In high school, I was a good girl and wanted to save myself for the right guy. Um, well, I guess the honest truth also includes the fact that I never knew any guy in high school who I either wanted or trusted to take my cherry. Mom always said to be honest.
I was a junior and it seemed that most of my friends had lost their virginity well before now. I couldn't help but hear so many of my friends talking about how wonderful sex was, how great it was to have your boyfriend eat you out, then fuck you good. Oh, I'd heard it all and, yes, I was envious and, yes, I was ready.
So, one day, when I was over at my best friend, Karen's, house, the subject got around to sex and I told her what had currently been on my mind.
"You know, I've always thought I would wait for 'Mister Right' to come along and that's who I would first have sex with. But, I don't know. Everybody talks about how great sex is, how it feels, how they love having their pussy licked, fucking non-stop, all that. And, all I've got are my fingers and Dianne's old vibrator." (Dianne is my older sister.)
"Well, Sara, all you need is a guy."
"Oh, brilliant. Any suggestions?"
"If you're really serious, I'd do it."
We both wheeled around and there was Ben, Karen's younger brother. Truthfully, Ben had always been somewhat of a pest growing up but, in the last year or two, he had gotten some height, some muscles and his wavy black hair and deep blue eyes were actually quite fetching. He stood there wearing just basketball shorts, bare-chested, he could have been a male model the last year or so.
"I couldn't help overhear what you said and I could do it."
"Look, twerp, you don't even know how to jack-off properly. Let her get a guy with some experience. Just leave, Ben," Karen barked at him.
"I've done it before and there's several girls that would tell you just how good I am in bed, Karen. I've done it a lot more than you think I have."
While they were going back and forth at each other, I was sitting there looking him over, yes, he had become a rather sexy young man. Nice, really nice.
"Well, maybe Ben's got more experience that you know, Karen," I added to the discussion.
"Well, at least it kind of keeps it in the family, in a way," Karen offered.
Well, he's pretty cute, I was thinking, he was right here, ready to go, so to speak, I was ready, as well, hmm.
"Show us what you've got, Ben, pull it out so we can see," said his sister.
"Um, I'll do that with Sara but not with you in the room."
"Well, look, what the hell, you two go have some fun," Karen said and I got up and asked Ben to show me where his room was.
We went down the hall into his room and closed the door where we both stood looking at each other.
"Um, Ben, I guess, if we're going to do this, we should get undressed, right?" and I began getting undressed and was soon standing naked in front of him still wearing his shorts.
"Ben, are you joining me?" and he jumped slightly and pulled down his shorts and stood there. His penis was large, I'd never seen one on a grown boy and it kind of hung down a bit, all long and pink.
"We'll need a condom, Ben, I'm not on the pill," as I watched his penis swaying slightly. I was now very interested in having sex with my best friend's brother.
"Um, oh, yes, I've got some. Right here," and he dug in the back of his drawer and pulled out a condom and opened the foil wrapper and rolled it on to his stiff penis and stood there.
I was now wondering if he really had any experience at all or if he was just bluffing his way into my panties. Nonetheless, his naked body was giving me rather wonderful feelings between my legs.
I got onto his bed and, when he just stood there, I said, "I'm ready, Ben, come join me," and he laid down next to me and I began rubbing on his sheathed penis and reached over, took his hand and led it between my legs where I told him it was okay to touch me there and he began rubbing my wet slit.
"You look beautiful without your clothes on, Sara. Really beautiful."
We rubbed each other for a few minutes, I knew that I was pretty wet inside so I whispered, "You can do it now, you know, we can have sex," and he got up between my legs and he held his penis as he shoved it against me, trying over and over to get it inside me.
"Let's do this," I said as I lifted my legs high and put them on his shoulders giving him a clear shot into me. He pressed up against me as his penis went in about half way, then he pushed again and went all the way in.
I was really wondering if he'd ever done this before, I was thinking, not.
"Uhh, uhh, uhh, oh, I've…".
It seemed that Ben had cummed less than a minute after putting it in me.
"Can you try some more, Ben?" I asked and he pushed, then pulled, then it just more or less collapsed and his dick came out all limp and floppy.
"I'm sorry, Sara. I just let you down, I'm so sorry."
I held him and felt him shaking slightly as I realized he was crying.
"I lied, I've never done it before, ever. And now, I can't even get a hard-on," and he slumped in my arms naked and sobbing. But naked. As I held him, I pulled his lean, muscled body tight against me, realizing that although he had a sexy body, he was just sixteen and inexperienced, now embarrassed in front of a seventeen-year old girl.
I held him and kissed his face, licking the tears away.
He reached down and pulled off the sagging condom filled so quickly with his cum, embarrassing evidence of his innocence and inexperience.
"I'm so sorry, Sara, so embarrassed, I'm such a failure. I can't even get a hard-on so I can satisfy you."
"Let's just take our time, Ben, it's okay. Karen will never know, I won't tell her, let's just relax and hold each other. It's nice being naked with me, right?"
"Oh, it's wonderful, you are so pretty, the prettiest of all Karen's friends. That's why I so much wanted to do this, it's why I lied about what I'd done with other girls. I hope you don't hate me."
"I think you're very sweet, Ben. It's nice that you thought about me like that. That you wanted me, you know, sexually."
"Oh, I've dreamed about you for so long. Every time I go to bed and, well, I think of you, and I, uh, I think of you a lot."
"Do you masturbate while you think about me? Is that what you're saying?"
"I hope you're not mad, but, yes, I do, I think of you every time I do it."
"How do you think of me, Ben, what are we doing when you are thinking of us together?"
"Like we're having sex or you're down, um, well, like, uh, giving me oral sex."
"Like this, Ben?" and I got up on my knees and lifted up his cock which, now that we were calmly talking about sex together, had gotten somewhat more erect and I lowered my lips over it and began sucking him. I could feel it grow and harden as I sucked and then I felt his hand on my butt, slowly rubbing up and down, so I widened my legs apart and his hand slipped between my thighs and started rubbing my wetness.
I sucked his penis for several more minutes, he was hard, very hard and his dick filled my mouth. Now I wanted it filling my pussy. I pulled up off him and asked, "Think we can try it again, Ben?" and he got another condom, put it on and pressed into me and began thrusting in and out.
"Mmm, Ben, you feel so good inside me. Is it good for you?"
"Oh, it's wonderful. This is how I've dreamed about being with you, like this," as he rubbed my breasts. I had my hands on his hips guiding him in and out of me and it was feeling wonderful. All my friends were right. Fucking is wonderful. The best.
I've masturbated many times so I know the signs of an orgasm when it begins to get close. And, that 'warm pussy' feeling was there, I knew my young lover was over his temporary lapse, he was good and hard inside me now and it felt wonderful.
"This is really nice, Ben, I'm glad we're doing this, are you?"
"Oh, I'm really glad. It's been something I've dreamed about for a long time. I hope we can do it more than just this once."
"Well, my parents don't get home 'til almost six every night. You could come over sometimes and, sure, we could do this more."
"I really want to, I want to get really good at it so I can make you happy, Sara, so I can give you a lot of orgasms. That's what I want to do."
"That's nice, Ben. I feel like you're gonna give me one pretty soon, really soon, the way you're going."
"I hope so, I really want to make you happy. That's what I want the most."
"You're really sweet, Ben" I whispered in his ear and I kissed him as his hips went back and forth, moving his dick in and out of my happy pussy. It was what I wanted.
"Mmm, this is nice, Ben, really nice. I'm glad you wanted to do this. You're just the right guy for my first."
"I really screwed up at first but this is wonderful. I can't believe how good you feel inside. It makes me feel so good."
"Mmm, me, too, really good. It feels so good when you go in and push hard when you get as far in as you can. Oh, yes, like that, it's really good."
It was feeling really good, like I was edging closer and closer to a climax, a strong one, too. I just loved rubbing my hands on his smooth chest as he stroked in and out of me, it was wonderful.
"I'm glad this is turning out better than it started, Sara. I really can't believe that I'm here with you naked and we're, you know, doing this."
"Fucking, Ben, you can say the word, I know what it is. And, yes, it's rather a surprise to me that we're fucking, it's not exactly what I'd planned on doing today. But, I'm glad we are. It's really wonderful. Well, the second time around is better. Don't you agree?"
"Oh, do I. I'd just as soon forget our first time. This is so better."
"Well, you may not agree but I think our first time was very sweet. Probably not what you want to hear, right?"
"Well, it was kind of embarrassing but, after all, it led to right now, our second time and this is wonderful. This is my first time, too, Sara, and I couldn't have any one better than you. It's everything I've ever dreamed of."
"Mmm, it's really feeling good, like I'm getting close…like really close. Just keep…UUH, UUH, OH, BEN, OH, BEN, oh, it feels so good, Ben. Don't stop, just keep going, oh, it feels so good."
My orgasm was worth everything. It was an earth-shattering climax that rang me like a bell. Ben was stroking in and out of me as he began to moan over and over, "Mmm, mmm, mmm. Oh, oh, it feels so good. I think…UUHN, UUHN, uh, uh, oh, Sara, oh, it is so wonderful. I love, you, Sara. I love you so much," and he collapsed over me, panting, slightly damp with perspiration.
I held him tightly as he slowly moved his hips up and down, keeping the feelings going, linking us physically and emotionally together.
"This is so wonderful, Sara, I love you so much. Thank you for everything," and he kissed me softly. I could still feel him inside me, I think I would leave him inside me forever if I could.
We must have fallen asleep for a while, it was about three in the afternoon when we both began to be aware that we were naked in each other's arms.
"Oh, it's not a dream, I was hoping it was real," he murmured sleepily.
"Yes, it's real, all right, Ben, very real. And wonderful."
"Do you want to do it again? I've got more condoms and I sure feel hard again."
"That's nice, Ben, you're a very eager lover. Yes, I feel just a bit sore but I also feel pretty sexy and would like to try it again. Maybe we can do it a different way this time."
"Well, there's from the back, it's called 'doggie-fashion' on the internet. You just get up on your hands and knees and…"
"Yes, Ben, I've heard some of my friends talk about it. Okay, let's try that," and I shifted around and got up and he positioned himself between my legs behind me as he put on another condom and pressed up against me.
I pushed back as he pressed forward and I felt him pop into me about a third of the way, it seemed.
"Are you okay, feel okay?" he asked and I nodded, so he pushed further inside me. Soon, he was taking wonderful, long strokes in and out of me from behind, his hands rubbing me along my butt cheeks and his hand would occasionally dip underneath me as I felt his fingers stroke along my slit, his cock going back and forth. Oh, it felt so sexy.
"Yes, Ben, it really feels wonderful. Is it good for you?"
"Oh, yes, anything with you, Sara, would be just wonderful. You've been so nice to me, I hope I'm making it up to you now."
"Mmm, you're doing just fine, Ben, just fine. This is so much nicer, I think we're both more relaxed now, don't you?"
"You really were understanding at the beginning and I'll never forget that, Sara, and, yes, it's a lot more normal now, more relaxed. I'd love to do this any time you want."
"Well, I don't have a boyfriend and this is so good that I do want to do it more, do it again, that I think you and I can do it if you want."
"Oh, I want to, I really want to."
I was loving getting it from behind. I can see why some of my friends love it this way. You'd think every position would feel the same but they don't. There's a lot to sex that I didn't know but it sure seemed fun learning. I guess I'm just like everybody else. Once they've done it, it's all they want to do.
"Ben, I think I'm getting really close, just keep…UUH, UUH, oh, that feels sooo…oh, oh," I dropped my head down on the bed as Ben fucked me from behind; it just felt so wonderful.
Then, he grunted and pushed hard into me as I felt warmth deep inside me as he emptied himself into me. Oh, this felt so good.
I slid down flat onto the bed, his cock still inside me, he was still moving in and out of me slowly.
"Mmm, I'll do this anytime you want, Sara. This is so perfect."
"It is nice, Ben. I'm glad you offered."
I looked over at the clock and it was after four-thirty.
"I guess we better get up, Ben. Look at the time."
He agreed and we were soon dressed and walking back into their den where Karen was waiting.
"If I heard correctly, sounds like you two had a great time."
"Oh, Karen, it was wonderful. Ben was the perfect choice. He made me so at ease and just helped me along. It was so nice having a guy with a lot of experience," and I smiled at Ben who was standing taller than usual.
I started to make sounds about going home and Ben volunteered to walk me the two blocks to my house.
About half way there, he said, "Sara, you are so great, you really made me look like a stud to my sister. I'll never know how to thank you enough for that, I really won't."
"Oh, I'll think of something, Ben, maybe if you come over in the morning, my parents both work, I'll try to figure out some way for you to thank me. And don't forget the condoms."
When we got to my house, we went around to the side and we kissed each other for several minutes.
"I'll stop on my way over tomorrow at the drug store, I've got to replenish my supply. I think I'll be needing more."
"I'll guarantee it, Ben, I'll guarantee it for sure," and gave him one last kiss.
Ben and I fucked three or four times a week until I went away to college. Even now, though, when I'm home, we manage to be together as much as we can. Every time, I remember that sweet moment, that first time together, when I held him as he wept in my arms. Then, we fuck each other silly.
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<a href="https://www.lushstories.com/stories/first-time/better-the-second-time.aspx">Better The Second Time</a>