I had felt a few seconds before. Moments later, I felt his balls rest against my bottom and I knew he was completely inside of me. He laid on top of me, remaining motionless, letting me get used to this very new sensation.

“Are you okay Melanie?”

“I’m all right.”

“I’m going to go really slow, and remember, if you want me to stop, just let me know.”

“Okay.”

I felt him begin to move backward and then slowly push forward again. There was still a little bit of discomfort, but not really much pain, so I could handle it. Very gradually, I could feel him picking up the pace and moving in and out of me a little more rapidly. I looked up and watched his face intently. His eyes were tightly closed and it looked like he was in another world. He began to let out little moans and grunts, and I could tell he was really getting into it.

“God you’re so fuckin’ tight’,” he said, almost to no one in particular, because he appeared to be off, somewhere else.

He began to thrust into me harder and I wasn’t entirely certain that he knew he was doing it because it seemed to be an almost unconscious act. As the hard thrusting continued, the discomfort increased, but I didn’t feel it was bad enough to make him stop and ruin this experience for him. He continued to slam into me and his body began to stiffen, and his breathing changed. His solid trusts turned into short little pumps and I thought he might be cumming, but I couldn’t be sure. Without warning, he collapsed on top of me.

I could feel him soften inside of me and a few seconds later his breathing returned to normal and he slipped out of me and rolled over to my side.

“God, that was good.”

“Yeah… it was ummm… really nice.”

“Did you cum?”

“I… I’m… not sure. I don’t think so.”

“It’ll get better, I promise.”

“It was really nice Anthony, and I enjoyed it.”

“Good.”

“I’m going to go into the bathroom and get dressed, okay.”

“Okay, I had better get going too, I don’t want to be late for dinner, or have your parents catch me here when they get off work.”

A slight smile split his lips.

“Yeah, we don’t need that.”

He turned, and walked out the door into the bathroom.

While I was getting my clothes on, I looked down at the bed and noticed a spot of blood on the towel I had been laying on. I had just finished putting on my blouse when Anthony entered the room.

“Do you want me to; umm… get rid of that?” I asked sheepishly while looking at the soiled towel.

“No Melanie, I’ll take care of it.”

“Okay.”

He walked over to me and gave me a hug and a little kiss.

“I know it wasn’t the greatest for you, and I promise it will be better next time.”

“It was nice Anthony, I liked it.”

“Well… Just let me know when you want to come over again.”

“It might be towards the end of the week, but I’ll let you know.”

I didn’t want to tell him, but I was sore already. I knew I’d need a couple days of respite before we tried this again.

I snuck out the back door and made my way home.

Day Two

It was Thursday and I was finally starting to get back to normal. When I had woken up Tuesday morning, I was so sore I didn’t think I would be able to move. I told my mom that I’d been up all night vomiting, and thankfully, she took mercy on me and let me stay home from school. I spent most of the day in bed, but by the evening I was starting to feel better. The next day, Wednesday, I was still a little bit sore but I was able to go to school and function normally again.

I woke up and texted Anthony and told him I’d be over today after school. There had to be more to this ‘sex’ business than I had experienced on Monday, and I was anxious to ‘get back in the saddle,’ and give it another go.

After school, I snuck around the back of Anthony’s house and knocked on the door.

“C’mon in Mel, let’s sit down and talk, okay?”

We walked into the kitchen and I sat down at the table. Anthony got me a big glass of iced water, and then sat next to me.

“I know what we did wasn’t that great for you,” he said hesitantly.

I looked down shyly.

“It was okay.”

“Look, I was really nervous because of your brothers. I’m still terrified of them finding out about this, you know…” He paused for several moments. “I guess my point is, if I could do it again, there would be things I’d do differently.”

I took a deep breath and collected my thoughts.

“Anthony, listen to me. First, my brothers aren’t going to find out what we’re doing, so please stop worrying about that. We’re sneaky, and being careful. Also, they aren’t that smart, okay?”

We smiled at each other, and for the first time, I really felt comfortable around him.

“Second, that’s why I… I came back. So we can hopefully make this better.”

“Your first time should have been good, and I made it shitty for you, and I’m sorry.”

“Let’s just put that behind us and figure out what we can do, going forward, to make it better.”

We sipped our water, and I watched as he thought for several moments.

“My girlfriend says it’s better without a condom, but she won’t let me do it with her without using one, and there’s no way in hell we’re risking that anyway.”

If this is going to work, I have to be honest with him.

“I’m on the pill, Anthony.”

His jaw dropped open.

“Why would a virgin be on the pill?” he asked incredulously.

I took a deep breath and tried to figure out how to proceed.

“I don’t want to gross you out, but my periods were really, really bad. My mom took me to see my gynecologist and she put me on the pill to help regulate it, and make it less severe.”

“So I… I… Don’t have to use a condom?”

“Well, from what I hear, that’s the other thing the pill is supposed to do, keep you from getting pregnant.”

“Smart ass.”

We smiled at each other.

“There are other things I know how to do that will make it better for you, if you’re willing to let me do them.”

“Anthony, I trust you, and I’m willing, okay?”

He took my hand and we proceeded to the living room. I took a few seconds to look around. Their house was a lot smaller than ours, but it felt really cozy. The living room was very tastefully decorated with nice paintings and various pictures of Anthony’s parents, and Anthony, at different stages of his life.

“You were a cute baby,” I said softly.

“Of course I was, and I’m still cute,” he said, giving my hand a little squeeze.

This experience was nothing like Monday. I felt so calm and comfortable. Anthony was really nice and really sweet. I realized that even though we hadn’t had many interactions, but when we did, he was always sweet to me. I just never gave him a chance, probably because of my brothers.

We went up the stairs and into his bedroom. Again, I took a second to look around. Like my brothers, he had a lot of posters on his walls of different NFL and NBA stars, as well as some posters of various rock bands. However, unlike my brothers, he had several posters of pretty girls in very small bikinis. That was something that my very religious mother didn’t allow.

“I’ll go into the bathroom and get undressed again.”

I squeezed his hand which stopped him.

“No, let’s get undressed here, together, okay?”

He smiled softly.

We began to undress in front of each other. Again, I felt calm and relaxed. My mom never allowed me to buy sexy lingerie, and this was the first time I wished she would have. I think she was afraid that if I did have racy underwear, I’d only want to show it off to guys, and of course, that was the last thing she wanted.

We slipped into bed together and I felt his naked body press against mine. He leaned in and we gently kissed. It felt really nice, and I realized what a good kisser he really was. Our tongues gently explored each other’s mouths and I felt his hand rest on my stomach. I was a little tense, just because I still wasn’t used to a guy’s hand on my body, but it was nothing like the debilitating nervousness I felt on Monday.

His motions were so tender and gentle, and it felt really nice. He broke our kiss and his mouth traveled down to my breast. His tongue gently flicked over my nipple and delightful waves of pleasure coursed through my body.

God, that feels good.

I could feel my nipples harden as he licked and gently sucked them.

Damn, this is kinda nice.

His mouth moved lower and he kissed my stomach which kinda tickled. But.. in a good way, a very good way.

He kissed a little lower and then got between my legs and I hesitantly opened them.

Oh God!! Is he going to kiss me there?

Suddenly, a surge of electricity went through my body as his tongue made contact with my vagina.

“Oh God,” I gasped.

He looked up and smiled from between my legs, then went back to work on me.

I could feel his tongue licking the lips of my pussy, and then it brushed over my clit which caused a delicious little tingle in the pit of my stomach. I had touched myself before, but his mouth felt much, much better.

I tightly gripped the sheets as the tip of his tongue made light, gentle circles on my clit.
“God Anthony, that feels really good,” I gasped.

I felt him gently slide a finger inside of me while the tip of his tongue continued to make those delicious little circles on my clit and…