My First Everything - Cover

My First Everything

Copyright© 2006 by Openbook

Chapter 21

Erotica Sex Story: Chapter 21 - A coming of age story for a group of early teens coming of age in the late 1950's. Larry enjoys the attentions of the girls in his school, and around his neighborhood.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   Romantic   Lesbian   BiSexual   Heterosexual   Fiction   Tear Jerker   Aunt   Nephew   Spanking   Rough   Humiliation   First   Masturbation   Exhibitionism   Caution   Violence  

"No, you do yourself and I'll do myself. If we tried to really do it like you said, it would get real painful for you, and messy too."

"Can we go in my bedroom though? We could kiss a little before we did the other. It would be more romantic for us."

We went into her room. It had a double bed and a single in it. Karen told me the single was for when she had friends over for sleepovers. Having two beds in the room made it seem too small to me. What I really liked was that there was a bathroom right next to her room. It was connected right to it, and also to the guest bedroom next door. She showed me that room, and it had another double bed. Being an only child, Karen's parents were protective of her, as well as indulgent. She wasn't able to go on dates until she turned fourteen, but she had hosted many sleepovers at her house where she and her guests took up both bedrooms and the floor. She told me that her sleepover party for her thirteenth birthday had fourteen girls sleeping at her house.

"I've been hearing some stories about what you girls do at sleepovers, Karen. I thought it was all innocent like when guys camp out together in tents in the back yard. I heard you girls practice kissing and do other stuff together too."

"I never did. Except for some kissing, when I was about eleven or twelve. There are some girls that like to do more, but they usually all hang around together, after awhile. Larry, let's take all of our clothes off and kiss on the bed." She didn't wait to see if I wanted to do that, unbuttoning her dress from the back and then lifting it off over her head like a pullover shirt. All she was wearing then were her panties and bra. She stood there, beside her bed, looking at me and waiting for me to start getting undressed. There was a look in her eyes, challenging me, almost daring me to undress with her. I started unbuttoning my shirt. Smiling, she reached back to unhook her bra. I took my slacks off, after first removing my shoes. I took my underpants off too, so that all that remained was my socks. Karen reached both hands into the waistband of her panties and pulled them down and completely off of her. I sat on the bed and removed my socks. When I was finished, Karen told me to scoot over to the inside of the bed, which I did.

Karen climbed onto the bed herself, moving over to where I was and laying down halfway on me, and halfway on the mattress. We started kissing. Kissing when you are both naked is a lot different than when you have clothes on. For one thing, wherever you touch there is bare skin, and for another, everything is open and available to your touch. We hadn't been kissing for more than two minutes before I had my finger between her legs, rubbing her pussy, and she had hers on my cock, softly stroking it. I started kissing both of her breasts, including pushing them together so that I could lick both areolas and nipples at the same time. Her breasts were big and firm, but very soft and rubbery too. I started sucking on one of her nipples, and she really seemed to like that a lot. I rolled with her until I was on top of her, still sucking on her nipple.

"Karen, can I just rub it on your pussy for a minute? I won't put it in you. I just want to feel what it's like."

"You can put it in if you want to, Larry, I told you that before."

I had my hand on my cock by now, and was trying to lean forward while balancing my body weight on my other hand and my toes and one knee. As soon as my cock touched Karen's pussy, she lifted her legs up in the air. When she did that, I looked down and saw that her pussy lips were opened. I could see that little tear in her hymen too. I put the head of my dick right where the tear was and then started moving it all up and down and around her pussy. When my arm got too tired from holding me up. I leaned up further, so that my dick was on her stomach, and lowered my body down on hers. We stayed like that for a long time kissing. At some point, I'm not sure which of us did it, but either she moved up higher on the bed, or I moved down lower, and my dick was back in contact with her pussy. She still had her legs held up, although her heels were back down on the mattress.

I know that I was the first one that started moving. We were kissing, and Karen's arms were wrapped around me, so that her hands were on my back. When I started moving up and back, it made my dick slide up and back on the top part of her pussy. Then, she moved up so that it was touching her pussy even more. The more I slid, the better it felt. One thing was certain, my dick had never been harder. Her pussy was pretty wet too, and my cock was definitely leaking something itself. My cock slid easily, even though I still had a lot of my weight on her. Karen lifted her legs up until her feet were way up above us, and this made even better contact for the two of us. I had never felt anything as good as what we were doing. I'm pretty sure that Karen felt the same, because every time I slid my body up, she helped me with her arms. Every time I slid back down, she helped to keep me pressed down firmly on her, so that we could both feel maximum contact. She was making a lot of noises too. Encouraging noises, and groaning in pleasure whenever I slid along her clit on my downward slide.

I was sliding up again when she suddenly lifted herself up even more, and my cock head pushed really hard against her pussy hole. Karen yelled at me to stop.

"Larry, stop! Ohh, that really hurt. You almost went in me that time."

"I'm sorry, Karen, you moved just when I was pressing down and moving forward. I didn't mean to hurt you."

"No, that's okay. I couldn't help moving like that. It feels so good when you do that other thing. It doesn't hurt any more. Do that other thing where you slide up and back. Can you maybe do it a little bit faster too?"

I settled back down like I had been before, this time I was careful to place the head of my dick above her clit so there was no way I could slip into her hole by accident. We went back to kissing and sliding, and then, Karen started cumming. This made both of us move around even faster, and, on accident, my dick slammed into her hole. This time, even though it had to really hurt her, Karen pressed me even more tightly against her. I could tell that she didn't want me to move. We stayed just like we were for a couple of minutes. I was about halfway in her, and I could feel her pussy still having little contractions around my dick.

"I better take it out. I don't have a rubber on."

"Just don't move for another minute. I'll tell you when to move it, all right?" I just nodded. I looked down at her face, and I swear she looked just like an angel. She was grinning at me, and her eyes had watered up. I don't think she was crying because it hurt her though. She seemed too happy for her to be in that much pain. "We did it, Larry. I'm not a virgin anymore."

I was thinking that it didn't really count for me yet, because I hadn't cum. I hadn't even done any real moving in and out. Just in, and only about halfway in. There was no question though that Karen wasn't a virgin anymore.

"If I leave it in, Karen, I should have a rubber on, because I'm leaking precum into your pussy."

"Take it out then, but go slow, because it still hurts a little."

Thinking it was like taking a band aid off, I decided it would be less painful if I just pulled it back out at the speed it had gone into her, fast. That's exactly what I did, which caused Karen to pout.

"It felt better when it was in me, Larry. Now it's starting to hurt worse. Can you put that rubber on and put it back just like before? Don't put any more in though."

This time, I had no trouble getting my rubber on. I guess the practice I'd had with Clara had helped me there. Karen winced a little as I was putting it back inside her. We went back to kissing, and, in a little while, Karen started moving her hands up and down on my back. I took it about halfway back and then started moving back and forth, in little two inch strokes. Now, I felt like we were really screwing. I started going in a little bit deeper, but not very quickly. It took awhile, but finally, it was almost all the way in, but I was hitting the bottom with her. When I started taking longer strokes, Karen started doing that thing again on my back, like she was urging me to do even more to her. I felt myself getting ready to cum, and really started going as hard and as fast as I could. I was at the point where all I could think about was cumming, and then I did.

I reached down to try to make sure the rubber came out when I pulled out of her. I went into the bathroom and took it off and flushed it down the toilet. I washed my dick off in the sink, and then took a pee. Karen came into the bathroom to watch me take the pee.

"I only ever saw my dad do that, back when I was a little kid." I smiled over at her. She had a little bit of blood on her thigh, probably from when I pulled my dick out. Other than that, she looked fine.

"Do you feel okay, Karen? I hope it didn't hurt you too much?"

"It didn't hurt as bad as I thought it would. It was like a really hard pinch at first, and then after, it felt like I was doing something when I was bruised. Mostly it felt really good, especially towards the end. I'm glad we did it."

"I'm glad too. At first, I wasn't sure about it, because of all that other stuff. When it happened though, it felt like it was right for us. I'm sure we'll both remember today."

"Now that I did it with you, are you still going to go out with other girls?"

I knew this was coming. I had known it before I ever put it in her. It was the way her mind worked. It wasn't like she had even tried to hide it.

"Why wouldn't I? I told you that I didn't want to go steady."

"But, that was before. I thought if I let you do it to me, so you could see how much I like you, that you would change your mind about that."

"Karen, that was my first time too. I enjoyed it more because it was with you, and not some girl that it wouldn't be as special for. That doesn't mean that we have to go steady. If you had said, you can do it to me if you want to go steady, I'd have said no. I did it because, right then, it felt like a good thing to do. If you did it only to try to force me to not go out with other girls, then you did it for the wrong reason."

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