If you're a guy, maybe you remember when you first started masturbating, I do. I was nine, my dick would get hard when I played with it and what guy didn't play with his dick, right? And I found that it felt so good when I rubbed it with this small piece of silken cloth that was in my Mom's scrap basket. Oh, that felt so good.
I used that piece of silk and would wash it out and put it up on my top shelf to dry so I could use it again. I was about ten when I learned that a squirt of hand lotion would also do the job quite nicely and was easier to clean up after. Just some tissues and that was all.
So, like many of us, I suppose, I became a prolific masturbator. When I was just ready to turn twelve, the feelings got lots better and I was now shooting white, cloudy, sticky cum.
My best friend, Eric, had also begun playing with himself at about nine and we would do it together when we were together sometimes in the afternoons or sleeping over at the other's house. We never did each other or anything like that, we were completely focused on girls and he had a couple of girly magazines that we drooled over as we beat-off.
If that sounds familiar, well, I've heard more than one guy say he grew up doing the same thing. Most of us played with our cocks and many did it with another boy or boys.
So, one Saturday morning, I showed up at Eric's house and his sister, Pam, came to the door.
"Hi, is Eric home?" I asked.
"Oh, he went with Mom to our aunt's for the day. Won't be back until late. I was just getting a Coke, would you like one?"
So, I told her I would and I followed her back to the kitchen while she got the cans out.
Now, before I go on, you need to know something about Pam. She was a senior in high school, eighteen, exactly four years older than I was and really pretty. She looked a lot like the girls in the magazines what we jerked-off to and she was wearing a cutoff teeshirt and shorts. I wasn't sure but it looked like she was bare under her top.
"Eric's told me about what you two do when you're together, that you play with your dicks."
I felt my face warm and my heart thump when she said that.
"Oh, look at you, your face is so red. You two do that, don't you?"
"I ... well, we ... did he really tell you that?"
"Oh, look, Mark, it's all right, I've watched him do it myself. It's cute to watch."
"Watch, you've watched him, you know, um, play with...".
"I've watched him jack-off, sure, it's fun to watch, I have him do it for me all the time, he seems to like doing it. Would you do it for me?"
"You want me to, you know, that's pretty, um, is there any one else here?" I asked as she slid her hand onto my leg and began to rub. Of course, this was all making my fourteen-year old dick get hard as a rock.
"See, you're all excited, just like my little brother, come on," and she took my hand and pulled me into the den and had me lay down on the sofa.
"Here, let's get you comfy," she said as she knelt down and undid my belt and zipped open my shorts.
If you're wondering if I said anything while this was happening, well, I was kind of in shock. She had just taken over and, well, my dick was eager and willing no matter how the rest of me felt at the time.
She tugged off my shorts, then pulled down my briefs.
"Oh, yours is bigger than Eric's, it's nice," she said as she put her fingers around it and began moving up and down as her other hand went under to feel my balls. "You've got a nice dick, Mark, ever had this inside a girl, inside her pussy? You know, fucking her with it?"
I'd never even felt a girl's tits and she's asking me if I'd fucked a girl yet, so I told her the truth.
"Is it something you'd like to do?" she asked as she knelt there stroking me.
"Oh, yeah, it's something I've dreamed about every time I jack ... um, masturbate."
"You can say, jack-off, Mark, it's okay, I know all those words, you know. Would you do it for me? While I watch?"
"You really want to see me do it?"
"I love watching boys jack-off, I've already told you I watch my brother all the time. Every time I see you when you come over, I want to see you jack-off, now, we're here alone and you can do it for me. Would you?" she asked as she leaned over and kissed me, putting her tongue in my mouth and moving it in and out. That was so sexy.
"Yeah," I told her, my heart pounding as she asked me if I wanted anything like some lotion like her brother used.
So, I told her that would be good and she got up and got it and handed me the bottle. I dribbled some on the top of my dick and began just like I did when I was home in bed. But this time, I had a beautiful eighteen-year old girl watching as I did it. I almost cummed with every stroke.
"You do it with your left hand, are you normally left-handed?" she asked.
"Oh, no, that's funny, huh? I'm right-handed but have always done this left-handed. I really don't know why, I just always have."
"Is it feeling good?"
"Yeah, real good, it's really hot having you here watching me do it."
"I love seeing a boy jack-off, I told you that, it's so hot to watch," and she bent over and kissed me again, her cool hand rubbing over my chest as my fist went up and down.
"Be sure and tell me when you're just about to cum, I don't ever want to miss seeing a boy cum, I love seeing it shoot out."
I was sure working to get her to see me shoot, the whole thing was really sexy, laying there naked for this older girl as she kissed me and caressed my chest while I masturbated for her entertainment ... and for mine.
Her wish was soon granted as I told her I was really close, then arcs of creamy, white cum went shooting up out of my cock as she hooted and howled, "OH, LOOK, LOOK, WOW, I LOVE IT, I LOVE IT, oh, Mark, you shoot farther than Eric, too. Can I lick it off, see if yours tastes different?"
"Sure," I said as she bent down, the first place she licked it off was right on the tip of my dick where some was still oozing out. When her tongue swiped across the head, my cock twitched in pleasure. Then, she licked it off my stomach and abdomen, giving my dick a quick suck as she finished.
"I like the taste of yours, it's a little salty but nice. Ever have a girl suck it?" she asked as she held it by two fingers.
"No, but I've heard it really feels good," I answered, hopefully giving her the idea.
"Maybe another time, it's something I really like doing. Have you ever given oral to a girl, ever eaten her out?"
"No, but I'd like to," I answered again hoping she'd say yes. And she did, "It's something I just love. It always gets me in the mood to be fucked, so, maybe that might interest you, Mark? Would you like to do oral on my pussy?"
"You sure we have all day?" I asked hesitantly as she told me that Eric and his Mom wouldn't be back until near midnight. "Yeah, I'd like to but I've never done it before so I might not do it right."
She stood up and began taking her clothes off as I watched intently as her breasts became exposed when her cutoff top dropped to the floor. Then her shorts and panties came down as she stood there beautifully naked.
Eric's sister was really pretty and her breasts were perfect. They just stood straight out, all nice and firm, each one tipped with a soft, pink nipple. Her pussy was bare except for a little mustache just above, of brown hair. She was a blond on her head so I figured that she must have it colored that way.
She had me get up so she could sit down on the sofa, spreading her legs open as I sat in front of her. She reached forward and took my face on each side, leading my mouth right to her pussy which I began to lick and suck on.
She tasted salty, kind of, but it was nice, and she sure did like what I was doing, immediately moaning and moving around.
"Mmm, good, open me with your fingers, Mark, then get your tongue up in and wiggle it around, lick all around my hole, make me go crazy."
I did everything she asked and even more as ideas would come into my mind. She was really getting into it big time as I tongued her like I was fucking her, poking my tongue in and out, then licking it all around her opening.
"Mmm, oh, Mark, omigod, you're gonna get me off, you are so good, oh, my pussy is going crazy," she cried out as she shook and trembled as I licked and tongued.
Then her legs locked around my head, pulling me into her pussy tightly, I almost couldn't breathe, and she humped up and down against my face as she shrieked, "OMIGOD, OH, OOH, OOH, UUH, UUH, uh, mmm, mmm, oh, Mark, you are so good, you really did my pussy good, oh, man, I still am rocking from it."
I looked up, my wet mouth smiling as she said, "Mmm, come up here. You said you haven't fucked a girl yet, right?"
I shook my head no and she pulled me up, opening wide to say, "Well, here's your chance. Here's your first pussy, Mark, have fun. You know what to do, right?"
I basically showed her that I had some ideas as I pushed my hard dick up into her and began what I've dreamed about so long. She spread open as wide as she could while I looked down and marveled at the sight of my cock sliding into its first pussy ever, that of a hot, eighteen-year old high school senior. I wasn't ever brave or foolish enough to imagine that this fourteen-year old eighth grader would be losing his cherry to such a hot, older girl. Heaven, yes, I was in heaven.
I think every boy and girl imagines how it's going to feel the first time you have sex, how it will feel as your cock slides back and forth or how it feels to have that cock slipping in and out of your eager pussy. Well, like most of us, I suppose, I only had masturbation as a measure and, well, as good as that could be, oh, this was so much better.
"You like it, Mark? You look pretty happy."
"Oh, I love it, it's just so better than I ever thought. Am I doing it okay? I can try whatever you like, just tell me what you want me to do, okay?" I told her panting as I went in and out.
"You're doing it just fine, this is your first time and I want it to be just the best for you. I love young guys like you, you're so cute and eager, so much fun when you're doing all this for the first time ever."
"So, you've been with guys my age before?"
"Oh, yeah, you're the fifth. One was, hmm, I'm not sure, one was fifteen and the rest were like you, fourteen. See, I like 'em young and eager and their dick's hard," she laughed as I plunged back and forth.
"If some are my age, maybe I go to school with some of them," I ventured.
"Well, I know one of them you know, it's my brother. He fucks me all the time and he loves to jack-off for me. I suck his dick, too, and he eats me out, just all the time. After this, I'll suck you nice and slow, boys love when I do it that way."
"So, you and Eric have been doing this? I really love doing this, I just never hoped I'd be able to, never dreamed you'd let me do this," I told her as I pumped back and forth.
"Well, I've been wanting to get you alone for months, Mark, my brother told me your dick was bigger than his and I've wanted it in me ever since he told me that. And, I really like it. Next, I want it in my mouth; just wait until I suck your dick, you'll love it."
I was fucking back and forth in and out of her upturned pussy, she had pulled her knees back up under her arms so I was up over her leading my long, thin dick down into her and then back up, all the way out, then back down inside her again. God, it was delicious feeling. Every time the tip of my dick slid in between her pussy lips down into her, it was just the best feeling, just incredible.
"Mmm, I like how you're taking it all the way out and putting it back in each time, that's awesome. I could let you fuck me like this just forever, I knew you'd be good. Mmm," she moaned.
I kept stroking in and out of her, penetrating her anew each time I went down, the feelings so good I could almost not stand it. It was that good.
"Mmm, you fuck good, Mark, for a first-timer. I'll bet you get better with practice and maybe I'll just arrange it so you can get lots of practice. Would you like that? Maybe come over after school and fuck me?"
I couldn't believe I was getting an offer like that from my best friend's older sister but I jumped at the chance, "Yeah, oh, yeah, that would be great. Um, Eric might find out, though, might wonder why I was coming over to see you."
"Oh, silly, I already fuck him most afternoons. You would just join in. I'd take care of both of you horny guys and you could do me as much as you two could. Oh, that makes me feel so hot just thinking about it."
"I think ... oh, yeah, I'm gonna cum. Are you protected, I'll take it out if you aren't?"
"Oh, you learned your sex-ed really well, Mark. But, I'm on the pill and you can just go ahead and cum, just shoot me full, it's okay," she told me and I just went on knowing I was very, very close.
And, then it happened - my very first ejaculation where it was meant to be, deep inside a pussy. Oh, my whole body convulsed as spurt after spurt emptied deep into her as she gripped my hips pulling me tight.
"Cum, Mark, cum in me, mmm, yes, oh, yes, oh, you're making me cum, mmm, fuck me, fuck me," she shouted as I began going as fast as I could.
Soon, we were laying there, breathing hard, kissing each other as I still slowly moved in and out of her while she kept her legs wrapped around me. It was heaven.
"Mmm, good, huh?" she murmured.
"Oh, I can't believe it happened, I'm so glad it did, Pam, it was the best first time I could ever have."